Organic electroluminescent element and electronic device

Abstract

The invention relates to an organic electroluminescent element and an electronic device. An organic electroluminescent element having a positive electrode, a negative electrode, and a light-emitting region located between the positive electrode and the negative electrode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer is directly adjacent to the second light-emitting layer, 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

[0001] This invention application is a divisional application of PCT patent application PCT / JP2019 / 040711, and the invention patent application named "Organic Electroluminescent Elements and Electronic Devices". The application number of the parent case entering China is 201980068418.7. Technical Field

[0002] The present invention relates to an organic electroluminescent element and an electronic device. Background Art

[0003] When voltage is applied to an organic electroluminescent element (hereinafter referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0004] An organic EL element includes a light-emitting layer between an anode and a cathode, and may also have a laminated structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

[0005] Patent Documents 1 to 4 disclose deuterated arylanthracene compounds that can be used in electronic applications, and electronic devices having active layers containing such deuterated compounds.

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: WO2010 / 099534

[0009] Patent Document 2: WO2010 / 135395

[0010] Patent Document 3: WO2011 / 028216

[0011] Patent document 4: WO2010 / 071362. Summary of the Invention

[0012] The object of the present invention is to provide an organic electroluminescent element and an electronic device with a long life using a deuterated compound.

[0013] According to one embodiment of the present invention, the following organic electroluminescent element is provided.

[0014] An organic electroluminescent element comprising:

[0015] anode,

[0016] cathode, and

[0017] a light emitting region located between the anode and the cathode,

[0018] The light-emitting region includes a first light-emitting layer and a second light-emitting layer.

[0019] The first light-emitting layer is directly adjacent to the second light-emitting layer.

[0020] The first light-emitting layer is located between the anode and the second light-emitting layer.

[0021] Either the first light-emitting layer or the second light-emitting layer contains a compound having at least one deuterium atom.

[0022] According to another aspect of the present invention, there is provided an electronic device having the organic electroluminescent element.

[0023] According to the present invention, a long-life organic electroluminescent element and electronic device can be provided using a deuterated compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 : A diagram showing a schematic configuration of an organic EL element according to a first embodiment of the present invention.

[0025] Figure 2 : A diagram showing a schematic configuration of an organic EL element according to a second embodiment of the present invention.

[0026] Figure 3 : A diagram showing a schematic configuration of an organic EL element according to a third embodiment of the present invention. DETAILED DESCRIPTION

[0027] [definition]

[0028] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0029] In the present specification, in chemical structural formulas, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a position capable of bonding that is not explicitly indicated by symbols such as "R" or "D" representing a deuterium atom.

[0030] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring structure. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" recorded below is also the same unless otherwise specified. For example, the number of ring carbon atoms of a benzene ring is 6, the number of ring carbon atoms of a naphthalene ring is 10, the number of ring carbon atoms of a pyridine ring is 5, and the number of ring carbon atoms of a furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0031] When a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring.

[0032] In this specification, the number of ring atoms represents the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a cyclic structure (e.g., a monocyclic ring, a condensed ring, a ring set). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is also the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. The hydrogen atoms bonded to the carbon atoms of the pyridine ring and the quinazoline ring and the atoms constituting the substituent are not included in the number of ring atoms.

[0033] In this specification, the term "a substituted or unsubstituted ZZ group having 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 number of carbon atoms in the substituent when it is substituted. Herein, "YY" is greater than "XX," and "XX" and "YY" each represent an integer greater than 1.

[0034] In this specification, the term "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" means the atomic number of the ZZ group when it is unsubstituted and does not include the atomic number of the substituent when it is substituted. Herein, "YY" is greater than "XX," and "XX" and "YY" each refer to an integer greater than 1.

[0035] "Unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted by a substituent and has a hydrogen atom bonded thereto. Alternatively, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0036] The substituents described in this specification are described below.

[0037] Unless otherwise specified in the present specification, the “unsubstituted aryl group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0038] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0039] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0040] Unless otherwise specified in the present specification, the "unsubstituted alkenyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0041] Unless otherwise specified in the present specification, the "unsubstituted alkynyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0042] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0043] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0044] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0045] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0046] Specific examples of the "substituted or unsubstituted aryl group" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups and substituted aryl groups. (Herein, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") Hereinafter, when "aryl" is mentioned alone, both "unsubstituted aryl groups" and "substituted aryl groups" are included.

[0047] A "substituted aryl group" is a case where an "unsubstituted aryl group" has a substituent, and examples of "unsubstituted aryl groups" and "substituted aryl groups" described below can be cited. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl group" described in this specification also includes a group where an "unsubstituted aryl group" has a substituent further has a substituent, and a group where a "substituted aryl group" has a further substituent.

[0048] Unsubstituted aryl:

[0049] Phenyl,

[0050] p-Biphenyl,

[0051] m-Biphenyl,

[0052] o-biphenyl,

[0053] 4-terphenyl-4-yl,

[0054] 4-terphenyl-3-yl,

[0055] 4-terphenyl-2-yl,

[0056] m-terphenyl-4-yl,

[0057] m-terphenyl-3-yl,

[0058] m-terphenyl-2-yl,

[0059] o-terphenyl-4-yl,

[0060] o-terphenyl-3-yl,

[0061] o-terphenyl-2-yl,

[0062] 1-naphthyl,

[0063] 2-naphthyl,

[0064] Anthracene,

[0065] Benzanthryl,

[0066] Fiki,

[0067] Triphenylene,

[0068] Phenalene,

[0069] Pyrene

[0070] base,

[0071] Benzo base,

[0072] triphenylene,

[0073] Benzotriphenylene,

[0074] tetraphenyl,

[0075] Pentaphenyl,

[0076] Fluorenyl,

[0077] 9,9'-spirobifluorenyl,

[0078] Benzofluorenyl,

[0079] Dibenzofluorenyl,

[0080] Fluoranthene base,

[0081] Benzofluoranthene,

[0082] Perylene.

[0083] Substituted aryl groups:

[0084] o-Tolyl,

[0085] m-Tolyl,

[0086] p-Tolyl,

[0087] p-Xylyl,

[0088] m-xylyl,

[0089] o-xylyl,

[0090] p-Isopropylphenyl,

[0091] m-isopropylphenyl,

[0092] o-isopropylphenyl,

[0093] tert-Butylphenyl,

[0094] m-tert-butylphenyl,

[0095] o-tert-butylphenyl,

[0096] 3,4,5-trimethylphenyl,

[0097] 9,9-dimethylfluorenyl,

[0098] 9,9-diphenylfluorenyl,

[0099] 9,9-bis(4-methylphenyl)fluorenyl,

[0100] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0101] 9,9-di(4-tert-butylphenyl)fluorenyl,

[0102] Cyanophenyl,

[0103] triphenylsilylphenyl,

[0104] trimethylsilylphenyl,

[0105] Phenyl naphthyl,

[0106] Naphthylphenyl.

[0107] The term "heterocyclic group" as used herein refers to a cyclic group containing at least one heteroatom among the ring atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0108] The "heterocyclic group" described in the present specification may be a monocyclic group or a condensed ring group.

[0109] The "heterocyclic group" described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.

[0110] Specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (Specific Example Group G2) include the following unsubstituted heterocyclic groups and substituted heterocyclic groups. (Herein, an unsubstituted heterocyclic group refers to a case where a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to a case where a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") Hereinafter, when a "heterocyclic group" is mentioned alone, both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0111] A "substituted heterocyclic group" is a case where an "unsubstituted heterocyclic group" has a substituent, and examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" described below can be cited. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes a group where an "unsubstituted heterocyclic group" has a substituent further has a substituent, and a group where a "substituted heterocyclic group" has a further substituent.

[0112] Unsubstituted heterocyclic groups containing nitrogen atoms:

[0113] Pyrrolyl,

[0114] Imidazole,

[0115] Pyrazolyl,

[0116] triazole,

[0117] Tetrazolyl,

[0118] Oxazolyl,

[0119] Isoxazolyl,

[0120] Oxadiazolyl,

[0121] Thiazolyl,

[0122] Isothiazolyl,

[0123] Thiadiazole,

[0124] Pyridyl,

[0125] Pyridazinyl,

[0126] Pyrimidine group,

[0127] Pyrazinyl,

[0128] Triazine group,

[0129] Indolyl,

[0130] Isoindolyl,

[0131] Indolizinyl,

[0132] Quinolizinyl,

[0133] Quinolinyl,

[0134] Isoquinolinyl,

[0135] Cinnoline,

[0136] Phthalocyanine,

[0137] Quinazoline,

[0138] Quinoxaline,

[0139] Benzimidazole,

[0140] Indazolyl,

[0141] Phenanthroline,

[0142] Phenanthridinyl,

[0143] Acridinyl,

[0144] Phenoxazine,

[0145] Carbazolyl,

[0146] Benzylcarbazolyl,

[0147] Morpholino,

[0148] Phenoxazine,

[0149] Phenothiazine,

[0150] Azacarbazolyl,

[0151] Diazacarbazolyl.

[0152] Unsubstituted heterocyclic groups containing oxygen atoms:

[0153] furanyl,

[0154] Oxazolyl,

[0155] Isoxazolyl,

[0156] Oxadiazolyl,

[0157] Xanthoxylum,

[0158] Benzofuranyl,

[0159] Isobenzofuranyl,

[0160] dibenzofuranyl,

[0161] naphthobenzofuranyl,

[0162] Benzoxazolyl,

[0163] Benzisoxazolyl,

[0164] Phenoxazine,

[0165] Morpholino,

[0166] dinaphthofuranyl,

[0167] Azadibenzofuranyl,

[0168] Diazadibenzofuranyl,

[0169] Azanaphthobenzofuranyl,

[0170] naphthyridinylbenzofuranyl.

[0171] Unsubstituted heterocyclic group containing a sulfur atom:

[0172] Thiphenyl,

[0173] Thiazolyl,

[0174] Isothiazolyl,

[0175] Thiadiazole,

[0176] benzothiophene,

[0177] Isobenzothiophene,

[0178] dibenzothiophene,

[0179] Naphthobenzothiophene,

[0180] Benzothiazolyl,

[0181] Benzisothiazolyl,

[0182] Phenothiazine,

[0183] dinaphthothienyl,

[0184] Azadibenzothiophene,

[0185] Diazadibenzothiophene,

[0186] Azanaphthobenzothiophene,

[0187] Diazinobenzothiophenyl.

[0188] Substituted heterocyclic groups containing nitrogen atoms:

[0189] (9-phenyl)carbazolyl,

[0190] (9-biphenyl)carbazolyl,

[0191] (9-phenyl)phenylcarbazolyl,

[0192] (9-naphthyl)carbazolyl,

[0193] Diphenylcarbazol-9-yl,

[0194] phenylcarbazol-9-yl,

[0195] Methylbenzimidazole,

[0196] Ethylbenzimidazolyl,

[0197] Phenyltriazine,

[0198] Biphenyl triazine group,

[0199] Diphenyltriazine,

[0200] Phenylquinazolinyl,

[0201] Biphenylquinazolinyl.

[0202] Substituted heterocyclic groups containing oxygen atoms:

[0203] Phenyldibenzofuranyl,

[0204] Methyldibenzofuranyl,

[0205] tert-Butyldibenzofuranyl,

[0206] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0207] Substituted heterocyclic groups containing a sulfur atom:

[0208] Phenyldibenzothiophene,

[0209] Methyldibenzothiophene,

[0210] tert-Butyldibenzothienyl,

[0211] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0212] A monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocycle containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and a monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocycle having a substituent:

[0213] [Chemistry 1]

[0214]

[0215] In formulas (XY-1) to (XY-18), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0216] The heterocycles represented by the above formulae (XY-1) to (XY-18) have a bond at an arbitrary position to form a monovalent heterocyclic group.

[0217] The monovalent group derived from the unsubstituted heterocycle represented by the above formulae (XY-1) to (XY-18) having a substituent means that the hydrogen atom bonded to the carbon atom constituting the skeleton in these formulae is replaced by a substituent, or X A 、Y A It is NH or CH2, and the hydrogen atom in these NH or CH2 is replaced by a substituent.

[0218] Specific examples of the "substituted or unsubstituted alkyl group" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups and substituted alkyl groups. (Herein, an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when "alkyl" is mentioned alone, both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0219] "Substituted alkyl" refers to a case where an "unsubstituted alkyl" has a substituent, and examples of "unsubstituted alkyl" and "substituted alkyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are merely examples, and "substituted alkyl" described in this specification also includes groups where an "unsubstituted alkyl" has a substituent and further has a substituent, and groups where a "substituted alkyl" has further substituents.

[0220] Unsubstituted alkyl groups:

[0221] methyl,

[0222] Ethyl,

[0223] n-propyl,

[0224] Isopropyl,

[0225] n-Butyl,

[0226] Isobutyl,

[0227] sec-butyl,

[0228] tert-butyl.

[0229] Substituted alkyl groups:

[0230] Heptafluoropropyl (including isomers),

[0231] Pentafluoroethyl,

[0232] 2,2,2-trifluoroethyl,

[0233] trifluoromethyl.

[0234] Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (Specific Example Group G4) include the following unsubstituted alkenyl groups and substituted alkenyl groups. (Herein, "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) Hereinafter, when "alkenyl group" is mentioned alone, both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0235] "Substituted alkenyl" refers to a case where an "unsubstituted alkenyl" has a substituent, and examples of "unsubstituted alkenyl" and "substituted alkenyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are merely examples, and "substituted alkenyl" described in this specification also includes "unsubstituted alkenyl" groups further having a substituent and "substituted alkenyl" groups further having a substituent.

[0236] Unsubstituted alkenyl and substituted alkenyl:

[0237] Vinyl,

[0238] Allyl,

[0239] 1-butenyl,

[0240] 2-Butenyl,

[0241] 3-Butenyl,

[0242] 1,3-Butadienyl,

[0243] 1-Methylvinyl,

[0244] 1-methylallyl,

[0245] 1,1-dimethylallyl,

[0246] 2-methylallyl,

[0247] 1,2-Dimethylallyl.

[0248] Specific examples of the "substituted or unsubstituted alkynyl group" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups. (Herein, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when referring to an "alkynyl group" alone, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0249] The "substituted alkynyl group" is a case where the "unsubstituted alkynyl group" has a substituent, and examples thereof include the following "unsubstituted alkynyl group" having a substituent.

[0250] Unsubstituted alkynyl:

[0251] Ethylene.

[0252] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups. (Herein, "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") Hereinafter, when "cycloalkyl group" is mentioned alone, both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are included.

[0253] "Substituted cycloalkyl" refers to a case where an "unsubstituted cycloalkyl" has a substituent. Examples of the following "unsubstituted cycloalkyl" and "substituted cycloalkyl" groups include substituent groups and substituted cycloalkyl groups. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are merely examples. The "substituted cycloalkyl" described in this specification also includes substituent groups where an "unsubstituted cycloalkyl" has a further substituent and substituent groups where a "substituted cycloalkyl" has a further substituent.

[0254] Unsubstituted aliphatic cyclic group:

[0255] Cyclopropyl,

[0256] Cyclobutyl,

[0257] Cyclopentyl,

[0258] Cyclohexyl,

[0259] 1-adamantyl,

[0260] 2-adamantyl,

[0261] 1-norbornyl,

[0262] 2-Norbornyl.

[0263] Substituted cycloalkyl:

[0264] 4-Methylcyclohexyl.

[0265] As described in this specification, -Si(R 901 )(R 902 )(R 903 Specific examples of the group represented by (specific example group G7) include:

[0266]

[0267]

[0268] In this article,

[0269] G1 is the "aryl group" described in Specific Example Group G1.

[0270] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0271] G3 is the "alkyl group" described in the specific example group G3.

[0272] G5 is the "alkynyl group" described in Specific Example Group G5.

[0273] G6 is the "cycloalkyl group" described in Specific Example Group G6.

[0274] As described in this specification, -O-(R 904 Specific examples of the group represented by (specific example group G8) include:

[0275] -O(G1),

[0276] -O(G2),

[0277] -O(G3),

[0278] -O(G6).

[0279] In this article,

[0280] G1 is the "aryl group" described in Specific Example Group G1.

[0281] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0282] G3 is the "alkyl group" described in the specific example group G3.

[0283] G6 is the "cycloalkyl group" described in Specific Example Group G6.

[0284] As -S-(R 905 Specific examples of the group represented by (specific example group G9) include:

[0285] -S(G1),

[0286] -S(G2),

[0287] -S(G3),

[0288] -S(G6).

[0289] In this article,

[0290] G1 is the "aryl group" described in Specific Example Group G1.

[0291] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0292] G3 is the "alkyl group" described in the specific example group G3.

[0293] G6 is the "cycloalkyl group" described in Specific Example Group G6.

[0294] As described in this specification, -N(R 906 )(R 907 Specific examples of the group represented by (specific example group G10) include:

[0295]

[0296]

[0297] In this article,

[0298] G1 is the "aryl group" described in Specific Example Group G1.

[0299] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0300] G3 is the "alkyl group" described in the specific example group G3.

[0301] G6 is the "cycloalkyl group" described in Specific Example Group G6.

[0302] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

[0303] Specific examples of "alkoxy" groups described herein are groups represented by -O(G3), where G3 is an "alkyl" group described in Specific Example Group G3. Unless otherwise specified herein, an "unsubstituted alkoxy" group has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0304] Specific examples of "alkylthio" described herein include -S(G3), where G3 represents an "alkyl" group as described in Specific Example Group G3. Unless otherwise specified herein, an "unsubstituted alkylthio" group has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0305] Specific examples of "aryloxy" described herein are groups represented by -O(G1), where G1 is an "aryl group" described in Specific Example Group G1. Unless otherwise specified herein, an "unsubstituted aryloxy" group has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0306] Specific examples of "arylthio" described herein are groups represented by -S(G1), where G1 is an "aryl group" described in Specific Example Group G1. Unless otherwise specified herein, an "unsubstituted arylthio" group has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0307] Specific examples of "aralkyl" groups described herein are groups represented by -(G3)-(G1). Here, G3 represents an "alkyl" group described in Specific Example Group G3, and G1 represents an "aryl" group described in Specific Example Group G1. Therefore, "aralkyl" is one embodiment of a "substituted alkyl" group substituted with an "aryl" group. Unless otherwise specified herein, an "unsubstituted alkyl" group substituted with an "unsubstituted aryl" group, i.e., an "unsubstituted aralkyl" group, has 7 to 50 carbon atoms, preferably 7 to 30, and more preferably 7 to 18 carbon atoms.

[0308] Specific examples of "aralkyl" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0309] Unless otherwise described in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, 9,9'-spirobifluorenyl, 9,9-diphenylfluorenyl, etc.

