WO2023210698A1 - 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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WO2023210698A1
WO2023210698A1 PCT/JP2023/016479 JP2023016479W WO2023210698A1 WO 2023210698 A1 WO2023210698 A1 WO 2023210698A1 JP 2023016479 W JP2023016479 W JP 2023016479W WO 2023210698 A1 WO2023210698 A1 WO 2023210698A1
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佑典 高橋
裕亮 糸井
将太 田中
拓人 深見
司 澤藤
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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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • 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 13 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.
  • Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom It is a heterocyclic group of number 5 to 30.
  • Ra and Rb may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure;
  • Ra and Rb are not bonded to each other and do not form a ring structure, at least one selected from Ra and Rb is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • R 1 to R 8 is a single bond bonded to *1;
  • One or more pairs of adjacent two or more selected from R 1 to R 8 that are not single bonds bonded to *1 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • Rc is 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.
  • R 11 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 11 to R 18 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They may not be bonded to form a ring.
  • R 21 to R 24 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 22 to R 24 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They may not be bonded to form a ring.
  • L 1 , L 2 and L 3 are each independently a single bond or an unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • Ar is a group represented by the following formula (1a), (1b), (1c), (1d), (1e) or (1f). (In formula (1a), *11 is the bonding position to L3 .
  • Rd and Rf are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom is a heterocyclic group of number 5 to 30; However, Rd and Rf may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure.
  • R 31 to R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
  • one selected from R 31 to R 38 is a single bond bonded to *12;
  • One or more pairs of adjacent two or more selected from R 31 to R 38 that are not single bonds bonded to *12 are bonded to each other to form one or more substituted or unsubstituted benzene rings.
  • 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 that are not a single bond bonded to *22 and R 106 to R 110 that are not a single bond bonded to *23 are each independently a hydrogen atom or a substituted or unsubstituted carbon number.
  • R 111 to R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms; However, two adjacent ones selected from R 111 to R 115 do not bond to each other and therefore do not form a ring. ) (In formula (1c), *24 is the bonding position to L3 .
  • R 121 to R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • 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.
  • *26 is the bonding position to L3 .
  • R 131 to R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • 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.
  • *28 is the bonding position to L3 .
  • R 151 to R 155 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 151 to R 155 is a single bond bonded to *29, and the other selected from R 151 to R 155 is a single bond bonded to *30;
  • Two adjacent ones selected from R 151 to R 155 that are neither a single bond bonded to *29 nor a single bond bonded to *30 do not bond to each other and therefore do not form a ring.
  • R 161 to R 165 and R 171 to R 175 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; However, one or more pairs of adjacent two or more selected from R 161 to R 165 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other.
  • 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 substituted or unsubstituted benzene rings, or may not be bonded to each other. It is not necessary to form a ring.
  • *31 is the bonding position to L3 .
  • R 181 to R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 181 to R 192 is a single bond bonded to *32, and two adjacent ones selected from R 181 to R 192 that are not bonded to *32 are not bonded to each other. and therefore do not form a ring. )]
  • the present invention provides a compound represented by the following formula (2).
  • N* is the central nitrogen atom.
  • Raa and Rbb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom It is a heterocyclic group of number 5 to 30.
  • Raa and Rbb may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure;
  • Raa and Rbb are not bonded to each other and do not form a ring structure, at least one selected from Raa and Rbb is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • R 51 to R 58 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • R 51 to R 58 is a single bond bonded to *51;
  • One or more pairs of adjacent two or more selected from R 51 to R 58 that are not single bonds bonded to *51 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • Rcc is 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.
  • R 61 to R 68 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 61 to R 68 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They may not be bonded to form a ring.
  • R 71 to R 75 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • R 71 to R 75 is a single bond bonded to *52;
  • One or more pairs of adjacent two or more selected from R 71 to R 75 that are not single bonds bonded to *52 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • L 21 , L 22 and L 23 are each independently a single bond or an unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • Ar 2 is a group represented by the following formula (2a), (2b), (2c), (2d), (2e) or (2f). (In formula (2a), *61 is the bonding position to L23 .
  • Rdd and Rff are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom is a heterocyclic group of number 5 to 30; However, Rdd and Rff may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure.
  • R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; is an aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
  • one selected from R 81 to R 88 is a single bond bonded to *62;
  • One or more pairs of adjacent two or more selected from R 81 to R 88 that are not single bonds bonded to *62 are bonded to each other to form one or more substituted or unsubstituted benzene rings.
  • *70 is the bonding position to L23 .
  • One selected from R 291 to R 295 is a single bond bonded to *71, one selected from R 301 to R 305 is a single bond bonded to *72, and one selected from R 306 to R 310
  • R 291 to R 295 that are not a single bond bonded to *71, R 301 to R 305 that are not a single bond bonded to *72, and R 306 to R 310 that are not a single bond bonded to *73 are , each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming carbon atom It is an aryl group of
  • R 311 to R 315 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • two adjacent ones selected from R 311 to R 315 do not bond to each other and therefore do not form a ring; m is 0 or 1, n is 0 or 1, p is 0 or 1; however, When m, n and p are 0, *73 represents the bonding position to L23 , When m and n are 0 and p is 1, *72 represents the bonding position to L23 , When m is 0 and n and p are 1, *71 represents the bonding position to L23 , When m and p are 0 and n is 1, *71 represents the bonding position to L 23 ,
  • R 321 to R 328 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms; However, one selected from R 321 to R 328 is a single bond bonded to *75, and two adjacent ones selected from R 321 to R 328 that are not bonded to *75 are not bonded to each other. and therefore do not form a ring.
  • R 331 to R 340 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 331 to R 340 is a single bond bonded to *77, and two adjacent ones selected from R 331 to R 340 that are not bonded to *77 are not bonded to each other. and therefore do not form a ring.
  • R 351 to R 355 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 351 to R 355 is a single bond bonded to *79, and the other selected from R 351 to R 355 is a single bond bonded to *80; Two adjacent ones selected from R 351 to R 355 that are neither a single bond bonded to *79 nor a single bond bonded to *80 do not bond to each other and therefore do not form a ring.
  • R 361 to R 365 and R 371 to R 375 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; However, one or more pairs of adjacent two or more selected from R 361 to R 365 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other.
  • R 381 to R 392 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 381 to R 392 is a single bond bonded to *82, and two adjacent ones selected from R 381 to R 392 that are not bonded to *82 are not bonded to each other. and therefore do not form a ring.
  • the present invention provides a material for an organic EL device containing a compound represented by the above formula (1) or a compound represented by the above formula (2).
  • 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 above formula (1) or a compound represented by the above formula (2) 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.
  • an organic EL device containing the compound represented by formula (2) 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 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 an 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 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.
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” 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 the case where "substituted cycloalkyl group” is used.
  • cycloalkyl group when simply referring to “cycloalkyl group”, it 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 Group represented by -Si(R 901 )(R 902 )(R 903 )
  • Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(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.
  • ⁇ “Substituted or unsubstituted haloalkyl group” means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group” are replaced 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.
  • “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; 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.
  • ⁇ “Substituted or unsubstituted alkoxy 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 the "substituted or unsubstituted alkoxy group” described in specific example group G3. "unsubstituted alkyl group”. 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.
  • the "substituted or unsubstituted arylene group” (specific example group G12), by removing one hydrogen atom on the aryl ring 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 pair 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 the structure of only the formed ring. Even if “one 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 the parent skeleton, or with a plurality of atoms of the 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 when 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 when 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 rings combine with each other to form a substituted or unsubstituted monocycle" and “one or more sets of two or more adjacent rings” 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 (1) the compound of the present invention represented by the below-mentioned formula included in formula (1)
  • invention compound (2) the compound of the present invention represented by the formula described below that is included in formula (2)
  • invention compound (1) the compound of the present invention represented by the formula described below that is included in formula (2)
  • invention compound (2) the compound of the present invention represented by the formula described below that is included in formula (2)
  • invention compound (1) to express the meaning of "invention compound (1) alone, invention compound (2) alone, or both invention compounds (1) and (2)"
  • invention compound (2) it is simply referred to as "invention compound”. There is.
  • the invention compound (1) according to one aspect of the present invention is represented by the following formula (1).
  • N* is the central nitrogen atom.
  • Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; It is an unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ra and Rb may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure;
  • Ra and Rb are not bonded to each other and do not form a ring structure, at least one selected from Ra and Rb is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Ra and Rb each independently preferably has 1 to 18 carbon atoms, more preferably 1 to 6 carbon atoms.
  • Examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Ra and Rb 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, or dodecyl group; Preferably, it is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group,
  • the number of ring carbon atoms in the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Ra and Rb is preferably 6 to 18, more preferably 6 to 12, each independently.
  • Examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Ra and Rb include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, anthryl group, benzanthryl group, and phenanthryl group.
  • a benzophenanthryl group a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;
  • it is a phenyl group, a biphenylyl group, a terphenylyl group, or a 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, it is a phenyl group, a 2-, 3-, or 4-b
  • examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that may be represented by Ra and Rb include any of the substituents described below, which are preferred among them.
  • the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Ra and Rb is a substituted or unsubstituted aromatic heterocyclic group (heteroaryl group) having 5 to 30 ring atoms; It is preferable that there be.
  • the number of ring atoms of the unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Ra and Rb is preferably 5 to 20, more preferably 5 to 13, each independently.
  • Examples of the unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Ra and Rb include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, and a pyrazinyl group.
  • triazinyl group imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group , phenanthrolinyl group, phenazinyl group,
  • heterocyclic group having 5 to 30 ring atoms that may be represented by Ra and Rb may include any of the substituents described below.
  • the ring structure may be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, For example, it is selected from a single ring, a fused ring, a bridged bicyclo ring, or a bridged tricyclo ring.
