Compound, organic electroluminescent element, and electronic device

Abstract

A compound represented by general formula (1). (In formula (1), Ra and Rb are heterocyclic groups or the like, ring A is a ring represented by formula (1a), at least one of R1-R4 and R9-R18 is Rx, Rx is a substituted or unsubstituted pyrenyl group or the like, at least one of R1-R4 and R9-R18 is a substituent Ry, Ry is a heterocyclic group or the like, and R1-R4 and R9-R18 other than Rx and Ry are heterocyclic groups or the like, the heterocyclic groups as Ra and Rb, the heterocyclic group as Ry, and the heterocyclic groups as R1-R4 and R9-R18 are heterocyclic groups containing only at least one atom selected from the group consisting of an oxygen atom, a sulfur atom and a silicon atom as a heteroatom, and a group consisting of two or more adjacent ones of R1-R4 and R9-R18 other than Rx and Ry do not bond to each other and do not form a ring. )

Description

Technical Field

[0001] This invention relates to compounds, organic electroluminescent elements, and electronic devices. Background Technology

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

[0003] Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime. For instance, Patent Document 1 describes research aimed at improving the performance of organic EL devices.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2019-169618 Summary of the Invention

[0007] The problem the invention aims to solve

[0008] The object of this invention is to provide novel compounds that can be used in organic electroluminescent devices. Another object of this invention is to provide compounds that can improve the device performance of organic electroluminescent devices, as well as organic electroluminescent devices containing the compounds and electronic devices equipped with the organic electroluminescent devices.

[0009] means for solving problems

[0010] According to one aspect of the present invention, a compound represented by the following general formula (1) is provided.

[0011]

Chemical Formula 1

[0012]

[0013] (In the above general formula (1),

[0014] By R a and R b Groups

[0015] They bond together to form substituted or unsubstituted monocyclic rings.

[0016] They bond together to form substituted or unsubstituted fused rings, or

[0017] are not bonded to each other,

[0018] R is not formed by the above-mentioned substituted or unsubstituted monocyclic ring and the above-mentioned substituted or unsubstituted fused ring a and R b each independently is

[0019] substituted or unsubstituted alkyl group having carbon number of 1 to 4,

[0020] substituted or unsubstituted aromatic group having ring-forming carbon number of 6 to 50, or

[0021] substituted or unsubstituted heterocyclic group having ring-forming atom number of 5 to 50,

[0022] wherein, as the above-mentioned heterocyclic group of R a and R b is a heterocyclic group containing only at least one selected from the group consisting of oxygen atom, sulfur atom and silicon atom as a hetero atom,

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

[0024] the ring represented by the above-mentioned general formula (1a) is fused with ring B of the above-mentioned general formula (1) at a, b, c or d position,

[0025] when the ring represented by the above-mentioned general formula (1a) is fused with ring B at a position, the ring represented by the above-mentioned general formula (1a) does not have R9and R 10 ,

[0026] when the ring represented by the above-mentioned general formula (1a) is fused with ring B at b position, the ring represented by the above-mentioned general formula (1a) does not have R 10 and R 11 ,

[0027] when the ring represented by the above-mentioned general formula (1a) is fused with ring B at c position, the ring represented by the above-mentioned general formula (1a) does not have R 11 and R 12 ,

[0028] when the ring represented by the above-mentioned general formula (1a) is fused with ring B at d position, the ring represented by the above-mentioned general formula (1a) does not have R 17 and R 18 ,

[0029] at least one of R1to R4and R9to R 18 is Rx,

[0030] each Rxindependently is

[0031] substituted or unsubstituted pyrenyl group,

[0032] substituted or unsubstituted benzo[a]anthracenyl group,

[0033] substituted or unsubstituted naphthobenzo furanyl group,

[0034] substituted or unsubstituted naphthobenzo furanyl group,

[0035] R1to R4and R9to R 18 at least one of R1to R4and R9to R

[0036] each of Ryis independently

[0037] substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[0038] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0039] wherein the aforementioned heterocyclic group as Ryis a heterocyclic group containing only at least any one selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom as a hetero atom,

[0040] R1to R4and R9to R 18 are each independently

[0041] a hydrogen atom,

[0042] substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0043] substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0044] substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[0045] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0046] wherein the aforementioned heterocyclic group as R1to R4and R9to R 18 is a heterocyclic group containing only at least any one selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom as a hetero atom,

[0047] a group consisting of adjacent 2 or more of R1to R4and R9to R 18 are not bonded to each other to form a ring.

[0048] According to one embodiment of the present application, there is provided an organic electroluminescent device containing a compound according to one embodiment of the present application as a first compound.

[0049] According to one embodiment of the present application, there is provided an electronic device equipped with an organic electroluminescent device according to one embodiment of the present application.

[0050] According to one embodiment of the present invention, a novel compound that can be used in an organic electroluminescent element can be provided. In addition, according to one embodiment of the present invention, a compound that can improve the element properties of an organic electroluminescent element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element can be provided. BRIEF DESCRIPTION OF DRAWINGS

[0051] Figure 1 FIG. 1 is a diagram showing the general structure of an example of an organic electroluminescent element according to one embodiment of the present invention.

[0052] Figure 2 FIG. 2 is a diagram showing the general structure of another example of an organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0053] [DEFINITIONS]

[0054] In the present specification, a hydrogen atom means to include isotopes different in the number of neutrons, i.e., protium, deuterium, and tritium.

[0055] In the present specification, in a chemical structural formula, the bondable positions of symbols such as "R" and "D" indicating a deuterium atom, which are not explicitly shown, are set to be bonded to a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom.

[0056] In the present specification, the ring-forming carbon number refers to the number of carbon atoms among atoms constituting a ring itself in a compound in which atoms are bonded in a ring shape (for example, a monocyclic compound, a fused ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon included in the substituent is not included in the ring-forming carbon number. The "ring-forming carbon number" described below is similarly set unless otherwise specified. For example, the ring-forming carbon number of a benzene ring is 6, the ring-forming carbon number of a naphthalene ring is 10, the ring-forming carbon number of a pyridine ring is 5, and the ring-forming carbon number of a furan ring is 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorene group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorene group is 25.

[0057] In addition, when an alkyl group is substituted as a substituent on a benzene ring, for example, the number of carbons of the alkyl group is not included in the ring-forming carbon number of the benzene ring. Thus, the ring-forming carbon number of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group is substituted as a substituent on a naphthalene ring, for example, the number of carbons of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Thus, the ring-forming carbon number of a naphthalene ring substituted with an alkyl group is 10.

[0058] In the present specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself in a compound having a structure in which atoms are bonded in a ring shape (e.g., monocyclic compounds, fused ring compounds, bridged ring compounds, carbocyclic compounds, and heterocyclic compounds) (e.g., monocyclic compounds, fused ring compounds, bridged ring compounds, carbocyclic compounds, and heterocyclic compounds). Atoms not constituting the ring (e.g., hydrogen atoms capping the bonds to the atoms constituting the ring), atoms contained in substituents when the ring is substituted with the substituents are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is similarly defined unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituents is not included in the number of ring-forming atoms of the pyridine ring. Thus, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6. In addition, for example, the number of hydrogen atoms bonded to the carbon atoms of the quinazoline ring or the number of atoms constituting the substituents is not included in the number of ring-forming atoms of the quinazoline ring. Thus, the number of ring-forming atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0059] In the present specification, "carbon number XX ~ YY of a ZZ group which is substituted or unsubstituted" in the expression means the carbon number of the ZZ group when it is unsubstituted, and the carbon number of the substituent is not included when substitution has occurred. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.

[0060] In the present specification, "atom number XX ~ YY of a ZZ group which is substituted or unsubstituted" in the expression means the atom number of the ZZ group when it is unsubstituted, and the atom number of the substituent is not included when substitution has occurred. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.

[0061] In the present specification, an unsubstituted ZZ group means the case where "a ZZ group which is substituted or unsubstituted" is "an unsubstituted ZZ group", and a substituted ZZ group means the case where "a ZZ group which is substituted or unsubstituted" is "a substituted ZZ group".

[0062] In the present specification, "unsubstituted" in the expression "a ZZ group which is substituted or unsubstituted" means that a hydrogen atom in the ZZ group has not been replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0063] In addition, in the present specification, "substitution" in the expression "a ZZ group which is substituted or unsubstituted" means that 1 or more hydrogen atoms in the ZZ group have been replaced with a substituent. "Substitution" in the expression "a BB group which is substituted with an AA group" also similarly means that 1 or more hydrogen atoms in the BB group have been replaced with an AA group.

[0064] "Substituent group described in the present specification"

[0065] The substituent group described in the present specification is explained below.

[0066] The ring-forming carbon number of "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.

[0067] The ring-forming atom number of "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.

[0068] The carbon number of "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.

[0069] The carbon number of "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.

[0070] The carbon number of "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.

[0071] The ring-forming carbon number of "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.

[0072] The ring-forming carbon number of "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.

[0073] The ring-forming atom number of "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.

[0074] The carbon number of "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.

[0075] • "Substituted or unsubstituted aryl group"

[0076] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in the present specification, the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) and the like can be given. (Here, the unsubstituted aryl group means the case where the "substituted or unsubstituted aryl group" is "unsubstituted aryl group", and the substituted aryl group means the case where the "substituted or unsubstituted aryl group" is "substituted aryl group".) In the present specification, only when described as "aryl group", both of "unsubstituted aryl group" and "substituted aryl group" are included.

[0077] The "substituted aryl group" means a group in which 1 or more hydrogen atoms of the "unsubstituted aryl group" have been replaced with a substituent. As the "substituted aryl group", for example, a group in which 1 or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A have been replaced with a substituent, and the examples of the substituted aryl groups of the following specific example group G1B and the like can be given. Note that the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only one example, and the "substituted aryl group" described in the present specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B has been further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted aryl group" of the following specific example group G1B has been further replaced with a substituent.

[0078] • Unsubstituted aryl groups (specific example group G1A):

[0079] phenyl,

[0080] p-biphenyl,

[0081] m-biphenyl,

[0082] o-biphenyl,

[0083] p-terphenyl-4-yl,

[0084] p-terphenyl-3-yl,

[0085] p-terphenyl-2-yl,

[0086] m-terphenyl-4-yl,

[0087] m-terphenyl-3-yl,

[0088] m-terphenyl-2-yl,

[0089] o-terphenyl-4-yl,

[0090] o-terphenyl-3-yl,

[0091] o-terphenyl-2-yl,

[0092] 1-naphthyl,

[0093] 2-naphthyl,

[0094] anthryl,

[0095] benzoanthryl,

[0096] phenanthryl,

[0097] benzo-phenanthryl,

[0098] phenalenyl,

[0099] pyrenyl,

[0100] chrysenyl,

[0101] benzo-chrysenyl,

[0102] triphenylenyl,

[0103] benzo-triphenylenyl,

[0104] tetracenyl,

[0105] pentacenyl,

[0106] fluorenyl,

[0107] 9,9'-spirobifluorenyl,

[0108] benzo-fluorenyl,

[0109] dibenzo-fluorenyl,

[0110] fluoranthenyl,

[0111] benzo-fluoranthenyl,

[0112] perylenyl, and

[0113] a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0114] [Chemical Formula 2]

[0115]

[0116] [Chemical Formula 3]

[0117]

[0118] • Substituted aryl group (Specific example group G1B):

[0119] o-tolyl,

[0120] m-tolyl,

[0121] p-tolyl,

[0122] p-xylyl,

[0123] m-xylyl group,

[0124] o-xylyl group,

[0125] p-isopropylphenyl group,

[0126] m-isopropylphenyl group,

[0127] o-isopropylphenyl group,

[0128] p-tert-butylphenyl group,

[0129] m-tert-butylphenyl group,

[0130] o-tert-butylphenyl group,

[0131] 3,4,5-trimethylphenyl group,

[0132] 9,9-dimethylfluorenyl group,

[0133] 9,9-diphenylfluorenyl group,

[0134] 9,9-bis(4-methylphenyl)fluorenyl group,

[0135] 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0136] 9,9-bis(4-tert-butylphenyl)fluorenyl group,

[0137] cyanophenyl group,

[0138] triphenylsilylphenyl group,

[0139] trimethylsilylphenyl group,

[0140] phenylnaphthyl group,

[0141] naphthylphenyl group, and

[0142] a group in which one or more hydrogen atoms of the monovalent group derived from the ring structure represented by General Formulae (TEMP-1) to (TEMP-15) described above are replaced with a substituent.

[0143] • "substituted or unsubstituted heterocyclic group"

[0144] The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom in a ring-forming atom. As specific examples of the hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom can be given.

[0145] The "heterocyclic group" described in the present specification is a monocyclic group or a fused ring group.

[0146] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0147] As specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) and the like can be given. (Here, the unsubstituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the substituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In the present specification, only the expression "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0148] The "substituted heterocyclic group" means a group in which 1 or more hydrogen atoms of the "unsubstituted heterocyclic group" have been replaced with a substituent. Specific examples of the "substituted heterocyclic group" can be given as a group in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A have been replaced, and a group in which the substituted heterocyclic groups of the following specific example group G2B have been replaced, and the like. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" given here are only one example, and the "substituted heterocyclic group" described in the present specification also includes a group in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself of the "substituted heterocyclic group" of the specific example group G2B have been further replaced with a substituent, and a group in which the hydrogen atoms of the substituents of the "substituted heterocyclic group" of the specific example group G2B have been further replaced with a substituent.

[0149] The specific example group G2A includes, for example, 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 1 hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0150] The specific example group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which 1 or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) have been replaced with a substituent (specific example group G2B4).

[0151] • unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):

[0152] a pyrrolyl group,

[0153] an imidazolyl group,

[0154] a pyrazolyl group,

[0155] Triazole group,

[0156] Tetrazolyl,

[0157] Oxazolyl,

[0158] Isoxazolyl,

[0159] Oxadiazole group,

[0160] Thiazole group,

[0161] Isothiazolyl,

[0162] Thiadiazole group,

[0163] pyridyl,

[0164] pyridazinyl,

[0165] Pyrimidine group,

[0166] Pyrazinyl,

[0167] Triazine group

[0168] Indole,

[0169] Isoindolyl,

[0170] Indazine group

[0171] Quinazine-based

[0172] Quinoline,

[0173] Isoquinoline,

[0174] Crenoline group

[0175] Phthaloazine

[0176] Quinazolinyl,

[0177] Quinoxaloyl,

[0178] Benzimidazole group,

[0179] Indazole group,

[0180] phenanthroline,

[0181] phenanthridine,

[0182] acridine group,

[0183] Phenazine group,

[0184] Carbazolyl,

[0185] Benzocarbazolyl,

[0186] Morpholinyl,

[0187] phenoxazinyl,

[0188] phenothiazinyl,

[0189] azacarbazolyl, and

[0190] diazacarbazolyl.

[0191] • unsubstituted heterocyclic groups comprising oxygen atoms (specific example group G2A2):

[0192] furanyl,

[0193] oxazolyl,

[0194] isoxazolyl,

[0195] oxadiazolyl,

[0196] xanthenyl,

[0197] benzofuranyl,

[0198] isobenzofuranyl,

[0199] dibenzofuranyl,

[0200] naphthobenzofuranyl,

[0201] benzoxazolyl,

[0202] benzisoxazolyl,

[0203] phenoxazinyl,

[0204] morpholinyl,

[0205] dinaphthofuranyl,

[0206] azadibenzofuranyl,

[0207] diazadibenzofuranyl,

[0208] azanaphthobenzofuranyl, and

[0209] diazanaphthobenzofuranyl.

[0210] • unsubstituted heterocyclic groups comprising sulfur atoms (specific example group G2A3):

[0211] thienyl,

[0212] thiazolyl,

[0213] isothiazolyl,

[0214] thiadiazolyl,

[0215] benzothienyl,

[0216] isobenzothienyl,

[0217] dibenzothienyl,

[0218] naphthobenzothienyl,

[0219] benzothiazolyl,

[0220] benzoisothiazolyl,

[0221] phenothiazinyl,

[0222] dinaphthothienyl,

[0223] azadibenzothienyl,

[0224] diazadibenzothienyl,

[0225] azanaphthobenzothienyl, and

[0226] diazanaphthobenzothienyl.

[0227] • a monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by General Formulae (TEMP-16) to (TEMP-33) below (Specific Example Group G2A4):

[0228] [Chemical Formula 4]

[0229]

[0230] [Chemical Formula 5]

[0231]

[0232] In General Formulae (TEMP-16) to (TEMP-33) above, X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.

[0233] In General Formulae (TEMP-16) to (TEMP-33) above, X A and Y AWhen at least any one of R1to R4in the above general formula (TEMP-16) to (TEMP-33) is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0234] • Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0235] (9-phenyl)carbazolyl,

[0236] (9-biphenyl)carbazolyl,

[0237] (9-phenyl)phenylcarbazolyl,

[0238] (9-naphthyl)carbazolyl,

[0239] diphenylcarbazol-9-yl,

[0240] phenylcarbazol-9-yl,

[0241] methylbenzoimidazolyl,

[0242] ethylbenzoimidazolyl,

[0243] phenyltriazinyl,

[0244] biphenyltriazinyl,

[0245] diphenyltriazinyl,

[0246] phenylquinazolinyl, and

[0247] biphenylquinazolinyl.

[0248] • Substituted heterocyclic group containing an oxygen atom (Specific example group G2B2):

[0249] phenyldibenzofuranyl,

[0250] methyldibenzofuranyl,

[0251] tert-butyldibenzofuranyl, and

[0252] a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0253] • Substituted heterocyclic group containing a sulfur atom (Specific example group G2B3):

[0254] phenyldibenzothiophenyl,

[0255] methyldibenzothiophenyl,

[0256] tert-butyldibenzothiophenyl, and

[0257] a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0258] • a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by General Formulae (TEMP-16) to (TEMP-33) described above have been replaced with a substituent (Specific Example Group G2B4):

[0259] The "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring- forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least either one of X A and Y A is NH, and the hydrogen atoms of the methylene group when one of X A and Y A is CH2.