[0310] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenyl)carbazolyl group phenyl)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]carbazole 1-jk]carbazolyl, dibenzothiophene, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxazolyl, pyrrolidinyl, piperidinyl, piperazinyl, imidazolidinyl, indolo[3,2,1-jk]carbazolyl, dibenzothiophene, and the like.

[0311] Unless otherwise specified in the present specification, the dibenzofuranyl group and dibenzothienyl group are specifically any of the following groups.

[0312] [Chemistry 2]

[0313]

[0314] In formulas (XY-76) to (XY-79), X B is an oxygen atom or a sulfur atom.

[0315] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0316] Unless otherwise specified, the term "substituted or unsubstituted arylene group" used herein refers to a group obtained by modifying the aforementioned "aryl group" into a divalent group. Specific examples of "substituted or unsubstituted arylene groups" (Specific Example Group G12) include groups obtained by modifying the "aryl group" described in Specific Example Group G1 into a divalent group. Specifically, specific examples of "substituted or unsubstituted arylene groups" (Specific Example Group G12) include groups obtained by removing one hydrogen atom bonded to a ring carbon of the "aryl group" described in Specific Example Group G1.

[0317] Specific examples of the "substituted or unsubstituted divalent heterocyclic group" described in this specification (Specific Example Group G13) include those obtained by modifying the "heterocyclic group" described in Specific Example Group G2 into a divalent group. Specifically, specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include those obtained by removing one hydrogen atom bonded to a ring-forming atom of the "heterocyclic group" described in Specific Example Group G2.

[0318] Specific examples of the "substituted or unsubstituted alkylene group" described in this specification (Specific Example Group G14) include groups obtained by replacing the "alkyl group" described in Specific Example Group G3 with a divalent group. That is, specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include groups obtained by removing one hydrogen atom bonded to a carbon atom forming an alkane structure from the "alkyl group" described in Specific Example Group G3.

[0319] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any of the following groups.

[0320] [Chemistry 3]

[0321]

[0322] In formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R 908 As a substituent.

[0323] m901 is an integer from 0 to 4. When m901 is 2 or more, multiple R 908 They may be the same as or different from each other.

[0324] [Chemistry 4]

[0325]

[0326] In formula (XY-30) to (XY-40), R909 Each independently represents a hydrogen atom or a substituent. 909 They may be bonded to each other via a single bond to form a ring.

[0327] [Chemistry 5]

[0328]

[0329] In formulas (XY-41) to (XY-46), R 910 As a substituent.

[0330] m902 is an integer from 0 to 6. When m902 is 2 or more, multiple R 910 They may be the same as or different from each other.

[0331] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any of the following groups.

[0332] [Chemistry 6]

[0333]

[0334] In formula (XY-50) to (XY-60), R 911 is a hydrogen atom or a substituent.

[0335] [Chemistry 7]

[0336]

[0337] In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.

[0338] In this specification, the case where "two or more adjacent groups are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring" is described by taking the case of an anthracene compound represented by the following formula (XY-80) whose parent skeleton is an anthracene ring as an example.

[0339] [Chemistry 8]

[0340]

[0341] For example, as R 921 ~R 930 In the case of "one or more adjacent two or more groups are bonded to each other to form a ring", the adjacent two groups in one group refer to R 921 With R 922 、R 922 With R 923 、R 923 With R 924 、R 924 With R930 、R 930 With R 925 、R 925 With R 926 、R 926 With R 927 、R 927 With R 928 、R 928 With R 929 , and R 929 With R 921 .

[0342] The above “one or more groups” means that two or more adjacent groups can form a ring at the same time. For example, R 921 With R 922 Bonded to each other to form ring A, while R 925 With R 926 When they are bonded to each other to form ring B, they are represented by the following formula (XY-81).

[0343] [Chemistry 9]

[0344]

[0345] When "two or more adjacent ones" form a ring, for example, R 921 With R 922 Bonded to each other to form ring A, R 922 With R 923 Bonded to each other to form ring C, formed by R 921 ~R 923 The three adjacent anthracene groups are fused to form a common R 922 The case of ring A and ring C is represented by the following formula (XY-82).

[0346] [Chemistry 10]

[0347]

[0348] Rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.

[0349] The "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.

[0350] For example, R shown in the above formula (XY-81) 921 With R 922 Ring A formed by mutual bonding means R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 A ring is formed by bonding the carbon atoms of the anthracene skeleton to one or more arbitrary elements. As a specific example, in the case where R 921 With R922 In the case of forming ring A, R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton is bonded to four carbon atoms to form an unsaturated ring, R 921 With R 922 The ring formed is a benzene ring. Alternatively, when a saturated ring is formed, it becomes a cyclohexane ring.

[0351] Herein, "arbitrary element" is preferably C element, N element, O element, or S element. In the case of an arbitrary element (e.g., C element or N element), bonds not involved in ring formation may be terminated with hydrogen atoms or the like, or may be substituted with any substituent. When an arbitrary element other than C element is contained, the formed ring becomes a heterocycle.

[0352] The number of “one or more arbitrary elements” constituting a saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0353] Specific examples of the aromatic hydrocarbon ring include structures in which the aryl groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0354] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0355] Specific examples of the aliphatic hydrocarbon ring include structures in which the cycloalkyl groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0356] When the above-mentioned "saturated or unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "saturated or unsaturated ring" has a substituent are the substituents described in the above section "Substituents described in this specification."

[0357] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (hereinafter sometimes referred to as "optional substituent") is selected from the following groups:

[0358] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0359] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0360] unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0361] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0362] -Si(R 901 )(R902 )(R 903 ),

[0363] -O-(R 904 ),

[0364] -S-(R 905 ),

[0365] -N(R 906 )(R 907 )

[0366] (In this article,

[0367] R 901 ~R 907 Each independently is:

[0368] hydrogen atoms,

[0369] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0370] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0371] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0372] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each may be the same or different. ), halogen atoms, cyano groups, nitro groups,

[0373] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0374] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0375] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0376] an alkyl group having 1 to 50 carbon atoms,

[0377] an aryl group having 6 to 50 ring carbon atoms, and

[0378] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0379] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0380] an alkyl group having 1 to 18 carbon atoms,

[0381] an aryl group having 6 to 18 ring carbon atoms, and

[0382] A monovalent heterocyclic group having 5 to 18 ring atoms.

[0383] Specific examples of each of the above-mentioned optional substituents are as described above.

[0384] In the present specification, unless otherwise specified, adjacent arbitrary substituents may form a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, more preferably a benzene ring).

[0385] In the present specification, unless otherwise specified, an arbitrary substituent may further have a substituent. Examples of the substituent that an arbitrary substituent may further have include the same substituents as those for the arbitrary substituents described above.

[0386] [Organic electroluminescent element]

[0387] The organic electroluminescent element according to the first aspect of the present invention has:

[0388] anode,

[0389] cathode, and

[0390] a light emitting region located between the anode and the cathode,

[0391] The light-emitting region includes a first light-emitting layer and a second light-emitting layer.

[0392] The first light-emitting layer is directly adjacent to the second light-emitting layer.

[0393] The first light-emitting layer is located between the anode and the second light-emitting layer.

[0394] Either the first light-emitting layer or the second light-emitting layer contains a compound having at least one deuterium atom.

[0395] Reference Figure 1 A schematic configuration of an organic EL device according to a first embodiment of the present invention will be described.

[0396] An organic EL element 1A according to one embodiment of the present invention includes 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 includes 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.

[0397] 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 and the second light-emitting layer 5B are adjacent to each other.

[0398] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0399] The present inventors have discovered that the lifetime of an organic EL device is improved by including a light-emitting layer in a light-emitting region and the light-emitting layer containing a compound having a deuterium atom.

[0400] In one embodiment, only one of the first emitting layer and the second emitting layer contains a compound having at least one deuterium atom, and the other does not substantially contain a compound having a deuterium atom.

[0401] Herein, "a compound containing substantially no deuterium atoms" means containing no deuterium atoms at all, or allowing the inclusion of deuterium atoms to a certain extent in the naturally occurring ratio. The naturally occurring ratio of deuterium atoms is, for example, 0.015% or less.

[0402] That is, “comprising a compound having at least one deuterium atom” herein means that the light-emitting layer comprises a compound having a deuterium atom in an amount exceeding the naturally occurring ratio.

[0403] Compounds containing deuterium atoms can be detected by mass spectrometry or 1 The binding position of the deuterium atom in the compound is confirmed by H-NMR analysis. 1 The identification was carried out by H-NMR analysis. Specifically, it is as follows.

[0404] When the mass spectrum of the target compound is compared with the corresponding compound whose hydrogen atoms are all protium atoms, the molecular weight increases by 1, which confirms that it contains 1 deuterium atom. 1 No signal was found in the H-NMR analysis, so the target compound was 1 The integral value obtained by H-NMR analysis can confirm the number of deuterium atoms contained in the molecule. 1 H-NMR analysis and signal attribution can identify the bonding position of the deuterium atom.

[0405] The ratio of the film thickness of the light-emitting layer containing a compound containing a deuterium atom (film thickness T1) to the film thickness of the light-emitting layer not containing a compound containing a deuterium atom (film thickness T2) is, for example, 0.05 < (T1 / (T1+T2)) < 0.9. From the perspective of avoiding the use of a large amount of a compound containing a deuterium atom (from a cost perspective), the ratio of the film thickness of the light-emitting layer containing a compound containing a deuterium atom (film thickness T1) to the film thickness of the light-emitting layer not containing a compound containing a deuterium atom (film thickness T2) 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, and for example 0.1 < (T1 / (T1+T2)) < 0.4. From the perspective of extending lifetime, the ratio of the film thickness of the light-emitting layer containing a compound having a deuterium atom (film thickness T1) to the film thickness of the light-emitting layer not containing a compound having a deuterium atom (film thickness T2) is preferably 0.1 ≤ (T1 / (T1+T2)), and more preferably 0.3 ≤ (T1 / (T1+T2)). Furthermore, (T1 / (T1+T2)) ≤ 0.9 is also preferred. Taking lifetime and cost into consideration, the ratio is preferably 0.2 ≤ (T1 / (T1+T2)) ≤ 0.7, and more preferably 0.2 ≤ (T1 / (T1+T2)) ≤ 0.5.

[0406] In one embodiment, the ratio of the thickness of the first light-emitting layer (thickness T1) to the thickness of the second light-emitting layer (thickness T2) is, for example, 0.05 < (T1 / (T1+T2)) < 0.9. The ratio of the thickness of the first light-emitting layer (thickness T1) to the thickness of the second light-emitting layer (thickness T2) is preferably 0.05 < (T1 / (T1+T2)) < 0.6, more preferably 0.1 < (T1 / (T1+T2)) < 0.5, and for example 0.1 < (T1 / (T1+T2)) < 0.4.

[0407] From the perspective of life, 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. In addition, it is also preferably 22.5 nm or less. On the other hand, from the perspective of avoiding the use of a large amount of compounds having deuterium atoms (cost perspective), the smaller the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom, the better, preferably 17.5 nm or less. It is further preferred that the film thickness T1 is 12.5 nm or less. It is further preferred that the film thickness T1 is 10 nm or less. If life and cost are taken into consideration, 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.

[0408] In one embodiment, the first emitting layer and the second emitting layer each independently comprise a host material and a dopant material. The dopant material is preferably a blue emitting dopant.

[0409] The compound having at least one deuterium atom may be a host material or a dopant material.

[0410] In one embodiment, the compound having at least one deuterium atom is the host material.

[0411] The content of the host material in the light-emitting layer is preferably 80% by mass or more and 99% by mass or less relative to the entire light-emitting layer.

[0412] The content of the dopant material in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less relative to the entire light-emitting layer.

[0413] The number of deuterium atoms in the compound having at least one deuterium atom is preferably 1-100, more preferably 1-80.

[0414] When the compound having at least one deuterium atom is used as a dopant material, the number of deuterium atoms is preferably 1 to 100, more preferably 1 to 80.

[0415] When a compound having at least one deuterium atom is used as a host material, the number of deuterium atoms is preferably 1-50, more preferably 1-40.

[0416] In one embodiment, the compound having at least one deuterium atom is the host material, and the host material is an anthracene skeleton, a pyrene skeleton, A compound containing at least one of a skeleton, a fluorene skeleton, and a fluorene skeleton.

[0417] In one embodiment, the compound having at least one deuterium atom is the host material, and the host material is a compound having an anthracene skeleton. The at least one deuterium atom may be any hydrogen atom constituting the compound having an anthracene skeleton.

[0418] In one embodiment, the compound having at least one deuterium atom is the host material, and the host material is a compound having an anthracene skeleton, and at least one of the hydrogen atoms bonded to a carbon atom on the anthracene skeleton is a deuterium atom.

[0419] In other embodiments, the compound having at least one deuterium atom is the host material, and the host material is a compound having an anthracene skeleton, and at least one of the hydrogen atoms bonded to carbon atoms other than carbon atoms on the anthracene skeleton is a deuterium atom. Carbon atoms other than carbon atoms on the anthracene skeleton are carbon atoms that constitute so-called side chain structures.

[0420] Furthermore, the at least one deuterium atom may be bonded to both a carbon atom on the anthracene skeleton and a carbon atom other than a carbon atom on the anthracene skeleton.

[0421] In one embodiment, the first light-emitting layer includes a compound having at least one deuterium atom.

[0422] In one embodiment, the first light-emitting layer contains only a compound having at least one deuterium atom as a host material.

[0423] When the light-emitting region has two light-emitting layers, the first light-emitting layer, which is the light-emitting layer on the anode side, preferably contains a compound containing at least one deuterium atom. The compound containing at least one deuterium atom can be either a host material or a dopant material, or both.

[0424] In one embodiment, the first light-emitting layer comprises a compound having at least one deuterium atom.

[0425] The second light-emitting layer comprises an anthracene skeleton, a pyrene skeleton, A compound having a skeleton or a fluorene skeleton.

[0426] In this case, the material of the second light-emitting layer preferably has an anthracene skeleton, a pyrene skeleton, or A compound with a skeleton or a fluorene skeleton.

[0427] In one embodiment, when the deuterium atoms in the host material of the first light-emitting layer are replaced with protium atoms, the chemical structure is the same as that of the host material of the second light-emitting layer.

[0428] In one embodiment, the dopant material of the first light-emitting layer is the same as the dopant material of the second light-emitting layer.

[0429] In one embodiment, at least one of the first light-emitting layer and the second light-emitting layer is a light-emitting layer containing one or more host materials.

[0430] When the light-emitting layer containing two or more host materials contains a host material containing a deuterium atom, only one of them may be a compound containing a deuterium atom and the other may be a compound not containing a deuterium atom, or both may be compounds containing a deuterium atom.

[0431] In one embodiment, the first light-emitting layer does not contain a metal complex.

[0432] In one embodiment, the second light-emitting layer does not contain a metal complex.

[0433] Specific examples of the "metal complex" include phosphorescent metal complexes such as iridium complexes. The "phosphorescent metal complex" functions as a phosphorescent dopant material.

[0434] In one embodiment, the first light-emitting layer and / or the second light-emitting layer do not contain a phosphorescent dopant material. In this case, the first light-emitting layer and / or the second light-emitting layer emits fluorescence.

[0435] In one embodiment, the first emitting layer and / or the second emitting layer does not contain a phosphorescent metal complex.

[0436] In one embodiment, the first light-emitting layer and / or the second light-emitting layer does not contain an iridium complex.

[0437] Specific examples of dopant materials suitable for the organic EL element according to one embodiment of the present invention will be described later.

[0438] In the organic EL device according to the second aspect of the present invention, the light-emitting region further comprises a third light-emitting layer.

[0439] The second light-emitting layer is directly adjacent to the third light-emitting layer.

[0440] The third light-emitting layer is located between the cathode and the second light-emitting layer.

[0441] In one embodiment, the light-emitting region further comprises a third light-emitting layer.

[0442] The second light-emitting layer is directly adjacent to the third light-emitting layer.

[0443] The third light-emitting layer is located between the cathode and the second light-emitting layer.

[0444] The second light-emitting layer contains a compound having at least one deuterium atom.

[0445] Reference Figure 2 The schematic configuration of the organic EL device according to the second embodiment of the present invention will be described.

[0446] Figure 2 The organic EL element 1B according to the second embodiment of the present invention shown in FIG. 1 includes 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 includes 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.

[0447] 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 and the second light-emitting layer 5B are adjacent to each other.

[0448] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0449] 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.

[0450] The second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0451] The organic EL element 1B of the second embodiment of the present invention has a light-emitting region 5 in which the first, second, and third light-emitting layers (5A, 5B, 5C) are adjacent to each other, and the second light-emitting layer (5B) is sandwiched between two other light-emitting layers (5A, 5C) adjacent to the second light-emitting layer (5B), and 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 arranged in a region not adjacent to peripheral layers such as a hole transport layer and an electron transport layer. As a result, even if the interface between these peripheral layers and the adjacent layers (i.e., the light-emitting layers (5A, 5C)) deteriorates, the layer containing the compound having at least one deuterium atom (i.e., the light-emitting layer (5B)) can be expected to avoid degradation.

[0452] The organic EL device according to the third embodiment of the present invention further comprises a third emitting layer and a fourth emitting layer between the second emitting layer and the cathode.

[0453] The third light-emitting layer is directly adjacent to the fourth light-emitting layer.

[0454] The fourth light-emitting layer is provided between the third light-emitting layer and the cathode,

[0455] Either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom.

[0456] In one embodiment of the organic EL device according to the third aspect of the present invention, the device further comprises a third light-emitting layer and a fourth light-emitting layer.

[0457] The third light-emitting layer is directly adjacent to the fourth light-emitting layer.

[0458] The fourth light-emitting layer is provided between the third light-emitting layer and the cathode,

[0459] Either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom,

[0460] A charge generating layer is provided between the second light-emitting layer and the third light-emitting layer.

[0461] Reference Figure 3 The schematic configuration of an organic EL device according to a third embodiment of the present invention will be described.

[0462] Figure 3The organic EL element 1C according to the third embodiment of the present invention shown in FIG. 1 includes 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 includes 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.

[0463] 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 and the second light-emitting layer 5B are adjacent to each other.

[0464] The light-emitting region 5 further includes a third light-emitting layer 5C and a fourth light-emitting layer 5D. The fourth light-emitting layer 5D is located 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 to each other. 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 can all be located on the cathode 4 side. Figure 3 3 shows the case where the third light-emitting layer 5C and the fourth light-emitting layer 5D are on the cathode 4 side.

[0465] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a material containing at least one deuterium atom, and either the third light-emitting layer 5C or the fourth light-emitting layer 5D contains a compound containing at least one deuterium atom.

[0466] Figure 3 In one embodiment of the third aspect of the present invention shown in , the organic EL element 1C further includes a charge generating layer 9 between the second light-emitting layer 5B and the third light-emitting layer 5C.

