WO2022210821A1 - 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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WO2022210821A1
WO2022210821A1 PCT/JP2022/015770 JP2022015770W WO2022210821A1 WO 2022210821 A1 WO2022210821 A1 WO 2022210821A1 JP 2022015770 W JP2022015770 W JP 2022015770W WO 2022210821 A1 WO2022210821 A1 WO 2022210821A1
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匡 羽毛田
将太 田中
佑典 高橋
拓人 深見
司 澤藤
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出光興産株式会社
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Priority to KR1020237032191A priority patent/KR20230162933A/ko
Publication of WO2022210821A1 publication Critical patent/WO2022210821A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • 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
    • H10K50/156—Hole transporting layers comprising a multilayered structure
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • 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 electroluminescence device, an organic electroluminescence device, and an electronic device including the organic electroluminescence device.
  • an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode.
  • an organic EL element 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. It emits light when the state returns to the ground state. Therefore, development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates recombination of electrons and holes is important for obtaining high-performance organic EL devices.
  • Patent Documents 1 to 4 disclose compounds used as materials for organic electroluminescence elements.
  • the present invention has been made to solve the above problems, and provides a compound that further improves the performance of an organic EL device, an organic EL device with improved device performance, and an electronic device containing such an organic EL device. intended to provide
  • organic EL devices containing the compound represented by the following formula (1) have better performance. found to be improved.
  • the present invention provides a compound represented by formula (1) below.
  • N * is the central nitrogen atom
  • one of R 1 and R 2 is an unsubstituted methyl group and the other is an unsubstituted phenyl group
  • R 1 and R 2 are not bonded to each other and thus do not form a ring structure.
  • R 3 and R 4 are each independently a hydrogen atom, an unsubstituted methyl group, or an unsubstituted phenyl group;
  • R3 and R4 are not bonded to each other and thus do not form a ring structure.
  • R 11 to R 16 and R 21 to R 27 are hydrogen atoms.
  • R 31 to R 35 are hydrogen atoms.
  • Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms.
  • the present invention provides an organic EL device material containing the compound represented by the formula (1).
  • the present invention is an organic electroluminescent device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least the organic layer
  • an organic electroluminescence device in which one layer contains the compound represented by the formula (1).
  • the present invention provides an electronic device including the organic electroluminescence element.
  • An organic EL device containing the compound represented by formula (1) 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 aspect of the present invention
  • FIG. 4 is a schematic diagram showing another example of the layer structure of the organic EL element according to one aspect of the present invention.
  • a hydrogen atom includes isotopes with different neutron numbers, ie, protium, deuterium, and tritium.
  • a hydrogen atom that is, a hydrogen atom, a deuterium atom, or Assume that the tritium atoms are bonded.
  • the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). represents the number of carbon atoms among the atoms that When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms
  • the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
  • the number of ring-forming carbon atoms in the benzene ring substituted with the alkyl group is 6.
  • the naphthalene ring substituted with an alkyl group has 10 ring-forming carbon atoms.
  • the number of ring-forming atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, bridged compounds, carbocyclic compound, and heterocyclic compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom that constitutes a ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of atoms forming the pyridine ring. Therefore, the number of ring-forming atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6.
  • the expression "substituted or unsubstituted XX to YY carbon number ZZ group” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in the substituents.
  • "YY” is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • "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 represents a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group is a "substituted or unsubstituted ZZ group”. is a "substituted ZZ group”.
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • a hydrogen atom in the "unsubstituted ZZ group” is a protium 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.
  • substituted in the case of "a 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-forming 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. .
  • the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2-50, preferably 2-20, more preferably 2-6, unless otherwise specified in the specification.
  • the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified. be.
  • the number of ring-forming carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified. .
  • the number of ring-forming 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 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified.
  • unsubstituted aryl group refers to the case where "substituted or unsubstituted aryl group” is “unsubstituted aryl group", and substituted aryl group is “substituted or unsubstituted aryl group” It refers to a "substituted aryl group”.
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
  • a "substituted aryl group” means a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group examples include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of Specific Example Group G1A below is replaced with a substituent, and a substituted aryl group of Specific Example Group G1B below.
  • Examples include:
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are only examples, and the “substituted aryl group” described herein includes the following specific examples A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group” of Group G1B is further replaced with a substituent, and the hydrogen atom of the substituent in the "substituted aryl group” of Specific Example Group G1B below Furthermore, groups substituted with substituents are also included.
  • aryl group (specific example group G1A): phenyl group, a p-biphenyl group, m-biphenyl group, an 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, benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chryseny
  • Substituted aryl group (specific example group G1B): an o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, an ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, an 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, a cyanophenyl group, a
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
  • a “heterocyclic group” as described herein is a monocyclic group or a condensed ring group.
  • a “heterocyclic group” as described herein is either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • specific examples of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups ( Specific example group G2B) and the like can be mentioned.
  • unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to “substituted or unsubstituted "Heterocyclic group” refers to a "substituted heterocyclic group”.
  • heterocyclic group refers to a "substituted heterocyclic group”.
  • a “substituted heterocyclic group” means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups of the following specific example group G2B. mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are only examples, and the "substituted heterocyclic group” described herein specifically includes A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" of Specific Example Group G2B A group in which the hydrogen atom of is further replaced with a substituent is also included.
