WO2023182323A1 - Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Download PDF

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WO2023182323A1
WO2023182323A1 PCT/JP2023/011074 JP2023011074W WO2023182323A1 WO 2023182323 A1 WO2023182323 A1 WO 2023182323A1 JP 2023011074 W JP2023011074 W JP 2023011074W WO 2023182323 A1 WO2023182323 A1 WO 2023182323A1
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司 澤藤
裕亮 糸井
佑典 高橋
将太 田中
拓人 深見
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device including the organic electroluminescent device.
  • an organic electroluminescent device (hereinafter sometimes referred to as an "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode.
  • an organic EL device When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes from the anode side into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state. Light is emitted when the state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate recombination of electrons and holes is important in obtaining high-performance organic EL devices.
  • Patent Documents 1 to 5 disclose compounds used as materials for organic electroluminescent devices.
  • the present invention was made to solve the above problems, and provides a compound that further improves the performance of an organic EL element, an organic EL element with further improved element performance, and an electronic device including such an organic EL element.
  • the purpose is to provide.
  • the present invention provides a compound represented by the following formula (1).
  • N* is the central nitrogen atom.
  • R 1 to R 6 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted ring It is an aryl group having 6 to 18 carbon atoms.
  • one or more pairs of adjacent two or more selected from R 1 to R 6 may be bonded to each other to form one or more unsubstituted benzene rings, or may be bonded to each other to form one or more unsubstituted benzene rings.
  • Ar 3 is an alkyl group-substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring carbon number 3 ⁇ 10 cycloalkyl groups.
  • R 11 to R 14 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted ring. It is an aryl group having 6 to 18 carbon atoms.
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
  • the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted ring having 6 to 12 carbon atoms. is an aryl group, and no ring is condensed with the phenylene group, biphenylene group, or naphthylene group.
  • Ar 1 and Ar 2 are each independently a group represented by the following formula (1a) or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; The aryl group of No.
  • the substituents in the substituted aryl group having 6 to 30 ring carbon atoms include a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. At least one type selected from the group consisting of substituted aryl groups having 6 to 12 ring carbon atoms. However, when two or more of the ring carbon atoms of the aryl group having 6 to 30 ring carbon atoms are substituted with an alkyl group, the two or more alkyl groups do not bond to each other and therefore do not form a ring.
  • *1 is the bonding position to one or both of L 1 and L 2 ;
  • X is an oxygen atom, a sulfur atom, NRa, or CRbRc;
  • Ra is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aryl group having 5 to 13 ring atoms; is an aromatic heterocyclic group;
  • Rb and Rc are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
  • Rb and Rc may be bonded to each other to form a ring structure having 8 or more ring atoms, or may not be bonded to each other to form a ring structure
  • the present invention provides a material for an organic EL device containing a compound represented by the above formula (1).
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a light-emitting layer, and at least one of the organic layers.
  • An organic electroluminescent device in which one layer contains a compound represented by the formula (1) is provided.
  • the present invention provides an electronic device including the organic electroluminescent device.
  • An organic EL device containing the compound represented by formula (1) above exhibits improved device performance.
  • FIG. 1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one embodiment of the present invention.
  • FIG. 3 is a schematic diagram illustrating another example of the layer structure of an organic EL element according to one embodiment of the present invention.
  • FIG. 3 is a schematic diagram illustrating another example of the layer structure of an organic EL element according to one embodiment of the present invention.
  • the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.
  • the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms.
  • a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound represents the number of carbon atoms among the atoms.
  • the carbon contained in the substituent is not included in the number of carbon atoms forming the ring.
  • the "number of ring-forming carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 carbon atoms
  • a naphthalene ring has 10 carbon atoms
  • a pyridine ring has 5 carbon atoms
  • a furan ring has 4 carbon atoms.
  • the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13
  • the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
  • the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring.
  • the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below is the same unless otherwise specified.
  • the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5.
  • the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group with carbon number XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in substituents.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • number of atoms XX to YY in the expression “substituted or unsubstituted ZZ group with number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY" means an integer of 2 or more.
  • an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "BB group substituted with AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. .
  • the number of ring atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of ring carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6. be.
  • the number of ring carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18. .
  • the number of ring atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc.
  • an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group”
  • a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group” is a "substituted or unsubstituted aryl group”
  • aryl group includes both “unsubstituted aryl group” and “substituted aryl group.”
  • “Substituted aryl group” means a group in which one or more hydrogen atoms of "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the “substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B.
  • Examples include:
  • the examples of "unsubstituted aryl group” and “substituted aryl group” listed here are just examples, and the "substituted aryl group” described in this specification includes the following specific examples.
