Organic electroluminescent element and electronic device using the same

Abstract

The compound represented by the following formula (A1) (R 1 ~R 7 , R 10 ~R 16 , R 21 and R 22 At least one of the atoms is a deuterium atom or a group having a deuterium atom). #imgabs0#

Description

Technical Field

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

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

[0003] Patent Documents 1 to 3 disclose the use of a compound having a specific fused ring structure as a material for a light-emitting layer of an organic EL device.

[0004] Prior art literature

[0005] Patent Literature

[0006] [Patent Document 1] International Publication No. 2018 / 151065

[0007] [Patent Document 2] International Publication No. 2017 / 175690

[0008] [Patent document 3] US10249832. Summary of the Invention

[0009] An object of the present invention is to provide a novel compound useful as a material for an organic EL device, an organic EL device with a long life, and an electronic device using the organic EL device.

[0010] According to the present invention, the following compounds, organic EL devices, and electronic devices can be provided.

[0011] 1. A compound represented by the following formula (A1).

[0012] [Chemistry 1]

[0013]

[0014] (In formula (A1),

[0015] R1~R7 and R 10 ~R 16 One or more adjacent two or more groups are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0016] R 21 and R 22 , R1 to R7 that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring, and R that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 10 ~R 16Each independently

[0017] hydrogen atoms, or

[0018] Substituent R.

[0019] The aforementioned substituent R is

[0020] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0021] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0022] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0023] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0024] -Si(R 901 )(R 902 )(R 903 ),

[0025] -O-(R 904 ),

[0026] -S-(R 905 ),

[0027] -N(R 906 )(R 907 ),

[0028] Halogen atoms, cyano, nitro,

[0029] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0030] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0031] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0032] R 901 ~R 907 Each independently

[0033] hydrogen atoms,

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

[0035] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0036] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0037] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0038] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0039] The hydrogen atoms of the substituted or unsubstituted saturated or unsaturated ring formed above,

[0040] When the substituted or unsubstituted saturated or unsaturated ring formed above is substituted, a hydrogen atom possessed by the substituent,

[0041] R as a hydrogen atom 21 and R 22 、

[0042] R1~R7 and R as hydrogen atoms 10 ~R 16 ,as well as

[0043] R as the aforementioned substituent R 21 、R 22 , R1~R7 and R 10 ~R 16 The hydrogen atoms

[0044] At least one of them is a deuterium atom.)

[0045] 2. A material for an organic electroluminescent device comprising the compound represented by the above formula (A1).

[0046] 3. An organic electroluminescent element having a cathode,

[0047] Anode, and

[0048] at least one organic layer disposed between the cathode and the anode,

[0049] At least one of the at least one organic layer contains the compound represented by the above formula (A1).

[0050] 4. An organic electroluminescent element having a cathode,

[0051] Anode, and

[0052] at least one organic layer disposed between the cathode and the anode,

[0053] The at least one organic layer comprises a light-emitting layer,

[0054] The light-emitting layer contains the compound represented by the above formula (A1) and the compound represented by the following formula (10).

[0055] [Chemistry 2]

[0056]

[0057] [In formula (10),

[0058] R 101 ~R 110 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring.

[0059] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 101 ~R 110 Each independently

[0060] hydrogen atoms,

[0061] Substituent R, or

[0062] A group represented by the following formula (11).

[0063] -L 101 -Ar 101 (11)

[0064] (In formula (11),

[0065] L 101 for

[0066] single bond,

[0067] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0068] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0069] Ar 101 for

[0070] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0071] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0072] The aforementioned substituent R is

[0073] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0074] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0075] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0076] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0077] -Si(R 901 )(R 902 )(R 903 ),

[0078] -O-(R 904 ),

[0079] -S-(R 905 ),

[0080] -N(R 906 )(R 907 ),

[0081] Halogen atoms, cyano groups, nitro groups,

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

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

[0084] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0085] R 901 ~R 907 Each independently

[0086] hydrogen atoms,

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

[0088] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0089] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0090] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0091] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0092] Among them, R does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 101 ~R 110 At least one of the groups is a group represented by the aforementioned formula (11). When there are two or more groups represented by the aforementioned formula (11), the two or more groups represented by the aforementioned formula (11) may be the same or different.]

[0093] 5. An electronic device comprising the organic electroluminescent element according to 3 or 4 above.

[0094] According to the present invention, a novel compound useful as a material for an organic EL device, an organic EL device with a long life, and an electronic device using the organic EL device can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0095] [ Figure 1 ] A diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0096] [definition]

[0097] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0098] In the present specification, in chemical structural formulas, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a position capable of bonding that is not explicitly indicated by symbols such as "R" or "D" representing a deuterium atom.

[0099] In this specification, the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded to form a ring structure. When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below shall also be the same unless otherwise specified. For example, the number of ring carbon atoms of a benzene ring is 6, the number of ring carbon atoms of a naphthalene ring is 10, the number of ring carbon atoms of a pyridine ring is 5, and the number of ring carbon atoms of a furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0100] Furthermore, when a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of a naphthalene ring substituted with an alkyl group is 10.

[0101] In this specification, the number of ring atoms refers to the number of atoms that constitute the ring itself in a compound (such as a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded to form a cyclic structure (such as a monocyclic ring, a condensed ring, and a ring assembly). Atoms that do not constitute a ring (such as hydrogen atoms that terminate the bonds of atoms that constitute the ring) and atoms contained in substituents when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" described below shall also be the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms that constitute the substituents are not included in the number of atoms that form the pyridine ring. Therefore, the number of ring atoms of a pyridine ring to which hydrogen atoms or substituents are bonded is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0102] In this specification, "carbon number XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" refers to the number of carbon atoms in the ZZ group when it is unsubstituted and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0103] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" indicates the number of atoms in the ZZ group when it is unsubstituted and does not include the number of atoms in the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0104] In this specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0105] In the present specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atom of the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0106] In this specification, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms of the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms of the BB group are replaced by an AA group.

[0107] "Substituents described in this specification"

[0108] The substituents described in this specification are described below.

[0109] Unless otherwise specified in the present specification, the “unsubstituted aryl group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0110] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0111] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0112] Unless otherwise specified in the present specification, the "unsubstituted alkenyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0113] Unless otherwise specified in the present specification, the "unsubstituted alkynyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0114] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0115] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0116] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0117] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0118] ・"Substituted or unsubstituted aryl group"

[0119] Specific examples of "substituted or unsubstituted aryl groups" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Herein, "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" alone includes both "unsubstituted aryl groups" and "substituted aryl groups."

[0120] A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by a substituent. Examples of "substituted aryl groups" include groups in which one or more hydrogen atoms of the "unsubstituted aryl groups" described in Specific Example Group G1A below are replaced by substituents, and examples of substituted aryl groups described in Specific Example Group G1B below are mentioned. The examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced by a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" described in Specific Example Group G1B below is further replaced by a substituent.

[0121] ・Unsubstituted aryl group (Specific example group G1A):

[0122] Phenyl,

[0123] p-Biphenyl,

[0124] m-Biphenyl,

[0125] o-biphenyl,

[0126] 4-terphenyl-4-yl,

[0127] 4-terphenyl-3-yl,

[0128] 4-terphenyl-2-yl,

[0129] m-terphenyl-4-yl,

[0130] m-terphenyl-3-yl,

[0131] m-terphenyl-2-yl,

[0132] o-terphenyl-4-yl,

[0133] o-terphenyl-3-yl,

[0134] o-terphenyl-2-yl,

[0135] 1-naphthyl,

[0136] 2-naphthyl,

[0137] Anthracene,

[0138] Benzanthryl,

[0139] Fiki,

[0140] Triphenylene,

[0141] Phenalene,

[0142] Pyrene base,

[0143] phenanthera,

[0144] Benzophenone,

[0145] triphenylene,

[0146] Benzotriphenylene,

[0147] tetraphenyl,

[0148] Pentaphenyl,

[0149] Fluorenyl,

[0150] 9,9'-spirobifluorenyl,

[0151] Benzofluorenyl,

[0152] Dibenzofluorenyl,

[0153] Fluoranthene group,

[0154] Benzofluoranthene,

[0155] Perylene, and

[0156] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0157] [Chemistry 3]

[0158]

[0159] [Chemistry 4]

[0160]

[0161] ・Substituted aryl (Specific example group G1B):

[0162] o-Tolyl,

[0163] m-Tolyl,

[0164] p-Tolyl,

[0165] p-Xylyl,

[0166] m-xylyl,

[0167] o-xylyl,

[0168] p-Isopropylphenyl,

[0169] m-isopropylphenyl,

[0170] o-isopropylphenyl,

[0171] tert-Butylphenyl,

[0172] m-tert-butylphenyl,

[0173] o-tert-butylphenyl,

[0174] 3,4,5-trimethylphenyl,

[0175] 9,9-dimethylfluorenyl,

[0176] 9,9-diphenylfluorenyl,

[0177] 9,9-bis(4-methylphenyl)fluorenyl,

[0178] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0179] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0180] Cyanophenyl,

[0181] triphenylsilylphenyl,

[0182] trimethylsilylphenyl,

[0183] Phenyl naphthyl,

[0184] naphthylphenyl, and

[0185] A group in which one or more hydrogen atoms of the monovalent group derived from the ring structure represented by the general formulae (TEMP-1) to (TEMP-15) are replaced by a substituent.

[0186] ・"Substituted or unsubstituted heterocyclic group"

[0187] The term "heterocyclic group" as used herein refers to a cyclic group containing at least one heteroatom among the ring atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0188] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0189] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0190] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (Specific Example Group G2) include the following unsubstituted heterocyclic groups (Specific Example Group G2A) and substituted heterocyclic groups (Specific Example Group G2B). (Herein, "unsubstituted heterocyclic group" refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups."

[0191] A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic groups" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of Specific Example Group G2A below are replaced, and examples of substituted heterocyclic groups of Specific Example Group G2B below are mentioned. Furthermore, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring atom of the heterocyclic group itself in the "substituted heterocyclic group" of Specific Example Group G2B is further replaced by a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" of Specific Example Group G2B is further replaced by a substituent.

[0192] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0193] Specific example group G2B includes, for example, the following heterocyclic groups containing a substituted nitrogen atom (specific example group G2B1), a heterocyclic group containing a substituted oxygen atom (specific example group G2B2), a heterocyclic group containing a substituted sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced by a substituent (specific example group G2B4).

[0194] ・Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0195] Pyrrolyl,

[0196] Imidazole,

[0197] Pyrazolyl,

[0198] triazole,

[0199] Tetrazolyl,

[0200] Oxazolyl,

[0201] Isoxazolyl,

[0202] Oxadiazolyl,

[0203] Thiazolyl,

[0204] Isothiazolyl,

[0205] Thiadiazole,

[0206] Pyridyl,

[0207] Pyridazinyl,

[0208] Pyrimidine group,

[0209] Pyrazinyl,

[0210] Triazine group,

[0211] Indolyl,

[0212] Isoindolyl,

[0213] Indolizinyl,

[0214] Quinolizinyl,

[0215] Quinolinyl,

[0216] Isoquinolinyl,

[0217] Cinnoline,

[0218] Phthalocyanine,

[0219] Quinazoline,

[0220] Quinoxaline,

[0221] Benzimidazole,

[0222] Indazolyl,

[0223] Phenanthroline,

[0224] Phenanthridinyl,

[0225] Acridinyl,

[0226] Phenoxazine,

[0227] Carbazolyl,

[0228] Benzylcarbazolyl,

[0229] Morpholino,

[0230] Phenoxazine,

[0231] Phenothiazine,

[0232] Azacarbazolyl, and

[0233] Diazacarbazolyl.

[0234] ・Unsubstituted heterocyclic group containing an oxygen atom (Specific example group G2A2):

[0235] furanyl,

[0236] Oxazolyl,

[0237] Isoxazolyl,

[0238] Oxadiazolyl,

[0239] Xanthoxylum,

[0240] Benzofuranyl,

[0241] Isobenzofuranyl,

[0242] dibenzofuranyl,

[0243] naphthobenzofuranyl,

[0244] Benzoxazolyl,

[0245] Benzisoxazolyl,

[0246] Phenoxazine,

[0247] Morpholino,

[0248] dinaphthofuranyl,

[0249] Azadibenzofuranyl,

[0250] Diazadibenzofuranyl,

[0251] azanaphthobenzofuranyl, and

[0252] naphthyridinylbenzofuranyl.

[0253] ・Unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3):

[0254] Thiphenyl,

[0255] Thiazolyl,

[0256] Isothiazolyl,

[0257] Thiadiazole,

[0258] benzothienyl group,

[0259] isobenzothienyl group,

[0260] dibenzothienyl group,

[0261] naphthobenzothienyl group,

[0262] Benzothiazolyl,

[0263] Benzisothiazolyl,

[0264] Phenothiazine,

[0265] dinaphthothienyl group,

[0266] azadibenzothienyl group,

[0267] diazadibenzothienyl group,

[0268] azanaphthobenzothienyl group, and

[0269] diazanaphthobenzothienyl group.