  • Specific example group G2A includes, for example, the following nitrogen atom-containing unsubstituted heterocyclic groups (specific example group G2A1), oxygen atom-containing unsubstituted heterocyclic groups (specific example group G2A2), sulfur atom-containing unsubstituted (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • nitrogen atom-containing unsubstituted heterocyclic groups specifically example group G2A1
  • oxygen atom-containing unsubstituted heterocyclic groups specifically example group G2A2
  • sulfur atom-containing unsubstituted specifically example group G2A3
  • a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures 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 group containing a nitrogen atom (specific example group G2B1), substituted heterocyclic group containing an oxygen atom (specific example group G2B2), substituted heterocyclic ring containing a sulfur atom group (specific example group G2B3), and 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) as a substituent Including substituted groups (example group G2B4).
  • an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, quinolyl group, an isoquinolyl group, cinnolyl group, a phthalazinyl group, a quinazolinyl
  • an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, azanaphthobenzofuranyl group and diazanaphthobenzofuranyl group;
  • thienyl group an unsubstituted heterocyclic group containing a sulfur atom
  • thienyl group a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothiopheny
  • 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 groups derived from the represented ring structures include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 .
  • a 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, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group and a biphenylylquinazolinyl group;
  • a 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].
  • a substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
  • the "one or more hydrogen atoms of the monovalent heterocyclic group” means that at least one of the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, XA and YA is NH.
  • unsubstituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is “unsubstituted alkyl group”
  • substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group” is It refers to a "substituted alkyl group”.
  • alkyl group includes both an "unsubstituted alkyl group” and a "substituted alkyl group”.
  • a “substituted alkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with substituents, and substituted alkyl groups (specific examples Examples of group G3B) and the like can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group.
  • the "unsubstituted alkyl group” includes a linear “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described herein includes specific example group G3B A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group” of Specific Example Group G3B is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group” of Specific Example Group G3B is further replaced by a substituent included.
  • 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): a 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" described in the specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) and the like.
  • unsubstituted alkenyl group refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group", "substituted alkenyl group” means "substituted or unsubstituted alkenyl group ” is a “substituted alkenyl group”.
  • alkenyl group simply referring to an “alkenyl group” includes both an “unsubstituted alkenyl group” and a “substituted alkenyl group”.
  • a “substituted alkenyl group” means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include groups in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, and substituted alkenyl groups (specific example group G4B). be done.
  • Unsubstituted alkenyl group (specific example group G4A): a 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, a 2-methylallyl group and a 1,2-dimethylallyl group;
  • Substituted or unsubstituted alkynyl group Specific examples of the "substituted or unsubstituted alkynyl group" described in the specification (specific example group G5) include the following unsubstituted alkynyl groups (specific example group G5A).
  • unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group” is "unsubstituted alkynyl group”.
  • alkynyl group means "unsubstituted includes both "alkynyl group” and "substituted alkynyl group”.
  • a “substituted alkynyl group” means a group in which one or more hydrogen atoms in an "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 substituents.
  • Substituted or unsubstituted cycloalkyl group Specific examples of the "substituted or unsubstituted cycloalkyl group” described in the specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A), and substituted cycloalkyl groups ( Specific example group G6B) and the like can be mentioned.
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group", and substituted cycloalkyl group refers to "substituted or unsubstituted It refers to the case where "cycloalkyl group” is “substituted cycloalkyl group”.
  • cycloalkyl group means "unsubstituted cycloalkyl group” and “substituted cycloalkyl group”. including both.
  • a “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with substituents, and substituted cycloalkyl groups (Specific example group G6B) and the like.
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are only examples, and the "substituted cycloalkyl group” described herein specifically includes A group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of Example Group G6B is replaced with a substituent, and in the “substituted cycloalkyl group” of Specific Example Group G6B A group in which a hydrogen atom of a substituent is further replaced with a substituent is also included.
  • cycloalkyl group (specific example group G6A): a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a 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 A 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 the specification include: -Si(G1)(G1)(G1), - Si (G1) (G2) (G2), - Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6) is 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 G1's in -Si(G1)(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -Si (G1) (G2) (G2) are the same or different from each other.
  • a plurality of G1's in -Si(G1)(G1)(G2) are the same or different from each other.
  • a plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.
  • a plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.
  • a plurality of G6 in -Si(G6)(G6)(G6) are the same or different from each other.
  • 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 A group represented by -S- (R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in the specification include: -S(G1), -S(G2), -S (G3) and -S (G6) is 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.
  • 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 G1's in -N(G1)(G1) are the same or different from each other.
  • a plurality of G2 in -N(G2)(G2) are the same or different from each other.
  • a plurality of G3s in -N(G3)(G3) are the same or different from each other.
  • - the plurality of G6 in N (G6) (G6) are the same or different from each other
  • halogen atom described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • the "substituted or unsubstituted fluoroalkyl group” described in this specification 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 fluorine atom. Also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with fluorine atoms.
  • the carbon number of the “unsubstituted fluoroalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of a “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 atoms of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and A group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted fluoroalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • Substituted or unsubstituted haloalkyl group "Substituted or unsubstituted haloalkyl group” described herein 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 Also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the carbon number of the “unsubstituted haloalkyl group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • a "substituted haloalkyl group” means a group in which one or more hydrogen atoms of a “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 atoms of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent group, and a “substituted A group in which one or more hydrogen atoms of the substituent in the "haloalkyl group of" is further replaced with a substituent is also included.
  • Specific examples of the "unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the above “alkyl group” (specific example group G3) are replaced with halogen atoms.
  • a haloalkyl group may be 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 alkyl group".
