Compound, organic electroluminescent element, and electronic device

Abstract

A compound represented by formula (1).

Description

Technology Field

[0001] The present invention relates to a novel compound, an organic electroluminescence device, and an electronic device. Background Technology

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter also referred to as an organic EL device), holes from the anode and electrons from the cathode are injected into the light-emitting layer, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Conventional organic EL devices have not yet had sufficient device performance. Although improvements to organic EL devices are gradually being made to increase device performance, further high performance is required.

[0004] Patent Document 1 discloses a compound having a specific structure used in organic EL devices. Prior art literature

[0005] Specification of Chinese Patent Application Publication No. 117263894

[0006] The objective of the present invention is to provide a higher performance organic EL device.

[0007] The inventors of the present invention completed the present invention by repeatedly conducting research to achieve the above objective and discovering that a high-performance organic EL device can be obtained by using a compound having a specific structure in at least one layer of the organic layer of an organic EL device.

[0008] According to the present invention, the following compounds are provided.

[0009] 1. A compound represented by formula (1).

[0010]

[0011] [In Equation (1),

[0012] X1 is O or S.

[0013] R1 to R8 are each independently

[0014] hydrogen atom,

[0015] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0016] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0017] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0018] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0019] -Si(R 901 )(R 902 )(R 903 ),

[0020] -O-(R 904 ),

[0021] -S-(R 905 ),

[0022] -N(R 906 )(R 907 ),

[0023] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0024] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0025] At least one of R1 to R8 is a deuterium atom.

[0026] R 11 ~R 19 Each independently

[0027] hydrogen atom,

[0028] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0029] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0030] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0031] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0032] -Si(R901 )(R 902 )(R 903 ),

[0033] -O-(R 904 ),

[0034] -S-(R 905 ), or

[0035] -N(R 906 )(R 907 )am.

[0036] L1 is

[0037] single bond, or

[0038] It is a substituted or unsubstituted ring-forming arylene group with 6 to 10 carbon atoms.

[0039] n1 is an integer from 0 to 3.

[0040] If n1 is 0, (L1) n1 is a single bond.

[0041] When n1 is 2 or more, 2 or more L1s are connected in series. When n1 is 2 or more, 2 or more L1s may be identical or different.

[0042] L2 is

[0043] single bond, or

[0044] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or

[0045] It is a divalent complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0046] n2 is an integer from 0 to 3.

[0047] If n2 is 0, (L2) n2 is a single bond.

[0048] When n2 is 2 or more, 2 or more L2s are connected in series. When n2 is 2 or more, 2 or more L2s may be identical or different.

[0049] Ar1 is

[0050] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0051] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0052] R 901 ~R 907 Each independently

[0053] hydrogen atom,

[0054] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0055] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0056] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0057] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0058] R 901 ~R 907 If there are 2 or more of these, 2 or more R 901 ~R 907 Each of these may be the same or different.

[0059] 2. The cathode and,

[0060] Positive poles and,

[0061] One or more organic layers disposed between the cathode and the anode

[0062] Having,

[0063] At least one of the above organic layers contains the compound described in 1.

[0064] Organic electroluminescence device.

[0065] 3. An electronic device having the organic electroluminescence element described in 2. above.

[0066] According to the present invention, a higher performance organic EL device can be provided. Brief explanation of the drawing

[0067] FIG. 1 is a diagram showing the schematic configuration of an organic EL device according to one embodiment of the present invention. Specific details for implementing the invention

[0068] [definition]

[0069] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0070] In this specification, in the chemical structural formula, at bondable positions where symbols such as "R" or "D" representing a deuterium atom are not specified, hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms are bonded.

[0071] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed-ring compounds, crosslinked compounds, carbon-ring compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbons included in the substituent are not included in the ring-forming carbon number. Unless otherwise noted, the "ring-forming carbon number" described below shall be the same. For example, the benzene ring has a ring-forming carbon number of 6, the naphthalene ring has a ring-forming carbon number of 10, the pyridine ring has a ring-forming carbon number of 5, and the furan ring has a ring-forming carbon number of 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25.

[0072] In addition, when a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the said alkyl group is not included in the number of carbon atoms forming the ring of the benzene ring. Therefore, the number of carbon atoms forming the ring of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group, the number of carbon atoms of said alkyl group is not included in the number of carbon atoms forming the ring of the naphthalene ring. Therefore, the number of carbon atoms forming the ring of the naphthalene ring substituted with an alkyl group is 10.

[0073] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a single ring, a condensed ring, and a ring assembly) (e.g., a single ring compound, a condensed ring compound, a cross-linked compound, a carbon ring compound, and a complex ring compound). Atoms that do not constitute a ring (e.g., a hydrogen atom terminating the bond of an atom constituting a ring) or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. Unless otherwise noted, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazolin ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of ring-forming atoms of a pyridine ring. For this reason, the number of ring-forming atoms of a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Also, for example, hydrogen atoms or atoms constituting substituents bonded to carbon atoms of a quinazoline ring are not included in the number of ring-forming atoms of the quinazoline ring. For this reason, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0074] In the present specification, in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms,” “XX to YY carbon atoms” indicates the number of carbon atoms when the ZZ group is unsubstituted and does not include the number of carbon atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

[0075] In the present specification, in the expression “ZZ group having XX to YY of substituted or unsubstituted atoms,” “number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted and does not include the number of atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

[0076] In this specification, the term "unsubstituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group," and the term "substituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "substituted ZZ group."

[0077] In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not substituted with substituents. The hydrogen atoms in the "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms.

[0078] In addition, in the present specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with substituents. Likewise, "substitution" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are substituted with AA groups.

[0079] "Substituents described in this specification"

[0080] The substituents described in this specification will be explained below.

[0081] The number of ring-forming carbons of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0082] The number of ring-forming atoms of the “unsubstituted complex circulators” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0083] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.

[0084] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.

[0085] The number of carbon atoms of the “unsubstituted alkynyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.

[0086] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification.

[0087] The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0088] The number of ring-forming atoms of the “unsubstituted divalent complex circulator” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0089] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.

[0090] · "Substitution or non-substitution aryl"

[0091] Examples of specific examples (Group of Specific Examples G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (Group of Specific Examples G1A) and substituted aryl group (Group of Specific Examples G1B). (Here, the term “unsubstituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “unsubstituted aryl group,” and the term “substituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group.”) In this specification, when simply referred to as “aryl group,” it includes both the “unsubstituted aryl group” and the “substituted aryl group.”

[0092] "Substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are substituted with substituents. Examples of "substituted aryl groups" include, for instance, a group in which one or more hydrogen atoms of an "unsubstituted aryl group" of the following specific example group G1A are substituted with substituents, and examples of substituted aryl groups of the following specific example group G1B. Furthermore, the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples, and the "substituted aryl groups" described in this specification include a group in which a hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent.

[0093] ·Muchan's Arilgi (Special Example Group G1A):

[0094] phenyl group,

[0095] p-biphenyl group,

[0096] m-biphenyl group,

[0097] o-biphenyl group,

[0098] p-terphenyl-4-diary,

[0099] p-terphenyl-3-diary,

[0100] p-terphenyl-2-diary,

[0101] m-terphenyl-4-diary,

[0102] m-terphenyl-3-diary,

[0103] m-terphenyl-2-diary,

[0104] o-terphenyl-4-diary,

[0105] o-terphenyl-3-diary,

[0106] o-terphenyl-2-diyl,

[0107] 1-Naphthyl group,

[0108] 2-Naphthyl group,

[0109] Anthrill,

[0110] Benzoanthryl group,

[0111] phenanthril group,

[0112] Benzophenanthrile group,

[0113] Penalenyl group,

[0114] Pyreneyl group,

[0115] Crysenyl group,

[0116] benzocrysenyl group,

[0117] triphenylenyl group,

[0118] benzotriphenylenyl group,

[0119] tetracenyl group,

[0120] Pentacenyl group,

[0121] Fluorenyl group,

[0122] 9,9'-spirobifluorenyl group,

[0123] benzofluorenyl group,

[0124] dibenzofluorenyl group,

[0125] Fluoranthenyl group,

[0126] benzofluranthenyl group,

[0127] perylenyl group, and

[0128] A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0129]

[0130]

[0131] · Substitution Aryl group (Specific example group G1B):

[0132] o-tollil group,

[0133] m-tolyl group,

[0134] p-tolyl group,

[0135] Para-xyl group,

[0136] meta-xyl group,

[0137] Ortho-xyl group,

[0138] para-isopropylphenyl group,

[0139] meta-isopropylphenyl group,

[0140] Ortho-isopropylphenyl group,

[0141] para-t-butylphenyl group,

[0142] meta-t-butylphenyl group,

[0143] Ortho-t-butylphenyl group,

[0144] 3,4,5-trimethylphenyl group,

[0145] 9,9-dimethylfluorenyl group,

[0146] 9,9-diphenylfluorenyl group,

[0147] 9,9-bis(4-methylphenyl)fluorenyl group,

[0148] 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0149] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0150] cyanophenyl group,

[0151] triphenylsilylphenyl group,

[0152] trimethylsilylphenyl group,

[0153] phenylnaphthyl group,

[0154] Naphthylphenyl group, and

[0155] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are substituted with substituents.

[0156] · "Substitutional or Non-substitutional Complex Recall"

[0157] The “complex circulating group” described in this specification is a cyclic group comprising at least one heteroatom in a ring-forming atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.

[0158] The “complex ring” described in this specification is a simple ring or a condensed ring.

[0159] The “complex generator” described in this specification is an aromatic complex generator or a non-aromatic complex generator.

[0160] Examples of specific examples (group of specific examples G2) of the “complex circulator with or without permutation” described in this specification include the following complex circulators with or without permutation (group of specific examples G2A) and complex circulators with permutation (group of specific examples G2B). (Here, a complex circulator with or without permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with or without permutation,” and a complex circulator with permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with permutation.”) In this specification, when simply referred to as a “complex circulator,” it includes both a “complex circulator with or without permutation” and a “complex circulator with permutation.”

[0161] "Substituted complex sphere" refers to a group in which one or more hydrogen atoms of a "non-substituted complex sphere" are substituted with substituents. Specific examples of a "substituted complex sphere" include a group in which a hydrogen atom of a "non-substituted complex sphere" of the following group of examples G2A is substituted, and examples of a substituted complex sphere of the following group of examples G2B. Furthermore, the examples of "non-substituted complex spheres" and "substituted complex spheres" listed herein are merely examples, and the "substituted complex sphere" described in this specification includes a group in which a hydrogen atom bonded to the ring-forming atom of the complex sphere itself in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent.

[0162] Specific example group G2A includes, for example, an unsubstituted complex group containing a nitrogen atom (Specific example group G2A1), an unsubstituted complex group containing an oxygen atom (Specific example group G2A2), an unsubstituted complex group containing a sulfur atom (Specific example group G2A3), and a monovalent complex group (Specific example group G2A4) derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).