[0260] • "substituted or unsubstituted alkyl group"

[0261] As specific examples of the "substituted or unsubstituted alkyl group" described in the present specification (Specific Example Group G3), the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B) can be given. (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, only when expressed as "alkyl group", both the "unsubstituted alkyl group" and the "substituted alkyl group" are included.

[0262] The "substituted alkyl group" refers to a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" have been replaced with a substituent. As specific examples of the "substituted alkyl group", examples of a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" (Specific Example Group G3A) described below have been replaced with a substituent, and examples of the substituted alkyl group (Specific Example Group G3B) can be given. In the present specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes both the straight-chain "unsubstituted alkyl group" and the branched-chain "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" given here are merely examples, and the "substituted alkyl group" described in the present specification also includes a group in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B have been further replaced with a substituent, and a group in which the hydrogen atoms of the substituent in the "substituted alkyl group" of Specific Example Group G3B have been further replaced with a substituent.

[0263] • unsubstituted alkyl group (Specific Example Group G3A):

[0264] methyl group,

[0265] ethyl group,

[0266] n-propyl group,

[0267] i-propyl group,

[0268] n-butyl group,

[0269] i-butyl group,

[0270] sec-butyl group, and

[0271] tert-butyl group.

[0272] • Substituted alkyl group (Specific Example Group G3B):

[0273] heptafluoropropyl group (including isomers),

[0274] pentafluoroethyl group,

[0275] 2,2,2-trifluoroethyl group, and

[0276] trifluoromethyl group.

[0277] • "Substituted or unsubstituted alkenyl group"

[0278] As specific examples of the "substituted or unsubstituted alkenyl group" described in the present specification (Specific Example Group G4), the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B) and the like can be given. (Here, the unsubstituted alkenyl group means the case where the "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and the substituted alkenyl group means the case where the "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In the present specification, only when expressed as "alkenyl group", both the "unsubstituted alkenyl group" and the "substituted alkenyl group" are included.

[0279] The "substituted alkenyl group" means a group in which 1 or more hydrogen atoms in the "unsubstituted alkenyl group" have been replaced with a substituent. As specific examples of the "substituted alkenyl group", examples of a group in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has a substituent and examples of the substituted alkenyl group (Specific Example Group G4B) and the like can be given. Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in the present specification also includes a group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B has been further replaced with a substituent and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" of Specific Example Group G4B has been further replaced with a substituent.

[0280] • Unsubstituted alkenyl group (Specific Example Group G4A):

[0281] vinyl group,

[0282] allyl group,

[0283] 1-butenyl group,

[0284] 2-butenyl group and

[0285] 3-butenyl group.

[0286] • Substituted alkenyl group (specific example group G4B):

[0287] 1,3-butadienyl group,

[0288] 1-methylethenyl group,

[0289] 1-methylallyl group,

[0290] 1,1-dimethylallyl group,

[0291] 2-methylallyl group and

[0292] 1,2-dimethylallyl group.

[0293] • "Substituted or unsubstituted alkynyl group"

[0294] As specific examples of the "substituted or unsubstituted alkynyl group" recited in the present specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) and the like can be given. (Here, the unsubstituted alkynyl group means the case where the "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) In the present specification, only when expressed as "alkynyl group", both "unsubstituted alkynyl group" and "substituted alkynyl group" are included.

[0295] The "substituted alkynyl group" means a group in which 1 or more hydrogen atoms in the "unsubstituted alkynyl group" have been replaced with a substituent group. As specific examples of the "substituted alkynyl group", a group in which 1 or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent group and the like can be given.

[0296] • Unsubstituted alkynyl group (specific example group G5A):

[0297] ethynyl group.

[0298] • "Substituted or unsubstituted cycloalkyl group"

[0299] As specific examples of the "substituted or unsubstituted cycloalkyl group" recited in the present specification (specific example group G6), the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B) and the like can be given. (Here, the unsubstituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the substituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group".) In the present specification, only when expressed as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are included.

[0300] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0301] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0302] Cyclopropyl

[0303] Cyclobutyl,

[0304] Cyclopentyl,

[0305] Cyclohexyl,

[0306] 1-Adamantyl,

[0307] 2-Adamantyl,

[0308] 1-norborneol and

[0309] 2-norborneol.

[0310] • Substituted cycloalkyl groups (specific example group G6B):

[0311] 4-Methylcyclohexyl.

[0312] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0313] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0314] -Si(G1)(G1)(G1),

[0315] -Si(G1)(G2)(G2)

[0316] -Si(G1)(G1)(G2),

[0317] -Si(G2)(G2)(G2),

[0318] -Si(G3)(G3)(G3) and

[0319] -Si(G6)(G6)(G6). Here.

[0320] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0321] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0322] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0323] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0324] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0325] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0326] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0327] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0328] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0329] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0330] ·“-O-(R 904 The group shown in the figure”

[0331] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0332] -O(G1)

[0333] -O(G2),

[0334] -O(G3) and

[0335] -O(G6).

[0336] Here,

[0337] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0338] G2 is "substituted or unsubstituted heterocyclic group" described in the group of specific examples G2.

[0339] G3 is "substituted or unsubstituted alkyl group" described in the group of specific examples G3.

[0340] G6 is "substituted or unsubstituted cycloalkyl group" described in the group of specific examples G6.

[0341] • a group represented by "-S-(R 905 ) group" described in the present specification, examples (group of specific examples G9) of which can include

[0342] • a group represented by "-S-(R 905 ) group" described in the present specification, examples (group of specific examples G9) of which can include

[0343] -S(G1),

[0344] -S(G2),

[0345] -S(G3), and

[0346] -S(G6).

[0347] Here,

[0348] G1 is "substituted or unsubstituted aryl group" described in the group of specific examples G1.

[0349] G2 is "substituted or unsubstituted heterocyclic group" described in the group of specific examples G2.

[0350] G3 is "substituted or unsubstituted alkyl group" described in the group of specific examples G3.

[0351] G6 is "substituted or unsubstituted cycloalkyl group" described in the group of specific examples G6.

[0352] • a group represented by "-N(R 906 )(R 907 ) group" described in the present specification, examples (group of specific examples G10) of which can include

[0353] • a group represented by "-N(R 906 )(R 907 ) group" described in the present specification, examples (group of specific examples G10) of which can include

[0354] -N(G1)(G1),

[0355] -N(G2)(G2),

[0356] -N(G1)(G2),

[0357] -N(G3)(G3), and

[0358] -N(G6)(G6).

[0359] In this specification,

[0360] G1 is "substituted or unsubstituted aryl" described in the specific example group G1.

[0361] G2 is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0362] G3 is "substituted or unsubstituted alkyl" described in the specific example group G3.

[0363] G6 is "substituted or unsubstituted cycloalkyl" described in the specific example group G6.

[0364] The plurality of G1 in -N(G1)(G1) are the same or different from each other.

[0365] The plurality of G2 in -N(G2)(G2) are the same or different from each other.

[0366] The plurality of G3 in -N(G3)(G3) are the same or different from each other.

[0367] The plurality of G6 in -N(G6)(G6) are the same or different from each other.

[0368] • "halogen atom"

[0369] As a specific example (specific example group G11) of the "halogen atom" described in the present specification, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and the like can be given.

[0370] • "substituted or unsubstituted fluoroalkyl group"

[0371] The "substituted or unsubstituted fluoroalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" has been replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" have been replaced with a fluorine atom (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" have been replaced with a substituent. Note that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom constituting an alkyl chain in the "substituted fluoroalkyl group" have been further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" have been further replaced with a substituent. As a specific example of the "unsubstituted fluoroalkyl group", examples in which one or more hydrogen atoms of the above "alkyl group" (specific example group G3) have been replaced with a fluorine atom, and the like can be given.

[0372] • "Substituted or unsubstituted haloalkyl group"

[0373] The "substituted or unsubstituted haloalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" has been replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" have been replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" have been replaced with a substituent. Note that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain of the "substituted haloalkyl group" have been further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent of the "substituted haloalkyl group" have been further replaced with a substituent. As specific examples of the "unsubstituted haloalkyl group", examples of a group in which one or more hydrogen atoms of the above-described "alkyl group" (specific example group G3) have been replaced with a halogen atom, and the like can be given. The haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0374] • "Substituted or unsubstituted alkoxy group"

[0375] As a specific example of the "substituted or unsubstituted alkoxy group" described in the present specification, a group represented by -O(G3) is given, where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0376] • "Substituted or unsubstituted alkylthio group"

[0377] As a specific example of the "substituted or unsubstituted alkylthio group" described in the present specification, a group represented by -S(G3) is given, where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0378] • "Substituted or unsubstituted aryloxy group"

[0379] As a specific example of the "substituted or unsubstituted aryloxy group" described in the present specification, a group represented by -O(G1) is given, where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The ring-constituting carbon number of the "unsubstituted aryloxy group" is, unless otherwise specified in the present specification, 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0380] • "substituted or unsubstituted arylthio group"

[0381] As a specific example of the "substituted or unsubstituted arylthio group" recited in the present specification, a group represented by -S(G1) is exemplified, where G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. The ring-forming carbon number of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless specifically stated otherwise in the present specification.

[0382] • "substituted or unsubstituted trialkylsilyl group"

[0383] As a specific example of the "trialkylsilyl group" recited in the present specification, a group represented by -Si(G3)(G3)(G3) is exemplified, where G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The carbon number of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless specifically stated otherwise in the present specification.

[0384] • "substituted or unsubstituted aralkyl group"

[0385] As a specific example of the "substituted or unsubstituted aralkyl group" recited in the present specification, a group represented by -(G3)-(G1) is exemplified, where G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. Thus, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced with the "aryl group" as a substituent, and is one of the "substituted alkyl groups". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with the "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless specifically stated otherwise in the present specification.

[0386] As a specific example of the "substituted or unsubstituted aralkyl group", benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-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, and the like can be given.

[0387] The substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an 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, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an 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 anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group, and the like, unless otherwise specified in the present specification.

[0388] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), 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 naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), a (9-biphenyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group, and the like, unless otherwise specified in the present specification.

[0389] In the present specification, the carbazolyl group is specifically any one of the following, unless otherwise specified in the present specification.

[0390] [Chemical Formula 6]

[0391]

[0392] In the present specification, the (9-phenyl)carbazolyl group is specifically any one of the following, unless otherwise specified in the present specification.

[0393] [Chemical Formula 7]

[0394]

[0395] In General Formulas (TEMP-Cz1) to (TEMP-Cz9) above, represents a bonding position.

[0396] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following, unless otherwise specified in the present specification.

[0397] [Chemical Formula 8]

[0398]

[0399] In General Formulae (TEMP-34) to (TEMP-41) above, represents a bonding site.

[0400] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise specified in the present specification.

[0401] • "Substituted or unsubstituted arylene"

[0402] The "substituted or unsubstituted arylene" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the aryl ring of the above "substituted or unsubstituted aryl group". As specific examples (specific example group G12) of the "substituted or unsubstituted arylene", there can be mentioned a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in the specific example group G1, and the like.

[0403] • "Substituted or unsubstituted divalent heterocyclic group"

[0404] The "substituted or unsubstituted divalent heterocyclic group" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above "substituted or unsubstituted heterocyclic group". As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", there can be mentioned a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the "substituted or unsubstituted heterocyclic group" described in the specific example group G2, and the like.

[0405] • "Substituted or unsubstituted alkylene"

[0406] The "substituted or unsubstituted alkylene" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above "substituted or unsubstituted alkyl group". As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene", there can be mentioned a divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in the specific example group G3, and the like.

[0407] The substituted or unsubstituted arylene described in the present specification is preferably any one of the groups of General Formulae (TEMP-42) to (TEMP-68), unless otherwise specified in the present specification.

[0408] [Chemical Formula 9]

[0409]

[0410] [Chemical Formula 10]

[0411]

[0412] In General Formulae (TEMP-42) to (TEMP-52) above, Q1to Q 10 each independently is a hydrogen atom or a substituent.

[0413] In General Formulae (TEMP-42) to (TEMP-52) above, represents a bonding position.

[0414] [Chemical Formula 11]

[0415]

[0416] In General Formulae (TEMP-53) to (TEMP-62) above, Q1to Q 10 each independently is a hydrogen atom or a substituent.

[0417] Q9and Q 10 may be bonded to each other via a single bond to form a ring.

[0418] In General Formulae (TEMP-53) to (TEMP-62) above, represents a bonding position.

[0419] [Chemical Formula 12]

[0420]

[0421] In General Formulae (TEMP-63) to (TEMP-68) above, Q1to Q8each independently is a hydrogen atom or a substituent.

[0422] In General Formulae (TEMP-63) to (TEMP-68) above, represents a bonding position.

[0423] The substituted or unsubstituted bivalent heterocyclic group described in the present specification is preferably any one of the groups of General Formulae (TEMP-69) to (TEMP-102) below, unless otherwise specified in the present specification.

[0424] [Chemical Formula 13]

[0425]

[0426] [Chemical Formula 14]

[0427]

[0428] [Chemical Formula 15]

[0429]

[0430] In General Formulas (TEMP-69) to (TEMP-82) above, Q1to Q9are each independently a hydrogen atom or a substituent.

[0431] [Chemical Formula 16]

[0432]

[0433] [Chemical Formula 17]

[0434]

[0435] [Chemical Formula 18]

[0436]

[0437] [Chemical Formula 19]

[0438]

[0439] In General Formulas (TEMP-83) to (TEMP-102) above, Q1to Q8are each independently a hydrogen atom or a substituent.

[0440] The above is a description of the "substituent described in the present specification".

[0441] • "case where bonded to form a ring"

[0442] In the present specification, the expression "one or more groups each 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 fused ring, or are not bonded to each other" means the case where "one or more groups each 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 each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring", and the case where "one or more groups each consisting of two or more adjacent groups are not bonded to each other".

[0443] Hereinafter, the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" in the present specification (hereinafter, these cases are sometimes collectively referred to as "case where bonded to form a ring") will be described. The case of an anthracene compound represented by the following General Formula (TEMP-103) in which the parent skeleton is an anthracene ring will be described.

[0444] [Chemical Formula 20]

[0445]

[0446] For example, in the case where "one or more groups out of two or more groups adjacent to each other are bonded to each other to form a ring" in the group represented by R 921 ~ R 930 , the group of two groups adjacent to each other as one group means a group in which R 921 and R 922 are bonded to each other to form a ring, a group in which R 922 and R 923 are bonded to each other to form a ring, a group in which R 923 and R 924 are bonded to each other to form a ring, a group in which R 924 and R 930 are bonded to each other to form a ring, a group in which R 930 and R 925 are bonded to each other to form a ring, a group in which R 925 and R 926 are bonded to each other to form a ring, a group in which R 926 and R 927 are bonded to each other to form a ring, a group in which R 927 and R 928 are bonded to each other to form a ring, a group in which R 928 and R 929 are bonded to each other to form a ring, and a group in which R 929 and R 921 are bonded to each other to form a ring.

[0447] The above "one or more groups" means that two or more groups out of the above two or more groups adjacent to each other can form a ring at the same time. For example, in the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 925 and R 926 are bonded to each other to form a ring Q B at the same time, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0448] [Chemical Formula 21]

[0449]

[0450] The case where "a group of two or more groups adjacent to each other" forms a ring includes not only the case where a group of "two" groups adjacent to each other is bonded as in the above example, but also the case where a group of "three or more" groups adjacent to each other is bonded. For example, it means that R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C, R 921 , R 922 , and R 923 ) are bonded to each other to form a ring and fused to the anthracene parent skeleton, in which case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring Q A and the ring Q C share R 922 .

[0451] [Chemical Formula 22]

[0452]

[0453] In the "monocyclic ring" or "fused ring" formed, as the structure of the ring formed alone, it can be a saturated ring or an unsaturated ring. Even in the case where "one group of the group of 2 groups adjacent to each other" forms the "monocyclic ring" or "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q A and the ring Q B are each a "monocyclic ring" or a "fused ring". In addition, in the above general formula (TEMP-105), the ring Q A and the ring Q C are "fused rings". The ring Q A of the above general formula (TEMP-105) and the ring Q C are fused to form a fused ring through the ring Q A and the ring Q C . The ring Q A of the above general formula (TEMP-104) is a monocyclic ring if it is a benzene ring. The ring Q A of the above general formula (TEMP-104) is a fused ring if it is a naphthalene ring. A A 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.

[0454] As specific examples of the aromatic hydrocarbon ring, structures in which the groups exemplified as specific examples in the specific example group G1 are capped with hydrogen atoms can be given.

[0455] As specific examples of the aromatic heterocyclic ring, structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are capped with hydrogen atoms can be given.

[0456] As specific examples of the aromatic heterocyclic ring, structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are capped with hydrogen atoms can be given.

[0457] ​As a specific example of the aliphatic hydrocarbon ring, a structure in which the group exemplified as a specific example in Group G6 is capped with a hydrogen atom can be given.

[0458] "Forming a ring" means forming a ring only from a plurality of atoms of the parent skeleton, or forming a ring from a plurality of atoms of the parent skeleton and one or more optional elements. For example, R 921 and R 922 bonded to each other to form a ring Q A means that the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more optional elements form a ring. As a specific example, in the case where R 921 and R 922 form a ring Q A , in the case where the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and 4 carbon atoms form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.

[0459] Here, the "optional element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in the present specification. In the optional element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring can be capped with a hydrogen atom or the like, or can be substituted with a "optional substituent" described later. In the case where the optional element includes an element other than a carbon element, the ring formed is a heterocycle.

[0460] The "one or more optional elements" constituting a monocyclic ring or a fused ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less, unless otherwise specified in the present specification.

[0461] The "monocyclic ring" is preferred to the "fused ring" in the present specification, unless otherwise specified.

[0462] The "saturated ring" is preferred to the "unsaturated ring" in the present specification, unless otherwise specified.

[0463] The "monocyclic ring" is preferably a benzene ring in the present specification, unless otherwise specified.

[0464] The "unsaturated ring" is preferably a benzene ring in the present specification, unless otherwise specified.

