Compound, organic electroluminescent element and electronic device

Abstract

A compound represented by formula (1) having at least one deuterium atom. In formula (1), n ​​is 1 to 4, L1 is a divalent group or a group shown in formula (11), and R... 111 ~R 119 and R 211 ~R 219 Each is an independent hydrogen atom or substituent. It should be noted that the compound shown in formula (1) does not have -N(R) 906 (R) 907 The group shown in the figure, R 906 and R 907 Each is independently a hydrogen atom or an alkyl group having 1 to 50 carbon atoms. In formula (11), X 13 Each of Y1 to Y8 is an oxygen or sulfur atom, and each of them is independently a CR atom. 300 Or nitrogen atom, R 300 Two of them are single bonds that bond with *a or other L1 bonds, or single bonds that bond with *b or other L1 bonds.

Description

Technical Field

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

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

[0003] To improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 to 5). Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0004] Prior art literature

[0005] Patent Literature

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

[0007] Patent Document 2: International Publication No. 2005 / 115950

[0008] Patent Document 3: International Publication No. 2011 / 077691

[0009] Patent Document 4: Japanese Patent Application Laid-Open No. 2018-125504

[0010] Patent Document 5: U.S. Patent Application Publication No. 2019 / 280209 Summary of the Invention

[0011] Problems to be solved by the invention

[0012] An object of the present invention is to provide a compound capable of extending life, an organic electroluminescent device using the compound, and an electronic device equipped with the organic electroluminescent device.

[0013] Means used to solve problems

[0014] According to one embodiment of the present invention, there is provided a compound represented by the following general formula (1) having at least one deuterium atom.

[0015]

Chemical Formula 1

[0016]

[0017] (In the above general formula (1), n ​​is 1, 2, 3 or 4. When n is 2, 3 or 4, a plurality of L1 are the same or different from each other.

[0018] L1 is free from selection

[0019] substituted or unsubstituted phenyl,

[0020] Substituted or unsubstituted biphenyl,

[0021] Substituted or unsubstituted terphenyl,

[0022] substituted or unsubstituted naphthyl,

[0023] Substituted or unsubstituted phenoxy,

[0024] Substituted or unsubstituted base,

[0025] Substituted or unsubstituted triphenylene,

[0026] substituted or unsubstituted fluorenyl,

[0027] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0028] Substituted or unsubstituted 9,9-dimethylfluorenyl, and

[0029] A divalent group derived by removing one hydrogen atom from any of the groups consisting of substituted or unsubstituted 9,9-diphenylfluorenyl, or

[0030] The group represented by the following general formula (11),

[0031] R 111 ~R 119 and R 211 ~R 219 Each independently

[0032] hydrogen atoms,

[0033] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0035] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0036] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0037] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0038] -Si(R 901 )(R902 )(R 903 ) shown in the group,

[0039] -O-(R 904 ) shown in the group,

[0040] -S-(R 905 ) shown in the group,

[0041] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0042] -C(=O)R 801 The groups shown,

[0043] -COOR 802 The groups shown,

[0044] Halogen atoms,

[0045] cyano,

[0046] Nitro,

[0047] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0048] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0049] The compound represented by the general formula (1) does not have -N(R 906 )(R 907 ) shown in the group, R 906 and R 907 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0050]

Chemical Formula 2

[0051]

[0052] (In the above general formula (11), X 13 is an oxygen atom or a sulfur atom, and Y1 to Y8 are each independently CR 300 or nitrogen atoms,

[0053] Multiple R 300 Same or different from each other,

[0054] Multiple R 300 One or more groups of two or more adjacent

[0055] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0056] bonded to each other to form a substituted or unsubstituted fused ring, or

[0057] Not bonded to each other,

[0058] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 300 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0059] R does not form the above-mentioned substituted or unsubstituted monocyclic ring, does not form the above-mentioned substituted or unsubstituted condensed ring, and is not a single bond to *a, *b or other L1 in the above-mentioned general formula (1); 300 are each independently a hydrogen atom,

[0060] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0061] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0062] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0063] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0064] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0065] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0066] -O-(R 904 ) shown in the group,

[0067] -S-(R 905 ) shown in the group,

[0068] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0069] -C(=O)R 801 The groups shown,

[0070] -COOR 802 The groups shown,

[0071] Halogen atoms,

[0072] cyano,

[0073] Nitro,

[0074] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0075] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0076] (In the compound represented by the above general formula (1), R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each independently

[0077] hydrogen atoms,

[0078] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0079] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0080] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0081] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0082] In R 901 When there are multiple R 901 Same or different from each other,

[0083] In R 902 When there are multiple R 902 Same or different from each other,

[0084] In R 903 When there are multiple R 903 Same or different from each other,

[0085] In R 904 When there are multiple R 904 Same or different from each other,

[0086] In R 905 When there are multiple R 905 Same or different from each other,

[0087] In R 801 When there are multiple R 801 Same or different from each other,

[0088] In R 802 When there are multiple R 802 Same as or different from each other.)

[0089] According to one embodiment of the present invention, there is provided an organic electroluminescent element comprising:

[0090] anode,

[0091] cathode, and

[0092] a light-emitting layer included between the anode and the cathode,

[0093] The light-emitting layer contains the compound according to one embodiment of the present invention as compound M2.

[0094] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to the above-mentioned aspect of the present invention.

[0095] According to one embodiment of the present invention, a compound capable of extending life, an organic electroluminescent device using the compound, and an electronic device equipped with the organic electroluminescent device can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0096] Figure 1 This is a diagram schematically showing the configuration of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0097] Figure 2 This is a diagram schematically showing the configuration of an example of an organic electroluminescent element according to a fourth embodiment of the present invention. DETAILED DESCRIPTION

[0098] [definition]

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

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

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

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

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

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

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

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

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

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

[0109] "Substituents described in this specification"

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

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

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

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

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

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

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

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

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

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

[0120] "Substituted or unsubstituted aryl"

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

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

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

[0124] Phenyl,

[0125] p-Biphenyl,

[0126] m-Biphenyl,

[0127] o-biphenyl,

[0128] 4-terphenyl-4-yl,

[0129] 4-terphenyl-3-yl,

[0130] 4-terphenyl-2-yl,

[0131] m-terphenyl-4-yl,

[0132] m-terphenyl-3-yl,

[0133] m-terphenyl-2-yl,

[0134] o-terphenyl-4-yl,

[0135] o-terphenyl-3-yl,

[0136] o-terphenyl-2-yl,

[0137] 1-naphthyl,

[0138] 2-naphthyl,

[0139] Anthracene,

[0140] Benzanthryl,

[0141] Fiki,

[0142] Triphenylene,

[0143] Phenalene,

[0144] Pyrene base,

[0145] base,

[0146] Benzo base,

[0147] triphenylene,

[0148] Benzotriphenylene,

[0149] tetraphenyl,

[0150] Pentaphenyl,

[0151] Fluorenyl,

[0152] 9,9'-spirobifluorenyl,

[0153] Benzofluorenyl,

[0154] Dibenzofluorenyl,

[0155] Fluoranthene group,

[0156] Benzofluoranthene,

[0157] Perylene and

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

[0159]

Chemical Formula 3

[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 a monovalent group derived from the ring structure represented by the above-mentioned general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

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

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

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

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

[0195] Pyrrolyl,

[0196] Imidazole,

[0197] pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenazinyl,

[0198] Carbazolyl,

[0199] Benzylcarbazolyl,

[0200] Morpholinyl,

[0201] Phenoxazine,

[0202] Phenothiazine,

[0203] Azacarbazolyl, and

[0204] Diazacarbazolyl.

[0205] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0206] furanyl,

[0207] Oxazolyl,

[0208] Isoxazolyl,

[0209] Oxadiazolyl,

[0210] Xanthoxylum,

[0211] Benzofuranyl,

[0212] Isobenzofuranyl,

[0213] dibenzofuranyl,

[0214] naphthobenzofuranyl,

[0215] Benzoxazolyl,

[0216] Benzisoxazolyl,

[0217] Phenoxazine,

[0218] Morpholinyl,

[0219] dinaphthofuranyl,

[0220] Azadibenzofuranyl,

[0221] Diazadibenzofuranyl,

[0222] Azanaphthobenzofuranyl and

[0223] naphthyridinylbenzofuranyl.

[0224] Unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3):

[0225] Thiphenyl,

[0226] Thiazolyl,

[0227] Isothiazolyl,

[0228] Thiadiazole,

[0229] benzothienyl,

[0230] Isobenzothienyl,

[0231] dibenzothienyl,

[0232] naphthobenzothienyl,

[0233] Benzothiazolyl,

[0234] Benzisothiazolyl,

[0235] Phenothiazine,

[0236] dinaphthothienyl,

[0237] azadibenzothienyl,

[0238] diazadibenzothienyl,

[0239] azanaphthobenzothienyl and

[0240] diazanaphthobenzothienyl.

[0241] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):

[0242]

Chemical Formula 5

[0243]

[0244]

Chemical Formula 6

[0245]

[0246] 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.

[0247] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0248] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0249] (9-phenyl)carbazolyl,

[0250] (9-biphenyl)carbazolyl,

[0251] (9-phenyl)phenylcarbazolyl,

[0252] (9-naphthyl)carbazolyl,

[0253] Diphenylcarbazol-9-yl,

[0254] phenylcarbazol-9-yl,

[0255] Methylbenzimidazole,

[0256] Ethylbenzimidazolyl,

[0257] Phenyltriazine,

[0258] Biphenyl triazine group,

[0259] Diphenyltriazine,

[0260] Phenylquinazolinyl, and

[0261] Biphenylquinazolinyl.

[0262] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0263] Phenyldibenzofuranyl,

[0264] Methyldibenzofuranyl,

[0265] tert-Butyldibenzofuranyl and

[0266] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0267] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0268] Phenyldibenzothiophene,

[0269] Methyldibenzothiophene,

[0270] tert-Butyldibenzothienyl and

[0271] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0272] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific Example Group G2B4):

[0273] The above-mentioned “one or more hydrogen atoms of the monovalent heterocyclic group” means one or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.

[0274] "Substituted or unsubstituted alkyl"

[0275] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, unsubstituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "unsubstituted alkyl groups," and substituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "substituted alkyl groups.") Hereinafter, when simply referring to "alkyl groups," both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0276] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0277] Unsubstituted alkyl (Specific example group G3A):

[0278] methyl,

[0279] Ethyl,

[0280] n-propyl,

[0281] Isopropyl,

[0282] n-Butyl,

[0283] Isobutyl,

[0284] sec-butyl and

[0285] tert-butyl.

[0286] Substituted alkyl (specific example group G3B): heptafluoropropyl (including isomers),

[0287] Pentafluoroethyl,

[0288] 2,2,2-trifluoroethyl and

[0289] trifluoromethyl.

[0290] "Substituted or unsubstituted alkenyl"

[0291] Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (Specific Example Group G4) include the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B). (Herein, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" alone includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups."

[0292] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0293] Unsubstituted alkenyl (Specific example Group G4A):

[0294] Vinyl,

[0295] Allyl,

[0296] 1-butenyl,

[0297] 2-Butenyl and

[0298] 3-Butenyl.

[0299] Substituted alkenyl (Specific example group G4B):

[0300] 1,3-butadienyl,

[0301] 1-Methylvinyl,

[0302] 1-methylallyl,

[0303] 1,1-dimethylallyl,

[0304] 2-methylallyl and

[0305] 1,2-dimethylallyl.

[0306] "Substituted or unsubstituted alkynyl"

[0307] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Herein, unsubstituted alkynyl groups refer to cases where "substituted or unsubstituted alkynyl groups" are "unsubstituted alkynyl groups.") When simply referring to "alkynyl groups" below, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0308] A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (Specific Example Group G5A) are replaced with a substituent.

[0309] Unsubstituted alkynyl (Specific example group G5A):

[0310] ethynyl

[0311] "Substituted or unsubstituted cycloalkyl"

[0312] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups (Specific Example Group G6A) and substituted cycloalkyl groups (Specific Example Group G6B). (Herein, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referring to a "cycloalkyl group", both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" are included.

[0313] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0314] Unsubstituted cycloalkyl (Specific example group G6A):

[0315] Cyclopropyl,

[0316] Cyclobutyl,

[0317] Cyclopentyl,

[0318] Cyclohexyl,

[0319] 1-adamantyl,

[0320] 2-adamantyl,

[0321] 1-Norbornyl and

[0322] 2-Norbornyl.

[0323] Substituted cycloalkyl (specific example group G6B):

[0324] 4-Methylcyclohexyl.

[0325] ·“-Si(R 901 )(R 902 )(R 903 )”

[0326] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as specific examples (specific example group G7), and include

[0327] -Si(G1)(G1)(G1),

[0328] -Si(G1)(G2)(G2),

[0329] -Si(G1)(G1)(G2),

[0330] -Si(G2)(G2)(G2),

[0331] -Si(G3)(G3)(G3) and

[0332] -Si(G6)(G6)(G6). Here,

[0333] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0334] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0335] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0336] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0337] A plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0338] A plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0339] A plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0340] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0341] Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0342] A plurality of G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0343] ·“-O-(R 904 )”

[0344] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and the following are examples:

[0345] -O(G1),

[0346] -O(G2),

[0347] -O(G3) and

[0348] -O(G6).

[0349] Here,

[0350] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0351] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0352] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0353] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0354] ·“-S-(R 905 )”

[0355] As -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0356] -S(G1),

[0357] -S(G2),

[0358] -S(G3) and

[0359] -S(G6).

[0360] Here,

[0361] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0362] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0363] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0364] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0365] ·“-N(R 906 )(R 907 )”

[0366] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0367] -N(G1)(G1),

[0368] -N(G2)(G2),

[0369] -N(G1)(G2),

[0370] -N(G3)(G3) and

[0371] -N(G6)(G6).

[0372] Here,

[0373] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0374] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0375] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0376] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0377] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0378] - A plurality of G2s in N(G2)(G2) are the same as or different from each other.

[0379] - A plurality of G3's in N(G3)(G3) are the same as or different from each other.

[0380] A plurality of G6's in -N(G6)(G6) are the same as or different from each other.

[0381] "Halogen atoms"

[0382] 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.

[0383] "Substituted or unsubstituted fluoroalkyl"

[0384] The “substituted or unsubstituted fluoroalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted fluoroalkyl group” refers to a group in which one or more hydrogen atoms of the “fluoroalkyl group” are replaced with a substituent. It should be noted that the “substituted fluoroalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted fluoroalkyl group” are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0385] "Substituted or unsubstituted haloalkyl"

[0386] The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with halogen atoms. The number of carbon atoms in the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted haloalkyl group” refers to a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. It should be noted that the “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted haloalkyl group” are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl groups" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0387] "Substituted or unsubstituted alkoxy"

[0388] A specific example of a "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0389] "Substituted or unsubstituted alkylthio"

[0390] A specific example of a "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in an "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0391] "Substituted or unsubstituted aryloxy group"

[0392] Specific examples of "substituted or unsubstituted aryloxy groups" described in this specification include groups represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring carbon atoms in the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0393] "Substituted or unsubstituted arylthio"

[0394] Specific examples of "substituted or unsubstituted arylthio groups" described in this specification include groups represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the number of ring carbon atoms in an "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0395] "Substituted or unsubstituted trialkylsilyl"

[0396] A specific example of a "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0397] "Substituted or unsubstituted aralkyl"

[0398] A specific example of a "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group." The number of carbon atoms in an "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0399] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0400] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0401] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthroline group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0402] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0403]

Chemical Formula 7

[0404]

[0405] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0406]

Chemical Formula 8

[0407]

[0408] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0409] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0410]

Chemical Formula 9

[0411]

[0412] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0413] 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.

[0414] "Substituted or unsubstituted arylene group"

[0415] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (Specific Example Group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in Specific Example Group G1 by removing one hydrogen atom from the aryl ring.

[0416] "Substituted or unsubstituted divalent heterocyclic group"

[0417] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 by removing one hydrogen atom from the heterocyclic ring.

[0418] "Substituted or unsubstituted alkylene"

[0419] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0420] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0421]

Chemical Formula 10

[0422]

[0423]

Chemical Formula 11

[0424]

[0425] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0426] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0427]

Chemical Formula 12

[0428]

[0429] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0430] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0431] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0432]

Chemical Formula 13

[0433]

[0434] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0435] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0436] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0437]

Chemical Formula 14

[0438]

[0439]

Chemical Formula 15

[0440]

[0441]

Chemical Formula 16

[0442]

[0443] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0444]

Chemical Formula 17

[0445]

[0446]

Chemical Formula 18

[0447]

[0448]

Chemical Formula 19

[0449]

[0450]

Chemical Formula 20

[0451]

[0452] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0453] The above is the description of the “substituents described in the present specification”.

[0454] "When bonding to form a ring"

[0455] In this specification, the expression "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring", "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted condensed ring", and "one or more of the adjacent groups of two or more are not bonded to each other".

[0456] The following describes the case where "one or more of a group of two or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of a group of two or more adjacent groups are bonded to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case where they are bonded to form a ring"). This description is based on the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring.

[0457]

Chemical Formula 21

[0458]

[0459] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups as one group refers to R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0460] The above “one or more groups” means that two or more groups of the above two or more adjacent groups can form a ring at the same time. 921 With R 922 bonded to form ring Q A And at the same time R 925 With R 926 bonded to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0461]

Chemical Formula 22

[0462]

[0463] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups is bonded as in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, R 921 With R 922 bonded to form ring Q A , and R 922 With R 923 bonded to form ring Q C , consisting of three adjacent (R 921 、R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0464]

Chemical Formula 23

[0465]

[0466] In the formed "monocyclic ring" or "condensed ring", the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q formed A and Ring Q B Each is a "monocyclic" or "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) is A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0467] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0468] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0469] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified in Specific Example Group G2 are terminated with hydrogen atoms.

[0470] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0471] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A Refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Formation of ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0472] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur, as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by a hydrogen atom or the like, or can be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocycle.

[0473] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0474] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0475] In this specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0476] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0477] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0478] In the case of "one or more groups consisting of two or more adjacent atoms" "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms bond to each other to form a substituted or unsubstituted "unsaturated ring" formed from multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0479] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in the present specification".

[0480] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0481] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" ("the case where they are bonded to form a ring").

[0482] Substituents when expressed as "substituted or unsubstituted"

[0483] In one embodiment of the present specification, the substituent described as "substituted or unsubstituted" (in this specification, sometimes referred to as "optional substituent") is, for example, selected from an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0484] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0485] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0486] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0487] -Si(R 901 )(R 902 )(R 903 ),

[0488] -O-(R 904 ),

[0489] -S-(R 905 ),

[0490] -N(R 906 )(R 907 ),

[0491] Halogen atoms, cyano groups, nitro groups,

[0492] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0493] unsubstituted heterocyclic group having 5 to 50 ring atoms

[0494] The groups in the group etc.

[0495] Here, R 901 ~R 907 Each independently

[0496] hydrogen atoms,

[0497] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0498] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0499] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0500] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0501] R 901 When there are two or more, two or more R 901 Same or different from each other,

[0502] R 902 When there are two or more, two or more R 902 Same or different from each other,

[0503] R 903 When there are two or more, two or more R 903 Same or different from each other,

[0504] R 904 When there are two or more, two or more R 904 Same or different from each other,

[0505] R 905 When there are two or more, two or more R 905 Same or different from each other,

[0506] R 906 When there are two or more, two or more R 906 Same or different from each other,

[0507] R 907 When there are two or more, two or more R907 Same as or different from each other.

