Compound, organic electroluminescent element, and electronic device

Abstract

A compound represented by general formula (1). # imgabs0 # in general formula (1), ring AX is a ring represented by general formula (1A-1) or (1A-2), the ring represented by general formula (1A-1) is fused to ring Cx at the position of a, the ring represented by general formula (1A-2) is fused to ring Cx at the position of b or c, ring BX is a ring represented by general formula (1B-1), the ring represented by general formula (1B-1) is fused to ring Cx at the position of d, e, f or g, and the ring represented by general formula (1A-2) is fused to ring Cx at the position of d, e, f or g. At least one aryl group Ar1 is bonded to at least one of the ring represented by general formula (1A-1), the ring represented by general formula (1A-2), and the ring represented by general formula (1B-1).

Description

Technical Field

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

[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays in mobile phones, televisions, and other applications. When voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, 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] Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, Patent Documents 1 and 2 describe studies aimed at improving the performance of an organic EL element.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Korean Patent Publication No. 10-2012-0116884

[0007] Patent Document 2: Japanese Patent Application Publication No. 2019-169618 Summary of the Invention

[0008] Problems to be solved by the invention

[0009] An object of the present invention is to provide a compound capable of improving the life of an organic electroluminescent element, and to provide an organic electroluminescent element containing the compound and an electronic device equipped with the organic electroluminescent element.

[0010] Means used to solve problems

[0011] According to one embodiment of the present invention, a compound represented by the following general formula (1) is provided.

[0012]

Chemical Formula 1

[0013]

[0014] (In the above general formula (1),

[0015] Group consisting of R1 and R2

[0016] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0017] bonded to each other to form a substituted or unsubstituted fused ring, or

[0018] Not bonded to each other,

[0019] R1 and R2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0020] a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms,

[0021] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0022] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0023] Ring A X is a ring represented by the above-mentioned general formula (1A-1) or (1A-2),

[0024] The ring represented by the above general formula (1A-1) is fused with the ring Cx at the position a,

[0025] The ring represented by the above general formula (1A-2) is fused with the ring Cx at the position b or c,

[0026] Ring B X is a ring represented by the above general formula (1B-1),

[0027] The ring represented by the above general formula (1B-1) is fused with the ring Cx at the position d, e, f or g,

[0028] One or more substituents represented by the following general formula (11) may be bonded to each of the ring represented by the above general formula (1A-1), the ring represented by the above general formula (1A-2), and the ring represented by the above general formula (1B-1), independently of each other.

[0029] One or more aryl groups Ar1 are bonded to at least one of the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1).

[0030] Ar1 is

[0031] Substituted or unsubstituted biphenyl,

[0032] Substituted or unsubstituted terphenyl,

[0033] substituted or unsubstituted naphthyl,

[0034] Substituted or unsubstituted benzanthryl,

[0035] Substituted or unsubstituted phenoxy,

[0036] Substituted or unsubstituted triphenylene group,

[0037] substituted or unsubstituted phenalenyl,

[0038] substituted or unsubstituted pyrenyl,

[0039] substituted or unsubstituted chrysyl,

[0040] Substituted or unsubstituted benzophenone,

[0041] Substituted or unsubstituted triphenylene,

[0042] Substituted or unsubstituted benzotriphenylene,

[0043] Substituted or unsubstituted naphthacene,

[0044] Substituted or unsubstituted pentacene,

[0045] substituted or unsubstituted fluorenyl,

[0046] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0047] Substituted or unsubstituted benzofluorenyl,

[0048] Substituted or unsubstituted dibenzofluorenyl,

[0049] substituted or unsubstituted fluoranthene group,

[0050] Substituted or unsubstituted benzofluoranthenyl, or

[0051] Substituted or unsubstituted perylenyl.)

[0052]

Chemical Formula 2

[0053]

[0054] (In the above general formula (11),

[0055] n 11 is 0, 1, 2, or 3,

[0056] L 11 For

[0057] substituted or unsubstituted phenyl,

[0058] Substituted or unsubstituted biphenyl,

[0059] Substituted or unsubstituted terphenyl,

[0060] substituted or unsubstituted naphthyl,

[0061] Substituted or unsubstituted benzanthryl,

[0062] Substituted or unsubstituted phenoxy,

[0063] Substituted or unsubstituted triphenylene group,

[0064] substituted or unsubstituted phenalenyl,

[0065] substituted or unsubstituted pyrenyl,

[0066] substituted or unsubstituted chrysyl,

[0067] Substituted or unsubstituted benzophenone,

[0068] Substituted or unsubstituted triphenylene,

[0069] Substituted or unsubstituted benzotriphenylene,

[0070] Substituted or unsubstituted naphthacene,

[0071] Substituted or unsubstituted pentacene,

[0072] substituted or unsubstituted fluorenyl,

[0073] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0074] Substituted or unsubstituted benzofluorenyl,

[0075] Substituted or unsubstituted dibenzofluorenyl,

[0076] substituted or unsubstituted fluoranthene group,

[0077] Substituted or unsubstituted benzofluoranthenyl, and

[0078] A divalent arylene group derived by removing one hydrogen atom from the aromatic ring of any of the substituted or unsubstituted perylene groups, or

[0079] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[0080] As L 11 The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom,

[0081] When n11 is 0, L 11 represents a single bond,

[0082] Ar 11 is a hydrogen atom, or

[0083] substituted or unsubstituted phenyl,

[0084] Substituted or unsubstituted biphenyl,

[0085] Substituted or unsubstituted terphenyl,

[0086] substituted or unsubstituted naphthyl,

[0087] Substituted or unsubstituted benzanthryl,

[0088] Substituted or unsubstituted phenoxy,

[0089] Substituted or unsubstituted triphenylene group,

[0090] substituted or unsubstituted phenalenyl,

[0091] substituted or unsubstituted pyrenyl,

[0092] substituted or unsubstituted chrysyl,

[0093] Substituted or unsubstituted benzophenone,

[0094] Substituted or unsubstituted triphenylene,

[0095] Substituted or unsubstituted benzotriphenylene,

[0096] Substituted or unsubstituted naphthacene,

[0097] Substituted or unsubstituted pentacene,

[0098] substituted or unsubstituted fluorenyl,

[0099] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0100] Substituted or unsubstituted benzofluorenyl,

[0101] Substituted or unsubstituted dibenzofluorenyl,

[0102] substituted or unsubstituted fluoranthene group,

[0103] Substituted or unsubstituted benzofluoranthenyl, or

[0104] Any one of substituted or unsubstituted perylenyl groups, or

[0105] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0106] As Ar 11 The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom,

[0107] Indicates the bonding position. )

[0108] According to one embodiment of the present invention, there is provided an organic electroluminescent device comprising the compound according to one embodiment of the present invention as a first compound.

[0109] 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.

[0110] According to one embodiment of the present invention, there are provided a compound capable of improving the life of an organic electroluminescent element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element. BRIEF DESCRIPTION OF THE DRAWINGS

[0111] Figure 1 This is a diagram schematically showing the configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0112] Figure 2 This is a diagram schematically showing the configuration of another example of an organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0113] [definition]

[0114] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0115] 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.

[0116] 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" described below is set in the same manner unless 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.

[0117] 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.

[0118] 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 cyclically bonded. 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.

[0119] 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.

[0120] 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.

[0121] 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".

[0122] 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.

[0123] 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.

[0124] "Substituents described in this specification"

[0125] The substituents described in this specification are described below.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] "Substituted or unsubstituted aryl"

[0136] 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."

[0137] 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.

[0138] Unsubstituted aryl (Specific example group G1A):

[0139] Phenyl,

[0140] p-Biphenyl,

[0141] m-Biphenyl,

[0142] o-biphenyl,

[0143] 4-terphenyl-4-yl,

[0144] 4-terphenyl-3-yl,

[0145] 4-terphenyl-2-yl,

[0146] m-terphenyl-4-yl,

[0147] m-terphenyl-3-yl,

[0148] m-terphenyl-2-yl,

[0149] o-terphenyl-4-yl,

[0150] o-terphenyl-3-yl,

[0151] o-terphenyl-2-yl,

[0152] 1-naphthyl,

[0153] 2-naphthyl,

[0154] Anthracene,

[0155] Benzanthryl,

[0156] Fiki,

[0157] Triphenylene,

[0158] Phenalene,

[0159] Pyrene base,

[0160] phenanthera,

[0161] Benzophenone,

[0162] triphenylene,

[0163] Benzotriphenylene,

[0164] tetraphenyl,

[0165] Pentaphenyl,

[0166] Fluorenyl,

[0167] 9,9'-spirobifluorenyl,

[0168] Benzofluorenyl,

[0169] Dibenzofluorenyl,

[0170] Fluoranthene group,

[0171] Benzofluoranthene,

[0172] Perylene and

[0173] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0174]

Chemical Formula 3

[0175]

[0176]

Chemical Formula 4

[0177]

[0178] Substituted aryl (Specific example group G1B):

[0179] o-Tolyl,

[0180] m-Tolyl,

[0181] p-Tolyl,

[0182] p-Xylyl,

[0183] m-xylyl,

[0184] o-xylyl,

[0185] p-Isopropylphenyl,

[0186] m-isopropylphenyl,

[0187] o-isopropylphenyl,

[0188] tert-Butylphenyl,

[0189] m-tert-butylphenyl,

[0190] o-tert-butylphenyl,

[0191] 3,4,5-trimethylphenyl,

[0192] 9,9-dimethylfluorenyl,

[0193] 9,9-diphenylfluorenyl,

[0194] 9,9-bis(4-methylphenyl)fluorenyl,

[0195] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0196] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0197] Cyanophenyl,

[0198] triphenylsilylphenyl,

[0199] trimethylsilylphenyl,

[0200] Phenyl naphthyl,

[0201] naphthylphenyl and

[0202] 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.

[0203] "Substituted or unsubstituted heterocyclic group"

[0204] 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.

[0205] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0206] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0207] 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."

[0208] 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.

[0209] 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).

[0210] 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).

[0211] Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0212] Pyrrolyl,

[0213] Imidazole,

[0214] Pyrazolyl,

[0215] triazole,

[0216] Tetrazolyl,

[0217] Oxazolyl,

[0218] Isoxazolyl,

[0219] Oxadiazolyl,

[0220] Thiazolyl,

[0221] Isothiazolyl,

[0222] Thiadiazole,

[0223] Pyridyl,

[0224] Pyridazinyl,

[0225] Pyrimidine group,

[0226] Pyrazinyl,

[0227] Triazine,

[0228] Indolyl,

[0229] Isoindolyl,

[0230] Indolizinyl,

[0231] Quinolizinyl,

[0232] Quinolinyl,

[0233] Isoquinolinyl,

[0234] Cinnoline,

[0235] Phthalocyanine,

[0236] Quinazoline,

[0237] Quinoxaline,

[0238] Benzimidazole,

[0239] Indazolyl,

[0240] Phenanthroline,

[0241] Phenanthridinyl,

[0242] Acridinyl,

[0243] Phenazine,

[0244] Carbazolyl,

[0245] benzocarbazolyl,

[0246] Morpholinyl,

[0247] Phenoxazinyl,

[0248] Phenothiazine,

[0249] Azacarbazolyl, and

[0250] Diazacarbazolyl.

[0251] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0252] furanyl,

[0253] Oxazolyl,

[0254] Isoxazolyl,

[0255] Oxadiazolyl,

[0256] Xanthoxylum,

[0257] Benzofuranyl,

[0258] Isobenzofuranyl,

[0259] dibenzofuranyl,

[0260] naphthobenzofuranyl,

[0261] benzoxazolyl,

[0262] Benzisoxazolyl,

[0263] Phenoxazine,

[0264] Morpholinyl,

[0265] dinaphthofuranyl,

[0266] Azadibenzofuranyl,

[0267] Diazadibenzofuranyl,

[0268] Azanaphthobenzofuranyl and

[0269] naphthyridinylbenzofuranyl.

[0270] Unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3):

[0271] Thiphenyl,

[0272] Thiazolyl,

[0273] Isothiazolyl,

[0274] Thiadiazole,

[0275] benzothienyl,

[0276] Isobenzothienyl,

[0277] dibenzothienyl,

[0278] naphthobenzothienyl,

[0279] Benzothiazolyl,

[0280] Benzisothiazolyl,

[0281] Phenothiazine,

[0282] dinaphthothienyl,

[0283] azadibenzothienyl,

[0284] diazadibenzothienyl,

[0285] azanaphthobenzothienyl and

[0286] diazanaphthobenzothienyl.

[0287] 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):

[0288]

Chemical Formula 5

[0289]

[0290]

Chemical Formula 6

[0291]

[0292] 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.

[0293] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least one of them 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.