  • the carbon number of the "unsubstituted alkoxy group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • 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), wherein G3 is the "substituted or unsubstituted alkyl group".
  • the carbon number of the “unsubstituted alkylthio group” is 1-50, preferably 1-30, more preferably 1-18, unless otherwise specified in the specification.
  • Substituted or unsubstituted aryloxy group Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification are groups represented by —O(G1), where G1 is the “substituted or an unsubstituted aryl group”.
  • the number of ring-forming carbon atoms in the "unsubstituted aryloxy group” is 6-50, preferably 6-30, more preferably 6-18, unless otherwise specified in the specification.
  • ⁇ "Substituted or unsubstituted trialkylsilyl group” Specific examples of the "trialkylsilyl group” described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the group described in Specific Example Group G3. It is a "substituted or unsubstituted alkyl group”. A plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1-50, preferably 1-20, more preferably 1-6, unless otherwise specified in the specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the 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 specific example group G1.
  • an "aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect 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 unless otherwise specified herein. , 7-50, preferably 7-30, more preferably 7-18.
  • substituted or unsubstituted aralkyl group include a 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.
  • a substituted or unsubstituted aryl group described herein is preferably a 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, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group,
  • substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenyl, unless otherwise stated herein.
  • nantholinyl 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-
  • a carbazolyl group is specifically any one of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any one of the following groups, unless otherwise stated in the specification.
  • a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t- butyl group and the like.
  • the "substituted or unsubstituted arylene group” described herein is derived from the above "substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. is the base of the valence.
  • Specific examples of the “substituted or unsubstituted arylene group” include the “substituted or unsubstituted aryl group” described in specific example group G1 by removing one hydrogen atom on the aryl ring. Induced divalent groups and the like can be mentioned.
  • Substituted or unsubstituted divalent heterocyclic group Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group” described herein is the above “substituted or unsubstituted heterocyclic group” except that one hydrogen atom on the heterocyclic ring is removed. 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 heterocyclic ring from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • Substituted or unsubstituted alkylene group Unless otherwise specified, the "substituted or unsubstituted alkylene group” described herein is derived from the above “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. is the base of the valence. Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include the “substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain. Induced divalent groups and the like can be mentioned.
  • the substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a binding position.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Formulas Q9 and Q10 may be linked together through a single bond to form a ring.
  • * represents a binding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents a binding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein 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.
  • R 921 and R 922 when “one or more pairs of two or more adjacent pairs of R 921 to R 930 are combined to form a ring", is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .
  • one or more pairs means that two or more of the groups consisting of two or more adjacent groups may form a ring at the same time.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 925 and R 926 are bonded together to form ring Q B
  • the general formula (TEMP-103) The represented anthracene compound is represented by the following general formula (TEMP-104).
  • a group consisting of two or more adjacent pairs forms a ring is not limited to the case where a group consisting of two adjacent "two” is combined as in the above example, but It also includes the case where a pair is combined.
  • R 921 and R 922 are bonded together to form ring Q A
  • R 922 and R 923 are bonded together to form ring Q C
  • the adjacent three R 921 , R 922 and R 923
  • the anthracene compound represented by the general formula (TEMP-103) has It is represented by the general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “condensed ring” to be formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one pair of adjacent pairs" forms a “single ring” or a “fused ring", the “single ring” or “fused ring” is a saturated ring, or Unsaturated rings can be formed.
  • 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”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) form a condensed ring by condensing the ring Q A and the ring Q C. If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is monocyclic. When the ring Q A of the general formula (TMEP-104) is a naphthalene ring, the ring Q A is a condensed ring.
  • Unsaturated ring means an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a “saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • Forming a ring means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements.
  • the ring Q A formed by combining R 921 and R 922 shown in the general formula (TEMP-104) has the carbon atom of the anthracene skeleton to which R 921 is bonded and the anthracene skeleton to which R 922 is bonded. It means a ring formed by a skeleton carbon atom 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 bound, the carbon atom of the anthracene skeleton to which R 922 is bound, and four carbon atoms and 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 “optional substituent” described later.
  • the ring formed is a heterocycle.
  • One or more arbitrary elements constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, unless otherwise specified in the present specification. , more preferably 3 or more and 5 or less.
  • “monocyclic ring” and “condensed ring” “monocyclic ring” is preferred, unless otherwise stated in the present specification.
  • the “saturated ring” and the “unsaturated ring” the “unsaturated ring” is preferred, unless otherwise specified in the present specification.
  • “monocyclic” is preferably a benzene ring.
  • the “unsaturated ring” is preferably a benzene ring.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above “monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section “Substituents described herein” above.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case where the above "monocyclic ring” or “condensed ring” has a substituent are the substituents described in the section "Substituents described herein" above. The above is the case where “one or more pairs of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring", and “one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted condensed ring"("combine 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, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an 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
  • the two or more R 901 are the same or different from each other, when two or more R 902 are present, the two or more R 902 are the same or different from each other; when two or more R 903 are present, the two or more R 903 are the same or different from each other, when two or more R 904 are present, the two or more R 904 are the same or different from each other; when two or more R 905 are present, the two or more R 905 are the same or different from each other, when two or more R 906 are present, the two or more R 906 are the same or different from each other; When two or more R 907 are present, the two or more R 907 are the same or different from each other.
  • the substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 50 carbon atoms, It is 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 substituents referred to above as "substituted or unsubstituted” are an alkyl group having 1 to 18 carbon atoms, It is 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 an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5 forming 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 have further substituents. Substituents further possessed by the optional substituents are the same as the above optional substituents.
