WO2022181076A1 - Composition, et élément luminescent mettant en œuvre celle-ci - Google Patents

Composition, et élément luminescent mettant en œuvre celle-ci Download PDF

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WO2022181076A1
WO2022181076A1 PCT/JP2022/000484 JP2022000484W WO2022181076A1 WO 2022181076 A1 WO2022181076 A1 WO 2022181076A1 JP 2022000484 W JP2022000484 W JP 2022000484W WO 2022181076 A1 WO2022181076 A1 WO 2022181076A1
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group
ring
formula
represented
compound
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元章 臼井
龍二 松本
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住友化学株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/357—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

Definitions

  • the present invention relates to a composition and a light-emitting device using the same.
  • a light-emitting element such as an organic electroluminescence element can be suitably used for display and lighting applications.
  • a light-emitting material used in a light-emitting layer of a light-emitting element for example, a composition containing a polymer compound containing a structural unit represented by the following formula and a phosphorescent compound is known (Patent Documents 1 and 2).
  • an object of the present invention is to provide a composition useful for manufacturing a light-emitting device having excellent luminance lifetime.
  • a composition comprising a compound represented by formula (C) and a polymer compound containing a structural unit represented by formula (Z).
  • Ring R 1C and ring R 2C each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings are substituted by an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. and these groups may further have a substituent.
  • substituents on the ring R 1C and multiple substituents on the ring R 2C they may be bonded together to form a ring together with the atoms to which they are attached.
  • Y a represents a group represented by —C(R Xa ) 2 — or a group represented by formula (C′).
  • R Xa represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups have substituents; may be When there are multiple such substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. Multiple R Xa 's may be the same or different.
  • Ring R 3C and ring R 4C each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings are substituted with an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. and these groups may further have a substituent. When there are multiple substituents on the ring R 3C and multiple substituents on the ring R 4C , they may be bonded together to form a ring together with the atoms to which they are attached.
  • R Xa has the same meaning as described above.
  • E11C , E12C , E13C , E14C , E21C , E22C , E23C , E24C , E31C , E32C , E33C , E34C , E41C , E42C , E43C and E44C are each independently represents a nitrogen atom or a carbon atom.
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C , R 24C , R 31C , R 32C , R 33C , R 34C , R 41C , R 42C , R 43C and R 44C are each Each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. When E 11C is a nitrogen atom, R 11C is absent.
  • E 12C is a nitrogen atom
  • R 12C is absent.
  • E 13C is a nitrogen atom
  • R 13C is absent.
  • E 14C is a nitrogen atom
  • R 14C is absent.
  • E 21C is a nitrogen atom
  • R 21C is absent.
  • E 22C is a nitrogen atom
  • R 22C is absent.
  • E 23C is a nitrogen atom
  • R 23C is absent.
  • E 24C is a nitrogen atom
  • R 24C is absent.
  • E 31C is a nitrogen atom
  • R 31C is absent.
  • E 32C is a nitrogen atom
  • R 32C is absent.
  • E 33C is a nitrogen atom
  • R 33C is absent.
  • E 34C is a nitrogen atom, R 34C is absent.
  • E 41C is a nitrogen atom
  • R 41C is absent.
  • E 42C is a nitrogen atom
  • R 42C is absent.
  • E 43C is a nitrogen atom
  • R 43C is absent.
  • E 44C is a nitrogen atom, R 44C is absent.
  • R 11C and R 12C , R 12C and R 13C , R 13C and R 14C , R 14C and R 34C , R 34C and R 33C , R 33C and R 32C , R 32C and R 31C , R 31C and R 41C , R 41C and R 42C , R 42C and R 43C , R 43C and R 44C , R 44C and R 24C , R 24C and R 23C , R 23C and R 22C , R 22C and R 21C , and R 21C and R 11C are each They may also be joined to form a ring with the carbon atoms to which they are attached.
  • At least one of the R 11C , the R 12C , the R 13C , the R 14C , the R 21C , the R 22C , the R 23C and the R 24C is an optionally substituted aryl group or The composition according to [5] or [6], which is an optionally substituted monovalent heterocyclic group.
  • the composition according to [8], wherein the phosphorescent compound is a metal complex represented by formula (M). [In the formula, M 1 represents an iridium atom or a platinum atom.
  • nM1 represents an integer of 1 or more
  • nM2 represents an integer of 0 or more
  • n M1 +n M2 is 3 when M 1 is an iridium atom
  • n M1 +n M2 is 2 when M 1 is a platinum atom.
  • E 1 and E 2 each independently represent a carbon atom or a nitrogen atom. However, at least one of E 1 and E 2 is a carbon atom.
  • Ring RM1 represents an aromatic heterocycle, and this ring may have a substituent. When there are multiple such substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. When multiple rings R M1 are present, they may be the same or different.
  • Ring RM2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When there are multiple such substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. When multiple rings R M2 are present, they may be the same or different.
  • the substituent that ring R M1 may have and the substituent that ring R M2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • -A D1 ---A D2 - represents an anionic bidentate ligand.
  • AD1 and AD2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to M1, and these atoms may be atoms constituting a ring. When there are a plurality of -A D1 ---A D2 -, they may be the same or different.
  • the composition according to . [11] A light-emitting device containing the composition according to any one of [1] to [9].
  • composition useful for manufacturing a light-emitting device with excellent luminance life it is possible to provide a composition useful for manufacturing a light-emitting device with excellent luminance life. Further, according to the present invention, a light-emitting device containing this composition can be provided.
  • Room temperature means 25°C.
  • Me is a methyl group
  • Et is an ethyl group
  • Bu is a butyl group
  • i-Pr is an isopropyl group
  • t-Bu is a tert-butyl group.
  • a hydrogen atom may be a deuterium atom or a protium atom.
  • solid lines representing bonds with the central metal mean covalent bonds or coordinate bonds.
  • a "low-molecular-weight compound” means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
  • a “polymer compound” means a polymer having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 or more (for example, 1 ⁇ 10 3 to 1 ⁇ 10 8 ).
  • a “structural unit” means a unit that exists at least one in a polymer compound. Two or more structural units contained in a polymer compound are generally called “repeating units".
  • the polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms.
  • the terminal group of the polymer compound is preferably a stable group, because if the polymerization active group remains as it is, the light-emitting properties may deteriorate when the polymer compound is used for the production of a light-emitting device.
  • the terminal group of the polymer compound is preferably a group conjugated to the main chain, for example, an aryl group or a monovalent heterocyclic group that binds to the main chain of the polymer compound via a carbon-carbon bond. is mentioned.
  • the "alkyl group” may be either linear or branched.
  • the number of carbon atoms in the linear alkyl group is generally 1-50, preferably 1-30, more preferably 1-20, not including the number of carbon atoms in the substituents.
  • the number of carbon atoms in the branched alkyl group is generally 3-50, preferably 3-30, more preferably 4-20, not including the number of carbon atoms in the substituent.
  • the alkyl group may have a substituent.
  • alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group and heptyl. octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl and dodecyl groups.
  • alkyl groups are groups in which some or all of the hydrogen atoms in these groups are substituted with substituents (e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.) (e.g., trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3-(4-methylphenyl)propyl group, 3-(3,5-di -hexylphenyl)propyl group, 6-ethyloxyhexyl group).
  • substituents e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.
  • substituents e.g., cycloalkyl groups, alkoxy groups, cyclo
  • the number of carbon atoms in the "cycloalkyl group” is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, not including the number of carbon atoms in substituents.
  • a cycloalkyl group may have a substituent.
  • Cycloalkyl groups include, for example, cyclohexyl groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
  • alkenyl group may be either linear or branched.
  • the straight-chain alkenyl group usually has 2 to 30 carbon atoms, preferably 3 to 20 carbon atoms, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the branched alkenyl group is usually 3-30, preferably 4-20, not including the number of carbon atoms in the substituents.
  • the alkenyl group may have a substituent.
  • alkenyl groups include vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl groups and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.
  • the number of carbon atoms in the "cycloalkenyl group” is usually 3-30, preferably 4-20, not including the number of carbon atoms in the substituents.
  • a cycloalkenyl group may have a substituent.