  • aryl group (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzocrysenyl group,
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsily
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
  • a “heterocyclic group” as described herein is a monocyclic group or a fused ring group.
  • a “heterocyclic group” as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B).
  • unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”
  • substituted heterocyclic group refers to "substituted or unsubstituted heterocyclic group”
  • Heterocyclic group refers to a "substituted heterocyclic group."
  • heterocyclic group refers to "unsubstituted heterocyclic group” and “substituted heterocyclic group.” including both.
  • “Substituted heterocyclic group” means a group in which one or more hydrogen atoms of "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom.
  • heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), and substituted heterocyclic groups containing a sulfur atom.
  • group Specific Example Group G2B3
  • one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituents.
  • Includes substituted groups (Example Group G2B4).
  • ⁇ Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, Tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl
  • ⁇ Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): frill group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .
  • Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
  • ⁇ Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • ⁇ Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, and at least one of XA and YA is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom in the case where XA and YA are CH2, and the hydrogen atom of the methylene group when one of XA and YA is CH2.
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ).
  • an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is (This refers to the case where it is a "substituted alkyl group.”)
  • alkyl group when it is simply referred to as an "alkyl group,” it includes both an "unsubstituted alkyl group” and a "substituted alkyl group.”
  • “Substituted alkyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkyl group” are replaced with a substituent.
  • substituted alkyl group examples include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group” (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples examples include group G3B).
  • the alkyl group in "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • ⁇ Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • ⁇ Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
  • “Substituted or unsubstituted alkenyl group” Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc.
  • the term "unsubstituted alkenyl group” refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group”
  • “substituted alkenyl group” refers to "substituted or unsubstituted alkenyl group”).
  • alkenyl group refers to a “substituted alkenyl group.”
  • alkenyl group includes both “unsubstituted alkenyl group” and “substituted alkenyl group.”
  • Substituted alkenyl group means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done.
  • ⁇ Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • ⁇ Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group and 1,2-dimethylallyl group.
  • ⁇ alkynyl group'' and ⁇ substituted alkynyl group means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with a substituent.
  • ⁇ “Substituted or unsubstituted cycloalkyl group” Specific examples of the "substituted or unsubstituted cycloalkyl group” (specific example group G6) described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group”, and the term “substituted cycloalkyl group” refers to “substituted or unsubstituted cycloalkyl group”).
  • cycloalkyl group refers to a "substituted cycloalkyl group.
  • simply “cycloalkyl group” refers to "unsubstituted cycloalkyl group” and “substituted cycloalkyl group.” including both.
  • Substituted cycloalkyl group means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned.
  • cycloalkyl group (specific example group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group.
  • G7 Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification (specific example group G7) include: -Si(G1)(G1)(G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
  • a plurality of G3's in Si(G3) (G3) are mutually the same or different.
  • - A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.
  • G8 Specific examples of the group represented by -O-(R 904 ) described in this specification (specific example group G8) include: -O(G1), -O(G2), -O (G3) and -O (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 Group represented by -S-(R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S (G3) and -S (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G10 Group represented by -N(R 906 )(R 907 )
  • Specific examples of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N (G1) (G2), -N (G3) (G3), and -N (G6) (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • -N(G1) A plurality of G1's in (G1) are mutually the same or different.
  • -N(G2) A plurality of G2's in (G2) are the same or different.
  • -N(G3) A plurality of G3's in (G3) are mutually the same or different.
  • -N(G6) A plurality of G6's in (G6) are mutually the same or different.
  • halogen atom specifically examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • substituted or unsubstituted fluoroalkyl group refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group).
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group” is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • the "unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • the "substituted or unsubstituted haloalkyl group” described herein is a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a halogen atom. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group” is further replaced with a substituent, and a “substituted haloalkyl group” Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group” are further replaced 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 replaced with a halogen atom.
  • a haloalkyl group is sometimes referred to as a halogenated alkyl group.
  • a specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkoxy group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted alkylthio group” A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group” described in specific example group G3. "unsubstituted alkyl group”.
  • the number of carbon atoms in the "unsubstituted alkylthio group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryloxy group” described in specific example group G1. or an unsubstituted aryl group.
  • the number of ring carbon atoms in the "unsubstituted aryloxy group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • the number of ring carbon atoms in the "unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted trialkylsilyl group” A specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group.” - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an "aralkyl group” is a group in which the hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one embodiment of a “substituted alkyl group.”
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms in the "unsubstituted aralkyl group” is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
  • substituted or unsubstituted aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ - Naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein.
  • Nanthrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 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)carbazole -4-yl group), (9-b
  • carbazolyl group is specifically any of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in the specification.
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the specification.
  • the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.
  • the "substituted or unsubstituted arylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. It is the basis of valence.
