Organic electroluminescent elements and electronic devices

Abstract

An organic electroluminescent element (1) comprises an anode (3), a cathode (4), a first light-emitting layer (51), and a second light-emitting layer (52) disposed between the first light-emitting layer (51) and the cathode (4); the first light-emitting layer (51) contains a first compound represented by the following general formula (1) and having at least one group represented by the following general formula (11) as a first host material; the second light-emitting layer (52) contains a second compound represented by the following general formula (2) as a second host material; and the first light-emitting layer (51) and the second light-emitting layer (52) are directly in contact with each other.

Description

Technical Field

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

[0002] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays in mobile phones, televisions, and other applications. When voltage is applied to an organic EL device, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer to form excitons. At this point, due to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%.

[0003] To improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 to 6). Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Laid-Open No. 2013-157552

[0007] Patent Document 2: International Publication No. 2004 / 018587

[0008] Patent Document 3: International Publication No. 2005 / 115950

[0009] Patent Document 4: International Publication No. 2011 / 077691

[0010] Patent Document 5: Japanese Patent Application Publication No. 2018-125504

[0011] Patent Document 6: U.S. Patent Application Publication No. 2019 / 280209 Summary of the Invention

[0012] Problems to be solved by the invention

[0013] One object of the present invention is to provide an organic electroluminescent element with improved performance. Another object of the present invention is to provide an organic electroluminescent element with improved luminous efficiency, and an electronic device equipped with the organic electroluminescent element.

[0014] Means used to solve problems

[0015] According to one embodiment of the present invention, an organic electroluminescent element is provided, which comprises an anode, a cathode, a first light-emitting layer arranged between the anode and the cathode, and a second light-emitting layer arranged between the first light-emitting layer and the cathode, wherein the first light-emitting layer contains a first compound represented by the following general formula (1) and having at least one group represented by the following general formula (11) as a first host material, the second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material, and the first light-emitting layer is directly connected to the second light-emitting layer.

[0016]

Chemical Formula 1

[0017]

[0018] (In the above general formula (1),

[0019] R 101 ~R 110 Each independently

[0020] hydrogen atoms,

[0021] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0022] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0023] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0024] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0025] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0026] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0027] -O-(R 904 ) shown in the group,

[0028] -S-(R 905 ) shown in the group,

[0029] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0030] -C(=O)R 801 The groups shown,

[0031] -COOR 802 The groups shown,

[0032] Halogen atoms,

[0033] cyano,

[0034] Nitro,

[0035] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0036] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[0037] The group represented by the above general formula (11)

[0038] Among them, R 101 ~R 110 At least one of them is a group represented by the above general formula (11),

[0039] When there are a plurality of groups represented by the general formula (11), the plurality of groups represented by the general formula (11) may be the same as or different from each other.

[0040] L 101 for

[0041] single bond,

[0042] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0043] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0044] Ar 101 for

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

[0046] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0047] mx is 0, 1, 2, 3, 4, or 5,

[0048] In L 101 If there are more than 2, more than 2 L 101 Same or different from each other,

[0049] In Ar 101 When there are two or more Ar 101 Same or different from each other,

[0050] * in the above general formula (11) represents the bonding position to the pyrene ring in the above general formula (1).

[0051]

Chemical Formula 2

[0052]

[0053] (In the above general formula (2),

[0054] R2 01 ~R2 08 Each independently

[0055] hydrogen atoms,

[0056] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0057] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0058] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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

[0060] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0061] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0062] -O-(R 904 ) shown in the group,

[0063] -S-(R 905 ) shown in the group,

[0064] -N(R 906 )(R 907 ) shown in the group,

[0065] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0066] -C(=O)R 801 The groups shown,

[0067] -COOR 802 The groups shown,

[0068] Halogen atoms,

[0069] cyano,

[0070] Nitro,

[0071] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0072] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0073] L 201 and L 202 Each independently

[0074] single bond,

[0075] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0076] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0077] Ar 201 and Ar 202 Each independently

[0078] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

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

[0080] (In the first compound represented by the above general formula (1) and the second compound represented by the above general formula (2), R 901 、R 902 、R 903 、R 904 、R 905 、R 906 、R 907 、R 801 and R 802 Each independently

[0081] hydrogen atoms,

[0082] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0083] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0084] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0085] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0086] In R 901 When there are multiple R 901 Same or different from each other,

[0087] In R 902 When there are multiple R 902 Same or different from each other,

[0088] In R 903 When there are multiple R 903 Same or different from each other,

[0089] In R 904 When there are multiple R 904 Same or different from each other,

[0090] In R 905 When there are multiple R905 Same or different from each other,

[0091] In R 906 When there are multiple R 906 Same or different from each other,

[0092] In R 907 When there are multiple R 907 Same or different from each other,

[0093] In R 801 When there are multiple R 801 Same or different from each other,

[0094] In R 802 When there are multiple R 802 Same as or different from each other.)

[0095] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to one aspect of the present invention.

[0096] According to one embodiment of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to one embodiment of the present invention, an organic electroluminescent element with improved luminous efficiency can be provided. Furthermore, according to one embodiment of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0097] Figure 1 This is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0098] [definition]

[0099] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0100] In this specification, in chemical structural formulas, any bondable position not explicitly indicating a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, ie, a protium atom, a deuterium atom, or a tritium atom.

[0101] In this specification, the ring carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound and a heterocyclic compound) in which atoms are cyclically bonded. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring carbon number. The "ring carbon number" recorded below is set in the same manner as long as it is not otherwise stated. For example, the ring carbon number of a benzene ring is 6, the ring carbon number of a naphthalene ring is 10, the ring carbon number of a pyridine ring is 5, and the ring carbon number of a furan ring is 4. In addition, for example, the ring carbon number of 9,9-diphenylfluorenyl is 13, and the ring carbon number of 9,9'-spirobifluorenyl is 25.

[0102] Furthermore, when a benzene ring is substituted with, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of a benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of a naphthalene ring substituted with an alkyl group is 10.

[0103] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape (such as a monocyclic ring, a condensed ring, and an aggregated ring). Atoms that do not constitute a ring (such as a hydrogen atom that terminates the bond of the atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not otherwise stated. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. For example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0104] In this specification, "carbon number XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" refers to the carbon number of the ZZ group when it is unsubstituted and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0105] In this specification, "atomic number XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" indicates the atomic number of the ZZ group when it is unsubstituted and does not include the atomic number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0106] In this specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0107] In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0108] In this specification, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0109] "Substituents described in this specification"

[0110] The substituents described in this specification are described below.

[0111] The number of ring carbon atoms in the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0112] The number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0113] The number of carbon atoms in the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0114] The number of carbon atoms in the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0115] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0116] The number of ring carbon atoms in the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in the present specification.

[0117] The number of ring carbon atoms in the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0118] The number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0119] The number of carbon atoms in the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0120] "Substituted or unsubstituted aryl"

[0121] Specific examples of the "substituted or unsubstituted aryl group" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Herein, an unsubstituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" alone includes both "unsubstituted aryl groups" and "substituted aryl groups."

[0122] A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent, as described in the following specific example group G1A, and examples of substituted aryl groups described in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of an aryl group in the "substituted aryl groups" in the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in a "substituted aryl group" in the following specific example group G1B is further replaced with a substituent.

[0123] Unsubstituted aryl (Specific example group G1A):

[0124] Phenyl,

[0125] p-Biphenyl,

[0126] m-Biphenyl,

[0127] o-biphenyl,

[0128] 4-terphenyl-4-yl,

[0129] 4-terphenyl-3-yl,

[0130] 4-terphenyl-2-yl,

[0131] m-terphenyl-4-yl,

[0132] m-terphenyl-3-yl,

[0133] m-terphenyl-2-yl,

[0134] o-terphenyl-4-yl,

[0135] o-terphenyl-3-yl,

[0136] o-terphenyl-2-yl,

[0137] 1-naphthyl,

[0138] 2-naphthyl,

[0139] Anthracene,

[0140] Benzanthryl,

[0141] Fiki,

[0142] Triphenylene,

[0143] Phenalene,

[0144] Pyrene base,

[0145] base,

[0146] Benzo base,

[0147] triphenylene,

[0148] Benzotriphenylene,

[0149] tetraphenyl,

[0150] Pentaphenyl,

[0151] Fluorenyl,

[0152] 9,9'-spirobifluorenyl,

[0153] Benzofluorenyl,

[0154] Dibenzofluorenyl,

[0155] Fluoranthene group,

[0156] Benzofluoranthene,

[0157] Perylene and

[0158] A monovalent aromatic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0159]

Chemical Formula 3

[0160]

[0161]

Chemical Formula 4

[0162]

[0163] Substituted aryl (Specific example group G1B):

[0164] o-Tolyl,

[0165] m-Tolyl,

[0166] p-Tolyl,

[0167] p-Xylyl,

[0168] m-xylyl,

[0169] o-xylyl,

[0170] p-Isopropylphenyl,

[0171] m-isopropylphenyl,

[0172] o-isopropylphenyl,

[0173] tert-Butylphenyl,

[0174] m-tert-butylphenyl,

[0175] o-tert-butylphenyl,

[0176] 3,4,5-trimethylphenyl,

[0177] 9,9-dimethylfluorenyl,

[0178] 9,9-diphenylfluorenyl,

[0179] 9,9-bis(4-methylphenyl)fluorenyl,

[0180] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0181] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0182] Cyanophenyl,

[0183] triphenylsilylphenyl,

[0184] trimethylsilylphenyl,

[0185] Phenyl naphthyl,

[0186] naphthylphenyl and

[0187] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above-mentioned general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0188] "Substituted or unsubstituted heterocyclic group"

[0189] The term "heterocyclic group" as used herein refers to a cyclic group containing at least one heteroatom among the ring atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0190] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0191] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0192] Specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (Specific Example Group G2) include the following unsubstituted heterocyclic groups (Specific Example Group G2A) and substituted heterocyclic groups (Specific Example Group G2B). (Herein, an unsubstituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups."

[0193] A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are replaced, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0194] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0195] Specific example group G2B includes, for example, the following heterocyclic groups containing a substituted nitrogen atom (specific example group G2B1), the following heterocyclic groups containing a substituted oxygen atom (specific example group G2B2), the following heterocyclic groups containing a substituted sulfur atom (specific example group G2B3), and the following groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0196] Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0197] Pyrrolyl,

[0198] Imidazole,

[0199] Pyrazolyl,

[0200] triazole,

[0201] Tetrazolyl,

[0202] Oxazolyl,

[0203] Isoxazolyl,

[0204] Oxadiazolyl,

[0205] Thiazolyl,

[0206] Isothiazolyl,

[0207] Thiadiazole,

[0208] Pyridyl,

[0209] Pyridazinyl,

[0210] Pyrimidine group,

[0211] Pyrazinyl,

[0212] Triazine,

[0213] Indolyl,

[0214] Isoindolyl,

[0215] Indolizinyl,

[0216] Quinolizinyl,

[0217] Quinolinyl,

[0218] Isoquinolinyl,

[0219] Cinnoline,

[0220] Phthalocyanine,

[0221] Quinazoline,

[0222] Quinoxaline,

[0223] Benzimidazole,

[0224] Indazolyl,

[0225] Phenanthroline,

[0226] Phenanthridinyl,

[0227] Acridinyl,

[0228] Phenazine,

[0229] Carbazolyl,

[0230] benzocarbazolyl,

[0231] Morpholinyl,

[0232] Phenoxazinyl,

[0233] Phenothiazine,

[0234] azacarbazolyl and diazacarbazolyl.

[0235] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0236] furanyl,

[0237] Oxazolyl,

[0238] Isoxazolyl,

[0239] Oxadiazolyl,

[0240] Xanthoxylum,

[0241] Benzofuranyl,

[0242] Isobenzofuranyl,

[0243] dibenzofuranyl,

[0244] naphthobenzofuranyl,

[0245] benzoxazolyl,

[0246] Benzisoxazolyl,

[0247] Phenoxazinyl,

[0248] Morpholinyl,

[0249] dinaphthofuranyl,

[0250] Azadibenzofuranyl,

[0251] Diazadibenzofuranyl,

[0252] Azanaphthobenzofuranyl and

[0253] naphthyridinylbenzofuranyl.

[0254] Unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3):

[0255] Thiphenyl,

[0256] Thiazolyl,

[0257] Isothiazolyl,

[0258] Thiadiazole,

[0259] benzothienyl,

[0260] Isobenzothienyl,

[0261] dibenzothienyl,

[0262] naphthobenzothienyl,

[0263] Benzothiazolyl,

[0264] Benzisothiazolyl,

[0265] Phenothiazine,

[0266] dinaphthothienyl,

[0267] azadibenzothienyl,

[0268] diazadibenzothienyl,

[0269] azanaphthobenzothienyl and

[0270] diazanaphthobenzothienyl.

[0271] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):

[0272]

Chemical Formula 5

[0273]

[0274]

Chemical Formula 6

[0275]

[0276] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0277] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0278] Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0279] (9-phenyl)carbazolyl,

[0280] (9-biphenyl)carbazolyl,

[0281] (9-phenyl)phenylcarbazolyl,

[0282] (9-naphthyl)carbazolyl,

[0283] Diphenylcarbazol-9-yl,

[0284] phenylcarbazol-9-yl,

[0285] Methylbenzimidazole,

[0286] Ethylbenzimidazolyl,

[0287] Phenyltriazine,

[0288] Biphenyl triazine group,

[0289] Diphenyltriazine,

[0290] Phenylquinazolinyl and

[0291] Biphenylquinazolinyl.

[0292] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0293] Phenyldibenzofuranyl,

[0294] Methyldibenzofuranyl,

[0295] tert-Butyldibenzofuranyl and

[0296] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0297] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0298] Phenyldibenzothiophene,

[0299] Methyldibenzothiophene,

[0300] tert-Butyldibenzothienyl and

[0301] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0302] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific Example Group G2B4):

[0303] The above-mentioned “one or more hydrogen atoms of the monovalent heterocyclic group” means one or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.

[0304] "Substituted or unsubstituted alkyl"

[0305] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, unsubstituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "unsubstituted alkyl groups," and substituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "substituted alkyl groups.") Hereinafter, when simply referring to "alkyl groups," both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0306] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0307] Unsubstituted alkyl (Specific example group G3A):

[0308] methyl,

[0309] Ethyl,

[0310] n-propyl,

[0311] Isopropyl,

[0312] n-Butyl,

[0313] Isobutyl,

[0314] sec-butyl and tert-butyl.

[0315] Substituted alkyl (Specific example group G3B):

[0316] Heptafluoropropyl (including isomers),

[0317] Pentafluoroethyl,

[0318] 2,2,2-trifluoroethyl and

[0319] trifluoromethyl.

[0320] "Substituted or unsubstituted alkenyl"

[0321] Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (Specific Example Group G4) include the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B). (Herein, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" alone includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups."

[0322] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0323] Unsubstituted alkenyl (Specific example Group G4A):

[0324] Vinyl,

[0325] Allyl,

[0326] 1-butenyl,

[0327] 2-Butenyl and

[0328] 3-Butenyl.

[0329] Substituted alkenyl (Specific example group G4B):

[0330] 1,3-butadienyl,

[0331] 1-Methylvinyl,

[0332] 1-methylallyl,

[0333] 1,1-dimethylallyl,

[0334] 2-methylallyl and

[0335] 1,2-dimethylallyl.

[0336] "Substituted or unsubstituted alkynyl"

[0337] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Herein, unsubstituted alkynyl groups refer to cases where "substituted or unsubstituted alkynyl groups" are "unsubstituted alkynyl groups.") When simply referring to "alkynyl groups" below, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0338] A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (Specific Example Group G5A) are replaced with a substituent.

[0339] Unsubstituted alkynyl (specific example group G5A): ethynyl

[0340] "Substituted or unsubstituted cycloalkyl"

[0341] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups (Specific Example Group G6A) and substituted cycloalkyl groups (Specific Example Group G6B). (Herein, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referring to a "cycloalkyl group", both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" are included.

[0342] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0343] Unsubstituted cycloalkyl (Specific example group G6A):

[0344] Cyclopropyl,

[0345] Cyclobutyl,

[0346] Cyclopentyl,

[0347] Cyclohexyl,

[0348] 1-adamantyl,

[0349] 2-adamantyl,

[0350] 1-Norbornyl and

[0351] 2-Norbornyl.

[0352] Substituted cycloalkyl (specific example group G6B):

[0353] 4-Methylcyclohexyl.

[0354] ·“-Si(R 901 )(R 902 )(R 903 )”

[0355] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as specific examples (specific example group G7), and include

[0356] -Si(G1)(G1)(G1),

[0357] -Si(G1)(G2)(G2),

[0358] -Si(G1)(G1)(G2),

[0359] -Si(G2)(G2)(G2),

[0360] -Si(G3)(G3)(G3) and

[0361] -Si(G6)(G6)(G6). Here,

[0362] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0363] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0364] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0365] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0366] A plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0367] A plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0368] A plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0369] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0370] Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0371] A plurality of G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0372] ·“-O-(R 904 )”

[0373] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and include

[0374] -O(G1),

[0375] -O(G2),

[0376] -O(G3) and

[0377] -O(G6).

[0378] Here,

[0379] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0380] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0381] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0382] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0383] ·“-S-(R 905 )”

[0384] As -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0385] -S(G1),

[0386] -S(G2),

[0387] -S(G3) and

[0388] -S(G6).

[0389] Here,

[0390] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0391] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0392] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0393] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0394] ·“-N(R 906 )(R 907 )”

[0395] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0396] -N(G1)(G1),

[0397] -N(G2)(G2),

[0398] -N(G1)(G2),

[0399] -N(G3)(G3) and

[0400] -N(G6)(G6).

[0401] Here,

[0402] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0403] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0404] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0405] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0406] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0407] - A plurality of G2s in N(G2)(G2) are the same as or different from each other.

[0408] - A plurality of G3's in N(G3)(G3) are the same as or different from each other.

[0409] A plurality of G6's in -N(G6)(G6) are the same as or different from each other.

[0410] "Halogen atoms"

[0411] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0412] "Substituted or unsubstituted fluoroalkyl"

[0413] The “substituted or unsubstituted fluoroalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted fluoroalkyl group” refers to a group in which one or more hydrogen atoms of the “fluoroalkyl group” are replaced with a substituent. It should be noted that the “substituted fluoroalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted fluoroalkyl group” are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0414] "Substituted or unsubstituted haloalkyl"

[0415] The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with halogen atoms. The number of carbon atoms in the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted haloalkyl group” refers to a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. It should be noted that the “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted haloalkyl group” are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl groups" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0416] "Substituted or unsubstituted alkoxy"

[0417] A specific example of a "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0418] "Substituted or unsubstituted alkylthio"

[0419] A specific example of a "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in an "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0420] "Substituted or unsubstituted aryloxy group"

[0421] Specific examples of "substituted or unsubstituted aryloxy groups" described in this specification include groups represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring carbon atoms in the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0422] "Substituted or unsubstituted arylthio"

[0423] Specific examples of "substituted or unsubstituted arylthio groups" described in this specification include groups represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the number of ring carbon atoms in an "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0424] "Substituted or unsubstituted trialkylsilyl"

[0425] A specific example of a "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0426] "Substituted or unsubstituted aralkyl"

[0427] A specific example of a "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group." The number of carbon atoms in an "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0428] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0429] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0430] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthroline group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0431] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0432]

Chemical Formula 7

[0433]

[0434] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0435]

Chemical Formula 8

[0436]

[0437] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0438] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0439]

Chemical Formula 9

[0440]

[0441] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0442] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0443] "Substituted or unsubstituted arylene group"

[0444] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (Specific Example Group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in Specific Example Group G1 by removing one hydrogen atom from the aryl ring.

[0445] "Substituted or unsubstituted divalent heterocyclic group"

[0446] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 by removing one hydrogen atom from the heterocyclic ring.

[0447] "Substituted or unsubstituted alkylene"

[0448] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0449] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0450]

Chemical Formula 10

[0451]

[0452]

Chemical Formula 11

[0453]

[0454] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0455] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0456]

Chemical Formula 12

[0457]

[0458] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0459] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0460] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0461]

Chemical Formula 13

[0462]

[0463] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0464] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0465] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0466]

Chemical Formula 14

[0467]

[0468]

Chemical Formula 15

[0469]

[0470]

Chemical Formula 16

[0471]

[0472] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0473]

Chemical Formula 17

[0474]

[0475]

Chemical Formula 18

[0476]

[0477]

Chemical Formula 19

[0478]

[0479]

Chemical Formula 20

[0480]

[0481] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0482] The above is the description of the “substituents described in the present specification”.

[0483] "When bonding to form a ring"

[0484] In this specification, the expression "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring", "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted condensed ring", and "one or more of the adjacent groups of two or more are not bonded to each other".

[0485] The following describes the case where "one or more of a group of two or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of a group of two or more adjacent groups are bonded to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case where they are bonded to form a ring"). This description is based on the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring.

[0486]

Chemical Formula 21

[0487]

[0488] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups as one group refers to R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0489] The above “one or more groups” means that two or more groups of the above two or more adjacent groups can form a ring at the same time. 921 With R 922 bonded to form ring Q A And at the same time R 925 With R 926 bonded to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0490]

Chemical Formula 22

[0491]

[0492] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups is bonded as in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, R 921 With R 922 bonded to form ring Q A , and R 922 With R 923 bonded to form ring Q C , consisting of three adjacent (R 921 、R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0493]

Chemical Formula 23

[0494]

[0495] In the formed "monocyclic ring" or "condensed ring", the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q formed A and Ring Q B Each is a "monocyclic" or "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C If the ring Q of the above general formula (TMEP-104) A is a benzene ring, then ring Q A If the ring Q of the above general formula (TMEP-104) A is a naphthalene ring, then ring Q A It is a fused ring.

[0496] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0497] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0498] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified in Specific Example Group G2 are terminated with hydrogen atoms.

[0499] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0500] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A Refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Formation of ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0501] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur, as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by a hydrogen atom or the like, or can be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocycle.

[0502] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0503] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0504] In this specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0505] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0506] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0507] In the case of "one or more groups consisting of two or more adjacent atoms" "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms bond to each other to form a substituted or unsubstituted "unsaturated ring" formed from multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0508] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in the present specification".

[0509] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0510] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" ("the case where they are bonded to form a ring").

[0511] Substituents when expressed as "substituted or unsubstituted"

[0512] In one embodiment of the present specification, the substituent group described as "substituted or unsubstituted" (in the present specification, sometimes referred to as "optional substituent group") is, for example, selected from

[0513] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0514] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0515] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0516] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0517] -Si(R 901 )(R 902 )(R 903 ),

[0518] -O-(R 904 ),

[0519] -S-(R905 ),

[0520] -N(R 906 )(R 907 ),

[0521] Halogen atoms, cyano groups, nitro groups,

[0522] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0523] unsubstituted heterocyclic group having 5 to 50 ring atoms

[0524] The groups in the group etc.

