WO2023176304A1 - Composé polymère et élément électroluminescent l'utilisant - Google Patents

Composé polymère et élément électroluminescent l'utilisant Download PDF

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WO2023176304A1
WO2023176304A1 PCT/JP2023/005677 JP2023005677W WO2023176304A1 WO 2023176304 A1 WO2023176304 A1 WO 2023176304A1 JP 2023005677 W JP2023005677 W JP 2023005677W WO 2023176304 A1 WO2023176304 A1 WO 2023176304A1
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group
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智裕 道堯
元章 臼井
美桜 白鳥
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/02—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor bodies
    • H01L33/26—Materials of the light emitting region
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present invention relates to a polymer compound and a light emitting device using the same.
  • Patent Document 1 describes a polymer compound containing a structural unit represented by the following formula.
  • an object of the present invention is to provide a polymer compound useful for manufacturing a light emitting element with excellent brightness life.
  • a represents an integer from 0 to 6.
  • R 1 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 a substituent. You can leave it there.
  • substituents When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • R 1 's When a plurality of R 1 's exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • R 0 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, or a halogen atom, and these groups are substituents. It may have. When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • a plurality of R 0 's may be the same or different. However, at least one of R 0 represents a group represented by formula (DA), formula (DB), or formula (DC). ]
  • DA formula
  • DB formula
  • DC formula
  • m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
  • GDA represents an aromatic hydrocarbon group, and the group may have a substituent. When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • Ar DA1 , Ar DA2 and Ar DA3 each independently represent an arylene group, and the group may have a substituent.
  • TDA represents an aryl group, and the group may have a substituent.
  • a plurality of substituents may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • a plurality of TDAs may be the same or different.
  • m DB1 , m DB2 , m DB3 , m DB4 , m DB5 , m DB6 and m DB7 each independently represent an integer of 0 or more.
  • G DB1 , G DB2 and G DB3 each independently represent an aromatic hydrocarbon group, and the group may have a substituent. When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • Ar DB1 , Ar DB2 , Ar DB3 , Ar DB4 , Ar DB5 , Ar DB6 and Ar DB7 each independently represent an arylene group, and the group may have a substituent.
  • substituents When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
  • TDB represents an aryl group, and the group may have a substituent.
  • a plurality of substituents When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded. A plurality of TDBs may be the same or different.
  • mDC1 represents an integer of 1 or more.
  • Ar DC1 represents an arylene group, and the group may have a substituent.
  • a plurality of Ar DC1s may be the same or different.
  • TDC represents an aryl group, and the group may have a substituent.
  • R A 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, or a halogen atom, and these groups are substituents. It may have.
  • R 1 and R 2 have the same meanings as above.
  • R 3 and R 4 each independently represent the same meaning as R 1 and R 2 and may be the same or different from R 1 and R 2 .
  • R 1 , R 2 , R 3 and R 4 may be the same or different.
  • [4] The polymer compound according to [3], wherein n is 2.
  • a polymer compound useful for manufacturing a light emitting element with excellent brightness life. Further, according to the present invention, a composition and a light emitting device containing the polymer compound can be provided.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • i-Pr represents an isopropyl group
  • t-Bu represents a tert-butyl group.
  • the hydrogen atom may be a deuterium atom or a light hydrogen atom.
  • the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.
  • polymer compound refers to a polymer having a molecular weight distribution and a number average molecular weight of 1 ⁇ 10 3 or more (for example, 1 ⁇ 10 3 to 1 ⁇ 10 8 ) in terms of polystyrene.
  • Low molecular compound means a compound that has no molecular weight distribution and has a molecular weight of 1 ⁇ 10 4 or less.
  • Structural unit means one or more units present in a polymer compound.
  • a structural unit that exists two or more in a polymer compound is generally also called a "repeat unit.”
  • the "alkyl group” may be linear or branched, and may have a substituent.
  • the number of carbon atoms in the straight chain alkyl group, not including the number of carbon atoms in substituents, is usually 1 to 50, preferably 1 to 30, and more preferably 1 to 20.
  • the number of carbon atoms in the branched alkyl group, not including the number of carbon atoms in substituents is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.
  • alkyl group examples 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 group.
  • the "cycloalkyl group” may have a substituent.
  • the number of carbon atoms in the cycloalkyl group, not including the number of carbon atoms in substituents, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.
  • Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.
  • Aryl group means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the aryl group may have a substituent.
  • the number of carbon atoms in the aryl group, not including the number of carbon atoms in substituents, is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10.
  • Examples of the aryl group include 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, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, and 4-phenylphenyl group.
  • the "alkoxy group” may be linear or branched, and may have a substituent.
  • the number of carbon atoms in the straight chain alkoxy group, not including the number of carbon atoms in substituents, is usually 1 to 40, preferably 4 to 10.
  • the number of carbon atoms in the branched alkoxy group, not including the number of carbon atoms in substituents is usually 3 to 40, preferably 4 to 10.
  • alkoxy group examples include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, -ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, and lauryloxy group.
  • the "cycloalkoxy group” may have a substituent.
  • the number of carbon atoms in the cycloalkoxy group is usually 3 to 40, preferably 4 to 10.
  • Examples of the cycloalkoxy group include a cyclohexyloxy group.
  • the "aryloxy group” may have a substituent.
  • the number of carbon atoms in the aryloxy group, not including the number of carbon atoms in substituents, is usually 6 to 60, preferably 6 to 48.
  • Examples of the aryloxy group include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, and 1-pyrenyloxy group.
  • a “p-valent heterocyclic group” (p represents an integer of 1 or more) refers to a heterocyclic compound in which p hydrogen atoms are directly bonded to carbon atoms or heteroatoms constituting the ring. means the remaining atomic group excluding the hydrogen atom. Among p-valent heterocyclic groups, it is an atomic group remaining after removing p hydrogen atoms from the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from an aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group” is preferred.
  • Aromatic heterocyclic compounds include oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, dibenzofuran, Compounds in which the heterocycle itself shows aromaticity, such as dibenzothiophene; and compounds in which the heterocycle itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran, etc. It means a ring-fused compound;
  • the monovalent heterocyclic group may have a substituent.