  • a "substituted or unsubstituted arylene group” (specific example group G12) one hydrogen atom on the aryl ring is removed from the "substituted or unsubstituted aryl group” described in specific example group G1. Examples include divalent groups derived from the derivatives.
  • the "substituted or unsubstituted divalent heterocyclic group” described herein refers to the "substituted or unsubstituted heterocyclic group" described above, in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • the "substituted or unsubstituted alkylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. It is the basis of valence.
  • a "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group” described in specific example group G3. Examples include divalent groups derived from the derivatives.
  • the substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • Formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents the bonding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • the set of two or more adjacent R 930 is one set. is a set of R 921 and R 922 , a set of R 922 and R 923 , a set of R 923 and R 924 , a set of R 924 and R 930 , a set of R 930 and R 925 , a set of R 925 and A set of R 926 , a set of R 926 and R 927 , a set of R 927 and R 928 , a set of R 928 and R 929 , and a set of R 929 and R 921 .
  • the above-mentioned "one or more sets” means that two or more sets of the above-mentioned two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring Q A
  • R 925 and R 926 combine with each other to form ring Q B
  • the above general formula (TEMP-103) The anthracene compound represented is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent items forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items” form a ring. This also includes the case where two sets are combined.
  • R 921 and R 922 combine with each other to form a ring Q A
  • R 922 and R 923 combine with each other to form a ring Q C
  • the three adjacent to each other (R 921 , R 922 and R 923 ) combine with each other to form a ring and are condensed to the anthracene mother skeleton.
  • anthracene compound represented by the general formula (TEMP-103) is as follows: It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
  • the "single ring” or “fused ring” that is formed may be a saturated ring or an unsaturated ring as a structure consisting only of the formed ring. Even if "a set of two adjacent rings” forms a “monocycle” or “fused ring,” the “monocycle” or “fused ring” is a saturated ring, or Can form unsaturated rings.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a "fused ring.”
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings”.
  • Ring Q A and ring Q C in the general formula (TEMP-105) are a fused ring by condensation of ring Q A and ring Q C.
  • ring Q A in the general formula (TEMP-104) is a benzene ring
  • ring Q A is a monocyclic ring.
  • ring Q A in the general formula (TEMP-104) is a naphthalene ring
  • ring Q A is a fused ring.
  • Unsaturated ring means an aromatic hydrocarbon ring or an aromatic heterocycle.
  • “Saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
  • Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
  • Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
  • Form a ring means to form a ring with only a plurality of atoms of a parent skeleton, or with a plurality of atoms of a parent skeleton and one or more arbitrary elements.
  • the ring Q A shown in the general formula (TEMP-104) formed by R 921 and R 922 bonding to each other is a carbon atom of the anthracene skeleton to which R 921 is bonded, and an anthracene bond to which R 922 is bonded. It means a ring formed by a carbon atom in the skeleton and one or more arbitrary elements.
  • R 921 and R 922 form a ring Q A
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms.
  • R 921 and R 922 form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary element” is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification.
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent” described below.
  • the ring formed is a heterocycle.
  • the number of "one or more arbitrary elements" constituting a monocyclic or condensed ring is preferably 2 to 15, more preferably 3 to 12. , more preferably 3 or more and 5 or less.
  • a “monocycle” is preferred among “monocycle” and “fused ring.” Unless otherwise specified herein, the "unsaturated ring” is preferred between the “saturated ring” and the “unsaturated ring”. Unless otherwise stated herein, a “monocycle” is preferably a benzene ring. Unless otherwise stated herein, an “unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent groups are “bonded with each other to form a substituted or unsubstituted monocycle” or “bonded with each other to form a substituted or unsubstituted fused ring”
  • one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms.
  • a substituted or unsubstituted "unsaturated ring” is formed with at least one element selected from the group consisting of the following carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • Specific examples of the substituent in the case where the above-mentioned “single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein” above.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • substituents in the case where the above-mentioned "single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein" above. The above applies to cases in which "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent groups” are combined with each other to form a substituted or unsubstituted condensed ring ("the case where they are combined to form a ring").
  • the substituent in the case of "substituted or unsubstituted” is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstituted alkenyl group having 2 to 50 carbon atoms, unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring
  • R 901s When two or more R 901s exist, the two or more R 901s are the same or different, When two or more R 902s exist, the two or more R 902s are the same or different, When two or more R 903s exist, the two or more R 903s are the same or different, When two or more R 904s exist, the two or more R 904s are the same or different, When two or more R 905s exist, the two or more R 905s are the same or different, When two or more R 906s exist, the two or more R 906s are the same or different, When two or more R 907s exist, the two or more R 907s are the same or different from each other.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 18 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may further have a substituent.
