Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element, which is an organic electroluminescent element comprising an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in sequence, wherein the second electron transport layer comprises a compound represented by the following formula (1), and the light-emitting layer comprises a compound represented by the following formula (10).

Description

Technical Field

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

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

[0003] An organic EL element includes a light-emitting layer between an anode and a cathode, and may also have a laminated structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

[0004] As documents disclosing such an organic EL element, for example, the following Patent Documents 1 to 4 can be cited.

[0005] Prior art literature

[0006] Patent Literature

[0007] [Patent Document 1] WO2005 / 113531

[0008] [Patent Document 2] US2016 / 0020405

[0009] [Patent Document 3] WO2016 / 126022

[0010] [Patent document 4] US2017 / 0018723. Summary of the invention

[0011] The object of the present invention is to provide a high-performance organic electroluminescent element. In particular, an organic electroluminescent element with high luminous efficiency, an organic electroluminescent element with long life, and an organic electroluminescent element with high luminous efficiency and long life are provided. In addition, the object of the present invention is to provide an electronic device using such an organic electroluminescent element.

[0012] According to the present invention, the following organic electroluminescent element and electronic device can be provided.

[0013] 1. An organic electroluminescent element, which is an organic electroluminescent element comprising an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in sequence,

[0014] The second electron transport layer comprises a compound represented by the following formula (1):

[0015] The light-emitting layer contains a compound represented by the following formula (10).

[0016] [Chemistry 1]

[0017]

[0018] [In formula (1),

[0019] FA is a substituted or unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings.

[0020] L 1 is a single bond, or is selected from

[0021] Substituted or unsubstituted phenylene,

[0022] Substituted or unsubstituted biphenylene,

[0023] Substituted or unsubstituted terphenylene,

[0024] Substituted or unsubstituted quaterphenylene,

[0025] an arylene group containing a substituted or unsubstituted condensed ring having 10 to 30 ring carbon atoms, and

[0026] A group in which 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted arylene groups having a condensed ring having 10 to 30 ring carbon atoms are linked via a single bond.

[0027] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.

[0028] X 1 ~X 3 Each independently is N or CR 1 Among them, X 1 ~X 3 Two or more of them are N. 1 Not adjacent to L 1 ,Ar 1 or Ar 2 The bonds form a ring.

[0029] R 1 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.]

[0030] [Chemistry 2]

[0031]

[0032] [In formula (10),

[0033] R 11 ~R 18 are each independently a hydrogen atom,

[0034] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0035] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0036] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0037] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0038] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0039] a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,

[0040] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0041] a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,

[0042] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0043] -Si(R 101 )(R 102 )(R 103 ),

[0044] -C(=O)R 104 ,

[0045] -COOR 105 ,

[0046] -N(R 106 )(R 107 ),

[0047] Halogen atoms, cyano, nitro,

[0048] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0049] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0050] R 101 ~R 107 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0051] R 101 ~R 107 When there are 2 or more, 2 or more R 101 ~R 107 They can be the same or different.

[0052] Ar 11 and Ar 12 At least one of them is a monovalent group represented by the following formula (11).

[0053] [Chemistry 3]

[0054]

[0055] (In formula (11),

[0056] R 21 ~R 28 One of them is the same as L 11 or L 12 Bonded bonding sites,

[0057] Not with L 11 or L 12 Bonded bonding position R 21 ~R 28 are each independently a hydrogen atom,

[0058] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0059] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0060] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0061] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0062] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0063] a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,

[0064] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0065] a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,

[0066] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0067] -Si(R 101 )(R 102 )(R 103 ),

[0068] -C(=O)R 104 ,

[0069] -COOR 105 ,

[0070] -N(R 106 )(R 107 ),

[0071] Halogen atoms, cyano, nitro,

[0072] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0073] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0074] R 101 ~R 107 As described above. ).

[0075] Ar which is not a monovalent group represented by the above formula (11) 11 or Ar 12 It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted by an unsubstituted alkyl group having 1 to 50 ring carbon atoms, or an aryl group having 6 to 50 ring carbon atoms substituted by an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0076] L 11 and L 12 Each is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, 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.].

[0077] 2. An electronic device comprising the organic electroluminescent element.

[0078] According to the present invention, a high-performance organic electroluminescent element can be provided. In particular, an organic electroluminescent element with high luminous efficiency, an organic electroluminescent element with long life, and an organic electroluminescent element with high luminous efficiency and long life can be provided. In addition, according to the present invention, an electronic device using such an organic electroluminescent element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0079] [ Figure 1 ] A diagram showing the schematic structure of an embodiment of an organic EL element according to the first mode of the present invention. DETAILED DESCRIPTION

[0080] [definition]

[0081] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0082] In this specification, the so-called ring carbon number refers to the number of carbon atoms in the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring structure. When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. As for the "ring carbon number" recorded below, unless otherwise specified, it has the same meaning. For example, the number of ring carbon atoms of the benzene ring is 6, the number of ring carbon atoms of the naphthalene ring is 10, the number of ring carbon atoms of the pyridine ring is 5, and the number of ring carbon atoms of the furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0083] When a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is included in the number of carbon atoms forming the ring.

[0084] In this specification, the so-called ring-forming atoms number, represents the number of atoms constituting the ring itself of the compound (such as monocyclic compound, condensed ring compound, bridged compound, carbocyclic compound, heterocyclic compound) whose atoms are bonded to form a cyclic structure (such as monocyclic, condensed ring, ring set). The atoms that do not constitute the ring (such as hydrogen atoms with the bonding position of the atoms constituting the ring as the terminal) and the substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. About the "ring-forming atoms number" recorded below, as long as there is no special explanation, it means the same meaning. For example, the number of ring-forming atoms of pyridine ring is 6, the number of ring-forming atoms of quinazoline ring is 10, and the number of ring-forming atoms of furan ring is 5. About the hydrogen atoms bonded respectively on the carbon atoms of pyridine ring and quinazoline ring, the atoms constituting the substituents are not included in the number of ring-forming atoms.

[0085] In this specification, "the number of carbon atoms is XX to YY" in the expression "a substituted or unsubstituted ZZ group having a carbon number of XX to YY" means the number of carbon atoms when the ZZ group is unsubstituted, and does not include the carbon number of the substituent when substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer greater than 1.

[0086] In this specification, "the number of atoms XX to YY" in the expression "ZZ group having XX to YY atoms which may be substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer greater than 1.

[0087] "Unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted by a substituent and is bonded with a hydrogen atom. Alternatively, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0088] The substituents described in this specification are described below.

[0089] Unless otherwise specified in the present specification, the number of carbon atoms in the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0090] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0091] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0092] Unless otherwise specified in the present specification, the “unsubstituted alkenyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0093] Unless otherwise specified in the present specification, the “unsubstituted alkynyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0094] Unless otherwise specified in the present specification, the number of carbon atoms in the ring of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0095] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0096] Unless otherwise specified in the present specification, the number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified in the present specification, the number of carbon atoms of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0097] As specific examples of the "substituted or unsubstituted aryl group" described in this specification (specific example group G1), the following unsubstituted aryl groups and substituted aryl groups can be cited. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) Hereinafter, when simply referred to as "aryl group", both "unsubstituted aryl group" and "substituted aryl group" are included.

[0098] When the "substituted aryl group" is an "unsubstituted aryl group" having a substituent, the following examples of "unsubstituted aryl groups" having a substituent, examples of substituted aryl groups, etc. can be cited. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are just examples, and the "substituted aryl group" described in this specification also includes groups such as "unsubstituted aryl groups" having a substituent further having a substituent, and "substituted aryl groups" further having a substituent.

[0099] Unsubstituted aryl:

[0100] Phenyl,

[0101] p-Biphenyl,

[0102] m-Biphenyl,

[0103] o-Biphenyl,

[0104] p-terphenyl-4-yl,

[0105] p-terphenyl-3-yl,

[0106] p-terphenyl-2-yl,

[0107] m-terphenyl-4-yl,

[0108] m-terphenyl-3-yl,

[0109] m-terphenyl-2-yl,

[0110] o-terphenyl-4-yl,

[0111] o-terphenyl-3-yl,

[0112] o-terphenyl-2-yl,

[0113] 1-naphthyl,

[0114] 2-naphthyl,

[0115] Anthracene,

[0116] Benzanthryl,

[0117] Fiki,

[0118] Triphenylene,

[0119] Phenyl,

[0120] Pyrene

[0121] Hexyl

[0122] Benzopheneyl,

[0123] Triphenylene,

[0124] Benzotriphenylene,

[0125] Tetraphenylene,

[0126] Pentaphenyl,

[0127] Fluorene,

[0128] 9,9'-Spirobifluorenyl,

[0129] Benzofluorenyl,

[0130] Dibenzofluorenyl,

[0131] Fluoranthene group,

[0132] Benzofluoranthene,

[0133] Peryl

[0134] Substituted aryl groups:

[0135] o-Toluyl,

[0136] m-Toluene

[0137] p-Tolyl,

[0138] p-Xylyl,

[0139] m-Xylyl,

[0140] o-Xylyl,

[0141] p-Isopropylphenyl,

[0142] m-isopropylphenyl,

[0143] o-isopropylphenyl,

[0144] 4-tert-Butylphenyl,

[0145] m-tert-butylphenyl,

[0146] o-tert-butylphenyl,

[0147] 3,4,5-Trimethylphenyl,

[0148] 9,9-dimethylfluorenyl,

[0149] 9,9-Diphenylfluorenyl

[0150] 9,9-di(4-methylphenyl)fluorenyl,

[0151] 9,9-di(4-isopropylphenyl)fluorenyl,

[0152] 9,9-di(4-tert-butylphenyl)fluorenyl,

[0153] Cyanophenyl,

[0154] Triphenylsilylphenyl,

[0155] Trimethylsilylphenyl,

[0156] Phenyl naphthyl,

[0157] Naphthylphenyl

[0158] The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among the atoms constituting the ring. 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.

[0159] The "heterocyclic group" described in the present specification may be a monocyclic group or a condensed ring group.

[0160] The "heterocyclic group" described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.

[0161] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic groups and substituted heterocyclic groups can be cited. (Herein, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) Hereinafter, when simply referred to as a "heterocyclic group", both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0162] "Substituted heterocyclic group" refers to the case where "unsubstituted heterocyclic group" has a substituent, and examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed below can be cited. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are just examples, and the "substituted heterocyclic group" described in this specification also includes groups such as "unsubstituted heterocyclic group" having a substituent further having a substituent, and "substituted heterocyclic group" further having a substituent.