  • Specific examples of the ring structure that may be formed by bonding Ra and Rb to each other are shown below, but the structure is not limited thereto. Note that * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.
  • the ring structure is preferably a substituted or unsubstituted hydrocarbon ring.
  • compound (1) as the ring structure that may be formed by Ra and Rb bonding to each other, the following ring structures are preferable among the specific examples described above.
  • R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one selected from R 1 to R 8 is a single bond bonded to *1;
  • One or more pairs of adjacent two or more selected from R 1 to R 8 that are not single bonds bonded to *1 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • compound (1) preferably one selected from R 2 to R 7 is a single bond bonded to *1, more preferably R 2 or R 7 is a single bond bonded to *1. be.
  • R 1 to R 8 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;
  • 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 preferred are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group; even more preferred are methyl group or t-butyl group. And; Even more preferred is t-butyl group.
  • Examples of the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 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, it is a cyclohexyl group, 1-norbornyl group, 2-norbornyl group, 1-adamantyl group, or 2-adamantyl group; More preferred is a cyclohexyl group, 1-adamantyl group, or 2-adamantyl group.
  • R 1 to R 8 examples 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, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a 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-terphenyly
  • Examples of the unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R 1 to R 8 include the above-mentioned Ra and Rb, except that the number of ring atoms is 5 to 13.
  • Examples of the heterocyclic group include; 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, a quinazolinyl group, a benzimidazolyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, and a dibenzofuranyl group.
  • nyl group is a nyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group; More preferred are a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
  • Rc is 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.
  • preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that Rc can represent include 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 A t-butyl group; more preferably a methyl group, an ethyl group, or a t-butyl group; still more preferably a methyl group.
  • substituents described below examples of the substituents described below.
  • preferable examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rc can represent are 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 4-biphenylyl group, or 1- or 2-naphthyl group; More preferred is a phenyl group.
  • examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rc may have include any of the substituents described below, and among them, preferably carbon It is an alkyl group of number 1 to 6; more preferably a methyl group or a t-butyl group.
  • R 11 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 11 to R 18 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They do not need to be bonded to form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 11 to R 18 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and still more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 11 to R 18 can represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 11 to R 18 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 11 to R 18 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 11 to R 18 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferable aryl group, a more preferable aryl group, an even more preferable aryl group, and an even more preferable aryl group.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 11 to R 18 may represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 1 to R 8 may represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 11 to R 18 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 21 to R 24 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 22 to R 24 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They may not be bonded to form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 21 to R 24 are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 1 to R 8 .
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, even more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 21 to R 24 can represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 21 to R 24 Details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 21 to R 24 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 21 to R 24 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 21 to R 24 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 21 to R 24 may represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 1 to R 8 may represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 21 to R 24 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • L 1 , L 2 and L 3 are each independently a single bond or an unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • the unsubstituted arylene group having 6 to 12 ring carbon atoms that can be represented by L 1 , L 2 , and L 3 is the same as described for Ra and Rb except that the ring carbon number is 6 to 12.
  • Examples include divalent groups obtained by removing one hydrogen atom from an unsubstituted aryl group, preferably an unsubstituted phenylene group, an unsubstituted naphthylene group, or an unsubstituted biphenylene group. ;More preferred is an unsubstituted phenylene group.
  • the unsubstituted phenylene group that L 1 , L 2 , and L 3 may represent is an o-phenylene group, a m-phenylene group, or a p-phenylene group.
  • the unsubstituted naphthylene group that L 1 , L 2 and L 3 may represent is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.
  • the unsubstituted biphenylene group that L 1 , L 2 , and L 3 may represent is preferably a 4,4'-biphenylene group or a 4,3'-biphenylene group (same as " 3,4'-biphenylene group”). ), or 4,2'-biphenylene group (same as "2,4'-biphenylene group”).
  • Ar is a group represented by the following formula (1a), (1b), (1c), (1d), (1e) or (1f).
  • *11 is the bonding position to L3 .
  • Rd and Rf are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or It is an unsubstituted heterocyclic group having 5 to 30 ring atoms; However, Rd and Rf may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure.
  • Rd and Rf may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 30 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rd and Rf may have include any of the substituents described below, and among them, preferred are is an alkyl group having 1 to 6 carbon atoms; more preferably a methyl group or a t-butyl group.
  • substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that Rd and Rf may represent include the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that Ra and Rb may represent. It is similar to what was explained; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 30 ring atoms that Rd and Rf can represent, and the more preferable types of heterocyclic groups, the explanation of Ra and Rb, respectively. It is similar to that exemplified in the passage; Furthermore, examples of the substituent that the heterocyclic group having 5 to 30 ring atoms that Rd and Rf may have include any substituents described below.
  • the details of the ring structure that may be formed by combining Rd and Rf with each other include the ring structure that may be formed by combining Ra and Rb with each other. It is similar to what was explained regarding the structure; Therefore, specific examples of ring structures that may be formed by Rd and Rf bonding with each other, and preferred ring structures thereof, are the same as those exemplified in the explanations of Ra and Rb. be.
  • compound (1) the group represented by the formula (1a) is preferably represented by the following formula.
  • the single bonds bonded to *11 and *12, which represent the bonding positions to L 3 , and R 31 to R 38 are omitted for simplification.
  • R 31 to R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one selected from R 31 to R 38 is a single bond bonded to *12;
  • One or more pairs of adjacent two or more selected from R 31 to R 38 that are not single bonds bonded to *12 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • compound preferably one selected from R 32 to R 37 is a single bond bonded to *12, and more preferably R 32 or R 37 is a single bond bonded to *12.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 31 to R 38 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, even more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 31 to R 38 can represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 31 to R 38 Details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 31 to R 38 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 31 to R 38 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • the details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that R 31 to R 38 may represent include the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that R 1 to R 8 may represent; It is similar to what was explained regarding the group; Therefore, the aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms that R 31 to R 38 can represent, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 31 to R 38 can represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 1 to R 8 can represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 31 to R 38 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • *21 is the bonding position to L3 .
  • one selected from 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 that are not a single bond bonded to *22 and R 106 to R 110 that are not a single bond bonded to *23 are each independently a hydrogen atom or a substituted or unsubstituted carbon number.
  • R 101 to R 105 and R 106 to R 110 may represent include the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is the same as that explained regarding the alkyl group; Therefore, R 101 to R 105 and R 106 to R 110 may represent an alkyl group, a preferred alkyl group, a more preferred alkyl group, a still more preferred alkyl group, and , even more preferable types of alkyl groups are the same as those exemplified in the explanations for R 1 to R 8 .
  • R 101 to R 105 and R 106 to R 110 may represent include the substituted or unsubstituted ring-forming group that R 1 to R 8 may represent.
  • the content is the same as that explained regarding the cycloalkyl group having 3 to 10 carbon atoms; Therefore, R 101 to R 105 and R 106 to R 110 may represent cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, preferred cycloalkyl groups, and more preferred cycloalkyl groups.
  • the types of groups are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 101 to R 105 and R 106 to R 110 may represent the substituted or unsubstituted ring-forming carbon atoms that R 1 to R 8 may represent.
  • the content is the same as that explained regarding the aryl group of numbers 6 to 18; Therefore, R 101 to R 105 and R 106 to R 110 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, and a still more preferred aryl group.
  • R 101 to R 105 and R 106 to R 110 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, and a still more preferred aryl group.
  • aryl groups are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • 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 cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; 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 details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 111 to R 115 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R 111 to R 115 may represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 111 to R 115 Details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 111 to R 115 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 111 to R 115 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 111 to R 115 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • 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 the bonding position to L3 .
  • 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 cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • 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.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 121 to R 128 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 121 to R 128 may represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 121 to R 128 Details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 121 to R 128 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 121 to R 128 may represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 121 to R 128 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • *26 is the bonding position to L3 .
  • 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 cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • 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.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 131 to R 140 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 131 to R 140 can represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 131 to R 140 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 131 to R 140 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 131 to R 140 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • *28 is the bonding position to L3 .
  • R 151 to R 155 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms.
  • R 151 to R 155 is a single bond bonded to *29, and the other selected from R 151 to R 155 is a single bond bonded to *30; Two adjacent ones selected from R 151 to R 155 that are neither a single bond bonded to *29 nor a single bond bonded to *30 do not bond to each other and therefore do not form a ring.
  • R 152 when L 3 is a single bond and R 152 is a single bond bonded to *29, R 151 , R 153 , or R 154 is a single bond bonded to *30.
  • R 155 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming group It may also be an aryl group having 10 to 18 carbon atoms.
  • R 151 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring forming carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. It may be a substituted aryl group having 10 to 18 ring carbon atoms.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 151 to R 155 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 1 to R 8 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 151 to R 155 can represent.
  • the types of are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 151 to R 155 Details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 151 to R 155 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 151 to R 155 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 151 to R 155 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that R 151 to R 155 may represent is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. It may be 10 to 18 aryl groups.
  • the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that may be represented by R 151 to R 155 is a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms. There may be.
  • R 161 to R 165 and R 171 to R 175 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 carbon number A cycloalkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; However, one or more pairs of adjacent two or more selected from R 161 to R 165 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other.
  • 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 substituted or unsubstituted benzene rings, or may not be bonded to each other. It is not necessary to form a ring.
  • R 161 to R 165 and R 171 to R 175 may represent include the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that may be represented by R 1 to R 8 above.
  • the content is the same as that explained regarding the alkyl group; Therefore, R 161 to R 165 and R 171 to R 175 may represent an alkyl group, a preferred alkyl group, a more preferred alkyl group, a still more preferred alkyl group, and , even more preferable types of alkyl groups are the same as those exemplified in the explanations for R 1 to R 8 .
  • R 161 to R 165 and R 171 to R 175 can represent include the substituted or unsubstituted ring-forming group that R 1 to R 8 can represent.