[0270] ・A monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0271] [Chemistry 5]

[0272]

[0273] [Chemistry 6]

[0274]

[0275] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0276] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least any one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the aforementioned general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0277] ・Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0278] (9-phenyl)carbazolyl,

[0279] (9-biphenyl)carbazolyl,

[0280] (9-phenyl)phenylcarbazolyl,

[0281] (9-naphthyl)carbazolyl,

[0282] Diphenylcarbazol-9-yl,

[0283] phenylcarbazol-9-yl,

[0284] Methylbenzimidazole,

[0285] Ethylbenzimidazolyl,

[0286] Phenyltriazine,

[0287] Biphenyl triazine group,

[0288] Diphenyltriazine,

[0289] Phenylquinazolinyl, and

[0290] Biphenylquinazolinyl.

[0291] ・Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0292] Phenyldibenzofuranyl,

[0293] Methyldibenzofuranyl,

[0294] tert-Butyldibenzofuranyl, and

[0295] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0296] ・Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0297] Phenyldibenzothiophene,

[0298] Methyldibenzothiophene,

[0299] tert-Butyldibenzothienyl, and

[0300] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0301] ・Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0302] The aforementioned “one or more hydrogen atoms of a monovalent heterocyclic group” refers to one or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.

[0303] ・"Substituted or unsubstituted alkyl"

[0304] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, references to "alkyl" alone include both "unsubstituted alkyl groups" and "substituted alkyl groups."

[0305] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In this specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes a straight-chain "unsubstituted alkyl" and a branched "unsubstituted alkyl". In addition, the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" described in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0306] ・Unsubstituted alkyl group (specific example group G3A):

[0307] methyl,

[0308] Ethyl,

[0309] n-propyl,

[0310] Isopropyl,

[0311] n-Butyl,

[0312] Isobutyl,

[0313] sec-butyl, and

[0314] tert-butyl.

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

[0316] Heptafluoropropyl (including isomers),

[0317] Pentafluoroethyl,

[0318] 2,2,2-trifluoroethyl, and

[0319] trifluoromethyl.

[0320] ・"Substituted or unsubstituted alkenyl"

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

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

[0323] ・Unsubstituted alkenyl (specific example group G4A):

[0324] Vinyl,

[0325] Allyl,

[0326] 1-butenyl,

[0327] 2-Butenyl, and

[0328] 3-Butenyl.

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

[0330] 1,3-Butadienyl,

[0331] 1-Methylvinyl,

[0332] 1-methylallyl,

[0333] 1,1-dimethylallyl,

[0334] 2-methylallyl, and

[0335] 1,2-Dimethylallyl.

[0336] ・"Substituted or unsubstituted alkynyl"

[0337] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Herein, "unsubstituted alkynyl group" refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, reference to "alkynyl group" alone includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups."

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

[0339] ・Unsubstituted alkynyl (Specific example group G5A):

[0340] Ethylene.

[0341] ・"Substituted or unsubstituted cycloalkyl"

[0342] Specific examples of "substituted or unsubstituted cycloalkyl groups" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups (Specific Example Group G6A) and substituted cycloalkyl groups (Specific Example Group G6B). (Herein, "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" alone includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups."

[0343] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). In addition, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes the "substituted cycloalkyl" of the specific example group G6B in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl itself are replaced by a substituent, and the "substituted cycloalkyl" of the specific example group G6B in which the hydrogen atom of the substituent is further replaced by a substituent.

[0344] ・Unsubstituted cycloalkyl (Specific example group G6A):

[0345] Cyclopropyl,

[0346] Cyclobutyl,

[0347] Cyclopentyl,

[0348] Cyclohexyl,

[0349] 1-adamantyl,

[0350] 2-adamantyl,

[0351] 1-norbornyl, and

[0352] 2-Norbornyl.

[0353] ・Substituted cycloalkyl (Specific example group G6B):

[0354] 4-Methylcyclohexyl.

[0355] ・“-Si(R 901 )(R 902 )(R 903 )”

[0356] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as a specific example (specific example group G7), and the following are examples:

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

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

[0359] -Si(G1)(G1)(G2),

[0360] -Si(G2)(G2)(G2),

[0361] -Si(G3)(G3)(G3), and

[0362] -Si(G6)(G6)(G6). Here,

[0363] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0364] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0365] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0366] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0367] A plurality of G1s in -Si(G1)(G1)(G1) may be the same as or different from each other.

[0368] Multiple G2s in -Si(G1)(G2)(G2) may be the same as or different from each other.

[0369] A plurality of G1s in -Si(G1)(G1)(G2) may be the same as or different from each other.

[0370] Multiple G2s in -Si(G2)(G2)(G2) may be the same as or different from each other.

[0371] Multiple G3s in -Si(G3)(G3)(G3) may be the same as or different from each other.

[0372] Multiple G6's in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0373] ・“-O-(R 904 )”

[0374] As the -O-(R 904 ) are shown as specific examples (specific example group G8), and the following are examples:

[0375] -O(G1),

[0376] -O(G2),

[0377] -O(G3), and

[0378] -O(G6).

[0379] Here,

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

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

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

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

[0384] ・“-S-(R 905 )”

[0385] As described in this specification, -S-(R 905 ) are shown as a specific example (specific example group G9), and the

[0386] -S(G1),

[0387] -S(G2),

[0388] -S(G3), and

[0389] -S(G6).

[0390] Here,

[0391] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0392] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0393] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0394] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0395] ・“-N(R 906 )(R 907 )”

[0396] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0397] -N(G1)(G1),

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

[0399] -N(G1)(G2),

[0400] -N(G3)(G3), and

[0401] -N(G6)(G6).

[0402] Here,

[0403] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0404] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0405] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0406] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0407] The multiple G1s in -N(G1)(G1) may be the same as or different from each other.

[0408] Multiple G2s in -N(G2)(G2) may be the same as or different from each other.

[0409] Multiple G3s in -N(G3)(G3) may be the same as or different from each other.

[0410] -N(G6)(G6) The multiple G6s in each of the two groups may be the same or different.

[0411] ・"Halogen atoms"

[0412] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0413] ・"Substituted or unsubstituted fluoroalkyl group"

[0414] The “substituted or unsubstituted fluoroalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a “substituted or unsubstituted alkyl group” is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in a “substituted or unsubstituted alkyl group” are replaced by fluorine atoms (perfluoro group). Unless otherwise stated in this specification, the number of carbon atoms in an “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A “substituted fluoroalkyl group” refers to a group in which one or more hydrogen atoms of a “fluoroalkyl group” are replaced by a substituent. In addition, the “substituted fluoroalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a “substituted fluoroalkyl group” are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in a “substituted fluoroalkyl group” are further replaced by a substituent. Specific examples of “unsubstituted fluoroalkyl groups” include examples of groups in which one or more hydrogen atoms in the aforementioned “alkyl group” (specific example group G3) are replaced by fluorine atoms.

[0415] ・"Substituted or unsubstituted haloalkyl"

[0416] The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a “substituted or unsubstituted alkyl group” is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a “substituted or unsubstituted alkyl group” are replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A “substituted haloalkyl group” refers to a group in which one or more hydrogen atoms in a “haloalkyl group” are replaced by a substituent. In addition, the “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a “substituted haloalkyl group” are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in a “substituted haloalkyl group” are further replaced by a substituent. Specific examples of “unsubstituted haloalkyl groups” include the examples of groups in which one or more hydrogen atoms in the aforementioned “alkyl group” (Specific Example Group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halides.

[0417] ・"Substituted or unsubstituted alkoxy group"

[0418] A specific example of a "substituted or unsubstituted alkoxy group" as used herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in Specific Example Group G3. Unless otherwise specified in this specification, an "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0419] ・"Substituted or unsubstituted alkylthio"

[0420] A specific example of a "substituted or unsubstituted alkylthio group" as used herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in Specific Example Group G3. Unless otherwise specified herein, an "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0421] ・"Substituted or unsubstituted aryloxy group"

[0422] A specific example of a "substituted or unsubstituted aryloxy group" as used herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in Specific Example Group G1. Unless otherwise specified herein, an "unsubstituted aryloxy group" has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0423] ・"Substituted or unsubstituted arylthio group"

[0424] A specific example of a "substituted or unsubstituted arylthio group" as used herein is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" as described in Specific Example Group G1. Unless otherwise specified herein, an "unsubstituted arylthio group" has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0425] ・"Substituted or unsubstituted trialkylsilyl group"

[0426] A specific example of a "trialkylsilyl group" as described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in Specific Example Group G3. Multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of a "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0427] ・"Substituted or unsubstituted aralkyl"

[0428] A specific example of a "substituted or unsubstituted aralkyl group" as described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" as described in Specific Example Group G3, and G1 is a "substituted or unsubstituted aryl group" as described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group." Unless otherwise specified in this specification, an "unsubstituted aralkyl group" has 7 to 50 carbon atoms, preferably 7 to 30, and more preferably 7 to 18 carbon atoms.

[0429] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0430] Unless otherwise described in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysyl group, a triphenylene group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and the like.

[0431] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthroline group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group, a benzothiophenyl ... benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophenyl, etc.

[0432] In the present specification, unless otherwise specified, the carbazolyl group is specifically any of the following groups.

[0433] [Chemistry 7]

[0434]

[0435] In the present specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[0436] [Chemistry 8]

[0437]

[0438] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0439] In the present specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0440] [Chemistry 9]

[0441]

[0442] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0443] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0444] ・"Substituted or unsubstituted arylene group"

[0445] Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (Specific Example Group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in Specific Example Group G1 by removing one hydrogen atom from the aryl ring.

[0446] ・"Substituted or unsubstituted divalent heterocyclic group"

[0447] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described herein is a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 by removing one hydrogen atom from the heterocyclic ring.

[0448] ・"Substituted or unsubstituted alkylene"

[0449] Unless otherwise specified, the "substituted or unsubstituted alkylene group" referred to in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0450] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68).

[0451] [Chemistry 10]

[0452]

[0453] [Chemistry 11]

[0454]

[0455] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0456] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0457] [Chemistry 12]

[0458]

[0459] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0460] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0461] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0462] [Chemistry 13]

[0463]

[0464] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0465] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0466] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0467] [Chemistry 14]

[0468]

[0469] [Chemistry 15]

[0470]

[0471] [Chemistry 16]

[0472]

[0473] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0474] [Chemistry 17]

[0475]

[0476] [Chemistry 18]

[0477]

[0478] [Chemistry 19]

[0479]

[0480] [Chemistry 20]

[0481]

[0482] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0483] The above is the description of the “substituents described in this specification”.

[0484] ・"When bonding to form a ring"

[0485] In this specification, the case where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other” means the case where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring”, the case where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring”, and the case where “one or more groups consisting of two or more adjacent groups are not bonded to each other”.

[0486] The following describes the case where "one or more adjacent groups of two or more are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more adjacent groups of two or more are bonded to form a substituted or unsubstituted fused ring" (hereinafter sometimes collectively referred to as "bonding to form a ring"). This description uses the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring as an example.

[0487] [Chemistry 21]

[0488] .

[0489] For example, R 921 ~R930 In the case of "one or more groups consisting of two or more adjacent groups are bonded to each other to form a ring", the group consisting of two adjacent groups forming one group is R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0490] The above “one or more groups” means that two or more groups of the above two or more adjacent groups can form a ring at the same time. 921 With R 922 Bonded to each other to form ring Q A , while R 925 With R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0491] [Chemistry 22]

[0492] .

[0493] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups is bonded as in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, it means: R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 、R 922 and R 923) are bonded to each other to form a ring, and the anthracene mother skeleton is fused. In this 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), ring Q A and Ring Q C Total R 922 .

[0494] [Chemistry 23]

[0495] .

[0496] The formed "monocyclic ring" or "condensed ring" is merely a ring structure formed, and may be a saturated ring or an unsaturated ring. Even when "a group consisting of two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and Ring Q B In addition, the ring Q formed in the above general formula (TEMP-105) is A , and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C If the ring Q of the general formula (TMEP-104) A is a benzene ring, then ring Q A If the ring Q of the above general formula (TMEP-104) A is a naphthalene ring, then ring Q A It is a fused ring.