[0163] Unsubstituted heterocyclic groups containing nitrogen atoms:

[0164] Pyrrolyl,

[0165] Imidazole,

[0166] Pyrazolyl,

[0167] Triazole,

[0168] Tetrazolyl,

[0169] Oxazolyl,

[0170] Isoxazolyl,

[0171] Oxadiazolyl,

[0172] Thiazolyl,

[0173] Isothiazolyl,

[0174] Thiadiazole,

[0175] Pyridyl,

[0176] Pyridazine

[0177] Pyrimidine,

[0178] Pyrazinyl,

[0179] Triazine,

[0180] Indolyl,

[0181] Isoindolyl,

[0182] Indolizinyl,

[0183] Quinolizinyl,

[0184] Quinoline,

[0185] Isoquinolinyl,

[0186] Cinnoline,

[0187] Phthalocyanine

[0188] Quinazoline,

[0189] Quinoxaline,

[0190] Benzimidazolyl,

[0191] Indazolyl,

[0192] Phenanthroline,

[0193] Phenanthridinyl,

[0194] Acridinium,

[0195] Phenazine,

[0196] Carbazolyl,

[0197] Benzocarbazolyl,

[0198] Morpholino,

[0199] Phenoxazine,

[0200] Phenothiazine,

[0201] Azacarbazolyl,

[0202] Diazacarbazolyl

[0203] Unsubstituted heterocyclic groups containing oxygen atoms:

[0204] Furanyl,

[0205] Oxazolyl,

[0206] Isoxazolyl,

[0207] Oxadiazolyl,

[0208] Xanthyl,

[0209] Benzofuranyl,

[0210] Isobenzofuranyl,

[0211] Dibenzofuranyl,

[0212] Naphthobenzofuranyl,

[0213] Benzoxazolyl,

[0214] Benzisoxazolyl,

[0215] Phenoxazine,

[0216] Morpholino,

[0217] dinaphthofuranyl,

[0218] Azadibenzofuranyl,

[0219] Diazadibenzofuranyl,

[0220] Azanaphthobenzofuranyl,

[0221] naphthyridinylbenzofuranyl

[0222] Unsubstituted heterocyclic groups containing a sulfur atom:

[0223] Thienyl,

[0224] Thiazolyl,

[0225] Isothiazolyl,

[0226] Thiadiazole,

[0227] Benzothiphenyl,

[0228] Isobenzothiophene,

[0229] Dibenzothiophene,

[0230] Naphthobenzothiophene,

[0231] Benzothiazolyl,

[0232] Benzisothiazolyl,

[0233] Phenothiazine,

[0234] Dinaphthothienyl,

[0235] Azadibenzothiophene,

[0236] Diazadibenzothiophene,

[0237] Azanaphthobenzothiophene,

[0238] naphthyridinylbenzothiophene

[0239] Substituted heterocyclic groups containing a nitrogen atom:

[0240] (9-phenyl)carbazolyl,

[0241] (9-biphenyl)carbazolyl,

[0242] (9-phenyl)phenylcarbazolyl,

[0243] (9-naphthyl)carbazolyl,

[0244] Diphenylcarbazole-9-yl,

[0245] Phenylcarbazol-9-yl,

[0246] Methylbenzimidazolyl,

[0247] Ethylbenzimidazolyl,

[0248] Phenyl triazine,

[0249] Biphenyl triazine,

[0250] Diphenyltriazine,

[0251] Phenylquinazolinyl,

[0252] Biphenylquinazoline

[0253] Substituted heterocyclic groups containing an oxygen atom:

[0254] Phenyldibenzofuranyl,

[0255] Methyldibenzofuranyl,

[0256] tert-Butyldibenzofuranyl,

[0257] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene]

[0258] Substituted heterocyclic groups containing a sulfur atom:

[0259] Phenyldibenzothiophene,

[0260] Methyldibenzothiophene,

[0261] tert-Butyldibenzothienyl,

[0262] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene]

[0263] A monovalent group consisting of the following unsubstituted heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and a group in which a monovalent group consisting of the following unsubstituted heterocyclic ring has a substituent:

[0264] [Chemistry 4]

[0265]

[0266] In formula (XY-1)~(XY-18), X A and Y A are independently an oxygen atom, a sulfur atom, NH, CH 2 Among them, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0267] The heterocyclic rings represented by the above formulae (XY-1) to (XY-18) have a bonding site at an arbitrary position to form a monovalent heterocyclic group.

[0268] The monovalent group formed by the unsubstituted heterocyclic ring represented by the above formulae (XY-1) to (XY-18) having a substituent means that the hydrogen atom bonded to the carbon atom of the skeleton in these formulae is replaced by a substituent, or X A , Y A NH or CH 2 , these NH or CH 2 The state in which the hydrogen atoms in the molecule are replaced by substituents.

[0269] As specific examples of the "substituted or unsubstituted alkyl group" described in this specification (specific example group G3), the following unsubstituted alkyl groups and substituted alkyl groups can be cited. (Here, unsubstituted alkyl groups refer to the case where "substituted or unsubstituted alkyl groups" are "unsubstituted alkyl groups", and substituted alkyl groups refer to the case where "substituted or unsubstituted alkyl groups" are "substituted alkyl groups".) Hereinafter, when simply referred to as "alkyl groups", both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0270] "Substituted alkyl" refers to the case where "unsubstituted alkyl" has a substituent, and examples of "unsubstituted alkyl" and substituted alkyl groups described below can be cited. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are just examples, and the "substituted alkyl" described in this specification also includes groups such as "unsubstituted alkyl" groups with substituents and further substituents, and "substituted alkyl" groups with further substituents.

[0271] Unsubstituted alkyl:

[0272] methyl,

[0273] Ethyl,

[0274] n-propyl,

[0275] Isopropyl,

[0276] n-Butyl,

[0277] Isobutyl

[0278] sec-butyl,

[0279] Tert-butyl

[0280] Substituted alkyl:

[0281] Heptafluoropropyl (including isomers),

[0282] Pentafluoroethyl,

[0283] 2,2,2-Trifluoroethyl,

[0284] Trifluoromethyl

[0285] As specific examples of the "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl and substituted alkenyl groups can be cited. (Here, unsubstituted alkenyl refers to the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) Hereinafter, when simply referred to as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0286] "Substituted alkenyl" refers to the case where "unsubstituted alkenyl" has a substituent, and examples of "unsubstituted alkenyl" and "substituted alkenyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are just examples, and the "substituted alkenyl" described in this specification also includes groups such as "unsubstituted alkenyl" having a substituent further having a substituent, and "substituted alkenyl" further having a substituent.

[0287] Unsubstituted alkenyl and substituted alkenyl:

[0288] Vinyl,

[0289] Allyl,

[0290] 1-Butenyl,

[0291] 2-Butenyl,

[0292] 3-Butenyl,

[0293] 1,3-Butadienyl,

[0294] 1-Methylvinyl,

[0295] 1-methylallyl,

[0296] 1,1-dimethylallyl,

[0297] 2-methylallyl,

[0298] 1,2-Dimethylallyl

[0299] As specific examples of the "substituted or unsubstituted alkynyl group" described in this specification (specific example group G5), the following unsubstituted alkynyl groups can be cited. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group".) Hereinafter, when simply referred to as an "alkynyl group", both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0300] The "substituted alkynyl group" is a case where the "unsubstituted alkynyl group" has a substituent, and examples thereof include the following groups where the "unsubstituted alkynyl group" has a substituent.

[0301] Unsubstituted alkynyl:

[0302] Ethylene

[0303] As specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6), the following unsubstituted cycloalkyl and substituted cycloalkyl can be cited. (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".) Hereinafter, when simply referred to as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0304] "Substituted cycloalkyl" refers to the case where "unsubstituted cycloalkyl" has a substituent, and examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are just examples, and the "substituted cycloalkyl" described in this specification also includes groups such as "unsubstituted cycloalkyl" having a substituent further having a substituent, and "substituted cycloalkyl" further having a substituent.

[0305] Unsubstituted aliphatic cyclic groups:

[0306] Cyclopropyl,

[0307] Cyclobutyl,

[0308] Cyclopentyl,

[0309] Cyclohexyl,

[0310] 1-adamantyl,

[0311] 2-adamantyl,

[0312] 1-Norborneol,

[0313] 2-Norbornyl

[0314] Substituted cycloalkyl:

[0315] 4-Methylcyclohexyl

[0316] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as follows (specific example group G7):

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

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

[0319] -Si(G1)(G1)(G2)

[0320] -Si(G2)(G2)(G2)

[0321] -Si(G5)(G5)(G5)

[0322] -Si(G6)(G6)(G6).

[0323] Here,

[0324] G1 is the "aryl group" described in Specific Example Group G1.

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

[0326] G3 is the "alkyl group" described in Specific Example Group G3.

[0327] G6 is the "cycloalkyl group" as described in Specific Example Group G6.

[0328] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and include

[0329] -O(G1)

[0330] -O(G2)

[0331] -O(G3)

[0332] -O(G6).

[0333] Here,

[0334] G1 is the "aryl group" described in Specific Example Group G1.

[0335] G2 is the "heterocyclic group" described in Specific Example Group G2.

[0336] G3 is the "alkyl group" described in Specific Example Group G3.

[0337] G6 is the "cycloalkyl group" as described in Specific Example Group G6.

[0338] As described in this specification, -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0339] -S(G1)

[0340] -S(G2)

[0341] -S(G3)

[0342] -S(G6).

[0343] Here,

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

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

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

[0347] G6 is the "cycloalkyl group" as described in Specific Example Group G6.

[0348] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0349] -N(G1)(G1)

[0350] -N(G2)(G2)

[0351] -N(G1)(G2)

[0352] -N(G3)(G3)

[0353] -N(G6)(G6).

[0354] Here,

[0355] G1 is the "aryl group" described in Specific Example Group G1.

[0356] G2 is the "heterocyclic group" described in Specific Example Group G2.

[0357] G3 is the "alkyl group" described in Specific Example Group G3.

[0358] G6 is the "cycloalkyl group" as described in Specific Example Group G6.

[0359] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

[0360] The "alkoxy group" described in this specification is a group represented by -O(G3), where G3 is, for example, an "alkyl group" as described in Specific Example Group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0361] The "alkylthio group" described in this specification is a group represented by -S(G3), where G3 is, for example, the "alkyl group" described in Specific Example Group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0362] The "aryloxy group" described in this specification is a group represented by -O(G1), where G1 is, for example, the "aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0363] The "arylthio group" described in this specification is a group represented by -S(G1), where G1 is, for example, the "aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0364] The "aralkyl" described in this specification is a group represented by -(G3)-(G1), where G3 is, for example, an "alkyl" described in Specific Example Group G3, and G1 is, for example, an "aryl" described in Specific Example Group G1. Therefore, the "aralkyl" is one form of a "substituted alkyl" substituted with an "aryl". Unless otherwise specified in this specification, the "unsubstituted alkyl" substituted with an "unsubstituted aryl", i.e., the "unsubstituted aralkyl", has 7 to 50 carbon atoms, preferably 7 to 30, and more preferably 7 to 18 carbon atoms.

[0365] Specific examples of the “aralkyl” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0366] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, chrysene, triphenylene, fluorenyl, 9,9'-spirobifluorenyl, 9,9-diphenylfluorenyl and the like.

[0367] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group, a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthiobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group, a (9-biphenyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazine group, a biphenyltriazine group, a diphenyltriazine group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group, and the like.

[0368] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group or the like.

[0369] Unless otherwise specified, the term "substituted or unsubstituted arylene group" used herein means that the above-mentioned "aryl group" forms a divalent group. Specific examples of "substituted or unsubstituted arylene group" (specific example group G12) include "aryl groups" described in specific example group G1 forming a divalent group.

[0370] Specific examples of the "substituted or unsubstituted divalent heterocyclic group" described in the present specification (Specific Example Group G13) include "heterocyclic groups" described in Specific Example Group G2 forming divalent groups.

[0371] Specific examples of the "substituted or unsubstituted alkylene group" described in the present specification (specific example group G14) include "alkyl groups" described in specific example group G3 forming a divalent group.

[0372] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any of the following groups.

[0373] [Chemistry 5]

[0374]

[0375] In formula (XY-20)~(XY-29), R 908 As a substituent.

[0376] m901 is an integer from 0 to 4. When m901 is 2 or more, multiple R 908 They may be the same as or different from each other.

[0377] [Chemistry 6]

[0378]

[0379] In formula (XY-30)~(XY-40), R 909 Each R is independently a hydrogen atom or a substituent. 909 They may be bonded to each other via a single bond to form a ring.

[0380] [Chemistry 7]

[0381]

[0382] In formula (XY-41)~(XY-46), R 910 As a substituent.

[0383] m902 is an integer from 0 to 6. When m902 is 2 or more, the multiple R 910 They may be the same as or different from each other.