[0294] Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0295] (9-phenyl)carbazolyl,

[0296] (9-biphenyl)carbazolyl,

[0297] (9-phenyl)phenylcarbazolyl,

[0298] (9-naphthyl)carbazolyl,

[0299] Diphenylcarbazol-9-yl,

[0300] phenylcarbazol-9-yl,

[0301] Methylbenzimidazole,

[0302] Ethylbenzimidazolyl,

[0303] Phenyltriazine,

[0304] Biphenyl triazine group,

[0305] Diphenyltriazine,

[0306] Phenylquinazolinyl, and

[0307] Biphenylquinazolinyl.

[0308] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0309] Phenyldibenzofuranyl,

[0310] Methyldibenzofuranyl,

[0311] tert-Butyldibenzofuranyl and

[0312] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0313] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0314] Phenyldibenzothiophene,

[0315] Methyldibenzothiophene,

[0316] tert-Butyldibenzothienyl and

[0317] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0318] 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):

[0319] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, X A and Y A When at least one of the nitrogen atoms is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0320] "Substituted or unsubstituted alkyl"

[0321] 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.

[0322] "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.

[0323] Unsubstituted alkyl (Specific example group G3A):

[0324] methyl,

[0325] Ethyl,

[0326] n-propyl,

[0327] Isopropyl,

[0328] n-Butyl,

[0329] Isobutyl,

[0330] sec-butyl and

[0331] tert-butyl.

[0332] Substituted alkyl (Specific example group G3B):

[0333] Heptafluoropropyl (including isomers),

[0334] Pentafluoroethyl,

[0335] 2,2,2-trifluoroethyl and

[0336] trifluoromethyl.

[0337] "Substituted or unsubstituted alkenyl"

[0338] 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."

[0339] "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.

[0340] Unsubstituted alkenyl (Specific example Group G4A):

[0341] Vinyl,

[0342] Allyl,

[0343] 1-butenyl,

[0344] 2-Butenyl and

[0345] 3-Butenyl.

[0346] Substituted alkenyl (Specific example group G4B):

[0347] 1,3-Butadienyl,

[0348] 1-Methylvinyl,

[0349] 1-methylallyl,

[0350] 1,1-dimethylallyl,

[0351] 2-methylallyl and

[0352] 1,2-Dimethylallyl.

[0353] "Substituted or unsubstituted alkynyl"

[0354] 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.

[0355] 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.

[0356] Unsubstituted alkynyl (Specific example group G5A):

[0357] Ethylene.

[0358] "Substituted or unsubstituted cycloalkyl"

[0359] 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.

[0360] "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.

[0361] Unsubstituted cycloalkyl (Specific example group G6A):

[0362] Cyclopropyl,

[0363] Cyclobutyl,

[0364] Cyclopentyl,

[0365] Cyclohexyl,

[0366] 1-adamantyl,

[0367] 2-adamantyl,

[0368] 1-Norbornyl and

[0369] 2-Norbornyl.

[0370] Substituted cycloalkyl (specific example group G6B):

[0371] 4-Methylcyclohexyl.

[0372] ·“-Si(R 901 )(R 902 )(R 903 )”

[0373] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as specific examples (specific example group G7), and include

[0374] -Si(G1)(G1)(G1),

[0375] -Si(G1)(G2)(G2),

[0376] -Si(G1)(G1)(G2),

[0377] -Si(G2)(G2)(G2),

[0378] -Si(G3)(G3)(G3) and

[0379] -Si(G6)(G6)(G6). Here,

[0380] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0381] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0382] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0383] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0384] A plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0385] A plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0386] A plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0387] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0388] Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0389] A plurality of G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0390] ·“-O-(R 904 )”

[0391] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and include

[0392] -O(G1),

[0393] -O(G2),

[0394] -O(G3) and

[0395] -O(G6).

[0396] Here,

[0397] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0398] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0399] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0400] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0401] ·“-S-(R 905 )”

[0402] As -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0403] -S(G1),

[0404] -S(G2),

[0405] -S(G3) and

[0406] -S(G6).

[0407] Here,

[0408] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0409] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0410] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0411] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0412] ·“-N(R 906 )(R 907 )”

[0413] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0414] -N(G1)(G1),

[0415] -N(G2)(G2),

[0416] -N(G1)(G2),

[0417] -N(G3)(G3) and

[0418] -N(G6)(G6).

[0419] Here,

[0420] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0421] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0422] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0423] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0424] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0425] - A plurality of G2s in N(G2)(G2) are the same as or different from each other.

[0426] - A plurality of G3's in N(G3)(G3) are the same as or different from each other.

[0427] A plurality of G6's in -N(G6)(G6) are the same as or different from each other.

[0428] "Halogen atoms"

[0429] 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.

[0430] "Substituted or unsubstituted fluoroalkyl"

[0431] 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.

[0432] "Substituted or unsubstituted haloalkyl"

[0433] 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.

[0434] "Substituted or unsubstituted alkoxy"

[0435] 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.

[0436] "Substituted or unsubstituted alkylthio"

[0437] 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.

[0438] "Substituted or unsubstituted aryloxy group"

[0439] 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.

[0440] "Substituted or unsubstituted arylthio"

[0441] 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.

[0442] "Substituted or unsubstituted trialkylsilyl"

[0443] 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.

[0444] "Substituted or unsubstituted aralkyl"

[0445] 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.

[0446] 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.

[0447] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysyl group, a triphenylene group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group.

[0448] 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.

[0449] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0450]

Chemical Formula 7

[0451]

[0452] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0453]

Chemical Formula 8

[0454]

[0455] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), Indicates the bonding position.

[0456] 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.

[0457]

Chemical Formula 9

[0458]

[0459] In the above general formulas (TEMP-34) to (TEMP-41), Indicates the bonding position.

[0460] 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.

[0461] "Substituted or unsubstituted arylene group"

[0462] 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.

[0463] "Substituted or unsubstituted divalent heterocyclic group"

[0464] 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.

[0465] "Substituted or unsubstituted alkylene"

[0466] 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.

[0467] 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.

[0468]

Chemical Formula 10

[0469]

[0470]

Chemical Formula 11

[0471]

[0472] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0473] In the above general formulas (TEMP-42) to (TEMP-52), Indicates the bonding position.

[0474]

Chemical Formula 12

[0475]

[0476] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0477] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0478] In the above general formulas (TEMP-53) to (TEMP-62), Indicates the bonding position.

[0479]

Chemical Formula 13

[0480]

[0481] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0482] In the above general formulas (TEMP-63) to (TEMP-68), Indicates the bonding position.

[0483] 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).

[0484]

Chemical Formula 14

[0485]

[0486]

Chemical Formula 15

[0487]

[0488]

Chemical Formula 16

[0489]

[0490] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0491]

Chemical Formula 17

[0492]

[0493]

Chemical Formula 18

[0494]

[0495]

Chemical Formula 19

[0496]

[0497]

Chemical Formula 20

[0498]

[0499] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0500] The above is the description of the “substituents described in the present specification”.

[0501] "When bonding to form a ring"

[0502] In this specification, the expression "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

[0503] The following describes the case where "one or more of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "the case where they are bonded to form a ring"). This description uses the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring as an example.

[0504]

Chemical Formula 21

[0505]

[0506] For example, in the 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups as one group means that 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.

[0507] 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).

[0508]

Chemical Formula 22

[0509]

[0510] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where adjacent "two" groups are bonded as in the above example, but also the case where adjacent "three or more" groups are bonded. For example, if 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 .

[0511]

Chemical Formula 23

[0512]

[0513] 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 The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) is A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0514] 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.

[0515] 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.

[0516] 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.

[0517] 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.

[0518] "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.

[0519] 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.

[0520] 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.

[0521] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0522] In this specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0523] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0524] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0525] In the case of "one or more groups consisting of two or more adjacent atoms of ..." "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 of ... 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.

[0526] 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".

[0527] 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".

[0528] The above is an explanation of the case where "one or more groups consisting of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0529] Substituents when expressed as "substituted or unsubstituted"

[0530] 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

[0531] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0532] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0533] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0534] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0535] -Si(R 901 )(R 902 )(R 903 ),

[0536] -O-(R 904 ),

[0537] -S-(R 905 ),

[0538] -N(R 906 )(R 907 ),

[0539] Halogen atoms, cyano, nitro,

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

[0541] unsubstituted heterocyclic group having 5 to 50 ring atoms

[0542] The groups in the group etc.

[0543] Here, R 901 ~R 907 Each independently

[0544] hydrogen atoms,

[0545] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0546] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0547] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0548] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0549] In R 901 When there are two or more, two or more R 901 Same or different from each other,

[0550] In R 902 When there are two or more, two or more R 902 Same or different from each other,

[0551] In R 903 When there are two or more, two or more R 903 Same or different from each other,

[0552] In R 904 When there are two or more, two or more R 904 Same or different from each other,

[0553] In R 905 When there are two or more, two or more R 905 Same or different from each other,

[0554] In R 906 When there are two or more, two or more R 906 Same or different from each other,

[0555] In R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0556] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0557] an alkyl group having 1 to 50 carbon atoms,

[0558] an aryl group having 6 to 50 ring carbon atoms and

[0559] A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0560] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0561] an alkyl group having 1 to 18 carbon atoms,

[0562] an aryl group having 6 to 18 ring carbon atoms and

[0563] A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0564] Specific examples of each of the above optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0565] 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.

[0566] 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.

[0567] 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.

[0568] [First embodiment]

[0569] (Compound)

[0570] The compound according to this embodiment is a compound represented by the following general formula (1).

[0571]

Chemical Formula 24

[0572]

[0573] (In the above general formula (1),

[0574] Group consisting of R1 and R2

[0575] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0576] bonded to each other to form a substituted or unsubstituted fused ring, or

[0577] Not bonded to each other,

[0578] R1 and R2 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

[0579] a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms,

[0580] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0581] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0582] Ring A X is a ring represented by the above-mentioned general formula (1A-1) or (1A-2),

[0583] The ring represented by the above general formula (1A-1) is fused with the ring Cx at the position a,

[0584] The ring represented by the above general formula (1A-2) is fused with the ring Cx at the position b or c,

[0585] Ring B X is a ring represented by the above general formula (1B-1),

[0586] The ring represented by the above general formula (1B-1) is fused with the ring Cx at the position d, e, f or g,

[0587] One or more substituents represented by the following general formula (11) may be bonded to each of the ring represented by the above general formula (1A-1), the ring represented by the above general formula (1A-2), and the ring represented by the above general formula (1B-1), independently of each other.

[0588] One or more aryl groups Ar1 are bonded to at least one of the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1).

[0589] Ar1 is

[0590] Substituted or unsubstituted biphenyl,

[0591] Substituted or unsubstituted terphenyl,

[0592] substituted or unsubstituted naphthyl,

[0593] Substituted or unsubstituted benzanthryl,

[0594] Substituted or unsubstituted phenoxy,

[0595] Substituted or unsubstituted triphenylene group,

[0596] substituted or unsubstituted phenalenyl,

[0597] substituted or unsubstituted pyrenyl,

[0598] substituted or unsubstituted chrysyl,

[0599] Substituted or unsubstituted benzophenone,

[0600] Substituted or unsubstituted triphenylene,

[0601] Substituted or unsubstituted benzotriphenylene,

[0602] Substituted or unsubstituted naphthacene,

[0603] Substituted or unsubstituted pentacene,

[0604] substituted or unsubstituted fluorenyl,

[0605] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0606] Substituted or unsubstituted benzofluorenyl,

[0607] Substituted or unsubstituted dibenzofluorenyl,

[0608] substituted or unsubstituted fluoranthene group,

[0609] Substituted or unsubstituted benzofluoranthenyl, or

[0610] Substituted or unsubstituted perylenyl.)

