Organic electroluminescent element and electronic device

Abstract

An organic EL element (1) in which a light-emitting region (5) includes a first light-emitting layer (51) containing a first host material and a second light-emitting layer (52) containing a second host material, the first host material being a first compound represented by general formula (1), the first host material and the second host material being different from each other, and the second host material being a second compound represented by general formula (2). A film thickness ratio, TCA / TAN, of a film thickness TAN of a layer disposed on the anode (3) side and a film thickness TCA of a layer disposed on the cathode (4) side among the first light-emitting layer (51) and the second light-emitting layer (52) is 0.3-1.5, inclusive, and at least one of the following configurations (i) and (ii) is provided. Configuration (i): The anode (3) is a light-reflective electrode having light reflectivity, and the cathode (4) is a translucent electrode having translucency. Configuration (ii): A color conversion unit is disposed on the light extraction side of the organic EL element (1). # imgabs0 #

Description

Technical Field

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

[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays such as mobile phones and televisions. When voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%.

[0003] In order to improve the performance of organic EL elements, for example, in Patent Documents 1 and 2, research has been conducted on stacking multiple light-emitting layers and compounds (such as pyrene compounds) used for stacking light-emitting layers. In addition, in order to achieve improved performance of organic EL elements, Patent Document 3 describes the phenomenon of two triplet excitons fusion by collision to generate singlet excitons (hereinafter sometimes referred to as Triplet-Triplet Fusion = TTF phenomenon).

[0004] Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, emission efficiency, driving voltage, and lifespan.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2019-161218

[0008] Patent Document 2: International Publication No. 2021 / 049663

[0009] Patent Document 3: International Publication No. 2010 / 134350 Summary of the invention

[0010] Problem that the invention aims to solve

[0011] If a pyrene compound as a host material is used in a stacked light-emitting layer, the wavelength of light emitted by the light-emitting layer may be lengthened or the half-peak width of light emission may be increased, thereby causing chromaticity deviation. If chromaticity deviation occurs, the interference of light emitted by each light-emitting layer is weakened, and the luminous efficiency is reduced. Therefore, it is sought to improve the luminous efficiency of an organic EL element having a stacked light-emitting layer.

[0012] An object of the present invention is to provide an organic electroluminescent element having improved light emission efficiency, and an electronic device equipped with the organic electroluminescent element.

[0013] Means used to solve problems

[0014] According to one embodiment of the present invention, an organic electroluminescent element is provided, the organic electroluminescent element comprising a substrate, an anode, a cathode and a light-emitting region arranged between the anode and the cathode, the substrate, the anode, the light-emitting region and the cathode being arranged in sequence, the light-emitting region comprising a first light-emitting layer and a second light-emitting layer, the first light-emitting layer comprising a first host material, the first host material being a first compound represented by the following general formula (1), the second light-emitting layer comprising a second host material, the first host material and the second host material being different from each other, and the film thickness T of the layer arranged on the anode side of the first light-emitting layer and the second light-emitting layer AN The film thickness T of the layer disposed on the cathode side is CA The film thickness ratio T CA / T AN The organic electroluminescent device has at least one of the following structures (i) and (ii).

[0015] Configuration (i): The anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmissivity.

[0016] Configuration (ii): A color conversion unit is disposed on the light extraction side of the organic electroluminescent element.

[0017]

Chemical formula 1

[0018]

[0019] (In the above general formula (1),

[0020] R1 to R5 and Ra are each independently

[0021] Hydrogen atoms,

[0022] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0023] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0024] a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

[0025] a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

[0026] The four Ra ​​are the same or different from each other.

[0027] L1 is

[0028] single bond

[0029] a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or

[0030] a substituted or unsubstituted divalent heterocyclic group having 5 to 20 ring atoms,

[0031] Ar1 is a group represented by the above general formula (11), (12) or (13),

[0032] In the above general formulas (11), (12) and (13),

[0033] X1 is an oxygen atom, a sulfur atom or C(Rb1)(Rb2),

[0034] The group consisting of Rb1 and Rb2

[0035] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0036] bonded to each other to form a substituted or unsubstituted condensed ring, or

[0037] Not bonded to each other,

[0038] R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0039] Hydrogen atoms,

[0040] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0041] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0042] a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

[0043] a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

[0044] Among them, R 101 ~R 110 One of them is a single bond to L1, R 111 ~R 120 One of them is a single bond to L1, R 121 ~R 130 One of them is a single bond to L1. )

[0045] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to one aspect of the present invention described above.

[0046] According to one aspect of the present invention, an organic electroluminescent element having improved light emission efficiency can be provided. According to one aspect of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 This is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to an embodiment of the present invention.

[0048] Figure 2 It is a diagram schematically showing the structure of another example of the organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0049] [definition]

[0050] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0051] In the present specification, in chemical structural formulas, a bondable position that does not clearly show a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

[0052] In this specification, the number of ring carbons refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbons. The "number of ring carbons" recorded below is set in the same manner unless otherwise stated. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

[0053] In addition, when a substituent such as an alkyl group is substituted on a benzene ring, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a substituent such as an alkyl group is substituted on a naphthalene ring, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

[0054] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not recorded separately. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0055] In this specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0056] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0057] In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0058] In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0059] In addition, in the present specification, "substituted" when expressing "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" when expressing "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0060] "Substituents described in this specification"

[0061] The substituents described in the present specification are described below.

[0062] The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0063] The number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0064] The carbon number of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0065] The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0066] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0067] The number of ring carbon atoms of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise described in the present specification.

[0068] The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0069] The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0070] The carbon number of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0071] "Substituted or unsubstituted aryl"

[0072] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when only "aryl" is expressed, both "unsubstituted aryl" and "substituted aryl" are included.

[0073] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent in the following specific example group G1A, and examples of substituted aryl in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl itself in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent.

[0074] Unsubstituted aryl (specific example group G1A):

[0075] Phenyl,

[0076] p-Biphenyl,

[0077] m-Biphenyl,

[0078] o-Biphenyl,

[0079] 4-terphenyl-4-yl,

[0080] 4-terphenyl-3-yl,

[0081] 4-terphenyl-2-yl,

[0082] m-terphenyl-4-yl,

[0083] m-terphenyl-3-yl,

[0084] m-terphenyl-2-yl,

[0085] o-terphenyl-4-yl,

[0086] o-terphenyl-3-yl,

[0087] o-terphenyl-2-yl,

[0088] 1-naphthyl,

[0089] 2-naphthyl,

[0090] Anthracene,

[0091] Benzanthryl,

[0092] Fiki,

[0093] Triphenylene,

[0094] Phenyl,

[0095] Pyrene

[0096] base,

[0097] Benzo base,

[0098] Triphenylene,

[0099] Benzotriphenylene,

[0100] Tetraphenylene,

[0101] Pentaphenyl,

[0102] Fluorene,

[0103] 9,9'-spirobifluorenyl,

[0104] Benzofluorenyl,

[0105] Dibenzofluorenyl,

[0106] Fluoranthene group,

[0107] Benzofluoranthene,

[0108] Perylene and

[0109] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-1) to (TEMP-15).

[0110]

Chemical formula 1

[0111]

[0112]

Chemical formula 2

[0113]

[0114] Substituted aryl (specific example group G1B):

[0115] o-Toluyl,

[0116] m-Toluene

[0117] p-Tolyl,

[0118] p-Xylyl,

[0119] m-Xylyl,

[0120] o-Xylyl,

[0121] p-Isopropylphenyl,

[0122] m-isopropylphenyl,

[0123] o-isopropylphenyl,

[0124] 4-tert-Butylphenyl,

[0125] m-tert-butylphenyl,

[0126] o-tert-butylphenyl,

[0127] 3,4,5-Trimethylphenyl,

[0128] 9,9-dimethylfluorenyl,

[0129] 9,9-diphenylfluorenyl,

[0130] 9,9-bis(4-methylphenyl)fluorenyl,

[0131] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0132] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0133] Cyanophenyl,

[0134] Triphenylsilylphenyl,

[0135] Trimethylsilylphenyl,

[0136] Phenyl naphthyl,

[0137] Naphthylphenyl and

[0138] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0139] "Substituted or unsubstituted heterocyclic group"

[0140] The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.

[0141] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0142] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0143] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0144] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" recorded in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0145] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0146] Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution (specific example group G2B2), sulfur atom substitution (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0147] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0148] Pyrrolyl,

[0149] Imidazole,

[0150] Pyrazolyl,

[0151] Triazole,

[0152] Tetrazolyl,

[0153] Oxazolyl,

[0154] Isoxazolyl,

[0155] Oxadiazolyl,

[0156] Thiazolyl,

[0157] Isothiazolyl,

[0158] Thiadiazole,

[0159] Pyridyl,

[0160] Pyridazine

[0161] Pyrimidine,

[0162] Pyrazinyl,

[0163] Triazine,

[0164] Indolyl,

[0165] Isoindolyl,

[0166] Indolizine

[0167] Quinolizinyl,

[0168] Quinoline,

[0169] Isoquinolinyl,

[0170] Cinnoline,

[0171] Phthalocyanine

[0172] Quinazoline,

[0173] Quinoxaline,

[0174] Benzimidazolyl,

[0175] Indazolyl,

[0176] Phenanthroline,

[0177] Phenanthridinyl,

[0178] Acridinium,

[0179] Phenazine,

[0180] Carbazolyl,

[0181] Benzocarbazolyl,

[0182] Morpholinyl,

[0183] Phenoxazine,

[0184] Phenothiazine,

[0185] Azacarbazolyl, and

[0186] Diazacarbazolyl.

[0187] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0188] Furanyl,

[0189] Oxazolyl,

[0190] Isoxazolyl,

[0191] Oxadiazolyl,

[0192] Cuckoo ton base,

[0193] Benzofuranyl,

[0194] Isobenzofuranyl,

[0195] Dibenzofuranyl,

[0196] Naphthobenzofuranyl,

[0197] Benzoxazolyl,

[0198] Benzisoxazolyl,

[0199] Phenoxazine,

[0200] Morpholinyl,

[0201] dinaphthofuranyl,

[0202] Azadibenzofuranyl,

[0203] Diazadibenzofuranyl,

[0204] Azanaphthobenzofuranyl and

[0205] naphthyridinylbenzofuranyl.

[0206] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0207] Thienyl,

[0208] Thiazolyl,

[0209] Isothiazolyl,

[0210] Thiadiazole,

[0211] benzothienyl,

[0212] Isobenzothienyl,

[0213] dibenzothienyl,

[0214] naphthobenzothienyl,

[0215] Benzothiazolyl,

[0216] Benzisothiazolyl,

[0217] Phenothiazine,

[0218] dinaphthothienyl,

[0219] azadibenzothienyl,

[0220] diazadibenzothienyl,

[0221] azanaphthobenzothienyl and

[0222] diazanaphthobenzothienyl.

[0223] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0224]

Chemical formula 3

[0225]

[0226]

Chemical formula 4

[0227]

[0228] In the above general formulas (TEMP-16) to (TEMP-33), 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.

[0229] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least any one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0230] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0231] (9-phenyl)carbazolyl,

[0232] (9-biphenyl)carbazolyl,

[0233] (9-phenyl)phenylcarbazolyl,

[0234] (9-naphthyl)carbazolyl,

[0235] Diphenylcarbazole-9-yl,

[0236] Phenylcarbazol-9-yl,

[0237] Methylbenzimidazolyl,

[0238] Ethylbenzimidazolyl,

[0239] Phenyl triazine,

[0240] Biphenyl triazine,

[0241] Diphenyltriazine,

[0242] Phenylquinazolinyl, and

[0243] Biphenylquinazolinyl.

[0244] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0245] Phenyldibenzofuranyl,

[0246] Methyldibenzofuranyl,

[0247] tert-Butyldibenzofuranyl and

[0248] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0249] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0250] Phenyldibenzothiophene,

[0251] Methyldibenzothiophene,

[0252] tert-Butyldibenzothienyl and

[0253] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0254] · Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific example group G2B4):

[0255] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, A and Y A When at least one of the nitrogen atoms is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0256] "Substituted or unsubstituted alkyl"

[0257] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

[0258] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent.

[0259] Unsubstituted alkyl (specific example group G3A):

[0260] methyl,

[0261] Ethyl,

[0262] n-propyl,

[0263] Isopropyl,

[0264] n-Butyl,

[0265] Isobutyl

[0266] sec-butyl and

[0267] Tert-butyl.

[0268] Substituted alkyl (specific example group G3B):

[0269] Heptafluoropropyl (including isomers),

[0270] Pentafluoroethyl,

[0271] 2,2,2-Trifluoroethyl and

[0272] Trifluoromethyl.

[0273] "Substituted or unsubstituted alkenyl"

[0274] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when simply expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0275] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0276] Unsubstituted alkenyl (specific example group G4A):

[0277] Vinyl,

[0278] Allyl,

[0279] 1-Butenyl,

[0280] 2-Butenyl and

[0281] 3-Butenyl.

[0282] Substituted alkenyl (specific example group G4B):

[0283] 1,3-Butadienyl,

[0284] 1-Methylvinyl,

[0285] 1-methylallyl,

[0286] 1,1-dimethylallyl,

[0287] 2-Methylallyl and

[0288] 1,2-Dimethylallyl.

[0289] "Substituted or unsubstituted alkynyl"

[0290] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) When simply expressed as "alkynyl" below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0291] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0292] Unsubstituted alkynyl (specific example group G5A):

[0293] Ethynyl.

[0294] "Substituted or unsubstituted cycloalkyl"

[0295] As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when only "cycloalkyl" is expressed, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0296] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0297] Unsubstituted cycloalkyl (specific example group G6A):

[0298] Cyclopropyl,

[0299] Cyclobutyl,

[0300] Cyclopentyl,

[0301] Cyclohexyl,

[0302] 1-adamantyl,

[0303] 2-adamantyl,

[0304] 1-Norbornyl and

[0305] 2-Norborneol.

[0306] Substituted cycloalkyl (specific example group G6B):

[0307] 4-Methylcyclohexyl.

[0308] ·“-Si(R 901 )(R 902 )(R 903 )"

[0309] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) as a specific example (specific example group G7), can be cited:

[0310] -Si(G1)(G1)(G1),

[0311] -Si(G1)(G2)(G2),

[0312] -Si(G1)(G1)(G2),

[0313] -Si(G2)(G2)(G2),

[0314] -Si(G3)(G3)(G3) and

[0315] -Si(G6)(G6)(G6). Here,

[0316] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0317] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0318] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0319] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0320] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0321] Multiple G2 in -Si(G1)(G2)(G2) are the same as or different from each other.

[0322] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0323] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0324] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0325] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0326] ·“-O-(R 904 )"

[0327] As described in this specification, -O-(R 904 ) as a specific example (specific example group G8), can be cited:

[0328] -O(G1),

[0329] -O(G2),

[0330] -O(G3) and

[0331] -O(G6).

[0332] Here,

[0333] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0334] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0335] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0336] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0337] ·“-S-(R 905 )"

[0338] As described in this specification, -S-(R 905 ) as a specific example (specific example group G9), can be cited:

[0339] -S(G1),

[0340] -S(G2),

[0341] -S(G3) and

[0342] -S(G6).

[0343] Here,

[0344] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0345] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0346] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0347] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0348] ·“-N(R 906 )(R 907 )"

[0349] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0350] -N(G1)(G1),

[0351] -N(G2)(G2),

[0352] -N(G1)(G2),

[0353] -N(G3)(G3) and

[0354] -N(G6)(G6).

[0355] Here,

[0356] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0357] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0358] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0359] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0360] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0361] - Multiple G2 in N(G2)(G2) are the same as or different from each other.

[0362] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0363] - A plurality of G6's in N(G6)(G6) are the same as or different from each other.

[0364] "Halogen atoms"

[0365] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0366] "Substituted or unsubstituted fluoroalkyl"

[0367] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0368] "Substituted or unsubstituted haloalkyl"

[0369] The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0370] "Substituted or unsubstituted alkoxy"

[0371] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0372] "Substituted or unsubstituted alkylthio"

[0373] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0374] "Substituted or unsubstituted aryloxy group"

[0375] A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0376] "Substituted or unsubstituted arylthio"

[0377] A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0378] "Substituted or unsubstituted trialkylsilyl"

[0379] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0380] "Substituted or unsubstituted aralkyl"

[0381] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by the "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0382] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0383] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0384] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazyl, (9-phenyl)phenylcarbazyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0385] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0386]

Chemical formula 5

[0387]

[0388] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0389]

Chemical formula 6

[0390]

[0391] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0392] In the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0393]

Chemical formula 7

[0394]

[0395] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0396] 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, unless otherwise described in the present specification.

[0397] "Substituted or unsubstituted arylene group"

[0398] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

[0399] "Substituted or unsubstituted divalent heterocyclic group"

[0400] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0401] "Substituted or unsubstituted alkylene"

[0402] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0403] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0404]

Chemical formula 8

[0405]

[0406]

Chemical formula 9

[0407]

[0408] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0409] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0410]

Chemical formula 10

[0411]

[0412] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0413] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0414] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0415]

Chemical formula 11

[0416]

[0417] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0418] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0419] The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102) unless otherwise described in the present specification.

[0420]

Chemical formula 12

[0421]

[0422]

Chemical formula 13

[0423]

[0424]

Chemical formula 14

[0425]

[0426] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0427]

Chemical formula 15

[0428]

[0429]

Chemical formula 16

[0430]

[0431]

Chemical formula 17

[0432]

[0433]

Chemical formula 18

[0434]

[0435] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0436] The above is the description of the “substituents described in the present specification”.

[0437] ・"When bonding to form a ring"

[0438] In the present specification, the expression "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

[0439] Hereinafter, the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring.") are described. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is described as an example.

[0440]

Chemical formula 19

[0441]

[0442] For example, in the 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", one group of two adjacent groups refers to R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0443] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned groups consisting of two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0444]

Chemical formula 20

[0445]

[0446] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups is bonded as in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q c Total R 922 .

[0447]

Chemical formula 21

[0448]

[0449] In the "monocyclic ring" or "condensed ring" formed, the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), the ring Q formed A and Ring Q B Each is a "single ring" or a "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A And Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q c By RingQ A With Ring Q c The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0450] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0451] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0452] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0453] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0454] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0455] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by hydrogen atoms or the like, or can be replaced by "optional substituents" described later. When an optional element other than carbon is included, the formed ring is a heterocycle.