[0465] In the case of "one or more selected from the group of two or more adjacent groups mutually linked to form a substituted or unsubstituted monocyclic ring" or "one or more selected from the group of two or more adjacent groups mutually linked to form a substituted or unsubstituted fused ring", unless otherwise specified in the specification, it is preferable that one or more selected from the group of two or more adjacent groups mutually linked to form a substituted or unsubstituted "unsaturated ring" formed of a plurality of atoms of the parent skeleton and one or more and 15 or less elements selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element.

[0466] The substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent is, for example, the "optional substituent" described later. Specific examples of the substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in the specification" above.

[0467] The substituent in the case where the above "saturated ring" or "unsaturated ring" has a substituent is, for example, the "optional substituent" described later. Specific examples of the substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in the specification" above.

[0468] The above is a description of the case of "one or more selected from the group of two or more adjacent groups mutually linked to form a substituted or unsubstituted monocyclic ring" and the case of "one or more selected from the group of two or more adjacent groups mutually linked to form a substituted or unsubstituted fused ring" ("the case of linked to form a ring").

[0469] • Substituents in the case of "substituted or unsubstituted"

[0470] In one embodiment of the specification, the above substituents in the case of "substituted or unsubstituted" (in the specification, sometimes referred to as "optional substituents") are, for example, selected from the group consisting of

[0471] unsubstituted alkyl group having a carbon number of 1 to 50,

[0472] unsubstituted alkenyl group having a carbon number of 2 to 50,

[0473] unsubstituted alkynyl group having a carbon number of 2 to 50,

[0474] unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,

[0475] -Si(R 901 )(R 902 )(R 903 ),

[0476] -O-(R 904 ),

[0477] -S-(R 905 )、

[0478] -N(R 906 )(R 907 )、

[0479] a halogen atom, a cyano group, a nitro group,

[0480] an unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, and

[0481] an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms

[0482] a group selected from the group consisting of a halogen atom, a cyano group, a nitro group,

[0483] In this case, R 901 to R 907 are each independently

[0484] a hydrogen atom,

[0485] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0486] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0487] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[0488] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0489] When two or more R 901 are present, the two or more R 901 are the same or different from each other,

[0490] When two or more R 902 are present, the two or more R 902 are the same or different from each other,

[0491] When two or more R 903 are present, the two or more R 903 are the same or different from each other,

[0492] When two or more R 904 are present, the two or more R 904 are the same or different from each other,

[0493] When two or more R 905 are present, the two or more R 905 are the same or different from each other,

[0494] When two or more R 906 are present, the two or more R 906 are the same or different from each other,

[0495] In R 907 When there are two or more, the two or more R 907 are the same or different from each other.

[0496] In one embodiment, the substituent in the case where the above expression "substituted or unsubstituted" is a group selected from the group consisting of

[0497] an alkyl group having a carbon number of 1 to 50,

[0498] an aryl group having a ring-forming carbon number of 6 to 50, and

[0499] a heterocyclic group having a ring-forming atom number of 5 to 50.

[0500] In one embodiment, the substituent in the case where the above expression "substituted or unsubstituted" is a group selected from the group consisting of

[0501] an alkyl group having a carbon number of 1 to 18,

[0502] an aryl group having a ring-forming carbon number of 6 to 18, and

[0503] a heterocyclic group having a ring-forming atom number of 5 to 18.

[0504] Specific examples of each of the above optional substituents are the specific examples of the substituents described in the above item "Substituents described in the present specification".

[0505] In the present specification, unless otherwise specified, "saturated ring" or "unsaturated ring" can be formed by adjacent optional substituents to each other, preferably substituted or unsubstituted saturated five-membered ring, substituted or unsubstituted saturated six-membered ring, substituted or unsubstituted unsaturated five-membered ring, or substituted or unsubstituted unsaturated six-membered ring, more preferably benzene ring.

[0506] In the present specification, unless otherwise specified, the optional substituent can further have a substituent. As the substituent further having the optional substituent, the same as the above optional substituent.

[0507] In the present specification, the numerical range represented by "AA to BB" means a range including the lower limit value of the numerical value AA recited in front of "AA to BB" as the lower limit value and the upper limit value of the numerical value BB recited in the back of "AA to BB" as the upper limit value.

[0508] [First Embodiment]

[0509] <Compound>

[0510] One mode of the compound to which the present embodiment relates is a compound represented by the following general formula (1).

[0511] [Chemical Formula 23]

[0512]

[0513] (in the above general formula (1),

[0514] R a and R b consisting of the group of

[0515] are bonded to each other to form a substituted or unsubstituted monocyclic,

[0516] are bonded to each other to form a substituted or unsubstituted fused ring, or

[0517] are not bonded to each other,

[0518] R a and R b are not formed into the above substituted or unsubstituted monocyclic and the above substituted or unsubstituted fused ring,

[0519] substituted or unsubstituted alkyl group having a carbon number of 1 to 4,

[0520] substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or

[0521] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,

[0522] wherein the above heterocyclic group as R a and R b is a heterocyclic group containing only at least one selected from the group consisting of an oxygen atom, a sulfur atom and a silicon atom as a heteroatom,

[0523] ring A is a ring represented by the above general formula (1a),

[0524] the ring represented by the above general formula (1a) is fused to ring B of the above general formula (1) at a, b, c or d position,

[0525] when the ring represented by the above general formula (1a) is fused to ring B at a position, the ring represented by the above general formula (1a) does not have R 10 ,

[0526] when the ring represented by the above general formula (1a) is fused to ring B at b position, the ring represented by the above general formula (1a) does not have R 10 and R 11 ,

[0527] when the ring represented by the above general formula (1a) is fused to ring B at c position, the ring represented by the above general formula (1a) does not have R 11 and R 12 ,

[0528] In the case where the ring represented by General Formula (1a) is fused to the ring B at the position of d, the ring represented by General Formula (1a) does not have R 17 and R 18 ,

[0529] at least one of R1to R4and R9to R 18 is Rx,

[0530] each of Rxindependently is

[0531] a substituted or unsubstituted pyrenyl group,

[0532] a substituted or unsubstituted benzo[a]anthracenyl group,

[0533] a substituted or unsubstituted benzoxanthlenyl group, or

[0534] a substituted or unsubstituted naphthobenzofuranyl group,

[0535] at least one of R1to R4and R9to R 18 is a substituent Ry,

[0536] each of Ryindependently is

[0537] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[0538] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0539] wherein the heterocyclic group as Ryis a heterocyclic group containing only at least one selected from the group consisting of an oxygen atom, a sulfur atom and a silicon atom as a heteroatom,

[0540] each of R1to R4and R9to R 18 other than Rxand Ryindependently is

[0541] a hydrogen atom,

[0542] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0543] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0544] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[0545] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[0546] wherein the heterocyclic group as R1to R4and R9to R 18 is a heterocyclic group containing only at least one selected from the group consisting of an oxygen atom, a sulfur atom and a silicon atom as a heteroatom,

[0547] R1 to R4 and R9 to R, excluding Rx and Ry 18 (A group consisting of two or more adjacent elements does not bond with each other and therefore does not form a loop.)

[0548] In the compounds involved in this embodiment, there is at least one of Rx and Ry.

[0549] In the compounds involved in this embodiment, regarding Rx, "R1 to R4 and R9 to R 18 At least one of them is Rx”, for example, in the ring shown in the above general formula (1a) there are no R9 and R 10 In the case of (i.e., the ring shown in the above general formula (1a) fused with ring B at position a), it is interpreted as "R1~R4 and R 11 ~R 18 At least one of them is Rx". The ring shown in the above general formula (1a) does not have R. 10 and R 11 The same applies to cases such as (i.e., the case where the ring shown in the above general formula (1a) is fused with the ring B at position b).

[0550] Furthermore, regarding the compounds involved in this embodiment, "R1 to R4 and R9 to R..." 18 At least one of them is a substituent Ry”, for example, in the ring shown in the above general formula (1a) without R9 and R 10 In the case of (i.e., the ring shown in the above general formula (1a) fused with ring B at position a), it is interpreted as "R1~R4 and R 11 ~R 18 At least one of them is a substituent Ry". The ring shown in the above general formula (1a) does not have R 10 and R 11 The same applies to cases such as (i.e., the case where the ring shown in the above general formula (1a) is fused with the ring B at position b).

[0551] In the compounds involved in this embodiment, (a) is R a and R b (a) a heterocyclic group, (b) a heterocyclic group as Ry, and (c) R1-R4 and R9-R as neither substituent Rx nor substituent Ry. 18 The statement that the heterocyclic group, as a heteroatom, contains only one atom selected from oxygen, sulfur, and silicon atoms means that the heteroatom can be multiple oxygen, sulfur, or silicon atoms. Specifically, the heteroatom of the heterocyclic group in (a) to (c) above, as a cyclic atom, contains only one or more of oxygen, sulfur, and silicon atoms. It should be noted that the heteroatom of the heterocyclic group in (a) to (c) above, as a cyclic atom, does not contain nitrogen atoms.

[0552] In the compound according to the present embodiment, the heterocyclic group in (a) to (c) above is a monocyclic group, or a fused ring group.

[0553] In the compound according to the present embodiment, the heterocyclic group in (a) to (c) above is an aromatic heterocyclic group, or a non-aromatic heterocyclic group.

[0554] In the compound according to the present embodiment, as the specific examples of the "substituted or unsubstituted heterocyclic group" (specific example group G2 above), there can be mentioned a heterocyclic group having only at least one kind of hetero atom selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom among the unsubstituted heterocyclic groups (specific example group G2A above) and the substituted heterocyclic groups (specific example group G2B above) and the like. (Here, the unsubstituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is the "unsubstituted heterocyclic group", and the substituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is the "substituted heterocyclic group".) In the present specification, the case where only "heterocyclic group" is mentioned includes both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group".

[0555] In the compound according to the present embodiment, the "substituted heterocyclic group" means a group in which 1 or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced with a substituent. The specific examples of the "substituted heterocyclic group" can be mentioned a heterocyclic group having only at least one kind of hetero atom selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom among the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the specific example group G2A above are replaced, and the examples of the substituted heterocyclic groups of the specific example group G2B above and the like. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" mentioned here are only one example, and the "substituted heterocyclic group" in the compound according to the present embodiment also includes a heterocyclic group having only at least one kind of hetero atom selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom among the groups in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B above is further replaced with a substituent, and the groups in which the hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B above is further replaced with a substituent.

[0556] In the compound according to the present embodiment, the specific example group G2A is, for example, the heterocyclic groups of (i), (ii), and (iii) mentioned below.

[0557] (i) the groups having only an oxygen atom as a hetero atom among the unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2 above), and the groups having only an oxygen atom and at least one kind of atom selected from the group consisting of a sulfur atom and a silicon atom as a hetero atom.

[0558] (ii) a group containing only sulfur atom as a hetero atom among the unsubstituted heterocyclic group (Specific Example Group G2A3), and a group containing only sulfur atom and at least one selected from the group consisting of oxygen atom and silicon atom as a hetero atom.

[0559] (iii) a group derived from removing one hydrogen atom from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4), and a group containing only one selected from the group consisting of oxygen atom, sulfur atom and silicon atom as a hetero atom, and a group containing only two of them as a hetero atom.

[0560] In the compound concerned in the present embodiment, the naphthobenzofuranyl group as Rx means a monovalent group derived by removing one hydrogen atom from the naphthobenzofuran structure represented by the following general formula (Rx-1), (Rx-2) or (Rx-3).

[0561] [Chemical Formula 24]

[0562]

[0563] In the compound concerned in the present embodiment, it is preferred that at least one of R1, R4, R9, R 12 , R 13 , R 16 , R 17 and R 18 be Ry.

[0564] In the compound concerned in the present embodiment, it is preferred that at least one of R 11 , R 12 , R 13 and R 14 be Ry, and more preferred that at least one of R 11 , R 13 and R 14 be Ry.

[0565] In the compound concerned in the present embodiment, it is preferred that the above pyrenyl group be a group represented by the following general formula (1b), the above benzo[a]anthracenyl group be a group represented by the following general formula (1c), the above benzoxanthlenyl group be a group represented by the following general formula (1d), and the above naphthobenzofuranyl group be a group represented by the following general formula (1e-1), (1e-2) or (1e-3).

[0566] [Chemical Formula 25]

[0567]

[0568] (In the above general formula (1b), R 19 to R 28one of R1to R4and R9to R12bonded to any one of the bonding sites, and R 18 R1to R4and R9to R12bonded to any one of the bonding sites, and R 19 R1to R4and R9to R12bonded to any one of the bonding sites, and R 28 each independently is a hydrogen atom or a substituent,

[0569] In the above general formula (1c), R 29 R1to R4and R9to R12bonded to any one of the bonding sites, and R 40 R1to R4and R9to R12bonded to any one of the bonding sites, and R 18 R1to R4and R9to R12bonded to any one of the bonding sites, and R 29 R1to R4and R9to R12bonded to any one of the bonding sites, and R 40 each independently is a hydrogen atom or a substituent,

[0570] In the above general formula (1d), R 41 R1to R4and R9to R12bonded to any one of the bonding sites, and R 50 R1to R4and R9to R12bonded to any one of the bonding sites, and R 18 R1to R4and R9to R12bonded to any one of the bonding sites, and R 41 R1to R4and R9to R12bonded to any one of the bonding sites, and R 50 each independently is a hydrogen atom or a substituent,

[0571] In the above general formula (1e-1), (1e-2) and (1e-3), R 51 R1to R4and R9to R12bonded to any one of the bonding sites, and R 60 R1to R4and R9to R12bonded to any one of the bonding sites, and R 18 R1to R4and R9to R12bonded to any one of the bonding sites, and R 51 R1to R4and R9to R12bonded to any one of the bonding sites, and R 60 each independently is a hydrogen atom or a substituent,

[0572] the above "substituent" which is not the above bonding site, R 19 R1to R4and R9to R12bonded to any one of the bonding sites, and R 28 R1to R4and R9to R12bonded to any one of the bonding sites, and R 29 R1to R4and R9to R12bonded to any one of the bonding sites, and R 40 R1to R4and R9to R12bonded to any one of the bonding sites, and R 41 R1to R4and R9to R12bonded to any one of the bonding sites, and R 50 R1to R4and R9to R12bonded to any one of the bonding sites, and R 51 R1to R4and R9to R12bonded to any one of the bonding sites, and R 60 each independently is

[0573] unsubstituted alkyl having 1 to 50 carbons,

[0574] unsubstituted alkenyl having 2 to 50 carbons,

[0575] unsubstituted alkynyl having 2 to 50 carbons,

[0576] unsubstituted cycloalkyl having 3 to 50 ring-forming carbons,

[0577] -Si(R 901 )(R902 (R) 903 The groups shown in the figure,

[0578] -S-(R 905 The groups shown in the figure,

[0579] Halogen atoms,

[0580] Nitro,

[0581] Unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0582] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0583] Among them, R, which is not one of the aforementioned bonding sites 19 ~R 28 R that is not one of the above-mentioned bonding positions 29 ~R 40 R that is not one of the above-mentioned bonding positions 41 ~R 50 and R that is not one of the above-mentioned bonding positions 51 ~R 60 The aforementioned heterocyclic group is a heterocyclic group whose heteroatom contains only one atom selected from oxygen, sulfur, and silicon.

[0584] R 901 ~R 903 and R 905 Each independently

[0585] hydrogen atom,

[0586] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0587] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0588] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0589] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0590] Among them, as R 901 ~R 903 and R 905 The aforementioned heterocyclic group is a heterocyclic group whose heteroatom contains only one atom selected from oxygen, sulfur, and silicon.

[0591] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0592] In R 902In the case where two or more exist, two or more of R 902 are the same or different from each other,

[0593] In the case where two or more exist, two or more of R 903 In the case where two or more exist, two or more of R 903 are the same or different from each other,

[0594] In the case where two or more exist, two or more of R 905 In the case where two or more exist, two or more of R 905 are the same or different from each other.

[0595] In the case where the ring represented by the above-described general formula (1a) is fused to the ring B at the position of a, the compound represented by the above-described general formula (1) is represented by the following general formula (1A-1) or (1A-2).

[0596] In the case where the ring represented by the above-described general formula (1a) is fused to the ring B at the position of b, the compound represented by the above-described general formula (1) is represented by the following general formula (1B-1) or (1B-2).

[0597] In the case where the ring represented by the above-described general formula (1a) is fused to the ring B at the position of c, the compound represented by the above-described general formula (1) is represented by the following general formula (1C-1) or (1C-2).

[0598] In the case where the ring represented by the above-described general formula (1a) is fused to the ring B at the position of d, the compound represented by the above-described general formula (1) is represented by the following general formula (1D).

[0599] [Chemical Formula 26]

[0600]

[0601] (In the above-described general formula (1A-1) and (1A-2), R a and R b , R1to R4, and R 11 to R 18 each independently have the same meaning as R a and R b , R1to R4, and R 11 to R 18 in the above-described general formula (1).

[0602] [Chemical Formula 27]

[0603]

[0604] (In the above-described general formula (1B-1) and (1B-2), R a and R bR1to R4, R9, and R 12 R1to R4, R9, and R 18 each independently have the same meaning as R a and R b R1to R4, R9, and R 12 R1to R4, R9, and R 18 each independently have the same meaning as R

[0605] [Chemical Formula 28]

[0606]

[0607] (in the above general formula (1C-1) and (1C-2), R a and R b R1to R4, R9, R 10 , and R 13 R1to R4, R9, and R 18 each independently have the same meaning as R a and R b R1to R4, R9, R 10 , and R 13 R1to R4, R9, and R 18 each independently have the same meaning as R

[0608] [Chemical Formula 29]

[0609]

[0610] (in the above general formula (1D), R a and R b R1to R4, and R9to R 16 each independently have the same meaning as R a and R b R1to R4, and R9to R 16 each independently have the same meaning as R

[0611] In the compounds according to the present embodiment, the compound represented by the above general formula (1) is preferably a compound represented by the following general formula (1A-1), (1A-2), or (1D), and more preferably a compound represented by the following general formula (1A-2) or (1D).