[0611]

Chemical Formula 25

[0612]

[0613] (In the above general formula (11),

[0614] n 11 is 0, 1, 2, or 3,

[0615] L 11 For

[0616] substituted or unsubstituted phenyl,

[0617] Substituted or unsubstituted biphenyl,

[0618] Substituted or unsubstituted terphenyl,

[0619] substituted or unsubstituted naphthyl,

[0620] Substituted or unsubstituted benzanthryl,

[0621] Substituted or unsubstituted phenoxy,

[0622] Substituted or unsubstituted triphenylene group,

[0623] substituted or unsubstituted phenalenyl,

[0624] substituted or unsubstituted pyrenyl,

[0625] substituted or unsubstituted chrysyl,

[0626] Substituted or unsubstituted benzophenone,

[0627] Substituted or unsubstituted triphenylene,

[0628] Substituted or unsubstituted benzotriphenylene,

[0629] Substituted or unsubstituted naphthacene,

[0630] Substituted or unsubstituted pentacene,

[0631] substituted or unsubstituted fluorenyl,

[0632] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0633] Substituted or unsubstituted benzofluorenyl,

[0634] Substituted or unsubstituted dibenzofluorenyl,

[0635] substituted or unsubstituted fluoranthene group,

[0636] Substituted or unsubstituted benzofluoranthenyl, and

[0637] A divalent arylene group derived by removing one hydrogen atom from the aromatic ring of any of the substituted or unsubstituted perylene groups, or

[0638] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[0639] As L 11 The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom,

[0640] When n11 is 0, L 11 represents a single bond,

[0641] Ar 11 is a hydrogen atom, or

[0642] substituted or unsubstituted phenyl,

[0643] Substituted or unsubstituted biphenyl,

[0644] Substituted or unsubstituted terphenyl,

[0645] substituted or unsubstituted naphthyl,

[0646] Substituted or unsubstituted benzanthryl,

[0647] Substituted or unsubstituted phenoxy,

[0648] Substituted or unsubstituted triphenylene group,

[0649] substituted or unsubstituted phenalenyl,

[0650] substituted or unsubstituted pyrenyl,

[0651] substituted or unsubstituted chrysyl,

[0652] Substituted or unsubstituted benzophenone,

[0653] Substituted or unsubstituted triphenylene,

[0654] Substituted or unsubstituted benzotriphenylene,

[0655] Substituted or unsubstituted naphthacene,

[0656] Substituted or unsubstituted pentacene,

[0657] substituted or unsubstituted fluorenyl,

[0658] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0659] Substituted or unsubstituted benzofluorenyl,

[0660] Substituted or unsubstituted dibenzofluorenyl,

[0661] substituted or unsubstituted fluoranthene group,

[0662] Substituted or unsubstituted benzofluoranthenyl, or

[0663] Any one of substituted or unsubstituted perylenyl groups, or

[0664] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0665] As Ar 11The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom,

[0666] Indicates the bonding position. )

[0667] In the compound according to this embodiment, when the ring represented by the general formula (1A-2) is fused with the ring Cx at the b position, the compound represented by the general formula (1) is represented by the following general formula (1A-2a). Furthermore, when the ring represented by the general formula (1A-2) is fused with the ring Cx at the c position, the compound represented by the general formula (1) is represented by the following general formula (1A-2b).

[0668]

Chemical Formula 26

[0669]

[0670] In the compounds according to this embodiment, for example, when the ring represented by the general formula (1B-1) is fused to the ring Cx at the d position, the compound represented by the general formula (1) is represented by the following general formula (1B-1a) or (1B-1b). Furthermore, for example, when the ring represented by the general formula (1B-1) is fused to the ring Cx at the e position, the compound represented by the general formula (1) is represented by the following general formula (1B-1c) or (1B-1d).

[0671]

Chemical Formula 27

[0672]

[0673] In the compounds according to this embodiment, Ring A X Preferred is the ring represented by the above-mentioned general formula (1A-1).

[0674] The compound according to this embodiment (the compound represented by the above general formula (1)) is preferably a compound represented by the following general formula (1C), (1D), (1E) or (1F), and more preferably a compound represented by the following general formula (1C).

[0675]

Chemical Formula 28

[0676]

[0677] In the above general formulae (1C), (1D), (1E) and (1F),

[0678] R1 and R2 are independently the same as R1 and R2 in the above general formula (1),

[0679] R3~R 18 Each independently

[0680] The above-mentioned aryl group Ar1,

[0681] The substituent represented by the above general formula (11), or

[0682] hydrogen atoms,

[0683] Among them, R3~R 18 At least one of them is the above-mentioned aryl group Ar1.

[0684] It should be noted that R3~R 18 The case of being a hydrogen atom means that both the aryl group Ar1 and the substituent represented by the general formula (11) are unsubstituted.

[0685] In the compound according to this embodiment, the aryl groups of R1 and R2 are preferably

[0686] substituted or unsubstituted phenyl,

[0687] Substituted or unsubstituted biphenyl,

[0688] Substituted or unsubstituted terphenyl,

[0689] substituted or unsubstituted naphthyl,

[0690] Substituted or unsubstituted phenoxy,

[0691] Substituted or unsubstituted triphenylene group,

[0692] substituted or unsubstituted phenalenyl,

[0693] substituted or unsubstituted chrysyl,

[0694] Substituted or unsubstituted benzophenone,

[0695] Substituted or unsubstituted triphenylene,

[0696] Substituted or unsubstituted benzotriphenylene,

[0697] Substituted or unsubstituted naphthacene,

[0698] Substituted or unsubstituted pentacene,

[0699] substituted or unsubstituted fluorenyl,

[0700] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0701] Substituted or unsubstituted benzofluorenyl,

[0702] Substituted or unsubstituted dibenzofluorenyl,

[0703] substituted or unsubstituted fluoranthene group,

[0704] Substituted or unsubstituted benzofluoranthenyl, or

[0705] a substituted or unsubstituted perylenyl group.

[0706] In the compound according to this embodiment, the heterocyclic group represented by R1 and R2 is preferably a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and more preferably a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0707] In the compound according to this embodiment, it is preferred that R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0708] In the compound according to this embodiment, preferably, R1 and R2 are each independently a methyl group or an ethyl group.

[0709] In the compound according to this embodiment, it is also preferred that R1 and R2 are each independently a substituted or unsubstituted phenyl group.

[0710] In the compound according to this embodiment, it is preferred that R1 and R2 are not bonded to each other and do not form a ring.

[0711] In the compound according to this embodiment, it is also preferred that as Ar 11 One or more of the hydrogen atoms are deuterium atoms.

[0712] In the compound according to this embodiment, it is preferred that Ar 11 The aryl group is a substituted or unsubstituted phenyl group.

[0713] In the compound according to this embodiment, preferably, as L 11 The heterocyclic group contains an oxygen atom or a silicon atom as a heteroatom.

[0714] In the compound according to this embodiment, preferably, as L 11 The heterocyclic group is a substituted or unsubstituted divalent heterocyclic group having 5 to 16 ring atoms.

[0715] In the compound according to this embodiment, n11 is preferably 0. When n11 is 0, Ar 11 It is directly bonded to a carbon atom constituting the ring represented by the above-mentioned general formula (1A-1), the ring represented by the above-mentioned general formula (1A-2), and the ring represented by the above-mentioned general formula (1B-1) via a single bond.

[0716] In the compound according to this embodiment, n11 is also preferably 1.

[0717] In the compound involved in this embodiment, it is preferred that no substituent represented by the general formula (11) is bonded to the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1).

[0718] In the compounds according to this embodiment, it is preferred that in ring A X or Ring B X Only one aryl group Ar1 is bonded to (that is, any one of the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1)).

[0719] In the compound according to this embodiment, it is also preferred that one aryl group Ar1 is bonded to ring A X .

[0720] In the compound according to this embodiment, it is also preferred that R4 in the above-mentioned general formulas (1C) and (1D) is an aryl group Ar1.

[0721] In the compound according to this embodiment, it is also preferred that R 13 is an aryl group Ar1.

[0722] In the compound according to this embodiment, it is also preferred that R9 in the above-mentioned general formula (1D) is an aryl group Ar1.

[0723] In the compound according to this embodiment, it is also preferred that one aryl group Ar1 is bonded to ring B X .

[0724] In the compound according to this embodiment, it is also preferred that R4 in the above-mentioned general formulae (1E) and (1F) is an aryl group Ar1.

[0725] In the compounds according to this embodiment, the aryl group Ar1 is also preferably

[0726] substituted or unsubstituted naphthyl,

[0727] Substituted or unsubstituted benzanthryl,

[0728] Substituted or unsubstituted phenoxy,

[0729] substituted or unsubstituted pyrenyl, or

[0730] substituted or unsubstituted triphenylene,

[0731] More preferably, it is substituted or unsubstituted naphthyl,

[0732] Substituted or unsubstituted benzanthryl, or

[0733] a substituted or unsubstituted pyrene group,

[0734] More preferably, it is a substituted or unsubstituted benzanthryl group, or

[0735] a substituted or unsubstituted pyrene group.

[0736] In the compound according to this embodiment, it is also preferred that at least one of the hydrogen atoms possessed by Ar1 is a deuterium atom.

[0737] In the compound according to this embodiment, it is also preferred that all hydrogen atoms possessed by Ar1 are deuterium atoms.

[0738] It is also preferred that the compound according to this embodiment has at least one deuterium atom.

[0739] In the compound according to one embodiment, all hydrogen atoms in the compound according to this embodiment are deuterium atoms.

[0740] The compound according to this embodiment preferably does not contain a heteroatom.

[0741] In the compound according to the present embodiment, it is also preferred that the substituent ("optional substituent") when expressed as "substituted or unsubstituted" is, for example, selected from

[0742] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0743] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0744] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0745] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0746] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0747] -S-(R 905 ) shown in the group,

[0748] Halogen atoms,

[0749] Nitro,

[0750] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0751] A group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms. 901 ~R 907 Each independently

[0752] hydrogen atoms,

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

[0754] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

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

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

[0757] In R 901 When there are two or more, two or more R 901 Same or different from each other,

[0758] In R 902 When there are two or more, two or more R 902 Same or different from each other,

[0759] In R 903 When there are two or more, two or more R 903 Same or different from each other,

[0760] In R 904 When there are two or more, two or more R 904 Same or different from each other,

[0761] In R 905 When there are two or more, two or more R 905 Same or different from each other,

[0762] In R 906 When there are two or more, two or more R 906 Same or different from each other,

[0763] In R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0764] In the compound according to this embodiment, it is preferred that the substituent group described as "substituted or unsubstituted" is selected from

[0765] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0766] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0767] A group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms.

[0768] In the compound according to this embodiment, it is more preferred that the substituent group described as "substituted or unsubstituted" is selected from

[0769] unsubstituted alkyl group having 1 to 18 carbon atoms,

[0770] unsubstituted aryl group having 6 to 18 ring carbon atoms, and

[0771] A group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 18 ring atoms.

[0772] In the compound according to this embodiment, it is preferred that the aryl group described as "substituted or unsubstituted aryl group" is

[0773] Phenyl,

[0774] p-Biphenyl,

[0775] m-Biphenyl,

[0776] o-biphenyl,

[0777] 4-terphenyl-4-yl,

[0778] 4-terphenyl-3-yl,

[0779] 4-terphenyl-2-yl,

[0780] m-terphenyl-4-yl,

[0781] m-terphenyl-3-yl,

[0782] m-terphenyl-2-yl,

[0783] o-terphenyl-4-yl,

[0784] o-terphenyl-3-yl,

[0785] o-terphenyl-2-yl,

[0786] 1-naphthyl,

[0787] 2-naphthyl,

[0788] Fiki,

[0789] Triphenylene,

[0790] Phenalene,

[0791] phenanthera,

[0792] Benzophenone,

[0793] triphenylene,

[0794] Benzotriphenylene,

[0795] tetraphenyl,

[0796] Pentaphenyl,

[0797] Fluorenyl,

[0798] 9,9'-spirobifluorenyl,

[0799] Benzofluorenyl,

[0800] Dibenzofluorenyl,

[0801] Fluoranthene group,

[0802] benzofluoranthenyl, or perylene.

[0803] In the compound according to this embodiment, it is preferred that all the groups described as "substituted or unsubstituted" are unsubstituted.

[0804] ·Method for producing the compound according to this embodiment

[0805] The compounds of this embodiment can be produced according to the synthesis methods described in the Examples below. Alternatively, the compounds of this embodiment can be produced by following the synthesis methods using known substitution reactions and raw materials corresponding to the target substances.

[0806] Specific examples of the compounds according to this embodiment

[0807] Specific examples of the compound according to this embodiment include the following compounds, but the present invention is not limited to these specific examples.

[0808] It should be noted that, in this specification, a deuterium atom is represented by D in a chemical formula, and a protium atom is represented by H or omitted.