[0467] The organic EL element 1C of the third embodiment of the present invention has a light-emitting region 5 comprising adjacent first and second light-emitting layers (5A, 5B), and adjacent third and fourth light-emitting layers (5C, 5D). Each of the first and second light-emitting layers (5A, 5B) and each of the third and fourth light-emitting layers (5C, 5D) contains a compound containing at least one deuterium atom. This structure has a so-called tandem structure in which two sets of light-emitting layers having a stacked structure are provided. By having such a tandem structure in the light-emitting region 5, high brightness and a long life can be expected. Furthermore, a white light-emitting element with a simple structure can be manufactured.

[0468] In one embodiment, the host material having at least one deuterium atom is a compound represented by the following formula (1).

[0469] [Chemistry 11]

[0470]

[0471] In formula (1),

[0472] R1 to R8 are each independently:

[0473] hydrogen atoms,

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

[0475] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0476] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0477] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

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

[0479] -O-(R 904 ),

[0480] -S-(R 905 ),

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

[0482] Halogen atoms, cyano groups, nitro groups,

[0483] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0484] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

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

[0486] hydrogen atoms,

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

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

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

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

[0491] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0492] Two or more adjacent groups of R1 to R4 and two or more adjacent groups of R5 to R8 are not bonded to each other to form a ring.

[0493] L1 and L2 are each independently:

[0494] single bond,

[0495] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0496] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0497] Ar1 and Ar2 are each independently:

[0498] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0499] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0500] At least one of the hydrogen atoms of R1 to R8, and one or more groups selected from R1 to R8 that are not hydrogen atoms, L1 that is not a single bond, L2 that is not a single bond, Ar1, and Ar2 is a deuterium atom.

[0501] The compound represented by the above formula (1) has one or more deuterium atoms at any position in the molecule.

[0502] In the aforementioned formula (1), at least one of R1 to R8 is a deuterium atom, or at least one hydrogen atom possessed by one or more groups selected from R1 to R8 that are not hydrogen atoms, L1 that is not a single bond, L2 that is not a single bond, Ar1, and Ar2 is a deuterium atom. Alternatively, at least one of R1 to R8 is a deuterium atom, and at least one hydrogen atom possessed by one or more groups selected from R1 to R8 that are not hydrogen atoms, L1 that is not a single bond, L2 that is not a single bond, Ar1, and Ar2 is a deuterium atom.

[0503] In the organic EL device of one embodiment of the present invention, the content ratio 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 a "light hydrogen form") in the light-emitting layer is preferably 99 mol% or less. The content ratio of the light hydrogen form is confirmed by mass spectrometry.

[0504] All of R1 to R8 may be deuterium atoms, or some (for example, one or two) may be deuterium atoms.

[0505] R1 to R8 that are not deuterium atoms are preferably protium atoms.

[0506] A first embodiment of the compound represented by the aforementioned formula (1) is a compound represented by the following formula (1A).

[0507] [Chemistry 12]

[0508]

[0509] In formula (1A),

[0510] R1 to R8 are each independently:

[0511] hydrogen atoms,

[0512] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0513] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0514] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0515] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0516] -Si(R 901 )(R 902 )(R 903 ),

[0517] -O-(R 904 ),

[0518] -S-(R 905 ),

[0519] -N(R 906 )(R 907 ),

[0520] Halogen atoms, cyano groups, nitro groups,

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

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

[0523] R 901 ~R 907 Each independently is:

[0524] hydrogen atoms,

[0525] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0526] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0527] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0528] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0529] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0530] At least one of R1 to R8 is a deuterium atom.

[0531] Two or more adjacent groups of R1 to R4 and two or more adjacent groups of R5 to R8 are not bonded to each other to form a ring.

[0532] L 1A and L 2A Each independently is:

[0533] single bond,

[0534] substituted or unsubstituted phenylene,

[0535] substituted or unsubstituted naphthylene,

[0536] Substituted or unsubstituted biphenylene,

[0537] Substituted or unsubstituted terphenylene,

[0538] Substituted or unsubstituted anthracene, or

[0539] Substituted or unsubstituted pyrazoline.

[0540] Ar 1A and Ar 2A Each independently is:

[0541] substituted or unsubstituted phenyl,

[0542] substituted or unsubstituted naphthyl,

[0543] Substituted or unsubstituted biphenyl,

[0544] Substituted or unsubstituted terphenyl,

[0545] Substituted or unsubstituted anthracenyl, or

[0546] Substituted or unsubstituted phenoxy.

[0547] L 1A 、L 2A 、Ar 1A and Ar 2A When there is a substituent, the substituent is:

[0548] an alkyl group having 1 to 50 carbon atoms,

[0549] an alkenyl group having 2 to 50 carbon atoms,

[0550] an alkynyl group having 2 to 50 carbon atoms,

[0551] a cycloalkyl group having 3 to 50 ring carbon atoms,

[0552] an alkylsilyl group having 1 to 50 carbon atoms,

[0553] Halogen atoms, or

[0554] cyano group.

[0555] All of R1 to R8 may be deuterium atoms, or some (for example, one or two) may be deuterium atoms.

[0556] R1 to R8 that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

[0557] In one embodiment, selected from L 1A and L 2A At least one of the hydrogen atoms in one or more of the above is a deuterium atom. 1A and L 2A More than one of:

[0558] an unsubstituted phenylene group in which at least one hydrogen atom is a deuterium atom,

[0559] an unsubstituted naphthylene group in which at least one hydrogen atom is a deuterium atom,

[0560] an unsubstituted biphenylene group in which at least one hydrogen atom is a deuterium atom,

[0561] an unsubstituted terphenylene group in which at least one hydrogen atom is a deuterium atom,

[0562] An unsubstituted anthracene group in which at least one hydrogen atom is a deuterium atom, or

[0563] An unsubstituted phenanthryl group in which at least one hydrogen atom is a deuterium atom.

[0564] In one embodiment, L 1A and L 2A Each independently represents a single bond, a substituted or unsubstituted phenylene group, or a naphthylene group. 1A and L 2A At least one of them is a single bond.

[0565] In one embodiment, selected from Ar 1A and Ar 2A At least one of the hydrogen atoms in one or more of the atoms is a deuterium atom. Specifically, in one embodiment, the selected 1A and Ar2A More than one of:

[0566] an unsubstituted phenyl group in which at least one hydrogen atom is a deuterium atom,

[0567] an unsubstituted naphthyl group in which at least one hydrogen atom is a deuterium atom,

[0568] an unsubstituted biphenyl group in which at least one hydrogen atom is a deuterium atom,

[0569] an unsubstituted terphenyl group in which at least one hydrogen atom is a deuterium atom,

[0570] An unsubstituted anthracene group in which at least one hydrogen atom is a deuterium atom, or

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

[0572] In one embodiment, Ar 1A and Ar 2A Each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted phenanthrenyl.

[0573] The compound represented by formula (1A) can be synthesized according to the synthesis method described in the Examples by using known substitution reactions and starting materials corresponding to the target product to thereby synthesize a compound within the scope of the present invention.

[0574] Specific examples of the compound represented by formula (1A) include the following compounds: In the following specific examples, D represents a deuterium atom.

[0575] [Chemistry 13]

[0576]

[0577] [Chemistry 14]

[0578]

[0579] [Chemistry 15]

[0580]

[0581] [Chemistry 16]

[0582]

[0583] [Chemistry 17]

[0584]

[0585] [Chemistry 18]

[0586]

[0587] [Chemistry 19]

[0588]

[0589] [Chemistry 20]

[0590]

[0591] A second embodiment of the compound represented by the aforementioned formula (1) is a compound represented by the following formula (1B).

[0592] [Chemistry 21]

[0593]

[0594] In formula (1B),

[0595] R1 to R8 are each independently:

[0596] hydrogen atoms,

[0597] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0598] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0599] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0600] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0601] -Si(R 901 )(R 902 )(R 903 ),

[0602] -O-(R 904 ),

[0603] -S-(R 905 ),

[0604] -N(R 906 )(R 907 ),

[0605] Halogen atoms, cyano groups, nitro groups,

[0606] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0607] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0608] R 901 ~R 907 Each independently is:

[0609] hydrogen atoms,

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

[0611] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0612] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0613] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0614] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0615] At least one of R1 to R8 is a deuterium atom.

[0616] Two or more adjacent groups of R1 to R4 and two or more adjacent groups of R5 to R8 are not bonded to each other to form a ring.

[0617] L 1B and L 2B Each independently is:

[0618] single bond,

[0619] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0620] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0621] Ar 2B for:

[0622] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0623] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0624] R 11B ~R 18B One of them is with L 1B Single bond bonding.

[0625] Not with L 1B R bonded to a single bond 11B ~R 18B Each independently is:

[0626] hydrogen atoms,

[0627] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0628] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0629] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0630] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0631] -Si(R 901 )(R 902 )(R 903 ),

[0632] -O-(R 904 ),

[0633] -S-(R 905 ),

[0634] -N(R 906 )(R 907 ),

[0635] Halogen atoms, cyano groups, nitro groups,

[0636] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0637] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0638] R 901 ~R 907 As defined in R1 to R8.

[0639] R 11B ~R 18B Two or more adjacent ones are not bonded to each other to form a ring.

[0640] All of R1 to R8 may be deuterium atoms, or some (for example, one or two or more) may be deuterium atoms.

[0641] R1 to R8 that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

[0642] In one embodiment, selected from L 1B and L 2B At least one of the hydrogen atoms in one or more of the above is a deuterium atom. 1B and L 2B One or more of them is an unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted divalent heterocyclic group having 5 to 30 ring atoms in which at least one hydrogen atom is a deuterium atom.

[0643] In one embodiment, L1B and L 2B Each independently represents a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. 1B and L 2B At least one of them is a single bond.

[0644] In one embodiment, R 11B ~R 18B It is not the same as L 1B Those bonded by single bonds are hydrogen atoms.

[0645] In one embodiment, R 11B ~R 18B It is not the same as L 1B At least one of the single bonds is a deuterium atom.

[0646] In one embodiment, Ar 2B At least one of the hydrogen atoms is a deuterium atom. Specifically, in one embodiment, Ar 2B It is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms in which at least one hydrogen atom is a deuterium atom.

[0647] Ar 2B It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably selected from the groups represented by the following formulae (a1B) to (a4B).

[0648] [Chemistry 22]

[0649]

[0650] In formulas (a1B) to (a4B), * is 2B Single bond bonding.

[0651] R 21B for:

[0652] Halogen atoms, cyano groups, nitro groups,

[0653] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0655] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0656] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0657] -Si(R 901 )(R 902 )(R903 ),

[0658] -O-(R 904 ),

[0659] -S-(R 905 ),

[0660] -N(R 906 )(R 907 ),

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

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

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

[0664] m1B is an integer from 0 to 4.

[0665] m2B is an integer from 0 to 5.

[0666] m3B is an integer from 0 to 7.

[0667] When m1B to m3B are each 2 or more, multiple R 21B They may be the same as or different from each other.

[0668] When m1B to m3B are each 2 or more, the adjacent multiple R 21B They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[0669] L 1B and L 2B Preferably, each independently represents a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. 1B and L 2B At least one of them is a single bond.

[0670] In one embodiment, the compound represented by formula (1B) is a compound represented by the following formula (1B-1).

[0671] [Chemistry 23]

[0672]

[0673] In formula (1B-1), R1 to R8, Ar 2B 、L 1B and L 2B As defined above in formula (1B).

[0674] In one embodiment, the compound represented by formula (1B) is a compound represented by the following formula (1B-2).

[0675] [Chemistry 24]

[0676]

[0677] In formula (1B-2), Ar2, L 1B and L 2B As defined above in formula (1B).

[0678] The compound represented by formula (1B) can be synthesized according to the synthesis method described in the Examples by using known substitution reactions and starting materials corresponding to the target product.

[0679] Specific examples of the compound represented by formula (1B) are shown below. In the following specific examples, D represents a deuterium atom.

[0680] [Chemistry 25]

[0681]

[0682] [Chemistry 26]

[0683]

[0684] [Chemistry 27]

[0685]

[0686] [Chemistry 28]

[0687]

[0688] [Chemistry 29]

[0689]

[0690] [Chemistry 30]

[0691]

[0692] [Chemistry 31]

[0693]

[0694] [Chemistry 32]

[0695]

[0696] [Chemistry 33]

[0697]

[0698] [Chemistry 34]

[0699]

[0700] [Chemistry 35]

[0701]

[0702] [Chemistry 36]

[0703]

[0704] [Chemistry 37]

[0705]

[0706] [Chemistry 38]

[0707]

[0708] [Chemistry 39]

[0709]

[0710] [Chemistry 40]

[0711]

[0712] [Chemistry 41]

[0713]

[0714] [Chemistry 42]

[0715]

[0716] [Chemistry 43]

[0717]

[0718] [Chemistry 44]

[0719]

[0720] [Chemistry 45]

[0721]

[0722] [Chemistry 46]

[0723]

[0724] A third embodiment of the compound represented by the aforementioned formula (1) is a compound represented by the following formula (1C).

[0725] [Chemistry 47]

[0726]

[0727] In formula (1C),

[0728] R1 to R8 are each independently:

[0729] hydrogen atoms,

[0730] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0731] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0732] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0733] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0734] -Si(R 901 )(R 902 )(R 903 ),

[0735] -O-(R 904 ),

[0736] -S-(R 905 ),

[0737] -N(R 906 )(R 907 ),

[0738] Halogen atoms, cyano groups, nitro groups,

[0739] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0740] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0741] R 901 ~R 907 Each independently is:

[0742] hydrogen atoms,

[0743] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0744] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

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

[0746] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0747] R 901 ~R 907 When there are two or more, two or more R901 ~R 907 They can be the same or different.

[0748] At least one of R1 to R8 is a deuterium atom.

[0749] Two or more adjacent groups of R1 to R4 and two or more adjacent groups of R5 to R8 are not bonded to each other to form a ring.

[0750] L 1C and L 2C Each independently is:

[0751] single bond,

[0752] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0753] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0754] Ar 2C for:

[0755] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0756] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0757] Ar 1C It is a monovalent group represented by the following formula (2C), (3C) or (4C).

[0758] [Chemistry 48]

[0759]

[0760] In formulas (2C) to (4C),

[0761] R 15C ~R 20C One or more adjacent two of 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.

[0762] R 15C ~R 20C When two or more adjacent groups of R 11C ~R 20C One of them is with L 1C Single bond bonding.

[0763] R 15C ~R 20CWhen two or more adjacent groups of R are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, R that does not form the substituted or unsubstituted saturated or unsaturated ring 15C ~R 20C , and R 11C ~R 14C One of them is with L 1C Single bond bonding.

[0764] Does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring and is not 1C R bonded to a single bond 11C ~R 20C Each independently is:

[0765] hydrogen atoms,

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

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

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

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

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

[0771] -O-(R 904 ),

[0772] -S-(R 905 ),

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

[0774] Halogen atoms, cyano groups, nitro groups,

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

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

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

[0778] All of R1 to R8 may be deuterium atoms, or some (for example, one or two or more) may be deuterium atoms.

[0779] R1 to R8 that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

[0780] In one embodiment, selected from L 1C and L 2C At least one of the hydrogen atoms in one or more of the above is a deuterium atom. Specifically, in one embodiment, the selected 1C and L 2C One or more of them is an unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted divalent heterocyclic group having 5 to 30 ring atoms in which at least one hydrogen atom is a deuterium atom.

[0781] In one embodiment, L 1C and L 2C Each independently represents a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. 1C and L 2C At least one of them is a single bond.

[0782] In one embodiment, R in formulas (2C) to (4C) 11C ~R 14C Any one of them is L 1C Single bond bonding.

[0783] In one embodiment, R in formulas (2C) to (4C) 15C ~R 20C One or more adjacent two of the groups are not bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[0784] In one embodiment, R in formulas (2C) to (4C) 11C ~R 20C In, not with L 1C Those that are bonded by single bonds and do not contribute to ring formation are preferably hydrogen atoms.

[0785] In one embodiment, R in formulas (2C) to (4C) 11C ~R 20C In, not with L 1C At least one of the single bonds that are bonded and do not contribute to ring formation is a deuterium atom.

[0786] In one embodiment, Ar 2C At least one of the hydrogen atoms is a deuterium atom. Specifically, in one embodiment, Ar 2C It is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms in which at least one hydrogen atom is a deuterium atom.

[0787] Ar2C It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably selected from the groups represented by the following formulae (a1C) to (a4C).

[0788] [Chemistry 49]

[0789]

[0790] In formulas (a1C) to (a4C), * is 2C Single bond bonding.

[0791] R 21C for:

[0792] Halogen atoms, cyano groups, nitro groups,

[0793] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0794] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0795] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0796] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0797] -Si(R 901 )(R 902 )(R 903 ),

[0798] -O-(R 904 ),

[0799] -S-(R 905 ),

[0800] -N(R 906 )(R 907 ),

[0801] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0802] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0803] R 901 ~R 907 As defined above in formula (1C).

[0804] m1C is an integer from 0 to 4.

[0805] m2C is an integer from 0 to 5.

[0806] m3C is an integer from 0 to 7.

[0807] When m1C to m3C are each greater than 2, multiple R 21C They may be the same as or different from each other.

[0808] When m1C to m3C are 2 or more, the adjacent multiple R 21 They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[0809] L 1C and L 2C Preferably, each independently represents a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. 1C and L 2C At least one of them is a single bond.

[0810] 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).

[0811] [Chemistry 50]

[0812]

[0813] In formulas (1C-1) to (1C-3), R1 to R8, Ar 2C 、L 1C and L 2C As defined above in formula (1C).

[0814] 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).

[0815] [Chemistry 51]

[0816]

[0817] In formulas (1C-11) to (1C-13), Ar 2C 、L 1C and L 2C As defined above in formula (1C).

[0818] The compound represented by formula (1C) can be synthesized according to the synthesis method described in the Examples by using known substitution reactions and starting materials corresponding to the target product.

[0819] Specific examples of the compound represented by formula (1C) are shown below. In the following specific examples, D represents a deuterium atom.