[0384] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any of the following groups.

[0385] [Chemistry 8]

[0386]

[0387] In formula (XY-50)~(XY-64), R 911 is a hydrogen atom or a substituent.

[0388] [Chemistry 9]

[0389]

[0390] In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.

[0391] The organic electroluminescent element as the first embodiment of the present invention (hereinafter sometimes referred to as the organic EL element of the first embodiment) is an organic electroluminescent element including an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in this order.

[0392] The second electron transport layer contains a compound represented by the following formula (1):

[0393] [Chemistry 10]

[0394]

[0395] The light-emitting layer contains a compound represented by the following formula (10).

[0396] [Chemistry 11]

[0397]

[0398] Each substituent in the above formula (1) and formula (10) is described below.

[0399] The organic EL element of the first mode comprises an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in sequence, wherein the second electron transport layer contains a compound of the above formula (1), and the light-emitting layer contains a compound of the above formula (10), thereby obtaining a high-performance organic electroluminescent element. In particular, an organic electroluminescent element with high luminous efficiency, an organic electroluminescent element with a long life, and an organic electroluminescent element with high luminous efficiency and long life can be obtained. It is speculated that this effect is obtained by improving the carrier balance factor due to this composition.

[0400] The first electron transport layer may or may not be directly adjacent to the light-emitting layer, but is preferably directly adjacent to the light-emitting layer.

[0401] The first electron transport layer and the second electron transport layer may or may not be directly adjacent to each other, but are preferably directly adjacent to each other.

[0402] When the light-emitting layer and the first electron transport layer, or the first electron transport layer and the second electron transport layer are not adjacent to each other, a third electron transport layer or the like may be provided between the layers.

[0403] The second electron transport layer may be directly adjacent to the cathode or may not be adjacent to the cathode. When the second electron transport layer is not adjacent to the cathode, other layers may be provided between the second electron transport layer and the cathode. The other layers provided between the second electron transport layer and the cathode are preferably electron injection layers. An electron injection layer is preferably provided between the second electron transport layer and the cathode. The electron injection layer material is described below.

[0404] In addition, an organic layer is preferably provided between the anode and the light-emitting layer. The organic layer between the anode and the light-emitting layer is preferably a hole injection layer, a hole transport layer, etc. The materials of the hole injection layer and the hole transport layer are described below.

[0405] Next, the compound represented by formula (1) is described.

[0406] [Chemistry 12]

[0407]

[0408] [In formula (1),

[0409] FA is a substituted or unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings.

[0410] L 1 is a single bond, or is selected from

[0411] Substituted or unsubstituted phenylene,

[0412] Substituted or unsubstituted biphenylene,

[0413] Substituted or unsubstituted terphenylene,

[0414] Substituted or unsubstituted quaterphenylene,

[0415] an arylene group containing a substituted or unsubstituted condensed ring having 10 to 30 ring carbon atoms, and

[0416] A group formed by linking 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted arylene groups containing a condensed ring having 10 to 30 ring carbon atoms via a single bond.

[0417] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.

[0418] X 1 ~X 3 Each independently is N or CR 1 Among them, X 1 ~X 3 Two or more of them are N. 1 Not adjacent to L 1 ,Ar 1 or Ar 2 The bonds form a ring.

[0419] R 1 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.]

[0420] In one embodiment, L in the above formula (1) 1 The arylene group is a divalent group formed by bonding two or more monocyclic rings by a single bond, a divalent group formed by bonding two or more condensed rings by a single bond, or a divalent group formed by bonding one or more monocyclic rings and one or more condensed rings by a single bond. For example, biphenylene as a divalent group containing two monocyclic rings, a group of a combination of phenylene and naphthylene as shown below as a divalent group containing one or more monocyclic rings and one or more condensed rings, etc. can be cited.

[0421] [Chemistry 13]

[0422] .

[0423] In one embodiment, FA in the above formula (1) is

[0424] an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings,

[0425] An aryl group having 13 to 50 ring carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0426] An aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, which is substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.

[0427] In one embodiment, FA is

[0428] An unsubstituted aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0429] In one embodiment, FA is a group selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysyl, and substituted or unsubstituted benzochrysyl.

[0430] Preferably, FA is a group selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted benzochrysyl. More preferably, FA is a group selected from 9-anthryl, 10-phenylanthracen-9-yl, 10-biphenylanthracen-9-yl, 10-terphenylanthracen-9-yl, 10-naphthylanthracen-9-yl, 9,10-diphenylanthracen-2-yl, 9,10-dinaphthylanthracen-2-yl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, 9-phenanthryl, benzochrysyl, triphenyl, fluoranthenyl, benzo[c]phenanthryl, benzo[a]phenanthryl, benzo[a]anthryl, and pyrenyl. More preferably, FA is a group selected from 9,9-diphenylfluoren-2-yl, 9,9-diphenylfluoren-4-yl, 10-naphthylanthracene-9-yl, 10-biphenylanthracene-9-yl, 9,10-diphenylanthracene-2-yl, and a group represented by the following formula.

[0431] [Chemistry 14]

[0432] .

[0433] In one embodiment, L in the above formula (1) 1 is a single bond, or is selected from

[0434] Substituted or unsubstituted phenylene,

[0435] Substituted or unsubstituted biphenylene, and

[0436] a substituted or unsubstituted naphthylene group,

[0437] L 1 When there is a substituent, the substituent is

[0438] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0439] A substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms (except carbazolyl).

[0440] In one embodiment, L 1 is a single bond or a group selected from divalent groups represented by the following formulae (a1) to (a3).

[0441] [Chemistry 15]

[0442] .

[0443] In one embodiment, L 1 is a single bond or a divalent group selected from the following formulae (a1-1) to (a1-3). The following formulae (a1-1) to (a1-3) more specifically represent the above formula (a1).

[0444] [Chemistry 16]

[0445] .

[0446] The above formulae (a2) and (a3) ​​are more specifically represented below as formulae (a2-1) to (a2-9) and formulae (a3-1) to (a3-6).

[0447] [Chemistry 17]

[0448]

[0449] [Chemistry 18]

[0450] .

[0451] In one embodiment, L 1 is a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. 1 The substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms is specifically a divalent group represented by the following formulae (aa1) to (aa3).

[0452] [Chemistry 19]

[0453]

[0454] In formula (aa1)~(aa3),

[0455] R 2 As a substituent.

[0456] n1 is an integer from 0 to 4, and n2 is an integer from 0 to 6.

[0457] When n1 and n2 are 2 or more, multiple R 2 The multiple R substituted on adjacent carbon atoms may be the same or different. 2 They are not bonded to each other to form a ring.

[0458] In the above formulas (aa1) to (aa3), R 2 The benzene ring or the naphthalene ring is bonded to any bondable position. The same applies to the following.

[0459] In one embodiment, L 1 for

[0460] unsubstituted arylene group having 6 to 12 ring carbon atoms,

[0461] an arylene group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0462] An arylene group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.

[0463] In one embodiment, as L 1 When the group has a substituent, particularly preferred substituents include a phenyl group, and an azine group such as a pyridyl group, a pyrimidyl group, and a triazine group.

[0464] In one embodiment, Ar in the above formula (1) 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.

[0465] In one embodiment, Ar 1 and Ar 2 The substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms preferably includes a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and an azinyl group such as a substituted or unsubstituted triazinyl group.

[0466] In one embodiment, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0467] In one embodiment, Ar 1 and Ar 2 Each independently represents a group selected from the monovalent groups represented by the following formulae (b1) to (b3).

[0468] [Chemistry 20]

[0469]

[0470] [In formulas (b1) to (b3),

[0471] R 5 are each independently a substituent.

[0472] p is an integer from 0 to 5.

[0473] q is an integer from 0 to 7.

[0474] m is an integer from 0 to 4.

[0475] When p, q or m is 2 or more, multiple R 5 They may be the same or different from each other. When p, q or m is 2 or more, the multiple R 5 They are not bonded to each other to form a ring.]

[0476] In the above formulas (b1) to (b3), R 5 The benzene ring or the naphthalene ring is bonded to any bondable position. The same applies to the following.

[0477] In one embodiment, Ar 1 and Ar 2 Each independently represents a group selected from the monovalent groups represented by the following formulae (b1-1) and (b3-1) to (b3-3).

[0478] [Chemistry 21]

[0479]

[0480] [In formulas (b1-1) and (b3-1) to (b3-3),

[0481] R 5 are each independently a substituent.

[0482] p is an integer from 0 to 5.

[0483] m is an integer from 0 to 4.

[0484] When p or m is 2 or more, multiple R 5 They may be the same or different from each other. When p or m is 2 or more, multiple R 5 They are not bonded to each other to form a ring. )]

[0485] In one embodiment, X in the above formula (1) 1 ~X 3 is N.

[0486] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (2).

[0487] [Chemistry 22]

[0488]

[0489] [In formula (2),

[0490] FAa for

[0491] an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings,

[0492] An aryl group having 13 to 50 ring carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0493] An aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms (excluding substituted or unsubstituted carbazolyl).

[0494] L 1a for

[0495] single bond,

[0496] unsubstituted arylene group having 6 to 12 ring carbon atoms,

[0497] an arylene group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0498] An arylene group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms (excluding a substituted or unsubstituted carbazolyl group).

[0499] Ar 1a and Ar 2a Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. ].

[0500] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (2-1).

[0501] [Chemistry 23]

[0502]

[0503] [In formula (2-1),

[0504] FA a for

[0505] an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings,

[0506] An aryl group having 13 to 50 ring carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0507] An aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms (excluding substituted or unsubstituted carbazolyl).

[0508] L 1a’ It is a single bond or an unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0509] Ar 1a and Ar 2a Each is independently a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.]

[0510] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (3).

[0511] [Chemistry 24]

[0512]

[0513] [In formula (3),

[0514] FA a for

[0515] an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings,

[0516] An aryl group having 13 to 50 ring carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0517] An aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms (excluding substituted or unsubstituted carbazolyl).

[0518] L 1b is a single bond or a group selected from divalent groups represented by the following formulae (a1) to (a3).

[0519] [Chemistry 25]

[0520]

[0521] The two unspecified bonding sites in the above formula (a2) are bonded to any two positions of the naphthalene ring. The unspecified bonding site in (a3) ​​is bonded to any bondable position of the benzene ring.

[0522] Ar 1b and Ar 2b Each independently represents a group selected from the monovalent groups represented by the following formulae (b1) to (b3).

[0523] [Chemistry 26]

[0524]

[0525] (In formulas (b1) to (b3),

[0526] R 5 are each independently a substituent.

[0527] p is an integer from 0 to 5.

[0528] q is an integer from 0 to 7.

[0529] m is an integer from 0 to 4.

[0530] When p, q or m is 2 or more, multiple R 5 They may be the same or different from each other. When p, q or m is 2 or more, the multiple R 5 They are not bonded to each other to form a ring. )]

[0531] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (4).

[0532] [Chemistry 27]

[0533]

[0534] [In formula (4),

[0535] FA c is a group selected from a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysyl group, and a substituted or unsubstituted benzochrysyl group.

[0536] L 1c It is a single bond or a divalent group selected from the following formulae (a1-1) to (a1-3).

[0537] [Chemistry 28]

[0538]

[0539] Ar 1c and Ar 2c Each independently represents a group selected from the monovalent groups represented by the following formulae (b1-1) and (b3-1) to (b3-3).

[0540] [Chemistry 29]

[0541]

[0542] (In formulas (b1-1) and (b3-1) to (b3-3),

[0543] R 5 are each independently a substituent.

[0544] p is an integer from 0 to 5.

[0545] m is an integer from 0 to 4.