[0508] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0509] an alkyl group having 1 to 50 carbon atoms,

[0510] an aryl group having 6 to 50 ring carbon atoms and

[0511] A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0512] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0513] an alkyl group having 1 to 18 carbon atoms,

[0514] an aryl group having 6 to 18 ring carbon atoms and

[0515] A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0516] Specific examples of each of the above-mentioned optional substituents are the same as the specific examples of the substituents described in the above-mentioned section "Substituents described in the present specification".

[0517] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0518] 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.

[0519] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit and the numerical value BB described after "AA to BB" as the upper limit.

[0520] [First embodiment]

[0521] [Compound]

[0522] The compound according to this embodiment is a compound represented by the following general formula (1) and having at least one deuterium atom.

[0523]

Chemical Formula 24

[0524]

[0525] (In the above general formula (1), n ​​is 1, 2, 3 or 4. When n is 2, 3 or 4, a plurality of L1 are the same or different from each other.

[0526] L1 is free from selection

[0527] substituted or unsubstituted phenyl,

[0528] Substituted or unsubstituted biphenyl,

[0529] Substituted or unsubstituted terphenyl,

[0530] substituted or unsubstituted naphthyl,

[0531] Substituted or unsubstituted phenoxy,

[0532] Substituted or unsubstituted base,

[0533] Substituted or unsubstituted triphenylene,

[0534] substituted or unsubstituted fluorenyl,

[0535] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[0536] Substituted or unsubstituted 9,9-dimethylfluorenyl, and

[0537] A divalent group derived by removing one hydrogen atom from any of the groups consisting of substituted or unsubstituted 9,9-diphenylfluorenyl groups, or

[0538] The group represented by the following general formula (11),

[0539] R 111 ~R 119 and R 2H ~R 219 Each independently

[0540] hydrogen atoms,

[0541] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0543] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0544] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0545] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0546] -Si(R 901 )(R 902 )(R903 ) shown in the group,

[0547] -O-(R 904 ) shown in the group,

[0548] -S-(R 905 ) shown in the group,

[0549] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0550] -C(=O)R 801 The groups shown,

[0551] -COOR 802 The groups shown,

[0552] Halogen atoms,

[0553] cyano,

[0554] Nitro,

[0555] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0556] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0557] The compound represented by the general formula (1) does not have -N(R 906 )(R 907 ) shown in the group, R 906 and R 907 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0558]

Chemical Formula 25

[0559]

[0560] (In the above general formula (11), X 13 is an oxygen atom or a sulfur atom, and Y1 to Y8 are each independently CR 300 or nitrogen atoms,

[0561] Multiple R 300 Same or different from each other,

[0562] Multiple R 300 One or more groups of two or more adjacent

[0563] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0564] bonded to each other to form a substituted or unsubstituted fused ring, or

[0565] Not bonded to each other,

[0566] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 300 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0567] R does not form the above-mentioned substituted or unsubstituted monocyclic ring, does not form the above-mentioned substituted or unsubstituted condensed ring, and is not a single bond to *a, *b or other L1 in the above-mentioned general formula (1); 300 are each independently a hydrogen atom,

[0568] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0569] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[0570] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0571] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0572] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0573] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0574] -O-(R 904 ) shown in the group,

[0575] -S-(R 905 ) shown in the group,

[0576] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0577] -C(=O)R 801 The groups shown,

[0578] -COOR 802 The groups shown,

[0579] Halogen atoms,

[0580] cyano,

[0581] Nitro,

[0582] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0583] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0584] (In the compound represented by the above general formula (1), R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each independently

[0585] hydrogen atoms,

[0586] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0587] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0588] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0589] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0590] In R 901 When there are multiple R 901 Same or different from each other,

[0591] In R 902 When there are multiple R 902 Same or different from each other,

[0592] In R 903 When there are multiple R 903 Same or different from each other,

[0593] In R 904 When there are multiple R 904 Same or different from each other,

[0594] In R 905 When there are multiple R 905 Same or different from each other,

[0595] In R 801 When there are multiple R 801 Same or different from each other,

[0596] In R 802 When there are multiple R 802 Same as or different from each other.)

[0597] In this specification, "a compound represented by the above general formula (1) and having at least one deuterium atom" means a compound (the compound represented by the above general formula (1)) in which not all hydrogen atoms are protium atoms.

[0598] In the present specification, among the total number of hydrogen atoms possessed by the compound (the compound represented by the above-mentioned general formula (1)), preferably 10% or more are deuterium atoms, preferably 20% or more are deuterium atoms, preferably 30% or more are deuterium atoms, preferably 40% or more are deuterium atoms, preferably 50% or more are deuterium atoms, preferably 60% or more are deuterium atoms, preferably 70% or more are deuterium atoms, and preferably 80% or more are deuterium atoms.

[0599] Methods for confirming the presence of deuterium atoms in compounds and methods for determining the bonding positions of deuterium atoms in compounds

[0600] Compounds containing deuterium atoms are analyzed by mass spectrometry or 1 The binding position of the deuterium atom in the compound was confirmed by H-NMR analysis. 1 The results were confirmed by H-NMR analysis.

[0601] Specifically, the target compound was subjected to mass spectrometry analysis and compared with a corresponding compound in which all hydrogen atoms were protium atoms. The molecular weight increased by 1, indicating that it contained one deuterium atom. 1 No signal was found in the H-NMR analysis, so the target compound was 1 The integral value obtained by H-NMR analysis was used to confirm the number of deuterium atoms contained in the molecule. 1 H-NMR analysis determines the bonding position of the deuterium atom by assigning the signals.

[0602] In the compound of this embodiment, n is preferably 1, 2 or 3.

[0603] In the compound of this embodiment, n is more preferably 1 or 2.

[0604] In the compounds of this embodiment, preferably, L1 is a divalent group derived by removing one hydrogen atom from any group selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group and a substituted or unsubstituted 9,9-diphenylfluorenyl group, or a group represented by the above-mentioned general formula (11).

[0605] In the compound of this embodiment, the group represented by the above-mentioned general formula (11) is preferably a group represented by the following general formula (12).

[0606]

Chemical Formula 26

[0607]

[0608] (In the above general formula (12), X 13 With X in the above general formula (11) 13 Same meaning,

[0609] R 311 ~R 318 One or more groups of two or more adjacent

[0610] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0611] bonded to each other to form a substituted or unsubstituted fused ring, or

[0612] Not bonded to each other,

[0613] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 311 ~R 318 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0614] R does not form the above-mentioned substituted or unsubstituted monocyclic ring, does not form the above-mentioned substituted or unsubstituted condensed ring, and is not a single bond to *a, *b or other L1 in the above-mentioned general formula (1); 311 ~R 318 Each independently and R3 in the above general formula (11) 00 Same meaning.)

[0615] Generally, it is known that when a compound is deuterated, the life of a device is prolonged.

[0616] The compound according to this embodiment is a deuterated compound, and the group connecting the two pyrene rings is a specific linking group L1, thereby achieving a longer device life. For example, compounds whose linking group L1 in the general formula (1) is an electron-rich substituent such as a carbazolyl group are prone to reaction during film formation for device fabrication. Therefore, even if deuterated, the effect of extending the device life may be limited, and therefore are excluded from the linking group L1 in the general formula (1).

[0617] On the other hand, in order to improve production efficiency when mass-producing organic EL elements, sometimes high speed (for example, evaporation speed) is used. ) to form an organic layer such as a light-emitting layer. For example, when the linking group L1 in the general formula (1) is a non-electron-rich substituent such as an aryl group, a reaction during film formation is avoided. Therefore, when the light-emitting layer is formed at a high speed, a further effect of extending the life due to deuteration can be expected.

[0618] It is believed that by setting the linking group L1 to a group represented by general formula (11) or a heteroarylene group such as a carbazolylene group, the compound represented by general formula (1) will not become electron-rich, and will be less likely to react during high-speed film formation, thereby easily improving the device life.

[0619] Therefore, the linking group L1 is preferably an arylene group. However, it has been found that among arylene groups, when a compound having a linking group with a small number of ring carbon atoms (small molecular weight) such as a 9,9-dimethylfluorene ring is used to form a light-emitting layer at a high speed, the effect of extending the lifespan due to deuteration is further demonstrated compared to when a compound having a linking group with a large number of ring carbon atoms (large molecular weight) such as a benzospirofluorene ring is used to form a light-emitting layer at a high speed.

[0620] It is believed that when an arylene group having a large number of ring carbon atoms (large molecular weight) is used as a connecting group, the compound represented by the general formula (1) is placed in an environment where thermal decomposition is more likely to occur during high-speed film formation, and thus is prone to thermal decomposition, resulting in a reduction in the life of the component.

[0621] On the other hand, it is believed that when an arylene group having a small number of ring carbon atoms (small molecular weight) is used as a connecting group, the compound represented by general formula (1) is less likely to undergo thermal decomposition even when placed in an environment where thermal decomposition is more likely to occur during high-speed film formation, resulting in an improved device life.

[0622] Therefore, according to the compound of this embodiment, by selecting a linking group with a small number of ring carbon atoms (for example, a linking group in which the total number of carbon atoms contained in -(L1)n- is 21 or less) among the linking groups L1, the effect of long life brought about by deuteration is further exhibited even when high-speed film formation is performed.

[0623] In the compound of this embodiment, from the viewpoint of further exhibiting the effect of extending the life due to deuteration even during high-speed film formation,

[0624] Preferably, L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted A divalent group derived by removing one hydrogen atom from any one of the groups consisting of a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group and a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[0625] In the compound of this embodiment, from the viewpoint of further exhibiting the effect of extending the life due to deuteration even during high-speed film formation,

[0626] More preferably, L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted A divalent group derived by removing one hydrogen atom from any one of the groups consisting of a phenylene group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted 9,9-dialkylfluorenyl group.

[0627] In the compound of this embodiment, from the viewpoint of further exhibiting the effect of long life due to deuteration even during high-speed film formation, it is further preferred that L1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted A divalent group derived by removing one hydrogen atom from any one of the groups consisting of a phenylene group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted 9,9-dimethylfluorenyl group.

[0628] In the compound of this embodiment, from the viewpoint of further exhibiting the effect of long life due to deuteration even during high-speed film formation, it is further preferred that L1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted A divalent group derived by removing one hydrogen atom from any one of the groups consisting of a 9,9-dimethylfluorenyl group and a substituted or unsubstituted 9,9-dimethylfluorenyl group.

[0629] In the compound of this embodiment, the total number of carbon atoms contained in -(L1)n- is more preferably 21 or less, and even more preferably 13 or less, from the viewpoint of further demonstrating the effect of life extension due to deuteration even during high-speed film formation.

[0630] The total number of carbon atoms contained in -(L1)n- is 21 or less. Compared with compounds having a connecting group with a large number of ring carbon atoms (large molecular weight) such as a benzospirofluorene ring between two pyrene rings, for example, when mass-producing organic EL elements, even if the evaporation speed when forming a film of the light-emitting layer using the compound represented by the above general formula (1) is increased, the effect of long life brought about by deuteration can be obtained. When the film of an organic layer such as a light-emitting layer is formed at a high speed, the compound used for film formation is placed in an environment where thermal decomposition is more likely to occur. Therefore, it is speculated that compounds having a connecting group with a large number of ring carbon atoms (large molecular weight) between two pyrene rings are prone to thermal decomposition during high-speed film formation, which results in a decrease in the life of the element.

[0631] Among the compounds of this embodiment, R 111 ~R 119 and R 211 ~R 219 The total number of carbon atoms contained is 21 or less.

[0632] Among the compounds of this embodiment, R 111 ~R 119 and R 211 ~R 219 , and the total number of carbon atoms contained in -(L1)n- is 21 or less, and preferably 13 or less.

[0633] In the compound of this embodiment, L1 is preferably a group represented by any one of the following general formulae (L-1) to (L-18).

[0634]

Chemical Formula 27

[0635]

[0636]

Chemical Formula 28

[0637]

[0638] (In the above general formulas (L-1) to (L-18), X 14 is an oxygen atom or a sulfur atom,

[0639] R 11 ~R 15 One or more groups of two or more adjacent

[0640] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0641] bonded to each other to form a substituted or unsubstituted fused ring, or

[0642] Not bonded to each other,

[0643] R21 ~R 28 One or more groups of two or more adjacent

[0644] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0645] bonded to each other to form a substituted or unsubstituted fused ring, or

[0646] Not bonded to each other,

[0647] R 31 ~R 40 One or more groups of two or more adjacent

[0648] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0649] bonded to each other to form a substituted or unsubstituted fused ring, or

[0650] Not bonded to each other,

[0651] R 41 ~R 48 One or more groups of two or more adjacent

[0652] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0653] bonded to each other to form a substituted or unsubstituted fused ring, or

[0654] Not bonded to each other,

[0655] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 ~R 15 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0656] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 21 ~R 28 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0657] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 31 ~R 40 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0658] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 41 ~R 50 Two of them are single bonds bonded to *a or other L1 in the above general formula (1), or single bonds bonded to *b or other L1 in the above general formula (1),

[0659] R does not form the above-mentioned substituted or unsubstituted monocyclic ring, does not form the above-mentioned substituted or unsubstituted condensed ring, and is not a single bond to *a, *b or other L1 in the above-mentioned general formula (1); 11 ~R 15 、R 21 ~R 28 、R 31 ~R 40 and R 41 ~R 50 Each independently of R in the above general formula (11) 300 Same meaning.)

[0660] In the compound of this embodiment, preferably, when n is 1, -(L1)n- is a group selected from the group consisting of groups represented by the above general formulae (L-1) to (L-18),

[0661] When n is 2, -(L1)n- is a group formed by mutually bonding two groups selected from the group consisting of groups represented by the above general formulae (L-1) to (L-18),

[0662] When n is 3, -(L1)n- is a group in which three groups selected from the group consisting of groups represented by the above-mentioned general formulae (L-1) to (L-18) are bonded to each other.

[0663] In the above general formulas (L-14) to (L-18), preferably,

[0664] R 41 ~R 48 Among the groups consisting of two or more adjacent groups, one or more groups do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring.

[0665] In the compound of this embodiment, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, when n is 1, -(L1)n- is preferably a group selected from the group consisting of groups represented by the above-mentioned general formulae (L-1) to (L-8) and (L-14) to (L-18).

[0666] When n is 2, -(L1)n- is preferably a group in which two groups selected from the group consisting of groups represented by the above-mentioned general formulae (L-1) to (L-8) and (L-14) to (L-18) are bonded to each other.

[0667] When n is 3, -(L1)n- is preferably a group in which three groups selected from the group consisting of groups represented by the above-mentioned general formulae (L-1) to (L-8) and (L-14) to (L-18) are bonded to each other.

[0668] Among the compounds of this embodiment, from the viewpoint of further demonstrating the effect of longer life due to deuteration even during high-speed film formation, it is more preferable to:

[0669] L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted a divalent group derived by removing one hydrogen atom from any one of the groups consisting of a phenyl group, a substituted or unsubstituted triphenylene group, a group represented by the above general formula (L-14), a group represented by the above general formula (L-15), a group represented by the above general formula (L-16), a group represented by the above general formula (L-17), and a group represented by the above general formula (L-18), and

[0670] The total number of carbon atoms contained in -(L1)n- is 21 or less.

[0671] In addition, it is further preferred that L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted a divalent group derived by removing one hydrogen atom from any one of the groups consisting of a group represented by the above general formula (L-14), a group represented by the above general formula (L-15), a group represented by the above general formula (L-16), a group represented by the above general formula (L-17), and a group represented by the above general formula (L-18), and

[0672] The total number of carbon atoms contained in -(L1)n- is 21 or less.

[0673] In this embodiment, preferably, when L1 is a divalent group derived by removing one hydrogen atom from any one of the groups selected from the group consisting of the group represented by the above general formula (L-14), the group represented by the above general formula (L-15), the group represented by the above general formula (L-16), the group represented by the above general formula (L-17), and the group represented by the above general formula (L-18),

[0674] In the above general formulas (L-14) to (L-18),

[0675] R 49 and R 50 Each independently

[0676] a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

[0677] R 41 ~R 48 Each independently

[0678] hydrogen atoms, or

[0679] a substituted or unsubstituted alkyl group,

[0680] R 41 ~R 48 Each independently

[0681] hydrogen atoms,

[0682] substituted or unsubstituted alkyl,

[0683] Substituted or unsubstituted haloalkyl,

[0684] substituted or unsubstituted alkenyl,

[0685] substituted or unsubstituted alkynyl,

[0686] substituted or unsubstituted cycloalkyl,

[0687] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0688] -O-(R 904 ) shown in the group,

[0689] -S-(R 905 ) shown in the group,

[0690] Substituted or unsubstituted aralkyl,

[0691] -C(=O)R 801 The groups shown,

[0692] -COOR 802 The groups shown,

[0693] Halogen atoms,

[0694] cyano,

[0695] Nitro,

[0696] substituted or unsubstituted aryl, or

[0697] a substituted or unsubstituted heterocyclic group,

[0698] R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each independently

[0699] hydrogen atoms,

[0700] substituted or unsubstituted alkyl,

[0701] substituted or unsubstituted cycloalkyl,

[0702] substituted or unsubstituted aryl, or

[0703] a substituted or unsubstituted heterocyclic group.

[0704] In the compound of this embodiment, L1 preferably has at least one deuterium atom.

[0705] In the compounds of this embodiment, preferably R 11 ~R 15 、R 21 ~R 28 、R 31 ~R 40 and R 41 ~R 50 At least one of them is a deuterium atom.

[0706] In the compound of this embodiment, preferably, R 11 ~R 15 、R 21 ~R 28 、R 31 ~R 40 and R 41 ~R 50 One or more of them are substituents, and R 11 ~R 15 、R 21 ~R 28 、R 31 ~R 40 and R 41 ~R 50 At least one of them independently has one or more deuterium atoms.

[0707] In the compound of this embodiment, -(L1)n- is preferably of the following general formula (L n -1)~(L n -18) is a group represented by any of the formulae.

[0708]

Chemical Formula 29

[0709]

[0710]

Chemical Formula 30

[0711]

[0712]

Chemical Formula 31

[0713]

[0714] (the above general formula (L n -1)~(L n -18) in X 15 and X 16 are each independently an oxygen atom, a sulfur atom or CR 15A R 16A ,

[0715] One or more groups of two or more adjacent Ra

[0716] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0717] bonded to each other to form a substituted or unsubstituted fused ring, or

[0718] Not bonded to each other,

[0719] One or more groups of two or more adjacent Rb

[0720] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0721] bonded to each other to form a substituted or unsubstituted fused ring, or

[0722] Not bonded to each other,

[0723] Multiple R 100 One or more groups of two or more adjacent

[0724] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0725] bonded to each other to form a substituted or unsubstituted fused ring, or

[0726] Not bonded to each other,

[0727] Multiple R 200 One or more groups of two or more adjacent

[0728] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0729] bonded to each other to form a substituted or unsubstituted fused ring, or

[0730] Not bonded to each other,

[0731] Multiple Ra are the same or different from each other.

