Organic electroluminescent element and electronic device

Abstract

The invention relates to an organic electroluminescent element and an electronic device. This organic electroluminescent element has a cathode, an anode, and an organic layer between the cathode and the anode, and is characterized in that the organic layer contains a compound represented by formula (1) and a compound represented by formula (11). # imgabs0 #

Description

[0001] This application is a divisional application of the PCT patent application PCT / JP2019 / 015035, with the invention title "Organic Electroluminescent Element and Electronic Device". The application number of the mother application entering China is 201980024558.4. Technical Field

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

[0003] When a 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, respectively. And, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0004] In Patent Documents 1 to 3, a fluoranthene derivative is disclosed as a dopant material for the light-emitting layer of an organic electroluminescent element.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: Japanese Patent Application Laid-Open No. 2015-195348

[0008] Patent Document 2: Japanese Patent Application Laid-Open No. 2015-164178

[0009] Patent Document 3: Japanese Patent Application Laid-Open No. 2013-157552. Summary of the Invention

[0010] An object of the present invention is to provide an organic electroluminescent element having a long life, high efficiency, or low voltage driving.

[0011] Another object of the present invention is to provide an electronic device using an organic electroluminescent element having a long life, high efficiency, or low voltage driving.

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

[0013] 1. An organic electroluminescent element, which is an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode (hereinafter sometimes referred to as "organic electroluminescent element 1"),

[0014] The organic layer contains a compound represented by the following formula (1) and a compound represented by the following formula (11).

[0015] [Chemical Formula 1]

[0016]

[0017] [In formula (1),

[0018] One or more of R1 to R8 is -L 13 -Ar 13 .

[0019] L 11 ~L 13 Each independently is

[0020] A single bond,

[0021] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0022] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0023] L 13 When there are two or more, two or more Ls 13 May be the same or different from each other.

[0024] Ar 11 ~Ar 13 Each independently is

[0025] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0026] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0027] Ar 13 When there are two or more, two or more Ars 13 May be the same or different from each other.

[0028] R1 to R8 that are not -L 13 -Ar 13 Each independently is

[0029] A hydrogen atom,

[0030] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0031] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0032] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0033] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0034] -Si(R 901 )(R 902 )(R 903 ),

[0035] -O-(R 904 )、

[0036] -S-(R 905 )、

[0037] -N(R 906 )(R 907 )、

[0038] a halogen atom, a cyano group, a nitro group,

[0039] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0040] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0041] R 901 ~R 907 are each independently

[0042] a hydrogen atom,

[0043] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0044] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

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

[0046] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are two or more R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 may be the same or different from each other.]

[0047] [Chemical Formula 2]

[0048]

[0049] [In Formula (11),

[0050] R 11 ~R 20 in one or more groups of two or more adjacent ones among them, R a1 ~R a5 in one or more groups of two or more adjacent ones among them, and R a6 ~R a10 in one or more groups of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms.

[0051] R 11 ~R 20 、Ra1 ~R a5 , and R a6 ~R a10 Each independently is

[0052] a hydrogen atom,

[0053] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0054] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0055] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0056] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0057] a substituted or unsubstituted amino group,

[0058] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0059] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0060] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0061] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0062] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0063] a substituted or unsubstituted phosphino group,

[0064] a substituted or unsubstituted phosphoryl group,

[0065] a substituted or unsubstituted silyl group,

[0066] a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms,

[0067] a cyano group, a nitro group, a carboxyl group, or

[0068] a halogen atom.]

[0069] 2. An organic electroluminescent element, which is an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode (hereinafter sometimes referred to as "organic electroluminescent element 2"),

[0070] wherein the organic layer contains a compound represented by the following formula (1) and

[0071] Compound A having a Stokes shift of 20 nm or less and an emission peak wavelength of 440 nm to 465 nm.

[0072] [Chemical Formula 3]

[0073]

[0074] [In Formula (1),

[0075] One or more of R1 to R8 is -L 13 -Ar 13 .

[0076] L 11 ~L 13 Each independently is

[0077] A single bond,

[0078] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0079] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0080] L 13 When there are two or more Ls, the two or more Ls 13 May be the same or different from each other.

[0081] Ar 11 ~Ar 13 Each independently is

[0082] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0083] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0084] Ar 13 When there are two or more Ar, the two or more Ar 13 May be the same or different from each other.

[0085] Not -L 13 -Ar 13 R1 to R8 each independently is

[0086] A hydrogen atom,

[0087] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0088] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0089] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0090] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0091] -Si(R 901 )(R902 )(R 903 )、

[0092] -O-(R 904 )、

[0093] -S-(R 905 )、

[0094] -N(R 906 )(R 907 )、

[0095] a halogen atom, a cyano group, a nitro group,

[0096] an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, or

[0097] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which may be substituted or unsubstituted.

[0098] R 901 ~R 907 each independently is

[0099] a hydrogen atom,

[0100] an alkyl group having 1 to 50 carbon atoms which may be substituted or unsubstituted,

[0101] a cycloalkyl group having 3 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted,

[0102] an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, or

[0103] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which may be substituted or unsubstituted. When there are two or more of R 901 ~R 907 two or more of R 901 ~R 907 may be the same or different from each other.]

[0104] 3. An electronic device including the organic electroluminescent element according to 1 or 2 above.

[0105] According to the present invention, an organic electroluminescent element with long life, high efficiency, or low-voltage driving can be provided.

[0106] According to the present invention, an electronic device using the organic electroluminescent element with long life, high efficiency, or low-voltage driving can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0107] Figure 1 FIG. is a diagram showing a schematic configuration of the organic EL element according to the first embodiment of the present invention.

[0108] Figure 2It is a diagram showing the schematic configuration of the organic EL element according to the second mode of the present invention.

[0109] Figure 3 It is a diagram showing the schematic configuration of the organic EL element according to the third mode of the present invention.

[0110] Figure 4 It is a diagram showing the schematic configuration of the organic EL element according to the fourth mode of the present invention.

[0111] Figure 5 It is a diagram showing the schematic configuration of the organic EL element according to the fifth mode of the present invention. Detailed Embodiments

[0112] [Definitions]

[0113] In this specification, a hydrogen atom includes isotopes with different numbers of neutrons, namely, protium, deuterium, and tritium.

[0114] In this specification, the number of ring-forming carbon atoms means the number of carbon atoms among the atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (for example, a monocyclic compound, a polycyclic compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. Regarding the "number of ring-forming carbon atoms" described below, unless otherwise specified, it means the same meaning. For example, the number of ring-forming carbon atoms in a benzene ring is 6, the number of ring-forming carbon atoms in a naphthalene ring is 10, the number of ring-forming carbon atoms in a pyridine ring is 5, and the number of ring-forming carbon atoms in a furan ring is 4. In addition, for example, the number of ring-forming carbon atoms in 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms in 9,9'-spirobifluorenyl is 25.

[0115] In addition, when an alkyl group is substituted as a substituent on a benzene ring or a naphthalene ring, the number of carbon atoms in the alkyl group is included in the number of ring-forming carbon atoms.

[0116] In this specification, the number of ring-forming atoms means the number of atoms constituting the ring itself in a compound in which atoms are bonded to form a ring structure (for example, a monocyclic ring, a polycyclic ring, a ring assembly). Atoms that do not form a ring (for example, hydrogen atoms that are terminated by the bonds of atoms forming the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. Regarding the "number of ring-forming atoms" described below, unless otherwise specified, it means the same meaning. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. Regarding the hydrogen atoms bonded to the carbon atoms in the pyridine ring and the quinazoline ring and the atoms constituting the substituent, they are not included in the number of ring-forming atoms.

[0117] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" represents the number of carbon atoms of the ZZ group when it is unsubstituted, and does not include the carbon atoms of the substituents when it is substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer of 1 or more.

[0118] In this specification, in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted", "XX to YY atoms" represents the number of atoms of the ZZ group when it is unsubstituted, and does not include the atoms of the substituents when it is substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer of 1 or more.

[0119] In the case of a "ZZ group which may be substituted or unsubstituted", "unsubstituted" means that the ZZ group is not substituted by a substituent and is bonded to a hydrogen atom. Alternatively, in the case of a "ZZ group which may be substituted or unsubstituted", "substituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. In the case of "substituted by an AA group to form a BB group", "substituted" similarly means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0120] Hereinafter, the substituents described in this specification will be described.

[0121] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0122] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18.

[0123] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0124] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0125] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0126] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6.

[0127] Unless otherwise specified in this specification, the ring-forming carbon atoms of the "unsubstituted arylene" described in this specification are 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0128] Unless otherwise specified in this specification, the ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification are 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the carbon atoms of the "unsubstituted alkylene" described in this specification are 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0129] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls and substituted aryls can be cited. (Here, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is the "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is the "substituted aryl".) Hereinafter, when simply referred to as "aryl", it includes both "unsubstituted aryl" and "substituted aryl".

[0130] When the "substituted aryl" has a substituent on the "unsubstituted aryl", groups in which the following "unsubstituted aryl" has a substituent, examples of the substituted aryl, etc. can be cited. It should be noted that the examples of the "unsubstituted aryl" and the "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the group in which the "unsubstituted aryl" has a substituent further has a substituent, groups in which the "substituted aryl" further has a substituent, etc.

[0131] Unsubstituted aryl:

[0132] Phenyl,

[0133] p-Biphenylyl,

[0134] m-Biphenylyl,

[0135] o-Biphenylyl,

[0136] p-Terphenyl-4-yl,

[0137] p-Terphenyl-3-yl, p-Terphenyl-2-yl, m-Terphenyl-4-yl, m-Terphenyl-3-yl, m-Terphenyl-2-yl, o-Terphenyl-4-yl, o-Terphenyl-3-yl, o-Terphenyl-2-yl, 1-Naphthyl, 2-Naphthyl, Anthryl, Benzoanthryl, Phenanthryl, Benzo[a]phenanthryl, Phenylenyl, yl, Benzo yl, Triphenylenyl, Benzo[a]triphenylenyl, Tetracenyl, Pentacenyl, Fluorenyl, 9,9'-Spirobi[fluorenyl], Benzo[b]fluorenyl, Dibenzofluorenyl, Fluoranthenyl, Benzo[k]fluoranthenyl, yl

[0138] Substituted aryl: o-tolyl, m-tolyl,

[0139] p-tolyl,

[0140] p-xylyl,

[0141] m-xylyl,

[0142] o-xylyl,

[0143] p-isopropylphenyl,

[0144] m-isopropylphenyl,

[0145] o-isopropylphenyl,

[0146] p-tert-butylphenyl,

[0147] m-tert-butylphenyl,

[0148] o-tert-butylphenyl,

[0149] 3,4,5-trimethylphenyl,

[0150] 9,9-dimethylfluorenyl,

[0151] 9,9-diphenylfluorenyl

[0152] 9,9-bis(4-methylphenyl)fluorenyl,

[0153] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0154] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0155] cyanophenyl,

[0156] triphenylsilylphenyl,

[0157] trimethylsilylphenyl,

[0158] phenylnaphthyl,

[0159] naphthylphenyl.

[0160] The "heterocyclic group" described in this specification is a cyclic group containing at least 1 heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0161] The "heterocyclic group" described in this specification may be a monocyclic group or a fused-ring group.

[0162] The "heterocyclic group" described in this specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.

[0163] As specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification, the following unsubstituted heterocyclic groups and substituted heterocyclic groups can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) Hereinafter, when simply referred to as a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".

[0164] The case where the "substituted heterocyclic group" is an unsubstituted heterocyclic group having a substituent includes groups such as the following unsubstituted heterocyclic groups having a substituent and examples of substituted heterocyclic groups. It should be noted that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are only one example, and the "substituted heterocyclic group" described in this specification also includes groups in which the group of the "unsubstituted heterocyclic group" having a substituent further has a substituent, groups in which the "substituted heterocyclic group" further has a substituent, and the like.

[0165] Unsubstituted heterocyclic groups containing a nitrogen atom:

[0166] Pyrrolyl,

[0167] Imidazolyl,

[0168] Pyrazolyl,

[0169] Triazolyl,

[0170] Tetrazolyl,

[0171] Oxazolyl,

[0172] Isoxazolyl,

[0173] Oxadiazolyl,

[0174] Thiazolyl,

[0175] Isothiazolyl,

[0176] Thiadiazolyl,

[0177] Pyridyl,

[0178] Pyridazinyl,

[0179] Pyrimidinyl,

[0180] Pyrazinyl,

[0181] Triazinyl,

[0182] Indolyl,

[0183] Isoindolyl,

[0184] Indolizinyl,

[0185] quinolizinyl,

[0186] quinolinyl,

[0187] isoquinolinyl,

[0188] cinnolinyl,

[0189] phthalazinyl,

[0190] quinazolinyl,

[0191] quinoxalinyl,

[0192] benzimidazolyl, indazolyl,

[0193] phenanthrolinyl,

[0194] phenanthridinyl,

[0195] acridinyl,

[0196] phenazinyl,

[0197] carbazolyl,

[0198] benzocarbazolyl, morpholinyl,

[0199] phenoxazinyl,

[0200] phenothiazinyl,

[0201] azacarbazolyl, diazacarbazolyl unsubstituted heterocyclic groups containing an oxygen atom: furyl,

[0202] oxazolyl,

[0203] isoxazolyl,

[0204] oxadiazolyl,

[0205] xanthenyl,

[0206] benzofuryl, isobenzofuryl, dibenzofuryl, naphthobenzofuryl, benzoxazolyl, benzisoxazolyl, phenoxazinyl,

[0207] morpholinyl,

[0208] dinaphthofuryl, azadibenzofuryl, diazadibenzofuryl, azanaphthobenzofuryl, diazanaphthobenzofuryl unsubstituted heterocyclic groups containing a sulfur atom: thienyl,

[0209] thiazolyl,

[0210] isothiazolyl,

[0211] thiadiazolyl,

[0212] Benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzothiazolyl, benzoisothiazolyl, phenothiazinyl,

[0213] Dinaphthothienyl, azadibenzothienyl, diazadibenzothienyl, azanaphthobenzothienyl, diazanaphthobenzothienyl, substituted heterocyclic groups containing a nitrogen atom:

[0214] (9-Phenyl)carbazolyl,

[0215] (9-Biphenyl)carbazolyl,

[0216] (9-Phenyl)phenylcarbazolyl,

[0217] (9-Naphthyl)carbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, methylbenzimidazolyl, ethylbenzimidazolyl,

[0218] Phenyltriazinyl,

[0219] Biphenyltriazinyl,

[0220] Diphenyltriazinyl,

[0221] Phenylquinazolinyl,

[0222] Biphenylquinazolinyl

[0223] Substituted heterocyclic groups containing an oxygen atom:

[0224] Phenyldibenzofuranyl,

[0225] Methyldibenzofuranyl,

[0226] tert-Butyldibenzofuranyl,

[0227] Monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene]

[0228] Substituted heterocyclic groups containing a sulfur atom:

[0229] Phenyldibenzothienyl,

[0230] Methyldibenzothienyl,

[0231] tert-Butyldibenzothienyl,

[0232] Monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0233] Monovalent groups formed from the following unsubstituted heterocycles containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and groups having substituents formed from the following unsubstituted heterocycles:

[0234] [Chemical formula 4]

[0235]

[0236] In formulas (XY-1) to (XY-18), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.

[0237] The heterocycle represented by the above formulas (XY-1) to (XY-18) has a bond at any position to form a monovalent heterocyclic group.