  • the numerical range represented using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit, and the numerical value BB described after “AA to BB” as the upper limit.
  • invention compounds The compounds of the present invention are described below.
  • the compound of the present invention is represented by the following formula (1).
  • the compounds of the present invention represented by formula (1) and formulas included in formula (1) described later may be simply referred to as "invention compounds”.
  • N * is the central nitrogen atom
  • one of R 1 and R 2 is an unsubstituted methyl group and the other is an unsubstituted phenyl group
  • R 1 and R 2 are not bonded to each other and thus do not form a ring structure
  • R 3 and R 4 are each independently a hydrogen atom, an unsubstituted methyl group, or an unsubstituted phenyl group
  • R3 and R4 are not bonded to each other and thus do not form a ring structure
  • R 11 to R 16 and R 21 to R 27 are hydrogen atoms.
  • R 31 to R 35 are hydrogen atoms.
  • Ar is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.
  • the unsubstituted aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group.
  • a benzoanthryl group a 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, a triphenylenyl group, and the like. mentioned.
  • phenyl group biphenylyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, triphenylenyl group and fluoranthenyl group are preferred.
  • the unsubstituted heterocyclic group is, for example, pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group , pyrimidinyl group, 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, cinnolyl group, phthalazinyl group, quin
  • the invention compound represented by formula (1) is preferably represented by the following formula (1-1) or (1-2).
  • N * , L, R 1 -R 4 , R 11 -R 16 , R 21 -R 27 , and R 31 -R 35 are as defined in formula (1).
  • R 41 to R 46 and R 51 to R 60 are Each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or It is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • one selected from R 41 to R 46 is a single bond that bonds to *a; one selected from R 51 to R 60 is a single bond that bonds to *b; Adjacent two selected from R 41 to R 46 which are not single bonds and adjacent two selected from R 51 to R 60 which are not single bonds are not bonded to each other and thus do not form a ring structure.
  • the invention compound represented by formula (1) is preferably represented by the following formula (1-3) or (1-4).
  • N * , L, R 1 -R 4 , R 11 -R 16 , R 21 -R 27 , and R 31 -R 35 are as defined in formula (1).
  • R 61 to R 68 and R 71 to R 78 are Each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or It is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • X is an oxygen atom, a sulfur atom, or CR a R b ;
  • R a and R b are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and R a and R b are It may be linked through a single bond.
  • one selected from R 61 to R 68 is a single bond that bonds to *c; one selected from R 71 to R 78 is a single bond that bonds to *d; Adjacent two selected from R 61 to R 68 which are not single bonds and adjacent two selected from R 71 to R 78 which are not single bonds are not bonded to each other and thus do not form a ring structure.
  • X is preferably an oxygen atom. In another aspect, X is preferably a sulfur atom.
  • R a and R b may combine with each other to form a substituted or unsubstituted ring. In another aspect of the present invention, R a and R b do not have to combine with each other to form a substituted or unsubstituted ring.
  • the invention compound represented by formula (1) is preferably represented by the following formula (1-5) or (1-6).
  • N * , L, R 1 -R 4 , R 11 -R 16 , R 21 -R 27 , and R 31 -R 35 are as defined in formula (1).
  • R 81 to R 90 and R 91 to R 102 are Each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or It is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
  • one selected from R 81 to R 90 is a single bond that bonds to *e; one selected from R 91 to R 102 is a single bond that bonds to *f; Adjacent two selected from R 81 to R 90 which are not single bonds and adjacent two selected from R 91 to R 102 which are not single bonds are not bonded to each other and thus do not form a ring structure.
  • R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 are each independently a hydrogen atom, substituted or unsubstituted is preferably an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R a , R b , R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 The details of the alkyl group having 1 to 50 carbon atoms are as described above in the section "Substituents described herein".
  • the unsubstituted alkyl groups represented by R a , R b , R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 is preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group or t-butyl group, more preferably methyl group, ethyl group or isopropyl group , or a t-butyl group, more preferably a methyl group or a t-butyl group.
  • the substituted or unsubstituted ring-forming carbon atoms of 3 to R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 represented by Details of the 50 cycloalkyl groups are as described above in the section entitled "Substituents Described herein.”
  • the unsubstituted cycloalkyl groups represented by R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 are preferably cyclo propyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group or 2-norbornyl group, more preferably cyclopropyl group, cyclobutyl group, cycl
  • halogen atoms represented by R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 are described in the specification. , preferably a fluorine atom.
  • R a , R b , R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 The details of the aryl group having 6 to 50 ring carbon atoms are as described in "Substituents described herein".
  • the unsubstituted aryl groups represented by R a , R b , R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 is preferably a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group, more preferably a phenyl group, a biphenylyl group or a naphthyl group, still more preferably a phenyl group.
  • the substituted or unsubstituted ring-forming atoms represented by R 41 to R 46 , R 51 to R 60 , R 61 to R 68 , R 71 to R 78 , R 81 to R 90 and R 91 to R 102 have 5 to Details of the heterocyclic group of 50 are as described in "Substituents described herein".
  • the unsubstituted heterocyclic group is preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, dibenzofuranyl or dibenzothiophenyl.
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms.
  • the unsubstituted arylene group is, for example, a phenylene group, a biphenyldiyl group, a terphenyldiyl group, a naphthylene group, an anthrylene group, a benzoant rylene group, phenanthrylene group, benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzochrysenylene group, triphenylenylene group, fluoranthenylene group, fluorenylene group, or 9, A 9'-spirobifluorenylene group can be mentioned.