[0163] Specific example group G2B includes, for example, a substituent complex group containing a nitrogen atom (Specific example group G2B1), a substituent complex group containing an oxygen atom (Specific example group G2B2), a substituent complex group containing a sulfur atom (Specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent complex group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituted with a substituent (Specific example group G2B4).

[0164] · Unsubstituted complex saturators containing nitrogen atoms (Specific example group G2A1):

[0165] pyrrolyl group,

[0166] Imidajorilgi,

[0167] pyrazolyl group,

[0168] triazolyl group,

[0169] tetrazolyl group,

[0170] Oxazoligi,

[0171] Isooxazolilgi,

[0172] Oxadiazolyl group,

[0173] Thiazolyl group,

[0174] isothiazolyl group,

[0175] Thiadiazolylgi,

[0176] Piridilgi,

[0177] Piridajinilgi,

[0178] pyrimidinyl group,

[0179] Pyrazinyl group,

[0180] triazinyl group,

[0181] Indolil,

[0182] Isoindolilgi,

[0183] Indolezinyl group,

[0184] Quinolidinyl group,

[0185] Quinolyl group,

[0186] isoquinolyl group,

[0187] Sinnolilgi,

[0188] Phthalaginyl group,

[0189] Quinazolinyl group,

[0190] Quinoxalinyl group,

[0191] benzimidazolyl group,

[0192] Indazolillgi,

[0193] phenanthrolinyl group,

[0194] phenanthridinyl group,

[0195] Acridinyl group,

[0196] phenazinyl group,

[0197] Carbazolyl group,

[0198] benzocarbazolyl group,

[0199] Morpolinogi,

[0200] phenoxazinyl group,

[0201] Phenothiazinyl group,

[0202] Azacarbazolyl group, and diazcarbazolyl group.

[0203] · Unsubstituted complex circulators containing oxygen atoms (specific example group G2A2):

[0204] Purilgi,

[0205] Oxazoligi,

[0206] Isooxazolilgi,

[0207] Oxadiazolyl group,

[0208] Xanten's Diary

[0209] benzofuranyl group,

[0210] isobenzofuranyl group,

[0211] dibenzofuranyl group,

[0212] Naphthobenzofuranyl group,

[0213] Benzooxazolyl group,

[0214] Benzoisoxolyl group,

[0215] phenoxazinyl group,

[0216] Morpolinogi,

[0217] dinaphthofranyl group,

[0218] Azadibenzofuranyl group,

[0219] Diazadibenzofuranyl group,

[0220] Azanaptobenzofuranyl group, and

[0221] Diazanaptobenzofuranyl group.

[0222] · Unsubstitutable complex circulators containing sulfur atoms (Specific example group G2A3):

[0223] thienyl group,

[0224] Thiazolyl group,

[0225] isothiazolyl group,

[0226] Thiadiazolylgi,

[0227] benzothiophenyl group (benzothienyl group),

[0228] isobenzothiophenyl group (isobenzothienyl group),

[0229] dibenzothiophenyl group (dibenzothienyl group),

[0230] Naphthobenzothiophenyl group (naphthobenzothienyl group),

[0231] benzothiazolyl group,

[0232] Benzoisothiazolyl group,

[0233] Phenothiazinyl group,

[0234] dinaphthothiophenyl group (dinaphthienyl group),

[0235] Azadibenzothiophenyl group (azadibenzothienyl group),

[0236] Diazadibenzothiophenyl group (diazadibenzothienyl group),

[0237] Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and

[0238] Diazanaptobenzothiophenyl group (diazanaptobenzothienyl group).

[0239] · A monovalent complex circulator derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0240]

[0241]

[0242] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0243] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A In cases where at least one of them is NH or CH2, the monovalent complex circulating group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0244] · Substitutional complex vacancies containing nitrogen atoms (Specific example group G2B1):

[0245] (9-phenyl)carbazolyl group,

[0246] (9-biphenylyl)carbazolyl group,

[0247] (9-phenyl)phenylcarbazolyl group,

[0248] (9-naphthyl)carbazolyl group,

[0249] Diphenylcarbazole-9-diary,

[0250] Phenylcarbazole-9-diary,

[0251] methylbenzimidazolyl group,

[0252] Ethylbenzimidazolyl group,

[0253] phenyltriazinyl group,

[0254] biphenyltriazinyl group,

[0255] diphenyltriazinyl group,

[0256] Phenylquinazolinyl group, and

[0257] Biphenylquinazolinyl group.

[0258] · Substitutional complex mutators containing oxygen atoms (Specific example group G2B2):

[0259] Phenyldibenzofuranyl group,

[0260] methyldibenzofuranyl group,

[0261] t-butyldibenzofuranyl group, and

[0262] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0263] · Complex substitutions containing sulfur atoms (Specific example group G2B3):

[0264] Phenyldibenzothiophenyl group,

[0265] methyldibenzothiophenyl group,

[0266] t-butyldibenzothiophenyl group, and

[0267] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0268] · A group in which one or more hydrogen atoms of a monovalent complex cyclic group derived from the above general formulas (TEMP-16) to (TEMP-33) are substituted with substituents (Specific Example Group G2B4):

[0269] The above "one or more hydrogen atoms of a monovalent complex group" refers to a hydrogen atom, X, bonded to a ring-forming carbon atom of this monovalent complex group. A and Y A A hydrogen atom bonded to a nitrogen atom and X when at least one of them is NH A and Y A It means one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the case where one of them is CH2.

[0270] · Substituted or unsubstituted alkyl group

[0271] Examples of specific examples (Group of Specific Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Specific Examples G3A) and substituted alkyl group (Group of Specific Examples G3B). (Here, the term “unsubstituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and the term “substituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”) Hereinafter, when simply referred to as “alkyl group,” both the “unsubstituted alkyl group” and the “substituted alkyl group” are included.

[0272] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Example Group G3A) are substituted with substituents, and examples of a substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a chain-type alkyl group. Accordingly, "unsubstituted alkyl group" includes straight-chain "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups." In addition, the examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed herein are merely examples, and the "substituted alkyl groups" described in this specification include groups in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.

[0273] · Unsubstituted alkyl group (Specific Example Group G3A):

[0274] methyl group,

[0275] ethyl group,

[0276] n-Profilter,

[0277] isopropyl group,

[0278] n-butyl group,

[0279] isobutyl group,

[0280] s-butyl group, and

[0281] t-butyl group.

[0282] · Substituted alkyl group (Specific Example Group G3B):

[0283] heptafluoropropyl group (including isomers),

[0284] pentafluoroethyl group,

[0285] 2,2,2-trifluoroethyl group, and

[0286] Trifluoromethyl group.

[0287] · "Substituted or unsubstituted alkenyl group"

[0288] Examples of specific examples (Group of Specific Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Specific Examples G4A) and substituted alkenyl group (Group of Specific Examples G4B). (Here, “unsubstituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group.”) In this specification, when simply referred to as “alkenyl group,” it includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group.”

[0289] "Substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are substituted with substituents. Specific examples of "substituted alkenyl groups" include the following "unsubstituted alkenyl groups" (Group of Specific Examples G4A) having substituents and examples of substituted alkenyl groups (Group of Specific Examples G4B). Furthermore, the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed herein are merely examples, and the "substituted alkenyl groups" described in this specification include a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with substituents.

[0290] · Non-substitutional alkenyl group (Special Example Group G4A):

[0291] vinyl,

[0292] Alilgi,

[0293] 1-butenyl group,

[0294] 2-butenyl group, and

[0295] 3-butenyl group.

[0296] · Substitutional alkenyl group (Specific example group G4B):

[0297] 1,3-butanedienyl group,

[0298] 1-methylvinyl group,

[0299] 1-methylallyl group,

[0300] 1,1-dimethylallyl group,

[0301] 2-methylallyl group, and

[0302] 1,2-dimethylallyl group.

[0303] · "Substituted or unsubstituted alkynyl group"

[0304] Examples of specific examples (Group of Examples G5) of the “substituted or unsubstituted alkynyl group” described in this specification include the following unsubstituted alkynyl group (Group of Examples G5A). (Here, the term “unsubstituted alkynyl group” refers to the case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group.”) Hereinafter, when simply referred to as “alkynyl group,” both the “unsubstituted alkynyl group” and the “substituted alkynyl group” are included.

[0305] "Substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are substituted with substituents. Specific examples of the "substituted alkynyl group" include the group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (Specific Example Group G5A) below are substituted with substituents.

[0306] · Unsubstituted alkynyl group (Specific example group G5A):

[0307] Ethinyl group.

[0308] · Substituted or unsubstituted cycloalkyl group

[0309] Specific examples of the “substituted or unsubstituted cycloalkyl group” described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, “unsubstituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and “substituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”) In this specification, when simply referred to as “cycloalkyl group,” it includes both “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”

[0310] "Substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are substituted with substituents. Specific examples of "substituted cycloalkyl groups" include a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (Specific Example Group G6A) are substituted with substituents, and examples of a substituted cycloalkyl group (Specific Example Group G6B). Furthermore, the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples, and the "substituted cycloalkyl groups" described in this specification include a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of Specific Example Group G6B are substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" of Specific Example Group G6B is further substituted with a substituent.

[0311] · Unsubstituted cycloalkyl group (Specific Example Group G6A):

[0312] cyclopropyl group,

[0313] cyclobutyl group,

[0314] Cyclopentyl group,

[0315] cyclohexyl group,

[0316] 1-adamantyl group,

[0317] 2-adamantyl group,

[0318] 1-norbornyl group, and

[0319] 2-Norbornilgi.

[0320] · Substituted cycloalkyl group (Specific Example Group G6B):

[0321] 4-methylcyclohexyl group.

[0322] ·「-Si(R 901 )(R 902 )(R 903 The device indicated by )

[0323] -Si(R as described in this specification 901 )(R 902 )(R 903 As for a specific example of the device indicated by ) (specific example group G7),

[0324] -Si(G1)(G1)(G1),

[0325] -Si(G1)(G2)(G2),

[0326] -Si(G1)(G1)(G2),

[0327] -Si(G2)(G2)(G2),

[0328] -Si(G3)(G3)(G3), and

[0329] -Si(G6)(G6)(G6)

[0330] ...can be cited. Here,

[0331] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0332] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0333] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0334] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0335] In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from each other.

[0336] In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from each other.

[0337] In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from each other.

[0338] In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from each other.

[0339] In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from each other.

[0340] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.

[0341] ·「-O-(R 904 The unit indicated by )

[0342] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),

[0343] -O(G1),

[0344] -O(G2),

[0345] -O(G3), and

[0346] -O(G6)

[0347] ...can be cited.

[0348] Here,

[0349] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0350] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0351] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0352] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0353] ·「-S-(R 905 The unit indicated by )

[0354] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),

[0355] -S(G1),

[0356] -S(G2),

[0357] -S(G3), and

[0358] -S(G6)

[0359] ...can be cited.