[0456] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0457] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0458] In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0459] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0460] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0461] In the case of "one or more groups consisting of two or more adjacent groups of ..." "bonded to each other to form a substituted or unsubstituted single ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferably one or more groups consisting of two or more adjacent groups of ... bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0462] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0463] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0464] The above is an explanation of the case where "one or more groups of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted single ring" and the case where "one or more groups of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0465] ·Substituents when expressed as "substituted or unsubstituted"

[0466] In one embodiment of the present specification, the substituent group described as "substituted or unsubstituted" (in the present specification, sometimes referred to as "optional substituent group") is, for example, selected from

[0467] unsubstituted alkyl having 1 to 50 carbon atoms,

[0468] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0469] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0470] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0471] -Si(R 901 )(R 902 )(R 903 ),

[0472] -O-(R 904 ),

[0473] -S-(R 905 ),

[0474] -N(R 906) (R 907 ),

[0475] Halogen atoms, cyano, nitro,

[0476] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0477] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0478] The groups in the group etc.

[0479] Here, R 901 ~R 907 Each independently

[0480] Hydrogen atoms,

[0481] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0482] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

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

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

[0485] In R 901 When there are two or more, two or more R 901 Same or different from each other,

[0486] In R 902 When there are two or more, two or more R 902 Same or different from each other,

[0487] In R 903 When there are two or more, two or more R 903 Same or different from each other,

[0488] In R 904 When there are two or more, two or more R 904 Same or different from each other,

[0489] In R 905 When there are two or more, two or more R 905 Same or different from each other,

[0490] In R 906 When there are two or more, two or more R 906 Same or different from each other,

[0491] In R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0492] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0493] an alkyl group having 1 to 50 carbon atoms,

[0494] An aryl group having 6 to 50 ring carbon atoms and

[0495] A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0496] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0497] an alkyl group having 1 to 18 carbon atoms,

[0498] An aryl group having 6 to 18 ring carbon atoms and

[0499] A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0500] Specific examples of each of the above optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0501] Unless otherwise stated in the present specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0502] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0503] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0504] In this specification, a mathematical expression represented by “A≥B” means that the value of A is equal to the value of B, or the value of A is greater than the value of B.

[0505] In this specification, a mathematical expression represented by “A≤B” means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.

[0506] [First embodiment]

[0507] [Organic electroluminescent element]

[0508] The organic electroluminescent element according to the present embodiment comprises a substrate, an anode, a cathode and a light-emitting region arranged between the anode and the cathode, wherein the substrate, the anode, the light-emitting region and the cathode are arranged in this order, the light-emitting region comprises a first light-emitting layer and a second light-emitting layer, the first light-emitting layer comprises a first host material, the first host material is a first compound represented by the following general formula (1), the second light-emitting layer comprises a second host material, the first host material and the second host material are different from each other, and the film thickness T of the layer arranged on the anode side of the first light-emitting layer and the second light-emitting layer is AN The film thickness T of the layer disposed on the cathode side is CA The film thickness ratio T CA / T AN The organic electroluminescent device has at least one of the following structures (i) and (ii).

[0509] Configuration (i): The anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmissivity.

[0510] Configuration (ii): A color conversion unit is disposed on the light extraction side of the organic electroluminescent element.

[0511] According to this embodiment, an organic electroluminescent element with improved light emission efficiency can be provided.

[0512] In an organic EL element having a stacked light-emitting layer, for example, a top-emitting organic EL element and an organic EL element having a color conversion portion on the light extraction side have the same technical problem as a bottom-emitting organic EL element not having a color conversion portion on the light extraction side in that they cannot achieve the high efficiency brought about by stacking the light-emitting layers.

[0513] When the main material contained in the first light-emitting layer is different from the main material contained in the second light-emitting layer, the intensity of the interaction between the main material and the light-emitting compound in each light-emitting layer is also different, so the light-emitting spectrum of the first light-emitting layer is difficult to completely overlap with the light-emitting spectrum of the second light-emitting layer. For example, due to the displacement of the peak wavelength of the light-emitting spectrum emitted by the first light-emitting layer and the second light-emitting layer, or the half-peak width of the light-emitting spectrum is widened, the overlap of the light-emitting spectrum is further reduced. That is, chromaticity deviation occurs. It is believed that if the overlap of the light-emitting spectrum is reduced, the proportion of the light-emitting spectrum outside the specific wavelength increases. Therefore, it is believed that by further reducing the light caused by the light-emitting spectrum outside the specific wavelength, the loss of light when extracting light from the organic EL element can be reduced.

[0514] By using the compound represented by the following general formula (1) in the first light-emitting layer, it is possible to suppress the emission wavelength from becoming longer and the emission half-width from becoming larger even in a top-emitting organic EL element and an organic EL element having a color conversion unit on the light extraction side. As a result, the overlap between the emission spectrum of the first light-emitting layer and the emission spectrum of the second light-emitting layer increases (chromaticity deviation is suppressed), light interference is enhanced, and light emission efficiency is improved.

[0515] According to one aspect of this embodiment, an organic electroluminescent element having improved luminous efficiency and a longer life can be provided.

[0516] In the organic EL element according to the present embodiment, the light extraction side may be the anode side or the cathode side.

[0517] The organic EL element according to the present embodiment also preferably has the above-mentioned configuration (i) and is a top emission type element in which light emitted from a light emitting region is extracted from a cathode side.

[0518] In the organic EL element according to this embodiment, it is also preferable to arrange a color conversion unit on the light extraction side. The color conversion unit is not particularly limited, and examples thereof include color filters and quantum dots.

[0519] The organic EL device according to this embodiment also preferably has the above-mentioned structures (i) and (ii).

[0520] The organic EL element according to the present embodiment also preferably has the configuration satisfying the above condition (ii) and is a bottom emission type element in which light emitted from a light emitting region is extracted from the substrate side.

[0521] (Luminous area)

[0522] The light emitting region is disposed between the anode and the cathode. In the organic EL element according to this embodiment, the light emitting region includes a first light emitting layer and a second light emitting layer.

[0523] The thickness T of the layer disposed on the anode side of the first light-emitting layer and the second light-emitting layer is AN The film thickness T of the layer arranged on the cathode side CA The film thickness ratio T c A / T AN It is preferably 0.5 or more and 1.5 or less, and more preferably 0.8 or more and 1.2 or less.

[0524] In the organic EL device of this embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical formula 1).

[0525] T1(H1)>T1(H2) …(Formula 1)

[0526] By satisfying the relationship of the above-mentioned mathematical formula (Math. 1), the light emission efficiency of the organic electroluminescent element can be improved.

[0527] In the past, triplet-triplet annihilation (Triplet-Triplet-Annihilation) (sometimes referred to as TTA) has been known as a technology for improving the luminous efficiency of organic electroluminescent elements. TTA is a mechanism in which triplet excitons collide with triplet excitons to generate singlet excitons. It should be noted that the TTA mechanism is sometimes referred to as the TTF mechanism as described in Patent Document 3.

[0528] The TTF phenomenon is explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As is known in the past, the spin state is a ratio of 25% for singlet excitons and 75% for triplet excitons. In the fluorescent elements known in the past, 25% of the singlet excitons emit light when they relax to the ground state, and the remaining 75% of the triplet excitons do not emit light but return to the ground state through the thermal deactivation process.

[0529] Therefore, it is said that the theoretical limit value of the internal quantum efficiency of conventional fluorescent elements is 25%.

[0530] On the other hand, the behavior of triplet excitons generated in organic matter has been studied theoretically. According to SM Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if it is assumed that a high-order exciton such as a quintet immediately returns to a triplet state, then in the case of a triplet exciton (hereinafter referred to as 3 A * ) gradually increases, triplet excitons collide with each other and the reaction shown in the following formula occurs. Here, 1 A represents the ground state, 1 A * represents the lowest excited singlet exciton.

[0531] 3 A*+3A*→(4 / 9) 1 A+(1 / 9) 1 A*+(13 / 9) 3 A*

[0532] That is, it becomes 5 3 A * →4 1 A+1A *, it is predicted that among the 75% of triplet excitons initially generated, 1 / 5, or 20%, will change into singlet excitons. Therefore, the singlet excitons that contribute in the form of light become 40%, which is obtained by adding 75%×(1 / 5)=15% to the 25% initially generated. At this time, the luminescence ratio (TTF ratio) derived from TTF in the total luminescence intensity becomes 15 / 40, or 37.5%. In addition, if the 75% of triplet excitons initially generated collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% can be obtained by adding 75%×(1 / 2)=37.5% to the 25% of singlet excitons initially generated. At this time, the TTF ratio is 37.5 / 62.5=60%.

[0533] According to an organic electroluminescent element involved in one scheme of the present embodiment, it is believed that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer, even if there are excess carriers at the interface between the first light-emitting layer and the directly connected organic layer, the triplet excitons present at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching caused by excess electrons can be considered. On the other hand, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching caused by excess holes can be considered.

[0534] An organic electroluminescent element involved in one scheme of the present embodiment has at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a specific relationship, and the triplet energy T1 (H1) of the first main material in the first light-emitting layer and the triplet energy T1 (H2) of the second main material in the second light-emitting layer satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 1).

[0535] By providing the first light-emitting layer and the second light-emitting layer so as to satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 1), the triplet excitons generated in the first light-emitting layer are not quenched by excess carriers and move to the second light-emitting layer, and the reverse movement from the second light-emitting layer to the first light-emitting layer can be suppressed. As a result, in the second light-emitting layer, the TTF mechanism is exhibited to efficiently generate singlet excitons, and the luminous efficiency is improved.

[0536] In this way, the organic electroluminescent element has a first light-emitting layer that mainly generates triplet excitons, and a second light-emitting layer that effectively utilizes triplet excitons moved from the first light-emitting layer and mainly exhibits the TTF mechanism as different regions. As the second main material in the second light-emitting layer, a compound with a smaller triplet energy than the first main material in the first light-emitting layer is used, and the triplet energy difference is set, thereby improving the luminous efficiency.

[0537] In the organic EL device according to the present embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical formula 1B).

[0538] T1(H1)-T1(H2)>0.03eV…(Formula 1B)

[0539] In this specification, "host material" refers to, for example, a material whose content is "50% by mass or more of the layer". Therefore, in the first light-emitting layer, for example, the content of the first host material is 50% by mass or more of the total mass of the first light-emitting layer. In the second light-emitting layer, for example, the content of the second host material is 50% by mass or more of the total mass of the second light-emitting layer.

[0540] In the organic EL device of this embodiment, the first light-emitting layer preferably includes a first host material and a first light-emitting compound, and the second light-emitting layer preferably includes a second host material and a second light-emitting compound. The first light-emitting compound and the second light-emitting compound may be the same or different from each other.

[0541] In the organic EL element according to the present embodiment, it is preferred that the maximum peak wavelength λ1 and the half-peak width FWHM1 of the PL spectrum of the first film formed by adding the first luminescent compound to the first host material, and the maximum peak wavelength λ2 and the half-peak width FWHM2 of the PL spectrum of the second film formed by adding the second luminescent compound to the second host material satisfy the following mathematical formulas (Mathematical Formula 15) and (Mathematical Formula 16). That is, the organic EL element according to the present embodiment preferably includes a light-emitting layer (a first light-emitting layer and a second light-emitting layer) having the same structure as two films (a first film and a second film) satisfying the relationship of the following mathematical formulas (Mathematical Formula 15) and (Mathematical Formula 16).

[0542] |λ1-λ2|≤3nm...(Mathematical formula 15)

[0543] |FWHM1-FWHM2|≤2nm...(Formula 16)

[0544] In the organic EL element of the first embodiment, the loss when extracting light from the upper electrode (cathode) or the lower electrode (anode) is reduced by setting the first film formed by the components of the first light-emitting layer and the second film formed by the components of the second light-emitting layer to a combination with a small change (difference) in the PL spectrum.

[0545] The maximum peak wavelength λ1 and half maximum width FWHM1 of the PL spectrum of the first film, and the maximum peak wavelength λ2 and half maximum width FWHM2 of the PL spectrum of the second film can be measured by the method described in Examples below.

[0546] In the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound are each independently preferably a compound that emits light with a maximum peak wavelength of 500 nm or less.

[0547] In the organic EL element according to this embodiment, the first light-emitting layer is preferably arranged between the anode and the second light-emitting layer.

[0548] In the organic EL element according to this embodiment, the first light-emitting layer may be disposed between the cathode and the second light-emitting layer.

[0549] In the organic EL element according to this embodiment, it is preferable that one of the first light-emitting layer and the second light-emitting layer is a layer disposed closest to the anode among a plurality of layers included in the light-emitting region.

[0550] In the organic EL element according to this embodiment, it is preferable that one of the first light-emitting layer and the second light-emitting layer is a layer disposed closest to the cathode among a plurality of layers included in the light-emitting region.

[0551] The organic EL element involved in this embodiment may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in sequence, and the order of the first light-emitting layer and the second light-emitting layer may also be reversed. That is, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode may be provided in sequence. In the case where the order of the first light-emitting layer and the second light-emitting layer is any one, by selecting a combination of materials satisfying the relationship of the above mathematical formula (Mathematical Formula 1), the effect brought about by the stacked structure of the first light-emitting layer and the second light-emitting layer can be expected.

[0552] (First light-emitting layer)

[0553] In the organic EL device according to this embodiment, the first light-emitting layer preferably contains a first host material and a first light-emitting compound. The first host material is a compound different from the second host material contained in the second light-emitting layer.

[0554] In the organic EL element involved in this embodiment, the first luminescent compound preferably exhibits luminescence with a maximum peak wavelength of less than 500nm, more preferably exhibits luminescence with a maximum peak wavelength of less than 480nm, further preferably exhibits luminescence with a maximum peak wavelength of less than 460nm, and further preferably exhibits luminescence with a maximum peak wavelength of less than 455nm.

[0555] In the organic EL device according to this embodiment, the first light-emitting compound preferably emits light with a maximum peak wavelength of 430 nm or longer, more preferably emits light with a maximum peak wavelength of 440 nm or longer, and further preferably emits light with a maximum peak wavelength of 445 nm or longer.

[0556] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a fluorescent compound.

[0557] In the organic EL element involved in this embodiment, the first luminescent compound preferably exhibits fluorescence emission with a maximum peak wavelength of less than 500nm, more preferably exhibits fluorescence emission with a maximum peak wavelength of less than 480nm, further preferably exhibits fluorescence emission with a maximum peak wavelength of less than 460nm, and further preferably exhibits fluorescence emission with a maximum peak wavelength of less than 455nm.

[0558] In the organic EL device according to this embodiment, the first light-emitting compound preferably emits fluorescence with a maximum peak wavelength of 430 nm or longer, more preferably emits fluorescence with a maximum peak wavelength of 440 nm or longer, and further preferably emits fluorescence with a maximum peak wavelength of 445 nm or longer.

[0559] The method for determining the maximum peak wavelength of a compound is as follows. A 5 μmol / L toluene solution of the compound to be determined is prepared and added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is set as luminescence intensity, and the horizontal axis is set as wavelength). The luminescence spectrum can be measured by a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

[0560] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is defined as the maximum peak wavelength. It should be noted that in this specification, the maximum peak wavelength of fluorescent emission may be referred to as the fluorescent emission maximum peak wavelength (FL-peak).

[0561] In the emission spectrum of the first luminescent compound, when the peak with the maximum emission intensity is set as the maximum peak and the height of the maximum peak is set as 1, the height of other peaks appearing in the emission spectrum is preferably less than 0.6. It should be noted that the peak in the emission spectrum is set as the maximum value.

[0562] In addition, in the emission spectrum of the first light emitting compound, the number of peaks is preferably less than 3.

[0563] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.

[0564] In the organic EL device according to this embodiment, the first light-emitting compound is preferably not a boron-containing complex, and the first light-emitting compound is more preferably not a complex.

[0565] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a metal complex. In addition, in the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a boron-containing complex.

[0566] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a phosphorescent material (dopant material).

[0567] In addition, the first light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include iridium complexes, osmium complexes, and platinum complexes.

[0568] In the organic EL element according to the present embodiment, the content of the first light-emitting compound in the first light-emitting layer is preferably 0.5% by mass or more. That is, in the first light-emitting layer, the content of the first light-emitting compound is preferably 0.5% by mass or more of the total mass of the first light-emitting layer, more preferably 1.0% by mass or more of the total mass of the first light-emitting layer, further preferably 1.2% by mass or more of the total mass of the first light-emitting layer, and further preferably 1.5% by mass or more of the total mass of the first light-emitting layer.

[0569] In the first light-emitting layer, the content of the first light-emitting compound is preferably less than 10 mass % of the total mass of the first light-emitting layer, more preferably less than 7 mass % of the total mass of the first light-emitting layer, and further preferably less than 5 mass % of the total mass of the first light-emitting layer.

[0570] In the organic EL element involved in this embodiment, in the first light-emitting layer, the content of the first compound as the first host material is preferably 60 mass% or more of the total mass of the first light-emitting layer, the content is more preferably 70 mass% or more of the total mass of the first light-emitting layer, the content is further preferably 80 mass% or more of the total mass of the first light-emitting layer, the content is further preferably 90 mass% or more of the total mass of the first light-emitting layer, and the content is particularly preferably 95 mass% or more of the total mass of the first light-emitting layer.

[0571] In the first light-emitting layer, the content of the first host material is preferably 99 mass % or less of the total mass of the first light-emitting layer.

[0572] However, when the first light-emitting layer contains the first host material and the first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100 mass %.

[0573] It should be noted that this embodiment does not exclude the inclusion of materials other than the first host material and the first light-emitting compound in the first light-emitting layer.

[0574] The first light-emitting layer may contain only one first host material, or may contain two or more first host materials. The first light-emitting layer may contain only one first light-emitting compound, or may contain two or more first host materials.

[0575] In the organic EL device according to this embodiment, the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first luminescent compound preferably satisfy the relationship of the following equation (Equation 5). The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.

[0576] S1(H1)>S1(D1)…(Formula 5)

[0577] When the first host material and the first luminescent compound satisfy the relationship of mathematical formula (Math. 5), the singlet excitons generated on the first host material can easily transfer energy from the first host material to the first luminescent compound, thereby contributing to the fluorescent emission of the first luminescent compound.

[0578] In the organic EL device according to this embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first light-emitting compound preferably satisfy the relationship of the following mathematical formula (Mathematical formula 6).

[0579] T1(D1)>T1(H1)…(Formula 6)

[0580] Because the first host material and the first luminescent compound satisfy the relationship of mathematical formula (Mathematical formula 6), the triplet excitons generated in the first luminescent layer move on the first host material rather than the first luminescent compound with higher triplet energy, and are therefore easily moved to the second luminescent layer.

[0581] The organic EL element according to the present embodiment preferably satisfies the relationship of the following mathematical formula (Mathematical formula 20B).