[0612] [Chemical Formula 30]

[0613]

[0614] (in the above general formula (1A-1), (1A-2), and (1D), R a and R b R1to R4, and R9to R 18 each independently have the same meaning as R aand R b , R1to R4, and R9to R 18 have the same meanings.

[0615] In the compound concerned in the present embodiment, it is preferable that any one of R a and R b do not form a ring by being bonded to each other.

[0616] In the compound concerned in the present embodiment, R a and R b are each independently preferably a substituted or unsubstituted alkyl group having a carbon number of 1 to 4, and more preferably a substituted or unsubstituted methyl group.

[0617] In the compound concerned in the present embodiment, Ryis each independently preferably a substituted or unsubstituted aromatic ring-forming group having a carbon number of 6 to 18, or a substituted or unsubstituted heterocyclic ring-forming group having an atom number of 5 to 18, and more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0618] In the compound concerned in the present embodiment, Rxis preferably a substituted or unsubstituted benzo[a]anthracenyl group, a substituted or unsubstituted benzoxanthlenyl group, or a substituted or unsubstituted naphthobenzofuranyl group.

[0619] In the compound concerned in the present embodiment, Rxis also preferably a substituted or unsubstituted pyrenyl group.

[0620] In the compound concerned in the present embodiment, it is preferable that any one of R1to R4be Rx, and more preferable that R2or R3be Rx.

[0621] In the compound concerned in the present embodiment, it is also preferable that any one of R1to R4be Rxand any one of R9to R 18 be Ry, and more preferable that any one of R1to R4be Rxand any one of R 11 , R 12 , R 13 , and R 14 be Ry, and further preferable that R2or R3be Rxand any one of R 11 , R 13 , and R 14 be Ry.

[0622] In the compound concerned in the present embodiment, it is preferable that Rxand Ryeach have one.

[0623] In the compound concerned in the present embodiment, it is preferable that R1to R4and R9to R 18 other than Rxand Rybe hydrogen atoms.

[0624] In the compounds according to the present embodiment, it is preferable that the substituents described as "substituted or unsubstituted" be

[0625] a halogen atom,

[0626] an unsubstituted alkyl group having a carbon number of 1 to 25,

[0627] an unsubstituted aryl group having a ring-forming carbon number of 6 to 25, or

[0628] an unsubstituted heterocyclic group having a ring-forming atom number of 5 to 25.

[0629] In the compounds according to the present embodiment, it is preferable that the substituents described as "substituted or unsubstituted" be

[0630] an unsubstituted alkyl group having a carbon number of 1 to 10,

[0631] an unsubstituted aryl group having a ring-forming carbon number of 6 to 12, or

[0632] an unsubstituted heterocyclic group having a ring-forming atom number of 5 to 12.

[0633] In the compounds according to the present embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" above be unsubstituted.

[0634] (Method for producing the compound according to the present embodiment)

[0635] The compound according to the present embodiment can be produced according to the synthesis method described in the Examples below. In addition, the compound according to the present embodiment can also be produced by imitating this synthesis method, using known alternative reactions and starting materials corresponding to the target substance.

[0636] (Specific examples of the compound according to the present embodiment)

[0637] As specific examples of the compound according to the present embodiment, for example, the following compounds can be given. Among them, the present application is not limited to these specific examples.

[0638] [Chemical Formula 31]

[0639]

[0640] [Chemical Formula 32]

[0641]

[0642] [Chemical Formula 33]

[0643]

[0644] [Chemical Formula 34]

[0645]

[0646] [Chemical Formula 35]

[0647]

[0648] [Chemical Formula 36]

[0649]

[0650] [Chemical Formula 37]

[0651]

[0652] [Chemical Formula 38]

[0653]

[0654] [Chemical Formula 39]

[0655]

[0656] [Chemical Formula 40]

[0657]

[0658] [Chemical Formula 41]

[0659]

[0660] [Chemical Formula 42]

[0661]

[0662] [Chemical Formula 43]

[0663]

[0664] [Chemical Formula 44]

[0665]

[0666] [Chemical Formula 45]

[0667]

[0668] [Chemical Formula 46]

[0669]

[0670] [Chemical Formula 47]

[0671]

[0672] [Chemical Formula 48]

[0673]

[0674] [Chem. 49]

[0675]

[0676] [Chem. 50]

[0677]

[0678] [Chem. 51]

[0679]

[0680] [Chem. 52]

[0681]

[0682] [Chem. 53]

[0683]

[0684] [Chem. 54]

[0685]

[0686] [Chem. 55]

[0687]

[0688] [Chem. 56]

[0689]

[0690] [Chem. 57]

[0691]

[0692] [Chem. 58]

[0693]

[0694] [Chem. 59]

[0695]

[0696] [Chem. 60]

[0697]

[0698] [Chem. 61]

[0699]

[0700] [Chemical Formula 62]

[0701]

[0702] [Chemical Formula 63]

[0703]

[0704] [Chemical Formula 64]

[0705]

[0706] [Chemical Formula 65]

[0707]

[0708] [Chemical Formula 66]

[0709]

[0710] [Chemical Formula 67]

[0711]

[0712] [Chemical Formula 68]

[0713]

[0714] [Chemical Formula 69]

[0715]

[0716] [Chemical Formula 70]

[0717]

[0718] [Chemical Formula 71]

[0719]

[0720] [Chemical Formula 72]

[0721]

[0722] [Chemical Formula 73]

[0723]

[0724] [Chemical Formula 74]

[0725]

[0726] [Chemical Formula 75]

[0727]

[0728] [Chemical Formula 76]

[0729]

[0730] [Chemical Formula 77]

[0731]

[0732] [Chemical Formula 78]

[0733]

[0734] [Chemical Formula 79]

[0735]

[0736] [Chemical Formula 80]

[0737]

[0738] [Chemical Formula 81]

[0739]

[0740] [Chemical Formula 82]

[0741]

[0742] [Chemical Formula 83]

[0743]

[0744] [Chemical Formula 84]

[0745]

[0746] [Chemical Formula 85]

[0747]

[0748] [Chemical Formula 86]

[0749]

[0750] [Chemical Formula 87]

[0751]

[0752] [Chemical Formula 88]

[0753]

[0754] [Chemical Formula 89]

[0755]

[0756] [Chem 2]

[0757]

[0758] [Chem 3]

[0759]

[0760] [Chem 4]

[0761]

[0762] [Chem 5]

[0763]

[0764] [Chem 6]

[0765]

[0766] [Chem 7]

[0767]

[0768] [Chem 8]

[0769]

[0770] [Chem 9]

[0771]

[0772] [Chem 10]

[0773]

[0774] [Chem 11]

[0775]

[0776] [Chem 12]

[0777]

[0778] [Chem 13]

[0779]

[0780] [Chem 14]

[0781]

[0782] [Chem 15]

[0783]

[0784] [Chem. 104]

[0785]

[0786] [Chem. 105]

[0787]

[0788] [Chem. 106]

[0789]

[0790] [Chem. 107]

[0791]

[0792] [Chem. 108]

[0793]

[0794] [Chem. 109]

[0795]

[0796] [Chem. 110]

[0797]

[0798] [Chem. 111]

[0799]

[0800] [Chem. 112]

[0801]

[0802] [Chem. 113]

[0803]

[0804] [Chem. 114]

[0805]

[0806] [Chem. 115]

[0807]

[0808] [Chem. 116]

[0809]

[0810] [Chem. 117]

[0811]

[0812] [Chem. 118]

[0813]

[0814] [Chem. 119]

[0815]

[0816] [Chem. 120]

[0817]

[0818] [Chem. 121]

[0819]

[0820] [Chem. 122]

[0821]

[0822] [Chem. 123]

[0823]

[0824] [Chem. 124]

[0825]

[0826] [Chem. 125]

[0827]

[0828] [Chem. 126]

[0829]

[0830] [Chem. 127]

[0831]

[0832] [Chem. 128]

[0833]

[0834] [Chem. 129]

[0835]

[0836] [Chem. 130]

[0837]

[0838] [Chemical Formula 131]

[0839]

[0840] [Chemical Formula 132]

[0841]

[0842] [Chemical Formula 133]

[0843]

[0844] [Chemical Formula 134]

[0845]

[0846] [Chemical Formula 135]

[0847]

[0848] [Chemical Formula 136]

[0849]

[0850] [Chemical Formula 137]

[0851]

[0852] [Chemical Formula 138]

[0853]

[0854] [Chemical Formula 139]

[0855]

[0856] [Chemical Formula 140]

[0857]

[0858] [Chemical Formula 141]

[0859]

[0860] [Chemical Formula 142]

[0861]

[0862] [Chemical Formula 143]

[0863]

[0864] [Chemical Formula 144]

[0865]

[0866] [Chemical Formula 145]

[0867]

[0868] [Chemical Formula 146]

[0869]

[0870] [Chemical Formula 147]

[0871]

[0872] [Chemical Formula 148]

[0873]

[0874] [Chemical Formula 149]

[0875]

[0876] [Chemical Formula 150]

[0877]

[0878] [Chemical Formula 151]

[0879]

[0880] [Chemical Formula 152]

[0881]

[0882] [Chemical Formula 153]

[0883]

[0884] [Chemical Formula 154]

[0885]

[0886] [Chemical Formula 155]

[0887]

[0888] [Chemical Formula 156]

[0889]

[0890] [Chemical Formula 157]

[0891]

[0892] [Chemical Formula 158]

[0893]

[0894] [Chemical Formula 159]

[0895]

[0896] [Chemical Formula 160]

[0897]

[0898] [Chemical Formula 161]

[0899]

[0900] [Chemical Formula 162]

[0901]

[0902] [Chemical Formula 163]

[0903]

[0904] [Chemical Formula 164]

[0905]

[0906] [Chemical Formula 165]

[0907]

[0908] [Chemical Formula 166]

[0909]

[0910] [Chemical Formula 167]

[0911]

[0912] [Chemical Formula 168]

[0913]

[0914] [Chemical Formula 169]

[0915]

[0916] [Chemical Formula 170]

[0917]

[0918] [Chemical Formula 171]

[0919]

[0920] [Chemical Formula 172]

[0921]

[0922] [Chemical Formula 173]

[0923]

[0924] [Chemical Formula 174]

[0925]

[0926] [Chemical Formula 175]

[0927]

[0928] [Chemical Formula 176]

[0929]

[0930] [Chemical Formula 177]

[0931]

[0932] [Chemical Formula 178]

[0933]

[0934] [Chemical Formula 179]

[0935]

[0936] [Chemical Formula 180]

[0937]

[0938] [Chemical Formula 181]

[0939]

[0940] [Chemical Formula 182]

[0941]

[0942] [Chemical Formula 183]

[0943]

[0944] [Chemical Formula 184]

[0945]

[0946] [Chemical Formula 185]

[0947]

[0948] [Chem. 186]

[0949]

[0950] [Chem. 187]

[0951]

[0952] [Chem. 188]

[0953]

[0954] [Chem. 189]

[0955]

[0956] [Chem. 190]

[0957]

[0958] [Chem. 191]

[0959]

[0960] [Chem. 192]

[0961]

[0962] [Chem. 193]

[0963]

[0964] [Chem. 194]

[0965]

[0966] [Chem. 195]

[0967]

[0968] [Chem. 196]

[0969]

[0970] [Chem. 197]

[0971]

[0972] [Chem. 198]

[0973]

[0974] [Chem. 199]

[0975]

[0976] [Chemical Formula 200]

[0977]

[0978] [Chemical Formula 201]

[0979]

[0980] [Chemical Formula 202]

[0981]

[0982] [Chemical Formula 203]

[0983]

[0984] [Chemical Formula 204]

[0985]

[0986] [Chemical Formula 205]

[0987]

[0988] [Chemical Formula 206]

[0989]

[0990] [Chemical Formula 207]

[0991]

[0992] [Chemical Formula 208]

[0993]

[0994] [Chemical Formula 209]

[0995]

[0996] [Chemical Formula 210]

[0997]

[0998] [Chemical Formula 211]

[0999]

[1000] [Chemical Formula 212]

[1001]

[1002] [Chemical Formula 213]

[1003]

[1004] [Chemical Formula 214]

[1005]

[1006] [Chemical Formula 215]

[1007]

[1008] [Chemical Formula 216]

[1009]

[1010] [Chemical Formula 217]

[1011]

[1012] [Chemical Formula 218]

[1013]

[1014] [Chemical Formula 219]

[1015]

[1016] [Chemical Formula 220]

[1017]

[1018] [Chemical Formula 221]

[1019]

[1020] [Chemical Formula 222]

[1021]

[1022] [Chemical Formula 223]

[1023]

[1024] [Chemical Formula 224]

[1025]

[1026] [Chemical Formula 225]

[1027]

[1028] [Chemical Formula 226]

[1029]

[1030] [Chem. 227]

[1031]

[1032] [Chem. 228]

[1033]

[1034] [Chem. 229]

[1035]

[1036] [Chem. 230]

[1037]

[1038] [Chem. 231]

[1039]

[1040] [Chem. 232]

[1041]

[1042] [Chem. 233]

[1043]

[1044] [Chem. 234]

[1045]

[1046] [Chem. 235]

[1047]

[1048] [Chem. 236]

[1049]

[1050] [Chem. 237]

[1051]

[1052] [Chem. 238]

[1053]

[1054] [Chem. 239]

[1055]

[1056] [Chem. 240]

[1057]

[1058] [Chemical Formula 241]

[1059]

[1060] [Chemical Formula 242]

[1061]

[1062] [Chemical Formula 243]

[1063]

[1064] [Chemical Formula 244]

[1065]

[1066] [Chemical Formula 245]

[1067]

[1068] [Chemical Formula 246]

[1069]

[1070] [Chemical Formula 247]

[1071]

[1072] [Chemical Formula 248]

[1073]

[1074] The compound according to the present embodiment has a fused ring fluorene structure in which a ring structure is fused to fluorene, and a prescribed group such as a pyrene group is substituted as a substituent Rx to the fused fluorene structure. According to the structure of the compound according to the present embodiment, intermolecular interaction and aggregation of molecules are inhibited, and thus, by using the compound according to the present embodiment for an organic EL element, it is possible to expect improvement in element performance, for example, it is possible to reduce the driving voltage. In addition, according to one mode of the compound according to the present embodiment, it is possible to increase the lifetime of an organic EL element.

[1075] The compound according to the present embodiment is suitably used as a host material of a light-emitting layer of an organic EL element.

[1076] [Second Embodiment]

[1077] (Material for Organic Electroluminescence Element)

[1078] The material for an organic EL element according to the present embodiment contains the compound according to the first embodiment. As one mode, a material for an organic EL element containing only the compound according to the first embodiment can be given. In addition, as another mode, a material for an organic EL element containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment can be given.

[1079] In the material for an organic EL element according to the present embodiment, it is preferable that the compound according to the first embodiment be a host material. At this time, the material for an organic EL element can contain the compound according to the first embodiment as a host material and another compound such as a dopant material.

[1080] The compound according to the first embodiment is useful as a material for an organic EL element, as a material for a light-emitting layer of an organic EL element, and particularly as a host material for a blue light-emitting layer.

[1081] 〔Third Embodiment〕

[1082] (Organic Electroluminescent Element)

[1083] An organic EL element according to the present embodiment will be described.

[1084] The organic EL element according to the present embodiment contains the compound according to the first embodiment as a first compound.

[1085] The organic EL element according to the present embodiment has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer contains at least one layer formed of an organic compound. Alternatively, the organic layer is formed of a plurality of layers of an organic compound stacked. The organic layer can further contain an inorganic compound.

[1086] In the organic EL element according to the present embodiment, at least one layer of the organic layer contains the first compound (the compound according to the first embodiment).

[1087] In the organic EL element according to the present embodiment, it is preferable that the organic layer have a light-emitting region. In the organic EL element according to the present embodiment, it is preferable that the light-emitting region contain at least one light-emitting layer. In one embodiment, the light-emitting layer contains the compound represented by the above general formula (1).

[1088] In the organic EL element according to the present embodiment, it is also preferable that the organic layer have a light-emitting region, the light-emitting region contain a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contain the above first compound as a first host material.

[1089] In the case where the light-emitting region includes the first light-emitting layer and the second light-emitting layer, the organic EL element according to the present embodiment can have, for example, an anode, the first light-emitting layer, the second light-emitting layer, and a cathode in this order. Alternatively, the order of the first light-emitting layer and the second light-emitting layer can be reversed, and the organic EL element can have, for example, an anode, the second light-emitting layer, the first light-emitting layer, and a cathode in this order.

[1090] In the case where the light-emitting region includes the first light-emitting layer and the second light-emitting layer, it is also preferable that the organic EL element according to the present embodiment include the second light-emitting layer between the anode and the cathode, and the first light-emitting layer be disposed between the anode and the second light-emitting layer.

[1091] In the case where the light-emitting region includes the first light-emitting layer and the second light-emitting layer, it is also preferable that the organic EL element according to the present embodiment include the first light-emitting layer between the anode and the cathode, and the second light-emitting layer be disposed between the anode and the first light-emitting layer.

[1092] (Emission wavelength of organic EL element)

[1093] The organic EL element according to the present embodiment preferably emits light having a maximum peak wavelength of 500 nm or less at the time of element driving, and more preferably emits light having a wavelength of 430 nm or more and 480 nm or less.

[1094] The measurement of the maximum peak wavelength of light emitted from the organic EL element at the time of element driving is performed as follows. The spectrophotometric emission luminance spectrum at the time when a voltage is applied to the organic EL element such that the current density is 10 mA / cm 2 at the time of element driving is measured using a spectrophotometric emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.). In the obtained spectrophotometric emission luminance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is the maximum is determined as the maximum peak wavelength (unit: nm).

[1095] The method for measuring the maximum peak wavelength of a compound in the present specification is shown below. A toluene solution of the compound to be measured as the object of measurement at 10 -6 mol / L or more and 10 -5 mol / L or less is prepared, and a quartz cuvette is added, and the emission spectrum of the sample is measured at normal temperature (300 K) (the vertical axis is set to the emission intensity, and the horizontal axis is set to the wavelength). The emission spectrum can be measured by a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here.