[0360] Here,

[0361] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0362] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0363] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

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

[0365] ·「-N(R 906 )(R 907 The unit indicated by )

[0366] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),

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

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

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

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

[0371] -N(G6)(G6)

[0372] ...can be cited.

[0373] Here,

[0374] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0375] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0376] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0377] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0378] In -N(G1)(G1), multiple G1s are identical or different from each other.

[0379] In -N(G2)(G2), multiple G2s are identical or different from each other.

[0380] In -N(G3)(G3), multiple G3s are either identical or different from each other.

[0381] In -N(G6)(G6), multiple G6s are either identical or different from each other.

[0382] · Halogen atom

[0383] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0384] · "Substituted or unsubstituted fluoroalkyl group"

[0385] 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 substituted with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are substituted with a substituent. In addition, the “substituted fluoroalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted fluoroalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted fluoroalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.

[0386] · "Substituted or unsubstituted haloalkyl group"

[0387] 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 substituted with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. In addition, the “substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted haloalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted haloalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. A haloalkyl group may be referred to as an alkyl halide group.

[0388] · "Substitutional or non-substitutional alkoxyl group"

[0389] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0390] · "Substituted or unsubstituted alkylthio groups"

[0391] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0392] · "Substituted or unsubstituted aryloxy groups"

[0393] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted aryloxy group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0394] · "Substitution or non-substitution arylthioge"

[0395] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted arylthio group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0396] · Substituted or unsubstituted trialkylsilyl group

[0397] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. In -Si(G3)(G3)(G3), the plurality of G3s may be identical or different from one another. 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.

[0398] · "Substitution or non-substitution Aralkilgi"

[0399] A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3, and G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Accordingly, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted with an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group.” The “unsubstituted aralkyl group” is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group,” and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0400] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl groups, 1-phenylethyl groups, 2-phenylethyl groups, 1-phenylisopropyl groups, 2-phenylisopropyl groups, phenyl-t-butyl groups, α-naphthylmethyl groups, 1-α-naphthylethyl groups, 2-α-naphthylethyl groups, 1-α-naphthylisopropyl groups, 2-α-naphthylisopropyl groups, β-naphthylmethyl groups, 1-β-naphthylethyl groups, 2-β-naphthylethyl groups, 1-β-naphthylisopropyl groups, and 2-β-naphthylisopropyl groups.

[0401] The substituted or unsubstituted aryl groups described in this specification are, unless otherwise specified in this specification, preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-4-yl groups, p-terphenyl-3-yl groups, p-terphenyl-2-yl groups, m-terphenyl-4-yl groups, m-terphenyl-3-yl groups, m-terphenyl-2-yl groups, o-terphenyl-4-yl groups, o-terphenyl-3-yl groups, o-terphenyl-2-yl groups, 1-naphthyl groups, 2-naphthyl groups, anthryl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, triphenylenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl groups, 9,9-dimethylfluorenyl groups, and 9,9-diphenylfluorenyl groups, etc.

[0402] The substituted or unsubstituted complex groups described herein, unless otherwise specified herein, are preferably pyridyl groups, pyrimidinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, quinazolinyl groups, benzimidazolyl groups, phenanthrolinyl groups, carbazolyl groups (1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups or 9-carbazolyl groups), benzocarbazolyl groups, azacarbazolyl groups, diazacarbazolyl groups, dibenzofuranyl groups, naphthobenzofuranyl groups, azadibenzofuranyl groups, diazadibenzofuranyl groups, dibenzothiophenyl groups, naphthobenzothiophenyl groups, azadibenzothiophenyl groups, diazadibenzothiophenyl groups, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group or (9-phenyl)carbazol-4-yl group), (9-biphenyllil)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylliltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0403] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.

[0404]

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

[0406]

[0407] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0408] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following groups, unless otherwise specified in this specification.

[0409]

[0410] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0411] The substituted or unsubstituted alkyl groups described in this specification are, unless otherwise specified in this specification, preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-butyl groups, etc.

[0412] · "Substitutional or non-substitutional arylen groups"

[0413] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” unless otherwise noted. Specific examples of the “substituted or unsubstituted arylene group” (Specific Example Group G12) include a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” described in Specific Example Group G1.

[0414] · "Divination of Substitution or Non-Substitution of a Bivalent Complex Call"

[0415] The “substituted or unsubstituted divalent complex ring” described in this specification is, unless otherwise noted, a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring”. Specific examples of the “substituted or unsubstituted divalent complex ring” (Specific Example Group G13) include a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring” described in Specific Example Group G2.

[0416] · "Substituted or unsubstituted alkylene group"

[0417] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (Specific Example Group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described in Specific Example Group G3.

[0418] The substituted or unsubstituted arylene groups described in this specification are, unless otherwise specified in this specification, preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0419]

[0420]

[0421] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0422] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0423]

[0424] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0425] Formula Q9 and Q 10 They may also join together through single bonds to form a ring.

[0426] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0427]

[0428] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0429] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0430] The bivalent complex ring with or without substitution described in this specification is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0431]

[0432]

[0433]

[0434] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.

[0435]

[0436]

[0437]

[0438]

[0439] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0440] The above is an explanation of the “substituents described in this specification.”

[0441] · "When combined to form a ring"

[0442] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring, combine to form a substituted or non-substituted condensed ring, or do not combine to each other” means the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring,” the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted condensed ring,” and the case where “one or more of two or more adjacent groups do not combine to each other.”

[0443] In this specification, the cases in which "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted single ring" and "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "combining to form a ring") are described below. The explanation is given by way of example by an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is ​​an anthracene ring.

[0444]

[0445] For example, R 921 ~R 930 In the case where "one or more sets of two or more adjacent groups combine to form a ring," the two adjacent groups that make up one set are R 921 and R 922 of, R 922 and R 923 of, R 923 and R 924 of, R 924 and R 930 of, R 930 and R 925 of, R 925 and R 926 of, R926 and R 927 of, R 927 and R 928 of, R 928 and R 929 of the group and R 929 and R 921 It is the group of.

[0446] The above "one or more sets" means that two or more sets of the above two or more adjacent sets may simultaneously form a ring. For example, R 921 and R 922 They combine with each other to form the ring Q A Forms, and simultaneously R 925 and R 926 These combine with each other to form the ring Q B In the case where it is formed, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0447]

[0448] The case where "a group consisting of two or more adjacent units" forms a ring includes not only the case where a group consisting of "two" adjacent units combines as in the example above, but also the case where a group consisting of "three or more" adjacent units combines. For example, R 921 and R 922 They combine with each other to form the ring Q A It forms, and also R 922 and R 923 These combine with each other to form the ring Q C Forming, three adjacent (R 921 , R 922 and R 923 This refers to the case where groups consisting of ) combine with each other to form a ring and condense onto the anthracene matrix, and in this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is R922 Share.

[0449]

[0450] The formed "single ring" or "condensed ring" is a structure consisting solely of the formed ring, and may be a saturated ring or an unsaturated ring. Even if "a set of two adjacent rings" forms a "single ring" or a "condensed ring," the said "single ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104). A and ring Q B are respectively a "single ring" or a "condensed ring." In addition, the ring Q formed in the above general formula (TEMP-105) A and ring Q C is a "condensed ring". The ring Q of the above general formula (TEMP-105) A and ring Q C is, ring Q A and ring Q C It becomes a condensed ring through condensation. The ring Q of the above general formula (TMEP-104) A If is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TMEP-104) A If is a naphthalene ring, then ring Q A is a condensed ring.

[0451] “Unsaturated ring” includes, in addition to aromatic hydrocarbon rings and aromatic heterocyclic rings, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double and / or triple bonds, in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.) and non-aromatic heterocyclic rings having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazolin, quinolizine, indoline, isoindoline, etc.). “Saturated ring” includes aliphatic hydrocarbon rings that do not have unsaturated bonds or non-aromatic heterocyclic rings that do not have unsaturated bonds.

[0452] As a specific example of an aromatic hydrocarbon ring, a structure in which the group cited as a specific example in specific example group G1 is terminated by a hydrogen atom can be cited.

[0453] As a specific example of an aromatic complex ring, a structure in which the aromatic complex ring group cited as a specific example in specific example group G2 is terminated by a hydrogen atom can be cited.

[0454] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group of specific examples in group G6 is terminated by a hydrogen atom can be cited.

[0455] "Forming a ring" means forming a ring with only multiple atoms of the matrix, or with multiple atoms of the matrix and one or more arbitrary atoms. For example, R represented in the above general formula (TEMP-104). 921 and R 922 A ring Q formed by the combination of each other A is, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 It refers to a ring formed by a carbon atom of the anthracene skeleton to which it bonds, and one or more arbitrary atoms. As a specific example, R 921 and R 922 Lo ring Q A In the case where it forms, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 In the case where it forms a monocyclic unsaturated ring with four carbon atoms and a carbon atom of the anthracene skeleton to which it bonds, R 921 and R 922 The ring formed by is a benzene ring.

[0456] Here, "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, unless otherwise specified in this specification. In any atom (e.g., carbon atoms or nitrogen atoms), bonds that do not form a ring may be terminated by hydrogen atoms, etc., or substituted by "any substituent" described below. When any atom other than a carbon atom is included, the ring formed is a complex ring.

[0457] Unless otherwise specified in this specification, “one or more atoms” constituting a single ring or a condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.

[0458] Unless otherwise specified in this specification, among "single ring" and "condensed ring," it is preferably "single ring".

[0459] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring."

[0460] Unless otherwise stated in this specification, "single ring" is preferably a benzene ring.

[0461] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0462] In the case where “one or more sets of two or more adjacent groups” combine with each other to form a substituted or unsubstituted single ring or “combine with each other to form a substituted or unsubstituted condensed ring,” unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of the matrix and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0463] In the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in this specification."

[0464] In the case where the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in this specification."

[0465] The above is an explanation regarding the case where “one or more of two or more adjacent groups combine to form a single ring with or without substitution” and the case where “one or more of two or more adjacent groups combine to form a condensed ring with or without substitution” (the case where they combine to form a ring).

[0466] · Substituents in the case of "substituent or non-substituent"

[0467] In one embodiment of this specification, the substituent in the case of "substituent or non-substituent" (which may be referred to as "optional substituent" in this specification) is, for example

[0468] Unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0469] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0470] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0471] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0472] -Si(R 901 )(R 902 )(R 903 ),

[0473] -O-(R 904 ),

[0474] -S-(R 905 ),

[0475] -N(R 906 )(R 907 ),

[0476] Halogen atom, cyano group, nitro group,

[0477] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0478] Unsubstituted complex circulators with 5 to 50 ring-forming atoms

[0479] It is a group selected from the group consisting of, and

[0480] Here, R 901 ~R 907 Each independently

[0481] hydrogen atom,

[0482] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0483] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0484] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0485] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0486] R 901 If there are 2 or more of these, 2 or more R 901 They are identical or different from each other,

[0487] R 902 If there are 2 or more, 2 or more R 902 are identical or different from each other,

[0488] R 903 If there are 2 or more of these, 2 or more R 903 They are identical or different from each other,

[0489] R 904 If there are 2 or more, 2 or more R 904are identical or different from each other,

[0490] R 905 If there are 2 or more, 2 or more R 905 are identical or different from each other,

[0491] R 906 If there are 2 or more of these, 2 or more R 906 They are identical or different from each other,

[0492] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.