  • Cycloalkenyl groups include, for example, 5-cyclohexenyl groups and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • alkynyl group may be either linear or branched.
  • the straight-chain alkynyl group usually has 2 to 20 carbon atoms, preferably 3 to 20 carbon atoms, not including substituent carbon atoms.
  • the number of carbon atoms in the branched alkynyl group is generally 4-30, preferably 4-20, not including the carbon atoms of the substituents.
  • the alkynyl group may have a substituent.
  • alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • the number of carbon atoms in the "cycloalkynyl group” is usually 4-30, preferably 4-20, not including the carbon atoms of the substituents.
  • a cycloalkynyl group may have a substituent.
  • Cycloalkynyl groups include, for example, 5-cyclohexynyl groups and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • alkoxy group may be either linear or branched.
  • the straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the branched alkoxy group is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.
  • the alkoxy group may have a substituent.
  • Alkoxy groups include, for example, methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and some or all of the hydrogen atoms in these groups are substituted groups (e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy group, aryl group, fluorine atom, etc.).
  • substituted groups e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy group, aryl group, fluorine atom, etc.
  • the number of carbon atoms in the "cycloalkoxy group” is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.
  • a cycloalkoxy group may have a substituent.
  • Cycloalkoxy groups include, for example, cyclohexyloxy groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
  • the number of carbon atoms in the "aryloxy group” is usually 6-60, preferably 6-48, not including the number of carbon atoms in the substituents.
  • the aryloxy group may have a substituent.
  • aryloxy groups include phenoxy, 1-naphthyloxy, 2-naphthyloxy, 1-anthracenyloxy, 9-anthracenyloxy, 1-pyrenyloxy groups, and these groups.
  • Examples thereof include groups in which some or all of hydrogen atoms are substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms, etc.).
  • “Aromatic hydrocarbon group” means a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon.
  • a group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon is also referred to as an "aryl group”.
  • a group obtained by removing two hydrogen atoms directly bonded to carbon atoms forming a ring from an aromatic hydrocarbon is also referred to as an "arylene group”.
  • the number of carbon atoms in the aromatic hydrocarbon group is generally 6-60, preferably 6-40, more preferably 6-20, not including the number of carbon atoms in the substituents.
  • aromatic hydrocarbon group includes, for example, monocyclic aromatic hydrocarbons (e.g., benzene), or polycyclic aromatic hydrocarbons (e.g., naphthalene, indene, naphthoquinone, indenone and tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthoquinone and fluorenone; benzoanthracene, benzophenanthrene, benzofluorene, pyrene and tetracyclic aromatic hydrocarbons such as fluoranthene; pentacyclic aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, perylene and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene aromatic hydrocarbon
  • Aryl groups include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and some or all of the hydrogen atoms in these groups are substituents
  • a group substituted with a substituted group eg, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, etc.
  • arylene groups include phenylene, naphthalenediyl, anthracenediyl, phenanthenediyl, dihydrophenanthenediyl, naphthacenediyl, fluorenediyl, pyrenediyl, perylenediyl, chrysenediyl groups, and Groups in which some or all of the hydrogen atoms are substituted with substituents are included.
  • the arylene group includes groups in which multiple of these groups are bonded.
  • Arylene groups are preferably groups represented by formulas (A-1) to (A-20).
  • R and Ra each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
  • Plural R and R a may be the same or different, and R a may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • a “heterocyclic group” means a group obtained by removing one or more hydrogen atoms directly bonded to atoms (carbon atoms or heteroatoms) constituting a ring from a heterocyclic compound.
  • an "aromatic heterocyclic group” which is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound, is preferred.
  • a group obtained by removing p hydrogen atoms (p represents an integer of 1 or more) directly bonded to atoms constituting a ring from a heterocyclic compound is also referred to as a "p-valent heterocyclic group".
  • a group obtained by removing p hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound is also referred to as a "p-valent aromatic heterocyclic group".
  • aromatic heterocyclic compounds include oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole Compounds in which the heterocycle itself exhibits aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, benzopyran, etc., even if the heterocycle itself does not exhibit aromaticity, the heterocyclic ring is condensed with an aromatic ring.
  • heterocyclic groups include, for example, monocyclic heterocyclic compounds such as furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, tetrazole, pyridine, diazabenzene and triazine, or Polycyclic heterocyclic compounds (e.g.
  • Heterocyclic groups include groups in which multiple of these groups are bonded.
  • a heterocyclic group may have a substituent (eg, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).
  • the monovalent heterocyclic group includes, for example, thienyl, pyrrolyl, furyl, pyridyl, piperidinyl, quinolinyl, isoquinolinyl, pyrimidinyl, triazinyl, and part of the hydrogen atoms in these groups, or Examples include groups that are entirely substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms) and the like.
  • substituents eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms
  • the number of carbon atoms in the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15, not including the number of carbon atoms in the substituents.
  • divalent heterocyclic groups include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, A divalent group obtained by removing two hydrogen atoms among hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting a ring from diazole or triazole.
  • Divalent heterocyclic groups include groups in which multiple of these groups are bonded.
  • the divalent heterocyclic group is preferably a group represented by formulas (AA-1) to (AA-34).
  • R and Ra represent the same meanings as described above.
  • Halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the "amino group” may have a substituent, preferably a substituted amino group (that is, a secondary amino group or a tertiary amino group, more preferably a tertiary amino group).
  • Preferred substituents for the amino group are alkyl groups, cycloalkyl groups, aryl groups and monovalent heterocyclic groups, and these groups may have substituents.
  • the amino group has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which each is bonded.
  • Substituted amino groups include, for example, a dialkylamino group, a dicycloalkylamino group, a diarylamino group, and those in which some or all of the hydrogen atoms are substituted (e.g., an alkyl group, a cycloalkyl group, an alkoxy group , a cycloalkoxy group, an aryl group, a fluorine atom, etc.).
  • substituted amino groups include dimethylamino group, diethylamino group, diphenylamino group, bis(methylphenyl)amino group, bis(3,5-di-tert-butylphenyl)amino group, and hydrogen in these groups.
  • Examples thereof include groups in which some or all of the atoms are substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.).
  • substituents eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.
  • crosslinking group is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, or the like, and is preferably a group represented by the formula ( B-1) to a group represented by any one of formulas (B-17). These groups may have a substituent.
  • the "substituent” includes, for example, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, Examples include alkenyl groups, cycloalkenyl groups, alkynyl groups, and cycloalkynyl groups.
  • a substituent may be a bridging group.
  • when multiple substituents are present they may be the same or different.
  • they may bond with each other to form a ring together with the atoms to which they are bonded, but preferably do not form a ring.
  • the molecular weight of the compound represented by formula (C) is preferably 2 ⁇ 10 2 to 1 ⁇ 10 4 , more preferably 3 ⁇ 10 2 to 5 ⁇ 10 3 , still more preferably 4 ⁇ 10 2 to 1 ⁇ 10 4 . 10 2 to 2.5 ⁇ 10 3 , particularly preferably 4 ⁇ 10 2 to 1.5 ⁇ 10 3 .
  • the number of carbon atoms in the aromatic hydrocarbon ring is usually 6 to 60, preferably 6 to 30, more preferably 6. ⁇ 18.
  • aromatic hydrocarbon rings in ring R 1C and ring R 2C include benzene ring, naphthalene ring, anthracene ring, indene ring, fluorene ring, spirobifluorene ring, phenanthrene ring, dihydrophenanthrene ring, pyrene ring and chrysene ring.
  • triphenylene ring preferably benzene ring, naphthalene ring, anthracene ring, fluorene ring, spirobifluorene ring, phenanthrene ring or dihydrophenanthrene ring, more preferably benzene ring, naphthalene ring, fluorene ring or spirobifluorene ring It is a ring, more preferably a benzene ring, and these rings may have a substituent.
  • the number of carbon atoms in the aromatic heterocyclic ring is usually 2 to 60, preferably 3 to 30, more preferably 4-15.