[1096] In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is the maximum is determined as the emission maximum peak wavelength. Note that in the present specification, the maximum peak wavelength is sometimes referred to as the fluorescence emission maximum peak wavelength (FL-peak).

[1097] In the organic EL element of this embodiment, the organic layer may consist only of a light-emitting layer. As an organic layer, it may further have at least one layer selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[1098] In the organic EL element of this embodiment, it is preferable to have a hole transport layer between the anode and the light-emitting region.

[1099] In the organic EL element according to this embodiment, it is preferable that the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and that when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, a hole transport layer is provided between the anode and the first light-emitting layer. Furthermore, it is preferable that when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer and the first light-emitting layer, a hole transport layer is provided between the anode and the second light-emitting layer.

[1100] In the organic EL element of this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting region.

[1101] In the organic EL element according to this embodiment, it is preferable that the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and that when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, an electron transport layer is provided between the cathode and the second light-emitting layer. Furthermore, it is preferable that when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer and the first light-emitting layer, an electron transport layer is provided between the cathode and the first light-emitting layer.

[1102] Figure 1 This illustrates the general configuration of an example of an organic EL element involved in this embodiment.

[1103] 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 the cathode 4. From the anode 3 side, the organic layer 10A sequentially includes a hole transport region 6, a light-emitting region 5A, and an electron transport region 7. From the anode 3 side, the hole transport region 6 sequentially includes a hole injection layer 61 and a hole transport layer 62. The light-emitting region 5A includes a single light-emitting layer 5. From the light-emitting region 5A side, the electron transport region 7 sequentially includes an electron transport layer 71 and an electron injection layer 72.

[1104] (Emitting layer)

[1105] The light-emitting layer 5 contains the compound involved in the first embodiment.

[1106] In the organic EL element 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above general formula (1).

[1107] (Luminescent compound)

[1108] In the organic EL element 1A, the light-emitting layer 5 preferably further contains a luminescent compound (preferably a compound having fluorescent light-emitting property).

[1109] (Compound represented by general formula (5))

[1110] In one embodiment of the organic EL element 1A, the luminescent compound contained in the light-emitting layer 5 is a compound represented by the following general formula (5).

[1111]

Chemical Formula 249

[1112]

[1113] (In the above general formula (5),

[1114] one or more groups selected from the group consisting of R 501 , R 507 , and R 511 , R 517 two or more adjacent groups among the above groups

[1115] are bonded to each other to form a substituted or unsubstituted monocyclic ring,

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

[1117] are not bonded to each other,

[1118] R 501 , R 507 , and R 511 , R 517 are each independently

[1119] a hydrogen atom,

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

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

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

[1123] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,

[1124] -Si(R 901 )(R 902 )(R903 a group represented by -O- (R

[1125] a group represented by -O- (R 904 a group represented by -O- (R

[1126] a group represented by -O- (R 905 a group represented by -O- (R

[1127] a group represented by -O- (R 906 a group represented by -O- (R 907 a group represented by -O- (R

[1128] a halogen atom,

[1129] a cyano group,

[1130] a nitro group,

[1131] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or

[1132] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.

[1133] R 521 and R 522 each independently are

[1134] a hydrogen atom,

[1135] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,

[1136] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,

[1137] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,

[1138] a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,

[1139] a group represented by -Si (R 901 )(R 902 )(R 903 ),

[1140] a group represented by -O- (R 904 ),

[1141] a group represented by -S- (R 905 ),

[1142] a group represented by -N (R 906 )(R 907 ),

[1143] a halogen atom,

[1144] a cyano group,

[1145] a nitro group,

[1146] substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1147] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[1148] In the light-emitting compound (general formula (5) described above, and general formulae (62), (42-2), and (3A) described later), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , and R 907 are each independently

[1149] a hydrogen atom,

[1150] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1151] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1152] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1153] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[1154] preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1155] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

[1156] In the case where a plurality of R 901 are present, the plurality of R 901 are the same as or different from each other,

[1157] In the case where a plurality of R 902 are present, the plurality of R 902 are the same as or different from each other,

[1158] In the case where a plurality of R 903 are present, the plurality of R 903 are the same as or different from each other,

[1159] In the case where a plurality of R 904 are present, the plurality of R 904 are the same as or different from each other,

[1160] In the case where a plurality of R 905 are present, the plurality of R 905 are the same as or different from each other,

[1161] In the case where a plurality of R 906 are present, the plurality of R 906identical or different from each other,

[1162] in R 907 in the case where a plurality of exists, a plurality of R 907 identical or different from each other.

[1163] "one group selected from the group consisting of 2 or more adjacent groups of R 501 ~R 507 and R 511 ~R 517 is, for example, a group consisting of R 501 and R 502 , a group consisting of R 502 and R 503 , a group consisting of R 503 and R 504 , a group consisting of R 505 and R 506 , a group consisting of R 506 and R 507 , a group consisting of R 501 and R 502 , a group consisting of R 503 and R

[1164] In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (52).

[1165] [Chemical Formula 250]

[1166]

[1167] (in the above general formula (52),

[1168] one group selected from the group consisting of 2 or more adjacent groups of R 531 ~R 534 and R 541 ~R 544 is, for example, a group consisting of R

[1169] are bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1170] are bonded to each other to form a substituted or unsubstituted fused ring, or

[1171] are not bonded to each other,

[1172] R 531 ~R 534 , R 541 ~R 544 , R 551 and R 552 are not formed into the above substituted or unsubstituted monocyclic ring and the above substituted or unsubstituted fused ring,

[1173] a hydrogen atom,

[1174] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or

[1175] a substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms,

[1176] R 561 ~R 564 each independently is

[1177] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or

[1178] a substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms.

[1179] (a compound represented by General Formula (6))

[1180] In one embodiment of the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by General Formula (6) below.

[1181]

Chemical Formula 251

[1182]

[1183] (In General Formula (6) above,

[1184] each of the a ring, the b ring, and the c ring is independently

[1185] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or

[1186] a substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms,

[1187] R 601 and R 602 each independently does not form a substituted or unsubstituted hetero ring, or is bonded to the a ring, the b ring, or the c ring to form a substituted or unsubstituted hetero ring,

[1188] R 601 and R 602 each independently is

[1189] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1190] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1191] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1192] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1193] substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or

[1194] substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms.

[1195] In one embodiment of the organic EL element, the a ring, the b ring, and the c ring are rings (substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms) fused to the central fused 2-ring structure of the above general formula (6) composed of a boron atom and 2 nitrogen atoms.

[1196] The "aromatic hydrocarbon ring" of the a ring, the b ring, and the c ring is the same structure as a compound in which a hydrogen atom is introduced to an "aryl group".

[1197] The "aromatic hydrocarbon ring" of the a ring includes 3 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms.

[1198] The "aromatic hydrocarbon ring" of the b ring and the c ring includes 2 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms.

[1199] As specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms", there can be mentioned a compound in which a hydrogen atom is introduced to the "aryl group" described in the specific example group G1, and the like.

[1200] The "hetero ring" of the a ring, the b ring, and the c ring is the same structure as a compound in which a hydrogen atom is introduced to the above "hetero ring group".

[1201] The "hetero ring" of the a ring includes 3 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms. The "hetero ring" of the b ring and the c ring includes 2 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms. As specific examples of the "substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms", there can be mentioned a compound in which a hydrogen atom is introduced to the "hetero ring group" described in the specific example group G2, and the like.

[1202] R 601 and R 602 Each independently can be bonded to the a ring, the b ring, or the c ring to form a substituted or unsubstituted hetero ring. The hetero ring at this time includes a nitrogen atom on the central fused 2-ring structure of the above general formula (6). The hetero ring at this time can also include a hetero atom other than a nitrogen atom. 601 and R 602 The bonding to the a ring, the b ring, or the c ring specifically means that an atom constituting the a ring, the b ring, or the c ring is bonded to an atom constituting R 601 and R 602 For example, it can also be the case where R 601bonded to the a ring to form a fused ring with a nitrogen-containing heterocycle having 2 or more rings (or 3 or more rings) fused with the a ring. As specific examples of the nitrogen-containing heterocycle, compounds corresponding to the nitrogen-containing 2 or more rings fused heterocyclic groups in Group G2, and the like can be given. 601

[1203] R 601 bonded to the b ring, R 602 bonded to the a ring, and R 602 bonded to the c ring are the same as above.

[1204] R 601 and R 602 each independently can not be bonded to the a ring, the b ring, or the c ring.

[1205] In one embodiment, the a ring, the b ring, and the c ring in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons.

[1206] In one embodiment, the a ring, the b ring, and the c ring in the above general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[1207] In one embodiment, R 601 and R 602 in the above general formula (6) are each independently

[1208] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or

[1209] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[1210] preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons.

[1211] In one embodiment, the compound represented by the above general formula (6) is a compound represented by the following general formula (62).

[1212]

Chemical Formula 252

[1213]

[1214] (in the above general formula (62),

[1215] R 601A is bonded to one or more selected from R 611 and R 621 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle,

[1216] R 602A is bonded to one or more selected from R 613 and R 614 ​one or more of the bonds in the above-described substituted or unsubstituted heterocycle is a single bond,

[1217] R which does not form the above-described substituted or unsubstituted heterocycle 601A and R 602A each independently is

[1218] substituted or unsubstituted alkyl having a carbon number of 1 to 50,

[1219] substituted or unsubstituted alkenyl having a carbon number of 2 to 50,

[1220] substituted or unsubstituted alkynyl having a carbon number of 2 to 50,

[1221] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,

[1222] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50, or

[1223] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,

[1224] a group represented by R 611 to R 621 one or more groups selected from the group consisting of two or more adjacent groups among R

[1225] are bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1226] are bonded to each other to form a substituted or unsubstituted fused ring, or

[1227] are not bonded to each other,

[1228] R which does not form the above-described substituted or unsubstituted heterocycle, does not form the above-described substituted or unsubstituted monocyclic ring, and does not form the above-described substituted or unsubstituted fused ring 611 to R 621 each independently is

[1229] a hydrogen atom,

[1230] substituted or unsubstituted alkyl having a carbon number of 1 to 50,

[1231] substituted or unsubstituted alkenyl having a carbon number of 2 to 50,

[1232] substituted or unsubstituted alkynyl having a carbon number of 2 to 50,

[1233] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,

[1234] a group represented by -Si(R 901 )(R 902 )(R 903 ),

[1235] -O-(R 904 ) a group represented by

[1236] -S-(R 905 ) a group represented by

[1237] -N(R 906 )(R 907 ) a group represented by

[1238] a halogen atom,

[1239] a cyano group,

[1240] a nitro group,

[1241] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or

[1242] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[1243] R 601A and R 602A each are a group corresponding to R 601 and R 602 of the above general formula (6), respectively.

[1244] For example, R 601A and R 611 may be bonded to form a 2-ring fused (or 3-ring or more fused) nitrogen-containing heterocyclic ring having a ring including them and a benzene ring corresponding to the a ring. As a specific example of the nitrogen-containing heterocyclic ring, a compound corresponding to the 2-ring or more fused heterocyclic group containing nitrogen in the specific example group G2, and the like can be given. R 601A and R 621 may be bonded, R 602A and R 613 may be bonded, and R 602A and R 614 may be bonded are the same as above.

[1245] One or more groups in a group consisting of two or more adjacent groups among R 611 to R 621 may be

[1246] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1247] bonded to each other to form a substituted or unsubstituted fused ring.

[1248] For example, R 611 and R 612 may beThe bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[1249] In one embodiment, the compound represented by the above general formula (6) is the compound represented by the following general formula (42-2).

[1250] [Chemical Formula 253]

[1251]

[1252] (In the above general formula (42-2), R) 611 ~R 617 R 601A and R 602A Each independently relates to R in the above general formula (62) 611 ~R 617 R 601A and R 602A Same meaning

[1253] X4 is an oxygen atom or a sulfur atom.

[1254] By R 701 ~R 704 One or more groups consisting of two or more adjacent elements.

[1255] They bond together to form substituted or unsubstituted monocyclic rings.

[1256] They bond together to form substituted or unsubstituted fused rings, or

[1257] They do not bond with each other.

[1258] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 701 ~R 704 Each independently

[1259] hydrogen atom,

[1260] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1261] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1262] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1263] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1264] -Si(R 901 (R) 902 (R)903 a group represented by the formula:

[1265] -O-(R 904 a group represented by the formula:

[1266] -S-(R 905 a group represented by the formula:

[1267] -N(R 906 (R 907 ) a group represented by the formula:

[1268] a halogen atom,

[1269] a cyano group,

[1270] a nitro group,

[1271] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or

[1272] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[1273] a compound represented by the formula (3A)

[1274] In one embodiment of the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following formula (3A).

[1275]

Chemical Formula 254

[1276]

[1277] (In the above formula (3A),

[1278] one or more groups consisting of 2 or more adjacent groups selected from the group consisting of Ra 301 , Ra 302 , Ra 303 , Ra 304 , Ra 305 , Ra 306 , Ra 307 , Ra 308 , Ra 309 , and Ra 310

[1279] are bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1280] are bonded to each other to form a substituted or unsubstituted fused ring, or

[1281] are not bonded to each other,

[1282] at least one of Ra 301 to Ra 310 is a monovalent group represented by the following formula (31A),​

[1283] Ra which is not the monovalent group represented by the following general formula (31A) and which is not the above-mentioned monocyclic ring and the above-mentioned fused ring 301 ~ Ra 310 each independently is

[1284] a hydrogen atom,

[1285] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,

[1286] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,

[1287] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,

[1288] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,

[1289] a group represented by -Si(R 901 )(R 902 )(R 903 ),

[1290] a group represented by -O-(R 904 ),

[1291] a group represented by -S-(R 905 ),

[1292] a group represented by -N(R 906 )(R 907 ),

[1293] a halogen atom,

[1294] a cyano group,

[1295] a nitro group,

[1296] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or

[1297] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.

[1298] [Chemical Formula 255]

[1299]

[1300] (in the above general formula (31A),

[1301] Ara 301 and Ara 302 each independently is

[1302] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or

[1303] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[1304] La 301 , La 302 and La 303 each independently is

[1305] a single bond,

[1306] substituted or unsubstituted arylene group having 6 to 30 ring-forming carbons, or

[1307] substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms,

[1308] represents the bonding position in the pyrene ring in General Formula (3A).

[1309] (Specific examples of the light-emitting compound)

[1310] Specific examples of the light-emitting compound are described below, and these are merely examples, and the light-emitting compound is not limited to the following specific examples.

[1311] [Chemical Formula 256]

[1312]

[1313] In the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is preferably a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission of 430 nm or more and 480 nm or less. In the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is preferably a compound that exhibits fluorescent light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent light emission of 430 nm or more and 480 nm or less.

[1314] In the organic EL element 1A, in the case where the light-emitting layer 5 contains the compound according to the first embodiment and the light-emitting compound, the compound according to the first embodiment (first compound) is preferably a host material (sometimes also referred to as a matrix material), and the light-emitting compound is preferably a dopant material (sometimes also referred to as a guest material, an emitter, or a light-emitting material).

[1315] In the present specification, the "host material" is, for example, a material having a content of "50% by mass or more of the layer". Thus, for example, in the case of the organic EL element 1A, in the light-emitting layer 5, the content of the compound represented by General Formula (1A) is 50% by mass or more of the total mass of the light-emitting layer.

[1316] (Film thickness of the light-emitting layer)

[1317] The film thickness of the light-emitting layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. If the film thickness of the light-emitting layer is 5 nm or more, the light-emitting layer is easily formed, and the chromaticity is easily adjusted. If the film thickness of the light-emitting layer is 50 nm or less, the increase in driving voltage is easily suppressed.

[1318] (Content ratio of compound in light-emitting layer)

[1319] In the case where the light-emitting layer 5 contains the compound according to the first embodiment and the light-emitting compound, the content ratio of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 is, for example, each preferably in the following range.

[1320] The content ratio 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 further preferably 95% by mass or more and 99% by mass or less.

[1321] The content ratio 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 further preferably 1% by mass or more and 5% by mass or less.

[1322] The upper limit of the total content ratio of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 is 100% by mass.

[1323] Note that the present embodiment does not exclude the inclusion of a material other than the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5.

[1324] The light-emitting layer 5 can contain only one kind of the compound according to the first embodiment, or can contain two or more kinds thereof. The light-emitting layer 5 can contain only one kind of the light-emitting compound, or can contain two or more kinds thereof.

[1325] Figure 2 A schematic configuration of an example of an organic EL element according to the present embodiment is shown.

[1326] Figure 2 The organic EL element 1B shown differs from the organic EL element 1A in that the organic layer 10B includes a first light-emitting region 5B, and is otherwise the same as the organic EL element 1A. The first light-emitting region 5B includes a first light-emitting layer 51 and a second light-emitting layer 52 in this order from the anode 3 side.

[1327] The first light-emitting layer 51 contains a first compound, and the second light-emitting layer 52 contains a second compound.

[1328] (First compound)

[1329] In the organic EL element 1B, the first compound is a compound according to the first embodiment.

[1330] In the organic EL element according to the present embodiment, the first compound is preferably a compound represented by the above general formula (1).

[1331] (Second compound)

[1332] In the organic EL element 1B, the second compound is not particularly limited, and for example, a second compound represented by the following general formula (2) or the like can be given.

[1333] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the following general formula (2).