[0582] T1(D1)>T1(H1)>T1(H2)…(Formula 20B)

[0583] <First main material>

[0584] In the organic EL device according to this embodiment, the first host material is a first compound represented by the following general formula (1).

[0585]

Chemical formula 23

[0586]

[0587] (In the above general formula (1),

[0588] R1 to R5 and Ra are each independently

[0589] Hydrogen atoms,

[0590] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0591] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0592] a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

[0593] a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

[0594] The four Ra ​​are the same or different from each other.

[0595] L1 is

[0596] single bond

[0597] a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or

[0598] a substituted or unsubstituted divalent heterocyclic group having 5 to 20 ring atoms,

[0599] Ar1 is a group represented by the above general formula (11), (12) or (13),

[0600] In the above general formulas (11), (12) and (13),

[0601] X1 is an oxygen atom, a sulfur atom or C(Rb1)(Rb2),

[0602] The group consisting of Rb1 and Rb2

[0603] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0604] bonded to each other to form a substituted or unsubstituted condensed ring, or

[0605] Not bonded to each other,

[0606] R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0607] Hydrogen atoms,

[0608] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0609] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0610] a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

[0611] a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

[0612] Among them, R 101 ~R 110 One of them is a single bond to L1, R 111 ~R 120 One of them is a single bond to L1, R 121 ~R 130 One of them is a single bond to L1. )

[0613] In the organic EL element involved in this embodiment, R1 to R5 and Ra of the first compound are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

[0614] In the organic EL element involved in this embodiment, R1~R5 and Ra of the first compound are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 10 ring atoms.

[0615] In the organic EL device according to this embodiment, the first compound is also preferably represented by the following general formula (101).

[0616]

Chemical formula 24

[0617]

[0618] (In the above general formula (101), R1 to R5, L1 and Ar1 are the same as those in the above general formula (1), and R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1).

[0619] In the organic EL device according to this embodiment, the first compound is also preferably represented by the following general formula (103) or (104).

[0620]

Chemical formula 25

[0621]

[0622] (In the above general formulae (103) and (104), R1 to R5, L1 and Ar1 are the same as those in the above general formula (1), and R6, R7, R8, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1).

[0623] In the organic EL element involved in this embodiment, Ar1 of the first compound is also preferably a group represented by the following general formula (11A), (11B), (11C), (11D), (12A), (12B), (12C), (12D), (13A), (13B), (13C) or (13D).

[0624]

Chemical formula 26

[0625]

[0626]

Chemical formula 27

[0627]

[0628]

Chemical formula 28

[0629]

[0630] (In the above general formulas (11A), (11B), (11C), (11D), (12A), (12B), (12C), (12D), (13A), (13B), (13C) and (13D),

[0631] X1 is an oxygen atom, a sulfur atom or C(Rb1)(Rb2),

[0632] The group consisting of Rb1 and Rb2

[0633] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0634] bonded to each other to form a substituted or unsubstituted condensed ring, or

[0635] Not bonded to each other,

[0636] R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0637] Hydrogen atoms,

[0638] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0639] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0640] a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

[0641] a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

[0642] * indicates the bonding position with L1. )

[0643] In the organic EL device according to this embodiment, Ar1 of the first compound is also preferably a group represented by the above-mentioned general formula (11C), (12C) or (13C).

[0644] In the organic EL device according to this embodiment, it is preferred that R 101 ~R 103 One of them is a single bond bonding to L1.

[0645] In the organic EL device according to this embodiment, it is preferred that R 111 ~R 113 One of them is a single bond bonding to L1.

[0646] In the organic EL device according to this embodiment, it is preferred that R 121 ~R 123 One of them is a single bond bonding to L1.

[0647] In the organic EL device according to this embodiment, Ar1 of the first compound is also preferably a group represented by the above-mentioned general formula (11A), (12A) or (13A).

[0648] In the organic EL device according to this embodiment, the first compound is also preferably represented by the following general formula (111), (121) or (131).

[0649]

Chemical formula 29

[0650]

[0651] (In the above general formulae (111), (121) and (131), R1 to R5 and L1 are defined as in the above general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1), X1, R 102 ~R 110 , R 112 ~R 120 and R 122 ~R 130 The definitions of are the same as those in the above general formulas (11) to (13).

[0652] In the organic EL device according to this embodiment, X1 of the first compound is also preferably an oxygen atom.

[0653] In the organic EL device according to this embodiment, the first compound is also preferably represented by the following general formula (141), (142) or (143).

[0654]

Chemical formula 30

[0655]

[0656] (In the above general formula (141), R1 to R5 and L1 are defined as in the above general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1), X1, R 111 , R 112 and R 114 ~R 120 The definitions of are the same as those in the above general formula (12).

[0657]

Chemical formula 31

[0658]

[0659] (In the above general formula (142), R1 to R5 and L1 are defined as in the above general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1), X1, R 101 , R 102 and R 104 ~R 110 The definitions of are the same as those in the above general formula (11).

[0660]

Chemical formula 32

[0661]

[0662] (In the above general formula (143), R1 to R5 and L1 are defined as in the above general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1), X1, R 121 , R 122 and R 124 ~R 130 The definitions of are the same as those in the above general formula (13).

[0663] In the above general formula (142), R 107 It is preferably a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.

[0664] In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (142A).

[0665]

Chemical formula 33

[0666]

[0667] (In the above general formula (142A), R1 to R5 and L1 are defined as in the above general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the above general formula (1), X1, R 101 , R 102 , R 104 ~R 106 and R 108 ~R 110 Each is the same as defined in the above general formula (11), R 151 ~R 155 Each is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0668] In the organic EL device according to this embodiment, X1 of the first compound is also preferably C(Rb1)(Rb2).

[0669] In the organic EL device according to this embodiment, Ar1 of the first compound is also preferably a group represented by the above-mentioned general formula (11B), (12B) or (13B).

[0670] In the organic EL device according to the present embodiment, L1 is also preferably any one group selected from the groups represented by the following general formulae (L1) to (L15).

[0671]

Chemical formula 34

[0672]

[0673] In the above general formulae (L1) to (L15), * represents a bonding position.

[0674] The groups represented by the above general formulae (L1) to (L15) may each independently have one or more of the above-mentioned "optional substituents", or may not have any "optional substituents". The groups represented by the above general formulae (L1) to (L15) may each independently have one or more deuterium atoms.

[0675] In the organic EL device according to the present embodiment, L1 in the first compound is preferably a single bond, or a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms.

[0676] In the organic EL device according to this embodiment, L1 in the first compound is preferably a single bond or a substituted or unsubstituted p-phenylene group.

[0677] In the organic EL device according to this embodiment, R1, R2, and R4 to R5 of the first compound are 10 When is a hydrogen atom, the compound represented by the above general formula (101) is represented by the following general formula (102).

[0678]

Chemical formula 35

[0679]

[0680] (In the above general formula (102), R3, L1 and Ar1 have the same definitions as in the above general formula (1).)

[0681] In the organic EL device according to this embodiment, it is preferred that R1, R2, R4 and R5 of the first compound are hydrogen atoms, and R3 is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0682] In the organic EL device according to this embodiment, Ra of the first compound is preferably a hydrogen atom.

[0683] In the organic EL device according to this embodiment, R5 to R7, R9 and R 10 Preferred is a hydrogen atom.

[0684] In the organic EL device according to this embodiment, it is preferred that R1, R2, R4, R5 and Ra of the first compound are hydrogen atoms, and R3 is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0685] In the organic EL device according to this embodiment, it is also preferred that R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0686] Hydrogen atoms,

[0687] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0688] a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

[0689] a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, or

[0690] A substituted or unsubstituted heterocyclic group having 5 to 10 ring atoms.

[0691] In the organic EL device according to this embodiment, the R of the first compound that is not a single bond bonded to L1 is 101 ~R 110 , R 111 ~R 120 and R 121 ~R 130 It is preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0692] In the organic EL device according to this embodiment, it is also preferred that the first compound contains at least one deuterium atom in the molecule.

[0693] In the organic EL device according to the present embodiment, it is also preferred that at least one of Ra and R1 to R5 in the first compound is a deuterium atom.

[0694] In the organic EL device according to this embodiment, it is also preferred that L1 of the first compound contains one or more deuterium atoms.

[0695] In the organic EL device according to this embodiment, it is also preferred that Ar1 of the first compound contains one or more deuterium atoms.

[0696] In the compound according to this embodiment, when the term "substituted or unsubstituted" is used, the substituent is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0697] In the organic EL device according to this embodiment, in the first compound, all groups expressed as “substituted or unsubstituted” are preferably “unsubstituted” groups.

[0698] (Method for producing the first compound)

[0699] The first compound according to this embodiment can be produced according to the synthesis method described in the Examples described below, or can be produced by following the synthesis method and using a known substitution reaction and raw materials corresponding to the target substance.

[0700] (Specific example of the first compound according to this embodiment)

[0701] As specific examples of the first compound involved in this embodiment, for example, the following compounds can be cited. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is marked as D in a chemical formula, and a protium atom is marked as H or omitted. In this specification, a methyl group is sometimes marked as Me, and a phenyl group is sometimes marked as Ph.

[0702]

Chemical formula 36

[0703]

[0704]

Chemical formula 37

[0705]

[0706]

Chemical formula 38

[0707]

[0708]

Chemical formula 39

[0709]

[0710]

Chemical formula 40

[0711]

[0712]

Chemical formula 41

[0713]

[0714]

Chemical formula 42

[0715]

[0716]

Chemical formula 43

[0717]

[0718]

Chemical formula 44

[0719]

[0720]

Chemical formula 45

[0721]

[0722]

Chemical formula 46

[0723]

[0724]

Chemical formula 47

[0725]

[0726]

Chemical formula 48

[0727]

[0728]

Chemical formula 49

[0729]

[0730]

Chemical formula 50

[0731]

[0732]

Chemical formula 51

[0733]

[0734]

Chemical formula 52

[0735]

[0736]

Chemical formula 53

[0737]

[0738]

Chemical formula 54

[0739]

[0740]

Chemical formula 55

[0741]

[0742]

Chemical formula 56

[0743]

[0744]

Chemical formula 57

[0745]

[0746]

Chemical formula 58

[0747]

[0748]

Chemical formula 59

[0749]

[0750]

Chemical formula 60

[0751]

[0752]

Chemical formula 61

[0753]

[0754]

Chemical formula 62

[0755]

[0756]

Chemical formula 63

[0757]

[0758]

Chemical formula 64

[0759]

[0760]

Chemical formula 65

[0761]

[0762]

Chemical formula 66

[0763]

[0764]

Chemical formula 67

[0765]

[0766]

Chemical formula 68

[0767]

[0768]

Chemical formula 69

[0769]

[0770]

Chemical formula 70

[0771]

[0772]

Chemical formula 71

[0773]

[0774]

Chemical formula 72

[0775]

[0776]

Chemical formula 73

[0777]

[0778]

Chemical formula 74

[0779]

[0780]

Chemical formula 75

[0781]

[0782]

Chemical formula 76

[0783]

[0784]

Chemical formula 77

[0785]

[0786]

Chemical formula 78

[0787]

[0788]

Chemical formula 79

[0789]

[0790]

Chemical formula 80

[0791]

[0792]

Chemical formula 81

[0793]

[0794]

Chemical formula 82

[0795]

[0796]

Chemical formula 83

[0797]

[0798]

Chemical formula 84

[0799]

[0800]

Chemical formula 85

[0801]

[0802]

Chemical formula 86

[0803]

[0804]

Chemical formula 87

[0805]

[0806]

Chemical formula 88

[0807]

[0808]

Chemical formula 89

[0809]

[0810] (Second light-emitting layer)

[0811] In the organic EL element involved in this embodiment, the second light-emitting layer preferably includes a second host material and a second light-emitting compound. The second host material is a compound different from the first host material contained in the first light-emitting layer. In the organic EL element involved in this embodiment, the first light-emitting compound and the second light-emitting compound are the same as or different from each other.

[0812] In the organic EL element involved in this embodiment, the second luminescent compound preferably exhibits luminescence with a maximum peak wavelength of less than 500nm, more preferably exhibits luminescence with a maximum peak wavelength of less than 480nm, further preferably exhibits luminescence with a maximum peak wavelength of less than 460nm, and further preferably exhibits luminescence with a maximum peak wavelength of less than 455nm.

[0813] In the organic EL device according to this embodiment, the second light-emitting compound preferably emits light with a maximum peak wavelength of 430 nm or longer, more preferably emits light with a maximum peak wavelength of 440 nm or longer, and further preferably emits light with a maximum peak wavelength of 445 nm or longer.

[0814] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a fluorescent compound.

[0815] In the organic EL element involved in this embodiment, the second luminescent compound preferably exhibits fluorescence with a maximum peak wavelength of less than 500nm, more preferably exhibits fluorescence with a maximum peak wavelength of less than 480nm, further preferably exhibits fluorescence with a wavelength of less than 460nm, and further preferably exhibits fluorescence with a wavelength of less than 455nm.

[0816] In the organic EL device according to this embodiment, the second light-emitting compound preferably emits fluorescence with a maximum peak wavelength of 430 nm or longer, more preferably emits fluorescence with a maximum peak wavelength of 440 nm or longer, and further preferably emits fluorescence with a maximum peak wavelength of 445 nm or longer.

[0817] The method for measuring the maximum peak wavelength of a compound is as described above.

[0818] In the organic EL device according to the present embodiment, the half-value width of the largest peak of the second light-emitting compound is preferably 1 nm or more and 20 nm or less.

[0819] In the organic EL device according to this embodiment, the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second light-emitting compound preferably satisfy the relationship of the following mathematical formula (Mathematical formula 7).

[0820] S1(H2)>S1(D2)…(Formula 7)

[0821] In the organic EL element involved in this embodiment, the second luminescent compound and the second main material satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 7). Therefore, since the singlet energy of the second luminescent compound is smaller than the singlet energy of the second main material, the singlet exciton generated by the TTF phenomenon transfers energy from the second main material to the second luminescent compound, which contributes to the fluorescent emission of the second luminescent compound.

[0822] In the organic EL device according to this embodiment, the triplet energy T1(D2) of the second light-emitting compound and the triplet energy T1(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical formula 8).

[0823] T1(D2)>T1(H2)…(Formula 8)

[0824] In the organic EL element involved in this embodiment, the second luminescent compound and the second host material satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 8), so that when the triplet excitons generated in the first luminescent layer move to the second luminescent layer, they do not transfer energy to the second luminescent compound having a higher triplet energy, but to the molecules of the second host material. In addition, the triplet excitons generated by the recombination of holes and electrons on the second host material do not move to the second luminescent compound having a higher triplet energy. The triplet excitons generated by the recombination on the molecules of the second luminescent compound quickly transfer energy to the molecules of the second host material.

[0825] The triplet excitons passing through the second host material do not move to the second light-emitting compound, but the triplet excitons efficiently collide with each other on the second host material by the TTF phenomenon, thereby generating singlet excitons.

[0826] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.

[0827] In the organic EL device according to this embodiment, the second light-emitting compound is preferably not a boron-containing complex, and the second light-emitting compound is more preferably not a complex.

[0828] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a metal complex. In addition, in the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a boron-containing complex.

[0829] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material).

[0830] In addition, the second light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include iridium complexes, osmium complexes, and platinum complexes.

[0831] In the organic EL element according to the present embodiment, the content of the second light-emitting compound in the second light-emitting layer is preferably 0.5 mass % or more. That is, in the second light-emitting layer, the content of the second light-emitting compound is preferably 0.5 mass % or more of the total mass of the second light-emitting layer, more preferably 1.0 mass % or more of the total mass of the second light-emitting layer, further preferably 1.2 mass % or more of the total mass of the second light-emitting layer, and further preferably 1.5 mass % or more of the total mass of the second light-emitting layer.

[0832] In the second light-emitting layer, the content of the second light-emitting compound is preferably less than 10 mass % of the total mass of the second light-emitting layer, more preferably less than 7 mass % of the total mass of the second light-emitting layer, and further preferably less than 5 mass % of the total mass of the second light-emitting layer.

[0833] In the second light-emitting layer, the content of the second compound as the second host material is preferably 60 mass % or more of the total mass of the second light-emitting layer, more preferably 70 mass % or more of the total mass of the second light-emitting layer, further preferably 80 mass % or more of the total mass of the second light-emitting layer, further preferably 90 mass % or more of the total mass of the second light-emitting layer, and particularly preferably 95 mass % or more of the total mass of the second light-emitting layer.

[0834] In the second light-emitting layer, the content of the second host material is preferably 99 mass % or less of the total mass of the second light-emitting layer.

[0835] When the second light-emitting layer contains the second host material and the second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100 mass %.

[0836] It should be noted that this embodiment does not exclude the inclusion of materials other than the second host material and the second light-emitting compound in the second light-emitting layer.

[0837] In the second light-emitting layer, the second host material may include only one type, or may include two or more types. In the second light-emitting layer, the second light-emitting compound may include only one type, or may include two or more types.

[0838] <Second main material>

[0839] In the organic EL device according to this embodiment, the second host material is not particularly limited, and examples thereof include a second compound represented by the following general formula (2).

[0840] (Second Compound)

[0841] In the organic EL device according to this embodiment, the second compound is preferably a compound represented by the following general formula (2). The second host material is preferably a second compound represented by the following general formula (2).

[0842]

Chemical formula 90

[0843]

[0844] (In the above general formula (2),

[0845] R 201 ~R 208 Each independently

[0846] Hydrogen atoms,

[0847] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0848] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0849] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0850] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0851] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0852] -Si(R 901 (R 902 )(R 903 ) shown in the group,

[0853] -O-(R 904 ) shown in the group,

[0854] -S-(R 905 ) shown in the group,

[0855] -N(R 906 )(R 907 ) shown in the group,

[0856] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0857] -C(=O)R 801 The groups shown,

[0858] -COOR 802 The groups shown,

[0859] Halogen atoms,

[0860] Cyano,

[0861] Nitro,

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

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

[0864] L 201 and L 202 Each independently

[0865] single bond,

[0866] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0867] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0868] Ar 201 and Ar 202 Each independently

[0869] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0870] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0871] In the above second host material, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each independently

[0872] Hydrogen atoms,

[0873] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0874] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0875] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0876] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0877] In R 901 If there are multiple R 901 Same or different from each other,

[0878] In R 902 If there are multiple R 902 Same or different from each other,

[0879] In R 903 If there are multiple R 903 Same or different from each other,

[0880] In R 904 If there are multiple R 904 Same or different from each other,

[0881] In R 905 If there are multiple R 905 Same or different from each other,

[0882] In R 906 If there are multiple R 906 Same or different from each other,

[0883] In R 907 If there are multiple R 907 Same or different from each other,

[0884] In R 801 If there are multiple R 801 Same or different from each other,

[0885] In R 802 If there are multiple R 802 Same as or different from each other.