[0497] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0498] Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0499] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0500] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0501] "Forming a ring" means that only multiple atoms of the parent skeleton, or multiple atoms of the parent skeleton further form a ring with one or more arbitrary elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A Refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 A ring formed by bonding the carbon atoms of the anthracene skeleton and one or more arbitrary elements. As a specific example, R 921 With R 922 Formation of ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0502] Here, unless otherwise specified in this specification, "arbitrary element" is preferably at least one element selected from carbon, nitrogen, oxygen, and sulfur. In the case of an arbitrary element (e.g., carbon or nitrogen), bonds that do not form a ring may be terminated with hydrogen atoms or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the resulting ring is a heterocycle.

[0503] Unless otherwise specified in the present specification, the number of "one or more arbitrary elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0504] Unless otherwise specified in the present specification, "monocyclic ring" and "condensed ring" are preferable.

[0505] Unless otherwise specified in the present specification, of "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

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

[0507] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0508] When “one or more groups consisting of two or more adjacent groups” are “bonded to each other to form a substituted or unsubstituted monocyclic ring” or “bonded to each other to form a substituted or unsubstituted condensed ring”, unless otherwise specified in this specification, one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen, and sulfur.

[0509] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "Substituents described in the present specification".

[0510] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the aforementioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the "Substituents described in this specification" section.

[0511] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0512] ・Substituents when referred to as "substituted or unsubstituted"

[0513] In one embodiment of the present specification, the substituent referred to as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituent") is selected from, for example

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

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

[0516] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0517] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0518] -Si(R 901 )(R 902 )(R 903 ),

[0519] -O-(R 904 ),

[0520] -S-(R 905 ),

[0521] -N(R 906 )(R 907 ),

[0522] Halogen atoms, cyano, nitro,

[0523] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0524] unsubstituted heterocyclic groups having 5 to 50 ring atoms, etc.

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

[0526] hydrogen atoms,

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

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

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

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

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

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

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

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

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

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

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

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

[0539] Alkyl groups with 1 to 50 carbon atoms,

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

[0541] A group in a heterocyclic group having 5 to 50 ring atoms.

[0542] In one embodiment, the substituents referred to as "substituted or unsubstituted" are selected from

[0543] Alkyl groups with 1 to 18 carbon atoms,

[0544] an aryl group having 6 to 18 ring carbon atoms, and

[0545] A group in a heterocyclic group having 5 to 18 ring atoms.

[0546] Specific examples of each of the aforementioned optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in this specification".

[0547] Unless otherwise stated in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.

[0548] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0549] In this specification, a numerical range expressed using “AA to BB” means a range including the numerical value AA described before “AA to BB” as the lower limit and the numerical value BB described after “AA to BB” as the upper limit.

[0550] [Compound represented by formula (A1)]

[0551] The compound according to one embodiment of the present invention is a compound represented by the following formula (A1).

[0552] [Chemistry 24]

[0553]

[0554] (In formula (A1),

[0555] R1~R7 and R 10 ~R16 One or more adjacent two or more groups are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0556] R 21 and R 22 , R1 to R7 that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring, and R that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 10 ~R 16 Each independently

[0557] hydrogen atoms, or

[0558] Substituent R.

[0559] The aforementioned substituent R is

[0560] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0561] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0562] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0563] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0564] -Si(R 901 )(R 902 )(R 903 ),

[0565] -O-(R 904 ),

[0566] -S-(R 905 ),

[0567] -N(R 906 )(R 907 ),

[0568] Halogen atoms, cyano, nitro,

[0569] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0570] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0571] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0572] R 901 ~R 907 Each independently

[0573] hydrogen atoms,

[0574] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0575] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0576] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0577] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0578] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0579] The hydrogen atoms of the substituted or unsubstituted saturated or unsaturated ring formed above,

[0580] When the substituted or unsubstituted saturated or unsaturated ring formed above is substituted, a hydrogen atom possessed by the substituent,

[0581] R as a hydrogen atom 21 and R 22 、

[0582] R1~R7 and R as hydrogen atoms 10 ~R 16 ,as well as

[0583] R as the aforementioned substituent R 21 、R 22 , R1~R7 and R 10 ~R 16 The hydrogen atoms

[0584] At least one of them is a deuterium atom.)

[0585] When the substituent R is a group having a substituent, the hydrogen atom possessed by the substituent may be a deuterium atom. That is, the compound represented by the above formula (A1) includes compounds in which the hydrogen atom possessed by the substituent R is a deuterium atom.

[0586] By using the compound represented by the above formula (A1), the life of the organic EL device can be prolonged.

[0587] An organic EL device using the compound represented by the above formula (A1), which will be described later, has an effect of improving its lifespan.

[0588] The compound represented by the above formula (A1) has at least one deuterium atom.

[0589] Compounds containing deuterium atoms are detected by mass spectrometry or 1 The H-NMR analysis method confirmed that the deuterium atom in the compound has a bonding position. 1 The determination was made by H-NMR analysis. The details are as follows.

[0590] By performing mass analysis on the target compound and comparing it with a corresponding compound whose hydrogen atoms are all protium atoms, if the molecular weight increases by 1, it can be confirmed that it contains 1 deuterium atom. 1 H-NMR analysis cannot output a signal, so the target compound is 1 The integral value obtained by H-NMR analysis can confirm the number of deuterium atoms contained in the molecule. 1 By assigning the signals in H-NMR analysis, the bonding position of the deuterium atom can be determined.

[0591] In one embodiment, R 21 and R 22 , R1 to R7 that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring, and R that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 10 ~R 16 At least one of the substituents R is the aforementioned substituent, and the rest are hydrogen atoms. The hydrogen atoms are protium atoms or deuterium atoms. In addition, the hydrogen atoms possessed by the substituents R are also protium atoms or deuterium atoms.

[0592] In one embodiment, the substituent R is

[0593] -N(R 906 )(R 907 )(R 906 and R 907 As defined in the above formula (A1). ),

[0594] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0595] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0596] In one embodiment, R1 to R7 and R 10 ~R 16 One or more of -N(R 906 )(R 907 ).

[0597] In one embodiment, R1 to R7 and R 10 ~R 16 Two or more of them are -N(R 906 )(R 907 ).

[0598] In one embodiment, the compound represented by the above formula (A1) is a compound represented by the following formula (A10).

[0599] [Chemistry 25]

[0600]

[0601] (In formula (A10),

[0602] R1~R4、R 10 ~R 13 、R 21 and R 22 As defined in the above formula (A1).

[0603] R A 、R B 、R C and R D Each independently

[0604] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[0605] A substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

[0606] In one embodiment, the compound represented by the above formula (A10) is a compound represented by the following formula (A11).

[0607] [Chemistry 26]

[0608]

[0609] (In formula (A11),

[0610] R 21 、R 22 、R A 、R B 、R C and R D As defined in the above formula (A10).

[0611] In one embodiment, R in the above formulas (A10) and (A11) A 、R B 、R C and R D Each is independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0612] In one embodiment, R in the above formulas (A10) and (A11) A 、R B 、R C and R DEach is independently a substituted or unsubstituted phenyl group.

[0613] In one embodiment, R in the above formula (A1) 21 and R 22 Each is independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted phenyl group.

[0614] In one embodiment, the compound represented by formula (A1) is a compound represented by the following formula (A13).

[0615] [Chemistry 27]

[0616]

[0617] In formula (A13), R5 to R7, R 14 ~R 16 、R 21 、R 22 、R A 、R B 、R C and R D As defined above in formula (A1) and formula (A10).

[0618] In one embodiment, the compound represented by formula (A13) is a compound represented by the following formula (A14).

[0619] [Chemistry 28]

[0620]

[0621] In formula (A14), R 21 、R 22 、R A 、R B 、R C and R D As defined above in formula (A1) and formula (A10).

[0622] In one embodiment, the compound represented by formula (A1) is a compound represented by the following formula (A15).

[0623] [Chemistry 29]

[0624]

[0625] In formula (A15), R5 to R7, R 14 ~R 16 、R 21 、R 22 、R A 、R B 、R C and R DAs defined above in formula (A1) and formula (A10).

[0626] In one embodiment, the compound represented by formula (A15) is a compound represented by the following formula (A16).

[0627] [Chemistry 30]

[0628]

[0629] In formula (A16), R 21 、R 22 、R A 、R B 、R C and R D As defined above in formula (A1) and formula (A10).

[0630] In one embodiment, the compound represented by the above formula (A10) is a compound represented by the following formula (A17).

[0631] [Chemistry 31]

[0632]

[0633] In formula (A17), R5 to R7, R 14 ~R 16 、R 21 、R 22 、R A 、R B 、R C and R D As defined above in formula (A1) and formula (A10).

[0634] In one embodiment, the compound represented by the above formula (A17) is a compound represented by the following formula (A18).

[0635] [Chemistry 32]

[0636]

[0637] In formula (A18), R 21 、R 22 、R A 、R B 、R C and R D As defined above in formula (A1) and formula (A10).

[0638] In one embodiment, R in formula (A1) 21 and R 22 Here, the hydrogen atom is a protium atom or a deuterium atom.

[0639] Details of each substituent in the above formulae, and when referred to as "substituted or unsubstituted", the substituent are as described in the [Definition] column of this specification.

[0640] According to the synthesis examples described below, the compound represented by formula (A1) can be synthesized using known substitution reactions and raw materials corresponding to the target product.

[0641] Specific examples of the compound represented by formula (A1) include the following compounds: In the following specific examples, Me represents a methyl group, and D represents a deuterium atom.

[0642]

[0643]

[0644]

[0645]

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655]

[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665]

[0666]

[0667]

[0668]

[0669]

[0670]

[0671]

[0672]

[0673] For example, the compound represented by formula (A1) can be synthesized by following the reactions in the synthesis examples described below, using known substitution reactions and starting materials corresponding to the target product.

[0674] Intermediate F used for synthesizing the compound represented by formula (A10) can be synthesized, for example, according to the following synthesis route.

[0675] [Chemistry 64]

[0676]

[0677] (In the above route, m is an integer of 0 to 10, n is an integer of 0 to 8, and p is an integer of 0 to 4. When p is an integer of 1 to 4, R corresponds to R1 to R4 in the above formula (A10) and R 10 ~R 13 For the case of substituent R.

[0678] DDQ is 2,3-dichloro-5,6-dicyano-p-benzoquinone.

[0679] Pd(PPh3)2Cl2 is [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II).

[0680] (dppf)PdCl2・CH2Cl2 is a [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex.

[0681] DMF is dimethylformamide.)

[0682] [Materials for organic EL devices]

[0683] The organic EL device material according to one embodiment of the present invention includes a compound represented by formula (A1).

[0684] In one embodiment, the compound represented by the aforementioned formula (A1) (hereinafter sometimes referred to as "deuterium body") and the compound having the same structure as the compound represented by the aforementioned formula (A1) except that it contains only protium atoms as hydrogen atoms (hereinafter sometimes referred to as "protium body"), the former corresponding to a total content ratio of 1 mol% or more.

[0685] In one embodiment, the deuterium content is 30 mol % or more, 60 mol % or more, 70 mol % or more, 90 mol % or more, 95 mol % or more, 98 mol % or more, or 99 mol % or more.

[0686] [Organic EL element]

[0687] An organic EL element according to one embodiment of the present invention has

[0688] cathode,

[0689] Anode, and

[0690] at least one organic layer disposed between the cathode and the anode,

[0691] At least one of the at least one organic layer contains the compound represented by the above formula (A1).

[0692] In one embodiment, the at least one organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound represented by the formula (A1).

[0693] In one embodiment, the compound represented by the formula (A1) is contained in the light-emitting layer as a dopant material.

[0694] Reference Figure 1 A schematic configuration of an organic EL device according to one embodiment of the present invention will be described.

[0695] An organic EL element 1 according to one embodiment of the present invention includes a substrate 2 , an anode 3 , a light-emitting layer 5 as an organic layer, a cathode 10 , an organic layer 4 between the anode 3 and the light-emitting layer 5 , and an organic layer 6 between the light-emitting layer 5 and the cathode 10 .

[0696] Each of the organic layer 4 and the organic layer 6 may be a single layer, or may include a plurality of layers.

[0697] In addition, the organic layer 4 may include a hole transport domain. The hole transport domain may include a hole injection layer, a hole transport layer, an electron barrier layer, etc. The organic layer 6 may include an electron transport domain. The electron transport domain may include an electron injection layer, an electron transport layer, a hole barrier layer, etc.

[0698] The compound represented by formula (A1) is contained in the organic layer 4, the light-emitting layer 5, or the organic layer 6. In one embodiment, the compound represented by formula (A1) is contained in the light-emitting layer 5. The compound represented by formula (A1) can function as a dopant material in the light-emitting layer 5.

[0699] The organic EL element of one embodiment of the present invention exhibits high element performance by having the above-mentioned configuration. Specifically, it is possible to provide an organic EL element with a long life.