[0525] Here, R 901 ~R 907 Each independently

[0526] hydrogen atoms,

[0527] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

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

[0531] R 901 When there are two or more, two or more R 901 Same or different from each other,

[0532] R 902 When there are two or more, two or more R 902 Same or different from each other,

[0533] R 903 When there are two or more, two or more R 903 Same or different from each other,

[0534] R 904 When there are two or more, two or more R 904 Same or different from each other,

[0535] R 905 When there are two or more, two or more R 905 Same or different from each other,

[0536] R 906 When there are two or more, two or more R 906 Same or different from each other,

[0537] R907 When there are two or more, two or more R 907 Same as or different from each other.

[0538] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0539] an alkyl group having 1 to 50 carbon atoms,

[0540] an aryl group having 6 to 50 ring carbon atoms and

[0541] Heterocyclic group having 5 to 50 ring atoms

[0542] The groups in the group.

[0543] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0544] an alkyl group having 1 to 18 carbon atoms,

[0545] an aryl group having 6 to 18 ring carbon atoms and

[0546] Heterocyclic group having 5 to 18 ring atoms

[0547] The groups in the group.

[0548] Specific examples of each of the above-mentioned optional substituents are the same as the specific examples of the substituents described in the above-mentioned section "Substituents described in the present specification".

[0549] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0550] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0551] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit and the numerical value BB described after "AA to BB" as the upper limit.

[0552] [First embodiment]

[0553] (Organic electroluminescent element)

[0554] The organic electroluminescent element involved in this embodiment comprises an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode. The first light-emitting layer contains a first compound represented by the following general formula (1) as a first host material and having at least one group represented by the following general formula (11), and the second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. In the organic EL element involved in this embodiment, the first light-emitting layer and the second light-emitting layer are directly in contact with each other.

[0555] The organic electroluminescent element according to this embodiment includes an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order.

[0556] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other" may include, for example, any of the following configurations (LS1), (LS2), and (LS3).

[0557] (LS1) A scheme in which a region where the first compound and the second compound are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[0558] (LS2) In the case where the first light-emitting layer and the second light-emitting layer contain light-emitting compounds, a region in which the first compound, the second compound, and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[0559] (LS3) In the case where the first light-emitting layer and the second light-emitting layer contain light-emitting compounds, a region formed by the light-emitting compound, a region formed by the first compound, or a region formed by the second compound is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

[0560] In this specification, the term "host material" refers to, for example, a material comprising "50% by mass or more of a layer." Thus, for example, the content of the first compound represented by the following general formula (1) in the first light-emitting layer is 50% by mass or more of the total mass of the first light-emitting layer. The content of the second compound represented by the following general formula (2) in the second light-emitting layer is 50% by mass or more of the total mass of the second light-emitting layer.

[0561] (Emission wavelength of organic EL element)

[0562] The organic electroluminescent element according to this embodiment preferably emits light having a main peak wavelength of 430 nm to 480 nm when the element is driven.

[0563] The main peak wavelength of light emitted by the organic EL element when the element is driven is measured as follows: A voltage is applied to the organic EL element so that the current density reaches 10 mA / cm 2 In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity reaches the maximum is measured and is defined as the main peak wavelength (unit: nm).

[0564] The organic EL element according to this embodiment may have one or more organic layers in addition to the first and second light-emitting layers. Examples of the organic layer include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0565] In the organic EL element involved in this embodiment, the organic layer can be composed only of the first light-emitting layer and the second light-emitting layer, or it can also have at least any one layer selected from, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer.

[0566] In the organic EL device according to this embodiment, it is preferable to include a hole transport layer between the anode and the first light-emitting layer.

[0567] In the organic EL device according to this embodiment, it is preferable to include an electron transport layer between the cathode and the second light-emitting layer.

[0568] Figure 1 A schematic configuration of an example of an organic EL element according to this embodiment is shown.

[0569] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is composed of a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9 stacked in this order from the anode 3 side.

[0570] (First Compound)

[0571] In the organic EL device according to this embodiment, the first compound is a compound represented by the following general formula (1).

[0572]

Chemical Formula 24

[0573]

[0574] (In the above general formula (1),

[0575] R 101 ~R 110 Each independently

[0576] hydrogen atoms,

[0577] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0578] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0579] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0580] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0581] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0582] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0583] -O-(R 904 ) shown in the group,

[0584] -S-(R 905 ) shown in the group,

[0585] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0586] -C(=O)R 801 The groups shown,

[0587] -COOR 802 The groups shown,

[0588] Halogen atoms,

[0589] cyano,

[0590] Nitro,

[0591] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0592] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[0593] The group represented by the above general formula (11)

[0594] Among them, R 101 ~R 110 At least one of them is a group represented by the above general formula (11),

[0595] When there are a plurality of groups represented by the general formula (11), the plurality of groups represented by the general formula (11) may be the same as or different from each other.

[0596] L 101 for

[0597] single bond,

[0598] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0599] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0600] Ar 101 for

[0601] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0602] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0603] mx is 0, 1, 2, 3, 4, or 5,

[0604] In L 101 If there are more than 2, more than 2 L 101 Same or different from each other,

[0605] In Ar 101 When there are two or more Ar 101 Same or different from each other,

[0606] * in the above general formula (11) represents the bonding position to the pyrene ring in the above general formula (1).

[0607] (In the first compound according to this embodiment, R 901 、R 902 、R 903 、R 904 、R 905 、R 906 、R 907 、R 801 and R 802 Each independently

[0608] hydrogen atoms,

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

[0610] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0611] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0612] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0613] In R 901 When there are multiple R 901 Same or different from each other,

[0614] In R 902 When there are multiple R 902 Same or different from each other,

[0615] In R 903 When there are multiple R 903 Same or different from each other,

[0616] In R 904 When there are multiple R 904 Same or different from each other,

[0617] In R 905 When there are multiple R 905 Same or different from each other,

[0618] In R 906 When there are multiple R 906 Same or different from each other,

[0619] In R 907 When there are multiple R 907 Same or different from each other,

[0620] In R 801 When there are multiple R 801 Same or different from each other,

[0621] In R 802 When there are multiple R 802 Same as or different from each other.)

[0622] In the organic EL device according to this embodiment, the pyrene ring in the first compound represented by the general formula (1) may be combined with Ar 101 The linking group (sometimes referred to as a connecting group) is represented by the following general formula (11X).

[0623]

Chemical Formula 25

[0624]

[0625] (In the above general formula (11X), L 101 and mx are respectively the same as L in the above general formula (11) 101 Same meaning as mx, * indicates the bonding position.)

[0626] In the organic electroluminescent device according to this embodiment, the first compound preferably has at least one deuterium atom. The compound represented by the above general formula (1) having at least one deuterium atom is sometimes referred to as a first deuterated compound.

[0627] An organic EL element whose light-emitting layer is composed of multiple layers (hereinafter sometimes referred to as a "stacked element") and an organic EL element whose light-emitting layer is composed of a single layer (hereinafter sometimes referred to as a "single-layer element") emit light using different mechanisms, and therefore, different issues arise from the perspective of extending the life of the element.

[0628] For example, in a single-layer device containing a pyrene compound such as that represented by the general formula (1) in the light-emitting layer, the triplet lifetime of the pyrene compound is short, the density of triplet excitons in the light-emitting layer does not increase, and so-called TTF (Triplet-Triplet Fusion) is less likely to occur. TTF is a mechanism in which triplet excitons collide with each other to generate singlet excitons (see, for example, International Publication No. 2010 / 134350).

[0629] On the other hand, in a stacked element such as the organic EL element involved in this embodiment, in which a pyrene compound such as that represented by the general formula (1) is contained in the first light-emitting layer and an anthracene compound such as that represented by the general formula (2) is contained in the second light-emitting layer, triplet excitons move from the pyrene compound to the anthracene compound, and TTF can be expected to occur in the anthracene compound. If TTF occurs in the anthracene compound, the pyrene compound present at the interface between the first light-emitting layer and the second light-emitting layer is exposed to high-order triplet excitons. Deuterated pyrene compounds such as the first deuterated compound are stable compared to non-deuterated pyrene compounds. Therefore, by using a deuterated pyrene compound in the first light-emitting layer, a sharp drop in luminous efficiency can be suppressed, and the drop in luminous efficiency can be delayed until a certain period of time has passed.

[0630] In one embodiment, the first compound is a compound having two or more pyrene rings in the molecule. In one embodiment, the first compound is a compound having two pyrene rings in the molecule.

[0631] For example, when using a compound such as the compound represented by the following general formula (101) in which pyrene rings are linked via a divalent group represented by the general formula (11X) (sometimes referred to as a bispyrene compound) to form a film at high speed, if the total number of carbon atoms contained in the divalent group represented by the general formula (11X) is large, thermal decomposition is likely to occur. When forming an organic layer such as a light-emitting layer at high speed, the compound used in the film formation is placed in an environment that is more prone to thermal decomposition.

[0632] For example, a bispyrene compound having a linking group with a large number of ring carbon atoms (large molecular weight) between two pyrene rings, such as compound R-BH1 and compound R-BH2 described later, is easily thermally decomposed during high-speed film formation. The compound produced by thermal decomposition is mixed into the organic layer as an impurity, and it is speculated that the performance of the organic EL element is easily degraded (a decrease in luminous efficiency and lifespan). It is speculated that such thermal decomposition is also likely to occur in deuterated bispyrene compounds such as the first deuterated compound. In the first deuterated compound, for example, by making the total number of carbon atoms contained in the group represented by the general formula (11X) less than 21, when mass-producing organic electroluminescent elements, even if the evaporation speed when forming the first luminous layer using the first compound is increased, the decrease in luminous efficiency and lifespan can be suppressed.

[0633] In one embodiment, the first compound is a compound having only one pyrene ring in the molecule (sometimes referred to as a monopyrene compound).

[0634] When the first compound is a monopyrene compound, if a fused ring formed by condensing four or more rings is directly bonded to a pyrene ring, hole mobility decreases. It is speculated that this decrease in hole mobility also occurs in deuterated monopyrene compounds like the first deuterated compound. If the hole mobility of the first compound contained in the first emitting layer decreases, it becomes difficult for holes to reach the interface between the first and second emitting layers, resulting in a decrease in the luminous efficiency of the organic EL device.

[0635] When the first compound is a monopyrene compound, the group directly bonded to the pyrene ring is preferably, for example, R 101 ~R 110 , the divalent group represented by the above general formula (11X) or Ar when mx is 0 101 It is not a condensed ring formed by condensing 4 or more rings. When the first compound is a monopyrene compound, the group directly bonded to the pyrene ring is preferably a group consisting of a single ring or a condensed ring formed by condensing 3 or less rings.

[0636] It should be noted that the monopyrene compound as the first compound may have a condensed ring formed by condensing four or more rings, and the condensed ring formed by condensing the pyrene ring and four or more rings is preferably connected through a connecting group composed of a single ring or a condensed ring formed by condensing three or less rings.

[0637] In the organic EL device according to this embodiment, the total number of carbon atoms contained in the group represented by the general formula (11X) in the first compound is preferably 21 or less, and more preferably 13 or less.

[0638] In the organic EL element according to this embodiment, it is not 101 The bonding position R 101~R 110 and R 111 ~R 120 The total number of carbon atoms contained is also preferably 21 or less.

[0639] In the organic EL element according to this embodiment, it is not 101 The bonding position R 101 ~R 110 and R 111 ~R 120 , and the total number of carbon atoms contained in the group represented by the above-mentioned general formula (11X) is also preferably 21 or less, and is also preferably 13 or less.

[0640] In the organic electroluminescent device according to this embodiment, R 101 ~R 110 At least one of them is preferably a deuterium atom.

[0641] In the organic electroluminescent element according to this embodiment, L 101 It is also preferred to have at least one deuterium atom.

[0642] In the organic electroluminescent element according to this embodiment, Ar 101 It is also preferred to have at least one deuterium atom.

[0643] In one embodiment, both the first light-emitting layer and the second light-emitting layer comprise a compound having at least one deuterium atom.

[0644] In one embodiment, only one of the first light-emitting layer and the second light-emitting layer contains a compound having at least one deuterium atom, and the other layer does not substantially contain a compound having a deuterium atom.

[0645] Here, "the light-emitting layer contains substantially no compound containing deuterium atoms" means that the light-emitting layer contains no deuterium atoms at all or allows the inclusion of deuterium atoms at a natural abundance ratio. The natural abundance ratio (molar fraction or atomic fraction) of deuterium atoms is, for example, 0.015% or less.

[0646] That is, the phrase “the light-emitting layer contains a compound containing at least one deuterium atom” herein means that the light-emitting layer contains the compound containing a deuterium atom in an amount exceeding the natural abundance ratio.

[0647] The presence of deuterium atoms in a compound is detected by mass spectrometry or 1 The H-NMR analysis method confirmed that the deuterium atom in the compound has a bonding position. 1 The determination was made by H-NMR analysis. Specifically, it is as follows.

[0648] When mass spectrometry is performed on the target compound, the presence of deuterium atoms can be confirmed by, for example, an increase in molecular weight by 1 compared to a corresponding compound in which all hydrogen atoms are protium atoms. 1 H-NMR analysis does not generate any signal, so the target compound can be analyzed by 1 The number of deuterium atoms contained in the molecule can be confirmed by the integral value obtained by H-NMR analysis. 1 The binding positions of the deuterium atoms were determined by H-NMR analysis and signal assignment.

[0649] In the organic electroluminescent device according to this embodiment, it is also preferable to use R 101 ~R 110 substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) represented by the group, -O-(R 904 ) represented by the group, -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The group shown, -COOR 802 At least one of the group shown, the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms has at least one deuterium atom.

[0650] In the organic EL device according to this embodiment, the group represented by the general formula (11) is preferably a group represented by the following general formula (111).

[0651]

Chemical Formula 26

[0652]

[0653] (In the above general formula (111),

[0654] X1 for CR 123 R 124 , oxygen atom, sulfur atom or NR 125 ,

[0655] L 111 and L 112 Each independently

[0656] single bond,

[0657] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0658] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0659] ma is 0, 1, 2, 3, or 4,

[0660] mb is 0, 1, 2, 3, or 4,

[0661] ma+mb is 0, 1, 2, 3 or 4,

[0662] Ar 101 Ar in the above general formula (11) 101 Same meaning,

[0663] R 121 、R 122 、R 123 、R 124 and R 125 Each independently

[0664] hydrogen atoms,

[0665] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0666] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0667] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0668] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0669] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0670] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0671] -O-(R 904 ) shown in the group,

[0672] -S-(R 905 ) shown in the group,

[0673] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0674] -C(=O)R 801 The groups shown,

[0675] -COOR 802 The groups shown,

[0676] Halogen atoms,

[0677] cyano,

[0678] Nitro,

[0679] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0680] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0681] mc is 3,

[0682] 3 Rs 121 Same or different from each other,

[0683] md is 3,

[0684] 3 Rs 122 Same as or different from each other.)

[0685] Among the carbon atoms *1 to *8 in the ring structure represented by the following general formula (111a) in the group represented by the general formula (111), L 111 Bonded at any position from *1 to *4, R 121 Bonded to the other three positions from *1 to *4, L 112 Bonded to any position from *5 to *8, R 122 Bonded to the remaining three positions from *5 to *8.

[0686]

Chemical Formula 27

[0687]

[0688] For example, in the group represented by the above general formula (111), L 111 The position of the carbon atom bonded to *2 in the ring structure represented by the general formula (111a), L 112 When the group is bonded to the carbon atom at *7 in the ring structure represented by the general formula (111a), the group represented by the general formula (111) is represented by the following general formula (111b).

[0689]

Chemical Formula 28

[0690]

[0691] (In the above general formula (111b),

[0692] X1, L 111 、L 112 、ma、mb、Ar 101 、R 121 、R 122 、R 123 、R 124 and R 125Each independently of X1, L in the above general formula (111) 111 、L 112 、ma、mb、Ar 101 、R 121 、R 122 、R 123 、R 124 and R 125 Same meaning,

[0693] Multiple R 121 Same or different from each other,

[0694] Multiple R 122 Same as or different from each other.)

[0695] In the organic EL device according to this embodiment, the group represented by the general formula (111) is preferably a group represented by the general formula (111b).

[0696] In the organic EL element according to this embodiment, it is preferable that

[0697] ma is 0, 1, or 2,

[0698] mb is 0, 1, or 2.

[0699] In the organic EL element according to this embodiment, it is preferable that

[0700] ma is 0 or 1,

[0701] mb is 0 or 1.

[0702] In the organic EL element according to this embodiment, Ar 101 It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0703] In the organic EL element according to this embodiment,

[0704] Ar 101 Preferably

[0705] substituted or unsubstituted phenyl,

[0706] substituted or unsubstituted naphthyl,

[0707] Substituted or unsubstituted biphenyl,

[0708] Substituted or unsubstituted terphenyl,

[0709] substituted or unsubstituted pyrenyl,

[0710] Substituted or unsubstituted phenanthracene, or

[0711] a substituted or unsubstituted fluorenyl group.

[0712] In the organic EL element according to this embodiment,

[0713] Ar 101 Also preferred are groups represented by the following general formula (12), general formula (13) or general formula (14).

[0714]

Chemical Formula 29

[0715]

[0716] (In the above general formulas (12), (13) and (14),

[0717] R 111 ~R 120 Each independently

[0718] hydrogen atoms,

[0719] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0720] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0721] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0722] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0723] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0724] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0725] -O-(R 904 ) shown in the group,

[0726] -S-(R 905 ) shown in the group,

[0727] -N(R 906 )(R 907 ) shown in the group,

[0728] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0729] -C(=O)R 124 The groups shown,

[0730] -COOR 125 The groups shown,

[0731] Halogen atoms,

[0732] cyano,

[0733] Nitro,

[0734] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0735] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0736] * in the above general formula (12), general formula (13) and general formula (14) represents the same as L in the above general formula (11). 101 The bonding position of, or with L in the above general formula (111) or general formula (111b) 112 bonding position.)

[0737] In the organic EL element according to this embodiment,

[0738] The first compound is preferably represented by the following general formula (101).

[0739]

Chemical Formula 30

[0740]

[0741] (In the above general formula (101),

[0742] R 101 ~R 120 Each independently

[0743] hydrogen atoms,

[0744] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0745] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0746] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0747] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0748] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0749] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0750] -O-(R 904 ) shown in the group,

[0751] -S-(R 905 ) shown in the group,

[0752] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0753] -C(=O)R 801 The groups shown,

[0754] -COOR 802 The groups shown,

[0755] Halogen atoms,

[0756] cyano,

[0757] Nitro,

[0758] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0759] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0760] Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position of

[0761] L 101 for

[0762] single bond,

[0763] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0764] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0765] mx is 0, 1, 2, 3, 4, or 5,

[0766] In L 101 If there are more than 2, more than 2 L 101 Same as or different from each other.)

[0767] In the organic EL element according to this embodiment, the first compound is preferably represented by the following general formula (1010), general formula (1011), general formula (1012), general formula (1013), general formula (1014), or general formula (1015).

[0768]

Chemical Formula 31

[0769]

[0770]

Chemical Formula 32

[0771]

[0772]

Chemical Formula 33

[0773]

[0774]

Chemical Formula 34

[0775]

[0776]

Chemical Formula 35

[0777]

[0778]

Chemical Formula 36

[0779]

[0780] (In the above general formulas (1010) to (1015),

[0781] R 101 ~R 120 Each independently

[0782] hydrogen atoms,

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

[0784] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0785] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0786] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0787] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0788] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0789] -O-(R 904 ) shown in the group,

[0790] -S-(R 905 ) shown in the group,

[0791] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0792] -C(=O)R 801 The groups shown,

[0793] -COOR 802 The groups shown,

[0794] Halogen atoms,

[0795] cyano,

[0796] Nitro,

[0797] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0798] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0799] L 101 for

[0800] single bond,

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

[0802] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0803] mx is 0, 1, 2, 3, 4, or 5,

[0804] In L 101 If there are more than 2, more than 2 L 101 Same as or different from each other.)

[0805] It should be noted that the compound represented by the above general formula (1010) is equivalent to R 103 Indicates that L 101 The bonding position, R 120 Indicates that L 101 The compound at the bonding position.

[0806] It should be noted that the compound represented by the above general formula (1011) is equivalent to R 103 Indicates that L 101 The bonding position, R 111 Indicates that L 101 The compound at the bonding position.

[0807] It should be noted that the compound represented by the above general formula (1012) is equivalent to R 103 Indicates that L 101 The bonding position, R 118 Indicates that L 101 The compound at the bonding position.

[0808] It should be noted that the compound represented by the above general formula (1013) is equivalent to R 102 Indicates that L 101 The bonding position, R 111 Indicates that L 101 The compound at the bonding position.

[0809] It should be noted that the compound represented by the above general formula (1014) is equivalent to R 102Indicates that L 101 The bonding position, R 118 Indicates that L 101 The compound at the bonding position.

[0810] It should be noted that the compound represented by the above general formula (1015) is equivalent to R 105 Indicates that L 101 The bonding position, R 118 Indicates that L 101 The compound at the bonding position.

[0811] In the organic EL device according to this embodiment, the first compound is preferably represented by the general formula (1010).

[0812] In the organic EL element according to this embodiment, mx is preferably 1, 2, or 3.

[0813] In the organic electroluminescent element according to this embodiment, it is preferred that the organic electroluminescent element is not 101 The bonding position R 101 ~R 110 At least one of them is a deuterium atom, not L 101 The bonding position R 111 ~R 120 At least one of them is a deuterium atom.

[0814] In the organic EL element according to this embodiment,

[0815] L 101 Preferably

[0816] Single button, or

[0817] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0818] In the organic electroluminescent element according to this embodiment, L 101 Preferably, it is any one of the following general formulae (TEMP-42) to (TEMP-44).

[0819]

Chemical Formula 37

[0820]

[0821] (In the above general formulas (TEMP-42) to (TEMP-44), Q1 to Q5 are each independently a hydrogen atom or a substituent.)

[0822] In the organic electroluminescent device according to this embodiment, it is preferred that at least one of Q1 to Q5 is a deuterium atom.

[0823] In the above general formula (TEMP-42), it is preferred that at least one of Q1 to Q4 is a deuterium atom.

[0824] In the above general formula (TEMP-43), it is preferred that at least one of Q1 to Q3 and Q5 is a deuterium atom.

[0825] In the above general formula (TEMP-44), it is preferred that at least one of Q1, Q2, Q4 and Q5 is a deuterium atom.

[0826] In the organic electroluminescent device according to this embodiment, it is preferred that one or more and four or less of Q1 to Q5 are substituents.

[0827] In the organic electroluminescent device according to this embodiment, preferably, one or more and four or less of Q1 to Q5 are substituents, and at least one of the one or more and four or less substituents has at least one deuterium atom.

[0828] In one embodiment,

[0829] In the above general formula (TEMP-42), one or more groups of two or more adjacent ones of Q1 to Q4 are present.

[0830] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0831] bonded to each other to form a substituted or unsubstituted fused ring, or

[0832] Not bonded to each other,

[0833] In the above general formula (TEMP-43), one or more groups of two or more adjacent ones of Q1 to Q3 are present.