  • the content is the same as that explained regarding the cycloalkyl group having 3 to 10 carbon atoms; Therefore, R 161 to R 165 and R 171 to R 175 may represent cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, preferred cycloalkyl groups, and more preferred cycloalkyl groups.
  • the types of groups are also the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 161 to R 165 and R 171 to R 175 can represent include the substituted or unsubstituted ring-forming carbon atoms that R 1 to R 8 can represent.
  • the content is the same as that explained regarding the aryl group of numbers 6 to 18; Therefore, R 161 to R 165 and R 171 to R 175 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, and a still more preferred aryl group.
  • aryl groups are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R 161 to R 165 and R 171 to R 175 is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. It may be a substituted aryl group having 10 to 18 ring carbon atoms.
  • a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms which can be represented by R 161 to R 165 and R 171 to R 175 is a substituted or unsubstituted aryl group having 10 ring carbon atoms. to 18 aryl groups.
  • R 151 to R 155 are neither a single bond bonded to *29 nor a single bond bonded to *30, and R 161 to R 165 and R 171 to R 175 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 3 to 10 carbon atoms; 10 cycloalkyl groups.
  • R 151 to R 155 which are neither a single bond bonded to *29 nor a single bond bonded to *30, and R 161 to R 165 and R 171 to R 175 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; It's okay.
  • the group represented by the formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5). However, when L 3 is a single bond, the group represented by the above formula (1e) is represented by the following formulas (1e-1), (1e-2), (1e-3) and (1e-5). Including groups that are
  • *31 is the bonding position to L3 .
  • R 181 to R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 181 to R 192 is a single bond bonded to *32, and two adjacent ones selected from R 181 to R 192 that are not bonded to *32 are not bonded to each other. and therefore do not form a ring.
  • R 181 to R 192 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 1 to R 8 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 181 to R 192 may represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 1 to R 8 , respectively.
  • R 181 to R 192 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 1 to R 8 .
  • compound (1) in formula (1), (1-1) All of R 1 to R 8 that are not single bonds bonded to *1 may be hydrogen atoms; (1-2) All of R 11 to R 18 may be hydrogen atoms; (1-3) All of R 21 to R 24 may be hydrogen atoms; (1-4) *All of R 31 to R 38 that are not single bonds bonded to *12 may be hydrogen atoms; (1-5) *All of R 101 to R 105 that are not single bonds bonded to *22 may be hydrogen atoms; (1-6) *All of R 106 to R 110 that are not single bonds bonded to *23 may be hydrogen atoms; (1-7) All of R 111 to R 115 may be hydrogen atoms; (1-8) *All of R 121 to R 128 that are not single bonds bonded to *25 may be hydrogen atoms; (1-9) *All of R 131 to R 140 that are not single bonds bonded to *27 may be hydrogen atoms; (1-10) All of R 151 to R 155 which are not single bonds
  • Ra and Rb are each independently preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms; both Ra and Rb is more preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms; it is even more preferred that both Ra and Rb are unsubstituted phenyl groups.
  • Rc is preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms, and more preferably an unsubstituted phenyl group. .
  • Ra, Rb and Rc are preferably each independently a substituted or unsubstituted phenyl group; all of Ra, Rb and Rc are substituted or more preferably an unsubstituted phenyl group; it is even more preferable that all of Ra, Rb and Rc are unsubstituted phenyl groups.
  • L 1 and L 2 are preferably each independently a single bond or an unsubstituted phenylene group; It is more preferable that both are a single bond or an unsubstituted phenylene group; it is even more preferable that both L 1 and L 2 are a single bond.
  • L 3 is preferably a single bond or an unsubstituted phenylene group; it is more preferable that L 3 is a single bond.
  • compound (1) in formula (1), all of L 1 , L 2 and L 3 are preferably single bonds or unsubstituted phenylene groups; L 1 , L It is even more preferable that all of 2 and L3 are single bonds.
  • Ar in formula (1) is preferably a group represented by formula (1a) or (1b).
  • Ar in the formula (1), Ar is a group represented by the formula (1a), and in the formula (1a), 1 selected from R 32 to R 37 is preferably a single bond bonded to *12;
  • Ar is a group represented by the above formula (1a), and in the above formula (1a), R 32 or R 37 is a single bond bonded to *12. More preferably, it is a bond.
  • L 3 is a single bond
  • Ar is a group represented by formula (1b)
  • R 101 or R 105 is preferably a single bond bonded to *22.
  • L 3 represents Preferably, the unsubstituted phenyl group is an o-phenylene group.
  • 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 (1) by using a deuterated compound as part or all of the raw material compounds. Therefore, in one embodiment of the present invention, the invention compound (1) contains at least one deuterium atom. That is, the invention compound (1) 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 for the sake of brevity.
  • One hydrogen atom or at least one hydrogen atom selected from two or more hydrogen atoms possessed by the substituent related to the above-mentioned "substituted or unsubstituted” may also be the deuterium atom.
  • a hydrogen atom possessed by an alkyl group, aryl group, or heterocyclic group that Rd in formula (1a) may represent;
  • a hydrogen atom possessed by an alkyl group, aryl group, or heterocyclic group that Rf in formula (1a) may represent;
  • One or more benzene rings that can be formed by bonding with one or more of a group of two or more adjacent ones selected from R 31 to R 38 that are not single bonds bonded to *12 in formula (1a) Hydrogen
  • Hydrogen atoms possessed by one or more benzene rings that can be formed by combining one or more of a group of two or more adjacent ones selected from R 161 to R 165 of formula (1e);
  • the invention compound (2) according to one embodiment of the present invention is represented by the following formula (2).
  • N* is the central nitrogen atom.
  • Raa and Rbb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or It is an unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Raa and Rbb may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure;
  • Raa and Rbb are not bonded to each other and do not form a ring structure, at least one selected from Raa and Rbb is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the number of carbon atoms in the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Raa and Rbb is preferably 1 to 18, more preferably 1 to 6, each independently.
  • Examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Ra and Rb 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, or dodecyl group; Preferably, it is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group
  • the number of ring carbon atoms in the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb is preferably 6 to 18, more preferably 6 to 12, each independently.
  • Examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, anthryl group, benzanthryl group, and phenanthryl group.
  • a benzophenanthryl group a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;
  • it is a phenyl group, a biphenylyl group, a terphenylyl group, or a 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, it is a phenyl group, a 2-, 3-, or 4-b
  • examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb may include any of the substituents described below, and among them, preferred are is an alkyl group having 1 to 6 carbon atoms; more preferably a methyl group or a t-butyl group.
  • the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Raa and Rbb is a substituted or unsubstituted aromatic heterocyclic group (heteroaryl group) having 5 to 30 ring atoms; It is preferable that there be.
  • the number of ring atoms of the unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Raa and Rbb is preferably 5 to 20, more preferably 5 to 13, each independently.
  • Examples of the unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Raa and Rbb include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, and a pyrazinyl group.
  • triazinyl group imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group , phenanthrolinyl group, phenazinyl group,
  • heterocyclic group having 5 to 30 ring atoms that may be represented by Raa and Rbb may include any substituents described below.
  • the ring structure may be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, For example, it is selected from a single ring, a fused ring, a bridged bicyclo ring, or a bridged tricyclo ring.
  • Specific examples of the ring structure that may be formed by bonding Raa and Rbb to each other are shown below, but the structure is not limited thereto. Note that * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.
  • the ring structure is preferably a substituted or unsubstituted hydrocarbon ring.
  • compound (2) as the ring structure that may be formed by Raa and Rbb bonding to each other, for example, the following ring structures are preferable among the specific examples described above.
  • R 51 to R 58 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one selected from R 51 to R 58 is a single bond bonded to *51;
  • One or more pairs of adjacent two or more selected from R 51 to R 58 that are not single bonds bonded to *51 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • compound (2) preferably one selected from R 52 to R 57 is a single bond bonded to *51, more preferably R 52 or R 57 is a single bond bonded to *51. be.
  • R 51 to R 58 can represent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group;
  • 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 preferred are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s
  • Examples of the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 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, it is a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group; More preferred is a cyclohexyl group, 1-adamantyl group, or 2-adamantyl group.
  • R 51 to R 58 can represent examples 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, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a 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-terpheny
  • Examples of the unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R 51 to R 58 include the above Raa and Rbb, except that the number of ring atoms is 5 to 13.
  • Examples of the heterocyclic group include; 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, a quinazolinyl group, a benzimidazolyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, and a dibenzofuranyl group.
  • nyl group is a nyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group; More preferred are a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
  • Rcc is 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.
  • Rcc The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rcc are the same as those explained for the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Raa and Rbb, The same applies to preferred embodiments thereof.
  • preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that Rcc can represent include 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 A t-butyl group; more preferably a methyl group, an ethyl group, or a t-butyl group; still more preferably a methyl group.
  • examples of the substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that may be represented by Rcc may include any of the substituents described below.
  • preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rcc can represent include phenyl, biphenylyl, terphenylyl, or naphthyl; 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 4-biphenylyl group, or 1- or 2-naphthyl group; More preferred is a phenyl group.
  • examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rcc may have include any of the substituents described below, and among them, preferably carbon It is an alkyl group of number 1 to 6; more preferably a methyl group or a t-butyl group.
  • R 61 to R 68 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one or more pairs of adjacent two or more selected from R 61 to R 68 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other to form one or more substituted or unsubstituted benzene rings. They may not be bonded to form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 61 to R 68 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups exemplified as the unsubstituted C1-C10 alkyl groups that R 61 to R 68 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 61 to R 68 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • R 61 to R 68 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 61 to R 68 may represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 51 to R 58 may represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 61 to R 68 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 71 to R 75 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one selected from R 71 to R 75 is a single bond bonded to *52;
  • One or more pairs of adjacent two or more selected from R 71 to R 75 that are not single bonds bonded to *52 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • R 72 , R 73 , or R 74 is preferably a single bond bonded to *52, and more preferably R 72 or R 74 is a single bond bonded to *52. It is.