[1334]

Chemical Formula 257

[1335]

[1336] (In the above general formula (2),

[1337] R 201 ~R 208 each independently is

[1338] a hydrogen atom,

[1339] substituted or unsubstituted alkyl having a carbon number of 1 to 50,

[1340] substituted or unsubstituted haloalkyl having a carbon number of 1 to 50,

[1341] substituted or unsubstituted alkenyl having a carbon number of 2 to 50,

[1342] substituted or unsubstituted alkynyl having a carbon number of 2 to 50,

[1343] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,

[1344] -Si(R 901 )(R 902 )(R 903 ) group,

[1345] -O-(R 904 ) group,

[1346] -S-(R 905 ) group,

[1347] -N(R 906 )(R 907 ) group,

[1348] substituted or unsubstituted aralkyl having a carbon number of 7 to 50,

[1349] -C(=O)R 801 the group represented by

[1350] -COOR 802 the group represented by

[1351] a halogen atom,

[1352] a cyano group,

[1353] a nitro group,

[1354] substituted or unsubstituted aryl having 6 to 50 ring-forming carbon atoms, or

[1355] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,

[1356] L 201 and L 202 each independently is

[1357] a single bond,

[1358] substituted or unsubstituted arylene having 6 to 50 ring-forming carbon atoms, or

[1359] substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

[1360] Ar 201 and Ar 202 each independently is

[1361] substituted or unsubstituted aryl having 6 to 50 ring-forming carbon atoms, or

[1362] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[1363] (in the above-mentioned second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 each independently is

[1364] a hydrogen atom,

[1365] substituted or unsubstituted alkyl having 1 to 50 carbon atoms,

[1366] substituted or unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms,

[1367] substituted or unsubstituted aryl having 6 to 50 ring-forming carbon atoms, or

[1368] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[1369] in R 901 in the case where a plurality of R 901 are the same or different from each other,

[1370] in R 902 in the case where a plurality of R 902 are the same or different from each other,

[1371] in R 903 in the case where a plurality of R 903 are the same or different from each other,

[1372] in R 904 in the case where a plurality of R 904 are the same or different from each other,

[1373] in R 905 in the case where a plurality of R 905 are the same or different from each other,

[1374] in R 906 in the case where a plurality of R 906 are the same or different from each other,

[1375] in R 907 in the case where a plurality of R 907 are the same or different from each other,

[1376] in R 801 in the case where a plurality of R 801 are the same or different from each other,

[1377] in R 802 in the case where a plurality of R 802 are the same or different from each other.

[1378] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the following general formula (HY1) in a molecule.

[1379]

Chemical Formula 258

[1380]

[1381] (in the above general formula (HY1),

[1382] R Y1 to R Y8 and R Y11 to R Y14 are each independently

[1383] a hydrogen atom,

[1384] a halogen atom,

[1385] a cyano group,

[1386] a nitro group,

[1387] substituted or unsubstituted alkyl of carbon number 1 to 50,

[1388] substituted or unsubstituted alkenyl of carbon number 2 to 50,

[1389] substituted or unsubstituted alkynyl of carbon number 2 to 50,

[1390] substituted or unsubstituted cycloalkyl of ring-forming carbon number 3 to 50,

[1391] a group represented by -Si(R 901 )(R 902 )(R 903 ),

[1392] a group represented by -O-(R 904 ),

[1393] a group represented by -S-(R 905 ),

[1394] a group represented by -N(R 906 )(R 907 ),

[1395] substituted or unsubstituted aryl of ring-forming carbon number 6 to 50, or

[1396] substituted or unsubstituted heterocyclic group of ring-forming atom number 5 to 50,

[1397] ny is 0 or 1,

[1398] wherein,

[1399] when ny is 0, one selected from R Y1 to R Y8 is a single bond to ey,

[1400] when ny is 1, one of R Y1 and R Y2 , R Y2 and R Y3 , or R Y3 and R Y4 is a single bond to cy, and the other of R Y1 and R Y2 , R Y2 and R Y3 , or R Y3 and R Y4 is a single bond to a single bond selected from R Y5 ~R Y8 , R Y11 ~R Y14 , and a single bond other than a single bond bonded to cyand dy Y1 ~R Y4 1 of R ey

[1401] Z2is an oxygen atom or a sulfur atom,

[1402] fyrepresents a bonding position to an atom in the second compound.

[1403] In one embodiment of the organic EL element 1B, when nyin the above general formula (HY1) is 0, the group represented by the above general formula (HY1) is represented by the following general formula (HY10).

[1404] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the following general formula (HY10) in a molecule.

[1405]

Chemical Formula 259

[1406]

[1407] (In the above general formula (HY10), R Y1 ~R Y8 and Z2each have the same meaning as R Y1 ~R Y8 and Z2in the above general formula (HY1),

[1408] 1 of R Y1 ~R Y8 is a single bond bonded to ey

[1409] fyrepresents a bonding position to an atom in the second compound.

[1410] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the above general formula (HY1) in a molecule and nyis 1.

[1411] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group selected from the group consisting of the groups represented by the following general formulas (HY11), (HY12), and (HY13) in a molecule.

[1412] [Chemical Formula 260]

[1413]

[1414] (In the above general formula (HY11), (HY12), and (HY13), R Y1 ~R Y8 , R Y11 ~R Y14 and Z2each have the same meaning as R Y1 ~R Y8 , R Y11 ~R Y14 and Z2in the above general formula (HY1),

[1415] wherein one of R Y1 ~R Y8 and R Y11 ~R Y14 is a single bond to be bonded to ey,

[1416] fy indicates a bonding position to an atom in the second compound.

[1417] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the above general formula (2), and at least one group represented by the above general formula (HY1) is included in the molecule of the compound represented by the general formula (2).

[1418] In one embodiment of the organic EL element 1B, at least one of Ar 201 and Ar 202 in the above general formula (2) is a group represented by the above general formula (HY1).

[1419] In one embodiment of the organic EL element 1B, Ar 201 or Ar 202 in the above general formula (2) is a group represented by the above general formula (HY1).

[1420] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the above general formula (2), and at least one group selected from the group consisting of the groups represented by the above general formula (HY11), (HY12), and (HY13) is included in the molecule of the compound represented by the general formula (2).

[1421] In one embodiment of the organic EL element 1B, at least one of Ar 201 and Ar 202 in the above general formula (2) is any one group selected from the group consisting of the groups represented by the above general formula (HY11), (HY12), and (HY13). ​

[1422] In one embodiment of the organic EL element 1B, Ar 201 or Ar 202 is any one selected from the group consisting of groups represented by the above general formula (HY11), (HY12), and (HY13).

[1423] In one embodiment of the organic EL element 1B, the second compound has at least one group selected from the group consisting of groups represented by the above general formula (HY1), general formula (HY10), general formula (HY11), general formula (HY12), and general formula (HY13) in the molecule, whereby the excitation resistance of the second compound is improved. By using such a second compound for the second light-emitting layer, the organic EL element is easily long-lived.

[1424] In one embodiment of the organic EL element 1B, all the groups described as "substituted or unsubstituted" in the second compound are "unsubstituted" groups.

[1425] (Method for producing the second compound)

[1426] The second compound according to the present embodiment can be produced by imitating a publicly known method, or by imitating the method by using a known alternative reaction and a raw material corresponding to the target substance.

[1427] (Specific examples of the second compound)

[1428] As specific examples of the second compound according to the present embodiment, for example, the following compounds can be given. The present application is not limited to these specific examples. In the present specification, a deuterium atom is denoted as D, and a protium atom is denoted as H or omitted from the description.

[1429] [Chemical Formula 261]

[1430]

[1431] [Chemical Formula 262]

[1432]

[1433] [Chemical Formula 263]

[1434]

[1435] [Chemical Formula 264]

[1436]

[1437] [Chemical Formula 265]

[1438]

[1439] [Chem. 266]

[1440]

[1441] [Chem. 267]

[1442]

[1443] [Chem. 268]

[1444]

[1445] [Chem. 269]

[1446]

[1447] [Chem. 270]

[1448]

[1449] [Chem. 271]

[1450]

[1451] [Chem. 272]

[1452]

[1453] [Chem. 273]

[1454]

[1455] [Chem. 274]

[1456]

[1457] [Chem. 275]

[1458]

[1459] [Chem. 276]

[1460]

[1461] [Chem. 277]

[1462]

[1463] [Chem. 278]

[1464]

[1465] [Chem. 279]

[1466]

[1467] [Chemical Formula 280]

[1468]

[1469] [Chemical Formula 281]

[1470]

[1471] [Chemical Formula 282]

[1472]

[1473] [Chemical Formula 283]

[1474]

[1475] [Chemical Formula 284]

[1476]

[1477] [Chemical Formula 285]

[1478]

[1479] [Chemical Formula 286]

[1480]

[1481] [Chemical Formula 287]

[1482]

[1483] [Chemical Formula 288]

[1484]

[1485] [Chemical Formula 289]

[1486]

[1487] [Chemical Formula 290]

[1488]

[1489] [Chemical Formula 291]

[1490]

[1491] [Chemical Formula 292]

[1492]

[1493] [Chemical Formula 293]

[1494]

[1495] [Chemical Formula 294]

[1496]

[1497] [Chemical Formula 295]

[1498]

[1499] [Chemical Formula 296]

[1500]

[1501] [Chemical Formula 297]

[1502]

[1503] [Chemical Formula 298]

[1504]

[1505] [Chemical Formula 299]

[1506]

[1507] [Chemical Formula 300]

[1508]

[1509] [Chemical Formula 301]

[1510]

[1511] [Chemical Formula 302]

[1512]

[1513] [Chemical Formula 303]

[1514]

[1515] [Chemical Formula 304]

[1516]

[1517] [Chemical Formula 305]

[1518]

[1519] [Chemical Formula 306]

[1520]

[1521] [Chemical Formula 307]

[1522]

[1523] [Chemical Formula 308]

[1524]

[1525] [Chemical Formula 309]

[1526]

[1527] [Chemical Formula 310]

[1528]

[1529] [Chemical Formula 311]

[1530]

[1531] [Chemical Formula 312]

[1532]

[1533] [Chemical Formula 313]

[1534]

[1535] [Chemical Formula 314]

[1536]

[1537] [Chemical Formula 315]

[1538]

[1539] In the specific examples of the following compounds, D represents a deuterium atom, z, z1, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer of 1 or more and 8 or less, z1 is an integer of 1 or more and 9 or less, z4 to z5 are each an integer of 1 or more and 5 or less, and z6 is an integer of 1 or more and 7 or less.

[1540] [Chemical Formula 316]

[1541]

[1542] [Chemical Formula 317]

[1543]

[1544] [Chemical Formula 318]

[1545]

[1546] [Chemical Formula 319]

[1547]

[1548] [Chemical Formula 320]

[1549]

[1550] [Chemical Formula 321]

[1551]

[1552] [Chemical Formula 322]

[1553]

[1554] [Chemical Formula 323]

[1555]

[1556] (first light-emitting compound and second light-emitting compound)

[1557] In the organic EL element 1B, the first light-emitting layer 51 also preferably contains a first light-emitting compound. The first light-emitting compound is preferably a fluorescent light-emitting compound.

[1558] In the organic EL element 1B, the second light-emitting layer 52 also preferably contains a second light-emitting compound. The second light-emitting compound is preferably a fluorescent light-emitting compound.

[1559] In the case where 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 are the same or different from each other.

[1560] As the first light-emitting compound and the second light-emitting compound, the same examples as the light-emitting compounds exemplified in the organic EL element 1A can be given.

[1561] In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 is preferably a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission of 430 nm or more and 480 nm or less.

[1562] In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 is preferably a compound that exhibits fluorescent light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent light emission of 430 nm or more and 480 nm or less.

[1563] In the organic EL element 1B, in the case where 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.

[1564] In addition, in the organic EL element 1B, in the case where 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.

[1565] In the organic EL element 1B, it is preferable that the second light-emitting layer 52 contain a second host material, and that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 1).

[1566] T1(H1) > T1(H2) … (Mathematical Expression 1)

[1567] In the past, as a technique for improving the emission efficiency of an organic EL element, Triplet-Triplet-Annihilation (sometimes referred to as TTA) has been known. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. Note that, as described in International Publication No. 2010 / 134350, the TTA mechanism is sometimes referred to as a TTF mechanism.

[1568] The TTF phenomenon will be described. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As known in the past, the spin state is such that the ratio of singlet excitons is 25% and the ratio of triplet excitons is 75%. In a fluorescent element known in the past, the 25% of singlet excitons relax to the ground state to emit light, and the remaining 75% of triplet excitons do not emit light but return to the ground state through a thermal deactivation process. Therefore, it is said that the theoretical limit value of the internal quantum efficiency of the fluorescent element in the past is 25%.

[1569] On the other hand, the behavior of triplet excitons generated inside an organic substance has been theoretically studied. According to S. M. Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if it is assumed that quintet or higher order excitons immediately return to the triplet state, when the density of triplet excitons (hereinafter referred to as ) gradually increases, the triplet excitons collide with each other to undergo the reaction shown in the following formula. Here, 1 A represents the ground state, and B represents the lowest excited singlet exciton.

[1570]

[1571] That is, to become It can be predicted that of the initially generated 75% of triplet excitons, 1 / 5, or 20%, will change into singlet excitons. Therefore, the singlet excitons contributing in the form of light become 40%, which is 75% × (1 / 5) = 15% added to the initially generated 25%. At this time, the proportion of light emitted from TTF (TTF ratio) in the total luminescence intensity becomes 15 / 40, or 37.5%. Furthermore, if the initially generated 75% of triplet excitons collide with each other to generate singlet excitons (two triplet excitons generate one singlet exciton), a very high internal quantum efficiency of 62.5% can be obtained, which is 75% × (1 / 2) = 37.5% added to the initially generated 25% of singlet excitons. At this time, the TTF ratio is 37.5 / 62.5 = 60%.

[1572] According to the organic EL device of this embodiment, it can be considered that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer, even if there are excess charge carriers at the interface between the first light-emitting layer and the directly adjacent organic layer, the triplet excitons at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, if 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, if 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.

[1573] The organic EL element 1B comprises 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. The first and second light-emitting layers 51 and 52 are configured such that the triplet state energy T1(H1) of the first compound in the first light-emitting layer 51 and the triplet state energy T1(H2) of the second compound in the second light-emitting layer 52 satisfy the aforementioned mathematical formula (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. Consequently, the TTF mechanism is manifested in the second light-emitting layer 52, thereby efficiently generating singlet excitons and improving luminescence efficiency.

[1574] Thus, 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 the triplet excitons that move from the first light-emitting layer 51 and mainly exhibits the TTF mechanism as different regions. As a second compound in the second light-emitting layer 52, a compound with a smaller triplet energy than the first compound in the first light-emitting layer is used to set the triplet energy difference, thereby improving the luminous efficiency.

[1575] (triplet energy T1)

[1576] As a method of measuring the triplet energy T1, the following method can be given.

[1577] A compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) so that the concentration was 10 -5 mol / L or more and 10 -4 mol / L or less to prepare a solution, and the solution was added to a quartz cuvette as a measurement sample. For the measurement sample, a phosphorescence spectrum was measured at a low temperature (77 [K]) (the vertical axis was set to the phosphorescence emission intensity, and the horizontal axis was set to the wavelength). A tangent line was drawn for the rise on the short wavelength side of the phosphorescence spectrum, and the wavelength value λ edge [nm] based on the intersection of the tangent line and the horizontal axis was calculated as the triplet energy T1 according to the following conversion formula (F1).

[1578] Conversion formula (F1): T1 [eV] = 1239.85 / λ edge

[1579] The tangent line for the rise on the short wavelength side of the phosphorescence spectrum was drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum until the maximum value on the shortest wavelength side among the maximum values of the spectrum, the tangent line at each point on the curve was considered toward the long wavelength side. The tangent line increases in the slope as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where the value of the slope takes a maximum value (i.e., the tangent line at the inflection point) was taken as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.

[1580] Note that the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-described maximum value on the shortest wavelength side, and the tangent line drawn at the point where the value of the slope takes a maximum value closest to the maximum value on the shortest wavelength side was taken as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.

[1581] The measurement of the phosphorescence can use an F-4500-type spectrophotofluorometer main unit manufactured by Hitachi High-Technologies Corporation. Note that the measurement device is not limited thereto, and the measurement can be performed by combining a cooling device and a low-temperature container, an excitation light source, and a light-receiving device.

[1582] In the organic EL element 1B, in the case where 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 following mathematical formula (Mathematical Formula 2).

[1583] S1(H1) > S1(D3) … (Mathematical Formula 2)

[1584] (singlet energy S1)

[1585] As a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be given.

[1586] 10 -5 mol / L or more and 10 -4 mol / L or less of toluene and added to a quartz cuvette, and the absorption spectrum of the sample (the vertical axis is set to the absorption intensity, and the horizontal axis is set to the wavelength) is measured at normal temperature (300 K). A tangent line is drawn for the drop on the long wavelength side of the absorption spectrum, and the wavelength value λ edge [nm] of the intersection of the tangent line and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the singlet energy S1.

[1587] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[1588] As an absorption spectrum measuring device, for example, a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd. can be given, but is not limited thereto.

[1589] The tangent line for the drop on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectrum curve in the long wavelength direction from the maximum value on the long wavelength side among the maximum values of the absorption spectrum, the tangent line at each point on the curve is considered. The tangent line decreases in slope repeatedly and then increases as the curve drops (i.e., as the value of the vertical axis decreases). The tangent line drawn at the point where the value of the slope takes a minimum value on the long wavelength side (where cases in which the absorbance is 0.1 or less are excluded) is taken as the tangent line for the drop on the long wavelength side of the absorption spectrum.

[1590] Note that the maximum point at which the value of the absorbance is 0.2 or less is not included in the above-mentioned maximum value on the long wavelength side.

[1591] In the organic EL element 1B, in the case where 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 following mathematical formula (Mathematical Formula 3).

[1592] S1 (H2) > S1 (D4) … (Mathematical Formula 3)

[1593] The first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a phosphorescent light-emitting material (dopant material).

[1594] In addition, the first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a heavy metal complex and a phosphorescent light-emitting rare earth metal complex. Here, as the heavy metal complex, for example, iridium complexes, osmium complexes, and platinum complexes can be given.

[1595] In addition, the first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a metal complex.

[1596] (Film thickness of light-emitting layer)

[1597] The film thickness of each of the first light-emitting layer 51 and the second light-emitting layer 52 in the organic EL element 1B is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. If the film thickness of the light-emitting layer is 5 nm or more, the light-emitting layer is easily formed, and the chromaticity is easily adjusted. If the film thickness of the light-emitting layer is 50 nm or less, the increase in driving voltage is easily suppressed.