  • aromatic heterocyclic rings in ring R 1C and ring R 2C include pyrrole ring, diazole ring, triazole ring, furan ring, thiophene ring, oxadiazole ring, thiadiazole ring, pyridine ring, diazabenzene ring, triazine ring, aza naphthalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilole ring, dibenzophosphole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, phenoxazine ring, phenothiazine
  • At least one of ring R 1C and ring R 2C is preferably an aromatic hydrocarbon ring, more preferably both are aromatic hydrocarbon rings.
  • the substituent that the ring R 1C and the ring R 2C may have is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group or a cycloalkyl group or an aryl group, and these groups may further have a substituent.
  • the aryl group includes, for example, a benzene ring, a naphthalene ring, anthracene ring, an indene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, and a dihydrophenanthrene.
  • the number of carbon atoms in the monovalent heterocyclic group is usually 2 to 60, not including the number of carbon atoms in the substituent, preferably , 3-30, more preferably 3-15.
  • the monovalent heterocyclic group includes, for example, pyrrole ring, diazole ring, triazole ring, furan ring, thiophene ring, oxadiazole ring, thiadiazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triaza phenanthrene ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilole ring, dibenzophosphole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, phenox
  • the substituent which the ring R 1C and the ring R 2C may further have is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. , more preferably an alkyl group, a cycloalkyl group or an aryl group, still more preferably an aryl group or a cycloalkyl group, and these groups may further have a substituent.
  • Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituent which the substituent which the ring R 1C and the ring R 2C may further have are respectively the ring R 1C and the ring The same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituents that R 2C may have.
  • R Xa is preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, since the light-emitting element of this embodiment has a superior luminance lifetime. and more preferably an aryl group, and these groups may further have a substituent.
  • the aryl group in R Xa is preferably represented by formula (DA), formula (D-B), or formula (D-C) described below, since the light-emitting device of the present embodiment has a superior luminance lifetime. and more preferably a group represented by formula (DA) or formula (DC).
  • the compound represented by formula (C) has no substituents in ring R 1C and ring R 2C , or ring R 1C and ring R 2C At least one preferably has an aryl group or a monovalent heterocyclic group as a substituent.
  • the total number of aryl groups and monovalent heterocyclic groups possessed by ring R 1C and ring R 2C is The number is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.
  • Ya is preferably a group represented by the formula (C′) because the light-emitting device of this embodiment has a superior luminance lifetime.
  • At least one of the ring R3C and the ring R4C is preferably an aromatic hydrocarbon ring, more preferably both are aromatic hydrocarbon rings. preferable.
  • Examples and preferred ranges of the aromatic hydrocarbon ring and aromatic heterocyclic ring represented by ring R 3C and ring R 4C are respectively the aromatic hydrocarbon ring and aromatic heterocyclic ring represented by ring R 1C and ring R 2C . It is the same as the examples and preferred ranges of the ring.
  • Examples and preferred ranges of substituents that ring R 3C and ring R 4C may have are the same as examples and preferred ranges of substituents that ring R 1C and ring R 2C may have.
  • Examples and preferred ranges of the substituents that the ring R 3C and the ring R 4C may further have are the substituents that the ring R 1C and the ring R 2C may have It is the same as the examples and preferred range of the substituent which may be further contained.
  • the total number of aryl groups and monovalent heterocyclic groups possessed by ring R 3C and ring R 4C is The number is preferably 1 to 5, more preferably 1 to 3, still more preferably 1 or 2.
  • At least one of ring R 1C , ring R 2C , ring R 3C and ring R 4C preferably has an aryl group as a substituent.
  • the aryl group in the substituents that the ring R 1C , ring R 2C , ring R 3C and ring R 4C may have is preferably an aryl group of the formula (D- A), a group represented by formula (DB) or formula (DC), more preferably a group represented by formula (DA) or formula (DC).
  • G DA is an aromatic hydrocarbon group
  • m DA1 is an integer of 1 or more, it is directly bonded to ring R 1C , ring R 2C , ring R 3C or ring R 4C
  • Ar DA1 is an arylene group.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 or greater.
  • GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Multiple GDAs may be the same or different.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent good.
  • TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple TDAs may be the same or different.
  • G DA is an aromatic hydrocarbon group
  • m DA1 is an integer of 1 or more, it is directly bonded to ring R 1C , ring R 2C , ring R 3C or ring R 4C
  • Ar DA1 is an arylene group.
  • mDA1 represents an integer of 0 or more.
  • Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple Ar DA1 , they may be the same or different.
  • TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. provided that when m DA1 is 0, T DA is an aryl group, and when m DA1 is an integer of 1 or more, Ar DA1 directly bonded to ring R 1C , ring R 2C , ring R 3C or ring R 4C is an arylene group.
  • m DA1 to m DA7 are usually integers of 10 or less, preferably 5 or less, more preferably 0 or 1.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
  • G DA is preferably a group represented by formulas (GDA-11) to (GDA-15), more preferably a group represented by formulas (GDA-11) to (GDA-14) More preferably, it is a group represented by formula (GDA-11) or formula (GDA-14), and particularly preferably a group represented by formula (GDA-11).
  • * represents a bond with Ar DA1 in formula (DA), Ar DA1 in formula (DB), Ar DA2 in formula (DB), or Ar DA3 in formula (DB).
  • ** represents a bond with Ar DA2 in formula ( DA), Ar DA2 in formula (D-B), Ar DA4 in formula (D-B), or Ar DA6 in formula (D-B).
  • *** represents a bond with Ar DA3 in formula ( DA), Ar DA3 in formula (D-B), Ar DA5 in formula (D-B), or Ar DA7 in formula (D-B). show.
  • RDA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are multiple RDAs , they may be the same or different. ]
  • RDA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have substituents.
  • Ar DA1 to Ar DA7 are preferably a phenylene group, a fluorenediyl group or a carbazoldiyl group, more preferably formulas (A-1) to (A-3), formula (A-8), formula ( A-9), a group represented by formula (AA-10), formula (AA-11), formula (AA-33) or formula (AA-34), more preferably formula (ArDA-1) ⁇ A group represented by formula (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to formula (ArDA-3), particularly preferably a group represented by formula (ArDA-1) or formula ( ArDA-2), and these groups may have a substituent.
  • RDA has the same meaning as above.
  • RDB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple RDBs , they may be the same or different. ]
  • R DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group;
  • the group may have a substituent.
  • TDA is preferably a group represented by formulas (TDA-1) to (TDA-3), more preferably a group represented by formula (TDA-1).
  • R DA and R DB have the same meanings as described above. ]
  • the group represented by formula (DA) is preferably a group represented by formula (D-A1).
  • R p1 and R p2 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When multiple R p1 and R p2 are present, they may be the same or different. np1 represents an integer of 0-5, and np2 represents an integer of 0-3. Multiple np1 may be the same or different. ]
  • the group represented by formula (D-B) is preferably a group represented by formula (D-B1).
  • R p1 and R p2 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When multiple R p1 and R p2 are present, they may be the same or different.
  • np1 represents an integer of 0-5, and np2 represents an integer of 0-3.
  • a plurality of np1 and np2 may be the same or different.
  • the group represented by formula (D-C) is preferably a group represented by formula (D-C1) to formula (D-C4), more preferably a group represented by formula (D-C1) to formula (D- C3), more preferably a group represented by formula (D-C1) or (D-C2), particularly preferably a group represented by formula (D-C1) .
  • R p4 and R p5 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are multiple R p4 and R p5 , they may be the same or different. np4 represents an integer of 0-5, and np5 represents an integer of 0-4. ]
  • np1 is preferably 0 or 1, more preferably 1.
  • np2 is preferably 0 or 1, more preferably 0.
  • np4 is preferably 0-2.
  • np5 is preferably 0-2, more preferably 0.
  • R p1 , R p2 , R p4 and R p5 are preferably alkyl groups or cycloalkyl groups.
  • Examples of the group represented by formula (DA) include formulas (DA-1) to (DA-4), formula (DA-7), and formula (DA-8 ) or a group represented by formula (DA-10).
  • R D is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy represents a group.
  • a plurality of RDs may be the same or different.
  • Examples of the group represented by formula (DB) include groups represented by formula (DB-1) or formula (DB-4).
  • Examples of the group represented by formula (D-C) include groups represented by formulas (D-C-1) to (D-C-13).