  • the number of carbon atoms in the monovalent heterocyclic group, not including the number of carbon atoms in substituents, is usually 2 to 60, preferably 4 to 20.
  • Examples of the monovalent heterocyclic group include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, and a triazinyl group.
  • Halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • the "amino group” may be either an amino group (-NH 2 ) or a substituted amino group, and preferably a substituted amino group.
  • a substituted amino group means a group in which one or two hydrogen atoms bonded to the nitrogen atom of an amino group are substituted with an organic group.
  • the organic group is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group.
  • Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
  • amino group examples include dimethylamino group, diethylamino group, diphenylamino group, bis(4-methylphenyl)amino group, bis(4-tert-butylphenyl)amino group, and bis(3,5-di-tert -butylphenyl)amino group.
  • alkenyl group may be linear or branched, and may have a substituent.
  • the number of carbon atoms in the straight chain alkenyl group, not including the number of carbon atoms in substituents, is usually 2 to 30, preferably 3 to 20.
  • the number of carbon atoms in the branched alkenyl group, not including the number of carbon atoms in substituents, is usually 3 to 30, preferably 4 to 20.
  • the "cycloalkenyl group” may have a substituent.
  • the number of carbon atoms in the cycloalkenyl group, not including the number of carbon atoms in substituents is usually 3 to 30, preferably 4 to 20.
  • alkenyl group and cycloalkenyl group examples include vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, -hexenyl group, 7-octenyl group, and 5-cyclohexenyl group.
  • alkynyl group may be either linear or branched, and may have a substituent.
  • the number of carbon atoms in the alkynyl group, not including the number of carbon atoms in substituents, is usually 2 to 20, preferably 3 to 20.
  • the number of carbon atoms in the branched alkynyl group, not including the number of carbon atoms in substituents is usually 4 to 30, preferably 4 to 20.
  • the "cycloalkynyl group” may have a substituent.
  • the number of carbon atoms in the cycloalkynyl group, not including the number of carbon atoms in substituents is usually 4 to 30, preferably 4 to 20.
  • alkynyl group and cycloalkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, -hexynyl group, and 5-cyclohexynyl group.
  • Arylene group means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon.
  • the arylene group may have a substituent.
  • the number of carbon atoms in the arylene group, not including the number of carbon atoms in substituents, is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.
  • arylene group examples include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylene diyl group, a chrysenediyl group, and a formula (A-1 ) to formula (A-20), preferably groups represented by formula (A-1) to formula (A-20).
  • the arylene group includes a group in which a plurality of these groups are bonded.
  • R and R a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group.
  • a plurality of R and R a may be the same or different, and R a may be bonded to each other to form a ring with the atoms to which they are bonded.
  • the divalent heterocyclic group may have a substituent.
  • the number of carbon atoms in the divalent heterocyclic group, not including the number of carbon atoms in substituents, is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15.
  • Examples of the divalent heterocyclic group 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 directly bonded to a carbon atom or a heteroatom constituting the ring from diazole or triazole; and formula (AA-1) to formula (AA- Groups represented by formulas (AA-1) to (AA-34) are preferred.
  • a "crosslinking group” is a group that can generate a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared ray irradiation, radical reaction, etc., and is preferably a group with the formula (XL -1) to a group represented by formula (XL-19).
  • R XL represents a methylene group, an oxygen atom, or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • R XL represents a methylene group, an oxygen atom, or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • *1 represents the bonding position.
  • These bridging groups may have a substituent, and when a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded. It's okay. ]
  • Substituent refers to a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, alkenyl group. , represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group.
  • the substituent may be a bridging group.
  • the polymer compound of this embodiment is a polymer compound containing at least two types of structural units represented by formula (0-1).
  • the number of types of structural units represented by formula (0-1) contained in the polymer compound of this embodiment is preferably 2 to 10 types, more preferably 2 to 5 types.
  • the structural unit represented by formula (0-1) is preferably a structural unit represented by formula (0-2).
  • the structural unit represented by formula (0-2) is preferably the structural unit represented by formula (1).
  • R 0 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably an alkyl group, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • group, a cycloalkyl group, or an aryl group, more preferably an aryl group, and these groups may have a substituent.
  • R 0 may have is preferably 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.
  • an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group are more preferred, and an alkyl group, a cycloalkyl group, or an aryl group is even more preferred.
  • These groups may further have a substituent.
  • At least one of the above R 0 is a group represented by formula (DA) or formula (DC), since the luminance life of the light emitting device using the polymer compound of the present embodiment is more excellent. is preferable, and a group represented by formula (DA) or formula (DB) is also preferable. Further, both of the above R 0 are preferably groups represented by the formula (DA) or the formula (DC), and are preferably groups represented by the formula (DA) or the formula (D-B). It is also preferable that it is a group.
  • At least one of the two or more types of structural units represented by the formula (0-1) contained in the polymer compound of the present embodiment is such that both of the above R 0 and the formula (D -A) or a group represented by formula (DB) is preferable.
  • a is 0 or 1, and more preferably 0, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • b is preferably 0 or 1, and more preferably 0, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • R 1 and R 2 are preferably an alkyl group, a cycloalkyl group, or an aryl group, and more preferably an alkyl group or a cycloalkyl group, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent. These groups may have a substituent.
  • Examples and preferred ranges of substituents that R 1 and R 2 may have are the same as the examples and preferred ranges of substituents that R 0 may have.
  • m DA1 to m DA3 are preferably 0 to 5, more preferably 0 to 3, and 0 or 1 because the luminance life of the light emitting element using the polymer compound of this embodiment is more excellent. It is more preferable that it be present, and it is especially preferable that it be zero.
  • m DB1 to m DB7 are preferably 0 to 5, more preferably 0 to 3, and 0 or 1 because the luminance life of the light emitting element using the polymer compound of this embodiment is more excellent. It is more preferable that it be present, and it is especially preferable that it be zero.
  • mDC1 is preferably 1 to 5, more preferably 1 to 4, and preferably 1 to 3, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent. More preferably, 1 or 2 is particularly preferred.