  • the substituent which the arbitrary substituent further has is the same as the above arbitrary substituent.
  • the numerical range expressed using "AA-BB” has the numerical value AA written before “AA-BB” as the lower limit, and the numerical value BB written after "AA-BB”. means a range that includes as an upper limit value.
  • invention compound As described above, the compound according to one embodiment of the present invention is represented by the following formula (1).
  • the compound of the present invention represented by the below-mentioned formula included in formula (1) may be referred to as an "invention compound”.
  • N* is the central nitrogen atom.
  • R 1 to R 6 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, Alternatively, it is an unsubstituted aryl group having 6 to 18 ring carbon atoms. However, one or more pairs of adjacent two or more selected from R 1 to R 6 may be bonded to each other to form one or more unsubstituted benzene rings, or may be bonded to each other to form one or more unsubstituted benzene rings. It is not necessary to form a ring.
  • R 1 to R 6 examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, and s-butyl group.
  • t-butyl group pentyl group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group; preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group , isobutyl group, s-butyl group, t-butyl group, pentyl group, or hexyl group; more preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s -butyl group or t-butyl group; more preferably methyl group or t-butyl group; still more preferably t-butyl group.
  • Examples of the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 6 may represent include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-norbornyl group, and a 2-norbornyl group.
  • 1-adamantyl group, or 2-adamantyl group preferably cyclohexyl group, 1-norbornyl group, 2-norbornyl group, 1-adamantyl group, or 2-adamantyl group; more preferably cyclohexyl group , 1-adamantyl group, or 2-adamantyl group; more preferably cyclohexyl group or 1-adamantyl group.
  • Examples of the unsubstituted aryl group having 6 to 18 ring carbon atoms that R 1 to R 6 may represent include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, anthryl group, benzanthryl group, Examples include phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, or triphenylenyl group; preferably phenyl group, biphenylyl group, terphenylyl group, or naphthyl group.
  • Ar 3 is an alkyl group-substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alkyl group. is a cycloalkyl group having 3 to 10 ring carbon atoms.
  • Examples of the unsubstituted aryl group having 6 to 18 ring carbon atoms that Ar 3 may represent include the same groups as the unsubstituted aryl group having 6 to 18 ring carbon atoms that R 1 to R 6 may represent; are preferred; phenyl group, biphenylyl group, terphenylyl group, or naphthyl group; more preferred are phenyl group, 2-, 3-, or 4-biphenylyl group, 2-, 3-, or 4-biphenylyl group; -o-terphenylyl group, 2-, 3-, or 4-m-terphenylyl group, 2-, 3-, or 4-p-terphenylyl group, or 1- or 2-naphthyl group; more preferably, A phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; even more preferably a phenyl group.
  • alkyl group which may be substituted with the unsubstituted aryl group having 6 to 18 ring carbon atoms that Ar 3 may represent include the unsubstituted aryl group having 1 to 10 ring carbon atoms that R 1 to R 6 may represent.
  • Examples include groups similar to alkyl groups; preferred are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, or pentyl.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by Ar 3 include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 1 to R 6 ; Preferably, it is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, or hexyl group; more preferably a methyl group , ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group; more preferably a methyl group or t-butyl group.
  • Examples of the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that Ar 3 may represent include the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 6 may represent; Similar groups include; preferably cyclohexyl group, 1-norbornyl group, 2-norbornyl group, 1-adamantyl group, or 2-adamantyl group; more preferably cyclohexyl group, 1-adamantyl group, or 2-adamantyl group; -adamantyl group; more preferably cyclohexyl group or 1-adamantyl group.
  • R 11 to R 14 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, Alternatively, it is an unsubstituted aryl group having 6 to 18 ring carbon atoms. However, one or more pairs of adjacent two or more selected from R 11 to R 14 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other. It is not necessary to form a ring.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 11 to R 14 include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 1 to R 6 .
  • Examples of the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 11 to R 14 can represent include the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 6 can represent; and cyclohexyl group, 1-norbornyl group, 2-norbornyl group, 1-adamantyl group, or 2-adamantyl group; more preferably cyclohexyl group, 1-adamantyl group, or 2-adamantyl group; more preferably cyclohexyl group or 1-adamantyl group.
  • Examples of the unsubstituted aryl group having 6 to 18 ring carbon atoms that R 11 to R 14 can represent include the unsubstituted aryl group having 6 to 18 ring carbon atoms that R 1 to R 6 can represent; Similar groups include; preferably phenyl, biphenylyl, terphenylyl, or naphthyl; more preferably phenyl, 2-, 3-, or 4-biphenylyl, 2-, 3- , or a 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group; Preferred are phenyl, 2-, 3-, or 4-biphenylyl, or 1- or 2-naphthyl; even more preferred is phenyl.