  • R 71 to R 75 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent above.
  • R 71 to R 75 may represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 71 to R 75 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 71 to R 75 may represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 51 to R 58 may represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 71 to R 75 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • L 21 , L 22 and L 23 are each independently a single bond or an unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • the unsubstituted arylene group having 6 to 12 ring carbon atoms that can be represented by L 21 , L 22 , and L 23 may be the same as described for Raa and Rbb except that the ring carbon number is 6 to 12.
  • Examples include divalent groups obtained by removing one hydrogen atom from an unsubstituted aryl group, preferably an unsubstituted phenylene group, an unsubstituted naphthylene group, or an unsubstituted biphenylene group.
  • the unsubstituted phenylene group that L 21 , L 22 , and L 23 may represent is an o-phenylene group, a m-phenylene group, or a p-phenylene group.
  • the unsubstituted naphthylene group that L 21 , L 22 and L 23 may represent is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.
  • the unsubstituted biphenylene group that L 21 , L 22 and L 23 may represent is preferably a 4,4'-biphenylene group or a 4,3'-biphenylene group (same as " 3,4'-biphenylene group”). ), or 4,2'-biphenylene group (same as "2,4'-biphenylene group”).
  • Ar 2 is a group represented by the following formula (2a), (2b), (2c), (2d), (2e) or (2f).
  • *61 is the bonding position to L23 .
  • Rdd and Rff are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or It is an unsubstituted heterocyclic group having 5 to 30 ring atoms; However, Rdd and Rff may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure.
  • Rdd and Rff The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rdd and Rff are the same as those explained regarding the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Raa and Rbb. can be; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 30 ring carbon atoms that Rdd and Rff can represent.
  • Rdd and Rff examples of the substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rdd and Rff may include any of the substituents described below.
  • Rdd and Rff may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 30 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • Rdd and Rff examples of the substituent that the unsubstituted aryl group having 6 to 30 ring carbon atoms that may be represented by Rdd and Rff include any of the substituents described below, which are preferred among them.
  • Rdd and Rff may represent include the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that Raa and Rbb may represent.
  • the group represented by the formula (2a) is preferably represented by the following formula.
  • the single bonds bonded to *61 and *62, which represent the bonding positions to L 23 , and R 81 to R 88 are omitted for simplification.
  • the group represented by formula (2a) is preferably not unsubstituted spirobifluorene.
  • L 23 is a single bond, it is more preferable that the group represented by the formula (2a) is not unsubstituted spirobifluorene.
  • R 81 to R 88 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • one selected from R 81 to R 88 is a single bond bonded to *62;
  • One or more pairs of adjacent two or more selected from R 81 to R 88 that are not single bonds bonded to *62 are bonded to each other to form one or more substituted or unsubstituted benzene rings. or may not be bonded to each other to form a ring.
  • compound (2) preferably one selected from R 82 to R 87 is a single bond bonded to *62, more preferably R 82 or R 87 is a single bond bonded to *62. be.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 81 to R 88 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and still more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 81 to R 88 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 81 to R 88 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • R 81 to R 88 may represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 81 to R 88 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 81 to R 88 may represent include the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that R 51 to R 58 may represent.
  • the content is the same as that explained regarding the heterocyclic group; Therefore, regarding the types of heterocyclic groups exemplified as the unsubstituted heterocyclic group having 5 to 13 ring atoms that R 81 to R 88 can represent, preferred heterocyclic groups, and more preferred heterocyclic groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • *70 is the bonding position to L23 .
  • one selected from R 291 to R 295 is a single bond bonded to *71
  • one selected from R 301 to R 305 is a single bond bonded to *72
  • One selected from 310 is a single bond bonded to *73
  • R 291 to R 295 that are not a single bond bonded to *71, R 301 to R 305 that are not a single bond bonded to *72, and R 306 to R 310 that are not a single bond bonded to *73 are , each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming carbon atom It is an aryl group of number 6 to 18; Two adjacent ones selected from R 291 to R 295 that are not single bonds bonded to *71 do not bond to each
  • R 291 to R 295 , R 301 to R 305 and R 306 to R 310 may represent include the substituted or unsubstituted alkyl group that may be represented by R 51 to R 58 above.
  • R 291 to R 295 , R 301 to R 305 and R 306 to R 310 may represent an alkyl group, a preferable alkyl group, a more preferable alkyl group, as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms, More preferred alkyl groups and even more preferred types of alkyl groups are also the same as those exemplified in the descriptions of R 51 to R 58 , respectively.
  • R 291 to R 295 , R 301 to R 305 and R 306 to R 310 are as follows: or the same as explained for the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms; Therefore, R 291 to R 295 , R 301 to R 305 and R 306 to R 310 may represent a cycloalkyl group exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a preferred cycloalkyl group, The more preferable types of cycloalkyl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 291 to R 295 , R 301 to R 305 and R 306 to R 310 The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R 291 to R 295 , R 301 to R 305 and R 306 to R 310 are as follows : The content is the same as that explained regarding the unsubstituted aryl group having 6 to 18 ring carbon atoms; Therefore, R 291 to R 295 , R 301 to R 305 and R 306 to R 310 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, and a more preferred aryl group. The groups, more preferred aryl groups, and even more preferred types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 311 to R 315 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; However, two adjacent ones selected from R 311 to R 315 do not bond to each other and therefore do not form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 311 to R 315 can represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R 51 to R 58 .
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R 311 to R 315 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 311 to R 315 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 311 to R 315 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 311 to R 315 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, a still more preferred aryl group, and an even more preferred aryl group.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • m is 0 or 1
  • n is 0 or 1
  • p is 0 or 1; however, When m, n and p are 0, *73 represents the bonding position to L23 , When m and n are 0 and p is 1, *72 represents the bonding position to L23 , When m is 0 and n and p are 1, *71 represents the bonding position to L23 , When m and p are 0 and n is 1, *71 represents the bonding position to L 23 , and one selected from R 301 to R 305 is a single bond bonded to *73, When m is 1 and n and p are 0, one selected from R 291 to R 295 is a single bond bonded to *73, When m and n are 1 and p is 0, one selected from R 301 to R 305 is a single bond bonded to *73.
  • compound (2) for example, the group represented by the formula (2b) can represent each group represented by the following formula.
  • R 291 to R 295 , R 301 to R 305 , R 306 to R 310 and R 311 to R 315 which are not single bonds, are omitted for simplicity.
  • *74 is the bonding position to L23 .
  • R 321 to R 328 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 321 to R 328 is a single bond bonded to *75, and two adjacent ones selected from R 321 to R 328 that are not bonded to *75 are not bonded to each other. and therefore do not form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 321 to R 328 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, even more preferred alkyl groups, and even more preferred alkyl groups as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R 321 to R 328 may represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 321 to R 328 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • the content is similar to that explained regarding the cycloalkyl group; Therefore, regarding the types of cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 321 to R 328 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 321 to R 328 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • *76 is the bonding position to L23 .
  • R 331 to R 340 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 331 to R 340 is a single bond bonded to *77, and two adjacent ones selected from R 331 to R 340 that are not bonded to *77 are not bonded to each other. and therefore do not form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 331 to R 340 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 331 to R 340 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 331 to R 340 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • R 331 to R 340 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • *78 is the bonding position to L23 .
  • R 351 to R 355 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms.
  • R 351 to R 355 is a single bond bonded to *79, and the other selected from R 351 to R 355 is a single bond bonded to *80;
  • Two adjacent ones selected from R 351 to R 355 that are neither a single bond bonded to *79 nor a single bond bonded to *80 do not bond to each other and therefore do not form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 351 to R 355 can represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 can represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, still more preferred alkyl groups, and even more preferred alkyl groups as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R 351 to R 355 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 351 to R 355 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • R 351 to R 355 can represent, preferred cycloalkyl groups, and more preferred cycloalkyl groups, They are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 351 to R 355 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 361 to R 365 and R 371 to R 375 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 carbon number group.
  • one or more pairs of adjacent two or more selected from R 361 to R 365 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may be bonded to each other.
  • One or more pairs of adjacent two or more selected from R 371 to R 375 may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other. It is not necessary to form a ring.
  • R 361 to R 365 and R 371 to R 375 may represent include the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that may be represented by R 51 to R 58 above.
  • the content is the same as that explained regarding the alkyl group; Therefore, R 361 to R 365 and R 371 to R 375 may represent an alkyl group, a preferred alkyl group, a more preferred alkyl group, a still more preferred alkyl group, and , even more preferable types of alkyl groups are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 361 to R 365 and R 371 to R 375 may represent include the substituted or unsubstituted ring-forming group that R 51 to R 58 may represent.
  • the content is the same as that explained regarding the cycloalkyl group having 3 to 10 carbon atoms; Therefore, R 361 to R 365 and R 371 to R 375 may represent cycloalkyl groups exemplified as the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, preferred cycloalkyl groups, and more preferred cycloalkyl groups.
  • the types of groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 361 to R 365 and R 371 to R 375 can represent include the substituted or unsubstituted ring-forming carbon atoms that R 51 to R 58 can represent.
  • the content is the same as that explained regarding the aryl group of numbers 6 to 18; Therefore, R 361 to R 365 and R 371 to R 375 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, and a still more preferred aryl group.
  • R 51 to R 58 may represent an aryl group exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, a preferred aryl group, a more preferred aryl group, and a still more preferred aryl group.
  • aryl groups are the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • the group represented by the formula (2e) includes groups represented by the following formulas (2e-1) to (2e-5).
  • *81 is the bonding position to L23 .