  • the aryl group in T DA to T DC is preferably a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, an n-spirobifluorenyl group or a pyrenyl group; or fluorenyl group is more preferable, and phenyl group is even more preferable. These groups may have a substituent.
  • Substituents that T DA to T DC may have include 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 group.
  • An atom is preferred, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group, or an aryl group is even more preferred, and an aryl group is particularly preferred.
  • These groups may further have a substituent.
  • Substituents that T DA to T DC may further include include alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, aryloxy groups, and monovalent groups.
  • a heterocyclic group, a substituted amino group, or a halogen atom is preferable, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group is more preferable, and an alkyl group, a cycloalkyl group, or an aryl group is even more preferable.
  • aryl groups are particularly preferred. Although these groups may further have a substituent, it is preferable that they have no further substituent.
  • the Ar DA1 to Ar DA3 , Ar DB1 to Ar DB7 , and Ar DC1 are arylene groups that may have a substituent, and may be the same or different.
  • the arylene group in Ar DA1 to Ar DA3 , Ar DB1 to Ar DB7 , and Ar DC1 includes a phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrenediyl group, dihydrophenanthenediyl group, naphthacenediyl group, fluorenediyl group, or pyrenediyl group. is preferred, more preferred than a phenylene group, naphthalenediyl group, or fluorenediyl group, and still more preferred is a phenylene group. These groups may have a substituent.
  • Examples and preferred ranges of substituents that Ar DA1 to Ar DA3 , Ar DB1 to Ar DB7 , and Ar DC1 may have are the same as examples and preferred ranges of substituents that T DA may have. .
  • Examples and preferred ranges of substituents that Ar DA1 to Ar DA3 , Ar DB1 to Ar DB7 , and Ar DC1 may further include the substituents that T DA may have.
  • the examples and preferred ranges of substituents that the group may further have are the same.
  • G DA and G DB1 to G DB3 are each independently a group represented by formula (GDA-11).
  • * represents the bonding position between G DA and Ar DA1 , the bonding position between G DB1 and Ar DB1 , the bonding position between G DB2 and Ar DB2 , or the bonding position between G DB3 and Ar DB3 .
  • ** represents the bonding position between G DA and Ar DA2 , the bonding position between G DB1 and Ar DB2 , the bonding position between G DB2 and Ar DB4 , or the bonding position between G DB3 and Ar DB6 .
  • R DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group. 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, or an aryl group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, even more preferably a hydrogen atom, and these groups are further substituted. It may have a group.
  • Examples and preferred ranges of substituents that R DA may have are the same as examples and preferred ranges of substituents that T DA may have.
  • n 2 because the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • c is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • d is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent. preferable.
  • R A is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably is 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.
  • R A may have is preferably 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.
  • an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group are more preferred, an alkyl group, a cycloalkyl group, or an aryl group are even more preferred, and an aryl group is particularly preferred.
  • These groups may further have a substituent.
  • examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, a spirobifluorenyl group, or a pyrenyl group.
  • a phenyl group, a naphthyl group, or a fluorenyl group is more preferable, a phenyl group or a fluorenyl group is even more preferable, and a fluorenyl group is particularly preferable.
  • These groups may have a substituent.
  • R A may further have include substituents that T DA may further have. Same as examples and preferred ranges.
  • R 3 and R 4 are preferably an alkyl group, a cycloalkyl group, or an aryl group, and more preferably an alkyl group or a cycloalkyl group, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent. These groups may have a substituent.
  • the total amount of the structural units represented by the formula (0-1) is determined based on the total amount of the structural units contained in the polymer compound, since the luminance life of the light emitting device using the polymer compound of this embodiment is better.
  • the amount is preferably 0.5 to 100 mol%, more preferably 5 to 100 mol%, even more preferably 10 to 100 mol%, particularly preferably 30 to 90 mol%, and particularly preferably is 60 to 90 mol%.
  • structural unit represented by formula (0-1) include structural units represented by formulas (0-101) to (0-163).
  • Ar Y1 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; The group may have a substituent.
  • the structural unit represented by formula (Y) is different from the structural unit represented by formula (0-1).
  • a 1 and a 2 each independently represent an integer of 0 or more.
  • Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
  • Ar X2 and Ar X4 each independently represent 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.
  • Ar X2 and Ar X4 When a plurality of Ar X2 and Ar X4 exist, they may be the same or different.
  • 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.
  • R X2 and R X3 may be the same or different.
  • the arylene group represented by Ar Y1 is more preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), or formula ( A-13) or formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9) or formula (A-19) These groups may have a substituent.
  • the divalent heterocyclic group represented by Ar Y1 is more preferably a formula (AA-4), a formula (AA-10), a formula (AA-13), a formula (AA-15), or a formula (AA-18). ) or a group represented by the formula (AA-20), particularly preferably a group represented by the formula (AA-4), the formula (AA-10), the formula (AA-18) or the formula (AA-20) These groups may have a substituent.
  • More preferred ranges of the arylene group and 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 still more preferred The ranges are the same as the more preferred ranges and more preferred ranges 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 represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded includes at least one of Ar X2 and Ar X4 in formula (X). Examples include those similar to divalent groups in which one type of arylene group and at least one type of divalent heterocyclic group are directly bonded.
  • 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 the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10), and the light-emitting element using the polymer compound of this embodiment
  • the structural units are preferably those represented by formulas (Y-1) to (Y-3), and from the viewpoint of electron transport properties, preferably the structural units are represented by formulas (Y-4) to (Y-3).
  • 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 Y1s may be the same or different, and adjacent R Y1s may be bonded to each other to form a ring 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 R Y11 's 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.
  • R Y1 represents the same meaning as above.
  • R Y2 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 Y2s may be the same or different, and R Y2s may be bonded to each other to form a ring 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. It's okay.
  • the combination of two R Y2s in the group represented by -C(R Y2 ) 2 - is preferably such that both are an alkyl group or a cycloalkyl group, both are an aryl group, and both are a monovalent hetero cyclic group, or one is an alkyl group or cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent.
  • R Y2s may be bonded to each other to form a ring with the atoms to which they are bonded, and when R Y2 forms a ring, as a group represented by -C(R Y2 ) 2 - is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. You may do so.