[0238] That the monovalent group formed by the unsubstituted heterocycle represented by the above formulas (XY-1) to (XY-18) has a substituent means that the hydrogen atom bonded to the carbon atom of the skeleton in these formulas is replaced by a substituent, or X A , Y A is NH or CH2, and the hydrogen atom in these NH or CH2 is in a state of being replaced by a substituent.

[0239] As specific examples (specific example group G3) of the "substituted or unsubstituted alkyl" described in this specification, the following unsubstituted alkyls and substituted alkyls can be cited. (Here, the unsubstituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is an "unsubstituted alkyl", and the substituted alkyl refers to the case where the "substituted or unsubstituted alkyl" is a "substituted alkyl".) Hereinafter, when simply referred to as "alkyl", it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0240] The "substituted alkyl" is the case where the "unsubstituted alkyl" has a substituent, and examples thereof include groups in which the following "unsubstituted alkyl" has a substituent, substituted alkyls, etc. It should be noted that the examples of the "unsubstituted alkyl" and the examples of the "substituted alkyl" listed here are only one example, and the "substituted alkyl" described in this specification also includes groups in which the group in which the "unsubstituted alkyl" has a substituent further has a substituent, groups in which the "substituted alkyl" further has a substituent, etc.

[0241] Unsubstituted alkyl:

[0242] Methyl,

[0243] Ethyl,

[0244] n-Propyl,

[0245] Isopropyl,

[0246] n-Butyl,

[0247] Isobutyl,

[0248] sec-butyl,

[0249] tert-butyl

[0250] substituted alkyl:

[0251] heptafluoropropyl (including isomers),

[0252] pentafluoroethyl,

[0253] 2,2,2-trifluoroethyl,

[0254] trifluoromethyl

[0255] As specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyls and substituted alkenyls can be cited. (Here, the unsubstituted alkenyl means the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and the "substituted alkenyl" means the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) Hereinafter, when simply referred to as "alkenyl", it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0256] When the "substituted alkenyl" is an "unsubstituted alkenyl" having a substituent, groups in which the following "unsubstituted alkenyl" has a substituent, examples of substituted alkenyls, etc. can be cited. It should be noted that the examples of the "unsubstituted alkenyl" and the "substituted alkenyl" listed here are only one example, and the "substituted alkenyl" described in this specification also includes groups in which the group in which the "unsubstituted alkenyl" has a substituent further has a substituent, groups in which the "substituted alkenyl" further has a substituent, etc.

[0257] Unsubstituted alkenyl and substituted alkenyl:

[0258] vinyl,

[0259] allyl,

[0260] 1-butenyl,

[0261] 2-butenyl,

[0262] 3-butenyl,

[0263] 1,3-butadienyl,

[0264] 1-methylethenyl,

[0265] 1-methylallyl,

[0266] 1,1-dimethylallyl,

[0267] 2-methylallyl,

[0268] 1,2-dimethylallyl

[0269] As a specific example (specific example group G5) of the "substituted or unsubstituted alkynyl" described in this specification, the following unsubstituted alkynyls and the like can be cited. (Here, the unsubstituted alkynyl refers to the case where the "substituted or unsubstituted alkynyl" is an "unsubstituted alkynyl".) Hereinafter, when simply referred to as "alkynyl", it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0270] The "substituted alkynyl" is a case where the "unsubstituted alkynyl" has a substituent, and groups in which the following "unsubstituted alkynyl" has a substituent and the like can be cited.

[0271] Unsubstituted alkynyl:

[0272] Ethynyl

[0273] As a specific example (specific example group G6) of the "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyls and substituted cycloalkyls and the like can be cited. (Here, the unsubstituted cycloalkyl refers to the case where the "substituted or unsubstituted cycloalkyl" is an "unsubstituted cycloalkyl", and the substituted cycloalkyl refers to the case where the "substituted or unsubstituted cycloalkyl" is a "substituted cycloalkyl".) Hereinafter, when simply referred to as "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0274] The "substituted cycloalkyl" is a case where the "unsubstituted cycloalkyl" has a substituent, and examples of groups in which the following "unsubstituted cycloalkyl" has a substituent, substituted cycloalkyls, and the like can be cited. It should be noted that the examples of the "unsubstituted cycloalkyl" and the "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes groups in which the group in which the "unsubstituted cycloalkyl" has a substituent further has a substituent, groups in which the "substituted cycloalkyl" further has a substituent, and the like.

[0275] Unsubstituted aliphatic cycloalkyl:

[0276] Cyclopropyl,

[0277] Cyclobutyl,

[0278] Cyclopentyl,

[0279] Cyclohexyl,

[0280] 1-Adamantyl,

[0281] 2-Adamantyl,

[0282] 1-Norbornanyl,

[0283] 2-Norbornanyl

[0284] Substituted cycloalkyl:

[0285] 4-Methylcyclohexyl

[0286] As a specific example (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ), examples include

[0287] -Si(G1)(G1)(G1),

[0288] -Si(G1)(G2)(G2),

[0289] -Si(G1)(G1)(G2),

[0290] -Si(G2)(G2)(G2),

[0291] -Si(G3)(G3)(G3),

[0292] -Si(G5)(G5)(G5),

[0293] -Si(G6)(G6)(G6).

[0294] Here,

[0295] G1 is the "aryl group" described in specific example group G1.

[0296] G2 is the "heterocyclic group" described in specific example group G2.

[0297] G3 is the "alkyl group" described in specific example group G3.

[0298] G5 is the "alkynyl group" described in specific example group G5.

[0299] G6 is the "cycloalkyl group" described in specific example group G6.

[0300] As a specific example (specific example group G8) of the group represented by -O-(R 904 ), examples include

[0301] -O(G1),

[0302] -O(G2),

[0303] -O(G3),

[0304] -O(G6).

[0305] Here,

[0306] G1 is the "aryl group" described in specific example group G1.

[0307] G2 is the "heterocyclic group" described in specific example group G2.

[0308] G3 is the "alkyl group" described in specific example group G3.

[0309] G6 is the "cycloalkyl group" described in specific example group G6.

[0310] As a specific example of the group represented by -S-(R 905 )(specific example group G9) described in this specification, examples include

[0311] -S(G1),

[0312] -S(G2),

[0313] -S(G3),

[0314] -S(G6).

[0315] Here,

[0316] G1 is the "aryl group" described in specific example group G1.

[0317] G2 is the "heterocyclic group" described in specific example group G2.

[0318] G3 is the "alkyl group" described in specific example group G3.

[0319] G6 is the "cycloalkyl group" described in specific example group G6.

[0320] As a specific example of the group represented by -N(R 906 )(R 907 )(specific example group G10) described in this specification, examples include

[0321] -N(G1)(G1),

[0322] -N(G2)(G2),

[0323] -N(G1)(G2),

[0324] -N(G3)(G3),

[0325] -N(G6)(G6).

[0326] Here,

[0327] G1 is the "aryl group" described in specific example group G1.

[0328] G2 is the "heterocyclic group" described in specific example group G2.

[0329] G3 is the "alkyl group" described in specific example group G3.

[0330] G6 is the "cycloalkyl group" described in specific example group G6.

[0331] As specific examples (specific example group G11) of the "halogen atom" described in this specification, fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be cited.

[0332] As a specific example of the "alkoxy group" described in this specification, it is a group represented by -O(G3), where G3 is the "alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0333] As a specific example of the "alkylthio group" described in this specification, it is a group represented by -S(G3), where G3 is the "alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0334] As a specific example of the "aryloxy group" described in this specification, it is a group represented by -O(G1), where G1 is the "aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0335] As a specific example of the "arylthio group" described in this specification, it is a group represented by -S(G1), where G1 is the "aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0336] As a specific example of the "aralkyl group" described in this specification, it is a group represented by -(G3)-(G1), where G3 is the "alkyl group" described in specific example group G3 and G1 is the "aryl group" described in specific example group G1. Therefore, the "aralkyl group" is a form of "substituted alkyl" substituted by "aryl". Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl" substituted by "unsubstituted aryl", that is, the "unsubstituted aralkyl group", is 7 to 50, preferably 7 to 30, more preferably 7 to 18.

[0337] As specific examples of the "aralkyl group", for example, benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, etc. can be cited.

[0338] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-diphenylfluorenyl, etc.

[0339] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl, benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl, (9-biphenylyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, phenyldibenzothiophenyl, etc.

[0340] Unless otherwise specified in this specification, the above dibenzofuranyl and dibenzothiophenyl are specifically any of the following groups.

[0341] [Chemical formula 5]

[0342]

[0343] In formulas (XY-76) to (XY-79), X B is an oxygen atom or a sulfur atom.

[0344] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl group described in this specification is preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0345] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification means that the above "aryl group" forms a divalent group. As a specific example (specific example group G12) of the "substituted or unsubstituted arylene group", a divalent group formed by the "aryl group" described in specific example group G1 can be cited, etc.

[0346] As a specific example (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" described in this specification, a divalent group formed by the "heterocyclic group" described in specific example group G2 can be cited, etc.

[0347] As a specific example (specific example group G14) of the "substituted or unsubstituted alkylene group" described in this specification, there can be mentioned that the "alkyl group" described in specific example group G3 forms a divalent group or the like.

[0348] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably any of the following groups.

[0349] [Chemical formula 6]

[0350]

[0351] In formulas (XY-20) to (XY-29), R 908 is a substituent.

[0352] m901 is an integer from 0 to 4. When m901 is 2 or more, multiple Rs 908 may be the same as or different from each other.

[0353] [Chemical formula 7]

[0354]

[0355] In formulas (XY-30) to (XY-40), each R 909 is independently a hydrogen atom or a substituent. Two Rs 909 are bonded to each other through a single bond to form a ring, or do not form a ring.

[0356] [Chemical formula 8]

[0357]

[0358] In formulas (XY-41) to (XY-46), R 910 is a substituent.

[0359] m902 is an integer from 0 to 6. When m902 is 2 or more, multiple Rs 910 may be the same as or different from each other.

[0360] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the following groups.

[0361] [Chemical formula 9]

[0362]

[0363] In formulas (XY-50) to (XY-60), R 911 is a hydrogen atom or a substituent.

[0364] [Chemical formula 10]

[0365]

[0366] In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.

[0367] In this specification, for the case of "one or more groups of two or more adjacent groups bonding to each other to form a substituted or unsubstituted saturated or unsaturated ring", the case of an anthracene compound represented by the following formula (XY-80) having an anthracene ring as the main skeleton is described as an example.

[0368] [Chemical Formula 11]

[0369]

[0370] For example, when "one or more groups of two or more adjacent groups bond to each other to form a ring" among R 921 to R 930 , the two adjacent ones that form a group refer to R 921 and R 922 , R 922 and R 923 , R 923 and R 924 , R 924 and R 930 , R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .

[0371] The above "one or more groups" means that two or more groups of the above two adjacent groups can form a ring simultaneously. For example, when R 921 and R 922 bond to each other to form ring A, and at the same time R 925 and R 926 bond to each other to form ring B, it is represented by the following formula (XY-81).

[0372] [Chemical Formula 12]

[0373]

[0374] When "two or more adjacent groups" form a ring, it means that, for example, R 921 and R 922 bond to each other to form ring A, R 922 and R 923 bond to each other to form ring C, and R 921 to R923 When three adjacent ones among them form ring A and ring C which are condensed to the anthracene main skeleton and share R 922 they are represented by the following formula (XY-82).

[0375] [Chemical Formula 13]

[0376]

[0377] The formed rings A to C in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.

[0378] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.

[0379] For example, the R shown in the above formula (XY-81) 921 bonded to R 922 to form ring A means a ring formed by the carbon atoms of the anthracene skeleton bonded by R 921 , the carbon atoms of the anthracene skeleton bonded by R 922 , and one or more arbitrary elements. As a specific example, when ring A is formed by R 921 bonded to R 922 , when the carbon atoms of the anthracene skeleton bonded by R 921 , the carbon atoms of the anthracene skeleton bonded by R 922 , and form an unsaturated ring with 4 carbon atoms, the ring formed by R 921 bonded to R 922 forms a benzene ring. In addition, when a saturated ring is formed, a cyclohexane ring is formed.

[0380] Here, the "arbitrary element" is preferably a C element, an N element, an O element, or an S element. Among the arbitrary elements (for example, when it is a C element or an N element), the carbon atoms constituting the anthracene main skeleton that do not form a ring can be terminated with a hydrogen atom or the like, or can be substituted with an arbitrary substituent. When an arbitrary element other than the C element is included, the formed ring forms a heterocyclic ring.

[0381] The "one or more arbitrary elements" constituting the saturated or unsaturated ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less.

[0382] The substituents when the above "saturated or unsaturated ring" has substituents are as described above.

[0383] In one embodiment of the present specification, the substituents (hereinafter sometimes referred to as "arbitrary substituents") when the foregoing is referred to as "substituted or unsubstituted" are selected from

[0384] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0385] an alkenyl group having 2 to 50 unsubstituted carbon atoms,

[0386] an alkynyl group having 2 to 50 unsubstituted carbon atoms,

[0387] a cycloalkyl group having 3 to 50 unsubstituted ring-forming carbon atoms,

[0388] -Si(R 901 )(R 902 )(R 903 ),

[0389] -O-(R 904 ),

[0390] -S-(R 905 ),

[0391] -N(R 906 )(R 907 )

[0392] (wherein,

[0393] R 901 to R 907 are each independently

[0394] a hydrogen atom,

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

[0396] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0397] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0398] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted. When there are two or more R 901 to R 907 , the two or more R 901 to R 907 may be the same or different from each other.).

[0399] a halogen atom, a cyano group, a nitro group,

[0400] an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and

[0401] a group selected from a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.

[0402] In one embodiment, the substituent in the above-mentioned "substituted or unsubstituted" is selected from an alkyl group having 1 to 50 carbon atoms,

[0403] an aryl group having 6 to 50 ring-forming carbon atoms, and

[0404] A group in a monovalent heterocyclic group having 5 to 50 ring atoms.

[0405] In one embodiment, when the aforementioned is referred to as "substituted or unsubstituted", the substituent is selected from an alkyl group having 1 to 18 carbon atoms,

[0406] an aryl group having 6 to 18 ring carbon atoms, and

[0407] a group in a monovalent heterocyclic group having 5 to 18 ring atoms.

[0408] Specific examples of each group of the above-mentioned arbitrary substituents are as described above.

[0409] In this specification, unless otherwise defined, a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, more preferably a benzene ring) may be formed between any adjacent substituents.

[0410] In this specification, unless otherwise defined, any substituent may further have a substituent. Examples of the substituent that any substituent further has include the same groups as the above-mentioned arbitrary substituents.

[0411] [Organic electroluminescent element 1]

[0412] The organic electroluminescent element 1 of the first aspect of the present invention is an organic electroluminescent element having a cathode, an anode, and an organic layer between the aforementioned cathode and the aforementioned anode, and is characterized in that

[0413] the aforementioned organic layer contains a compound represented by the following formula (1) and a compound represented by the following formula (11).

[0414] [Chemical formula 14]

[0415]

[0416] Each substituent in the above formulas (1) and (2) will be described later.

[0417] Refer to Figure 1 to illustrate the schematic configuration of the organic EL element of the first aspect.

[0418] The organic EL element 1 of the first aspect has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10.

[0419] The compound represented by the above formula (1) and the compound represented by the above formula (11) are contained in the organic layers 4 to 6 between the anode 3 and the cathode 10, and are preferably contained in the light-emitting layer 5.