  • R 381 to R 392 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. group, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
  • one selected from R 381 to R 392 is a single bond bonded to *82, and two adjacent ones selected from R 381 to R 392 that are not bonded to *82 are not bonded to each other. and therefore do not form a ring.
  • the details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 381 to R 392 may represent are as explained above with respect to the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that R 51 to R 58 may represent.
  • the content is similar; Therefore, the alkyl groups, preferred alkyl groups, more preferred alkyl groups, even more preferred alkyl groups, and even more preferred alkyl groups as exemplified as the unsubstituted alkyl group having 1 to 10 carbon atoms that R 381 to R 392 can represent.
  • the types of are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • R 381 to R 392 may represent include the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that R 51 to R 58 may represent.
  • R 381 to R 392 may represent aryl groups exemplified as the unsubstituted aryl group having 6 to 18 ring carbon atoms, preferred aryl groups, more preferred aryl groups, still more preferred aryl groups, and even more preferred aryl groups.
  • the types of aryl groups are also the same as those exemplified in the explanations of R 51 to R 58 , respectively.
  • the invention compound (2) when L 21 is a single bond and Ar 2 is represented by the formula (2b), the invention compound (2) has a structure having a fluorene skeleton bonded to the *51. is not unsubstituted spirobifluorene.
  • Ar 2 when L 21 is a single bond, Ar 2 is represented by formula (2b), and all of R 51 to R 58 that are not single bonds bonded to *51 are hydrogen atoms, Raa and Rbb are each an unsubstituted phenyl group, and the two unsubstituted phenyl groups do not bond to each other to form the following ring structure.
  • * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.
  • the structure having a fluorene skeleton bonded to *51 is an unsubstituted Preferably it is not spirobifluorene.
  • L 21 is an unsubstituted arylene group having 6 to 12 ring carbon atoms
  • Ar 2 is represented by formula (2b)
  • the single bond bonded to *51 is If all of R 51 to R 58 that are not It is preferable that the two unsubstituted phenyl groups do not bond to each other to form the ring structure.
  • L 21 is an unsubstituted arylene group having 6 to 12 ring carbon atoms, and all of R 51 to R 58 that are not single bonds bonded to *51 are hydrogen atoms. In the case of It is more preferable that these do not combine with each other to form the above-mentioned ring structure.
  • the invention compound (2) satisfies at least one requirement selected from the following requirements (I) and (II) in formula (2);
  • Requirement (I): R 61 to R 68 and at least one selected from R 71 to R 75 that is not a single bond bonded to *52 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms;
  • compound (2) in formula (2), (2-1) All of R 51 to R 58 that are not single bonds bonded to *51 may be hydrogen atoms; (2-2) All of R 61 to R 68 may be hydrogen atoms; (2-3) *All of R 71 to R 75 that are not single bonds bonded to *52 may be hydrogen atoms; (2-4) *All of R 81 to R 88 that are not single bonds bonded to *62 may be hydrogen atoms; (2-5) *All of R 291 to R 295 that are not single bonds bonded to 71 may be hydrogen atoms; (2-6) *All of R 301 to R 305 that are not single bonds bonded to *72 may be hydrogen atoms; (2-7) *All of R 306 to R 310 that are not single bonds bonded to 73 may be hydrogen atoms; (2-8) All of R 311 to R 315 may be hydrogen atoms; (2-9) *All of R 321 to R 328 that are not single bonds bonded to *75 may be hydrogen atoms;
  • compound (2) in formula (2), R 51 to R 58 which are not single bonds bonded to *51, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or R 61 to R 68 which are not unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted ring carbon atoms 3 It is preferable that all of R 71 to R 75 that are not cycloalkyl groups of ⁇ 10 and are not single bonds bonded to *52 are hydrogen atoms.
  • compound (2) in formula (2), at least one selected from R 61 to R 68 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring.
  • Raa and Rbb are each independently preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms; both Raa and Rbb is more preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms; it is even more preferred that both Raa and Rbb are unsubstituted phenyl groups.
  • Rcc is preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms, and more preferably an unsubstituted phenyl group. .
  • Raa, Rbb and Rcc are preferably each independently a substituted or unsubstituted phenyl group; all of Raa, Rbb and Rcc are substituted. or more preferably an unsubstituted phenyl group; it is even more preferable that all of Raa, Rbb and Rcc are unsubstituted phenyl groups.
  • L 21 and L 22 are preferably each independently a single bond or an unsubstituted phenylene group; It is more preferable that both are a single bond or an unsubstituted phenylene group; it is even more preferable that both L 21 and L 22 are a single bond.
  • L 23 is preferably a single bond or an unsubstituted phenylene group; it is more preferable that L 23 is a single bond.
  • compound (2) in formula (2), all of L 21 , L 22 and L 23 are preferably a single bond or an unsubstituted phenylene group; L 21 , L It is even more preferable that all of 22 and L 23 are single bonds.
  • Ar 2 in formula (2) is preferably a group represented by formula (2a) or (2b).
  • Ar 2 in the formula (2) is a group represented by the formula (2a), and in the formula (2a), it is selected from R 82 to R 87 . It is preferable that one is a single bond bonded to *62; Ar 2 is a group represented by the above formula (2a), and in the above formula (2a), R 82 or R 87 is bonded to *62 More preferably, it is a single bond.
  • L 23 is a single bond
  • Ar 2 is a group represented by the formula (2b), and in the formula (2b), m, n and p are 0, or L 23 is a single bond
  • Ar 2 is a group represented by the above formula (2b), and in the above formula (2b), m is 1, and n and p are 0, R 291 or R 295 is a single bond bonded to *73, or L 23 is a single bond
  • Ar 2 is a group represented by the above formula (2b), and in the above formula (2b), n is 1, and m and p are 0, and R 301 or R 305 is a single bond bonded to *73, or L 23 is a single bond
  • Ar 2 is a group represented by the above formula (2b), and in the above formula (2b), m and n are 0, and p is 1, and R 306 or It is preferable that R 310 is a single bond bonded to *73.
  • 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 (2) by using a deuterated compound as part or all of the raw material compounds. Therefore, in one embodiment of the present invention, the invention compound (2) contains at least one deuterium atom. That is, the invention compound (2) may be a compound represented by formula (2), 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 for the sake of brevity.
  • One hydrogen atom or at least one hydrogen atom selected from two or more hydrogen atoms possessed by the substituent related to the above-mentioned "substituted or unsubstituted” may also be the deuterium atom.
  • a hydrogen atom possessed by an alkyl group, aryl group, or heterocyclic group that Rdd in formula (2a) may represent; A hydrogen atom contained in an alkyl group, aryl group, or heterocyclic group that can be represented by Rff in formula (2a); A hydrogen atom contained in a ring structure that can be formed by combining Rdd and Rff of formula (2a) with each other; A hydrogen atom that can be represented by any of R 81 to R 88 that is not a single bond bonded to *62 in formula (2a); A hydrogen atom possessed by an alkyl group, cycloalkyl group, aryl group, or heterocyclic group that can be represented by any of R 81 to R 88 that is not a single bond bonded to *62 in formula (2a); One or more benzene rings that can be formed by bonding with one or more of a group of two or more adjacent ones selected from R 81 to R 88 that are not single bonds bonded to *62 in formula (2a
  • Hydrogen atoms possessed by one or more benzene rings that can be formed by bonding one or more of a group of two or more adjacent ones selected from R 361 to R 365 of formula (2e);
  • 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.
  • 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 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.
  • 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. is as described in "Substituent in the case of "substituted or unsubstituted”", and is preferably an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or a cycloalkyl group having 3 to 10 ring carbon atoms.
  • the alkyl group having 1 to 10 carbon atoms is preferably a methyl group or a t-butyl group.
  • the aryl group having 6 to 18 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.
  • the material for organic EL device which is one embodiment of the present invention, contains an inventive compound.
  • the content of the invention compound in the organic EL element material is 1% by mass or more (including 100% by mass), preferably 10% by mass or more (including 100% by mass), and 50% by mass or more (including 100% by mass). It is more preferably 80% by mass or more (including 100% by mass), and particularly preferably 90% by mass or more (including 100% by mass).
  • the content of the invention compound in the organic EL element material is 1 to 100% by mass, preferably 10 to 100% by mass, more preferably 50 to 100% by mass, More preferably 80 to 100% by weight, particularly preferably 90 to 100% by weight.
  • the organic EL element material that is one embodiment of the present invention is useful for manufacturing organic EL elements.
  • the organic EL element material is preferably a hole transport layer material.
  • Organic EL Element An organic EL element that is one embodiment of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes an inventive compound.
  • organic layers containing the inventive compound include hole transport zones (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, and the light emitting layer. , a space layer, an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer, but is not limited thereto.
  • the invention compound is preferably a material for a hole transport zone or a light emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for a hole transport zone, and even more preferably a hole injection layer, a hole transport layer, an electron blocking layer, or an excitation layer. It is used as a material for a child blocking layer, particularly preferably a hole injection layer or a hole transport layer.
  • the organic EL device of the present invention may be a monochromatic fluorescent or phosphorescent type light emitting device, a fluorescent/phosphorescent hybrid type white light emitting device, or a simple type having a single light emitting unit.
  • the device may be of a tandem type having a plurality of light emitting units, and is preferably a fluorescent light emitting device.
  • the "light-emitting unit” refers to a minimum unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by recombining injected holes and electrons.
  • the light-emitting unit may be a multilayer type having a plurality of phosphorescence-emitting layers or fluorescent light-emitting layers.
  • a space layer may be provided for the purpose of preventing excitons from diffusing into the fluorescent light emitting layer.
  • a typical layer structure of a simple light emitting unit is shown below. Layers in parentheses are optional.
  • Each of the phosphorescent or fluorescent light-emitting layers may emit light of a different color from each other.