[0809]

Chemical Formula 29

[0810]

[0811]

Chemical Formula 30

[0812]

[0813]

Chemical Formula 31

[0814]

[0815]

Chemical Formula 32

[0816]

[0817]

Chemical Formula 33

[0818]

[0819]

Chemical Formula 34

[0820]

[0821]

Chemical Formula 35

[0822]

[0823]

Chemical Formula 36

[0824]

[0825]

Chemical Formula 37

[0826]

[0827]

Chemical Formula 38

[0828]

[0829]

Chemical Formula 39

[0830]

[0831]

Chemical Formula 40

[0832]

[0833]

Chemical Formula 41

[0834]

[0835]

Chemical Formula 42

[0836]

[0837]

Chemical Formula 43

[0838]

[0839]

Chemical Formula 44

[0840]

[0841]

Chemical Formula 45

[0842]

[0843]

Chemical Formula 46

[0844]

[0845]

Chemical Formula 47

[0846]

[0847]

Chemical Formula 48

[0848]

[0849]

Chemical Formula 49

[0850]

[0851]

Chemical Formula 50

[0852]

[0853]

Chemical Formula 51

[0854]

[0855]

Chemical Formula 52

[0856]

[0857]

Chemical Formula 53

[0858]

[0859]

Chemical Formula 54

[0860]

[0861]

Chemical Formula 55

[0862]

[0863]

Chemical Formula 56

[0864]

[0865]

Chemical Formula 57

[0866]

[0867]

Chemical Formula 58

[0868]

[0869]

Chemical Formula 59

[0870]

[0871]

Chemical Formula 60

[0872]

[0873]

Chemical Formula 61

[0874]

[0875]

Chemical Formula 62

[0876]

[0877]

Chemical Formula 63

[0878]

[0879]

Chemical Formula 64

[0880]

[0881]

Chemical Formula 65

[0882]

[0883]

Chemical Formula 66

[0884]

[0885]

Chemical Formula 67

[0886]

[0887]

Chemical Formula 68

[0888]

[0889]

Chemical Formula 69

[0890]

[0891]

Chemical Formula 70

[0892]

[0893]

Chemical Formula 71

[0894]

[0895]

Chemical Formula 72

[0896]

[0897]

Chemical Formula 73

[0898]

[0899]

Chemical Formula 74

[0900]

[0901]

Chemical Formula 75

[0902]

[0903]

Chemical Formula 76

[0904]

[0905]

Chemical Formula 77

[0906]

[0907]

Chemical Formula 78

[0908]

[0909]

Chemical Formula 79

[0910]

[0911]

Chemical Formula 80

[0912]

[0913]

Chemical Formula 81

[0914]

[0915]

Chemical Formula 82

[0916]

[0917]

Chemical Formula 83

[0918]

[0919]

Chemical Formula 84

[0920]

[0921]

Chemical Formula 85

[0922]

[0923]

Chemical Formula 86

[0924]

[0925]

Chemical Formula 87

[0926]

[0927]

Chemical Formula 88

[0928]

[0929]

Chemical Formula 89

[0930]

[0931]

Chemical Formula 90

[0932]

[0933]

Chemical Formula 91

[0934]

[0935]

Chemical Formula 92

[0936]

[0937]

Chemical Formula 93

[0938]

[0939]

Chemical Formula 94

[0940]

[0941]

Chemical Formula 95

[0942]

[0943]

Chemical Formula 96

[0944]

[0945]

Chemical Formula 97

[0946]

[0947]

Chemical Formula 98

[0948]

[0949] The compound involved in this embodiment has a fused fluorene structure having a ring structure fused on fluorene, and therefore has excellent excitation tolerance. The compound involved in this embodiment has a structure in which the ring shown in the above-mentioned general formula (1B-1) formed by four six-membered rings is fused with ring Cx. Therefore, the compound involved in this embodiment has an improved excitation tolerance compared to the compound having a structure in which an aromatic ring (such as a phenanthrene ring) formed by three six-membered rings is fused with ring Cx. By using the compound involved in this embodiment for an organic EL element, it is possible to expect to improve the life of the element. The compound involved in this embodiment can be suitably used as a host material for the light-emitting layer of an organic EL element.

[0950] [Second embodiment]

[0951] (Materials for organic electroluminescent devices)

[0952] The organic EL device material according to this embodiment contains the compound according to the first embodiment. As one embodiment, an organic EL device material containing only the compound according to the first embodiment can be used. Alternatively, an organic EL device material containing the compound according to the first embodiment and a compound different from the compound according to the first embodiment can be used.

[0953] In the organic EL device material of this embodiment, the compound according to the first embodiment is preferably used as a host material. In this case, the organic EL device material may contain the compound according to the first embodiment as a host material and other compounds such as a dopant material.

[0954] The compound according to the first embodiment is useful as a material for an organic EL device, useful as a material for a light-emitting layer of an organic EL device, and particularly useful as a host material for a blue light-emitting layer.

[0955] [Third embodiment]

[0956] (Organic electroluminescent element)

[0957] The organic EL element according to this embodiment will be described.

[0958] The organic EL device according to this embodiment contains the compound according to the first embodiment as a first compound.

[0959] The organic EL element involved in this embodiment comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises at least one layer formed of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers formed of organic compounds. The organic layer may further comprise an inorganic compound.

[0960] In the organic EL device according to this embodiment, at least one of the organic layers contains the first compound (the compound according to the first embodiment).

[0961] In the organic EL element of this embodiment, preferably, at least one of the organic layers has a light-emitting region. In the organic EL element of this embodiment, preferably, the light-emitting region includes at least one light-emitting layer. In one embodiment, the light-emitting layer includes the compound represented by the above-mentioned general formula (1).

[0962] In the organic EL device according to this embodiment, it is also preferable that the organic layer has a light-emitting region, the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contains the first compound as the first host material.

[0963] When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element according to this embodiment may include, for example, an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. Alternatively, the order of the first and second light-emitting layers may be reversed, and the organic EL element may include, for example, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.

[0964] (Emission wavelength of organic EL element)

[0965] The organic EL element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less, and more preferably emits light having a wavelength of 430 nm to 480 nm or less, when the element is driven.

[0966] The maximum peak wavelength of light emitted by the organic EL element when the element is driven is measured as follows: A voltage is applied to the organic EL element so that the current density is 10 mA / cm 2 The spectral emission brightness spectrum at the time of φ was measured using a spectral emission brightness meter CS-2000 (manufactured by Konica Minolta Co., Ltd.). In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity reaches the maximum was measured and defined as the maximum peak wavelength (unit: nm).

[0967] The method for measuring the maximum peak wavelength of the compound in this specification is as follows. -6 mol / L and above 10 -5 A quartz colorimetric cell is added to a toluene solution of less than 1 mol / L, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is set as luminescence intensity, and the horizontal axis is set as wavelength). The luminescence spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

[0968] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is referred to as the maximum emission peak wavelength. Note that in this specification, the maximum peak wavelength may be referred to as the fluorescence emission maximum peak wavelength (FL-peak).

[0969] In the organic EL element involved in this embodiment, the organic layer can be composed only of a light-emitting layer, and as an organic layer, it can also have at least one layer selected from the group consisting of 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.

[0970] The organic EL element according to this embodiment preferably includes a hole transport layer between the anode and the light-emitting region.

[0971] In the organic EL element according to this embodiment, it is preferred that the light-emitting region include a first light-emitting layer and a second light-emitting layer, and when the first light-emitting layer and the second light-emitting layer are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, a hole transport layer be provided between the anode and the first light-emitting layer. Furthermore, it is preferred that the hole transport layer be provided between the anode and the second light-emitting layer when the first light-emitting layer and the second light-emitting layer are stacked in the order of the second light-emitting layer and the first light-emitting layer from the anode side.

[0972] The organic EL element according to this embodiment preferably includes an electron transport layer between the cathode and the light-emitting region.

[0973] In the organic EL element according to this embodiment, it is preferred that the light-emitting region include a first light-emitting layer and a second light-emitting layer, and when the first light-emitting layer and the second light-emitting layer are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, an electron transport layer be provided between the cathode and the second light-emitting layer. Furthermore, it is preferred that when the first light-emitting layer and the second light-emitting layer are stacked in the order of the second light-emitting layer and the first light-emitting layer from the anode side, an electron transport layer be provided between the cathode and the first light-emitting layer.

[0974] Figure 1 A schematic configuration of an example of an organic EL element according to this embodiment is shown.

[0975] Figure 1 The organic EL element 1A shown includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and cathode 4. The organic layer 10A includes, in order from the anode 3 side, a hole-transporting region 6, a light-emitting region 5A, and an electron-transporting region 7. The hole-transporting region 6 includes, in order from the anode 3 side, a hole-injection layer 61 and a hole-transporting layer 62. The light-emitting region 5A includes a single light-emitting layer 5. The electron-transporting region 7 includes, in order from the light-emitting region 5A side, an electron-transporting layer 71 and an electron-injection layer 72.

[0976] (Luminescent layer)

[0977] The light-emitting layer 5 contains the compound according to the first embodiment.

[0978] In the organic EL device 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above general formula (1C), (1D), (1E) or (1F), and more preferably a compound represented by the above general formula (1C).

[0979] (Luminescent Compound)

[0980] In the organic EL device 1A, the light-emitting layer 5 preferably further contains a light-emitting compound (preferably a fluorescent compound).

[0981] (Compound represented by general formula (5))

[0982] In one embodiment of the organic EL device 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (5).

[0983]

Chemical Formula 99

[0984]

[0985] (In the above general formula (5),

[0986] By R 501 ~R 507 and R 511 ~R 517 One or more of the adjacent groups of two or more

[0987] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0988] bonded to each other to form a substituted or unsubstituted fused ring, or

[0989] Not bonded to each other,

[0990] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 501 ~R 507 and R 511 ~R 517 Each independently

[0991] hydrogen atoms,

[0992] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0993] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0994] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0995] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0996] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0997] -O-(R 904 ) shown in the group,

[0998] -S-(R 905 ) shown in the group,

[0999] -N(R 906 )(R 907) shown in the group,

[1000] Halogen atoms,

[1001] cyano,

[1002] Nitro,

[1003] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1004] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1005] R 521 and R 522 Each independently

[1006] hydrogen atoms,

[1007] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1008] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1009] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1010] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1011] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1012] -O-(R 904 ) shown in the group,

[1013] -S-(R 905 ) shown in the group,

[1014] -N(R 906 )(R 907 ) shown in the group,

[1015] Halogen atoms,

[1016] cyano,

[1017] Nitro,

[1018] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1019] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1020] In the luminescent compound (the above-mentioned general formula (5), and the general formulas (62), (42-2), and (3A) described later), R 901 、R 902 、R 903、R 904 、R 905 、R 906 and R 907 Each independently

[1021] hydrogen atoms,

[1022] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1023] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1024] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1025] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1026] Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1027] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1028] In R 901 When there are multiple R 901 Same or different from each other,

[1029] In R 902 When there are multiple R 902 Same or different from each other,

[1030] In R 903 When there are multiple R 903 Same or different from each other,

[1031] In R 904 When there are multiple R 904 Same or different from each other,

[1032] In R 905 When there are multiple R 905 Same or different from each other,

[1033] In R 906 When there are multiple R 906 Same or different from each other,

[1034] In R 907 When there are multiple R 907 Same as or different from each other.

[1035] “By R 501 ~R 507 and R 511 ~R 517One of the groups of two or more adjacent ones is, for example, R 501 With R 502 The group composed of R 502 With R 503 The group composed of R 503 With R 504 The group composed of R 505 With R 506 The group composed of R 506 With R 507 The group composed of R 501 With R 502 With R 503 Composition of groups etc.

[1036] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52).

[1037]

Chemical Formula 100

[1038]

[1039] (In the above general formula (52),

[1040] By R 531 ~R 534 and R 541 ~R 544 One or more of the adjacent groups of two or more

[1041] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1042] bonded to each other to form a substituted or unsubstituted fused ring, or

[1043] Not bonded to each other,

[1044] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 531 ~R 534 、R 541 ~R 544 and R 551 and R 552 Each independently

[1045] hydrogen atoms,

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

[1047] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1048] R 561 ~R 564 Each independently

[1049] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1050] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1051] (Compound represented by general formula (6))

[1052] In one embodiment of the organic EL device 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (6).

[1053] Chemical Formula 101

[1054]

[1055] (In the above general formula (6),

[1056] Ring a, ring b and ring c are each independently

[1057] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1058] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1059] R 601 With R 602 Each independently does not form a substituted or unsubstituted heterocyclic ring, or forms a substituted or unsubstituted heterocyclic ring by bonding with the above-mentioned a ring, b ring or c ring,

[1060] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 601 and R 602 Each independently

[1061] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1062] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1063] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1064] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1065] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1066] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1067] In one embodiment of the organic EL element, ring a, ring b, and ring c are rings fused to the central fused bicyclic structure of the 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).

[1068] The "aromatic hydrocarbon rings" of the a ring, the b ring, and the c ring have the same structure as a compound in which a hydrogen atom is introduced into an "aryl group".

[1069] 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.

[1070] 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.

[1071] 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.

[1072] 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".

[1073] 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.

[1074] 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 Bonded to a ring to form a fused 601 A nitrogen-containing heterocyclic ring fused with two (or more) nitrogen-containing rings of ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group fused with two or more rings in Specific Example Group G2.

[1075] 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.

[1076] R 601 and R 602 Each independently may not be bonded to the a ring, b ring or c ring.

[1077] 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.

[1078] 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.

[1079] In one embodiment, R in the above general formula (6) 601 and R 602 Each independently

[1080] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1081] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1082] It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1083] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62).

[1084]

Chemical Formula 102

[1085]

[1086] (In the above general formula (62),

[1087] 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,

[1088] 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,

[1089] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 601A and R602A Each independently

[1090] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1091] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1092] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1093] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1094] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1095] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1096] By R 611 ~R 621 One or more of the adjacent groups of two or more

[1097] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1098] bonded to each other to form a substituted or unsubstituted fused ring, or

[1099] Not bonded to each other,

[1100] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted condensed ring. 611 ~R 621 Each independently

[1101] hydrogen atoms,

[1102] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1103] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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

[1105] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1106] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1107] -O-(R 904 ) shown in the group,

[1108] -S-(R 905 ) shown in the group,

[1109] -N(R 906 )(R 907 ) shown in the group,

[1110] Halogen atoms,

[1111] cyano,

[1112] Nitro,

[1113] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1114] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1115] R in the above general formula (62) 601A and R 602A Each is the same as R in the above general formula (6) 601 and R 602 The corresponding group.