[0834] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0835] bonded to each other to form a substituted or unsubstituted fused ring, or

[0836] Not bonded to each other,

[0837] In the above general formula (TEMP-44), one or more groups consisting of two or more adjacent ones of Q1, Q2, Q4, and Q5

[0838] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0839] bonded to each other to form a substituted or unsubstituted fused ring, or

[0840] Not bonded to each other,

[0841] Q1 to Q5 that do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0842] hydrogen atoms,

[0843] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0844] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0845] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0846] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0847] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0848] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0849] -O-(R 904 ) shown in the group,

[0850] -S-(R 905 ) shown in the group,

[0851] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0852] -C(=O)R 801 The groups shown,

[0853] -COOR 802 The groups shown,

[0854] Halogen atoms,

[0855] cyano,

[0856] Nitro,

[0857] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0858] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0859] In the organic EL element according to this embodiment,

[0860] The first compound is preferably represented by the following general formula (102).

[0861]

Chemical Formula 38

[0862]

[0863] (In the above general formula (102),

[0864] R 101~R 120 Each independently of R in the above general formula (101) 101 ~R 120 Same meaning,

[0865] Among them, R 101 ~R 110 One of them represents L 111 The bonding position, R 111 ~R 120 One of them represents L 112 The bonding position of

[0866] X1 for CR 123 R 124 , oxygen atom, sulfur atom or NR 125 ,

[0867] L 111 and L 112 Each independently

[0868] single bond,

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

[0870] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0871] ma is 0, 1, 2, 3, or 4,

[0872] mb is 0, 1, 2, 3, or 4,

[0873] ma+mb is 0, 1, 2, 3 or 4,

[0874] R 121 、R 122 、R 123 、R 124 and R 125 Each independently

[0875] hydrogen atoms,

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

[0877] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0878] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0879] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0880] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0881] -Si(R 901 )(R902 )(R 903 ) shown in the group,

[0882] -O-(R 904 ) shown in the group,

[0883] -S-(R 905 ) shown in the group,

[0884] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0885] -C(=O)R 801 The groups shown,

[0886] -COOR 802 The groups shown,

[0887] Halogen atoms,

[0888] cyano,

[0889] Nitro,

[0890] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0891] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0892] mc is 3,

[0893] 3 Rs 121 Same or different from each other,

[0894] md is 3,

[0895] 3 Rs 122 Same as or different from each other.)

[0896] Among the compounds represented by the above general formula (102), preferably,

[0897] ma is 0, 1, or 2,

[0898] mb is 0, 1, or 2.

[0899] Among the compounds represented by the above general formula (102), preferably,

[0900] ma is 0 or 1,

[0901] mb is 0 or 1.

[0902] In the organic EL element according to this embodiment, it is also preferable that mx is 1, 2, 3, 4 or 5, and L 101 It is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0903] In the organic EL element according to this embodiment, R 101 ~R 110 Two or more of them are preferably groups represented by the above-mentioned general formula (11).

[0904] In the organic electroluminescent element according to this embodiment, it is preferred that the organic electroluminescent element is not 111 The bonding position R 101 ~R 110 At least one of them is a deuterium atom, not L 112 The bonding position R 111 ~R 120 At least one of them is a deuterium atom.

[0905] In the organic EL element according to this embodiment,

[0906] Preferably, R 101 ~R 110 Two or more of them are groups represented by the above general formula (11) and Ar 101 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0907] In the organic EL element according to this embodiment, it is preferable that

[0908] Ar 101 is not a substituted or unsubstituted pyrenyl group,

[0909] L 101 is not a substituted or unsubstituted pyrene group,

[0910] R other than the group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is not a substituted or unsubstituted pyrenyl group.

[0911] In the organic EL element according to this embodiment, it is preferable that

[0912] R is not a group represented by the above general formula (11) 101 ~R 110 Each independently

[0913] hydrogen atoms,

[0914] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0915] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0916] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0917] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0918] In the organic EL element according to this embodiment, it is preferable that

[0919] R is not a group represented by the above general formula (11) 101 ~R 110 Each independently

[0920] hydrogen atoms,

[0921] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0922] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0923] In the organic EL device according to this embodiment, R 101 ~R 110 Preferred is a hydrogen atom.

[0924] In the first compound and the second compound, the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.

[0925] In the organic EL element according to this embodiment,

[0926] For example, R in the first compound represented by the above general formula (1) 101 to R 110 Two of them are groups represented by the general formula (11).

[0927] In the organic EL element according to this embodiment,

[0928] For example, R in the first compound represented by the above general formula (1) 101 to R 110 Three of them are groups represented by the general formula (11).

[0929] In the organic EL element according to this embodiment,

[0930] For example, R in the first compound represented by the above general formula (1) 101 to R 110 Among them, four are groups represented by the general formula (11).

[0931] In the organic EL element according to this embodiment,

[0932] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), and mx is 1 or greater.

[0933] In the organic EL element according to this embodiment,

[0934] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 is a substituted or unsubstituted aryl group.

[0935] In the organic EL element according to this embodiment,

[0936] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 is a substituted or unsubstituted heterocyclic group containing a nitrogen atom.

[0937] In the organic EL element according to this embodiment,

[0938] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 is a substituted or unsubstituted heterocyclic group containing a sulfur atom.

[0939] In the organic EL element according to this embodiment,

[0940] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 Substituted or unsubstituted

[0941] furanyl,

[0942] Oxazolyl,

[0943] Isoxazolyl,

[0944] Oxadiazolyl,

[0945] Xanthoxylum,

[0946] Benzofuranyl,

[0947] Isobenzofuranyl,

[0948] dibenzofuranyl,

[0949] benzoxazolyl,

[0950] Benzisoxazolyl,

[0951] Phenoxazinyl,

[0952] Morpholinyl,

[0953] dinaphthofuranyl,

[0954] Azadibenzofuranyl,

[0955] Diazadibenzofuranyl,

[0956] Azanaphthobenzofuranyl and

[0957] naphthyridinylbenzofuranyl.

[0958] In the organic EL element according to this embodiment,

[0959] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 To select from unsubstituted

[0960] furanyl,

[0961] Oxazolyl,

[0962] Isoxazolyl,

[0963] Oxadiazolyl,

[0964] Xanthoxylum,

[0965] Benzofuranyl,

[0966] Isobenzofuranyl,

[0967] dibenzofuranyl,

[0968] benzoxazolyl,

[0969] Benzisoxazolyl,

[0970] Phenoxazine,

[0971] Morpholinyl,

[0972] dinaphthofuranyl,

[0973] Azadibenzofuranyl,

[0974] Diazadibenzofuranyl,

[0975] Azanaphthobenzofuranyl and

[0976] At least one group selected from the group consisting of naphthyridinylbenzofuranyl groups.

[0977] In the organic EL element according to this embodiment,

[0978] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 is a substituted or unsubstituted dibenzofuranyl group.

[0979] In the organic EL element according to this embodiment,

[0980] For example, R in the first compound represented by the above general formula (1) 101 to R 110 One of them is a group represented by the general formula (11), mx is 0, Ar 101 It is an unsubstituted dibenzofuranyl group.

[0981] In the organic EL element according to this embodiment,

[0982] For example, mx in the first compound represented by the above general formula (101) is 2 or greater.

[0983] In the organic EL element according to this embodiment,

[0984] For example, in the first compound represented by the general formula (101), mx is 1 or more, and L 101 It is an arylene group having 6 to 24 ring carbon atoms, or a divalent heterocyclic group having 5 to 24 ring atoms.

[0985] In the organic EL element according to this embodiment,

[0986] For example, in the first compound represented by the general formula (101), mx is 1 or more, and L 101 It is an arylene group having 6 to 18 ring carbon atoms, or a divalent heterocyclic group having 5 to 18 ring atoms.

[0987] (Method for producing the first compound)

[0988] The first compound can be produced by a known method. Alternatively, the first compound can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[0989] (Specific example of the first compound)

[0990] Specific examples of the first compound include the following compounds: However, the present invention is not limited to these specific examples of the first compound.

[0991]

Chemical Formula 39

[0992]

[0993]

Chemical Formula 40

[0994]

[0995]

Chemical Formula 41

[0996]

[0997]

Chemical Formula 42

[0998]

[0999]

Chemical Formula 43

[1000]

[1001]

Chemical Formula 44

[1002]

[1003]

Chemical Formula 45

[1004]

[1005]

Chemical Formula 46

[1006]

[1007]

Chemical Formula 47

[1008]

[1009]

Chemical Formula 48

[1010]

[1011]

Chemical Formula 49

[1012]

[1013]

Chemical Formula 50

[1014]

[1015]

Chemical Formula 51

[1016]

[1017]

Chemical Formula 52

[1018]

[1019]

Chemical Formula 53

[1020]

[1021]

Chemical Formula 54

[1022]

[1023]

Chemical Formula 55

[1024]

[1025]

Chemical Formula 56

[1026]

[1027]

Chemical Formula 57

[1028]

[1029]

Chemical Formula 58

[1030]

[1031]

Chemical Formula 59

[1032]

[1033]

Chemical Formula 60

[1034]

[1035]

Chemical Formula 61

[1036]

[1037]

Chemical Formula 62

[1038]

[1039]

Chemical Formula 63

[1040]

[1041]

Chemical Formula 64

[1042]

[1043]

Chemical Formula 65

[1044]

[1045]

Chemical Formula 66

[1046]

[1047]

Chemical Formula 67

[1048]

[1049]

Chemical Formula 68

[1050]

[1051]

Chemical Formula 69

[1052]

[1053]

Chemical Formula 70

[1054]

[1055]

Chemical Formula 71

[1056]

[1057]

Chemical Formula 72

[1058]

[1059]

Chemical Formula 73

[1060]

[1061]

Chemical Formula 74

[1062]

[1063]

Chemical Formula 75

[1064]

[1065]

Chemical Formula 76

[1066]

[1067]

Chemical Formula 77

[1068]

[1069]

Chemical Formula 78

[1070]

[1071]

Chemical Formula 79

[1072]

[1073]

Chemical Formula 80

[1074]

[1075]

Chemical Formula 81

[1076]

[1077]

Chemical Formula 82

[1078]

[1079]

Chemical Formula 83

[1080]

[1081]

Chemical Formula 84

[1082]

[1083]

Chemical Formula 85

[1084]

[1085]

Chemical Formula 86

[1086]

[1087]

Chemical Formula 87

[1088]

[1089]

Chemical Formula 88

[1090]

[1091]

Chemical Formula 89

[1092]

[1093]

Chemical Formula 90

[1094]

[1095]

Chemical Formula 91

[1096]

[1097]

Chemical Formula 92

[1098]

[1099]

Chemical Formula 93

[1100]

[1101]

Chemical Formula 94

[1102]

[1103]

Chemical Formula 95

[1104]

[1105]

Chemical Formula 96

[1106]

[1107]

Chemical Formula 97

[1108]

[1109]

Chemical Formula 98

[1110]

[1111]

Chemical Formula 99

[1112]

[1113]

Chemical Formula 100

[1114]

[1115] Chemical Formula 101

[1116]

[1117]

Chemical Formula 102

[1118]

[1119]

Chemical Formula 103

[1120]

[1121]

Chemical Formula 104

[1122]

[1123]

Chemical Formula 105

[1124]

[1125]

Chemical Formula 106

[1126]

[1127]

Chemical Formula 107

[1128]

[1129]

Chemical Formula 108

[1130]

[1131]

Chemical Formula 109

[1132]

[1133]

Chemical Formula 110

[1134]

[1135]

Chemical Formula 111

[1136]

[1137]

Chemical Formula 112

[1138]

[1139]

Chemical Formula 113

[1140]

[1141]

Chemical Formula 114

[1142]

[1143]

Chemical Formula 115

[1144]

[1145] (Second Compound)

[1146] In the organic EL device according to this embodiment, the second compound is a compound represented by the following general formula (2).

[1147]

Chemical Formula 116

[1148]

[1149] (In the above general formula (2),

[1150] R 201 ~R 208 Each independently

[1151] hydrogen atoms,

[1152] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1153] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[1154] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1155] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1156] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1157] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1158] -O-(R 904 ) shown in the group,

[1159] -S-(R 905 ) shown in the group,

[1160] -N(R 906 )(R 907 ) shown in the group,

[1161] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1162] -C(=O)R 801 The groups shown,

[1163] -COOR 802 The groups shown,

[1164] Halogen atoms,

[1165] cyano,

[1166] Nitro,

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

[1168] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1169] L 201 and L 202 Each independently

[1170] single bond,

[1171] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1172] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1173] Ar 201 and Ar 202 Each independently

[1174] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1175] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1176] (In the second compound according to this embodiment, R 901、R 902 、R 903 、R 904 、R 905 、R 906 、R 907 、R 801 and R 802 Each independently

[1177] hydrogen atoms,

[1178] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1179] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1180] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1181] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1182] In R 901 When there are multiple R 901 Same or different from each other,

[1183] In R 902 When there are multiple R 902 Same or different from each other,

[1184] In R 903 When there are multiple R 903 Same or different from each other,

[1185] In R 904 When there are multiple R 904 Same or different from each other,

[1186] In R 905 When there are multiple R 905 Same or different from each other,

[1187] In R 906 When there are multiple R 906 Same or different from each other,

[1188] In R 907 When there are multiple R 907 Same or different from each other,

[1189] In R 801 When there are multiple R 801 Same or different from each other,

[1190] In R 802 When there are multiple R802 Same as or different from each other.)

[1191] In the organic EL element according to this embodiment, it is preferable that

[1192] R 201 ~R 208 Each independently

[1193] hydrogen atoms,

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

[1195] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[1196] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1197] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1198] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1199] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1200] -O-(R 904 ) shown in the group,

[1201] -S-(R 905 ) shown in the group,

[1202] -N(R 906 )(R 907 ) shown in the group,

[1203] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1204] -C(=O)R 801 The groups shown,

[1205] -COOR 802 The groups shown,

[1206] Halogen atoms,

[1207] cyano, or

[1208] Nitro,

[1209] L 201 and L 202 Each independently

[1210] single bond,

[1211] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1212] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1213] Ar 201 and Ar 202 Each independently

[1214] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1215] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1216] In the organic EL element according to this embodiment, it is preferable that

[1217] L 201 and L 202 Each independently

[1218] Single button or

[1219] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[1220] Ar 201 and Ar 202 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1221] In the organic EL element according to this embodiment,

[1222] Ar 201 and Ar 202 Each independently preferably

[1223] Phenyl,

[1224] Naphthyl,

[1225] Fiki,

[1226] Biphenyl,

[1227] terphenyl,

[1228] Diphenylfluorenyl,

[1229] Dimethylfluorenyl,

[1230] Benzodiphenylfluorenyl,

[1231] Benzodimethylfluorenyl,

[1232] dibenzofuranyl,

[1233] dibenzothiophene,

[1234] naphthobenzofuranyl, or

[1235] Naphthobenzothienyl.

[1236] In the organic EL element involved in this embodiment, the second compound represented by the above-mentioned general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209).

[1237]

Chemical Formula 117

[1238]

[1239]

Chemical Formula 118

[1240]

[1241]

Chemical Formula 119

[1242]

[1243]

Chemical Formula 120

[1244]

[1245]

Chemical Formula 121

[1246]

[1247]

Chemical Formula 122

[1248]

[1249]

Chemical Formula 123

[1250]

[1251]

Chemical Formula 124

[1252]

[1253]

Chemical Formula 125

[1254]

[1255] (In the above general formulas (201) to (209),

[1256] L 201 and Ar 201 and L in the above general formula (2) 201 and Ar 201 Same meaning,

[1257] R 201~R 208 Each independently of R in the above general formula (2) 201 ~R 208 Same meaning.)

[1258] The second compound represented by the above-mentioned general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) or general formula (229).

[1259]

Chemical Formula 126

[1260]

[1261]

Chemical Formula 127

[1262]

[1263]

Chemical Formula 128

[1264]

[1265]

Chemical Formula 129

[1266]

[1267]

Chemical Formula 130

[1268]

[1269]

Chemical Formula 131

[1270]

[1271]

Chemical Formula 132

[1272]

[1273]

Chemical Formula 133

[1274]

[1275]

Chemical Formula 134

[1276]

[1277] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228) and (229),

[1278] R 201 and R203 ~R 208 Each independently of R in the above general formula (2) 201 and R 203 ~R 208 Same meaning,

[1279] L 201 and Ar 201 Respectively with L in the above general formula (2) 201 and Ar 201 Same meaning,

[1280] L 203 and L in the above general formula (2) 201 Same meaning,

[1281] L 203 With L 201 Same or different from each other,

[1282] Ar 203 and Ar in the above general formula (2) 201 Same meaning,

[1283] Ar 203 with Ar 201 Same as or different from each other.)

[1284] The second compound represented by the above-mentioned general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) or general formula (249).

[1285]

Chemical Formula 135

[1286]

[1287]

Chemical Formula 136

[1288]

[1289]

Chemical Formula 137

[1290]

[1291]

Chemical Formula 138

[1292]

[1293]

Chemical Formula 139

[1294]

[1295]

Chemical Formula 140

[1296]

[1297]

Chemical Formula 141

[1298]

[1299]

Chemical Formula 142

[1300]

[1301]

Chemical Formula 143

[1302]

[1303] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248) and (249),

[1304] R 201 、R 202 and R 204 ~R 208 Each independently of R in the above general formula (2) 201 、R 202 and R 204 ~R 208 Same meaning,

[1305] L 203 and L in the above general formula (2) 201 Same meaning,

[1306] L 203 With L 201 Same or different from each other,

[1307] Ar 203 and Ar in the above general formula (2) 201 Same meaning,

[1308] Ar 203 with Ar 201 Same as or different from each other.)

[1309] In the second compound represented by the above general formula (2), R which is not a group represented by the above general formula (21) 201 ~R 208 Each independently preferably

[1310] hydrogen atoms,

[1311] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[1313] -Si(R 901 )(R 902 )(R 903 ) shown in the group.

[1314] Preferred L 101 for

[1315] Single button or

[1316] an unsubstituted arylene group having 6 to 22 ring carbon atoms,

[1317] Ar 101 It is a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.

[1318] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), from the viewpoint of preventing the inhibition of intermolecular interaction and suppressing the decrease in electron mobility, R as a substituent of the anthracene skeleton is 201 ~R 208 Preferably a hydrogen atom, but R 201 ~R 208 It may also be a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1319] R 201 ~R 208 In the case of a high steric hindrance substituent such as an alkyl group or a cycloalkyl group, the interaction between molecules is suppressed, the electron mobility decreases relative to the first compound, and there is a possibility that the relationship μH2>μH1 described in the following mathematical formula (Mathematical Formula 3) will not be satisfied. When the second compound is used in the second light-emitting layer, it can be expected that by satisfying the relationship μH2>μH1, the decrease in the ability of holes and electrons to recombine in the first light-emitting layer and the decrease in the luminous efficiency can be suppressed. It should be noted that as a substituent, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by the group, -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906 )(R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups, and nitro groups may form high steric hindrance, and alkyl groups and cycloalkyl groups may form even higher steric hindrance.

[1320] In the second compound represented by the above general formula (2), R as a substituent of the anthracene skeleton is201 ~R 208 It is preferably not a high steric hindrance substituent, preferably not an alkyl group or a cycloalkyl group, more preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by the group, -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906 )(R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups and nitro groups.

[1321] In the organic EL element according to this embodiment,

[1322] In the second compound represented by the above general formula (2), R 201 ~R 208 Each independently

[1323] hydrogen atoms,

[1324] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1325] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1326] -Si(R 901 )(R 902 )(R 903 ) shown in the group.

[1327] In the organic EL element according to this embodiment,

[1328] In the second compound represented by the above general formula (2), R 201 ~R 208 Preferred is a hydrogen atom.

[1329] In the above second compound, R 201 ~R 208 When the substituent is expressed as "substituted or unsubstituted", it is also preferred that the substituents mentioned above which may form high steric hindrance are not included, and in particular, substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups are not included. 201 ~R 208When the substituent is expressed as "substituted or unsubstituted", by not including substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups, the inhibition of intermolecular interactions caused by the presence of highly sterically hindered substituents such as alkyl groups and cycloalkyl groups can be prevented, thereby preventing a decrease in electron mobility. In addition, when such a second compound is used in the second light-emitting layer, a decrease in the recombination ability of holes and electrons in the first light-emitting layer and a decrease in the luminous efficiency can be suppressed.

[1330] More preferably, R as a substituent of the anthracene skeleton is 201 ~R 208 It is not a high steric hindrance substituent. R 201 ~R 208 is unsubstituted. In addition, R as a substituent of the anthracene skeleton 201 ~R 208 In the case of a non-high steric hindrance substituent, R 201 ~R 208 When a substituent is bonded to the phosphine group, the substituent is preferably not a high steric hindrance substituent. 201 ~R 208 The substituent bonded to the above is preferably not an alkyl group or a cycloalkyl group, more preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ) represented by the group, -O-(R 904 ) represented by the group, -S-(R 905 ) represented by the group, -N(R 906 )(R 907 ) represented by a group, an aralkyl group, -C(=O)R 801 The group shown, -COOR 802 The groups shown, halogen atoms, cyano groups and nitro groups.

[1331] In the second compound described above, any group described as "substituted or unsubstituted" is preferably an "unsubstituted" group.

[1332] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 is a substituted or unsubstituted dibenzofuranyl group.

[1333] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 It is an unsubstituted dibenzofuranyl group.

[1334] In the organic EL device according to this embodiment, for example, the second compound represented by the general formula (2) has at least one hydrogen atom, and at least one of the hydrogen atom is deuterium.

[1335] In the organic EL device according to this embodiment, the second compound preferably has at least one deuterium atom.

[1336] In the organic EL element according to this embodiment, it is preferable that R 201 ~R 208 At least one of them is a deuterium atom.

[1337] In the organic EL element according to this embodiment, it is preferable that L 201 and L 202 At least any one of has at least one deuterium atom.

[1338] In the organic electroluminescent element according to this embodiment, Ar 201 and Ar 202 At least any one of has at least one deuterium atom.

[1339] In the organic EL device according to this embodiment, for example, L in the second compound represented by the general formula (2) 201 TEMP-63 to TEMP-68.

[1340]

Chemical Formula 144

[1341]

[1342] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 is selected from substituted or unsubstituted anthracenyl,

[1343] Benzanthryl,

[1344] Fiki,

[1345] Triphenylene,

[1346] Phenalene,

[1347] Pyrene base,

[1348] base,

[1349] Benzo base,

[1350] triphenylene,

[1351] Benzotriphenylene,

[1352] tetraphenyl,

[1353] Pentaphenyl,

[1354] Fluoranthene group,

[1355] Benzofluoranthene and

[1356] At least one group selected from the group consisting of a perylenyl group.

[1357] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 is a substituted or unsubstituted fluorenyl group.

[1358] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 is a substituted or unsubstituted xanthene group.

[1359] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 It is benzoxanthene.

[1360] (Method for producing the second compound)

[1361] The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[1362] (Specific example of the second compound)

[1363] Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.