  • (hole injection layer/) hole transport layer/first phosphorescent layer (red light emitting layer)/second phosphorescent light emitting layer (green light emitting layer)/space layer/fluorescent light emitting layer examples include a layer structure such as a layer (blue light emitting)/electron transport layer.
  • an electron blocking layer may be provided between each light emitting layer and the hole transport layer or space layer, as appropriate.
  • a hole blocking layer may be provided between each light emitting layer and the electron transport layer as appropriate.
  • the hole transport layer has a multilayer structure including two or more hole transport layers
  • a hole transport layer adjacent to the light emitting layer in the multilayer structure for example, a second hole transport layer in the two layer structure.
  • the layer or the third hole transport layer of the three-layer structure may have a function as an electron blocking layer. That is, when the hole transport layer has a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light emitting layer in the multilayer structure can also be used as an electron blocking layer.
  • Typical device configurations of tandem type organic EL devices include the following device configurations.
  • the first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units, for example.
  • the intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, or intermediate insulating layer, and supplies electrons to the first light emitting unit and holes to the second light emitting unit. Any known material configuration can be used.
  • FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element of the present invention.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 10 has a light emitting layer 5.
  • a hole transport zone 6 (hole injection layer, hole transport layer, etc.) is formed between the light emitting layer 5 and the anode 3
  • an electron transport zone 7 electron injection layer, electron transport layer, etc.
  • an electron blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5.
  • FIG. 2 is a schematic diagram showing another configuration of the organic EL element of the present invention.
  • the organic EL element 11 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 20 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 20 has a light emitting layer 5.
  • the hole transport zone disposed between the anode 3 and the light emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c.
  • the electron transport zone arranged between the light emitting layer 5 and the cathode 4 is formed from the first electron transport layer 7a and the second electron transport layer 7b.
  • FIG. 3 is a schematic diagram showing another configuration of the organic EL element of the present invention.
  • the organic EL element 12 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 30 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 30 has a light emitting layer 5.
  • the hole transport zone arranged between the anode 3 and the light emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. has been done.
  • the electron transport zone arranged between the light emitting layer 5 and the cathode 4 is formed from the first electron transport layer 7a and the second electron transport layer 7b.
  • a host combined with a fluorescent dopant material is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant material is referred to as a phosphorescent host.
  • Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host refers to a material containing a phosphorescent dopant that forms a phosphorescent layer, and does not mean that it cannot be used as a material to form a fluorescent layer. The same applies to fluorescent hosts.
  • the substrate is used as a support for the organic EL element.
  • a plate of glass, quartz, plastic, etc. can be used.
  • a flexible substrate may be used.
  • the flexible substrate include plastic substrates made of polyimide, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride.
  • an inorganic vapor-deposited film can also be used.
  • Anode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) for the anode formed on the substrate.
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) for the anode formed on the substrate.
  • ITO indium oxide-tin oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • indium oxide containing tungsten oxide and zinc oxide examples include graphene.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • nitrides of the above metals eg, titanium nitride
  • These materials are usually deposited using a sputtering method.
  • a sputtering method For example, for indium oxide-zinc oxide, use a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and for indium oxide containing tungsten oxide and zinc oxide, 0.5 to 5 wt% of tungsten oxide is added to indium oxide. %, and by using a target containing 0.1 to 1 wt % zinc oxide, it can be formed by a sputtering method. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.
  • the organic layer may include a hole transport zone between the anode and the light emitting layer.
  • the hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like.
  • the hole transport zone contains the inventive compound. It is preferable that at least one of these layers constituting the hole transport layer contains the invention compound, and it is particularly preferable that the hole transport layer contains the invention compound.
  • the hole injection layer formed in contact with the anode is formed using a material that can easily inject holes regardless of the work function of the anode. , alloys, electrically conductive compounds, mixtures thereof, and elements belonging to Group 1 or Group 2 of the Periodic Table of Elements). Elements belonging to Group 1 or Group 2 of the periodic table of elements, which are materials with a small work function, such as alkali metals such as lithium (Li) and cesium (Cs), as well as magnesium (Mg), calcium (Ca), and strontium.
  • Alkaline earth metals such as (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), alloys containing these, etc. can also be used.
  • a vacuum evaporation method or a sputtering method can be used.
  • silver paste or the like a coating method, an inkjet method, etc. can be used.
  • Hole injection layer is a layer containing a material with high hole injection property (hole injection material), and is located between the anode and the light emitting layer or, if present, with the hole transport layer. Formed between the anodes.
  • Hole-injecting materials other than the invention compounds include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. oxide, tungsten oxide, manganese oxide, etc. can be used.
  • High molecular compounds oligomers, dendrimers, polymers, etc.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino ⁇ phenyl) methacrylamide]
  • PTPDMA poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine]
  • Polymer compounds such as Poly-TPD
  • a polymer compound to which an acid is added such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrene sulfonic acid) (PAni/PSS), is used. You can also do that.
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
  • HAT hexaazatriphenylene
  • R 221 to R 226 are each independently a cyano group, -CONH 2 , a carboxyl group, or -COOR 227 (R 227 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms)
  • R 227 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms
  • two adjacent groups selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 bond to each other to form a group represented by -CO-O-CO-.
  • R 227 examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group.
  • the hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is located between the anode and the light emitting layer or, if present, between the hole injection layer and the hole transport layer. It is formed between the light emitting layers.
  • the compounds of the invention may be used alone or in combination with the compounds listed below in the hole transport layer.
  • the hole transport layer may have a single layer structure or a multilayer structure including two or more layers.
  • the hole transport layer may have a two-layer structure including a first hole transport layer (on the anode side) and a second hole transport layer (on the cathode side). That is, the hole transport zone may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side.
  • the hole transport layer may have a three-layer structure including, in order from the anode side, a first hole transport layer, a second hole transport layer, and a third hole transport layer. That is, the third hole transport layer may be arranged between the second hole transport layer and the light emitting layer.
  • the single-layer hole transport layer is adjacent to the light emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the two-layer structure
  • the second hole transport layer and the third hole transport layer having the three-layer structure are preferably adjacent to the light emitting layer.
  • the below-mentioned electron A blocking layer or the like may be interposed.
  • the hole transport layer adjacent to the light emitting layer in the multilayer structure can also be used as an electron blocking layer. .
  • the second hole transport layer is preferably adjacent to the light emitting layer as described above. That is, the organic layer includes a hole transport zone between the anode and the light emitting layer, and the hole transport zone includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side. In the case of a layered structure, it is preferable that the light emitting layer and the second hole transport layer are in direct contact with each other. In one embodiment of the present invention, when the hole transport layer has a two-layer structure, it is preferable that at least one of the first hole transport layer and the second hole transport layer contains the inventive compound.
  • the invention compound is preferably contained only in the first hole transport layer, only in the second hole transport layer, or in both the first hole transport layer and the second hole transport layer.
  • the inventive compound is included in the second hole transport layer. That is, it is more preferable that the invention compound is contained only in the second hole transport layer, or that the invention compound is contained in the first hole transport layer and the second hole transport layer.
  • the hole transport layer when the hole transport layer has a three-layer structure, it is preferable that the third hole transport layer is adjacent to the light emitting layer, as described above. That is, the organic layer includes a hole transport zone between the anode and the light emitting layer, and the hole transport zone includes a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. In the case of a three-layer structure including a transport layer, it is preferable that the light emitting layer and the third hole transport layer are in direct contact with each other. In one embodiment of the present invention, when the hole transport layer has a three-layer structure, it is preferable that at least one of the first to third hole transport layers contains the inventive compound.
  • the inventive compound is present in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer); Only two layers selected from the third hole transport layer (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer) and the third hole transport layer) or in all of the first to third hole transport layers.
  • the inventive compound is more preferably contained in the third hole transport layer. That is, it is more preferable that the invention compound is contained only in the third hole transport layer, or that the invention compound is contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer. preferable.
  • the invention compound contained in each of the hole transport layers is preferably a light hydrogen compound from the viewpoint of manufacturing cost.
  • the light hydrogen compound refers to an invention compound in which all hydrogen atoms are light hydrogen atoms. Therefore, in one embodiment of the present invention, one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), and at least one of the first to third hole transport layers are substantially It is preferable that the organic EL device contains an inventive compound consisting only of a light hydrogen compound.
  • invention compound consisting essentially only of light hydrogen bodies means that the content ratio of light hydrogen bodies to the total amount of the invention compounds is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each 100 mol%).
  • the "invention compound consisting essentially only of light hydrogen bodies” means that the content ratio of light hydrogen bodies to the total amount of the invention compounds is 90 to 100 mol%, preferably This means 95 to 100 mol%, more preferably 99 to 100 mol%.
  • aromatic amine compounds for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.
  • aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N'-bis(3-methylphenyl)-N , N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N -diphenylamino)triphen
  • carbazole derivatives examples include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and Examples include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
  • anthracene derivatives examples include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and , 9,10-diphenylanthracene (abbreviation: DPAnth).
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • compounds other than those mentioned above may be used as long as they have higher hole transport properties than electron transport properties.
  • the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12). is preferred.
  • one or both of the first hole transport layer and the second hole transport layer is 1 represented by the following formula (11) or (12). Preferably, it contains one or more compounds.
  • the organic EL device of the present invention having a hole transport layer with an n-layer structure n is an integer of 4 or more
  • at least one of the first hole transport layer to the (n-1)th hole transport layer has the following formula: It is preferable that one or more compounds represented by (11) or formula (12) are included.
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted arylene group is a divalent heterocyclic group having 5 to 50 ring atoms, k is 1, 2, 3 or 4, When k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; When k is 2, 3 or 4, 2, 3 or 4 L E2 are the same or different, When k is 2, 3 or 4, the plurality of L E2s are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsub
  • a 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming aryl group
  • R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms
  • a 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 are preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibensofuranyl group, substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
  • At least one of A 1 , B 1 and C 1 and in formula (12), at least one of A 2 , B 2 , C 2 and D 2 is , substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibensofuranyl group, or substituted or unsubstituted dibenzo A thiophenyl group or a substituted or unsubstituted carbazolyl group.