  • R D is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group, more preferably a tert-butyl group.
  • the compound represented by the formula (C) is the compound represented by the formula (C'-2) or the compound represented by the formula (C-2), since the light-emitting element of the present embodiment has a superior luminance lifetime. is preferred, and a compound represented by formula (C'-2) is more preferred.
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C are preferably a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, a hydrogen atom, an aryl It is more preferably a group or a monovalent heterocyclic group, more preferably a hydrogen atom or an aryl group, and these groups may further have a substituent.
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C are all hydrogen atoms, or R 11C , R 12C , R At least one of 13C , R 14C , R 21C , R 22C , R 23C and R 24C is preferably an aryl group or a monovalent heterocyclic group (more preferably an aryl group).
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C is an aryl group or A monovalent heterocyclic group is preferred, and at least one is more preferably an aryl group.
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C when at least one of R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C has an aryl group or a monovalent heterocyclic group, At least one of R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C is preferably an aryl group or a monovalent heterocyclic group, and R 11C , R 12C , At least one of R 13C , R 21C , R 22C and R 23C is more preferably an aryl group or a monovalent heterocyclic group, and R 13C or R 23C is an aryl group or a monovalent heterocyclic group is more preferred, and it is particularly preferred that R 13C and R 23C are an aryl group or a
  • R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C is an aryl group or a monovalent heterocyclic group;
  • at least one of R 11C , R 12C , R 13C , R 14C , R 21C , R 22C , R 23C and R 24C is preferably an aryl group or a monovalent heterocyclic group
  • R 11C At least one of R 12C , R 21C and R 22C is more preferably an aryl group or a monovalent heterocyclic group, more preferably R 21C or R 22C is an aryl group or a monovalent heterocyclic group. preferable.
  • R 31C , R 32C , R 33C , R 34C , R 41C , R 42C , R 43C and R 44C are preferably a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, a hydrogen atom, an aryl It is more preferably a group or a monovalent heterocyclic group, more preferably a hydrogen atom or an aryl group, and these groups may further have a substituent.
  • R 31C , R 32C , R 33C , R 34C , R 41C , R 42C , R 43C and R 44C has an aryl group or a monovalent heterocyclic group
  • R 31C , R 32C , R 33C , R 34C , R 41C , R 42C , R 43C and R 44C at least one is preferably an aryl group or a monovalent heterocyclic group, and among R 31C , R 32C , R 41C and R 42C
  • At least one is more preferably an aryl group or a monovalent heterocyclic group, more preferably R 31C or R 32C is an aryl group or a monovalent heterocyclic group, R 32C is an aryl group or a monovalent A heterocyclic group is particularly preferred.
  • R 11C and R 12C , R 12C and R 13C , R 13C and R 14C , R 14C and R 34C , R 34C and R 33C , R 33C and R 32C , R 32C and R 31C , R 31C and R 41C , R 41C and R 42C , R 42C and R 43C , R 43C and R 44C , R 44C and R 24C , R 24C and R 23C , R 23C and R 22C , R 22C and R 21C , and R 21C and R 11C are each They may combine to form a ring with the carbon atoms to which they are bonded, but preferably do not form a ring.
  • Examples of compounds represented by formula (C) include compounds represented by formulas (C-101) to (C-147).
  • X represents a group represented by —O— or —S—, and when there are multiple Xs, they may be the same or different.
  • X is preferably a group represented by -S-.
  • the number of carbon atoms constituting the ring is usually 1 to 60, preferably 2 to 30, more preferably 3 to 15, more preferably 3 to 5.
  • diazanaphthalene ring triazana a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a phthalene ring
  • azaanthracene ring diazaanthracene ring
  • triazaanthracene ring azaphenanthrene ring
  • diazaphenanthrene ring or triazaphenanthrene ring is particularly preferably a group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting the ring from a pyridine ring, a diazabenzene ring or a triazine ring, and particularly preferably a triazine ring constituting the ring It is a group excluding two hydrogen atoms directly bonded to a carbon atom, and these groups may have a substituent.
  • Substituents that Ar Z may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent A cyclic group, a substituted amino group or a halogen atom is preferred, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group, An aryl group or a monovalent heterocyclic group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, and an aryl group is particularly preferred, and these groups may further have a substituent.
  • the substituents that Ar 2 Z may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and a monovalent heterocyclic ring. or a substituted amino group, more preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an aryl group or a monovalent heterocyclic group, particularly preferably an aryl group, and these groups are further substituted You may have a group.
  • Ar 2 Z When there are a plurality of substituents that Ar 2 Z may have, it is preferred that they are not bonded together to form a ring together with the atoms to which they are bonded.
  • Substituents which Ar Z may further have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent heterocyclic ring.
  • an alkyl group a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent is more preferred, an alkyl group or an aryl group is particularly preferred, and an alkyl group is particularly preferred, and these groups may further have a substituent.
  • Ar Z is preferably a group represented by formulas (ArZ-1) to (ArZ-12), more preferably a group represented by formula (ArZ- 1) to a group represented by the formula (ArZ-9), more preferably a group represented by the formula (ArZ-1) to the formula (ArZ-5), particularly preferably a group represented by the formula (ArZ- 1), a group represented by formula (ArZ-2) or formula (ArZ-4), particularly preferably a group represented by formula (ArZ-4).
  • R 1Z represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a bond; , these groups may have a substituent.
  • Multiple R 1Z may be the same or different. However, two of the plurality of R 1Z are bonds.
  • R 1Z is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent a heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, still more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or It is an aryl group, particularly preferably a hydrogen atom or an aryl group, and these groups may have a substituent.
  • the light-emitting element of the present embodiment has superior luminance lifetime .
  • a heterocyclic group or a substituted amino group more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably a hydrogen atom, an aryl group or a monovalent heterocyclic group and particularly preferably a hydrogen atom or an aryl group, and these groups may have a substituent.
  • Examples and preferred ranges of the substituents that R 1Z may have are the same as the examples and preferred ranges of the substituents that the substituents that Ar 2 Z may further have.
  • the arylene groups in Ar Z1 and Ar Z2 are preferably represented by formulas (A-1) to (A-10), formula (A-19) or formula (A -20), more preferably groups represented by formulas (A-1) to (A-7), formula (A-9) or formula (A-19), and further Preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), particularly preferably formula (A -1) or a group represented by formula (A-2).
  • Examples and preferred ranges of the divalent heterocyclic group for Ar Z1 and Ar Z2 are the same as the examples and preferred range of the divalent heterocyclic group represented by Ar Y1 described later.
  • Examples and preferred ranges of the substituents that Ar Z1 and Ar Z2 may have are the same as the examples and preferred ranges of the substituents that Ar Z may have above.
  • Examples and preferred ranges of substituents that Ar Z1 and Ar Z2 may further have are the same as the examples and preferred ranges of the preferred substituents.
  • Ar Z1 and Ar Z2 are preferably optionally substituted arylene groups.
  • n Z1 and n Z2 are preferably integers of 0 or more and 3 or less, more preferably 1 or 2, still more preferably 1.
  • the structural unit represented by the formula (Z) is preferably the structural unit represented by the formula (ZA), since the light-emitting device of the present embodiment has a more excellent luminance lifetime.
  • R 2Z and R 3Z each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom; , these groups may have a substituent.
  • R 2Z is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a substituted amino group, since it facilitates synthesis of a polymer compound.
  • R 2Z is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since the light-emitting device of the present embodiment has a superior luminance lifetime. , more preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an aryl group or a monovalent heterocyclic group, particularly preferably an aryl group, these groups further It may have a substituent.
  • R 3Z is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, these groups having a substituent; may
  • Structural units represented by formula (ZA) are preferably structural units represented by formulas (Z-A1) to (Z-A4), since the light-emitting device of the present embodiment has superior luminance lifetime. , more preferably a structural unit represented by formula (Z-A1) or (Z-A3), still more preferably a structural unit represented by formula (Z-A1).
  • Examples of the structural unit represented by the formula (Z) include structural units represented by the formulas (Z-1) to (Z-46), preferably the structural units represented by the formulas (Z-1) to (Z -28) or structural units represented by formulas (Z-40) to (Z-46).