[0886] In the organic EL element according to this embodiment, it is preferred that R 201 ~R 208 Each independently

[0887] Hydrogen atoms,

[0888] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0889] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0890] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0891] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0892] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0893] -Si(R 901) (R 902 )(R 903 ) shown in the group,

[0894] -O-(R 904 ) shown in the group,

[0895] -S-(R 905 ) shown in the group,

[0896] -N(R 906) (R 907 ) shown in the group,

[0897] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0898] -C(=O)R 801 The groups shown,

[0899] -COOR 802 The groups shown,

[0900] Halogen atoms,

[0901] Cyano or

[0902] Nitro,

[0903] L 201 and L 202 Each independently

[0904] single bond,

[0905] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0906] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0907] Ar 201 and Ar 202 Each independently

[0908] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0909] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0910] In the organic EL element according to this embodiment, it is preferred that L 201 and L 202 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Ar 201 and Ar 202 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0911] In the organic EL element according to this embodiment, it is preferred that Ar 201 and Ar 202Each is independently a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.

[0912] In the organic EL element involved in this embodiment, the second compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209).

[0913]

Chemical formula 91

[0914]

[0915]

Chemical formula 92

[0916]

[0917]

Chemical formula 93

[0918]

[0919]

Chemical formula 94

[0920]

[0921]

Chemical formula 95

[0922]

[0923]

Chemical formula 96

[0924]

[0925]

Chemical formula 97

[0926]

[0927]

Chemical formula 98

[0928]

[0929]

Chemical formula 99

[0930]

[0931] (In the above general formulas (201) to (209),

[0932] L 201 and Ar 201 and L in the above general formula (2) 201 and Ar201 The same meaning,

[0933] R 201 ~R 208 Each independently of R in the above general formula (2) 201 ~R 208 Same meaning.)

[0934] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) or general formula (229).

[0935]

Chemical Formula 100

[0936]

[0937]

Chemical Formula 101

[0938]

[0939]

Chemical Formula 102

[0940]

[0941]

Chemical Formula 103

[0942]

[0943]

Chemical Formula 104

[0944]

[0945]

Chemical Formula 105

[0946]

[0947]

Chemical formula 106

[0948]

[0949]

Chemical formula 107

[0950]

[0951]

Chemical formula 108

[0952]

[0953] (In the above general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) and general formula (229),

[0954] R 201 and R 203 ~R 208 Each independently of R in the above general formula (2) 201 and R 203 ~R 208 The same meaning,

[0955] L 201 and Ar 201 Each of them is the same as L in the above general formula (2) 201 and Ar 201 The same meaning,

[0956] L 203 and L in the above general formula (2) 201 The same meaning,

[0957] L 203 With L 201 Same or different from each other,

[0958] Ar 203 and Ar in the above general formula (2) 201 The same meaning,

[0959] Ar 203 with Ar 201 Same as or different from each other.)

[0960] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) or general formula (249).

[0961]

Chemical formula 109

[0962]

[0963]

Chemical Formula 110

[0964]

[0965]

Chemical Formula 111

[0966]

[0967]

Chemical Formula 112

[0968]

[0969]

Chemical formula 113

[0970]

[0971]

Chemical formula 114

[0972]

[0973]

Chemical Formula 115

[0974]

[0975]

Chemical formula 116

[0976]

[0977]

Chemical formula 117

[0978]

[0979] (In the above general formulae (241), (242), (243), (244), (245), (246), (247), (248) and (249),

[0980] R 201 , R 202 and R 204 ~R 208 Each independently of R in the above general formula (2) 201 , R 202 and R 204 ~R 208 The same meaning,

[0981] L 201 and Ar 201 Each of them is the same as L in the above general formula (2) 201 and Ar 201 The same meaning,

[0982] L 203 and L in the above general formula (2) 201 The same meaning,

[0983] L 203 With L 201 Same or different from each other,

[0984] Ar 203 and Ar in the above general formula (2) 20 The same meaning,

[0985] Ar 203 with Ar 201Same as or different from each other.)

[0986] In the second compound represented by the above general formula (2), R 201 ~R 208 Each of them is independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -Si(R 901 )(R 902 )(R 903 ) shown in the figure.

[0987] Preferably, L 201 is a single bond, or an unsubstituted arylene group having 6 to 22 ring carbon atoms, Ar 201 It is a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.

[0988] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), from the viewpoint of preventing the inhibition of the interaction between molecules and suppressing the decrease in electron mobility, R as a substituent of the anthracene skeleton is 201 ~R 208 Preferably a hydrogen atom, but R 201 ~R 208 It may be a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0989] R 201 ~R 208 In the case of a high steric hindrance substituent such as an alkyl group or a cycloalkyl group, the interaction between molecules is suppressed, the electron mobility decreases relative to the first host material, and the relationship of μe(H2)>μe(H1) described in the following mathematical formula (Mathematical Formula 30) may not be satisfied. When the second compound is used in the second light-emitting layer, it can be expected that by satisfying the relationship of μe(H2)>μe(H1), the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in the light-emitting efficiency can be suppressed. It should be noted that as a substituent, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906) (R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups and nitro groups may form high steric hindrance, and alkyl groups and cycloalkyl groups may form even higher steric hindrance.

[0990] In the second compound represented by the general formula (2), R as a substituent of the anthracene skeleton is 201 ~R 208 It is preferably not a high steric hindrance substituent, preferably not an alkyl group or a cycloalkyl group, and more preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906) (R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups and nitro groups.

[0991] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), it is also preferred that R 201 ~R 20s are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -Si(R 901 )(R 902 )(R 903 ) shown in the figure.

[0992] In the organic EL device according to this embodiment, in the second compound represented by the above general formula (2), R 201 ~R 208 Preferred is a hydrogen atom.

[0993] In the second compound, R 201 ~R 208 When the substituent is expressed as "substituted or unsubstituted", it is also preferred that the substituents described above that may form high steric hindrance do not include substituents, especially substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208 When the substituent is expressed as "substituted or unsubstituted", by not including substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups, the intermolecular interactions caused by the presence of high steric hindrance substituents such as alkyl groups and cycloalkyl groups can be prevented from being inhibited, thereby preventing a decrease in electron mobility. In addition, when such a second compound is used for the second light-emitting layer, a decrease in the recombination ability of holes and electrons in the first light-emitting layer and a decrease in the luminous efficiency can be suppressed.

[0994] It is further preferred that R as a substituent of the anthracene skeleton201 ~R 208 It is not a high steric hindrance substituent. R 201 ~R 208 is unsubstituted. In addition, in R as a substituent of the anthracene skeleton 201 ~R 208 In the case of a non-highly hindered substituent, when R is a lowly hindered substituent 201 ~R 208 When a substituent is bonded to the spherical surface, the substituent is preferably not a high steric hindrance substituent. 201 ~R 208 The substituent bonded to the above is preferably not an alkyl group or a cycloalkyl group, and more preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906 )(R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups and nitro groups.

[0995] In the second compound, all groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.

[0996] (Method for producing the second compound)

[0997] The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method by using a known substitution reaction and raw materials corresponding to the target substance.

[0998] (Specific example of the second compound)

[0999] Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.

[1000]

Chemical formula 118

[1001]

[1002]

Chemical formula 119

[1003]

[1004]

Chemical Formula 120

[1005]

[1006]

Chemical Formula 121

[1007]

[1008]

Chemical formula 122

[1009]

[1010]

Chemical Formula 123

[1011]

[1012]

Chemical formula 124

[1013]

[1014]

Chemical formula 125

[1015]

[1016]

Chemical formula 126

[1017]

[1018]

Chemical formula 127

[1019]

[1020]

Chemical formula 128

[1021]

[1022]

Chemical formula 129

[1023]

[1024]

Chemical Formula 130

[1025]

[1026]

Chemical Formula 131

[1027]

[1028]

Chemical formula 132

[1029]

[1030]

Chemical formula 133

[1031]

[1032]

Chemical formula 134

[1033]

[1034]

Chemical formula 135

[1035]

[1036]

Chemical formula 136

[1037]

[1038]

Chemical formula 137

[1039]

[1040]

Chemical formula 138

[1041]

[1042]

Chemical formula 139

[1043]

[1044]

Chemical formula 140

[1045]

[1046]

Chemical Formula 141

[1047]

[1048]

Chemical formula 142

[1049]

[1050]

Chemical formula 143

[1051]

[1052]

Chemical formula 144

[1053]

[1054]

Chemical formula 145

[1055]

[1056]

Chemical formula 146

[1057]

[1058] In the organic EL element involved in this embodiment, the triplet energy T1(DX) of the first luminescent compound or the second luminescent compound, the triplet energy T1(H1) of the first main material and the triplet energy T1(H2) of the second main material also preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 9), and also preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 10).

[1059] 2.7eV>T1(DX)>T1(H1)>T1(H2)…(Formula 9)

[1060] 2.6eV>T1(DX)>T1(H1)>T1(H2)…(Formula 10)

[1061] The triplet energy T1(D1) of the first light-emitting compound also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 9A), and also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 10A).

[1062] 2.7V>T1(D1)>T1(H1)>T1(H2)…(Formula 9A)

[1063] 2.6eV>T1(D1)>T1(H1)>T1(H2)…(Formula 10A)

[1064] The triplet energy T1(D2) of the second light-emitting compound also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 9B), and preferably satisfies the relationship of the following mathematical formula (Mathematical formula 10B).

[1065] 2.7eV>T1(D2)>T1(H1)>T1(H2)…(Formula 9B)

[1066] 2.6eV>T1(D2)>T1(H1)>T1(H2)…(Formula 10B)

[1067] In the organic EL device according to this embodiment, the triplet energy T1(DX) of the first light-emitting compound or the second light-emitting compound and the triplet energy T1(H1) of the first host material preferably satisfy the relationship of the following mathematical formula (Math. 11).

[1068] 0eV<T1(DX)-T1(H1)<0.6eV…(Formula 11)

[1069] The triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical formula 11A).

[1070] 0eV<T1(D1)-T1(H1)<0.6eV…(Formula 11A)

[1071] The triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical formula 11B).

[1072] 0eV<T1(D2)-T1(H2)<0.8eV…(Formula 11B)

[1073] In the organic EL device according to the present embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Mathematical formula 12).

[1074] T1(H1)>2.0eV…(Formula 12)

[1075] In the organic EL device according to this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Mathematical formula 12A) and also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 12B).

[1076] T1(H1)>2.10eV…(Formula 12A)

[1077] T1(H1)>2.15eV…(Formula 12B)

[1078] In the organic EL element according to the present embodiment, the triplet energy T1(H1) of the first host material satisfies the relationship of the above-mentioned mathematical formula (Mathematical formula 12A) or the above-mentioned mathematical formula (Mathematical formula 12B), so that triplet excitons generated in the first light-emitting layer are easily moved to the second light-emitting layer, and reverse movement from the second light-emitting layer to the first light-emitting layer is easily suppressed. As a result, singlet excitons are efficiently generated in the second light-emitting layer, and the luminous efficiency is improved.

[1079] In the organic EL device according to this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (Mathematical formula 12C) and also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 12D).

[1080] 2.08eV>T1(H1)>1.87eV…(Mathematical formula 12C)

[1081] 2.05eV>T1(H1)>1.90eV…(Formula 12D)

[1082] In the organic EL element involved in this embodiment, the triplet energy T1(H1) of the first main material satisfies the relationship of the above mathematical formula (Mathematical Formula 12C) or the above mathematical formula (Mathematical Formula 12D), thereby reducing the energy of the triplet excitons generated in the first light-emitting layer, and the organic EL element can be expected to have a longer life.

[1083] In the organic EL device according to this embodiment, the triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical formula 14A) and also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 14B).

[1084] 2.60eV>T1(D1)…(Formula 14A)

[1085] 2.50eV>T1(D1)…(Formula 14B)

[1086] When the first light-emitting layer contains the first light-emitting compound satisfying the relationship of the above-mentioned mathematical formula (Math. 14A) or (Math. 14B), the life of the organic EL device is prolonged.

[1087] In the organic EL device according to this embodiment, the triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following mathematical formula (Mathematical formula 14C) and also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 14D).

[1088] 2.60eV>T1(D2)…(Mathematical formula 14C)

[1089] 2.50eV>T1(D2)…(Formula 14D)

[1090] When the second light-emitting layer contains a compound satisfying the relationship of the above-mentioned mathematical formula (Math. 14C) or (Math. 14D), the life of the organic EL element is prolonged.

[1091] In the organic EL device according to the present embodiment, the triplet energy T1(H2) of the second host material also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 13).

[1092] T1(H2)>1.9eV…(Formula 13)

[1093] In the organic EL device according to the present embodiment, the triplet energy T1(H2) of the second host material also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 13A).

[1094] 1.9eV ≥ T1(H2) ≥ 1.8eV…(Formula 13A)

[1095] (Luminescent Compound)

[1096] In the organic EL element involved in this embodiment, the luminescent compounds such as the first luminescent compound and the second luminescent compound are not particularly limited. For example, they are preferably each independently selected from one or more compounds represented by the following general formula (4), the following general formula (5) and the following general formula (6).

[1097] (Compound represented by general formula (4))

[1098] The compound represented by the general formula (4) will be described.

[1099]

Chemical formula 147

[1100]

[1101] (In the above general formula (4),

[1102] Z is independently CRa or a nitrogen atom,

[1103] Ring A1 and ring A2 are each independently

[1104] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1105] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1106] When there are multiple Ra, one or more groups of two or more adjacent Ra

[1107] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1108] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1109] Not bonded to each other,

[1110] n21 and n22 are each independently 0, 1, 2, 3 or 4,

[1111] When there are multiple Rb, one or more groups of two or more adjacent Rb

[1112] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1113] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1114] Not bonded to each other,

[1115] When there are multiple Rc, c One or more of the groups of two or more adjacent

[1116] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1117] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1118] Not bonded to each other,

[1119] Ra, Rb and Rc which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[1120] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1121] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1122] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1123] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1124] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1125] -O-(R 904 ) shown in the group,

[1126] -S-(R 905 ) shown in the group,

[1127] -N(R 906) (R 907 ) shown in the group,

[1128] Halogen atoms,

[1129] Cyano,

[1130] Nitro,

[1131] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1132] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1133] (Specific examples of compounds represented by general formula (4))

[1134] As specific examples of the compound represented by the general formula (4), for example, the following compounds can be cited: In the present specification, in the specific examples of the compound, Ph sometimes represents a phenyl group, Me represents a methyl group, D represents a deuterium atom, tBu represents a tert-butyl group, and tAm represents a tert-amyl group.

[1135]

Chemical formula 148

[1136]

[1137]

Chemical formula 149

[1138]

[1139]

Chemical formula 150

[1140]

[1141]

Chemical formula 151

[1142]

[1143]

Chemical formula 152

[1144]

[1145]

Chemical formula 153

[1146]

[1147]

Chemical formula 154

[1148]

[1149]

Chemical formula 155

[1150]

[1151]

Chemical formula 156

[1152]

[1153]

Chemical formula 157

[1154]

[1155] (Compound represented by general formula (5))

[1156] The compound represented by the general formula (5) will be described.

[1157]

Chemical formula 158

[1158]

[1159] (In the above general formula (5),

[1160] By R 501 ~R 507 and R 511 ~R 517 One or more of the groups of two or more adjacent

[1161] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1162] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1163] Not bonded to each other,

[1164] R521 , R 522 , and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 501 ~R 507 and R 511 ~R 517 Each independently

[1165] Hydrogen atoms,

[1166] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1167] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1168] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1169] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1170] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1171] -O-(R 904 ) shown in the group,

[1172] -S-(R 905 ) shown in the group,

[1173] -N(R 906 )(R 907 ) shown in the group,

[1174] Halogen atoms,

[1175] Cyano,

[1176] Nitro,

[1177] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1178] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1179] (Specific examples of compounds represented by general formula (5))

[1180] As specific examples of the compound represented by the general formula (5), the following compounds can be mentioned.

[1181]

Chemical formula 159

[1182]

[1183]

Chemical formula 160

[1184]

[1185]

Chemical formula 161

[1186]

[1187]

Chemical formula 162

[1188]

[1189]

Chemical formula 163

[1190]

[1191]

Chemical formula 164

[1192]

[1193]

Chemical formula 165

[1194]

[1195]

Chemical formula 166

[1196]

[1197]

Chemical formula 167

[1198]

[1199]

Chemical formula 168

[1200]

[1201]

Chemical formula 169

[1202]

[1203]

Chemical formula 170

[1204]

[1205]

Chemical formula 171

[1206]

[1207]

Chemical formula 172

[1208]

[1209]

Chemical formula 173

[1210]

[1211]

Chemical formula 174

[1212]

[1213] (Compound represented by general formula (6))

[1214] The compound represented by the general formula (6) will be described.

[1215]

Chemical formula 175

[1216]

[1217] (In the above general formula (6),

[1218] Ring a, ring b and ring c are each independently

[1219] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1220] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1221] R 601 and R 602 Each independently bonds to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

[1222] R which does not form the above substituted or unsubstituted heterocyclic ring 601 and R 602 Each independently

[1223] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1224] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1225] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1226] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1227] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1228] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1229] (Specific examples of compounds represented by general formula (6))

[1230] Specific examples of the compound represented by the general formula (6) are described below. These are merely illustrative and the compound represented by the general formula (6) is not limited to the following specific examples.

[1231]

Chemical formula 176

[1232]

[1233]

Chemical formula 177

[1234]

[1235]

Chemical formula 178

[1236]

[1237]

Chemical formula 179

[1238]

[1239]

Chemical formula 180

[1240]

[1241]

Chemical formula 181

[1242]

[1243]

Chemical formula 182

[1244]

[1245]

Chemical formula 183

[1246]

[1247]

Chemical formula 184

[1248]

[1249]

Chemical formula 185

[1250]

[1251]

Chemical formula 186

[1252]

[1253]

Chemical formula 187

[1254]

[1255]

Chemical formula 188

[1256]

[1257]

Chemical formula 189

[1258]

[1259] In the first light-emitting compound and the second light-emitting compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each independently

[1260] Hydrogen atoms,

[1261] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1262] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1263] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1264] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1265] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1266] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1267] In R 901 If there are multiple R 901 Same or different from each other,

[1268] In R 902 If there are multiple R 902 Same or different from each other,

[1269] In R 903 If there are multiple R 903 Same or different from each other,

[1270] In R 904 If there are multiple R 904 Same or different from each other,

[1271] In R 905 If there are multiple R 905 Same or different from each other,

[1272] In R 906 If there are multiple R 906 Same or different from each other,

[1273] In R 907 If there are multiple R 907 Same as or different from each other.