[1364]

Chemical Formula 145

[1365]

[1366]

Chemical Formula 146

[1367]

[1368]

Chemical Formula 147

[1369]

[1370]

Chemical Formula 148

[1371]

[1372]

Chemical Formula 149

[1373]

[1374]

Chemical Formula 150

[1375]

[1376]

Chemical Formula 151

[1377]

[1378]

Chemical Formula 152

[1379]

[1380]

Chemical Formula 153

[1381]

[1382]

Chemical Formula 154

[1383]

[1384]

Chemical Formula 155

[1385]

[1386]

Chemical Formula 156

[1387]

[1388]

Chemical Formula 157

[1389]

[1390]

Chemical Formula 158

[1391]

[1392]

Chemical Formula 159

[1393]

[1394]

Chemical Formula 160

[1395]

[1396]

Chemical Formula 161

[1397]

[1398]

Chemical Formula 162

[1399]

[1400]

Chemical Formula 163

[1401]

[1402]

Chemical Formula 164

[1403]

[1404]

Chemical Formula 165

[1405]

[1406]

Chemical Formula 166

[1407]

[1408]

Chemical Formula 167

[1409]

[1410]

Chemical Formula 168

[1411]

[1412]

Chemical Formula 169

[1413]

[1414]

Chemical Formula 170

[1415]

[1416]

Chemical Formula 171

[1417]

[1418]

Chemical Formula 172

[1419]

[1420]

Chemical Formula 173

[1421]

[1422]

Chemical Formula 174

[1423]

[1424]

Chemical Formula 175

[1425]

[1426]

Chemical Formula 176

[1427]

[1428]

Chemical Formula 177

[1429]

[1430]

Chemical Formula 178

[1431]

[1432]

Chemical Formula 179

[1433]

[1434]

Chemical Formula 180

[1435]

[1436]

Chemical Formula 181

[1437]

[1438] (Third compound and fourth compound)

[1439] In the organic EL device according to this embodiment, it is also preferred that the first light-emitting layer further contain a third fluorescent compound.

[1440] In the organic EL device according to this embodiment, it is also preferred that the second light-emitting layer further contain a fourth fluorescent compound.

[1441] When the first light-emitting layer contains the third compound and the second light-emitting layer contains the fourth compound, the third compound and the fourth compound may be the same as or different from each other.

[1442] The third compound and the fourth compound are each independently selected from

[1443] The compound represented by the following general formula (3),

[1444] The compound represented by the following general formula (4),

[1445] The compound represented by the following general formula (5),

[1446] The compound represented by the following general formula (6),

[1447] The compound represented by the following general formula (7),

[1448] The compound represented by the following general formula (8),

[1449] The compound represented by the following general formula (9) and

[1450] One or more compounds selected from the group consisting of compounds represented by the following general formula (10).

[1451] (Compound represented by general formula (3))

[1452] The compound represented by the general formula (3) will be described.

[1453]

Chemical Formula 182

[1454]

[1455] (In the above general formula (3),

[1456] R 301 ~R 310 One or more groups of two or more adjacent

[1457] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1458] bonded to each other to form a substituted or unsubstituted fused ring, or

[1459] Not bonded to each other,

[1460] R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31),

[1461] R does not form the above-mentioned monocyclic ring, does not form the above-mentioned condensed ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently

[1462] hydrogen atoms,

[1463] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1464] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1465] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1466] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1467] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1468] -O-(R 904 ) shown in the group,

[1469] -S-(R 905 ) shown in the group,

[1470] -N(R 906 )(R 907 ) shown in the group,

[1471] Halogen atoms,

[1472] cyano,

[1473] Nitro,

[1474] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1475] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1476]

Chemical Formula 183

[1477]

[1478] (In the above general formula (31),

[1479] Ar 301 and Ar 302 Each independently

[1480] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1481] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1482] L 301 ~L 303 Each independently

[1483] single bond,

[1484] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1485] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1486] * represents the bonding position in the pyrene ring in the above general formula (3).

[1487] In the third and fourth compounds, R 901 、R 902 、R 903 、R 904 、R 905 、R 906 and R 907 Each independently

[1488] hydrogen atoms,

[1489] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1490] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1491] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1492] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1493] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1494] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1495] In R 901 When there are multiple R 901 Same or different from each other,

[1496] In R 902 When there are multiple R 902 Same or different from each other,

[1497] In R 903 When there are multiple R 903 Same or different from each other,

[1498] In R 904 When there are multiple R 904 Same or different from each other,

[1499] In R 905 When there are multiple R 905 Same or different from each other,

[1500] In R 906 When there are multiple R 906 Same or different from each other,

[1501] In R 907 When there are multiple R 907 Same as or different from each other.

[1502] In the above general formula (3), preferably R 301 ~R 310 Two of them are groups represented by the above-mentioned general formula (31).

[1503] In one embodiment, the compound represented by the general formula (3) is a compound represented by the following general formula (33).

[1504]

Chemical Formula 184

[1505]

[1506] (In the above general formula (33),

[1507] R 311 ~R 318 Each independently of the monovalent group R in the general formula (3) other than the monovalent group represented by the general formula (31) 301 ~R310 Same meaning,

[1508] L 311 ~L 316 Each independently

[1509] single bond,

[1510] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1511] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1512] Ar 312 、Ar 313 、Ar 315 and Ar 316 Each independently

[1513] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1514] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1515] In the above general formula (31), L 301 Preferably, it is a single bond, L 302 and L 303 It is preferably a single bond.

[1516] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or (35).

[1517]

Chemical Formula 185

[1518]

[1519] (In the above general formula (34),

[1520] R 311 ~R 318 Each independently of the monovalent group R in the general formula (3) other than the monovalent group represented by the general formula (31) 301 ~R 310 Same meaning,

[1521] L 312 , L 313 , L 315 and L 316 Each independently of L in the above general formula (33) 312 , L 313 , L 315 and L 316 Same meaning,

[1522] Ar 312 、Ar313 、Ar 315 and Ar 316 Each independently and Ar in the above general formula (33) 312 、Ar 313 、Ar 315 and Ar 316 Same meaning.)

[1523]

Chemical Formula 186

[1524]

[1525] (In the above general formula (35),

[1526] R 311 ~R 318 Each independently of the monovalent group R in the general formula (3) other than the monovalent group represented by the general formula (31) 301 ~R 310 Same meaning,

[1527] Ar 312 、Ar 313 、Ar 315 and Ar 316 Each independently and Ar in the above general formula (33) 312 、Ar 313 、Ar 315 and Ar 316 Same meaning.)

[1528] In the above general formula (31), preferably, Ar 301 and Ar 302 At least one of them is a group represented by the following general formula (36).

[1529] In the above general formulas (33) to (35), it is preferred that Ar 312 and Ar 313 At least one of them is a group represented by the following general formula (36).

[1530] In the above general formulas (33) to (35), it is preferred that Ar 315 and Ar 316 At least one of them is a group represented by the following general formula (36).

[1531]

Chemical Formula 187

[1532]

[1533] (In the above general formula (36),

[1534] X3 represents an oxygen atom or a sulfur atom,

[1535] R 321 ~R 327 One or more groups of two or more adjacent

[1536] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1537] bonded to each other to form a substituted or unsubstituted fused ring, or

[1538] Not bonded to each other,

[1539] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 321 ~R 327 Each independently

[1540] hydrogen atoms,

[1541] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1542] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1543] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1544] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1545] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1546] -O-(R 904 ) shown in the group,

[1547] -S-(R 905 ) shown in the group,

[1548] -N(R 906 )(R 907 ) shown in the group,

[1549] Halogen atoms,

[1550] cyano,

[1551] Nitro,

[1552] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1553] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1554] *Indicates the same as L 302 、L 303 、L 312 、L 313 、L 315 or L316 bonding position.)

[1555] X3 is preferably an oxygen atom.

[1556] R 321 ~R 327 At least one of them is preferably

[1557] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1558] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1559] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1560] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1561] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1562] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1563] In the above general formula (31), preferably, Ar 301 is a group represented by the above general formula (36), Ar 302 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1564] In the above general formulas (33) to (35), it is preferred that Ar 312 is a group represented by the above general formula (36), Ar 313 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1565] In the above general formulas (33) to (35), it is preferred that Ar 315 is a group represented by the above general formula (36), Ar 316 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1566] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).

[1567]

Chemical Formula 188

[1568]

[1569] (In the above general formula (37),

[1570] R 311 ~R 318 Each independently of the monovalent group R in the general formula (3) other than the monovalent group represented by the general formula (31) 301 ~R310 Same meaning,

[1571] R 321 ~R 327 One or more groups of two or more adjacent

[1572] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1573] bonded to each other to form a substituted or unsubstituted fused ring, or

[1574] Not bonded to each other,

[1575] R 341 ~R 347 One or more groups of two or more adjacent

[1576] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1577] bonded to each other to form a substituted or unsubstituted fused ring, or

[1578] Not bonded to each other,

[1579] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 321 ~R 327 and R 341 ~R 347 Each independently

[1580] hydrogen atoms,

[1581] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1582] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1583] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1584] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1585] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1586] -O-(R 904 ) shown in the group,

[1587] -S-(R 905 ) shown in the group,

[1588] -N(R 906 )(R 907 ) shown in the group,

[1589] Halogen atoms,

[1590] cyano,

[1591] Nitro,

[1592] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1593] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1594] R 331 ~R 335 and R 351 ~R 355 Each independently

[1595] hydrogen atoms,

[1596] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1597] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1598] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1599] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1600] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1601] -O-(R 904 ) shown in the group,

[1602] -S-(R 905 ) shown in the group,

[1603] -N(R 906 )(R 907 ) shown in the group,

[1604] Halogen atoms, cyano groups, nitro groups,

[1605] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1606] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1607] Specific examples of the compound represented by the general formula (3) include the following compounds.

[1608]

Chemical Formula 189

[1609]

[1610]

Chemical Formula 190

[1611]

[1612]

Chemical Formula 191

[1613]

[1614]

Chemical Formula 192

[1615]

[1616]

Chemical Formula 193

[1617]

[1618] (Compound represented by general formula (4))

[1619] The compound represented by the general formula (4) will be described.

[1620]

Chemical Formula 194

[1621]

[1622] (In the above general formula (4),

[1623] Z is each independently CRa or a nitrogen atom,

[1624] Ring A1 and ring A2 are each independently

[1625] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1626] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1627] When there are multiple Ra, one or more groups of two or more adjacent Ra

[1628] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1629] bonded to each other to form a substituted or unsubstituted fused ring, or

[1630] Not bonded to each other,

[1631] n21 and n22 are each independently 0, 1, 2, 3 or 4,

[1632] When there are multiple Rb, one or more groups of two or more adjacent Rb

[1633] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1634] bonded to each other to form a substituted or unsubstituted fused ring, or

[1635] Not bonded to each other,

[1636] When there are multiple Rcs, one or more groups of two or more adjacent Rcs are selected.

[1637] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1638] bonded to each other to form a substituted or unsubstituted fused ring, or

[1639] Not bonded to each other,

[1640] Ra, Rb and Rc which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

[1641] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1642] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1643] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1644] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1645] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1646] -O-(R 904 ) shown in the group,

[1647] -S-(R 905 ) shown in the group,

[1648] -N(R 906 )(R 907 ) shown in the group,

[1649] Halogen atoms,

[1650] cyano,

[1651] Nitro,

[1652] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1653] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1654] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group".

[1655] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms in the central condensed bicyclic structure of the above general formula (4) as ring-constituting atoms.

[1656] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

[1657] The "heterocycle" of the A1 ring and the A2 ring has the same structure as a compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

[1658] The "heterocycle" of the A1 ring and the A2 ring contains two carbon atoms in the central fused bicyclic structure of the above general formula (4) as ring atoms.

[1659] Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds obtained by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2.

[1660] Rb is bonded to any carbon atom forming the aromatic hydrocarbon ring as the A1 ring, or any atom forming the heterocyclic ring as the A1 ring.

[1661] Rc is bonded to any carbon atom forming the aromatic hydrocarbon ring as the A2 ring, or any atom forming the heterocyclic ring as the A2 ring.

[1662] Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and at least two are more preferably groups represented by the following general formula (4a).

[1663]

Chemical Formula 195

[1664] *-L 401 -Ar 401 (4a)

[1665] (In the above general formula (4a),

[1666] L 401 for

[1667] single bond,

[1668] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1669] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1670] Ar 401 for

[1671] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1672] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1673] A group represented by the following general formula (4b).

[1674]

Chemical Formula 196

[1675]

[1676] (In the above general formula (4b),

[1677] L 402 and L 403 Each independently

[1678] single bond,

[1679] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1680] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1681] Ar 402 and Ar 403 The group

[1682] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1683] bonded to each other to form a substituted or unsubstituted fused ring, or

[1684] Not bonded to each other,

[1685] Ar which does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 402 and Ar 403 Each independently

[1686] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1687] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1688] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).

[1689]

Chemical Formula 197

[1690]

[1691] (In the above general formula (42),

[1692] R 401 ~R 411 One or more groups of two or more adjacent

[1693] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1694] bonded to each other to form a substituted or unsubstituted fused ring, or

[1695] Not bonded to each other,

[1696] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 401 ~R 411 Each independently

[1697] hydrogen atoms,

[1698] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1699] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1700] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1701] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1702] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1703] -O-(R 904 ) shown in the group,

[1704] -S-(R 905 ) shown in the group,

[1705] -N(R 906 )(R 907 ) shown in the group,

[1706] Halogen atoms,

[1707] cyano,

[1708] Nitro,

[1709] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1710] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1711] R 401 ~R 411 Among them, at least one is preferably a group represented by the above-mentioned general formula (4a), and at least two are more preferably groups represented by the above-mentioned general formula (4a).

[1712] R 404 and R 411 Preferred is a group represented by the above-mentioned general formula (4a).

[1713] In one embodiment, the compound represented by the general formula (4) is a compound in which the structure represented by the following general formula (4-1) or (4-2) is bonded to the A1 ring.

[1714] In one embodiment, the compound represented by the general formula (42) is 404 ~R 407 A compound in which a structure represented by the following general formula (4-1) or (4-2) is bonded to the bonded ring.

[1715]

Chemical Formula 198

[1716]

[1717] (In the above general formula (4-1), the two * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring as the A1 ring in the above general formula (4), or to R 404 ~R 407 Any bond in

[1718] The three * in the general formula (4-2) are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring as the A1 ring in the general formula (4), or to R in the general formula (42). 404 ~R 407 Any bond in

[1719] R 421 ~R 427 One or more groups of two or more adjacent

[1720] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1721] bonded to each other to form a substituted or unsubstituted fused ring, or

[1722] Not bonded to each other,

[1723] R 431 ~R 438 One or more groups of two or more adjacent

[1724] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1725] bonded to each other to form a substituted or unsubstituted fused ring, or

[1726] Not bonded to each other,

[1727] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 421 ~R 427 and R431 ~R 438 Each independently

[1728] hydrogen atoms,

[1729] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1730] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1731] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1732] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1733] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1734] -O-(R 904 ) shown in the group,

[1735] -S-(R 905 ) shown in the group,

[1736] -N(R 906 )(R 907 ) shown in the group,

[1737] Halogen atoms,

[1738] cyano,

[1739] Nitro,

[1740] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1741] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1742] In one embodiment, the compound represented by the general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5).

[1743]

Chemical Formula 199

[1744]

[1745]

Chemical Formula 200

[1746]

[1747]

Chemical Formula 201

[1748]

[1749] (In the above general formula (41-3), formula (41-4) and formula (41-5),

[1750] The A1 ring has the same definition as in the above general formula (4),

[1751] R 421 ~R 427 Each independently of R in the above general formula (4-1) 421 ~R 427 Same meaning,

[1752] R 440 ~R 448 Each independently of R in the above general formula (42) 401 ~R 411 Same meaning.)

[1753] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms as the A1 ring of the general formula (41-5) is

[1754] Substituted or unsubstituted naphthalene ring or

[1755] a substituted or unsubstituted fluorene ring.

[1756] In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms as the A1 ring of the general formula (41-5) is

[1757] a substituted or unsubstituted dibenzofuran ring,

[1758] Substituted or unsubstituted carbazole ring or

[1759] a substituted or unsubstituted dibenzothiophene ring.

[1760] In one embodiment, the compound represented by the above general formula (4) or the above general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).

[1761]

Chemical Formula 202

[1762]

[1763]

Chemical Formula 203

[1764]

[1765]

Chemical Formula 204

[1766]

[1767]

Chemical Formula 205

[1768]

[1769]

Chemical Formula 206

[1770]

[1771] (In the above general formulas (461), (462), (463), (464), (465), (466) and (467),

[1772] R 421 ~R 427 Each independently of R in the above general formula (4-1) 421 ~R 427 Same meaning,

[1773] R 431 ~R 438 Each independently of R in the above general formula (4-2) 431 ~R 438 Same meaning,

[1774] R 440 ~R 448 and R 451 ~R 454 Each independently of R in the above general formula (42) 401 ~R 411 Same meaning,

[1775] X4 is an oxygen atom, NR 801 or C(R 802 )(R 803 ),

[1776] R 801 、R 802 and R 803 Each independently

[1777] hydrogen atoms,

[1778] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1779] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1780] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1781] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1782] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1783] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1784] In R801 When there are multiple R 801 Same or different from each other,

[1785] In R 802 When there are multiple R 802 Same or different from each other,

[1786] In R 803 When there are multiple R 803 Same as or different from each other.)

[1787] In one embodiment, for the compound represented by the general formula (42), R 401 ~R 411 Among the groups consisting of two or more adjacent ones, one or more groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring. This embodiment is described in detail as a compound represented by the following general formula (45).

[1788] (Compound represented by general formula (45))

[1789] The compound represented by the general formula (45) will be described.

[1790]

Chemical Formula 207

[1791]

[1792] (In the above general formula (45),

[1793] Choose from R 461 With R 462 The group composed of 462 With R 463 The group composed of 464 With R 465 The group composed of 465 With R 466 The group composed of 466 With R 467 The group composed of 468 With R 469 The group composed of 469 With R 470 The group composed of R 470 With R 471 Two or more groups in the large group formed by the groups are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

[1794] in,

[1795] R 461 With R 462The group and R 462 With R 463 The groups formed do not simultaneously form a ring;

[1796] R 464 With R 465 The group and R 465 With R 466 The groups formed do not simultaneously form a ring;

[1797] R 465 With R 466 The group and R 466 With R 467 The groups formed do not simultaneously form a ring;

[1798] R 468 With R 469 The group and R 469 With R 470 The groups do not simultaneously form a ring; and

[1799] R 469 With R 470 The group and R 470 With R 471 The groups do not form a ring at the same time.

[1800] R 461 ~R 471 The two or more rings formed are identical or different from each other,

[1801] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 461 ~R 471 Each independently

[1802] hydrogen atoms,

[1803] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1804] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1805] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1806] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1807] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1808] -O-(R 904 ) shown in the group,

[1809] -S-(R 905) represented by the group, -N(R 906 )(R 907 ) shown in the group,

[1810] Halogen atoms,

[1811] cyano,

[1812] Nitro,

[1813] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1814] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1815] In the above general formula (45), R n With R n+1 (n represents an integer selected from 461, 462, 464 to 466 and 468 to 470) are bonded to each other and R n and R n+1 The two carbon atoms bonded to the ring together form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.

[1816] The number of the ring structures in the compound represented by the general formula (45) is, for example, 2, 3, or 4. The two or more ring structures may each be present on the same benzene ring on the parent skeleton of the general formula (45), or may be present on different benzene rings. For example, in the case of three ring structures, one ring structure may be present on each of the three benzene rings of the general formula (45).

[1817] Examples of the ring structure in the compound represented by the general formula (45) include structures represented by the following general formulae (451) to (460).

[1818]

Chemical Formula 208

[1819]

[1820] (In the above general formulas (451) to (457),

[1821] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R n and R n+1 The two ring-forming carbon atoms bonded to

[1822] R nThe bonded ring carbon atoms may be any one of the two ring carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[1823] X 45 C(R 4512 )(R 4513 ),NR 4514 , oxygen atoms or sulfur atoms,

[1824] R 4501 ~R 4506 and R 4512 ~R 4513 One or more groups of two or more adjacent

[1825] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1826] bonded to each other to form a substituted or unsubstituted fused ring, or

[1827] Not bonded to each other,

[1828] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 4501 ~R 4514 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.)

[1829]

Chemical Formula 209

[1830]

[1831] (In the above general formulas (458) to (460),

[1832] *1 and *2 as well as *3 and *4 represent R n and R n+1 The two ring-forming carbon atoms bonded to

[1833] R n The ring-forming carbon atom to which the bond is attached may be any one of the two ring-forming carbon atoms represented by *1 and *2 or *3 and *4.

[1834] X 45 C(R 4512 )(R 4513 ),NR 4514 , oxygen atoms or sulfur atoms,

[1835] R 4512 ~R 4513 and R 4515 ~R 4525One or more groups of two or more adjacent

[1836] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1837] bonded to each other to form a substituted or unsubstituted fused ring, or

[1838] Not bonded to each other,

[1839] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 4512 ~R 4513 、R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.)

[1840] In the above general formula (45), preferably R 462 、R 464 、R 465 、R 470 and R 471 At least one (preferably R 462 、R 465 and R 470 At least one of, more preferably R 462 ) is a group that does not form a ring structure.

[1841] (i) In the above general formula (45), R n With R n+1 When the formed ring structure has a substituent,

[1842] (ii) R in the above general formula (45) that does not form a ring structure 461 ~R 471 as well as

[1843] (iii) R in formulas (451) to (460) 4501 ~R 4514 、R 4515 ~R 4525 Preferably, each independently selected from

[1844] hydrogen atoms,

[1845] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1846] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1847] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1848] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1849] -N(R 906 )(R 907 ) shown in the group,

[1850] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1851] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1852] Any group selected from the group consisting of groups represented by the following general formulae (461) to (464).

[1853]

Chemical Formula 210

[1854]

[1855] (In the above general formulas (461) to (464),

[1856] R d Each independently

[1857] hydrogen atoms,

[1858] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1859] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1860] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1861] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1862] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1863] -O-(R 904 ) shown in the group,

[1864] -S-(R 905 ) shown in the group,

[1865] -N(R 906 )(R 907 ) shown in the group,

[1866] Halogen atoms,

[1867] cyano,

[1868] Nitro,

[1869] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1870] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1871] X 46 C(R 801 )(R 802 ),NR 803 , oxygen atoms or sulfur atoms,

[1872] R 801 、R 802 and R 803 Each independently

[1873] hydrogen atoms,

[1874] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1875] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1876] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1877] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1878] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1879] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1880] In R 801 When there are multiple R 801 Same or different from each other,

[1881] In R 802 When there are multiple R 802 Same or different from each other,

[1882] In R 803 When there are multiple R 803 Same or different from each other,

[1883] p1 is 5,

[1884] p2 is 4,

[1885] p3 is 3,

[1886] p4 is 7,

[1887] In the above general formulae (461) to (464), * each independently represents a bonding position to the ring structure.

[1888] In the third and fourth compounds, R901 ~R 907 Same definition as above.

[1889] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).

[1890]

Chemical Formula 211

[1891]

[1892]

Chemical Formula 212

[1893]

[1894] (In the above general formulas (45-1) to (45-6),

[1895] Rings d to i are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

[1896] R 461 ~R 471 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.)

[1897] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).

[1898]

Chemical Formula 213

[1899]

[1900]

Chemical Formula 214

[1901]

[1902] (In the above general formulas (45-7) to (45-12),

[1903] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring.

[1904] R 461 ~R 471 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.)