  • phenylene group, biphenyldiyl group and terphenyldiyl group are preferred.
  • the unsubstituted divalent heterocyclic group is, for example, pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole , isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isoindole, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran,
  • L is preferably a single bond. In another aspect, L is preferably selected from a phenylene group, a biphenyldiyl group and a naphthylene group.
  • R 41 to R 46 that are not single bonds bonded to *a may all be hydrogen atoms
  • R 51 to R 60 that are not single bonds bonded to *b may all be hydrogen atoms
  • R A-3) R 61 to R 68 that are not single bonds bonded to *c may all be hydrogen atoms
  • R 71 to R 78 that are not single bonds bonded to *d may all be hydrogen atoms
  • R 81 to R 90 that are not single bonds bonded to *e may all be hydrogen atoms
  • A-6) R 91 to R 102 which are not single bonds bonded to *f may all be hydrogen atoms.
  • hydrogen atom as used herein includes protium, deuterium, and tritium atoms. Accordingly, invention compounds may contain naturally occurring deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into the invention compound A by using a deuterated compound as part or all of the raw material compound. Accordingly, in one aspect of the invention, the compounds of the invention contain at least one deuterium atom. That is, the compound of the invention 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.
  • the deuteration rate of the invention compound depends on the deuteration rate of the starting compound used. Even if a raw material with a given deuteration rate is used, it may still contain a certain proportion of natural proton isotopes. Therefore, the aspect of the deuteration rate of the compound of the invention shown below is the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula, and the ratio in consideration of trace isotopes derived from nature. included.
  • the deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.
  • Invention compounds may be mixtures containing deuterated and non-deuterated compounds, mixtures 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, still more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. %.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, and 100 % or less.
  • Invention compounds can be easily produced by those skilled in the art by referring to the following synthesis examples and known synthesis methods.
  • D represents a deuterium atom.
  • the organic EL device material that is one aspect of the present invention contains the invention compound.
  • the content of the invention compound in the organic EL device material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), and 50% by mass or more (including 100% more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).
  • the organic EL device material, which is one aspect of the present invention, is useful for manufacturing organic EL devices.
  • Organic EL Element that is one aspect of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layers comprise a light-emitting layer, and at least one layer of the organic layers comprises an invention compound.
  • the organic layer containing the compound of the invention include a hole-transporting zone provided between the anode and the light-emitting layer (hole-injection layer, hole-transporting layer, electron-blocking layer, exciton-blocking layer, etc.), light-emitting layer .
  • the inventive compound is preferably a material for the hole-transporting zone or light-emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for the hole-transporting zone, even more preferably a hole-injecting layer, a hole-transporting layer, an electron-blocking layer, or an excitation layer. It is used as a material for electron-blocking layers, particularly preferably as a material for hole-injecting layers or hole-transporting layers.
  • the organic EL device may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent/phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. However, it may be of a tandem type having a plurality of light-emitting units, and among these, it is preferably a fluorescent light-emitting device.
  • the term “light-emitting unit” refers to a minimum unit that includes organic layers, at least one layer of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.
  • the light-emitting unit may be of a multilayer type having a plurality of phosphorescent-emitting layers or fluorescent-emitting layers.
  • a space layer may be provided for the purpose of preventing the excitons from diffusing into the fluorescence-emitting layer.
  • a typical layer structure of a simple light-emitting unit is shown below. Layers in brackets are optional.
  • Each of the phosphorescent or fluorescent light-emitting layers may exhibit different emission colors.
  • (hole injection layer/) hole transport layer/first phosphorescent-emitting layer (red emission)/second phosphorescent-emitting layer (green emission)/space layer/fluorescence emission examples thereof include a layer structure such as layer (blue light emitting)/electron transport layer.
  • An electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or space layer.
  • a hole-blocking layer may be appropriately provided between each light-emitting layer and the electron-transporting layer.
  • an electron-blocking layer or a hole-blocking layer By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined in the light-emitting layer, the probability of charge recombination in the light-emitting layer can be increased, and the light-emitting efficiency can be improved.
  • the first light-emitting unit and the second light-emitting unit can be independently selected from the light-emitting units described above, for example.
  • the intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron withdrawal layer, a connection layer, or an intermediate insulating layer, and provides electrons to the first light-emitting unit and holes to the second light-emitting unit.
  • Known material configurations can be used to supply.
  • FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention.
  • the organic EL element 1 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 10 arranged between the anode 3 and the cathode 4 .
  • the light-emitting unit 10 has a light-emitting layer 5 .
  • a hole transport zone 6 (a hole injection layer, a hole transport layer, etc.) is provided between the light emitting layer 5 and the anode 3
  • an electron transport zone 7 an electron injection layer, an electron transport layer, etc. is provided between the light emitting layer 5 and the cathode 4. etc.).
  • an electron blocking layer (not shown) and a hole blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5 and the cathode 4 side of the light emitting layer 5, respectively.
  • electrons and holes can be confined in the light-emitting layer 5, and the exciton generation efficiency in the light-emitting layer 5 can be further increased.
  • FIG. 2 is a schematic diagram showing another configuration of the organic EL element according to one aspect of the present invention.
  • the organic EL element 11 has a substrate 2 , an anode 3 , a cathode 4 , and a light emitting unit 20 arranged between the anode 3 and the cathode 4 .
  • the light-emitting unit 20 has a light-emitting layer 5 .