[1274] (Other layers of organic EL element)

[1275] The organic EL element involved in this embodiment may have one or more layers composed of organic compounds in addition to the first light-emitting layer and the second light-emitting layer. As the layer composed of organic compounds, for example, it may have at least one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer and an electron transport layer. The layer composed of organic compounds may further include an inorganic compound.

[1276] In the organic EL element involved in this embodiment, the organic layer can be composed only of the first light-emitting layer and the second light-emitting layer, or it can also have at least one layer selected from, for example, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer and an electron transport layer.

[1277] In the organic EL element involved in this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, the electron mobility μe(H1) of the first main material and the electron mobility μe(H2) of the second main material satisfy the relationship of the following mathematical formula (Mathematical Formula 30).

[1278] μe(H2)>μe(H1)...(Mathematical formula 30)

[1279] When the first host material and the second host material satisfy the relationship of the above-mentioned mathematical formula (Mathematical formula 30), the recombination ability of holes and electrons in the first light-emitting layer is improved.

[1280] In the organic EL element involved in the present embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, the hole mobility μh(H1) of the first main material and the hole mobility μh(H2) of the second main material also preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 31).

[1281] μh(H1)>μh(H2)...(Mathematical formula 31)

[1282] In the organic EL element involved in the present embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, the hole mobility μh(H1) of the first main material, the electron mobility μe(H1) of the first main material, the hole mobility μh(H2) of the second main material and the electron mobility μe(H2) of the second main material also preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 32).

[1283] (μe(H2) / μh(H2))>(μe(H1) / μh(H1))...(Math 32)

[1284] The electron mobility can be measured by performing impedance measurement using a mobility evaluation element produced according to the following procedure. The mobility evaluation element is produced, for example, according to the following procedure.

[1285] On a glass substrate with an aluminum electrode (anode), the compound Target, which is the object of electron mobility measurement, is deposited in a manner covering the aluminum electrode to form a measurement object layer. On the measurement object layer, the following compound ET-A is deposited to form an electron transport layer. LiF is deposited on the film of the electron transport layer to form an electron injection layer. Metal aluminum (Al) is deposited on the film of the electron injection layer to form a metal cathode.

[1286] The above-mentioned mobility evaluation element configuration is briefly shown as follows.

[1287] glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / A1(50)

[1288] In addition, the numbers in parentheses represent film thickness (nm).

[1289]

Chemical formula 190

[1290]

[1291] The mobility evaluation element of the electron mobility is set in an impedance measuring device to perform impedance measurement. The impedance measurement is performed by scanning the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element at an AC amplitude of 0.1 V. The modulus M is calculated based on the measured impedance Z using the relationship of the following calculation formula (C1).

[1292] Calculation formula (C1): M = jωZ

[1293] In the above calculation formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s].

[1294] In a Bode plot having the imaginary part of the modulus M as the vertical axis and the frequency [Hz] as the horizontal axis, the electrical time constant τ of the mobility evaluation element was determined from the frequency fmax showing a peak using the following calculation formula (C2).

[1295] Calculation formula (C2): τ = 1 / (2πfmax)

[1296] In the above calculation formula (C2), π is the symbol representing pi.

[1297] The electron mobility μe is calculated using the above τ according to the relationship of the following calculation formula (C3-1).

[1298] Calculation formula (C3-1): μe = d 2 / (Vτ)

[1299] In the above calculation formula (C3-1), d is the total film thickness of the organic thin films constituting the device. In the case of a device for evaluating the mobility of electron mobility, d=210 [nm].

[1300] The hole mobility can be measured by impedance measurement using a mobility evaluation element produced according to the following procedure. The mobility evaluation element is produced, for example, according to the following procedure.

[1301] On a glass substrate with an ITO transparent electrode (anode), the following compound HA-2 was deposited in a manner covering the transparent electrode to form a hole injection layer. The following compound HT-A was deposited on the film of the hole injection layer to form a hole transport layer. Subsequently, the compound Target, which is the measurement object of the hole mobility, was deposited to form a measurement object layer. Metal aluminum (A1) was deposited on the measurement object layer to form a metal cathode.

[1302] The above-mentioned mobility evaluation element configuration is briefly shown below.

[1303] ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80)

[1304] In addition, the numbers in parentheses represent film thickness (nm).

[1305]

Chemical formula 191

[1306]

[1307] The mobility evaluation element of the hole mobility is placed in an impedance measuring device to perform impedance measurement. The impedance measurement is performed while scanning the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element while the AC amplitude is 0.1 V. Based on the measured impedance Z, the modulus M is calculated using the relationship of the above calculation formula (C1).

[1308] The electrical time constant τ of the mobility evaluation element is determined from the frequency fmax showing a peak in a Bode plot having the imaginary part of the modulus M as the vertical axis and the frequency [Hz] as the horizontal axis by the above calculation formula (C2).

[1309] Using τ obtained by the above calculation formula (C2), the hole mobility μh is calculated from the relationship of the following calculation formula (C3-2).

[1310] Calculation formula (C3-2): μh = d 2 / (Vτ)

[1311] In the above calculation formula (C3-2), d is the total film thickness of the organic thin films constituting the device. In the case of a device for evaluating the mobility of the hole mobility, d=215 [nm].

[1312] The electron mobility and hole mobility in this specification are the square root of the electric field strength E 1 / 2 =500[V 1 / 2 / cm 1 / 2 ] value. The square root of the electric field strength E 1 / 2 It can be calculated from the relationship of the following calculation formula (C4).

[1313] Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2

[1314] The impedance measurement is performed using a 1260-type impedance measuring device manufactured by Solartron. For higher accuracy, a 1296-type dielectric constant measuring interface manufactured by Solartron may be used in combination.

[1315] In the organic EL element according to this embodiment, the first light-emitting layer and the second light-emitting layer are preferably in direct contact with each other.

[1316] In the present specification, the layer structure in which “the first light-emitting layer and the second light-emitting layer are directly in contact with each other” may include, for example, any one of the following aspects (LS1), (LS2), and (LS3).

[1317] (LS1) A scheme in which a region where the first host material and the second host material are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[1318] (LS2) In the case where the first light-emitting layer and the second light-emitting layer contain light-emitting compounds, a region in which the first main material, the second main material and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[1319] (LS3) In the case where the first light-emitting layer and the second light-emitting layer contain light-emitting compounds, a region formed by the light-emitting compound, a region formed by the first main material, or a region formed by the second main material is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[1320] (General Structure of Organic EL Element)

[1321] Figure 1 Detailed description of the structure of an example of the organic EL element according to the present embodiment is shown in FIG. Figure 1 The organic EL element 1 shown is a top emission type organic EL element, and the light extraction side is the cathode 4 side.

[1322] The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is composed of a hole injection layer 61, a hole transport layer 62, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 71, and an electron injection layer 72 stacked in this order from the anode 3 side. The anode 3 of the organic EL element 1 includes a conductive layer 31 and a light-reflecting layer 32, and the conductive layer 31 is disposed between the light-reflecting layer 32 and the hole injection layer 61. In the organic EL element 1, the anode 3 is equivalent to a light-reflective electrode. In the organic EL element 1, the cathode 4 is equivalent to a light-transmitting electrode. The light-emitting region 5 of the organic EL element 1 includes a first light-emitting layer 51 on the anode 3 side and a second light-emitting layer 52 on the cathode 4 side.

[1323] Figure 2 2 shows a schematic structure of another example of the organic EL element according to the present embodiment. Figure 2 The organic EL element 1A shown is a bottom emission type organic EL element, and the light extraction side is the anode 3A side.

[1324] The organic EL element 1A includes a light-transmitting substrate 2A, an anode 3A, a cathode 4A, and an organic layer 10 disposed between the anode 3A and the cathode 4A. The organic layer 10 is formed by stacking a hole injection layer 61, a hole transport layer 62, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 71, and an electron injection layer 72 in this order from the anode 3A side. In addition, the organic EL element 1A includes a color conversion section 8 that transmits light emitted from the first light-emitting layer 51 and the second light-emitting layer 52. In the organic EL element 1A, the color conversion section 8 is a color filter. The color conversion section 8 is disposed on the anode 3A side of the organic EL element 1A, which is the light extraction side. Figure 2 In the example shown, it is arranged on a surface of the substrate 2A opposite to the surface facing the anode 3A.

[1325] The organic EL element according to this embodiment is not limited to Figure 1 and Figure 2 The structure of the organic EL element shown.

[1326] As an organic EL element of another structure, for example, there can be mentioned an organic EL element including an organic layer in which a hole injection layer, a hole transport layer, a second light emitting layer, a first light emitting layer, an electron transport layer, and an electron injection layer are stacked in this order from the anode side.

[1327] In addition, as an organic EL element of another configuration, for example, there can be mentioned an organic EL element in which a color conversion unit is arranged on the cathode side as the light extraction side in a top emission type organic EL element. In the case of this scheme, for example, a color conversion unit (such as a color filter and quantum dots) is arranged on the cathode.

[1328] As an example of an organic EL element having another structure, there can be mentioned an organic EL element in which a light reflecting layer, a substrate, and a conductive layer are arranged in this order in a top emission type organic EL element.

[1329] As an example of an organic EL element having another structure, there can be mentioned an organic EL element in which a color conversion section is disposed between a substrate and an anode in a bottom emission type organic EL element.

[1330] The structure of the organic EL element will be further described. In the following, reference numerals may be omitted.

[1331] In the organic EL element according to this embodiment, an organic layer may be disposed between the first light-emitting layer and the second light-emitting layer.

[1332] (Interlayer)

[1333] The organic EL element according to this embodiment may include an intervening layer as an organic layer disposed between the first light-emitting layer and the second light-emitting layer.

[1334] In this embodiment, in order to prevent the Singlet light-emitting region and the TTF light-emitting region from overlapping each other, the interlayer does not contain a light-emitting compound to such an extent that this can be achieved.

[1335] For example, the content of the luminescent compound in the interlayer is not just 0 mass %. For example, when the luminescent compound is a component accidentally mixed in the manufacturing process or a component contained as an impurity in the raw material, the interlayer is allowed to contain these components.

[1336] For example, when all materials constituting the interlayer are material A, material B and material C, the content of each of material A, material B and material C in the interlayer is greater than 10 mass %, and the total content of material A, material B and material C is 100 mass %.

[1337] Hereinafter, the interlayer may be referred to as a “non-doped layer.” In addition, the layer containing a light-emitting compound may be referred to as a “doped layer.”

[1338] Generally speaking, when the light-emitting layer is formed into a stacked structure, it is considered that the light-emitting efficiency can be improved because the Singlet light-emitting region and the TTF light-emitting region can be easily separated.

[1339] In the organic EL element of this embodiment, when an interlayer (non-doped layer) is disposed between the first light-emitting layer and the second light-emitting layer in the light-emitting region, the region where the singlet light-emitting region overlaps with the TTF light-emitting region is reduced, and it is expected that the decrease in TTF efficiency caused by the collision between triplet excitons and carriers is suppressed. In other words, it is believed that the insertion of the interlayer (non-doped layer) between the light-emitting layers helps to improve the efficiency of TTF light emission.

[1340] The interlayer is a non-doped layer.

[1341] The interlayer does not contain metal atoms. Therefore, the interlayer does not contain metal complexes.

[1342] The interlayer comprises an interlayer material, and the interlayer material is not a light-emitting compound.

[1343] The interlayer material is not particularly limited as long as it is a material other than the light-emitting compound.

[1344] Examples of interlayer materials include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and the like; 3) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[1345] The interlayer material may be one or both of the first host material and the second host material. There is no particular limitation as long as the material can separate the Singlet emission region from the TTF emission region and does not impair the Singlet emission and TTF emission.

[1346] In the organic EL device according to the present embodiment, in the interlayer, the content of all the materials constituting the interlayer is 10% by mass or more.

[1347] The interlayer includes the above-mentioned interlayer material as a material constituting the interlayer.

[1348] In the interlayer, the content of the above-mentioned interlayer material is preferably more than 60 mass % of the total mass of the interlayer, the content is more preferably more than 70 mass % of the total mass of the interlayer, the content is further preferably more than 80 mass % of the total mass of the interlayer, the content is further preferably more than 90 mass % of the total mass of the interlayer, and the content is particularly preferably more than 95 mass % of the total mass of the interlayer.

[1349] The interlayer may include only one interlayer material, or may include two or more interlayer materials.

[1350] When the interlayer contains two or more interlayer materials, the upper limit of the total content of the two or more interlayer materials is 100 mass %.

[1351] It should be noted that this embodiment does not exclude the inclusion of materials other than the interlayer material in the interlayer.

[1352] The interlayer may be composed of a single layer or a stack of two or more layers.

[1353] The thickness of the interlayer is not particularly limited as long as it can suppress the overlap of the Singlet light emitting region and the TTF light emitting region, but is preferably 3 nm to 15 nm, more preferably 5 nm to 10 nm per layer.

[1354] When the thickness of the interlayer is 3 nm or more, it is easy to separate the Singlet light-emitting region from the light-emitting region derived from TTF.

[1355] When the thickness of the interlayer is 15 nm or less, it is easy to suppress the phenomenon that the host material of the interlayer emits light.

[1356] The interlayer preferably comprises an interlayer material as a material constituting the interlayer, the triplet energy T1(H1) of the first host material, the triplet energy T1(H2) of the second host material, and the triplet energy T1(M2) of at least one interlayer material. mid ) satisfies the relationship of the following mathematical formula (Mathematical Formula 21).

[1357] T1(H1)≥T1(M mid )≥T1(H2)…(Formula 21)

[1358] In the case where the interlayer contains two or more interlayer materials as materials constituting the interlayer, it is more preferable that the triplet energy T1(H1) of the first host material, the triplet energy T1(H2) of the second host material, and the triplet energy T1(M2) of each interlayer material EA) satisfies the relationship of the following mathematical formula (Mathematical Formula 21A).

[1359] T1(H1)≥T1(M EA )≥T1(H2)…(Mathematical formula 21A)

[1360] (Substrate)

[1361] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent. For example, a plastic substrate can be mentioned. As the material forming the plastic substrate, for example, polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

[1362] (anode)

[1363] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: IndiumTinOxide, indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti) or nitrides of metal materials (such as titanium nitride) can be cited.

[1364] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target to which zinc oxide of 1 mass % or more and 10 mass % or less is added relative to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % or more and 5 mass % or less of tungsten oxide and 0.1 mass % or more and 1 mass % or less of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[1365] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that can easily inject holes regardless of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

[1366] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form an anode, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste, a coating method, an inkjet method, etc. can be used.

[1367] When the organic EL element is a bottom emission type, the anode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits the light emitted from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting more than 50% (preferably more than 80%) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the above-mentioned anode item. The light-transmitting or semi-transmitting metal material can also be a material listed later as a material for the conductive layer (or transparent conductive layer).

[1368] In the case where the organic EL element is a top emission type, the anode is a light reflective electrode having a light reflective layer. The light reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity refers to the property of reflecting more than 50% (preferably more than 80%) of the light emitted from the light emitting layer. The metal material having light reflectivity can be appropriately selected and used from the materials listed in the above-mentioned item of the anode.

[1369] As the metal material used for the light reflecting layer, for example, there can be mentioned: a single material of any metal selected from Al, Ag, Ta, Zn, Mo, W, Ni and Cr, or an alloy material with any metal selected from them as the main component (preferably more than 50 mass % of the whole); an amorphous alloy selected from NiP, NiB, CrP and CrB; a microcrystalline alloy selected from NiAl and silver alloys; and the like.

[1370] In addition, as a metal material for the light reflecting layer, at least one alloy selected from APC (an alloy of silver, palladium and copper), ARA (an alloy of silver, rubidium and gold), MoCr (an alloy of molybdenum and chromium) and NiCr (an alloy of nickel and chromium) can be used.

[1371] The light reflecting layer may be a single layer or a multi-layer layer.

[1372] The anode as a light-reflective electrode may be composed only of a light-reflective layer, or may be a multilayer structure having a light-reflective layer and a conductive layer (preferably a transparent conductive layer). In the case where the anode has a light-reflective layer and a conductive layer, the conductive layer is preferably arranged between the reflective layer and the layer included in the hole transport region (e.g., a hole injection layer or a hole transport layer). In addition, the anode may be a multilayer structure in which a light-reflective layer is arranged between two conductive layers (a first conductive layer and a second conductive layer). In the case of such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or of different materials.

[1373] The material for the conductive layer can be appropriately selected from the materials listed in the above-mentioned anode. In addition, metals, alloys, conductive compounds and mixtures thereof with large work functions (specifically 4.0 eV or more) can also be used as the conductive layer (transparent conductive layer) of the transparent electrode.

[1374] In addition, the conductive layer may also use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys containing at least one selected from alkali metals and alkaline earth metals (such as MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals.

[1375] (cathode)

[1376] The cathode preferably uses a metal, alloy, conductive compound, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1377] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[1378] It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1379] When the organic EL element is a bottom-emitting type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can also be appropriately selected and used from the materials listed in the above-mentioned item of the cathode. In addition, the metal material having light reflectivity can also be the material listed as the metal material for the light reflective layer mentioned above.

[1380] When the organic EL element is a top emission type, the cathode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits the light emitted from the light-emitting layer. Light-transmitting or semi-transmitting means the property of transmitting more than 50% (preferably more than 80%) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can also be appropriately selected and used from the materials listed in the above-mentioned cathode item. The light-transmitting or semi-transmitting metal material can also be the above-mentioned material listed as the material for the conductive layer (or transparent conductive layer).

[1381] (Capping Layer)

[1382] The top emission type organic EL element may include a capping layer on the upper part of the cathode. The capping layer may be arranged on the surface of the cathode opposite to the surface facing the anode.

[1383] The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide).

[1384] In addition, the capping layer may contain at least one compound selected from, for example, aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives.

[1385] Furthermore, a laminated body in which two or more layers containing these compounds which can be used for the capping layer are laminated can also be used as the capping layer.

[1386] (Color conversion unit)

[1387] The color conversion unit is provided on the light extraction side of the organic EL element, and plays a role of converting light extracted from the light extraction side into light of a desired color.

[1388] The color conversion unit is preferably arranged on the electrode (transparent electrode) arranged on the light extraction side among the anode and the cathode.

[1389] The color conversion unit may be, for example, a color filter, a material including quantum dots, or a configuration using a combination of a color filter and a material including quantum dots.