[1905] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).

[1906]

Chemical Formula 215

[1907]

[1908]

Chemical Formula 216

[1909]

[1910]

Chemical Formula 217

[1911]

[1912] (In the above general formulas (45-13) to (45-21),

[1913] Rings d to k are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

[1914] R 461 ~R 471 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.)

[1915] When the ring g or the ring h further has a substituent, examples of the substituent include:

[1916] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1917] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1918] The group represented by the above general formula (461),

[1919] The group represented by the above general formula (463) or

[1920] The group represented by the above-mentioned general formula (464).

[1921] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).

[1922]

Chemical Formula 218

[1923]

[1924] (In the above general formulas (45-22) to (45-25),

[1925] X 46 and X 47 Each independently is C(R 801 )(R 802 ),NR 803 , oxygen atoms or sulfur atoms,

[1926] R 461 ~R 471 and R 481 ~R 488 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.

[1927] R 801 、R 802 and R 803 Each independently

[1928] hydrogen atoms,

[1929] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1930] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1931] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1932] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1933] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1934] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1935] In R 801 When there are multiple R 801 Same or different from each other,

[1936] In R 802 When there are multiple R 802 Same or different from each other,

[1937] In R 803 When there are multiple R 803 Same as or different from each other.)

[1938] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formula (45-26).

[1939]

Chemical Formula 219

[1940]

[1941] (In the above general formula (45-26),

[1942] X 46 C(R 801 )(R 802 ),NR803 , oxygen atoms or sulfur atoms,

[1943] R 463 、R 464 、R 467 、R 468 、R 471 and R 481 ~R 492 Each independently of R in the above general formula (45) 461 ~R 471 Same meaning.

[1944] R 801 、R 802 and R 803 Each independently

[1945] hydrogen atoms,

[1946] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1947] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1948] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1949] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1950] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1951] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1952] In R 801 When there are multiple R 801 Same or different from each other,

[1953] In R 802 When there are multiple R 802 Same or different from each other,

[1954] In R 803 When there are multiple R 803 Same as or different from each other.)

[1955] Specific examples of the compound represented by the general formula (4) include the following compounds: In the following specific examples, Ph represents a phenyl group, and D represents a deuterium atom.

[1956]

Chemical Formula 220

[1957]

[1958]

Chemical Formula 221

[1959]

[1960]

Chemical Formula 222

[1961]

[1962]

Chemical Formula 223

[1963]

[1964]

Chemical Formula 224

[1965]

[1966]

Chemical Formula 225

[1967]

[1968]

Chemical Formula 226

[1969]

[1970]

Chemical Formula 227

[1971]

[1972]

Chemical Formula 228

[1973]

[1974]

Chemical Formula 229

[1975]

[1976] (Compound represented by general formula (5))

[1977] The compound represented by the general formula (5) is described below. The compound represented by the general formula (5) corresponds to the compound represented by the general formula (41-3) described above.

[1978]

Chemical Formula 230

[1979]

[1980] (In the above general formula (5),

[1981] R 501 ~R 507 and R 511 ~R 517 One or more groups of two or more adjacent

[1982] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1983] bonded to each other to form a substituted or unsubstituted fused ring, or

[1984] Not bonded to each other,

[1985] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 501 ~R 507 and R 511 ~R 517 Each independently

[1986] hydrogen atoms,

[1987] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1988] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1989] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1990] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1991] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1992] -O-(R 904 ) shown in the group,

[1993] -S-(R 905 ) shown in the group,

[1994] -N(R 906 )(R 907 ) shown in the group,

[1995] Halogen atoms,

[1996] cyano,

[1997] Nitro,

[1998] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1999] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2000] R 521 and R 522 Each independently

[2001] hydrogen atoms,

[2002] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2003] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2004] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2005] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2006] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2007] -O-(R 904 ) shown in the group,

[2008] -S-(R 905 ) shown in the group,

[2009] -N(R 906 )(R 907 ) shown in the group,

[2010] Halogen atoms,

[2011] cyano,

[2012] Nitro,

[2013] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2014] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2015] “R 501 ~R 507 and R 511 ~R 517 One of the groups consisting of two or more adjacent ones is, for example, R 501 With R 502 The group composed of 502 With R 503 The group composed of 503 With R 504 The group composed of 505 With R 506 The group composed of 506 With R 507 The group composed of 501 With R 502 With R 503 The groups formed are combined.

[2016] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of the 906 )(R 907) shown in the group.

[2017] In one embodiment, R 501 ~R 507 and R 511 ~R 517 Each independently

[2018] hydrogen atoms,

[2019] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2020] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2021] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52).

[2022]

Chemical Formula 231

[2023]

[2024] (In the above general formula (52),

[2025] R 531 ~R 534 and R 541 ~R 544 One or more groups of two or more adjacent

[2026] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2027] bonded to each other to form a substituted or unsubstituted fused ring, or

[2028] Not bonded to each other,

[2029] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 531 ~R 534 、R 541 ~R 544 , and R 551 and R 552 Each independently

[2030] hydrogen atoms,

[2031] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2032] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2033] R 561 ~R 564 Each independently

[2034] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2035] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2036] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53).

[2037]

Chemical Formula 232

[2038]

[2039] (In the above general formula (53), R 551 、R 552 and R 561 ~R 564 Each independently of R in the above general formula (52) 551 、R 552 and R 561 ~R 564 Same meaning.)

[2040] In one embodiment, R in the above general formula (52) and general formula (53) 561 ~R 564 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[2041] In one embodiment, R in the above general formula (5) 521 and R 522 , R in the above general formula (52) and general formula (53) 551 and R 552 A hydrogen atom.

[2042] In one embodiment, the substituents in the above formulae (5), (52) and (53) when expressed as "substituted or unsubstituted" are

[2043] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2044] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2045] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2046] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2047] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2048] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2049] Specific examples of the compound represented by the general formula (5) include the following compounds.

[2050]

Chemical Formula 233

[2051]

[2052]

Chemical Formula 234

[2053]

[2054]

Chemical Formula 235

[2055]

[2056]

Chemical Formula 236

[2057]

[2058]

Chemical Formula 237

[2059]

[2060]

Chemical Formula 238

[2061]

[2062]

Chemical Formula 239

[2063]

[2064]

Chemical Formula 240

[2065]

[2066]

Chemical Formula 241

[2067]

[2068]

Chemical Formula 242

[2069]

[2070]

Chemical Formula 243

[2071]

[2072]

Chemical Formula 244

[2073]

[2074]

Chemical Formula 245

[2075]

[2076]

Chemical Formula 246

[2077]

[2078]

Chemical Formula 247

[2079]

[2080]

Chemical Formula 248

[2081]

[2082] (Compound represented by general formula (6))

[2083] The compound represented by the general formula (6) will be described.

[2084]

Chemical Formula 249

[2085]

[2086] (In the above general formula (6),

[2087] Ring a, ring b and ring c are each independently

[2088] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2089] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[2090] R 601 and R 602 Each independently bonds to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

[2091] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 601 and R 602 Each independently

[2092] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2093] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2094] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2095] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2096] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2097] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2098] Ring a, ring b and ring c are rings fused to the central fused bicyclic structure of the above general formula (6) composed of a boron atom and two nitrogen atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

[2099] The "aromatic hydrocarbon rings" of ring a, ring b, and ring c have the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "aryl group".

[2100] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms in the central fused bicyclic structure of the above general formula (6) as ring-constituting atoms.

[2101] The "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms in the central condensed bicyclic structure of the above general formula (6) as ring-constituting atoms.

[2102] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

[2103] The "heterocycles" of ring a, ring b, and ring c have the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

[2104] The "heterocycle" of ring a contains three carbon atoms in the central fused bicyclic structure of the general formula (6) as ring atoms. The "heterocycle" of ring b and ring c contains two carbon atoms in the central fused bicyclic structure of the general formula (6) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom is introduced into the "heterocyclic group" described in Specific Example Group G2.

[2105] R 601 and R 602 Each independently can be bonded to ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring includes the nitrogen atom on the fused two-ring structure at the center of the general formula (6). In this case, the heterocyclic ring may also contain heteroatoms other than nitrogen atoms. R 601 and R 602 Specifically, the atoms constituting the a ring, the b ring or the c ring are bonded to the atoms constituting the R 601 and R 602 For example, it can also be R 601 It is bonded to the a ring to form a fused ring containing R 601 A nitrogen-containing heterocyclic ring fused with two (or more) nitrogen-containing heterocyclic rings of the ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group fused with two or more nitrogen rings in Specific Example Group G2.

[2106] R 601 When bonded to the b ring, R 602 When bonded to the a ring and R 602 The bonding to the C ring is the same as above.

[2107] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

[2108] In one embodiment, the ring a, ring b and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

[2109] In one embodiment, R in the above general formula (6) 601 and R 602 Each independently

[2110] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2111] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2112] It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2113] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62).

[2114]

Chemical Formula 250

[2115]

[2116] (In the above general formula (62),

[2117] R 601A and selected from R 611 and R 621 One or more of them are bonded to form a substituted or unsubstituted heterocyclic ring, or no substituted or unsubstituted heterocyclic ring is formed,

[2118] R 602A and selected from R 613 and R 614 One or more of them are bonded to form a substituted or unsubstituted heterocyclic ring, or no substituted or unsubstituted heterocyclic ring is formed,

[2119] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 601A and R 602A Each independently

[2120] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2121] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2122] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2123] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2124] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2125] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2126] R 611 ~R 621 One or more groups of two or more adjacent

[2127] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2128] bonded to each other to form a substituted or unsubstituted fused ring, or

[2129] Not bonded to each other,

[2130] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned monocyclic ring, and does not form the above-mentioned condensed ring 611 ~R 621 Each independently

[2131] hydrogen atoms,

[2132] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2133] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2134] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2135] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2136] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2137] -O-(R 904 ) shown in the group,

[2138] -S-(R 905 ) shown in the group,

[2139] -N(R 906 )(R 907 ) shown in the group,

[2140] Halogen atoms,

[2141] cyano,

[2142] Nitro,

[2143] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2144] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2145] R in the above general formula (62) 601A and R 602A are respectively the same as R in the above general formula (6) 601 and R 602 The corresponding group.

[2146] For example, you can R 601A With R 611 The nitrogen-containing heterocyclic ring is bonded to form a 2-ring condensed (or 3-ring condensed or more) nitrogen-containing heterocyclic ring containing the ring and the benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the 2-ring condensed or more heterocyclic groups containing nitrogen in the specific example group G2. 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.

[2147] R 611 ~R 621 One or more of the groups of two or more adjacent ones can be

[2148] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2149] They are bonded to each other to form a substituted or unsubstituted fused ring.

[2150] For example, you can R 611 With R 612 They are bonded to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring is condensed with the six-membered ring to which they are bonded, and the formed condensed ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

[2151] In one embodiment, R not involved in ring formation 611 ~R 621 Each independently

[2152] hydrogen atoms,

[2153] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2154] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2155] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2156] In one embodiment, R not involved in ring formation 611 ~R 621 Each independently

[2157] hydrogen atoms,

[2158] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2159] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2160] In one embodiment, R not involved in ring formation 611 ~R 621 Each independently

[2161] Hydrogen atoms or

[2162] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2163] In one embodiment, R not involved in ring formation 611 ~R 621 Each independently

[2164] Hydrogen atoms or

[2165] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2166] R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2167] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63).

[2168]

Chemical Formula 251

[2169]

[2170] (In the above general formula (63),

[2171] R 631 With R 646 bonded to form a substituted or unsubstituted heterocyclic ring, or not to form a substituted or unsubstituted heterocyclic ring,

[2172] R 633 With R 647 bonded to form a substituted or unsubstituted heterocyclic ring, or not to form a substituted or unsubstituted heterocyclic ring,

[2173] R 634 With R 651 bonded to form a substituted or unsubstituted heterocyclic ring, or not to form a substituted or unsubstituted heterocyclic ring,

[2174] R 641 With R 642 bonded to form a substituted or unsubstituted heterocyclic ring, or not to form a substituted or unsubstituted heterocyclic ring,

[2175] R 631 ~R 651 One or more groups of two or more adjacent

[2176] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2177] bonded to each other to form a substituted or unsubstituted fused ring, or

[2178] Not bonded to each other,

[2179] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned monocyclic ring, and does not form the above-mentioned condensed ring 631 ~R 651 Each independently

[2180] hydrogen atoms,

[2181] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2182] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2183] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2184] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2185] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2186] -O-(R 904 ) shown in the group,

[2187] -S-(R 905 ) shown in the group,

[2188] -N(R 906 )(R 907 ) shown in the group,

[2189] Halogen atoms,

[2190] cyano,

[2191] Nitro,

[2192] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2193] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2194] R 631 Can be used with R 646 bonded to form a substituted or unsubstituted heterocyclic ring. 631 With R 646 Bonded to form a fused R 646 The benzene ring to which the ring is bonded, the ring containing N and the benzene ring corresponding to the a ring are fused with three or more nitrogen-containing heterocyclic rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the heterocyclic group containing three or more nitrogen-containing rings fused in the specific example group G2. 633 With R 647 Bonding situation, R 634 With R 651 Bonding conditions and R 641 With R 642 The bonding situation is the same as above.

[2195] In one embodiment, R not involved in ring formation 631 ~R 651 Each independently

[2196] hydrogen atoms,

[2197] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2198] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2199] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2200] In one embodiment, R not involved in ring formation 631 ~R 651 Each independently

[2201] hydrogen atoms,

[2202] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2203] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2204] In one embodiment, R not involved in ring formation 631 ~R 651 Each independently

[2205] Hydrogen atoms or

[2206] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2207] In one embodiment, R not involved in ring formation 631 ~R 651 Each independently

[2208] Hydrogen atoms or

[2209] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2210] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2211] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A).

[2212]

Chemical Formula 252

[2213]

[2214] (In the above general formula (63A),

[2215] R 661 for

[2216] hydrogen atoms,

[2217] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2218] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2219] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2220] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[2221] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2222] R 662 ~R 665 Each independently

[2223] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2224] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2225] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2226] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[2227] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2228] In one embodiment, R 661 ~R 665 Each independently

[2229] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[2230] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2231] In one embodiment, R 661 ~R 665 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2232] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B).

[2233]

Chemical Formula 253

[2234]

[2235] (In the above general formula (63B),

[2236] R 671 and R 672 Each independently

[2237] hydrogen atoms,

[2238] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2239] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2240] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2241] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2242] -N(R 906 )(R 907 ) or

[2243] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2244] R 673 ~R 675 Each independently

[2245] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2246] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2247] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2248] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2249] -N(R 906 )(R 907 ) or

[2250] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2251] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B').

[2252]

Chemical Formula 254

[2253]

[2254] (In the above general formula (63B'), R 672 ~R 675 Each independently of R in the above general formula (63B) 672 ~R 675 Same meaning.)

[2255] In one embodiment, R 671 ~R 675 At least one of them is

[2256] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2257] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2258] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2259] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2260] -N(R 906 )(R 907 ) or

[2261] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2262] In one embodiment,

[2263] R 672 for

[2264] hydrogen atoms,

[2265] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2266] -N(R 906 )(R 907) or

[2267] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2268] R 671 and R 673 ~R 675 Each independently

[2269] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2270] -N(R 906 )(R 907 ) or

[2271] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2272] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C).

[2273]

Chemical Formula 255

[2274]

[2275] (In the above general formula (63C),

[2276] R 681 and R 682 Each independently

[2277] hydrogen atoms,

[2278] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2279] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2280] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2281] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[2282] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2283] R 683 ~R 686 Each independently

[2284] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2285] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2286] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2287] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[2288] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2289] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C′).

[2290]

Chemical Formula 256

[2291]

[2292] (In the above general formula (63C'), R 683 ~R 686 Each independently of R in the above general formula (63C) 683 ~R 686 Same meaning.)

[2293] In one embodiment, R 681 ~R 686 Each independently

[2294] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[2295] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2296] In one embodiment, R 681 ~R 686 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2297] For the compound represented by the general formula (6), the rings a, b and c can be connected by a connecting group (containing NR 601 Groups and groups containing NR 602 The intermediate is produced by bonding with a group (containing a boron atom) to produce a first intermediate (first reaction), and then the a, b, and c rings are bonded using a linking group (a group containing a boron atom) to produce the final product (second reaction). An amination reaction such as the Buchwald-Hartwig reaction can be used in the first reaction. A tandem hetero Friedel-Crafts reaction can be used in the second reaction.

[2298] Although specific examples of the compound represented by the general formula (6) are described below, these are merely examples, and the compound represented by the general formula (6) is not limited to the following specific examples.

[2299]

Chemical Formula 257

[2300]

[2301]

Chemical Formula 258

[2302]

[2303]

Chemical Formula 259

[2304]

[2305]

Chemical Formula 260

[2306]

[2307]

Chemical Formula 261

[2308]

[2309]

Chemical Formula 262

[2310]

[2311]

Chemical Formula 263

[2312]

[2313]

Chemical Formula 264

[2314]

[2315]

Chemical Formula 265

[2316]

[2317]

Chemical Formula 266

[2318]

[2319]

Chemical Formula 267

[2320]

[2321]

Chemical Formula 268

[2322]

[2323] (Compound represented by general formula (7))

[2324] The compound represented by the general formula (7) will be described.

[2325]

Chemical Formula 269

[2326]

[2327]

Chemical Formula 270

[2328]

[2329] (In the above general formula (7),

[2330] The r ring is a ring represented by the above general formula (72) or (73) fused at any position of the adjacent ring,

[2331] The q ring and the s ring are each independently a ring represented by the above general formula (74) fused at any position of the adjacent rings,

[2332] The p ring and the t ring are each independently a structure represented by the above general formula (75) or general formula (76) fused at any position of the adjacent rings,

[2333] X7 is an oxygen atom, a sulfur atom or NR 702 .

[2334] In R 701 When there are multiple adjacent R 701

[2335] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2336] bonded to each other to form a substituted or unsubstituted fused ring, or

[2337] Not bonded to each other,

[2338] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 701 and R 702 Each independently

[2339] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2340] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2341] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2342] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2343] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2344] -O-(R 904 ) shown in the group,

[2345] -S-(R 905 ) shown in the group,

[2346] -N(R 906 )(R 907) shown in the group,

[2347] Halogen atoms,

[2348] cyano,

[2349] Nitro,

[2350] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2351] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2352] Ar 701 and Ar 702 Each independently

[2353] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2354] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2355] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2356] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2357] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2358] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2359] L 701 for

[2360] a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

[2361] a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

[2362] a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

[2363] a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

[2364] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[2365] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[2366] m1 is 0, 1, or 2,

[2367] m2 is 0, 1, 2, 3 or 4,

[2368] m3 are each independently 0, 1, 2 or 3,

[2369] m4 are each independently 0, 1, 2, 3, 4 or 5,

[2370] In R 701 When there are multiple R 701 Same or different from each other,

[2371] When there are multiple X7, the multiple X7 are the same or different from each other.

[2372] In R 702 When there are multiple R 702 Same or different from each other,

[2373] In Ar 701 When there are multiple Ar 701 Same or different from each other,

[2374] In Ar 702 When there are multiple Ar 702 Same or different from each other,

[2375] In L 701 When there are multiple L 701 Same as or different from each other.)

[2376] In the general formula (7), each of the rings p, q, r, s, and t is fused to the adjacent ring so as to share two carbon atoms. The position and direction of fusion are not limited and fusion can be performed at any position and direction.

[2377] In one embodiment, in the above general formula (72) or general formula (73) as the r ring, m1=0 or m2=0.

[2378] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).

[2379]

Chemical Formula 271

[2380]

[2381]

Chemical Formula 272

[2382]

[2383]

Chemical Formula 273

[2384]

[2385]

Chemical Formula 274

[2386]

[2387]

Chemical Formula 275

[2388]

[2389]

Chemical Formula 276

[2390]

[2391] (In the above general formulas (71-1) to (71-6), R 701 、X7、Ar 701 、Ar 702 、L 701 , m1 and m3 are respectively the same as R in the above general formula (7) 701 、X7、Ar 701 、Ar 702 、L 701 , m1 and m3 have the same meaning.)

[2392] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).

[2393]

Chemical Formula 277

[2394]

[2395]

Chemical Formula 278

[2396]

[2397]

Chemical Formula 279

[2398]

[2399] (In the above general formulas (71-11) to (71-13), R 701 、X7、Ar 701 、Ar 702 、L 701 , m1, m3 and m4 are respectively the same as R in the above general formula (7) 701 、X7、Ar 701 、Ar 702 、L 701 , m1, m3 and m4 have the same meaning.)

[2400] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-21) to (71-25).

[2401]

Chemical Formula 280

[2402]

[2403]

Chemical Formula 281

[2404]

[2405]

Chemical Formula 282

[2406]

[2407]

Chemical Formula 283

[2408]

[2409]

Chemical Formula 284

[2410]

[2411] (In the above general formulas (71-21) to (71-25), R 701 、X7、Ar 701 、Ar 702 、L 701 , m1 and m4 are respectively the same as R in the above general formula (7) 701 、X7、Ar 701 、Ar 702 、L 701 , m1 and m4 have the same meaning.)

[2412] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-31) to (71-33).

[2413]

Chemical Formula 285

[2414]

[2415]

Chemical Formula 286

[2416]

[2417]

Chemical Formula 287

[2418]

[2419] (In the above general formulas (71-31) to (71-33), R 701 、X7、Ar 701 、Ar 702 、L 701 , m2~m4 are respectively the same as R in the above general formula (7) 701 、X7、Ar 701 、Ar 702 、L 701 、m2~m4 have the same meaning.)

[2420] In one embodiment, Ar 701 and Ar 702 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2421] In one embodiment, Ar 701 and Ar 702 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Ar 701 and Ar 702 The other one of the groups is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2422] Specific examples of the compound represented by the general formula (7) include the following compounds.

[2423]

Chemical Formula 288

[2424]

[2425]

Chemical Formula 289

[2426]

[2427]

Chemical Formula 290

[2428]

[2429]

Chemical Formula 291

[2430]

[2431]

Chemical Formula 292

[2432]

[2433]

Chemical Formula 293

[2434]

[2435] (Compound represented by general formula (8))

[2436] The compound represented by the general formula (8) will be described.

[2437]

Chemical Formula 294

[2438]

[2439] (In the above general formula (8),

[2440] R 801 With R 802 、R 802 With R 803and R 803 With R 804 At least one group of them is bonded to each other to form a divalent group represented by the following general formula (82),

[2441] R 805 With R 806 、R 806 With R 807 and R 807 With R 808 At least one group of them is bonded to each other to form a divalent group represented by the following general formula (83).