[0493] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0494] alkyl group having 1 to 50 carbon atoms,

[0495] A ring-forming aryl group having 6 to 50 carbon atoms, and

[0496] Complex circulators with 5 to 50 ring-forming atoms

[0497] It is a group selected from a group consisting of

[0498] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0499] alkyl group having 1 to 18 carbon atoms,

[0500] A ring-forming aryl group having 6 to 18 carbon atoms, and

[0501] Complex circulators with 5 to 18 ring-forming atoms

[0502] It is a group selected from a group consisting of

[0503] Specific examples of each of the above-mentioned arbitrary substituents are specific examples of substituents described in the above-mentioned section "Substituents described in this specification".

[0504] Unless otherwise specified in this specification, any adjacent 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, and more preferably a benzene ring.

[0505] Unless otherwise stated in this specification, any substituent may have additional substituents. Any additional substituents of any substituent are the same as said arbitrary substituent.

[0506] In the present specification, the numerical range indicated using “AA to BB” means a range that includes the numerical value AA listed before “AA to BB” as a lower limit and the numerical value BB listed after “AA to BB” as an upper limit.

[0507] [New Compound]

[0508] A compound according to one embodiment of the present invention is represented by formula (1).

[0509]

[0510] [In Equation (1),

[0511] X1 is O or S.

[0512] R1 to R8 are each independently

[0513] hydrogen atom,

[0514] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

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

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

[0517] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0518] -Si(R 901 )(R 902 )(R903 ),

[0519] -O-(R 904 ),

[0520] -S-(R 905 ),

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

[0522] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0523] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0524] At least one of R1 to R8 is a deuterium atom.

[0525] R 11 ~R 19 Each independently

[0526] hydrogen atom,

[0527] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0528] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0529] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0530] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0531] -Si(R 901 )(R 902 )(R 903 ),

[0532] -O-(R 904 ),

[0533] -S-(R 905 ), or

[0534] -N(R 906 )(R 907 )am.

[0535] L1 is

[0536] single bond, or

[0537] It is a substituted or unsubstituted ring-forming arylene group with 6 to 10 carbon atoms.

[0538] n1 is an integer from 0 to 3.

[0539] If n1 is 0, (L1) n1 is a single bond.

[0540] When n1 is 2 or more, 2 or more L1s are connected in series. When n1 is 2 or more, 2 or more L1s may be identical or different.

[0541] L2 is

[0542] single bond, or

[0543] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or

[0544] It is a divalent complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0545] n2 is an integer from 0 to 3.

[0546] If n2 is 0, (L2) n2 is a single bond.

[0547] When n2 is 2 or more, 2 or more L2s are connected in series. When n2 is 2 or more, 2 or more L2s may be identical or different.

[0548] Ar1 is

[0549] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0550] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0551] R 901 ~R 907 Each independently

[0552] hydrogen atom,

[0553] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0554] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

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

[0556] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0557] R 901 ~R 907 If there are 2 or more of these, 2 or more R 901 ~R 907 Each of these may be the same or different.

[0558] A compound according to one embodiment of the present invention can improve the performance of an organic EL device when used in an organic layer of an organic EL device. For example, an organic EL device with a long lifespan can be realized.

[0559] At least one of R1 to R8 is a deuterium atom.

[0560] In one embodiment, R1 to R8 are all deuterium atoms.

[0561] In one embodiment, R1 to R8 are each independently hydrogen atoms. In this case, at least one of the hydrogen atoms R1 to R8 is a deuterium atom.

[0562] In one embodiment, X1 is O.

[0563] In one embodiment, R 11 ~R 19 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0564] In one embodiment, R 11 ~R 19 is a hydrogen atom.

[0565] In one embodiment, R 11 ~R 19 They are all light hydrogen atoms.

[0566] In one embodiment, Ar1 is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[0567] In one embodiment, Ar1 is a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.

[0568] In one embodiment, Ar1 is

[0569] Substituted or unsubstituted phenyl group,

[0570] Substituted or unsubstituted biphenyl groups, or

[0571] It is a substituted or unsubstituted naphthyl group.

[0572] In one embodiment, Ar1 is a substituted or unsubstituted phenyl group.

[0573] In one embodiment, all hydrogen atoms in Ar1 are light hydrogen atoms.

[0574] In one embodiment, L1 is

[0575] single bond,

[0576] A substituted or unsubstituted phenylene group, or

[0577] It is a Naphthalene diary of substitution or non-substitution.

[0578] In one embodiment, L1 is a single bond.

[0579] In equation (1), n1 is an integer from 0 to 3.

[0580] If n1 is 0, (L1) n1 It is a single bond, and Ar1 and the anthracene backbone are directly bonded.

[0581] When n1 is 1, Ar1 and the anthracene skeleton bind through L1.

[0582] When n1 is 2 or 3, 2 or 3 L1s are connected in series. In this case, Ar1 and the anthracene skeleton each bind to the L1 that is furthest from each other among the L1s connected in series.

[0583] In one embodiment, n1 is 0, 1, or 2.

[0584] In one embodiment, n1 is 0 or 1.

[0585] In one embodiment, n1 is 0.

[0586] In one embodiment, L2 is

[0587] single bond, or

[0588] It is a substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms.

[0589] In one embodiment, L2 is

[0590] single bond, or

[0591] It is a substituted or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms.

[0592] In one embodiment, L2 is

[0593] single bond,

[0594] A substituted or unsubstituted phenylene group, or

[0595] It is a Naphthalene diary of substitution or non-substitution.

[0596] In one embodiment, L2 is a single bond.

[0597] In equation (1), n2 is an integer from 0 to 3.

[0598] If n2 is 0, (L2) n2 It is a single bond, and the tetracyclic condensation structure (naphthobenzofuran backbone or naphthobenzothiophen backbone) and the anthracene backbone are directly bonded.

[0599] When n2 is 1, the tetracyclic condensation structure and the anthracene backbone are connected through L2.

[0600] When n2 is 2 or 3, 2 or 3 L2s are connected in series. In this case, the tetracyclic condensation structure and the anthracene backbone are each connected to the L2s that are furthest apart from each other among the L2s connected in series.

[0601] In one embodiment,

[0602] R1 to R8 are all deuterium atoms, and

[0603] R 11 ~R 19 They are all light hydrogen atoms,

[0604] All the hydrogen atoms in Ar1 are light hydrogen atoms.

[0605] In this specification, a specific hydrogen atom (or R, which is a hydrogen atom) x "(X is an integer used to identify the substituent)) is a deuterium atom" means that in the hydrogen atom, the ratio of deuterium atoms to the sum of light hydrogen atoms and deuterium atoms is greater than the natural abundance.

[0606] Regarding the sum of light hydrogen atoms and deuterium atoms, the fact that the proportion of deuterium atoms is greater than the natural abundance can be confirmed by a nuclear magnetic resonance device.

[0607] In this specification, a specific hydrogen atom (or R, which is a hydrogen atom) X "X (meaning a number or symbol for identifying the substituent) is a 'light hydrogen atom'" means that in the hydrogen atom, the ratio of deuterium atoms to the sum of light hydrogen atoms and deuterium atoms is less than or equal to the natural abundance.

[0608] With respect to the sum of light hydrogen atoms and deuterium atoms, it can be confirmed by a nuclear magnetic resonance device that the ratio of deuterium atoms is less than the natural abundance.

[0609] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3).

[0610]

[0611] [In formulas (1-1) to (1-3), X1, L1, L2, Ar1, R1 to R8, and R 11 ~R 19 is as defined in the above equation (1).

[0612] 4 Rs a Among them, two or more adjacent sets of at least one combine to form a saturated or unsaturated ring with or without substitution, or do not form a saturated or unsaturated ring with or without substitution.

[0613] 4 Rs b Among them, two or more adjacent sets of at least one combine to form a saturated or unsaturated ring with or without substitution, or do not form a saturated or unsaturated ring with or without substitution.

[0614] R that does not form the above ring a and R b Each independently

[0615] hydrogen atom,

[0616] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0617] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0618] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0619] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0620] -Si(R 901 )(R 902 )(R 903 ),

[0621] -O-(R 904 ),

[0622] -S-(R 905 ),

[0623] -N(R 906 )(R 907 ),

[0624] Halogen atom, cyano group, nitro group,

[0625] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0626] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0627] R 901 ~R 907 [It is as defined in the above equation (1).]

[0628] In one embodiment, 4 R a Among them, two or more adjacent sets of at least one do not form a saturated or unsaturated ring of substitution or non-substitution.

[0629] In one embodiment, 4 R b Among them, two or more adjacent sets of at least one do not form a saturated or unsaturated ring of substitution or non-substitution.

[0630] In one embodiment, the compound represented by formula (1) is a compound represented by the following formula (1-11) or formula (1-12).

[0631]

[0632] [In Equation (1-11), X1 and Ar1 are as defined in Equation (1) above.

[0633] In Equation (1-12), X1 and Ar1 are as defined in Equation (1) above. L 21 It is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group.

[0634] D represents a deuterium atom.

[0635] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-21) to (1-23).

[0636]

[0637] [In Equation (1-21), X1 and Ar1 are as defined in Equation (1) above.

[0638] In Equation (1-22), X1 and Ar1 are as defined in Equation (1) above. L 21 It is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group.

[0639] In Equation (1-23), X1 and Ar1 are as defined in Equation (1) above.

[0640] D represents a deuterium atom.

[0641] In one embodiment, the substituent in the case of “substituent or non-substituent” in Formula (1) is,

[0642] alkyl group having 1 to 50 carbon atoms,

[0643] Alkenyl groups having 2 to 50 carbon atoms,

[0644] Alkynyl group having 2 to 50 carbon atoms,

[0645] Ring-forming cycloalkyl group having 3 to 50 carbon atoms,

[0646] -Si(R 901 )(R 902 )(R 903 ),

[0647] -O-(R 904 ),

[0648] -S-(R 905 ),

[0649] -N(R 906 )(R 907 ),

[0650] Halogen atom, cyano group, nitro group,

[0651] A ring-forming aryl group having 6 to 50 carbon atoms, or

[0652] It is a complex circulator with 5 to 50 ring-forming atoms.