[1390] Color filter

[1391] Examples of the material for the color filter include the following pigments, or solid materials obtained by dissolving or dispersing the pigments in a binder resin.

[1392] Red (R) Pigment:

[1393] A single product selected from perylene pigments, lake pigments, azo pigments, quinacridone pigments, anthraquinone pigments, anthracene pigments, isoindoline pigments and isoindolinone pigments, or a mixture of two or more thereof can be used.

[1394] Green (G) Pigment:

[1395] A single substance consisting of one selected from halogen polysubstituted phthalocyanine pigments, halogen polysubstituted copper phthalocyanine pigments, triphenylmethane basic dyes, isoindoline pigments, isoindolinone pigments, etc., or a mixture of two or more thereof can be used.

[1396] Blue (B) Pigment:

[1397] A single product consisting of one selected from copper phthalocyanine pigments, indanthrone pigments, indophenol pigments, cyanine pigments, dioxazine pigments, etc., or a mixture containing two or more of them can be used.

[1398] As a binder resin that can be used as a material for a color filter, a transparent material is preferably used, for example, a material having a transmittance of 50% or more in a visible light region is preferably used.

[1399] The binder resin of the material that can be used for the color filter is preferably a transparent resin (polymer), etc. The binder resin of the material that can be used for the color filter is preferably one selected from polymethyl methacrylate, polyacrylate, polycarbonate, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxyethyl cellulose and carboxymethyl cellulose, or a mixture containing two or more thereof.

[1400] ·Quantum dots

[1401] As a material containing quantum dots, for example, a material in which quantum dots are dispersed in a resin can be cited. For example, the quantum dots can be at least one selected from CdSe, ZnSe, CdS, CdSeS / ZnS, InP, InP / ZnS, CdS / CdSe, CdS / ZnS, PbS, and CdTe.

[1402] The color conversion section may include a red conversion region that converts blue light into red light, a green conversion region that converts blue light into green light, and a blue transmission region that transmits blue light. The color conversion section is also preferably configured to obtain three colors of light or mixed colors thereof from the organic EL element. For example, when the half-peak width of the emission peak of the blue light emitted by the first light-emitting layer and the second light-emitting layer is narrow and has high color purity, the emitted light passing through the red conversion region is converted into red light with high color purity, and the emitted light passing through the green conversion region is converted into green light with high color purity.

[1403] (Hole Injection Layer)

[1404] The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1405] In addition, as a substance with high hole injection property, 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl]biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Aromatic amine compounds such as 3-[(1-phenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[1406] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD) and other polymer compounds can be mentioned. In addition, polymer compounds with acid added, such as poly (3, 4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (PAni / PSS) can also be used.

[1407] (Hole Transport Layer)

[1408] The hole transport layer is a layer containing a substance having a high hole transport property. In the organic EL device according to this embodiment, the hole transport layer preferably contains a third compound.

[1409] In the organic EL element according to this embodiment, a hole transport layer is preferably disposed between the anode and the light emitting region.

[1410] In the organic EL device according to this embodiment, the hole transport layer preferably contains a third compound represented by the following general formula (H1) or the following general formula (H2).

[1411]

Chemical formula 192

[1412]

[1413] (In the above general formula (H1),

[1414] L 31 , L 32 and L 33 Each independently

[1415] Single key, or

[1416] a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms,

[1417] Ar 31 ,Ar 32 and Ar 33 Each independently

[1418] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1419] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[1420] -Si(RC1 )(R C2 )(R C3 ),

[1421] R C1 , R C2 and R c3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1422] In R C1 If there are multiple R C1 Same or different from each other,

[1423] In R C2 If there are multiple R C2 Same or different from each other,

[1424] In R C3 If there are multiple R c3 The same or different from each other.)

[1425]

Chemical formula 193

[1426]

[1427] (In the above general formula (H2),

[1428] A 41 and A 42 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[1429] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1430] By R 410 ~R 414 One or more groups of two or more adjacent groups

[1431] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1432] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1433] Not bonded to each other,

[1434] By R 420 ~R 424 One or more groups of two or more adjacent groups

[1435] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1436] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1437] Not bonded to each other,

[1438] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 410 ~R 414 and R 420 ~R 424 Each independently

[1439] Hydrogen atoms,

[1440] Cyano,

[1441] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1442] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1443] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1444] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1445] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1446] -O-(R 904 ) shown in the group,

[1447] Halogen atoms,

[1448] Nitro,

[1449] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1450] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1451] m1 is 3, 3 R 410 Same or different from each other,

[1452] m2 is 3, 3 R 420 Same or different from each other,

[1453] L 41 and L 42 Each independently

[1454] single bond,

[1455] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1456] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1457] (In the third compound represented by the above general formula (H2), R 901, R 902 , R 903 and R 904 Each independently

[1458] Hydrogen atoms,

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

[1460] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1461] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1462] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1463] In R 901 If there are multiple R 901 Same or different from each other,

[1464] In R 902 If there are multiple R 902 Same or different from each other,

[1465] In R 903 If there are multiple R 903 Same or different from each other,

[1466] In R 904 If there are multiple R 904 The same or different from each other.)

[1467] In the organic EL device according to this embodiment, the hole transport layer also preferably contains a compound represented by the following general formula (H3) as the third compound.

[1468]

Chemical formula 194

[1469]

[1470] (In the above general formula (H3),

[1471] L 34 , L 35 , L 36 and L 37 Each independently

[1472] Single key, or

[1473] a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms,

[1474] n2 is 1, 2, 3 or 4,

[1475] When n2 is 1, L38 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms,

[1476] When n2 is 2, 3 or 4, multiple L 38 Same or different from each other,

[1477] When n2 is 2, 3 or 4, multiple L 38

[1478] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1479] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1480] Not bonded to each other,

[1481] L does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 38 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms,

[1482] Ar 34 ,Ar 35 ,Ar 36 and Ar 37 Each independently

[1483] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1484] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[1485] -Si(R C1 )(R C2 )(R C3 ),

[1486] R C1 , R C2 and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1487] In R C1 If there are multiple R C1 Same or different from each other,

[1488] In R c2 If there are multiple R C2 Same or different from each other,

[1489] In R C3 If there are multiple R c3 The same or different from each other.)

[1490] In the organic EL device according to this embodiment, it is also preferred that Ar of the third compound 31 ,Ar 32 and Ar 33 At least one of them is a group represented by the following general formula (H11).

[1491] In the organic EL device according to this embodiment, it is also preferred that Ar of the third compound 34 ,Ar 35 ,Ar 36 and Ar 37 At least one of them is a group represented by the following general formula (H11).

[1492]

Chemical formula 195

[1493]

[1494] (In the above general formula (H11),

[1495] X3 is an oxygen atom, a sulfur atom, NR 319 or C(R 320 )(R 321 ),

[1496] By R 311 ~R 318 A group of two or more adjacent

[1497] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1498] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1499] Not bonded to each other,

[1500] By R 320 and R 321 Group

[1501] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1502] bonded to each other to form a substituted or unsubstituted condensed ring, or

[1503] Not bonded to each other,

[1504] R 311 ~R 321 One of them is a single bond to *a, or R 311 ~R 318 The carbon atom constituting the ring skeleton of the above-mentioned substituted or unsubstituted monocyclic ring or the above-mentioned substituted or unsubstituted condensed ring formed by two or more adjacent groups of the above-mentioned substituted or unsubstituted monocyclic rings is bonded to *a through a single bond, or R 320 and R 321The carbon atom constituting the ring skeleton of the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring formed by the groups of the above-mentioned substituted or unsubstituted monocyclic rings bonded to *a via a single bond,

[1505] R which does not form the above-mentioned substituted or unsubstituted monocyclic ring or the above-mentioned substituted or unsubstituted condensed ring and is not a single bond bonded to *a 311 ~R 318 Each independently

[1506] Hydrogen atoms,

[1507] a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

[1508] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or

[1509] a substituted or unsubstituted heterocyclic group having 5 to 10 ring atoms,

[1510] R that is not a single bond to *a 319 for

[1511] Hydrogen atoms,

[1512] a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or

[1513] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,

[1514] R which is not a single bond bonded to *a and does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 320 and R 321 Each independently

[1515] Hydrogen atoms,

[1516] a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or

[1517] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,

[1518] **Each is independently L 31 , L 32 or L 33 The bonding position and L 34 , L 35 , L 36 or L 37 or the bonding position to the nitrogen atom of the amino group. )

[1519] In at least one group represented by the general formula (H11) in the third compound, it is also preferred that R 311 ~R 318At least one of the adjacent two or more groups is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring.

[1520] In at least one group represented by the general formula (H11) in the third compound, it is also preferred that R 311 ~R 318 At least one of the groups of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted benzene ring.

[1521] In at least one group represented by the general formula (H11) in the third compound, it is also preferred that R 311 ~R 318 Among the groups of two or more adjacent groups, one or two groups are bonded to each other to form a substituted or unsubstituted benzene ring.

[1522] In at least one group represented by the general formula (H11) in the third compound, it is also preferred that R 311 ~R 318 Any adjacent groups of two or more thereof are not bonded to each other.

[1523] In the organic EL device according to this embodiment, the third compound is also preferably at least one amine compound selected from the group consisting of:

[1524] A monoamine compound having one substituted or unsubstituted amino group in the molecule,

[1525] A diamine compound having two substituted or unsubstituted amino groups in the molecule,

[1526] A triamine compound having three substituted or unsubstituted amino groups in the molecule, and

[1527] A tetraamine compound having four substituted or unsubstituted amino groups in the molecule.

[1528] In the compound represented by the above general formula (H1) and the compound represented by the above general formula (H3), when the substituent is expressed as "substituted or unsubstituted", it is also preferred that the substituent is not -N(R C6 )(R C7 ) shown in the group. C6 )(R C7 ) in the group represented by C6 and R C7 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring 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 heterocyclic group having 5 to 50 ring atoms.

[1529] In the organic EL device according to the present embodiment, the third compound is also preferably at least one amine compound selected from the group consisting of monoamine compounds and diamine compounds.

[1530] In the organic EL device according to this embodiment, the third compound is also preferably a monoamine compound.

[1531] In the organic EL element involved in this embodiment, the hole transport layer can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 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-phenylfluorene-9-yl)triphenylamine (abbreviated as: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-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'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) and the like. The substances described here are mainly aromatic amine compounds having 10 -6 cm 2 / (V·s) or more.

[1532] The hole transport layer may use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA), anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[1533] As long as the hole-transporting property is higher than the electron-transporting property, other substances may be used. It should be noted that the layer containing the substance with high hole-transporting property may be not only a single layer but also a stack of two or more layers formed of the above substances.

[1534] (Specific example of the third compound)

[1535] Specific examples of the third compound include the following compounds. However, the present invention is not limited to these specific examples of the third compound.

[1536]

Chemical formula 196

[1537]

[1538]

Chemical formula 197

[1539]

[1540]

Chemical formula 198

[1541]

[1542]

Chemical formula 199

[1543]

[1544]

Chemical Formula 200

[1545]

[1546]

Chemical Formula 201

[1547]

[1548]

Chemical Formula 202

[1549]

[1550]

Chemical Formula 203

[1551]

[1552]

Chemical formula 204

[1553]

[1554]

Chemical Formula 205

[1555]

[1556]

Chemical formula 206

[1557]

[1558]

Chemical formula 207

[1559]

[1560]

Chemical formula 208

[1561]

[1562]

Chemical formula 209

[1563]

[1564]

Chemical Formula 210

[1565]

[1566]

Chemical Formula 211

[1567]

[1568]

Chemical Formula 212

[1569]

[1570]

Chemical Formula 213

[1571]

[1572]

Chemical formula 214

[1573]

[1574]

Chemical Formula 215

[1575]

[1576]

Chemical Formula 216

[1577]

[1578] (Electron blocking layer)

[1579] The electron blocking layer is preferably a layer that transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) that is closer to the anode side than the electron blocking layer. The compound contained in the electron blocking layer is, for example, a known compound for an electron blocking layer, preferably at least one compound selected from aromatic amine compounds and carbazole derivatives. In addition, the compound contained in the electron blocking layer may be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. In addition, the compound contained in the electron blocking layer may be a compound having a substituted or unsubstituted carbazole group and one substituted or unsubstituted amino group in the molecule.

[1580] The electron blocking layer may be a layer that blocks excitons generated in the light-emitting layer from moving to layers on the anode side (such as a hole transport layer and a hole injection layer) to prevent the excitation energy from leaking from the light-emitting layer to the peripheral layers.

[1581] (Hole Blocking Layer)

[1582] The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer (such as an electron transport layer) that is closer to the cathode side than the hole blocking layer. The compound contained in the hole blocking layer is, for example, a known compound for a hole blocking layer. The compound contained in the hole blocking layer is, for example, the same as the compound that can be used for the electron transport layer described later, preferably at least one compound selected from a metal complex, a heteroaromatic compound and a polymer compound. In addition, the compound contained in the hole blocking layer can be, for example, at least one compound selected from imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives.

[1583] The hole blocking layer is also preferably a layer that prevents excitons generated in the light-emitting layer from moving to layers on the cathode side (such as the electron transport layer and the electron injection layer) to prevent the excitation energy from leaking from the light-emitting layer to the peripheral layers.

[1584] (Electron Transport Layer)

[1585] The electron transport layer is a layer containing a substance having a high electron transport property. In the organic EL device according to this embodiment, the electron transport layer preferably contains the fourth compound.

[1586] In the organic EL element according to this embodiment, it is preferable that an electron transport layer is disposed between the light emitting region and the cathode.

[1587] In the organic EL device according to this embodiment, the electron transport layer preferably contains a fourth compound represented by the following general formula (E1).

[1588]

Chemical Formula 217

[1589]

[1590] (In the above general formula (E1),

[1591] X 51 , X 52 and X 53 are each independently a nitrogen atom or CR5,

[1592] Among them, X 51 , X 52 and X 53 At least one of them is a nitrogen atom,

[1593] R5 is

[1594] Hydrogen atoms,

[1595] Cyano,

[1596] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1597] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1598] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1599] -O-(R 904 ) shown in the group,

[1600] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1601] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1602] Ax is

[1603] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[1604] a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,

[1605] Bx is

[1606] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[1607] a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,

[1608] L5

[1609] single bond,

[1610] a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms,

[1611] a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or

[1612] a (n+1)-valent group formed by bonding two or three groups selected from a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,

[1613] n is 1, 2 or 3. In the case where n is 2 or 3, L5 is not a single bond.

[1614] Cx are independently

[1615] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[1616] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1617] When there are multiple Cx, the multiple Cx are the same as or different from each other.)

[1618] (In the fourth compound above, R 901 , R 902 , R 903 and R 904 Each independently

[1619] Hydrogen atoms,

[1620] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1621] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1622] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1623] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1624] In R 901 If there are multiple R 901 Same or different from each other,

[1625] In R 902 If there are multiple R 902 Same or different from each other,

[1626] In R 903 If there are multiple R 903 Same or different from each other,

[1627] In R 904 If there are multiple R 904 The same or different from each other.)

[1628] In the organic EL device according to this embodiment, it is preferred that X of the fourth compound 51 , X 52 and X 53 Two or three of them are nitrogen atoms.

[1629] In the organic EL device according to this embodiment, the fourth compound is preferably a compound represented by the following general formula (E11), (E12), (E13) or (E14).

[1630]

Chemical formula 218

[1631]

[1632] (In the above general formulae (E11) to (E14), Ax, Bx, Cx, R5, L5 and n are each the same as defined in the above general formula (E1).)

[1633] In the organic EL device according to the present embodiment, the substituent described as "substituted or unsubstituted" is preferably a group selected from an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[1634] In the organic EL device according to the present embodiment, the substituent described as "substituted or unsubstituted" is preferably a group selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[1635] In the organic EL element involved in this embodiment, the electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as: Almq3), bis (10-hydroxybenzo [h] quinoline) beryllium (abbreviated as: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) may also be used. In this embodiment, benzimidazole compounds may be suitably used. The substances described herein are mainly compounds having 10 -6 cm 2 / (V·s) or more. It should be noted that as long as the electron transport property is higher than the hole transport property, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can also be composed of a single layer, or it can be composed of two or more layers formed by the above substances.

[1636] In addition, a polymer compound may be used in the electron transport layer, for example, 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), etc. may be used.

[1637] (Specific example of the fourth compound)

[1638] Specific examples of the fourth compound include the following compounds. However, the present invention is not limited to these specific examples of the fourth compound.

[1639]

Chemical formula 219

[1640]

[1641]

Chemical Formula 220

[1642]

[1643]

Chemical Formula 221

[1644]

[1645]

Chemical Formula 222

[1646]

[1647]

Chemical Formula 223

[1648]

[1649]

Chemical formula 224

[1650]

[1651]

Chemical Formula 225

[1652]

[1653]

Chemical formula 226

[1654]

[1655]

Chemical formula 227

[1656]

[1657]

Chemical formula 228

[1658]

[1659]

Chemical formula 229

[1660]

[1661]

Chemical Formula 230

[1662]

[1663]

Chemical Formula 231

[1664]

[1665]

Chemical formula 232

[1666]

[1667]

Chemical formula 233

[1668]

[1669]

Chemical formula 234

[1670]

[1671] (Electron Injection Layer)

[1672] The electron injection layer is a layer containing a substance with high electron injecting properties.

[1673] In the organic EL element involved in this embodiment, alkali metals, alkaline earth metals or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx) etc. can be used in the electron injection layer. In addition, materials made by containing alkali metals, alkaline earth metals or their compounds in substances with electron transport properties can also be used, and specifically, materials made by containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently at this time.

[1674] Alternatively, a composite material mixed with an organic compound and an electron donor (donor) can also be used in the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. At this time, as an organic compound, it is preferably a material with excellent transmission of the generated electrons. Specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, it is as long as it is a substance that shows electron donating properties for organic compounds. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[1675] (Layer Formation Method)

[1676] The method for forming each layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above, and known methods such as dry film forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, immersion, flow coating, and inkjet can be used.

[1677] (film thickness)

[1678] The thickness of each organic layer of the organic EL element of this embodiment is not limited except for the cases specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated, and if the film thickness is too thick, a high applied voltage is required, and the efficiency is deteriorated. Therefore, the film thickness of each organic layer of the organic EL element is preferably in the range of several nm to 1 μm.

[1679] (Light emission wavelength of organic EL element)

[1680] The organic electroluminescent element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is driven.

[1681] The organic electroluminescent element according to the present embodiment more preferably emits light having a maximum peak wavelength of 430 nm to 480 nm inclusive when the element is driven.