[1598] (Content ratio of compound in light-emitting layer)

[1599] In the case where the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the content ratio of each of the first compound and the first light-emitting compound in the first light-emitting layer 51 is preferably, for example, in the following range.

[1600] The content ratio 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 further preferably 95% by mass or more and 99% by mass or less.

[1601] The content ratio of the first 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 further preferably 1% by mass or more and 5% by mass or less.

[1602] The upper limit of the total content ratio of the first compound and the first light-emitting compound in the first light-emitting layer 51 is 100% by mass.

[1603] Note that the present embodiment does not exclude the inclusion of a material other than the first compound and the first light-emitting compound in the first light-emitting layer 51.

[1604] The first light-emitting layer 51 can contain only one kind of first compound, or can contain two or more kinds. The first light-emitting layer 51 can contain only one kind of first light-emitting compound, or can contain two or more kinds.

[1605] In the case where the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the content ratio of each of the second compound and the second light-emitting compound in the second light-emitting layer 52 is preferably, for example, in the following range.

[1606] The content ratio 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 further preferably 95% by mass or more and 99% by mass or less.

[1607] The content ratio of the second 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 further preferably 1% by mass or more and 5% by mass or less.

[1608] The upper limit of the total content ratio of the second compound and the second light-emitting compound in the second light-emitting layer 52 is 100% by mass.

[1609] Note that the present embodiment does not exclude a material other than the second compound and the second light-emitting compound from being contained in the second light-emitting layer 52.

[1610] The second light-emitting layer 52 can contain only one kind of second compound, or can contain two or more kinds of second compounds. The second light-emitting layer 52 can contain only one kind of second light-emitting compound, or can contain two or more kinds of second light-emitting compounds.

[1611] In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 directly adjoins the second light-emitting layer 52.

[1612] In the organic EL element 1B, in the case where the first light-emitting layer 51 directly adjoins the second light-emitting layer 52, the layer structure in which the first light-emitting layer 51 directly adjoins the second light-emitting layer 52 can include any one of the following modes (LS1), (LS2), and (LS3), for example.

[1613] (LS1) a mode in which, during a process of vapor deposition of a compound involved in the first light-emitting layer 51 and a process of vapor deposition of a compound involved in the second light-emitting layer 52, a region in which both a first compound (hereinafter sometimes referred to as a “first host material”) serving as a host material and a second compound (hereinafter sometimes referred to as a “second host material”) serving as a host material are mixed is generated, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[1614] (LS2) a mode in which, in the case where the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, during a process of vapor deposition of a compound involved in the first light-emitting layer 51 and a process of vapor deposition of a compound involved in the second light-emitting layer 52, a region in which a first host material, a second host material, and a light-emitting compound are mixed is generated, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[1615] (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 of the light-emitting compound, a region formed of the first host material, or a region formed of the second host material is generated in the process of the evaporation process of the compound involved in the first light-emitting layer 51 and the evaporation 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.

[1616] In the case where the organic EL element 1B contains the third light-emitting layer, it is preferable that the first light-emitting layer 51 directly adjoins the second light-emitting layer 52, and the second light-emitting layer 52 directly adjoins the above-described third light-emitting layer.

[1617] In the organic EL element 1B, in the case where the "second light-emitting layer 52 directly adjoins the third light-emitting layer", the layer structure of the "second light-emitting layer 52 directly adjoins the third light-emitting layer" can also contain any of the following modes (LS4), (LS5), and (LS6).

[1618] (LS4) In the process of the evaporation process of the compound involved in the second light-emitting layer 52 and the evaporation process of the compound involved in the third light-emitting layer, a region in which both the second host material and the third host material (a host material contained in the third light-emitting layer) are mixed is generated, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[1619] (LS5) In the case where the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region in which the second host material, the third host material, and the light-emitting compound are mixed is generated in the process of the evaporation process of the compound involved in the second light-emitting layer 52 and the evaporation 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.

[1620] (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 of the light-emitting compound, a region formed of the second host material, or a region formed of the third host material is generated in the process of the evaporation process of the compound involved in the second light-emitting layer 52 and the evaporation 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.

[1621] The organic EL element 1B also preferably further has a spacer layer.

[1622] In the case where the organic EL element 1B has a spacer layer, the above-described spacer layer is preferably arranged between the first light-emitting layer 51 and the second light-emitting layer 52.

[1623] (Spacer layer)

[1624] The interlayer is preferably a non-doped layer. The interlayer preferably does not contain metal atoms.

[1625] The interlayer contains an interlayer material. The interlayer material is preferably other than a light-emitting compound.

[1626] There is no particular limitation on the interlayer material, and it is preferably a material other than a light-emitting compound.

[1627] As the interlayer material, for example, there can be mentioned: 1) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 2) a fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a perylene derivative, or 3) an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative.

[1628] The interlayer material can be a compound that is one or both of a first compound contained in the first light-emitting layer 51 and a second compound contained in the second light-emitting layer 52.

[1629] In the case where the interlayer contains a plurality of interlayer materials, the content ratio of each of the interlayer materials is preferably 10% by mass or more of the total mass of the interlayer.

[1630] In the interlayer, the content of the above-described interlayer material is preferably 60% by mass or more of the total mass of the interlayer, more preferably 70% by mass or more, further preferably 80% by mass or more, even further preferably 90% by mass or more, and particularly preferably 95% by mass or more.

[1631] The interlayer can contain only one kind of interlayer material, or can contain two or more kinds of interlayer materials.

[1632] In the case where the interlayer contains two or more kinds of interlayer materials, the upper limit of the total content of the two or more kinds of interlayer materials is 100% by mass.

[1633] Note that the present embodiment does not exclude a material other than the interlayer material from being contained in the interlayer.

[1634] The interlayer can be composed of a single layer, or can be composed of two or more layers stacked.

[1635] The film thickness of the interlayer is not particularly limited, and is preferably 3 nm or more and 15 nm or less per layer, and more preferably 5 nm or more and 10 nm or less.

[1636] Further description is made on the constitution of each layer common to the organic EL element 1A and the organic EL element 1B. Hereinafter, the description of symbols is sometimes omitted.

[1637] (Substrate)

[1638] The substrate 2 is used as a support of the organic EL element. As the substrate 2, for example, glass, quartz, plastic, and the like can be used. In addition, a flexible substrate can be used. The flexible substrate refers to a substrate that can be bent (flexible). For example, a plastic substrate or the like can be given. As a material forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate, or the like can be given. In addition, an inorganic vapor deposition film can also be used.

[1639] (Anode)

[1640] The anode 3 formed on the substrate preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene, or the like can be given. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or a nitride of a metal material (for example, titanium nitride), or the like can be given.

[1641] These materials are generally formed by a sputtering method. For example, indium zinc oxide can be formed by using a target in which 1% by mass or more and 10% by mass or less of zinc oxide is added to indium oxide, using a sputtering method. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by using a target in which 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 are contained in indium oxide, using a sputtering method. In addition, it can also be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.

[1642] 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 easily injects holes regardless of the work function of the anode, and thus a material that can be used as an electrode material (for example, a metal, an alloy, a conductive compound, and a mixture thereof, and in addition, an element belonging to Group 1 or Group 2 of the periodic table) can be used.

[1643] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, and the like, as materials having a small work function. Note that when an alkali metal, an alkaline earth metal, and an alloy containing them are used to form an anode, a vacuum evaporation method or a sputtering method can be used. Further, when silver paste or the like is used, a coating method or an inkjet method can be used, for example.

[1644] (Cathode)

[1645] The cathode 4 preferably uses a metal, an alloy, a conductive compound, and the like, and a mixture thereof, each having a small work function (specifically, 3.8 eV or less). As specific examples of such a cathode material, elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them, and the like, can be given.

[1646] Note that when an alkali metal, an alkaline earth metal, and an alloy containing them are used to form a cathode, a vacuum evaporation method or a sputtering method can be used. Further, when silver paste or the like is used, a coating method or an inkjet method can be used, for example.

[1647] Note that by providing an electron injection layer, it is possible to form a cathode using Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, and the like, regardless of the size of the work function. These conductive materials can be deposited by a sputtering method, an inkjet method, a spin coating method, or the like.

[1648] (Hole injection layer)

[1649] The hole injection layer 61 is a layer containing a substance having high hole-injection property. As the substance having high hole-injection property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, and the like can be used.

[1650] Further, as a substance having high hole-injection property, 4,4',4"-tris(N,N- diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N- phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4- diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3- methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5- tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9- phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and the like aromatic amine compounds, and dinaphtho[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11- hexacarbonitrile (HAT-CN) can be given.

[1651] Further, as a substance having high hole-injection property, a high molecular compound (oligomer, dendrimer, and polymer, etc.) can be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4- diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), and the like high molecular compounds can be given. Further, poly(3,4- ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), and the like high molecular compounds to which an acid is added can be used.

[1652] (Hole transport layer)

[1653] The hole-transporting layer 62 is a layer containing a substance having a high hole-transporting property. The hole-transporting layer 62 can use an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like. Specifically, 4,4'-bis[N-(l-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[l,l'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), and the like can be used. The substances described here are mainly substances having a hole mobility of 10 -6 cm 2 (V s) or more.

[1654] The hole-transporting layer 62 can also use a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), and an anthracene derivative such as t-BuDNA, DNA, and DPAnth. A high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[1655] Note that a substance having a higher hole-transporting property than an electron-transporting property can be used as long as it is not one of the above substances. Note that the layer containing a substance having a high hole-transporting property is not necessarily formed to be a single layer, but can be formed to be a stack of two or more layers formed of the above substances.

[1656] (Specific examples of hole-transporting region materials)

[1657] As specific examples of the hole-transporting region material, the following compounds can be given, for example. Note that the present application is not limited to these specific examples of the hole-transporting region material.

[1658] [Chemical Formula 324]

[1659]

[1660] (Electron-transporting layer)

[1661] The electron transport layer 71 is a layer containing a substance having 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) high molecular compounds. Specifically, as an organic compound of a small molecule, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition, in addition to the metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can be used. In this embodiment, a benzimidazole compound can be appropriately used. The substances described here are mainly substances having an electron mobility of 10 -6 cm 2 (V·s) or more. Note that a substance other than the above can be used as the electron transport layer as long as the substance has higher electron transport properties than hole transport properties. In addition, the electron transport layer can be formed of a single layer or two or more layers of layers formed of the above substances.

[1662] In addition, a high molecular compound can be used for the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), or the like can be used.

[1663] Specific examples of the electron transport material

[1664] As specific examples of the electron transport material which can be used for the electron transport layer, the following compounds can be given, for example. Note that the present application is not limited to these specific examples of the electron transport material.

[1665] Chemical Formula 325

[1666]

[1667]

Chemical Formula 326

[1668]

[1669] (electron injection layer)

[1670] The electron injection layer 72 is a layer containing a substance having high electron injection property. The electron injection layer 72 can use alkali metals, alkaline earth metals, or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). In addition, a material in which a substance having electron transport property contains an alkali metal, an alkaline earth metal, or a compound thereof can also be used, and specifically, a material in which Alq contains magnesium (Mg) or the like can be used. Note that in this case, electron injection from the cathode can be performed more efficiently.

[1671] Alternatively, the electron injection layer 72 can use a composite material in which an organic compound and an electron donor (donor) are mixed. Such a composite material generates electrons in the organic compound by the electron donor, and thus has excellent electron injection property and electron transport property. In this case, as the organic compound, a material having excellent transport of generated electrons is preferable, and specifically, for example, the above-described substance (metal complex and heteroaromatic compound, etc.) that forms the electron transport layer can be used. As the electron donor, a substance that exhibits electron-donating property with respect to the organic compound is sufficient. Specifically, an alkali metal, an alkaline earth metal, and a rare earth metal are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. In addition, an alkali metal oxide, an alkaline earth metal oxide is preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. In addition, a Lewis base such as magnesium oxide can be used. In addition, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

[1672] (layer formation method)

[1673] As a method for forming each layer of the organic EL element of this embodiment, there is no limitation except for those specifically mentioned above, and a publicly known method such as a dry film formation method such as vacuum evaporation, sputtering, plasma, ion plating, a wet film formation method such as spin coating, dipping, flow coating, inkjet, and the like can be employed.

[1674] (film thickness)

[1675] The film thickness of each organic layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above. In general, if the film thickness is too thin, defects such as pinholes are easily generated, and if the film thickness is too thick, a high applied voltage is required, and the efficiency is poor, and thus the film thickness of each organic layer of the organic EL element is preferably in the range of several nm to 1 μm.

[1676] According to the present embodiment, it is possible to expect an improvement in the element performance of the organic electroluminescent element, for example, a reduction in the driving voltage. In addition, according to one embodiment of the organic electroluminescent element according to the present embodiment, it is possible to make the element long-lived.

[1677] [Fourth Embodiment]

[1678] (Electronic device)

[1679] The electronic device according to the present embodiment is equipped with the organic electroluminescent element according to the third embodiment. As the electronic device, for example, a display device and a light-emitting device, and the like can be given. As the display device, for example, a display component (for example, an organic EL panel module, and the like), a television, a mobile phone, a tablet, a personal computer, and the like can be given. As the light-emitting device, for example, a lighting and a vehicle lamp, and the like can be given. The light-emitting device can also be used for a display device, for example, can also be used as a backlight of a display device.

[1680] [Variation of Embodiment]

[1681] Note that the present application is not limited to the above-described embodiments, and modifications, improvements, and the like within a scope that achieves the object of the present application are included in the present application.

[1682] For example, the number of light-emitting layers of the organic EL element is not limited to one layer or two layers, and three or more light-emitting layers can be stacked. In the case where the 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) satisfy the conditions described in the above-described embodiments. For example, the other light-emitting layer can be a light-emitting layer of a fluorescent light-emitting type or a light-emitting layer of a phosphorescent light-emitting type using light emission based on an electronic transition from a triplet excited state to a ground state.

[1683] In addition, in the case where the organic EL element has a plurality of light-emitting layers, the light-emitting layers can be arranged adjacent to each other, or can be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked with an intermediate layer therebetween.

[1684] In addition, for example, a barrier layer can be arranged adjacent to at least one of the anode side and the cathode side of the light-emitting layer. It is preferable that the barrier layer be arranged in contact with the light-emitting layer to block at least any one of holes, electrons, and excitons.

[1685] For example, in the case where the barrier layer is arranged in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (for example, an electron transport layer) on the cathode side of the barrier layer. In the case where the organic EL element includes an electron transport layer, it is preferable that the barrier layer be included between the light-emitting layer and the electron transport layer.

[1686] Further, in the case where a barrier layer is provided in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching a layer (e.g., a hole-transporting layer) on the anode side of the barrier layer. In the case where the organic EL element includes a hole-transporting layer, it is preferable to include the barrier layer between the light-emitting layer and the hole-transporting layer.

[1687] Further, in order to prevent energy from leaking from the light-emitting layer to the surrounding layers, a barrier layer can be provided adjacent to the light-emitting layer. The barrier layer prevents excitons generated in the light-emitting layer from moving to a layer (e.g., an electron-transporting layer and a hole-transporting layer) on the electrode side of the barrier layer.

[1688] It is preferable that the light-emitting layer be in contact with the barrier layer.

[1689] Further, in the implementation of the present application, specific structures and shapes, and the like can be other structures and the like within a range capable of achieving the object of the present application.

[1690] Examples

[1691] Hereinafter, the present application will be further described with reference to examples. The present application is not limited by these examples.

[1692] <Compound>

[1693] Hereinafter, the structures of the compounds represented by General Formula (1) used in the production of the organic EL element related to Example 1 and Example 2 are shown.

[1694] [Chemical Formula 327]

[1695]

[1696] Hereinafter, the structures of the comparative compounds used in the production of the organic EL element related to Comparative Example 1 are shown.

[1697] [Chemical Formula 328]

[1698]

[1699] Hereinafter, the structures of other compounds used in the production of the organic EL element related to Example 1 and Example 2 and Comparative Example 1 are shown.

[1700] [Chemical Formula 329]

[1701]

[1702] [Chemical Formula 330]

[1703]

[1704] <Production of Organic EL Element>

[1705] [Example 1]

[1706] An organic EL element related to Example 1 involving a compound BH1-1 in the light-emitting layer was produced as follows.

[1707] 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 Corporation) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm.

[1708] The cleaned glass substrate with the transparent electrode line was mounted on a substrate holder of a vacuum deposition apparatus, and first, compound HA-1 was deposited on the side of the face on which the transparent electrode line was formed so as to cover the transparent electrode, forming a hole injection layer (HI) with a film thickness of 5 nm.

[1709] After the formation of the hole injection layer, compound HT-1 was deposited, forming a first hole transport layer with a film thickness of 80 nm.

[1710] After the formation of the first hole transport layer, compound HT-2 was deposited, forming a second hole transport layer (also referred to as an electron-blocking layer) with a film thickness of 10 nm.

[1711] 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-deposited so that the proportion of compound BD-1 was 2 mass%, forming a first light-emitting layer with a film thickness of 5 nm.

[1712] On the first light-emitting layer, compound BH-2 as a second compound and compound BD-1 as a second light-emitting compound were co-deposited so that the proportion of compound BD-1 was 2 mass%, forming a second light-emitting layer with a film thickness of 20 nm.

[1713] On the second light-emitting layer, compound ET-1 was deposited, forming a first electron transport layer (also referred to as a hole-blocking layer) with a film thickness of 10 nm.

[1714] On the first electron transport layer, compound ET-2 was deposited, forming a second electron transport layer with a film thickness of 15 nm.

[1715] On the second electron transport layer, LiF was deposited, forming an electron injection layer with a film thickness of 1 nm.

[1716] On the electron injection layer, metal Al was deposited, forming a cathode with a film thickness of 80 nm.

[1717] The element configuration of Example 1 is expressed in abbreviated form as shown below.

[1718] 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)

[1719] Note that the numbers in parentheses indicate film thickness (unit: nm).

[1720] Likewise, the numbers in parentheses, expressed in percentages (98%:2%), indicate the ratio (mass %) of the compound BH1-1 or the compound BH-2 to the compound BD-1 in the first light-emitting layer or the second light-emitting layer.