[1116] 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) 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 heterocyclic group 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.

[1117] By R 611 ~R 621 One or more of the adjacent groups of two or more can

[1118] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1119] They are bonded to each other to form a substituted or unsubstituted fused ring.

[1120] 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.

[1121] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (42-2).

[1122]

Chemical Formula 103

[1123]

[1124] (In the above general formula (42-2), R 611 ~R 617 、R 601A and R 602A Each independently of R in the above general formula (62) 611 ~R 617 、R 601A and R 602A Same meaning,

[1125] X4 is an oxygen atom or a sulfur atom,

[1126] By R 701 ~R 704 One or more of the adjacent groups of two or more

[1127] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1128] bonded to each other to form a substituted or unsubstituted fused ring, or

[1129] Not bonded to each other,

[1130] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 701 ~R 704 Each independently

[1131] hydrogen atoms,

[1132] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1133] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1134] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1135] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1136] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1137] -O-(R 904 ) shown in the group,

[1138] -S-(R 905 ) shown in the group,

[1139] -N(R 906 )(R907 ) shown in the group,

[1140] Halogen atoms,

[1141] cyano,

[1142] Nitro,

[1143] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1144] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1145] (Compound represented by general formula (3A))

[1146] In one embodiment of the organic EL device 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (3A).

[1147]

Chemical Formula 104

[1148]

[1149] (In the above general formula (3A),

[1150] By Ra 301 、Ra 302 、Ra 303 、Ra 304 、Ra 305 、Ra 306 、Ra 307 、Ra 308 、Ra 309 and Ra 310 One or more of the adjacent groups of two or more

[1151] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1152] bonded to each other to form a substituted or unsubstituted fused ring, or

[1153] Not bonded to each other,

[1154] Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following general formula (31A),

[1155] Ra 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 (31A) 301 ~Ra 310 Each independently

[1156] hydrogen atoms,

[1157] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1158] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1159] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1160] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1161] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1162] -O-(R 904 ) shown in the group,

[1163] -S-(R 905 ) shown in the group,

[1164] -N(R 906 )(R 907 ) shown in the group,

[1165] Halogen atoms,

[1166] cyano,

[1167] Nitro,

[1168] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1169] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1170]

Chemical Formula 105

[1171]

[1172] (In the above general formula (31A),

[1173] Ara 301 and Ara 302 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] La 301 、La 302 and La 303 Each independently

[1177] single bond,

[1178] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1179] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1180] represents the bonding position in the pyrene ring in the above general formula (3A).

[1181] (Specific examples of luminescent compounds)

[1182] Specific examples of the light-emitting compound are described below. These are merely examples, and the light-emitting compound is not limited to the following specific examples.

[1183]

Chemical Formula 106

[1184]

[1185]

Chemical Formula 107

[1186]

[1187]

Chemical Formula 108

[1188]

[1189]

Chemical Formula 109

[1190]

[1191]

Chemical Formula 110

[1192]

[1193]

Chemical Formula 111

[1194]

[1195]

Chemical Formula 112

[1196]

[1197]

Chemical Formula 113

[1198]

[1199]

Chemical Formula 114

[1200]

[1201]

Chemical Formula 115

[1202]

[1203]

Chemical Formula 116

[1204]

[1205] In the organic EL element 1A, the luminescent compound contained in the luminescent layer 5 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits light at a wavelength of 430 nm to 480 nm or less. In the organic EL element 1A, the luminescent compound contained in the luminescent layer 5 is preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescence at a wavelength of 430 nm to 480 nm or less.

[1206] In the organic EL element 1A, when the light-emitting layer 5 contains the compound involved in the first embodiment and the light-emitting compound, the compound involved in the first embodiment (first compound) is preferably a host material (sometimes also called a matrix material), and the light-emitting compound is preferably a dopant material (sometimes also called a guest material, an emitter or a light-emitting material).

[1207] In this specification, a "host material" is, for example, a material comprising "50% by mass or more of the layer." Thus, for example, in the case of organic EL element 1A, the content of the compound represented by general formula (1A) in light-emitting layer 5 is 50% by mass or more of the total mass of the light-emitting layer.

[1208] (Thickness of the light-emitting layer)

[1209] The thickness of the light-emitting layer 5 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.

[1210] (Content of Compound in Light Emitting Layer)

[1211] When the light-emitting layer 5 contains the compound according to the first embodiment and a light-emitting compound, the contents of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 are preferably within the following ranges, for example.

[1212] The content of the compound according to the first embodiment 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.

[1213] The content of the light-emitting 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.

[1214] However, the upper limit of the total content of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 is 100 mass %.

[1215] It should be noted that this embodiment does not exclude the inclusion of materials other than the compound and the light-emitting compound according to the first embodiment in the light-emitting layer 5 .

[1216] The light-emitting layer 5 may contain only one kind of the compound according to the first embodiment, or may contain two or more kinds. The light-emitting layer 5 may contain only one kind of the light-emitting compound, or may contain two or more kinds.

[1217] Figure 2 A schematic configuration of an example of an organic EL element according to this embodiment is shown.

[1218] Figure 2 The organic EL element 1B shown differs from the organic EL element 1A in that the organic layer 10B includes a first luminescent region 5B, but is otherwise the same as the organic EL element 1A. The first luminescent region 5B includes a first luminescent layer 51 and a second luminescent layer 52 in this order from the anode 3 side.

[1219] The first light-emitting layer 51 contains a first compound, and the second light-emitting layer 52 contains a second compound.

[1220] (First Compound)

[1221] In the organic EL device 1B, the first compound is the compound according to the first embodiment.

[1222] In the organic EL device according to this embodiment, the first compound is preferably a compound represented by the above-mentioned general formula (1).

[1223] (Second Compound)

[1224] In the organic EL device 1B, the second compound is not particularly limited, and examples thereof include a second compound represented by the following general formula (2).

[1225] In one embodiment of the organic EL device 1B, the second compound is a compound represented by the following general formula (2).

[1226]

Chemical Formula 117

[1227]

[1228] (In the above general formula (2),

[1229] R 201 ~R 208 Each independently

[1230] hydrogen atoms,

[1231] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1232] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[1233] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1234] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1235] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1236] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1237] -O-(R 904 ) shown in the group,

[1238] -S-(R 905 ) shown in the group,

[1239] -N(R 906 )(R 907 ) shown in the group,

[1240] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1241] -C(=O)R 801 The groups shown,

[1242] -COOR 802 The groups shown,

[1243] Halogen atoms,

[1244] cyano,

[1245] Nitro,

[1246] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1247] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1248] L 201 and L 202 Each independently

[1249] single bond,

[1250] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1251] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1252] Ar 201 and Ar 202 Each independently

[1253] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1254] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1255] (In the above second compound, R 901 、R 902 、R 903 、R 904 、R 905 、R 906 、R 907 、R 801 and R 802 Each independently

[1256] hydrogen atoms,

[1257] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1258] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1259] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1260] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1261] In R 901 When there are multiple R 901 Same or different from each other,

[1262] In R 902 When there are multiple R 902 Same or different from each other,

[1263] In R 903 When there are multiple R 903 Same or different from each other,

[1264] In R 904 When there are multiple R 904 Same or different from each other,

[1265] In R 905 When there are multiple R 905 Same or different from each other,

[1266] In R 906 When there are multiple R 906 Same or different from each other,

[1267] In R 907 When there are multiple R 907 Same or different from each other,

[1268] In R 801 When there are multiple R 801 Same or different from each other,

[1269] In R 802 When there are multiple R 802 Same as or different from each other.)

[1270] In one embodiment of the organic EL device 1B, the second compound is a compound having at least one group represented by the following general formula (HY1) in its molecule.

[1271]

Chemical Formula 118

[1272]

[1273] (In the above general formula (HY1),

[1274] R Y1 ~R Y8 and R Y11 ~R Y14 Each independently

[1275] hydrogen atoms,

[1276] Halogen atoms,

[1277] cyano,

[1278] Nitro,

[1279] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1280] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1281] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1282] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1283] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1284] -O-(R 904 ) shown in the group,

[1285] -S-(R 905 ) shown in the group,

[1286] -N(R906 )(R 907 ) shown in the group,

[1287] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1288] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1289] ny is 0 or 1,

[1290] in,

[1291] When ny is 0, select R Y1 ~R Y8 One of them is ey-bonded single bonds,

[1292] When ny is 1, R Y1 With R Y2 、R Y2 With R Y3 or R Y3 With R Y4 One of them is Cy-bonded single bond, R Y1 With R Y2 、R Y2 With R Y3 or R Y3 With R Y4 The other one is dy bonded single bond, selected from R Y5 ~R Y8 、R Y11 ~R Y14 , and not cy and dy bonded single bond R Y1 ~R Y4 One of them is ey-bonded single bonds,

[1293] Z2 is an oxygen atom or a sulfur atom,

[1294] fy represents the bonding position to an atom in the second compound.)

[1295] In one embodiment of the organic EL element 1B, when ny in the general formula (HY1) is 0, the group represented by the general formula (HY1) is represented by the following general formula (HY10).

[1296] In one embodiment of the organic EL device 1B, the second compound is a compound having at least one group represented by the following general formula (HY10) in its molecule.

[1297]

Chemical Formula 119

[1298]

[1299] (In the above general formula (HY10), R Y1 ~R Y8 and Z2 are each R in the above general formula (HY1) Y1 ~R Y8 Same meaning as Z2,

[1300] Among them, selected from R Y1 ~R Y8 One of them is ey-bonded single bonds,

[1301] fy represents the bonding position to an atom in the second compound.)

[1302] In one embodiment of the organic EL device 1B, the second compound is a compound having at least one group represented by the general formula (HY1) in the molecule and ny is 1.

[1303] In one embodiment of the organic EL device 1B, the second compound is a compound having at least one group selected from the group consisting of groups represented by the following general formulae (HY11), (HY12), and (HY13) in its molecule.

[1304]

Chemical Formula 120

[1305]

[1306] (In the above general formulas (HY11), (HY12) and (HY13), R Y1 ~R Y8 、R Y11 ~R Y14 and Z2 are each R in the above general formula (HY1) Y1 ~R Y8 、R Y11 ~R Y14 Same meaning as Z2,

[1307] Among them, R Y1 ~R Y8 and R Y11 ~R Y14 One of them is ey-bonded single bonds,

[1308] fy represents the bonding position to an atom in the second compound.)

[1309] In one embodiment of the organic EL device 1B, the second compound is a compound represented by the general formula (2), and the compound represented by the general formula (2) has at least one group represented by the general formula (HY1) in its molecule.

[1310] In one embodiment of the organic EL element 1B, Ar in the above general formula (2) 201 and Ar 202 At least one of them is a group represented by the above-mentioned general formula (HY1).

[1311] In one embodiment of the organic EL element 1B, Ar in the above general formula (2) 201 or Ar 202 It is a group represented by the above-mentioned general formula (HY1).

[1312] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the above-mentioned general formula (2), and the compound represented by the above-mentioned general formula (2) has at least one group selected from the group consisting of groups represented by the above-mentioned general formulas (HY11), (HY12) and (HY13) in its molecule.

[1313] In one embodiment of the organic EL element 1B, Ar in the above general formula (2) 201 and Ar 202 At least one of the groups is any one selected from the group consisting of groups represented by the above-mentioned general formulae (HY11), (HY12) and (HY13).

[1314] In one embodiment of the organic EL element 1B, Ar in the above general formula (2) 201 or Ar 202 It is any one group selected from the group consisting of groups represented by the above-mentioned general formulae (HY11), (HY12) and (HY13).

[1315] In one embodiment of the organic EL device 1B, the second compound includes at least one group selected from the group consisting of groups represented by the aforementioned general formulas (HY1), (HY10), (HY11), (HY12), and (HY13) in its molecule, thereby improving the excitation resistance of the second compound. By using such a second compound in the second light-emitting layer, the life of the organic EL device can be easily extended.

[1316] In one embodiment of the organic EL device 1B, all groups described as “substituted or unsubstituted” in the second compound are “unsubstituted” groups.

[1317] (Method for producing the second compound)

[1318] The second compound according to this embodiment can be produced by following a known method, or can be produced by following this method and using a known substitution reaction and raw materials corresponding to the target substance.

[1319] (Specific example of the second compound)

[1320] Specific examples of the second compound according to this embodiment include the following compounds, but the present invention is not limited to these specific examples.