  • the fluorenyl group that A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 can have may have a substituent at the 9-position, for example, 9,9-dimethylfluorenyl group. It may be a nyl group or a 9,9-diphenylfluorenyl group. Further, the substituents at the 9-position may form a ring, for example, the substituents at the 9-position may form a fluorene skeleton or a xanthene skeleton.
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • the light emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used.
  • a fluorescent material or a phosphorescent material can be used as a dopant material.
  • Fluorescent materials are compounds that emit light from a singlet excited state
  • phosphorescent materials are compounds that emit light from a triplet excited state.
  • the light emitting layer is preferably a single layer.
  • the light-emitting layer preferably includes a first light-emitting layer and a second light-emitting layer.
  • Pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used as blue fluorescent materials that can be used in the light-emitting layer.
  • N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H -carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBAPA).
  • Aromatic amine derivatives and the like can be used as green fluorescent materials that can be used in the light emitting layer.
  • 2PCAPA N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine
  • 2PCABPhA N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine
  • 2DPAPA N-(9,10-diphenyl-2-anthryl)-N,N ',N'-triphenyl-1,4-phenylenediamine
  • 2DPAPA N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N' , N'-triphenyl-1,4-phenylenediamine
  • 2DPABPhA N-[9,10-bis(1,1'-biphenyl-2
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light emitting layer.
  • N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine abbreviation: p-mPhTD
  • 7,14-diphenyl-N,N,N' examples include N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
  • the light-emitting layer contains a fluorescent material (fluorescent dopant material).
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue-based phosphorescent materials that can be used in the light-emitting layer.
  • An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer.
  • Tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate ( Abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir(bzz)2(acac)), and the like.
  • Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red-colored phosphorescent materials that can be used in the light-emitting layer.
  • bis[2-(2′-benzo[4,5- ⁇ ]thienyl)pyridinato-N,C3′]iridium(III) acetylacetonate abbreviation: Ir(btp)2(acac)
  • Bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate abbreviation: Ir(piq)2(acac)
  • (acetylacetonato)bis[2,3-bis(4-fluoro) phenyl)quinoxalinato]iridium(III) abbreviation: Ir(Fdpq)2(acac)
  • tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)
  • tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline) europium (III) (abbreviation: Eu(DBM)3(Phen)
  • tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) europium(III) (abbreviation: Eu( Rare earth metal complexes such as TTA)3(Phen) can be used as phosphorescent materials because they emit light from rare earth metal ions (electronic transition between different multiplicities).
  • the light emitting layer may have a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material that has a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.
  • LUMO level lowest unoccupied orbital level
  • HOMO level lowest occupied orbital level
  • host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives are used.
  • tris(8-quinolinolato)aluminum(III) (abbreviation: Alq)
  • tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3)
  • bis(10-hydroxybenzo[h]quinolinato)beryllium (II) (abbreviation: BeBq2)
  • bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) abbreviation: BAlq
  • bis(8-quinolinolato)zinc(II) (abbreviation: Znq)
  • bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), etc.
  • anthracene compound in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.
  • the organic EL element when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer contains the second light-emitting layer. It is different from the constituent components.
  • the dopant material contained in the first light emitting layer may be different from the dopant material contained in the second light emitting layer, or the host material contained in the first light emitting layer may be different from the host material contained in the second light emitting layer. Different aspects are mentioned.
  • the light-emitting layer may contain a light-emitting compound (hereinafter sometimes simply referred to as a "fluorescent compound”) that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.
  • a light-emitting compound hereinafter sometimes simply referred to as a "fluorescent compound” that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.
  • the lower limit of the main peak wavelength is not particularly limited as long as the effects of the present invention can be achieved, but in one embodiment of the organic EL element, the lower limit of the main peak wavelength may be 400 nm, for example. Therefore, in one embodiment of the organic EL element, the main peak wavelength may be, for example, 400 to 500 nm.
  • the method for measuring the main peak wavelength of a compound is as follows. A 5 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. Note that in this specification, the main peak wavelength may be referred to as fluorescence main peak wavelength (FL-peak).
  • the fluorescent compound may be the dopant material or the host material.
  • the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent compound, or both may be the fluorescent compound.
  • the light emitting layer includes a first light emitting layer (anode side) and a second light emitting layer (cathode side)
  • only one of the first light emitting layer and the second light emitting layer contains the fluorescent compound.
  • both light-emitting layers may contain the fluorescent compound.
  • the first light-emitting layer contains the fluorescent compound
  • only one of the dopant material and the host material contained in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.
  • the second light-emitting layer contains the fluorescent compound
  • only one of the dopant material and the host material contained in the second light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound. It may be a sexual compound.
  • Electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light emitting layer and the cathode or, if present, between the electron injection layer and the light emitting layer. Ru.
  • the electron transport layer may have a single layer structure or a multilayer structure including two or more layers.
  • the electron transport layer may have a two-layer structure including a first electron transport layer (on the anode side) and a second electron transport layer (on the cathode side).
  • the electron transport layer of the single layer structure is preferably adjacent to the light emitting layer, and the electron transport layer of the multilayer structure closest to the anode, for example, the electron transport layer of the two layer structure is adjacent to the light emitting layer.
  • the electron transport layer of the two layer structure is adjacent to the light emitting layer.
  • one electron transport layer is adjacent to the light emitting layer.
  • the hole blocking layer described below is provided between the electron transport layer and the light emitting layer of the single layer structure, or between the electron transport layer and the light emitting layer closest to the light emitting layer in the multilayer structure. A layer or the like may be interposed.
  • the electron transport layer includes, for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, (3) High molecular compounds can be used.
  • Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes
  • Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives
  • High molecular compounds can be used.
  • metal complexes examples include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato).
  • Beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq) ), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), (8- quinolinolato) lithium (abbreviation: Liq).
  • heteroaromatic compound examples include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5 -(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4 -biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4 - Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzo
  • polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9, 9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
  • the above material has an electron mobility of 10 ⁇ 6 cm 2 /Vs or more. Note that materials other than those mentioned above may be used for the electron transport layer as long as they have higher electron transport properties than hole transport properties.
  • the electron injection layer is a layer containing a material with high electron injection properties.
  • the electron injection layer contains alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), europium (Eu), and ytterbium (Yb).
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), europium (Eu), and ytterbium (Yb).
  • Rare earth metals such as these and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, and rare earth metal oxides.
  • Examples include rare earth metal halides, and rare earth metal-containing organic complexes. Moreover, a plurality of these compounds can also be used in combination.
  • a material having an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically a material containing magnesium (Mg) in Alq may be used. Note that in this case, electron injection from the cathode can be performed more efficiently.
  • a composite material made of a mixture of an organic compound and an electron donor may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from an electron donor.
  • the organic compound is preferably a material that is excellent in transporting received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) are used. be able to.
  • the electron donor may be any material as long as it exhibits electron donating properties to organic compounds.
  • alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferable, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like.
  • Lewis bases such as magnesium oxide can also be used.
  • organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • Cathode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less) for the cathode.
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca). ), alkaline earth metals such as strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • the cathode when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using silver paste or the like, a coating method, an inkjet method, etc. can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can do. These conductive materials can be formed into films using a sputtering method, an inkjet method, a spin coating method, or the like.
  • Insulating Layer Organic EL elements are prone to pixel defects due to leaks and short circuits because an electric field is applied to an ultra-thin film.
  • an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
  • materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. , germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. Note that a mixture or a laminate of these may also be used.
  • the above-mentioned space layer is, for example, for the purpose of preventing excitons generated in the phosphorescent layer from diffusing into the fluorescent layer or adjusting carrier balance when a fluorescent layer and a phosphorescent layer are stacked.
  • This is a layer provided between a fluorescent layer and a phosphorescent layer.
  • a space layer can also be provided between a plurality of phosphorescence-emitting layers. Since the space layer is provided between the light-emitting layers, it is preferably made of a material that has both electron-transporting properties and hole-transporting properties. Further, in order to prevent triplet energy from diffusing in adjacent phosphorescent emitting layers, it is preferable that the triplet energy is 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the hole transport layer described above.
  • Blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, an exciton blocking layer, etc. may be provided adjacent to the light emitting layer.
  • the electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer.
  • the exciton blocking layer has the function of preventing excitons generated in the light emitting layer from diffusing into surrounding layers and confining the excitons within the light emitting layer.
  • Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like.
  • vapor deposition methods such as vacuum evaporation method and molecular beam evaporation method (MBE method), or dipping method, spin coating method, casting method, bar coating method, roll coating method, etc. using a solution of a compound forming a layer. It can be formed by a known coating method.
  • the film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and on the other hand, if the film thickness is too thick, a high driving voltage will be required and efficiency will deteriorate, so it is usually 5 nm to 10 ⁇ m. More preferably 10 nm to 0.2 ⁇ m.
  • the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or more.
  • the thickness is more preferably 40 nm or more and 130 nm or less.
  • the thickness of the second hole transport layer having a two-layer structure or a three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, and particularly preferably 35 nm or more. and preferably 100 nm or less.
  • the thickness of the second hole transport layer having a two-layer structure or a three-layer structure is, for example, preferably 5 to 100 nm, more preferably 20 to 100 nm, and still more preferably 25 to 100 nm. 100 nm, particularly preferably 35 to 100 nm. Further, in one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and Preferably it is 100 nm or less.
  • the thickness of the hole transport layer adjacent to the light emitting layer is, for example, preferably 5 to 100 nm, more preferably 20 to 100 nm, even more preferably 25 to 100 nm, particularly preferably It is 30 to 100 nm.