[0653] R 901 ~R 907 Each independently

[0654] hydrogen atom,

[0655] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0656] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0657] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0658] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0659] In one embodiment, the substituent in the case of “substituent or non-substituent” in Formula (1) is,

[0660] alkyl group having 1 to 50 carbon atoms,

[0661] A ring-forming aryl group having 6 to 50 carbon atoms, and

[0662] Complex circulators with 5 to 50 ring-forming atoms

[0663] It is a group selected from the group consisting of

[0664] In one embodiment, the substituent in the case of “substituent or non-substituent” in Formula (1) is,

[0665] alkyl group having 1 to 18 carbon atoms,

[0666] A ring-forming aryl group having 6 to 18 carbon atoms, and

[0667] Complex circulators with 5 to 18 ring-forming atoms

[0668] It is a group selected from the group consisting of

[0669] A compound according to one aspect of the present invention can be synthesized, depending on the example, by using a known alternative reaction or raw material suited to the target object.

[0670] Specific examples of compounds according to one embodiment of the present invention are described below, but these are merely examples and compounds according to one embodiment of the present invention are not limited to the following specific examples.

[0671]

[0672]

[0673]

[0674]

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682]

[0683]

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691]

[0692]

[0693]

[0694]

[0695]

[0696]

[0697] [Materials for Organic Electroluminescence Devices]

[0698] A compound according to one embodiment of the present invention is useful as a material for an organic EL device, and is useful as a material used in the light-emitting layer of an organic EL device, for example.

[0699] [Organic EL Device]

[0700] An organic EL device according to one embodiment of the present invention will be described.

[0701] An organic EL device according to one embodiment of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers comprises a compound according to one embodiment of the present invention (a compound represented by formula (1)).

[0702] An organic EL device according to one embodiment of the present invention can improve performance by having the above configuration.

[0703] In one embodiment, an anode, a light-emitting layer, and a cathode are included in this order, and at least one layer of the organic layer in the light-emitting layer comprises a compound according to one aspect of the present invention.

[0704] In one embodiment, an organic EL device according to one aspect of the present invention further comprises a light-emitting layer comprising a compound represented by any one of the following formulas (D11) to (D41).

[0705]

[0706] Formulas (D11) to (D41) will be described later.

[0707] (Compound represented by formula (D11))

[0708] A compound represented by formula (D11) is described.

[0709]

[0710] [In Equation (D11),

[0711] The three Zs are each independently CR a Or it is a nitrogen atom.

[0712] Ring A1 and Ring A2 are each independently

[0713] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or

[0714] It is a complex ring with 5 to 50 atoms forming a ring, either substituted or unsubstituted.

[0715] R a If there are multiple instances of , multiple R a One or more of the groups consisting of two or more adjacent groups,

[0716] They combine with each other to form a substituted or unsubstituted single ring,

[0717] They combine with each other to form substituted or unsubstituted condensed rings, or

[0718] They do not combine with each other.

[0719] nD11 and nD12 are each independently 0, 1, 2, 3, or 4.

[0720] R b If there are multiple instances of , multiple R b One or more of the groups consisting of two or more adjacent groups,

[0721] They combine with each other to form a substituted or unsubstituted single ring,

[0722] They combine with each other to form substituted or unsubstituted condensed rings, or

[0723] They do not combine with each other.

[0724] R c If there are multiple instances of , multiple R c One or more of the groups consisting of two or more adjacent groups,

[0725] They combine with each other to form a substituted or unsubstituted single ring,

[0726] They combine with each other to form substituted or unsubstituted condensed rings, or

[0727] They do not combine with each other.

[0728] R that does not form the above single ring and the above condensed ring a , R b , and R c Each independently

[0729] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0730] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0731] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0732] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0733] -Si(R 901 )(R 902 )(R 903 ),

[0734] -O-(R 904 ),

[0735] -S-(R 905 ),

[0736] -N(R 906 )(R 907 ),

[0737] Halogen atom, cyano group, nitro group,

[0738] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0739] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0740] R 901 ~R 907 [It is as defined in the above equation (1).]

[0741] The “aromatic hydrocarbon ring” of the A1 ring and A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned “ring-forming aryl group having 6 to 50 carbon atoms.”

[0742] The “aromatic hydrocarbon ring” of the A1 ring and A2 ring includes two carbon atoms on the condensed two-ring structure at the center of the above formula (D11) as ring-forming atoms.

[0743] Specific examples of “substituted or unsubstituted ring-forming aromatic hydrocarbons having 6 to 50 carbon atoms” include compounds in which a hydrogen atom is introduced into a “substituted or unsubstituted aryl group” described in Specific Example Group G1.

[0744] The “complex ring” of the A1 ring and A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned “complex ring group having 5 to 50 ring-forming atoms.”

[0745] The “complex ring” of the A1 ring and A2 ring includes two carbon atoms on the condensed two-ring structure at the center of the above formula (D11) as ring-forming atoms.

[0746] Specific examples of “a complex ring having 5 to 50 substituent or non-substituent ring-forming atoms” include compounds in which a hydrogen atom is introduced into a “substituent or non-substituent complex ring group” described in Specific Example Group G2.

[0747] Rb is bonded to any one of the carbon atoms forming an aromatic hydrocarbon ring as an A1 ring, or to any one of the atoms forming a heterocyclic ring as an A1 ring.

[0748] Rc is bonded to any one of the carbon atoms forming an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms forming a heterocyclic ring as an A2 ring.

[0749] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a).

[0750] In one embodiment, at least two of Ra, Rb, and Rc are represented by the following formula (D11a).

[0751]

[0752] [In Equation (D11a),

[0753] L D101 silver

[0754] single bond,

[0755] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or

[0756] It is a divalent complex circulator with 5 to 30 atoms forming a ring, either substituent or unsubstituent.

[0757] Ar D101 silver

[0758] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,

[0759] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or

[0760] It is represented by the following equation (D11b).

[0761]

[0762] (In Equation (D11b),

[0763] L D102 and L D103 Each independently

[0764] single bond,

[0765] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or

[0766] It is a divalent complex circulator with 5 to 30 atoms forming a ring, either substituent or unsubstituent.

[0767] Ar D102 and Ar D103 A group consisting of

[0768] They combine with each other to form a substituted or unsubstituted single ring,

[0769] They combine with each other to form substituted or unsubstituted condensed rings, or

[0770] They do not combine with each other.

[0771] Ar that does not form the above-mentioned single ring or condensed ringD102 and Ar D103 Each independently

[0772] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0773] It is a complex circulator with 5 to 50 substitutive or unsubstitutive ring-forming atoms.

[0774] Specific examples of the compound represented by Formula (D11) are described below, but these are merely examples and the compound represented by Formula (D11) is not limited to the following specific examples.

[0775]

[0776] (Compound represented by formula (D21))

[0777] A compound represented by formula (D21) is described.

[0778]

[0779] [In Equation (D21),

[0780] R D201 and R D202 , R D202 and R D203 , and R D203 and R D204 At least one of the sets combines with each other to form a divalent group represented by the following formula (D22).

[0781] R D205 and R D206 , R D206 and R D207 , and R D207 and R D208 At least one of the sets combines with each other to form a divalent group represented by the following formula (D23).

[0782]

[0783] (R D211 ~R D214 , and R that does not form a divalent group represented by equation (D22). D201 ~R D204At least one of them is a univalent group represented by the following formula (D24).

[0784] R D221 ~R D224 , and R that does not form a divalent group represented by equation (D23). D205 ~R D208 At least one of them is a univalent group represented by the following formula (D24).

[0785] X D2 is an oxygen atom, a sulfur atom, or NR D209 am.

[0786] R that does not form a divalent group represented by the above equations (D22) and (D23), and also is not a monovalent group represented by the above equation (D24). D201 ~R D208 , R that is not a monovalent group represented by the above equation (D24). D211 ~R D214 and R D221 ~R D224 , and R D209 Each independently

[0787] hydrogen atom,

[0788] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0789] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0790] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0791] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0792] -Si(R 901 )(R 902 )(R 903 ),

[0793] -O-(R 904 ),

[0794] -S-(R 905 ),

[0795] -N(R 906 )(R 907 ),

[0796] Halogen atom, cyano group, nitro group,

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

[0798] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0799]

[0800] (In Equation (D24),

[0801] Ar D201 and Ar D202 Each independently

[0802] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0803] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0804] L D201 ~L D203 Each independently

[0805] single bond,

[0806] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms,

[0807] A divalent complex circulator with 5 to 30 atoms forming a ring, either substituted or unsubstituted, or

[0808] It is a divalent linker formed by combining 2 to 4 groups selected from the group consisting of a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 30 atoms.

[0809] * indicates the ring structure represented by the above formula (D21), or the connection position of the roof tile represented by formula (D22) or formula (D23).

[0810] R 901 ~R 907 [It is as defined in the above equation (1).]

[0811] In Equation (D21), the location where the divalent group represented by Equation (D22) and the divalent group represented by Equation (D23) are formed is not particularly limited, and R D201 ~R D208 The device can be formed in a possible location.

[0812] As for the compound represented by formula (D21), in addition to the compound described in International Publication No. 2014 / 104144, for example, the compound shown below may be cited as specific examples, but these are merely examples and the compound represented by formula (21) is not limited to the following specific examples.

[0813]

[0814] (Compound represented by formula (D31))

[0815] A compound represented by formula (D31) is described.

[0816]

[0817] [In Equation (D31),

[0818] R D301 ~R D307 and R D311 ~R D317 One or more sets consisting of two or more adjacent rings may combine to form a substituted or non-substituted ring, combine to form a substituted or non-substituted condensed ring, or not combine with each other.

[0819] R that does not form the above single ring and the above condensed ring D301 ~R D307 and R D311 ~R D317 Each independently

[0820] hydrogen atom,

[0821] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0822] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0823] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0824] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0825] -Si(R 901 )(R 902 )(R 903 ),

[0826] -O-(R 904 ),

[0827] -S-(R 905 ),

[0828] -N(R 906 )(R 907 ),

[0829] Halogen atom, cyano group, nitro group,

[0830] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0831] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0832] R D321 and R D322 Each independently

[0833] hydrogen atom,

[0834] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0835] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0836] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0837] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0838] -Si(R 901 )(R 902 )(R 903 ),

[0839] -O-(R 904 ),

[0840] -S-(R 905 ),

[0841] -N(R906 )(R 907 ),

[0842] Halogen atom, cyano group, nitro group,

[0843] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0844] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0845] R 901 ~R 907 [It is as defined in the above equation (1).]

[0846] "R D301 ~R D307 and R D311 ~R D317 A “set consisting of two or more adjacent items” is, for example, R D301 and R D302 A group consisting of, R D302 and R D303 A group consisting of, R D303 and R D304 A group consisting of, R D305 and R D306 A group consisting of, R D306 and R D307 A group consisting of, R D301 and R D302 and R D303 It is a combination of groups, etc., consisting of

[0847] In one embodiment, R D301 ~R D307 and R D311 ~R D317 At least one of them is -N(R 906 )(R 907 )am.

[0848] In one embodiment, R D301 ~R D307 and R D311 ~R D317 Two of them are -N(R 906 )(R 907 )am.

[0849] In one embodiment, RD301 ~R D307 and R D311 ~R D317 Each independently

[0850] hydrogen atom,

[0851] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0852] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0853] Specific examples of the compound represented by Formula (D31) are described below, but these are merely examples and the compound represented by Formula (D31) is not limited to the following specific examples.