[1321]

Chemical Formula 121

[1322]

[1323]

Chemical Formula 122

[1324]

[1325]

Chemical Formula 123

[1326]

[1327]

Chemical Formula 124

[1328]

[1329]

Chemical Formula 125

[1330]

[1331]

Chemical Formula 126

[1332]

[1333]

Chemical Formula 127

[1334]

[1335]

Chemical Formula 128

[1336]

[1337]

Chemical Formula 129

[1338]

[1339]

Chemical Formula 130

[1340]

[1341]

Chemical Formula 131

[1342]

[1343]

Chemical Formula 132

[1344]

[1345]

Chemical Formula 133

[1346]

[1347]

Chemical Formula 134

[1348]

[1349]

Chemical Formula 135

[1350]

[1351]

Chemical Formula 136

[1352]

[1353]

Chemical Formula 137

[1354]

[1355]

Chemical Formula 138

[1356]

[1357]

Chemical Formula 139

[1358]

[1359]

Chemical Formula 140

[1360]

[1361]

Chemical Formula 141

[1362]

[1363]

Chemical Formula 142

[1364]

[1365]

Chemical Formula 143

[1366]

[1367]

Chemical Formula 144

[1368]

[1369]

Chemical Formula 145

[1370]

[1371]

Chemical Formula 146

[1372]

[1373]

Chemical Formula 147

[1374]

[1375]

Chemical Formula 148

[1376]

[1377]

Chemical Formula 149

[1378]

[1379]

Chemical Formula 150

[1380]

[1381]

Chemical Formula 151

[1382]

[1383]

Chemical Formula 152

[1384]

[1385]

Chemical Formula 153

[1386]

[1387]

Chemical Formula 154

[1388]

[1389]

Chemical Formula 155

[1390]

[1391]

Chemical Formula 156

[1392]

[1393]

Chemical Formula 157

[1394]

[1395]

Chemical Formula 158

[1396]

[1397]

Chemical Formula 159

[1398]

[1399]

Chemical Formula 160

[1400]

[1401]

Chemical Formula 161

[1402]

[1403]

Chemical Formula 162

[1404]

[1405]

Chemical Formula 163

[1406]

[1407]

Chemical Formula 164

[1408]

[1409]

Chemical Formula 165

[1410]

[1411]

Chemical Formula 166

[1412]

[1413]

Chemical Formula 167

[1414]

[1415]

Chemical Formula 168

[1416]

[1417]

Chemical Formula 169

[1418]

[1419]

Chemical Formula 170

[1420]

[1421]

Chemical Formula 171

[1422]

[1423]

Chemical Formula 172

[1424]

[1425]

Chemical Formula 173

[1426]

[1427]

Chemical Formula 174

[1428]

[1429]

Chemical Formula 175

[1430]

[1431] In the specific examples of the following compounds, D represents a deuterium atom, z, z1, z2, z3, z4, z5 and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer greater than or equal to 1 and less than or equal to 8, z1 is an integer greater than or equal to 1 and less than or equal to 9, z2 to z5 are each an integer greater than or equal to 1 and less than or equal to 5, and z6 is an integer greater than or equal to 1 and less than or equal to 7.

[1432]

Chemical Formula 176

[1433]

[1434]

Chemical Formula 177

[1435]

[1436]

Chemical Formula 178

[1437]

[1438]

Chemical Formula 179

[1439]

[1440]

Chemical Formula 180

[1441]

[1442]

Chemical Formula 181

[1443]

[1444]

Chemical Formula 182

[1445]

[1446]

Chemical Formula 183

[1447]

[1448]

Chemical Formula 184

[1449]

[1450]

Chemical Formula 185

[1451]

[1452]

Chemical Formula 186

[1453]

[1454]

Chemical Formula 187

[1455]

[1456] (First Light-Emitting Compound and Second Light-Emitting Compound)

[1457] In the organic EL device 1B, the first light-emitting layer 51 also preferably contains a first light-emitting compound. The first light-emitting compound is preferably a fluorescent compound.

[1458] In the organic EL device 1B, the second light-emitting layer 52 also preferably contains a second light-emitting compound. The second light-emitting compound is preferably a fluorescent compound.

[1459] When the first light-emitting layer 51 contains a first light-emitting compound and the second light-emitting layer 52 contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound may be the same as or different from each other.

[1460] Examples of the first light-emitting compound and the second light-emitting compound include the same light-emitting compounds as exemplified in the organic EL device 1A.

[1461] In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 preferably emits light with a maximum peak wavelength of 500 nm or less, more preferably emits light at 430 nm to 480 nm.

[1462] In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 is preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less, more preferably a compound that emits fluorescence at 430 nm to 480 nm.

[1463] In the organic EL element 1B, when the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the first compound is preferably a first host material, and the first light-emitting compound is preferably a first dopant material.

[1464] In the organic EL element 1B, when the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the second compound is preferably a second host material, and the second light-emitting compound is preferably a second dopant material.

[1465] In the organic EL element 1B, the second light-emitting layer 52 preferably contains a second host material, and the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material preferably satisfy the relationship expressed by the following equation (Equation 1).

[1466] T1(H1)>T1(H2) …(Formula 1)

[1467] Tripret-Tripret-Annhilation (sometimes referred to as TTA) is a technique for improving the luminous efficiency of organic EL devices. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. It should be noted that the TTA mechanism is sometimes also referred to as the TTF mechanism, as described in International Publication No. 2010 / 134350.

[1468] The TTF phenomenon is explained. Holes injected from the anode and electrons injected from the cathode recombine within the light-emitting layer to form excitons. As previously known, their spin states are split between singlet excitons (25%) and triplet excitons (75%). In conventional fluorescent devices, 25% of the singlet excitons relax to the ground state and emit light, while the remaining 75% of the triplet excitons undergo thermal deactivation and return to the ground state without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent devices is said to be 25%.

[1469] On the other hand, the behavior of triplet excitons generated in organic matter has been studied theoretically. According to SM Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if it is assumed that high-order excitons such as quintet immediately return to triplet state, then in the case of triplet excitons (hereinafter referred to as 3 A ) gradually increases, triplet excitons collide with each other and the reaction shown in the following formula occurs. Here, 1 A represents the ground state, 1 A represents the lowest excited singlet exciton.

[1470] 3 A ＊ + 3 A ＊ →(4 / 9) 1 A+(1 / 9) 1 A ＊+(13 / 9) 3 A ＊

[1471] That is, it becomes 5 3 A →4 1 A+1A , it is estimated that of the 75% of triplet excitons initially generated, 1 / 5, or 20%, will transform into singlet excitons. Therefore, the singlet excitons that contribute to light become 40%, which is the sum of the 25% initially generated plus 75% × (1 / 5) = 15%. At this point, the proportion of light emission from TTF (TTF ratio) in the total luminescence intensity becomes 15 / 40, or 37.5%. Furthermore, if the 75% of triplet excitons initially generated collide with each other to form singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% can be achieved, which is the sum of the 25% of singlet excitons initially generated plus 75% × (1 / 2) = 37.5%. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[1472] According to the organic EL element involved in this embodiment, it is believed that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer, even if there are excess carriers at the interface between the first light-emitting layer and the directly connected organic layer, the triplet excitons present at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching due to excess electrons can be considered. On the other hand, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching due to excess holes can be considered.

[1473] The organic EL element 1B includes at least two light-emitting layers (i.e., a first light-emitting layer 51 and a second light-emitting layer 52) that satisfy a predetermined relationship. Furthermore, the first light-emitting layer 51 and the second light-emitting layer 52 are configured such that the triplet energy T1(H1) of the first compound in the first light-emitting layer 51 and the triplet energy T1(H2) of the second compound in the second light-emitting layer 52 satisfy the relationship described in the above-mentioned mathematical formula (Mathematical Formula 1). As a result, triplet excitons generated in the first light-emitting layer 51 are not quenched by excess carriers but instead migrate to the second light-emitting layer 52. Furthermore, reverse migration from the second light-emitting layer 52 to the first light-emitting layer 51 is suppressed. As a result, singlet excitons are efficiently generated in the second light-emitting layer 52 through the TTF mechanism, thereby improving luminous efficiency.

[1474] In this way, the organic EL element 1B has a first light-emitting layer 51 that mainly generates triplet excitons, and a second light-emitting layer 52 that effectively utilizes triplet excitons moved from the first light-emitting layer 51 and mainly exhibits a TTF mechanism as different regions. As the second compound in the second light-emitting layer 52, a compound having a smaller triplet energy than the first compound in the first light-emitting layer is used, and the difference in triplet energy is set, thereby improving the luminous efficiency.

[1475] (Triplet energy T1)

[1476] As a method for measuring the triplet energy T1, the following method can be mentioned.

[1477] The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 -5 mol / L and above 10 -4 A solution was prepared with a concentration of 1 mol / L or less, and this solution was added to a quartz colorimetric cell as a measurement sample. The phosphorescence spectrum of this measurement sample was measured at a low temperature (77[K]) (the vertical axis represents phosphorescence intensity, and the horizontal axis represents wavelength). A tangent line was drawn on the short-wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis was calculated. edge [nm], and the energy calculated by the following conversion formula (F1) is referred to as triplet energy T1.

[1478] Conversion formula (F1): T1 [eV] = 1239.85 / λ edge

[1479] The tangent line to the short-wavelength rise of the phosphorescence spectrum is derived as follows. As the spectrum curve moves from the short-wavelength side of the phosphorescence spectrum to the shortest-wavelength maximum among the spectral maxima, the tangent line at each point on the curve is considered toward the long-wavelength side. The slope of this tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where this slope reaches its maximum (i.e., the tangent line at the inflection point) is used as the tangent line to the short-wavelength rise of the phosphorescence spectrum.

[1480] It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

[1481] Phosphorescence can be measured using the F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Co., Ltd. The measuring device is not limited thereto, and measurement can be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[1482] In the organic EL element 1B, when the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the first light-emitting compound preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2).

[1483] S1(H1)>S1(D3)…(Formula 2)

[1484] (Singlet energy S1)

[1485] 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.

[1486] Preparation of 10 compounds to be measured -5 mol / L and above 10 -4 mol / L or less toluene solution and add it to a quartz colorimetric cell, and measure the absorption spectrum of the sample at room temperature (300K) (the vertical axis is the absorption intensity, the horizontal axis is the wavelength). Draw a tangent line on the long wavelength side of the absorption spectrum, and the wavelength value λ of the intersection of the tangent line and the horizontal axis is edge [nm] is substituted into the conversion formula (F2) shown below to calculate the singlet energy S1.

[1487] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[1488] 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.

[1489] 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.

[1490] 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.

[1491] In the organic EL element 1B, when the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the second compound is preferably a host material, and the second light-emitting compound is preferably a dopant material.

[1492] In the organic EL element 1B, when the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the second light-emitting compound preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3).

[1493] S1(H2)>S1(D4)…(Formula 3)

[1494] It is preferable that the first light-emitting layer 51 and the second light-emitting layer 52 do not contain a phosphorescent material (dopant material).

[1495] In addition, the first light-emitting layer 51 and the second light-emitting layer 52 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.

[1496] Furthermore, the first light-emitting layer 51 and the second light-emitting layer 52 also preferably do not contain a metal complex.

[1497] (Thickness of the light-emitting layer)

[1498] The thickness of the first light-emitting layer 51 and the second light-emitting layer 52 in the organic EL element 1B is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. When the thickness of the light-emitting layer is 5 nm or greater, it is easier to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easier to suppress an increase in the driving voltage.

[1499] (Content of Compound in Light Emitting Layer)

[1500] When the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the contents of the first compound and the first light-emitting compound in the first light-emitting layer 51 are preferably within the following ranges, for example.

[1501] 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.

[1502] The content of the first light-emitting compound is preferably 1 mass % to 10 mass %, more preferably 1 mass % to 7 mass %, and even more preferably 1 mass % to 5 mass %.

[1503] However, the upper limit of the total content of the first compound and the first light-emitting compound in the first light-emitting layer 51 is 100 mass %.

[1504] It should be noted that this embodiment does not exclude the inclusion of materials other than the first compound and the first light-emitting compound in the first light-emitting layer 51 .

[1505] The first light-emitting layer 51 may contain only one first compound, or may contain two or more first compounds. The first light-emitting layer 51 may contain only one first light-emitting compound, or may contain two or more first compounds.

[1506] When the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the contents of the second compound and the second light-emitting compound in the second light-emitting layer 52 are preferably within the following ranges, for example.

[1507] 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.

[1508] The content of the second light-emitting compound is preferably 1 mass % to 10 mass %, more preferably 1 mass % to 7 mass %, and even more preferably 1 mass % to 5 mass %.

[1509] However, the upper limit of the total content of the second compound and the second light-emitting compound in the second light-emitting layer 52 is 100 mass %.

[1510] It should be noted that this embodiment does not exclude the inclusion of materials other than the second compound and the second light-emitting compound in the second light-emitting layer 52 .

[1511] The second light-emitting layer 52 may contain only one second compound, or may contain two or more second compounds. The second light-emitting layer 52 may contain only one second light-emitting compound, or may contain two or more second compounds.