  • R Y2s in the group represented by -C(R Y2 ) 2 -C(R Y2 ) 2 - are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is.
  • a plurality of R Y2 may be bonded to each other to form a ring with the atoms to which they are bonded, and when R Y2 forms a ring, -C(R Y2 ) 2 -C(R Y2 ) 2 -
  • the group represented is preferably a group represented by formula (Y-B1) to formula (Y-B5), more preferably a group represented by formula (Y-B3), and these groups are It may have a substituent.
  • R Y2 represents the same meaning as above. ]
  • the structural unit represented by formula (Y-2) is preferably a structural unit represented by formula (Y-2'). [In the formula, R Y1 and X Y1 represent the same meanings as above. ]
  • the structural unit represented by formula (Y-3) is preferably a structural unit represented by formula (Y-3'). [In the formula, R Y11 and X Y1 represent the same meanings as above. ]
  • R Y1 represents the same meaning as above.
  • R Y3 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 Y3 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. It's okay.
  • the structural unit represented by formula (Y-4) is preferably a structural unit represented by formula (Y-4'), and the structural unit represented by formula (Y-6) is preferably a structural unit represented by formula (Y-4'). -6') is preferable.
  • R Y1 and R Y3 represent the same meanings as above.
  • RY1 represents the same meaning as above.
  • R Y4 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 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. It's okay.
  • Examples of the structural unit represented by formula (Y) include structural units consisting of arylene groups represented by formulas (Y-101) to (Y-139), and structural units of formulas (Y-201) to (Y- 209), at least one arylene group and at least one divalent heterocyclic group represented by formulas (Y-301) to (Y-306)
  • a structural unit consisting of a divalent group directly bonded to a group can be mentioned.
  • the structural unit represented by formula (Y) in which Ar Y1 is an arylene group is not included in the polymer compound because the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • the amount is preferably from 0.5 to 80 mol%, more preferably from 30 to 60 mol%, based on the total amount of structural units contained.
  • Only one type of structural unit represented by formula (Y) may be contained in the polymer compound, or two or more types may be contained in the polymer compound.
  • [Constituent unit represented by formula (X)] a1 is preferably 2 or less, more preferably 1, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • a2 is preferably 2 or less, and more preferably 0, since the luminance life of the light emitting device using the polymer compound of this embodiment is more excellent.
  • 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.
  • the arylene group represented by Ar X1 and Ar may have a substituent.
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by formula (AA-1), formula (AA-2) or formula (AA-7) to formula (AA-26) These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably arylene groups which may have a substituent.
  • the more preferable range of the divalent heterocyclic group represented by Ar X2 and Ar X4 is the same as the more preferable range of the divalent heterocyclic group represented by Ar X1 and Ar X3 .
  • the more preferable ranges are the same as the more preferable ranges and still more preferable ranges of the arylene group and divalent heterocyclic group represented by Ar X1 and Ar X3 , respectively.
  • R XX 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.
  • R XX is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent.
  • Ar X2 and Ar X4 are preferably arylene groups which may have substituents.
  • 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-3) to formula (X -7), more preferably structural units represented by formulas (X-3) to (X-6).
  • R X4 and R represents a group, and these groups may have a substituent.
  • a plurality of R X4 's may be the same or different.
  • a plurality of R X5s may be the same or different, and adjacent R X5s may be bonded to each other to form a ring with the carbon atom to which they are bonded.
  • R X4 and R represents a group, and these groups may have a substituent.
  • a plurality of R X4 's may be the same or different.
  • a plurality of R X5s may be the same or different, and adjacent R X5s may be bonded to each other to form a ring with the carbon atom to which they are bonded.
  • the structural unit represented by formula (X) has excellent hole transport properties, it is preferably 0.1 to 50 mol%, more preferably 0.1 to 50 mol%, based on the total amount of structural units contained in the polymer compound.
  • the content is 1 to 40 mol%, more preferably 5 to 30 mol%.
  • Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-23), preferably formula (X1-2) or formula (X1-2). -6) ⁇ A structural unit represented by formula (X1-14).
  • polymer compounds P-1 to P-4 examples include polymer compounds P-1 to P-4 shown in Table 1.
  • “other structural units” means structural units other than the structural units represented by formula (0-1), formula (X), and formula (Y).
  • the terminal group of the polymer compound of this embodiment is preferable because if the polymerization active group remains as it is, the luminescence characteristics and brightness life may deteriorate when the polymer compound is used for producing a light emitting device. is a stable group.
  • the terminal group is preferably a group that is conjugated to the main chain, and includes a group that is bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.
  • the polymer compound of this embodiment may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may be of any other form; A copolymer formed by copolymerizing raw material monomers is preferable.
  • the polymer compound of the present embodiment includes, for example, a compound represented by formula (M-0), a compound represented by formula (MY), and/or a compound represented by formula (MX). , can be produced by condensation polymerization.
  • the compounds used for producing the polymer compound of this embodiment may be collectively referred to as "raw material monomers.”
  • a, R 1 , Ar Y1 , a 1 , a 2 , Ar X1 to Ar X4 and R X1 to R X3 have the same meanings as above.
  • Z C1 to Z C6 each independently represent a group selected from the group consisting of substituent group A and substituent group B. ]
  • Z C1 and Z C2 are groups selected from substituent group A
  • Z C3 , Z C4 , Z C5 and Z C6 are groups selected from substituent group B.
  • Z C and Z C2 are groups selected from substituent group B
  • Z C3 , Z C4 , Z C5 and Z C6 are groups selected from substituent group A.
  • ⁇ Substituent group A> Chlorine atom, bromine atom, iodine atom, and -OS( O) 2 R C1 (wherein R C1 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups have a substituent ).
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent.
  • a plurality of R C2 is A group that may be the same or different, and may be linked to each other to form a ring structure with the oxygen atom to which each is bonded; - A group represented by BF 3 Q' (wherein Q' represents Li, Na, K, Rb or Cs); - A group represented by MgY' (wherein Y' represents a chlorine atom, a bromine atom, or an iodine atom); - a group represented by ZnY'' (wherein Y'' represents a chlorine atom, a bromine atom or an iodine atom); and -Sn(R C3 ) 3 (wherein R C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent.