[0420] Each of the compound represented by the above formula (1) and the compound represented by the above formula (11) contained in the above organic layer may be a single kind or two or more kinds.

[0421] In formula (1), one or more of R1 to R8 are -L1-Ar1. That is, the anthracene compound of formula (1) has a structure substituted with three or more -L1-Ar1 groups. (Hereinafter, the compound represented by formula (1) is sometimes referred to as "3-substituted anthracene compound (1)" or "3-substituted anthracene-based host material (1)".)

[0422] There are known conventional anthracene-based host materials having two substituents corresponding to the above -L1-Ar1 group. (Hereinafter, it is sometimes referred to as "2-substituted anthracene compound".)

[0423] The inventors of the present invention used the 3-substituted anthracene compound (1) as the host material of the light-emitting layer and the fluoranthene compound represented by the formula (11) (hereinafter sometimes referred to as "fluoranthene-based compound (11)" or "fluoranthene-based dopant material (11)") as the dopant material, and as a result, it was found that the element lifetime was improved.

[0424] The organic EL element of the first aspect has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer is preferably a light-emitting layer. By containing the compound represented by the above formula (1) (hereinafter sometimes referred to as "3-substituted anthracene compound (1)" or "3-substituted anthracene-based host material (1)") and the compound represented by the above formula (11), the effect of improving the element lifetime is obtained. Furthermore, an organic EL element with a long element lifetime is obtained. The reason for speculation is described below.

[0425] Compared with the 2-substituted anthracene compound, the 3-substituted anthracene compound (1) has a high electron mobility and excess electrons, resulting in the deterioration of the surrounding materials, so a sufficient element lifetime cannot be obtained. On the other hand, it is considered that the compound represented by the above formula (11) can suppress the electron mobility by combining with the 3-substituted anthracene compound (1) having strong electron trapping properties, so the element lifetime is improved.

[0426] In addition, the inventors of the present invention also studied the combination of materials constituting the layer adjacent to the light-emitting layer containing the 3-substituted anthracene-based host material (1) and the fluoranthene-based dopant material (11). It was found that when using the compound represented by the following formula (21) (hereinafter sometimes referred to as an azine-based hole blocking layer material (21)) or the compound represented by the formula (31) (hereinafter sometimes referred to as a fluoranthene-based hole blocking layer material (31)) in the hole blocking layer adjacent to the light-emitting layer, a more excellent effect of improving the element lifetime is obtained.

[0427] Furthermore, it was also found that when a compound represented by the following formula (41) (hereinafter sometimes referred to as "monoamine-based electron blocking layer material (41)") is used in the electron blocking layer adjacent to the above-mentioned light-emitting layer, a long-life organic EL element is obtained, and the present invention is completed.

[0428] The organic EL element of the second aspect of the present invention is an organic EL element including the compound represented by the above formula (1) and the compound represented by the above formula (11) in the light-emitting layer, which is an embodiment of the organic EL element of the first aspect, and is characterized in that

[0429] The aforementioned organic layer further includes a hole blocking layer adjacent to the aforementioned light-emitting layer,

[0430] The aforementioned hole blocking layer contains any one or both of the compound represented by the following formula (21) and the compound represented by the following formula (31).

[0431] [Chemical formula 15]

[0432]

[0433] Each of the substituents in the above formulas (21) and (31) will be described later.

[0434] Refer to Figure 2 The schematic configuration of the organic EL element of the second aspect will be described.

[0435] The organic EL element 1a of the second aspect has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. In the organic layer 6 between the light-emitting layer 5 and the cathode 10, there is a hole blocking layer 6a adjacent to the light-emitting layer 5.

[0436] Each of the compound represented by the above formula (21) and the compound represented by the above formula (31) contained in the above hole blocking layer may be a single type or two or more types.

[0437] The organic EL element of the third aspect of the present invention is an organic EL element including the compound represented by the above formula (1) and the compound represented by the above formula (11) in the light-emitting layer, which is an embodiment of the organic EL element of the first aspect, and is characterized in that

[0438] The aforementioned organic layer further includes an electron blocking layer adjacent to the aforementioned light-emitting layer,

[0439] The aforementioned electron blocking layer contains any one or both of the compound represented by the following formula (41) and the compound represented by the following formula (51).

[0440] [Chemical formula 16]

[0441]

[0442] The substituents in the above formulas (41) and (51) will be described later.

[0443] Refer to Figure 3 Describe the schematic configuration of the organic EL element of the third mode.

[0444] The organic EL element 1b of the third mode has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. In the organic layer 4 between the anode 3 and the light-emitting layer 5, there is an electron blocking layer 4b adjacent to the light-emitting layer 5.

[0445] Each of the compound represented by the above formula (41) and the compound represented by the above formula (51) contained in the above electron blocking layer may be a single species or two or more species.

[0446] The organic EL element of the fourth mode of the present invention is an organic EL element that is an embodiment of the organic EL element of the first mode and contains the compound represented by the above formula (1) and the compound represented by the above formula (11) in the light-emitting layer, and is characterized in that

[0447] The aforementioned organic layer further includes a hole blocking layer adjacent to the aforementioned light-emitting layer,

[0448] The aforementioned hole blocking layer contains either one or both of the compound represented by the above formula (21) and the compound represented by the above formula (31),

[0449] The aforementioned organic layer further includes an electron blocking layer adjacent to the aforementioned light-emitting layer,

[0450] The aforementioned electron blocking layer contains either one or both of the compound represented by the above formula (41) and the compound represented by the above formula (51).

[0451] Refer to Figure 4 Describe the organic EL element of the fourth mode of the present invention.

[0452] The organic EL element 1c of the fourth mode, which is an embodiment of the organic EL elements of the first to third modes, has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. In the organic layer 6 between the light-emitting layer 5 and the cathode 10, there is a hole blocking layer 6a adjacent to the light-emitting layer 5, and in the organic layer 4 between the anode 3 and the light-emitting layer 5, there is an electron blocking layer 4b adjacent to the light-emitting layer 5.

[0453] The organic layer includes a light-emitting layer 5, a hole-blocking layer 6a, and an electron-blocking layer 4b, and contains specific compounds in each layer, whereby an improvement effect in the element lifetime can be obtained.

[0454] The organic EL element according to the fifth aspect of the present invention has a so-called tandem structure having two or more light-emitting layers. By having such a tandem structure, a white light-emitting element with a simple structure can be manufactured.

[0455] The organic EL element according to one aspect of the present invention can be, for example, a monochromatic light-emitting element of fluorescence or phosphorescence light emission type, or a white light-emitting element of fluorescence / phosphorescence hybrid type. Further, it can be a single type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units.

[0456] Herein, the "light-emitting unit" means a minimum unit that contains an organic layer, at least one layer of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0457] In addition, the "light-emitting layer" described in this specification means an organic layer having a light-emitting function. The light-emitting layer can be, for example, a phosphorescent light-emitting layer, a fluorescent light-emitting layer, etc., and can be one layer or multiple layers.

[0458] The light-emitting unit can be a stacked type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, for example, a spacer layer for preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer can be provided between each light-emitting layer.

[0459] As a single-type organic EL element, for example, an element configuration such as an anode / light-emitting unit / cathode can be cited.

[0460] A representative layer configuration of the light-emitting unit is shown below. The layers in parentheses are optional.

[0461] (a) (Hole injection layer / ) / Hole transport layer / Fluorescent light-emitting layer( / Electron transport layer / Electron injection layer)

[0462] (b) (Hole injection layer / ) / Hole transport layer / Phosphorescent light-emitting layer( / Electron transport layer / Electron injection layer)

[0463] (c) (Hole injection layer / ) / Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer( / Electron transport layer / Electron injection layer)

[0464] (d) (Hole injection layer / ) / Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer( / Electron transport layer / Electron injection layer) (e) (Hole injection layer / ) / Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / Fluorescent light-emitting layer( / Electron transport layer / Electron injection layer)

[0465] (f) (Hole injection layer / ) Hole transport layer / First phosphorescent emission layer / Second phosphorescent emission layer / Spacer layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0466] (g) (Hole injection layer / ) Hole transport layer / First phosphorescent emission layer / Spacer layer / Second phosphorescent emission layer / Spacer layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0467] (h) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Spacer layer / First fluorescent emission layer / Second fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0468] (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0469] (j) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent emission layer ( / Electron transport layer / Electron injection layer)

[0470] (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0471] (l) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent emission layer ( / Electron transport layer / Electron injection layer)

[0472] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[0473] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer ( / First electron transport layer / Second electron transport layer / Electron injection layer)

[0474] (o) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer ( / Electron transport layer / Electron injection layer)

[0475] (p) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer ( / First electron transport layer / Second electron transport layer / Electron injection layer)

[0476] (q) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Hole blocking layer ( / Electron transport layer / Electron injection layer)

[0477] (r) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Hole blocking layer ( / Electron transport layer / Electron injection layer)

[0478] (s) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Exciton blocking layer ( / Electron transport layer / Electron injection layer)

[0479] (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Exciton blocking layer ( / Electron transport layer / Electron injection layer)

[0480] Among them, the layer structure of the organic EL element according to one embodiment of the present invention is not limited thereto. For example, when the organic EL element has a hole injection layer and a hole transport layer, it is preferable to provide a hole injection layer between the hole transport layer and the anode. In addition, when the organic EL element has an electron injection layer and an electron transport layer, it is preferable to provide an electron injection layer between the electron transport layer and the cathode. In addition, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or multiple layers.

[0481] The plurality of phosphorescent emission layers and the phosphorescent emission layer and the fluorescent emission layer may each be emission layers having different colors. For example, the aforementioned light emitting unit (f) may be a hole transport layer / first phosphorescent emission layer (red emission) / second phosphorescent emission layer (green emission) / spacer layer / fluorescent emission layer (blue emission) / electron transport layer.

[0482] It should be noted that an electron blocking layer may be provided between each emission layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be provided between each emission layer and the electron transport layer. By providing the electron blocking layer and the hole blocking layer, electrons or holes can be confined within the emission layer, increasing the recombination probability of charges in the emission layer and improving the emission efficiency.

[0483] As a representative element structure of the tandem organic EL element, for example, an element structure such as anode / first light emitting unit / intermediate layer / second light emitting unit / cathode can be cited.

[0484] The first light emitting unit and the second light emitting unit can each be independently selected from the above-mentioned light emitting units, for example.

[0485] The intermediate layer is usually also referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, a connector layer, or an intermediate insulating layer. The intermediate layer is a layer that supplies electrons to the first light emitting unit and holes to the second light emitting unit, and can be formed of a known material.

[0486] Refer to Figure 5 Explain the schematic structure of one embodiment of the organic EL element according to the fifth embodiment of the present invention.

[0487] Figure 5The organic EL element 1d according to the fifth embodiment of the present invention shown has a substrate 2, an anode 3, a cathode 10, and an organic layer between the anode 3 and the cathode 10. The organic layer has a first light-emitting unit 5A, a second light-emitting unit 5B between the first light-emitting unit 5A and the cathode 10, an organic layer 4a between the anode 3 and the first light-emitting unit 5A, and an organic layer 6b between the second light-emitting unit 5B and the cathode 10. A charge generation layer 8 is provided between the first light-emitting unit 5A and the second light-emitting unit 5B.

[0488] [Organic electroluminescent element 2]

[0489] An organic electroluminescent element 2 according to another embodiment of the present invention is an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, and is characterized in that

[0490] the organic layer contains the compound represented by the foregoing formula (1), and

[0491] a compound A having a Stokes shift of 20 nm or less and an emission peak wavelength of 440 nm to 465 nm.

[0492] Here, the "Stokes shift (SS)" is the difference between the maximum wavelength of the absorption spectrum and the maximum wavelength of the fluorescence spectrum, and can be measured by the method described in the examples.

[0493] Each substituent in the above formula (1) and the compound A will be described later.

[0494] In addition, instead of the compound represented by formula (11) in the above organic EL element 1, compound A is used. Except for this, the configuration of the organic EL element of the above first to fifth embodiments is the same as that of the organic EL element 2.

[0495] It has been found that when the compound represented by the above formula (1) is combined with a compound A having a small Stokes shift (SS) and blue emission, compared with the case of combining with a compound having a large Stokes shift (SS) and blue emission, energy transfer can be easily caused and the efficiency can be sufficiently improved. Therefore, it can be applied as an organic EL element for blue fluorescence. In addition, it has been found that compared with the case of combining a 2-substituted anthracene compound and compound A, a blue fluorescent organic EL element with long life can be obtained by driving at a low voltage.

[0496] In one embodiment, the Stokes shift of the foregoing compound A is 15 nm or less. The smaller the Stokes shift, the further the energy transfer efficiency is improved.

[0497] [Compound represented by formula (1)]

[0498] Next, the compound represented by formula (1) will be described.

[0499] [Chemical Formula 17]

[0500]

[0501] [In formula (1),

[0502] One or more of R1 to R8 is -L 13 -Ar 13 .

[0503] L 11 ~L 13 Each independently is

[0504] A single bond,

[0505] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0506] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0507] L 13 When there are two or more Ls, the two or more Ls 13 May be the same or different from each other.

[0508] Ar 11 ~Ar 13 Each independently is

[0509] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0510] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0511] Ar 13 When there are two or more Ar, the two or more Ar 13 May be the same or different from each other.

[0512] Those of R1 to R8 that are not -L 13 -Ar 13 Each independently is

[0513] A hydrogen atom,

[0514] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0515] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0516] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0517] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0518] -Si(R 901 )(R 902)(R 903 )、

[0519] -O-(R 904 )、

[0520] -S-(R 905 )、

[0521] -N(R 906 )(R 907 )、

[0522] a halogen atom, a cyano group, a nitro group,

[0523] an aryl group having 6 to 50 ring-constituting carbon atoms which is substituted or unsubstituted, or

[0524] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which is substituted or unsubstituted.

[0525] R 901 ~R 907 are each independently

[0526] a hydrogen atom,

[0527] an alkyl group having 1 to 50 carbon atoms which is substituted or unsubstituted,

[0528] a cycloalkyl group having 3 to 50 ring-constituting carbon atoms which is substituted or unsubstituted,

[0529] an aryl group having 6 to 50 ring-constituting carbon atoms which is substituted or unsubstituted, or

[0530] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which is substituted or unsubstituted. When there are two or more of R 901 ~R 907 two or more of R 901 ~R 907 may be the same or different from each other.]

[0531] It should be noted that R1 to R8 of -L 11 -Ar 11 , -L 12 -Ar 12 , -L 13 -Ar 13 , and -L 13 -Ar 13 do not bond to each other to form a ring condensed into an anthracene ring.

[0532] In one embodiment, L 11 ~L 13 in the aforementioned formula (1) are each independently a single bond, or

[0533] an arylene group having 6 to 50 ring-constituting carbon atoms which is substituted or unsubstituted.

[0534] In one embodiment, L in the aforementioned formula (1) 11 ~L 13 are each independently a single bond or selected from

[0535] a substituted or unsubstituted phenylene group,

[0536] a substituted or unsubstituted biphenylene group,

[0537] a substituted or unsubstituted terphenyl group,

[0538] a substituted or unsubstituted quaterphenyl group, and

[0539] a substituted or unsubstituted naphthylene group.

[0540] In one embodiment, Ar in the aforementioned formula (1) 11 ~Ar 13 are each independently an aryl group having 6 to 30 ring carbon atoms which may be substituted or unsubstituted.