[0732] Multiple Rb are the same as or different from each other,

[0733] Multiple R 100 Same or different from each other,

[0734] Multiple R 200 Same or different from each other,

[0735] Ra, Rb, R do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring 100 、R 200 、R 15A and R 16A Each independently of R in the above general formula (11) 300 Same meaning,

[0736] The above general formula (L n -1)~(L n -18), one of the two * represents a bonding position to *a in the above general formula (1), and the other * represents a bonding position to *b in the above general formula (1).

[0737] In the compound of this embodiment, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, -(L1)n- is preferably selected from the group consisting of the general formula (L n -1)~(L n -8) and (L n -18) is a group selected from the group consisting of the groups shown in FIG.

[0738] In the compound of this embodiment, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, it is more preferable that -(L1)n- is a member selected from the group consisting of n -9)~(L n -17) in the case of a group consisting of a group represented by the general formula (L n -9)~(L n -17) does not have a divalent group derived from a substituted or unsubstituted 9,9'-spirobifluorenyl group by removing one hydrogen atom, and does not have a divalent group derived from a substituted or unsubstituted 9,9-diphenylfluorenyl group by removing one hydrogen atom.

[0739] In the compound of this embodiment, it is preferred that multiple Ra, multiple Rb, multiple R100 , multiple R 200 、R 15A and R 16A At least one of them is a deuterium atom.

[0740] In the compound of this embodiment, preferably, multiple Ra, multiple Rb, multiple R 100 , multiple R 200 、R 15A and R 16A One or more of them are substituents, and Ra, Rb, R 100 、R 200 、R 15A and R 16A At least one of them independently has one or more deuterium atoms.

[0741] In the compound of this embodiment, preferably, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0742] In the compound of this embodiment, preferably, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

[0743] In the compound of this embodiment, more preferably, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted naphthyl group, an unsubstituted anthracenyl group, an unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, an unsubstituted 9,9-diphenylfluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted naphthobenzofuranyl group, an unsubstituted dibenzothienyl group, or an unsubstituted naphthobenzothienyl group.

[0744] In the compound of this embodiment, preferably, R 111 ~R 119 and R 211 ~R 219 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0745] -Si(R 901 )(R 902 )(R 903 ) in the group represented by 901 、R 902 and R 903 Each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0746] In the compound of this embodiment, more preferably, R 111 ~R 119 and R 211 ~R 219 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, -Si(R 901 )(R 902 )(R 903), a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms,

[0747] -Si(R 901 )(R 902 )(R 903 ) in the group represented by 901 、R 902 and R 903 Each is independently an unsubstituted alkyl group having 1 to 18 carbon atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0748] In the compounds of this embodiment, preferably R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 At least one of them is a deuterium atom.

[0749] In the compound of this embodiment, preferably, R 111 ~R 119 is a deuterium atom, or R 211 ~R 219 A deuterium atom.

[0750] In the compounds of this embodiment, preferably R 111 ~R 119 and R 211 ~R 219 A deuterium atom.

[0751] In the compound of this embodiment, preferably, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 One or more of them are substituents, and R 111 ~R 119 、R 211 ~R 219 、R 300 、R 901 、R902 、R 903 、R 904 、R 905 、R 801 and R 802 At least one of them independently has one or more deuterium atoms.

[0752] In the compound of this embodiment, L1, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 311 ~R 318 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 When the expression "substituted or unsubstituted" is used, the substituents are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, substituted or unsubstituted 9-carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted diazacarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted diazadibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted azadibenzothiophenyl, or substituted or unsubstituted diazadibenzothiophenyl.

[0753] In the compound of this embodiment, L1, R 111 ~R 119 、R 211 ~R 219 、R 300、R 311 ~R 318 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 When the substituent is expressed as "substituted or unsubstituted", it is more preferred that each of the substituents independently be a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[0754] In the compound of this embodiment, L1, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 311 ~R 318 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 When the expression "substituted or unsubstituted" is used, the substituents are preferably all "unsubstituted" groups.

[0755] In the compound of this embodiment, L1, R 111 ~R 119 、R 211 ~R 219 、R 300 、R 311 ~R 318 、R 901 、R 902 、R 903 、R 904 、R 905 、R 801 and R 802 When the substituent is expressed as "substituted or unsubstituted", it is more preferable that each substituent is independently an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthroline group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.

[0756] In one embodiment, the compound represented by the above general formula (1) and having at least one deuterium atom is preferably a compound according to the following schemes A to D.

[0757] [Compounds involved in Scheme A]

[0758] The compound involved in Scheme A is represented by the following general formula (120-1): The compound represented by the following general formula (120-1) has at least one deuterium atom.

[0759]

Chemical Formula 32

[0760]

[0761] (In the above general formula (120-1),

[0762] R1 to R4 are each independently

[0763] hydrogen atoms,

[0764] The group represented by the following general formula (120A),

[0765] The group represented by the following general formula (120B),

[0766] A group represented by the following general formula (120C), or

[0767] A group represented by the following general formula (120D),

[0768] Among them, R1 to R4 are not hydrogen atoms at the same time.

[0769] L1 and L2 are each independently

[0770] single bond,

[0771] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0772] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0773] R 102 ~R 119 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0774] When L1 and L2 are described as "substituted or unsubstituted", the substituents are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0775]

Chemical Formula 33

[0776]

[0777] (In the above general formulas (120A) to (120C),

[0778] Rx1 to Rx5 and Ry1 to Ry8 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl , a substituted or unsubstituted 3-carbazolyl, a substituted or unsubstituted 4-carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted azacarbazolyl, a substituted or unsubstituted diazacarbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted naphthobenzofuranyl, a substituted or unsubstituted azadibenzofuranyl, a substituted or unsubstituted diazadibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzothiophenyl, a substituted or unsubstituted azadibenzothiophenyl, or a substituted or unsubstituted diazadibenzothiophenyl,

[0779] At least one of Rx1 to Rx5 is not a hydrogen atom, and * in the above general formulae (120A), (120B), and (120C) represents a bonding position.

[0780] (In the above general formula (120D),

[0781] X 13 For oxygen atoms, sulfur atoms, NR 39 or CR 39A R 39B ,

[0782] R 31 ~R 38 One or more groups of two or more adjacent

[0783] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0784] bonded to each other to form a substituted or unsubstituted fused ring, or

[0785] Not bonded to each other,

[0786] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 31 ~R 38 Any one of them is a single bond bonded to at least any one of R1, R2, R3 and R4,

[0787] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 31 ~R 39 Each independently has the same meaning as Rx1 to Rx5 and Ry1 to Ry8,

[0788] R 39A and R 39B Group

[0789] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0790] bonded to each other to form a substituted or unsubstituted fused ring, or

[0791] Not bonded to each other,

[0792] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 39A and R 39B Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0793] In the compound according to the embodiment A, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, it is more preferable to combine two pyrene rings (having R 111 ~R 119 The pyrene ring and R 102 ~R 110 The total number of carbon atoms contained in the group connected to the pyrene ring is 21 or less.

[0794] In the above general formula (120-1), the group connecting two pyrene rings is a group consisting of L1, a phenylene group having R1 to R4, and L2.

[0795] In the compounds involved in Scheme A, preferably, Rx1 to Rx5, Ry1 to Ry8 and R 31 ~R 39Each is independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[0796] In the compounds involved in Scheme A, preferably, Rx1 to Rx5, Ry1 to Ry8 and R 31 ~R 39 At least one of them is a deuterium atom.

[0797] Among the compounds involved in Scheme A, preferably, R 31 ~R 38 One or more of the groups consisting of two or more adjacent ones of the ...

[0798] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 31 ~R 38 Each is independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[0799] Among the compounds involved in Scheme A, it is preferred that the compound represented by the above general formula (120-1) is represented by the following general formula (121), (122), (123), (124) or (125).

[0800]

Chemical Formula 34

[0801]

[0802]

Chemical Formula 35

[0803]

[0804] (In the above general formulae (121) to (125), R1 to R3 are independently the same as R1 to R3 in the above general formula (120-1), wherein R1 to R3 are not hydrogen atoms, L1 and L2 are independently the same as L1 and L2 in the above general formula (120-1), and R 102 ~R 119 Each independently and R in the above general formula (120-1) 102 ~R 119 Same meaning.)

[0805] In the compound according to Scheme A, preferably, L1 and L2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0806] In the compound of this embodiment, it is more preferred that L1 and L2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.

[0807] In the compound according to Scheme A, preferably, L1 and L2 are each independently a single bond or a group represented by any one of the following general formulae (141) to (150).

[0808]

Chemical Formula 36

[0809]

[0810] (In the above general formulae (141) to (150), Ra1 to Ra5, Rb1 to Rb7, and Rc1 to Rc8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * indicates a bonding position.)

[0811] In the compounds contemplated in Scheme A, preferably L1 has at least one deuterium atom. Preferably L2 has at least one deuterium atom.

[0812] In the compound according to Scheme A, at least one of R1 to R4 is preferably a deuterium atom. Preferably, at least one of R1 to R4 is a substituent, and at least one of R1 to R4 as a substituent is independently one or more deuterium atoms.

[0813] In the above general formulae (141) to (150), it is preferred that at least one of Ra1 to Ra5, Rb1 to Rb7, and Rc1 to Rc8 is a deuterium atom.

[0814] In the above general formulae (141) to (150), it is preferred that at least one of Ra1 to Ra5, Rb1 to Rb7, and Rc1 to Rc8 is a substituent, and the substituents Ra, Rb, R 100 、R 200 、R 15A and R 16A At least one of them is independently one or more deuterium atoms.

[0815] Among the compounds involved in Scheme A, preferably, R 102 ~R119 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0816] Among the compounds involved in Scheme A, preferably, R 102 ~R 110 is a deuterium atom, or R 111 ~R 119 is a deuterium atom. 102 ~R 119 is a deuterium atom. Preferably, R 102 ~R 119 One or more of them are substituents, and R 102 ~R 119 At least one of them is independently one or more deuterium atoms.

[0817] [Compounds involved in Scheme B]

[0818] The compound involved in Scheme B is represented by the following general formula (120-2): The compound represented by the following general formula (120-2) has at least one deuterium atom.

[0819]

Chemical Formula 37

[0820]

[0821] (In the above general formula (120-2),

[0822] Group of R1 and R2

[0823] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0824] bonded to each other to form a substituted or unsubstituted fused ring, or

[0825] Not bonded to each other,

[0826] In the case where the group of R1 and R2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, the monocyclic ring is not a heterocyclic ring, and in the case where the group of R1 and R2 are bonded to each other to form a substituted or unsubstituted condensed ring, the condensed ring is not a heterocyclic ring,

[0827] R1 that does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, or substituted or unsubstituted 9,9-diphenylfluorenyl,

[0828] R2 which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, or substituted or unsubstituted 9,9-diphenylfluorenyl,

[0829] R 102 ~R 119 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 50 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and Rx, Ry and Rz in Si(Rx)(Ry)(Rz) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0830] In the compound according to the embodiment B, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, it is more preferable to combine two pyrene rings (having R 111 ~R 119 The pyrene ring and R 102 ~R 110 The total number of carbon atoms contained in the group connected to the pyrene ring is 21 or less.

[0831] In the above general formula (120-2), the group connecting two pyrene rings refers to a phenylene group having R1 to R2.

[0832] In the compounds of Scheme B, preferably the groups R1 and R2 are not bonded to each other.

[0833] In the compound according to Scheme B, when the groups of R1 and R2 are not bonded to each other, the compound represented by the above general formula (120-2) is preferably represented by the following general formula (121) or (122).

[0834]

Chemical Formula 38

[0835]

[0836] (In the above general formulas (121) and (122), R 1A and R 2A Each independently has the same meaning as R1 and R2 in the above general formula (120-2), wherein R 1A and R 2A is a substituent, R 102 ~R 119 Each independently of R in the above general formula (120-2) 102 ~R 119 Same meaning.)

[0837] In the compounds involved in Scheme B, preferably, R1 is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, substituted or unsubstituted 9-carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted diazacarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted diazadibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted azadibenzothiophenyl, or substituted or unsubstituted diazadibenzothiophenyl.

[0838] In the compounds involved in Scheme B, preferably, R2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, substituted or unsubstituted 9-carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted diazacarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted diazadibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted azadibenzothiophenyl, or substituted or unsubstituted diazadibenzothiophenyl.

[0839] In the compound according to Scheme B, it is also preferred that the groups of R1 and R2 are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring.

[0840] In the compound according to Scheme B, at least one of R1 and R2 is preferably a deuterium atom. Preferably, at least one of R1 and R2 is a substituent, and at least one of R1 and R2 as a substituent is each independently one or more deuterium atoms.

[0841] In the compound involved in Scheme B, it is preferred that the group of R1 and R2 is bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring, and the monocyclic ring or the condensed ring is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted 9,9'-spirobifluorene ring, a substituted or unsubstituted 9,9-diphenylfluorene ring, or a substituted or unsubstituted 9,9-dimethylfluorene ring.

[0842] In the compounds involved in Scheme B, it is preferred that when the groups of R1 and R2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, the compound represented by the above general formula (120-2) is represented by the following general formula (123) or (124).

[0843]

Chemical Formula 39

[0844]

[0845] (In the above general formulas (123) and (124),

[0846] R 102 ~R 119 Each independently of R in the above general formula (120-2) 102 ~R 119 Same meaning,

[0847] R 11 ~R 14 A group of two or more adjacent ones and R 17 and R 18 One or more of the groups

[0848] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0849] bonded to each other to form a substituted or unsubstituted fused ring, or

[0850] Not bonded to each other,

[0851] R 21 ~R 24 and R 26 One or more groups of two or more adjacent

[0852] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0853] bonded to each other to form a substituted or unsubstituted fused ring, or

[0854] Not bonded to each other,

[0855] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 ~R 18 and R 21 ~R 26 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl.

[0856] In the above general formulas (121) to (124), R 1A ~R 2A 、R11 ~R 16 and R 21 ~R 26 At least one of them is a deuterium atom.

[0857] In the above general formulas (121) to (124), preferably, R 1A ~R 2A 、R 11 ~R 16 and R 21 ~R 26 One or more of them are substituents, and R 1A ~R 2A 、R 11 ~R 16 and R 21 ~R 26 At least one of them is independently one or more deuterium atoms.

[0858] In the compounds involved in Scheme B, preferably, R 102 ~R 119 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring carbon atoms. Preferably, Rx, Ry, and Rz in Si(Rx)(Ry)(Rz) are each independently an unsubstituted alkyl group having 1 to 18 carbon atoms, or an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0859] Among the compounds involved in Scheme B, R 102 ~R 119 A hydrogen atom.

[0860] In the compounds involved in Scheme B, preferably, R 102 ~R 110 is a deuterium atom, or R 111 ~R 119 is a deuterium atom. 102 ~R 119 is a deuterium atom. Preferably, R 102 ~R 119 One or more of them are substituents, and R 102 ~R 119 At least one of them is independently one or more deuterium atoms.

[0861] [Compounds involved in Scheme C]

[0862] The compound involved in Scheme C is represented by the following general formula (120-3): The compound represented by the following general formula (120-3) has at least one deuterium atom.

[0863]

Chemical Formula 40

[0864]

[0865] (In the above general formula (120-3), L1 is a group represented by any one of the following general formulas (11) to (13), and L2 is a group represented by any one of the following general formulas (11A) to (13A),

[0866] R 102 ~R 119 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 50 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0867] Rx, Ry and Rz in Si(Rx)(Ry)(Rz) are each independently

[0868] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

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

[0870] R 102 ~R 119 When the expression "substituted or unsubstituted" is used, the substituents are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl.

[0871]

Chemical Formula 41

[0872]

[0873] (In the above general formulas (11) to (13) and (11A) to (13A), R 11 ~R 15 、R 21 ~R 27 、R31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 50 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, wherein Rx, Ry and Rz in Si(Rx)(Ry)(Rz) each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0874] R 11 ~R 15 、R 21 ~R 27 and R 31 ~R 37 When the expression "substituted or unsubstituted" is used, the substituents are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, or substituted or unsubstituted 9,9-diphenylfluorenyl,

[0875] R 11 ~R 15 Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0876] R 11A ~R 15A Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0877] R 21 ~R 27 Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0878] R 21A ~R27A Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0879] R 31 ~R 37 Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0880] R 31A ~R 37A Among the groups consisting of two or more adjacent groups, one or more groups are not bonded to each other to form a substituted or unsubstituted monocyclic ring and are not bonded to each other to form a substituted or unsubstituted condensed ring,

[0881] In the above general formulae (11) to (13) as L1, * represents the bonding position to *a in the above general formula (120-3), and R 11 ~R 15 、R 21 ~R 27 and R 31 ~R 37 Any one of is a single bond bonded to L2,

[0882] In the above general formulae (11A) to (13A) as L2, * represents the bonding position to *b in the above general formula (120-3), and R 11A ~R 15A 、R 21A ~R2 7A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0883] Among them, R in L1 12 or R 14 When it is a single bond to L2, R 11A 、R 13A 、R 15A 、R 21A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0884] R in L1 11 or R 15 When it is a single bond to L2, R 12A 、R 13A 、R 14A 、R 21A ~R 27A and R 31A ~R37A Any one of is a single bond bonded to L1,

[0885] R in L1 13 When it is a single bond to L2, R 11A 、R 12A 、R 14A 、R 15A 、R 21A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0886] R in L1 21 When it is a single bond to L2, R 11A ~R 15A 、R 22A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0887] R in L1 22 When it is a single bond to L2, R 11A ~R 15A 、R 21A 、R 23A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0888] R in L1 23 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 22A 、R 24A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0889] R in L1 24 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 23A 、R 25A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0890] R in L1 25When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 24A 、R 26A ~R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0891] R in L1 26 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 25A 、R 27A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0892] R in L1 27 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 26A and R 31A ~R 37A Any one of is a single bond bonded to L1,

[0893] R in L1 31 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A and R 32A ~R 37A Any one of is a single bond bonded to L1,

[0894] R in L1 32 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A 、R 31A and R 33A ~R 37A Any one of is a single bond bonded to L1,

[0895] R in L1 33 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A 、R 31A ~R 32A and R 34A ~R37A Any one of is a single bond bonded to L1,

[0896] R in L1 34 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A 、R 31A ~R 33A and R 35A ~R 37A Any one of is a single bond bonded to L1,

[0897] R in L1 35 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A 、R 31A ~R 34A and R 36A ~R 37A Any one of is a single bond bonded to L1,

[0898] R in L1 36 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A 、R 31A ~R 35A and R 37A Any one of is a single bond bonded to L1,

[0899] R in L1 37 When it is a single bond to L2, R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 36A Any one of them is a single bond bonded to L1.)

[0900] In the compound according to the embodiment C, from the viewpoint of further demonstrating the effect of long life due to deuteration even in high-speed film formation, it is more preferable to combine two pyrene rings (having R 111 ~R 119 The pyrene ring and R 102 ~R 110 The total number of carbon atoms contained in the group connected to the pyrene ring is 21 or less.

[0901] In the above general formula (120-3), the group linking two pyrene rings is a group represented by -L1-L2-.

[0902] In the compound according to Scheme C, -L1-L2- is preferably a group represented by any one of the following general formulae (13-1) to (13-69).