[0820] [Chemistry 52]

[0821]

[0822] [Chemistry 53]

[0823]

[0824] [Chemistry 54]

[0825]

[0826] [Chemistry 55]

[0827]

[0828] [Chemistry 56]

[0829]

[0830] [Chemistry 57]

[0831]

[0832] [Chemistry 58]

[0833]

[0834] [Chemistry 59]

[0835]

[0836] [Chemistry 60]

[0837]

[0838] [Chemistry 61]

[0839]

[0840] [Chemistry 62]

[0841]

[0842] [Chemistry 63]

[0843]

[0844] [Chemistry 64]

[0845]

[0846] [Chemistry 65]

[0847]

[0848] [Chemistry 66]

[0849]

[0850] [Chemistry 67]

[0851]

[0852] [Chemistry 68]

[0853]

[0854] [Chemistry 69]

[0855]

[0856] [Chemistry 70]

[0857]

[0858] [Chemistry 71]

[0859]

[0860] [Chemistry 72]

[0861]

[0862] [Chemistry 73]

[0863]

[0864] [Chemistry 74]

[0865]

[0866] [Chemistry 75]

[0867]

[0868] [Chemistry 76]

[0869]

[0870] [Chemistry 77]

[0871]

[0872] [Chemistry 78]

[0873]

[0874] [Chemistry 79]

[0875]

[0876] [Chemistry 80]

[0877]

[0878] [Chemistry 81]

[0879]

[0880] [Chemistry 82]

[0881]

[0882] [Chemistry 83]

[0883]

[0884] [Chemistry 84]

[0885]

[0886] [Chemistry 85]

[0887]

[0888] [Chemistry 86]

[0889]

[0890] [Chemistry 87]

[0891]

[0892] [Chemistry 88]

[0893]

[0894] [Chemistry 89]

[0895]

[0896] [Chemistry 90]

[0897]

[0898] [Chemistry 91]

[0899]

[0900] [Chemistry 92]

[0901]

[0902] [Chemistry 93]

[0903]

[0904] [Chemistry 94]

[0905]

[0906] [Chemistry 95]

[0907]

[0908] [Chemistry 96]

[0909]

[0910] [Chemistry 97]

[0911]

[0912] [Chemistry 98]

[0913]

[0914] [Chemistry 99]

[0915]

[0916] [Chemistry 100]

[0917]

[0918] The dopant material is not particularly limited, but preferably does not contain a phosphorescent dopant material as described above. Examples of the dopant material include compounds represented by the following formulas (11), (21), (31), (41), (51), (61), (71), (81), and (91). The compound represented by the following formula (11) is preferred.

[0919] (Compound represented by formula (11))

[0920] The compound represented by formula (11) is described.

[0921] [Chemistry 101]

[0922]

[0923] In formula (11),

[0924] R 101 ~R 110 One or more adjacent groups of two or more of 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.

[0925] R 101 ~R 110 At least one of them is a monovalent group represented by the following formula (12).

[0926] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring and is not a monovalent group represented by the following formula (12): 101 ~R 110 Each independently is:

[0927] hydrogen atoms,

[0928] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0929] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0930] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0931] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0932] -Si(R 901 )(R 902 )(R 903 ),

[0933] -O-(R 904 ),

[0934] -S-(R 905 ),

[0935] -N(R 906 )(R 907 ),

[0936] Halogen atoms, cyano groups, nitro groups,

[0937] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0938] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0939] R 901 ~R 907 As defined in formula (1) above.

[0940] [Chemistry 102]

[0941]

[0942] In formula (12), Ar 101 and Ar 102 Each independently is:

[0943] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0944] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0945] L 101 ~L 103 Each independently is:

[0946] single bond,

[0947] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0948] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0949] In formula (11), preferably R 101 ~R 110 Two of them are groups represented by formula (12).

[0950] In one embodiment, the compound represented by formula (11) is represented by the following formula (13).

[0951] [Chemistry 103]

[0952]

[0953] In formula (13), R 111 ~R 118 R in the above formula (11) which is not a monovalent group represented by formula (12) 101 ~R 110 Same. 101 、Ar 102 、L 101 、L 102 and L 103 As defined in formula (12) above.

[0954] In formula (11), L 101 Preferably, it is a single bond, L 102 and L 103 It is preferably a single bond.

[0955] In one embodiment, the compound represented by formula (11) is represented by the following formula (14) or (15).

[0956] [Chemistry 104]

[0957]

[0958] In formula (14), R 111 ~R 118 As defined in the above formula (13). 101 、Ar 102 、L 102 and L 103 As defined in formula (12) above.

[0959] [Chemistry 105]

[0960]

[0961] In formula (15), R 111 ~R 118As defined in the above formula (13). 101 and Ar 102 As defined in formula (12) above.

[0962] In formula (11) and formula (12), Ar is preferably 101 and Ar 102 At least one of them is a group represented by the following formula (16).

[0963] [Chemistry 106]

[0964]

[0965] In formula (16),

[0966] X 101 represents an oxygen atom or a sulfur atom.

[0967] R 121 ~R 127 Among them, one or more adjacent two or more groups are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0968] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 121 ~R 127 Each independently is:

[0969] hydrogen atoms,

[0970] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0971] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0972] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0973] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0974] -Si(R 901 )(R 902 )(R 903 ),

[0975] -O-(R 904 ),

[0976] -S-(R 905 ),

[0977] -N(R 906 )(R 907 ),

[0978] Halogen atoms, cyano groups, nitro groups,

[0979] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0980] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0981] R 901 ~R 907 As defined in formula (1) above.

[0982] X 101 An oxygen atom is preferred.

[0983] R 121 ~R 127 At least one of the following is preferably:

[0984] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0986] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0987] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0988] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0989] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0990] In formula (11) (formula (12)), Ar is preferably 101 is a group represented by formula (16), Ar 102 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0991] In one embodiment, the compound represented by formula (11) is represented by the following formula (17).

[0992] [Chemistry 107]

[0993]

[0994] In formula (17), R 111 ~R 118 As defined in the above formula (13). 121 ~R 127 As defined in formula (16) above.

[0995] R 131 ~R 135 Each independently is:

[0996] hydrogen atoms,

[0997] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0998] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0999] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1000] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1001] -Si(R 901 )(R 902 )(R 903 ),

[1002] -O-(R 904 ),

[1003] -S-(R 905 ),

[1004] -N(R 906 )(R 907 ),

[1005] Halogen atoms, cyano groups, nitro groups,

[1006] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1007] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1008] R 901 ~R 907 As defined in formula (1) above.

[1009] As specific examples of the compound represented by formula (11), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1010] [Chemistry 108]

[1011]

[1012] [Chemistry 109]

[1013]

[1014] [Chemistry 110]

[1015]

[1016] [Chemistry 111]

[1017]

[1018] [Chemistry 112]

[1019]

[1020] [Chemistry 113]

[1021]

[1022] [Chemistry 114]

[1023]

[1024] (Compound represented by formula (21))

[1025] The compound represented by formula (21) is described.

[1026] [Chemistry 115]

[1027]

[1028] In formula (21),

[1029] Z is independently CR a or N.

[1030] Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1031] R a When there are multiple, multiple R a One or more adjacent two or more of the groups may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1032] R b When there are multiple, multiple R b One or more adjacent two or more of the groups may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1033] R c When there are multiple, multiple R c One or more adjacent two or more of the groups may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1034] n21 and n22 are each independently an integer of 0-4.

[1035] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring a ~R c Each independently is:

[1036] hydrogen atoms,

[1037] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1038] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1039] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1040] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1041] -Si(R 901 )(R 902 )(R 903 ),

[1042] -O-(R 904 ),

[1043] -S-(R 905 ),

[1044] -N(R 906 )(R 907 ),

[1045] Halogen atoms, cyano groups, nitro groups,

[1046] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1047] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1048] R 901 ~R 907 As defined in formula (1) above.

[1049] 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 two carbon atoms in the fused bicyclic structure at the center of formula (21) as ring atoms. Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds formed by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

[1050] 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 contains two carbon atoms in the fused bicyclic structure at the center of formula (21) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2.

[1051] R bIt is bonded to any carbon atom of the aromatic hydrocarbon ring forming the A1 ring, or is bonded to any atom of the heterocyclic ring forming the A1 ring.

[1052] R c It is bonded to any carbon atom of the aromatic hydrocarbon ring forming the A2 ring, or is bonded to any atom of the heterocyclic ring forming the A2 ring.

[1053] Preferred R a ~R c At least one (preferably two) of them is a group represented by the following formula (21a).

[1054] -L 201 -Ar 201 (21a)

[1055] In formula (21a),

[1056] L 201 for:

[1057] single bond,

[1058] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1059] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1060] Ar 201 for:

[1061] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1062] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1063] A group represented by the following formula (21b).

[1064] [Chemistry 116]

[1065]

[1066] In formula (21b),

[1067] L 211 and L 212 Each independently is:

[1068] single bond,

[1069] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1070] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1071] Ar 211 and Ar212 They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1072] Ar does not form a substituted or unsubstituted saturated or unsaturated ring 211 and Ar 212 Each independently is:

[1073] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1074] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1075] In one embodiment, the compound represented by formula (21) is represented by the following formula (22).

[1076] [Chemistry 117]

[1077]

[1078] In formula (22),

[1079] R 201 ~R 211 One or more adjacent groups of two or more of 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.

[1080] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 201 ~R 211 Each independently is:

[1081] hydrogen atoms,

[1082] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1083] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1084] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1085] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1086] -Si(R 901 )(R 902 )(R 903 ),

[1087] -O-(R 904 ),

[1088] -S-(R 905 ),

[1089] -N(R906 )(R 907 ),

[1090] Halogen atoms, cyano groups, nitro groups,

[1091] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1092] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1093] R 901 ~R 907 As defined in formula (1) above.

[1094] Preferred R 201 ~R 211 At least one (preferably two) of them is a group represented by the above formula (21a). 204 and R 211 It is a group represented by the above formula (21a).

[1095] In one embodiment, the compound represented by formula (21) is a compound having a structure represented by the following formula (21-1) or (21-2) bonded to the A1 ring. In another embodiment, the compound represented by formula (22) is R 204 ~R 207 A compound having a structure represented by the following formula (21-1) or (21-2) is bonded to the bonded ring.

[1096] [Chemistry 118]

[1097]

[1098] In formula (21-1), the two bonds * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring of the A1 ring of formula (21), or to R 204 ~R 207 Any one of the bonding.

[1099] The three bonds * in formula (21-2) are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring of the A1 ring in formula (22), or to R 204 ~R 207 Any one of the bonding.

[1100] R 221 ~R 227 and R 231 ~R 239 One or more adjacent groups of two or more of 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.

[1101] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 221 ~R 227 and R 231 ~R 239 Each independently is:

[1102] hydrogen atoms,

[1103] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1104] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1105] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1106] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1107] -Si(R 901 )(R 902 )(R 903 ),

[1108] -O-(R 904 ),

[1109] -S-(R 905 ),

[1110] -N(R 906 )(R 907 ),

[1111] Halogen atoms, cyano groups, nitro groups,

[1112] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1113] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1114] R 901 ~R 907 As defined in formula (1) above.

[1115] 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).

[1116] [Chemistry 119]

[1117]

[1118] In formula (21-3), formula (21-4) and formula (21-5),

[1119] The A1 ring is as defined in formula (21).

[1120] R 2401 ~R 2407 R of formula (21-1) and (21-2) 221 ~R 227 Same. 2410 ~R 2417 Compared with R in formula (22) 201 ~R 211 same.

[1121] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring.

[1122] In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[1123] 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).

[1124] [Chemistry 120]

[1125]

[1126] In formulas (21-6-1) to (21-6-7),

[1127] R 2421 ~R 2427 R of formula (21-1) and (21-2) 221 ~R 227 Same. 2430 ~R 2437 and R 2441 ~R 2444 Compared with R in formula (22) 201 ~R 211 same.

[1128] X is O or NR 901 , or C(R 902 )(R 903 ).

[1129] R 901 ~R 903 As defined in formula (1) above.

[1130] In one embodiment, in the compound represented by formula (22), R 201 ~R 211One or more adjacent groups of two or more of them are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. This embodiment will be described in detail as shown in the following formula (25).

[1131] (Compound represented by formula (25))

[1132] The compound represented by formula (25) will be described.

[1133] [Chemistry 121]

[1134]

[1135] In formula (25),

[1136] Selected from R 251 With R 252 、R 252 With R 253 、R 254 With R 255 、R 255 With R 256 、R 256 With R 257 、R 258 With R 259 、R 259 With R 260 , and R 260 With R 261 Two or more pairs of the pairs in the amine group are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[1137] Among them, R 251 With R 252 The pair composed of R 252 With R 253 A pair consisting of R 254 With R 255 The pair composed of R 255 With R 256 A pair consisting of R 255 With R 256 The pair composed of R 256 With R 257 A pair consisting of R 258 With R 259 The pair composed of R 259 With R 260 and the pair consisting of R 259 With R 260 The pair composed of R 260 With R 261 The composed pairs do not form rings at the same time.

[1138] R 251 ~R 261The two or more rings formed may be the same or different.

[1139] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 251 ~R 261 Each independently is:

[1140] hydrogen atoms,

[1141] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1142] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1143] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1144] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1145] -Si(R 901 )(R 902 )(R 903 ),

[1146] -O-(R 904 ),

[1147] -S-(R 905 ),

[1148] -N(R 906 )(R 907 ),

[1149] Halogen atoms, cyano groups, nitro groups,

[1150] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1151] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1152] R 901 ~R 907 As defined in formula (1) above.

[1153] In formula (25), R n With R n+1 (n represents an integer selected from 251, 252, 254 to 256 and 258 to 260) are bonded to each other and R n and R n+1 The two carbon atoms bonded to the ring together form a substituted or unsubstituted saturated or unsaturated ring. The ring is preferably composed of atoms selected from C atoms, O atoms, S atoms and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

[1154] The number of the above-mentioned ring structures in the compound represented by formula (25) is, for example, 2, 3, or 4. The two or more ring structures may each be present on the same benzene ring on the mother skeleton of formula (25), or may be present on different benzene rings. For example, when there are three ring structures, each of the three benzene rings of formula (25) may have one ring structure.

[1155] Examples of the ring structure in the compound represented by formula (25) include structures represented by the following formulae (251) to (260).

[1156] [Chemistry 122]

[1157]

[1158] In formulas (251) to (257), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 each represent R n With R n+1 The two aforementioned ring carbon atoms bonded to R n The bonded ring carbon atoms may be any of two ring 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.

[1159] X 2501 C(R 2512 )(R 2513 ),NR 2514 , O or S.

[1160] R 2501 ~R 2506 and R 2512 ~R 2513 One or more adjacent groups of two or more of 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.

[1161] R does not form a substituted or unsubstituted saturated or unsaturated ring 2501 ~R 2514 With the aforementioned R 251 ~R 261 same.

[1162] [Chemistry 123]

[1163]

[1164] In formulas (258) to (260), *1 and *2, and *3 and *4 each represent R n With R n+ 1 is bonded to the aforementioned two ring-forming carbon atoms, Rn The ring-constituting carbon atoms to be bonded may be any of the two ring-constituting carbon atoms represented by *1 and *2, or *3 and *4.

[1165] X 2501 C(R 2512 )(R 2513 ),NR 2514 , O or S.

[1166] R 2515 ~~R 2525 One or more adjacent groups of two or more of 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.

[1167] R does not form a substituted or unsubstituted saturated or unsaturated ring 2515 ~R 2521 and R 2522 ~R 2525 With the aforementioned R 251 ~R 261 same.

[1168] In formula (25), R 252 、R 254 、R 255 、R 260 and R 261 At least one (preferably R 252 、R 255 and R 260 At least one of, more preferably R 252 ) is a group that does not form a ring structure.

[1169] (i) In formula (25), R n With R n+1 When the formed ring structure has a substituent,

[1170] (ii) In formula (25), R that does not form a ring structure 251 ~R 261 ,and

[1171] (iii) R in formulas (251) to (260) 2501 ~R 2514 、R 2515 ~~R 2525 Preferably, they are independently:

[1172] hydrogen atoms,

[1173] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1174] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1175] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1176] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1177] -N(R 906 )(R 907 ),

[1178] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1179] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1180] Any one selected from the following groups.

[1181] [Chemistry 124]

[1182]

[1183] In formulas (261) to (264), R d Each independently is:

[1184] hydrogen atoms,

[1185] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1186] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1187] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1188] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1189] -Si(R 901 )(R 902 )(R 903 ),

[1190] -O-(R 904 ),

[1191] -S-(R 905 ),

[1192] -N(R 906 )(R 907 ),

[1193] Halogen atoms, cyano groups, nitro groups,

[1194] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1195] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1196] X is C(R 901 )(R 902 ),NR 903 , O or S.

[1197] R 901 ~R 907 As defined in formula (1) above.

[1198] p1 is an integer of 0-5, p2 is an integer of 0-4, p3 is an integer of 0-3, and p4 is an integer of 0-7.

[1199] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-1) to (25-6).

[1200] [Chemistry 125]

[1201]

[1202] In formulae (25-1) to (25-6), rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring. 251 ~R 261 Same as the above formula (25).

[1203] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulae (25-7) to (25-12).

[1204] [Chemistry 126]

[1205]

[1206] In formulae (25-7) to (25-12), rings d to f, k, and j are each independently a substituted or unsubstituted saturated or unsaturated ring. 251 ~R 261 Same as the above formula (25).

[1207] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-13) to (25-21).

[1208] [Chemistry 127]

[1209]

[1210] In formulae (25-13) to (25-21), rings d to k are each independently a substituted or unsubstituted saturated or unsaturated ring. 251 ~R 261 Same as the above formula (25).

[1211] When the ring g or h further has a substituent, examples of the substituent include:

[1212] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1213] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1214] A group represented by the above formula (261), (263) or (264).

[1215] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-22) to (25-25).

[1216] [Chemistry 128]

[1217]

[1218] In formulas (25-22) to (25-25), X 250 Each independently is C(R 901 )(R 902 ),NR 903 , O or S. R 251 ~R 261 、R 271 ~R 278 R of the above formula (25) 251 ~R 261 Same. 901 ~R 903 As defined in formula (1) above.

[1219] In one embodiment, the compound represented by formula (25) is represented by the following formula (25-26).

[1220] [Chemistry 129]

[1221]

[1222] In formula (25-26), X 250 C(R 901 )(R 902 ),NR 903 , O or S. R 253 、R 254 、R 257 、R 258 、R 261 , and R 271 ~R 282 R of the above formula (25) 251 ~R 261 Same. 901 ~R 903 As defined in formula (1) above.

[1223] As specific examples of the compound represented by formula (21), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1224] In the specific example here, there is no Ph and D.

[1225] [Chemistry 130]

[1226]

[1227] [Chemistry 131]

[1228]

[1229] [Chemistry 132]

[1230]

[1231] [Chemistry 133]

[1232]

[1233] [Chemistry 134]

[1234]

[1235] [Chemistry 135]

[1236]

[1237] [Chemistry 136]

[1238]

[1239] [Chemistry 137]

[1240]

[1241] [Chemistry 138]

[1242]

[1243] [Chemistry 139]

[1244]

[1245] (Compound represented by formula (31))

[1246] The compound represented by formula (31) is described below. The compound represented by formula (31) corresponds to the compound represented by formula (21-3).