  • Z 3 represents a group represented by -O- or a group represented by -S-. A plurality of Z3 may be the same or different.
  • the content of the structural unit represented by formula (Z) is such that the content of the structural unit contained in the polymer compound containing the structural unit represented by formula (Z) is higher than the luminance lifetime of the light-emitting device of the present embodiment. It is preferably 0.1 to 50 mol %, more preferably 1 to 30 mol %, still more preferably 5 to 15 mol % of the total amount.
  • the polymer compound containing the structural unit represented by the formula (Z) has a more excellent luminance lifetime of the light-emitting device of the present embodiment
  • the structural unit represented by the formula (Y) (formula (Z) It is different from the structural unit represented by.) is preferably included.
  • the polymer compound containing the structural unit represented by the formula (Z) has excellent hole-transporting properties, it is preferable that the polymer compound further contains the structural unit represented by the formula (X) described below.
  • the polymer compound containing the structural unit represented by the formula (Z) has excellent hole-transport properties and the luminance lifetime of the light-emitting device of the present embodiment is more excellent, it is further represented by the formula (X) It preferably contains a structural unit and a structural unit represented by formula (Y).
  • Ar Y represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups may have a substituent.
  • the arylene group represented by Ar Y1 is more preferably represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula A group represented by (A-20), more preferably formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19) ), and these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar Y1 is more preferably represented by formulas (AA-10) to (AA-15), formulas (AA-18) to formulas (AA-21), formulas (AA- 33) or a group represented by formula (AA-34), more preferably represented by formula (AA-10), formula (AA-12), formula (AA-14) or formula (AA-33) These groups may have a substituent.
  • a more preferred range of the arylene group and the divalent heterocyclic group in the divalent group represented by Ar Y1 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded more preferably The range is the same as the more preferred range and the more preferred range of the arylene group and divalent heterocyclic group represented by Ar Y1 described above, respectively.
  • the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded” includes, for example, groups represented by the following formulas, which have a substituent You may have
  • the substituent that the group represented by Ar Y1 may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.
  • Examples of structural units represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-6). is preferably a structural unit represented by formulas (Y-1) to (Y-3), and from the viewpoint of hole transport properties, preferably formulas (Y-4) to (Y-6) is a structural unit represented by
  • R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent .
  • a plurality of R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.
  • the structural unit represented by formula (Y-1) is preferably a structural unit represented by formula (Y-1').
  • R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of RY11 may be the same or different.
  • R Y11 is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.
  • RY1 has the same meaning as above.
  • RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of RY2 may be the same or different, and the RY2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent.
  • the combination of two R Y2 in the group represented by —C(R Y2 ) 2 — is preferably both an alkyl group or a cycloalkyl group, both an aryl group, and both a monovalent a cyclic group, or one of which is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group; may have a substituent.
  • R Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R Y2 forms a ring, the group represented by -C(R Y2 ) 2 - is preferably a group represented by formulas (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), these groups having a substituent You may have
  • the structural unit represented by formula (Y-2) is preferably a structural unit represented by formula (Y-2').
  • the structural unit represented by formula (Y-3) is preferably a structural unit represented by formula (Y-3').
  • R Y1 has the same meaning as above.
  • RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent.
  • Examples of structural units represented by formula (Y) include structural units composed of arylene groups represented by formulas (Y-101) to (Y-121), formulas (Y-201) to (Y- 206), a structural unit in which at least one arylene group represented by the formula (Y-301) and at least one divalent heterocyclic group are directly bonded 2 Structural units consisting of valent groups can be mentioned.
  • the content of the structural unit represented by the formula (Y) in which Ar 2 Y1 is an arylene group is represented by the formula (Z) because the luminance lifetime of the light-emitting device of this embodiment is superior. It is preferably 0.5 to 99 mol %, more preferably 50 to 95 mol %, relative to the total amount of structural units contained in the polymer compound containing structural units.
  • the content of the structural unit that is the group of is more than the total amount of the structural units contained in the polymer compound containing the structural unit represented by formula (Z). preferably 0.5 to 30 mol %, more preferably 3 to 20 mol %.
  • R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple R X2 and R X3 are present, they may be the same or different. ]
  • a X1 is preferably 2 or less, more preferably 1, because the light-emitting element of this embodiment has an excellent luminance lifetime.
  • aX2 is preferably 2 or less, more preferably 0, because the light-emitting element of this embodiment has an excellent luminance lifetime.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent; good too.
  • Arylene groups represented by Ar X1 and Ar X3 are more preferably groups represented by formula (A-1) or formula (A-9), more preferably represented by formula (A-1) groups, and these groups may have a substituent.
  • the arylene groups represented by Ar X2 and Ar X4 are more preferably those of formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11) ) or a group represented by formula (A-19), and these groups may have a substituent.
  • the more preferable range of the bivalent heterocyclic groups represented by Ar 1 X2 and Ar 2 X4 is the same as the more preferable range of the bivalent heterocyclic groups represented by Ar 1 X1 and Ar 2 X3 .
  • At least one arylene group represented by Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded
  • at least Examples thereof include the same divalent groups in which one arylene group and at least one divalent heterocyclic group are directly bonded.
  • Ar X2 and Ar X4 are preferably arylene groups optionally having substituents.
  • the substituents that the groups represented by Ar X1 to Ar X4 and R X1 to R X3 may have are preferably alkyl groups, cycloalkyl groups or aryl groups, and these groups further have substituents. You may have
  • the structural unit represented by formula (X) is preferably a structural unit represented by formula (X-1) to formula (X-7), more preferably a structural unit represented by formula (X-1) to formula (X- 6), more preferably structural units represented by formulas (X-3) to (X-6).
  • R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano represents a group, and these groups may have a substituent.
  • Multiple R X4 may be the same or different.
  • a plurality of R 1 X5 may be the same or different, and adjacent R 1 X5 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • the total amount of the structural units contained in the polymer compound containing the structural unit represented by the formula (Z) is It is preferably 0.1 to 50 mol %, more preferably 1 to 40 mol %, still more preferably 5 to 30 mol %.
  • Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-11), preferably formulas (X1-3) to (X1 -10) is a structural unit.
  • Polymer compounds containing structural units represented by formula (Z) include, for example, polymer compounds (P-1) to (P-8).
  • the “other” structural unit means a structural unit other than the structural unit represented by the formula (Z), the structural unit represented by the formula (Y), and the structural unit represented by the formula (X). do.
  • a polymer compound containing a structural unit represented by formula (Z) may be a block copolymer, a random copolymer, an alternating copolymer, or a graft copolymer. However, it is preferably a copolymer.
  • the polystyrene equivalent number average molecular weight of the polymer compound containing the structural unit represented by formula (Z) is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 to 5 ⁇ 10 5 . and more preferably 3 ⁇ 10 4 to 1.5 ⁇ 10 5 .
  • the method of charging the monomers includes a method of charging the entire amount of the monomers into the reaction system at once, a method of charging a part of the monomers and reacting them, and then charging the remaining monomers all at once. Examples thereof include a method of continuously or dividedly charging, a method of continuously or dividingly charging a monomer, and the like.
  • transition metal catalysts examples include palladium catalysts and nickel catalysts.
  • the post-treatment of the polymerization reaction is performed by a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., is performed singly or in combination.
  • a method of removing water-soluble impurities by liquid separation adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., is performed singly or in combination.
  • the purity of the polymer compound containing the structural unit represented by formula (Z) is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.
  • a "phosphorescent compound” usually means a compound that exhibits phosphorescence at room temperature, preferably a metal complex that exhibits luminescence from a triplet excited state at room temperature.
  • a metal complex that exhibits emission from this triplet excited state has a central metal atom and ligands.
  • the central metal atom includes, for example, an atom with an atomic number of 40 or more, a metal atom that has a spin-orbital interaction in the complex and can cause intersystem crossing between the singlet state and the triplet state.
  • the metal atom include ruthenium atom, rhodium atom, palladium atom, iridium atom and platinum atom, and the iridium atom or platinum atom is preferable because the light-emitting element of this embodiment has excellent luminance lifetime.