[0903]

Chemical Formula 42

[0904]

[0905]

Chemical Formula 43

[0906]

[0907]

Chemical Formula 44

[0908]

[0909]

Chemical Formula 45

[0910]

[0911]

Chemical Formula 46

[0912]

[0913]

Chemical Formula 47

[0914]

[0915]

Chemical Formula 48

[0916]

[0917]

Chemical Formula 49

[0918]

[0919]

Chemical Formula 50

[0920]

[0921]

Chemical Formula 51

[0922]

[0923] (In the above general formulas (13-1) to (13-69), R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R31A ~R 37A Each independently of R in the above general formulas (11) to (13) and (11A) to (13A) 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A The meanings are the same. *1 in the above general formulas (13-1) to (13-69) indicates the bonding position to *a in the above general formula (120-3), and *2 indicates the bonding position to *b in the above general formula (120-3).

[0924] Among the compounds according to Scheme C, the compound represented by the above general formula (120-3) is preferably represented by any one of the following general formulas (121) to (131).

[0925]

Chemical Formula 52

[0926]

[0927]

Chemical Formula 53

[0928]

[0929]

Chemical Formula 54

[0930]

[0931]

Chemical Formula 55

[0932]

[0933]

Chemical Formula 56

[0934]

[0935]

Chemical Formula 57

[0936]

[0937] (In the above general formulas (121) to (131),

[0938] R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A~R 15A 、R 21A ~R 27A and R 31A ~R 37A Each independently of R in the above general formulas (11) to (13) and (11A) to (13A) 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A Same meaning, R 102 ~R 119 Each independently of R in the above general formula (120-3) 102 ~R 119 Same meaning.)

[0939] Among the compounds involved in Scheme C, preferably, R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A 、R 31A ~R 37A and R 102 ~R 119 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring carbon atoms. Preferably, Rx, Ry, and Rz in Si(Rx)(Ry)(Rz) are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0940] Among the compounds involved in Scheme C, preferably, R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A 、R31A ~R 37A and R 102 ~R 119 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, substituted or unsubstituted 9-carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted diazacarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted diazadibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted azadibenzothiophenyl, or substituted or unsubstituted diazadibenzothiophenyl.

[0941] Among the compounds involved in Scheme C, preferably, R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A and R 102 ~R 119 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[0942] Among the compounds involved in Scheme C, preferably, R11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A A hydrogen atom.

[0943] Among the compounds involved in Scheme C, preferably, R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A At least one of them is a deuterium atom. Preferably, R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A One or more of them are substituents, and R 11 ~R 15 、R 21 ~R 27 、R 31 ~R 37 、R 11A ~R 15A 、R 21A ~R 27A and R 31A ~R 37A At least one of them is independently one or more deuterium atoms.

[0944] Among the compounds involved in Scheme C, preferably, R 102 ~R 119 A hydrogen atom.

[0945] Among the compounds involved in Scheme C, preferably, R 102 ~R 110 is a deuterium atom, or R 111 ~R 119is a deuterium atom. Preferably, R 102 ~R 119 is a deuterium atom. Preferably, R i02 ~R 119 One or more of them are substituents, and R 102 ~R 119 At least one of them is independently one or more deuterium atoms.

[0946] [Compounds involved in Scheme D]

[0947] The compound involved in Scheme D is a compound represented by the following general formula (120X), (120Y), or (120Z). The compound represented by the following general formula (120X), (120Y), or (120Z) has at least one deuterium atom.

[0948]

Chemical Formula 58

[0949]

[0950] (In the above general formulas (120X), (120Y) and (120Z),

[0951] R 111 ~R 119 and R 211 ~R 219 Each independently

[0952] hydrogen atoms,

[0953] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0954] a substituted or unsubstituted cycloalkyl group having 1 to 50 carbon atoms,

[0955] A group represented by Si(Rx)(Ry)(Rz),

[0956] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0957] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0958] Rx, Ry and Rz in Si(Rx)(Ry)(Rz) are each independently

[0959] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0960] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0961] In the above general formula (120X),

[0962] By R 11 and R12 Group, R 13 and R 14 Group, R 21 and R 22 Group, R 23 and R 24 One or more groups in a group consisting of

[0963] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0964] bonded to each other to form a substituted or unsubstituted fused ring, or

[0965] Not bonded to each other,

[0966] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 、R 13 、R 21 and R 23 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, or a group represented by the following general formula (4),

[0967] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 12 、R 14 、R 22 and R 24 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, or a group represented by the following general formula (4),

[0968] Among them, R 11 ~R 14 and R 21 ~R 24 At least one of them is not a hydrogen atom,

[0969] In the above general formulas (120Y) and (120Z),

[0970] R 31 ~R 33 、R 41 ~R 43 、R 51 ~R 54 and R 61 ~R 64 One or more groups of two or more adjacent

[0971] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0972] bonded to each other to form a substituted or unsubstituted fused ring, or

[0973] Not bonded to each other,

[0974] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 and R 61 ~R 64 Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a group represented by the following general formula (4),

[0975] Among them, R 31 ~R 34 and R 41 ~R 44 At least one of them is not a hydrogen atom,

[0976] R 51 ~R 54 and R 61 ~R 64 At least one of them is not a hydrogen atom,

[0977] In the compound represented by the above general formula (120X), R 11 and R 13 The group and R 21 and R 23 The groups are different from each other, or R 12 and R 14 The group and R 22 and R 24 The groups are different from each other.

[0978] In the compound represented by the above general formula (120Y), R 31 and R 41 The group and selected from R 32 and R 42 Group, R 33 and R 43 The group and R 34 and R 44 At least one of the groups is different from each other,

[0979] In the compound represented by the above general formula (120Z), R 51 and R 61 The group and selected from R 52 and R 62 Group, R 53 and R 63 The group and R 54 and R 64 At least one of the groups is different from each other.)

[0980]

Chemical Formula 59

[0981]

[0982] (In the above general formula (4), X 13 is an oxygen atom, a sulfur atom or NR 319 ,

[0983] R 311 ~R 318 One or more groups of two or more adjacent

[0984] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0985] bonded to each other to form a substituted or unsubstituted fused ring, or

[0986] Not bonded to each other,

[0987] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 311 ~R 319 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl,

[0988] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 311 ~R 319 Any one of them is the same as R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R44 、R 51 ~R 54 and R 61 ~R 64 At least one of the bonds is a single bond.)

[0989] (In the above general formulas (120X), (120Y) and (120Z), R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 、R 111 ~R 119 、R 211 ~R 219 and R 311 ~R 319 When the expression "substituted or unsubstituted" is used, the substituents are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl.

[0990]

Chemical Formula 60

[0991]

[0992] In the above general formula (120X), "R 11 and R 13 The group and R 21 and R 23 The following general formulas (1a), (1b) and (1c) represent the partial structures of the general formula (120X).

[0993]

Chemical Formula 61

[0994]

[0995] (In the above general formulas (1a), (1b) and (1c),

[0996] R12 、R 14 、R 22 and R 24 Each independently of R in the above general formula (120X) 12 、R 14 、R 22 and R 24 Same meaning.

[0997] *a1 represents the bonding position with *11 in the above general formula (120X),

[0998] *a2 represents the bonding position to *12 in the above general formula (120X).

[0999] For example, in R 11 "A", R 13 In the case of "B",

[1000] R 11 and R 13 The group and R 21 and R 23 The groups are the same group means that

[1001] R 21 "A", R 23 is "B" (the above general formula (1a)), or R 21 "B", R 23 The case of "A" (the above general formula (1b)).

[1002] Here, "A" and "B" are different from each other.

[1003] In addition, in R 11 and R 13 When both are "A",

[1004] R 11 and R 13 The group and R 21 and R 23 The groups are the same group means that

[1005] R 21 and R 23 The case of "A" at the same time (the above general formula (1c)).

[1006] That is, R 11 and R 13 The group and R 21 and R 23 The groups of which are different from each other are, for example, 11 "A", R 13 is "B", and

[1007] R21 and R 23 At the same time,

[1008] R 21 and R 23 Both "B" or R 21 and R 23 If at least one of the two is "C" which is different from "A" and "B",

[1009] In addition, we can also cite: R 11 and R 13 is "A" at the same time, and

[1010] R 21 and R 23 If at least one of the following is "B",

[1011] R 21 and R 23 For example, at least one of them is "C" which is different from "A".

[1012] In the above general formula (120X), for "R 12 and R 14 The group and R 22 and R 24 The same is true for "groups are different from each other".

[1013]

Chemical Formula 62

[1014]

[1015] In the above general formula (120Y), regarding "R 31 and R 41 The group and selected from R 32 and R 42 Group, R 33 and R 43 The group and R 34 and R 44 At least one of the groups is different from each other", for example, "R 31 and R 41 The group and R 32 and R 42 The following general formulas (2a), (2b) and (2c) represent the partial structures of the above general formula (120Y).

[1016]

Chemical Formula 63

[1017]

[1018] (In the above general formulas (2a), (2b) and (2c),

[1019] R 33 、R 34 、R 43 and R 44 Each independently of R in the above general formula (120Y) 33 、R 34 、R 43 and R 44 Same meaning.

[1020] *b1 represents the bonding position with *21 in the above general formula (120Y),

[1021] *b2 represents the bonding position to *22 in the above general formula (120Y).

[1022] For example, in R 31 "A", R 41 In the case of group "B",

[1023] R 31 and R 41 The group and R 32 and R 42 The groups are the same group means that

[1024] R 32 "A", R 42 is "B" (the above general formula (2a)), or R 32 "B", R 42 The case of "A" (the above general formula (2b)).

[1025] Here, "A" and "B" are different from each other.

[1026] In addition, in R 31 and R 41 When both are "A",

[1027] R 31 and R 41 The group and R 32 and R 42 The groups are the same group means that

[1028] R 32 and R 42 The case of "A" at the same time (the above general formula (2c)).

[1029] That is, R 31 and R 41 The group and R 32 and R 42 The groups of which are different from each other are, for example, 31 "A", R 41 is "B", and

[1030] R 32 and R 42 At the same time,

[1031] R 32 and R 42 Both "B" or R 32 and R 42 If at least one of the two is "C" which is different from "A" and "B",

[1032] In addition, we can also cite: R 31 and R 41 is "A" at the same time, and

[1033] R 32 and R 42 If at least one of the following is "B",

[1034] R 32 and R 42 For example, at least one of them is "C" which is different from "A".

[1035] In the above general formula (120Y), for "R 31 and R 41 The group and R 33 and R 43 The same is true for "the groups are different from each other". 31 and R 41 The group and R 34 and R 44 The same is true for "groups are different from each other".

[1036]

Chemical Formula 64

[1037]

[1038] In the above general formula (120Z), regarding "R 51 and R 61 The group and selected from R 52 and R 62 Group, R 53 and R 63 The group and R 54 and R 64 At least one of the groups is different from each other", for example, "R 51 and R 61 The group and R 52 and R 62 The following general formulas (3a), (3b) and (3c) represent the partial structures of the general formula (120Z).

[1039]

Chemical Formula 65

[1040]

[1041] (In the above general formulas (3a), (3b) and (3c),

[1042] R 53 、R 54 、R 63 and R 64 Each independently of R in the above general formula (120Z) 53 、R 54 、R 63 and R 64 Same meaning.

[1043] *c1 represents the bonding position with *31 in the above general formula (120Z),

[1044] *c2 represents the bonding position to *32 in the above general formula (120Z).

[1045] For example, in R 51 "A", R 61 In the case of group "B",

[1046] R 51 and R 61 The group and R 52 and R 62 The groups are the same group means that

[1047] R 52 "A", R 62 is "B" (the above general formula (3a)), or R 52 "B", R 62 The case of "A" (the above general formula (3b)).

[1048] Here, "A" and "B" are different from each other.

[1049] In addition, in R 51 and R 61 When both are "A", R 51 and R 61 The group and R 52 and R 62 The groups are the same group means that

[1050] R 52 and R 62 The case where the groups are all "A" at the same time (the above general formula (3c)).

[1051] That is, R 51 and R 61 The group and R 52 and R 62 The groups of which are different from each other are, for example,51 "A", R 61 is "B", and

[1052] R 52 and R 62 At the same time,

[1053] R 52 and R 62 Both "B" or R 52 and R 62 If at least one of the two is "C" which is different from "A" and "B",

[1054] In addition, we can also cite: R 51 and R 61 is "A" at the same time, and

[1055] R 52 and R 62 If at least one of the following is "B",

[1056] R 52 and R 62 For example, at least one of them is "C" which is different from "A".

[1057] In the above general formula (120Z), for "R 51 and R 61 The group and R 53 and R 63 The same is true for "the groups are different from each other". 51 and R 61 The group and R 54 and R 64 The same is true for "groups are different from each other".

[1058] In the compound according to the embodiment D, from the viewpoint of further demonstrating the effect of long life due to deuteration even during high-speed film formation, it is more preferable to combine two pyrene rings (having R 111 ~R 119 The pyrene ring and R 211 ~R 219 The total number of carbon atoms contained in the group connected to the pyrene ring is 21 or less.

[1059] In the case of the compound represented by the above general formula (120X), the group connecting two pyrene rings is composed of 11 ~R 14 Phenylene and R 21 ~R 24 In the case of the compound represented by the above general formula (120Y), it refers to a group composed of a phenylene group having R 31 ~R 34Phenylene and R 41 ~R 44 In the case of the compound represented by the above general formula (120Z), it refers to a group composed of a phenylene group having R 51 ~R 54 Phenylene and R 61 ~R 64 A group composed of phenylene.

[1060] Among the compounds involved in Scheme D, preferably, R 111 ~R 119 and R 211 ~R 219 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring carbon atoms. Preferably, Rx, Ry, and Rz in Si(Rx)(Ry)(Rz) are each independently an unsubstituted alkyl group having 1 to 18 carbon atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[1061] Among the compounds involved in Scheme D, preferably, R 111 ~R 119 and R 211 ~R 219 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[1062] Among the compounds involved in Scheme D, preferably, R 111 ~R 119 and R 211 ~R 219 A hydrogen atom.

[1063] Among the compounds involved in Scheme D, preferably, R 11 and R 12 Group, R 13 and R 14 Group, R 21 and R 22 Group, R 23 and R 24 One or more groups of the group consisting of are not bonded to each other, R 31 ~R 33 、R 41 ~R43 、R 51 ~R 54 and R 61 ~R 64 Among the groups consisting of two or more adjacent ones, one or more groups are not bonded to each other.

[1064] The compound involved in Scheme D is preferably represented by the following general formula (1-1), (2-1) or (3-1).

[1065]

Chemical Formula 66

[1066]

[1067] (In the above general formulas (1-1), (2-1) and (3-1), R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 Each independently of R in the above general formulas (120X), (120Y) and (120Z) 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 Same meaning.)

[1068] Among the compounds involved in Scheme D, preferably, R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 and R 61 ~R 64each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[1069] Among them, R 12 、R 14 、R 22 and R 24 It is not a substituted or unsubstituted phenyl group.

[1070] Among the compounds involved in Scheme D, preferably, R 11 and R 12 Group, R 13 and R 14 Group, R 21 and R 22 Group, R 23 and R 24 One or more of the groups consisting of are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

[1071] R 31 ~R 33 、R 41 ~R 43 、R 51 ~R 54 and R 61 ~R 64 Among the groups consisting of two or more adjacent ones, one or more groups are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring.

[1072] The compound according to Scheme D is preferably represented by any one of the following general formulae (1-2), (2-2) to (2-3), and (3-2) to (3-4).

[1073]

Chemical Formula 67

[1074]

[1075]

Chemical Formula 68

[1076]

[1077] (In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), R 13 ~R 14 、R 21 ~R22 、R 31 、R 33 、R 34 、R 41 、R 43 、R 44 、R 51 ~R 54 and R 61 ~R 64 Each independently of R in the above general formulas (120X), (120Y) and (120Z) 13 ~R 14 、R 21 ~R 22 、R 31 、R 33 、R 34 、R 41 、R 43 、R 44 、R 51 ~R 54 and R 61 ~R 64 Same meaning, R 301 ~R 308 Each independently of R in the above general formulas (120X), (120Y) and (120Z) 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 and R 61 ~R 64 Same meaning.)

[1078] In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), it is preferred that R 13 ~R 14 、R 21 ~R 22 、R 31 、R 33 、R 34 、R 41 、R 43 、R 44 、R 51 ~R 54 、R 61 ~R 64 and R 301 ~R 308each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[1079] Among them, R 14 and R 22 It is not a substituted or unsubstituted phenyl group.

[1080] Among the compounds involved in Scheme D, preferably, R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 and R 301 ~R 308 At least one of them is a deuterium atom.

[1081] Among the compounds involved in Scheme D, preferably, R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 and R 301 ~R 308 One or more of them are substituents, and R 11 ~R 14 、R 21 ~R 24 、R 31 ~R 34 、R 41 ~R 44 、R 51 ~R 54 、R 61 ~R 64 and R 301 ~R 308 At least one of them is independently one or more deuterium atoms.

[1082] Among the compounds involved in Scheme D, preferably, R 111 ~R 119 is a deuterium atom, or R 211 ~R 219 is a deuterium atom. Preferably, R 111 ~R 119 and R 211 ~R 219 is a deuterium atom. Preferably, R 111 ~R 119 and R 211 ~R 219 One or more of them are substituents, and R 111 ~R 119 and R 211 ~R 219 At least one of them is independently one or more deuterium atoms.

[1083] In the compounds according to Scheme A, Scheme B, Scheme C and Scheme D, it is preferred that the substituents described as "substituted or unsubstituted" are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, substituted or unsubstituted 9-carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted diazacarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted diazadibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted azadibenzothiophenyl, or substituted or unsubstituted diazadibenzothiophenyl.

[1084] In the compounds according to Scheme A, Scheme B, Scheme C and Scheme D, it is more preferred that the substituents when expressed as "substituted or unsubstituted" are each independently a substituted or unsubstituted C1-18 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.

[1085] In the compounds according to Scheme A, Scheme B, Scheme C, and Scheme D, it is further preferred that the substituents when expressed as "substituted or unsubstituted" are each independently an unsubstituted C 1-18 alkyl group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthroline group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.

[1086] (Method for producing the compound according to this embodiment)

[1087] The compounds of this embodiment (compounds represented by the above-mentioned general formula (1)) and the compounds of Schemes A, B, C, and D can be produced by known methods. Furthermore, the compounds of this embodiment and the compounds of Schemes A, B, C, and D can also be produced by following known methods using known substitution reactions and raw materials corresponding to the target substances.

[1088] Specific examples of the compound according to this embodiment (the compound represented by the above general formula (1)), and the compounds according to Scheme A, Scheme B, Scheme C, and Scheme D include the following compounds. However, the present invention is not limited to these specific examples. D represents a deuterium atom.