[1721] [Example 2]

[1722] The organic EL element according to Example 2 was produced in the same manner as in Example 1 except that the compound BH1-1 in the first light-emitting layer was changed to the compound BH1-2.

[1723] [Comparative Example 1]

[1724] The organic EL element according to Comparative Example 1 was produced in the same manner as in Example 1 except that the compound BH1-1 in the first light-emitting layer was changed to the compound BH1-Ref.

[1725] <Evaluation of Organic EL Element>

[1726] The organic EL elements produced in Examples 1 to 2 and Comparative Example 1 were subjected to the following evaluations. The evaluation results are shown in Table 1.

[1727] (Driving Voltage)

[1728] The organic EL elements produced in each example were subjected to current application between the anode and the cathode so that the current density was 10 mA / cm 2 The voltage (unit: V) at this time was measured. Table 1 shows the difference AV in the driving voltage of each example from the driving voltage of Comparative Example 1, which was calculated based on the following mathematical expression (Mathematical Expression X1).

[1729] AV = (driving voltage of each example) - (driving voltage of Comparative Example 1)... (Mathematical Expression X1)

[1730] (Lifetime LT95)

[1731] The organic EL elements produced in each example were subjected to voltage application so that the current density was 50 mA / cm 2The time (LT95 (unit: hours)) until the luminance reached 95% relative to the initial luminance was measured as the lifetime. The luminance was measured using a spectrophotometric emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.).

[1732] Table 1 shows the relative values of LT95 calculated based on the following mathematical expression (Mathematical Expression X2). The unit of the relative value of LT95 is %.

[1733] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) x 100... (Mathematical Expression X2)

[1734]

Table 1

[1735]

[1736] The organic EL elements of Examples 1 to 2 contain the compound represented by General Formula (1) as the host material of the first light-emitting layer.

[1737] As a result, the organic EL elements of Examples 1 to 2 have a driving voltage lower than that of the organic EL element of Comparative Example 1 and have a lifetime of the same degree or more.

[1738] < Evaluation of Compounds >

[1739] (triplet energy T1)

[1740] A solution was prepared by dissolving the compound to be measured in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (by volume)) so that the concentration reached 10 μmol / L, and the solution was added to a quartz cuvette as a measurement sample.

[1741] For the measurement sample, a phosphorescence spectrum was measured at low temperature (77 [K]) (the vertical axis was set to the phosphorescence emission intensity, and the horizontal axis was set to the wavelength.), a tangent line was drawn for the rise on the short wavelength side of the phosphorescence spectrum, and the wavelength value λ edge [nm] calculated based on the following conversion formula (F1) was taken as the triplet energy T1. The results are shown in Table 1.

[1742] Note that the triplet energy T1 can have an error of about 0.02 eV up or down depending on the measurement conditions.

[1743] Conversion Formula (F1): T1 [eV] = 1239.85 / λedge

[1744] The tangent line for the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. While moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum up to the maximum value on the shortest wavelength side among the maximum values of the spectrum, the tangent line at each point on the curve is considered toward the long wavelength side. The tangent line drawn at the point where the value of the slope takes a maximum value (i.e., the tangent line at the inflection point) is taken as the tangent line for the rise of the short wavelength side of the phosphorescence spectrum.

[1745] Note that the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-described maximum value on the shortest wavelength side, and the tangent line drawn at the point where the value of the slope takes a maximum value closest to the maximum value on the shortest wavelength side is taken as the tangent line for the rise of the short wavelength side of the phosphorescence spectrum.

[1746] The measurement of phosphorescence used an F-4500-type spectrophotofluorometer main unit manufactured by Hitachi High-Tech Corporation.

[1747] <SYNTHESIS EXAMPLES>

[1748] [Synthesis Example 1: Synthesis of Compound BH1-1]

[1749] Compound BH1-1 was synthesized using the following synthesis route.

[1750] [Chemical Formula 331]

[1751]

[1752] (Synthesis of Intermediate M-a)

[1753] Under a nitrogen atmosphere, 11-chloro-13,13-dimethyl-13H-indeno[l,2- ]phenanthrene (6.0 g, 18.3 mmol), DMF (N,N-dimethylformamide) (180 mL), and NBS (N-bromosuccinimide) (3.3 g, 18.3 mmol) were added to a 300 mL three-necked flask, and stirred overnight while heating at 45°C. Further, NBS (2.5 g, 13.9 mmol) was added, and stirred for 24 hours while heating at 45°C. Further, NBS (3.3 g, 18.3 mmol) was added, and stirred for 24 hours while heating at 45°C. An aqueous sodium sulfite solution was added to the reaction solution, and the precipitated solid was filtered. The obtained solid was purified using silica gel chromatography, to obtain 4.5 g of a white solid. The white solid was identified as Intermediate M-a (yield 61%) by analysis using ASAP-MS (mass spectrometry using an atmospheric pressure solid probe).

[1754] Note that ASAP-MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[1755] (Synthesis of intermediate M-b)

[1756] Under a nitrogen atmosphere, intermediate M-a (5.8 g, 14.2 mmol), benzeneboronic acid (1.73 g, 14.2 mmol), dichloro[l,l'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (232 mg, 0.284 mmol), potassium carbonate (3.93 g, 28.4 mmol), 1,2-dimethoxyethane (57 mL), and water (17 mL) were added to a 500 mL three-necked flask and refluxed for 7 hours. The reaction mixture was extracted with dichloromethane and concentrated. The resulting brown solid was purified by silica gel chromatography to obtain 4.4 g of a white solid. The white solid was identified as intermediate M-b (yield 76%) by analysis by ASAP-MS.

[1757] (Synthesis of compound BH1-1)

[1758] Under a nitrogen atmosphere, intermediate M-b (2.3 g, 5.68 mmol), pyrene-1-boronic acid (1.4 g, 5.68 mmol), Xphos Pd G4 (100 mg, 0.116 mmol), potassium carbonate (1.2 g, 8.68 mmol), 1,2-dimethoxyethane (45 mL), and water (11 mL) were added to a 100 mL three-necked flask and heated to reflux for 5 hours. Methanol was added to the reaction mixture and the precipitated solid was filtered. The resulting solid was purified by silica gel chromatography and recrystallization to obtain 2.0 g of a white solid. The white solid was identified as compound BH1-1 (yield 62%) by analysis by ASAP-MS.

[1759] [Synthesis Example 2: Synthesis of compound BH1-2]

[1760] Compound BH1-2 was synthesized using the following synthesis route.

[1761] [Chemical Formula 332]

[1762]

[1763] (Synthesis of intermediate M-c)

[1764] In a 500 mL three-necked flask, 4-phenylphenyl (10.6 g, 41.7 mmol), dichloromethane (180 mL) and bromine (6.7 g, 41.7 mmol) were added under nitrogen atmosphere and stirred overnight. Further bromine (1.5 g, 9.39 mmol) was added and stirred for 2 hours. After quenching with aqueous sodium sulfite solution, the reaction mixture was extracted with dichloromethane and concentrated. The resulting brown solid was purified by silica gel chromatography to give 7.7 g of brown solid. The brown solid was identified as intermediate M-c (yield 55%) by analysis of ASAP-MS and 2D-NMR.

[1765] (Synthesis of intermediate M-d)

[1766] In a 200 mL three-necked flask, intermediate M-c (7.7 g, 23.1 mmol), methyl 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (6.9 g, 23.1 mmol), dichloro[1,1’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (566 mg, 0.693 mmol), potassium carbonate (4.8 g, 34.7 mmol), 1,2-dimethoxyethane (62 mL) and water (15 mL) were added under nitrogen atmosphere and refluxed for 7 hours. The reaction mixture was extracted with dichloromethane and concentrated. The resulting brown solid was purified by silica gel chromatography to give 7.5 g of yellowish solid. The yellowish solid was identified as intermediate M-d (yield 77%) by analysis of ASAP-MS.

[1767] (Synthesis of intermediate M-e)

[1768] In a 200 mL three-necked flask, intermediate M-d (7.5 g, 17.7 mmol) and THF (tetrahydrofuran) (60 mL) were added under nitrogen atmosphere and stirred while ice-cooled. To this, methylmagnesium bromide (3 M in diethyl ether) (17.7 mL) was added dropwise and stirred at room temperature overnight. After quenching the reaction mixture with aqueous ammonium chloride solution, it was extracted with ethyl acetate and concentrated. The resulting brown solid 7.5 g was used as such in the next reaction without purification. The brown solid was identified as intermediate M-e by analysis of ASAP-MS.

[1769] (Synthesis of intermediate M-f)

[1770] Under a nitrogen atmosphere, a 300 mL three-necked flask was charged with intermediate M-e (7.5 g, 17.7 mmol), p-toluenesulfonic acid monohydrate (675 mg, 3.55 mmol), and toluene (120 mL), and heated to reflux for 5 hours. Further p-toluenesulfonic acid monohydrate (3.0 g, 15.8 mmol) was added, and heated to reflux for 5 hours. The reaction mixture was purified by silica gel column chromatography to give 6.0 g of a white solid. The white solid was identified as intermediate M-f (yield 82%) by analysis by ASAP-MS.

[1771] (Synthesis of compound BH1-2)

[1772] Under a nitrogen atmosphere, a 100 mL three-necked flask was charged with intermediate M-f (5.9 g, 14.5 mmol), pyrene-1-boronic acid (3.5 g, 14.2 mmol), Xphos Pd G4 (250 mg, 0.289 mmol), potassium carbonate (3.0 g, 21.7 mmol), 1,2-dimethoxyethane (120 mL), and water (30 mL), and heated to reflux for 6 hours. Methanol was added to the reaction mixture, and the precipitated solid was filtered. The resulting pale yellow solid was purified by silica gel chromatography and recrystallization to give 2.1 g of a white solid. The white solid was identified as compound BH1-2 (yield 25%) by analysis by ASAP-MS.

[1773] BRIEF DESCRIPTION OF DRAWINGS

[1774] 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-transporting region, 61 … hole-injection layer, 62 … hole-transporting layer, 7 … electron-transporting region, 71 … electron-transporting layer, 72 … electron-injection layer.

Claims

1. A compound represented by the following general formula (1), ###0001### wherein, in the general formula (1), ring B is a ring represented by the following general formula (la), ###0002### the ring represented by the general formula (la) is fused to ring B at a position of a, b, c, or d, Rx is each independently a substituted or unsubstituted group selected from the group consisting of a pyrene group, a benzo[a]anthracene group, a benzoxanthene group, and a naphthobenzofuran group, Ry is each independently a substituted or unsubstituted group selected from the group consisting of a substituted or unsubstituted aryl group having a ring- forming carbon number of 6 to 50, and a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50, and the heterocyclic group as Ry is a heterocyclic group having only at least one selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom as a heteroatom, hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50, a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.

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 (1A-1), (1A-2), or (1D), ###0003### ###0004### ###0005### consisting of R a and R b consisting of R 3. The compound according to claim 1 or 2, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0006### ###0007### ###0008### 4. The compound according to any one of claims 1 to 3, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0009### ###0010### ###0011### 5. The compound according to any one of claims 1 to 4, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1A-1), (1A-2), or (1D), ###0012### ###0013### ###0014### R is formed by the formation of said substituted or unsubstituted monocyclic ring and said substituted or unsubstituted fused ring a and R b each independently is 6. The compound according to any one of claims 1 to 5, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0015### ###0016### ###0017### 7. The compound according to any one of claims 1 to 6, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0018### ###0019### ###0020### 8. The compound according to any one of claims 1 to 7, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0021### ###0022### ###0023### wherein, as R a and R b the heterocyclic group as R is a heterocyclic group containing as a hetero atom at least any one of an oxygen atom, a sulfur atom and a silicon atom, 9. The compound according to any one of claims 1 to 8, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0024### ###0025### ###0026### 10. The compound according to any one of claims 1 to 9, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1B-1), (1B-2), or (1B-3), ###0027### ###0028### ###0029### In the case where the ring represented by the general formula (1a) is fused with the ring B at the position of a, the ring represented by the general formula (1a) does not have R9and R 10 , In the case where the ring represented by the general formula (1a) is fused with the ring B at the position of b, the ring represented by the general formula (1a) does not have R 10 and R 11 , In the case where the ring represented by the general formula (1a) is fused with the ring B at the position of c, the ring represented by the general formula (1a) does not have R 11 and R 12 , In the case where the ring represented by the general formula (1a) is fused with the ring B at the position of d, the ring represented by the general formula (1a) does not have R 17 and R 18 , R1to R4and R9to R 18 at least one of among R1to R4and R9to R ​ ​ ​ ​ ​ R1to R4and R9to R 18 at least one of R1to R4and R9to R ​ ​ ​ ​ R1to R4and R9to R11except Rxand Ry 18 each independently is ​ ​ ​ ​ ​ wherein the heterocyclic group as R1to R4and R9to R 18 is a heterocyclic group containing at least any one atom selected from an oxygen atom, a sulfur atom and a silicon atom as a heteroatom, R1to R4and R9to R10other than Rxand Ry 18 a group consisting of 2 or more adjacent groups selected from the group consisting of R1to R4and R9to R10other than Rxand Ryis not bonded to each other and does not form a ring. ​ R1, R4, R9, R 12 , R 13 , R 16 , R 17 and R 18 are each independently H or Ry. ​ R 11 , R 13 , and at least one of R 14 is Ry. ​ ​ ​ ​ ​ In the general formula (1b), R 19 ~R 28 one of which is a bonding site bonded at any one of positions of R1to R4and R9to R 18 R1to R4and R9to R 19 ~R 28 each independently is a hydrogen atom or a substituent, In the general formula (1c), R 29 ~R 40 one of R 18 ~R 29 ~R 40 each independently is a hydrogen atom or a substituent, In the general formula (1d), R 41 ~R 50 one of which is a bonding site bonded at any one of positions of R1to R4and R9to R 18 R1to R4and R9to R 41 ~R 50 each independently is a hydrogen atom or a substituent, In the general formula (1e-1), (1e-2), and (1e-3), R 51 ~R 60 one of which is a bonding site that bonds at any one of positions of R1to R4and R9to R 18 R1to R4and R9to R 51 ~R 60 each independently is a hydrogen atom or a substituent, R which is not the bonding site 19 ~R 28 R which is not the bonding site 29 ~R 40 R which is not the bonding site 41 ~R 50 R which is not the bonding site 51 ~R 60 each independently ​ ​ ​ ​ -Si(R 901 )(R 902 )(R 903 ) shown in the formula (1), -S-(R 905 ) a group represented by formula: ​ ​ ​ ​ wherein R 19 ~R 28 , R 29 ~R 40 , R 41 ~R 50 , and R 51 ~R 60 which are not the bonding site are each independently a heterocyclic group having a heteroatom selected from the group consisting of an oxygen atom, a sulfur atom, and a silicon atom, R 901 ~R 903 and R 905 each independently is ​ ​ ​ ​ ​ wherein the heterocyclic group as R 901 ~R 903 and R 905 is a heterocyclic group having at least any one atom selected from an oxygen atom, a sulfur atom and a silicon atom as a heteroatom, In R 901 In case there are 2 or more, the 2 or more R 901 are the same or different from each other, In R 902 In the case where two or more R 902 are the same or different from each other, In R 903 In case there are 2 or more, the 2 or more R 903 are the same or different from each other, In R 905 In case of 2 or more, the 2 or more R 905 are the same or different from each other. ​ ​ In the general formulae (1A-1), (1A-2) and (1D), the meanings of R a and R b , R1to R4, and R9to R 18 are each independently the same as the meanings of R a and R b , R1to R4, and R9to R 18 in the general formula (1). ​ consisting of R a and R b are not bonded to each other to form a ring. ​ R a and R b each independently is substituted or unsubstituted alkyl of carbo n number 1 to 4. ​ R a and R b each independently is substituted or unsubstituted methyl. ​ ​ ​ ​ 10. The compound according to any one of claims 1 to 9, wherein each Ryis independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted dibenzofuranyl.

11. The compound according to any one of claims 1 to 10, wherein Rxis substituted or unsubstituted benzo[a]anthracenyl, substituted or unsubstituted benzoxanthlenyl, or substituted or unsubstituted naphthobenzofuranyl.

12. The compound according to any one of claims 1 to 11, wherein any one of R1to R4is Rx.

13. The compound according to any one of claims 1 to 12, wherein R2or R3is Rx.

14. The compound according to any one of claims 1 to 13, wherein any one of R1to R4is Rx, and any one of R9to R 18 is Ry.

15. The compound according to any one of claims 1 to 14, wherein any one of R1to R4is Rx, and R 11 , R 13 , and any one of R 14 is Ry.

16. The compound according to any one of claims 1 to 15, wherein R2or R3is Rx, and R 11 , R 13 , and R 14 is Ry.

17. The compound according to any one of claims 1 to 16, wherein each of Rxand Ryhas 1.

18. The compound according to any one of claims 1 to 17, wherein R1to R4and R9to R11except Rxand Ryare each a hydrogen atom. 18 are each a hydrogen atom.

19. The compound according to any one of claims 1 to 18, wherein all of the groups set as "substituted or unsubstituted" are unsubstituted.

20. An organic electroluminescent device comprising the compound according to any one of claims 1 to 19 as a first compound.

21. The organic electroluminescent device according to claim 20, which has an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers contains the first compound.

22. The organic electroluminescent device according to claim 21, 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.

23. The organic electroluminescent device according to claim 22, wherein the first light-emitting layer includes a first light-emitting compound, the first light-emitting compound is a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less.

24. The organic electroluminescent device according to claim 22 or 23, wherein the second light-emitting layer contains a second host material, a triplet energy T1(H1) of the first host material and a triplet energy T1(H2) of the second host material satisfy the following mathematical formula (Mathematical Formula 1), T1(H1) > T1(H2)... (Mathematical Formula 1).

25. The organic electroluminescent device according to any one of claims 22 to 24, wherein a hole-transporting layer is provided between the anode and the light-emitting region.

26. The organic electroluminescent device according to any one of claims 22 to 25, wherein an electron-transporting layer is provided between the cathode and the light-emitting region.

27. An electronic device equipped with the organic electroluminescent device according to any one of claims 20 to 26.

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