  • a hole-transporting zone located between the anode 3 and the light-emitting layer 5 is formed from a hole-injecting layer 6a, a first hole-transporting layer 6b and a second hole-transporting layer 6c.
  • the electron-transporting zone located between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.
  • a host combined with a fluorescent dopant is called a fluorescent host
  • a host combined with a phosphorescent dopant is called a phosphorescent host.
  • Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host means a material that contains a phosphorescent dopant and forms a phosphorescent light-emitting layer, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same is true for fluorescent hosts.
  • the substrate is used as a support for the organic EL element.
  • a plate of glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic deposition films can also be used.
  • Anode For the anode formed on the substrate, 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).
  • 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).
  • ITO Indium Tin Oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • indium oxide containing tungsten oxide and zinc oxide Graphene etc.
  • 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 for example, titanium nitride
  • indium oxide-zinc oxide is a target in which 1 to 10 wt% of zinc oxide is added to indium oxide
  • indium oxide containing tungsten oxide and zinc oxide is a target in which 0.5 to 5 wt% of tungsten oxide is added to indium oxide. %, and 0.1 to 1 wt % of zinc oxide
  • it can be formed by a sputtering method.
  • it may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. , alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Groups 1 and 2 of the Periodic Table of the Elements) can be used.
  • Elements belonging to group 1 or 2 of the periodic table which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as europium (Eu) and ytterbium (Yb)
  • Yb ytterbium
  • alloys containing these can also be used.
  • the hole-injection layer is a layer containing a material with high hole-injection properties (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 invention compounds include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. material, tungsten oxide, manganese oxide, or the like can be used.
  • Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • poly(N-vinylcarbazole) (abbreviation: PVK)
  • poly(4-vinyltriphenylamine) (abbreviation: PVTPA)
  • 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).
  • polymer compounds added with acids such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS) are used.
  • PDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).
  • HAT hexaazatriphenylene
  • R 201 to R 206 are each independently a cyano group, —CONH 2 , a carboxyl group, or —COOR 207 (R 207 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms).
  • R 207 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group and the like.
  • Hole-transporting layer is a layer containing a material with high hole-transporting properties (hole-transporting material), and is located between the anode and the light-emitting layer or, if present, with the hole-injecting layer. It is formed between the light emitting layers.
  • Invention compounds may be used in the hole-transporting layer alone or in combination with the following compounds.
  • 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 (anode side) and a second hole transport layer (cathode side).
  • the hole-transporting layer having the single-layer structure is preferably adjacent to the light-emitting layer, and the hole-transporting layer closest to the cathode in the multilayer structure, for example, the two-layer structure is preferably adjacent to the light-emitting layer.
  • an electron A blocking layer or the like may be interposed between the hole-transporting layer and the light-emitting layer in the single-layer structure, or between the hole-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.
  • the invention compound may be contained in either the first hole transport layer or the second hole transport layer, or may be contained in both of them.
  • the invention compound is preferably contained only in the first hole-transport layer, and in another aspect, the invention compound is preferably contained only in the second hole-transport layer.
  • the compound of the invention is preferably contained in the first hole-transporting layer and the second hole-transporting layer.
  • the invention compound contained in one or both of the first hole-transport layer and the second hole-transport layer is preferably a hydrogen compound from the viewpoint of production cost.
  • the light hydrogen compound is an invention compound in which all hydrogen atoms in the invention compound are hydrogen atoms. Therefore, the organic EL device according to one aspect of the present invention is an organic EL device in which one or both of the first hole-transporting layer and the second hole-transporting layer are substantially composed of a light hydrogen compound. is preferably The term "invention compound consisting essentially of a light hydrogen body" means that the content of the light hydrogen body in the total amount of the invention compounds is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%).
  • aromatic amine compounds examples 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)triphenylamine
  • carbazole derivatives examples include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 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: DAnth).
  • 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)
  • a compound other than the above may be used as long as the compound has higher hole-transporting property than electron-transporting property.
  • the light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used.
  • a fluorescent light-emitting material or a phosphorescent light-emitting material can be used as the dopant material.
  • a fluorescent light-emitting material is a compound that emits light from a singlet excited state
  • a phosphorescent light-emitting material is a compound that emits light from a triplet excited state.
  • a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used as a blue fluorescent light-emitting material 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) and the like.
  • An aromatic amine derivative or the like can be used as a greenish fluorescent light-emitting material that can be used in the light-emitting layer.
  • N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA)
  • N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine abbreviation: 2PCABPhA
  • a tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light-emitting material 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', and N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine abbreviation: p-mPhAFD.
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer.
  • An iridium complex or the like is used as a greenish 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 ( Abbreviations: 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(bzq)2(acac)) and the like.
  • Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the 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 (acetylacetonate) (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 light-emitting materials because they emit light from rare-earth metal ions (electronic transitions between different multiplicities).
  • the light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material whose lowest unoccupied molecular orbital level (LUMO level) is higher than that of the dopant material and whose highest occupied molecular orbital level (HOMO level) is lower.
  • LUMO level lowest unoccupied molecular orbital level
  • HOMO level highest occupied molecular orbital level
  • host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; (4) Aromatic amine compounds such as triarylamine derivatives or condensed 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)
  • other metal complexes 2-(4-biphenylyl)-5-(
  • anthracene compound as the host material.
  • the electron-transporting layer is a layer containing a material with high electron-transporting properties (electron-transporting material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron-injecting layer and the light-emitting layer.