[0700] In addition, according to an organic EL element of one embodiment, a method for improving the performance of an organic EL element can also be provided by using a compound represented by the above-mentioned formula (A1) in the light-emitting layer of the organic EL element. According to other embodiments of the organic EL element, a method for improving the performance of an organic EL element can also be provided by combining the compound represented by the above-mentioned formula (A1) and the compound represented by the formula (10) described later in the light-emitting layer of the organic EL element. Specifically, this method can improve the performance of the organic EL element, especially compared with the case where a compound having the same structure as the compound represented by formula (A1) except that only protium atoms are included as hydrogen atoms (hereinafter also referred to as "protium body") is used as a dopant material. In addition, when a protium body is used, it means that as a dopant material in the light-emitting layer, only the protium body is used (the ratio of the protium body to the total of the compound represented by formula (A1) and the protium body is 90 mol% or more, 95 mol% or more, or 99 mol% or more).

[0701] That is, by using a compound (compound represented by formula (A1)) in which at least one hydrogen atom of a protium body is replaced with a deuterium atom as a dopant material instead of or in addition to a protium body, the performance can be improved.

[0702] In one embodiment, the light-emitting layer contains the compound represented by the aforementioned formula (A1) (deuterium) and a compound (protium) having the same structure as the compound represented by the aforementioned formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 1% by mass or more.

[0703] In one embodiment, the light-emitting layer contains the compound represented by the aforementioned formula (A1), namely, a deuterium body and a protium body, and the proportion of the deuterium body in the aforementioned light-emitting layer relative to the total is 30 mass% or more, 60 mass% or more, 70 mass% or more, 90 mass% or more, 95 mass% or more, 98 mass% or more, or 99 mass% or more.

[0704] An organic EL element according to one embodiment of the present invention has

[0705] cathode,

[0706] Anode, and

[0707] at least one organic layer disposed between the cathode and the anode,

[0708] The at least one organic layer comprises a light-emitting layer,

[0709] The light-emitting layer contains the compound represented by the above formula (A1) and the compound represented by the following formula (10).

[0710] The compound represented by formula (A1) is as described above.

[0711] By using the compound represented by the aforementioned formula (A1) and the compound represented by the following formula (10) in the light-emitting layer, the life of the organic EL device can be improved.

[0712] <Compound represented by formula (10)>

[0713] The compound represented by formula (10) will be described.

[0714] [Chemistry 65]

[0715]

[0716] [In formula (10),

[0717] R 101 ~R 110 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring.

[0718] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 101 ~R 110 Each independently

[0719] hydrogen atoms,

[0720] Substituent R, or

[0721] A group represented by the following formula (11).

[0722] -L 101 -Ar 101 (11)

[0723] (In formula (11),

[0724] L 101 for

[0725] single bond,

[0726] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0727] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0728] Ar 101 for

[0729] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0730] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0731] The aforementioned substituent R is

[0732] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0733] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0734] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0735] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0736] -Si(R 901 )(R 902 )(R 903 ),

[0737] -O-(R 904 ),

[0738] -S-(R 905 ),

[0739] -N(R 906 )(R 907 ),

[0740] Halogen atoms, cyano, nitro,

[0741] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0742] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0743] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0744] R 901 ~R 907 Each independently

[0745] hydrogen atoms,

[0746] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0747] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0748] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0749] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0750] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0751] Among them, R does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 101 ~R 110 At least one of the groups is a group represented by the aforementioned formula (11). When there are two or more of the aforementioned formula (11), the two or more groups represented by the aforementioned formula (11) may be the same or different.]

[0752] The compound represented by the above formula (10) may have a deuterium atom as a hydrogen atom.

[0753] In one embodiment, Ar in the above formula (10) 101 At least one of the aryl groups is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0754] In one embodiment, Ar in the above formula (10) 101 At least one of the groups is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0755] In one embodiment, all Ar in the above formula (10) 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 They can be the same or different from each other.

[0756] In one embodiment, Ar in the above formula (10) 101 One of them is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and the remaining Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 They can be the same or different from each other.

[0757] In one embodiment, L in the above formula (10) 101 At least one of them is a single bond.

[0758] In one embodiment, L in the above formula (10) 101 All are single keys.

[0759] In one embodiment, L in the above formula (10) 101 At least one of the arylene groups is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0760] In one embodiment, L in the above formula (10) 101 At least one of them is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0761] In one embodiment, -L in the above formula (10) 101 -Ar 101 The groups shown are selected from

[0762] substituted or unsubstituted phenyl,

[0763] substituted or unsubstituted naphthyl,

[0764] Substituted or unsubstituted biphenyl,

[0765] Substituted or unsubstituted phenoxy,

[0766] Substituted or unsubstituted triphenylene group,

[0767] substituted or unsubstituted fluorenyl,

[0768] Substituted or unsubstituted benzofluorenyl,

[0769] substituted or unsubstituted dibenzofuranyl,

[0770] substituted or unsubstituted naphthobenzofuranyl,

[0771] Substituted or unsubstituted dibenzothiophenyl, and

[0772] a substituted or unsubstituted carbazolyl group.

[0773] In one embodiment, the substituents R in the above formula (10) are each independently

[0774] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0775] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0776] -Si(R 901 )(R 902 )(R 903 ),

[0777] -O-(R 904 ),

[0778] -S-(R 905 ),

[0779] -N(R 906 )(R 907 ),

[0780] Halogen atoms, cyano groups, nitro groups, or

[0781] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0782] R 901 ~R 907 As defined in formula (10) above.

[0783] In one embodiment, the "substituted or unsubstituted" substituents in the aforementioned formula (10) are each independently

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

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

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

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

[0788] -Si(R 901 )(R 902 )(R 903 ),

[0789] -O-(R 904 ),

[0790] -S-(R 905 ),

[0791] -N(R 906 )(R 907 ),

[0792] Halogen atoms, cyano, nitro,

[0793] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0794] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0795] R 901 ~R 907 As defined in formula (10) above.

[0796] In one embodiment, the "substituted or unsubstituted" substituents in the aforementioned formula (10) are each independently

[0797] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0798] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0799] -Si(R 901 )(R 902 )(R 903 ),

[0800] -O-(R 904 ),

[0801] -S-(R 905 ),

[0802] -N(R 906 )(R 907 ),

[0803] Halogen atoms, cyano groups, nitro groups, or

[0804] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0805] R 901 ~R 907 As defined in formula (10) above.

[0806] In one embodiment, the substituents referred to as "substituted or unsubstituted" in the above formula (10) are selected from

[0807] Alkyl groups with 1 to 18 carbon atoms,

[0808] an aryl group having 6 to 18 ring carbon atoms, and

[0809] A monovalent heterocyclic group having 5 to 18 ring atoms.

[0810] In one embodiment, the substituent referred to as "substituted or unsubstituted" in the above formula (10) is an alkyl group having 1 to 5 carbon atoms.

[0811] In one embodiment, the compound represented by the aforementioned formula (10) is a compound represented by the following formula (20).

[0812] [Chemistry 66]

[0813]

[0814] (In formula (20), R 101 ~R 108 , L 101 and Ar 101 As defined in the above formula (10).

[0815] The compound represented by the above formula (20) may have a deuterium atom as a hydrogen atom.

[0816] That is, in one embodiment, the compound represented by the above formula (10) or (20) has at least two groups represented by the above formula (11).

[0817] In one embodiment, the compound represented by the aforementioned formula (10) or formula (20) has two or three groups represented by the aforementioned formula (11).

[0818] In one embodiment, R in the above formulas (10) and (20) 101 ~R 110 The aforementioned substituted or unsubstituted saturated or unsaturated ring is not formed.

[0819] In one embodiment, R in the above formulas (10) and (20) 101 ~R 110 A hydrogen atom.

[0820] In one embodiment, the compound represented by the aforementioned formula (20) is a compound represented by the following formula (30).

[0821] [Chemistry 67]

[0822]

[0823] (In formula (30), L 101 and Ar 101 As defined in formula (10) above.

[0824] R 101A ~R 108A The two adjacent groups do not form a substituted or unsubstituted saturated or unsaturated ring.

[0825] R 101A ~R 108A Each independently

[0826] hydrogen atoms, or

[0827] Substituent R.

[0828] The substituent R is as defined in the above formula (10).

[0829] That is, the compound represented by the above formula (30) is a compound having two groups represented by the above formula (11).

[0830] The compound represented by the above formula (30) has substantially only protium atoms as hydrogen atoms.

[0831] Furthermore, “having substantially only hydrogen atoms” means that the ratio of a compound having the same structure and having only hydrogen atoms as hydrogen atoms (protide) to the total of the protide and the compound having deuterium atoms (deuteride) is 90 mol % or more, 95 mol % or more, or 99 mol % or more.

[0832] In one embodiment, the compound represented by the aforementioned formula (30) is a compound represented by the following formula (31).

[0833] [Chemistry 68]

[0834]

[0835] (In formula (31), L 101 and Ar 101 As defined in formula (10) above.

[0836] R 101A ~R 108A As defined in formula (30) above.

[0837] X b O, S, N (R 131 ), or C(R 132 )(R 133 ).

[0838] R 121 ~R 128 , and R 131 ~R 133 One of them is L 101 Single bond bonding.

[0839] Not with L 101 R bonded to a single bond 121 ~R 128 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring.

[0840] Not with L 101 R is a single bond bonded to the ring and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 121 ~R 128 Each independently

[0841] hydrogen atoms, or

[0842] Substituent R.

[0843] The substituent R is as defined in the above formula (10).

[0844] Not with L 101 R bonded to a single bond 131 ~R133 Each independently

[0845] hydrogen atoms,

[0846] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0848] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0849] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0850] R 131 ~R 133 When there are two or more, two or more R 131 ~R 133 They can be the same or different.)

[0851] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (32).

[0852] [Chemistry 69]

[0853]

[0854] (In formula (32), R 101A ~R 108A , L 101 、Ar 101 、R 121 ~R 128 、R 132 and R 133 As defined in the above formula (31).

[0855] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (33).

[0856] [Chemistry 70]

[0857]

[0858] (In formula (33), R 101A ~R 108A , L 101 、Ar 101 , and R 121 ~R 128 As defined in formula (31) above.

[0859] X c O, S, or NR 131 .

[0860] R 131 As defined in the above formula (31).

[0861] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (34).

[0862] [Chemistry 71]

[0863]

[0864] (In formula (34), R 101A ~R 108A , L 101 and Ar 101 As defined in formula (31) above.

[0865] X c O, S or NR 131 .

[0866] R 131 As defined in formula (31) above.

[0867] R 121A ~R 128A One of them is L 101 Single bond bonding.

[0868] Not with L 101 R bonded to a single bond 121A ~R 128A One or more adjacent groups of two or more of them do not form a substituted or unsubstituted saturated or unsaturated ring.

[0869] Not with L 101 R bonded to a single bond 121A ~R 128A Each independently

[0870] hydrogen atoms, or

[0871] Substituent R.

[0872] The substituent R is as defined in the above formula (10).

[0873] In one embodiment, the compound represented by the aforementioned formula (31) is a compound represented by the following formula (35).

[0874] [Chemistry 72]

[0875]

[0876] [In formula (35), R 101A ~R 108A , L 101 、Ar 101and X b As defined in formula (31) above.

[0877] R 121A ~R 124A One or more adjacent groups of two or more of the rings are bonded to each other without forming a substituted or unsubstituted saturated or unsaturated ring.

[0878] R 125B and R 126B 、R 126B and R 127B , and R 127B and R 128B Any one of the groups in the formula (35a) and (35b) may be bonded to each other to form a ring represented by the following formula (35a) or (35b).

[0879] [Chemistry 73]

[0880]

[0881] (In formulas (35a) and (35b),

[0882] 2* each with R 125B and R R126B 、R 126B and R 127B , and R 127B and R 128B Any one of the bonding groups.

[0883] R 141 ~R 144 Each independently

[0884] hydrogen atoms, or

[0885] Substituent R.

[0886] The substituent R is as defined in the above formula (10).

[0887] X d is O or S.)

[0888] R 121A ~R 124A , R which does not form a ring represented by the above formula (35a) or (35b) 125B ~R 128B , and R 141 ~R 144 One of them is L 101 Single bond bonding.

[0889] Not with L 101 R bonded to a single bond 121A ~R 124A , and not with L 101R is a single bond that is bonded to R and does not form a ring represented by the above formula (35a) or (35b). 125B ~R 128B Each independently

[0890] hydrogen atoms, or

[0891] Substituent R.

[0892] The aforementioned substituent R is as defined in the aforementioned formula (10).]

[0893] In one embodiment, the compound represented by the aforementioned formula (35) is a compound represented by the following formula (36).

[0894] [Chemistry 74]

[0895]

[0896] (In formula (36), R 101A ~R 108A , L 101 、Ar 101 , and R 125B ~R 128B As defined in the above formula (35).