  • a plurality of R C3 is The groups may be the same or different, and may be linked to each other to form a ring structure together with the tin atom
  • Examples of the group represented by -B(OR C2 ) 2 include groups represented by the following formula.
  • a compound having a group selected from substituent group A and a compound having a group selected from substituent group B are condensed together by a known coupling reaction to form a group selected from substituent group A and a substituent group B. Carbon atoms that are bonded to groups selected from are bonded to each other. Therefore, if a compound having two groups selected from substituent group A and a compound having two groups selected from substituent group B are subjected to a known coupling reaction, the condensation of these compounds will occur through condensation polymerization. Polymers can be obtained.
  • Condensation polymerization is usually carried out in the presence of a catalyst, a base, and a solvent, but if necessary, it may be carried out in the presence of a phase transfer catalyst.
  • the catalyst examples include bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and tris(dibenzylideneacetone).
  • Dipalladium(0) palladium complexes such as palladium acetate, tetrakis(triphenylphosphine)nickel(0), [1,3-bis(diphenylphosphino)propane)nickel(II) dichloride, bis(1,4- Transition metal complexes such as nickel complexes such as cyclooctadiene)nickel(0); these transition metal complexes can further be used to form triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, Examples include complexes having ligands such as 1,3-bis(diphenylphosphino)propane and bipyridyl.
  • the catalysts may be used alone or in combination of two or more.
  • the amount of catalyst used is usually 0.00001 to 3 molar equivalents as the amount of transition metal relative to the total number of moles of raw material monomers.
  • bases and phase transfer catalysts include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; tetrabutylammonium fluoride, tetraethylammonium hydroxide, and tetraethylammonium hydroxide.
  • examples include organic bases such as butylammonium; phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide.
  • the base and the phase transfer catalyst may be used alone or in combination of two or more.
  • the amounts of the base and phase transfer catalyst used are usually 0.001 to 100 molar equivalents, respectively, based on the total number of moles of the raw material monomers.
  • the solvent examples include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N,N-dimethylacetamide, and N,N-dimethylformamide, and water.
  • organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N,N-dimethylacetamide, and N,N-dimethylformamide, and water.
  • the solvents may be used alone or in combination of two or more.
  • the amount of the solvent used is usually 10 to 100,000 parts by mass based on the total of 100 parts by mass of the raw material monomers.
  • the reaction temperature for condensation polymerization is usually -100 to 200°C.
  • the reaction time for condensation polymerization is usually 1 hour or more.
  • Post-treatment of the polymerization reaction can be carried out by known methods, such as removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying. Use these methods alone or in combination. If the purity of the polymer compound is low, it can be purified by conventional methods such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.
  • composition of this embodiment includes at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a luminescent material, an antioxidant, and a solvent; Contains a high molecular compound.
  • composition containing the polymer compound and solvent of this embodiment (hereinafter sometimes referred to as "ink") is suitable for producing light emitting elements using printing methods such as inkjet printing and nozzle printing. .
  • the viscosity of the ink can be adjusted depending on the type of printing method, but when applied to printing methods such as inkjet printing in which the solution passes through a discharge device, it is necessary to adjust the viscosity of the ink to prevent clogging and deflection during discharge. , preferably 1 to 20 mPa ⁇ s at 25°C.
  • the solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink.
  • the solvent 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; toluene, 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 bicyclohexy
  • 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 , N-dimethylformamide and the like.
  • the solvents may be used alone or in combination of two or more.
  • the amount of the solvent blended is usually 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass, based on 100 parts by mass of the polymer compound of the present embodiment.
  • Hole transport materials are classified into low molecular weight compounds and high molecular weight compounds, with high molecular weight compounds being preferred, and high molecular weight compounds having a crosslinking group being more preferred.
  • polymer compound examples include polyvinylcarbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof.
  • the polymer compound may be a compound to which an electron-accepting site is bonded.
  • the electron-accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, with fullerene being preferred.
  • the blending amount of the hole transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound of this embodiment. .
  • the hole transport materials may be used alone or in combination of two or more.
  • Electron transport materials are classified into low molecular compounds and high molecular compounds.
  • the electron transport material may have a crosslinking group.
  • low-molecular compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and , diphenoquinone, and derivatives thereof.
  • polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
  • the polymer compound may be doped with metal.
  • the amount of the electron transport material blended is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound of the present embodiment.
  • the electron transport materials may be used alone or in combination of two or more.
  • Hole-injecting materials and electron-injecting materials are classified into low-molecular compounds and high-molecular compounds, respectively.
  • the hole injection material and the electron injection material may have a crosslinking group.
  • 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 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, etc. conductive polymers.
  • the amount of the hole-injecting material and the electron-injecting material is usually 1 to 400 parts by mass, preferably 5 parts by mass, per 100 parts by mass of the polymer compound of this embodiment. ⁇ 150 parts by mass.
  • the hole injection material and the electron injection material may each be used singly or in combination of two or more.
  • the electrical conductivity of the conductive polymer is preferably 1 ⁇ 10 ⁇ 5 S/cm to 1 ⁇ 10 3 S/cm.
  • the conductive polymer can be doped with an appropriate amount of ions.
  • the type of ion to be doped is an anion if it is a hole injection material, and a cation if it is an electron injection material.
  • anions include polystyrene sulfonate ions, alkylbenzenesulfonate ions, and camphor sulfonate ions.
  • cations include lithium ions, sodium ions, potassium ions, and tetrabutylammonium ions.
  • the number of ions to be doped may be one type or two or more types.
  • Luminescent materials are classified into low molecular compounds and high molecular compounds.
  • the luminescent material may have a crosslinking group.
  • low-molecular compounds examples include naphthalene and its derivatives; anthracene and its derivatives; pyrene and its derivatives; glycene and its derivatives; perylene and its derivatives; and triplet luminescent complexes having iridium, platinum or europium as the central metal; can be mentioned.
  • Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a structural unit represented by formula (X), a carbazolediyl group, a phenoxazinediyl group, and a phenothiazine group.
  • Examples include polymeric compounds containing a diyl group, anthracenediyl group, pyrenediyl group, and the like.