[0546] When p or m is 2 or more, multiple R 5 They may be the same or different from each other. When p or m is 2 or more, multiple R 5 They are not bonded to each other to form a ring. )]

[0547] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (5).

[0548] [Chemistry 30]

[0549]

[0550] [In formula (5), FA, L 1 and X 1 ~X 3 The same as the above formula (1).

[0551] R 6 Each is independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.

[0552] r is an integer of 0 to 5 independently. When r is 2 to 5, multiple R 6 They may be the same or different. 6 When there are multiple R 6 They are not bonded to each other to form a ring.]

[0553] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (6).

[0554] [Chemistry 31]

[0555]

[0556] [In formula (6), X 1 ~X 3 As defined in formula (1) above.

[0557] FA a for

[0558] an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings,

[0559] An aryl group having 13 to 50 ring carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0560] An aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, which is substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.

[0561] L 1d for

[0562] single bond,

[0563] unsubstituted arylene group having 6 to 12 ring carbon atoms,

[0564] an arylene group having 6 to 12 ring carbon atoms substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0565] An arylene group having 6 to 12 ring carbon atoms substituted with an unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.

[0566] Ar 1d and Ar 2d Each independently

[0567] unsubstituted aryl group having 6 to 12 ring carbon atoms,

[0568] an unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms,

[0569] an aryl group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0570] an aryl group having 6 to 12 ring carbon atoms substituted with a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms,

[0571] a monovalent heterocyclic group having 5 to 12 ring atoms substituted with a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0572] A monovalent heterocyclic group having 5 to 12 ring atoms substituted by a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms.]

[0573] In one embodiment, the substituent referred to as "substituted or unsubstituted" as R 2 and R 5 The substituents are selected from

[0574] Alkyl groups having 1 to 50 carbon atoms,

[0575] Alkenyl having 2 to 50 carbon atoms,

[0576] Alkynyl having 2 to 50 carbon atoms,

[0577] Cycloalkyl having 3 to 50 ring carbon atoms,

[0578] Alkoxy having 1 to 50 carbon atoms,

[0579] Alkylthio having 1 to 50 carbon atoms,

[0580] an aryloxy group having 6 to 50 ring carbon atoms,

[0581] an arylthio group having 6 to 50 ring carbon atoms,

[0582] Aralkyl having 7 to 50 carbon atoms,

[0583] -Si(R 41 )(R 42 )(R 43 ),

[0584] -C(=O)R 44 ,

[0585] -COOR 45 ,

[0586] -S(=O) 2 R 46 ,

[0587] -P(=O)(R 47 )(R 48 ),

[0588] -Ge(R 49 )(R 50 )(R 51 ),

[0589] -N(R 52 )(R 53 )(Here, R 41 ~R 53 Each independently represents a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms (except carbazolyl). 41 ~R 53 When there are 2 or more, 2 or more R 41 ~R 53 Each may be the same or different. ), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms (except for carbazolyl).

[0590] In one embodiment, the substituent referred to as "substituted or unsubstituted" as R 2 and R 5 The substituents are alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 12 ring carbon atoms, and monovalent heterocyclic groups having 5 to 12 ring atoms.

[0591] Specific examples of the compound represented by the above formula (1) are described below, but the compound is not limited to these.

[0592] [Chemistry 32]

[0593]

[0594] [Chemistry 33]

[0595]

[0596] [Chemistry 34]

[0597]

[0598] [Chemistry 35]

[0599]

[0600] [Chemistry 36]

[0601]

[0602] [Chemistry 37]

[0603]

[0604] Next, the compound represented by the following formula (10) is described.

[0605] [Chemistry 38]

[0606]

[0607] [In formula (10),

[0608] R 11 ~R 18 are each independently a hydrogen atom,

[0609] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0610] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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

[0612] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0613] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0614] a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,

[0615] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0616] a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,

[0617] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0618] -Si(R 101 )(R 102 )(R 103 ),

[0619] -C(=O)R 104 ,

[0620] -COOR 105 ,

[0621] -N(R 106 )(R 107 ),

[0622] Halogen atoms, cyano, nitro,

[0623] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0624] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0625] R 101 ~R 107 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0626] R 101 ~R 107 When there are two or more, two or more R 101 ~R 107 They can be the same or different.

[0627] Ar 11 and Ar 12 At least one of them is a monovalent group represented by the following formula (11).

[0628] [Chemistry 39]

[0629]

[0630] (In formula (11),

[0631] R 21 ~R 28 One of them is the same as L 11 or L 12 Bonded bonding sites,

[0632] Not with L 11 or L 12 Bonded bonding position R 21 ~R 28 Each is independently a hydrogen atom,

[0633] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0634] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0635] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0636] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0637] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0638] a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,

[0639] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0640] a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,

[0641] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0642] -Si(R 101 )(R 102 )(R 103 ),

[0643] -C(=O)R 104 ,

[0644] -COOR 105 ,

[0645] -N(R 106 )(R 107 ),

[0646] Halogen atoms, cyano, nitro,

[0647] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0648] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0649] R 101 ~R 107 As described above.)

[0650] Ar which is not a monovalent group represented by the above formula (11) 11 or Ar 12 It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted by an unsubstituted alkyl group having 1 to 50 ring carbon atoms, or an aryl group having 6 to 50 ring carbon atoms substituted by an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0651] L 11 and L 12 Each is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, 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.].

[0652] In one embodiment, the compound represented by the above formula (10) is a compound represented by the following formula (10-1).

[0653] [Chemistry 40]

[0654]

[0655] [In formula (10-1), R 11 ~R 18 ,Ar 11 , L 11 , L 12 , R 21 and R 23 ~R 28 As defined in the above formula (10). ].

[0656] In one embodiment, the compound represented by the above formula (10) is a compound represented by the following formula (10-2).

[0657] [Chemistry 41]

[0658]

[0659] [In formula (10-2), L 11 is a single bond, R 11 ~R 18 ,Ar 11 , L 12 , and R 21 ~R 28 As defined above in formula (10).]

[0660] In one embodiment, the compound represented by the above formula (10) is a compound represented by the following formula (10-3).

[0661] [Chemistry 42]

[0662]

[0663] [In formula (10-3), L 11 is a single bond, R 11 ~R 18 ,Ar 11 , L 12 , R 21 and R 23 ~R 28 As defined in the above formula (10). ].

[0664] In one embodiment, in the above formulas (10), (10-1), (10-2) and (10-3), L 11 Bonded bonding position R 21 ~R 28 A hydrogen atom.

[0665] In one embodiment, in the above formulas (10), (10-1), (10-2) and (10-3), R 11 ~R 18 A hydrogen atom.

[0666] In one embodiment, the compound represented by the above formula (10) is a compound represented by the following formula (10-4).

[0667] [Chemistry 43]

[0668]

[0669] [In formula (10-4), L 11 is a single bond, Ar 11 and L 12 As defined in formula (1) above.]

[0670] In one embodiment, the substituents referred to as "substituted or unsubstituted" in the above formulae (10), (10-1), (10-2), (10-3) and (10-4) are selected from an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43)、-C(=O)R 44 、-COOR 45 、-S(=O) 2 R 46 、-P(=O)(R 47 )(R 48 )、-Ge(R 49 )(R 50 )(R 51 )、-N(R 52 )(R 53 )(Here, R 41 ~R 53 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. 41 ~R 53 When there are 2 or more, 2 or more R 41 ~R 53 Each of them may be the same or different. ), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0671] In one embodiment, the substituent referred to as "substituted or unsubstituted" in the above formulas (10), (10-1), (10-2), (10-3) and (10-4) is 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.

[0672] In one embodiment, the substituent referred to as "substituted or unsubstituted" in the above formulas (10), (10-1), (10-2), (10-3) and (10-4) is 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.

[0673] Specific examples of the compound represented by the above formula (10) are described below, but the compound is not limited to these.

[0674] [Chemistry 44]

[0675]

[0676] [Chemistry 45]

[0677]

[0678] [Chemistry 46]

[0679] .

[0680] In one embodiment, the second electron transport layer further contains one or more selected from alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals. Among the above compounds, organic complexes containing alkali metals are preferred, and Liq (8-hydroxyquinoline-lithium) is particularly preferred.

[0681] In one embodiment, the first electron transport layer includes a compound represented by the following formula (30).

[0682] [Chemistry 47]

[0683]

[0684] In formula (30),

[0685] X 11 is a nitrogen atom, CH or CR 83 .

[0686] X 11 CR 83 When R 82 ~R 84 Two adjacent ones of the rings may be bonded to each other to form, together with the two ring carbon atoms to which they are bonded, a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 32 ring atoms.

[0687] R 81 , R that does not form the above ring 82 ~R 84 Each is independently a group represented by any one of the following formulae (31) to (34).

[0688] [Chemistry 48]

[0689]

[0690] (In formulas (31) to (34),

[0691] L 31 , L 33 , L 36 , L 38 and L 39 Each is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms.

[0692] L 32 , L 34 and L35 Each is independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 32 ring atoms.

[0693] L 37 It is a substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group having 5 to 32 ring atoms.)]

[0694] In one embodiment, the compound represented by the above formula (30) is a compound represented by the following formula (30a) or a compound represented by the following formula (30b). 11 is N or CH.

[0695] [Chemistry 49]

[0696]

[0697] (In formulas (30a) and (30b), R 81 , R 82 and R 84 As defined in the above formula (30).

[0698] In one embodiment, the compound represented by the above formula (30) is a compound represented by the following formula (30c). 11 CR 83 .

[0699] [Chemistry 50]

[0700]

[0701] (In formula (30c), R 81 ~R 84 As defined in the above formula (30).

[0702] R 82 ~R 84 The two adjacent bonds in the 82 With R 83 , or R 83 With R 84 Mutual bonding situation.

[0703] In one embodiment, R 82 ~R 84 When two adjacent rings in the formula (R) are bonded to each other to form an aromatic hydrocarbon ring having 10 to 30 ring carbon atoms or a heterocyclic ring having 5 to 32 ring atoms, 82 ~R 84 The structure formed by two adjacent ones of the above-mentioned groups being bonded to each other is selected from the following group. The following structure may have a substituent.

[0704] [Chemistry 51]

[0705]

[0706] (In the above formula, * represents R 82 With R 83 , or R 83 With R 84 bonding position. ).

[0707] In one embodiment, R 82 ~R 84 The structure formed by two adjacent ones of the above-mentioned groups being bonded to each other is selected from the following group. The following structure may have a substituent.

[0708] [Chemistry 52]

[0709]

[0710] (In the above formula, * represents R 82 With R 83 , or R 83 With R 84 bonding position. ).

[0711] In one embodiment, L in formulas (31) to (34) 31 ~L 39 The substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms are substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, respectively.

[0712] As L in the above formulas (31) to (34), 31 ~L 39 Specific examples of the aromatic hydrocarbon ring having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, arylene group and trivalent aromatic hydrocarbon ring group include benzene, biphenyl, terphenyl (including isomers), quaterphenyl (including isomers), naphthalene, fluorene, acenaphthylene, anthracene, benzanthracene, aceanthrene, phenanthrene, triphenylene, phenalene, pentacene, chrysene, pentaphenylene, pyrene, chrysene, benzochrysene, s-indene, as-indene, fluoranthene, benzofluoranthene, perylene, triphenylene, benzotriphenylene, spirofluorene and the like. The above rings may have a substituent.

[0713] In one embodiment, L 31 ~L 39 The aromatic hydrocarbon ring having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group is selected from the following group. The following rings may have a substituent.

[0714] [Chemistry 53]

[0715]

[0716] As L 31 , L 33 , L 36 , L 38 and L 39 Specific examples of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms include a monovalent residue obtained by removing one hydrogen atom from the above aromatic hydrocarbon ring, and the monovalent residue may have a substituent.