  • the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3 ⁇ D2/D1 ⁇ 4.0, more preferably 0.5 ⁇ D2/D1 ⁇ 3.5, still more preferably 0.75 ⁇ D2/D1 ⁇ 3.0.
  • Preferred embodiments of the organic EL device of the present invention include, for example, (1) Organic EL device having a two-layered hole transport layer - A first embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer does not contain the inventive compound; - A second embodiment in which both the first hole transport layer and the second hole transport layer contain the inventive compound; - A third embodiment in which the first hole transport layer contains the invention compound and the second hole transport layer does not contain the invention compound; (2) an organic EL device having a three-layered hole transport layer; a fourth embodiment in which the first hole transport layer contains the inventive compound and the second and third hole transport layers do not contain the inventive compound; - A fifth embodiment in which the second hole transport layer contains the invention compound and the first and third hole transport layers do not contain the invention compound; - A sixth embodiment in which the third hole transport layer contains the invention compound and the first and second hole transport layers do not contain the invention compound; - A seventh embodiment in which the first and second hole transport layers contain the invention compound and the third hole transport layer does not contain the invention compound;
  • the organic EL element can be used in, for example, display parts such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic equipment such as lighting devices and light emitting devices for vehicle lamps. That is, an electronic device that is one embodiment of the present invention includes the organic EL element.
  • the mass ratio of compound HT-1-1 and compound HA was 97:3.
  • compound HT-1-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 40 nm.
  • the invention compound Inv-1 was deposited on this first hole transport layer to form a second hole transport layer with a thickness of 45 nm.
  • compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated onto this second hole transport layer to form a light emitting layer with a thickness of 20 nm.
  • the mass ratio of compound BH-1 and compound BD-1 was 99:1.
  • compound ET-1 was deposited to form a first electron transport layer with a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 25 nm.
  • the mass ratio of compound ET-2 and Liq (ET-2:Liq) was 50:50.
  • Yb was deposited on the second electron transport layer to form an electron injection electrode with a thickness of 1 nm.
  • metal Al was deposited on this electron injection electrode to form a metal cathode having a thickness of 50 nm.
  • the layer structure (device structure (I)) of the organic EL device (I) thus obtained is shown below.
  • Comparative examples 1 and 2 Example 1 except that Comparative Compound Ref-1 or Comparative Compound Ref-2 was used instead of Inventive Compound Inv-1 used as the second hole transport layer material, as shown in Table 1 below.
  • An organic EL device (I) was produced in the same manner.
  • Organic EL Element (I) (1) Measurement of External Quantum Efficiency (EQE) The obtained organic EL element (I) was driven at a constant DC current at a current density of 10 mA/cm 2 at room temperature. Luminance was measured using a luminance meter (Spectroluminance radiometer CS-1000 manufactured by Minolta), and the external quantum efficiency (%) was determined from the results. The results are shown in Table 1 below.
  • the invention compound Inv-1 can provide an organic EL device with higher external quantum efficiency than the comparative compounds Ref-1 and Comparative compounds Ref-2.
  • the mass ratio of compound HT-1-2 and compound HA was 97:3.
  • compound HT-1-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 40 nm.
  • the invention compound Inv-2 was deposited on this first hole transport layer to form a second hole transport layer with a thickness of 40 nm.
  • compound HT-3 was deposited to form a third hole transport layer with a thickness of 5 nm.
  • compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated onto this third hole transport layer to form a light emitting layer with a thickness of 20 nm.
  • the mass ratio of compound BH-1 and compound BD-1 was 99:1.
  • compound ET-1 was deposited to form a first electron transport layer with a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 25 nm.
  • the mass ratio of compound ET-2 and Liq was 50:50.
  • Yb was deposited on the second electron transport layer to form an electron injection electrode with a thickness of 1 nm.
  • metal Al was deposited on this electron injection electrode to form a metal cathode having a thickness of 50 nm.
  • the layer structure (device structure (II)) of the organic EL device (II) thus obtained is shown below.
  • the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.
  • Comparative example 3 An organic EL device (II) was prepared in the same manner as in Example 2, except that the comparative compound Ref-3 was used instead of the invention compound Inv-2 used as the second hole transport layer material, as shown in Table 2 below. Created.
  • Organic EL Element (II) (1) Measurement of External Quantum Efficiency (EQE) The obtained organic EL element (II) was driven at a constant DC current at a current density of 10 mA/cm 2 at room temperature. Luminance was measured using a luminance meter (Spectroluminance radiometer CS-1000 manufactured by Minolta), and the external quantum efficiency (%) was determined from the results. The results are shown in Table 2 below.
  • the mass ratio of compound HT-1-3 and compound HA was 97:3.
  • compound HT-1-3 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 30 nm.
  • the invention compound Inv-5 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 40 nm.
  • compound HT-4 was deposited on the second hole transport layer to form a third hole transport layer with a thickness of 15 nm.
  • compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated onto this third hole transport layer to form a light emitting layer with a thickness of 20 nm.
  • the mass ratio of compound BH-2 and compound BD-2 was 98:2.
  • compound ET-3 was deposited to form a first electron transport layer with a thickness of 10 nm.
  • the compound ET-4 and Li were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 20 nm.
  • the mass ratio of compound ET-4 and Li was 96:4.
  • metal Al was deposited on this second electron transport layer to form a metal cathode having a thickness of 80 nm.
  • the layer structure (device structure (III)) of the organic EL device (III) thus obtained is shown below.
  • inventive compound Inv-6, inventive compound Inv-7, or inventive compound Inv-8 was used instead of inventive compound Inv-5 used as the second hole transport layer material.
  • An organic EL device (III) was produced in the same manner as in Example 3.
  • Comparative examples 4 to 6 Except that Comparative Compound Ref-4, Comparative Compound Ref-5, or Comparative Compound Ref-6 was used instead of Inventive Compound Inv-5 used as the second hole transport layer material, as shown in Table 3 below.
  • An organic EL device (III) was produced in the same manner as in Example 3.
  • Organic EL Element (III) (1) Measurement of External Quantum Efficiency (EQE) The obtained organic EL element (III) was driven at a constant DC current at a current density of 10 mA/cm 2 at room temperature. Luminance was measured using a luminance meter (Spectroluminance radiometer CS-1000 manufactured by Minolta), and the external quantum efficiency (%) was determined from the results. The results are shown in Table 3 below.
  • inventive compounds Inv-5 to Inv-8 can provide organic EL devices with higher external quantum efficiency than comparative compounds Ref-4 to Comparative compounds Ref-6. .
  • N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine 5.26 g (10.0 mmol), 9-(3-bromo phenyl)-9-phenyl-9H-fluorene 3.97g (10.0mmol), tris(dibenzylideneacetone)dipalladium(0) 0.183g (0.200mmol), tri-tert-butylphosphonium tetrafluoroborate 0
  • a mixture of .232 g (0.800 mmol), 4.2 mL of sodium t-pentoxide (40% toluene solution), and 67 mL of toluene was refluxed at the boiling point for 6 hours.
  • the reaction solution was cooled to room temperature, it was concentrated under reduced pressure.
  • the obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.76 g of white solid. The yield was 33%.
  • the obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.65 g of white solid. The yield was 56%.
  • a white solid was obtained by carrying out the same operation as in Synthesis Example 1 except that Intermediate B was used in place of 9-(3-bromophenyl)-9-phenyl-9H-fluorene used in Synthesis Example 1.

Abstract

La présente invention concerne un composé qui est représenté par la formule (1) ou (2) (où chaque symbole figurant dans les formules (1) et (2) est tel que défini dans la description), un élément électroluminescent organique qui comprend ledit composé représenté par la formule (1) ou (2), et un dispositif électronique qui comprend ledit élément électroluminescent organique.
PCT/JP2023/016479 2022-04-26 2023-04-26 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2023210698A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112250585A (zh) * 2019-07-22 2021-01-22 南京高光半导体材料有限公司 一种空穴传输材料及使用该种材料的有机电致发光器件
WO2021045590A1 (fr) * 2019-09-06 2021-03-11 Duk San Neolux Co., Ltd. Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci et dispositif électronique associé
CN113045434A (zh) * 2021-03-03 2021-06-29 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的有机电致发光器件和电子装置
WO2021149998A1 (fr) * 2020-01-20 2021-07-29 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant celui-ci
CN113563205A (zh) * 2020-04-29 2021-10-29 株式会社东进世美肯 新型化合物以及包含上述新型化合物的有机发光元件
WO2022080715A1 (fr) * 2020-10-12 2022-04-21 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR102407840B1 (ko) * 2021-01-06 2022-06-13 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN115160272A (zh) * 2021-09-15 2022-10-11 陕西莱特光电材料股份有限公司 一种含氮化合物及使用其的电子元件和电子装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112250585A (zh) * 2019-07-22 2021-01-22 南京高光半导体材料有限公司 一种空穴传输材料及使用该种材料的有机电致发光器件
WO2021045590A1 (fr) * 2019-09-06 2021-03-11 Duk San Neolux Co., Ltd. Composé pour élément électronique organique, élément électronique organique faisant appel à celui-ci et dispositif électronique associé
WO2021149998A1 (fr) * 2020-01-20 2021-07-29 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant celui-ci
CN113563205A (zh) * 2020-04-29 2021-10-29 株式会社东进世美肯 新型化合物以及包含上述新型化合物的有机发光元件
WO2022080715A1 (fr) * 2020-10-12 2022-04-21 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR102407840B1 (ko) * 2021-01-06 2022-06-13 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN113045434A (zh) * 2021-03-03 2021-06-29 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的有机电致发光器件和电子装置
CN115160272A (zh) * 2021-09-15 2022-10-11 陕西莱特光电材料股份有限公司 一种含氮化合物及使用其的电子元件和电子装置

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