[0854]

[0855]

[0856] (Compound represented by formula (D41))

[0857] A compound represented by formula (D41) is described.

[0858]

[0859] [In Equation (D41),

[0860] Ring a, ring b, and ring c are each independently

[0861] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or,

[0862] It is a complex ring with 5 to 50 atoms forming a ring, either substituted or unsubstituted.

[0863] R D401 and R D402 Each of them independently combines with the above-mentioned a, b, or c ring to form a substitutive or non-substitutive complex ring, or does not combine.

[0864] R that does not form the above complex ring D401 and R D402 Each independently

[0865] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0866] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0867] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0868] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

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

[0870] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0871] Ring a, ring b and ring c are rings that condense into a condensed 2-ring structure at the center of formula (D41) consisting of a B atom and two N atoms (a substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex ring with 5 to 50 atoms).

[0872] The “aromatic hydrocarbon ring” of the a, b, and c rings has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned “aryl group.” The “aromatic hydrocarbon ring” of the a ring contains three carbon atoms in the condensed two-ring structure at the center of Formula (D41) as ring-forming atoms. The “aromatic hydrocarbon ring” of the b and c rings contains two carbon atoms in the condensed two-ring structure at the center of Formula (D41) as ring-forming atoms. Specific examples of the “substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in Specific Example Group G1.

[0873] The “complex ring” of the a, b, and c rings has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned “complex group.” The “complex ring” of the a ring contains three carbon atoms in the condensed two-ring structure at the center of Formula (D41) as ring-forming atoms. The “complex ring” of the b and c rings contains two carbon atoms in the condensed two-ring structure at the center of Formula (D41) as ring-forming atoms. Specific examples of the “complex ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include compounds in which a hydrogen atom is introduced into the “complex group” described in Specific Example Group G2.

[0874] R D401 and R D402 Each may independently combine with the a ring, b ring, or c ring to form a substitutive or unsubstitutive complex ring. In this case, the complex ring contains a nitrogen atom on the condensed two-ring structure at the center of Equation (D41). In this case, the complex ring may contain heteroatoms other than nitrogen atoms. R D401 and R D402 That G bonds with the a ring, b ring, or c ring means, specifically, that the atoms constituting the a ring, b ring, or c ring and R D401 and R D402 It means that the atoms constituting it bond. For example, R D401 Combined with this a ring, R D401 A nitrogen-containing heterocyclic ring of dicyclic condensation (or tricyclic condensation or higher) formed by the condensation of a ring containing and a ring may be formed. Specific examples of said nitrogen-containing heterocyclic rings include compounds corresponding to a nitrogen-containing dicyclic condensation or higher heterocyclic group among the specific example group G2.

[0875] R D401 When this b ring combines, R D402 When a combines with a ring, and R D402 The same applies when a c is combined with a ring.

[0876] In one embodiment, the a ring, b ring, and c ring in formula (D41) are each independently substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms.

[0877] In one embodiment, the ring a, ring b, and ring c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0878] In one embodiment, R in formula (D41) D401 and R D402 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms, preferably a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[0879] In one embodiment, the compound represented by formula (D41) is a compound represented by the following formula (D42).

[0880]

[0881] (In Equation (D42),

[0882] R D401A is R D411 and R D421 Combines with 1 or more selected from the group consisting of to form a permuted or unpermuted complex ring, or does not combine. R D402A is R D413 and R D414 It combines with 1 or more selected from the group consisting of to form a permuted or non-permuted complex ring, or does not combine.

[0883] R that does not form the above-mentioned or non-substitutive complex ring D401A and R D402A Each independently

[0884] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0885] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0886] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0887] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0888] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0889] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0890] R D411 ~R D421 Among them, two or more adjacent sets of at least one may combine with each other to form a substituted or non-substituted saturated or unsaturated ring, or not combine with each other.

[0891] R that does not form the above-mentioned or non-substituent complex ring or the above-mentioned saturated or unsaturated ring D411 ~R D421 Each independently

[0892] hydrogen atom,

[0893] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0894] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0895] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0896] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0897] -Si(R 901 )(R 902 )(R 903 ),

[0898] -O-(R 904 ),

[0899] -S-(R 905 ),

[0900] -N(R 906 )(R 907 ),

[0901] Halogen atom, cyano group, nitro group,

[0902] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0903] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0904] R 901 ~R 907 is as defined in the above equation (1).

[0905] R of Equation (D42) D401A and R D402A is R of equation (D41) D401 and R D402 It is a corresponding unit.

[0906] For example, R D401A and R D411 By combining, a nitrogen-containing heterocyclic ring of dicyclic condensation (or tricyclic condensation or higher) may be formed by the condensation of a ring containing these elements and a benzene ring corresponding to the α-ring. Specific examples of said nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing heterocyclic condensation or higher heterocyclic group among Specific Example Group G2. R D401A and R D412 When combining, R D402A and R D413 In the case of this combination, and R D402A and R D414 The case where it is combined is the same as above.

[0907] R D411 ~R D421 Among them, at least one set of two or more adjacent elements may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R D411 and R D412 A benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring may be condensed to form a structure with respect to the six-membered ring to which they are bonded, and the formed condensed ring becomes a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring.

[0908] In one embodiment, R that does not contribute to ring formation D411 ~R D421 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms.

[0909] In one embodiment, R that does not contribute to ring formation D411 ~R D421 Each is independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent complex circulator having 5 to 50 atoms.

[0910] In one embodiment, R that does not contribute to ring formation D411 ~R D421 Each is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0911] In one embodiment, R that does not contribute to ring formation D411 ~R D421 Each is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D411 ~R D421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0912] In one embodiment, the compound represented by the formula (D42) is a compound represented by the following formula (D43).

[0913]

[0914] (In Equation (D43),

[0915] R D431 is R D446 Combines with to form a permuted or unpermuted complex, or does not combine. R D433 is R D447Combines with to form a permuted or unpermuted complex, or does not combine. R D434 is R D451 Combines with to form a permuted or unpermuted complex, or does not combine. R D441 is R D442 Combines with to form a substitutive or non-substitutive complex, or does not combine.

[0916] R D431 ~R D451 Two or more adjacent sets of at least one of each combine to form a substituted or non-substituted saturated or unsaturated ring, or do not combine with each other.

[0917] R that does not form the above-mentioned or non-substituent complex ring or the above-mentioned saturated or unsaturated ring D431 ~R D451 Each independently

[0918] hydrogen atom,

[0919] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0920] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0921] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0922] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0923] -Si(R 901 )(R 902 )(R 903 ),

[0924] -O-(R 904 ),

[0925] -S-(R 905 ),

[0926] -N(R 906 )(R 907 ),

[0927] Halogen atom, cyano group, nitro group,

[0928] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[0929] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[0930] R 901 ~R 907 is as defined in the above equation (1).

[0931] R D431 is R D446 It may be combined with to form a permuted or non-permuted complex ring. For example, R D431 and R D446 This combination R D446 It is also possible to form a nitrogen-containing heterocyclic ring formed by the condensation of the bonding benzene ring, a ring containing N, and a benzene ring corresponding to the a ring. Specific examples of said nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing heterocyclic condensed heterocyclic group of specific examples G2. R D433 and R D447 In this case, R D434 and R D451 In the case of this combination, and R D441 and R D442 The case where it is combined is the same as above.

[0932] In one embodiment, R that does not contribute to ring formation D431 ~R D451 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms.

[0933] In one embodiment, R that does not contribute to ring formation D431 ~R D451 Each is independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent complex circulator having 5 to 50 atoms.

[0934] In one embodiment, R that does not contribute to ring formation D431 ~R D451 Each is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0935] In one embodiment, R that does not contribute to ring formation D431 ~R D451 Each is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D431 ~R D451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0936] In one embodiment, the compound represented by the above formula (D43) is a compound represented by the following formula (D43A).

[0937]

[0938] (In Equation (D43A),

[0939] R D461 silver

[0940] hydrogen atom,

[0941] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0942] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0943] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0944] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or

[0945] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0946] R D462 ~R D465 Each independently

[0947] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0948] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0949] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0950] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or

[0951] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0952] In one embodiment, R D461 ~R D465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[0953] In one embodiment, R D461 ~R D465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0954] In one embodiment, the compound represented by the above formula (D43) is a compound represented by the following formula (D43B).

[0955]

[0956] (In Equation (D43B),

[0957] R D471 and R D472 Each independently

[0958] hydrogen atom,

[0959] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0960] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0961] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0962] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0963] -N(R 906 )(R 907 ), or

[0964] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0965] R D473 ~R D475 Each independently

[0966] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0967] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0968] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0969] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0970] -N(R 906 )(R 907 ), or

[0971] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0972] R 906 and R 907 is as defined in the above equation (1).

[0973] In one embodiment, the compound represented by the above formula (D43) is a compound represented by the following formula (D43B').

[0974]

[0975] (In equation (D43B'), R D472 ~R D475 is as defined in the above equation (D43B).

[0976] In one embodiment, R D471 ~R D475 At least one of them

[0977] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0978] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0979] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0980] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0981] -N(R 906 )(R 907 ), or

[0982] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0983] In one embodiment,

[0984] R D472 Is

[0985] hydrogen atom,

[0986] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0987] -N(R 906 )(R 907 ), or

[0988] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0989] R D471 and R D473 ~R D475 Each independently

[0990] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0991] -N(R 906 )(R 907 ), or

[0992] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[0993] In one embodiment, the compound represented by the formula (D43) is a compound represented by the following formula (D43C).

[0994]

[0995] (In Equation (D43C),

[0996] R D481 and R D482 Each independently

[0997] hydrogen atom,

[0998] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0999] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1000] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1001] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or

[1002] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[1003] R D483 ~R D486 Each independently

[1004] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1005] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1006] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1007] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or

[1008] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[1009] In one embodiment, the compound represented by the formula (D43) is a compound represented by the following formula (D43C').

[1010]

[1011] (In equation (D43C'), R D483 ~R D486 is as defined in the above equation (D43C).

[1012] In one embodiment, R D481 ~R D486 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[1013] In one embodiment, RD481 ~R D486 Each is independently a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.

[1014] In one embodiment, the compound represented by the above formula (D41) is a compound represented by the following formula (D44).

[1015]

[1016] (In Equation (D44),

[1017] X D401 is O or S.

[1018] R D401B is R D487 and R D497 Combines with 1 or more selected from the group consisting of to form a permuted or unpermuted complex ring, or does not combine. R D402B is R D489 and R D490 It combines with 1 or more selected from the group consisting of to form a permuted or non-permuted complex ring, or does not combine.

[1019] R that does not form the above-mentioned or non-substitutive complex ring D401B and R D402B Each independently

[1020] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1021] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1022] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1023] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

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

[1025] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[1026] RD487 ~R D497 Among them, two or more adjacent sets of at least one may combine with each other to form a substituted or non-substituted saturated or unsaturated ring, or not combine with each other.