[1682] The maximum peak wavelength of light emitted by the organic EL element when the element is driven is measured as follows. A voltage is applied to the organic EL element so that the current density is 10 mA / cm 2The spectral emission brightness spectrum at this time was measured using a spectral emission brightness meter CS-2000 (manufactured by Konica Minolta Co., Ltd.) In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum with the maximum luminescence intensity was measured and taken as the maximum peak wavelength (unit: nm).

[1683] [Second embodiment]

[1684] (Electronic equipment)

[1685] The electronic device involved in this embodiment is equipped with any organic EL element in the above-mentioned embodiment. As electronic devices, for example, display devices and light-emitting devices can be cited. As display devices, for example, display components (such as organic EL panel modules, etc.), televisions, mobile phones, tablet computers and personal computers can be cited. As light-emitting devices, for example, lighting and vehicle lamps can be cited. The light-emitting device can also be used in a display device, for example, it can also be used as a backlight for a display device.

[1686] [Variations of Embodiments]

[1687] It should be noted that the present invention is not limited to the above-described embodiments, and modifications, improvements, and the like within the scope that can achieve the object of the present invention are included in the present invention.

[1688] For example, the number of light-emitting layers of the organic EL element is not limited to 2 layers, and more than 3 light-emitting layers may be stacked. In the case where the organic EL element has more than 3 light-emitting layers, at least 2 light-emitting layers (the first light-emitting layer and the second light-emitting layer) satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers, or phosphorescent light-emitting layers that utilize light emission based on electron transition directly from a triplet excited state to a ground state.

[1689] When the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem type organic EL element may be formed in which a plurality of light-emitting units are stacked with an intermediate layer interposed therebetween.

[1690] In addition, the specific structure and shape in the implementation of the present invention may be set to other structures and the like within the scope that can achieve the purpose of the present invention.

[1691] Example

[1692] The present invention is further described in detail below with reference to examples, but the present invention is not limited to these examples.

[1693] <Compound>

[1694] The structures of the compounds represented by the general formula (1) used for producing the organic EL devices according to Examples 1 to 32 are shown below.

[1695]

Chemical formula 235

[1696]

[1697]

Chemical formula 236

[1698]

[1699] The structures of comparative compounds used in the production of the organic EL devices according to Comparative Examples 1 and 2 are shown below.

[1700]

Chemical formula 237

[1701]

[1702] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 32 and Comparative Examples 1 and 2 are shown below.

[1703]

Chemical formula 238

[1704]

[1705] <Production of organic EL elements (1)>

[1706] An organic EL device was produced and evaluated as follows.

[1707] (Example 1)

[1708] An APC (Ag-Pd-Cu) layer with a thickness of 100 nm as a silver alloy layer and an indium oxide-zinc oxide (IZO) layer with a thickness of 10 nm were sequentially formed on a glass substrate by sputtering. Thus, a conductive material layer formed by the APC layer and the IZO layer was obtained. The APC layer is a light reflecting layer, and the IZO layer is a transparent conductive layer. IZO is a registered trademark.

[1709] Next, using conventional photolithography techniques, the conductive material layer formed by the light reflective layer and the transparent conductive layer was patterned by etching using a resist pattern through a mask to form an anode. The substrate formed with the lower electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes.

[1710] Next, the compound HT1 and the compound HA1 were co-deposited on the lower electrode (anode) by vacuum deposition to form a hole injection layer with a thickness of 10 nm. The proportion of the compound HT1 in the hole injection layer was 97% by mass, and the proportion of the compound HA1 was 3% by mass.

[1711] Next, compound HT1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 114 nm.

[1712] Next, compound EB1 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. The second hole transport layer is sometimes referred to as an electron blocking layer.

[1713] Next, compound BH1-1 (first host material) and compound BD (first luminescent compound) were co-evaporated on the second hole transport layer to form a first luminescent layer with a thickness of 10 nm. The proportion of compound BH1-1 in the first luminescent layer was set to 99% by mass, and the proportion of compound BD was set to 1% by mass.

[1714] Next, compound BH2 (second host material) and compound BD (second luminescent compound) were co-evaporated on the first luminescent layer to form a second luminescent layer with a thickness of 10 nm. The proportion of compound BH2 in the second luminescent layer was set to 99% by mass, and the proportion of compound BD was set to 1% by mass.

[1715] Next, compound HB1 was deposited on the second light-emitting layer to form a first electron transport layer with a thickness of 5 nm. The first electron transport layer is sometimes referred to as a hole blocking layer.

[1716] A second electron transport layer with a thickness of 25 nm was formed by co-evaporation of compound ET1 and compound Liq on the first electron transport layer. The proportion of compound ET1 in the second electron transport layer was set to 50% by mass, and the proportion of compound Liq was set to 50% by mass. It should be noted that Liq is the abbreviation of (8-quinolinolato)lithium.

[1717] On the second electron transport layer, ytterbium (Yb) was vapor-deposited to form an electron injection layer having a thickness of 1 nm.

[1718] On the electron injection layer, Mg and Ag were deposited at a mixing ratio (mass %) of 10:90 to form a film, thereby forming a semi-transparent upper electrode (cathode) made of a MgAg alloy with a film thickness of 12 nm.

[1719] The compound Cap was formed into a film on the upper electrode (cathode) by vacuum deposition to form a capping layer with a film thickness of 65 nm.

[1720] The top emission type organic EL device according to Example 1 was produced by performing the operations described above.

[1721] The component structure of Example 1 is shown in abbreviated form as follows.

[1722] APC(100) / IZO(10) / HT1:HA1(10,97%:3%) / HT1(114) / EB1(5) / BH1-1:BD(10,99%:1%) / BH 2: BD (10, 99%: 1%) / HB1 (5) / ET1: Liq (25, 50%: 50%) / Yb (1) / Mg: Ag (12, 10%: 90%) / Cap (65)

[1723] In addition, in the above-mentioned element structure, the figure in a parenthesis represents a film thickness (unit: nm).

[1724] Regarding the element configuration of Example 1, in the same brackets, the number expressed as a percentage (97%:3%) indicates the ratio (mass %) of compound HT1 to compound HA1 in the hole injection layer, the number expressed as a percentage (99%:1%) indicates the ratio (mass %) of the main material (compound BH1-1 or BH2) to the luminescent compound (compound BD) in the light-emitting layer, the number expressed as a percentage (50%:50%) indicates the ratio (mass %) of compound ET1 to Liq in the second electron transport layer, and the number expressed as a percentage (10%:90%) indicates the mixing ratio (mass %) of Mg to Ag in the upper electrode (cathode). Hereinafter, the symbols are set in the same manner.

[1725] The film thickness T of the first light-emitting layer disposed on the anode side of the first light-emitting layer and the second light-emitting layer is AN The thickness T of the second light-emitting layer disposed on the cathode side CA The film thickness ratio T CA / T AN is 1.0.

[1726] (Examples 2 to 16)

[1727] The organic EL devices of Examples 2 to 16 were each produced in the same manner as the organic EL device of Example 1 except that the compound BH1-1 used as the first host material in forming the first light-emitting layer was changed to a compound shown in Table 1.

[1728] (Comparative Example 1)

[1729] The organic EL device of Comparative Example 1 was produced in the same manner as the organic EL device of Example 1, except that the compound BH1-1 used as the first host material in forming the first light-emitting layer was changed to a compound shown in Table 1.

[1730] <Evaluation of Organic EL Devices (1)>

[1731] The following evaluations were performed on the produced organic EL device. The evaluation results are shown in Table 1.

[1732] (Current efficiency L / J and "L / J / CIEy")

[1733] A voltage was applied to the organic EL element so that the current density was 10.00 mA / cm 2 , the spectral emission brightness spectrum at this time is measured using a spectral emission brightness meter CS-1000 (manufactured by Konica Minolta Co., Ltd.). Based on the obtained spectral emission brightness spectrum, the CIE1931 chromaticity coordinates (CIEx and CIEy), current efficiency L / J (unit: cd / A) and "L / J / CIEy" are calculated. The value of "L / J / CIEy" is calculated by dividing the value of the current efficiency L / J by the value of CIEy. The value of "L / J / CIEy" is sometimes referred to as the blue index (BI). In this evaluation, the value of the blue index (BI) is used as an indicator of luminous efficiency.

[1734] (Lifespan LT95)

[1735] A voltage was applied to the organic EL element so that the current density was 50 mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured as the life. The brightness was measured using a spectroscopic emission brightness meter CS-2000 (manufactured by Konica Minolta Co., Ltd.).

[1736] (Δλ and ΔFWHM)

[1737] The first film and the second film are prepared by the method described below, and the maximum peak wavelength λ1 and half-maximum width FWHM1 of the PL spectrum of the first film (with the same structure as the first light-emitting layer) and the maximum peak wavelength λ2 and half-maximum width FWHM2 of the PL spectrum of the second film (with the same structure as the second light-emitting layer) are measured.

[1738] Δλ (unit: nm) is calculated from the obtained maximum peak wavelengths λ1 and λ2 (unit: nm) and the following mathematical formula (mathematical formula X1).

[1739] Δλ=|λ1-λ2| ...(mathematical formula X1)

[1740] ΔFWHM (unit: nm) was calculated from the obtained half-maximum widths FWHM1 and FWHM2 (unit: nm) and the following mathematical formula (mathematical formula X2).

[1741] ΔFWHM=|FWHM1-FWHM2| …(Formula X2)

[1742] The maximum peak wavelength λ1 and the half maximum width FWHM1 of the PL spectrum of the first film, and the maximum peak wavelength λ2 and the half maximum width FWHM2 of the PL spectrum of the second film were measured by the following method.

[1743] First, in order to form the first film into the same structure as the first light-emitting layer, a sample for measuring the first film is prepared by the following method. In order to form the second film into the same structure as the second light-emitting layer, a sample for measuring the second film is prepared by the following method. "The same structure as the first light-emitting layer" means that the first film is made using the same material as the first light-emitting layer in the same mass ratio. Specifically, in the case where the first light-emitting layer contains a first host material and a first light-emitting compound, it means that the ratio of the first light-emitting compound contained in the first light-emitting layer to the first host material (based on mass) (first light-emitting compound / first host material) is the same as the ratio of the first light-emitting compound contained in the first film to the first host material (based on mass) (first light-emitting compound / first host material). The same is true for "the same structure as the second light-emitting layer".

[1744] The first host material and the first luminescent compound were co-evaporated on a quartz substrate (25 mm × 25 mm) so that the ratio of the first luminescent compound to the first host material (based on mass) (first luminescent compound / first host material) was the same as that contained in the first luminescent layer, to form a first film with a thickness of 50 nm. A coating type desiccant (OleDry-P2 manufactured by Futaba Electronics Co., Ltd.) was applied on the first film, and the sealing glass (outer dimensions 17 × 17 mm, inner diameter 13 × 13 mm, and digging depth 0.5 mm) after coating was sealed with an ultraviolet curing resin (TB3124N (IE) manufactured by Threebond FineChemical Co., Ltd.) to seal the first film. The first film measurement sample was prepared in this way. The second film measurement sample was also prepared in the same manner as the first film measurement sample.

[1745] A fluorescence spectrometer (spectrofluorimeter F-7000 (manufactured by Hitachi High-Tech Scientific Co., Ltd.)) was used for the PL spectrum measurement.

[1746] The PL spectrum measurement conditions are as follows.

[1747] The film measurement sample is excited at a specific wavelength (a value 30nm shorter than the maximum peak wavelength of the absorption spectrum) to obtain a PL spectrum, and the maximum peak wavelength λ (unit: nm) and half-peak width FWHM (unit: nm) of the film are calculated from the PL spectrum. FWHM is the abbreviation of full width at half maximum.

[1748]

Table 1

[1749]

[1750] According to the results shown in Table 1, Examples 1 to 16 using the compound represented by the general formula (1) as the first host material have smaller values ​​of Δλ and ΔFWHM than Comparative Example 1, that is, the change in luminescent color (chromaticity deviation) is small. As shown in Examples 1 to 16, the less the change in luminescent color, the less the light loss when extracting light from the top-emitting organic EL element, and the higher the luminescent efficiency and the longer the life. Among the examples using the compound represented by the general formula (1) in which X1 in the general formula (11) to (13) is an oxygen atom, the organic EL elements of Examples 1, 2, 3, 5, 7 and 14 have higher luminescent efficiency and longer life than the organic EL elements of Examples 4 and 6. This is believed to be because the electron mobility of the compound involved in the first host material used in Examples 1, 2, 3, 5, 7 and 14 is high, and the exciton generation region is localized on the pyrene ring of the first host material, thereby suppressing the deactivation of triplet excitons (triplet).

[1751] <Production of organic EL elements (2)>

[1752] An organic EL device was produced and evaluated as follows.

[1753] (Example 17)

[1754] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO (Indium Tin Oxide) transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[1755] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device, and first, a hole injection layer with a thickness of 10 nm was formed by co-evaporating compounds HT1 and HA1 on the surface of the side where the transparent electrode lines were formed in a manner covering the transparent electrode using a vacuum evaporation method. The proportion of compound HT1 in the hole injection layer was set to 97% by mass, and the proportion of compound HA1 was set to 3% by mass.

[1756] Next, compound HT1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 85 nm.

[1757] Next, compound EB1 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. The second hole transport layer is sometimes referred to as an electron blocking layer.

[1758] Next, compound BH1-1 (first host material) and compound BD (first luminescent compound) were co-evaporated on the second hole transport layer to form a first luminescent layer with a thickness of 10 nm. The proportion of compound BH1-1 in the first luminescent layer was set to 99% by mass, and the proportion of compound BD was set to 1% by mass.

[1759] Next, compound BH2 (second host material) and compound BD (second luminescent compound) were co-evaporated on the first luminescent layer to form a second luminescent layer with a thickness of 10 nm. The proportion of compound BH2 in the second luminescent layer was set to 99% by mass, and the proportion of compound BD was set to 1% by mass.

[1760] Next, compound HB1 was deposited on the second light-emitting layer to form a first electron transport layer with a thickness of 5 nm. The first electron transport layer is sometimes referred to as a hole blocking layer.

[1761] On the first electron transport layer, compound ET1 and compound Liq were co-evaporated to form a second electron transport layer with a thickness of 25 nm. The proportion of compound ET1 in the second electron transport layer was 50% by mass, and the proportion of compound Liq was 50% by mass.

[1762] The compound Liq was evaporated on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[1763] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1764] In the above manner, a bottom emission type organic EL element according to Example 17 was produced.

[1765] The component structure of Example 17 is expressed in abbreviated form as follows.

[1766] ITO (130) / HT1: HA1 (10, 97%: 3%) / HT1 (85) / EB1 (5) / BH1-1: BD (10, 99%: 1%) / BH2: BD (10, 99%: 1%) / HB1 (5) / ET1: Liq (25, 50%: 50%) / Liq (1) / Al (80)

[1767] In Example 17, the thickness T of the first light-emitting layer disposed on the anode side of the first light-emitting layer and the second light-emitting layer is AN The thickness T of the second light-emitting layer disposed on the cathode side CA The film thickness ratio T CA / T AN Also 1.0.

[1768] (Examples 18 to 32)

[1769] The organic EL devices of Examples 18 to 32 were each produced in the same manner as the organic EL device of Example 17, except that the compound BH1-1 used as the first host material in forming the first light-emitting layer was changed to a compound shown in Table 2.

[1770] (Comparative Example 2)

[1771] The organic EL device of Comparative Example 2 was produced in the same manner as the organic EL device of Example 17, except that the compound BH1-1 used as the first host material in forming the first light-emitting layer was changed to a compound shown in Table 2.

[1772] <Evaluation of Organic EL Devices (2)>

[1773] The following evaluations were performed on the produced organic EL device. The evaluation results are shown in Table 2.

[1774] (External quantum efficiency EQE)

[1775] First, the external quantum efficiency EQE (unit: %) of the organic EL element before mounting the color filter was measured by the following method.

[1776] The current density was measured by applying a voltage to the device so that the current density reached 10 mA / cm 2 From the obtained spectral emission brightness spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation (lambertian radiation) was performed.

[1777] Next, a color filter is mounted on the glass substrate of the organic EL element using a transparent adhesive.

[1778] As the color filter, a gelatin color filter (manufactured by Edmund Optics Japan, No. 47 dark blue, product number #53-700) was used.

[1779] After the color filter was mounted on the organic EL element, voltage was applied again so that the current density reached 10.0 mA / cm 2 The spectral emission brightness spectrum at this time was measured using a spectral emission brightness meter CS-2000. Based on the obtained spectral emission brightness spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed.

[1780] The relative value (unit: %) of EQE after color filter installation relative to EQE before color filter installation was calculated for each organic EL element in Examples 17 to 32 and Comparative Example 2 using the following formula (Formula X3). A color filter may be abbreviated as CF.

[1781] EQE relative value = (EQE after CF installation / EQE before CF installation) × 100… (Mathematical formula X3)

[1782]

Table 2

[1783]

[1784] According to the results shown in Table 2, Examples 17 to 32 using the compound represented by the general formula (1) as the first host material have smaller values ​​of Δλ and ΔFWHM, that is, less change in luminescent color (chromaticity deviation), compared to Comparative Example 2. As shown in Examples 17 to 32, the less change in luminescent color, the less light loss when extracting light from a bottom-emitting organic EL element using a color filter, and the higher the luminous efficiency.

[1785] <Evaluation of Compounds>

[1786] (Triplet energy T1)

[1787] The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) to a concentration of 10 μmol / L to obtain a solution, which was added to a quartz colorimetric cell as a measurement sample. For this measurement sample, the phosphorescence spectrum was measured at a low temperature (77 [K]) (the vertical axis was set to phosphorescence emission intensity, and the horizontal axis was set to wavelength.), and the wavelength value λ based on the intersection of the tangent and the horizontal axis was set to the rise tangent line on the short wavelength side of the phosphorescence spectrum. edge [nm], and the energy calculated by the following conversion formula (F1) is referred to as triplet energy T1. It should be noted that the triplet energy T1 may have an error of about 0.02 eV depending on the measurement conditions.

[1788] Conversion formula (F1): T1 [eV] = 1239.85 / λ edge

[1789] The tangent line for the rise on the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values ​​of the spectrum, the tangent line at each point on the curve is considered toward the long wavelength side. The slope of the tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where the slope value takes the maximum value (i.e., the tangent line at the inflection point) is used as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.

[1790] It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

[1791] For the measurement of phosphorescence, a spectrofluorophotometer model F-4500 manufactured by Hitachi High-Technologies Corporation was used.