  • 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 (anode side) and a second electron transport layer (cathode side).
  • the single-layer electron-transporting layer is preferably adjacent to the light-emitting layer, and the electron-transporting layer closest to the anode in the multilayer structure, for example, the second electron-transporting layer of the two-layer structure. 1
  • the electron-transporting layer is preferably adjacent to the light-emitting layer.
  • a hole-blocking layer as described below is provided between the electron-transporting layer and the light-emitting layer in the single-layer structure, or between the electron-transporting layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. A layer or the like may be interposed.
  • metal complexes such as aluminum complexes, beryllium complexes and zinc complexes
  • heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives
  • Polymer 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), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
  • Alq tris(8-quinolinolato)aluminum
  • heteroaromatic compounds 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), 4,4'-bis(5-methylbenzoxa
  • 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 is a material having an electron mobility of 10 ⁇ 6 cm 2 /Vs or more. Materials other than those described above may be used for the electron transport layer as long as the material has 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)
  • Eu europium
  • Yb ytterbium
  • Rare earth metals such as 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.
  • 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.
  • electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (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 the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the received electrons.
  • the material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above is used. be able to.
  • the electron donor any material can be used as long as it exhibits an electron donating property with respect to the organic compound.
  • 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 preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide.
  • Lewis bases such as magnesium oxide can also be used.
  • An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • Cathode For the 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).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca ), alkaline earth metals such as strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • a vacuum deposition method and a sputtering method can be used.
  • a coating method, an inkjet method, or the like can be used.
  • a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. can do. These conductive materials can be deposited using a sputtering method, an inkjet method, a spin coating method, or the like.
  • 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. A mixture or laminate of these materials may also be used.
  • the space layer is, for example, when a fluorescent-emitting layer and a phosphorescent-emitting layer are laminated, for the purpose of preventing excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or adjusting the carrier balance. It is a layer provided between the fluorescent-emitting layer and the phosphorescent-emitting layer. A space layer can also be provided between a plurality of phosphorescent-emitting layers. Since the space layer is provided between the light-emitting layers, it is preferably made of a material having both electron-transporting properties and hole-transporting properties. Moreover, the triplet energy is preferably 2.6 eV or more in order to prevent diffusion of the triplet energy in the adjacent phosphorescent-emitting layer. Materials used for the space layer include those similar to those used for the above-described hole transport layer.
  • Blocking layers such as electron blocking layers, hole blocking layers, exciton blocking layers, 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-transporting layer
  • the hole-blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron-transporting layer.
  • the exciton-blocking layer has the function of preventing the excitons generated in the light-emitting layer from diffusing to 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.
  • a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like using a solution of a compound forming a layer.
  • MBE method molecular beam vapor deposition 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. 10 nm to 0.2 ⁇ m is more preferable.
  • the organic EL elements can be suitably used for display parts such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as light emitting devices for lighting and vehicle lamps.
  • Preparation Example 1 of Organic EL Device A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was set to 130 nm. The washed glass substrate with the transparent electrode is mounted on a substrate holder of a vacuum deposition apparatus, and the compound HA and the compound 1 are co-deposited on the surface on which the transparent electrode is formed so as to cover the transparent electrode, A hole injection layer having a thickness of 10 nm was formed. The mass ratio of compound 1 to compound HA (compound 1:HA) was 97:3.
  • compound 1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 75 nm.
  • HT2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 15 nm.
  • a BH (host material):BD (dopant material) film having a thickness of 20 nm was formed on the second hole transport layer.
  • This BH:BD film functions as a light-emitting layer.
  • BH compounds BH1 and BH2 (both are host materials) contained in the light-emitting layer has a mass ratio of 1:1, and the concentration of BD is 2% by mass with respect to the entire light-emitting layer.
  • the compound ET1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 3 nm.
  • compound ET2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 30 nm.
  • the mass ratio of compound ET2 and Liq (ET2:Liq) was 67:33.
  • LiF and Yb were co-deposited on the second electron transport layer to form an electron injecting electrode with a thickness of 1 nm.
  • the mass ratio of LiF and Yb (LiF:Yb) was 50:50.
  • EQE External Quantum Efficiency
  • Comparative example 1 An organic EL device was produced in the same manner as in Example 1, except that Comparative Compound 1 was used as the material for the first hole transport layer, and the external quantum efficiency was measured. Table 1 shows the results.
  • Example 2 A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was set to 130 nm. The washed glass substrate with the transparent electrode is mounted on a substrate holder of a vacuum deposition apparatus, and the compound HA and the compound 2 are co-deposited on the surface on which the transparent electrode is formed so as to cover the transparent electrode, A hole injection layer having a thickness of 10 nm was formed. The mass ratio of compound 2 to compound HA (compound 2:HA) was 97:3.
  • compound 2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm.
  • HT3 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
  • a BH3 (host material):BD2 (dopant material) film having a thickness of 25 nm was formed on the second hole transport layer.
  • This BH3:BD2 film functions as a light-emitting layer.
  • the mass ratio (BH3:BD2) of BH3 and BD2 contained in the light-emitting layer was 96:4, and the concentration of BD was 4% by mass with respect to the entire light-emitting layer.
  • the compound ET3 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm.
  • compound ET4 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 20 nm.
  • the mass ratio of compounds ET4 and Liq (ET4:Liq) was 50:50.
  • LiF was vapor-deposited on the second electron-transporting layer to form an electron-injecting electrode with a film thickness of 1 nm.
  • metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.