[0717] In one embodiment, L 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the substituted or unsubstituted aryl group is a monovalent residue obtained by removing one hydrogen atom from a ring carbon of an aromatic hydrocarbon ring selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthrene, substituted or unsubstituted anthracene, substituted or unsubstituted triphenylene, substituted or unsubstituted benzochrysene, substituted or unsubstituted fluoranthene, substituted or unsubstituted pyrene, substituted or unsubstituted spirofluorene, substituted or unsubstituted 9,9-diphenylfluorene, and substituted or unsubstituted 9,9-dimethylfluorene. The monovalent residue may have a substituent.

[0718] In one embodiment, L 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in is selected from the following group. The following groups may have a substituent.

[0719] [Chemistry 54]

[0720]

[0721] As L 32 , L 34 and L 35 Specific examples of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms include a divalent residue obtained by removing one hydrogen atom from each of two ring carbon atoms of the above aromatic hydrocarbon ring. The divalent residue may have a substituent.

[0722] In one embodiment, L 32 , L 34 and L 35The substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms in the divalent residue obtained by removing one hydrogen atom from each of two ring carbon atoms of an aromatic hydrocarbon ring selected from substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirofluorene, and substituted or unsubstituted anthracene.

[0723] In one embodiment, the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms is selected from the following group: The following divalent group may have a substituent.

[0724] [Chemistry 55]

[0725]

[0726] As L 37 Specific examples of the substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms include trivalent residues obtained by removing one hydrogen atom from each of the three ring carbon atoms of the aromatic hydrocarbon ring. The trivalent residue may have a substituent.

[0727] In one embodiment, L 37 The substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms is a trivalent residue obtained by removing one hydrogen atom from each of three ring carbon atoms of an aromatic hydrocarbon ring selected from substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and substituted or unsubstituted anthracene.

[0728] In one embodiment, L 37 The substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms is a trivalent residue of substituted or unsubstituted benzene.

[0729] In one embodiment, L 37 The substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms in is benzene-1,3,5-triyl. The trivalent group may have a substituent.

[0730] In one embodiment, L in formulas (31) to (34) 31 ~L 39 The substituted or unsubstituted monovalent to trivalent heterocyclic group having 5 to 32 ring atoms is a monovalent to trivalent residue obtained by removing one hydrogen atom from each of 1 to 3 ring atoms having 5 to 32 ring atoms.

[0731] In one embodiment, L in formulas (31) to (34) 31 ~L 39The substituted or unsubstituted 1- to 3-valent heterocyclic group having 5 to 32 ring atoms is a substituted or unsubstituted 1- to 3-valent heterocyclic group having 5 to 18 ring atoms.

[0732] In one embodiment, L 31 ~L 39 The substituted or unsubstituted monovalent to trivalent heterocyclic group having 5 to 32 ring atoms contains 1 to 5, 1 to 3 or 1 to 2 ring heteroatoms such as nitrogen atoms, sulfur atoms and oxygen atoms.

[0733] As L in the above formulas (31) to (34), 31 ~L 39 Specific examples of the heterocyclic ring having 5 to 32 ring atoms of the substituted or unsubstituted monovalent to trivalent heterocyclic group having 5 to 32 ring atoms include pyrrole, imidazole, imidazoline, pyrazole, triazole, furan, thiophene, thiazole, isothiazole, oxazole, isoxazole, oxadiazole, thiadiazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, bipyrrole, terpyrrole, bithiophene, terthiophene, bipyridine, terpyridine, indole, isoindole, benzene The heterocyclic rings include benzofuran, isobenzofuran, benzothiophene, indolizine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, indazole, benzisoxazole, benzisothiazole, benzofuran, dibenzofuran, naphthiobenzofuran, benzothiophene, dibenzothiophene, naphthiobenzothiophene, carbazole, benzocarbazole, phenanthridine, acridine, phenanthroline, phenazine, phenothiazine, phenoxazine, and xanthene. The above heterocyclic rings may have a substituent.

[0734] In one embodiment, L 31 ~L 39 The heterocyclic ring having 5 to 32 ring atoms of the substituted or unsubstituted monovalent to trivalent heterocyclic group having 5 to 32 ring atoms is selected from the following group. The following ring may have a substituent.

[0735] [Chemistry 56]

[0736]

[0737] As L 31 , L 33 , L 36 , L 38 and L 39 Specific examples of the substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms include a monovalent residue obtained by removing one hydrogen atom from one ring atom of the above heterocyclic ring. The monovalent residue may have a substituent.

[0738] In one embodiment, L 31 , L 33 , L 36 , L 38and L 39 The substituted or unsubstituted monovalent heteroatom group having 5 to 32 ring atoms in the substituted or unsubstituted group is a monovalent residue obtained by removing one hydrogen atom from a ring atom of a heterocyclic ring selected from substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted bipyridine, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted phenanthroline, and substituted or unsubstituted quinoline.

[0739] In one embodiment, L 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms in the group is selected from the following group. The following groups may have a substituent.

[0740] [Chemistry 57]

[0741]

[0742] As L 32 , L 34 and L 35 Specific examples of the substituted or unsubstituted divalent heteroatom group having 5 to 32 ring atoms include a divalent residue obtained by removing one hydrogen atom from each of two ring atoms of the heterocycle. The divalent residue may have a substituent.

[0743] In one embodiment, L 32 , L 34 and L 35The substituted or unsubstituted divalent heterocyclic group having 5 to 32 ring atoms is selected from substituted or unsubstituted indole, substituted or unsubstituted isoindole, substituted or unsubstituted benzofuran, substituted or unsubstituted isobenzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted indolizine, substituted or unsubstituted quinolizine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted cinnoline, substituted or unsubstituted phthalazine, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzisothiazole, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted naphthobenzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted carbazole, substituted or unsubstituted benzocarbazole, substituted or unsubstituted phenanthridine, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline, substituted or unsubstituted phenazine, substituted or unsubstituted phenothiazine, substituted or unsubstituted phenoxazine, and a divalent residue obtained by removing one hydrogen atom from each of two ring atoms of the heterocyclic ring in substituted or unsubstituted xanthene.

[0744] In one embodiment, L 32 , L 34 and L 35 The substituted or unsubstituted divalent heterocyclic group having 5 to 32 ring atoms is a divalent residue obtained by removing one hydrogen atom from each of two ring atoms of a heterocyclic ring selected from substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazole.

[0745] In one embodiment, L 32 , L 34 and L 35 The substituted or unsubstituted divalent heterocyclic group having 5 to 32 ring atoms in is a divalent residue obtained by removing one hydrogen atom from each of two ring atoms selected from substituted or unsubstituted pyridine and substituted or unsubstituted carbazole.

[0746] As L 37 Specific examples of the substituted or unsubstituted trivalent heterocyclic group having 5 to 32 ring atoms include trivalent residues obtained by removing one hydrogen atom from each of the three ring atoms of the heterocyclic ring. The trivalent residue may have a substituent.

[0747] In one embodiment, L 37The substituted or unsubstituted trivalent heterocyclic group having 5 to 32 ring atoms is a trivalent residue obtained by removing one hydrogen atom from each of three ring atoms of a heterocyclic ring selected from substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuran, and substituted or unsubstituted benzothiophene.

[0748] Specific examples of the compound represented by the above formula (30) are described below, but the compound is not limited to these.

[0749] [Chemistry 58]

[0750]

[0751] [Chemistry 59]

[0752]

[0753] [Chemistry 60]

[0754]

[0755] [Chemistry 61]

[0756]

[0757] [Chemistry 62]

[0758]

[0759] [Chemistry 63]

[0760]

[0761] The organic EL device of the first embodiment comprises at least anode / light-emitting layer / first electron transport layer / second electron transport layer / cathode, wherein the light-emitting layer contains the compound (10) and the second electron transport layer contains the compound (1).

[0762] When a light-emitting layer containing compound (10), a first electron transport layer, and a second electron transport layer containing compound (1) are provided, other layers may be provided between the light-emitting layer and the cathode, and one or more layers may be provided between the light-emitting layer and the anode.

[0763] Figure 1 A schematic configuration of an embodiment of an organic EL element according to a first aspect is shown.

[0764] The organic EL element 1 includes a first electron transport layer 7 and a second electron transport layer 8 as the substrate 2 , the anode 3 , the light-emitting layer 5 , and the organic layer 6 located between the light-emitting layer 5 and the cathode 10 .

[0765] The organic layer 6 located between the cathode 10 and the light-emitting layer 5 functions as an electron injection and transport layer.

[0766] The organic EL element 1 may include an organic layer 4 between the anode 3 and the light-emitting layer 5. The organic layer 4 functions as a hole injection / transport layer.

[0767] Here, the term “electron injection / transport layer” refers to “at least one of an electron injection layer and an electron transport layer”, and the term “hole injection / transport layer” refers to “at least one of a hole injection layer and a hole transport layer”.

[0768] Furthermore, an electron barrier layer is provided on the anode 3 side of the light-emitting layer 5 , and a hole barrier layer is provided on the cathode 4 side of the light-emitting layer 5 .

[0769] Thus, electrons and holes are confined in the light-emitting layer 5 , and the probability of generating excitons in the light-emitting layer 5 can be increased.

[0770] Figure 1 In the embodiment, two layers of the first electron transport layer 7 and the second electron transport layer 8 are depicted between the cathode 10 and the light-emitting layer 5, but there may be three or more organic layers. When there are three or more organic layers, the compound represented by the above formula (1) is contained in the organic layer closest to the cathode 10.

[0771] Furthermore, a layer other than the organic layer may be provided between the second electron transport layer 8 and the cathode 10. Examples of the layer other than the organic layer include inorganic layers such as LiF and Yb.

[0772] In one embodiment, the organic electroluminescent element includes at least one organic layer between the anode and the light-emitting layer.

[0773] In one embodiment, at least one layer of the organic layer 4 (hole injection / transport layer) located between the anode 3 and the light-emitting layer 5 contains a compound represented by the following formula (20).

[0774] [Chemistry 64]

[0775]

[0776] [In formula (20),

[0777] R 31 ~R 38 Two or more adjacent groups may form a substituted or unsubstituted saturated or unsaturated ring, and R not participating in the ring formation 31 ~R 38 are each independently a hydrogen atom,

[0778] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0779] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0780] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0781] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0782] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0783] a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,

[0784] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0785] a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,

[0786] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0787] -Si(R 201 )(R 202 )(R 203 ),

[0788] -C(=O)R 204 ,

[0789] -COOR 205 ,

[0790] Halogen atoms, cyano, nitro,

[0791] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0792] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0793] R 201 ~R 205 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0794] R 201 ~R 205 When there are 2 or more, 2 or more R 201 ~R 205 They can be the same or different.

[0795] L 21 ~L 24Each is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, 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.

[0796] Ar 21 and Ar 22 Each is 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. ].

[0797] In compound (20), L 23 and L 24 The position relationship on the benzene ring to which the bond is attached may be any of the ortho position (o), meta position (m) or para position (p). The ortho position or meta position is preferred, and the meta position is particularly preferred.

[0798] Here, for the compound represented by formula (20), “R 31 ~R 38 One or more groups of two or more adjacent rings may form a substituted or unsubstituted saturated or unsaturated ring."

[0799] “R 31 ~R 38 "a group of two or more adjacent groups" is, for example, R 31 With R 32 , R 32 With R 33 , R 33 With R 34 , R 34 With R 35 , R 35 With R 36 , R 36 With R 37 , R 37 With R 38 , R 31 , R 32 With R 33 , R 32 , R 33 With R 34 And other combinations.