  • the luminescent material may include a low molecular compound and a high molecular compound.
  • triplet light-emitting complex examples include known complexes, such as metal complexes described in JP-A No. 2022-13757.
  • the content of the luminescent material is usually 0.1 to 400 parts by mass based on 100 parts by mass of the polymer compound of the present embodiment.
  • the antioxidant may be any compound that is soluble in the same solvent as the polymer compound of this embodiment and does not inhibit luminescence and charge transport, such as phenolic antioxidants and phosphorus antioxidants. .
  • the amount of antioxidant added is usually 0.001 to 10 parts by mass based on 100 parts by mass of the polymer compound of the present embodiment.
  • the antioxidants may be used alone or in combination of two or more.
  • the membrane contains the polymer compound of this embodiment.
  • the membrane also includes an insolubilized membrane in which the polymer compound of this embodiment is made insoluble in a solvent by crosslinking.
  • the insolubilized film is a film obtained by crosslinking the polymer compound of this embodiment by external stimuli such as heating and light irradiation. Since the insolubilized film is substantially insoluble in a solvent, it can be suitably used for laminating light emitting devices.
  • the heating temperature for crosslinking the membrane is usually 25 to 300°C, preferably 50 to 250°C, and more preferably 150 to 200°C.
  • the types of light used for light irradiation to crosslink the film are, for example, ultraviolet light, near ultraviolet light, and visible light.
  • the film is suitable as a light emitting layer, a hole transport layer, or a hole injection layer in a light emitting device.
  • the film can be formed using ink, such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, and screen printing. , a flexographic printing method, an offset printing method, an inkjet printing method, a capillary coating method, or a nozzle coating method.
  • ink such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, and screen printing.
  • a flexographic printing method an offset printing method, an inkjet printing method, a capillary coating method, or a nozzle coating method.
  • the thickness of the film is usually 1 nm to 10 ⁇ m.
  • the light-emitting element of this embodiment is a light-emitting element such as an organic electroluminescent element obtained using the polymer compound of this embodiment, and the light-emitting element includes, for example, a light-emitting element containing the polymer compound of this embodiment.
  • the light emitting element in which the polymer compound of this embodiment is crosslinked intramolecularly, intermolecularly, or both.
  • the structure of the light emitting element of this embodiment includes, for example, electrodes consisting of an anode and a cathode, and a layer obtained using the polymer compound of this embodiment provided between the electrodes.
  • the layer obtained using the polymer compound of this 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 it is a light emitting layer.
  • These layers each include a luminescent material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material.
  • These layers are formed by dissolving a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material in the above-mentioned solvent, preparing an ink, and using the above-mentioned film preparation. It can be formed using the same method.
  • a light emitting element has a light emitting layer between an anode and a cathode.
  • the light emitting device of this 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, From the viewpoint of electron injection properties and electron transport properties, it is preferable to have at least one layer of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.
  • Materials for the hole transport layer, electron transport layer, light emitting layer, hole injection layer, and electron injection layer include the above-mentioned hole transport materials, electron transport materials, and the polymer compound of this embodiment. Examples include light-emitting materials, hole-injecting materials, and electron-injecting materials.
  • the material for the hole transport layer, the material for the electron transport layer, and the material for the light emitting layer are used when forming the hole transport layer, the electron transport layer, and the layer adjacent to the light emitting layer, respectively, in producing the light emitting device.
  • the material When the material is dissolved in a solvent, it is preferable that the material has a crosslinking group in order to prevent the material from dissolving in the solvent. After each layer is formed using a material having a crosslinking group, the layer can be made insolubilized by crosslinking the crosslinking group.
  • the method for forming each layer such as the light-emitting layer, hole-transporting layer, electron-transporting layer, hole-injecting layer, and electron-injecting layer includes, for example, when using a low-molecular compound, vacuum formation from powder.
  • Examples include a vapor deposition method, a method of forming a film from a solution or a molten state, and when a polymer compound is used, for example, a method of forming a film from a solution or a molten state.
  • the order, number, and thickness of the laminated layers may be adjusted in consideration of luminous efficiency and device life.
  • the substrate in the light emitting element may be any substrate as long as it is capable of forming an electrode and is not chemically changed during the formation of an organic layer, and is, for example, a substrate made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, it is preferred that the electrode furthest from the substrate be transparent or translucent.
  • Examples of the material for the anode include conductive metal oxides, translucent alloys, and translucent metals, preferably indium oxide, zinc oxide, tin oxide (NESA), indium tin oxide (conductive compounds such as ITO), indium, zinc, and oxide; composites of silver, palladium, and copper (APC); and metals such as gold, platinum, silver, and copper.
  • conductive metal oxides preferably indium oxide, zinc oxide, tin oxide (NESA), indium tin oxide (conductive compounds such as ITO), indium, zinc, and oxide; composites of silver, palladium, and copper (APC); and metals such as gold, platinum, silver, and copper.
  • Examples of the cathode material include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these; and one of them. Examples include alloys of at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; graphite; and graphite intercalation compounds. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. 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 displays, lighting, and the like.
  • the number average molecular weight (Mn) in terms of polystyrene and the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound were determined using one of the following size exclusion chromatography (SEC) methods using tetrahydrofuran as a moving phase. It was calculated by In addition, each measurement condition of SEC is as follows.
  • the 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.
  • TSKguardcolumn SuperAW-H TSKgel Super AWM-H
  • TSKgel SuperAW3000 all manufactured by Tosoh
  • a UV-VIS detector manufactured by Tosoh, trade name: UV-8320GPC was used as a detector.
  • NMR NMR was measured by the following method. 5 to 10 mg of the measurement sample was mixed with about 0.5 mL of deuterated chloroform (CDCl 3 ), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 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 Chemical Industry Co., Ltd.) or an ODS column having equivalent performance.
  • a photodiode array detector manufactured by Shimadzu Corporation, trade name: SPD-M20A was used as a detector.
  • the obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was purified by silica gel column chromatography (n-hexane solvent) and dried under reduced pressure at 50° C. to obtain Compound 1A (278.2 g).
  • the HPLC area percentage value of Compound 1A was greater than 99.5%.