  • the ligand is, for example, a neutral or anionic monodentate ligand that forms at least one bond selected from the group consisting of coordinate bonds and covalent bonds with the central metal atom, or Neutral or anionic multidentate ligands can be mentioned. Bonds between the central metal atom and the ligands include, for example, metal-nitrogen bonds, metal-carbon bonds, metal-oxygen bonds, metal-phosphorus bonds, metal-sulfur bonds and metal-halogen bonds.
  • a polydentate ligand generally means a ligand having two or more and six dentate or less.
  • the phosphorescent compound is preferably a metal complex represented by Formula (M).
  • M1 is preferably an iridium atom because the light - emitting device of this embodiment has a superior luminance lifetime.
  • nM1 is preferably 2 or 3, more preferably 3.
  • nM1 is preferably 2 when M1 is a platinum atom.
  • E 1 and E 2 are preferably carbon atoms.
  • Ring R M1 is preferably a 5- or 6-membered aromatic heterocyclic ring having 1 or more and 4 or less nitrogen atoms as ring-constituting atoms, such as pyridine ring, diazabenzene ring, triazine ring, quinoline ring and isoquinoline ring.
  • Ring R M2 is preferably a 5- or 6-membered aromatic hydrocarbon ring or a 5- or 6-membered aromatic heterocyclic ring, such as a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyridine ring, More preferably a diazabenzene ring, triazine ring, pyrrole ring, furan ring or thiophene ring, more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyridine ring or a diazabenzene ring, a benzene ring or a pyridine ring or a pyrimidine ring, particularly preferably a benzene ring, and these rings may have a substituent.
  • substituents that the ring R M1 and the ring R M2 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group-substituted amino group, or A halogen atom is preferred, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
  • a cyclic group is more preferred, an alkyl group or an aryl group is particularly preferred, and an aryl group is particularly preferred, and these groups may further have a substituent.
  • the substituents which the ring R M1 and the ring R M2 may further have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent hetero
  • a cyclic group or a substituted amino group is preferable, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group is more preferable, an alkyl group or a cycloalkyl group is more preferable, and these groups may further have a substituent. .
  • the substituent that ring R M1 may have and the substituent that ring R M2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded. It is preferred not to form
  • the aryl group, monovalent heterocyclic group, or substituted amino group in the substituents that the ring R M1 and the ring R M2 may have is preferable because the light-emitting device of the present embodiment has a superior luminance lifetime.
  • (DA') a group represented by formula (DB') or formula (DC'), more preferably a group represented by formula (DA').
  • m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
  • GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
  • Ar DA1 , Ar DA2 and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
  • TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple TDAs may be the same or different.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 or greater.
  • GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. Multiple GDAs may be the same or different.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent good.
  • TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple TDAs may be the same or different.
  • mDA1 represents an integer of 0 or more.
  • Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple Ar DA1 , they may be the same or different.
  • TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are usually 10 or less. is an integer of, preferably an integer of 5 or less, more preferably 0 or 1.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
  • G DA is preferably a group represented by formula (GDA-11) to formula (GDA-15). is, more preferably a group represented by formulas (GDA-11) to (GDA-14), more preferably a group represented by formula (GDA-11) or formula (GDA-14) , and particularly preferably a group represented by the formula (GDA-11).
  • RDA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have substituents.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 are preferably A phenylene group, a fluorenediyl group or a carbazoldiyl group, more preferably formulas (A-1) to (A-3), formulas (A-8), formulas (A-9) and formulas (AA-10) ), a group represented by the formula (AA-11), the formula (AA-33) or the formula (AA-34), more preferably represented by the formulas (ArDA-1) to (ArDA-5) groups, particularly preferably groups represented by formulas (ArDA-1) to (ArDA-3), particularly preferably groups represented by formula (ArDA-1) or formula (ArDA-2) and these groups may have a substituent.
  • RDA has the same meaning as above.
  • RDB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple RDBs , they may be the same or different. ]
  • R DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group;
  • the group may have a substituent.
  • TDA is preferably a group represented by formulas (TDA-1) to (TDA-3). and more preferably a group represented by formula (TDA-1).
  • R DA and R DB have the same meanings as described above. ]
  • the group represented by formula (DA′) is preferably a group represented by formula (D-A1) to formula (D-A3), more preferably represented by formula (D-A1) is the base.
  • R p1 , R p2 and R p3 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When multiple R p1 and R p2 are present, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. Multiple np1 may be the same or different. ]
  • the group represented by formula (D-B') is preferably a group represented by formula (D-B1) to formula (D-B3), more preferably represented by formula (D-B1) is the base.
  • R p1 , R p2 and R p3 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When multiple R p1 and R p2 are present, they may be the same or different.
  • np1 represents an integer of 0 to 5
  • np2 represents an integer of 0 to 3
  • np3 represents 0 or 1.
  • a plurality of np1 and np2 may be the same or different.
  • the group represented by formula (D-C') is preferably a group represented by formula (D-C1) to formula (D-C4), more preferably a group represented by formula (D-C1) to formula (D -C3), more preferably a group represented by formula (D-C1) or formula (D-C2), particularly preferably a group represented by formula (D-C1) be.
  • R p4 and R p5 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are multiple R p4 and R p5 , they may be the same or different. np4 represents an integer of 0-5, and np5 represents an integer of 0-4. ]
  • np1 is preferably 0 or 1, more preferably 1.
  • np2 is preferably 0 or 1, more preferably 0.
  • np3 is preferably zero.
  • np4 is preferably 0-2.
  • np5 is preferably 0-2, more preferably 0.
  • R p1 , R p2 , R p3 , R p4 and R p5 are preferably alkyl groups or cycloalkyl groups.
  • Examples of the group represented by formula (DA') include groups represented by formulas (DA-1) to (DA-12).
  • R D is a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy represents a group.
  • a plurality of RDs may be the same or different.
  • Examples of the group represented by formula (D-B') include groups represented by formulas (D-B-1) to (D-B-4).
  • Examples of the group represented by formula (D-C') include groups represented by formulas (D-C-1) to (D-C-13).
  • R D is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group, more preferably a tert-butyl group.
  • At least one ring selected from the group consisting of ring R M1 and ring R M2 preferably has a substituent because it has excellent solubility.
  • the substituent of at least one ring selected from the group consisting of ring R 1 M1 and ring R 2 M2 is preferably an alkyl group, a cycloalkyl group, or formulas (DA') to (D-C' ), more preferably an alkyl group, or a group represented by formulas (DA′) to (DC′), more preferably a group represented by formula (DA ') to a group represented by the formula (D-C'), particularly preferably a group represented by the formula (DA'), and these groups may have a substituent. .
  • anionic bidentate ligand represented by -A D1 ---A D2 - examples include ligands represented by the following formulae.
  • metal complex represented by formula (M) metal complexes represented by formulas Ir-1 to Ir-5 are preferable, and metal complexes represented by formulas Ir-1 to Ir-3 are more preferable.
  • a metal complex represented by formula Ir-1 or formula Ir-2 is more preferred, and a metal complex represented by formula Ir-1 is particularly preferred.
  • R D1 to R D8 , R D11 to R D26 , and R D31 to R D37 are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an alkoxy group, since the light-emitting element of the present embodiment has a superior luminance lifetime.
  • a cycloalkoxy group an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or a group represented by formulas (DA') to (D-C'), particularly preferably a hydrogen atom or a formula ( DA') to the groups represented by the formulas (DC'), and these groups may have a substituent.
  • R D22 and R D33 are preferably alkyl groups, cycloalkyl groups, or represented by formulas (DA') to (D-C'), since the light-emitting element of this embodiment has a superior luminance lifetime.
  • R D1 to R D8 , R D11 to R D26 and R D31 to R D37 may have are the substituents that ring R M1 and ring R M2 may have It is the same as the example and preferred range of the substituent that the group may further have.
  • R D36 and R D37 are not bonded together to form a ring together with the atoms to which
  • the metal complexes represented by Formula Ir-1 are preferably metal complexes represented by Formulas Ir-11 to Ir-13.
  • the metal complex represented by Formula Ir-2 is preferably a metal complex represented by Formula Ir-21.