[2442]

Chemical Formula 295

[2443]

[2444] (R does not form a divalent group represented by the above general formula (82) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84),

[2445] R does not form a divalent group represented by the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),

[2446] X8 is an oxygen atom, a sulfur atom or NR 809 ,

[2447] R does not form a divalent group represented by the above general formula (82) and the general formula (83) and is not a monovalent group represented by the above general formula (84) 801 ~R 808 , R is not a monovalent group represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 , and R 809 Each independently

[2448] hydrogen atoms,

[2449] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2450] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2451] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2452] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2453] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2454] -O-(R 904 ) shown in the group,

[2455] -S-(R 905 ) shown in the group,

[2456] -N(R 906 )(R 907 ) shown in the group,

[2457] Halogen atoms,

[2458] cyano,

[2459] Nitro,

[2460] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2461] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2462]

Chemical Formula 296

[2463]

[2464] (In the above general formula (84),

[2465] Ar 801 and Ar 802 Each independently

[2466] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2467] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2468] L 801 ~L 803 Each independently

[2469] single bond,

[2470] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[2471] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[2472] a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[2473] * in the above general formula (84) represents the bonding position to the ring structure represented by the above general formula (8), the group represented by the general formula (82) or the general formula (83).

[2474] In the general formula (8), the positions of the divalent groups represented by the general formula (82) and the divalent groups represented by the general formula (83) are not particularly limited, and can be 801 ~R 808 The possible positions of the group are formed.

[2475] In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).

[2476]

Chemical Formula 297

[2477]

[2478]

Chemical Formula 298

[2479]

[2480]

Chemical Formula 299

[2481]

[2482] (In the above general formulas (81-1) to (81-6),

[2483] X8 has the same meaning as X8 in the above general formula (8),

[2484] R 801 ~R 824 At least two of them are monovalent groups represented by the above general formula (84),

[2485] R is not a monovalent group represented by the above general formula (84) 801 ~R 824 Each independently

[2486] hydrogen atoms,

[2487] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2488] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2489] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2490] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2491] -Si(R 901 )(R 902 )(R903 ) shown in the group,

[2492] -O-(R 904 ) shown in the group,

[2493] -S-(R 905 ) shown in the group,

[2494] -N(R 906 )(R 907 ) shown in the group,

[2495] Halogen atoms,

[2496] cyano,

[2497] Nitro,

[2498] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2499] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2500] In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).

[2501]

Chemical Formula 300

[2502]

[2503]

Chemical Formula 301

[2504]

[2505]

Chemical Formula 302

[2506]

[2507]

Chemical Formula 303

[2508]

[2509]

Chemical Formula 304

[2510]

[2511]

Chemical Formula 305

[2512]

[2513] (In the above general formulas (81-7) to (81-18),

[2514] X8 has the same meaning as X8 in the above general formula (8),

[2515] * is a single bond bonded to the monovalent group represented by the above general formula (84),

[2516] R 801 ~R 824 Each independently of the R of the above general formulae (81-1) to (81-6) which is not a monovalent group represented by the above general formula (84) 801 ~R 824 Same meaning.)

[2517] R does not form a divalent group represented by the above general formula (82) and the general formula (83) and is not a monovalent group represented by the above general formula (84) 801 ~R 808 , and R which is not a monovalent group represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 Preferably, each independently

[2518] hydrogen atoms,

[2519] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2520] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2521] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2522] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2523] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2524] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2525] The monovalent group represented by the above-mentioned general formula (84) is preferably represented by the following general formula (85) or (86).

[2526]

Chemical Formula 306

[2527]

[2528] (In the above general formula (85),

[2529] R 831 ~R 840 Each independently

[2530] hydrogen atoms,

[2531] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2532] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2533] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2534] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2535] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2536] -O-(R 904 ) shown in the group,

[2537] -S-(R 905 ) shown in the group,

[2538] -N(R 906 )(R 907 ) shown in the group,

[2539] Halogen atoms,

[2540] cyano,

[2541] Nitro,

[2542] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2543] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2544] The * in the above general formula (85) has the same meaning as that in the above general formula (84).

[2545]

Chemical Formula 307

[2546]

[2547] (In the above general formula (86),

[2548] Ar 801 , L 801 and L 803 and Ar in the above general formula (84) 801 , L 801 and L 803 Same meaning,

[2549] HAr 801 It is a structure represented by the following general formula (87).

[2550]

Chemical Formula 308

[2551]

[2552] (In the above general formula (87),

[2553] X 81 is an oxygen atom or a sulfur atom,

[2554] R 841 ~R 848 Any one of them is L 803 Bonded single bonds,

[2555] R is not a single bond 841 ~R 848 Each independently

[2556] hydrogen atoms,

[2557] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2558] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2559] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2560] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2561] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2562] -O-(R 904 ) shown in the group,

[2563] -S-(R 905 ) shown in the group,

[2564] -N(R 906 )(R 907 ) shown in the group,

[2565] Halogen atoms,

[2566] cyano,

[2567] Nitro,

[2568] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2569] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2570] Specific examples of the compound represented by the general formula (8) include the compounds described in International Publication No. 2014 / 104144 and the compounds shown below.

[2571]

Chemical Formula 309

[2572]

[2573]

Chemical Formula 310

[2574]

[2575]

Chemical Formula 311

[2576]

[2577]

Chemical Formula 312

[2578]

[2579]

Chemical Formula 313

[2580]

[2581]

Chemical Formula 314

[2582]

[2583] (Compound represented by general formula (9))

[2584] The compound represented by the general formula (9) will be described.

[2585]

Chemical Formula 315

[2586]

[2587] (In the above general formula (9),

[2588] A 91 Ring and A 92 The rings are independently

[2589] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2590] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[2591] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to * of the structure represented by the following general formula (92).

[2592]

Chemical Formula 316

[2593]

[2594] (In the above general formula (92),

[2595] A 93 Ring

[2596] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2597] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[2598] X9 for NR 93 、C(R 94 )(R 95 )、Si(R 96 )(R 97 )、Ge(R 98 )(R 99 ), oxygen atoms, sulfur atoms or selenium atoms,

[2599] R 91 and R 92

[2600] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2601] bonded to each other to form a substituted or unsubstituted fused ring, or

[2602] Not bonded to each other,

[2603] R does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 91 and R 92 , and R 93 ~R 99 Each independently

[2604] hydrogen atoms,

[2605] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2606] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2607] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2608] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2609] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2610] -O-(R 904 ) shown in the group,

[2611] -S-(R 905 ) shown in the group,

[2612] -N(R 906 )(R 907 ) shown in the group,

[2613] Halogen atoms,

[2614] cyano,

[2615] Nitro,

[2616] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2617] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2618] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to * of the structure represented by the above general formula (92). That is, in one embodiment, A 91 The ring-forming carbon atom of the aromatic hydrocarbon ring or the ring-forming atom of the heterocyclic ring is bonded to * of the structure represented by the general formula (92). In one embodiment, A 92 A carbon atom constituting the aromatic hydrocarbon ring or a ring atom constituting the heterocyclic ring is bonded to * in the structure represented by the general formula (92).

[2619] In one embodiment, the group represented by the following general formula (93) is bonded to A 91 Ring and A 92 One or both of the rings.

[2620]

Chemical Formula 317

[2621]

[2622] (In the above general formula (93),

[2623] Ar 91 and Ar 92 Each independently

[2624] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2625] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2626] L 91 ~L 93 Each independently

[2627] single bond,

[2628] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[2629] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[2630] a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[2631] In the above general formula (93), * represents 91 Ring and A 92 The bonding position of any ring in the ring.)

[2632] In one embodiment, in addition to A 91 In addition to the ring, there is A 92 The ring carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocyclic ring is bonded to * of the structure represented by the general formula (92). In this case, the structures represented by the general formula (92) may be the same as or different from each other.

[2633] In one embodiment, R 91 and R 92 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2634] In one embodiment, R 91 and R 92 They bond with each other to form a fluorene structure.

[2635] In one embodiment, Ring A 91 and Ring A 92 Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[2636] In one embodiment, Ring A 93 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[2637] In one embodiment, X9 is an oxygen atom or a sulfur atom.

[2638] Specific examples of the compound represented by the general formula (9) include the following compounds.

[2639]

Chemical Formula 318

[2640]

[2641]

Chemical Formula 319

[2642]

[2643]

Chemical Formula 320

[2644]

[2645]

Chemical Formula 321

[2646]

[2647] (Compound represented by general formula (10))

[2648] The compound represented by the general formula (10) will be described.

[2649]

Chemical Formula 322

[2650]

[2651]

Chemical Formula 323

[2652]

[2653] (In the above general formula (10),

[2654] The Ax1 ring is a ring represented by the above general formula (10a) fused at any position of the adjacent ring,

[2655] The Ax2 ring is a ring represented by the above general formula (10b) fused at any position of the adjacent ring,

[2656] The two * in the above general formula (10b) are bonded to any position of the Ax3 ring,

[2657] X A and X B Each independently is C(R 1003 )(R 1004 )、Si(R 1005 )(R 1006 ), oxygen atoms or sulfur atoms,

[2658] Ax3 ring is

[2659] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2660] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[2661] Ar 1001 for

[2662] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2663] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2664] R 1001 ~R 1006 Each independently

[2665] hydrogen atoms,

[2666] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2667] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2668] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2669] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2670] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2671] -O-(R 904 ) shown in the group,

[2672] -S-(R 905 ) shown in the group,

[2673] -N(R 906 )(R 907 ) shown in the group,

[2674] Halogen atoms,

[2675] cyano,

[2676] Nitro,

[2677] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2678] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2679] mx1 is 3, mx2 is 2,

[2680] Multiple R 1001 Same or different from each other,

[2681] Multiple R 1002 Same or different from each other,

[2682] ax is 0, 1, or 2,

[2683] When ax is 0 or 1, the structures in the brackets shown by "3-ax" are the same or different from each other.

[2684] When ax is 2, multiple Ar 1001 Same as or different from each other.)

[2685] In one embodiment, Ar 1001 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2686] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[2687] In one embodiment, R 1003 and R 1004 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2688] In one embodiment, ax is 1.

[2689] Specific examples of the compound represented by the general formula (10) include the following compounds.

[2690]

Chemical Formula 324

[2691]

[2692] In one embodiment, in the light-emitting layer, at least one of the third compound and the fourth compound contains a compound selected from the group consisting of

[2693] The compound represented by the above general formula (4),

[2694] The compound represented by the above general formula (5),

[2695] The compound represented by the above general formula (7),

[2696] The compound represented by the above general formula (8),

[2697] The compound represented by the above general formula (9) and

[2698] One or more compounds selected from the group consisting of compounds represented by the following general formula (63a).

[2699]

Chemical Formula 325

[2700]

[2701] (In the above general formula (63a),

[2702] R 631 With R 646 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[2703] R 633 With R 647 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[2704] R 634 With R 651They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[2705] R 641 With R 642 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[2706] R 631 ~R 651 One or more groups of two or more adjacent

[2707] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2708] bonded to each other to form a substituted or unsubstituted fused ring, or

[2709] Not bonded to each other,

[2710] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned monocyclic ring, and does not form the above-mentioned condensed ring 631 ~R 651 Each independently

[2711] hydrogen atoms,

[2712] Halogen atoms,

[2713] cyano,

[2714] Nitro,

[2715] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2716] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2717] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2718] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2719] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2720] -O-(R 904 ) shown in the group,

[2721] -S-(R 905 ) shown in the group,

[2722] -N(R 906 )(R 907 ) shown in the group,

[2723] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2724] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2725] It should be noted that R does not form the above-mentioned substituted or unsubstituted heterocycle, does not form the above-mentioned monocycle, and does not form the above-mentioned condensed ring. 631 ~R 651 At least one of

[2726] Halogen atoms,

[2727] cyano,

[2728] Nitro,

[2729] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2730] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2731] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2732] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2733] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2734] -O-(R 904 ) shown in the group,

[2735] -S-(R 905 ) shown in the group,

[2736] -N(R 906 )(R 907 ) shown in the group,

[2737] Halogen atoms,

[2738] cyano,

[2739] Nitro,

[2740] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2741] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2742] In one embodiment, the compound represented by the general formula (4) is a compound represented by the general formula (41-3), the general formula (41-4) or the general formula (41-5), and the A1 ring in the general formula (41-5) is a substituted or unsubstituted fused aromatic hydrocarbon ring with 10 to 50 ring carbon atoms or a substituted or unsubstituted fused heterocycle with 8 to 50 ring atoms.

[2743] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formula (41-3), the general formula (41-4) and the general formula (41-5) is

[2744] a substituted or unsubstituted naphthalene ring,

[2745] Substituted or unsubstituted anthracene ring or

[2746] a substituted or unsubstituted fluorene ring,

[2747] The substituted or unsubstituted fused heterocyclic ring having 8 to 50 ring atoms is

[2748] a substituted or unsubstituted dibenzofuran ring,

[2749] Substituted or unsubstituted carbazole ring or

[2750] a substituted or unsubstituted dibenzothiophene ring.

[2751] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formula (41-3), the general formula (41-4) or the general formula (41-5) is

[2752] Substituted or unsubstituted naphthalene ring or

[2753] a substituted or unsubstituted fluorene ring,

[2754] The substituted or unsubstituted fused heterocyclic ring having 8 to 50 ring atoms is

[2755] a substituted or unsubstituted dibenzofuran ring,

[2756] Substituted or unsubstituted carbazole ring or

[2757] a substituted or unsubstituted dibenzothiophene ring.

[2758] In one embodiment, the compound represented by the general formula (4) is selected from

[2759] The compound represented by the following general formula (461),

[2760] The compound represented by the following general formula (462),

[2761] The compound represented by the following general formula (463),

[2762] The compound represented by the following general formula (464),

[2763] The compound represented by the following general formula (465),

[2764] The compound represented by the following general formula (466) and

[2765] A group consisting of compounds represented by the following general formula (467).

[2766]

Chemical Formula 326

[2767]

[2768]

Chemical Formula 327

[2769]

[2770]

Chemical Formula 328

[2771]

[2772]

Chemical Formula 329

[2773]

[2774]

Chemical Formula 330

[2775]

[2776] (In the above general formulas (461) to (467),

[2777] R 421 ~R 427 、R 431 ~R 436 、R 440 ~R 448 and R 451 ~R 454 One or more groups of two or more adjacent

[2778] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[2779] bonded to each other to form a substituted or unsubstituted fused ring, or

[2780] Not bonded to each other,

[2781] R 437 、R 438 , and R which does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring 421 ~R 427 、R 431 ~R 436 、R 440 ~R 448 and R 451 ~R 454 Each independently

[2782] hydrogen atoms,

[2783] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2784] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2785] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2786] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2787] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2788] -O-(R 904 ) shown in the group,

[2789] -S-(R 905 ) shown in the group,

[2790] -N(R 906 )(R 907 ) shown in the group,

[2791] Halogen atoms,

[2792] cyano,

[2793] Nitro,

[2794] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2795] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2796] X4 is an oxygen atom, NR 801 or C(R 802 )(R 803 ),

[2797] R 801 、R 802 and R 803 Each independently

[2798] hydrogen atoms,

[2799] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2800] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2801] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2802] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2803] is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[2804] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2805] In R 801 When there are multiple R 801 Same or different from each other,

[2806] In R 802 When there are multiple R 802 Same or different from each other,

[2807] In R 803 When there are multiple R 803 Same as or different from each other.)

[2808] In one embodiment, R 421 ~R 427 and R 440 ~R 448 Each independently

[2809] hydrogen atoms,

[2810] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2811] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2812] In one embodiment, R 421 ~R 427 and R 440 ~R 447 Independently choose freedom

[2813] hydrogen atoms,

[2814] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms and

[2815] A group consisting of a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[2816] In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-1).

[2817]

Chemical Formula 331

[2818]

[2819] (In the above general formula (41-3-1), R 423 、R 425 、R 426 、R 442 、R 444and R 445 Each independently of R in the above general formula (41-3) 423 、R 425 、R 426 、R 442 、R 444 and R 445 Same meaning.)

[2820] In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-2).

[2821]

Chemical Formula 332

[2822]

[2823] (In the above general formula (41-3-2), R 421 ~R 427 and R 440 ~R 448 Each independently of R in the above general formula (41-3) 421 ~R 427 and R 440 ~R 448 Same meaning,

[2824] It should be noted that R 421 ~R 427 and R 440 ~R 446 At least one of them is -N(R 906 )(R 907 )

[2825] In one embodiment, R in the above formula (41-3-2) 421 ~R 427 and R 440 ~R 446 Any two of -N(R 906 )(R 907 ) shown in the group.

[2826] In one embodiment, the compound represented by the above formula (41-3-2) is a compound represented by the following formula (41-3-3).

[2827]

Chemical Formula 333

[2828]

[2829] (In the above general formula (41-3-3), R 421 ~R 424 、R 440 ~R 443 、R447 and R 448 Each independently of R in the above general formula (41-3) 421 ~R 424 、R 440 ~R 443 、R 447 and R 448 Same meaning,

[2830] R A 、R B 、R C and R D Each independently

[2831] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[2832] A substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[2833] In one embodiment, the compound represented by the above formula (41-3-3) is a compound represented by the following formula (41-3-4).

[2834]

Chemical Formula 334

[2835]

[2836] (In the above general formula (41-3-4), R 447 、R 448 、R A 、R B 、R C and R D Each independently of R in the above formula (41-3-3) 447 、R 448 、R A 、R B 、R C and R D Same meaning.)

[2837] In one embodiment, R A 、R B 、R C and R D Each is independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[2838] In one embodiment, R A 、R B 、R C and R D Each is independently a substituted or unsubstituted phenyl group.

[2839] In one embodiment, R 447 and R448 A hydrogen atom.

[2840] In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

[2841] unsubstituted alkyl group having 1 to 50 carbon atoms,

[2842] unsubstituted alkenyl having 2 to 50 carbon atoms,

[2843] unsubstituted alkynyl having 2 to 50 carbon atoms,

[2844] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2845] -Si(R 901a )(R 902a )(R 903a ),

[2846] -O-(R 904a ),

[2847] -S-(R 905a ),

[2848] -N(R 906a )(R 907a ),

[2849] Halogen atoms,

[2850] cyano,

[2851] Nitro,

[2852] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2853] an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2854] R 901a ~R 907a Each independently

[2855] hydrogen atoms,

[2856] unsubstituted alkyl group having 1 to 50 carbon atoms,

[2857] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2858] an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2859] In R 901a If there are two or more, two or more R 901a Same or different from each other,

[2860] In R 902aIf there are two or more, two or more R 902a Same or different from each other,

[2861] In R 903a If there are two or more, two or more R 903a Same or different from each other,

[2862] In R 904a If there are two or more, two or more R 904a Same or different from each other,

[2863] In R 905a If there are two or more, two or more R 905a Same or different from each other,

[2864] In R 906a If there are two or more, two or more R 906a Same or different from each other,

[2865] In R 907a If there are two or more, two or more R 907a Same as or different from each other.

[2866] In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

[2867] unsubstituted alkyl group having 1 to 50 carbon atoms,

[2868] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2869] An unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2870] In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

[2871] unsubstituted alkyl group having 1 to 18 carbon atoms,

[2872] unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[2873] An unsubstituted heterocyclic group having 5 to 18 ring atoms.

[2874] In the organic EL device according to this embodiment, the second emitting layer preferably further contains a fourth fluorescent compound, wherein the fourth compound is a compound that emits light with a main peak wavelength of 430 nm to 480 nm.

[2875] In the organic EL device according to this embodiment, the first emitting layer preferably further contains a third fluorescent compound, and the third compound is a compound that emits light with a main peak wavelength of 430 nm to 480 nm.

[2876] The method for measuring the main peak wavelength of a compound is as follows. 10 - 6 mol / L and above 10 -5 A toluene solution of less than 1 mol / L is added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (luminescence intensity on the vertical axis and wavelength on the horizontal axis). The luminescence spectrum can be measured using a spectrophotometer (F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

[2877] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is referred to as the main emission peak wavelength. Note that in this specification, the main peak wavelength may be referred to as the fluorescence main peak wavelength (FL-peak).

[2878] In the organic EL element involved in this embodiment, when the first light-emitting layer contains a first compound and a third compound, the first compound is preferably a host material (sometimes also called a matrix material), and the third compound is preferably a dopant material (sometimes also called a guest material, an emitter, or a light-emitting material).

[2879] In the organic EL element involved in this embodiment, when the first light-emitting layer contains the first compound and the third compound, the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the third compound preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1).

[2880] S1(H1)>S1(D3)...(Mathematical formula 1)

[2881] The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.

[2882] In the organic EL element involved in this embodiment, when the second light-emitting layer contains a second compound and a fourth compound, the second compound is preferably a host material (sometimes called a matrix material), and the fourth compound is preferably a dopant material (sometimes called a guest material, an emitter or a light-emitting material).

[2883] In the organic EL element involved in this embodiment, when the second light-emitting layer contains the second compound and the fourth compound, the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the fourth compound preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2).

[2884] S1(H2)>S1(D4)...(Mathematical formula 2)

[2885] (Singlet energy S1)

[2886] As a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be mentioned.

[2887] Prepare 10 of the compound to be measured -5 mol / L and above 10 -4 A toluene solution with a concentration of less than 1 mol / L was added to a quartz colorimetric cell, and the absorption spectrum of the sample was measured at room temperature (300K) (absorption intensity on the vertical axis, wavelength on the horizontal axis). A tangent line was drawn on the long-wavelength side of the absorption spectrum, and the wavelength λedge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the singlet energy.

[2888] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[2889] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310) can be cited, but the device is not limited thereto.

[2890] The tangent line for the long-wavelength drop of the absorption spectrum is derived as follows. As the spectrum curve moves along the long-wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum maximum, the tangent line at each point on the curve is considered. As the curve drops (i.e., as the value on the vertical axis decreases), the slope of this tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope reaches its minimum on the longest wavelength side (excluding absorbance values ​​of 0.1 or less) is considered the tangent line for the long-wavelength drop of the absorption spectrum.

[2891] It should be noted that the maximum point where the absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

[2892] In the organic EL device according to this embodiment, it is also preferable that the electron mobility μH1 of the first compound and the electron mobility μH2 of the second compound satisfy the relationship represented by the following mathematical formula (Mathematical Formula 3).

[2893] μH2>μH1...(Formula 3)

[2894] When the first compound and the second compound satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 3), the recombination ability of holes and electrons in the first light-emitting layer is improved.

[2895] The electron mobility can be measured using impedance spectroscopy by the following method.

[2896] The anode and cathode are used to clamp the measurement object layer with a thickness of 100nm to 200nm, and a small AC voltage of less than 100mV is applied while applying a bias DC voltage. The AC current value (absolute value and phase) flowing at this time is measured. This measurement is performed while changing the frequency of the AC voltage, and the complex impedance (Z) is calculated based on the current value and the voltage value. At this time, the frequency dependence of the imaginary part (ImM) of the modulus M=iωZ (i: imaginary unit, ω: angular frequency) is obtained, and the reciprocal of the frequency ω at which ImM reaches the maximum value is defined as the response time of the electrons conducted in the measurement object layer. Then, the electron mobility is calculated by the following formula.

[2897] Electron mobility = (thickness of the layer to be measured) 2 / (Response time·Voltage)

[2898] The first light-emitting layer and the second light-emitting layer preferably do not contain a phosphorescent material (dopant material).

[2899] In addition, the first and second light-emitting layers preferably do not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[2900] In addition, it is also preferred that the first light-emitting layer and the second light-emitting layer do not contain a metal complex.

[2901] (Thickness of the light-emitting layer)

[2902] The thickness of the light-emitting layer of the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. If the thickness of the light-emitting layer is 5 nm or greater, it is easy to form the light-emitting layer and adjust the chromaticity. If the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the increase in the driving voltage.