[1089]

Chemical Formula 69

[1090]

[1091]

Chemical Formula 70

[1092]

[1093]

Chemical Formula 71

[1094]

[1095]

Chemical Formula 72

[1096]

[1097]

Chemical Formula 73

[1098]

[1099]

Chemical Formula 74

[1100]

[1101]

Chemical Formula 75

[1102]

[1103]

Chemical Formula 76

[1104]

[1105]

Chemical Formula 77

[1106]

[1107]

Chemical Formula 78

[1108]

[1109]

Chemical Formula 79

[1110]

[1111]

Chemical Formula 80

[1112]

[1113]

Chemical Formula 81

[1114]

[1115]

Chemical Formula 82

[1116]

[1117]

Chemical Formula 83

[1118]

[1119]

Chemical Formula 84

[1120]

[1121]

Chemical Formula 85

[1122]

[1123]

Chemical Formula 86

[1124]

[1125]

Chemical Formula 87

[1126]

[1127]

Chemical Formula 88

[1128]

[1129]

Chemical Formula 89

[1130]

[1131]

Chemical Formula 90

[1132]

[1133]

Chemical Formula 91

[1134]

[1135]

Chemical Formula 92

[1136]

[1137]

Chemical Formula 93

[1138]

[1139]

Chemical Formula 94

[1140]

[1141]

Chemical Formula 95

[1142]

[1143]

Chemical Formula 96

[1144]

[1145]

Chemical Formula 97

[1146]

[1147]

Chemical Formula 98

[1148]

[1149]

Chemical Formula 99

[1150]

[1151]

Chemical Formula 100

[1152]

[1153] Chemical Formula 101

[1154]

[1155]

Chemical Formula 102

[1156]

[1157]

Chemical Formula 103

[1158]

[1159]

Chemical Formula 104

[1160]

[1161]

Chemical Formula 105

[1162]

[1163]

Chemical Formula 106

[1164]

[1165]

Chemical Formula 107

[1166]

[1167]

Chemical Formula 108

[1168]

[1169]

Chemical Formula 109

[1170]

[1171]

Chemical Formula 110

[1172]

[1173]

Chemical Formula 111

[1174]

[1175]

Chemical Formula 112

[1176]

[1177]

Chemical Formula 113

[1178]

[1179]

Chemical Formula 114

[1180]

[1181]

Chemical Formula 115

[1182]

[1183]

Chemical Formula 116

[1184]

[1185]

Chemical Formula 117

[1186]

[1187]

Chemical Formula 118

[1188]

[1189]

Chemical Formula 119

[1190]

[1191]

Chemical Formula 120

[1192]

[1193]

Chemical Formula 121

[1194]

[1195]

Chemical Formula 122

[1196]

[1197]

Chemical Formula 123

[1198]

[1199]

Chemical Formula 124

[1200]

[1201]

Chemical Formula 125

[1202]

[1203]

Chemical Formula 126

[1204]

[1205]

Chemical Formula 127

[1206]

[1207]

Chemical Formula 128

[1208]

[1209]

Chemical Formula 129

[1210]

[1211]

Chemical Formula 130

[1212]

[1213]

Chemical Formula 131

[1214]

[1215]

Chemical Formula 132

[1216]

[1217]

Chemical Formula 133

[1218]

[1219]

Chemical Formula 134

[1220]

[1221]

Chemical Formula 135

[1222]

[1223]

Chemical Formula 136

[1224]

[1225]

Chemical Formula 137

[1226]

[1227]

Chemical Formula 138

[1228]

[1229]

Chemical Formula 139

[1230]

[1231]

Chemical Formula 140

[1232]

[1233] [Second embodiment]

[1234] [Materials for organic EL devices]

[1235] The organic EL device material according to the second embodiment contains the compound according to the first embodiment (the compound represented by the above-mentioned general formula (1)).

[1236] According to the second embodiment, a material for an organic EL element capable of extending its life can be obtained.

[1237] It should be noted that the organic EL device material according to the second embodiment may further contain other compounds. When the organic EL device material according to the second embodiment further contains other compounds, the other compounds may be solid or liquid.

[1238] [Third embodiment]

[1239] [Organic EL element]

[1240] Hereinafter, the configuration of the organic EL element according to the third embodiment will be described.

[1241] The organic EL element according to the third embodiment includes an anode, a cathode, and a light-emitting layer included between the anode and the cathode.

[1242] The light-emitting layer contains the compound according to the first embodiment (the compound represented by the above general formula (1)) as the compound M2. Preferably, the light-emitting layer contains the compound represented by the above general formula (1) as a host material.

[1243] In this specification, "host material" means, for example, a material whose content is "50% by mass or more of the layer." Thus, for example, the compound represented by the general formula (1) contained in the light-emitting layer accounts for 50% by mass or more of the total mass of the light-emitting layer.

[1244] In the third embodiment, compound M2 (the compound represented by the above general formula (1)) has at least one deuterium atom. In the following description, "compound M2 having at least one deuterium atom" may be referred to as "deuterated compound M2." In addition, "a compound in which all deuterium atoms in compound M2 are replaced with protium atoms" may be referred to as "non-deuterated compound M2."

[1245] In the third embodiment, the content of the non-deuterated compound m2 is 99 mol % or less relative to the total of the deuterated compound M2 and the non-deuterated compound m2 contained in the light-emitting layer. The content of the non-deuterated compound m2 is confirmed by mass spectrometry.

[1246] In the third embodiment, preferably, the content ratio of the deuterated compound M2 relative to the total of the deuterated compound M2 and the non-deuterated compound m2 contained in the light-emitting layer is 30 mol% or more, 50 mol% or more, 70 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more or 100 mol%.

[1247] In the fourth embodiment described below, the content ratio of the non-deuterated compound m2 and the content ratio of the deuterated compound M2 relative to the total of the deuterated compound M2 and the non-deuterated compound m2 contained in the first or second emitting layer are also preferably within the same range.

[1248] (Emission wavelength of organic EL element)

[1249] The organic EL element according to this embodiment preferably emits light having a main peak wavelength of 430 nm to 480 nm when the element is driven.

[1250] The main peak wavelength of light emitted by the organic EL element when the element is driven is measured as follows: A voltage is applied to the organic EL element so that the current density is 10 mA / cm 2 The spectral emission brightness spectrum at the time of φ was measured using a spectral emission brightness meter CS-2000 (manufactured by Konica Minolta). In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity reaches the maximum was determined and defined as the main peak wavelength (unit: nm).

[1251] The organic EL element according to this embodiment may have one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer. It should be noted that the light-emitting layer may also have two or more layers.

[1252] In the organic EL element involved in this embodiment, the organic layer can be composed of only a light-emitting layer, or it can further have at least one layer selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer.

[1253] In the organic EL device according to this embodiment, it is preferred that a hole transport layer be provided between the anode and the light-emitting layer.

[1254] In the organic EL device according to this embodiment, it is preferable to include an electron transport layer between the anode and the light-emitting layer.

[1255] Figure 1 1 shows a schematic configuration of an example of an organic EL element according to this embodiment.

[1256] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is composed of a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 stacked in this order from the anode 3 side. The light-emitting layer 5 contains the compound according to the first embodiment (the compound represented by the above general formula (1)) as the compound M2.

[1257] (Compound M2)

[1258] In the organic EL device 1 according to this embodiment, the compound M2 is a compound represented by the above-mentioned general formula (1).

[1259] (Compound M1)

[1260] In the organic EL device 1 according to this embodiment, it is preferred that the light-emitting layer 5 further contain a fluorescent compound M1.

[1261] In the organic EL element 1 involved in this embodiment, it is preferred that the fluorescent compound M1 is one or more compounds selected from the group consisting of a compound represented by the following general formula (10), a compound represented by the following general formula (11), a compound represented by the following general formula (21), a compound represented by the following general formula (31), a compound represented by the following general formula (41), a compound represented by the following general formula (51), a compound represented by the following general formula (61), a compound represented by the following general formula (71) and a compound represented by the following general formula (81).

[1262] (Compound represented by general formula (10))

[1263] The compound represented by the general formula (10) will be described.

[1264]

Chemical Formula 141

[1265]

[1266] (In general formula (10),

[1267] R 11 ~R 16 A group of two or more adjacent ones, R 17 ~R 20 A group of two or more adjacent ones, R a1 ~R a5 A group of two or more adjacent ones and R a6 ~R a10Among the groups consisting of two or more adjacent ones of the two or more rings, one or more of the two or more adjacent ones may be bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms, or may not be bonded to each other.

[1268] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 ~R 20 、R a1 ~R a5 and R a6 ~R a10 Each independently

[1269] hydrogen atoms,

[1270] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1271] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1272] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1273] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[1274] Substituted or unsubstituted amino,

[1275] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1276] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1277] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1278] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1279] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1280] Substituted or unsubstituted phosphoalkyl,

[1281] substituted or unsubstituted phosphoryl,

[1282] a substituted or unsubstituted silyl group,

[1283] a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms,

[1284] Cyano, nitro, carboxyl, or

[1285] Halogen atoms.)

[1286] For “R 11 ~R 16A group of two or more adjacent ones, R 17 ~R 20 A group of two or more adjacent ones, R a1 ~R a5 A group of two or more adjacent ones and R a6 ~R a10 Specific examples of "one or more groups of two or more adjacent groups thereof" being bonded to each other to form a substituted or unsubstituted monocyclic or condensed ring having 3 to 30 ring atoms will be described.

[1287] As a specific example of a group of two or more adjacent groups bonded to each other to form a fused ring, if R in the above general formula (10) 17 ~R 20 For example, the compound represented by the following general formula (10A) can be cited. In the compound represented by the following general formula (10A), adjacent R 18 With R 19 With R 20 These three molecules are bonded to each other to form a fused ring.

[1288]

Chemical Formula 142

[1289]

[1290] (In the general formula (10A), R a1 ~R a10 and R 11 ~R 17 Each independently of R in the above general formula (10) a1 ~R a10 and R 11 ~R 17 Same meaning.)

[1291] In addition, as a specific example of a group of two or more adjacent groups bonded to each other to form a monocyclic ring, if R 11 ~R 16 For example, the compound represented by the following general formula (10B) can be cited. In the compound represented by the following general formula (10B), R 12 and R 13 With R 14 and R 15 These two groups are bonded to each other to form two independent monocyclic rings.

[1292]

Chemical Formula 143

[1293]

[1294] (In the general formula (10B), R a1~R a10 、R 11 and R 16 ~R 20 Each independently of R in the above general formula (10) a1 ~R a10 、R 11 and R 16 ~R 20 Same meaning.)

[1295] In one embodiment, the compound represented by the general formula (10) is a compound represented by the following general formula (10-1).

[1296]

Chemical Formula 144

[1297]

[1298] (In the above general formula (10-1), R 11 ~R 12 、R 14 ~R 20 and R a1 ~R a10 Each independently of R in the above general formula (10) 11 ~R 12 、R 14 ~R 20 and R a1 ~R a10 Same meaning,

[1299] n 10 is 0, 1, 2, or 3,

[1300] L 100 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1301] In n 10 When it is 2, multiple L 100 Same or different from each other,

[1302] In n 10 When it is 3, multiple L 100 Same or different from each other,

[1303] Ar 100 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a cyano group, or a substituted silyl group.

[1304] In the above general formula (10-1), it is preferred that n 10 0, 1, or 2.

[1305] In the above general formula (10-1), preferably, L 100 for

[1306] Single key, or selected from

[1307] substituted or unsubstituted phenyl,

[1308] Substituted or unsubstituted biphenyl,

[1309] Substituted or unsubstituted terphenyl,

[1310] substituted or unsubstituted naphthyl,

[1311] substituted or unsubstituted anthracenyl,

[1312] Substituted or unsubstituted phenoxy,

[1313] substituted or unsubstituted fluorenyl,

[1314] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[1315] substituted or unsubstituted 9,9-dimethylfluorenyl,

[1316] Substituted or unsubstituted 9,9-diphenylfluorenyl,

[1317] substituted or unsubstituted dibenzofuranyl,

[1318] substituted or unsubstituted naphthobenzofuranyl,

[1319] Substituted or unsubstituted dibenzothiophenyl, and

[1320] A divalent group derived by removing one hydrogen atom from any group consisting of a substituted or unsubstituted naphthobenzothiophenyl group.

[1321] In the above general formula (10-1), preferably, Ar 100 for

[1322] cyano,

[1323] Substituted silyl groups,

[1324] substituted or unsubstituted phenyl,

[1325] Substituted or unsubstituted biphenyl,

[1326] Substituted or unsubstituted terphenyl,

[1327] substituted or unsubstituted naphthyl,

[1328] substituted or unsubstituted anthracenyl,

[1329] Substituted or unsubstituted phenoxy,

[1330] substituted or unsubstituted fluorenyl,

[1331] Substituted or unsubstituted 9,9'-spirobifluorenyl,

[1332] substituted or unsubstituted 9,9-dimethylfluorenyl,

[1333] Substituted or unsubstituted 9,9-diphenylfluorenyl,

[1334] substituted or unsubstituted dibenzofuranyl,

[1335] substituted or unsubstituted naphthobenzofuranyl,

[1336] Substituted or unsubstituted dibenzothiophenyl, or

[1337] a substituted or unsubstituted naphthobenzothienyl group.

[1338] In the above general formula (10-1),

[1339] R 11 ~R 12 、R 14 ~R 16 and R 17 ~R 20 A group of two or more adjacent ones, R a1 ~R a5 A group of two or more adjacent ones, and R a6 ~R a10 Among the groups consisting of two or more adjacent ones of the two or more rings, one or more of the two or more adjacent ones may be bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms, or may not be bonded to each other.

[1340] In one embodiment, R in the above general formula (10) 12 and R 13 They are bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms.

[1341] In one embodiment, the compound represented by the general formula (10) is a compound represented by the following formula (10-2).

[1342]

Chemical Formula 145

[1343]

[1344] (In the general formula (10-2), Xc is an oxygen atom, a sulfur atom or CR c1 R c2 , R 11、R 14 ~R 20 、R a1 ~R a10 and R c3 ~R c8 Each independently of R in the above general formula (10) 11 ~R 20 Same meaning,

[1345] R c1 and R c2 Each independently

[1346] hydrogen atoms,

[1347] unsubstituted alkyl group having 1 to 50 carbon atoms,

[1348] unsubstituted alkenyl having 2 to 50 carbon atoms,

[1349] unsubstituted alkynyl having 2 to 50 carbon atoms,

[1350] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1351] -Si(R 901 )(R 902 )(R 903 ),

[1352] -O-(R 904 ),

[1353] AS-(R 905 ),

[1354] -N(R 906 )(R 907 ),

[1355] Halogen atoms, cyano groups, nitro groups,

[1356] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1357] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1358] R 901 ~R 907 Each independently

[1359] hydrogen atoms,

[1360] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1361] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1362] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1363] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1364] In R 901 When there are multiple R 901 The same as or different from each other. 902 When there are multiple R 902 The same as or different from each other. 903 When there are multiple R 903 The same as or different from each other. 904 When there are multiple R 904 The same as or different from each other. 905 When there are multiple R 905 The same as or different from each other. 906 When there are multiple R 906 Same as or different from each other.

[1365] In R 907 When there are multiple R 907 Same as or different from each other.)

[1366] In the above general formula (10-2),

[1367] R 14 ~R 16 and R 17 ~R 20 A group of two or more adjacent ones, R a1 ~R a5 A group of two or more adjacent ones, R a6 ~R a10 A group of two or more adjacent ones, R c3 ~R c8 A group of two or more adjacent ones, and R c1 and R c2 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms, or may not be bonded to each other.

[1368] In one embodiment, R in the above general formula (10) 18 ~R 20 Two or more of them are bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms.

[1369] In one embodiment, the compound represented by the general formula (10) is a compound represented by the following general formula (10-3).

[1370]

Chemical Formula 146

[1371]

[1372] (In general formula (10-3), R 11 ~R 17 、R a1 ~R a10 and Rd1~R d7 Each independently of R in the above general formula (10) 11 ~R 20 Same meaning.)

[1373] In the above general formula (10-3),

[1374] R 11 ~R 16 A group of two or more adjacent ones, R 17 and R d1 ~R d7 A group of two or more adjacent ones, R a1 ~R a5 A group of two or more adjacent ones, and R a6 ~R a10 Among the groups consisting of two or more adjacent ones of the two or more rings, one or more of the two or more adjacent ones may be bonded to each other to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms, or a substituted or unsubstituted condensed ring having 3 to 30 ring atoms, or may not be bonded to each other.

[1375] In one embodiment, R in the above general formulas (10) and (10-1) to (10-3) that does not participate in the ring formation 11 ~R 20 、R a1 ~R a5 、R a6 ~R a10 、R c1 ~R c8 and R d1 ~R d7 Each independently

[1376] hydrogen atoms,

[1377] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1378] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1379] Specific examples of the compound represented by the general formula (10) include the following compounds.

[1380]

Chemical Formula 147

[1381]

[1382]

Chemical Formula 148

[1383]

[1384]

Chemical Formula 149

[1385]

[1386]

Chemical Formula 150

[1387]

[1388]

Chemical Formula 151

[1389]

[1390]

Chemical Formula 152

[1391]

[1392]

Chemical Formula 153

[1393]

[1394] (Compound represented by general formula (11))

[1395] The compound represented by the general formula (11) will be described.

[1396]

Chemical Formula 154

[1397]

[1398] (In general formula (11),

[1399] R 101 ~R 110 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1400] R 101 ~R 110 At least one of them is a monovalent group represented by the following general formula (12).

[1401] R does not form the above-mentioned substituted or unsubstituted monocyclic ring, does not form the above-mentioned substituted or unsubstituted condensed ring, and is not a monovalent group represented by the following general formula (12): 101 ~R 110 Each independently

[1402] hydrogen atoms,

[1403] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1404] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1405] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1406] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1407] -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 ),

[1408] -S-(R 905 ),

[1409] -N(R 906 )(R 907 ),

[1410] Halogen atoms, cyano groups, nitro groups,

[1411] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1412] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1413] R 901 ~R 907 Each independently

[1414] hydrogen atoms,

[1415] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1416] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1417] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1418] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1419] In R 901 When there are multiple R 901 Same as or different from each other.

[1420] In R 902 When there are multiple R 902 Same as or different from each other.

[1421] In R 903 When there are multiple R 903 Same as or different from each other.

[1422] In R 904 When there are multiple R 904 Same as or different from each other.

[1423] In R 905 When there are multiple R 905 Same as or different from each other.

[1424] In R 906 When there are multiple R 906 Same as or different from each other.

[1425] In R 907 When there are multiple R 907 Same as or different from each other.)

[1426]

Chemical Formula 155

[1427]

[1428] (In general formula (12), Ar 101 and Ar 102 Each independently

[1429] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1430] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1431] L 101 ~L 103 Each independently

[1432] a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1433] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1434] In the general formula (11), preferably, R 101 ~R 110 Two of them are groups represented by the general formula (12).

[1435] In one embodiment, the compound represented by the general formula (11) is represented by the following general formula (13).

[1436]

Chemical Formula 156

[1437]

[1438] (In general formula (13), R 111 ~R 118 Each independently of the monovalent group R in the general formula (11) other than the monovalent group represented by the general formula (12) 101 ~R 110 Same meaning. 101 、Ar 102 、L 101 、L 102 and L 103 and Ar in the above general formula (12) 101 、Ar 102 、L 101 、L 102 and L 103 Same meaning.)

[1439] In the general formula (11), L 101 Preferably, it is a single bond, L 102 and L 103 It is preferably a single bond.

[1440] In one embodiment, the compound represented by the general formula (11) is represented by the following general formula (14) or (15).

[1441]

Chemical Formula 157

[1442]

[1443] (In general formula (14), R 111 ~R 118 Each independently of R in the above general formula (13) 111 ~R 118 Same meaning. 101 、Ar 102 、L 102 and L 103 Each independently and Ar in the above general formula (12) 101 、Ar 102 、L 102 and L 103 Same meaning.)

[1444]

Chemical Formula 158

[1445]

[1446] (In general formula (15), R 111 ~R 118 Each independently of R in the above general formula (13) 111 ~R 118Same meaning, Ar 101 and Ar 102 Each independently and Ar in the above general formula (12) 101 and Ar 102 Same meaning.)