  • Metal complexes represented by Formula Ir-3 are preferably metal complexes represented by Formulas Ir-31 to Ir-33.
  • Metal complexes represented by Formula Ir-4 are preferably metal complexes represented by Formulas Ir-41 to Ir-43.
  • Metal complexes represented by Formula Ir-5 are preferably metal complexes represented by Formulas Ir-51 to Ir-53.
  • n D2 represents 1 or 2; D represents a group represented by formulas (DA') to (D-C').
  • a plurality of D may be the same or different.
  • RDC represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple RDCs may be the same or different.
  • RDD represents an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple RDDs may be the same or different.
  • Examples of phosphorescent compounds include metal complexes shown below.
  • Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp. , American Dye Source, and others. Also, Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985), Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984), International Publication No. 2011/024761, International Publication No. 2002/44189, and JP-A-2006-188673.
  • the content of the phosphorescent compound is a polymer compound containing a structural unit represented by formula (Z) and a compound represented by formula (C).
  • the total of and the phosphorescent compound is 100 parts by mass, it is usually 0.01 to 99 parts by mass, preferably 0.1 to 90 parts by mass, more preferably 1 to 75 parts by mass. , more preferably 5 to 50 parts by mass, particularly preferably 20 to 40 parts by mass.
  • the content of the compound represented by formula (C) is a polymer compound containing a structural unit represented by formula (Z), the compound represented by formula (C), and phosphorescence emission. (If the composition does not contain a phosphorescent compound, the sum of the polymer compound containing the structural unit represented by formula (Z) and the compound represented by formula (C)) is 100
  • the sum of the polymer compound containing the structural unit represented by formula (Z) and the compound represented by formula (C) is 100
  • it is usually 0.01 to 99 parts by mass, preferably 0.1 to 90 parts by mass, more preferably 0.5 to 70 parts by mass, and still more preferably 1 to 50 parts by mass. Parts by mass, particularly preferably 3 to 30 parts by mass.
  • each of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound may be used alone. You may use 2 or more types together.
  • the lowest excited triplet state (T 1 ) possessed by the polymer compound containing the structural unit represented by formula (Z) and T 1 possessed by the compound represented by formula (C) determine the luminance of the light-emitting device of this embodiment.
  • An energy level equivalent to or higher than T 1 of the phosphorescent compound is preferable because the lifetime is excellent.
  • the phosphorescent compound can be dissolved. is preferably soluble in a solvent capable of
  • the composition of the present embodiment may further contain at least one selected from the group consisting of hole transport materials, hole injection materials, electron transport materials, electron injection materials, light emitting materials, and antioxidants. good.
  • the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material are polymer compounds containing structural units represented by the above formula (Z), and are represented by the above formula (C). It is different from the compound and said phosphorescent compound.
  • the viscosity of the ink may be adjusted depending on the type of printing method, but when applying to a printing method such as an inkjet printing method in which a solution passes through an ejection device, it is necessary to prevent clogging and flight deflection during ejection. , preferably 1 to 20 mPa ⁇ s at 25°C.
  • the solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink.
  • solvents include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents
  • polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol
  • alcohol solvents such as isopropyl alcohol and cyclohexanol
  • sulfoxide solvents such as dimethyl sulfoxide
  • N-methyl-2-pyrrolidone N , and N-dimethylformamide.
  • the blending amount of the solvent is 100 parts by mass in total of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound. It is usually 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass.
  • the solvent may be used singly or in combination of two or more.
  • the hole-transporting material is classified into a low-molecular-weight compound and a high-molecular-weight compound, preferably a high-molecular-weight compound, and more preferably a high-molecular-weight compound having a cross-linking group.
  • Polymer compounds include, for example, polyvinylcarbazole and its derivatives; polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain.
  • a polymer compound may be a compound having an electron-accepting site attached thereto. Examples of electron-accepting moieties include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, preferably fullerene.
  • the amount of the hole-transporting material is the sum of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound.
  • the amount of the hole-transporting material is the sum of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound.
  • the hole transport materials may be used singly or in combination of two or more.
  • Electron transport materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.
  • the electron transport material may have a cross-linking group.
  • low-molecular-weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and , diphenoquinone, and derivatives thereof.
  • polymer compounds examples include polyphenylene, polyfluorene, and derivatives thereof.
  • the polymeric compounds may be doped with metals.
  • the electron-transporting materials may be used singly or in combination of two or more.
  • Hole-injecting materials and electron-injecting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds, respectively.
  • the hole-injecting material and the electron-injecting material may have cross-linking groups.
  • low-molecular compounds examples include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • metal phthalocyanines such as copper phthalocyanine
  • carbon such as carbon
  • metal oxides such as molybdenum and tungsten
  • metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • Polymer compounds include, for example, polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, polyquinoxaline, and derivatives thereof; polymers containing an aromatic amine structure in the main chain or side chain; of conductive polymers.
  • the compounding amounts of the hole-injecting material and the electron-injecting material are respectively the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and phosphorescence.
  • the total amount with the luminescent compound is 100 parts by mass, it is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, more preferably 5 to 150 parts by mass.
  • each of the hole injection material and the electron injection material may be used alone or in combination of two or more.
  • the electrical conductivity of the conductive polymer is preferably between 1 ⁇ 10 ⁇ 5 S/cm and 1 ⁇ 10 3 S/cm.
  • the conductive polymer can be doped with an appropriate amount of ions in order to set the electrical conductivity of the conductive polymer within this range.
  • the types of ions to be doped are anions for hole-injection materials and cations for electron-injection materials.
  • anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions.
  • cations include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
  • the ions to be doped may be one kind or two or more kinds.
  • Light-emitting materials (different from phosphorescent compounds) are classified into low-molecular-weight compounds and high-molecular-weight compounds.
  • the luminescent material may have a cross-linking group.
  • low-molecular compounds examples include naphthalene and its derivatives, anthracene and its derivatives, and perylene and its derivatives.
  • Polymer compounds include, for example, phenylene group, naphthalenediyl group, fluorenediyl group, phenanthrenediyl group, dihydrophenanthrenediyl group, group represented by formula (X), carbazoldiyl group, phenoxazinediyl group, phenothiazinediyl , anthracenediyl group, pyrenediyl group, and the like.
  • the content of the light-emitting material is the sum of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound.
  • the content of the light-emitting material is the sum of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound.
  • it is usually 0.1 to 1000 parts by mass, preferably 0.1 to 400 parts by mass.
  • the luminescent materials may be used singly or in combination of two or more.
  • the antioxidant may be a compound that is soluble in the same solvent as the polymer compound containing the structural unit represented by formula (Z) and does not inhibit light emission and charge transport.
  • examples include phenolic antioxidants, Phosphorus-based antioxidants can be mentioned.
  • the blending amount of the antioxidant is the sum of the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (C), and the phosphorescent compound.
  • 100 parts by mass it is usually 0.001 to 10 parts by mass.
  • the antioxidants may be used singly or in combination of two or more.
  • the membrane contains the composition of the present embodiments.
  • the film is suitable as a light-emitting layer in a light-emitting device.
  • the film is formed by using ink, for example, spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing. , flexographic printing, offset printing, inkjet printing, capillary coating, and nozzle coating.
  • the thickness of the film is usually 1 nm to 10 ⁇ m.
  • the light-emitting device of this embodiment is a light-emitting device containing the composition of this embodiment.
  • the structure of the light-emitting device of this embodiment includes, for example, electrodes composed of an anode and a cathode, and a layer containing the composition of this embodiment provided between the electrodes.
  • the layer containing the composition of the present embodiment is usually one or more layers selected from a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer and an electron injection layer, preferably a light emitting layer. . These layers each contain a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. These layers are formed by dissolving the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material in the above-described solvent, preparing an ink, and using the ink in the same manner as in the above-described film formation. method.
  • a light-emitting element has a light-emitting layer between an anode and a cathode.
  • the light emitting device of the present embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer.
  • Materials for the hole-transporting layer, electron-transporting layer, light-emitting layer, hole-injecting layer, and electron-injecting layer include, for example, the composition of the present embodiment, and the hole-transporting material, electron-transporting material, and light-emitting material described above. materials, hole-injection materials and electron-injection materials.