[1247] [Chemistry 140]

[1248]

[1249] In formula (31),

[1250] R 301 ~R 307 and R 311 ~R 317 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1251] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 301 ~R 307 and R 311 ~R 317 Each independently is:

[1252] hydrogen atoms,

[1253] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1254] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1255] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1256] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1257] -Si(R 901 )(R 902 )(R 903 ),

[1258] -O-(R 904 ),

[1259] -S-(R 905 ),

[1260] -N(R 906 )(R 907 ),

[1261] Halogen atoms, cyano groups, nitro groups,

[1262] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1263] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1264] R 321 and R 322 Each independently is:

[1265] hydrogen atoms,

[1266] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1267] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1268] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1269] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1270] -Si(R 901 )(R 902 )(R 903 ),

[1271] -O-(R 904 ),

[1272] -S-(R 905 ),

[1273] -N(R 906 )(R 907 ),

[1274] Halogen atoms, cyano groups, nitro groups,

[1275] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1276] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1277] R 901 ~R 907 As defined in formula (1) above.

[1278] “R 301 ~R 307 and R 311 ~R 317 "A group of two or more adjacent" is, for example, R 301 With R 302 、R 302 With R 303 、R 303 With R 304 、R 305 With R 306 、R 306 With R 307 、R 301 With R 302 With R 303 etc. combination.

[1279] In one embodiment, R 301 ~R 307 and R 311 ~R 317 At least one, preferably two, of the906 )(R 907 ) shown in the group.

[1280] In one embodiment, R 301 ~R 307 and R 311 ~R 317 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1281] In one embodiment, the compound represented by formula (31) is a compound represented by the following formula (32).

[1282] [Chemistry 141]

[1283]

[1284] In formula (32),

[1285] R 331 ~R 334 and R 341 ~R 344 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1286] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 331 ~R 334 、R 341 ~R 344 , and R 351 and R 352 Each independently is:

[1287] hydrogen atoms,

[1288] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1289] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1290] R 361 ~R 364 Each independently is:

[1291] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1292] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1293] In one embodiment, the compound represented by formula (31) is a compound represented by the following formula (33).

[1294] [Chemistry 142]

[1295]

[1296] In formula (33), R 351 、R 352 and R 361 ~R 364 As defined in formula (32) above.

[1297] In one embodiment, R in formulas (32) and (33) 361 ~R 364 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[1298] In one embodiment, R in formula (31) 321 and R 322 , R in formula (32) and (33) 351 and R 352 A hydrogen atom.

[1299] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formulas (31) to (33) is:

[1300] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1301] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1302] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1303] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1304] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1305] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1306] Specific examples of the compound represented by formula (31) include the following compounds.

[1307] [Chemistry 143]

[1308]

[1309] [Chemistry 144]

[1310]

[1311] [Chemistry 145]

[1312]

[1313] [Chemistry 146]

[1314]

[1315] [Chemistry 147]

[1316]

[1317] [Chemistry 148]

[1318]

[1319] (Compound represented by formula (41))

[1320] The compound represented by formula (41) is described.

[1321] [Chemistry 149]

[1322]

[1323] In formula (41),

[1324] Ring a, ring b and ring c are each independently:

[1325] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1326] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1327] R 401 and R 402 Each independently bonds to the aforementioned a ring, the aforementioned b ring, or the aforementioned c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.

[1328] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring 401 and R 402 Each independently is:

[1329] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1330] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1331] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1332] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1333] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1334] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1335] Ring a, ring b and ring c are rings fused to the central fused bicyclic structure of formula (41) composed of a B atom and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

[1336] The "aromatic hydrocarbon rings" of the a-ring, b-ring, and c-ring have the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of the a-ring contains three carbon atoms in the fused bicyclic structure at the center of the formula (41) as ring atoms. The "aromatic hydrocarbon rings" of the b-ring and c-ring contain two carbon atoms in the fused bicyclic structure at the center of the formula (41) as ring atoms. Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds formed by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

[1337] The "heterocycle" of the a ring, b ring and c ring has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "heterocyclic group". The "heterocycle" of the a ring contains three carbon atoms in the fused bicyclic structure at the center of the formula (41) as ring atoms. The "heterocycle" of the b ring and c ring contains two carbon atoms in the fused bicyclic structure at the center of the formula (41) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2.

[1338] R 401 and R 402 Each of them can independently bond to the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case contains the nitrogen atom on the fused bicyclic structure in the center of formula (41). The heterocyclic ring in this case may also contain heteroatoms other than nitrogen atoms. R 401 and R 402 Specifically, the atoms constituting the a ring, the b ring or the c ring are bonded to the atoms constituting the R 401 and R 402 For example, R 401 Can be bonded to a ring to form a 401 A nitrogen-containing heterocyclic ring having two or more nitrogen rings fused therein, wherein the ring of the ring is fused to the ring of the ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having two or more nitrogen rings fused therein in the specific example group G2.

[1339] R 401 When bonded to the b ring, R 402 When bonded to the a ring, and R 402 The case of bonding to the C ring is the same as above.

[1340] In one embodiment, the ring a, ring b, and ring c in formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

[1341] In one embodiment, the ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

[1342] In one embodiment, R in formula (41) 401 and R 402 Each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1343] In one embodiment, the compound represented by formula (41) is a compound represented by the following formula (42).

[1344] [Chemistry 150]

[1345]

[1346] In formula (42),

[1347] R 401A and selected from R 411 and R 421 One or more of them may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. 402A and selected from R 413 and R 414 One or more of them may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1348] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring 401A and R 402A Each independently is:

[1349] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1350] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1351] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1352] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1353] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1354] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1355] R 411 ~R 421 One or more adjacent groups of two or more of 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.

[1356] 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:

[1357] hydrogen atoms,

[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 carbon atoms,

[1362] -Si(R 901 )(R 902 )(R 903 ),

[1363] -O-(R 904 ),

[1364] -S-(R 905 ),

[1365] -N(R 906 )(R 907 ),

[1366] Halogen atoms, cyano groups, nitro groups,

[1367] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1368] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1369] R 901 ~R 907 As defined in formula (1) above.

[1370] R in formula (42) 401A and R 402A is the same as R in formula (41) 401 and R 402 The corresponding group.

[1371] For example, R 401A With R 411These rings may be bonded to form a nitrogen-containing heterocyclic ring having two rings (or three rings or more) fused together with the benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocyclic rings include compounds corresponding to the nitrogen-containing heterocyclic rings having two or more rings fused together in the specific example group G2. 401A With R 412 Bonding situation, R 402A With R 413 Bonding situation, and R 402A With R 414 The bonding situation is the same as above.

[1372] R 411 ~R 421 Two or more adjacent groups of R may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. 411 With R 412 They can be bonded to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring is fused to the 6-membered ring to which they are bonded, and the formed fused ring becomes a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring.

[1373] In one embodiment, R 411 ~R 421 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1374] In one embodiment, R 411 ~R 421 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1375] In one embodiment, R 411 ~R 421 Each is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1376] In one embodiment, R 411 ~R 421 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 411 ~R 421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1377] In one embodiment, the compound represented by the aforementioned formula (42) is a compound represented by the following formula (43).

[1378] [Chemistry 151]

[1379]

[1380] In formula (43),

[1381] R 431 With R 446 The R groups may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. 433 With R 447 The R groups may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. 434 With R 451 The R groups may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. 441 With R 442 The bonds may form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1382] R 431 ~R 451 One or more adjacent groups of two or more of 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.

[1383] R that does not form the aforementioned substituted or unsubstituted heterocyclic ring or the aforementioned substituted or unsubstituted saturated or unsaturated ring 431 ~R 451 Each independently is:

[1384] hydrogen atoms,

[1385] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1386] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1387] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1388] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1389] -Si(R 901 )(R 902 )(R 903 ),

[1390] -O-(R 904 ),

[1391] -S-(R 905 ),

[1392] -N(R 906 )(R907 ),

[1393] Halogen atoms, cyano groups, nitro groups,

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

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

[1396] R 901 ~R 907 As defined in formula (1) above.

[1397] R 431 Can be used with R 446 bonded to form a substituted or unsubstituted heterocyclic ring. For example, R 431 With R 446 Can bond to form R 46 A nitrogen-containing heterocyclic ring having three or more rings fused together by condensing a benzene ring, a ring containing N, and a benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more rings fused together in Specific Example Group G2. 433 With R 447 Bonding situation, R 434 With R 451 Bonding situation, and R 441 With R 442 The bonding situation is the same as above.

[1398] In one embodiment, R 431 ~R 451 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1399] In one embodiment, R 431 ~R 451 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1400] In one embodiment, R 431 ~R 451 Each is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1401] In one embodiment, R 431 ~R 451are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 431 ~R 451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1402] In one embodiment, the compound represented by the aforementioned formula (43) is a compound represented by the following formula (43A).

[1403] [Chemistry 152]

[1404]

[1405] In formula (43A),

[1406] R 461 for:

[1407] hydrogen atoms,

[1408] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1409] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1410] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1411] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1412] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1413] R 462 ~R 465 Each independently is:

[1414] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1415] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1416] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1417] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1418] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1419] In one embodiment, R 461 ~R 465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1420] In one embodiment, R461 ~R 465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1421] In one embodiment, the compound represented by the aforementioned formula (43) is a compound represented by the following formula (43B).

[1422] [Chemistry 153]

[1423]

[1424] In formula (43B),

[1425] R 471 and R 472 Each independently is:

[1426] hydrogen atoms,

[1427] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1428] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1429] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1430] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1431] -N(R 906 )(R 907 ),or

[1432] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1433] R 473 ~R 475 Each independently is:

[1434] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1435] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1436] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1437] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1438] -N(R 906 )(R 907 ),or

[1439] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1440] R 906 and R907 As defined in formula (1) above.

[1441] In one embodiment, the compound represented by the aforementioned formula (43) is a compound represented by the following formula (43B').

[1442] [Chemistry 154]

[1443]

[1444] In formula (43B'), R 472 ~R 475 As defined above in formula (43B).

[1445] In one embodiment, R 471 ~R 475 At least one of the following is:

[1446] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1447] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1448] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1449] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1450] -N(R 906 )(R 907 ),or

[1451] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1452] In one embodiment,

[1453] R 472 for:

[1454] hydrogen atoms,

[1455] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1456] -N(R 906 )(R 907 ),or

[1457] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1458] R 471 and R 473 ~R 475 Each independently is:

[1459] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1460] -N(R 906 )(R 907 ),or

[1461] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1462] In one embodiment, the compound represented by the aforementioned formula (43) is a compound represented by the following formula (43C).

[1463] [Chemistry 155]

[1464]

[1465] In formula (43C),

[1466] R 481 and R 482 Each independently is:

[1467] hydrogen atoms,

[1468] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1469] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1470] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1471] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1472] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1473] R 483 ~R 486 Each independently is:

[1474] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1475] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1476] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1477] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1478] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1479] In one embodiment, the compound represented by the aforementioned formula (43) is a compound represented by the following formula (43C′).

[1480] [Chemistry 156]

[1481]

[1482] In formula (43C'), R 483 ~R 486 As defined above in formula (43C).

[1483] In one embodiment, R 481 ~R 486 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1484] In one embodiment, R 481 ~R 486 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1485] The compound represented by formula (41) can be prepared by first bonding rings a, b, and c with a linker (a group containing N-R1 and a group containing N-R2) to produce an intermediate (first reaction), and then bonding rings a, b, and c with a linker (a group containing B) to produce a final product (second reaction). In the first reaction, an amination reaction such as the Buchwald–Hartwig reaction can be applied. In the second reaction, a tandem Friedel–Crafts reaction can be applied.

[1486] Although specific examples of the compound represented by formula (41) are described below, these are merely illustrative and the compound represented by formula (41) is not limited to the following specific examples. In the following specific examples, Me represents a methyl group and tBu represents a tert-butyl group.

[1487] [Chemistry 157]

[1488]

[1489] [Chemistry 158]

[1490]

[1491] [Chemistry 159]

[1492]

[1493] [Chemistry 160]

[1494]

[1495] [Chemistry 161]

[1496]

[1497] [Chemistry 162]

[1498]

[1499] [Chemistry 163]

[1500]

[1501] [Chemistry 164]

[1502]

[1503] [Chemistry 165]

[1504]

[1505] [Chemistry 166]

[1506]

[1507] [Chemistry 167]

[1508]

[1509] [Chemistry 168]

[1510]

[1511] [Chemistry 169]

[1512]

[1513] [Chemistry 170]

[1514]

[1515] [Chemistry 171]

[1516]

[1517] (Compound represented by formula (51))

[1518] The compound represented by formula (51) is described.

[1519] [Chemistry 172]

[1520]

[1521] In formula (51),

[1522] The r ring is a ring represented by formula (52) or formula (53) fused at any position of an adjacent ring.

[1523] The q ring and the s ring are each independently a ring represented by the formula (54) fused at any position of the adjacent rings.

[1524] The p ring and the t ring are each independently a structure represented by formula (55) or formula (56) fused at any position of the adjacent rings.

[1525] R 501 When there are multiple adjacent R 501 They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1526] X 501 is an oxygen atom, a sulfur atom or NR 502 .

[1527] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 501 and R 502 for:

[1528] hydrogen atoms,

[1529] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1530] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1531] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1532] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1533] -Si(R 901 )(R 902 )(R 903 ),

[1534] -O-(R 904 ),

[1535] -S-(R 905 ),

[1536] -N(R 906 )(R 907 ),

[1537] Halogen atoms, cyano groups, nitro groups,

[1538] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1539] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1540] R 901 ~R 907 As defined in formula (1) above.

[1541] Ar 501 and Ar 502 Each independently is:

[1542] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1543] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1544] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1545] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1546] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1547] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1548] L 501 for:

[1549] a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

[1550] a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

[1551] a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

[1552] a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

[1553] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1554] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[1555] m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is an integer of 0 to 3, and m4 is an integer of 0 to 5. 501 When there are multiple, multiple R 501 They may be the same as or different from each other.

[1556] In formula (51), each of the rings p to t shares two carbon atoms with the adjacent ring and is fused. The position and direction of fusion are not limited, and the rings can be fused at any position and direction.

[1557] In one embodiment, in the formula (52) or (53) of the r ring, R 501 A hydrogen atom.

[1558] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-1) to (51-6).

[1559] [Chemistry 173]

[1560]

[1561] In formulas (51-1) to (51-6), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m3 are as defined in the aforementioned formula (51).

[1562] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-11) to (51-13).

[1563] [Chemistry 174]

[1564]

[1565] In formulas (51-11) to (51-13), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1, m3 and m4 are as defined in the aforementioned formula (51).

[1566] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-21) to (51-25).

[1567] [Chemistry 175]

[1568]

[1569] In formulas (51-21) to (51-25), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m4 are as defined in the aforementioned formula (51).

[1570] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-31) to (51-33).

[1571] [Chemistry 176]

[1572]

[1573] In formulas (51-31) to (51-33), R 501 、X 501 、Ar 501 、Ar 502 、L501 , m2~m4 are as defined in the above formula (51).

[1574] In one embodiment, Ar 501 and Ar 502 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1575] In one embodiment, Ar 501 and Ar 502 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1576] As specific examples of the compound represented by formula (51), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1577] [Chemistry 177]

[1578]

[1579] [Chemistry 178]

[1580]

[1581] [Chemistry 179]

[1582]

[1583] [Chemistry 180]

[1584]

[1585] [Chemistry 181]

[1586]

[1587] [Chemistry 182]

[1588]

[1589] (Compound represented by formula (61))

[1590] The compound represented by formula (61) is described.

[1591] [Chemistry 183]

[1592]

[1593] In formula (61),

[1594] R 601 With R 602 、R 602 With R603 , and R 603 With R 604 At least one group of them is bonded to each other to form a divalent group represented by the following formula (62).

[1595] R 605 With R 606 、R 606 With R 607 , and R 607 With R 608 At least one group of them is bonded to each other to form a divalent group represented by the following formula (63).

[1596] [Chemistry 184]

[1597]

[1598] R 601 ~R 604 Those that do not form a divalent group represented by the above formula (62), and R 611 ~R 614 At least one of them is a monovalent group represented by the following formula (64).

[1599] R 605 ~R 608 Those that do not form a divalent group represented by the above formula (63), and R 621 ~R 624 At least one of them is a monovalent group represented by the following formula (64).

[1600] X 601 is an oxygen atom, a sulfur atom or NR 609 .

[1601] R does not form a divalent group represented by the above formulae (62) and (63) and is not a monovalent group represented by the above formula (64) 601 ~R 608 , R is not a monovalent group represented by the above formula (64) 611 ~R 614 and R 621 ~R 624 , and R 609 Each independently is:

[1602] hydrogen atoms,

[1603] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1604] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1605] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1606] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1607] -Si(R 901 )(R 902 )(R 903 ),

[1608] -O-(R 904 ),

[1609] -S-(R 905 ),

[1610] -N(R 906 )(R 907 ),

[1611] Halogen atoms, cyano groups, nitro groups,

[1612] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1613] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1614] R 901 ~R 907 As defined in formula (1) above.

[1615] [Chemistry 185]

[1616]

[1617] In formula (64), Ar 601 and Ar 602 Each independently is:

[1618] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1619] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1620] L 601 ~L 603 Each independently is:

[1621] single bond,

[1622] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[1623] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[1624] These are a divalent linking group formed by bonding 2 to 4 of them.

[1625] 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 they can be formed in R 601 ~R 608 The possible positions of the group are formed.

[1626] In one embodiment, the compound represented by formula (61) is represented by any one of the following formulas (61-1) to (61-6).

[1627] [Chemistry 186]

[1628]

[1629] In formulas (61-1) to (61-6), X 601 As defined in formula (61) above.

[1630] R 601 ~R 624 At least two of them are monovalent groups represented by the above formula (64).

[1631] R is not a monovalent group represented by the above formula (64) 601 ~R 624 Each independently is:

[1632] hydrogen atoms,

[1633] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1634] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1635] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1636] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1637] -Si(R 901 )(R 902 )(R 903 ),

[1638] -O-(R 904 ),

[1639] -S-(R 905 ),

[1640] -N(R 906 )(R 907 ),

[1641] Halogen atoms, cyano groups, nitro groups,

[1642] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1643] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1644] R 901 ~R 907 As defined in formula (1) above.

[1645] In one embodiment, the compound represented by formula (61) is represented by any one of the following formulae (61-7) to (61-18).

[1646] [Chemistry 187]

[1647]

[1648] In formulas (61-7) to (61-18), X 601 As defined in the above formula (61). * is a single bond bonded to the monovalent group represented by the above formula (64). 601 ~R 624 and R which is not a monovalent group represented by the above formula (64) 601 ~R 624 same.