[1792] (Singlet energy S1)

[1793] A 10 μmol / L toluene solution of the compound to be measured was prepared and added to a quartz colorimetric cell, and the absorption spectrum of the sample was measured at room temperature (300 K) (the vertical axis was set as the absorption intensity, and the horizontal axis was set as the wavelength). For the downward tangent on the long wavelength side of the absorption spectrum, the wavelength value λedge [nm] of the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the singlet energy.

[1794] Conversion formula (F2): S1[eV]=1239.85 / λedge

[1795] As an absorption spectrum measuring apparatus, a spectrophotometer manufactured by Hitachi, Ltd. (apparatus name: U3310) was used.

[1796] The tangent line for the long wavelength side of the absorption spectrum is drawn as follows. When moving along the long wavelength direction on the spectrum curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum, the tangent line at each point on the curve is considered. As the curve falls (that is, as the value of the vertical axis decreases), the slope of the tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope value is the minimum on the longest wavelength side (excluding the case where the absorbance is less than 0.1) is used as the tangent line for the long wavelength side of the absorption spectrum.

[1797] It should be noted that a maximum point where the absorbance value is 0.2 or less is not included in the above-mentioned maximum value on the longest wavelength side.

[1798] (Measurement of the maximum peak wavelength of fluorescence emission (FL-peak))

[1799] The compound to be measured was concentrated at 4.9×10 -6 The toluene solution was prepared by dissolving the toluene solution in a concentration of mol / L. The fluorescence maximum peak wavelength λ (unit: nm) when the toluene solution was excited at 390 nm was measured using a fluorescence spectrometer (spectrofluorimeter F-7000 (manufactured by Hitachi High-Tech Sciences, Ltd.)).

[1800] The maximum peak wavelength λ of the fluorescence emission of compound BD is 455 nm.

[1801]

Table 3

[1802]

[1803] <Synthesis of Compounds>

[1804] (Synthesis example 1)

[1805] (Synthesis of Intermediate M1-C)

[1806]

Chemical formula 239

[1807]

[1808] Under an argon atmosphere, intermediate M1-A: 3.66 g (10.0 mmol), intermediate M1-B: 1.56 g (10.0 mmol), dichlorobisAmphos palladium (II): 0.14 g (0.2 mmol), 2M sodium carbonate aqueous solution: 15.0 ml (30.0 mmol) and 1,2-dimethoxyethane: 100 ml were put into a flask and heated and stirred at 75°C for 8 hours. After cooling to room temperature (25°C), the reaction solution was concentrated and toluene: 500 ml was added. After the obtained solution was fully stirred, the water layer was removed. The remaining organic layer was concentrated and the residue was purified by silica gel column chromatography to obtain 3.29 g of a white solid (yield 75%). According to LC-MS analysis, the white solid was identified as intermediate M1-C. Tf represents trifluoromethanesulfonyl. LC-MS is the abbreviation for Liquid Chromatography-Mass Spectrometry.

[1809] (Synthesis of Compound BH1-1)

[1810]

Chemical Formula 240

[1811]

[1812] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M1-C and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B to obtain 1.12 g of a white solid (yield 48%). The white solid was identified as compound BH1-1 by LC-MS analysis.

[1813] (Synthesis example 2)

[1814] (Synthesis of Compound BH1-2)

[1815]

Chemical Formula 241

[1816]

[1817] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M1-C and intermediate M2-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 2.30 g of a white solid (yield 39%). The white solid was identified as compound BH1-2 by LC-MS analysis.

[1818] (Synthesis example 3)

[1819] (Synthesis of Intermediate M3-B)

[1820]

Chemical formula 242

[1821]

[1822] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M3-A was used instead of intermediate M1-A to obtain 3.58 g of a white solid (yield 66%). The white solid was identified as intermediate M3-B by LC-MS analysis.

[1823] (Synthesis of Compound BH1-3)

[1824]

Chemical formula 243

[1825]

[1826] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M3-B and intermediate M2-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.73 g of a white solid (yield 52%). The white solid was identified as compound BH1-3 by LC-MS analysis.

[1827] (Synthesis Example 4)

[1828] (Synthesis of Intermediate M4-B)

[1829]

Chemical formula 244

[1830]

[1831] A white solid (1.34 g, yield 73%) was obtained by the same method as that of intermediate M1-C except that intermediate M4-A was used instead of intermediate M1-A in the synthesis of intermediate M1-C. The white solid was identified as intermediate M4-B by LC-MS analysis.

[1832] (Synthesis of Compound BH1-4)

[1833]

Chemical Formula 245

[1834]

[1835] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M4-B and intermediate M2-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.98 g of a white solid (yield 32%). The white solid was identified as compound BH1-4 by LC-MS analysis.

[1836] (Synthesis Example 5)

[1837] (Synthesis of Compound BH1-5)

[1838]

Chemical formula 246

[1839]

[1840] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M2-A was used instead of intermediate M1-B to obtain 2.16 g (yield 53%) of a white solid. The white solid was identified as compound BH1-5 by LC-MS analysis.

[1841] (Synthesis Example 6)

[1842] (Synthesis of Intermediate M6-B)

[1843]

Chemical formula 247

[1844]

[1845] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M6-A was used instead of intermediate M1-A to obtain 2.11 g of a white solid (yield 76%). The white solid was identified as intermediate M6-B by LC-MS analysis.

[1846] (Synthesis of Compound BH1-6)

[1847]

Chemical formula 248

[1848]

[1849] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M6-B and intermediate M2-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.26 g of a white solid (yield 41%). The white solid was identified as compound BH1-6 by LC-MS analysis.

[1850] (Synthesis Example 7)

[1851] (Synthesis of Intermediate M7-B)

[1852]

Chemical formula 249

[1853]

[1854] A white solid (1.73 g, 64% yield) was obtained by the same method as that of the intermediate M1-C except that the intermediate M7-A was used instead of the intermediate M1-A in the synthesis of the intermediate M1-C. The white solid was identified as the intermediate M7-B by LC-MS analysis.

[1855] (Synthesis of Compound BH1-7)

[1856]

Chemical Formula 250

[1857]

[1858] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M7-B and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.33 g of a white solid (yield 46%). The white solid was identified as compound BH1-7 by LC-MS analysis.

[1859] (Synthesis Example 8)

[1860] (Synthesis of Compound BH1-8)

[1861]

Chemical Formula 251

[1862]

[1863] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M8-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B to obtain 0.73 g (yield 58%) of a white solid. The white solid was identified as compound BH1-8 by LC-MS analysis.

[1864] (Synthesis Example 9)

[1865] (Synthesis of Compound BH1-9)

[1866]

Chemical formula 252

[1867]

[1868] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M9-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.08 g of a white solid (yield 63%). The white solid was identified as compound BH1-9 by LC-MS analysis.

[1869] (Synthesis Example 10)

[1870] (Synthesis of Compound BH1-10)

[1871]

Chemical formula 253

[1872]

[1873] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M10-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.98 g of a white solid (yield 60%). The white solid was identified as compound BH1-10 by LC-MS analysis.

[1874] (Synthesis Example 11)

[1875] (Synthesis of Compound BH1-11)

[1876]

Chemical formula 254

[1877]

[1878] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M11-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.88 g of a white solid (yield 30%). The white solid was identified as compound BH1-11 by LC-MS analysis.

[1879] (Synthesis Example 12)

[1880] (Synthesis of Compound BH1-12)

[1881]

Chemical formula 255

[1882]

[1883] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M12-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.82 g of a white solid (yield 28%). The white solid was identified as compound BH1-12 by LC-MS analysis.

[1884] (Synthesis Example 13)

[1885] (Synthesis of Compound BH1-13)

[1886]

Chemical formula 256

[1887]

[1888] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M13-A and intermediate M1-D were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.10 g of a white solid (yield 68%). The white solid was identified as compound BH1-13 by LC-MS analysis.

[1889] (Synthesis Example 14)

[1890] (Synthesis of Compound BH1-14)

[1891]

Chemical formula 257

[1892]

[1893] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M1-C and intermediate M14-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 1.01 g of a white solid (yield 61%). The white solid was identified as compound BH1-14 by LC-MS analysis.

[1894] (Synthesis Example 15)

[1895] (Synthesis of Compound BH1-15)

[1896]

Chemical formula 258

[1897]

[1898] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M9-A and intermediate M14-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.99 g of a white solid (yield 57%). The white solid was identified as compound BH1-15 by LC-MS analysis.

[1899] (Synthesis Example 16)

[1900] (Synthesis of Compound BH1-16)

[1901]

Chemical formula 259

[1902]

[1903] The same method as that for the synthesis of intermediate M1-C was used except that intermediate M11-A and intermediate M14-A were used instead of intermediate M1-A and intermediate M1-B in the synthesis of intermediate M1-C to obtain 0.75 g of a white solid (yield 26%). The white solid was identified as compound BH1-16 by LC-MS analysis.

[1904] Explanation of symbols

[1905] 1, 1A…organic EL element, 10…organic layer, 2, 2A···substrate, 3, 3A···anode, 31…conductive layer, 32…light reflecting layer, 4, 4A…cathode, 5…light emitting region, 51…first light emitting layer, 52…second light emitting layer, 61…hole injection layer, 62…hole transport layer, 71…electron transport layer, 72…electron injection layer, 8…color conversion unit.

Claims

1. An organic electroluminescent element, the organic electroluminescent element having substrate, anode, cathode, and a light emitting region disposed between the anode and the cathode, The substrate, the anode, the light emitting region and the cathode are arranged in sequence, The light-emitting region includes a first light-emitting layer and a second light-emitting layer, The first light-emitting layer contains a first host material, The first host material is a first compound represented by the following general formula (1): The second light-emitting layer contains a second host material, The first host material and the second host material are different from each other, The thickness T of the layer disposed on the anode side of the first light-emitting layer and the second light-emitting layer is AN The film thickness T of the layer arranged on the cathode side CA The film thickness ratio T CA / T AN is 0.3 or more and 1.5 or less, The organic electroluminescent element comprises at least one of the following structures (i) and (ii): Configuration (i): the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmissivity, Configuration (ii): a color conversion unit is arranged on the light extraction side of the organic electroluminescent element, In the general formula (1), R1 to R5 and Ra are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms, The four Ra ​​are the same or different from each other. L1 is single bond, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 20 ring atoms, Ar1 is a group represented by the general formula (11), (12) or (13), In the general formulae (11), (12) and (13), X1 is an oxygen atom, a sulfur atom or C(Rb1)(Rb2), The group consisting of Rb1 and Rb2 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms, in, R 101 ~R 110 One of them is a single bond to L1, R 111 ~R 120 One of them is a single bond to L1, R 121 ~R 130 One of them is a single bond bonding to L1. 2 . The organic electroluminescent element according to claim 1 , which is a top emission type element having the configuration (i) and in which light emitted from the light emitting region is extracted from the cathode side. 3 . The organic electroluminescent element according to claim 1 , which is a bottom emission type element having the configuration (ii) and in which light emitted from the light emitting region is extracted from the substrate side.

4. The organic electroluminescent element according to any one of claims 1 to 3, wherein R1 to R5 and Ra are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

5. The organic electroluminescent element according to any one of claims 1 to 4, wherein The first compound is represented by the following general formula (101): In the general formula (101), R1 to R5, L1 and Ar1 are defined as in the general formula (1), and R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the general formula (1).

6. The organic electroluminescent element according to any one of claims 1 to 5, wherein Ar1 of the first compound is a group represented by the following general formula (11A), (11B), (11C), (11D), (12A), (12B), (12C), (12D), (13A), (13B), (13C) or (13D), In the general formulae (11A), (11B), (11C), (11D), (12A), (12B), (12C), (12D), (13A), (13B), (13C) and (13D), X1 is an oxygen atom, a sulfur atom or C(Rb1)(Rb2), The group consisting of Rb1 and Rb2 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R 101 ~R 110 , R 111 ~R 120 , R 121 ~R 130 , and Rb1 and Rb2 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms, * indicates the bonding position to L1.

7. The organic electroluminescent element according to claim 6, wherein: Ar1 of the first compound is a group represented by the general formula (11C), (12C) or (13C).

8. The organic electroluminescent element according to any one of claims 1 to 5, wherein R 101 ~R 103 One of them is a single bond to L1, R 111 ~R 113 One of them is a single bond to L1, R 121 ~R 123 One of them is a single bond bonding to L1.

9. The organic electroluminescent element according to any one of claims 1 to 8, wherein X1 is an oxygen atom.

10. The organic electroluminescent element according to any one of claims 1 to 8, wherein X1 is C(Rb1)(Rb2).

11. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first compound is represented by the following general formula (111), (121) or (131), In the general formulae (111), (121) and (131), R1 to R5 and L1 are defined as in the general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the general formula (1), X1, R 102 ~R 110 , R 112 ~R 120 and R 122 ~R 130 The definitions of are the same as those in the above-mentioned general formulae (11) to (13).

12. The organic electroluminescent element according to claim 11, wherein X1 is an oxygen atom.

13. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first compound is represented by the following general formula (141), (142) or (143), In the general formula (141), R1 to R5 and L1 are defined as in the general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the general formula (1), X1, R 111 , R 112 and R 114 ~R 120 The definitions of are the same as those in the general formula (12), In the general formula (142), R1 to R5 and L1 are defined as in the general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the general formula (1), X1, R 101 , R 102 and R 104 ~R 110 The definitions of are the same as those in the general formula (11), In the general formula (143), R1 to R5 and L1 are defined as in the general formula (1), R6, R7, R9 and R 10 Each independently has the same meaning as Ra in the general formula (1), X1, R 121 , R 122 and R 124 ~R 130 The definitions of are the same as those in the general formula (13).

14. The organic electroluminescent element according to claim 13, wherein X1 is C(Rb1)(Rb2).

15. The organic electroluminescent element according to any one of claims 1 to 14, wherein L1 in the first compound is a single bond, or a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms.

16. The organic electroluminescent element according to any one of claims 1 to 15, wherein L1 in the first compound is a single bond or a substituted or unsubstituted p-phenylene group.

17. The organic electroluminescent element according to any one of claims 1 to 16, wherein R1, R2, R4, R5 and Ra are hydrogen atoms, and R3 is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

18. The organic electroluminescent element according to any one of claims 1 to 17, wherein R is not a single bond to L1 101 ~R 110 , R 111 ~R 120 and R 121 ~R 130 It is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

19. The organic electroluminescent element according to any one of claims 1 to 18, wherein The first compound contains at least one deuterium atom in the molecule.

20. The organic electroluminescent element according to any one of claims 1 to 19, wherein In the first compound, the groups expressed as "substituted or unsubstituted" are all "unsubstituted" groups.

21. The organic electroluminescent element according to any one of claims 1 to 20, wherein The first light-emitting layer includes the first host material and a first light-emitting compound, The second light-emitting layer includes the second host material and a second light-emitting compound, The first luminescent compound and the second luminescent compound are the same as or different from each other.

22. The organic electroluminescent element according to claim 21, wherein The first light-emitting compound and the second light-emitting compound are each independently a compound that emits light with a maximum peak wavelength of 500 nm or less.

23. The organic electroluminescent element according to any one of claims 1 to 22, wherein The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical formula 1), T1(H1)>T1(H2)…(Formula 1).

24. The organic electroluminescent element according to any one of claims 1 to 23, wherein The first light-emitting layer is disposed between the anode and the second light-emitting layer.

25. The organic electroluminescent element according to any one of claims 1 to 24, wherein The second host material is a second compound represented by the following general formula (2): In the general formula (2), R 201 ~R 208 Each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 201 and L 202 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 Each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the second host material, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each independently 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 heterocyclic group having 5 to 50 ring atoms, In R 901 If there are multiple R 901 Same or different from each other, In R 902 If there are multiple R 902 Same or different from each other, In R 903 If there are multiple R 903 Same or different from each other, In R 904 If there are multiple R 904 Same or different from each other, In R 905 If there are multiple R 905 Same or different from each other, In R 906 If there are multiple R 906 Same or different from each other, In R 907 If there are multiple R 907 Same or different from each other, In R 801 If there are multiple R 801 Same or different from each other, In R 802 If there are multiple R 802 Same as or different from each other.

26. The organic electroluminescent element according to any one of claims 1 to 25, wherein A hole transport layer is arranged between the anode and the light emitting region. The hole transport layer contains a third compound represented by the following general formula (H1) or the following general formula (H2), In the general formula (H1), L 31 , L 32 and L 33 Each independently Single key, or a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, Ar 31 ,Ar 32 and Ar 33 Each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or -Si(R C1 )(R C2 )(R C3 ), R C1 , R C2 and R C3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, In R C1 If there are multiple R C1 Same or different from each other, In R C2 If there are multiple R C2 Same or different from each other, In R c3 If there are multiple R C3 Same or different from each other, In the general formula (H2), A 41 and A 42 Each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, By R 410 ~R 414 One or more groups of two or more adjacent groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, By R 420 ~R 424 One or more groups of two or more adjacent groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 410 ~R 414 and R 420 ~R 424 Each independently Hydrogen atoms, Cyano, 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 ) shown in the group, -O-(R 904 ) shown in the group, Halogen atoms, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, m1 is 3, 3 R 410 Same or different from each other, m2 is 3, 3 R 420 Same or different from each other, L 41 and L 42 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, In the third compound represented by the general formula (H2), R 901 , R 902 , R 903 and R 904 Each independently 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 heterocyclic group having 5 to 50 ring atoms, In R 901 If there are multiple R 901 Same or different from each other, In R 902 If there are multiple R 902 Same or different from each other, In R 903 If there are multiple R 903 Same or different from each other, In R 904 If there are multiple R 904 Same as or different from each other.

27. The organic electroluminescent element according to any one of claims 1 to 26, wherein An electron transport layer is arranged between the light emitting region and the cathode, The electron transport layer contains a fourth compound represented by the following general formula (E1), In the general formula (E1), X 51 , X 52 and X 53 are each independently a nitrogen atom or CR5, Among them, X 51 , X 52 and X 53 At least one of them is a nitrogen atom, R5 is Hydrogen atoms, Cyano, 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, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ax is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, Bx is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, L5 single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group formed by bonding two or three groups selected from a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, n is 1, 2 or 3. In the case where n is 2 or 3, L5 is not a single bond. Cx are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, When there are multiple Cx, the multiple Cx are the same or different from each other. In the fourth compound, R 901 , R 902 , R 903 and R 904 Each independently 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 heterocyclic group having 5 to 50 ring atoms, In R 901 If there are multiple R 901 Same or different from each other, In R 902 If there are multiple R 902 Same or different from each other, In R 903 If there are multiple R 903 Same or different from each other, In R 904 If there are multiple R 904 Same as or different from each other.

28. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 27.

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