[0541] In one embodiment, Ar in the aforementioned formula (1) 11 ~Ar 13 are each independently selected from

[0542] a substituted or unsubstituted phenyl group,

[0543] a substituted or unsubstituted naphthyl group,

[0544] a substituted or unsubstituted fluorenyl group,

[0545] a substituted or unsubstituted 9,9'-spirobifluorenyl group,

[0546] a substituted or unsubstituted benzofluorenyl group,

[0547] a substituted or unsubstituted phenanthryl group, and

[0548] a substituted or unsubstituted benzo[ghi]phenanthryl group.

[0549] In one embodiment, one or more of Ar in the aforementioned formula (1) 11 ~Ar 13 are each independently a monovalent heterocyclic group having 5 to 30 ring atoms which may be substituted or unsubstituted.

[0550] In one embodiment, the group represented by -L 13 -Ar 13 in the aforementioned formula (1) is selected from

[0551] a substituted or unsubstituted phenyl group,

[0552] a substituted or unsubstituted naphthyl group,

[0553] Substituted or unsubstituted biphenyl,

[0554] substituted or unsubstituted phenanthryl,

[0555] substituted or unsubstituted benzophenanthryl,

[0556] substituted or unsubstituted fluorenyl,

[0557] substituted or unsubstituted benzofluorenyl,

[0558] substituted or unsubstituted dibenzofuranyl,

[0559] substituted or unsubstituted naphthobenzofuranyl,

[0560] substituted or unsubstituted dibenzothiophenyl, and

[0561] substituted or unsubstituted carbazolyl.

[0562] In one embodiment, the compound represented by the foregoing formula (1) is the compound represented by the following formula (1-1).

[0563] [Chemical 18]

[0564]

[0565] [In formula (1-1), L 11 ~L 13 , Ar 11 ~Ar 13 , R1, R3, R4, and R5~R8 are as defined in the foregoing formula (1).]

[0566] In one embodiment, the compound represented by the foregoing formula (1) is the compound represented by the following formula (1-1H).

[0567] [Chemical 19]

[0568]

[0569] [In formula (1-1H), L 11 ~L 13 and Ar 11 ~Ar 13 are as defined in the foregoing formula (1).]

[0570] In one embodiment, the compound represented by the foregoing formula (1) is selected from the compounds represented by the following formula (1-2), the compounds represented by the following formula (1-3), and the compounds represented by the following formula (1-4).

[0571] [Chemical 20]

[0572]

[0573] In Formulae (1-2) to (1-4), L 11 , L 12 , Ar 11 , Ar 12 , R1, R3, R4, and R5 to R8 are as defined in the aforementioned Formula (1).

[0574] In one embodiment, R1 to R8 in the aforementioned Formula (1) that are not -L 13 -Ar 13 are hydrogen atoms.

[0575] Details of each substituent in the above Formula (1) are as described in the [Definition] section of this specification. Hereinafter, the same applies to each substituent in the above Formulae (11), (21), (31), (41), and (51).

[0576] Specific examples of the compound represented by Formula (1) are described below, but these are merely illustrative, and the compound represented by Formula (1) is not limited to the following specific examples.

[0577] [Chemical Formula 21]

[0578]

[0579] [Chemical Formula 22]

[0580]

[0581] [Chemical Formula 23]

[0582]

[0583] [Chemical Formula 24]

[0584]

[0585] [Chemical Formula 25]

[0586]

[0587] [Chemical Formula 26]

[0588]

[0589] [Chemical Formula 27]

[0590]

[0591] [Chemical Formula 28]

[0592]

[0593] [Chemical Formula 29]

[0594]

[0595] [Chemical formula 30]

[0596]

[0597] [Chemical formula 31]

[0598]

[0599] [Chemical formula 32]

[0600]

[0601] [Chemical formula 33]

[0602]

[0603] [Chemical formula 34]

[0604]

[0605] [Chemical formula 35]

[0606]

[0607] [Chemical formula 36]

[0608]

[0609] [Chemical formula 37]

[0610]

[0611] [Chemical formula 38]

[0612]

[0613] [Chemical formula 39]

[0614]

[0615] [Chemical formula 40]

[0616]

[0617] [Chemical formula 41]

[0618]

[0619] [Chemical formula 42]

[0620]

[0621] [Chemical formula 43]

[0622]

[0623] [Chemical Formula 44]

[0624]

[0625] [Chemical Formula 45]

[0626]

[0627] [Chemical Formula 46]

[0628]

[0629] [Chemical Formula 47]

[0630]

[0631] [Chemical Formula 48]

[0632]

[0633] [Chemical Formula 49]

[0634]

[0635] [Chemical Formula 50]

[0636]

[0637] [Chemical Formula 51]

[0638]

[0639] [Chemical Formula 52]

[0640]

[0641] [Chemical Formula 53]

[0642]

[0643] [Chemical Formula 54]

[0644]

[0645] [Chemical Formula 55]

[0646]

[0647] [Chemical Formula 56]

[0648]

[0649] [Chemical Formula 57]

[0650]

[0651] [Chemical Formula 58]

[0652]

[0653] [Chemical formula 59]

[0654]

[0655] [Chemical formula 60]

[0656]

[0657] [Chemical formula 61]

[0658]

[0659] [Chemical formula 62]

[0660]

[0661] [Chemical formula 63]

[0662]

[0663] [Chemical formula 64]

[0664]

[0665] [Chemical formula 65]

[0666]

[0667] [Chemical formula 66]

[0668]

[0669] [Chemical formula 67]

[0670]

[0671] [Chemical formula 68]

[0672]

[0673] [Chemical formula 69]

[0674]

[0675] [Chemical formula 70]

[0676]

[0677] [Chemical formula 71]

[0678]

[0679] [Chemical formula 72]

[0680]

[0681] [Chemical Formula 73]

[0682]

[0683] [Chemical Formula 74]

[0684]

[0685] [Chemical Formula 75]

[0686]

[0687] [Chemical Formula 76]

[0688]

[0689] [Chemical Formula 77]

[0690]

[0691] [Chemical Formula 78]

[0692]

[0693] [Chemical Formula 79]

[0694]

[0695] [Chemical Formula 80]

[0696]

[0697] [Chemical Formula 81]

[0698]

[0699] [Chemical Formula 82]

[0700]

[0701] [The compound shown in Formula (11)]

[0702] Next, the compound shown in Formula (11) will be described.

[0703] [Chemical Formula 83]

[0704]

[0705] [In Formula (11),

[0706] R 11 ~R 20 One or more groups of two or more adjacent to each other among R a1 ~Ra5 One or more groups of two or more that are adjacent to each other, and R a6 ~R a10 Any one or more of the one or more groups of two or more that are adjacent to each other are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring atoms, which may be substituted or unsubstituted.

[0707] R that does not participate in the ring formation 11 ~R 20 、R a1 ~R a5 、and R a6 ~R a10 are each independently

[0708] a hydrogen atom,

[0709] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0710] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0711] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0712] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0713] a substituted or unsubstituted amino group,

[0714] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0715] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0716] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0717] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0718] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0719] a substituted or unsubstituted phosphino group,

[0720] a substituted or unsubstituted phosphoryl group,

[0721] a substituted or unsubstituted silyl group,

[0722] a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms,

[0723] a cyano group, a nitro group, a carboxyl group, or

[0724] a halogen atom.]

[0725] R 11 ~R16 and R 17 to R 20 and R a1 to R a5 and R a6 to R a10 Any two or more of them that are adjacent to each other are bonded to each other to form at least one ring.

[0726] Regarding "R 11 to R 20 One or more groups of two or more that are adjacent to each other, R a1 to R a5 One or more groups of two or more that are adjacent to each other, and R a6 to R a10 One or more groups of two or more that are adjacent to each other" are bonded to each other to form a specific example of a saturated or unsaturated ring with 3 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[0727] As a specific example of two or more adjacent to each other being bonded to form a ring, taking R 17 to R 20 in the above formula (11) as an example, the following partial structures can be cited. In the following partial structures, the adjacent R 18 and R 19 and R 20 bond to each other to form a ring.

[0728] [Chemical Formula 84]

[0729]

[0730] In addition, as a specific example of "one or more groups of two or more that are adjacent to each other" being bonded to form a ring, taking R 11 to R 16 in the above formula (11) as an example, the following partial structures can be cited. In the following partial structures, R 12 and R 13 and R 14 and R 15 bond to each other in two groups to form another two rings.

[0731] [Chemical Formula 85]

[0732]

[0733] In one embodiment, R 12 and R 13 in the above formula (11) bond to each other to form a saturated or unsaturated ring with 3 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[0734] In one embodiment, the compound represented by the aforementioned formula (11) is the compound represented by the following formula (11-1).

[0735] [Chemical Formula 86]

[0736]

[0737] [In formula (11-1), R 11 , R 14 ~R 20 are as defined in the aforementioned formula (11).

[0738] R c1 and R c2 are each independently

[0739] a hydrogen atom,

[0740] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0741] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0742] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0743] an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0744] -Si(R 901 )(R 902 )(R 903 ),

[0745] -O-(R 904 ),

[0746] -S-(R 905 ),

[0747] -N(R 906 )(R 907 ),

[0748] a halogen atom, a cyano group, a nitro group,

[0749] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0750] a monovalent heterocyclic group having 5 to 50 ring atoms.

[0751] R 901 ~R 907 are each independently

[0752] a hydrogen atom,

[0753] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0754] A cycloalkyl group having 3 to 50 ring carbon atoms, which may or may not be substituted,

[0755] an aryl group having 6 to 50 ring carbon atoms, which may or may not be substituted, or

[0756] a monovalent heterocyclic group having 5 to 50 ring atoms, which may or may not be substituted. R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 may be the same or different from each other. ]

[0757] In one embodiment, two or more of R 18 ~R 20 in the foregoing formula (11) are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring atoms, which may or may not be substituted.

[0758] In one embodiment, the compound represented by the foregoing formula (11) is a compound represented by the following formula (11-2).

[0759] [Chemical formula 87]

[0760]

[0761] [In formula (11-2), R 11 ~R 17 is as defined in the foregoing formula (11). ]

[0762] In one embodiment, R 11 ~R 20 , R a1 ~R a5 , and R a6 ~R a10 not participating in ring formation in the foregoing formula (11) are each independently

[0763] a hydrogen atom,

[0764] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0765] an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0766] In one embodiment, the foregoing organic layer includes a light-emitting layer,

[0767] the foregoing light-emitting layer includes the compound represented by the foregoing formula (1), and the compound represented by the foregoing formula (11). At this time, the compound represented by the foregoing formula (1) functions as a host material of the light-emitting layer, and the compound represented by the foregoing formula (11) functions as a dopant material of the light-emitting layer.

[0768] Specific examples of the compound represented by formula (11) are described below, but these are merely illustrative, and the compound represented by formula (11) is not limited to the following specific examples.

[0769] [Chemical formula 88]

[0770]

[0771] [Chemical formula 89]

[0772]

[0773] [Chemical formula 90]

[0774]

[0775] [Chemical formula 91]

[0776]

[0777] [Chemical formula 92]

[0778]

[0779] [Chemical formula 93]

[0780]

[0781] [Chemical formula 94]

[0782]

[0783] [Chemical formula 95]

[0784]

[0785] [Chemical formula 96]

[0786]

[0787] [Chemical formula 97]

[0788]

[0789] [Chemical formula 98]

[0790]

[0791] [Chemical formula 99]

[0792]

[0793] [Compound A]

[0794] Compound A with a Stokes shift of 20 nm or less and an emission peak wavelength of 440 nm to 465 nm is described below.

[0795] Compound A is not particularly limited as long as the Stokes shift and the emission peak wavelength are within the above ranges, and it can be a compound having any chemical structure.

[0796] Generally, a molecule with a rigid structure in the molecule, in a state where rotational motion and interatomic vibration are suppressed, tends to have a smaller Stokes shift. By adopting such a highly rigid structural design, a compound with a Stokes shift of 20 nm or less can be obtained.

[0797] In one embodiment, the aforementioned organic layer includes a light-emitting layer.

[0798] The aforementioned light-emitting layer includes the compound represented by the aforementioned formula (1) and the aforementioned compound A. At this time, the compound represented by the aforementioned formula (1) functions as the host material of the light-emitting layer, and the aforementioned compound A functions as the dopant material of the light-emitting layer.

[0799] In one embodiment, the aforementioned compound A is one or more selected from the compounds represented by the following formula (A-1) and the compounds represented by the following formula (A-2).

[0800] [Compound represented by formula (A-1)]

[0801] [Chemical formula 100]

[0802]

[0803] (In formula (A-1),

[0804] Ring a, ring b, and ring c are each independently

[0805] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.

[0806] X 61 is B or N.

[0807] Y 62 and Y 63 are each independently NR d , O, S, or a single bond.

[0808] Among them, when X 61 is B, Y 62 and Y 63 are each independently NR d , O or S. When X 61 is N, Y 62 and Y 63 are a single bond.

[0809] R dBonded to the aforementioned a-ring, b-ring or c-ring to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle.

[0810] R that does not form the aforementioned substituted or unsubstituted heterocycle d Each independently is

[0811] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0812] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0813] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0814] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0815] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0816] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.)

[0817] In one embodiment, the compound represented by the aforementioned formula (A-1) is the compound represented by the following formula (A-1-1).

[0818] [Chemical formula 101]

[0819]

[0820] (In formula (A-1-1),

[0821] R f Is a substituent.

[0822] m1 is an integer from 0 to 5.

[0823] m2 is an integer from 0 to 4.

[0824] m3 is an integer from 0 to 3.

[0825] When m1 to m3 are 2 or more, two or more Rs f May be the same or different from each other.)

[0826] In one embodiment, R f Each independently is

[0827] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0828] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0829] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0830] A cycloalkyl group having 3 to 50 ring carbon atoms, which may be substituted or unsubstituted,

[0831] -Si(R 901 )(R 902 )(R 903 ),

[0832] -O-(R 904 ),

[0833] -S-(R 905 ),

[0834] -N(R 906 )(R 907 ),

[0835] a halogen atom, a cyano group, a nitro group,

[0836] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted, or

[0837] a monovalent heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted.

[0838] R 901 to R 907 are each independently

[0839] a hydrogen atom,

[0840] an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[0841] a cycloalkyl group having 3 to 50 ring carbon atoms, which may be substituted or unsubstituted,

[0842] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted, or

[0843] a monovalent heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted. When there are two or more R 901 to R 907 , two or more R 901 to R 907 may be the same or different from each other.

[0844] Specific examples of the compound represented by the following formula (A-1) are shown below, but these are only illustrative, and the compound represented by formula (A-1) is not limited to the following specific examples.

[0845] [Chemical formula 102]

[0846]

[0847] [Compound represented by formula (A-2)]

[0848] [Chemical formula 103]

[0849]

[0850] (In formula (A-2),

[0851] d ring is a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, or

[0852] a substituted or unsubstituted heterocyclic ring having 12 to 50 ring-forming atoms.

[0853] L 71 to L 74 are each independently

[0854] a single bond,

[0855] a substituted or unsubstituted arylene having 6 to 50 ring-forming carbon atoms, or

[0856] a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted.

[0857] Ar 71 to Ar 74 are each independently

[0858] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0859] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0860] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0861] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted.

[0862] Among them, when d ring is a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, two or more of Ar 71 to Ar 74 are aryl groups having 6 to 50 ring-forming carbon atoms substituted with alkyl groups having 1 to 50 carbon atoms, or monovalent heterocyclic groups having 5 to 50 ring-forming atoms substituted with alkyl groups having 1 to 50 carbon atoms.)

[0863] In one embodiment, the compound represented by the aforementioned formula (A-2) is the compound represented by the following formula (A-2-1).