[0800] The "substituted or unsubstituted" substituent on the saturated or unsaturated ring is as described later with respect to the formula (20).

[0801] "Saturated or unsaturated ring" refers to, for example, R 31 With R 32 When forming a ring, R 31 The carbon atom to which it is bonded, R 32 The carbon atom to which the bond is attached forms a ring with one or more arbitrary elements. Specifically, R31 With R 32 When forming a ring, R 31 The carbon atom to which it is bonded, R 32 When the carbon atom to which it is bonded forms an unsaturated ring with four carbon atoms, R 31 With R 32 The ring formed is a benzene ring.

[0802] The "arbitrary element" is preferably a C element, an N element, an O element, or an S element. In the case of an arbitrary element (for example, a C element or an N element), a bonding position not involved in ring formation may be terminated with a hydrogen atom or the like.

[0803] The “one or more arbitrary elements” are preferably two or more and fifteen or less, more preferably three or more and twelve or less, and still more preferably three or more and five or less arbitrary elements.

[0804] R 32 , R 33 With R 34 When one group of R forms a ring, the compound represented by formula (20) is, for example, a compound represented by the following formula (20-10). 61 When it is phenyl, R 32 , R 33 With R 34 1 group forms a substituted ring.

[0805] [Chemistry 65]

[0806]

[0807] [In formula (20-10), R 31 , R 35 ~R 38 , L 21 ~L 24 ,Ar 21 and Ar 22 As defined in the above formula (20), R 61 ~R 66 The substituent referred to as "substituted or unsubstituted" in the compound (20) described later (the optional substituent of the compound (20)) has the same meaning as that of the substituent referred to as "substituted or unsubstituted" in the compound (20) described later.].

[0808] "One or more groups" means that, for example, 31 With R 32 While forming a ring R 37 With R 38 In this case, the compound represented by formula (20) is, for example, a compound represented by the following formula (20-11). In the following formula (20-11), for example, R 71 When it is phenyl, R 31 With R32 A substituted ring is formed.

[0809] [Chemistry 66]

[0810]

[0811] [In formula (20-11), R 33 ~R 36 , L 21 ~L 24 ,Ar 21 and Ar 22 As defined in the above formula (20), R 71 ~R 78 The substituent referred to as "substituted or unsubstituted" in the compound (2) described later (the optional substituent of the compound (2)) has the same meaning as that of the substituent referred to as "substituted or unsubstituted" in the compound (2) described later.]

[0812] In one embodiment, compound (20) preferably includes either or both of a compound represented by the following formula (20a) and a compound represented by the following formula (20b) (hereinafter referred to as compounds (20a) and (20b)).

[0813] [Chemistry 67]

[0814]

[0815] [In formulas (20a) and (20b), R 31 ~R 38 , L 21 ~L 24 ,Ar 21 and Ar 22 As defined in formula (20) above. ].

[0816] In one embodiment, compound (20) is preferably compound (20a), that is, L 23 With L 24 They replace each other at the meta position of the benzene ring.

[0817] In one embodiment, L in compound (20) 24 Preferred is a single bond.

[0818] In one embodiment, L in compound (20) 23 Preferred is a single bond.

[0819] In one embodiment, it is preferred that Ar in compound (20) 21 and Ar 22 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0820] In one embodiment, R in compound (20) 31 ~R 38 Preferred is a hydrogen atom.

[0821] In one embodiment, compound (20) is a compound represented by the following formula (20a-1) and / or the following formula (20b-1).

[0822] [Chemistry 68]

[0823]

[0824] [In formulas (20a-1) and (20b-1), L 24 is a single bond, R 31 ~R 38 , L 21 ~L 23 ,Ar 21 and Ar 22 As defined in formula (20) above. ].

[0825] In one embodiment, compound (20) is a compound represented by the following formula (20a-2) and / or the following formula (20b-2).

[0826] [Chemistry 69]

[0827]

[0828] [In formulas (20a-2) and (20b-2), L 23 is a single bond, R 31 ~R 38 , L 21 , L 22 , L 24 ,Ar 21 and Ar 22 As defined in formula (20) above. ].

[0829] In one embodiment, compound (20) is a compound represented by the following formula (20a-3) and / or the following formula (20b-3).

[0830] [Chemistry 70]

[0831]

[0832] [In formulas (20a-3) and (20b-3), L 21 ~L 24 ,Ar 21 and Ar 22 As defined in formula (20) above. ].

[0833] In one embodiment, compound (20) is a compound represented by the following formula (20a-4).

[0834] [Chemistry 71]

[0835]

[0836] [In formula (20a-4), L 23 is a single bond, L 21 , L 22 , L 24 ,Ar 21 and Ar 22 As defined in formula (20) above. ].

[0837] Examples of the substituents referred to as "substituted or unsubstituted" in compounds (20), (20a), (20b), (20a-1), (20b-1), (20a-2), (20b-2), (20a-3), (20b-3) and (20a-4) (hereinafter also referred to as arbitrary substituents of compound (20)) include alkyl groups having 1 to 50 carbon atoms, alkenyl groups having 2 to 50 carbon atoms, alkynyl groups having 2 to 50 carbon atoms, cycloalkyl groups having 3 to 50 ring carbon atoms, alkoxy groups having 1 to 50 carbon atoms, alkylthio groups having 1 to 50 carbon atoms, aryloxy groups having 6 to 50 ring carbon atoms, arylthio groups having 6 to 50 ring carbon atoms, aralkyl groups having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 )、-C(=O)R 44 、-COOR 45 、-S(=O) 2 R 46 、-P(=O)(R 47 )(R 48 )、-Ge(R 49 )(R 50 )(R 51 )(Here, R 41 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. 41 ~R 51 When there are two or more, two or more R 41 ~R 51Each may be the same or different. ), hydroxyl, halogen atom, cyano, nitro, aryl group having 6 to 50 ring carbon atoms, and heterocyclic group having 5 to 50 ring atoms. Among them, alkyl group having 1 to 50 carbon atoms, aryl group having 6 to 50 ring carbon atoms, or heterocyclic group having 5 to 50 ring atoms is preferred, and alkyl group having 1 to 18 carbon atoms, aryl group having 6 to 18 ring carbon atoms, or heterocyclic group having 5 to 18 ring atoms is more preferred.

[0838] Specific examples of each substituent, optional substituent and halogen atom in these compounds (20) are the same as the above examples, but each substituent and optional substituent in compound (20) do not include substituted or unsubstituted amino groups. Therefore, in compound (20), there is only one amino group.

[0839] Specific examples of the compound (20) include the following compounds.

[0840] [Chemistry 72]

[0841]

[0842] In addition to the above-mentioned layers, an organic semiconductor layer, an adhesion improving layer, an insulating layer, etc. may be provided between the light-emitting layer and the anode, or between the light-emitting layer and the cathode.

[0843] In one embodiment, the compound (10) is preferably a host material of the light-emitting layer.

[0844] In addition, the light-emitting layer containing compound (10) may be a phosphorescent light-emitting layer or a fluorescent light-emitting layer, or may be a multilayer. The light-emitting layer containing compound (10) is preferably a fluorescent light-emitting layer. When there are multiple light-emitting layers, in order to prevent the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer, a spacer layer may be provided between each light-emitting layer.

[0845] In one embodiment, the light-emitting layer further includes one or both of a fluorescent dopant and a phosphorescent dopant.

[0846] The light-emitting layer containing the compound (10) may further contain one or both of a fluorescent dopant and a phosphorescent dopant. The light-emitting layer containing the compound (10) preferably contains a fluorescent dopant.

[0847] Examples of the fluorescent dopant and the phosphorescent dopant include fluorescent materials and phosphorescent materials that are guest materials for the light-emitting layer described later.

[0848] The organic EL element of the first mode comprises an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in sequence as described above, wherein the second electron transport layer comprises compound (1), and the light-emitting layer comprises compound (10). Otherwise, conventionally known materials and element structures may be applied without impairing the effects of the present invention.

[0849] The following describes the components and compounds (1) and (10) that can be used in one embodiment of the organic EL device of the first embodiment and the materials other than compound (20) that can be used arbitrarily in the layer between the anode and the light-emitting layer.

[0850] (Substrate)

[0851] The substrate is used as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a substrate that can be bent (flexible), for example, a plastic substrate formed of polycarbonate, polyvinyl chloride, etc. can be cited.

[0852] (anode)

[0853] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, examples thereof include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, examples thereof include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).

[0854] (Hole Injection Layer)

[0855] The hole injection layer is a layer containing a substance with high hole injection property. As a substance with high hole injection property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compound, or polymer compound (oligomer, dendrimer, polymer, etc.) can also be used.

[0856] (Hole Transport Layer)

[0857] The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used as the hole transport layer. Polymer compounds such as poly (N-vinyl carbazole) (abbreviated as: PVK) and poly (4-vinyl triphenylamine) (abbreviated as: PVTPA) can also be used. Among them, as long as the substance has a higher hole transport property than the electron transport property, substances other than them can be used. It should be noted that the layer containing a substance with high hole transport properties is not only a single layer, but the layer formed by the above-mentioned substance can also be stacked with two or more layers.

[0858] (Guest Material of Light Emitting Layer)

[0859] The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as a highly luminescent substance, a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.

[0860] As the blue fluorescent luminescent material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. As the green fluorescent luminescent material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. As the red fluorescent luminescent material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used.

[0861] As the blue phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. As the green phosphorescent material that can be used in the light-emitting layer, iridium complexes can be used. As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used.

[0862] (Host material of light-emitting layer)

[0863] As the light-emitting layer, the above-mentioned high-luminescent substance (guest material) can be dispersed in other substances (host material). As the substance for dispersing the high-luminescent substance, various substances can be used, preferably a substance having a high minimum unoccupied orbital energy level (LUMO energy level) and a low maximum occupied orbital energy level (HOMO energy level) compared to the high-luminescent substance.

[0864] As the substance (host material) for dispersing the highly luminescent substance, 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives can be used.

[0865] (Electron Transport Layer)

[0866] The electron transport layer is a layer containing a substance with high electron transport properties. Examples of the electron transport layer include 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.

[0867] (Electron Injection Layer)

[0868] The electron injection layer is a layer containing a substance with high electron injection properties. Lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), metal complex compounds such as 8-hydroxyquinoline-lithium (Liq), lithium oxide (LiO x ) or other alkali metals, alkaline earth metals, or compounds thereof.

[0869] (cathode)

[0870] The cathode preferably uses a metal, alloy, conductive compound, and mixture thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, 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), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys thereof.

[0871] In the organic EL element of the first embodiment, the method for forming each layer is not particularly limited. A formation method based on a conventionally known vacuum evaporation method, spin coating method, etc. can be used. Each layer such as the light-emitting layer can be formed by a known method based on a coating method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or a solution immersion method dissolved in a solvent, a spin coating method, a casting method, a rod coating method, a roller coating method, etc.

[0872] In the organic EL element of the first embodiment, the film thickness of each layer is not particularly limited, but is generally preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency.

[0873] An electronic device according to a second aspect of the present invention is characterized by comprising the organic electroluminescent element according to the first aspect.

[0874] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps. Example

[0875] Next, the present invention will be described in further detail with reference to Examples and Comparative Examples, but the present invention is not limited at all to the contents of these Examples.

[0876] Example 1

[0877] (Fabrication of organic EL elements)

[0878] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was 130 nm.

[0879] The washed glass substrate with a transparent electrode was placed on a substrate holder of a vacuum deposition device, and first, compounds HT and HI were deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode and to form a HI film with a thickness of 10 nm in such a manner that the ratio (mass ratio) of compound HI reached 3%. The HI film functioned as a hole injection layer.