  • the obtained organic layer was washed with ion-exchanged water and an aqueous sodium hydrogen carbonate solution, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was recrystallized from toluene and ethanol and dried under reduced pressure at 50° C. to obtain Compound 1D (197.4 g).
  • the HPLC area percentage value of Compound 1D was greater than 99.5%.
  • the obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was recrystallized with a mixed solvent of toluene/ethanol and dried under reduced pressure at 50° C. to obtain Compound 3C (22.0 g).
  • the LC area percentage value of Compound 3C was greater than 99.5%. This operation was repeated to obtain the required amount of compound 3C.
  • ⁇ Synthesis examples PM6 to PM10 Synthesis of compounds PM6 to PM10>
  • Compound PM6 was synthesized according to the method described in JP-A-2012-144722.
  • Compound PM7 was synthesized according to the method described in International Publication No. 2002/092723.
  • Compound PM8 was synthesized according to the method described in JP-A-2011-174062.
  • Compound PM9 was synthesized according to the method described in JP-A-2004-143419.
  • Compound PM10 was synthesized according to the method described in JP-A-2010-031259.
  • the polymer compound IP1 is composed of 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, according to the theoretical value determined from the amount of raw materials to be charged.
  • the copolymer is composed of units and structural units derived from the monomer PM4 in a molar ratio of 50:30:12.5:7.5.
  • Step 2 A 20% by mass aqueous tetraethylammonium hydroxide solution (83 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3 hours.
  • Step 3 After the reaction, phenylboronic acid (0.10 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.15 mg) were added thereto, and the mixture was refluxed for 3 hours.
  • Step 4 After that, the reaction solution was cooled to room temperature, the aqueous layer was removed, and then once with ion-exchanged water and once with 0.15% by mass aqueous solution of sodium N,N-diethyldithiocarbamate at 10% by mass. It was washed twice with hydrochloric acid, twice with a 3% by mass ammonia aqueous solution, and twice with ion-exchanged water. The obtained solution was dehydrated under reduced pressure to obtain a toluene solution from which water was removed. This toluene solution was purified by passing it through an alumina column through which toluene was passed in advance.
  • the polymer compound P1 has a composition of 50: It is a copolymer composed of a molar ratio of 20:30.
  • Step 1 Synthesis of polymer compound P2 (Step 1) in the synthesis of polymer compound P1 was performed as follows: After creating an inert gas atmosphere in the reaction vessel, compound 2D (2.57 g), compound 2C (1. 18g), Compound 3E (2.00g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.22mg) and toluene (180mL) were added and heated to 80°C. By performing the same synthesis as P1, 2.60 g of polymer compound P2 was obtained. The Mn of the polymer compound P2 was 8.9 ⁇ 10 3 and the Mw was 2.7 ⁇ 10 4 .
  • the polymer compound P2 has a composition of 50: It is a copolymer composed of a molar ratio of 20:30.
  • Step 1 Synthesis of polymer compound P3 (Step 1) After creating an inert gas atmosphere in the reaction vessel, compound 2D (0.641 g), compound 3E (0.438 g), and compound PM3 (0.0699 g) , compound PM9 (0.0280 g), compound PM10 (0.0738 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (0.64 mg) and toluene (30 mL) were added, and the mixture was heated to 80°C. (Step 2) A 20% by mass aqueous tetraethylammonium hydroxide solution (20 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3 hours and 30 minutes.
  • the polymer compound P3 is composed of a structural unit derived from compound 2D, a structural unit derived from compound 3E, a structural unit derived from compound PM3, and a structural unit derived from compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • the polymer compound P4 is composed of a structural unit derived from compound 1E, a structural unit derived from compound PM7, a structural unit derived from compound PM3, and a structural unit derived from compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • Step 1 Synthesis of polymer compound P5 (Step 1) in the synthesis of polymer compound P3 was performed as follows: After creating an inert gas atmosphere in the reaction vessel, compound 4C (0.750 g), compound PM7 (0. 414 g), compound PM3 (0.0899 g), compound PM9 (0.0360 g), compound PM10 (0.0948 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (0.79 mg) and toluene (30 mL) were added. , and heated to 80°C.'' 0.71 g of polymer compound P5 was obtained in the same manner as the synthesis of polymer compound P3. The Mn of the polymer compound P5 was 8.7 ⁇ 10 4 and the Mw was 1.9 ⁇ 10 5 .
  • the polymer compound P5 is composed of a structural unit derived from compound 4C, a structural unit derived from compound PM7, a structural unit derived from compound PM3, and a structural unit derived from compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • the polymer compound CP2 is composed of a structural unit derived from compound PM8, a structural unit derived from compound 1D, a structural unit derived from compound PM3, and a structural unit derived from compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • the polymer compound CP3 is composed of a structural unit derived from the compound PM8, a structural unit derived from the compound PM7, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • Step 1 Synthesis of polymer compound CP4 (Step 1) After creating an inert gas atmosphere in the reaction vessel, compound PM8 (1.52 g), compound PM6 (0.829 g), compound PM3 (0.226 g) , compound PM9 (0.0889 g), compound PM10 (0.236 g), dichlorobis(triphenylphosphine) palladium (1.40 mg) and toluene (47 mL) were added, and the mixture was heated to 80°C. (Step 2) A 20% by mass aqueous tetraethylammonium hydroxide solution (6.6 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3 hours.
  • Step 2 A 20% by mass aqueous tetraethylammonium hydroxide solution (6.6 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3 hours.
  • phenylboronic acid (24.4 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.71 mg) were added thereto, and the mixture was refluxed for 3 hours. Thereafter, the reaction solution was cooled to room temperature, the aqueous layer was removed, the temperature was raised to 85°C, and the mixture was stirred with a 0.05% by mass aqueous solution of sodium N,N-diethyldithiocarbamate for 2 hours, and then diluted with ion-exchanged water. It was washed twice with a 3% by mass acetic acid aqueous solution and twice with ion-exchanged water.
  • the polymer compound CP4 is composed of a structural unit derived from the compound PM8, a structural unit derived from the compound PM6, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM9, according to the theoretical value determined from the amount of raw materials.