[0897] In one embodiment, the compound represented by the aforementioned formula (34) is a compound represented by the following formula (37).

[0898] [Chemistry 75]

[0899]

[0900] (In formula (37), R 101A ~R 108A 、R 125A ~R 128A , L 101 and Ar 101 As defined in the above formula (34).

[0901] In one embodiment, R in the above formulas (30) to (37) 101A ~R 108A A hydrogen atom.

[0902] In one embodiment, the compound represented by the aforementioned formula (10) is a compound represented by the following formula (40).

[0903] [Chemistry 76]

[0904]

[0905] (In formula (40), L 101 and Ar 101As defined in formula (10) above.

[0906] R 101A , and R 103A ~R 108A One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring.

[0907] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 101A , and R 103A ~R 108A Each independently

[0908] hydrogen atoms, or

[0909] Substituent R.

[0910] The substituent R is as defined in the above formula (10).

[0911] That is, the compound represented by the above formula (40) is a compound having three groups represented by the above formula (11). In addition, the compound represented by the above formula (40) has substantially only protium atoms as hydrogen atoms.

[0912] In one embodiment, the compound represented by the aforementioned formula (40) is represented by the following formula (41).

[0913] [Chemistry 77]

[0914]

[0915] (In formula (41), L 101 and Ar 101 As defined in the above formula (40).

[0916] In one embodiment, the compound represented by the aforementioned formula (40) is a compound represented by any one of the following formulas (42-1) to (42-3).

[0917] [Chemistry 78]

[0918]

[0919] (In formulas (42-1) to (42-3), R 101A ~R 108A , L 101 and Ar 101 As defined in the above formula (40).

[0920] In one embodiment, the compound represented by the aforementioned formulae (42-1) to (42-3) is a compound represented by any one of the following formulae (43-1) to (43-3).

[0921] [Chemistry 79]

[0922]

[0923] (In formulas (43-1) to (43-3), L 101 and Ar 101 As defined in the above formula (40).

[0924] In one embodiment, -L in the above formulae (40), (41), (42-1) to (42-3), and (43-1) to (43-3) 101 -Ar 101 The groups shown are selected from

[0925] substituted or unsubstituted phenyl,

[0926] substituted or unsubstituted naphthyl,

[0927] Substituted or unsubstituted biphenyl,

[0928] Substituted or unsubstituted phenoxy,

[0929] Substituted or unsubstituted triphenylene group,

[0930] substituted or unsubstituted fluorenyl,

[0931] substituted or unsubstituted benzofluorenyl,

[0932] substituted or unsubstituted dibenzofuranyl,

[0933] substituted or unsubstituted naphthobenzofuranyl,

[0934] Substituted or unsubstituted dibenzothienyl, and

[0935] a substituted or unsubstituted carbazolyl group.

[0936] In one embodiment, the compounds represented by the above formula (10) or (20) include compounds in which at least one of the hydrogen atoms possessed by these compounds is a deuterium atom.

[0937] In one embodiment, in the above formula (20)

[0938] R as a hydrogen atom 101 ~R 108 、

[0939] R as the aforementioned substituent R 101 ~R 108 The hydrogen atoms

[0940] L 101 The hydrogen atoms

[0941] L 101 The hydrogen atom possessed by the substituent of

[0942] Ar 101 The hydrogen atoms and

[0943] Ar 101 The hydrogen atom possessed by the substituent

[0944] At least one of them is a deuterium atom.

[0945] The compounds represented by the aforementioned formulae (30) to (37) include compounds in which at least one of the hydrogen atoms possessed by these compounds is a deuterium atom.

[0946] In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the aforementioned formulae (30) to (37) is a deuterium atom.

[0947] In one embodiment, the compound represented by the aforementioned formula (30) is a compound represented by the following formula (30D).

[0948] [Chemistry 80]

[0949]

[0950] (In formula (30D), R 101A ~R 108A , L 101 and Ar 101 As defined in formula (30) above.

[0951] Among them, R as a hydrogen atom 101A ~R 108A 、

[0952] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms

[0953] L 101 The hydrogen atoms

[0954] L 101 The hydrogen atom possessed by the substituent of

[0955] Ar 101 The hydrogen atoms and

[0956] Ar 101 The hydrogen atom possessed by the substituent

[0957] At least one of them is a deuterium atom.)

[0958] That is, the compound represented by the above formula (30D) is a compound in which at least one of the hydrogen atoms possessed by the compound represented by the above formula (30) is a deuterium atom.

[0959] In one embodiment, R in the above formula (30D) is a hydrogen atom. 101A ~R 108A At least one of them is a deuterium atom.

[0960] In one embodiment, the compound represented by the aforementioned formula (30D) is a compound represented by the following formula (31D).

[0961] [Chemistry 81]

[0962]

[0963] (In formula (31D), R 101A ~R 108A , L 101 and Ar 101 As defined above in formula (30D).

[0964] X d O or S.

[0965] R 121 ~R 128 One of them is L 101 Single bond bonding.

[0966] Not with L 101 R bonded to a single bond 121 ~R 128 One or more adjacent groups of two or more of them form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0967] Not with L 101 R is a single bond bonded to the ring and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 121 ~R 128 Each independently

[0968] hydrogen atoms, or

[0969] Substituent R.

[0970] The substituent R is as defined in the above formula (10).

[0971] Among them, R as a hydrogen atom 101A ~R 108A 、

[0972] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms

[0973] L 101 The hydrogen atoms

[0974] L 101 The hydrogen atom possessed by the substituent of

[0975] Ar 101 The hydrogen atoms

[0976] Ar 101 The hydrogen atom possessed by the substituent

[0977] R as a hydrogen atom 121 ~R 128 ,and

[0978] R as the aforementioned substituent R 121 ~R 128 The hydrogen atoms

[0979] At least one of them is a deuterium atom.)

[0980] In one embodiment, the compound represented by the aforementioned formula (31D) is a compound represented by the following formula (32D).

[0981] [Chemistry 82]

[0982]

[0983] (In formula (32D), R 101A ~R 108A 、R 125A ~R 128A , L 101 and Ar 101 As defined above in formula (31D).

[0984] in,

[0985] R as a hydrogen atom 101A ~R 108A 、

[0986] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms

[0987] R as a hydrogen atom 125A ~R 128A 、

[0988] R as the aforementioned substituent R 125A ~R 128A The hydrogen atoms

[0989] The hydrogen atom bonded to the carbon atom of the dibenzofuran skeleton in formula (32D),

[0990] L 101 The hydrogen atoms

[0991] L 101 The hydrogen atom possessed by the substituent of

[0992] Ar 101 The hydrogen atoms and

[0993] Ar 101 The hydrogen atom possessed by the substituent

[0994] At least one of them is a deuterium atom.)

[0995] In one embodiment, the compound represented by the aforementioned formula (32D) is a compound represented by the following formula (32D-1) or (32D-2).

[0996] [Chemistry 83]

[0997]

[0998]

[0999] (In formulas (32D-1) and (32D-2), R 101A ~R 108A 、R 125A ~R 128A , L 101 and Ar 101 As defined above in formula (32D).

[1000] in,

[1001] R as a hydrogen atom 101A ~R 108A 、

[1002] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms

[1003] R as a hydrogen atom 125A ~R 128A 、

[1004] R as the aforementioned substituent R 125A ~R 128A The hydrogen atoms

[1005] The hydrogen atoms bonded to the carbon atoms of the dibenzofuran skeleton in formulas (32D-1) and (32D-2),

[1006] L 101 The hydrogen atoms

[1007] L 101 The hydrogen atom possessed by the substituent of

[1008] Ar 101 The hydrogen atoms and

[1009] Ar 101 The hydrogen atom possessed by the substituent

[1010] At least one of them is a deuterium atom.)

[1011] In one embodiment, at least one of the hydrogen atoms in the compound represented by the aforementioned formula (40), (41), (42-1) to (42-3), or (43-1) to (43-3) is a deuterium atom.

[1012] In one embodiment, the hydrogen atom (R as a hydrogen atom) bonded to the carbon atom constituting the anthracene skeleton in the compound represented by the aforementioned formula (41) 101A ~R 108A ) is a deuterium atom.

[1013] In one embodiment, the compound represented by the aforementioned formula (40) is a compound represented by the following formula (40D).

[1014] [Chemistry 84]

[1015]

[1016] (In formula (40D), L 101 and Ar 101 As defined in formula (10) above.

[1017] R 101A , and R 103A ~R 108A One or more adjacent groups of two or more of them do not form a substituted or unsubstituted saturated or unsaturated ring.

[1018] R 101A , and R 103A ~R 108A Each independently

[1019] hydrogen atoms, or

[1020] Substituent R.

[1021] The substituent R is as defined in the above formula (10).

[1022] Among them, R as a hydrogen atom 101A , and R 103A ~R 108A 、

[1023] R as the aforementioned substituent R 101A , and R 103A ~R 108A The hydrogen atoms

[1024] L 101 The hydrogen atoms

[1025] L 101 The hydrogen atom possessed by the substituent of

[1026] Ar 101 The hydrogen atoms and

[1027] Ar 101 The hydrogen atom possessed by the substituent of

[1028] At least one of them is a deuterium atom.)

[1029] In one embodiment, R in the aforementioned formula (40D) 101A , and R 103A ~R 108A At least one of them is a deuterium atom.

[1030] In one embodiment, the compound represented by the aforementioned formula (40D) is a compound represented by the following formula (41D).

[1031] [Chemistry 85]

[1032]

[1033] (In formula (41D), L 101 and Ar 101 As defined above in formula (40D).

[1034] Among them, in formula (41D)

[1035] The hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton,

[1036] L 101 The hydrogen atoms

[1037] L 101 The hydrogen atom possessed by the substituent of

[1038] Ar 101 The hydrogen atoms and

[1039] Ar 101 The hydrogen atom possessed by the substituent of

[1040] At least one of them is a deuterium atom.)

[1041] In one embodiment, the compound represented by the aforementioned formula (40D) is a compound represented by any one of the following formulas (42D-1) to (42D-3).

[1042] [Chemistry 86]

[1043]

[1044] (In formulas (42D-1) to (42D-3), R 101A ~R 108A , L 101 and Ar 101 As defined above in formula (40D).

[1045] Among them, in the above formula (42D-1)

[1046] R as a hydrogen atom 101A , and R 103A ~R 108A 、

[1047] R as the aforementioned substituent R 101A , and R 103A ~R 108A The hydrogen atoms

[1048] L 101 The hydrogen atoms

[1049] L 101 The hydrogen atom possessed by the substituent of

[1050] Ar 101 The hydrogen atoms

[1051] Ar 101 a hydrogen atom possessed by a substituent of

[1052] At least one of the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in the aforementioned formula (42D-1) is a deuterium atom.

[1053] In the above formula (42D-2), R is a hydrogen atom. 101A , and R 103A ~R 108A 、

[1054] R as the aforementioned substituent R 101A , and R 103A ~R 108A The hydrogen atoms

[1055] L 101 The hydrogen atoms

[1056] L 101 The hydrogen atom possessed by the substituent of

[1057] Ar 101 The hydrogen atoms

[1058] Ar 101 a hydrogen atom possessed by a substituent of

[1059] At least one of the hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (42D-2) is a deuterium atom.

[1060] In the above formula (42D-3), R is a hydrogen atom. 101A , and R 103A ~R 108A 、

[1061] R as the aforementioned substituent R 101A , and R 103A ~R 108A The hydrogen atoms

[1062] L 101 The hydrogen atoms

[1063] L 101 The hydrogen atom possessed by the substituent of

[1064] Ar 101 The hydrogen atoms

[1065] Ar 101 a hydrogen atom possessed by a substituent of

[1066] The hydrogen atom bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (42D-3)

[1067] At least one of them is a deuterium atom.)

[1068] In one embodiment, the compound represented by the aforementioned formulae (42D-1) to (42D-3) is a compound represented by any one of the following formulae (43D-1) to (43D-3).

[1069] [Chemistry 87]

[1070]

[1071] (In formulas (43D-1) to (43D-3), L 101 and Ar 101 As defined above in formula (40D).

[1072] The hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the aforementioned formula (43D-1)

[1073] L 101 The hydrogen atoms

[1074] L 101 The hydrogen atom possessed by the substituent of

[1075] Ar 101 The hydrogen atoms

[1076] Ar 101 The hydrogen atom possessed by the substituent of

[1077] At least one of the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in the aforementioned formula (43D-1) is a deuterium atom.

[1078] The hydrogen atom bonded to the carbon atom constituting the anthracene skeleton in the aforementioned formula (43D-2),

[1079] L 101 The hydrogen atoms

[1080] L 101 The hydrogen atom possessed by the substituent of

[1081] Ar 101 The hydrogen atoms

[1082] Ar 101 The hydrogen atom possessed by the substituent of

[1083] At least one of the hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (43D-2) is a deuterium atom.