  • the layer structure of the organic EL device of Example 2 thus obtained is shown below.
  • Example 3 An organic EL device was produced in the same manner as in Example 2 except that Compound 3 was used as the material for the first hole transport layer, and the external quantum efficiency was measured. Table 1 shows the results.
  • Comparative example 2 An organic EL device was produced in the same manner as in Example 2, except that Comparative Compound 2 was used as the material for the first hole transport layer, and the external quantum efficiency was measured. Table 1 shows the results.
  • Example 4 A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was set to 130 nm. After washing, the glass substrate with the transparent electrode is mounted on a substrate holder of a vacuum deposition apparatus, and HT4 and compound HA are co-deposited on the surface on which the transparent electrode is formed so as to cover the transparent electrode, A hole injection layer having a thickness of 10 nm was formed. The mass ratio of HT4 to compound HA (HT4:HA) was 97:3.
  • HT4 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 35 nm.
  • Compound 1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 40 nm.
  • HT2 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 7.5 nm.
  • a BH1 (host material):BH2 (host material):BD3 (dopant material) film having a thickness of 20 nm was formed on the third hole transport layer. This BH1:BH2:BD3 film functions as a light-emitting layer.
  • BH1:BH2:BD3 contained in the light-emitting layer has a mass ratio of 60:40:2.
  • the compound ET5 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 3 nm.
  • compound ET2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 30 nm.
  • the mass ratio of compound ET2 and Liq (ET2:Liq) was 67:33.
  • LiF and Yb were co-deposited on the second electron transport layer to form an electron injecting electrode with a thickness of 1 nm.
  • the mass ratio of LiF and Yb (LiF:Yb) was 50:50.
  • Example 5 An organic EL device was produced in the same manner as in Example 4 except that Compound 4 was used as the material for the second hole transport layer, and the external quantum efficiency was measured. Table 1 shows the results.
  • Comparative example 3 An organic EL device was produced in the same manner as in Example 4, except that Comparative Compound 3 was used as the material for the second hole transport layer, and the external quantum efficiency was measured. Table 1 shows the results.
  • the organic EL device containing the invention compound (compound 1) is more effective than the organic EL device containing the comparative compound 1, and the organic EL device containing the invention compounds (compound 2 and compound 3). is superior to the organic EL device containing the comparative compound 2, and the organic EL device containing the invention compounds (compound 1, compound 4) is superior to the organic EL device containing the comparative compound 3 in terms of external quantum efficiency. I know there is.
  • N-(9,9-diphenyl-9H- Compound 2 was synthesized in a similar manner using fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine.
  • N-(9,9-diphenyl-9H- Compound 3 was synthesized in a similar manner using fluoren-2-yl)-2-dibenzothiophenamine.
  • N-(9,9-dimethyl-9H- Compound 4 was synthesized in a similar manner using fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine.
  • Reference Signs List 1 11 organic EL element 2 substrate 3 anode 4 cathode 5 light emitting layer 6 hole transport zone (hole transport layer) 6a hole injection layer 6b first hole transport layer 6c second hole transport layer 7 electron transport zone (electron transport layer) 7a first electron transport layer 7b second electron transport layer 10, 20 light emitting unit

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Abstract

L'invention concerne : un composé qui améliore les performances d'un élément électroluminescent organique ; un élément électroluminescent organique ayant une performance d'élément améliorée ; et un dispositif électronique comprenant un tel élément électroluminescent organique, le composé étant représenté par la formule (1) (dans la formule (1), les définitions de N*, Ar, L, R1 à R2, R3 à R4, R11 à R16, R21 à R27 et R31 à R36 sont tels que définis dans la description). L'invention concerne également : un élément électroluminescent organique qui comprend le composé et un dispositif électronique qui comprend l'élément électroluminescent organique.
PCT/JP2022/015770 2021-03-31 2022-03-30 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2022210821A1 (fr)

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KR1020237032191A KR20230162933A (ko) 2021-03-31 2022-03-30 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기

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JP2018505133A (ja) * 2015-10-26 2018-02-22 エルジー・ケム・リミテッド アミン化合物およびこれを含む有機発光素子
KR20180040079A (ko) * 2016-10-11 2018-04-19 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기 발광 소자
KR20180043726A (ko) * 2016-10-20 2018-04-30 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기 발광 소자
WO2020225071A1 (fr) * 2019-05-03 2020-11-12 Merck Patent Gmbh Dispositif électronique
JP2021506822A (ja) * 2017-12-15 2021-02-22 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスに使用するための置換芳香族アミン

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KR101730275B1 (ko) 2012-08-31 2017-04-25 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 이것을 이용한 유기 전기발광 소자
KR102111149B1 (ko) 2016-11-11 2020-05-14 주식회사 엘지화학 유기 발광 소자
KR102192367B1 (ko) 2018-01-11 2020-12-17 주식회사 엘지화학 유기 발광 소자

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Publication number Priority date Publication date Assignee Title
JP2018505133A (ja) * 2015-10-26 2018-02-22 エルジー・ケム・リミテッド アミン化合物およびこれを含む有機発光素子
KR20180040079A (ko) * 2016-10-11 2018-04-19 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기 발광 소자
KR20180043726A (ko) * 2016-10-20 2018-04-30 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기 발광 소자
JP2021506822A (ja) * 2017-12-15 2021-02-22 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスに使用するための置換芳香族アミン
WO2020225071A1 (fr) * 2019-05-03 2020-11-12 Merck Patent Gmbh Dispositif électronique

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