[0880] Compound HT was then deposited on the HI film to form an HT film with a thickness of 80 nm on the HI film. The HT film functioned as a first hole transport layer.

[0881] Compound EB was then deposited on the HT film to form a 5 nm thick EB film on the HT film. This EB film functioned as a second hole transport layer.

[0882] Compound BH-1 (host material) and compound BD (dopant material) were co-deposited on the EB film so that the ratio (mass ratio) of compound BD was 4%, forming a 20 nm thick BH-1:BD film. This BH-1:BD film functioned as a light-emitting layer.

[0883] Compound HB-1 was evaporated on the light-emitting layer to form a HB-1 film with a thickness of 5 nm. The HB-1 film functions as the first electron transport layer. Compound E-1 and Liq were co-evaporated on the HB-1 film in such a way that the ratio of Liq (mass ratio) reached 50%, forming an E-1:Liq film with a thickness of 20 nm. The E-1:Liq film functions as the second electron transport layer. Liq was evaporated on the E-1:Liq film to form a Liq film with a thickness of 1 nm. Metal Al was evaporated on the Liq film to form a metal cathode with a thickness of 80 nm to produce an organic EL element.

[0884] (Evaluation of organic EL elements)

[0885] At a current density of 10 mA / cm 2 A voltage was applied to the obtained organic EL element in a manner of , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Conika Minolta Co., Ltd.). The external quantum efficiency EQE (%) was calculated from the obtained spectroradiometric brightness spectrum. The results are shown in Table 1.

[0886] Further, the current density was 50 mA / cm 2 Voltage was applied to the organic EL element in a manner to measure the time it took for the brightness to reach 95% of the initial brightness (LT95@50mA / cm 2 ) and the obtained life LT95 (hr) results are shown in Table 1.

[0887] Examples 2 to 39 and Comparative Examples 1 to 7

[0888] An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Tables 1 to 4 were used as the host material of the light-emitting layer and the materials of the electron transport layer and the electron injection layer.

[0889] The compounds used in Examples and Comparative Examples are shown below.

[0890] [Chemistry 73]

[0891]

[0892] [Chemistry 74]

[0893] .

[0894] [Table 1]

[0895]

[0896] The results in Table 1 show that the devices of Examples 1 to 9 using the compound represented by formula (1) for the second electron transport layer and the compound represented by formula (10) as the host material of the light emitting layer have high external quantum efficiency EQE and improved device life.

[0897] On the other hand, in Comparative Examples 1 and 2 in which the compound represented by the formula (1) was not used in the second electron transport layer, the external quantum efficiency EQE was poor and the device life was also short.

[0898] It is found that in Comparative Examples 3 and 4 in which a single organic layer is provided between the cathode and the light-emitting layer, the external quantum efficiency EQE is poor even when the compound represented by formula (1) is used.

[0899] It is found that even though there are two organic layers between the cathode and the light-emitting layer, the external quantum efficiency EQE of Comparative Example 5 in which the materials of the electron transport layer and the second electron transport layer are exchanged is poor.

[0900] It is found that in Comparative Examples 6 and 7 in which the compound represented by the formula (10) was not used as the host material of the light-emitting layer, both the external quantum efficiency EQE and the device life were significantly deteriorated.

[0901] [Table 2]

[0902]

[0903] From the results in Table 2, it can be seen that in Examples 10 to 18, even when different electron transport layer materials from those in Examples 1 to 9 are used, the external quantum efficiency EQE is high and the device life is improved.

[0904] On the other hand, it is found that in Comparative Example 2, in which only the material of the second electron transport layer was changed to the compound EC-1 which is not the compound represented by the formula (1), the device life was short.

[0905] [Table 3]

[0906]

[0907] From the results in Table 3, it can be seen that Examples 19 to 27 in which the material of the second electron transport layer is the compound represented by formula (1) and the host material of the light emitting layer is the compound represented by formula (10) have high external quantum efficiency EQE and improved device life.

[0908] [Table 4]

[0909]

[0910] From the results in Table 4, it can be seen that Examples 28 to 39 in which the material of the second electron transport layer is the compound represented by formula (1) and the main material of the light-emitting layer is the compound represented by formula (10) have high external quantum efficiency EQE and improved device life.

[0911] Several embodiments and / or examples of the present invention are described in detail above, and those skilled in the art can easily make more changes to these illustrative embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these more changes are also included in the scope of the present invention. The documents recorded in this specification and the contents of the applications that serve as the basis for the priority of the Paris Convention based on this application are all cited.

Claims

1. An organic electroluminescent element, which is an organic electroluminescent element comprising an anode, a light-emitting layer, a first electron transport layer, a second electron transport layer, and a cathode in sequence, The first electron transport layer comprises a compound represented by the following formula (30): The second electron transport layer includes a compound represented by the following formula (1): The second electron transport layer further contains one or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals, The light-emitting layer contains a compound represented by the following formula (10): [Chemistry 75] In formula (1), FA is a substituted or unsubstituted aryl group having a fused ring formed by condensing three or more hydrocarbon rings and having 13 to 50 ring carbon atoms. When FA has a substituent, the substituent is an aryl group having 6 to 30 ring carbon atoms. L1 is a single bond, or is selected from Phenylene, Biphenylene, Terphenylene, Quaterphenylene, an arylene group containing a condensed ring having 10 to 30 ring carbon atoms, and A group formed by connecting 1 to 3 phenylene groups and 1 to 3 arylene groups containing a condensed ring having 10 to 30 ring carbon atoms via a single bond, wherein Ar1 and Ar2 are each independently an aryl group having 6 to 12 ring carbon atoms, X1~X3 are N; [Chemistry 76] In formula (10), R 11 ~R 18 is a hydrogen atom, Ar 11 and Ar 12 At least one of them is a monovalent group represented by the following formula (11); [Chemistry 77] In formula (11), R 21 ~R 28 One of them is the same as L 11 or L 12 Bonded bonding sites, Not with L 11 or L 12 Bonded bonding position R 21 ~R 28 is a hydrogen atom; Ar which is not a monovalent group represented by the above formula (11) 11 or Ar 12 is an unsubstituted aryl group having 6 to 50 ring carbon atoms, L 11 and L 12 are each independently a single bond, or an arylene group having 6 to 50 ring carbon atoms, [Chemistry 96] In formula (30), X 11 is a nitrogen atom or CH, R 81 , R 82 and R 84 Each is independently a group represented by any one of the following formulae (31) to (34), [Chemistry 97] -L 31 (31) -L 32 -L 33 (32) -L 34 -L 35 -L 36 (33) In formulas (31) to (34), L 31 , L 33 , L 36 , L 38 and L 39 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms, 31 , L 33 , L 36 , L 38 and L 39 When the aryl group having 6 to 30 ring carbon atoms has a substituent, the substituent is an alkyl group having 1 to 50 carbon atoms; when the monovalent heterocyclic group having 5 to 32 ring atoms has a substituent, the substituent is an aryl group having 6 to 12 ring carbon atoms, L 32 , L 34 and L 35 are each independently an arylene group having 6 to 30 ring carbon atoms, L 37 It is a trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms.

2. The organic electroluminescent element according to claim 1, wherein FA is an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, or An aryl group having 13 to 50 ring carbon atoms and substituted with an aryl group having 6 to 30 ring carbon atoms and containing a condensed ring in which three or more hydrocarbon rings are condensed.

3. The organic electroluminescent element according to claim 1 or 2, wherein: FA is an unsubstituted aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings substituted with an aryl group having 6 to 30 ring carbon atoms.

4. The organic electroluminescent element according to claim 3, wherein FA is an unsubstituted aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group containing a condensed ring having 13 to 30 ring carbon atoms formed by condensing three or more hydrocarbon rings substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms.

5. The organic electroluminescent element according to claim 1 or 2, wherein: FA is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted and substituted or unsubstituted benzo Groups in a group.

6. The organic electroluminescent element according to claim 5, wherein FA is selected from unsubstituted fluorenyl, unsubstituted anthracenyl, unsubstituted phenanthrenyl, unsubstituted fluoranthenyl, unsubstituted triphenylene, unsubstituted pyrenyl, unsubstituted benzoic acid, and unsubstituted benzoic acid Groups in a group.

7. The organic electroluminescent element according to claim 1 or 2, wherein: FA is selected from 9-anthryl, 10-phenylanthryl, 10-biphenylanthryl, 10-terphenylanthryl, 10-naphthylanthryl, 9,10-diphenylanthryl, 9,10-dinaphthylanthryl, 9,9-diphenylfluorenyl, 9-phenanthrenyl, benzophenanthryl, The invention also includes groups selected from the group consisting of benzo[c]phenanthrenyl, benzo[a]phenanthrenyl, benzo[a]anthryl, and pyrene.

8. The organic electroluminescent element according to claim 1 or 2, wherein: FA is a group selected from 9,9-diphenylfluoren-2-yl, 9,9-diphenylfluoren-4-yl, 10-naphthylanthracene-9-yl, 10-biphenylanthracene-9-yl, 9,10-diphenylanthracene-2-yl, and a group represented by the following formula:

9. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond, or is selected from Phenylene, Biphenylene, and The group in the naphthylene group.

10. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond or a group selected from divalent groups represented by the following formulae (aa1) to (aa3), In formulas (aa1) to (aa3), R2 is an aryl group having 6 to 30 ring carbon atoms or a monovalent heterocyclic group having 5 to 30 ring atoms, except for carbazolyl; n1 is 0 and n2 is 0.

11. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond or a group selected from divalent groups represented by the following formulae (a1) to (a3), [Chemistry 78] 12. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond or a divalent group selected from the following formulae (a1-1) to (a1-3), [Chemistry 79] 13. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond or a group selected from divalent groups represented by the following formulae (a2-1) to (a2-9), 14. The organic electroluminescent element according to claim 1 or 2, wherein: L1 is a single bond or a group selected from divalent groups represented by the following formulae (a3-1) to (a3-6), 15. The organic electroluminescent element according to claim 1 or 2, wherein: Ar1 and Ar2 are each independently an aryl group having 6 to 12 ring carbon atoms.

16. The organic electroluminescent element according to claim 1 or 2, wherein: Ar1 and Ar2 are each independently a group selected from monovalent groups represented by the following formulae (b1) to (b3), [Chemistry 80] In formulas (b1) to (b3), R5 is each independently a substituent, p is 0, q is 0, m is 0.

17. The organic electroluminescent element according to claim 1 or 2, wherein: Ar1 and Ar2 are each independently a group selected from monovalent groups represented by the following formulae (b1-1) and (b3-1) to (b3-3), [Chemistry 81] In formulas (b1-1) and (b3-1) to (b3-3), R5 are each independently a substituent, p is 0, m is 0.

18. The organic electroluminescent element according to claim 1, wherein FA is an unsubstituted aryl group containing a fused ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, L1 is a single bond, or is selected from Phenylene, Biphenylene, Terphenylene, Quaterphenylene, an arylene group containing a condensed ring having 10 to 30 ring carbon atoms, and A group formed by connecting 1 to 3 phenylene groups and 1 to 3 arylene groups containing a condensed ring having 10 to 30 ring carbon atoms via a single bond, wherein Ar1 and Ar2 are each independently an unsubstituted aryl group having 6 to 12 ring carbon atoms.

19. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the aforementioned formula (1) is a compound represented by the following formula (2), [Chemistry 82] In formula (2), FA a is an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group having 13 to 50 ring carbon atoms and substituted with an aryl group having 6 to 30 ring carbon atoms, L 1a is a single bond, or is selected from Phenylene, Biphenylene, Terphenylene, Quaterphenylene, and an arylene group containing a condensed ring having 10 to 30 ring carbon atoms, Ar 1a and Ar 2a Each is independently an aryl group having 6 to 12 ring carbon atoms.