[1447] In the general formula (11) (general formula (12)), preferably, Ar 101 and Ar 102 At least one of them is a group represented by the following general formula (16).

[1448]

Chemical Formula 159

[1449]

[1450] (In general formula (16),

[1451] X 101 represents an oxygen atom or a sulfur atom.

[1452] R 121 ~R 127 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1453] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 121 ~R 127 Each independently

[1454] hydrogen atoms,

[1455] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1456] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1457] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1458] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1459] -Si(R 901 )(R 902 )(R 903 ),

[1460] -O-(R 904 ),

[1461] -S-(R 905 ),

[1462] -N(R 906 )(R 907 ),

[1463] Halogen atoms, cyano groups, nitro groups,

[1464] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1465] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1466] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1467] X 101 An oxygen atom is preferred.

[1468] Preferably, R 121 ~R 127 At least one of

[1469] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1470] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1471] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1472] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1473] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1474] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1475] In the general formula (11) (general formula (12)), preferably, Ar 101 is a group represented by the general formula (16), Ar 102 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1476] In one embodiment, the compound represented by the general formula (11) is represented by the following general formula (17).

[1477]

Chemical Formula 160

[1478]

[1479] (In general formula (17), R 111 ~R 118 Each independently of R in the above general formula (13) 111 ~R 118 Same meaning, R 121 ~R 127Each independently of R in the above general formula (16) 121 ~R 127 Same meaning.

[1480] R 131 ~R 135 Each independently

[1481] hydrogen atoms,

[1482] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1483] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1484] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1485] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1486] -Si(R 901 )(R 902 )(R 903 ),

[1487] -O-(R 904 ),

[1488] -S-(R 905 ),

[1489] -N(R 906 )(R 907 ),

[1490] Halogen atoms, cyano groups, nitro groups,

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

[1492] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1493] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1494] Specific examples of the compound represented by the general formula (11) include the following compounds.

[1495]

Chemical Formula 161

[1496]

[1497]

Chemical Formula 162

[1498]

[1499]

Chemical Formula 163

[1500]

[1501]

Chemical Formula 164

[1502]

[1503]

Chemical Formula 165

[1504]

[1505]

Chemical Formula 166

[1506]

[1507] (Compound represented by general formula (21))

[1508] The compound represented by the general formula (21) will be described.

[1509]

Chemical Formula 167

[1510]

[1511] (In general formula (21),

[1512] Z is independently CR a or N.

[1513] Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1514] In R a When there are multiple R a Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1515] In R b When there are multiple R b Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1516] In R c When there are multiple R c Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1517] n21 and n22 are each independently an integer of 0-4.

[1518] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring a ~R c Each independently

[1519] hydrogen atoms,

[1520] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1521] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1522] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1523] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1524] -Si(R 901 )(R 902 )(R 903 ),

[1525] -O-(R 904 ),

[1526] -S-(R 905 ),

[1527] -N(R 906 )(R 907 ),

[1528] Halogen atoms, cyano groups, nitro groups,

[1529] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1530] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1531] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1532] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as a compound formed by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1. The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring includes two carbon atoms in the fused bicyclic structure at the center of the general formula (21) as ring atoms. Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds formed by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

[1533] The "heterocycle" of the A1 ring and the A2 ring has the same structure as a compound formed by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2. The "heterocycle" of the A1 ring and the A2 ring contains two carbon atoms in the fused bicyclic structure at the center of the general formula (21) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2.

[1534] Rb is bonded to any carbon atom forming an aromatic hydrocarbon ring of the A1 ring, or any atom forming a heterocyclic ring of the A1 ring.

[1535] Rc is bonded to any carbon atom forming an aromatic hydrocarbon ring of the A2 ring, or any atom forming a heterocyclic ring of the A2 ring.

[1536] Preferably, R a ~R c At least one (preferably two) of them is a group represented by the following general formula (21a).

[1537] -L 201 -Ar 201 (21a)

[1538] (In general formula (21a),

[1539] L 201 for

[1540] single bond,

[1541] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1542] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1543] Ar 201 for

[1544] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1545] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1546] A group represented by the following general formula (21b).

[1547]

Chemical Formula 168

[1548]

[1549] (In general formula (21b),

[1550] L 211and L 212 Each independently

[1551] single bond,

[1552] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1553] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1554] Ar 211 and Ar 212 They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1555] Ar2 does not form a substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 and Ar 212 Each independently

[1556] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1557] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1558] In one embodiment, the compound represented by general formula (21) is represented by the following general formula (22).

[1559]

Chemical Formula 169

[1560]

[1561] (In general formula (22),

[1562] R 201 ~R 211 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1563] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 201 ~R 211 Each independently

[1564] hydrogen atoms,

[1565] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1566] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1567] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1568] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1569] -Si(R 901 )(R 902 )(R 903 ),

[1570] -O-(R 904 ),

[1571] -S-(R 905 ),

[1572] -N(R 906 )(R 907 ),

[1573] Halogen atoms, cyano groups, nitro groups,

[1574] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1575] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1576] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1577] Preferably, R 201 ~R 211 At least one (preferably two) of them is a group represented by the above general formula (21a). 204 and R 211 It is a group represented by the above-mentioned general formula (21a).

[1578] In one embodiment, the compound represented by the general formula (21) is a compound in which the structure represented by the following general formula (21-1) or (21-2) is bonded to the A1 ring. In another embodiment, the compound represented by the general formula (22) is a compound in which the structure represented by the following general formula (21-1) or (21-2) is bonded to the A1 ring. 204 ~R 207 A compound in which a structure represented by the following general formula (21-1) or (21-2) is bonded to the bonded ring.

[1579]

Chemical Formula 170

[1580]

[1581] (In the general formula (21-1), the two * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring of the A1 ring of the general formula (21), or to R 204 ~R 207Any one of the bonds.

[1582] The three * in the general formula (21-2) are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring of the A1 ring in the general formula (22), or to R 204 ~R 207 Any one of the bonds.

[1583] R 221 ~R 227 and R 231 ~R 239 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1584] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 221 ~R 227 and R 231 ~R 239 Each independently

[1585] hydrogen atoms,

[1586] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1587] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1588] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1589] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1590] -Si(R 901 )(R 902 )(R 903 ),

[1591] -O-(R 904 ),

[1592] -S-(R 905 ),

[1593] -N(R 906 )(R 907 ),

[1594] Halogen atoms, cyano, nitro,

[1595] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1596] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1597] R901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1598] In one embodiment, the compound represented by general formula (21) is a compound represented by the following general formula (21-3), general formula (21-4) or general formula (21-5).

[1599]

Chemical Formula 171

[1600]

[1601] (In general formula (21-3), general formula (21-4) and general formula (21-5), the A1 ring has the same meaning as the A1 ring in the above general formula (21).

[1602] R 2401 ~R 2407 Each independently of R in the general formula (21-1) and (21-2) 221 ~R 227 Same meaning, R 2410 ~R 2417 Each independently of R in the general formula (22) 201 ~R 211 Same meaning.)

[1603] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms in the A1 ring of the general formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring.

[1604] In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in the A1 ring of the general formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[1605] In one embodiment, the compound represented by the general formula (21) or the general formula (22) is selected from the group consisting of compounds represented by the following general formulae (21-6-1) to (21-6-7).

[1606]

Chemical Formula 172

[1607]

[1608] (In general formulas (21-6-1) to (21-6-7), R 2421 ~R 2427 Each independently of R in the above general formula (21-1) and (21-2) 221 ~R 227 Same meaning, R2430 ~R 2437 and R 2441 ~R 2444 Each independently of R in the above general formula (22) 201 ~R 211 Same meaning.)

[1609] X is O or NR 901 or C(R 902 )(R 903 ).

[1610] R 901 ~R 903 Each independently of R in the above general formula (11) 901 ~R 903 Same meaning.)

[1611] In one embodiment, in the compound represented by general formula (22), R 201 ~R 211 One or more of the groups of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring. This embodiment is described in detail by the following general formula (25).

[1612] (Compound represented by general formula (25))

[1613] The compound represented by the general formula (25) will be described.

[1614]

Chemical Formula 173

[1615]

[1616] (In general formula (25),

[1617] Choose from R 251 and R 252 Group, R 252 and R 253 Group, R 254 and R 255 Group, R 255 and R 256 Group, R 256 and R 257 Group, R 258 and R 259 Group, R 259 and R 260 The group, and R 260 and R 261 Two or more groups in the group consisting of the groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring.

[1618] Among them, R251 and R 252 The group composed of R 252 and R 253 The groups composed of R do not form a single ring or a condensed ring at the same time. 254 and R 255 The group composed of R 255 and R 256 The groups composed of R do not form a single ring or a condensed ring at the same time. 255 and R 256 The group composed of R 256 and R 257 The groups composed of R do not form a single ring or a condensed ring at the same time. 258 and R 259 The group composed of R 259 and R 260 The groups composed of R do not form a single ring or a condensed ring at the same time. 259 and R 260 The group composed of R 260 and R 261 The composed groups do not simultaneously form a single ring or a condensed ring.

[1619] R 251 ~R 261 The two or more monocyclic rings formed may be the same or different. 251 ~R 261 The two or more fused rings formed may be the same or different.

[1620] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 251 ~R 261 Each independently

[1621] hydrogen atoms,

[1622] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1623] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1624] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1625] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1626] -Si(R 901 )(R 902 )(R 903 ),

[1627] -O-(R 904 ),

[1628] -S-(R 905 ),

[1629] -N(R 906 )(R 907 ),

[1630] Halogen atoms, cyano groups, nitro groups,

[1631] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1632] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1633] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1634] In the general formula (25), R n and R n+1 (n represents an integer selected from 251, 252, 254 to 256 and 258 to 260) are bonded to each other and R n and R n+1 The two ring-forming carbon atoms to which the ring is bonded together form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring. The monocyclic or condensed ring is preferably composed of atoms selected from C atoms, O atoms, S atoms, and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

[1635] The number of the above-mentioned ring structures in the compound represented by general formula (25) is, for example, 2, 3, or 4. The two or more ring structures may be present on the same benzene ring on the mother skeleton of general formula (25), or on different benzene rings. For example, when there are three ring structures, one ring structure may be present on each of the three benzene rings of general formula (25).

[1636] Examples of the ring structure in the compound represented by the general formula (25) include structures represented by the following general formulae (251) to (260).

[1637]

Chemical Formula 174

[1638]

[1639] (In general formulas (251) to (257), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R n and R n+1 The two ring carbon atoms bonded to R nThe bonded ring carbon atoms may be any of two ring carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[1640] X 2501 C(R 2512 )(R 2513 ),NR 2514 , O or S.

[1641] R 2501 ~R 2506 and R 2512 ~R 2513 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1642] R does not form a substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 2501 ~R 2514 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning.)

[1643]

Chemical Formula 175

[1644]

[1645] (In general formulas (258) to (260), *1 and *2, and *3 and *4 represent R n and R n+1 The two ring carbon atoms bonded to R n The ring-constituting carbon atom to which the ring is bonded may be any one of the two ring-constituting carbon atoms represented by *1 and *2, or *3 and *4.

[1646] X 2501 C(R 2512 )(R 2513 ),NR 2514 , O or S.

[1647] R 2515 ~R 2525 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1648] R does not form a substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 2515 ~R 2521 and R 2522 ~R 2525Each independently of R in the above general formula (25) 251 ~R 261 Same meaning.)

[1649] In the general formula (25), preferably R 252 、R 254 、R 255 、R 260 and R 261 At least one (preferably R 252 、R 255 and R 260 At least one of, more preferably R 252 ) is a group that does not form a ring structure.

[1650] (i) In the general formula (25), R n and R n+1 When the formed ring structure has a substituent,

[1651] (ii) In the general formula (25), R that does not form a ring structure 251 ~R 261 ,as well as

[1652] (iii) R in general formulas (251) to (260) 2501 ~R 2514 、R 2515 ~R 2525 Preferably, each independently is a hydrogen atom,

[1653] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1654] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1655] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1656] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1657] -N(R 906 )(R 907 ),

[1658] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1659] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1660] Any one of the groups selected from the following groups.

[1661]

Chemical Formula 176

[1662]

[1663] (In general formulas (261) to (264), R d Each independently

[1664] hydrogen atoms,

[1665] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1666] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1667] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1668] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1669] -Si(R 901 )(R 902 )(R 903 ),

[1670] -OA(R 904 ),

[1671] -S-(R 905 ),

[1672] -N(R 906 )(R 907 ),

[1673] Halogen atoms, cyano groups, nitro groups,

[1674] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1675] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1676] X is C(R 901 )(R 902 ),NR 903 , O or S.

[1677] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.

[1678] p1 is an integer from 0 to 5, p2 is an integer from 0 to 4, p3 is an integer from 0 to 3, and p4 is an integer from 0 to 7.)

[1679] In one embodiment, the compound represented by the general formula (25) is represented by any one of the following general formulae (25-1) to (25-6).

[1680]

Chemical Formula 177

[1681]

[1682] (In general formulae (25-1) to (25-6), rings d to i are each independently a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring. R 251 ~R 261 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning.)

[1683] In one embodiment, the compound represented by the general formula (25) is represented by any one of the following general formulae (25-7) to (25-12).

[1684]

Chemical Formula 178

[1685]

[1686] (In general formulae (25-7) to (25-12), rings d to f, ring k, and ring j are each independently a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring. R 251 ~R 261 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning.)

[1687] In one embodiment, the compound represented by the general formula (25) is represented by any one of the following general formulae (25-13) to (25-21).

[1688]

Chemical Formula 179

[1689]

[1690] (In general formulae (25-13) to (25-21), rings d to k are each independently a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring. R 251 ~R 261 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning.)

[1691] When the ring g or ring h further has a substituent, examples of the substituent include:

[1692] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1693] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1694] A group represented by the above-mentioned general formula (261), (263) or (264).

[1695] In one embodiment, the compound represented by the general formula (25) is represented by any one of the following general formulae (25-22) to (25-25).

[1696]

Chemical Formula 180

[1697]

[1698] (In general formulas (25-22) to (25-25), X 250 C(R 901 )(R 902 ),NR 903 , O or S. R 251 ~R 261 、R 271 ~R 278 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning. 901 ~R 903 Each independently of R in the above general formula (11) 901 ~R 903 Same meaning.)

[1699] In one embodiment, the compound represented by the general formula (25) is represented by the following general formula (25-26).

[1700]

Chemical Formula 181

[1701]

[1702] (In general formula (25-26), X 250 C(R 901 )(R 902 ),NR 903 , O or S. R 253 、R 254 、R 257 、R 258 、R 261 and R 271 ~R 282 Each independently of R in the above general formula (25) 251 ~R 261 Same meaning. 901 ~R 903 Each independently of R in the above general formula (11) 901 ~R 903 Same meaning.)

[1703] Specific examples of the compound represented by the general formula (21) include the following compounds.

[1704]

Chemical Formula 182

[1705]

[1706]

Chemical Formula 183

[1707]

[1708]

Chemical Formula 184

[1709]

[1710]

Chemical Formula 185

[1711]

[1712] (Compound represented by general formula (31))

[1713] The compound represented by the general formula (31) will be described. The compound represented by the general formula (31) corresponds to the compound represented by the general formula (21-3) described above.

[1714]

Chemical Formula 186

[1715]

[1716] (In general formula (31),

[1717] R 301 ~R 307 and R 311 ~R 317 Among the groups consisting of two or more adjacent ones, one or more groups form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or are not bonded to each other.

[1718] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 301 ~R 307 and R 311 ~R 317 Each independently

[1719] hydrogen atoms,

[1720] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1721] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1722] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1723] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1724] -Si(R901 )(R 902 )(R 903 ),

[1725] -O-(R 904 ),

[1726] -S-(R 905 ),

[1727] -N(R 906 )(R 907 ),

[1728] Halogen atoms, cyano groups, nitro groups,

[1729] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1730] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1731] R 321 and R 322 Each independently

[1732] hydrogen atoms,

[1733] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1734] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1735] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1736] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1737] -Si(R 901 )(R 902 )(R 903 ),

[1738] -O-(R 904 ),

[1739] -S-(R 905 ),

[1740] -N(R 906 )(R 907 ),

[1741] Halogen atoms, cyano groups, nitro groups,

[1742] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1743] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1744] R 901~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1745] “R 301 ~R 307 and R 311 ~R 317 One of the groups of two or more adjacent ones is, for example, R 301 and R 302 Group, R 302 and R 303 Group, R 303 and R 304 Group, R 305 and R 306 Group, R 306 and R 307 The group and R 301 and R 302 and R 303 The combination of groups.

[1746] In one embodiment, R 301 ~R 307 and R 311 ~R 317 At least one, preferably two, of the 906 )(R 907 ) shown in the group.

[1747] In one embodiment, R 301 ~R 307 and R 311 ~R 317 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1748] In one embodiment, the compound represented by the general formula (31) is a compound represented by the following general formula (32).

[1749]

Chemical Formula 187

[1750]

[1751] (In general formula (32),

[1752] R 331 ~R 334 and R 341 ~R 344 Among the groups consisting of two or more adjacent ones, one or more groups form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or are not bonded to each other.

[1753] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 331 ~R 334 、R 341 ~R 344 , and R 351 and R 352 Each independently

[1754] hydrogen atoms,

[1755] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1756] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1757] R 361 ~R 364 Each independently

[1758] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1759] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1760] In one embodiment, the compound represented by the general formula (31) is a compound represented by the following general formula (33).

[1761]

Chemical Formula 188

[1762]

[1763] (In general formula (33), R 351 、R 352 and R 361 ~R 364 Each independently of R in the above general formula (32) 351 、R 352 and R 361 ~R 364 Same meaning.)

[1764] In one embodiment, R in formulas (32) and (33) 361 ~R 364 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[1765] In one embodiment, R in the general formula (31) 321 and R 322 , R in general formulas (32) and (33) 351 and R 352 A hydrogen atom.

[1766] In one embodiment, the substituents in the formulae (31) to (33) when expressed as "substituted or unsubstituted" are

[1767] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1768] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1769] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1770] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1771] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1772] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1773] Specific examples of the compound represented by the general formula (31) include the following compounds.

[1774]

Chemical Formula 189

[1775]

[1776]

Chemical Formula 190

[1777]

[1778]

Chemical Formula 191

[1779]

[1780]

Chemical Formula 192

[1781]

[1782]

Chemical Formula 193

[1783]

[1784]

Chemical Formula 194

[1785]

[1786]

Chemical Formula 195

[1787]

[1788]

Chemical Formula 196

[1789]

[1790]

Chemical Formula 197

[1791]

[1792]

Chemical Formula 198

[1793]

[1794]

Chemical Formula 199

[1795]

[1796]

Chemical Formula 200

[1797]

[1798] (Compound represented by general formula (41))

[1799] The compound represented by the general formula (41) will be described.

[1800]

Chemical Formula 201

[1801]

[1802] (In general formula (41),

[1803] Ring a, ring b and ring c are each independently

[1804] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1805] R 401 and R 402 Each independently bonds to the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring, or does not bond to form a substituted or unsubstituted heterocyclic ring.