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
  • the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted ring having 6 to 12 carbon atoms. is an aryl group, and no ring is condensed with the phenylene group, biphenylene group, or naphthylene group.
  • the unsubstituted phenylene group that L 1 and L 2 can represent is an o-phenylene group, a m-phenylene group, or a p-phenylene group.
  • the unsubstituted naphthylene group that L 1 and L 2 may represent is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.
  • the unsubstituted biphenylene group that L 1 and L 2 may represent is preferably a 4,4'-biphenylene group or a 3,4'-biphenylene group.
  • the unsubstituted alkyl group having 1 to 6 carbon atoms that can be the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is preferably a methyl group, an ethyl group, or an n-propyl group. , isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group; more preferably methyl group, ethyl group, isopropyl group, or t-butyl group; still more preferably methyl group or a t-butyl group; even more preferably a t-butyl group.
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms that can be the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is preferably a phenyl group, a biphenyl group, or a naphthyl group. is a group; more preferably a phenyl group or a naphthyl group; still more preferably a phenyl group.
  • Ar 1 and Ar 2 are each independently a group represented by the following formula (1a) or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
  • the aryl group having 6 to 30 ring carbon atoms consists of only a 6-membered ring, and the substituent in the substituted aryl group having 6 to 30 ring carbon atoms is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are each independently a group represented by the following formula (1a) or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
  • the aryl group having 6 to 30 ring carbon atoms consists of only a 6-membered ring, and the substituent in the substituted aryl group having 6 to 30 ring carbon atoms is a substituted or unsubstitute
  • *1 is a bonding position to one or both of L 1 and L 2 ;
  • X is an oxygen atom, a sulfur atom, NRa, or CRbRc
  • Ra is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aryl group having 5 to 13 ring atoms
  • the unsubstituted alkyl group having 1 to 6 carbon atoms that can be represented by Ra is preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t- A butyl group; more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group; still more preferably a methyl group or a t-butyl group.
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms that can be represented by Ra is preferably a phenyl group, a biphenyl group, or a naphthyl group; more preferably a phenyl group or a naphthyl group; still more preferably a phenyl group It is.
  • the unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms that can be represented by Ra is preferably a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, or a quinazolinyl group. group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group (benzothienyl group), dibenzofuranyl group, or dibenzothiophenyl group (dibenzothienyl group).
  • Ra is more preferably an unsubstituted phenyl group or an unsubstituted naphthyl group (1-naphthyl group or 2-naphthyl group).
  • Rb and Rc are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
  • Examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that Rb and Rc can represent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, Examples include t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, and dodecyl group; preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s
  • Examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rb and Rc may represent include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group, a benzanthryl group, and a phenanthryl group.
  • benzophenanthryl group phenalenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, fluorenyl group, fluoranthenyl group, perylenyl group, or triphenylenyl group; preferably phenyl group, Biphenylyl group, terphenylyl group, or naphthyl group; more preferably phenyl group, 2-, 3-, or 4-biphenylyl group, 2-, 3-, or 4-o-terphenylyl group, 2-, 3 -, or 4-m-terphenylyl group, 2-, 3-, or 4-p-terphenylyl group, or 1- or 2-naphthyl group; more preferably phenyl group, 2-, 3-, or A 4-biphenylyl group or a 1- or 2-naphthyl group; even more preferably a phenyl group.
  • examples of the substituent of the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rb and Rc include any substituents described below. Further, examples of the substituent of the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rb and Rc include, for example, any substituents described below, but among them, preferably 1 -6 alkyl group; more preferably t-butyl group.
  • Rb and Rc may be bonded to each other to form a ring structure having 8 or more ring atoms, or may not be bonded to each other to form a ring structure;
  • Rb and Rc when at least one of Rb and Rc is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Rb and Rc may be bonded to each other to form a ring, or may be bonded to each other.
  • Rb and Rc are both substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or one of Rb and Rc is a hydrogen atom, and the other is a hydrogen atom.
  • Rb and Rc may be bonded to each other to form a ring structure having 8 or more ring atoms, or may not be bonded to each other to form a ring structure. Does not need to form a structure;
  • Rb and Rc combine with each other to form a ring structure having 8 or more ring atoms, the number of ring atoms includes the carbon atom at the 9-position of the fluorene skeleton.
  • the number of ring forming atoms is 10.
  • the number of ring-forming atoms in the ring structure formed by Rb and Rc bonding to each other includes atoms that bridge atoms within one ring or on multiple rings, and which themselves are one Also included are atoms that are part of atoms forming a closed ring.