[1649] R does not form a divalent group represented by the above formulae (62) and (63) and is not a monovalent group represented by the above formula (64) 601 ~R 608 , and R which is not a monovalent group represented by the above formula (64) 611 ~R 614 and R 621 ~R 624 Preferably, they are independently:

[1650] hydrogen atoms,

[1651] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1652] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1653] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1654] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1655] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1656] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1657] The monovalent group represented by formula (64) is preferably represented by the following formula (65) or (66).

[1658] [Chemistry 188]

[1659]

[1660] In formula (65), R 631 ~R 640 Each independently is:

[1661] hydrogen atoms,

[1662] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1663] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1664] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1665] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1666] -Si(R 901 )(R 902 )(R 903 ),

[1667] -O-(R 904 ),

[1668] -S-(R 905 ),

[1669] -N(R 906 )(R 907 ),

[1670] Halogen atoms, cyano groups, nitro groups,

[1671] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1672] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1673] R 901 ~R 907 As defined in formula (1) above.

[1674] [Chemistry 189]

[1675]

[1676] In formula (66), Ar 601 、L 601 and L 603 As defined in the above formula (64). 601 It is a structure represented by the following formula (67).

[1677] [Chemistry 190]

[1678]

[1679] In formula (67), X 602 is an oxygen atom or a sulfur atom.

[1680] R 641 ~R 648 Any one of them is the same as L 603 Single bond bonding.

[1681] R is not a single bond 641 ~R 648 Each independently is:

[1682] hydrogen atoms,

[1683] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1684] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1685] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1686] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1687] -Si(R 901 )(R 902 )(R 903 ),

[1688] -O-(R 904 ),

[1689] -S-(R 905 ),

[1690] -N(R 906 )(R 907 ),

[1691] Halogen atoms, cyano groups, nitro groups,

[1692] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1693] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1694] R 901 ~R 907 As defined in formula (1) above.

[1695] As the compound represented by formula (61), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds can be given as specific examples. In the following specific examples, Me represents a methyl group.

[1696] [Chemistry 191]

[1697]

[1698] [Chemistry 192]

[1699]

[1700] [Chemistry 193]

[1701]

[1702] [Chemistry 194]

[1703]

[1704] [Chemistry 195]

[1705]

[1706] [Chemistry 196]

[1707]

[1708] [Chemistry 197]

[1709]

[1710] [Chemistry 198]

[1711]

[1712] [Chemistry 199]

[1713]

[1714] [Chemistry 200]

[1715]

[1716] [Chemistry 201]

[1717]

[1718] [Chemistry 202]

[1719]

[1720] [Chemistry 203]

[1721]

[1722] [Chemistry 204]

[1723]

[1724] [Chemistry 205]

[1725]

[1726] [Chemistry 206]

[1727]

[1728] [Chemistry 207]

[1729]

[1730] [Chemistry 208]

[1731]

[1732] [Chemistry 209]

[1733]

[1734] [Chemistry 210]

[1735]

[1736] [Chemistry 211]

[1737]

[1738] [Chemistry 212]

[1739]

[1740] [Chemistry 213]

[1741]

[1742] [Chemistry 214]

[1743]

[1744] [Chemistry 215]

[1745]

[1746] [Chemistry 216]

[1747]

[1748] [Chemistry 217]

[1749]

[1750] (Compound represented by formula (71))

[1751] The compound represented by formula (71) is described.

[1752] [Chemistry 218]

[1753]

[1754] In formula (71),

[1755] A 701 Ring and A 702 The rings are each independently:

[1756] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1757] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1758] Selected from A 701 Ring and A 702 One or more of the rings are bonded to a bonding bond * of the structure represented by the following formula (72).

[1759] [Chemistry 219]

[1760]

[1761] In formula (72),

[1762] A 703 The rings are each independently:

[1763] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1764] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1765] X 701 NR 703 、C(R 704 )(R 705 )、Si(R 706 )(R 707 )、Ge(R 708 )(R 709 ), O, S or Se.

[1766] R 701 and R 702 They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[1767] R does not form a substituted or unsubstituted saturated or unsaturated ring 701 and R 702 , and R 703 ~R 709 Each independently is:

[1768] hydrogen atoms,

[1769] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1770] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1771] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1772] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1773] -Si(R 901 )(R 902 )(R 903 ),

[1774] -O-(R 904 ),

[1775] -S-(R 905 ),

[1776] -N(R 906 )(R 907 ),

[1777] Halogen atoms, cyano groups, nitro groups,

[1778] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1779] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1780] R 901 ~R 907 As defined in formula (1) above.

[1781] Selected from A 701 Ring and A 702 One or more of the rings is bonded to the bonding bond * of the structure represented by formula (72). That is, in one embodiment, A 701 The carbon atoms of the aromatic hydrocarbon ring or the heterocyclic ring are bonded to the bonding bond * of the structure represented by formula (72). In one embodiment, A 702 A carbon atom constituting the aromatic hydrocarbon ring or a ring atom constituting the heterocyclic ring is bonded to the bonding bond * of the structure represented by formula (72).

[1782] In one embodiment, the group represented by the following formula (73) and A 701 Ring and A 702 Either or both of the rings are bonded.

[1783] [Chemistry 220]

[1784]

[1785] In formula (73), Ar 701 and Ar 702 Each independently is:

[1786] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1787] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1788] L 701 ~L 703 Each independently is:

[1789] single bond,

[1790] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[1791] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[1792] These are a divalent linking group formed by bonding 2 to 4 of them.

[1793] In one embodiment, except A 701 Outside the ring, A 702 The carbon atoms of the aromatic hydrocarbon ring or the heterocyclic ring are bonded to the bonding bond * of the structure represented by formula (72). In this case, the structures represented by formula (72) may be the same or different.

[1794] In one embodiment, R 701 and R 702 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1795] In one embodiment, R 701 and R 702 They bond with each other to form a fluorene structure.

[1796] In one embodiment, Ring A 701 and Ring A 702 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[1797] In one embodiment, Ring A 703 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[1798] In one embodiment, X 701 O or S.

[1799] As specific examples of the compound represented by formula (71), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1800] [Chemistry 221]

[1801]

[1802] [Chemistry 222]

[1803]

[1804] [Chemistry 223]

[1805]

[1806] [Chemistry 224]

[1807]

[1808] (Compound represented by formula (81))

[1809] The compound represented by formula (81) is described.

[1810] [Chemistry 225]

[1811]

[1812] In formula (81),

[1813] A 801 The ring is a ring represented by formula (82) fused at any position of adjacent rings.

[1814] A 802 The ring is a ring represented by formula (83) fused at any position of adjacent rings. 2 bonding bonds * and A 803 Bonding at any position of the ring.

[1815] X 801 and X 802 Each independently is C(R 803 )(R 804 )、Si(R 805 )(R 806 ), oxygen atom, sulfur atom.

[1816] A 803 The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1817] Ar 801 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1818] R 801 ~R 806 Each independently is:

[1819] hydrogen atoms,

[1820] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1821] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1822] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1823] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1824] -Si(R 901 )(R 902 )(R 903 ),

[1825] -O-(R 904 ),

[1826] -S-(R 905 ),

[1827] -N(R 906 )(R 907 ),

[1828] Halogen atoms, cyano groups, nitro groups,

[1829] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1830] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1831] R 901 ~R 907 As defined in formula (1) above.

[1832] m801 and m802 are each independently an integer from 0 to 2. When they are 2, multiple R 801 or R 802 They may be the same as or different from each other.

[1833] a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in the brackets shown by "3-a801" may be the same or different. When a801 is 2, Ar 801 They may be the same as or different from each other.

[1834] In one embodiment, Ar 801 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1835] In one embodiment, Ring A 803 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[1836] In one embodiment, R 803 and R 804 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1837] In one embodiment, a801 is 1.

[1838] Specific examples of the compound represented by formula (81) include the following compounds.

[1839] [Chemistry 226]

[1840]

[1841] Specific examples of each group in formulae (A1) to (D1) and the like are described in the [Definition] column of this specification.

[1842] (Compound represented by formula (91))

[1843] The compound represented by formula (91) is described.

[1844] [Chemistry 227]

[1845]

[1846] In formula (91),

[1847] R 951 ~R 960 One or more groups of two or more adjacent ones, R a1 ~R a5 One or more groups of two or more adjacent ones, and R a6 ~R a10 Among one or more groups of two or more adjacent groups in the , any one or more groups are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring having 3 to 30 ring atoms.

[1848] R not participating in the ring 951 ~R 960 、R a1 ~R a5 , and R a6 ~R a10 Each independently is:

[1849] hydrogen atoms,

[1850] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1851] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1852] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1853] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[1854] Substituted or unsubstituted amino,

[1855] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1856] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1857] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1858] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1859] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1860] a substituted or unsubstituted phosphine group,

[1861] substituted or unsubstituted phosphoryl,

[1862] a substituted or unsubstituted silyl group,

[1863] a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms,

[1864] Cyano, nitro, carboxyl, or

[1865] Halogen atoms.

[1866] 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.

[1867] Regarding “R 951 ~R 960 One or more groups of two or more adjacent ones, R a1 ~R a5 One or more groups of two or more adjacent ones, and R a6 ~R a10Specific examples of "one or more groups of two or more adjacent ring atoms in the above" being bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms will be described.

[1868] As a specific example of two or more adjacent rings bonded to each other, if R 957 ~R 960 For example, the following partial structures can be cited. In the following partial structures, adjacent R 958 、R 959 With R 960 These three are bonded to each other to form a ring.

[1869] [Chemistry 228]

[1870]

[1871] In addition, as a specific example of "one or more groups of two or more adjacent groups" bonding to each other to form a ring, if R 951 ~R 956 For example, the following partial structures can be cited. In the following partial structures, R 952 With R 953 , and R 954 With R 955 These two groups are bonded to each other to form another two rings.

[1872] [Chemistry 229]

[1873]

[1874] In one embodiment, R in the above formula (91) 952 With R 953 They are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms.

[1875] In one embodiment, the compound represented by the above formula (91) is a compound represented by the following formula (91-1).

[1876] [Chemistry 230]

[1877]

[1878] In formula (91-1), R 951 、R 954 ~R 960 As defined in formula (91) above.

[1879] R c1 and R c2 Each independently is:

[1880] hydrogen atoms,

[1881] unsubstituted alkyl group having 1 to 50 carbon atoms,

[1882] unsubstituted alkenyl having 2 to 50 carbon atoms,

[1883] unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1884] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1885] -Si(R 901 )(R 902 )(R 903 ),

[1886] -O-(R 904 ),

[1887] -S-(R 905 ),

[1888] -N(R 906 )(R 907 ),

[1889] Halogen atoms, cyano groups, nitro groups,

[1890] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1891] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1892] R 901 ~R 907 Each independently is:

[1893] hydrogen atoms,

[1894] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1895] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1896] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1897] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[1898] In one embodiment, R in the above formula (91) 958 ~R 960Two or more of them are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms.

[1899] In one embodiment, the compound represented by the above formula (91) is a compound represented by the following formula (91-2).

[1900] [Chemistry 231]

[1901]

[1902] In formula (91-2), R 951 ~R 957 As defined in formula (91) above.

[1903] In one embodiment, the R in the aforementioned formula (91) that does not participate in the ring formation is 951 ~R 960 、R a1 ~R a5 , and R a6 ~R a10 Each independently is:

[1904] hydrogen atoms,

[1905] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1906] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1907] Although specific examples of the compound represented by formula (91) are described below, these are merely illustrative and the compound represented by formula (91) is not limited to the following specific examples.

[1908] [Chemistry 232]

[1909]

[1910] [Chemistry 233]

[1911]

[1912] [Chemistry 234]

[1913]

[1914] [Chemistry 235]

[1915]

[1916] [Chemistry 236]

[1917]

[1918] [Chemistry 237]

[1919]

[1920] [Chemistry 238]

[1921]

[1922] [Chemistry 239]

[1923]

[1924] [Chemistry 240]

[1925]

[1926] [Chemistry 241]

[1927]

[1928] [Chemistry 242]

[1929]

[1930] [Chemistry 243]

[1931]

[1932] [Chemistry 244]

[1933]

[1934] [Chemistry 245]

[1935]

[1936] [Chemistry 246]

[1937]

[1938] [Chemistry 247]

[1939]

[1940] [Chemistry 248]

[1941]

[1942] [Chemistry 249]

[1943]

[1944] [Chemistry 250]

[1945]

[1946] [Chemistry 251]

[1947]

[1948] [Chemistry 252]

[1949]

[1950] [Chemistry 253]

[1951]

[1952] [Chemistry 254]

[1953]

[1954] The organic EL device according to one embodiment of the present invention has:

[1955] anode,

[1956] cathode, and

[1957] a light emitting region located between the anode and the cathode,

[1958] The light-emitting region includes a first light-emitting layer and a second light-emitting layer.

[1959] The first light-emitting layer is directly adjacent to the second light-emitting layer.

[1960] The first light-emitting layer is located between the anode and the second light-emitting layer.

[1961] Either the first emitting layer or the second emitting layer may include a compound containing at least one deuterium atom, and any conventionally known materials and device configurations may be used as long as the effects of the present invention are not impaired.

[1962] Hereinafter, the layer structure of the organic EL element according to one embodiment of the present invention will be described.

[1963] An organic EL element according to one embodiment of the present invention comprises an organic layer between a pair of electrodes consisting of a cathode and an anode. The organic layer comprises a plurality of layers comprising organic compounds. The organic layer may comprise a layer consisting solely of one or more organic compounds. The organic layer may comprise a layer comprising both organic compounds and inorganic compounds. The organic EL element may comprise a layer consisting solely of one or more inorganic compounds.

[1964] The layers that can be used in the layer structure of the organic EL element are not particularly limited, and examples thereof include a hole transport region (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer, etc.) arranged 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.) arranged between the cathode and the light-emitting layer, etc.

[1965] The organic EL element according to one embodiment of the present invention may be a single-color fluorescent or phosphorescent light-emitting element, or a fluorescent / phosphorescent mixed white light-emitting element. Furthermore, it may be a single type having a single light-emitting unit or a tandem type having multiple light-emitting units.

[1966] The term "light-emitting unit" refers to a minimum unit including organic layers, at least one of which is a light-emitting layer, and which emits light by recombination of injected holes and electrons.

[1967] In addition, the "light-emitting layer" described in this specification refers to an organic layer having a light-emitting function. The light-emitting layer may be, for example, a phosphorescent light-emitting layer or a fluorescent light-emitting layer, and may be a single layer or multiple layers.

[1968] The light-emitting unit may be a stacked type having multiple phosphorescent and fluorescent light-emitting layers. In this case, a spacer layer may be provided between the light-emitting layers to prevent excitons generated in the phosphorescent layer from diffusing to the fluorescent layer.

[1969] Examples of a single-type organic EL element include an element structure of anode / light-emitting unit / cathode.

[1970] A representative layer structure of the light-emitting unit is shown below. The layers in parentheses are optional.

[1971] (c) (hole injection layer / hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1972] (d) (hole injection layer / hole transport layer / first phosphorescent emitting layer / second phosphorescent emitting layer ( / electron transport layer / electron injection layer)

[1973] (f) (Hole injection layer / )Hole transport layer / First phosphorescent emitting layer / Second phosphorescent emitting layer / Spacer layer / Fluorescent emitting layer ( / Electron transport layer / Electron injection layer)

[1974] (h) (Hole injection layer / )Hole transport layer / Phosphorescent emitting layer / Spacer layer / First fluorescent emitting layer / Second fluorescent emitting layer ( / Electron transport layer / Electron injection layer)

[1975] (i) (Hole injection layer / )Hole transport layer / Electron blocking layer / Fluorescent light emitting layer / Fluorescent light emitting layer ( / Electron transport layer / Electron injection layer)

[1976] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent emitting layer / phosphorescent emitting layer ( / electron transport layer / electron injection layer)

[1977] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light-emitting layer / fluorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1978] (1) (hole injection layer / hole transport layer / exciton blocking layer / phosphorescent light emitting layer / phosphorescent light emitting layer / electron transport layer / electron injection layer)

[1979] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / fluorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1980] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / fluorescent light-emitting layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[1981] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light-emitting layer / phosphorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1982] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light-emitting layer / phosphorescent light-emitting layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[1983] (q) (hole injection layer / ) hole transport layer / fluorescent emitting layer / fluorescent emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[1984] (r) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / phosphorescent emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[1985] (s) (hole injection layer / ) hole transport layer / fluorescent emitting layer / fluorescent emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[1986] (t) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / phosphorescent emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[1987] Among them, 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, a hole injection layer is preferably provided between the hole transport layer and the anode. In addition, when the organic EL element has an electron injection layer and an electron transport layer, an electron injection layer is preferably provided between the electron transport layer and the cathode. In addition, the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer may each be composed of one layer or a plurality of layers.

[1988] Multiple phosphorescent light-emitting layers, and each phosphorescent light-emitting layer and fluorescent light-emitting layer can be a light-emitting layer of a different color. For example, the light-emitting unit (f) can be configured as a hole transport layer / first phosphorescent light-emitting layer (red light-emitting) / second phosphorescent light-emitting layer (green light-emitting) / spacer layer / fluorescent light-emitting layer (blue light-emitting) / electron transport layer.

[1989] It should be noted that an electron-blocking layer may be provided between each light-emitting layer and the hole-transporting layer or spacer layer. Alternatively, a hole-blocking layer may be provided between each light-emitting layer and the electron-transporting layer. These electron-blocking and hole-blocking layers can confine electrons and holes within the light-emitting layer, increasing the probability of charge recombination within the light-emitting layer and improving luminous efficiency.

[1990] A typical element structure of a tandem organic EL element is, for example, an element structure of anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode.

[1991] The first light-emitting unit and the second light-emitting unit can be independently selected from the above-mentioned light-emitting units, for example.

[1992] The intermediate layer is also commonly 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 supplies electrons to the first light-emitting unit and holes to the second light-emitting unit and can be formed from known materials.

[1993] Hereinafter, the functions and materials of each layer of the organic EL element described in this specification will be described.

[1994] (Substrate)

[1995] The substrate is used as a support for the organic EL element. The substrate preferably has a transmittance of 50% or more for light in the visible light region with a wavelength of 400 to 700 nm, and is also preferably a smooth substrate. Examples of the material for the substrate include soda-lime glass, aluminosilicate glass, quartz glass, and plastic. In addition, a flexible substrate can be used as the substrate. A flexible substrate refers to a (flexible) substrate that can be bent, and examples thereof include a plastic substrate. Specific examples of materials forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.

[1996] (anode)

[1997] As the anode, preferably used are metals, alloys, conductive compounds, and mixtures thereof having a high work function (specifically, 4.0 eV or greater). Specific examples of anode materials include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide or zinc oxide, and graphene. Other examples include gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (e.g., titanium nitride).