  • the materials for the hole-transporting layer, the electron-transporting layer, and the light-emitting layer are selected from the solvents used in forming the layers adjacent to the hole-transporting layer, the electron-transporting layer, and the light-emitting layer, respectively, in the manufacture of the light-emitting device.
  • the material has cross-linking groups to avoid dissolving the material in the solvent. After forming each layer using a material having a cross-linking group, the layer can be made insoluble by cross-linking the cross-linking group.
  • each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer
  • a low molecular compound for example, vacuum from powder A vapor deposition method
  • a method of forming a film from a solution or a molten state, and a method of forming a film from a solution or a molten state can be used when using a polymer compound.
  • the order, number and thickness of the layers to be laminated are adjusted in consideration of the external quantum efficiency and luminance lifetime.
  • the substrate in the light emitting device may be a substrate on which an electrode can be formed and which does not change chemically when the organic layer is formed.
  • the electrodes furthest from the substrate be transparent or translucent.
  • Examples of materials for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium-tin-oxide (ITO), indium-zinc-oxide, etc. conductive compounds of; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, copper.
  • conductive metal oxides and translucent metals preferably indium oxide, zinc oxide, tin oxide; indium-tin-oxide (ITO), indium-zinc-oxide, etc.
  • cathode materials include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of them; alloys of one or more species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, tin; and graphite and graphite intercalation compounds.
  • alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.
  • Each of the anode and the cathode may have a laminated structure of two or more layers.
  • the light-emitting device of this embodiment is useful for, for example, displays and lighting.
  • the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by any of the following size exclusion chromatography (SEC) using tetrahydrofuran as a moving bed. obtained by The SEC measurement conditions are as follows.
  • a polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 ⁇ L was injected into SEC. The mobile phase was run at a flow rate of 0.6 mL/min.
  • TSKguard column Super AW-H, TSKgel Super AWM-H, and TSKgel Super AW3000 were connected in series and used.
  • a UV-VIS detector manufactured by Tosoh, trade name: UV-8320GPC was used as a detector.
  • NMR was measured by the following method. 5 to 10 mg of a measurement sample is added to about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethylsulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol. Alternatively, it was dissolved in methylene dichloride and measured using an NMR device (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).
  • HPLC high performance liquid chromatography
  • the column used was Kaseisorb LC ODS 2000 (manufactured by Tokyo Kasei Kogyo) or an ODS column with equivalent performance.
  • a photodiode array detector manufactured by Shimadzu Corporation, trade name: SPD-M20A was used as the detector.
  • the polymer compound IP1 has a structural unit derived from the monomer PM1, a structural unit derived from the monomer PM2, and a structural unit derived from the monomer PM3. It is a copolymer composed of units and structural units derived from the monomer PM4 in a molar ratio of 50:30:12.5:7.5.
  • HM-1c (13.3 g) was obtained as a white solid.
  • the HPLC area percentage value of compound HM-1c was 99.9% or more.
  • the results of 1 H-NMR measurement of compound HM-1c were as follows.
  • Compound HM-2 was synthesized according to the method described in WO2012/048820.
  • Compound HM-3 was synthesized according to the method described in WO2013/045410.
  • Compound HM-4 was synthesized according to the method described in WO2013/045408.
  • Compound HM-5 was purchased from Luminescence Technology.
  • Compound HM-6 was synthesized according to the method described in WO2005/049546.
  • HM-7b (53.9 g) was obtained as a white solid.
  • the HPLC area percentage value of compound HM-7b was greater than 99.8%.
  • Example D1> (Formation of anode and hole injection layer) An anode was formed by forming an ITO film with a thickness of 45 nm on a glass substrate by a sputtering method. A film of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed on the anode by spin coating to a thickness of 65 nm, and heated on a hot plate at 240° C. for 15 minutes in an air atmosphere. A hole injection layer was thus formed. (Formation of hole transport layer) A polymer compound IP1 was dissolved in xylene at a concentration of 0.60% by mass.
  • a film having a thickness of 90 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150° C. for 10 minutes in a nitrogen gas atmosphere. .
  • a vapor deposition machine After reducing the pressure of the substrate on which the light-emitting layer is formed to 1.0 ⁇ 10 ⁇ 4 Pa or less in a vapor deposition machine, sodium fluoride of about 4 nm is deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer. About 80 nm of aluminum was evaporated. After vapor deposition, the light-emitting device D1 was produced by sealing with a glass substrate.
  • Example D2 Fabrication of Light Emitting Device D2
  • Example D3 Fabrication of light-emitting device D3
  • Example D4 Fabrication of Light-Emitting Device D4
  • Example D5 Fabrication of Light-Emitting Device D5
  • Example D7 Fabrication of Light-Emitting Device D7
  • composition useful for manufacturing a light-emitting device with excellent luminance life and a light-emitting device containing this composition.

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  • Medicinal Chemistry (AREA)
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  • Electroluminescent Light Sources (AREA)
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Abstract

L'invention fournit une composition qui est avantageuse pour la fabrication d'un élément luminescent d'une excellente durée de vie en termes de luminance.　Cette composition comprend un composé représenté par la formule (C), et un composé de masse moléculaire élevée contenant une unité constitutive représentée par la formule (Z). [Dans la formule, un cylce (Ｒ１Ｃ) et un cycle (Ｒ２Ｃ) représentent chacun indépendamment un cycle hydrocarbure aromatique ou un hétérocycle aromatique, Ｙａ représente un groupe représenté par －Ｃ（ＲＸａ）２－ ou un groupe représenté par la formule (C').] [Dans la formule, un cycle Ｒ３Ｃ et un cycle Ｒ４Ｃ représentent chacun indépendamment un cycle hydrocarbure aromatique ou un hétérocycle aromatique.] [Dans la formule, ＡｒＺ représente un groupe hétérocyclique divalent possédant un groupe représenté par －Ｎ＝ à l'intérieur d'un cycle. ＡｒＺ１ et ＡｒＺ２ représentent chacun indépendamment un groupe arylène ou un groupe hétérocyclique divalent.ｎＺ１ et ｎＺ２ représentent chacun indépendamment un entier supérieur ou égal à 0 et inférieur ou égal à 5.]
PCT/JP2022/000484 2021-02-25 2022-01-11 Composition, et élément luminescent mettant en œuvre celle-ci WO2022181076A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012036388A (ja) * 2010-07-16 2012-02-23 Sumitomo Chemical Co Ltd 高分子化合物及び該高分子化合物を含有する組成物
JP2012131993A (ja) * 2010-11-30 2012-07-12 Sumitomo Chemical Co Ltd 高分子化合物及びその製造方法、並びに発光素子
JP2014001349A (ja) * 2012-06-20 2014-01-09 Sumitomo Chemical Co Ltd 組成物、高分子化合物およびそれらを用いた発光素子
JP2018078286A (ja) * 2016-10-28 2018-05-17 住友化学株式会社 組成物及びそれを用いた発光素子
JP2018188515A (ja) * 2017-04-28 2018-11-29 住友化学株式会社 組成物及び発光素子
JP2019527257A (ja) * 2016-06-28 2019-09-26 メルク パテント ゲーエムベーハー 有機機能材料の調合物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012036388A (ja) * 2010-07-16 2012-02-23 Sumitomo Chemical Co Ltd 高分子化合物及び該高分子化合物を含有する組成物
JP2012131993A (ja) * 2010-11-30 2012-07-12 Sumitomo Chemical Co Ltd 高分子化合物及びその製造方法、並びに発光素子
JP2014001349A (ja) * 2012-06-20 2014-01-09 Sumitomo Chemical Co Ltd 組成物、高分子化合物およびそれらを用いた発光素子
JP2019527257A (ja) * 2016-06-28 2019-09-26 メルク パテント ゲーエムベーハー 有機機能材料の調合物
JP2018078286A (ja) * 2016-10-28 2018-05-17 住友化学株式会社 組成物及びそれを用いた発光素子
JP2018188515A (ja) * 2017-04-28 2018-11-29 住友化学株式会社 組成物及び発光素子

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