[1806] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 401 and R 402 Each independently

[1807] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1808] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1809] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1810] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1811] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1812] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1813] Ring a, ring b and ring c are rings fused to the central fused bicyclic structure of the general formula (41) composed of a B atom and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

[1814] The "aromatic hydrocarbon rings" of the a ring, the b ring, and the c ring have the same structure as the compound formed by introducing a hydrogen atom into the "aryl group" described in the specific example group G1. The "aromatic hydrocarbon ring" of the a ring contains three carbon atoms on the fused two-ring structure at the center of the general formula (41) as ring atoms. The "aromatic hydrocarbon rings" of the b ring and the c ring contain two carbon atoms on the fused two-ring structure at the center of the general formula (41) as ring atoms. Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds formed by introducing a hydrogen atom into the "aryl group" described in the specific example group G1.

[1815] The "heterocycle" of the a ring, b ring and c ring has the same structure as the compound formed by introducing a hydrogen atom into the "heterocyclic group" described in the specific example group G2. The "heterocycle" of the a ring contains three carbon atoms on the fused two-ring structure at the center of the general formula (41) as ring atoms. The "heterocycle" of the b ring and c ring contains two carbon atoms on the fused two-ring structure at the center of the general formula (41) as ring atoms. As specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms", there can be mentioned compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in the specific example group G2.

[1816] R 401 and R 402 Each independently can be bonded to ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring includes the nitrogen atom on the fused two-ring structure at the center of the general formula (41). In this case, the heterocyclic ring may also contain heteroatoms other than nitrogen atoms. R 401 and R 402 Specifically, the atoms constituting the a ring, the b ring or the c ring are bonded to the atoms constituting the R 401 and R 402 For example, it can also be R 401 Bonded to a ring to form a fused 401 A nitrogen-containing heterocyclic ring in which two rings of the ring and the a ring are fused (or three or more rings are fused). Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group of two or more fused rings in Specific Example Group G2.

[1817] R 401 When bonded to the b ring, R 402 When bonded to a ring and R402 The bonding to the C ring is the same as above.

[1818] In one embodiment, the ring a, ring b, and ring c in the general formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

[1819] In one embodiment, the ring a, ring b and ring c in the general formula (41) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

[1820] In one embodiment, R in the general formula (41) 401 and R 402 Each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1821] In one embodiment, the compound represented by the general formula (41) is a compound represented by the following general formula (42).

[1822]

Chemical Formula 202

[1823]

[1824] (In general formula (42),

[1825] R 401A With the selection of R 411 and R 421 One or more of the groups consisting of R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 402A With the selection of R 413 and R 414 One or more of the groups may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring.

[1826] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring 401A and R 402A Each independently

[1827] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1828] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1829] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1830] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1831] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1832] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1833] R 411 ~R 421 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1834] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring or the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 411 ~R 421 Each independently

[1835] hydrogen atoms,

[1836] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1837] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1838] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1839] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1840] -Si(R 901 )(R 902 )(R 903 ),

[1841] -O-(R 904 ),

[1842] -S-(R 905 ),

[1843] -N(R 906 )(R 907 ),

[1844] Halogen atoms, cyano groups, nitro groups,

[1845] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1846] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1847] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1848] R in general formula (42) 401A and R 402Ais the same as R in general formula (41) 401 and R 402 The corresponding group.

[1849] For example, you can R 401A and R 411 The nitrogen-containing heterocyclic ring is bonded to form a 2-ring condensed (or 3-ring condensed) nitrogen-containing heterocyclic ring containing the ring and the benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the 2-ring condensed heterocyclic group containing nitrogen in the specific example group G2. 401A and R 412 Bonding situation, R 402A and R 413 Bonding conditions and R 402A and R 414 The bonding situation is the same as above.

[1850] R 411 ~R 421 One or more of the groups of two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. 11 and R 12 These six-membered rings are bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring is condensed with each other, and the condensed ring formed becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[1851] In one embodiment, R not involved in ring formation 411 ~R 421 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1852] In one embodiment, R not involved in ring formation 411 ~R 421 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1853] In one embodiment, R not involved in ring formation 411 ~R 421 Each independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1854] In one embodiment, R not involved in ring formation 411 ~R 421 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 411~R 421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1855] In one embodiment, the compound represented by the general formula (42) is a compound represented by the following general formula (43).

[1856]

Chemical Formula 203

[1857]

[1858] (In general formula (43),

[1859] R 431 With R 446 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 433 With R 447 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 434 With R 451 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 441 With R 442 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring.

[1860] R 431 ~R 451 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1861] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring or the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 431 ~R 451 Each independently

[1862] hydrogen atoms,

[1863] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1864] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1865] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1866] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1867] -Si(R 901 )(R 902 )(R 903 ),

[1868] -O-(R 904 ),

[1869] -S-(R 905 ),

[1870] -N(R 906 )(R 907 ),

[1871] Halogen atoms, cyano groups, nitro groups,

[1872] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1873] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1874] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[1875] R 431 Can be used with R 446 bonded to form a substituted or unsubstituted heterocyclic ring. 431 and R 446 The groups are bonded to form a fused R 46 A nitrogen-containing heterocyclic ring having three or more condensed rings, a benzene ring, a ring containing N, and a benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. 433 and R 447 In the case of combination bonding, R 434 and R 451 The combination of bonding and R 441 and R 442 The situation of group bonding is the same as above.

[1876] In one embodiment, R not involved in ring formation 431 ~R 451 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1877] In one embodiment, R not involved in ring formation 431 ~R 451 Each is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1878] In one embodiment, R not involved in ring formation 431 ~R 451 Each independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1879] In one embodiment, R not involved in ring formation 431 ~R 451 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 431 ~R 451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1880] In one embodiment, the compound represented by the general formula (43) is a compound represented by the following general formula (43A).

[1881]

Chemical Formula 204

[1882]

[1883] (In the general formula (43A), R 461 for

[1884] hydrogen atoms,

[1885] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1886] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1887] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1888] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1889] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1890] R 462 ~R 465 Each independently

[1891] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1892] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1893] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1894] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1895] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1896] In one embodiment, R461 ~R 465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1897] In one embodiment, R 461 ~R 465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1898] In one embodiment, the compound represented by the general formula (43) is a compound represented by the following general formula (43B).

[1899]

Chemical Formula 205

[1900]

[1901] (In general formula (43B), R 471 and R 472 Each independently

[1902] hydrogen atoms,

[1903] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1904] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1905] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1906] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1907] -N(R 906 )(R 907 ),or

[1908] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1909] R 473 ~R 475 Each independently

[1910] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1911] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1912] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1913] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1914] -N(R 906 )(R 907 ),or

[1915] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1916] R 906 and R 907 Each independently of R in the above general formula (11) 906 and R 907 Same meaning.)

[1917] In one embodiment, the compound represented by the general formula (43) is a compound represented by the following general formula (43B').

[1918]

Chemical Formula 206

[1919]

[1920] (In the general formula (43B'), R 472 ~R 475 Each independently of R in the above general formula (43B) 472 ~R 475 Same meaning.)

[1921] In one embodiment, R 471 ~R 475 At least one of

[1922] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1923] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1924] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1925] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1926] -N(R 906 )(R 907 ),or

[1927] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1928] In one embodiment, R 472 for

[1929] hydrogen atoms,

[1930] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1931] -N(R 906 )(R 907 ),or

[1932] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1933] R 471 and R 473 ~R 475 Each independently

[1934] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1935] -N(R 906 )(R 907 ),or

[1936] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1937] In one embodiment, the compound represented by the general formula (43) is a compound represented by the following general formula (43C).

[1938]

Chemical Formula 207

[1939]

[1940] (In general formula (43C),

[1941] R 481 and R 482 Each independently

[1942] hydrogen atoms,

[1943] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1944] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1945] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1946] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1947] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1948] R 483 ~R 486 Each independently

[1949] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1950] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1951] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1952] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1953] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1954] In one embodiment, the compound represented by the general formula (43) is a compound represented by the following general formula (43C′).

[1955]

Chemical Formula 208

[1956]

[1957] (In the general formula (43C'), R 483 ~R 486 Each independently of R in the above general formula (43C) 483 ~R 486 Same meaning.)

[1958] In one embodiment, R 481 ~R 486 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1959] In one embodiment, R 481 ~R 486 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1960] For the compound represented by general formula (41), the rings a, b, and c can be first bonded using a linking group (a group containing N-R1 and a group containing N-R2) to produce an intermediate (first reaction), and then the rings a, b, and c can be bonded using a linking group (a group containing B) to produce the final product (second reaction). An amination reaction such as the Buchwald-Hartwig reaction can be used in the first reaction. A tandem hetero Friedel-Crafts reaction can be used in the second reaction.

[1961] Specific examples of the compound represented by the general formula (41) include the following compounds.

[1962]

Chemical Formula 209

[1963]

[1964]

Chemical Formula 210

[1965]

[1966]

Chemical Formula 211

[1967]

[1968]

Chemical Formula 212

[1969]

[1970]

Chemical Formula 213

[1971]

[1972] (Compound represented by general formula (51))

[1973] The compound represented by the general formula (51) will be described.

[1974]

Chemical Formula 214

[1975]

[1976] (In general formula (51),

[1977] The r ring is a ring represented by the general formula (52) or the general formula (53) fused at any position of the adjacent ring.

[1978] The q ring and the s ring are each independently a ring represented by the general formula (54) fused at any position of the adjacent rings.

[1979] The p ring and the t ring are each independently fused at any position of the adjacent rings and have a structure represented by the general formula (55) or the general formula (56).

[1980] In R 501 When there are multiple adjacent R 501 They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1981] X 501 is an oxygen atom, a sulfur atom or NR 502 .

[1982] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 501 and R 502 Each independently

[1983] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1984] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1985] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1986] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1987] -Si(R 901 )(R 902 )(R903 ),

[1988] -O-(R 904 ),

[1989] -S-(R 905 ),

[1990] -N(R 906 )(R 907 ),

[1991] Halogen atoms, cyano groups, nitro groups,

[1992] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1993] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1994] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.

[1995] Ar 501 and Ar 502 Each independently

[1996] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1997] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1998] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1999] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2000] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2001] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2002] L 501 for

[2003] a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

[2004] a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

[2005] a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

[2006] a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

[2007] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[2008] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[2009] m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is an integer of 0 to 3, and m4 is an integer of 0 to 5. 501 When there are multiple R 501 They may be the same or different from each other.)

[2010] In the general formula (51), each of the rings p to t is fused to share two carbon atoms with the adjacent ring. The position and direction of fusion are not limited and fusion can be performed at any position and direction.

[2011] In one embodiment, in the general formula (52) or the general formula (53) of the r ring, R 501 A hydrogen atom.

[2012] In one embodiment, the compound represented by the general formula (51) is represented by any one of the following general formulae (51-1) to (51-6).

[2013]

Chemical Formula 215

[2014]

[2015] (In general formulas (51-1) to (51-6), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m3 are each independently the same as R in the above general formula (51) 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m3 have the same meaning.)

[2016] In one embodiment, the compound represented by the general formula (51) is represented by any one of the following general formulae (51-11) to (51-13).

[2017]

Chemical Formula 216

[2018]

[2019] (In general formulas (51-11) to (51-13), R 501 、X 501 、Ar 501 、Ar 502 、L501 , m1, m3 and m4 are each independently the same as R in the above general formula (51) 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1, m3 and m4 have the same meaning.)

[2020] In one embodiment, the compound represented by the general formula (51) is represented by any one of the following general formulae (51-21) to (51-25).

[2021]

Chemical Formula 217

[2022]

[2023] (In general formulas (51-21) to (51-25), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m4 are each independently the same as R in the above general formula (51) 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 and m4 have the same meaning.)

[2024] In one embodiment, the compound represented by the general formula (51) is represented by any one of the following general formulae (51-31) to (51-33).

[2025]

Chemical Formula 218

[2026]

[2027] (In general formulas (51-31) to (51-33), R 501 、X 501 、Ar 501 、Ar 502 、L 501 , m1 to m4 are each independently the same as R in the above general formula (51) 501 、X 501 、Ar 501 、Ar 502 、L 501 、m1~m4 have the same meaning.)

[2028] In one embodiment, Ar 501 and Ar 502 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2029] In one embodiment, Ar 501 and Ar 502 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2030] Specific examples of the compound represented by the general formula (51) include the following compounds.

[2031]

Chemical Formula 219

[2032]

[2033]

Chemical Formula 220

[2034]

[2035]

Chemical Formula 221

[2036]

[2037]

Chemical Formula 222

[2038]

[2039]

Chemical Formula 223

[2040]

[2041] (Compound represented by general formula (61))

[2042] The compound represented by the general formula (61) will be described.

[2043]

Chemical Formula 224

[2044]

[2045] (In general formula (61),

[2046] R 601 and R 602 Group, R 602 and R 603 The group and R 603 and R 604 At least one of the groups is bonded to each other to form a divalent group represented by the following general formula (62).

[2047] R 605 and R 606 Group, R 606 and R 607 The group and R 607 and R 608At least one of the groups is bonded to each other to form a divalent group represented by the following general formula (63).

[2048]

Chemical Formula 225

[2049]

[2050] R 601 ~R 604 The group that does not form the divalent group represented by the above general formula (62) and R 611 ~R 614 At least one of them is a monovalent group represented by the following general formula (64).

[2051] R 605 ~R 608 The group that does not form the divalent group represented by the above general formula (63) and R 621 ~R 624 At least one of them is a monovalent group represented by the following general formula (64).

[2052] X 601 is an oxygen atom, a sulfur atom or NR 609 .

[2053] R does not form a divalent group represented by the above general formulae (62) and (63) and is not a monovalent group represented by the above general formula (64). 601 ~R 608 , R is not a monovalent group represented by the above general formula (64) 611 ~R 614 and R 621 ~R 624 , and R 609 Each independently

[2054] hydrogen atoms,

[2055] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2056] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2057] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2058] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2059] -Si(R 901 )(R 902 )(R 903 ),

[2060] -O-(R 904 ),

[2061] -S-(R905 ),

[2062] -N(R 906 )(R 907 ),

[2063] Halogen atoms, cyano groups, nitro groups,

[2064] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2065] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2066] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.

[2067]

Chemical Formula 226

[2068]

[2069] In the general formula (64), Ar 601 and Ar 602 Each independently

[2070] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2071] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2072] L 601 ~L 603 Each independently

[2073] single bond,

[2074] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[2075] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[2076] A divalent linking group formed by bonding 2 to 4 of these groups.

[2077] In the general formula (61), the positions where the divalent group represented by the general formula (62) and the divalent group represented by the general formula (63) are formed are not particularly limited, and can be 601 ~R 608 The possible positions of the group are formed.

[2078] In one embodiment, the compound represented by the general formula (61) is represented by any one of the following general formulae (61-1) to (61-6).

[2079]

Chemical Formula 227

[2080]

[2081] (In general formulas (61-1) to (61-6), X 601 and X in the above general formula (61) 601 Same meaning.

[2082] R 601 ~R 624 At least two of them are monovalent groups represented by the above general formula (64).

[2083] R is not a monovalent group represented by the above general formula (64) 601 ~R 624 Each independently

[2084] hydrogen atoms,

[2085] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2086] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2087] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2088] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2089] -Si(R 901 )(R 902 )(R 903 ),

[2090] -O-(R 904 ),

[2091] -S-(R 905 ),

[2092] -N(R 906 )(R 907 ),

[2093] Halogen atoms, cyano groups, nitro groups,

[2094] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2095] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2096] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[2097] In one embodiment, the compound represented by the general formula (61) is represented by any one of the following general formulae (61-7) to (61-18).

[2098]

Chemical Formula 228

[2099]

[2100] (In general formulas (61-7) to (61-18), X 601 and X in the above general formula (61) 601 The meanings are the same. * is a single bond bonded to the monovalent group represented by the above general formula (64). 601 ~R 624 Each independently of R other than the monovalent group represented by the general formula (64) 601 ~R 624 Same meaning.)

[2101] R does not form a divalent group represented by the above general formulae (62) and (63) and is not a monovalent group represented by the above general formula (64). 601 ~R 608 , and R which is not a monovalent group represented by the above general formula (64) 611 ~R 614 and R 621 ~R 624 Preferably, each independently

[2102] hydrogen atoms,

[2103] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2104] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2105] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2106] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2107] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2108] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2109] The monovalent group represented by the general formula (64) is preferably represented by the following general formula (65) or (66).

[2110]

Chemical Formula 229

[2111]

[2112] (In general formula (65), R 631 ~R 640Each independently

[2113] hydrogen atoms,

[2114] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2115] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2116] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2117] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2118] -Si(R 901 )(R 902 )(R 903 ),

[2119] -O-(R 904 ),

[2120] -S-(R 905 ),

[2121] -N(R 906 )(R 907 ),

[2122] Halogen atoms, cyano groups, nitro groups,

[2123] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2124] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2125] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[2126]

Chemical Formula 230

[2127]

[2128] (In general formula (66), Ar 601 、L 601 and L 603 Each independently and Ar in the above general formula (64) 601 、L 601 and L 603 Same meaning. 601 It is a structure represented by the following general formula (67).

[2129]

Chemical Formula 231

[2130]

[2131] (In general formula (67), X 602 is an oxygen atom or a sulfur atom.

[2132] R 641 ~R 648 Any one of them is L 603 Single bond bonding.

[2133] R is not a single bond 641 ~R 648 Each independently

[2134] hydrogen atoms,

[2135] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2136] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2137] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2138] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2139] -Si(R 901 )(R 902 )(R 903 ),

[2140] -O-(R 904 ),

[2141] -S-(R 905 ),

[2142] -N(R 906 )(R 907 ),

[2143] Halogen atoms, cyano, nitro,

[2144] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2145] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2146] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[2147] Specific examples of the compound represented by the general formula (61) include the compounds described in International Publication No. 2014 / 104144 and the compounds shown below.

[2148]

Chemical Formula 232

[2149]

[2150]

Chemical Formula 233

[2151]

[2152]

Chemical Formula 234

[2153]

[2154]

Chemical Formula 235

[2155]

[2156] (Compound represented by general formula (71))

[2157] The compound represented by the general formula (71) will be described.

[2158]

Chemical Formula 236

[2159]

[2160] (In general formula (71),

[2161] A7 01 Ring and A7 02 The rings are independently

[2162] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2163] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[2164] Choose from A7 01 Ring and A7 02 One or more of the ring-forming groups are bonded to * in the structure represented by the following general formula (72).

[2165]

Chemical Formula 237

[2166]

[2167] (In general formula (72),

[2168] A 703 Ring

[2169] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[2170] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[2171] X701 NR 703 、C(R 704 )(R 705 )、Si(R 706 )(R 707 )、Ge(R 708 )(R 709 ), O, S or Se.

[2172] R 701 and R 702 They may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[2173] R does not form a substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 701 and R 702 , and R 703 ~R 709 Each independently

[2174] hydrogen atoms,

[2175] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2176] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2177] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2178] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2179] -Si(R 901 )(R 902 )(R 903 ),

[2180] -O-(R 904 ),

[2181] -S-(R 905 ),

[2182] -N(R 906 )(R 907 ),

[2183] Halogen atoms, cyano, nitro,

[2184] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2185] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2186] R 901 ~R 907 Each independently of R in the above general formula (11)901 ~R 907 Same meaning.)