  • atoms that do not form a single closed ring and are not incorporated into the ring structure, such as atoms included in substituents of any of the atoms forming the ring are not included in the number of ring-forming atoms. do not have.
  • Examples of ring structures having 8 or more ring atoms that may be formed by bonding Rb and Rc to each other include, but are not limited to, the ring structures shown below. Note that * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.
  • R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring-forming alkyl group having 6 to 12 carbon atoms. is an aryl group; Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 21 to R 28 include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 1 to R 6 .
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms that R 21 to R 28 may represent is preferably a phenyl group, a biphenyl group, or a naphthyl group; more preferably a phenyl group or a naphthyl group; Preferably it is a phenyl group.
  • the biphenyl group includes o-biphenyl group, m-biphenyl group and p-biphenyl group; preferably m-biphenyl group or p-biphenyl group; more preferably p-biphenyl group.
  • the naphthyl group includes 1-naphthyl group and 2-naphthyl group; preferably 1-naphthyl group.
  • one selected from R 21 to R 28 , Rb and Rc is a single bond that binds to *a, and Ra does not bind to *a; Two adjacent ones selected from R 21 to R 28 that are not single bonds bonded to *a do not bond to each other and therefore do not form a ring.
  • the group represented by formula (1a) is more specifically the following formula (1a-1), formula (1a-2), formula (1a-3), or It is a group represented by formula (1a-4).
  • the aryl group having 6 to 30 ring carbon atoms consists of only a 6-membered ring
  • the substituent in the aryl group having 6 to 30 carbon atoms is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • the two or more alkyl groups do not bond to each other and therefore do not form a ring.
  • the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Ar 1 and Ar 2 include the same unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rb and Rc. Examples include phenyl, biphenylyl, terphenylyl, naphthyl, or phenanthryl groups.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted with the unsubstituted aryl group having 6 to 30 ring carbon atoms which Ar 1 and Ar 2 may represent include R 1 to R Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which 6 can represent; preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s -butyl group, t-butyl group, pentyl group, or hexyl group; more preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or It is a t-butyl group; more preferably a methyl group or a t-butyl group, even more preferably
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms which may be substituted with the unsubstituted aryl group having 6 to 30 ring carbon atoms which Ar 1 and Ar 2 may represent is preferably a phenyl group. , biphenyl group, or naphthyl group; more preferably phenyl group or naphthyl group; still more preferably phenyl group.
  • Ar 1 and Ar 2 are each independently represented by the following formula (1a), (1b), (1c), (1d) or (1e). It is preferable that it is a group.
  • *21 is a bonding position to one or both of L 1 and L 2 ;
  • R 101 to R 105 is a single bond bonded to *22, and one selected from R 106 to R 110 is a single bond bonded to *23;
  • R 101 to R 105 and R 106 to R 110 which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring-forming alkyl group having 6 to 12 carbon atoms.
  • R 101 to R 105 and R 106 to R 110 are not single bonds
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 101 to R 105 and R 106 to R 110 , which are not single bonds, include the unsubstituted ring-forming carbon atoms that can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms, which may be substituted with 6 to 30 aryl groups; preferred embodiments thereof are also the same.
  • Examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms that can be represented by R 101 to R 105 and R 106 to R 110 , which are not single bonds, include the unsubstituted ring that can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted aryl group having 6 to 12 ring carbon atoms, which may be substituted with an aryl group having 6 to 30 carbon atoms; preferred embodiments thereof are also the same.
  • R 111 to R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring-forming alkyl group having 6 to 12 carbon atoms. is an aryl group; However, two adjacent ones selected from R 111 to R 115 do not bond to each other and therefore do not form a ring;
  • the unsubstituted alkyl group having 1 to 10 carbon atoms which can be represented by R 111 to R 115 is, for example, substituted with the unsubstituted aryl group having 6 to 30 ring carbon atoms which can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the above-mentioned unsubstituted alkyl group having 1 to 10 carbon atoms; preferred embodiments thereof are also the same.
  • Examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms which can be represented by R 111 to R 115 include the unsubstituted aryl group having 6 to 30 ring carbon atoms which can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted aryl group having 6 to 12 ring carbon atoms, which may be substituted with , and preferred embodiments thereof are also the same.
  • m is 0 or 1
  • n is 0 or 1; however, When m and n are 0, *23 represents the bonding position to one or both of L1 and L2 , When m is 0 and n is 1, *22 represents the bonding position to one or both of L 1 and L 2 , When m is 1 and n is 0, one selected from R 101 to R 105 is a single bond bonded to *23.