[0864] [Chemical 104]

[0865]

[0866] (In formula (A-2-1), L 71 to L 74 and Ar 71 to Ar 74 are defined as in the aforementioned formula (A-2).

[0867] d A The ring is an aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms which is substituted or unsubstituted.)

[0868] In one embodiment, d A The ring is a substituted or unsubstituted pyrene ring.

[0869] In one embodiment, d A The substituent of the ring is

[0870] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0871] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0872] -Si(R 901 )(R 902 )(R 903 ),

[0873] a halogen atom, a cyano group, or a nitro group.

[0874] R 901 ~R 903 are each independently

[0875] a hydrogen atom,

[0876] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0877] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

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

[0879] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted. When there are two or more R 901 ~R 903 When there are two or more, two or more R 901 ~R 903 may be the same or different from each other.

[0880] In another embodiment of the foregoing formula (A-2), the compound represented by the foregoing formula (A-2) is a compound represented by the following formula (A-2-2).

[0881] [Chemical formula 105]

[0882]

[0883] (In formula (A-2-2), L 71 ~L 74 and Ar 71 ~Ar 74As defined in the aforementioned formula (A-2).

[0884] d B The ring is a hetero ring having 12 to 50 ring-forming atoms which is substituted or unsubstituted.)

[0885] In one embodiment, d B The ring is selected from substituted or unsubstituted hetero rings having the following structures.

[0886] [Chemical formula 106]

[0887]

[0888] In one embodiment, d B The substituent of the ring is

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

[0890] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0891] -Si(R 901 )(R 902 )(R 903 ),

[0892] a halogen atom, a cyano group, or a nitro group.

[0893] R 901 ~R 903 are each independently

[0894] a hydrogen atom,

[0895] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0896] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

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

[0898] a substituted or unsubstituted monovalent hetero ring group having 5 to 50 ring-forming atoms. R 901 ~R 903 When there are two or more, two or more R 901 ~R 903 may be the same or different from each other.

[0899] Specific examples of the compound represented by the following formula (A-2) are described below, but these are merely illustrative, and the compound represented by the formula (A-2) is not limited to the following specific examples.

[0900] [Chemical formula 107]

[0901]

[0902] In the organic EL element of the second embodiment of the present invention,

[0903] the organic layer further includes a hole blocking layer adjacent to the light emitting layer,

[0904] and the hole blocking layer contains any one or both of the compounds represented by the following formula (21) and the compounds represented by the following formula (31).

[0905] Here, the "hole blocking layer" is a layer provided between the light emitting layer and the electron transport layer for the function of preventing holes from leaking from the light emitting layer to the electron transport layer, and is also a layer having the function of transporting electrons injected from the cathode to the light emitting layer as an electron transport layer.

[0906] [Compound represented by formula (21)]

[0907] The compound represented by formula (21) will be described below.

[0908] [Chemical formula 108]

[0909]

[0910] [In formula (21),

[0911] X1 to X3 are each independently N or CR b . Among them, one or more of X1 to X3 are N.

[0912] R b is

[0913] a hydrogen atom,

[0914] a halogen atom,

[0915] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0916] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0917] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0918] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0919] R b When there are 2, the two Rs b may be the same or different from each other. R b does not bond with the adjacent Rs 21 to R 23 to form a ring.

[0920] R 21 to R23 Each independently is

[0921] -(L2) m -(Ar2) n 、

[0922] a hydrogen atom,

[0923] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0924] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0925] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0926] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0927] -Si(R 901 )(R 902 )(R 903 ),

[0928] -O-(R 904 ),

[0929] -S-(R 905 ),

[0930] -N(R 906 )(R 907 ),

[0931] a halogen atom, a cyano group, a nitro group,

[0932] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0933] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0934] R 901 ~R 907 Each independently is

[0935] a hydrogen atom,

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

[0937] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0938] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0939] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are two or more R 901 ~R 907 When there are two or more, two or more R 901 ~R907 They may be the same or different from each other.

[0940] L2 is

[0941] a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or

[0942] a divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.

[0943] m is an integer from 0 to 2. When m is 0, L2 is a single bond. When m is 2, the two L2s may be the same or different from each other.

[0944] Ar2 is

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

[0946] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.

[0947] n is an integer of 1 or 2. When n is 2, the two Ar2s may be the same or different from each other. Among them, when n is 2, m is 1 or more.

[0948] In one embodiment, two of X1 to X3 in the aforementioned formula (21) are N. That is, the central skeleton is a pyrimidine ring.

[0949] In one embodiment, R in the aforementioned formula (21) 21 ~R 23 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0950] In one embodiment, the compound represented by the aforementioned formula (21) is the compound represented by the following formula (21-1).

[0951] [Chemical 109]

[0952]

[0953] [In formula (21-1), R 21 、R 22 and X3 are as defined in the aforementioned formula (21).

[0954] R 51 ~R 55 are each independently

[0955] a hydrogen atom,

[0956] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0957] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0958] An alkynyl group having 2 to 50 unsubstituted carbon atoms,

[0959] a cycloalkyl group having 3 to 50 unsubstituted ring-forming carbon atoms,

[0960] -Si(R 901 )(R 902 )(R 903 ),

[0961] -O-(R 904 ),

[0962] -S-(R 905 ),

[0963] -N(R 906 )(R 907 ),

[0964] a halogen atom, a cyano group, a nitro group,

[0965] an aryl group having 6 to 50 unsubstituted ring-forming carbon atoms, or

[0966] a monovalent heterocyclic group having 5 to 50 unsubstituted ring-forming atoms.

[0967] Two or more of adjacent R 51 to R 55 bond to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or do not form a ring.

[0968] R 901 to R 907 are each independently

[0969] a hydrogen atom,

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

[0971] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0972] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0973] a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. When there are two or more of R 901 to R 907 , two or more of R 901 to R 907 may be the same or different.]

[0974] In one embodiment, the compound represented by the aforementioned formula (21-1) is the compound represented by the following formula (21-2).

[0975] [Chemical Formula 110]

[0976]

[0977] [In formula (21-2), R 22 , X3 and R 51 ~R 55 are defined as in the aforementioned formula (21-1).

[0978] R 56 ~R 60 are each independently

[0979] a hydrogen atom,

[0980] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0981] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0982] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0983] an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0984] -Si(R 901 )(R 902 )(R 903 ),

[0985] -O-(R 904 ),

[0986] -S-(R 905 ),

[0987] -N(R 906 )(R 907 ),

[0988] a halogen atom, a cyano group, a nitro group,

[0989] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0990] a monovalent heterocyclic group having 5 to 50 ring atoms.

[0991] R 901 ~R 907 are each independently

[0992] a hydrogen atom,

[0993] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0994] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0995] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0996] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted. R 901 ~R 907 When there are two or more, two or more R's 901 ~R 907 may be the same or different from each other.]

[0997] In one embodiment, the compound represented by the aforementioned formula (21-2) is the compound represented by the following formula (21-3).

[0998] [Chemical Formula 111]

[0999]

[1000] [In formula (21-3), R 22 , X3 and R 56 ~R 60 are as defined in the aforementioned formula (21-2). Y 1a ~Y 8a are each independently CR 61a or N.

[1001] Y 1b ~Y 8b are each independently CR 61b or N.

[1002] X 4a is O, S or NR 61a .

[1003] X 4b is O, S or NR 61b .

[1004] R 61a and R 61b are each independently

[1005] a hydrogen atom,

[1006] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[1007] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1008] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1009] an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

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

[1011] -O-(R 904 ),

[1012] -S-(R 905 )、

[1013] -N(R 906 )(R 907 )、

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

[1015] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1016] an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1017] R 901 ~R 907 each independently is

[1018] a hydrogen atom,

[1019] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1020] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1021] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1022] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are two or more R 901 ~R 907 two or more R 901 ~R 907 may be the same or different from each other.

[1023] R 61a When there are a plurality of R 61a they may be the same or different from each other.

[1024] R 61b When there are a plurality of R 61b they may be the same or different from each other.

[1025] Two or more groups of R 61a substituted on adjacent atoms are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms, or do not form a ring.

[1026] Two or more groups of R 61b substituted on adjacent atoms are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms, or do not form a ring.

[1027] Among them, one R 61aA single bond bonded to *1, or R substituted on adjacent atoms as described above 61a Two or more groups of two or more of the above are bonded to each other to form a ring, and one atom constituting the ring is bonded to *1 by a single bond.

[1028] One R 61b A single bond bonded to *2, or R substituted on adjacent atoms as described above 61b Two or more groups of two or more of the above are bonded to each other to form a ring, and one atom constituting the ring is bonded to *2 by a single bond.]

[1029] Here, as "one R 61a is a single bond bonded to a benzene ring, or R 61c is a single bond bonded to *1", specific examples of the group composed of X 4a and Y 1a to Y 8a are, for example, the following groups.

[1030] [Chemical Formula 112]

[1031]

[1032] In addition, as "R substituted on adjacent atoms as described above 61a Two or more groups of two or more of which are bonded to each other to form a ring, and one atom constituting the ring is bonded to a carbon atom of a benzene ring by a single bond", specific examples of the group composed of X 4a and Y 1a to Y 8a are, for example, the following groups.

[1033] [Chemical Formula 113]

[1034]

[1035] In one embodiment, the compound represented by the above formula (21) is the compound represented by the following formula (21-4).

[1036] [Chemical Formula 114]

[1037]

[1038] [In formula (21-4), X1 to X3, R 21 , R 22 , L2, m and n are as defined in the above formula (21).

[1039] Y1 to Y8 are each independently CR 61e or N.

[1040] X4 is O, S or NR 61e .

[1041] R 61e each independently is

[1042] a hydrogen atom,

[1043] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[1044] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1045] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1046] an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1047] -Si(R 901 )(R 902 )(R 903 ),

[1048] -O-(R 904 ),

[1049] -S-(R 905 ),

[1050] -N(R 906 )(R 907 ),

[1051] a halogen atom, a cyano group, a nitro group,

[1052] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1053] a monovalent heterocyclic group having 5 to 50 ring atoms.

[1054] R 901 to R 907 each independently is

[1055] a hydrogen atom,

[1056] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1057] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1058] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1059] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 to R 907 When there are two or more, two or more R 901 to R 907 may be the same or different from each other.

[1060] R 61eWhen there are multiple, multiple Rs 61e They may be the same as or different from each other.

[1061] Rs substituted on adjacent atoms 61e Two or more groups of two or more of them are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms which may be substituted or unsubstituted, or no ring is formed.

[1062] Among them, one of the Rs 61e is a single bond bonded to *3, or two or more groups of two or more of the aforementioned Rs substituted on adjacent atoms 61e are bonded to each other to form a ring, and one of the atoms constituting the ring is bonded to *3 through a single bond.

[1063] Specific examples of the compound represented by the following formula (21) are described below, but these are merely illustrative, and the compound represented by the formula (21) is not limited to the following specific examples.

[1064] [Chemical formula 115]

[1065]

[1066] [Compound represented by formula (31)]

[1067] The compound represented by the formula (31) is described below.

[1068] [Chemical formula 116]

[1069]

[1070] [In formula (31),

[1071] One or more of the Rs 31 to R 40 are -(L3) p -Ar3. When there are two or more -(L3) p -Ar3s, two or more -(L3) p -Ar3s may be the same as or different from each other.

[1072] L3 is

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

[1074] a divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.

[1075] p is an integer of 0 to 3. When p is 0, L3 is a single bond. When p is 2 or more, multiple L3s may be the same as or different from each other.

[1076] Ar3 is

[1077] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1078] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1079] Not -(L3) p -Ar3's R 31 ~R 36 、and not -(L3) p -Ar3's R 37 ~R 40 Two or more groups of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms, or do not form a ring.

[1080] R that does not participate in the ring formation 31 ~R 40 Each independently is

[1081] A hydrogen atom,

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

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

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

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

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

[1087] -O-(R 904 ),

[1088] -S-(R 905 ),

[1089] -N(R 906 )(R 907 ),

[1090] A halogen atom, a cyano group, a nitro group,

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

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

[1093] R 901 ~R 907 Each independently is

[1094] A hydrogen atom,

[1095] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[1096] A cycloalkyl group having 3 to 50 ring-constituting carbon atoms, which may or may not be substituted,

[1097] An aryl group having 6 to 50 ring-constituting carbon atoms, which may or may not be substituted, or

[1098] A monovalent heterocyclic group having 5 to 50 ring-constituting atoms, which may or may not be substituted. When there are two or more R 901 ~R 907 When there are two or more, the two or more R 901 ~R 907 may be the same or different from each other.]

[1099] In one embodiment, p in the aforementioned formula (31) is preferably 0 or 1.

[1100] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (31-1).

[1101] [Chemical formula 117]

[1102]

[1103] [In formula (31-1), L3, p, Ar3, R 31 , R 32 , and R 34 ~R 40 are as defined in the aforementioned formula (31).]

[1104] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (31-1H).

[1105] [Chemical formula 118]

[1106]

[1107] [In formula (31-1H), L3, p, and Ar3 are as defined in the aforementioned formula (31).]

[1108] Specific examples of the compound represented by formula (31) are described below, but these are merely illustrative, and the compound represented by formula (31) is not limited to the following specific examples.

[1109] [Chemical formula 119]

[1110]

[1111] The organic EL element according to the third aspect of the present invention is characterized in that the aforementioned organic layer further includes an electron blocking layer adjacent to the aforementioned light-emitting layer,

[1112] The foregoing electron blocking layer contains any one or both of the compounds represented by the following formula (41) and the compounds represented by the following formula (51).

[1113] Herein, the "electron blocking layer" refers to a layer provided between the light-emitting layer and the hole transport layer for the function of preventing electrons from leaking from the light-emitting layer to the hole transport layer, and is also a layer having the function of transporting holes injected from the anode to the light-emitting layer as a hole transport layer.

[1114] [Compound represented by formula (41)]

[1115] The compound represented by formula (41) will be described below.

[1116] [Chemical formula 120]

[1117]

[1118] [In formula (41),

[1119] L 41 ~L 43 Each independently is

[1120] A single bond,

[1121] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1122] A divalent heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted.

[1123] Ar 41 ~Ar 43 Each independently is

[1124] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1125] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1126] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1127] A monovalent heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted.]

[1128] In one embodiment, the compound represented by the foregoing formula (41) is the compound represented by the following formula (41-1).

[1129] [Chemical formula 121]

[1130]

[1131] [In formula (41-1), Ar 41 ~Ar 43and L 41 as defined in the aforementioned formula (41).

[1132] Ar 42 and Ar 43 are each bonded to any carbon atom constituting the substituted phenyl group, respectively.

[1133] In one embodiment, the compound represented by the aforementioned formula (41) is the compound represented by the following formula (41-2).

[1134] [Chemical Formula 122]

[1135]

[1136] [In formula (41-2), Ar 41 and L 41 are as defined in the aforementioned formula (41).

[1137] X5 and X6 are each independently O, S, or N(R 906 ).

[1138] R 906 is

[1139] a hydrogen atom,

[1140] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1141] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1142] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1143] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are 2 R 906 s, the 2 R 906 s may be the same or different respectively.

[1144] Any one of the carbon atoms constituting one benzene ring of the monovalent heterocyclic group containing X5 or X6 is bonded to any one of the carbon atoms constituting the phenyl group substituted at the central nitrogen atom.

[1145] In one embodiment, the compound represented by the aforementioned formula (41) is the compound represented by the following formula (41-3).