[1998] The anode can generally be formed by forming a film of these materials on a substrate by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target material containing 1-10% by mass of zinc oxide added to indium oxide. Alternatively, indium oxide containing tungsten oxide or zinc oxide can be formed by sputtering using a target material containing 0.5-5% by mass of tungsten oxide or 0.1-1% by mass of zinc oxide added to indium oxide.

[1999] Other methods for forming the anode include, for example, vacuum deposition, coating, inkjet, and spin coating. For example, when silver paste is used, coating, inkjet, and the like can be used.

[2000] 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 anode's work function and facilitates hole injection. Therefore, the anode can use conventional electrode materials, such as metals, alloys, conductive compounds, and mixtures thereof. Specifically, materials with low work functions, such as 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; and alloys containing rare earth metals, can also be used for the anode.

[2001] (Hole Injection Layer)

[2002] 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 to 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.) can be mentioned. Among them, aromatic amine compounds and acceptor compounds are preferred, and acceptor compounds are more preferred.

[2003] Specific examples of the aromatic amine compound include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNAB). TPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as: PCzPCN1), etc.

[2004] As acceptor compounds, preferred are, for example, heterocyclic derivatives having an electron-withdrawing group, quinone derivatives having an electron-withdrawing group, aryl borane derivatives, heteroaryl borane derivatives, and the like. Specific examples include hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation: F4TCNQ), and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane.

[2005] When an acceptor compound is used, the hole injection layer preferably further contains a host material. As the host material, any known material for organic EL devices can be used, and for example, an electron-donating (donor) compound is preferably used.

[2006] (Hole Transport Layer)

[2007] The hole transport layer is a layer containing a substance with a high hole transport property, and has a function of transporting holes from the anode to the organic layer.

[2008] As a substance with high hole transport property, preferably one having 10 -6 cm 2 Examples of substances having a hole mobility of 100 nm / (V·s) or higher include aromatic amine compounds, carbazole derivatives, anthracene derivatives, and polymer compounds.

[2009] Specific examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), triphenylamine (abbreviated as: MTDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as: 4,4'-bis[N-(spiro-9,9'-difluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as: MTDATA), 4,4'-bis[N-(spiro-9,9'-difluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as: BSPB), etc.

[2010] Specific examples of carbazole derivatives include 4,4′-bis(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[2011] Specific examples of anthracene derivatives include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[2012] Specific examples of the polymer compound include poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA).

[2013] As long as the compound has a higher hole-transporting property than an electron-transporting property, substances other than those listed above may be used for the hole-transporting layer.

[2014] The hole transport layer may be a single layer or a stack of two or more layers. In this case, it is preferable to arrange a layer containing a substance with a large energy gap among substances with high hole transport properties on the side close to the light emitting layer.

[2015] (Luminescent layer)

[2016] The light-emitting layer is a layer containing a highly luminescent substance (dopant material). As a dopant material, various materials can be used, for example, fluorescent compounds (fluorescent dopants), phosphorescent compounds (phosphorescent dopants), etc. can be used. A fluorescent compound refers to a compound that can emit light from a singlet excited state, and a light-emitting layer containing such a compound is called a fluorescent light-emitting layer. In addition, a phosphorescent compound refers to a compound that can emit light from a triplet excited state, and a light-emitting layer containing such a compound is called a phosphorescent light-emitting layer.

[2017] The light-emitting layer typically contains a dopant material and a host material that enables efficient light emission. The dopant material is sometimes referred to as a guest material, emitter, or luminescent material, depending on the literature. Furthermore, the host material is sometimes referred to as a matrix material, depending on the literature.

[2018] A single light-emitting layer may contain multiple dopant materials and multiple host materials.

[2019] In this specification, a host material combined with a fluorescent dopant is referred to as a "fluorescent host," and a host material combined with a phosphorescent dopant is referred to as a "phosphorescent host." It should be noted that the distinction between fluorescent hosts and phosphorescent hosts is not solely based on molecular structure. A phosphorescent host is a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, but this does not mean it cannot be used as a material for a fluorescent light-emitting layer. The same applies to fluorescent hosts.

[2020] The content of the dopant material in the light-emitting layer is not particularly limited. From the viewpoint of sufficient luminescence and concentration quenching, it is, for example, preferably 0.1 to 70 mass%, more preferably 0.1 to 30 mass%, further preferably 1 to 30 mass%, further preferably 1 to 20 mass%, and particularly preferably 1 to 10 mass%.

[2021] <Fluorescent dopant>

[2022] Examples of the fluorescent dopant include fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, and carbazole derivatives, among which fused ring amine derivatives, boron-containing compounds, and carbazole derivatives are preferred.

[2023] Examples of the fused ring amine derivatives include diaminopyrene derivatives, diamino derivatives, diaminoanthracene derivatives, diaminofluorene derivatives, diaminofluorene derivatives in which one or more benzofurano skeletons are fused, and the like.

[2024] Examples of the boron-containing compound include pyrromethene derivatives and triphenylborane derivatives.

[2025] Examples of blue fluorescent dopants include pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: YGAPA), and 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA).

[2026] Examples of green fluorescent dopants include aromatic amine derivatives. Specific examples include N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAP), and N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA). A), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as: DPhAPhA), etc.

[2027] Examples of red fluorescent dopants include butacene derivatives and diamine derivatives. Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)butacene-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[2028] <Phosphorescent dopant>

[2029] Examples of the phosphorescent dopant include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.

[2030] Examples of the heavy metal complex include iridium complexes, osmium complexes, platinum complexes, etc. The heavy metal complex is preferably an ortho-metalated complex of a metal selected from iridium, osmium, and platinum.

[2031] Examples of rare earth metal complexes include terbium complexes and europium complexes. Specific examples include terbium(III) tris(acetylacetonato)(monophenanthroline) (abbreviated as Tb(acac)3(Phen)), europium(III) tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline) (abbreviated as Eu(DBM)3(Phen)), and europium(III) tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) (abbreviated as Eu(TTA)3(Phen)). These rare earth metal complexes are suitable as phosphorescent dopants because rare earth metal ions emit light due to electron migration between different multiplets.

[2032] Examples of blue phosphorescent dopants include iridium complexes, osmium complexes, and platinum complexes. Specific examples include iridium(III) bis[2-(4',6'-difluorophenyl)pyridine-N,C2']tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), iridium(III) bis[2-(4',6'-difluorophenyl)pyridine-N,C2']picolinate (abbreviated as FIrpic), iridium(III) bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']picolinate (abbreviated as Ir(CF3ppy)2(pic)), and iridium(III) bis[2-(4',6'-difluorophenyl)pyridine-N,C2']acetylacetonate (abbreviated as FIracac).

[2033] Examples of green phosphorescent dopants include iridium complexes. Specifically, they include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III) acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinolinol)iridium(III) acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[2034] Examples of red phosphorescent dopants include iridium complexes, platinum complexes, terbium complexes, and europium complexes. Specific examples include iridium(III) bis[2-(2'-benzo[4,5-α]thienyl)pyridinium-N,C3']acetylacetonate (abbreviated as Ir(btp)2(acac)), iridium(III) bis(1-phenylisoquinolinium-N,C2')acetylacetonate (abbreviated as Ir(piq)2(acac)), iridium(III) (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline] (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[2035] <Main material>

[2036] As the host material, 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; naphthalene derivatives, triphenylene derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Derivatives, tetracene derivatives, fluoranthene derivatives and other condensed aromatic compounds; triarylamine derivatives, condensed polycyclic aromatic amine derivatives and other aromatic amine compounds. Multiple host materials can be used in combination.

[2037] Specific examples of the metal complex include tris(8-hydroxyquinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinolinolato)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[2038] Specific examples of heterocyclic compounds 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), bathocuproin (abbreviation: BCP), and the like.

[2039] Specific examples of the condensed aromatic compound include: 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 9,9'-(phenylethylene-3,3'-diyl)phenanthrene (DPNS), 9,9'-(phenylethylene-4,4'-diyl)phenanthrene (DPNS2), 3,3',3"-(phenyl-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl wait.

[2040] Specific examples of the aromatic amine compound include N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl- 2-Anthracenyl)-N,9-diphenyl-9H-carbazole-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'-difluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc.

[2041] As the fluorescent host, a compound having a higher singlet energy level than the fluorescent dopant is preferred, and examples thereof include heterocyclic compounds and fused aromatic compounds. As the fused aromatic compound, anthracene derivatives, pyrene derivatives, derivatives, tetracene derivatives, etc.

[2042] The phosphorescent host is preferably a compound having a triplet energy level higher than that of the phosphorescent dopant, and examples thereof include metal complexes, heterocyclic compounds, and condensed aromatic compounds. Among them, preferred are 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, and fluoranthene derivatives.

[2043] (Electron Transport Layer)

[2044] The electron transport layer is a layer containing a substance with high electron transport properties. -6 cm 2 Examples of substances having an electron mobility of 1 / Vs or higher include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, and polymer compounds.

[2045] Examples of the metal complex include aluminum complexes, beryllium complexes, and zinc complexes. Specific examples include tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ).

[2046] Examples of aromatic heterocyclic compounds include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazolephenanthridine derivatives; oxazine derivatives such as pyrimidine derivatives and triazine derivatives; and compounds containing a nitrogen-containing six-membered ring structure such as quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives (including those having a phosphine oxide-based substituent on the heterocyclic ring). Specific examples include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), and the like.

[2047] Examples of the aromatic hydrocarbon compound include anthracene derivatives and fluoranthene derivatives.

[2048] Specific examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), and the like.

[2049] As long as the compound has a higher electron-transporting property than a hole-transporting property, substances other than those listed above may be used for the electron-transporting layer.

[2050] The electron transport layer may be a single layer or a stack of two or more layers. In this case, it is preferable to arrange a layer containing a substance with a large energy gap among substances with high electron transport properties on the side close to the light emitting layer.

[2051] The electron transport layer may include, for example, metals such as alkali metals, magnesium, alkaline earth metals, and alloys containing two or more of these metals; metal compounds such as alkali metal compounds and alkaline earth metal compounds such as 8-hydroxyquinoline lithium (abbreviated as: Liq). When a metal such as an alkali metal, magnesium, alkaline earth metal, or an alloy containing two or more of these metals is included in the electron transport layer, its content is not particularly limited, but is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and even more preferably 1 to 10% by mass.

[2052] When a metal compound such as an alkali metal compound or an alkaline earth metal compound is included in the electron transport layer, its content is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. In addition, when the electron transport layer is multilayered, the layer located on the light-emitting layer side may be formed solely of these metal compounds.

[2053] (Electron Injection Layer)

[2054] The electron injection layer is a layer containing a substance with high electron injection properties, which has the function of efficiently injecting electrons from the cathode to the light-emitting layer. As a substance with high electron injection properties, for example, alkali metals, magnesium, alkaline earth metals, and compounds thereof can be mentioned. Specifically, lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, lithium oxide, etc. can be mentioned. In addition, substances containing alkali metals, magnesium, alkaline earth metals, or compounds thereof in substances with electron transport properties can be used. For example, substances containing magnesium in Alq can be used.

[2055] Alternatively, a composite material containing an organic compound and a donor compound may 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 and electron transport properties.

[2056] As the organic compound, a substance having excellent properties of transporting the received electrons is preferable. For example, the above-mentioned substances having high electron transport properties, ie, metal complexes and aromatic heterocyclic compounds, can be used.

[2057] As a donor compound, any substance capable of donating electrons to an organic compound may be used, and examples thereof include alkali metals, magnesium, alkaline earth metals, and rare earth metals. Specific examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and specific examples include lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide may also be used. Furthermore, organic compounds such as tetrathiafulvalene (TTF) may also be used.

[2058] (cathode)

[2059] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof with a low 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; and alloys containing rare earth metals.

[2060] The cathode is usually formed by vacuum deposition or sputtering. When silver paste is used, coating or inkjet methods can be used.

[2061] When an electron injection layer is provided, the cathode can be formed using various conductive materials, regardless of the work function, such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films using methods such as sputtering, inkjet, and spin coating.

[2062] (Insulation layer)

[2063] Organic EL devices are susceptible to pixel defects due to leakage and short circuits caused by the application of an electric field across thin films. To prevent this, a thin film insulating layer can be inserted between a pair of electrodes.

[2064] Specific examples of the substance used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture of these substances may be used for the insulating layer, and a laminate containing a plurality of layers of these substances may be used.

[2065] (Spacer layer)

[2066] For example, when stacking a fluorescent and phosphorescent layer, a spacer layer can be placed between the two layers to prevent excitons generated in the phosphorescent layer from diffusing into the fluorescent layer or to adjust carrier balance. A spacer layer can also be placed between multiple phosphorescent layers.

[2067] Since the spacer layer is provided between multiple light-emitting layers, it is preferably formed of a material having both electron-transporting and hole-transporting properties. In addition, from the perspective of preventing the diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more.

[2068] As the substance used for the spacer layer, there can be mentioned the same substances as those used for the hole transport layer described above.

[2069] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[2070] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer.

[2071] An electron-blocking layer blocks electrons from leaking from the light-emitting layer to the hole-transporting layer. A hole-blocking layer blocks holes from leaking from the light-emitting layer to the electron-transporting layer. An exciton-blocking layer blocks excitons generated in the light-emitting layer from diffusing to adjacent layers, thereby confining the excitons within the light-emitting layer.

[2072] (Middle layer)

[2073] An intermediate layer is provided in a tandem organic EL element.

[2074] (Layer Formation Method)

[2075] If not otherwise described, the formation method of each layer of the organic EL element is not particularly limited. As the formation method, known methods such as dry film forming method and wet film forming method can be used. As a specific example of the dry film forming method, vacuum evaporation method, sputtering method, plasma method, ion plating method, etc. can be mentioned. As a specific example of the wet film forming method, various coating methods such as spin coating method, immersion method, flow coating method, ink jet method, etc. can be mentioned.

[2076] (film thickness)

[2077] Unless otherwise specified, the 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 luminous brightness cannot be achieved. On the other hand, if the film thickness is too large, a high driving voltage is required, which reduces efficiency. From this perspective, the film thickness is generally preferably 1 nm to 10 μm, and more preferably 1 nm to 0.2 μm.

[2078] [Electronic equipment]

[2079] An electronic device according to one embodiment of the present invention includes the organic EL element according to one embodiment of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules; display devices for televisions, mobile phones, smartphones, and personal computers; and light-emitting devices for lighting and automotive lamps.

[2080] Example

[2081] Next, the present invention will be described in further detail with reference to Examples and Comparative Examples, but the present invention is not limited in any way to the contents of these Examples.

[2082] <Compound>

[2083] The compounds (host materials) having a deuterium atom and represented by formula (1) used in the production of the organic EL devices of Examples 1 to 42 are shown below.

[2084] [Chemistry 255]

[2085]

[2086] The compounds (host materials) not having a deuterium atom used in the production of the organic EL devices of Examples 1 to 42 and Comparative Examples 1 to 15 are shown below.

[2087] [Chemistry 256]

[2088]

[2089] The dopant materials used in the production of the organic EL devices of Examples 1 to 42 and Comparative Examples 1 to 15 are shown below.

[2090] [Chemistry 257]

[2091]

[2092] Other compounds used in the production of the organic EL devices of Examples 1 to 42 and Comparative Examples 1 to 15 are shown below.

[2093] [Chemistry 258]

[2094]

[2095] <Fabrication of Organic EL Devices 1>

[2096] Organic EL devices were produced and evaluated as follows.

[2097] Example 1

[2098] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to achieve an ITO film thickness of 130 nm.

[2099] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, the compound HI was deposited onto the surface with the transparent electrode, covering the transparent electrode. A 5 nm thick film of the compound HI was formed. This HI film functioned as a hole injection layer.

[2100] After forming the HI film, the compound HT was then vapor-deposited to form an 80 nm thick HT film on the HI film. The HT film functioned as a first hole transport layer.

[2101] After the HT film was formed, the compound EBL was then vapor-deposited to form a 10 nm thick EBL film on the HT film. This EBL film functioned as a second hole transport layer.

[2102] D-BH-1 (host material) and BD-1 (dopant material) were co-evaporated on the EBL film so that the ratio (mass ratio) of BD-1 was 4%, thereby forming a first light-emitting layer with a thickness of 7.5 nm.

[2103] On the first emitting layer, BH-1 (host material) and BD-1 (dopant material) were co-deposited so that the ratio (mass ratio) of BD-1 was 4%, thereby forming a 17.5 nm thick second emitting layer.

[2104] HBL was evaporated on the second emitting layer to form a 10nm-thick electron transport layer. ET, an electron injection material, was evaporated on the electron transport layer to form a 15nm-thick electron injection layer. LiF was evaporated on the electron injection layer to form a 1nm-thick LiF film. Metal Al was evaporated on the LiF film to form an 80nm-thick metal cathode.

[2105] An organic EL device was produced as described above. The layer structure of the device is as follows.

[2106] ITO(130nm) / HI(5nm) / HT(80nm) / EBL(10nm) / D-BH-1:BD-1(7.5nm:4%) / BH-1:BD-1(17.5nm:4%) / HBL(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2107] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2108] (Evaluation of Organic EL Device 1)

[2109] The organic EL device was subjected to a current density of 50 mA / cm 2 The voltage was applied in a manner of , and the time until the luminance reached 90% of the initial luminance (LT90 (unit: hours)) was measured. The results are shown in Table 1.

[2110] Comparative Example 1

[2111] An organic EL device was prepared and evaluated in the same manner as in Example 1, except that the compound shown in Table 1 was used as the host material of the light-emitting layer.

[2112] [Table 1]

[2113]

[2114] Example 2 and Comparative Example 2

[2115] An organic EL device was prepared and evaluated in the same manner as in Example 1, except that the compound shown in Table 2 was used as the host material of the light-emitting layer.

[2116] [Table 2]

[2117]

[2118] It can be seen from the results in Tables 1 and 2 that the elements of Examples 1 and 2, in which a first light-emitting layer comprising a main material having deuterium atoms and a second light-emitting layer comprising a main material not having deuterium atoms are stacked in the light-emitting region, have improved lifespans compared to the elements of Comparative Examples 1 and 2 having a single light-emitting layer comprising a main material not having deuterium atoms.

[2119] The thickness of the light-emitting layers of Examples 1 and 2 and Comparative Examples 1 and 2, when viewed as a whole, was the same. This indicates that even when the entire light-emitting region does not contain host materials containing deuterium atoms, i.e., D-BH-1 or D-BH-2, the lifetime is improved as long as the light-emitting layer contains host materials containing deuterium atoms, i.e., D-BH-1 or D-BH-2, in only a portion of the light-emitting region.