[2187] Choose from A7 01 Ring and A7 02 One or more of the ring groups are bonded to * of the structure represented by general formula (72). That is, in one embodiment, A 701 The carbon atoms of the aromatic hydrocarbon ring or the heterocyclic ring are bonded to the * of the structure represented by the general formula (72). 702 A carbon atom constituting the aromatic hydrocarbon ring or a ring atom constituting the heterocyclic ring is bonded to * of the structure represented by the general formula (72).

[2188] In one embodiment, the group represented by the following general formula (73) is bonded to A 701 Ring and A7 02 One or both of the rings.

[2189]

Chemical Formula 238

[2190]

[2191] (In general formula (73), Ar 701 and Ar 702 Each independently

[2192] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2193] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2194] L 701 ~L 703 Each independently

[2195] single bond,

[2196] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[2197] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[2198] A divalent linking group formed by bonding 2 to 4 of these groups.

[2199] In one embodiment, in addition to A 701 In addition to the ring, there is A 702 A carbon atom of the aromatic hydrocarbon ring or a ring atom of the heterocyclic ring is bonded to * of the structure represented by the general formula (72). In this case, the structures represented by the general formula (72) may be the same or different.

[2200] In one embodiment, R 701 and R 702 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2201] In one embodiment, R 701 and R 702 They bond with each other to form a fluorene structure.

[2202] In one embodiment, Ring A 701 and Ring A 702 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[2203] In one embodiment, Ring A7 03 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[2204] In one embodiment, X 701 O or S.

[2205] Specific examples of the compound represented by the general formula (71) include the following compounds.

[2206]

Chemical Formula 239

[2207]

[2208]

Chemical Formula 240

[2209]

[2210]

Chemical Formula 241

[2211]

[2212]

Chemical Formula 242

[2213]

[2214] (Compound represented by general formula (81))

[2215] The compound represented by the general formula (81) will be described.

[2216]

Chemical Formula 243

[2217]

[2218] (In general formula (81),

[2219] A 801 The ring is a ring represented by the general formula (82) in which adjacent rings are fused at arbitrary positions.

[2220] A 802 The ring is a ring represented by the general formula (83) fused at any position of the adjacent ring. 803 The ring is bonded at any position.

[2221] X 801 and X 802 Each independently is C(R 803 )(R 804 )、Si(R 805 )(R 806 ), oxygen atom or sulfur atom.

[2222] A 803 The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[2223] Ar 801 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2224] R 801 ~R 806 Each independently

[2225] hydrogen atoms,

[2226] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2227] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2228] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2229] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2230] -Si(R 901 )(R 902 )(R 903 ),

[2231] -O-(R 904 ),

[2232] -S-(R 905 ),

[2233] -N(R 906 )(R 907 ),

[2234] Halogen atoms, cyano, nitro,

[2235] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2236] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2237] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.

[2238] m801 and m802 are each independently an integer of 0 to 2. When they are 2, multiple R 801 or R 802 They may be the same as or different from each other.

[2239] a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in the parentheses shown as "3-a801" may be the same or different. When a801 is 2, Ar 801 They may be the same or different from each other.)

[2240] In one embodiment, Ar 801 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[2241] In one embodiment, Ring A 803 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[2242] In one embodiment, R 803 and R 804 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[2243] In one embodiment, a801 is 1.

[2244] Specific examples of the compound represented by the general formula (81) include the following compounds.

[2245]

Chemical Formula 244

[2246]

[2247] In one embodiment, the light-emitting layer contains

[2248] The compound represented by the above general formula (1), and

[2249] One or more compounds selected from the group consisting of the compound represented by the above general formula (10), the compound represented by the above general formula (11), the compound represented by the above general formula (21), the compound represented by the above general formula (31), the compound represented by the above general formula (41), the compound represented by the above general formula (51), the compound represented by the above general formula (61) and the compound represented by the above general formula (81).

[2250] In one embodiment, the compound represented by the general formula (21) is a compound represented by the following general formula (21-3), general formula (21-4) or general formula (21-5).

[2251]

Chemical Formula 245

[2252]

[2253] (In general formula (21-3), general formula (21-4) and general formula (21-5),

[2254] The A1a ring is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocyclic ring having 8 to 50 ring atoms.

[2255] R 2401 ~R 2407 and R 2410 ~R 2416 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[2256] R 2417 , R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 2401 ~R 2407 and R 2410 ~R 2416 Each independently

[2257] hydrogen atoms,

[2258] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2259] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2260] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2261] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2262] -Si(R 901 )(R 902 )(R 903 ),

[2263] -O-(R 904 ),

[2264] -S-(R 905 ),

[2265] -N(R 906 )(R 907 ),

[2266] Halogen atoms, cyano, nitro,

[2267] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2268] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2269] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 Same meaning.)

[2270] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formulas (21-1) to (21-3) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[2271] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formulas (21-1) to (21-3) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[2272] In one embodiment, the compound represented by the general formula (21) is selected from the group consisting of a compound represented by the following general formula (21-6-1), a compound represented by the following general formula (21-6-2), a compound represented by the following general formula (21-6-3), a compound represented by the following general formula (21-6-4), a compound represented by the following general formula (21-6-5), a compound represented by the following general formula (21-6-6) and a compound represented by the following general formula (21-6-7).

[2273]

Chemical Formula 246

[2274]

[2275] (In general formulas (21-6-1) to (21-6-7),

[2276] R 2421 ~R 2427 、R 2430 ~R 2436 and R 2441 ~R 2444 Among the groups consisting of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[2277] R 2437 , R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 2421 ~R 2427 、R 2430 ~R 2436 and R 2441 ~R 2444 Each independently

[2278] hydrogen atoms,

[2279] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2280] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2281] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2282] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2283] -Si(R 901 )(R 902 )(R 903 ),

[2284] -O-(R 904 ),

[2285] -S-(R 905 ),

[2286] -N(R 906 )(R 907 ),

[2287] Halogen atoms, cyano, nitro,

[2288] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2289] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2290] X is O or NR 901, or C(R 902 )(R 903 ).

[2291] R 901 ~R 903 Each independently of R in the above general formula (11) 901 ~R 903 Same meaning.)

[2292] In one embodiment, R 2401 ~R 2407 and R 2410 ~R 2417 Each independently

[2293] hydrogen atoms,

[2294] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2295] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2296] In one embodiment, R 2401 ~R 2407 and R 2410 ~R 2417 Independently choose freedom

[2297] hydrogen atoms,

[2298] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and

[2299] A group consisting of a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[2300] In one embodiment, the compound represented by the general formula (21-3) is a compound represented by the following general formula (21-3-1).

[2301]

Chemical Formula 247

[2302]

[2303] (In the general formula (21-3-1), R 2403 、R 2405 、R 2406 、R 2412 、R 2414 and R 2415 Each independently of R in the above general formula (21-3) 2403 、R 2405 、R 2406 、R 2412 、R 2414 and R 2415 Same meaning.)

[2304] In one embodiment, the compound represented by the general formula (21-3) is a compound represented by the following general formula (21-3-2).

[2305]

Chemical Formula 248

[2306]

[2307] (In the general formula (21-3-2), R 2401 ~R 2407 and R 2410 ~R 2417 Each independently of R in the above general formula (21-3) 2401 ~R 2407 and R 2410 ~R 2417 Same meaning.

[2308] It should be noted that R 2401 ~R 2407 and R 2410 ~R 2416 At least one of them is -N(R 906 )(R 907 ).

[2309] R 906 and R 907 Each independently of R in the above general formula (11) 906 and R 907 Same meaning.)

[2310] In one embodiment, R in the above general formula (21-3-2) 2401 ~R 2407 and R 2410 ~R 2416 Any two of -N(R 906 )(R 907 )(R 906 and R 907 Each independently of R in the above general formula (11) 906 and R 907 Same meaning. ).

[2311] In one embodiment, the compound represented by the general formula (21-3-2) is a compound represented by the following general formula (21-3-3).

[2312]

Chemical Formula 249

[2313]

[2314] (In the general formula (21-3-3), R 2401 ~R 2404 、R2410 ~R 2413 and R 2417 Each independently of R in the above general formula (21-3) 2401 ~R 2404 、R 2410 ~R 2413 and R 2417 Same meaning.

[2315] R A 、R B 、R C and R D Each independently

[2316] a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[2317] A substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

[2318] In one embodiment, the compound represented by the general formula (21-3-3) is a compound represented by the following general formula (21-3-4).

[2319]

Chemical Formula 250

[2320]

[2321] (In the above general formula (21-3-4), R 2417 、R A 、R B 、R C and R D Each independently of R in the above general formula (21-3-3) 2417 、R A 、R B 、R C and R D Same meaning.)

[2322] In one embodiment, R A 、R B 、R C and R D Each is independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[2323] In one embodiment, R A 、R B 、R C and R D Each is independently a substituted or unsubstituted phenyl group.

[2324] In one embodiment, the above two R 2417 are hydrogen atoms respectively.

[2325] In one embodiment, the light-emitting layer contains

[2326] The compound represented by the above general formula (1), and

[2327] One or more compounds selected from the group consisting of the compound represented by the above general formula (10), the compound represented by the above general formula (21), the compound represented by the above general formula (31), the compound represented by the above general formula (51), the compound represented by the above general formula (61), the compound represented by the above general formula (71) and the compound represented by the following general formula (43a).

[2328]

Chemical Formula 251

[2329]

[2330] (In the above general formula (43a),

[2331] R 431 With R 446 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 433 With R 447 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 434 With R 451 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring. 441 With R 442 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not be bonded to form a substituted or unsubstituted heterocyclic ring.

[2332] R 431 ~R 451 One or more pairs of two or more adjacent ones of these may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[2333] R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted condensed ring. 431 ~R 451 Each independently

[2334] Hydrogen atom, halogen atom, cyano group, nitro group,

[2335] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2336] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2337] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2338] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2339] -Si(R 901 )(R 902 )(R 903 ),

[2340] -O-(R 904 ),

[2341] -S-(R 905 ),

[2342] -N(R 906 )(R 907 ),

[2343] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2344] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2345] R 901 ~R 907 Each independently of R in the above general formula (11) 901 ~R 907 It should be noted that R does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted condensed ring. 431 ~R 451 At least one of

[2346] Halogen atoms, cyano groups, nitro groups,

[2347] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2348] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2349] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2350] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2351] -Si(R 901 )(R 902 )(R 903 ),

[2352] -O-(R 904 ),

[2353] -S-(R 905 ),

[2354] -N(R 906 )(R 907 ),

[2355] Halogen atoms, cyano groups, nitro groups,

[2356] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2357] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[2358] In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

[2359] unsubstituted alkyl group having 1 to 50 carbon atoms,

[2360] unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2361] An unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2362] In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

[2363] unsubstituted alkyl group having 1 to 18 carbon atoms,

[2364] unsubstituted aryl group having 6 to 18 ring carbon atoms, or

[2365] An unsubstituted heterocyclic group having 5 to 18 ring atoms.

[2366] In the organic EL device according to this embodiment, it is preferred that the light-emitting layer further contain a fluorescent compound M1, wherein the compound M1 is a compound that emits light with a main peak wavelength of 430 nm to 480 nm.

[2367] The method for measuring the main peak wavelength of a compound is as follows. 10 - 6 mol / L and above 10 -5 A toluene solution of less than 1 mol / L is added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is luminescence intensity, and the horizontal axis is wavelength). The luminescence spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

[2368] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is referred to as the main emission peak wavelength. Note that in this specification, the main peak wavelength may be referred to as the fluorescence main peak wavelength (FL-peak).

[2369] In the organic EL element involved in this embodiment, when the light-emitting layer contains compound M2 (the compound represented by the above-mentioned general formula (1)) and fluorescent compound M1, compound M2 is preferably a host material (sometimes also called a matrix material), and compound M1 is preferably a dopant material (sometimes also called a guest material, an emitter or a light-emitting material).

[2370] In the organic EL element involved in this embodiment, it is preferred that when the light-emitting layer contains compound M2 (the compound represented by the above general formula (1)) and fluorescent compound M1, the singlet energy S1(M2) of the above compound M2 and the singlet energy S1(M1) of the above compound M1 satisfy the relationship of the following mathematical formula (Mathematical Formula 1).

[2371] The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.

[2372] S1(M2)>S1(M1)…(Formula 1)

[2373] (Singlet energy S1)

[2374] As a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be mentioned.

[2375] Prepare 10 of the compound to be measured -5 mol / L and above 10 -4 A toluene solution with a concentration of less than 1 mol / L was added to a quartz colorimetric cell, and the absorption spectrum of the sample was measured at room temperature (300K) (absorption intensity on the vertical axis, wavelength on the horizontal axis). A tangent line was drawn on the long-wavelength side of the absorption spectrum, and the wavelength λedge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the singlet energy.

[2376] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[2377] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310) can be cited, but the device is not limited thereto.

[2378] The tangent line for the long-wavelength drop of the absorption spectrum is derived as follows. As the spectrum curve moves along the long-wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum maximum, the tangent line at each point on the curve is considered. As the curve drops (i.e., as the value on the vertical axis decreases), the slope of this tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope reaches its minimum on the longest wavelength side (excluding absorbance values ​​of 0.1 or less) is considered the tangent line for the long-wavelength drop of the absorption spectrum.

[2379] It should be noted that the maximum point where the absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

[2380] The light-emitting layer preferably does not contain a phosphorescent material (dopant material).

[2381] In addition, the light-emitting layer preferably does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[2382] In addition, the light-emitting layer preferably does not contain a metal complex.

[2383] (Thickness of the light-emitting layer)

[2384] The thickness of the light-emitting layer of the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. If the thickness of the light-emitting layer is 5 nm or greater, it is easy to form the light-emitting layer and adjust the chromaticity. If the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the increase in the driving voltage.

[2385] (Content of Compound in Light Emitting Layer)

[2386] When the light-emitting layer contains compound M2 (the compound represented by the above general formula (1)) and fluorescent compound M1, the contents of compound M2 and compound M1 in the light-emitting layer are preferably within the following ranges, for example.

[2387] The content of the compound M2 is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

[2388] The content of the compound M1 is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

[2389] However, the upper limit of the total content of the compound M2 and the compound M1 in the light-emitting layer is 100 mass %.

[2390] It should be noted that this embodiment does not exclude the inclusion of materials other than the compound M2 and the compound M1 in the light-emitting layer.

[2391] The light-emitting layer may contain only one compound M2 or two or more compounds. The light-emitting layer may contain only one compound M1 or two or more compounds.

[2392] The following further describes the structure of the organic EL element 1. In the following, reference numerals may be omitted.

[2393] (Substrate)

[2394] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, and plastic can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent. For example, a plastic substrate can be mentioned. As materials forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

[2395] (anode)

[2396] 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-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[2397] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target to which zinc oxide is added at 1% by mass or more and 10% by mass or less relative to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target to which tungsten oxide is added at 0.5% by mass or less and 5% by mass or less relative to indium oxide and zinc oxide is added at 0.1% by mass or less and 1% by mass or less relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[2398] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode. Therefore, materials that can serve as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

[2399] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys thereof. It should be noted that when forming the anode using alkali metals, alkaline earth metals, and alloys thereof, vacuum evaporation or sputtering can be used. In addition, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

[2400] (cathode)

[2401] The cathode is preferably made of a metal, alloy, conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group I or Group II of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[2402] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, vacuum deposition or sputtering can be used. Furthermore, when silver paste is used, coating or inkjet methods can be used.

[2403] It should be noted that by providing an electron injection layer, a variety of conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide can be used to form the cathode regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[2404] (Hole Injection Layer)

[2405] The hole injection layer is a layer containing a substance with high hole injectability. Examples of substances with high hole injectability include moly...

Claims

1. A compound represented by the following general formula (1), which has at least one deuterium atom, and 50% or more of the total number of hydrogen atoms in the compound represented by the general formula (1) are deuterium atoms, In the general formula (1), n ​​is 1, L1 is a group represented by any one of the following general formulas (L-1) to (L-3), R 111 ~R 119 and R 211 ~R 219 is a deuterium atom, In the general formulas (L-1) to (L-3), The two *s are bonding positions to *a in the general formula (1), or bonding positions to *b in the general formula (1), R 11 ~R 15 Each independently Hydrogen atoms, Unsubstituted phenyl, or Unsubstituted naphthyl.

2. The compound according to claim 1, wherein L1 has at least 1 deuterium atom.

3. The compound according to claim 1, wherein L1 is a group represented by the general formula (L-1).

4. The compound according to claim 1, wherein R 11 ~R 15 At least one of them is a deuterium atom.

5. The compound according to claim 1, wherein R 11 ~R 15 At least one of them is a substituent, and R 11 ~R 15 At least one of them independently has one or more deuterium atoms.

6. The compound according to claim 1, wherein -(L1)n- is the following general formula (L n -18) shown in the group, The general formula (L n -18), Ra is a hydrogen atom, The general formula (L n -18), one of the two * represents a bonding position to *a in the general formula (1), and the other * represents a bonding position to *b in the general formula (1).

7. The compound according to claim 1, wherein The total number of carbon atoms contained in -(L1)n- is 21 or less.

8. The compound according to claim 1, wherein The total number of carbon atoms contained in -(L1)n- is 13 or less.

9. The compound according to claim 1, wherein The compound represented by the general formula (1) is represented by the following general formula (121), (122), (123), (124) or (125), In the general formulae (121) to (125), R1 to R3 are each independently an unsubstituted phenyl group or an unsubstituted naphthyl group, L1 and L2 are single bonds, and R 102 ~R 119 A deuterium atom.

10. The compound according to any one of claims 1 to 9, wherein In the compound represented by the general formula (1), 60% or more of the total number of hydrogen atoms are deuterium atoms.

11. The compound according to any one of claims 1 to 9, wherein In the compound represented by the general formula (1), 70% or more of the total number of hydrogen atoms are deuterium atoms.

12. The compound according to any one of claims 1 to 9, wherein In the compound represented by the general formula (1), 80% or more of the total number of hydrogen atoms are deuterium atoms.

13. The compound according to any one of claims 1 to 9, wherein Compounds containing deuterium atoms are analyzed by mass spectrometry or 1 H-NMR analysis confirmed that The bonding position of the deuterium atom in a compound is determined by 1 H-NMR analysis was used to determine According to the 1 The integrated value obtained by H-NMR analysis confirms the number of deuterium atoms contained in the molecule.

14. A compound, which is any one of the following compounds, wherein D represents a deuterium atom, 。 15. A compound, which is any one of the following compounds, wherein D represents a deuterium atom, 。 16. An organic electroluminescent element, comprising: anode, cathode, and a light-emitting layer included between the anode and the cathode, The light-emitting layer contains the compound according to any one of claims 1 to 15 as compound M2.

17. The organic electroluminescent element according to claim 16, wherein: The light-emitting layer further comprises a fluorescent compound M1.

18. The organic electroluminescent element according to claim 17, wherein The singlet energy S1(M2) of the compound M2 and the singlet energy S1(M1) of the compound M1 satisfy the relationship of the following mathematical formula (Mathematical formula 1): S1(M2)>S1(M1)…(Mathematical formula 1).

19. The organic electroluminescent element according to any one of claims 16 to 18, wherein The light-emitting layer does not contain a metal complex.

20. The organic electroluminescent element according to any one of claims 16 to 18, wherein A hole transport layer is provided between the anode and the light emitting layer.

21. The organic electroluminescent element according to any one of claims 16 to 18, wherein An electron transport layer is provided between the cathode and the light emitting layer. 22 . An electronic device comprising the organic electroluminescent element according to claim 16 .

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