[1146] [Chemical Formula 123]

[1147]

[1148] [In formula (41-3), Ar 41 , Ar 42 and L 41 to L 43As defined in the aforementioned formula (41).

[1149] X7 is O, S or NR 89 .

[1150] R 81 ~R 89 Each independently is

[1151] a hydrogen atom,

[1152] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[1153] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1154] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1155] an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1156] -Si(R 901 )(R 902 )(R 903 ),

[1157] -O-(R 904 ),

[1158] -S-(R 905 ),

[1159] -N(R 906 )(R 907 ),

[1160] a halogen atom, a cyano group, a nitro group,

[1161] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1162] a monovalent heterocyclic group having 5 to 50 ring atoms.

[1163] R 901 ~R 907 Each independently is

[1164] a hydrogen atom,

[1165] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[1167] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1168] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907When there are two or more, two or more Rs 901 ~R 907 may be the same or different from each other.

[1169] Rs substituted on adjacent atoms 81 ~R 89 Two or more groups of two or more of them are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms which may be substituted or unsubstituted, or do not form a ring.

[1170] Among them, one of Rs 81 ~R 89 is a single bond bonded to *6, or two or more groups of two or more of the aforementioned Rs substituted on adjacent atoms 81 ~R 89 are bonded to each other to form a ring, and one of the atoms constituting the ring is bonded to *6 through a single bond.)]

[1171] Specific examples of the compound represented by formula (41) are described below, but these are merely illustrative, and the compound represented by formula (41) is not limited to the following specific examples.

[1172] [Chemical formula 124]

[1173]

[1174] [Compound represented by formula (51)]

[1175] Next, the compound represented by formula (51) will be described.

[1176] [Chemical formula 125]

[1177]

[1178] [In formula (51),

[1179] R 62 ~R 79 each independently is

[1180] a hydrogen atom,

[1181] an unsubstituted alkyl group having 1 to 50 carbon atoms,

[1182] an unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1183] an unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1184] an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1185] -Si(R 901 )(R 902 )(R 903)、

[1186] -O-(R 904 )、

[1187] -S-(R 905 )、

[1188] -N(R 906 )(R 907 )、

[1189] a halogen atom, a cyano group, a nitro group,

[1190] an unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1191] an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1192] R 901 ~R 907 each independently is

[1193] a hydrogen atom,

[1194] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1195] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1196] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1197] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 may be the same or different from each other.

[1198] Two or more of R 62 ~R 70 substituted on adjacent atoms bond to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms, or do not form a ring.

[1199] Two or more of R 71 ~R 79 substituted on adjacent atoms bond to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms, or do not form a ring.

[1200] Among them, one of R 62 ~R 70 is a single bond bonded to *4, or the aforementioned R 62 ~R 70Two or more groups of one or more are bonded to each other to form a ring, and one atom constituting the ring is bonded to *4 by a single bond.

[1201] R 71 ~R 79 One of them is a single bond bonded to *5, or R substituted on adjacent atoms as described above 71 ~R 79 Two or more groups of one or more are bonded to each other to form a ring, and one atom constituting the ring is bonded to *5 by a single bond. In addition, R that is not bonded to *5 71 ~R 79 One of them is a single bond bonded to L 52 or R substituted on adjacent atoms as described above 71 ~R 79 Two or more groups of one or more are bonded to each other to form a ring, and another atom among the atoms constituting the ring is bonded to L by a single bond 52 bonded.

[1202] L 51 Each independently is

[1203] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1204] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[1205] q is an integer from 0 to 3. When q is 2 or more, R existing in two or more 62 ~R 70 may be the same or different from each other. Among them, when q is 0, it is the hydrogen atom of the terminal L 51 bonded.

[1206] r is an integer from 0 to 2. When r is 0, L 51 is a single bond. When r is 2, the two Ls 51 may be the same or different from each other. Among them, when q is 2 or more, r is 1 or 2.

[1207] L 52 is

[1208] a single bond,

[1209] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1210] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[1211] Ar 52 is

[1212] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1213] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[1214] In one embodiment, the compound represented by the aforementioned formula (51) is a compound represented by the following formula (51-1).

[1215] [Chemical Formula 126]

[1216]

[1217] [In formula (51-1), R 62 ~R 70 , R 72 ~R 79 , *4, *5, q, L 51 , r, L 52 and Ar 52 are as defined in the aforementioned formula (51).

[1218] In one embodiment, q in the aforementioned formula (51) is 1.

[1219] In one embodiment, the compound represented by the aforementioned formula (51) is a compound represented by the following formula (51-2).

[1220] [Chemical Formula 127]

[1221]

[1222] [In formula (51-2), R 62 , L 51 , r, L 52 and Ar 52 are as defined in the aforementioned formula (51).

[1223] In one embodiment, the compound represented by the aforementioned formula (51) is selected from the compounds represented by the following formula (51-3a), the compound represented by the following formula (51-3b), and the compound represented by the following formula (51-3c).

[1224] [Chemical Formula 128]

[1225]

[1226] [In formulas (51-3a) to (51-3c), R 62 , L 51 , r, L 52 and Ar 52 are as defined in the aforementioned formula (51).

[1227] Specific examples of the compound represented by formula (51) are described below, but these are merely illustrative, and the compound represented by formula (51) is not limited to the following specific examples.

[1228] [Chemical formula 129]

[1229]

[1230] In one embodiment, when the substituents in the compounds represented by the aforementioned formulas (1), (11), (21), (31), (41) and (51) are referred to as "substituted or unsubstituted", the substituents are selected from

[1231] unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1232] unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1233] unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1234] unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[1235] -Si(R 901 )(R 902 )(R 903 ),

[1236] -O-(R 904 ),

[1237] -S-(R 905 ),

[1238] -N(R 906 )(R 907 )

[1239] (Herein,

[1240] R 901 to R 907 are each independently

[1241] a hydrogen atom,

[1242] substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1243] substituted or unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms,

[1244] substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms, or

[1245] substituted or unsubstituted monovalent heterocyclic groups having 5 to 50 ring atoms. When there are two or more of R 901 to R 907 , the two or more R 901 to R 907 may be the same or different from each other.).

[1246] a halogen atom, a cyano group, a nitro group,

[1247] an aryl group having 6 to 50 ring-constituting carbon atoms, and

[1248] a group in a monovalent heterocyclic group having 5 to 50 ring-constituting atoms.

[1249] In one embodiment, in the compounds represented by the aforementioned formulas (1), (11), (21), (31), (41), and (51), when the aforementioned "substituted or unsubstituted" is mentioned, the substituent is selected from

[1250] an alkyl group having 1 to 50 carbon atoms,

[1251] an aryl group having 6 to 50 ring-constituting carbon atoms, and

[1252] a group in a monovalent heterocyclic group having 5 to 50 ring-constituting atoms.

[1253] In one embodiment, in the compounds represented by the aforementioned formulas (1), (11), (21), (31), (41), and (51), when the aforementioned "substituted or unsubstituted" is mentioned, the substituent is selected from

[1254] an alkyl group having 1 to 18 carbon atoms,

[1255] an aryl group having 6 to 18 ring-constituting carbon atoms, and

[1256] a group in a monovalent heterocyclic group having 5 to 18 ring-constituting atoms.

[1257] Specific examples of the above-mentioned groups are as described in the [Definition] column of this specification.

[1258] As described above, the organic EL element of the first mode has a cathode, an anode, and an organic layer between the aforementioned cathode and the aforementioned anode. The aforementioned organic layer contains the compound represented by the aforementioned formula (1) and the compound represented by the aforementioned formula (11). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1259] As described above, the organic EL element of the second mode has a cathode, an anode, and an organic layer between the aforementioned cathode and the aforementioned anode. The aforementioned organic layer contains a light-emitting layer. The aforementioned light-emitting layer contains the compound represented by the aforementioned formula (1) and the compound represented by the aforementioned formula (11). The hole blocking layer adjacent to the aforementioned light-emitting layer contains the compound represented by the aforementioned formula (21) and / or the compound represented by the aforementioned formula (31). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1260] As described above, the organic EL element of the third mode has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes a light-emitting layer. The light-emitting layer includes the compound represented by the formula (1) and the compound represented by the formula (11). The electron blocking layer adjacent to the light-emitting layer includes the compound represented by the formula (41). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1261] As described above, the organic EL element of the fourth mode has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes a light-emitting layer. The light-emitting layer includes the compound represented by the formula (1) and the compound represented by the formula (11). The hole blocking layer adjacent to the light-emitting layer includes the compound represented by the formula (21) and / or the compound represented by the formula (31). The electron blocking layer adjacent to the light-emitting layer includes the compound represented by the formula (41). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1262] As described above, the organic EL element of the fifth mode has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes two or more light-emitting layers. One or more of the two or more light-emitting layers include the compound represented by the formula (1) and the compound represented by the formula (11). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1263] In addition, as described above, another organic EL element of the fifth mode has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes two or more light-emitting layers. One or more of the two or more light-emitting layers include

[1264] the compound represented by the formula (1), and

[1265] Compound A having a Stokes shift of 20 nm or less and an emission peak wavelength of 440 nm to 465 nm. In addition, as long as the effects of the present invention are not impaired, conventionally known materials and element configurations can be applied.

[1266] Hereinafter, components that can be used in an embodiment of the organic EL element of the first to fifth modes, and materials other than the compounds represented by the formulas (1), (11), (21), (31), (41), and (51) constituting each layer will be described.

[1267] (Substrate)

[1268] The substrate serves 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.

[1269] (Anode)

[1270] In the anode formed on the substrate, it is preferable to use a metal, alloy, conductive compound, and a mixture thereof, etc. having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. can be cited. In addition, gold (Au), platinum (Pt), or a nitride of a metal material (for example, titanium nitride), etc. can be cited.

[1271] (Hole injection layer)

[1272] 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 a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used.

[1273] (Hole transport layer)

[1274] The hole transport layer is a layer containing a substance with high hole transport property. As substances that can be used in the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. Among them, as long as it is a substance with higher hole transport property compared to electron transport property, substances other than them can be used. It should be noted that the layer containing a substance with high hole transport property is not only a single layer, but layers formed of the above substances can also be laminated in two or more layers.

[1275] (Guest material of the light-emitting layer)

[1276] The light-emitting layer is a layer containing a substance with high luminescence property, and various materials can be used. For example, as a substance with high luminescence property, 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.

[1277] As a blue-based fluorescent light-emitting material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. As a green fluorescent light-emitting material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. As a red fluorescent light-emitting material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used.

[1278] As a blue phosphorescent light-emitting 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 a green phosphorescent light-emitting material that can be used in the light-emitting layer, iridium complexes, etc. can be used. As a red phosphorescent light-emitting 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.

[1279] (Host material of the light-emitting layer)

[1280] As the light-emitting layer, it can be a structure in which the above-mentioned highly light-emitting substance (guest material) is dispersed in other substances (host material). As the substance for dispersing the highly light-emitting substance, various substances can be used, and a substance having a higher lowest unoccupied molecular orbital energy level (LUMO energy level) and a lower highest occupied molecular orbital energy level (HOMO energy level) than the highly light-emitting substance is preferably used.

[1281] As the substance (host material) for dispersing the highly light-emitting 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 derivatives, etc., 3) triarylamine derivatives, or aromatic amine compounds such as condensed polycyclic aromatic amine derivatives.

[1282] (Electron transport layer)

[1283] The electron transport layer is a layer containing a substance with high electron transportability. In the electron transport layer, 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, 3) polymer compounds can be used.

[1284] (Electron injection layer)

[1285] The electron injection layer is a layer containing a substance with high electron injectability. In the electron injection layer, metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 8-hydroxyquinolate (Liq), etc., alkali metals, alkaline earth metals, or their compounds such as lithium oxide (LiO x ) can be used.

[1286] (Intermediate layer)

[1287] In a tandem organic EL element, an intermediate layer is provided.

[1288] (Cathode)

[1289] The cathode preferably uses a metal, alloy, conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[1290] In the organic EL element of the first mode, the formation method of each layer is not particularly limited. A formation method based on a conventionally known vacuum evaporation method, spin coating method, or the like can be used. Each layer such as a light-emitting layer can be formed by a known method based on a vacuum evaporation method, molecular beam epitaxy (MBE) method, or a coating method such as a solution dipping method, spin coating method, casting method, bar coating method, or roll coating method in which it is dissolved in a solvent.

[1291] In the organic EL element of the first mode, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes and maintain a low applied voltage, and improve luminous efficiency, it is usually preferably in the range of several nm to 1 μm.

[1292] [Electronic device]

[1293] The electronic device of the fifth mode of the present invention is characterized by including the organic electroluminescent element of the first to fifth modes described above.

[1294] As specific examples of the electronic device, display components such as an organic EL panel module, display devices such as a television, a mobile phone, or a personal computer, and light-emitting devices such as lighting or vehicle lamps can be cited.

[1295] Examples

[1296] Next, examples and comparative examples will be given to further illustrate the present invention in detail, but the present invention is not limited by the content described in these examples in any way.

[1297] The compounds used in the following Examples 1 to 7 and Comparative Examples 1 to 2 are as described below.

[1298] [Chemical formula 130]

[1299]

[1300] Example 1

[1301] (Fabrication of Organic EL Device)

[1302] (Fabrication of Organic EL Device)

[1303] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then subjected to UV-ozone washing for 30 minutes. The film thickness of ITO was 130 nm.

[1304] The washed glass substrate with the transparent electrode was loaded onto the substrate holder of a vacuum evaporation apparatus. First, compound HI was evaporated on the surface with the transparent electrode formed thereon in a manner to cover the transparent electrode, forming an HI film with a thickness of 5 nm. This HI film functions as a hole injection layer.

[1305] On the deposition of this HI film, compound HT was continuously evaporated to form an HT film with a thickness of 80 nm on the HI film. This HT film functions as a hole transport layer (the first hole transport layer).

[1306] On the deposition of the HT film, compound EBL-1 was continuously evaporated to form an EBL-1 film with a thickness of 10 nm on the HT film. This EBL-1 film functions as an electron blocking layer (the second hole transport layer).

[1307] On the EBL-1 film, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated such that the proportion of compound BD-1 reached 2 mass%, forming a BH-1:BD-1 film with a thickness of 25 nm. This BH-1:BD-1 film functions as a light-emitting layer.

[1308] On this light-emitting layer, compound ET was evaporated to form an ET film with a thickness of 15 nm. This ET film functions as an electron transport layer. On this ET film, LiF was evaporated to form a LiF film with a thickness of 1 nm. On this LiF film, metal Al was evaporated to form a metal cathode with a thickness of 80 nm, fabricating an organic EL device.

[1309] The layer structure of the obtained organic EL device is as described below.

[1310] ITO(130) / HI(5) / HT(80) / EBL-1(10) / BH-1:BD-1(25:2 mass%) / ET(15) / LiF(1) / Al(80)

[1311] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1312] (Evaluation of Organic EL Device)

[1313] When the current density reaches 50 mA / cm 2A voltage was applied to the organic EL element in the following manner, and the time until the luminance reached 95% of the initial luminance (LT95@50 mA / cm 2 ) was measured. The results of the obtained lifetime LT95 (hr) are shown in Table 1.

[1314] Example 2

[1315] (Fabrication of Organic EL Element)

[1316] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then subjected to UV ozone washing for 30 minutes. The film thickness of ITO was 130 nm.

[1317] The washed glass substrate with the transparent electrode was loaded on the substrate holder of a vacuum evaporation apparatus. First, compound HI was evaporated on the surface with the transparent electrode formed thereon in a manner to cover the transparent electrode, forming an HI film with a film thickness of 5 nm. This HI film functions as a hole injection layer.