[2120] <Fabrication of Organic EL Devices 2>

[2121] Example 3

[2122] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Diomatech) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to a thickness of 130 nm.

[2123] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device. First, compound HA1 was evaporated on the surface on which the transparent electrode lines were formed to cover the transparent electrode, forming a hole injection layer (HI) with a thickness of 5 nm.

[2124] After the hole injection layer was formed, compound HT1 was evaporated to form a first hole transport layer (HT) with a thickness of 80 nm.

[2125] After the first hole transport layer was formed, compound HT2 was evaporated to form a second hole transport layer (also referred to as electron barrier layer) (EBL) with a thickness of 10 nm.

[2126] 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% by mass to form a first light-emitting layer with a thickness of 10 nm.

[2127] 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 ratio of compound BD-2 became 2 mass % to form a second light-emitting layer with a thickness of 15 nm.

[2128] Compound ET1 was evaporated on the second light-emitting layer to form an electron transport layer with a thickness of 10 nm.

[2129] On the electron transport layer, the compound nCGL and metal Li were co-evaporated to form an electron injection layer having a thickness of 30 nm so that the ratio of metal Li was 4 mass %.

[2130] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 50 nm.

[2131] The component structure of Example 3 is briefly shown below.

[2132] 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))

[2133] In addition, the numbers in parentheses represent film thickness (unit: nm).

[2134] Similarly, the percentages in parentheses (98%:2%) represent the ratio (mass %) of the first host material (compound BH1 or compound BH2) to compound BD1 in the first and second light-emitting layers, and the percentages (96%:4%) represent the ratio (mass %) of compound nCGL to metallic Li in the hole injection layer. The same notation will be used hereinafter.

[2135] Example 4

[2136] The organic EL device of Example 4 was produced in the same manner as in Example 3, except that the first and second light-emitting layers of Example 3 were changed to the compounds and film thicknesses described in Table 3.

[2137] Comparative Example 3

[2138] The organic EL device of Comparative Example 3 was produced in the same manner as in Example 3, except that only the first light-emitting layer was formed as described in Table 3.

[2139] (Evaluation of Organic EL Device 2)

[2140] The organic EL devices obtained in Examples 3 to 4 and Comparative Example 3 were heated to a current density of 50 mA / cm 2 The voltage was applied in a manner of , and the time until the luminance reached 95% of the initial luminance (LT95 (unit: hours)) was measured. The results are shown in Table 3.

[2141] [Table 3]

[2142]

[2143] A comparison of Example 4 and Comparative Example 3 in Table 3, which differ only in whether the host material in the first light-emitting layer contains deuterium atoms, shows that the device of Example 4 has an improved lifespan compared to the device of Comparative Example 3.

[2144] <Fabrication of Organic EL Devices 3>

[2145] Example 5

[2146] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to achieve an ITO film thickness of 130 nm.

[2147] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, the compound HI was deposited onto the surface with the transparent electrode, covering the transparent electrode. A 5 nm thick film of the compound HI was formed. This HI film functioned as a hole injection layer.

[2148] After forming the HI film, the compound HT was then vapor-deposited to form an 80 nm thick HT film on the HI film. The HT film functioned as a first hole transport layer.

[2149] After the HT film was formed, the compound EBL-2 was then vapor-deposited to form a 10 nm thick EBL-2 film on the HT film. This EBL-2 film functioned as a second hole transport layer.

[2150] D-BH-1 (host material) and BD-1 (dopant material) were co-evaporated on the EBL-2 film so that the ratio (mass ratio) of BD-1 was 4%, thereby forming a first light-emitting layer with a thickness of 7.5 nm.

[2151] On the first emitting layer, BH-1 (host material) and BD-1 (dopant material) were co-deposited so that the ratio (mass ratio) of BD-1 was 4%, thereby forming a 17.5 nm thick second emitting layer.

[2152] HBL-2 ​​was vapor-deposited on the second emitting layer to form a 10nm-thick electron transport layer. ET, an electron injection material, was vapor-deposited on the electron transport layer to form a 15nm-thick electron injection layer. LiF was vapor-deposited on the electron injection layer to form a 1nm-thick LiF film. Metal Al was vapor-deposited on the LiF film to form an 80nm-thick metal cathode.

[2153] An organic EL device was produced as described above. The layer structure of the device is as follows.

[2154] ITO(130nm) / HI(5nm) / HT(80nm) / EBL-2(10nm) / D-BH-1:BD-1(7.5nm:4%) / BH-1:BD-1(17.5nm:4%) / HBL-2(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2155] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2156] Examples 6 to 11 and Comparative Examples 4 to 5

[2157] An organic EL device was prepared in the same manner as in Example 5, except that the compound shown in Table 4 was used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was set to the film thickness shown in Table 4.

[2158] (Evaluation of Organic EL Device 3)

[2159] The organic EL device was subjected to a current density of 50 mA / cm 2 Voltage was applied in a manner consistent with the initial luminance, and the time required for the luminance to reach 90% of the initial luminance (LT90 (unit: hours)) was measured. The LT90 value of the device of Comparative Example 4, which had a single emitting layer containing a host material without deuterium atoms, was set to 1. The relative LT90 values ​​for the Examples and Comparative Examples are shown in Table 4.

[2160] [Table 4]

[2161]

[2162] As can be seen from the results in Table 4, the elements of Examples 5 to 11, in which a first light-emitting layer comprising a main material D-BH-1 having deuterium atoms and a second light-emitting layer comprising a main material BH-1 not having deuterium atoms are stacked in the light-emitting region, have improved lifespan compared to the element of Comparative Example 4 having a single light-emitting layer comprising a main material BH-1 not having deuterium atoms.

[2163] Furthermore, it is found that the devices of Examples 6 to 11 have comparable lifetimes to the device of Comparative Example 5 having a single light-emitting layer containing the host material D-BH-1 having deuterium atoms.

[2164] Example 12

[2165] An organic EL device was prepared and evaluated in the same manner as in Example 5, except that the host material of the first emitting layer was changed to D-BH-2, the host material of the second emitting layer was changed to BH-2, and the film thickness of each emitting layer was set to the film thickness shown in Table 5. The results are shown in Table 5.

[2166] The layer structure of the element produced as described above is as follows.

[2167] ITO(130nm) / HI(5nm) / HT(80nm) / EBL-2(10nm) / D-BH-2:BD-1(2.5nm:4%) / BH-2:BD-1(22.5nm:4%) / HBL-2(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2168] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2169] Examples 13 to 20 and Comparative Examples 6 to 7

[2170] An organic EL device was prepared in the same manner as in Example 12, except that the compounds shown in Table 5 were used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was set to the film thickness shown in Table 5. The evaluation was performed in the same manner as in Example 5. The results are shown in Table 5.

[2171] [Table 5]

[2172]

[2173] As can be seen from the results in Table 5, the elements of Examples 12 to 20, in which a first light-emitting layer comprising a main material D-BH-2 having deuterium atoms and a second light-emitting layer comprising a main material BH-2 not having deuterium atoms are stacked in the light-emitting region, have improved lifespan compared to the element of Comparative Example 6 having a single light-emitting layer comprising a main material BH-2 not having deuterium atoms.

[2174] Furthermore, it is found that the devices of Examples 14 to 20 have comparable lifetimes to the device of Comparative Example 7 having a single light-emitting layer containing a host material D-BH-2 having deuterium atoms.

[2175] Example 21

[2176] An organic EL device was produced 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 set to the thickness shown in Table 6. The device was evaluated in the same manner as in Example 5. The results are shown in Table 6.

[2177] The layer structure of the element produced as described above is as follows.

[2178] ITO(130nm) / HI(5nm) / HT(80nm) / EBL(10nm) / D-BH-1:BD-2(5nm:2%) / BH-1:BD-2(20nm:2%) / HBL(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2179] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2180] Examples 22 to 28 and Comparative Example 8

[2181] Organic EL devices were prepared and evaluated in the same manner as in Example 21, except that the compounds shown in Table 6 were used as host materials for the light-emitting layers and the film thickness of each light-emitting layer was set to the film thickness shown in Table 6. The results are shown in Table 6.

[2182] [Table 6]

[2183]

[2184] As can be seen from the results in Table 6, even if the dopant material of the light-emitting layer is changed to BD-2, the elements of Examples 21 to 28, which are a stack of a first light-emitting layer comprising a main material D-BH-1 having deuterium atoms and a second light-emitting layer comprising a main material BH-1 not having deuterium atoms, have improved lifespan compared to the element of Comparative Example 8 having a single light-emitting layer comprising a main material BH-1 not having deuterium atoms.

[2185] Example 29

[2186] An organic EL device was produced 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-3, the proportion of BD-3 was changed to 2 mass%, and the film thickness of each light-emitting layer was set to the thickness shown in Table 7. The device was evaluated in the same manner as in Example 5. The results are shown in Table 7.

[2187] The layer structure of the element produced as described above is as follows.

[2188] ITO(130nm) / HI(5nm) / HT(80nm) / EBL(10nm) / D-BH-1:BD-3(5nm:2%) / BH-1:BD-3(20nm:2%) / HBL(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2189] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2190] Examples 30 to 36 and Comparative Example 9

[2191] An organic EL device was prepared and evaluated in the same manner as in Example 29, except that the compound shown in Table 7 was used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was set to the film thickness shown in Table 7. The results are shown in Table 7.

[2192] [Table 7]

[2193]

[2194] As can be seen from the results in Table 7, even if the dopant material of the light-emitting layer is changed to BD-3, the elements of Examples 29 to 36, in which a first light-emitting layer comprising a main material D-BH-1 having deuterium atoms and a second light-emitting layer comprising a main material BH-1 not having deuterium atoms are stacked, have improved lifespan compared to the element of Comparative Example 9 having a single light-emitting layer comprising a main material BH-1 not having deuterium atoms.

[2195] Example 37

[2196] An organic EL device was prepared in the same manner as in Example 1, except that the host material of the second emitting layer was changed to BH-2 and the thickness of the first and second emitting layers was set to 12.5 nm, and evaluated in the same manner as in Example 5. The results are shown in Table 8.

[2197] The layer structure of the element produced as described above is as follows.

[2198] ITO(130nm) / HI(5nm) / HT(80nm) / EBL(10nm) / D-BH-1:BD-1(12.5nm:4%) / BH-2:BD-1(12.5nm:4%) / HBL(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2199] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2200] Comparative Examples 10-11

[2201] An organic EL device was prepared and evaluated in the same manner as in Example 37, except that the compound shown in Table 8 was used as the host material of the light-emitting layer.

[2202] [Table 8]

[2203]

[2204] From the results in Table 8, it can be seen that the element of Example 37, in which the first light-emitting layer contains the main material D-BH-1 having deuterium atoms and the second light-emitting layer contains the main material BH-2 having a structure different from that of the main material D-BH-1 in the first light-emitting layer, has an improved lifespan compared to the element of Comparative Example 10, in which the first light-emitting layer contains the main material BH-1 without deuterium atoms and the second light-emitting layer contains the main material BH-2.

[2205] Furthermore, it is found that the device of Example 37 has a device life comparable to that of the device of Comparative Example 11 in which the first and second light-emitting layers respectively contain host materials D-BH-1 and D-BH-2 containing deuterium atoms.

[2206] Example 38

[2207] An organic EL device was prepared in the same manner as in Example 1, except that the host material of the first emitting layer was changed to D-BH-2 and the thickness of the first and second emitting layers was set to 12.5 nm, and evaluated in the same manner as in Example 5. The results are shown in Table 9.

[2208] The layer structure of the element produced as described above is as follows.

[2209] ITO(130nm) / HI(5nm) / HT(80nm) / EBL(10nm) / D-BH-2:BD-1(12.5nm:4%) / BH-1:BD-1(12.5nm:4%) / HBL(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2210] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2211] Comparative Examples 12-13

[2212] An organic EL device was prepared and evaluated in the same manner as in Example 38, except that the compound shown in Table 9 was used as the host material of the light-emitting layer.

[2213] [Table 9]

[2214]

[2215] From the results in Table 9, it can be seen that the element of Example 38, in which the first light-emitting layer contains the main material D-BH-2 having deuterium atoms and the second light-emitting layer contains the main material BH-1 having a structure different from that of the main material D-BH-2 in the first light-emitting layer, has an improved lifespan compared to the element of Comparative Example 12, in which the first light-emitting layer contains the main material BH-2 not having deuterium atoms and the second light-emitting layer contains the main material BH-1.

[2216] Furthermore, it is found that the device of Example 38 has a device life comparable to that of the device of Comparative Example 13 in which the first and second light-emitting layers contain host materials D-BH-2 and D-BH-1 containing deuterium atoms, respectively.

[2217] Example 39

[2218] An organic EL device was prepared and evaluated in the same manner as in Example 5, except that the host material of the first emitting layer was changed to D-BH-4, the host material of the second emitting layer was changed to BH-2, and the film thickness of the first and second emitting layers was set to 12.5 nm. The results are shown in Table 10.

[2219] The layer structure of the element produced as described above is as follows.

[2220] ITO(130nm) / HI(5nm) / HT(80nm) / EBL-2(10nm) / D-BH-4:BD-1(12.5nm:4%) / BH-2:BD-1(12.5nm:4%) / HBL-2(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2221] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2222] Example 40 and Comparative Example 14

[2223] An organic EL device was prepared and evaluated in the same manner as in Example 39, except that the compound shown in Table 10 was used as the host material of the light-emitting layer.

[2224] [Table 10]

[2225]

[2226] As can be seen from the results in Table 10, the element of Example 39, in which the first light-emitting layer contains the main material D-BH-4 having deuterium atoms and the second light-emitting layer contains the main material BH-2 having a structure different from that of the main material D-BH-4 in the first light-emitting layer, has an improved lifespan compared to the element of Comparative Example 14, in which the first light-emitting layer contains the main material BH-4 not having deuterium atoms and the second light-emitting layer contains the main material BH-2.

[2227] Furthermore, it is found that the device of Example 40, in which the first emitting layer contains the host material BH-4 having no deuterium atoms and the second emitting layer contains the host material D-BH-2 having deuterium atoms, has an improved lifespan compared to the device of Comparative Example 14.

[2228] Example 41

[2229] An organic EL device was prepared and evaluated in the same manner as in Example 5, except that the host material of the second emitting layer was changed to BH-4 and the thickness of the first and second emitting layers was set to 12.5 nm. The results are shown in Table 11.

[2230] The layer structure of the element produced as described above is as follows.

[2231] ITO(130nm) / HI(5nm) / HT(80nm) / EBL-2(10nm) / D-BH-1:BD-1(12.5nm:4%) / BH-4:BD-1(12.5nm:4%) / HBL-2(10nm) / ET(15nm) / LiF(1nm) / Al(80nm)

[2232] In parentheses, the numbers expressed as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2233] Example 42 and Comparative Example 15

[2234] An organic EL device was prepared and evaluated in the same manner as in Example 41, except that the compound shown in Table 11 was used as the host material of the light-emitting layer.

[2235] [Table 11]

[2236]

[2237] As can be seen from the results in Table 11, the element of Example 41, in which the first light-emitting layer contains the main material D-BH-1 having deuterium atoms and the second light-emitting layer contains the main material BH-4 having a structure different from that of the main material D-BH-1 in the first light-emitting layer, has an improved lifespan compared to the element of Comparative Example 15, in which the first light-emitting layer contains the main material BH-1 without deuterium atoms and the second light-emitting layer contains the main material BH-4.

[2238] Furthermore, it is found that the device of Example 42, in which the first emitting layer contains the host material BH-1 having no deuterium atoms and the second emitting layer contains the host material D-BH-4 having deuterium atoms, has an improved lifespan compared to the device of Comparative Example 15.

[2239] While several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art may readily make numerous modifications to these illustrative embodiments and / or examples without materially departing from the novel teachings and effects of the present invention. Therefore, these numerous modifications are intended to be within the scope of the present invention.

[2240] The contents of the documents described in this specification and the applications on which the Paris Convention priority claim of the present application is based are incorporated herein by reference in their entirety.

Claims

1. An organic electroluminescent element comprising: anode, 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 is directly adjacent to the second light-emitting layer, The first light-emitting layer is located between the anode and the second light-emitting layer. Either or both of the first light-emitting layer and the second light-emitting layer contain a compound having at least one deuterium atom as a host material, One or both of the first and second light-emitting layers contain a compound represented by the following formula (1A) having at least one deuterium atom, and the other contains a compound represented by the following formula (1A) having or not having a deuterium atom. In formula (1A), R1 to R8 are each independently: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 Each independently is: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different; At least one of R1 to R8 is a deuterium atom; Two or more adjacent groups of R1 to R4 and two or more adjacent groups of R5 to R8 are not bonded to each other to form a ring; L 1A and L 2A Each independently is: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, Substituted or unsubstituted biphenylene, Substituted or unsubstituted terphenylene, Substituted or unsubstituted anthracene, or substituted or unsubstituted yaphids; Ar 1A and Ar 2A Each independently is: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted biphenyl, Substituted or unsubstituted terphenyl, Substituted or unsubstituted anthracenyl, or substituted or unsubstituted pheni; L 1A , L 2A 、Ar 1A and Ar 2A When there is a substituent, the substituent is: an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkylsilyl group having 1 to 50 carbon atoms, Halogen atoms, or cyano group.

2. The organic electroluminescent element according to claim 1, wherein The first light-emitting layer and the second light-emitting layer each independently contain a host material and a dopant material.

3. The organic electroluminescent element according to claim 1 or 2, wherein Only one of the first light-emitting layer and the second light-emitting layer contains a compound having at least one deuterium atom as a host material.

4. The organic electroluminescent element according to any one of claims 1 to 3, wherein The content of the host material in the light-emitting layer is 80 mass % or more and 99 mass % or less relative to the entire light-emitting layer.

5. The organic electroluminescent element according to any one of claims 2 to 4, wherein The content of the dopant material in the light-emitting layer is 1 mass % or more and 20 mass % or less relative to the entire light-emitting layer.

6. The organic electroluminescent element according to any one of claims 1 to 5, wherein The number of deuterium atoms in the compound having at least one deuterium atom is 1-100.

7. The organic electroluminescent element according to any one of claims 1 to 6, wherein The number of deuterium atoms in the compound having at least one deuterium atom is 1-80.

8. The organic electroluminescent element according to any one of claims 1 to 7, wherein When the compound having at least one deuterium atom is the host material, the number of deuterium atoms is 1 to 50.

9. The organic electroluminescent element according to any one of claims 1 to 8, wherein When the compound having at least one deuterium atom is the host material, the number of deuterium atoms is 1 to 40.

10. The organic electroluminescent element according to any one of claims 1 to 9, wherein Some of R1 to R8 in the above formula (1A) are deuterium atoms.

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