  • the group represented by the formula (1b) includes each group represented by the following formula. However, in the following formula, R 101 to R 105 , R 106 to R 110 and R 111 to R 115 , which are not single bonds, are omitted for simplification.
  • *24 is a bonding position to one or both of L 1 and L 2 ;
  • R 121 to R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring having 6 to 12 carbon atoms. is an aryl group; However, one selected from R 121 to R 128 is a single bond bonded to *25, and two adjacent ones selected from R 121 to R 128 that are not bonded to *25 are not bonded to each other. and therefore do not form a ring.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which can be represented by R 121 to R 128 which are not single bonds include the unsubstituted aryl having 6 to 30 ring forming carbon atoms which can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms, which may be substituted with a group; preferred embodiments thereof are also the same.
  • Examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms that can be represented by R 121 to R 128 that are not single bonds include the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted aryl group having 6 to 12 ring carbon atoms, which may be substituted with the aryl group; preferred embodiments thereof are also the same.
  • *26 is a bonding position to one or both of L 1 and L 2 ;
  • R 131 to R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring-forming alkyl group having 6 to 12 carbon atoms. is an aryl group; However, one selected from R 131 to R 140 is a single bond bonded to *27, and two adjacent ones selected from R 131 to R 140 that are not bonded to *27 are not bonded to each other. and therefore do not form a ring.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which can be represented by R 131 to R 140 which are not single bonds include the unsubstituted aryl having 6 to 30 ring forming carbon atoms which can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms, which may be substituted with a group; preferred embodiments thereof are also the same.
  • Examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms that can be represented by R 131 to R 140 that are not single bonds include the unsubstituted 6 to 30 ring carbon atoms that Ar 1 and Ar 2 can represent.
  • Examples include the same groups as the unsubstituted aryl group having 6 to 12 ring carbon atoms, which may be substituted with the aryl group; preferred embodiments thereof are also the same.
  • *30 is a bonding position to one or both of L 1 and L 2 ;
  • R 151 to R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group; However, one selected from R 151 to R 155 is a single bond bonded to *31, and the other selected from R 151 to R 155 is a single bond bonded to *32; Two adjacent ones selected from R 151 to R 155 that are neither a single bond bonded to *31 nor a single bond bonded to *32 do not bond to each other and therefore do not form a ring; Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which can be represented by R 151 to R 155 which are not single bonds include the unsubstituted aryl having 6 to 30 ring forming carbon atoms which can be represented by Ar 1 and Ar 2 . Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms, which may be substituted
  • R 161 to R 165 and R 171 to R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms; However, one or more pairs of two or more adjacent groups selected from R 161 to R 165 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other. Does not need to form a ring; One or more pairs of adjacent two or more selected from R 171 to R 175 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. It does not need to be formed.
  • Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which can be represented by R 161 to R 165 and R 171 to R 175 include the unsubstituted alkyl group having 6 to 10 ring forming carbon atoms which can be represented by Ar 1 and Ar 2 .
  • Examples include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms, which may be substituted with 30 aryl groups; preferred embodiments thereof are also the same.
  • the group represented by the formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5).
  • All of R 1 to R 6 may be hydrogen atoms; (1-2) All of R 11 to R 14 may be hydrogen atoms; (1-3) *All of R 21 to R 28 that are not single bonds bonded to a may be hydrogen atoms; (1-4) *All of R 101 to R 105 that are not single bonds bonded to *22 may be hydrogen atoms; (1-5) *All of R 106 to R 110 that are not single bonds bonded to *23 may be hydrogen atoms; (1-6) All of R 111 to R 115 may be hydrogen atoms; (1-7) *All of R 121 to R 128 that are not single bonds bonded to *25 may be hydrogen atoms; (1-8) *All of R 131 to R 140 that are not single bonds bonded to *27 may be hydrogen atoms; (1-9) All of R 151 to R 155 which are not single bonds bonded to *31 or single bonds bonded to *32 may be hydrogen atoms; (1-10) All of R 161
  • At least one of Ar 1 and Ar 2 is preferably a group represented by the above formula (1a), and both Ar 1 and Ar 2 are the group represented by the above formula (1a).
  • a group represented by formula (1a) is more preferred.
  • one of Ar 1 or Ar 2 is a group represented by the above formula (1a), and the other one is a group represented by the above formula (1b). It is preferable that there be.
  • X in the formula (1a) is preferably CRbRc. That is, the group represented by the formula (1a) is preferably a group represented by the formula (1a-4).
  • the group represented by the formula (1a-4) is preferably represented by the following formula. However, in the following formula, *1 representing the bonding position to one or both of L 1 and L 2 , the single bond bonded to *a, and R 21 to R 28 are omitted for the sake of simplification.