[1084] The hydrogen atom bonded to the carbon atom constituting the anthracene skeleton in the aforementioned formula (43D-3),

[1085] L 101 The hydrogen atoms

[1086] L 101 The hydrogen atom possessed by the substituent of

[1087] Ar 101 The hydrogen atoms

[1088] Ar 101 The hydrogen atom possessed by the substituent of

[1089] The hydrogen atom bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (43D-3)

[1090] At least one of them is a deuterium atom.)

[1091] As specific examples of the compound represented by formula (10), for example, the following compounds can be cited. The compound represented by formula (10) is not limited to these specific examples. In the following specific examples, Me represents a methyl group, and D represents a deuterium atom.

[1092]

[1093]

[1094]

[1095]

[1096]

[1097]

[1098]

[1099]

[1100]

[1101]

[1102]

[1103]

[1104] Specific examples of each group in formula (A1) and formula (10) and the like are described in the [Definition] column of this specification.

[1105] The organic EL element of one embodiment of the present invention comprises a cathode, an anode, and at least one organic layer arranged between the cathode and the anode, as described above, at least one of the at least one organic layer comprises a compound represented by formula (A1). Apart from this, conventionally known materials and elements may be used as long as the effects of the present invention are not impaired.

[1106] In addition, the organic EL element of one embodiment of the present invention has a cathode, an anode and at least one organic layer arranged between the cathode and the anode as described above, the at least one organic layer includes a light-emitting layer, and the light-emitting layer contains a compound represented by the aforementioned formula (A1) and a compound represented by the following formula (10). In addition, as long as the effects of the present invention are not impaired, conventionally known materials and elements can be used.

[1107] Hereinafter, members that can be used in the organic EL device of one embodiment of the present invention and materials constituting each layer other than the above-mentioned compounds will be described.

[1108] (Substrate)

[1109] The substrate can serve as a support for the light-emitting element. Examples of substrates include glass, quartz, and plastic. Furthermore, flexible substrates can also be used. A flexible substrate is a bendable (flexible) substrate, and examples thereof include plastic substrates made of polycarbonate and polyvinyl chloride.

[1110] (anode)

[1111] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or greater). Specifically, examples include indium oxide-tin oxide (ITO), indium oxide-zinc oxide, tungsten oxide, and graphene. These electrodes may further contain other elements. For example, silicon, iron, copper, chromium, and nickel are examples of other elements. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).

[1112] (Hole Injection Layer)

[1113] The hole injection layer is a layer containing a substance with high hole injection properties. As the substance with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can be used.

[1114] (Hole Transport Layer)

[1115] The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly (N-vinyl carbazole) (abbreviated as: PVK) and poly (4-vinyl triphenylamine) (abbreviated as: PVTPA) can also be used. Among them, as long as it is a compound with higher hole transport properties than electron transport properties, substances other than them can be used. In addition, the layer containing a substance with high hole transport properties can be not only a single layer, but also a layer stacked with two or more layers formed by the above substances.

[1116] (Guest Material of Light-Emitting Layer)

[1117] The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, highly luminescent substances include fluorescent compounds that emit fluorescence and phosphorescent compounds that emit phosphorescence. Fluorescent compounds are compounds that emit light from a singlet excited state, while phosphorescent compounds are compounds that emit light from a triplet excited state.

[1118] As blue fluorescent materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. As green fluorescent materials that can be used in the light-emitting layer, aromatic amine derivatives can be used. As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used.

[1119] As blue-based phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. As green-based phosphorescent materials that can be used in the light-emitting layer, iridium complexes can be used. As red-based phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used.

[1120] (Host material of light-emitting layer)

[1121] The light-emitting layer may be a structure in which the above-mentioned high-luminescent substance (guest material) is dispersed in another substance (host material). As the material for dispersing the high-luminescent substance, various substances can be used, but preferably a substance having a higher lowest unoccupied molecular orbital energy level (LUMO energy level) and a lower highest occupied molecular orbital energy level (HOMO energy level) than the high-luminescent substance is used.

[1122] As a substance (host material) for dispersing a highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.

[1123] (Electron Transport Layer)

[1124] The electron transport layer is a layer containing a substance with high electron transport properties. Examples of materials that can be used in the electron transport layer include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds.

[1125] (Electron Injection Layer)

[1126] The electron injection layer is a layer containing a substance with high electron injection properties. The electron injection layer can use the compounds that can be used for the electron transport layer, lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline-lithium (Liq) and other metal complex compounds, lithium oxide (LiO x) and other alkali metals, alkaline earth metals, or compounds thereof.

[1127] (cathode)

[1128] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1129] In the organic EL element of one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known formation methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by a known coating method such as vacuum evaporation, molecular beam evaporation (MBE), or dipping a solution in a solvent, spin coating, casting, rod coating, or roller coating.

[1130] In the organic EL device of one embodiment of the present invention, the thickness of each layer is not particularly limited, but is generally preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency.

[1131] [Electronic equipment]

[1132] An electronic device according to one embodiment of the present invention is characterized by including the organic EL element according to one embodiment of the present invention.

[1133] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps. Example

[1134] Next, the present invention will be described in further detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples at all.

[1135] Compounds

[1136] The compound represented by formula (A1) used for producing the organic EL device in the example is shown below.

[1137]

[1138] The comparative compounds used in the production of the organic EL devices of Comparative Examples are shown below.

[1139]

[1140] The compounds represented by formula (10) used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[1141]

[1142]

[1143]

[1144] Other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[1145]

[1146] Production of organic EL devices

[1147] Organic EL devices were produced and evaluated as follows.

[1148] Example 1-1

[1149] (Fabrication of Organic EL Devices)

[1150] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1151] The cleaned glass substrate with a transparent electrode was placed on the substrate holder of a vacuum evaporation apparatus. First, compound HI was deposited onto the surface of the transparent electrode, covering the transparent electrode. This HI film formed a 5 nm thick compound HI film. This HI film functioned as a hole injection layer.

[1152] Compound HT1 was then deposited on the HI film to form an 80 nm thick HT1 film on the HI film. This HT1 film functioned as a first hole transport layer.

[1153] Compound HT2 was then deposited on the HT1 film to form a 10 nm thick HT2 film on the HT1 film. This HT2 film functioned as a second hole transport layer.

[1154] Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the HT2 film so that the proportion (weight ratio) of compound BD-1 reached 2%, forming a light-emitting layer with a thickness of 25 nm.

[1155] Compound HBL was vapor-deposited on the light-emitting layer to form a 10nm-thick electron-transporting layer. Compound ET, an electron-injecting material, was vapor-deposited on the electron-transporting layer to form a 15nm-thick electron-injecting layer. LiF was vapor-deposited on the electron-injecting layer to form a 1nm-thick LiF film. Metal Al was vapor-deposited on the LiF film to form an 80nm-thick metal cathode.

[1156] The device structure of the organic EL device of Example 1 is shown in simplified form as follows.

[1157] ITO(130) / HI(5) / HT1(80) / HT2(10) / BH-1: BD-1(25; 2%) / HBL(10) / ET(15) / LiF(1) / Al(80)

[1158] In addition, the numbers in parentheses represent film thickness (unit: nm).

[1159] (Evaluation of Organic EL Devices)

[1160] At room temperature, at a DC constant current of 50 mA / cm 2 The life characteristics of the obtained organic EL device were measured while driving.

[1161] With a current density of 50 mA / cm 2 Voltage was applied to the resulting organic EL devices in a manner such that the time required for the luminance to reach 95% of the initial luminance was measured. The results are shown in Table 1. The LT95 (hr) values ​​in the table represent relative values, with the LT95 (hr) value of the organic EL device produced in the corresponding comparative example being 100.

[1162] Comparative Example 1-1

[1163] An organic EL device was produced and evaluated in the same manner as in Example 1-1 except that the compound Ref. BD-1 was used as the dopant material. The results are shown in Table 1-1.

[1164] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-1 or Ref. BD-1 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1165]

[1166]

[1167]

[1168]

[1169] Example 2-1 and Comparative Example 1-1

[1170] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-2 or Ref. BD-1 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 12-1.

[1171] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-2 or Ref. BD-1 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1172]

[1173]

[1174]

[1175]

[1176] Example 3-1 and Comparative Example 3-1

[1177] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-3 or Ref. BD-3 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 23-1.

[1178] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-3 or Ref. BD-3 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1179]

[1180]

[1181]

[1182]

[1183] Example 4-1 and Comparative Example 3-1

[1184] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-4 or Ref. BD-3 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 34-1.

[1185] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-4 or Ref. BD-3 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1186]

[1187]

[1188]

[1189]

[1190] Example 5-1 and Comparative Example 5-1

[1191] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-5 or Ref. BD-5 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 45-1.

[1192] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-5 or Ref. BD-5 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1193]

[1194]

[1195]

[1196]

[1197] Example 6-1 and Comparative Example 6-1

[1198] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-6 or Ref. BD-6 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 56-1.

[1199] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-6 or Ref. BD-6 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1200]

[1201]

[1202]

[1203]

[1204] Example 7-1 and Comparative Example 7-1

[1205] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that compound BD-7 or Ref. BD-7 was used as the dopant material and compound BH-1 was used as the host material. The results are shown in Table 67-1.

[1206] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-7 or Ref. BD-7 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1207]

[1208]

[1209]

[1210]

[1211] Example 8-1 and Comparative Example 8-1

[1212] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that compound BD-8 or Ref. BD-8 was used as the dopant material and compound BH-1 was used as the host material. The results are shown in Table 78-1.

[1213] Organic EL devices were prepared and evaluated in the same manner as in Example 1-1, except that compound BD-8 or Ref. BD-8 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1214]

[1215]

[1216]

[1217]

[1218] Example 9-1 and Comparative Example 1-1

[1219] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that Compound BD-9 or Ref. BD-1 was used as the dopant material and Compound BH-1 was used as the host material. The results are shown in Table 89-1.

[1220] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-9 or Ref. BD-1 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1221]

[1222]

[1223]

[1224]

[1225] Example 10-1 and Comparative Example 1-1

[1226] An organic EL device was prepared and evaluated in the same manner as in Example 1-1, except that compound BD-10 or Ref. BD-1 was used as the dopant material and compound BH-1 was used as the host material. The results are shown in Table 100-1.

[1227] Organic EL devices were prepared and evaluated using the same method as in Example 1-1, except that compound BD-10 or Ref. BD-1 was used as the dopant material and the compounds shown in the following tables were used as the host material. The results are shown in the following tables.

[1228]

[1229]

[1230]

[1231]

[1232]

[1233] As shown in the results in the tables above, compounds BD-1 to BD-10 represented by formula (A1) have deuterium atoms and therefore exhibit longer lifespans than their protium-containing counterparts, Ref. BD-1, Ref. BD-3, Ref. BD-5, Ref. BD-6, Ref. BD-7, and Ref. BD-8. This is presumably due to the improved stability of the compounds due to the presence of deuterium atoms.

[1234] <Synthesis of Compounds>

[1235] Synthesis Example 1: Synthesis of Compound BD-1

[1236] Compound BD-1 was synthesized by the following synthetic route.

[1237] [Chemistry 106]

[1238]

[1239] Synthesis of intermediate 1-1

[1240] Under an argon atmosphere, 1-bromobenzene-2,3,4,5,6-d5 (15.0 g, 92.5 mmol), aniline (12.9 g, 138 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 1.27 g, 1.39 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 1.73 g, 2.78 mmol), and NaOt-Bu (17.8 g, 185 mmol) were dissolved in xylene (280 mL) and heated with stirring at 100°C for 5 hours. After the reaction, toluene was added, the mixture was filtered through celite, and the solvent was distilled off. The resulting solid was purified by column chromatography to obtain a white solid (7.40 g, 46% yield). The resulting solid was the target intermediate 1-1. Mass spectrometry analysis revealed an m / e value of 174, corresponding to a molecular weight of 174.

[1241] Synthesis of compound BD-1

[1242] Under an argon atmosphere, the known intermediate 1-2 (synthesized using the method described in US Pat. No. 10,249,832, 739 mg, 1.06 mmol), intermediate 1-1 (387 mg, 2.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 48 mg, 0.053 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 101 mg, 0.211 mmol) were dissolved in xylene (60 mL). A 1M solution of lithium bis(trimethylsilyl)amide (LHMDS) in tetrahydrofuran (2.6 mL, 2.6 mmol) was added, and the mixture was refluxed for 5 hours. After completion of the reaction, methanol was added, the mixture was filtered, and the resulting solid was purified by column chromatography to obtain a yellow solid (681 mg, 86% yield). The obtained solid was the target compound BD-1, and the results of mass spectrometry analysis showed that m / e=748 relative to a molecular weight of 748.