[2903] (Content of Compound in Light Emitting Layer)

[2904] When the first light-emitting layer contains the first compound and the third compound, the contents of the first compound and the third compound in the first light-emitting layer are preferably each within the following ranges, for example.

[2905] The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2906] The content of the third compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2907] However, the upper limit of the total content of the first compound and the third compound in the first light-emitting layer is 100 mass %.

[2908] It should be noted that this embodiment does not exclude the inclusion of materials other than the first compound and the third compound in the first light-emitting layer.

[2909] The first light-emitting layer may contain only one first compound or two or more thereof. The first light-emitting layer may contain only one third compound or two or more thereof.

[2910] When the second light-emitting layer contains the second compound and the fourth compound, the contents of the second compound and the fourth compound in the second light-emitting layer are preferably each within the following ranges, for example.

[2911] The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2912] The content of the fourth compound is preferably 1 mass % or more and 10 mass % or less, more preferably 1 mass % or more and 7 mass % or less, and even more preferably 1 mass % or more and 5 mass % or less.

[2913] However, the upper limit of the total content of the second compound and the fourth compound in the second light-emitting layer is 100 mass %.

[2914] It should be noted that this embodiment does not exclude the inclusion of materials other than the second compound and the fourth compound in the second light-emitting layer.

[2915] The second light-emitting layer may contain only one second compound or two or more second compounds. The second light-emitting layer may contain only one fourth compound or two or more fourth compounds.

[2916] The structure of the organic EL element 1 will be further described. In the following, reference numerals may be omitted.

[2917] (Substrate)

[2918] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, and plastic can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent. For example, a plastic substrate can be mentioned. As materials forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

[2919] (anode)

[2920] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or greater). Specifically, examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[2921] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target to which zinc oxide is added at 1% by mass or more and 10% by mass or less relative to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target to which tungsten oxide is added at 0.5% by mass or less and 5% by mass or less relative to indium oxide and zinc oxide is added at 0.1% by mass or less and 1% by mass or less relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[2922] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode. Therefore, materials that can serve as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

[2923] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys thereof. It should be noted that when forming the anode using alkali metals, alkaline earth metals, and alloys thereof, vacuum evaporation or sputtering can be used. In addition, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

[2924] (cathode)

[2925] The cathode is preferably made of a metal, alloy, conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group I or Group II 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 thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[2926] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, vacuum deposition or sputtering can be used. Furthermore, when silver paste is used, coating or inkjet methods can be used.

[2927] It should be noted that by providing an electron injection layer, a variety of conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide can be used to form the cathode regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[2928] (Hole Injection Layer)

[2929] The hole injection layer is a layer containing a substance with high hole injectability. Examples of substances with high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[2930] In addition, as substances with high hole injection properties, low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl}-N-phenylamino]biphenyl (abbreviation: DNTPD), Aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[2931] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD) and the like polymer compounds. In addition, a polymer compound to which an acid is added, such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly (styrene sulfonic acid) (PAni / PSS) can also be used.

[2932] (Hole Transport Layer)

[2933] The hole transport layer is a layer containing a substance with high hole transport properties. The hole transport layer can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N -phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) and the like. The substances described here are mainly aromatic amine compounds having 10 -6 cm 2 / (V·s) or more.

[2934] Carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA), and anthracene derivatives such as t-BuDNA, DNA, and DPAnth can also be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) and poly(4-vinyltriphenylamine) (abbreviated: PVTPA) can also be used.

[2935] It should be noted that as long as the hole transport property is higher than that of the electron, other substances may also be used. It should be noted that the layer containing the substance with high hole transport property may be not only a single layer but also a stack of two or more layers formed by stacking the above substances.

[2936] (Electron Transport Layer)

[2937] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as: Almq3), bis (10-hydroxybenzo [h] quinoline) beryllium (abbreviated as: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be suitably used. The substances described herein are mainly 10 -6 cm 2 / (V·s) or more. It should be noted that as long as the electron transport property is higher than the hole transport property, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can also be composed of a single layer or a stack of two or more layers formed by the above substances.

[2938] Furthermore, polymer compounds may be used in the electron transport layer. Examples include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[2939] (Electron Injection Layer)

[2940] The electron injection layer is a layer comprising a substance having high electron injection. Alkali metals, alkaline earth metals or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx) etc. can be used in the electron injection layer. In addition, a material formed by containing an alkali metal, alkaline earth metal or a compound thereof in a substance having electron transportability can also be used, specifically a material formed by containing magnesium (Mg) in Alq etc. can be used. It should be noted that electron injection from the cathode can be more efficiently performed at this time.

[2941] Alternatively, a composite material mixed with an organic compound and an electron donor (donor) can also be used in the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because it generates electrons in the organic compound through the electron donor. At this time, as an organic compound, it is preferably a material with excellent transport of the generated electrons. Specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, it is as long as it is a substance that shows electron donating properties for the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[2942] (Layer Formation Method)

[2943] The method for forming each layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above, and well-known methods such as dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film-forming methods such as spin coating, dip coating, flow coating, and inkjet can be used.

[2944] (film thickness)

[2945] The thickness of each organic layer in the organic EL element of this embodiment is not limited except for the cases specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are likely to occur, while if the film thickness is too thick, a high applied voltage is required, which degrades efficiency. Therefore, the film thickness of each organic layer in an organic EL element is generally preferably in the range of several nanometers to 1 μm.

[2946] According to this embodiment, an organic electroluminescent element with improved luminous efficiency can be provided.

[2947] In the organic EL element involved in this embodiment, the first light-emitting layer containing the first compound shown in the above-mentioned general formula (1) as the first host material is directly connected to the second light-emitting layer containing the second compound shown in the above-mentioned general formula (2) as the second host material. By stacking the first light-emitting layer and the second light-emitting layer like this, the generated singlet excitons and triplet excitons can be effectively utilized, and as a result, the luminous efficiency of the organic EL element can be improved. In one embodiment, by using a first compound having a deuterium atom as the first host material, the organic EL element emits light with a long life, and by using a first compound having a deuterium atom as the first host material and using a second compound having a deuterium atom as the second host material, the organic EL element further emits light with a long life.

[2948] [Second embodiment]

[2949] (Electronic equipment)

[2950] The electronic device involved in this embodiment is equipped with any of the organic EL elements in the above-mentioned embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (such as organic EL flat panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[2951] [Variations of the Embodiments]

[2952] It should be noted that the present invention is not limited to the above-described embodiment, and modifications, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

[2953] For example, the number of light-emitting layers is not limited to two, and more than two light-emitting layers may be stacked. In the case where the organic EL element has more than two light-emitting layers, it is sufficient as long as at least two of the light-emitting layers meet the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission based on direct electron transition from a triplet excited state to a ground state.

[2954] When the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem organic EL element may be used in which a plurality of light-emitting units are stacked with an intermediate layer interposed therebetween.

[2955] Furthermore, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably provided in contact with the light-emitting layer to block at least one of holes, electrons, and excitons.

[2956] For example, when a blocking layer is disposed in contact with the cathode side of a light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer closer to the cathode side than the blocking layer (e.g., an electron transport layer). When an organic EL element includes an electron transport layer, the blocking layer is preferably included between the light-emitting layer and the electron transport layer.

[2957] Furthermore, when a blocking layer is disposed in contact with the anode side of the light-emitting layer, the blocking layer transports holes and prevents electrons from reaching a layer closer to the anode side than the blocking layer (e.g., a hole transport layer). When an organic EL element includes a hole transport layer, the blocking layer is preferably included between the light-emitting layer and the hole transport layer.

[2958] Furthermore, to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers, a blocking layer can be provided adjacent to the light-emitting layer to prevent excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (e.g., electron transport layer and hole transport layer).

[2959] It is preferred that the light-emitting layer be in contact with the blocking layer.

[2960] Furthermore, specific structures and shapes in the implementation of the present invention may be other structures and shapes within the scope of achieving the purpose of the present invention.

[2961] Example

[2962] The present invention will be further described in detail below with reference to the following examples, but the present invention is not limited by these examples.

[2963] <Compound>

[2964] The structure of the compound represented by the general formula (1) used in the production of the organic EL device according to the Examples is shown below.

[2965]

Chemical Formula 335

[2966]

[2967]

Chemical Formula 336

[2968]

[2969]

Chemical Formula 337

[2970]

[2971]

Chemical Formula 338

[2972]

[2973]

Chemical Formula 339

[2974]

[2975]

Chemical Formula 340

[2976]

[2977]

Chemical Formula 341

[2978]

[2979]

Chemical Formula 342

[2980]

[2981]

Chemical Formula 343

[2982]

[2983]

Chemical Formula 344

[2984]

[2985]

Chemical Formula 345

[2986]

[2987]

Chemical Formula 346

[2988]

[2989]

Chemical Formula 347

[2990]

[2991]

Chemical Formula 348

[2992]

[2993]

Chemical Formula 349

[2994]

[2995]

Chemical Formula 350

[2996]

[2997]

Chemical Formula 351

[2998]

[2999]

Chemical Formula 352

[3000]

[3001]

Chemical Formula 353

[3002]

[3003]

Chemical Formula 354

[3004]

[3005]

Chemical Formula 355

[3006]

[3007]

Chemical Formula 356

[3008]

[3009]

Chemical Formula 357

[3010]

[3011]

Chemical Formula 358

[3012]

[3013]

Chemical Formula 359

[3014]

[3015]

Chemical Formula 360

[3016]

[3017]

Chemical Formula 361

[3018]

[3019]

Chemical Formula 362

[3020]

[3021]

Chemical Formula 363

[3022]

[3023]

Chemical Formula 364

[3024]

[3025]

Chemical Formula 365

[3026]

[3027]

Chemical Formula 366

[3028]

[3029]

Chemical Formula 367

[3030]

[3031]

Chemical Formula 368

[3032]

[3033]

Chemical Formula 369

[3034]

[3035]

Chemical Formula 370

[3036]

[3037]

Chemical Formula 371

[3038]

[3039] The structure of the compound represented by the general formula (2) used in the production of the organic EL device according to the Examples is shown below.

[3040]

Chemical Formula 372

[3041]

[3042]

Chemical Formula 373

[3043]

[3044]

Chemical Formula 374

[3045]

[3046]

Chemical Formula 375

[3047]

[3048]

Chemical Formula 376

[3049]

[3050]

Chemical Formula 377

[3051]

[3052]

Chemical Formula 378

[3053]

[3054]

Chemical Formula 379

[3055]

[3056]

Chemical Formula 380

[3057]

[3058]

Chemical Formula 381

[3059]

[3060]

Chemical Formula 382

[3061]

[3062]

Chemical Formula 383

[3063]

[3064]

Chemical Formula 384

[3065]

[3066]

Chemical Formula 385

[3067]

[3068]

Chemical Formula 386

[3069]

[3070] The structures of other compounds used in the production of organic EL devices according to Examples, Reference Examples, and Comparative Examples are shown below.

[3071]

Chemical Formula 387

[3072]

[3073]

Chemical Formula 388

[3074]

[3075]

Chemical Formula 389

[3076]

[3077]

Chemical Formula 390

[3078]

[3079]

Chemical Formula 391

[3080]

[3081]

Chemical Formula 392

[3082]

[3083]

Chemical Formula 393

[3084]

[3085]

Chemical Formula 394

[3086]

[3087]

Chemical Formula 395

[3088]

[3089]

Chemical Formula 396

[3090]

[3091]

Chemical Formula 397

[3092]

[3093]

Chemical Formula 398

[3094]

[3095]

Chemical Formula 399

[3096]

[3097] Chemical Formula 400

[3098]

[3099]

Chemical Formula 401

[3100]

[3101] <Fabrication of Organic EL Element 1>

[3102] Organic EL devices were produced and evaluated as follows.

[3103] [Example 1]

[3104] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[3105] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus. Compound HA1 was first deposited on the surface where the transparent electrode lines were formed so as to cover the transparent electrode, forming a hole injection layer (HI) with a thickness of 5 nm.

[3106] After forming the hole injection layer, compound HT1 was evaporated to form a first hole transport layer (HT) having a thickness of 80 nm.

[3107] Following the formation of the first hole transport layer, compound HT2 was evaporated to form a second hole transport layer (also referred to as electron blocking layer) (EBL) having a thickness of 10 nm.

[3108] Compound BH1 (first host material (BH)) and compound BD1 (dopant material (BD)) were co-evaporated on the second hole transport layer so that the proportion of compound BD1 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm.

[3109] Compound BH2 (second host material (BH)) and compound BD1 (dopant material (BD)) were co-evaporated on the first light-emitting layer so that the proportion of compound BD1 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 20 nm.

[3110] Compound ET1 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) (HBL) having a thickness of 10 nm.

[3111] Compound ET2 was evaporated on the first electron transport layer to form a second electron transport layer (ET) with a thickness of 15 nm.

[3112] LiF was vapor-deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.

[3113] Metal Al was evaporated on the electron injection layer to form a cathode having a film thickness of 80 nm.

[3114] The element structure of Example 1 is briefly shown below.

[3115] ITO(130) / HA1(5) / HT1(80) / HT2(10) / BH1:BD1(5,98%:2%) / BH2:BD1(20,98%:2%) / ET1(10) / ET2(15) / LiF(1) / Al(80)

[3116] In addition, the numbers in parentheses represent film thickness (unit: nm).

[3117] Similarly, the percentage numbers in parentheses (98%:2%) represent the ratio (mass %) of the host material (compound BH1 or compound BH2) to compound BD1 in the first or second emitting layer.

[3118] [Comparative Example 1]

[3119] The organic EL device of Comparative Example 1 was produced in the same manner as in Example 1 except that a first emitting layer with a thickness of 25 nm was formed as the emitting layer as described in Table 1, the second emitting layer was not formed, and the first electron transport layer was formed on the first emitting layer.

[3120] [Comparative Example 2]

[3121] The organic EL device of Comparative Example 2 was produced in the same manner as in Example 1, except that the first emitting layer was not formed as described in Table 1, and a second emitting layer with a thickness of 25 nm was formed on the second hole transport layer as the emitting layer.

[3122] <Evaluation of Organic EL Devices>

[3123] The organic EL devices produced in Examples, Reference Examples, and Comparative Examples were evaluated as follows. The evaluation results are shown in Tables 1 to 47.

[3124] In addition, in this specification, the evaluation results of a certain Example may be described in multiple tables, and the evaluation results of a certain Comparative Example may be described in multiple tables.

[3125] External quantum efficiency EQE

[3126] The device was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) by applying a voltage to the device so that the current density reached 10 mA / cm 2 From the obtained spectral emission brightness spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation occurred.

[3127] Lifespan LT90

[3128] A voltage was applied to the obtained organic EL element so that the current density reached 50 mA / cm 2 The time required for the brightness to reach 90% of the initial brightness (LT90 (unit: hour)) was measured. The results are shown in Table 1.

[3129] Lifespan LT95

[3130] A voltage was applied to the obtained organic EL element so that the current density reached 50 mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[3131] Main peak wavelength λp when the element is driven

[3132] The organic EL device was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta Co., Ltd.). A voltage was applied to the device so that the current density reached 10 mA / cm 2 The peak wavelength λ of the main peak is calculated based on the obtained spectral emission brightness spectrum. p (Unit: nm).

[3133] Driving voltage

[3134] A current density of 10 mA / cm2 was applied between the anode and cathode. 2 The voltage (unit: V) is measured when

[3135]

Table 1

[3136]

[3137] As shown in Table 1, the organic EL device according to Example 1, which comprises a first emitting layer containing a first compound as a first host material and a second emitting layer containing a second compound as a second host material, directly in contact with each other, emits light with higher luminous efficiency than the organic EL devices according to Comparative Examples 1 and 2, each comprising only one of the emitting layers. Furthermore, the organic EL device according to Example 1 has a longer lifespan than the organic EL devices according to Comparative Examples 1 and 2.

[3138] [Examples 2 to 20]

[3139] The organic EL devices of Examples 2 to 20 were produced in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer was changed to the first compound described in Table 2.

[3140] [Comparative Examples 3 to 21]

[3141] The organic EL devices of Comparative Examples 3 to 21 were produced in the same manner as in Comparative Example 1, except that the compound BH1 (first host material) in the first emitting layer was changed to the first compound described in Table 3.

[3142]

Table 2

[3143]

[3144]

Table 3

[3145]

[3146] [Example 21]

[3147] The organic EL device of Example 21 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 4.

[3148] [Examples 22-23]

[3149] The organic EL devices of Examples 22 and 23 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 4.

[3150] [Comparative Example 22]

[3151] The organic EL device of Comparative Example 22 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 4.

[3152]

Table 4

[3153]

[3154] [Example 24]

[3155] The organic EL device of Example 24 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 5.

[3156] [Examples 25-26]

[3157] The organic EL devices of Examples 25 and 26 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 5.

[3158] [Comparative Example 23]

[3159] The organic EL device of Comparative Example 23 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 5.

[3160]

Table 5

[3161]

[3162] [Example 27]

[3163] The organic EL device of Example 27 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 6.

[3164] [Examples 28-29]

[3165] The organic EL devices of Examples 28 and 29 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 6.

[3166] [Comparative Example 24]

[3167] The organic EL device of Comparative Example 24 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 6.

[3168]

Table 6

[3169]

[3170] [Example 30]

[3171] The organic EL device of Example 30 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 7.

[3172] [Examples 31-32]

[3173] The organic EL devices of Examples 31 and 32 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 7.

[3174] [Comparative Example 25]

[3175] The organic EL device of Comparative Example 25 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 7.

[3176]

Table 7

[3177]

[3178] [Example 33]

[3179] The organic EL device of Example 33 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 8.

[3180] [Examples 34-35]

[3181] The organic EL devices of Examples 34 and 35 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 8.

[3182] [Comparative Example 26]

[3183] The organic EL device of Comparative Example 26 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 8.

[3184]

Table 8

[3185]

[3186] [Example 36]

[3187] The organic EL device of Example 36 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 9.

[3188] [Examples 37-38]

[3189] The organic EL devices of Examples 37 and 38 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 9.

[3190] [Comparative Example 27]

[3191] The organic EL device of Comparative Example 27 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 9.

[3192]

Table 9

[3193]

[3194] [Example 39]

[3195] The organic EL device of Example 39 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 10.

[3196] [Examples 40-41]

[3197] The organic EL devices of Examples 40 and 41 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 10.

[3198] [Comparative Example 28]

[3199] The organic EL device of Comparative Example 28 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 10.

[3200]

Table 10

[3201]

[3202] [Example 42]

[3203] The organic EL device of Example 42 was produced in the same manner as in Example 1, except that the compound BH2 (second host material) in the second light-emitting layer was changed to the compound described in Table 11.

[3204] [Examples 43-44]

[3205] The organic EL devices of Examples 43 and 44 were prepared in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were changed to the compounds listed in Table 11.

[3206] [Comparative Example 29]

[3207] The organic EL device of Comparative Example 29 was produced in the same manner as in Comparative Example 2, except that the compound BH2 (second host material) in the second emitting layer was changed to the compound described in Table 11.

[3208]

Table 11

[3209]

[3210] [Example 45]

[3211] The organic EL device of Example 45 was produced in the same manner as in Example 1, except that compound BD1 in the first emitting layer and compound BD1 in the second emitting layer were changed to the compounds described in Table 12.

[3212] [Examples 46-47]

[3213] The organic EL devices of Examples 46 and 47 were prepared in the same manner as in Example 1, except that compound BH1 (first host material) and compound BD1 in the first emitting layer and compound BD1 in the second emitting layer were replaced with the compounds listed in Table 12.

[3214] [Comparative Example 30]

[3215] The organic EL device of Comparative Example 30 was produced in the same manner as in Comparative Example 1, except that the compound BD1 in the first light-emitting layer was changed to a compound described in Table 12.

[3216] [Comparative Example 31]

[3217] The organic EL device of Comparative Example 31 was produced in the same manner as in Comparative Example 2, except that the compound BD1 in the second light-emitting layer was changed to a compound described in Table 12.

[3218]

Table 12

[3219]

[3220] [Example 48]

[3221] The organic EL device of Example 48 was produced in the same manner as in Example 1, except that compound BD1 in the first emitting layer and compound BD1 in the second emitting layer were changed to the compounds described in Table 13.

[3222] [Examples 49-50]

[3223] The organic EL devices of Examples 49 to 50 were prepared in the same manner as in Example 1, except that compound BH1 (first host material) and compound BD1 in the first emitting layer and compound BD1 in the second emitting layer were replaced with the compounds listed in Table 13.

[3224] [Comparative Example 32]

[3225] The organic EL device of Comparative Example 32 was produced in the same manner as in Comparative Example 1, except that the compound BD1 in the first light-emitting layer was changed to a compound described in Table 13.

[3226] [Comparative Example 33]

[3227] The organic EL device of Comparative Example 33 was produced in the same manner as in Comparative Example 2, except that the compound BD1 in the second light-emitting layer was changed to a compound described in Table 13.

[3228]

Table 13

[3229]

[3230] [Examples 51 to 69]

[3231] The organic EL devices of Examples 51 to 69 were produced in the same manner as in Example 1, except that the compound BH1 (first host material) in the first emitting layer was changed to the compounds described in Table 14.

[3232]

Table 14

[3233]

[3234] [Comparative Examples 34 to 51]

[3235] The organic EL devices of Comparative Examples 34 to 51 were produced in the same manner as in Comparative Example 1, except that the compound BH1 (first host material) in the first emitting layer was changed to the compounds described in Table 15.

[3236]

Table 15

[3237]

[3238] <Fabrication of Organic EL Device 2>

[3239] Organic EL devices were produced and evaluated as follows.

[3240] [Example 70]

[3241] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[3242] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus. Compound HA1 was first deposited on the surface where the transparent electrode lines were formed so as to cover the transparent electrode, forming a hole injection layer (HI) with a thickness of 5 nm.

[3243] After forming the hole injection layer, compound HT3 was evaporated to form a first hole transport layer (HT) having a thickness of 80 nm.

[3244] Following the formation of the first hole transport layer, compound HT4 was evaporated to form a second hole transport layer (also referred to as electron blocking layer) (EBL) having a thickness of 10 nm.

[3245] Compound BH1-21 (first host material (BH)) and compound BD1 (dopant material (BD)) were co-evaporated on the second hole transport layer so that the proportion of compound BD1 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm.

[3246] Compound BH2 (second host material (BH)) and compound BD1 (dopant material (BD)) were co-evaporated on the first light-emitting layer so that the proportion of compound BD1 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 20 nm.

[3247] Compound ET4 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) (HBL) having a thickness of 10 nm.

[3248] Compound ET2 was evaporated on the first electron transport layer to form a second electron transport layer (ET) with a thickness of 15 nm.

[3249] LiF was vapor-deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.

[3250] Metal Al was evaporated on the electron injection layer to form a cathode having a film thickness of 80 nm.

[3251] The component structure of Example 70 is briefly shown as follows.

[3252] ITO(130) / HA1(5) / HT3(80) / HT4(10) / BH1-21: BD1(5, 98%: 2%) / BH2: BD1(20, 98%: 2%) / ET4(10) / ET2(15) / LiF(1) / Al(80)

[3253] In addition, the numbers in parentheses represent film thickness (unit: nm).