[1027] R that does not form the above-mentioned or non-substituent complex ring or the above-mentioned saturated or unsaturated ring D487 ~R D497 Each independently

[1028] hydrogen atom,

[1029] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1030] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1031] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1032] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[1033] -Si(R 901 )(R 902 )(R 903 ),

[1034] -O-(R 904 ),

[1035] -S-(R 905 ),

[1036] -N(R 906 )(R 907 ),

[1037] Halogen atom, cyano group, nitro group,

[1038] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or

[1039] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.

[1040] R 901 ~R 907 is as defined in the above equation (1).

[1041] In one embodiment, RD401B and R D402B Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[1042] In one embodiment, R D487 ~R D497 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[1043] The compound represented by formula (D41) first has a ring a, a ring b, and a ring c linked by a linker (NR D401 The group including and NR D402 An intermediate can be prepared by combining with a group (containing B) (first reaction), and a final product can be prepared by combining the a ring, b ring, and c ring with a linker (a group containing B) (second reaction). In the first reaction, an amination reaction such as the Buchwald-Hartwig reaction can be applied. In the second reaction, a tandem hetero-Friedel-Crafts reaction can be applied.

[1044] Specific examples of the compound represented by Formula (D41) are described below, but these are merely examples and the compound represented by Formula (D41) is not limited to the following specific examples.

[1045]

[1046]

[1047]

[1048]

[1049]

[1050]

[1051]

[1052]

[1053]

[1054]

[1055]

[1056]

[1057]

[1058] In addition, the light-emitting layer may use compounds such as those shown below, in addition to the compounds represented by the aforementioned formulas (D11), (D21), (D31), or (D41).

[1059]

[1060] In one embodiment, the light-emitting layer contains a compound represented by the aforementioned formula (D41).

[1061] In one embodiment, an organic EL device according to one aspect of the present invention has a hole transport band between the anode and the light-emitting layer.

[1062] In one embodiment, an organic EL device according to one aspect of the present invention has an electron transport band between the cathode and the light-emitting layer.

[1063] A schematic configuration of an organic EL device of one embodiment of the present invention will be explained with reference to FIG. 1.

[1064] An organic EL element (1) according to one embodiment of the present invention has a substrate (2), an anode (3), a light-emitting layer (5), a cathode (10), a hole transport band (4) between the anode (3) and the light-emitting layer (5), and an electron transport band (6) between the light-emitting layer (5) and the cathode (10).

[1065] As a representative device configuration of the organic EL device of the present invention, a structure in which the following structure is stacked on a substrate is exemplified.

[1066] (1) Anode / Luminous layer / Cathode

[1067] (2) Anode / hole transport band / emissive layer / cathode

[1068] (3) Anode / emissive layer / electron transport band / cathode

[1069] (4) Anode / Hole transport band / Emitting layer / Electron transport band / Cathode

[1070] (「 / 」 indicates that each layer is stacked adjacently.)

[1071] The hole transport band is a collective term for one or more layers disposed between the anode and the light-emitting layer. The hole transport band is composed of, for example, layers called the electron blocking layer, the hole transport layer, and the hole injection layer described below, starting from the light-emitting layer side; it may be a stacked structure including all of these, or it may be composed of only some of these layers. In addition, for each of the above layers, two or more types of layers may be used, for example, two types of hole transport layers with different compositions may be stacked.

[1072] Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.

[1073] The electron transport band is a collective term for one or more layers disposed between the cathode and the light-emitting layer. The electron transport band is composed of, for example, each layer called a hole blocking layer, an exciton blocking layer, an electron transport layer, and an electron injection layer, as described below, from the light-emitting layer side. It may be a stacked structure including all of these, or it may be composed of only some of these layers. In addition, for each of the above layers, two or more types of layers may be used, for example, two types of electron transport layers with different compositions may be stacked.

[1074] Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.

[1075] Hereinafter, a component that can be used in an organic EL device according to one embodiment of the present invention, and a material other than the compound constituting each layer, will be described.

[1076] (Circuit board)

[1077] A substrate is used as a support for a light-emitting element. For example, glass, quartz, plastic, etc. may be used as the substrate. In addition, a flexible substrate may be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.

[1078] (anode)

[1079] For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride) may be used.

[1080] (Hole injection layer)

[1081] The hole injection layer is a layer containing a material with high hole injection properties. Materials with high hole injection properties may include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.).

[1082] (Pure transport layer)

[1083] The hole transport layer is a layer containing a material with high hole transportability. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., may be used for the hole transport layer. Polymeric compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) or poly(4-vinyltriphenylamine) (abbreviated: PVTPA) may also be used. However, if the material has higher hole transportability than electron transportability, materials other than these may be used. Furthermore, the layer containing a material with high hole transportability may not only be a single layer, but may also be a layer made of the above material stacked in two or more layers.

[1084] (Guest (dopant) material of the emissive layer)

[1085] The emissive layer is a layer containing a material with high luminescence, and various materials can be used. For example, as the material with high luminescence, fluorescent compounds that emit fluorescence or phosphorescent compounds that emit phosphorescence can be used. Fluorescent compounds are compounds capable of emitting light from a singlet excited state, and phosphorescent compounds are compounds capable of emitting light from a triplet excited state.

[1086] As blue fluorescent light-emitting materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. As green fluorescent light-emitting materials that can be used in the light-emitting layer, aromatic amine derivatives, etc., can be used. As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc., can be used.

[1087] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the emissive layer. Iridium complexes are used as green phosphorescent materials that can be used in the emissive layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the emissive layer.

[1088] (Host material of the light-emitting layer)

[1089] As for the emissive layer, it may be configured such that the aforementioned highly luminescent material (guest material) is dispersed in another material (host material). Various materials may be used as the material for dispersing the highly luminescent material, and it is preferable to use a material that has a lower empty orbit level (LUMO level) and a lower highest occupied orbit level (HOMO level) than the highly luminescent material.

[1090] As a material (host material) for dispersing a highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 3) a condensed aromatic compound such as a carbazole derivative, anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

[1091] In addition, a compound with delayed fluorescence (thermally activated delayed fluorescence) may be used as a host material. It is also preferable that the light-emitting layer comprises the material used in the present invention described above and a host compound with delayed fluorescence.

[1092] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[1093] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc., may be provided adjacent to the light-emitting layer.

[1094] An electron blocking layer is a layer that prevents electrons from leaking from the emissive layer to the hole transport layer. A hole blocking layer is a layer that prevents holes from leaking from the emissive layer to the electron transport layer. An exciton blocking layer is a layer that prevents excitons generated in the emissive layer from diffusing into adjacent layers and confines the excitons within the emissive layer.

[1095] (Electron transport layer)

[1096] The electron transport layer is a layer containing a material with high electron transport capacity. In the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) complex aromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds may be used.

[1097] (Electron injection layer)

[1098] The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer includes metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinolinolato-lithium (Liq), and lithium oxide (LiO2). x Alkali metals, alkaline earth metals, or compounds thereof such as ) can be used.

[1099] (cathode)

[1100] For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof that have a small work function (specifically 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[1101] In an organic EL device according to one embodiment of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and improve luminous efficiency, a range of several nm to 1 μm is preferred.

[1102] In an organic EL device according to one embodiment of the present invention, the method of forming each layer is not particularly limited. Conventionally known formation methods such as vacuum deposition and spin coating may be used. Each layer, such as a light-emitting layer, may be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or dipping of a solution dissolved in a solvent, spin coating, casting, bar coating, or roll coating.

[1103] [Electronic devices]

[1104] An electronic device according to one embodiment of the present invention is characterized by having an organic EL element according to one embodiment of the present invention.

[1105] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lighting fixtures.

[1106] Examples

[1107] <Compounds>

[1108] The compound represented by formula (1) used in the manufacture of the organic EL devices of Examples 1 to 7 is shown below.

[1109]

[1110] Comparative example compounds used in the manufacture of organic EL devices of Comparative Examples 1 to 4 are shown below.

[1111]

[1112] The structures of other compounds used in the manufacture of the organic EL devices of Examples 1 to 7 and Comparative Examples 1 to 4 are shown below.

[1113]

[1114] Example 1

[1115] Fabrication of Organic EL Devices

[1116] An organic EL device was fabricated as follows.

[1117] A glass substrate (manufactured by Geomatic Co., Ltd.) equipped with an ITO transparent electrode (anode) with a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[1118] A glass substrate equipped with a transparent electrode after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and first, the transparent electrode was placed over the side on which the transparent electrode was formed, so that compound HT-1 and compound HI-1 were co-deposited such that the ratio of compound HI-1 was 3 mass%, thereby forming a hole injection layer with a film thickness of 10 nm.

[1119] Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm.

[1120] Compound EB-1 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1121] Compound Inv-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer such that the ratio of compound BD-1 was 2 mass%, and an emissive layer with a thickness of 5 nm was formed.

[1122] Compound aET-1 was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1123] On the first electron transport layer, compound bET-1 and Liq were co-deposited such that the ratio of Liq was 50 mass%, and a second electron transport layer with a thickness of 31 nm was formed.

[1124] Liq was deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1125] Metal Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1126] The device configuration of the organic EL device of Example 1 can be briefly represented as follows.

[1127] ITO(130) / HT-1:HI-1(10:3%) / HT-1(85) / EB-1(5) / Inv-1:BD-1(5:2%) / aET-1(5) / bET-1:Liq(31:50%) / Liq(1) / Al(80)

[1128] The number in parentheses indicates the film thickness (unit: nm). Also, the number in parentheses indicated by a percentage represents the proportion (mass%) of the latter compound in the layer.

[1129] Evaluation of Organic EL Devices

[1130] ·Component lifespan

[1131] At room temperature, a voltage was applied to an organic EL device such that the current density was 30 mA / cm², and the time until the brightness reached 95% of the initial brightness (LT95 (unit: h)) was measured.

[1132] Example 2

[1133] An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that a compound listed in Table 1 was used instead of Inv-1 as the host material for the light-emitting layer. The results are shown in Table 1.

[1134] Comparative Examples 1-3

[1135] An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that a compound listed in Table 1 was used instead of Inv-1 as the host material for the light-emitting layer. The results are shown in Table 1.

[1136]

[1137] Example 3

[1138] Fabrication of Organic EL Devices

[1139] An organic EL device was fabricated as follows.

[1140] A glass substrate (manufactured by Geomatic Co., Ltd.) equipped with an ITO transparent electrode (anode) with a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[1141] A glass substrate equipped with a transparent electrode after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and first, the transparent electrode was placed over the side on which the transparent electrode was formed, so that compound HT-2 and compound HI-1 were co-deposited such that the ratio of compound HI-1 was 3 mass%, thereby forming a hole injection layer with a film thickness of 10 nm.

[1142] Compound HT-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm.

[1143] Compound EB-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1144] Compound Inv-2 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer such that the ratio of compound BD-1 was 2 mass%, and an emissive layer with a thickness of 5 nm was formed.