  • X is CRbRc, and at least one of Rb and Rc is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • R 26 in the formula (1a) is preferably a single bond bonded to *a.
  • Ar 1 and Ar 2 in formula (1) are both represented by formula (1a), they may be the same or different.
  • Ar 3 is preferably a cyclohexyl group, an adamantyl group, a phenyl group substituted with or unsubstituted with an alkyl group having 1 to 4 carbon atoms, or a naphthyl group.
  • the phenyl group substituted with an alkyl group having 1 to 4 carbon atoms is preferably a phenyl group substituted with one or more t-butyl groups; more preferably 3,5-di-t- It is a butylphenyl group.
  • one or both of L 1 and L 2 is preferably a single bond.
  • all of R 1 to R 6 and R 11 to R 14 are preferably hydrogen atoms.
  • one or more selected from the requirements of each of the preferred embodiments described above can be combined, and this embodiment is also a preferred embodiment of the invention compound.
  • one of Ar 1 or Ar 2 is a group represented by the above formula (1a), and the other one is a group represented by the above formula (1b).
  • R 1 to R 6 and R 11 to R 14 may be hydrogen atoms.
  • hydrogen atom as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Accordingly, the compounds of the invention may contain naturally occurring deuterium atoms. Further, a deuterium atom may be intentionally introduced into the invention compound A by using a deuterated compound as part or all of the raw material compounds. Thus, in one aspect of the invention, the inventive compounds contain at least one deuterium atom. That is, the invention compound may be a compound represented by formula (1), in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.
  • At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom.
  • “substituted or unsubstituted” the number of carbon atoms, and the number of atoms are omitted.
  • the deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally derived light hydrogen isotopes may be included. Therefore, the aspect of the deuteration rate of the invention compound shown below is the ratio calculated by simply counting the number of deuterium atoms represented by the chemical formula, but the ratio takes into account trace amounts of naturally occurring isotopes. included.
  • the deuteration rate of the invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more. Moreover, the deuteration rate of the invention compound is 100% or less. In other words, in one aspect of the present invention, the deuteration rate of the invention compound is preferably 1 to 100%, more preferably 3 to 100%, even more preferably 5% to 100%, even more preferably 10%. ⁇ 100%, more preferably 50 ⁇ 100%.
  • the invention compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates.
  • the deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. less than %.
  • the deuteration rate of the mixture is preferably 1% or more and less than 100%, more preferably 3% or more and less than 100%, even more preferably 5% or more and less than 100%, and more preferably 3% or more and less than 100%.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and 100% or more. % or less.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound is preferably 1 to 100%, more preferably 3 to 100%, and even more preferably 5% to 100%, even more preferably 10 to 100%.
  • substituted XX group included in the definitions of each of the above formulas is a substituted XX group
  • the details of the substituent are those not specifically mentioned in the above explanation.
  • the alkyl group having 1 to 6 carbon atoms is preferably a methyl group or a t-butyl group.
  • the aryl group having 6 to 12 ring carbon atoms is preferably a phenyl group.
  • the compounds of the invention can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

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Abstract

La présente invention concerne un composé représenté par la formule (1) (chaque symbole dans la formule (1) est tel que défini dans la description), un élément électroluminescent organique qui comprend ledit composé, et un dispositif électronique qui comprend ledit élément électroluminescent organique.
PCT/JP2023/011074 2022-03-25 2023-03-22 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2023182323A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018188433A (ja) * 2017-05-10 2018-11-29 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． アミン化合物及びこれを含む有機ｅｌ素子
US20200119282A1 (en) * 2018-10-12 2020-04-16 Samsung Display Co., Ltd. Organic electroluminescence device and amine compound for organic electroluminescence device
US20200168797A1 (en) * 2018-11-23 2020-05-28 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
WO2021193654A1 (fr) * 2020-03-25 2021-09-30 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2021200876A1 (fr) * 2020-03-31 2021-10-07 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US20230111469A1 (en) * 2019-08-02 2023-04-13 Duk San Neolux Co., Ltd. Organic Electronic Device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018188433A (ja) * 2017-05-10 2018-11-29 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． アミン化合物及びこれを含む有機ｅｌ素子
US20200119282A1 (en) * 2018-10-12 2020-04-16 Samsung Display Co., Ltd. Organic electroluminescence device and amine compound for organic electroluminescence device
US20200168797A1 (en) * 2018-11-23 2020-05-28 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US20230111469A1 (en) * 2019-08-02 2023-04-13 Duk San Neolux Co., Ltd. Organic Electronic Device
WO2021193654A1 (fr) * 2020-03-25 2021-09-30 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2021200876A1 (fr) * 2020-03-31 2021-10-07 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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