[1512] In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other.

[1513] In the organic EL element 1B, when "the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other", the layer structure of "the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other" may include any one of the following schemes (LS1), (LS2) and (LS3).

[1514] (LS1) A scheme in which a region in which a first compound serving as a main material (hereinafter sometimes referred to as "first main material") and a second compound serving as a main material (hereinafter sometimes referred to as "second main material") are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[1515] (LS2) In the case where the first light-emitting layer 51 and the second light-emitting layer 52 contain light-emitting compounds, a region in which the first main material, the second main material and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[1516] (LS3) In the case where the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, a region formed by the light-emitting compound, a region formed by the first main material, or a region formed by the second main material is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[1517] When the organic EL element 1B includes a third light-emitting layer, it is preferred that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other, and the second light-emitting layer 52 and the third light-emitting layer are in direct contact with each other.

[1518] In the organic EL element 1B, in the case where "the second light-emitting layer 52 is directly in contact with the third light-emitting layer", the layer structure of "the second light-emitting layer 52 is directly in contact with the third light-emitting layer" may include, for example, any one of the following schemes (LS4), (LS5) and (LS6).

[1519] (LS4) A scheme in which a region where the second main material and the third main material (the main material contained in the third light-emitting layer) are mixed is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[1520] (LS5) In the case where the second light-emitting layer 52 and the third light-emitting layer contain light-emitting compounds, a region in which the second main material, the third main material and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[1521] (LS6) In the case where the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region formed by the light-emitting compound, a region formed by the second main material, or a region formed by the third main material is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[1522] The organic EL element 1B preferably further includes an interlayer.

[1523] When the organic EL element 1B includes an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer 51 and the second light-emitting layer 52 .

[1524] (Interlayer)

[1525] The interlayer is preferably an undoped layer. The interlayer preferably does not contain metal atoms.

[1526] The interlayer comprises an interlayer material, which is preferably not a light-emitting compound.

[1527] The interlayer material is not particularly limited, but is preferably a material other than a light-emitting compound.

[1528] Examples of interlayer materials include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[1529] The interlayer material may be one or both of the first compound contained in the first light-emitting layer 51 and the second compound contained in the second light-emitting layer 52 .

[1530] When the interlayer contains a plurality of interlayer materials, the content of each interlayer material is preferably 10% by mass or more of the total mass of the interlayer.

[1531] In the interlayer, the content of the above-mentioned interlayer material is preferably more than 60 mass % of the total mass of the interlayer, more preferably more than 70 mass % of the total mass of the interlayer, further preferably more than 80 mass % of the total mass of the interlayer, further preferably more than 90 mass % of the total mass of the interlayer, and especially preferably more than 95 mass % of the total mass of the interlayer.

[1532] The interlayer may contain only one interlayer material, or may contain two or more interlayer materials.

[1533] When the interlayer contains two or more interlayer materials, the upper limit of the total content of the two or more interlayer materials is 100% by mass.

[1534] It should be noted that this embodiment does not exclude the inclusion of materials other than the interlayer material in the interlayer.

[1535] The interlayer may be composed of a single layer or a stack of two or more layers.

[1536] The thickness of the interlayer is not particularly limited, but is preferably 3 nm to 15 nm, and more preferably 5 nm to 10 nm, per layer.

[1537] The configuration of each layer common to the organic EL element 1A and the organic EL element 1B will be further described.

[1538] (Substrate)

[1539] The substrate 2 is used as a support for the organic EL element. As the substrate 2, 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.

[1540] (anode)

[1541] The anode 3 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). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing 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).

[1542] 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 containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[1543] Among the organic layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that is easy to inject holes regardless of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

[1544] 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.

[1545] (cathode)

[1546] The cathode 4 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 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1547] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, vacuum evaporation or sputtering can be used. In addition, when a silver paste is used, coating or inkjet methods can be used.

[1548] 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.

[1549] (Hole Injection Layer)

[1550] The hole injection layer 61 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.

[1551] Examples of substances with high hole-injecting properties include 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), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl]biphenyl (abbreviation: Aromatic amine compounds such as 1-[(1-[(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole)]- ...

[1552] In addition, as a substance with high hole-injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. Examples include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[1553] (Hole Transport Layer)

[1554] The hole transport layer 62 is a layer containing a substance with high hole transport properties. The hole transport layer 62 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- Aromatic amine compounds such as [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 with 10 -6 cm 2 / (V·s) or more.

[1555] The hole transport layer 62 may also use 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), or anthracene derivatives such as t-BuDNA, DNA, or DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[1556] It should be noted that as long as the hole transport property is higher than the electron transport property, 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 layers of the above substances.

[1557] (Specific Examples of Hole Transport Zone Materials)

[1558] Specific examples of hole transport region materials include the following compounds: However, the present invention is not limited to these specific examples of hole transport region materials.

[1559]

Chemical Formula 188

[1560]

[1561] (Electron Transport Layer)

[1562] The electron transport layer 71 is a layer containing a substance with high electron transport properties. The electron transport layer 71 uses 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition, 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), bathocuproine (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 heteroaromatic compounds having 10 -6 cm 2 / (V·s) or more. It should be noted that as long as the electron transport property is higher than the hole transport property, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can also be composed of a single layer or a stack of two or more layers formed by the above substances.

[1563] Alternatively, a polymer compound may be used for the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-c-o(pyridine-3,5-diyl)] (abbreviated as PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-c-o(2,2′-bipyridine-6,6′-diyl)] (abbreviated as PF-BPy) may be used.

[1564] (Specific examples of electron transport materials)

[1565] Specific examples of electron transport materials that can be used in the electron transport layer include the following compounds. However, the present invention is not limited to these specific examples of electron transport materials.

[1566]

Chemical Formula 189

[1567]

[1568]

Chemical Formula 190

[1569]

[1570] (Electron Injection Layer)

[1571] The electron injection layer 72 is a layer containing a substance with high electron injection properties. The electron injection layer 72 can use alkali metals, alkaline earth metals or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc. In addition, a material containing an alkali metal, alkaline earth metal or their compound in a substance with electron transport properties can also be used. Specifically, a material containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently at this time.

[1572] Alternatively, the electron injection layer 72 may also use a composite material mixed with an organic compound and an electron donor (donor). Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. At this time, as an organic compound, it is preferably a material with excellent transport of the generated electrons. Specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. As an electron donor, it is sufficient to be 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.

[1573] (Layer Formation Method)

[1574] 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, immersion, flow coating, and inkjet can be used.

[1575] (film thickness)

[1576] The thickness of each organic layer in the organic EL element of this embodiment is not limited except as 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, resulting in reduced 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.

[1577] According to this embodiment, an organic electroluminescent element having an improved lifespan can be provided.

[1578] [Fourth embodiment]

[1579] (Electronic equipment)

[1580] The electronic device involved in this embodiment is equipped with the organic electroluminescent element involved in the third embodiment. As electronic devices, for example, display devices and light-emitting devices can be given. As display devices, for example, display components (such as organic EL panel modules, etc.), televisions, mobile phones, tablet computers and personal computers can be given. As light-emitting devices, for example, lighting and vehicle lamps can be given. The light-emitting device can also be used in a display device, for example, it can also be used as a backlight for a display device.

[1581] [Variations of the Embodiments]

[1582] 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.

[1583] For example, the number of light-emitting layers in an organic EL element is not limited to one or two layers, and three or more light-emitting layers may be stacked. In the case where an organic EL element has two or more light-emitting layers, at least two light-emitting layers (a first light-emitting layer and a second light-emitting layer) may satisfy the conditions described in the above embodiment. For example, the other light-emitting layer may be a fluorescent light-emitting layer, or a phosphorescent light-emitting layer that utilizes light emission based on electron transition from a triplet excited state directly to a ground state.

[1584] 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.

[1585] 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.

[1586] Example

[1587] 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.

[1588] <Compound>

[1589] The structures of the compounds represented by the general formula (1) used in the production of the organic EL devices according to the Examples and the structures of the compounds represented by the general formula (1) according to the Synthesis Examples are shown below.

[1590]

Chemical Formula 191

[1591]

[1592]

Chemical Formula 192

[1593]

[1594]

Chemical Formula 193

[1595]

[1596]

Chemical Formula 194

[1597]

[1598]

Chemical Formula 195

[1599]

[1600] The structures of comparative compounds used in the production of organic EL devices according to Comparative Examples are shown below.

[1601]

Chemical Formula 196

[1602]

[1603] The structures of other compounds used in the organic EL devices according to Examples and Comparative Examples are shown below.

[1604]

Chemical Formula 197

[1605]

[1606] <Fabrication of organic EL elements (1)>

[1607] Organic EL devices were produced and evaluated as follows.

[1608] [Example 1]

[1609] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO (Indium Tin Oxide) transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then cleaned with UV ozone for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[1610] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation apparatus. Compound HA-1 was first deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a hole injection layer (HI) with a thickness of 5 nm.

[1611] Following the formation of the hole injection layer, compound HT-1 was evaporated to form a first hole transport layer having a thickness of 80 nm.

[1612] Following the formation of the first hole transport layer, compound HT-2 was evaporated to form a second hole transport layer (also referred to as an electron blocking layer) having a thickness of 10 nm.

[1613] On the second hole transport layer, compound BH1-1 as a first compound and compound BD-1 as a first light-emitting compound were co-evaporated to form a first light-emitting layer with a thickness of 5 nm so that the ratio of compound BD-1 was 2% by mass.

[1614] On the first emitting layer, compound BH-2 as a second compound and compound BD-1 as a second emitting compound were co-deposited so that the ratio of compound BD-1 was 2% by mass to form a second emitting layer with a thickness of 20 nm.

[1615] Compound ET-1 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a thickness of 10 nm.

[1616] Compound ET-2 was evaporated on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm.

[1617] LiF was evaporated on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.

[1618] Metal Al was evaporated on the electron injection layer to form a cathode having a film thickness of 80 nm.

[1619] The component structure of Example 1 is abbreviated as follows.

[1620] ITO(130) / HA-1(5) / HT-1(80) / HT-2(10) / BH1-1: BD-1(5, 98%: 2%) / BH-2: BD-1(20, 98%: 2%) / ET-1(10) / ET-2(15) / LiF(1) / Al(80)

[1621] In addition, the numbers in parentheses represent film thickness (unit: nm).

[1622] Similarly, the numbers expressed in percentages in parentheses (98%:2%) represent the ratio (mass %) of compound BH1-1 or compound BH-2 to compound BD-1 in the first or second light-emitting layer.

[1623] [Examples 2 to 8]

[1624] The organic EL devices of Examples 2 to 8 were produced in the same manner as in Example 1, except that the first compound of the first light-emitting layer was changed to the compound described in Table 1.

[1625] [Comparative Example 1]

[1626] The organic EL device of Comparative Example 1 was produced in the same manner as in Example 1, except that the first compound of the first light-emitting layer was changed to the compound described in Table 1.

[1627] <Evaluation of organic EL elements (1)>

[1628] The following evaluations were performed on the organic EL devices produced in Examples 1 to 8 and Comparative Example 1. The evaluation results are shown in Table 1.

[1629] Lifespan (LT95)

[1630] A voltage was applied to the obtained organic EL element so that the current density reached 50 mA / cm 2The time it takes for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured. Brightness was measured using a CS-2000 spectrophotometer (manufactured by Konica Minolta Co., Ltd.). "LT95 (relative value)" was calculated from the measured values ​​using the following formula (Formula 1X).

[1631] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 (Formula 1X)

[1632]

Table 1

[1633]

[1634] The organic EL devices of Examples 1 to 8 contain the compound represented by the general formula (1) as a host material of the first light-emitting layer.

[1635] As a result, the organic EL elements of Examples 1 to 8 had longer lifespans than the organic EL element of Comparative Example 1.

[1636] <Evaluation of Compounds>

[1637] (Triplet energy T1)

[1638] The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to prepare a solution, which was then added to a quartz colorimetric cell as a measurement sample.

[1639] For this measurement sample, a phosphorescence spectrum (the vertical axis is the phosphorescence intensity, the horizontal axis is the wavelength) is measured at a low temperature (77 [K]). A tangent line is drawn on the short wavelength side of the phosphorescence spectrum, and the wavelength value λ based on the intersection of the tangent line and the horizontal axis is set. edge The energy calculated by the following conversion formula (F1) is the triplet energy T1. The results are shown in Table 1.

[1640] It should be noted that the triplet energy T1 may have an error of approximately 0.02 eV depending on the measurement conditions.

[1641] Conversion formula (F1): T1 [eV] = 1239.85 / λedge

[1642] The tangent line to the short-wavelength rise of the phosphorescence spectrum is drawn as follows. As the spectrum curve moves from the short-wavelength side of the phosphorescence spectrum to the shortest-wavelength maximum among the spectral maxima, the tangent line at each point on the curve is considered toward the long-wavelength side. The slope of this tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where this slope reaches its maximum (i.e., the tangent line at the inflection point) is used as the tangent line to the short-wavelength rise of the phosphorescence spectrum.