[3254] Similarly, the percentage numbers in parentheses (98%:2%) represent the ratio (mass %) of the host material (Compound BH1-21 or Compound BH2) to Compound BD1 in the first or second emitting layer.

[3255] [Examples 71 to 78]

[3256] The organic EL devices of Examples 71 to 78 were produced in the same manner as in Example 70, except that the compound BH1-21 (first host material) in the first emitting layer was changed to the first compound described in Table 16.

[3257] [Comparative Examples 52 to 59]

[3258] The organic EL elements of Comparative Examples 52 to 59 were produced in the same manner as in Example 70, except that a first light-emitting layer with a film thickness of 25 nm was formed as the light-emitting layer instead of a second light-emitting layer, a first electron transport layer was formed on the first light-emitting layer, and the first compound (first main material) in the first light-emitting layer was changed to the first compound described in Table 16.

[3259] [Comparative Example 60]

[3260] The organic EL device of Comparative Example 60 was produced in the same manner as in Example 70, except that the first emitting layer was not formed and a second emitting layer with a thickness of 25 nm was formed on the second hole transport layer as described in Table 16.

[3261] Table 16

[3262]

[3263] <Fabrication of Organic EL Device 3>

[3264] Organic EL devices were produced and evaluated as follows.

[3265] [Example 79]

[3266] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[3267] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus. Compound HA1 was first deposited on the surface where the transparent electrode lines were formed so as to cover the transparent electrode, forming a hole injection layer (HI) with a thickness of 5 nm.

[3268] After forming the hole injection layer, compound HT3 was evaporated to form a first hole transport layer (HT) having a thickness of 80 nm.

[3269] Following the formation of the first hole transport layer, compound HT4 was evaporated to form a second hole transport layer (also referred to as electron blocking layer) (EBL) having a thickness of 10 nm.

[3270] Compound BH1-29 (first host material (BH)) and compound BD1 (dopant material (BD)) were co-evaporated on the second hole transport layer so that the proportion of compound BD1 was 2% by mass, thereby forming a first light-...

Claims

1. An organic electroluminescent element having anode, cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode, The first light-emitting layer contains a first compound represented by the following general formula (101) as a first host material, The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material, The first light-emitting layer is directly in contact with the second light-emitting layer. In the general formula (101), R 101 ~R 120 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, in, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position of L 101 for a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms, mx is 1, 2, or 3, In L 101 If there are more than 2, more than 2 L 101 Same or different from each other, wherein the first compound has at least one deuterium atom, The total number of carbon atoms contained in the group represented by the following general formula (11X) in the first compound is 21 or less, In the general formula (11X), * represents the bonding position, In the general formula (2), R 201 ~R 208 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 201 and L 202 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 Each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the first compound represented by the general formula (101) and the second compound represented by the general formula (2), R 901 、R 902 、R 903 、R 904 、R 905 、R 906 、R 907 、R 801 and R 802 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 When there are multiple R 901 Same or different from each other, In R 902 When there are multiple R 902 Same or different from each other, In R 903 When there are multiple R 903 Same or different from each other, In R 904 When there are multiple R 904 Same or different from each other, In R 905 When there are multiple R 905 Same or different from each other, In R 906 When there are multiple R 906 Same or different from each other, In R 907 When there are multiple R 907 Same or different from each other, In R 801 When there are multiple R 801 Same or different from each other, In R 802 When there are multiple R 802 Same as or different from each other.

2. The organic electroluminescent element according to claim 1, wherein Not with L 101 The bonding position R 101 ~R 110 At least one of them is a deuterium atom.

3. The organic electroluminescent element according to claim 1, wherein L 101 Having at least one deuterium atom.

4. The organic electroluminescent element according to claim 1, wherein As R 101 ~R 110 substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) represented by the group, -O-(R 904 ) represented by the group, -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The group shown, -COOR 802 At least one of the group shown, the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms has at least one deuterium atom.

5. The organic electroluminescent element according to claim 1, wherein The second compound has at least one deuterium atom. The organic electroluminescent element according to claim 1 , wherein: R 201 ~R 208 At least one of them is a deuterium atom.

7. The organic electroluminescent element according to claim 1, wherein L 201 and L 202 At least any one of has at least one deuterium atom.

8. The organic electroluminescent element according to claim 1, wherein Ar 201 and Ar 202 At least any one of has at least one deuterium atom.

9. The organic electroluminescent element according to any one of claims 1 to 4, wherein Both the first light-emitting layer and the second light-emitting layer contain a compound having at least one deuterium atom.

10. The organic electroluminescent element according to any one of claims 1 to 4, wherein The second light-emitting layer does not substantially contain a compound containing deuterium atoms.

11. The organic electroluminescent element according to any one of claims 1 to 4, wherein The total number of carbon atoms contained in the group represented by the general formula (11X) in the first compound is 13 or less.

12. The organic electroluminescent element according to any one of claims 1 and 3 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 At least one of them is a deuterium atom, Not with L 101 The bonding position R 111 ~R 120 At least one of them is a deuterium atom.

13. The organic electroluminescent element according to any one of claims 1 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 and R 111 ~R 120 The total number of carbon atoms contained is 21 or less.

14. The organic electroluminescent element according to any one of claims 1 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 and R 111 ~R 120 , and the total number of carbon atoms contained in the group represented by the general formula (11X) is 21 or less.

15. The organic electroluminescent element according to claim 14, wherein Not with L 101 The bonding position R 101 ~R 110 and R 111 ~R 120 , and the total number of carbon atoms contained in the group represented by the general formula (11X) is 13 or less.

16. The organic electroluminescent element according to any one of claims 1 to 8, wherein In the first compound represented by the general formula (101), mx is 2 or greater.

17. The organic electroluminescent element according to any one of claims 1 to 8, wherein L 101 It is an unsubstituted arylene group having 6 to 18 ring carbon atoms, or an unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.

18. The organic electroluminescent element according to any one of claims 1 to 8, wherein L 101 It is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.

19. The organic electroluminescent element according to any one of claims 1 to 8, wherein L 101 is any one of the following general formulas (TEMP-42) to (TEMP-44), In the general formulas (TEMP-42) to (TEMP-44), Q1 to Q5 are each independently a hydrogen atom or a substituent.

20. The organic electroluminescent element according to claim 19, wherein At least one of Q1 to Q5 is a deuterium atom.

21. The organic electroluminescent element according to claim 19, wherein L 101 The group is represented by the general formula (TEMP-42), wherein at least one of Q1 to Q4 is a deuterium atom.

22. The organic electroluminescent element according to claim 19, wherein L 101 The group is represented by the general formula (TEMP-43), wherein at least one of Q1 to Q3 and Q5 is a deuterium atom.

23. The organic electroluminescent element according to claim 19, wherein L 101 The group is represented by the general formula (TEMP-44), wherein at least one of Q1, Q2, Q4, and Q5 is a deuterium atom.

24. The organic electroluminescent element according to claim 19, wherein One or more and four or less of Q1 to Q5 are substituents, At least one of the one or more and four or less substituents has at least one deuterium atom.

25. The organic electroluminescent element according to claim 19, wherein In the general formula (TEMP-42), one or more groups of two or more adjacent ones of Q1 to Q4 are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (TEMP-43), one or more groups of two or more adjacent ones of Q1 to Q3 are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (TEMP-44), one or more groups consisting of two or more adjacent ones of Q1, Q2, Q4, and Q5 are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Q1 to Q5 that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently hydrogen atoms, unsubstituted alkyl group having 1 to 6 carbon atoms, unsubstituted phenyl, unsubstituted 1-naphthyl or unsubstituted 2-naphthyl.

26. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first compound is represented by the following general formula (1010), general formula (1011), general formula (1012), general formula (1013), general formula (1014) or general formula (1015), In the general formulas (1010) to (1015), R 101 ~R 120 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 101 for a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms, mx is 1, 2, or 3, In L 101 If there are more than 2, more than 2 L 101 Same or different from each other, The total number of carbon atoms contained in the group represented by the general formula (11X) in the first compound is 21 or less.

27. The organic electroluminescent element according to any one of claims 1 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

28. The organic electroluminescent element according to any one of claims 1 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

29. The organic electroluminescent element according to any one of claims 1 to 3 and 5 to 8, wherein Not with L 101 The bonding position R 101 ~R 110 A hydrogen atom.

30. The organic electroluminescent element according to any one of claims 1 to 8, wherein R 201 ~R 208 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, cyano, or Nitro, L 201 and L 202 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 Each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

31. The organic electroluminescent element according to any one of claims 1 to 8, wherein L 201 and L 202 Each independently Single button or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Ar 201 and Ar 202 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

32. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar 201 and Ar 202 Each independently Phenyl, Naphthyl, Fiki, Biphenyl, terphenyl, Diphenylfluorenyl, Dimethylfluorenyl, Benzodiphenylfluorenyl, Benzodimethylfluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl, or Naphthobenzothienyl.

33. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 is a substituted or unsubstituted dibenzofuranyl group.

34. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 It is an unsubstituted dibenzofuranyl group.

35. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 To choose freedom substituted or unsubstituted anthracenyl, Substituted or unsubstituted benzanthryl, Substituted or unsubstituted phenoxy, Substituted or unsubstituted triphenylene group, substituted or unsubstituted phenalenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysyl, Substituted or unsubstituted benzophenone, Substituted or unsubstituted triphenylene, Substituted or unsubstituted benzotriphenylene, Substituted or unsubstituted naphthacene, Substituted or unsubstituted pentacene, substituted or unsubstituted fluoranthene group, Substituted or unsubstituted benzofluoranthenyl and At least one group selected from the group consisting of substituted or unsubstituted perylenyl groups.

36. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 is a substituted or unsubstituted fluorenyl group.

37. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 is a substituted or unsubstituted xanthene group.

38. The organic electroluminescent element according to any one of claims 1 to 8, wherein Ar in the second compound 201 It is benzoxanthene.

39. The organic electroluminescent element according to any one of claims 1 to 8, wherein The second compound represented by the general formula (2) is a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209), In the general formulas (201) to (209), L 201 and Ar 201 and L in the general formula (2) 201 and Ar 201 Same meaning, R 201 ~R 208 Each independently of R in the general formula (2) 201 ~R 208 Same meaning.

40. The organic electroluminescent element according to any one of claims 1 to 8, wherein The second compound represented by the general formula (2) is a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) or general formula (229), In the general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) and general formula (229), R 201 and R 203 ~R 208 Each independently of R in the general formula (2) 201 and R 203 ~R 208 Same meaning, L 201 and Ar 201 respectively with L in the general formula (2) 201 and Ar 201 Same meaning, L 203 and L in the general formula (2) 201 Same meaning, L 203 With L 201 Same or different from each other, Ar 203 and Ar in the general formula (2) 201 Same meaning, Ar 203 with Ar 201 Same as or different from each other.

41. The organic electroluminescent element according to any one of claims 1 to 8, wherein The second compound represented by the general formula (2) is a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) or general formula (249), In the general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) and general formula (249), R 201 、R 202 and R 204 ~R 208 Each independently of R in the general formula (2) 201 、R 202 and R 204 ~R 208 Same meaning, L 203 and L in the general formula (2) 201 Same meaning, L 203 With L 201 Same or different from each other, Ar 203 and Ar in the general formula (2) 201 Same meaning, Ar 203 with Ar 201 Same as or different from each other.

42. The organic electroluminescent element according to any one of claims 1 to 8, wherein In the second compound represented by the general formula (2), R 201 ~R 208 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -Si(R 901 )(R 902 )(R 903 ) shown in the group.

43. The organic electroluminescent element according to any one of claims 1 to 8, wherein In the second compound represented by the general formula (2), R 201 ~R 208 A hydrogen atom.

44. The organic electroluminescent element according to any one of claims 1 to 8, wherein R 201 ~R 208 When the term "substituted or unsubstituted" is used, the substituent does not include substituted or unsubstituted alkyl and substituted or unsubstituted cycloalkyl.

45. The organic electroluminescent element according to any one of claims 1 to 8, wherein L in the second compound represented by the general formula (2) 201 Selected from TEMP-63 to TEMP-68, In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent, and * represents a bonding position.

46. ​​The organic electroluminescent element according to any one of claims 1 to 8, wherein In the first compound and the second compound, groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

47. The organic electroluminescent element according to claim 1, wherein The first light-emitting layer further contains a third fluorescent compound.

48. The organic electroluminescent element according to claim 47, wherein The third compound is a compound that emits light with a main peak wavelength of 430 nm to 480 nm.

49. The organic electroluminescent element according to claim 47, wherein The first compound is a host material, and the third compound is a dopant material.

50. The organic electroluminescent element according to claim 47, wherein The singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 1): S1(H1)>S1(D3)…(Mathematical formula 1).

51. The organic electroluminescent element according to claim 47, wherein The content of the first compound in the first light-emitting layer is 80 mass % or more and 99 mass % or less.

52. The organic electroluminescent element according to claim 47, wherein The content of the third compound in the first light-emitting layer is 1 mass % or more and 10 mass % or less.

53. The organic electroluminescent element according to claim 1, wherein The second light-emitting layer further contains a fourth fluorescent compound.

54. The organic electroluminescent element according to claim 53, wherein The fourth compound is a compound that emits light with a main peak wavelength of 430 nm to 480 nm.

55. The organic electroluminescent element according to claim 53, wherein The second compound is a host material, and the fourth compound is a dopant material.

56. The organic electroluminescent element according to claim 53, wherein The singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the fourth compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2): S1(H2)>S1(D4)…(Mathematical formula 2).

57. The organic electroluminescent element according to claim 53, wherein The content of the second compound in the second light-emitting layer is 80 mass % or more and 99 mass % or less.

58. The organic electroluminescent element according to claim 53, wherein The content of the fourth compound in the second light-emitting layer is 1 mass % or more and 10 mass % or less.

59. The organic electroluminescent element according to any one of claims 47 to 58, wherein The third compound or the fourth compound is independently selected from The compound represented by the following general formula (3), The compound represented by the following general formula (4), The compound represented by the following general formula (5), The compound represented by the following general formula (6), The compound represented by the following general formula (7), The compound represented by the following general formula (8), The compound represented by the following general formula (9) and One or more compounds selected from the group consisting of compounds represented by the following general formula (10), In the general formula (3), R 301 ~R 310 One or more groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31), R does not form the monocyclic ring, does not form the condensed ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (31), Ar 301 and Ar 302 Each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 301 ~L 303 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, * represents the bonding position in the pyrene ring in the general formula (3), In the general formula (4), Z is each independently CRa or a nitrogen atom, Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, When there are multiple Ra, one or more groups of two or more adjacent Ra bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, n21 and n22 are each independently 0, 1, 2, 3 or 4, When there are multiple Rb, one or more groups of two or more adjacent Rb bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, When there are multiple Rcs, one or more groups of two or more adjacent Rcs are selected. bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra, Rb and Rc that do not form the monocyclic ring and the condensed ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (5), R 501 ~R 507 and R 511 ~R 517 One or more groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R that does not form the monocyclic ring and does not form the condensed ring 501 ~R 507 and R 511 ~R 517 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 521 and R 522 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (6), Ring a, ring b and ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 601 and R 602 Each independently bonds to the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, R that does not form the substituted or unsubstituted heterocyclic ring 601 and R 602 Each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (7), The r ring is a ring represented by the general formula (72) or (73) fused at any position of the adjacent ring, The q ring and the s ring are each independently a ring represented by the general formula (74) fused at any position of the adjacent rings, The p ring and the t ring are each independently a structure represented by the general formula (75) or (76) fused at any position of the adjacent rings, X7 is an oxygen atom, a sulfur atom or NR 702 , In R 701 When there are multiple adjacent R 701 bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R that does not form the monocyclic ring and does not form the condensed ring 701 and R 702 Each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Ar 701 and Ar 702 Each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 701 for a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, m1 is 0, 1, or 2, m2 is 0, 1, 2, 3 or 4, m3 are each independently 0, 1, 2 or 3, m4 are each independently 0, 1, 2, 3, 4 or 5, In R 701 When there are multiple R 701 Same or different from each other, When there are multiple X7, the multiple X7 are the same or different from each other. In R 702 When there are multiple R 702 Same or different from each other, In Ar 701 When there are multiple Ar 701 Same or different from each other, In Ar 702 When there are multiple Ar 702 Same or different from each other, In L 701 When there are multiple L 701 Same or different from each other, In the general formula (8), R 801 With R 802 、R 802 With R 803 and R 803 With R 804 At least one group of them is bonded to each other to form a divalent group represented by the following general formula (82), R 805 With R 806 、R 806 With R 807 and R 807 With R 808 At least one group of them is bonded to each other to form a divalent group represented by the following general formula (83), R does not form a divalent group represented by the general formula (82) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R does not form a divalent group represented by the general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84), X8 is an oxygen atom, a sulfur atom or NR 809 , R does not form a divalent group represented by the general formula (82) and the general formula (83) and is not a monovalent group represented by the general formula (84) 801 ~R 808 , R is not a monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 , and R 809 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (84), Ar 801 and Ar 802 Each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 801 ~L 803 Each independently single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, * in the general formula (84) represents the bonding position to the ring structure represented by the general formula (8), the group represented by the general formula (82) or the general formula (83), In the general formula (9), A 91 Ring and A 92 The rings are independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to * of the structure represented by the following general formula (92), In the general formula (92), A 93 Ring a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, X9 for NR 93 、C(R 94 )(R 95 )、Si(R 96 )(R 97 )、Ge(R 98 )(R 99 ), oxygen atoms, sulfur atoms or selenium atoms, R 91 and R 92 for bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R that does not form the monocyclic ring and does not form the condensed ring 91 and R 92 , and R 93 ~R 99 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (10), The Ax1 ring is a ring represented by the general formula (10a) fused at any position of the adjacent ring, The Ax2 ring is a ring represented by the general formula (10b) fused at any position of the adjacent ring, The two * in the general formula (10b) are bonded to any position of the Ax3 ring, X A and X B Each independently is C(R 1003 )(R 1004 )、Si(R 1005 )(R 1006 ), oxygen atoms or sulfur atoms, Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, Ar 1001 for a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 1001 ~R 1006 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, -N(R 906 )(R 907 ) shown in the group, Halogen atoms, cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx1 is 3, mx2 is 2, Multiple R 1001 Same or different from each other, Multiple R 1002 Same or different from each other, ax is 0, 1, or 2, When ax is 0 or 1, the structures in the brackets shown by "3-ax" are the same or different from each other. When ax is 2, multiple Ar 1001 Same or different from each other, In the third compound or the fourth compound, R 901 、R 902 、R 903 、R 904 、R 905 、R 906 and R 907 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 When there are multiple R 901 Same or different from each other, In R 902 When there are multiple R 902 Same or different from each other, In R 903 When there are multiple R 903 Same or different from each other, In R 904 When there are multiple R 904 Same or different from each other, In R 905 When there are multiple R 905 Same or different from each other, In R 906 When there are multiple R 906 Same or different from each other, In R 907 When there are multiple R 907 Same as or different from each other.

60. The organic electroluminescent element according to any one of claims 1 to 8, wherein When the term "substituted or unsubstituted" is used, the substituent is unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstituted aryl group having 6 to 50 ring carbon atoms, or An unsubstituted heterocyclic group having 5 to 50 ring atoms.

61. The organic electroluminescent element according to any one of claims 1 to 8, wherein When the term "substituted or unsubstituted" is used, the substituent is unsubstituted alkyl group having 1 to 18 carbon atoms, unsubstituted aryl group having 6 to 18 ring carbon atoms, or An unsubstituted heterocyclic group having 5 to 18 ring atoms.

62. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first light-emitting layer and the second light-emitting layer do not contain a phosphorescent material.

63. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first light-emitting layer and the second light-emitting layer do not contain a heavy metal complex and a phosphorescent rare earth metal complex.

64. The organic electroluminescent element according to any one of claims 1 to 8, wherein The first light-emitting layer and the second light-emitting layer do not include a metal complex.

65. The organic electroluminescent element according to claim 1, wherein The first host material is a compound selected from the group consisting of compounds BH1-84, BH1-85, BH1-86 and BH1-88, The second host material is a compound selected from the group consisting of compounds BH2, BH2-3, BH2-30 and BH2-31, 。 66. The organic electroluminescent element according to claim 48 or 54, wherein The main peak wavelength of the compound is 10 -6 mol / L and above 10 -5 mol / L or less toluene solution is added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at 300K. The peak wavelength of the luminescence spectrum where the luminescence intensity reaches the maximum is obtained, wherein the vertical axis of the luminescence spectrum is the luminescence intensity and the horizontal axis is the wavelength.

67. The organic electroluminescent element according to claim 50 or 56, wherein 10 of the compound to be measured for the singlet energy S1 was prepared -5 mol / L and above 10 -4 mol / L or less toluene solution is added to a quartz colorimetric cell, and the absorption spectrum of the sample is measured at 300K. A tangent line is drawn on the long-wavelength side of the absorption spectrum, and the wavelength value λedge of the intersection of the tangent line and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the singlet energy, wherein the vertical axis of the absorption spectrum is absorption intensity, the horizontal axis is wavelength, the unit of λedge is nm, and the unit of S1 is eV. Conversion formula (F2): S1 = 1239.85 / λedge.

68. The organic electroluminescent element according to any one of claims 1 to 8, wherein The electron mobility μH1 of the first compound and the electron mobility μH2 of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3): μH2>μH1…(Mathematical formula 3).

69. The organic electroluminescent element according to claim 68, wherein Electron mobility was measured using impedance spectroscopy using the following method: A layer to be measured with a thickness of 100 nm to 200 nm is clamped between an anode and a cathode. A small AC voltage of less than 100 mV is applied while a bias DC voltage is applied. The absolute value and phase of the AC current flowing at this time are measured. This measurement is performed while changing the frequency of the AC voltage. The complex impedance Z is calculated from the current and voltage values. At this time, the frequency dependence of the imaginary part ImM of the modulus M = iωZ is determined, where i is the imaginary unit and ω is the angular frequency. The reciprocal of the frequency ω at which ImM reaches a maximum value is defined as the response time of electrons conducted within the layer to be measured. Then, the electron mobility is calculated using the following formula: Electron mobility = (thickness of the layer to be measured) 2 / (response time·voltage).

70. The organic electroluminescent element according to any one of claims 1 to 8, wherein The organic electroluminescent element emits light having a main peak wavelength of 430 nm to 480 nm inclusive when the element is driven.

71. The organic electroluminescent element according to claim 70, wherein The luminance of the organic electroluminescent element was measured by a spectrophotometer. A voltage was applied to the organic electroluminescent element so that the current density reached 10 mA / cm 2 The spectral emission brightness spectrum is obtained, and in the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum where the luminescence intensity reaches the maximum is measured, and it is taken as the main peak wavelength of the light emitted by the organic electroluminescent element when the element is driven, and the unit of the main peak wavelength is nm.

72. The organic electroluminescent element according to any one of claims 1 to 8, wherein A hole transport layer is provided between the anode and the first light-emitting layer.

73. The organic electroluminescent element according to any one of claims 1 to 8, wherein An electron transport layer is provided between the cathode and the second light emitting layer.

74. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 73.

Images