[1318] On the deposition of this HI film, compound HT was continuously evaporated to form an HT film with a film thickness of 80 nm on the HI film. This HT film functions as a hole transport layer (the first hole transport layer).

[1319] On the deposition of the HT film, compound EBL-1 was continuously evaporated to form an EBL-1 film with a film thickness of 10 nm on the HT film. This EBL-1 film functions as an electron blocking layer (the second hole transport layer).

[1320] On the EBL-1 film, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated in such a manner that the proportion of compound BD-1 reached 2% by mass to form a BH-1:BD-1 film with a film thickness of 25 nm. This BH-1:BD-1 film functions as a light-emitting layer.

[1321] On this light-emitting layer, compound HBL-1 was evaporated to form an HBL-1 film with a film thickness of 10 nm. This HBL-1 film functions as a hole blocking layer (the first electron transport layer). On the deposition of the HBL-1 film, compound ET was continuously evaporated to form an ET film with a film thickness of 15 nm. This ET film functions as an electron transport layer (the second electron transport layer). On this ET film, LiF was evaporated to form a LiF film with a film thickness of 1 nm. On this LiF film, metal Al was evaporated to form a metal cathode with a film thickness of 80 nm, thereby fabricating an organic EL element.

[1322] The layer structure of the obtained organic EL element is as described below.

[1323] ITO(130) / HI(5) / HT(80) / EBL-1(10) / BH-1:BD-1(25:2 mass%) / HBL-1(10) / ET(15) / LiF(1) / Al(80)

[1324] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1325] Example 3 and Comparative Example 1

[1326] Using the compounds shown in Table 1 as the host material, dopant material, and hole blocking layer material of the light-emitting layer, an organic EL element was fabricated and evaluated in the same manner as in Example 2 except for this. The results are shown in Table 1.

[1327] [Table 1]

[1328]

[1329] From the results in Table 1, it can be seen that the element lifetime of Example 1 using a trisubstituted anthracene compound (BH-1) was significantly improved compared to Comparative Example 1 using a disubstituted anthracene compound (BHC-1).

[1330] In addition, it can be seen that in Examples 2 and 3, by using compound HBL-1 or HBL-4 in the hole blocking layer, the element lifetime was further improved compared to Example 1 without a hole blocking layer. In contrast, it can be seen that in Comparative Example 1, even when a hole blocking layer using the same compound HBL-1 as in Example 1 was provided, the element lifetime was very poor.

[1331] Example 4

[1332] Using the host material and dopant material shown in Table 2 below, an organic EL element was fabricated and evaluated in the same manner as in Example 1 except for this. The results are shown in Table 2.

[1333] The layer structure of the obtained organic EL element is as follows.

[1334] ITO(130) / HI(5) / HT(80) / EBL-1(10) / BH-1:BD-3(25:2 mass%) / ET(15) / LiF(1) / Al(80)

[1335] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1336] Examples 5 to 7 and Comparative Example 2

[1337] Using the host material, dopant material, and hole blocking layer material shown in Table 2 below, an organic EL element was fabricated and evaluated in the same manner as in Example 2 except for this. The results are shown in Table 2.

[1338] The layer structure of the obtained organic EL element is as follows.

[1339] ITO(130) / HI(5) / HT(80) / EBL-1(10) / BH-1:BD-3(25:2 mass%) / HBL-1 to HBL-3(10) / ET(15) / LiF(1) / Al(80)

[1340] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1341] [Table 2]

[1342]

[1343] From the results of Table 2, it can be seen that compared with Comparative Example 2 using the 2-substituted anthracene compound BHC-1, the element life of Examples 4 to 7 using the 3-substituted anthracene compound (BH-1) is significantly improved.

[1344] In addition, it can be seen that in Examples 5 to 7, by using the compounds HBL-1 to HBL-3 in the hole blocking layer, the element life is further improved compared with Example 4 without a hole blocking layer. In contrast, it can be seen that in Comparative Example 2, even when a hole blocking layer using the same compound HBL-1 as in Example 5 is provided, the element life is very poor.

[1345] <Compound>

[1346] The compound represented by the formula (1) used in the manufacture of the organic EL element in Examples after Example 8 is shown below. It should be noted that the following 3BH-1 is the same compound as BH-1 used in Examples 1 to 7.

[1347] [Chemical formula 131]

[1348]

[1349] The compound represented by the formula (11) used in the manufacture of the organic EL element in Examples after Example 8 is shown below.

[1350] [Chemical formula 132]

[1351]

[1352] The compound represented by the formula (A-1) used in the manufacture of the organic EL element in Examples after Example 8 is shown below.

[1353] [Chemical formula 133]

[1354]

[1355] The compounds represented by formula (A-2) used in the production of the organic EL elements of the examples after Example 8 are shown below.

[1356] [Chemical formula 134]

[1357]

[1358] In the production of the organic EL elements of the comparative examples after Comparative Example 3, the compounds used as the host material of the light-emitting layer are shown below. It should be noted that the following Ref.2BH-1 is the same compound as BHC-1 used in Comparative Examples 1 and 2.

[1359] [Chemical formula 135]

[1360]

[1361] In the production of the organic EL elements of the comparative examples after Comparative Example 3, the compounds used as the dopant material of the light-emitting layer are shown below.

[1362] [Chemical formula 136]

[1363]

[1364] The structures of the other compounds used in the production of the organic EL elements of the examples after Example 8 and the comparative examples after Comparative Example 3 are shown below.

[1365] [Chemical formula 137]

[1366]

[1367] <Fabrication of Organic EL Element>

[1368] The organic EL element was fabricated as follows and evaluated.

[1369] Example 8

[1370] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then subjected to UV ozone washing for 30 minutes. The film thickness of ITO was 130 nm.

[1371] The washed glass substrate with the transparent electrode was loaded on the substrate holder of a vacuum evaporation apparatus, and first, compound HI was evaporated on the surface with the transparent electrode formed thereon to form a 5-nm-thick HI film. This HI film functions as a hole injection layer.

[1372] On the formed HI film, compound HT was further deposited by evaporation to form an HT film with a film thickness of 80 nm. This HT film functions as a hole transport layer (the first hole transport layer).

[1373] On the formed HT film, compound EBL-1 was further deposited by evaporation to form an EBL-1 film with a film thickness of 10 nm. This EBL-1 film functions as an electron blocking layer (the second hole transport layer).

[1374] On the EBL-1 film, compound 3BH-2 (host material) and compound BD-1 (dopant material) were co-evaporated such that the proportion of compound BD-1 reached 2% by mass to form a 3BH-2:BD-1 film with a film thickness of 25 nm. This 3BH-2:BD-1 film functions as a light-emitting layer.

[1375] On this light-emitting layer, compound HBL-1 was deposited by evaporation to form an HBL-1 film with a film thickness of 10 nm. This HBL-1 film functions as a hole blocking layer (the first electron transport layer). On the formed HBL-1 film, compound ET was further deposited by evaporation to form an ET film with a film thickness of 15 nm. This ET film functions as an electron transport layer (the second electron transport layer). On this ET film, LiF was deposited by evaporation to form a LiF film with a film thickness of 1 nm. On this LiF film, metal Al was deposited by evaporation to form a metal cathode with a film thickness of 80 nm, and an organic EL element was fabricated.

[1376] The layer structure of the obtained organic EL element is as described below.

[1377] ITO(130) / HI(5) / HT(80) / EBL-1(10) / 3BH-2:BD-1(25: 2% by mass) / HBL-1(10) / ET(15) / LiF(1) / Al(80)

[1378] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1379] Examples 9 to 14

[1380] The organic EL elements of Examples 9 to 14 were fabricated in the same manner as in Example 8, except that the dopant material of the light-emitting layer in Example 8 was replaced with the dopant materials described in Table 3.

[1381] Comparative Example 3

[1382] The organic EL element of Comparative Example 3 was fabricated in the same manner as in Example 8, except that the dopant material of the light-emitting layer in Example 8 was replaced with the dopant materials described in Table 3 and co-evaporation was performed such that its proportion reached 4% by mass.

[1383] <Evaluation of Organic EL Element>

[1384] For the organic EL elements fabricated in Examples 8 to 14 and Comparative Example 3, the following evaluations were conducted. The evaluation results are shown in Table 3. In addition, the Stokes shift values of the dopant materials used in Examples 8 to 14 and the respective dopant materials used in Comparative Example 3 are also shown in Table 3.

[1385] · External quantum efficiency EQE (%)

[1386] A voltage was applied to the organic EL element so that the current density reached 10 mA / cm 2 . The EL emission spectrum was measured using a spectro-radiance meter CS-1000 (manufactured by Konica Minolta, Inc.). Based on the obtained spectro-radiance spectrum, the external quantum efficiency EQE (%) was calculated.

[1387] · Stokes shift (SS) (nm) of the dopant material

[1388] The dopant material was dissolved in toluene at a concentration of 10 -5 mol / L or more and 10 -4 mol / L or less to prepare a measurement sample. The measurement sample placed in a quartz cell was irradiated with continuous light in the ultraviolet-visible light region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) was measured. In the absorption spectrum measurement, a spectrophotometer U-3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation was used. In addition, the dopant material was dissolved in toluene at a concentration of 10 -6 mol / L or more and 10 -5 mol / L or less to prepare a measurement sample. The measurement sample placed in a quartz cell was irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) was measured. In the fluorescence spectrum measurement, a spectrofluorometer F-7000 type manufactured by Hitachi High-Tech Science Corporation was used.

[1389] Based on these absorption spectra and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength was calculated to obtain the Stokes shift (SS).

[1390] · Emission peak wavelength λ (nm)

[1391] A voltage was applied to the organic EL element so that the current density reached 10 mA / cm 2 . The EL emission spectrum was measured using a spectro-radiance meter CS-1000 (manufactured by Konica Minolta, Inc.). Based on the obtained spectro-radiance spectrum, the emission peak wavelength was obtained.

[1392] [Table 3]

[1393]

[1394] As can be seen from the results in Table 3, for the 3-substituted anthracene compound 3BH-2 shown in Formula (1), compared with Comparative Example 3 combined with the compound Ref.WBD-1 having a large Stokes shift (SS) and blue emission, the device efficiency (external quantum efficiency) of Examples 8 to 14 combined with the compound A (BD-1 to BD-7) having a small Stokes shift (SS) and blue emission is high.

[1395] <Fabrication and Evaluation of Organic EL Devices>

[1396] The organic EL devices of Examples 15 to 20 and Comparative Example 4 were fabricated as follows and evaluated.

[1397] Examples 15, 16, and 18

[1398] For the organic EL devices of Examples 15, 16, and 18, the materials of the light-emitting layer in Example 8 were replaced with the host material and dopant material described in Table 4, and otherwise fabricated and evaluated in the same manner as in Example 8.

[1399] Examples 17, 19, 20, and Comparative Example 4

[1400] For the organic EL devices of Examples 17, 19, 20, and Comparative Example 4, the materials of the light-emitting layer in Example 8 were replaced with the host material and dopant material described in Table 4, and co-evaporation was performed such that the proportion of the dopant material reached 4% by mass, and otherwise fabricated and evaluated in the same manner as in Example 8.

[1401] [Table 4]

[1402]

[1403] As can be seen from the results in Table 4, compared with Comparative Example 4 in which the 3-substituted anthracene compound 3BH-1 shown in Formula (1) is combined with the compound Ref.WBD-1 having a large Stokes shift (SS) and blue emission, the device efficiency (external quantum efficiency) of Examples 15 to 20 combined with the compound A (BD-3, BD-6, and BD-8 to 11) having a small Stokes shift (SS) and blue emission is high.

[1404] Based on the results in Tables 3 and 4 above, compared with the combinations of the 3-substituted anthracene compounds 3BH-2 and 3BH-1 shown in Formula (1) with the compounds having a large Stokes shift (SS) and blue emission, in the combinations with the compound A having a small Stokes shift (SS) and blue emission, energy transfer is likely to occur, the device efficiency (external quantum efficiency) becomes high, and it can be applied as an organic EL device for blue fluorescence.

[1405] <Fabrication of Organic EL Devices>

[1406] An organic EL element is fabricated as follows.

[1407] Examples 21 to 22 and Comparative Examples 5 to 6

[1408] For the organic EL elements of Examples 21 to 22 and Comparative Examples 5 to 6, the host material and dopant material of the light-emitting layer in Example 8 were replaced with the host material and dopant material described in Table 5 or Table 6, and they were fabricated in the same manner as in Example 8 except for this.

[1409] <Evaluation of organic EL element>

[1410] For the organic EL elements fabricated in Examples 21 to 22 and Comparative Examples 5 to 6, the following evaluations were performed. The evaluation results are shown in Tables 5 and 6.

[1411] · Driving voltage (V)

[1412] The initial characteristics of the obtained organic EL element were measured at room temperature with a DC (direct current) constant current of 10 mA / cm 2 for driving.

[1413] · Element lifetime (LT90)

[1414] A voltage was applied to the organic EL element such that the current density reached 50 mA / cm 2 and the time until the luminance reached 90% of the initial luminance was measured.

[1415] · For the Stokes shift (SS) and emission peak wavelength λ, the method described in Example 4 was used for measurement.

[1416] [Table 5]

[1417]

[1418] [Table 6]

[1419]

[1420] From the results of Tables 5 and 6, it can be seen that the combination of the 3-substituted anthracene compound 3BH-1 or 3BH-3 shown in formula (1) with the compound A having a small Stokes shift (SS) and blue emission, i.e., BD-6, can obtain an element with blue fluorescence that can be driven at a low voltage and has a long lifetime compared to the case of combination with the 2-substituted anthracene compound Ref.2BH-1 or Ref.2BH-2.

[1421] <Fabrication of organic EL element>

[1422] An organic EL element was fabricated as follows and evaluated.

[1423] Examples 23 to 25 and Comparative Examples 7 to 8

[1424] For the organic EL elements of Examples 23 to 25 and Comparative Examples 7 to 8, the host material and dopant material of the light-emitting layer in Example 8 were replaced with the host material and dopant material described in Table 7 or Table 8, and co-evaporation was carried out so that the proportion of the dopant material reached 4% by mass. Except for this, they were fabricated in the same manner as in Example 8 and evaluated in the same manner as in Example 21.

[1425] [Table 7]

[1426]

[1427] [Table 8]

[1428]

[1429] From the results in Table 7 and Table 8, it can be seen that, compared with the combination of the 3-substituted anthracene compound 3BH-1, 3BH-2 or 3BH-4 shown in formula (1) and the compound A with a small Stokes shift (SS) and blue light emission, namely compound BD-8, and the combination with the 2-substituted anthracene compound Ref.2BH-1 or Ref.2BH-3, an element that can be driven at a low voltage and has a long lifespan of blue fluorescence can be obtained.

[1430] <Fabrication of Organic EL Element>

[1431] The organic EL element was fabricated as follows and evaluated.

[1432] Examples 26 to 27 and Comparative Example 9

[1433] For the organic EL elements of Examples 26 to 27 and Comparative Example 9, the light-emitting layer in Example 8 was replaced with the dopant material described in Table 9, and co-evaporation was carried out so that its proportion reached 4% by mass. Except for this, they were fabricated in the same manner as in Example 8 and evaluated in the same manner as in Example 21.