20. The organic electroluminescent element according to claim 19, wherein The compound represented by the above formula (1) is a compound represented by the following formula (2-1), [Chemistry 83] In formula (2-1), FA a is an unsubstituted aryl group having a condensed ring of 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group having a condensed ring of 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings substituted with an aryl group having 6 to 30 ring carbon atoms, L 1a’ is a single bond, or is selected from Phenylene, Biphenylene, Terphenylene, Quaterphenylene, and an arylene group containing a condensed ring having 10 to 30 ring carbon atoms, Ar 1a and Ar 2a Each is independently an aryl group having 6 to 12 ring carbon atoms.

21. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (1) is a compound represented by the following formula (3), [Chemistry 84] In formula (3), FA a is an unsubstituted aryl group having a condensed ring of 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group having a condensed ring of 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings substituted with an aryl group having 6 to 30 ring carbon atoms, L 1b is a single bond, or a group selected from divalent groups represented by the following formulae (a1) to (a3), [Chemistry 85] Ar 1b and Ar 2b are each independently a group selected from the monovalent groups represented by the following formulae (b1) to (b3), [Chemistry 86] In formulas (b1) to (b3), R5 are each independently a substituent, p is 0, q is 0, m is 0.

22. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (1) is a compound represented by the following formula (4), [Chemistry 87] In formula (4), FA c is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted and substituted or unsubstituted benzo The group in the group, FA c When there is a substituent, the substituent is an aryl group having 6 to 30 ring carbon atoms, L 1c is a single bond, or a group selected from divalent groups represented by the following formulae (a1-1) to (a1-3), [Chemistry 88] Ar 1c and Ar 2c Each independently represents a group selected from the monovalent groups represented by the following formulae (b1-1) and (b3-1) to (b3-3); [Chemistry 89] In formulas (b1-1) and (b3-1) to (b3-3), R5 are each independently a substituent, p is 0, m is 0.

23. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (1) is a compound represented by the following formula (5), [Chemistry 90] In formula (5), FA, L1 and X1 to X3 are the same as those in the above formula (1). R6 is each independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 12 ring atoms, r is 0.

24. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (1) is a compound represented by the following formula (6), [Chemistry 91] In formula (6), X1 to X3 are as defined in formula (1) above, FA a is an unsubstituted aryl group containing a condensed ring having 13 to 50 ring carbon atoms formed by condensing three or more hydrocarbon rings, or an aryl group having 13 to 50 ring carbon atoms and substituted with an aryl group having 6 to 30 ring carbon atoms, L 1d is a single bond, or is selected from Phenylene, Biphenylene, Terphenylene, Quaterphenylene, and an arylene group containing a condensed ring having 10 to 30 ring carbon atoms, Ar 1d and Ar 2d Each is independently an unsubstituted aryl group having 6 to 12 ring carbon atoms.

25. The organic electroluminescent element according to claim 1, wherein The compound represented by the above formula (1) is selected from the following group, 26. The organic electroluminescent element according to claim 1, wherein The compound represented by the above formula (1) is selected from the following E-1 to E-9, 27. The organic electroluminescent element according to claim 1, wherein L 11 and L 12 Each is independently a single bond or an arylene group having 6 to 30 ring carbon atoms.

28. The organic electroluminescent element according to claim 1, wherein L 11 and L 12 Each is independently a single bond or an arylene group having 6 to 18 ring carbon atoms.

29. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the aforementioned formula (10) is a compound represented by the following formula (10-1), [Chemistry 92] In formula (10-1), R 11 ~R 18 ,Ar 11 , L 11 , L 12 , R 21 and R 23 ~R 28 As defined in formula (10) above.

30. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the aforementioned formula (10) is a compound represented by the following formula (10-2), [Chemistry 93] In formula (10-2), L 11 is a single bond, R 11 ~R 18 ,Ar 11 , L 12 , and R 21 ~R 28 As defined in formula (10) above.

31. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the aforementioned formula (10) is a compound represented by the following formula (10-3), [Chemistry 94] In formula (10-3), L 11 is a single bond, R 11 ~R 18 ,Ar 11 , L 12 , R 21 and R 23 ~R 28 As defined in formula (10) above.

32. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the aforementioned formula (10) is a compound represented by the following formula (10-4), [Chemistry 95] In formula (10-4), L 11 is a single bond, Ar 11 and L 12 As defined in formula (10) above.

33. The organic electroluminescent element according to claim 1, wherein L 11 and L 12 Each is independently a single bond or an unsubstituted arylene group having 6 to 50 ring carbon atoms.

34. The organic electroluminescent element according to claim 1, wherein L 11 and L 12 Each is independently a single bond or a phenylene group.

35. The organic electroluminescent element according to claim 1, wherein The compound represented by the above formula (10) is selected from the following group, 36. The organic electroluminescent element according to claim 1, wherein The compound represented by the above formula (10) is selected from the following BH-1 to BH-4, 37. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulas (31) to (34), L 31 ~L 39 The substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms are substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, respectively.

38. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulae (31) to (34), L in the above formulae (31) to (34) is 31 ~L 39 The substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms and the aromatic hydrocarbon ring having 6 to 30 ring carbon atoms are benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, acenaphthylene, anthracene, benzanthracene, aceanthrene, phenanthrene, triphenylene, phenalene, pentacene, pyrene, pentaphenylene, pyrene, Benzo s-indene, as-indene, fluoranthene, benzofluoranthene, perylene, triphenylene, benzotriphenylene, or spirofluorene.

39. The organic electroluminescent element according to claim 1 or 2, wherein: Composition 31 ~L 39 The substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms is selected from the following group:

40. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (31) to (34) 31 , L 33 , L 36 , L 38 and L 39 The aryl group having 6 to 30 ring carbon atoms is selected from benzene, biphenyl, terphenyl, naphthalene, fluorene, phenanthrene, anthracene, triphenylene, benzophenone, A monovalent residue obtained by removing one hydrogen atom from a ring carbon of an aromatic hydrocarbon ring in fluoranthene, pyrene, and spirofluorene.

41. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (31) to (34) 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is selected from the following group, 42. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (32) and (33) 32 , L 34 and L 35 The arylene group having 6 to 30 ring carbon atoms is a divalent residue obtained by removing one hydrogen atom from each of two ring carbon atoms of an aromatic hydrocarbon ring selected from benzene, naphthalene, biphenyl, terphenyl, quaterphenyl, spirofluorene, and anthracene.

43. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (32) and (33) 32 , L 34 and L 35 The arylene group having 6 to 30 ring carbon atoms is selected from the following group, 44. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formula (34) 37 The trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms in is a trivalent residue obtained by removing one hydrogen atom from each of three ring carbon atoms of an aromatic hydrocarbon ring selected from benzene, naphthalene, and anthracene.

45. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formula (34) 37 The trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms is a trivalent residue of benzene.

46. ​​The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formula (34) 37 The trivalent aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms is benzene-1,3,5-triyl.

47. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulas (31) to (34), L 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms is a substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

48. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulas (31) to (34), L 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms contains 1 to 5 ring hetero atoms.

49. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulae (31) to (34), L in the above formulae (31) to (34) is 31 , L 33 , L 36 , L 38 and L 39 The heterocyclic ring having 5 to 32 ring atoms of the substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms is selected from pyrrole, imidazole, imidazoline, pyrazole, triazole, furan, thiophene, thiazole, isothiazole, oxazole, isoxazole, oxadiazole, thiadiazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, bipyrrole, terpyrrole, bithiophene, terthiophene, bipyridine, terpyridine, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, indolizine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, indazole, benzisoxazole, benzisothiazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazole, benzocarbazole, phenanthridine, acridine, phenanthroline, phenazine, phenothiazine, phenoxazine, and xanthene.

50. The organic electroluminescent element according to claim 1 or 2, wherein: In the above formulas (31) to (34), the constituent L 31 , L 33 , L 36 , L 38 and L 39 The heterocyclic ring having 5 to 32 ring atoms of the substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms is selected from the following group, 51. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (31) to (34) 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted monovalent heteroatom group having 5 to 32 ring atoms is a monovalent residue obtained by removing one hydrogen atom from a ring atom of a heterocyclic ring selected from substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted bipyridine, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted phenanthroline, and substituted or unsubstituted quinoline. When the monovalent heterocyclic group having 5 to 32 ring atoms has a substituent, the substituent is an aryl group having 6 to 12 ring carbon atoms.

52. The organic electroluminescent element according to claim 1 or 2, wherein: L in the above formulas (31) to (34) 31 , L 33 , L 36 , L 38 and L 39 The substituted or unsubstituted monovalent heterocyclic group having 5 to 32 ring atoms is selected from the following group:

53. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (30) is selected from the following group, 54. The organic electroluminescent element according to claim 1 or 2, wherein: The compound represented by the above formula (30) is selected from the following HB-1 to HB-5, 55. The organic electroluminescent element according to claim 1 or 2, wherein: At least one organic layer is further included between the anode and the light-emitting layer.

56. The organic electroluminescent element according to claim 55, wherein The at least one organic layer contains a compound represented by the following formula (20): In formula (20), R not involved in the ring 31 ~R 38 are each independently a hydrogen atom, 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, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 201 )(R 202 )(R 203 )、 -C(=O)R 204 、 -COOR 205 、 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, R 201 ~R 205 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 201 ~R 205 When there are two or more, two or more R 201 ~R 205 They can be the same or different. L 21 ~L 24 each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, 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 21 and Ar 22 are 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, The substituents in the compound (20) referred to as "substituted or unsubstituted" are alkyl having 1 to 50 carbon atoms, alkenyl having 2 to 50 carbon atoms, alkynyl having 2 to 50 carbon atoms, cycloalkyl having 3 to 50 ring carbon atoms, alkoxy having 1 to 50 carbon atoms, alkylthio having 1 to 50 carbon atoms, aryloxy having 6 to 50 ring carbon atoms, arylthio having 6 to 50 ring carbon atoms, aralkyl having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 、-COOR 45 、-S(=O)2R 46 ,-P(=O)(R 47 )(R 48 )、-Ge(R 49 )(R 50 )(R 51 ), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms, Here, R 41 ~R 51 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms, and R 41 ~R 51 When there are two or more, two or more R 41 ~R 51 They can be the same or different.

57. The organic electroluminescent element according to claim 56, wherein L 24 For a single key.

58. The organic electroluminescent element according to claim 56, wherein L 23 For a single key.

59. The organic electroluminescent element according to claim 56, wherein Ar 21 and Ar 22 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

60. The organic electroluminescent element according to claim 56, wherein: R 31 ~R 38 A hydrogen atom.

61. The organic electroluminescent element according to claim 56, wherein: Compound (20) includes either or both of a compound represented by the following formula (20a) and a compound represented by the following formula (20b), In formulas (20a) and (20b), R 31 ~R 38 , L 21 ~L 24 ,Ar 21 and Ar 22 As defined above in formula (20).

62. The organic electroluminescent element according to claim 56, wherein: The substituent referred to as "substituted or unsubstituted" in compound (20) is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms.

63. The organic electroluminescent element according to claim 56, wherein: The substituent referred to as "substituted or unsubstituted" in compound (20) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, or a heterocyclic group having 5 to 18 ring atoms.

64. The organic electroluminescent element according to claim 56, wherein: The compound represented by the above formula (20) is selected from the following group, 65. The organic electroluminescent element according to claim 56, wherein: The compound represented by the above formula (20) is the following compound EB, 66. The organic electroluminescent element according to claim 1 or 2, wherein: The light-emitting layer further includes either or both of a fluorescent dopant and a phosphorescent dopant.

67. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 66.

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