[1643] It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

[1644] Phosphorescence was measured using a F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation.

[1645] <Synthesis Example>

[1646] [Synthesis Example 1: Synthesis of Compound BH1-1]

[1647] Compound BH1-1 was synthesized using the following synthetic route.

[1648]

Chemical Formula 198

[1649]

[1650] (Synthesis of Intermediate Ma)

[1651] Under a nitrogen atmosphere, benzo[c]phenanthrene-5-ylboronic acid (145g, 533mmol), tetrakis(triphenylphosphine)palladium (12.4g, 10.7mmol), sodium carbonate (113g, 1066mmol), 1,2-dimethoxyethane (3.3L), and water (800ml) were added to a 5L three-necked flask and heated under reflux for 5 hours. The reaction solution was extracted with dichloromethane and purified by column chromatography to obtain 117g of a white solid. ASAP-MS analysis identified the white solid as intermediate Ma (yield 50%).

[1652] It should be noted that ASAP-MS is the abbreviation of Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[1653] (Synthesis of Intermediate Mb)

[1654] Under a nitrogen atmosphere, intermediate Ma (117 g, 267 mmol) and tetrahydrofuran (1.2 L) were added to a 2 L three-necked flask and cooled to 0 ° C. After adding 1 M methylmagnesium bromide (800 mL), the mixture was heated under reflux for 7 hours. An aqueous ammonium chloride solution was added to the reaction solution to quench the reaction and extracted with dichloromethane. After the resulting solution was concentrated, it was refined using silica gel chromatography to obtain 70 g of brown oil. By ASAP-MS analysis, the brown oil was identified as intermediate Mb (yield 60%).

[1655] (Synthesis of Intermediate Mc)

[1656] Under a nitrogen atmosphere, intermediate Mb (70 g, 160 mmol) and chloroform (700 mL) were added to a 2L three-necked flask and cooled to 0°C. Boron trifluoride diethyl ether complex (98 g, 208 mmol) was added thereto and stirred at room temperature to 35°C for 6 hours. The reaction solution was concentrated, extracted with dichloromethane, and further purified by silica gel chromatography to obtain 34 g of a white solid. The white solid was identified as intermediate Mc by ASAP-MS analysis (yield 50%).

[1657] (Synthesis of Compound BH1-1)

[1658] Under a nitrogen atmosphere, the intermediate Mc (4.2 g, 10 mmol), 1-pyreneboronic acid (2.58 g, 10.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (183 mg, 0.20 mmol), SPhos (328 mg, 0.80 mmol), 2M sodium carbonate aqueous solution (12.5 mL, 25 mmol), and 1,4-dioxane (67 mL) were added to a 250 mL three-necked flask and heated under reflux for 5 hours. The reaction solution was extracted with dichloromethane and purified by column chromatography to obtain 4.6 g of a white solid. The white solid was identified as compound BH1-1 by ASAP-MS analysis (yield 84%).

[1659] [Synthesis Example 2: Synthesis of Compound BH1-2]

[1660] Compound BH1-2 was synthesized using the following synthetic route.

[1661]

Chemical Formula 199

[1662]

[1663] (Synthesis of Compound BH1-2)

[1664] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that the intermediate Md was used instead of 1-pyreneboronic acid, to obtain 4.69 g of a white solid. This white solid was identified as Compound BH1-2 by ASAP-MS analysis (yield 82%).

[1665] [Synthesis Example 3: Synthesis of Compound BH1-3]

[1666] Compounds BH1-3 were synthesized using the following synthetic route.

[1667]

Chemical Formula 200

[1668]

[1669] (Synthesis of Compound BH1-3)

[1670] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that 2-naphthaleneboronic acid was used instead of 1-pyreneboronic acid, to obtain 3.29 g of a white solid. This white solid was identified as Compound BH1-3 by ASAP-MS analysis (yield 70%).

[1671] [Synthesis Example 4: Synthesis of Compound BH1-4]

[1672] Compounds BH1-4 were synthesized using the following synthetic route.

[1673]

Chemical Formula 201

[1674]

[1675] (Synthesis of Compound BH1-4)

[1676] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that the intermediate Me was used instead of 1-pyreneboronic acid, to obtain 2.52 g of a white solid. This white solid was identified as Compound BH1-4 by ASAP-MS analysis (yield 46%).

[1677] [Synthesis Example 5: Synthesis of Compound BH1-5]

[1678] Compound BH1-5 was synthesized using the following synthetic route.

[1679]

Chemical Formula 202

[1680]

[1681] (Synthesis of Compound BH1-5)

[1682] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that the intermediate Mf was used instead of 1-pyreneboronic acid, to obtain 3.13 g of a white solid. This white solid was identified as Compound BH1-5 by ASAP-MS analysis (yield 54%).

[1683] [Synthesis Example 6: Synthesis of Compound BH1-6]

[1684] Compounds BH1-6 were synthesized using the following synthetic route.

[1685]

Chemical Formula 203

[1686]

[1687] (Synthesis of Compound BH1-6)

[1688] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that the intermediate Mg was used instead of 1-pyreneboronic acid, to obtain 3.44 g of a white solid. This white solid was identified as Compound BH1-6 (yield 56%) by ASAP-MS analysis.

[1689] [Synthesis Example 7: Synthesis of Compound BH1-7]

[1690] Compound BH1-7 was synthesized using the following synthetic route.

[1691]

Chemical Formula 204

[1692]

[1693] (Synthesis of Intermediate Mh)

[1694] Intermediate Mh was synthesized according to the method of "(Synthesis of Intermediate Mb)" in Synthesis Example 1, except that phenylmagnesium bromide was used instead of methylmagnesium bromide.

[1695] (Synthesis of Intermediate Mi)

[1696] Intermediate Mi was synthesized according to the method of "(Synthesis of Intermediate Mc)" in Synthesis Example 1, except that intermediate Mh was used instead of intermediate Mb.

[1697] (Synthesis of Compound BH1-7)

[1698] The same synthesis method as in "(Synthesis of Compound BH1-1)" was used, except that Intermediate Mi (5.47 g) was used instead of Intermediate Mc, to obtain 3.89 g of a white solid. This white solid was identified as Compound BH1-7 (yield 58%) by ASAP-MS analysis.

[1699] [Synthesis Example 8: Synthesis of Compound BH1-8]

[1700] Compound BH1-8 was synthesized using the following synthetic route.

[1701]

Chemical Formula 205

[1702]

[1703] (Synthesis of Compound BH1-8)

[1704] Synthesis was performed using the same method as described in "(Synthesis of Compound BH1-1)" except that intermediate Mi (5.47 g) was used instead of intermediate Mc, and intermediate Md was used instead of 1-pyreneboronic acid. This yielded 2.99 g of a white solid. ASAP-MS analysis identified this white solid as compound BH1-8 (yield 43%).

[1705] [Synthesis Example 9: Synthesis of Compound BH-Ref1]

[1706] Compound BH-Ref1 was synthesized using the following synthetic route.

[1707]

Chemical Formula 206

[1708]

[1709] (Synthesis of Compound BH-Ref1)

[1710] Under nitrogen atmosphere, 2-(13,13-dimethyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (3.56 g, 8.47 mmol), 1-bromopyrene (bromo pyrene) (2.38 g, 8.47 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride (240 mg, 339 mmol), 2M aqueous sodium carbonate solution (12.7 mL and 1,2-dimethoxyethane (100 mL) were stirred at 70°C overnight. The reaction mixture was extracted with toluene and concentrated. The obtained solid was purified by recrystallization and silica gel chromatography to obtain 1.5 g of a white solid. The white solid was identified as compound BH-Ref1 by ASAP-MS analysis (yield 36%).

[1711] Explanation of symbols

[1712] 1A, 1B…organic EL element, 2…substrate, 3…anode, 4…cathode, 5A, 5B…light-emitting region, 5…light-emitting layer, 51…first light-emitting layer, 52…second light-emitting layer, 6…hole-transport region, 61…hole-injection layer, 62…hole-transport layer, 7…electron-transport region, 71…electron-transport layer, 72…electron-injection layer.

Claims

1. A compound represented by the following general formula (1), In the general formula (1), Group consisting of R1 and R2 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 and R2 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently a substituted or unsubstituted alkyl group having 1 to 4 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, Ring A X is a ring represented by the general formula (1A-1) or (1A-2), The ring represented by the general formula (1A-1) is fused with the ring Cx at position a, The ring represented by the general formula (1A-2) is fused with the ring Cx at the position b or c, Ring B X is the ring represented by the general formula (1B-1), The ring represented by the general formula (1B-1) is fused with the ring Cx at the position d, e, f or g, The ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) are each independently bonded with or not bonded with one or more substituents represented by the following general formula (11), One or more aryl groups Ar1 are bonded to at least one of the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1). Ar1 is Substituted or unsubstituted biphenyl, Substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, 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 fluorenyl, Substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted fluoranthene group, Substituted or unsubstituted benzofluoranthenyl, or a substituted or unsubstituted perylenyl group, In the general formula (11), n 11 is 0, 1, 2, or 3, L 11 For substituted or unsubstituted phenyl, Substituted or unsubstituted biphenyl, Substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted benzanthryl, Substituted or unsubstituted phenoxy, Substituted or unsubstituted triphenylene group, substituted or unsubstituted phenalkenyl, 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 fluorenyl, Substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted fluoranthene group, Substituted or unsubstituted benzofluoranthenyl, and A divalent arylene group derived by removing one hydrogen atom from the aromatic ring of any of the substituted or unsubstituted perylene groups, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, As L 11 The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom, When n11 is 0, L 11 represents a single bond, Ar 11 is a hydrogen atom, or substituted or unsubstituted phenyl, Substituted or unsubstituted biphenyl, Substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted benzanthryl, Substituted or unsubstituted phenoxy, Substituted or unsubstituted triphenylene group, substituted or unsubstituted phenalkenyl, 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 fluorenyl, Substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted fluoranthene group, Substituted or unsubstituted benzofluoranthenyl and Any one of substituted or unsubstituted perylenyl groups, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, As Ar 11 The heterocyclic group contains at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom as a heteroatom, Indicates the bonding position.

2. The compound according to claim 1, wherein The compound represented by the general formula (1) is a compound represented by the following general formula (1C), (1D), (1E) or (1F), In the general formulae (1C), (1D), (1E) and (1F), R1 and R2 are independently the same as R1 and R2 in the general formula (1), R3~R 18 Each independently The aryl group Ar1, The substituent represented by the general formula (11), or hydrogen atoms, Among them, R3~R 18 At least one of them is the aryl group Ar1.

3. The compound according to claim 1 or 2, wherein R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

4. The compound according to any one of claims 1 to 3, wherein R1 and R2 are each independently a methyl group or an ethyl group.

5. The compound according to any one of claims 1 to 4, wherein R1 and R2 are not bonded to each other and do not form a ring.

6. The compound according to any one of claims 1 to 5, wherein The aryl group Ar1 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzanthryl group.

7. The compound according to any one of claims 1 to 6, wherein As Ar 11 One or more of the hydrogen atoms is a deuterium atom.

8. The compound according to any one of claims 1 to 7, wherein As L 11 The heterocyclic group is a substituted or unsubstituted divalent heterocyclic group having 5 to 16 ring atoms.

9. The compound according to any one of claims 1 to 8, wherein n11 is 0 or 1.

10. The compound according to any one of claims 1 to 9, wherein The substituent represented by the general formula (11) is not bonded to the ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1).

11. The compound according to any one of claims 1 to 10, wherein All groups described as "substituted or unsubstituted" are unsubstituted. 12 . An organic electroluminescent device comprising the compound according to claim 1 as a first compound.

13. The organic electroluminescent element according to claim 12, comprising anode, cathode, and an organic layer disposed between the anode and the cathode, At least one of the organic layers contains the first compound.

14. The organic electroluminescent element according to claim 13, wherein The organic layer has a light-emitting region, The light-emitting region includes a first light-emitting layer and a second light-emitting layer, The first light-emitting layer contains the first compound as a first host material.

15. The organic electroluminescent element according to claim 14, wherein The first light-emitting layer comprises a first light-emitting compound, The first light-emitting compound is a compound that emits light with a maximum peak wavelength of 500 nm or less.

16. The organic electroluminescent element according to claim 14 or 15, wherein The second light-emitting layer contains a second host material, The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 1): T1(H1)>T1(H2) ...(Mathematical formula 1).

17. The organic electroluminescent element according to any one of claims 14 to 16, wherein A hole transport layer is provided between the anode and the light emitting region.

18. The organic electroluminescent element according to any one of claims 14 to 17, wherein An electron transport layer is provided between the cathode and the light emitting region.

19. An electronic device comprising the organic electroluminescent element according to any one of claims 12 to 18.

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