[1434] [Table 9]

[1435]

[1436] From the results in Table 9, it can be seen that, compared with the combination of the 3-substituted anthracene compound 3BH-1 or 3BH-2 shown in formula (1) and the compound A with a small Stokes shift (SS) and blue light emission, namely BD-11, and the combination with the 2-substituted anthracene compound Ref.2BH-1, an element that can be driven at a low voltage and has a long lifespan of blue fluorescence can be obtained.

[1437] Examples 28 and 30

[1438] Using the host material and dopant material shown in Table 10 below, other than this, an organic EL element was fabricated in the same manner as in Example 1, and evaluation was conducted in the same manner as in Example 1. The results are shown in Table 10.

[1439] Examples 29 and 31, and Comparative Example 10

[1440] Using the host material, dopant material, and material for the hole blocking layer shown in Table 10 below, other than this, an organic EL element was fabricated in the same manner as in Example 2, and evaluation was conducted in the same manner as in Example 1. The results are shown in Table 10.

[1441] [Table 10]

[1442]

[1443] From the results in Table 10, it can be seen that the element lifetimes of Examples 28 to 31 using a trisubstituted anthracene compound (3BH-1 or 3BH-2) were significantly improved compared to Comparative Example 10 using a disubstituted anthracene compound Ref.2BH-1.

[1444] Furthermore, it was found that in Examples 29 and 31, by using compound HBL-5 in the hole blocking layer, the element lifetimes were further improved compared to Examples 28 and 30 without a hole blocking layer. In contrast, it was found that in Comparative Example 10, even when a hole blocking layer using the same compound HBL-5 as in Examples 29 and 31 was provided, the element lifetime was very poor.

[1445] Examples 32 and 34

[1446] Using the host material and dopant material shown in Table 11 below, other than this, an organic EL element was fabricated in the same manner as in Example 1, and the lifetime (LT90) was evaluated in the same manner as in Example 21. The results are shown in Table 11.

[1447] Examples 33 and 35, and Comparative Example 11

[1448] Using the host material, dopant material, and material for the hole blocking layer shown in Table 11 below, other than this, an organic EL element was fabricated in the same manner as in Example 2, and the lifetime (LT90) was evaluated in the same manner as in Example 21. The results are shown in Table 11.

[1449] [Table 11]

[1450]

[1452] From the results in Table 11, it can be seen that the element lifetimes of Examples 32 to 35 using a trisubstituted anthracene compound (3BH-1, 2) were significantly improved compared to Comparative Example 11 using a disubstituted anthracene compound 2BH-1.

[1453] In addition, it can be seen that in Examples 33 and 35, by using Compound HBL-5 in the hole blocking layer, the element lifetime is further improved compared to Examples 32 and 34 without a hole blocking layer. In contrast, it can be seen that in Comparative Example 11, even when a hole blocking layer using the same Compound HBL-5 as in Examples 33 and 35 is provided, the element lifetime is very poor.

[1454] Example 36 and Comparative Example 12

[1455] The host material and dopant material shown in Table 12 below were used, and in other respects, an organic EL element was fabricated in the same manner as in Example 8 and evaluated in the same manner as in Example 21. The results are shown in Table 12.

[1456] [Table 12]

[1457]

[1458] From the results in Table 12, it can be seen that the combination of the 3-substituted anthracene compound 3BH-5 represented by formula (1) and Compound A (BD-3) with a small Stokes shift (SS) and blue emission can provide an element with blue fluorescence that can be driven at a low voltage and has a long lifetime, compared to the case of combining with the 2-substituted anthracene compound Ref.2BH-4.

[1459] Example 37

[1460] <Fabrication of tandem organic EL element>

[1461] The aforementioned glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then subjected to UV ozone washing for 1 minute. The film thickness of the ITO was 130 nm.

[1462] · Formation of the first light-emitting unit

[1463] The washed glass substrate with a transparent electrode was loaded on the substrate holder of a vacuum evaporation apparatus. First, Compound HT-2 and Compound HI-2 were evaporated on the surface with the transparent electrode formed thereon so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The concentration of Compound HT-2 in the hole injection layer was 97% by mass, and the concentration of Compound HI-2 was 3% by mass.

[1464] Next, Compound HT-2 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 70 nm.

[1465] Next, Compound EBL-2 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

[1466] Next, compound 3BH-2 and compound BD-7 are co-evaporated on the second hole transport layer to form a blue fluorescent emission layer as the first emission layer with a film thickness of 25 nm. The concentration of compound 3BH-2 in the blue fluorescent emission layer is 98% by mass, and the concentration of compound BD-7 is 2% by mass.

[1467] Next, compound HBL-2 is evaporated on the blue fluorescent emission layer to form an electron transport layer with a film thickness of 10 nm.

[1468] · Formation of the first charge generation layer

[1469] Next, compound ET-2 and lithium (Li) are co-evaporated on the electron transport layer to form a first N layer with a film thickness of 10 nm. The concentration of compound ET-2 in the first N layer is 96% by mass, and the concentration of Li is 4% by mass.

[1470] Next, compound HT-2 and compound HI-2 are co-evaporated on the first N layer to form a first P layer with a film thickness of 10 nm. The concentration of compound HT-2 in the first P layer is 90% by mass, and the concentration of compound HI-2 is 10% by mass.

[1471] · Formation of the second light-emitting unit

[1472] Next, compound EBL-2 is evaporated on the first P layer to form a first hole transport layer with a film thickness of 10 nm.

[1473] Next, compound PGH-1 and compound PGD-1 are co-evaporated on the first hole transport layer to form a yellow phosphorescent emission layer as the second emission layer with a film thickness of 48 nm. The concentration of compound PGH-1 in the yellow phosphorescent emission layer is 80% by mass, and the concentration of compound PGD-1 is 20% by mass.

[1474] Next, compound ET is evaporated on the yellow phosphorescent emission layer to form an electron transport layer with a film thickness of 10 nm.

[1475] · Formation of the second charge generation layer

[1476] Next, compound ET-2 and lithium (Li) are co-evaporated on the electron transport layer to form a second N layer with a film thickness of 35 nm. The concentration of compound ET-2 in the second N layer is 96% by mass, and the concentration of Li is 4% by mass.

[1477] Next, compound HT-2 and compound HI-2 are co-evaporated on the second N layer to form a second P layer with a film thickness of 10 nm. The concentration of compound HT-2 in the second P layer is 90% by mass, and the concentration of compound HI-2 is 10% by mass.

[1478] · Formation of the third light-emitting unit

[1479] Next, compound HT-2 was vapor-deposited on the 2P layer to form a first hole transport layer with a film thickness of 70 nm.

[1480] Next, compound EBL-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

[1481] Next, compounds 3BH-2 and BD-7 were co-vapor-deposited on the second hole transport layer to form a blue fluorescent light-emitting layer as a third light-emitting layer with a film thickness of 25 nm. The concentration of compound 3BH-2 in the blue fluorescent light-emitting layer was 98% by mass, and the concentration of compound BD-7 was 2% by mass.

[1482] Next, compound HBL-2 was vapor-deposited on the blue fluorescent light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1483] Next, compound ET was vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 10 nm.

[1484] Next, lithium fluoride (LiF) was vapor-deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1485] And metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode with a film thickness of 80 nm.

[1486] As described above, a bottom-emitting type organic EL element was fabricated.

[1487] The layer structure of the obtained organic EL element is as follows.

[1488] ITO(130) / HT-2:HI-2(10, 97%:3%) / HT-2(70) / EBL-2(10) / 3BH-2:BD-7(25, 98%:2%) / HBL-2(10) / ET-2:Li(10, 96%:4%) / HT-2:HI-2(10, 90%:10%) / EBL-2(10) / PGH-1:PGD-1(48, 80%:20%) / ET(10) / ET-2:Li(35, 96%:4%) / HT-2:HI-2(10, 90%:10%) / HT-2(70) / EBL-2(10) / 3BH-2:BD-7(25, 98%:2%) / HBL-2(10) / ET(10) / LiF(1) / Al(80)

[1489] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[1490] Within the same parentheses, when the numbers represented by the parameters are, for example, HT-2:HI-2 (10, 97%:3%), it means that the ratio (mass %) of the compound HT-2 and the compound HI-2 in the hole injection layer is HT-1:HI-2 = 97 mass %:3 mass %.

[1491] <Evaluation of Organic EL Element>

[1492] · Driving voltage (V)

[1493] The initial characteristics of the obtained organic EL element were measured at room temperature with a DC (direct current) constant current of 10 mA / cm 2 for driving.

[1494] · For the Stokes shift (SS) and the emission peak wavelength λ, the measurement was carried out using the method described in Example 8.

[1495] Examples 38 to 40, and Comparative Examples 13 and 14

[1496] Using the host material and dopant material shown in Table 13 below, except for this, an organic EL element was fabricated in the same manner as in Example 37, and evaluated in the same manner as in Example 37.

[1497] [Table 13]

[1498]

[1499] The combination of the 3-substituted anthracene compounds 3BH-2 and 3BH-6 shown in Formula (1) and the compounds A having a small Stokes shift (SS) and blue emission, namely the compounds BD-7 and BD-13, can obtain a blue fluorescent element that can be driven at a low voltage compared with the case of combination with the 2-substituted anthracene compound Ref.2BH-1.

[1500] An organic EL element was fabricated as follows and evaluated.

[1501] Examples 41 to 43 and Comparative Example 15

[1502] For the organic EL elements of Examples 41 to 43 and Comparative Example 15, the materials of the light-emitting layer in Example 8 were replaced with the host material and dopant material shown in Table 14. Except for this, they were fabricated in the same manner as in Example 8 and evaluated. The results are shown in Table 14.

[1503] [Table 14]

[1504]

[1505] As can be seen from the results in Table 14, compared with Comparative Example 15 in which the 3-substituted anthracene compound 3BH-6 shown in Formula (1) is combined with the compound Ref.WBD-1 having a large Stokes shift (SS) and blue emission, the device efficiencies (external quantum efficiencies) of Examples 41 to 43 combined with the compounds A (i.e., BD-1, BD-8, and BD-9) having a small Stokes shift (SS) and blue emission are high.

[1506] As can be seen from the results in Table 14 above, compared with the combination of the 3-substituted anthracene compound 3BH-6 shown in Formula (1) and the compound having a large Stokes shift (SS) and blue emission, in the combination with the compound A having a small Stokes shift (SS) and blue emission, energy transfer is likely to occur, the device efficiency (external quantum efficiency) becomes high, and it can be applied to an organic EL device for blue fluorescence.

[1507] Examples 44 to 46 and Comparative Examples 16 to 18

[1508] For the organic EL devices of Examples 44 to 46 and Comparative Examples 16 to 18, the materials of the light-emitting layer in Example 8 were replaced with the host materials and dopant materials described in Tables 15 to 17, and otherwise, they were fabricated in the same manner as in Example 8 and evaluated in the same manner as in Example 21. The results are shown in Tables 15 to 17.

[1509] [Table 15]

[1510]

[1511] [Table 16]

[1512]

[1513] [Table 17]

[1514]

[1515] As can be seen from the results in Tables 15 to 17, for the combination of the 3-substituted anthracene compound 3BH-6 shown in Formula (1) and the compounds A (i.e., compounds BD-1, BD-8, and BD-9) having a small Stokes shift (SS) and blue emission, compared with the case of combination with the 2-substituted anthracene compound Ref.2BH-1, a device for blue fluorescence that can be driven at a low voltage and has a long lifetime can be obtained.

[1516] Several embodiments and / or examples of the present invention have been described in detail above. Those skilled in the art can easily make more changes to these illustrated embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these more changes are also included within the scope of the present invention.

[1517] All the documents described in this specification and the content of the application that is the basis of the priority of the Paris Convention based on this application are incorporated by reference.

Claims

1. An organic electroluminescent element, which is an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer contains a compound represented by the following formula (1) and a compound represented by the following formula (11), [Chemical formula 1] In formula (1), One or more of R1 to R8 is -L 13 -Ar 13 , L 11 ~L 13 Each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a divalent heterocyclic group having 5 to 50 ring atoms, L 13 When there are more than two, more than two Ls 13 They may be the same as each other or different Ar 11 ~Ar 13 Each independently is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, Ar 13 When there are two or more, two or more Ars 13 may be the same as or different from each other, Not-L 13 -Ar 13 Each of R1 to R8 is 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, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 may be the same or different from each other; [Chemical formula 2] In formula (11), R 11 ~R 20 One or more groups of two or more adjacent ones among R a1 ~R a5 One or more groups of two or more adjacent ones among, and R a6 ~R a10 Any one or more groups among one or more groups of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring atoms. R not involved in the ring 11 ~R 20 , R a1 ~R a5 , and R a6 ~R a10 Each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted phosphino group, a substituted or unsubstituted phosphoryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms, a cyano group, a nitro group, a carboxyl group, or a halogen atom.

2. The organic electroluminescent element according to claim 1, wherein, L in the foregoing formula (1) 11 ~L 13 Each independently represents a single bond, or A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

3. The organic electroluminescent element according to claim 1 or 2, wherein, L in the foregoing formula (1) 11 ~L 13 Each independently represents a single bond or is selected from A substituted or unsubstituted phenylene group, A substituted or unsubstituted biphenylene group, A substituted or unsubstituted terphenylene group, A substituted or unsubstituted quaterphenylene group, and Groups in a substituted or unsubstituted naphthylene group.

4. The organic electroluminescent element according to claim 1 or 2, wherein, Ar in the aforementioned formula (1) 11 ~Ar 13 Each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

5. The organic electroluminescent element according to any one of claims 1 to 3, wherein, Ar in the foregoing formula (1) 11 ~Ar 13 Each independently selected from A substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, A substituted or unsubstituted fluorenyl group, A substituted or unsubstituted 9,9'-spirobifluorenyl group, A substituted or unsubstituted benzofluorenyl group, A substituted or unsubstituted phenanthryl group, and A substituted or unsubstituted benzo[a]phenanthryl group.

6. The organic electroluminescent element according to any one of claims 1 to 3, wherein, Ar in the aforementioned formula (1) 11 ~Ar 13 One or more of them are each independently a monovalent heterocyclic group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted.

7. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The compound represented by the aforementioned formula (1) is a compound represented by the following formula (1-1), [Chemical formula 3] In formula (1-1), L 11 ~L 13 , Ar 11 ~Ar 13 , R1, R3, R4, and R5~R8 are defined as in the aforementioned formula (1).

8. The organic electroluminescent element according to any one of claims 1 to 7, wherein, The compound represented by the aforementioned formula (1) is a compound represented by the following formula (1-1H), [Chemical formula 4] In formula (1-1H), L 11 ~L 13 and Ar 11 ~Ar 13 are defined as in the aforementioned formula (1).

9. The organic electroluminescent element according to any one of claims 1 to 8, wherein, -L in the foregoing formula (1) 13 -Ar 13 The groups shown are selected from A substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, A substituted or unsubstituted biphenyl group, A substituted or unsubstituted phenanthryl group, A substituted or unsubstituted benzo[a]phenanthryl group, A substituted or unsubstituted fluorenyl group, A substituted or unsubstituted benzofluorenyl group, A substituted or unsubstituted dibenzofuranyl group, Substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.

10. The organic electroluminescent element according to any one of claims 1 to 9, wherein, The compound represented by the aforementioned formula (1) is selected from the compounds represented by the following formula (1-2), the compounds represented by the following formula (1-3), and the compounds represented by the following formula (1-4), [Chemical formula 5] In formulas (1-2) to (1-4), L 11 、L 12 、Ar 11 、Ar 12 、R1, R3, R4, and R5 to R8 are as defined in the aforementioned formula (1).

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