[1145] Compound aET-1 was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1146] On the first electron transport layer, compound bET-1 and Liq were co-deposited such that the ratio of Liq was 50 mass%, and a second electron transport layer with a thickness of 31 nm was formed.

[1147] Liq was deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[1148] Metal Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1149] The device configuration of the organic EL device of Example 3 is briefly represented as follows.

[1150] ITO(130) / HT-2:HI-1(10:3%) / HT-2(85) / EB-2(5) / Inv-2:BD-1(5:2%) / aET-1(5) / bET-1:Liq(31:50%) / Liq(1) / Al(80)

[1151] The number in parentheses indicates the film thickness (unit: nm). Also, the number in parentheses indicated by a percentage represents the proportion (mass%) of the latter compound in the layer.

[1152] Evaluation of Organic EL Devices

[1153] For the obtained device, the device lifespan was evaluated in the same manner as in Example 1. The results are shown in Table 2.

[1154] Examples 4-7

[1155] An organic EL device was fabricated and evaluated in the same manner as in Example 3, except that a compound listed in Table 1 was used instead of Inv-2 as the host material for the light-emitting layer. The results are shown in Table 2.

[1156] Comparative Example 4

[1157] An organic EL device was fabricated and evaluated in the same manner as in Example 3, except that a compound listed in Table 1 was used instead of Inv-2 as the host material for the light-emitting layer. The results are shown in Table 2.

[1158]

[1159] Synthesis of Compounds

[1160] (Synthesization Example 1) Synthesis of Inv-1

[1161] Inv-1 was synthesized using the following synthesis path.

[1162] (1) Synthesis of intermediate A

[1163]

[1164] · Synthesis of Intermediate A-2

[1165] Under an argon atmosphere, a mixture of 20.0 g (104.0 mmol) of intermediate A-1 and 346 mL of THF was cooled to -5°C, 78 mL of 1.6 M n-butyllithium hexane solution was added dropwise, and the mixture was stirred at -5°C for 3 hours. After cooling the reaction mixture to -40°C, 35.7 mL (156.0 mmol) of triisopropylborate was added dropwise. After raising the temperature of the reaction mixture to 0°C, 100 mL of 4 M hydrochloric acid was added dropwise, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, the organic phase was washed with saturated saline solution, dehydrated with magnesium sulfate, and then concentrated under reduced pressure to obtain 20.7 g of intermediate A-2.

[1166] · Synthesis of Intermediate A-3

[1167] Under an argon atmosphere, a mixture of 20.7 g (87.0 mmol) of intermediate A-2, 16.3 g (87.0 mmol) of 1-bromo-2-methoxybenzene, 1.60 g (1.75 mmol) of tris(dibenzylideneacetone)dipalladium(0), 2.87 g (6.99 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(SPhos), 55.6 g (262 mmol) of potassium phosphate, 374 mL of 1,4-dioxane, and 62 mL of water was heated at 90°C for 5 hours. After cooling the reaction mixture to room temperature, toluene was added, the organic phase was washed with saturated saline solution, dehydrated with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 11.3 g of intermediate A-3.

[1168] · Synthesis of Intermediate A-4

[1169] Under an argon atmosphere, a mixture of 12.1 g (40.6 mmol) of intermediate A-3 and 135 mL of dichloromethane was cooled to 0°C, and then 81 mL of 1 M boron tribromide dichloromethane solution was added dropwise. After stirring the reaction mixture at room temperature for 4 hours, the mixture was cooled to 0°C, and 100 mL of water was added dropwise. By filtering the precipitated solid, 8.92 g of intermediate A-4 was obtained.

[1170] · Synthesis of Intermediate A

[1171] A mixture of 8.92 g (33.0 mmol) of intermediate A-4, 11.35 g (11.4 mmol) of p-toluenesulfonic acid monohydrate, and 165 mL of toluene was refluxed to the boiling point for 5 hours. After cooling the reaction mixture to room temperature, water was added and the mixture was filtered. The organic phase of the filtrate was washed with saturated saline solution, dehydrated with magnesium sulfate, and concentrated under reduced pressure to obtain 5.75 g of intermediate A.

[1172] (2) Synthesis of Compound Inv-1

[1173]

[1174] Under an argon atmosphere, a mixture of 4.00 g (11.9 mmol) of intermediate A, 5.82 g (19.0 mmol) of (10-phenylanthracene-9-yl-1,2,3,4,5,6,7,8-d8)boronic acid, 0.29 g (0.32 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.52 g (1.27 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(SPhos), 10.1 g (47.5 mmol) of potassium phosphate, 68 mL of 1,4-dioxane, and 11 mL of water was heated at 90°C for 20 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.43 g of compound Inv-1 as a white solid. The result obtained was, based on mass spectrum analysis, compound Inv-1, with a molecular weight of 478.62 and m / z=479.

[1175] (Synthesization Example 2) Synthesis of Intermediate B

[1176] Intermediate B was synthesized via the following synthesis pathway.

[1177]

[1178] (1) Synthesis of intermediate B-1

[1179] Under an argon atmosphere, a mixture of 2.53 g (10.0 mmol) of intermediate A, 3.81 g (15.0 mmol) of bis(pinacholate)diborone, 0.18 g (0.20 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.33 g (0.80 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(SPhos), 2.94 g (30.0 mmol) of potassium acetate, and 35 mL of 1,4-dioxane was heated at 90°C for 16 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 2.08 g of intermediate B-1.

[1180] (2) Synthesis of intermediate B

[1181] Under an argon atmosphere, a mixture of 1.72 g (5.00 mmol) of intermediate B-1, 1.41 g (5.00 mmol) of 1-bromo-3-iodobenzene, 0.27 g (0.3 mmol) of tetrakis(triphenylphosphine)palladium (0), 12.5 mL of 2 M aqueous sodium carbonate solution, and 25 mL of 1,2-dimethoxyethane was heated at 90°C for 16 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 1.53 g of intermediate B.

[1182] (Synthesis Examples 3–4) Synthesis of Intermediates C and D

[1183] Intermediates C and D were synthesized in the same manner as Synthesis Example 2, except that 1-bromo-3-iodobenzene was replaced with the compound of Table 3 in the synthesis of intermediate B.

[1184]

[1185] (Synthesis Examples 5–10) Synthesis of Inv-2–Inv-7

[1186] In the synthesis reaction of Inv-1, Inv-2 to Inv-7 were synthesized in the same manner as Synthesis Example 1, except that intermediate A and (10-phenylanthracene-9-yl-1,2,3,4,5,6,7,8-d8)boronic acid were each replaced with the compounds in Table 4.

[1187]

[1188] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will easily make many modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Accordingly, such many modifications are included within the scope of the present invention.

[1189] All of the documents described in this specification and the contents of the application forming the basis of the priority under the Paris Convention of this Application are adopted.

Claims

Claim 1 A compound represented by the following formula (1). [In formula (1), X1 is O or S. R1 to R8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ),-O-(R 904 ),-S-(R 905 ),-N(R 906 )(R 907 ), a ring-forming aryl group having 6 to 50 carbon atoms, either substituent or unsubstituent, or a monovalent complex ring-forming group having 5 to 50 atoms. At least one of R1 to R8 is a deuterium atom. R 11 ~R 19 Each independently consists of a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 ),-O-(R 904 ),-S-(R 905 ), or-N(R 906 )(R 907 ) is. L1 is a single-bonded, or substituted or unsubstituted, ring-forming arylene group having 6 to 10 carbon atoms. n1 is an integer from 0 to 3. If n1 is 0, (L1) n1 ... is a single bond. If n1 is 2 or more, 2 or more L1s are connected in series. If n1 is 2 or more, 2 or more L1s may be identical or different. L2 is a single bond, a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex ring group having 5 to 50 atoms. n2 is an integer from 0 to 3. If n2 is 0, (L2) n2 is a single bond. If n2 is 2 or more, 2 or more L2s are connected in series. If n2 is 2 or more, 2 or more L2s may be identical or different. Ar1 is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent complex cyclic group having 5 to 50 atoms. R 901 ~R 907 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming monovalent heterocyclic group with 5–50 atoms. 901 ~R 907 If there are 2 or more of these, 2 or more R 901 ~R 907 Each of these may be the same or different. Claim 2 A compound in which X1 is O, in paragraph 1. Claim 3 A compound according to claim 1 or 2, wherein L1 is a single bond, substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group. Claim 4 A compound according to any one of paragraphs 1 to 3, wherein L1 is a single bond. Claim 5 A compound according to any one of claims 1 to 4, wherein L2 is a single bond, substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group. Claim 6 A compound according to any one of claims 1 to 5, wherein L2 is a single bond. Claim 7 A compound according to any one of claims 1 to 6, wherein Ar1 is a disubstituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group. Claim 8 A compound according to any one of claims 1 to 7, wherein Ar1 is a substituted or unsubstituted phenyl group. Claim 9 A compound according to any one of claims 1 to 8, wherein R1 to R8 are all deuterium atoms. Claim 10 In any one of paragraphs 1 through 9, R 11 ~R 19 A compound in which all atoms are light hydrogen. Claim 11 A compound according to any one of claims 1 to 10, wherein all of the hydrogen atoms of Ar1 are light hydrogen atoms. Claim 12 A compound according to claim 1, wherein the compound represented by the above formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3). [In formulas (1-1) to (1-3), X1, L1, L2, Ar1, R1 to R8, and R 11 ~R 19 is as defined in the above equation (1). 4 R a Among them, two or more adjacent sets of at least one combine to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. 4 R b Among them, two or more adjacent sets of at least one combine to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R that does not form the above ring a and R b Each independently consists of a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 ),-O-(R 904 ),-S-(R 905 ),-N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a monovalent complex circulating group having 5 to 50 atoms forming a substituted or unsubstituted ring. R 901 ~R 907 [It is as defined in the above equation (1).] Claim 13 A compound according to claim 1, wherein the compound represented by the above formula (1) is a compound represented by the following formula (1-11) or formula (1-12). [In Equation (1-11), X1 and Ar1 are as defined in Equation (1). In Equation (1-12), X1 and Ar1 are as defined in Equation (1). L 21 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group. D represents a deuterium atom. Claim 14 A compound according to claim 1, wherein the compound represented by the above formula (1) is a compound represented by any one of the following formulas (1-21) to (1-23). [In Equation (1-21), X1 and Ar1 are as defined in Equation (1). In Equation (1-22), X1 and Ar1 are as defined in Equation (1). L 21 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group. In Formula (1-23), X1 and Ar1 are as defined in Formula (1). D represents a deuterium atom. Claim 15 An organic electroluminescence device having a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound described in any one of claims 1 to 14. Claim 16 An organic electroluminescence device according to claim 15, comprising an anode, a light-emitting layer, and a cathode in this order, wherein at least one layer of the organic layer in the light-emitting layer comprises the compound. Claim 17 An electronic device having an organic electroluminescence element as described in paragraph 15 or 16.

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