[1243] Synthesis Example 2: Synthesis of Compound BD-2

[1244] Compound BD-2 was synthesized by the following synthetic route.

[1245] [Chemistry 107]

[1246]

[1247] Synthesis of intermediate 2-1

[1248] Under an argon atmosphere, 1-bromobenzene-2,3,4,5,6-d5 (20.8 g, 128 mmol), phenyl-d5-amine (18.9 g, 193 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 1.76 g, 1.93 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 2.40 g, 3.85 mmol), and NaOt-Bu (24.7 g, 257 mmol) were dissolved in xylene (386 mL) and heated with stirring at 100°C for 18 hours. After completion of the reaction, toluene was added, the mixture was filtered through celite, and the solvent was distilled off. The resulting solid was purified by column chromatography to obtain a white solid (9.50 g, 41% yield). The resulting solid was the target intermediate 2-1. Mass spectrometry analysis revealed an m / e value of 179, corresponding to a molecular weight of 179.

[1249] Synthesis of compound BD-2

[1250] Under an argon atmosphere, intermediate 1-2 (739 mg, 1.06 mmol), intermediate 2-1 (398 mg, 2.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 48 mg, 0.053 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 101 mg, 0.211 mmol) were dissolved in xylene (60 mL), and a 1M solution of lithium bis(trimethylsilyl)amide (LHMDS) in tetrahydrofuran (2.6 mL, 2.6 mmol) was added, and the mixture was refluxed for 4 hours. After the reaction was completed, methanol was added, the mixture was filtered, and the resulting solid was purified by column chromatography to obtain a yellow solid (405 mg, yield 51%). The resulting solid was the target compound BD-2, and mass spectrometry analysis showed m / e = 758 relative to a molecular weight of 758.

[1251] Synthesis Example 3: Synthesis of Compound BD-3

[1252] Compound BD-3 was synthesized by the following synthetic route.

[1253] [Chemistry 108]

[1254]

[1255] Synthesis of intermediate 3-1

[1256] Under an argon atmosphere, 4-isopropylphenyltrifluoromethanesulfonic acid (28.7 g, 107 mmol), phenyl-d5-amine (21.0 g, 214 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 1.47 g, 1.60 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 1.53 g, 3.21 mmol), and tripotassium phosphate (45.4 g, 214 mmol) were dissolved in xylene (500 mL) and heated with stirring at 100°C for 20 hours. After the reaction, toluene was added, the mixture was filtered through celite, and the solvent was distilled off. The resulting solid was purified by column chromatography to obtain a white solid (9.50 g, 41% yield). The resulting solid was the target intermediate 3-1. Mass spectrometry analysis revealed an m / e value of 216, corresponding to a molecular weight of 216.

[1257] Synthesis of compound BD-3

[1258] Under an argon atmosphere, intermediate 1-2 (1.60 g, 2.28 mmol), intermediate 3-1 (1.04 g, 4.79 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 104 mg, 0.114 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 218 mg, 0.456 mmol) were dissolved in xylene (120 mL), and a 1M solution of lithium bis(trimethylsilyl)amide (LHMDS) in tetrahydrofuran (5.7 mL, 5.7 mmol) was added, and the mixture was refluxed for 5 hours. After the reaction was completed, methanol was added, the mixture was filtered, and the resulting solid was purified by column chromatography to obtain a yellow solid (1.31 g, yield 69%). The resulting solid was the target compound BD-3, and the results of mass spectrometry analysis showed m / e = 833 relative to a molecular weight of 833.

[1259] Synthesis Example 4: Synthesis of Compound BD-4

[1260] Compound BD-4 was synthesized by the following synthetic route.

[1261] [Chemistry 109]

[1262]

[1263] Compound BD-4 was synthesized in the same manner as in the synthesis of compound BD-3, except that bromobenzene-d5 was used instead of 4-isopropylphenyltrifluoromethanesulfonic acid and 4-isopropylaniline-2,3,5,6-d4 was used instead of benzene-d5-amine as the reaction raw materials.

[1264] Synthesis Example 5: Synthesis of Compound BD-5

[1265] Compound BD-5 was synthesized by the following synthetic route.

[1266] [Chemistry 110]

[1267]

[1268] Compound BD-5 was synthesized in the same manner as compound BD-3, except that bromobenzene-d5 was used instead of 4-isopropylphenyltrifluoromethanesulfonic acid and 5-(tert-butyl)-(1,1′-biphenyl)-2-amine was used instead of benzene-d5-amine as reaction raw materials.

[1269] Synthesis Example 6: Synthesis of Compound BD-6

[1270] Compound BD-6 was synthesized by the following synthetic route.

[1271] [Chemistry 111]

[1272]

[1273] Under an argon atmosphere, the known intermediate 1-3 (1.00 g, 2.11 mmol), phenyl-d5-boronic acid (1.34 g, 10.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 97 mg, 0.106 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 403 mg, 0.845 mmol) and tripotassium phosphate (K3PO4, 2.69 g, 12.7 mmol) were dissolved in xylene (100 mL) and refluxed for 10 hours. After the reaction was completed, methanol was added, filtered, and the resulting solid was purified by column chromatography to obtain a yellow solid (0.45 g, yield 38%). The resulting solid was the target compound BD-6, and the results of mass spectrometry analysis showed m / e = 566 relative to a molecular weight of 566.

[1274] Synthesis Example 7: Synthesis of Compound BD-7

[1275] Compound BD-7 was synthesized by the following synthetic route.

[1276] (1) Synthesis of intermediate B-1

[1277] [Chemistry 112]

[1278]

[1279] The known intermediate A (9.00 g) and 4-tert-butylcyclohexane-1-one (5.38 g) were added to acetic acid (35 mL) and stirred under an argon atmosphere while heating at 100 ° C for 6 hours. Dichloromethane and water were added to the reaction solution, the organic phase was separated, and washed with sodium bicarbonate aqueous solution. After concentration under reduced pressure, column chromatography was used to purify the intermediate B-1 (5.94 g, 50% yield).

[1280] (2) Synthesis of intermediate C-1

[1281] [Chemistry 113]

[1282]

[1283] Intermediate B-1 (6.32 g) and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ; 8.42 g) were added to toluene (90 mL) and heated at 100°C for 3 hours while stirring under an argon atmosphere. The reaction solution was filtered through Celite and purified by column chromatography to obtain Intermediate C-1 (5.50 g, 88% yield).

[1284] (3) Synthesis of intermediate D-1

[1285] [Chemistry 114]

[1286]

[1287] Intermediate C-1 (5.80 g), bis(pinacolato)diboron (13.12 g), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2; 0.25 g), and potassium acetate (3.38 g) were added to 1,4-dioxane (120 mL) and heated at 100°C for 4 hours while stirring under an argon atmosphere. The reaction solution was filtered through celite, the solvent was distilled off, and the resulting solid was purified by column chromatography and recrystallization to obtain intermediate D-1 (3.65 g, 55% yield).

[1288] (4) Synthesis of intermediate E-1

[1289] [Chemistry 115]

[1290]

[1291] Intermediate D-1 (8.37 g), 1,4-dibromo-2,5-diiodobenzene (4.30 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex ((dppf)PdCl2・CH2CH2; 0.29 g), and potassium carbonate (3.66 g) were added to a mixed solvent of toluene (129 mL) and water (65 mL). The mixture was heated at 90°C for 7 hours while stirring under an argon atmosphere. Toluene and water were added to the reaction solution, and the mixture was stirred at room temperature. The organic phase was separated, loaded onto a column chromatography column, and then washed with toluene to obtain Intermediate E-1 (4.42 g, 67% yield).

[1292] (5) Synthesis of intermediate F-1

[1293] [Chemistry 116]

[1294]

[1295] Intermediate E-1 (5.04 g), copper (I) iodide (0.13 g), 1,10-phenanthroline monohydrate (0.24 g), and potassium carbonate (2.33 g) were added to dimethylformamide (DMF; 135 mL) and heated at 100°C for 3 hours while stirring under an argon atmosphere. Water (150 mL) was added to the reaction solution, and the solid was filtered and purified by column chromatography to obtain Intermediate F-1 (3.54 g, 90% yield).

[1296] (6) Synthesis of compound BD-7

[1297] [Chemistry 117]

[1298]

[1299] Compound BD-7 was synthesized in the same manner as in the synthesis of compound BD-6, except that intermediate (F-1) was used as a reaction raw material instead of intermediate (1-3).

[1300] Synthesis Example 8: Synthesis of Compound BD-8

[1301] Compound BD-8 was synthesized by the following synthetic route.

[1302] [Chemistry 118]

[1303]

[1304] To a toluene (80 mL) suspension of intermediate F-1 (1.00 g), bis(phenyl-d5)amine (643 mg), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 78 mg), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (163 mg) was added dropwise a toluene solution of lithium bis(trimethylsilyl)amide (LHMDS) (1 M, 3.5 mL), and the mixture was stirred under an argon atmosphere at 100° C. for 3 hours. The reaction solution was allowed to cool to room temperature, and then purified by column chromatography to obtain compound BD-8 (1.10 g, yield 74%). The molecular weight of compound BD-8 was 871, and the mass spectrometric analysis result of the obtained compound was m / e=871.

[1305] Synthesis Example 9: Synthesis of Compound BD-9

[1306] Compound BD-9 was synthesized by the following synthetic route.

[1307] (1) Synthesis of intermediate F-2

[1308] [Chemistry 119]

[1309]

[1310] Intermediate (F-2) was synthesized by the same method as in Synthesis Example 7 (1) Synthesis of Intermediate B-1 to (5) Synthesis of Intermediate F-1, except that cyclohexanone-d10 was used instead of 4-tert-butylcyclohexane-1-one as the reaction raw material.

[1311] (2) Synthesis of compound BD-9

[1312] [Chemistry 120]

[1313]

[1314] Compound BD-9 was synthesized in the same manner as in the synthesis of compound BD-1, except that intermediate (F-2) was used instead of intermediate (1-2) and diphenylamine was used instead of intermediate (1-1) as reaction raw materials.

[1315] Synthesis Example 10: Synthesis of Compound BD-10

[1316] Compound BD-10 was synthesized by the following synthetic route.

[1317] [Chemistry 121]

[1318]

[1319] Benzene-d6 (20 mL) was added to the known compound Ref. BD-1 (1.00 g) and aluminum chloride (36 mg), and the mixture was heated at 80°C for 30 hours while stirring under an argon atmosphere. The reaction solution was filtered through celite, the solvent was distilled off, and the resulting solid was purified by column chromatography to obtain compound BD-10 (0.34 g, 33% yield).

[1320] While several embodiments and / or examples of the present invention have been described in detail above, it is readily apparent to those skilled in the art that further modifications to these illustrated embodiments and / or examples may be made without departing substantially from the novel teachings and effects of the present invention. Therefore, these further modifications are also encompassed within the scope of the present invention.

[1321] The contents of the documents described in this specification and the applications serving as the basis for the Paris Convention priority claim of this application are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the following formula (A1), [Chemistry 122] In formula (A1), R 21 , R 22 , R1, R2, R4, R6, R7, R 10 , R 11 , R 13 , R 15 and R 16 is a hydrogen atom, R3 and R 12 is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, R5 and R 14 -N(R 906 )(R 907 ) or an unsubstituted aryl group having 6 to 18 ring carbon atoms, R 906 and R 907 are each independently a phenyl group substituted with an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted phenyl group, R 906 and R 907 When there are two or more, two or more R 906 and R 907 Each can be the same or different; R as a hydrogen atom 21 , R 22 , R1, R2, R4, R6, R7, R 10 , R 11 , R 13 , R 15 and R 16 , and R3, R5, R 12 and R 14 One or more of the hydrogen atoms present is a deuterium atom.

2. The compound according to claim 1, wherein R5 and R in formula (A1) 14 It is an unsubstituted aryl group having 6 to 18 ring carbon atoms.

3. The compound according to claim 1, wherein R5 and R in formula (A1) 14 -N(R 906 )(R 907 ), 2-N(R 906 )(R 907 ) 906 , and 2 R 907 The same as each other.

4. The compound according to claim 1 or 2, wherein R3 and R in formula (A1) 12 A hydrogen atom.

5. The compound according to claim 1, wherein The compound represented by formula (A1) is a compound represented by the following formula (A10); [Chemistry 123] In formula (A10), R1~R4、R 10 ~R 13 , R 21 and R 22 As defined in formula (A1) of claim 1; R A , R B , R C and R D Each independently represents a phenyl group substituted with an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted phenyl group.

6. The compound according to claim 5, wherein The compound represented by formula (A10) is a compound represented by the following formula (A11), [Chemistry 124] In formula (A11), R 21 , R 22 , R A , R B , R C and R D As defined in formula (A10) of claim 5.

7. The compound according to claim 5, wherein R A , R B , R C and R D Each independently represents a phenyl group substituted with an unsubstituted alkyl group having 1 to 6 carbon atoms.

8. The compound according to claim 5, wherein R A , R B , R C and R D Each is independently an unsubstituted phenyl group.

9. The compound according to claim 1, wherein In formula (A1), R5 and R 14 -N(R 906 )(R 907 ), R3 and R 12 is a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, R 21 and R 22 is a deuterium atom, R 906 and R 907 As defined in formula (A1) of claim 1.

10. The compound according to claim 1 or 2, wherein In formula (A1), R is a hydrogen atom. 21 and R 22 A deuterium atom.

11. The compound according to claim 1 or 2, wherein In formula (A1), R3 and R4 are unsubstituted alkyl groups having 1 to 6 carbon atoms. 12 One or more of the hydrogen atoms present is a deuterium atom.

12. The compound according to claim 1 or 2, wherein R5 and R 14 One or more of the hydrogen atoms present is a deuterium atom.

13. The compound according to claim 1, wherein The compound represented by formula (A1) is selected from the following compounds, [Chemistry 33] [Chemistry 39] [Chemistry 40] [Chemistry 45] [Chemistry 46] [Chemistry 47] [Chemistry 49] [Chemistry 51] [Chemistry 52] [Chemistry 53] [Chemistry 54] [Chemistry 55] [Chemistry 56] [Chemistry 57] [Chemistry 58] [Chemistry 59] 14. The compound according to claim 1, wherein The compound represented by formula (A1) is selected from the following compounds: 。 15 . A material for an organic electroluminescent device, comprising the compound represented by the formula (A1) according to claim 1 .

16. The material for an organic electroluminescent element according to claim 15, comprising a compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, wherein the content ratio of the former relative to the total is 1 mol% or more.

17. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that the compound contains only protium atoms as hydrogen atoms, the former corresponding to a total content ratio of 30 mol% or more.

18. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, the former corresponding to a total content ratio of 60 mol% or more.

19. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that the compound contains only protium atoms as hydrogen atoms, the former corresponding to a total content ratio of 70 mol% or more.

20. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that only protium atoms are contained as hydrogen atoms, the former corresponding to a total content ratio of 90 mol% or more.

21. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that the compound contains only protium atoms as hydrogen atoms, the former corresponding to a total content ratio of 95 mol% or more.

22. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that only protium atoms are contained as hydrogen atoms are included, and the former corresponds to a total content ratio of 98 mol% or more.

23. The material for an organic electroluminescent element according to claim 15 or 16, wherein The compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that only protium atoms are contained as hydrogen atoms are contained, and the former corresponds to a total content ratio of 99 mol% or more.

24. An organic electroluminescent element having cathode, Anode, and At least one organic layer is disposed between the cathode and the anode, At least one of the at least one organic layer contains the compound represented by the formula (A1) according to any one of claims 1 to 14.

25. The organic electroluminescent element according to claim 24, wherein At least one of the organic layers includes a light-emitting layer, The light-emitting layer contains the compound represented by formula (A1).

26. The organic electroluminescent element according to claim 24 or 25, wherein: The compound represented by formula (A1) functions as a dopant in the light-emitting layer.

27. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 1 mass % or more.

28. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 30 mass % or more.

29. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 60 mass % or more.

30. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 70 mass % or more.

31. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 90 mass % or more.

32. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 95 mass % or more.

33. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 98 mass % or more.

34. The organic electroluminescent element according to claim 24 or 25, wherein: The light-emitting layer contains the compound represented by formula (A1) and a compound having the same structure as the compound represented by formula (A1) except that it contains only protium atoms as hydrogen atoms, and the content ratio of the former relative to the total is 99 mass % or more.

35. An organic electroluminescent element having cathode, Anode, and At least one organic layer is disposed between the cathode and the anode, At least one of the organic layers includes a light-emitting layer, The light-emitting layer contains the compound represented by the formula (A1) according to any one of claims 1 to 14, and A compound represented by the following formula (30); [Chemistry 125] In formula (30), R 101A ~R 108A are each independently a hydrogen atom, L 101 for Single key, or An unsubstituted arylene group having 6 to 18 ring carbon atoms; Ar 101 for unsubstituted aryl group having 6 to 18 ring carbon atoms, or An unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

36. The organic electroluminescent element according to claim 35, wherein The compound represented by formula (30) is a compound in which at least one of the hydrogen atoms possessed by the compound is a deuterium atom.

37. The organic electroluminescent element according to claim 35, wherein Ar in formula (30) 101 At least one of the aryl groups is an unsubstituted aryl group having 6 to 18 ring carbon atoms.

38. The organic electroluminescent element according to claim 35, wherein: Ar in formula (30) 101 At least one of the groups is an unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

39. The organic electroluminescent element according to claim 35, wherein: All Ar in formula (30) 101 is an unsubstituted aryl group having 6 to 18 ring carbon atoms, and multiple Ar 101 They can be the same or different from each other.

40. The organic electroluminescent element according to claim 35, wherein Ar in formula (30) 101 One of them is an unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms, and the remaining Ar 101 is an unsubstituted aryl group having 6 to 18 ring carbon atoms, and multiple Ar 101 They can be the same or different from each other.

41. The organic electroluminescent element according to claim 35, wherein L in formula (30) 101 At least one of them is a single bond.

42. The organic electroluminescent element according to claim 35, wherein: L in formula (30) 101 All are single keys.

43. The organic electroluminescent element according to claim 35, wherein: L in formula (30) 101 At least one of the groups is an unsubstituted arylene group having 6 to 18 ring carbon atoms.

44. The organic electroluminescent element according to claim 35, wherein L in formula (30) 101 At least one of them is an unsubstituted phenylene group or an unsubstituted naphthylene group.

45. The organic electroluminescent element according to claim 35, wherein -L in formula (30) 101 -Ar 101 The groups shown are selected from Unsubstituted phenyl, Unsubstituted naphthyl, Unsubstituted biphenyl, Unreplaced Fiki, unsubstituted dibenzofuranyl, and Unsubstituted naphthobenzofuranyl.

46. ​​The organic electroluminescent element according to claim 35, wherein The compound represented by the formula (30) contains substantially only protium atoms as hydrogen atoms.

47. The organic electroluminescent element according to claim 35, wherein: The compound represented by formula (30) is a compound represented by the following formula (30D), [Chemistry 80] In formula (30D), R 101A ~R 108A , L 101 and Ar 101 As defined in formula (30) of claim 35, Among them, R as a hydrogen atom 101A ~R 108A , L 101 The hydrogen atoms and Ar 101 The hydrogen atoms At least one of them is a deuterium atom.

48. The organic electroluminescent element according to claim 47, wherein In formula (30D), R is a hydrogen atom. 101A ~R 108A At least one of them is a deuterium atom.

49. The organic electroluminescent element according to claim 35, wherein The compound represented by formula (30) is a compound represented by the following formula (31), [Chemistry 68] In formula (31), L 101 and Ar 101 As defined in formula (30) of claim 35, R 101A ~R 108A As defined in formula (30) of claim 35, X b is O, or S, R 121 ~R 128 One of them is the same as L 101 Bonded single bonds, Not with L 101 R of the bonded single bond 121 ~R 128 In one or more groups of two or more adjacent groups, one or more of them form an unsubstituted saturated or unsaturated ring, or do not form an unsubstituted saturated or unsaturated ring, Not with L 101 R is a single bond that is bonded to the alkylene group and does not form an unsubstituted saturated or unsaturated ring. 121 ~R 128 are each independently a hydrogen atom.

50. The organic electroluminescent element according to claim 47, wherein The compound represented by formula (30D) is a compound represented by the following formula (31D), [Chemistry 81] In formula (31D), R 101A ~R 108A , L 101 and Ar 101 As defined in formula (30D) of claim 47, X d is O or S, R 121 ~R 128 One of them is the same as L 101 Bonded single bonds, Not with L 101 R of the bonded single bond 121 ~R 128 In one or more groups of two or more adjacent groups, one or more groups form an unsubstituted saturated or unsaturated ring, or do not form an unsubstituted saturated or unsaturated ring, Not with L 101 R is a single bond that is bonded to the alkylene group and does not form an unsubstituted saturated or unsaturated ring. 121 ~R 128 are each independently a hydrogen atom, Among them, R as a hydrogen atom 101A ~R 108A , L 101 The hydrogen atoms Ar 101 The hydrogen atoms and R as a hydrogen atom 121 ~R 128 At least one of them is a deuterium atom.

51. The organic electroluminescent element according to claim 50, wherein: The compound represented by formula (31D) is a compound represented by the following formula (32D), [Chemistry 82] In formula (32D), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 As defined in formula (31D) of claim 50, in, R as a hydrogen atom 101A ~R 108A , R as a hydrogen atom 125A ~R 128A , The hydrogen atom bonded to the carbon atom of the dibenzofuran skeleton in formula (32D), L 101 The hydrogen atoms and Ar 101 The hydrogen atoms At least one of them is a deuterium atom.

52. The organic electroluminescent element according to claim 51, wherein The compound represented by formula (32D) is a compound represented by the following formula (32D-1) or (32D-2), [Chemistry 83] In formula (32D-1) and (32D-2), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is defined in formula (32D) of claim 51, in, R as a hydrogen atom 101A ~R 108A , R as a hydrogen atom 125A ~R 128A , The hydrogen atom bonded to the carbon atom of the dibenzofuran skeleton in formula (32D-1) and (32D-2), L 101 The hydrogen atoms and Ar 101 The hydrogen atoms At least one of them is a deuterium atom.

53. The organic electroluminescent element according to claim 49, wherein The compound represented by formula (31) is a compound represented by the following formula (33), [Chemistry 70] In formula (33), R 101A ~R 108A , L 101 ,Ar 101 , and R 121 ~R 128 As defined in formula (31) of claim 49, X c For O, R 131 As defined in formula (31) of claim 49.

54. The organic electroluminescent element according to claim 49, wherein The compound represented by formula (31) is a compound represented by the following formula (35), [Chemistry 72] In formula (35), R 101A ~R 108A , L 101 ,Ar 101 and X b As defined in formula (31) of claim 49, R 121A ~R 124A Two or more adjacent groups of R are not bonded to each other to form an unsubstituted saturated or unsaturated ring, 125B and R 126B , R 126B and R 127B , and R 127B and R 128B Any one of the groups in the formula (35a) is bonded to each other to form a ring represented by the following formula (35a), [Chemistry 73] In formula (35a), 2* each with R 125B and R R126B , R 126B and R 127B , and R 127B and R 128B For any bond in R 141 ~R 144 are each independently a hydrogen atom, R 121A ~R 124A , and R which does not form a ring represented by formula (35a) 125B ~R 128B One of them is the same as L 101 Bonded single bonds, Not with L 101 R of the bonded single bond 121A ~R 124A , and not with L 101 R is a single bond that is bonded to the ring represented by formula (35a) and does not form 125B ~R 128B are each independently a hydrogen atom.

55. The organic electroluminescent element according to claim 54, wherein The compound represented by formula (35) is a compound represented by the following formula (36), [Chemistry 74] In formula (36), R 101A ~R 108A , L 101 ,Ar 101 , and R 125B ~R 128B As defined in formula (35) of claim 54.

56. The organic electroluminescent element according to claim 49, wherein The compound represented by formula (31) is a compound represented by the following formula (37), [Chemistry 75] In formula (37), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 As defined in formula (31) of claim 49.

57. The organic electroluminescent element according to any one of claims 35 to 56, wherein The compounds represented by formulae (30) to (33) and (35) to (37) include compounds in which at least one of the hydrogen atoms possessed by these compounds is a deuterium atom.

58. The organic electroluminescent element according to any one of claims 35 to 56, wherein In the compounds represented by formulae (30) to (33) and (35) to (37), at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton is a deuterium atom.

59. The organic electroluminescent element according to claim 35, wherein The compound represented by formula (10) is a compound selected from the following group, [Chemistry 88] [Chemistry 89] [Chemistry 90] [Chemistry 91] [Chemistry 92] [Chemistry 93] [Chemistry 94] [Chemistry 95] [Chemistry 96] [Chemistry 97] [Chemistry 98] [Chemistry 99] 60. The organic electroluminescent element according to claim 35, wherein: The compound represented by formula (10) is a compound selected from the following group, [Chemistry 102] [Chemistry 103] [Chemistry 104] 61. The organic electroluminescent element according to claim 24 or 35, wherein: There is a hole transport domain between the anode and the light-emitting layer.

62. The organic electroluminescent element according to claim 24 or 35, wherein: An electron transport domain is provided between the cathode and the light emitting layer.

63. An electronic device comprising the organic electroluminescent element according to any one of claims 24 to 62.

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