  • This is a copolymer in which the structural unit derived from the compound PM10 and the structural unit derived from the compound PM10 are comprised in a molar ratio of 50:32:10:3:5.
  • ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • Example D1 Production and evaluation of light emitting element D1
  • polymer compound P1 and fluorescent compound G1 95% by mass/5% by mass
  • concentration of the xylene solution was further increased to 1.2% by mass.
  • Light-emitting element D1 was produced in the same manner as Comparative Example CD1 except that the content was changed from 1.6% by mass.
  • the maximum peak wavelength of the emission spectrum of the light emitting element D1 was 445 nm.
  • the relative value of LT90 to light emitting element CD1 when driven at constant current with an initial luminance of 30 cd/m 2 was 4342.
  • a light emitting device D2 was produced in the same manner as Example D1. The maximum peak wavelength of the emission spectrum of light emitting element D2 was 460 nm. LT90 was measured when driving at constant current with an initial luminance of 100 cd/m 2 .
  • Example D1-2 Fabrication and evaluation of light emitting device D1-2
  • Light emitting device D1-2 was fabricated in the same manner as Example D1 except that the thickness of the light emitting layer in Example D1 was changed from 35 nm to 60 nm. did.
  • the maximum peak wavelength of the emission spectrum of the light emitting element D1-2 was 465 nm.
  • the relative value of LT90 to light emitting element D2 when driven at constant current with an initial luminance of 100 cd/m 2 was 8.
  • Table 2 shows the LT90 values of the light emitting element D2 when the LT90 of Example D1-2 was standardized to the LT90 of Example D1. This standardization process makes it possible to compare Examples D1 and D2 and Comparative Example CD1.
  • a light emitting device D4 was produced in the same manner as in Example D1. The maximum peak wavelength of the emission spectrum of light emitting element D4 was 515 nm. LT90 was measured when driving at constant current with an initial luminance of 1000 cd/m 2 .
  • Example D3-2 Fabrication and evaluation of light emitting device D3-2
  • Light emitting device D3-2 was fabricated in the same manner as Example D3, except that the thickness of the light emitting layer in Example D3 was changed from 35 nm to 60 nm. did.
  • the maximum peak wavelength of the emission spectrum of light emitting element D3-2 was 515 nm.
  • the relative value of LT90 to light emitting element D4 when driven at constant current with an initial luminance of 1000 cd/m 2 was 2.4.
  • Table 3 shows the LT90 values of light emitting element D4 when the LT90 of Example D3-2 was standardized to the LT90 of Example D3. This standardization process makes it possible to compare Examples D3 and D4 and Comparative Example CD2.
  • ⁇ Comparative Example CD5 Production and evaluation of light emitting device CD5 (formation of anode and hole injection layer) An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by sputtering. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, is formed into a film with a thickness of 35 nm by spin coating, and heated on a hot plate at 240° C. for 15 minutes in an air atmosphere. A hole injection layer was thereby formed.
  • ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • a polymer compound CP4 was dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film with a thickness of 60 nm was formed by spin coating on the hole transport layer, and the film was heated at 170°C for 10 minutes on a hot plate in a nitrogen gas atmosphere to emit light. formed a layer.
  • Example D5 Production and evaluation of light emitting element D5
  • Light emitting element D5 was produced in the same manner as comparative example CD5, except that polymer compound P3 was used instead of polymer compound CP4 in comparative example CD5.
  • the maximum peak wavelength of the emission spectrum of light emitting element D5 was 465 nm.
  • the relative value of LT80 to light emitting element CD5 when driven at constant current with an initial luminance of 2100 cd/m 2 was 1.39. The results are shown in Table 4.
  • Example D6 Production and evaluation of light-emitting element D6
  • Light-emitting element D6 was produced in the same manner as Comparative Example CD5, except that polymer compound P4 was used instead of polymer compound CP4 in Comparative Example CD5.
  • the maximum peak wavelength of the emission spectrum of light emitting element D6 was 465 nm.
  • the relative value of LT80 to light emitting element CD5 when driven at constant current with an initial luminance of 2100 cd/m 2 was 3.23. The results are shown in Table 4.
  • Example D7 Production and evaluation of light emitting element D7
  • Light emitting element D7 was produced in the same manner as comparative example CD5, except that polymer compound P5 was used instead of polymer compound CP4 in comparative example CD5.
  • the maximum peak wavelength of the emission spectrum of light emitting element D7 was 465 nm.
  • the relative value of LT80 to light emitting element CD5 when driven at constant current with an initial luminance of 2100 cd/m 2 was 1.78. The results are shown in Table 4.

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Abstract

L'invention concerne un composé polymère qui est utile dans la fabrication d'éléments électroluminescents ayant des durées de vie de luminance exceptionnelles.　La présente invention porte sur un composé polymère comprenant deux types ou plus du motif constitutif représenté dans la formule (0-1). [Dans la formule, a représente un nombre entier compris entre 0 et 6 ; et R1 représente un groupe alkyle, un groupe cycloalkyle, un groupe alcoxy, un groupe cycloalcoxy, un groupe aryle, un groupe aryloxy, un groupe hétérocyclique monovalent, un groupe amino substitué ou un atome d'halogène, et ces groupes peuvent avoir des groupes substituants. S'il y a une pluralité de R1, ceux-ci peuvent être identiques ou différents. R0 représente un atome d'hydrogène, un groupe alkyle, un groupe cycloalkyle, un groupe alcoxy, un groupe cycloalcoxy, un groupe aryle et un groupe aryloxy, un groupe hétérocyclique monovalent, un groupe amino substitué ou un atome d'halogène, et ces groupes peuvent avoir des groupes substituants. Les plusieurs R0 peuvent être identiques ou différents. Au moins l'un des R0 représente un groupe aryle ayant une structure spécifique.]
PCT/JP2023/005677 2022-03-14 2023-02-17 Composé polymère et élément électroluminescent l'utilisant WO2023176304A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007519800A (ja) * 2004-01-30 2007-07-19 エス ケー コーポレイション ９，９−ジ（フルオレニル）−２，７−フルオレニル単位を有する有機エレクトロルミネッセント高分子およびこれを用いて製造される有機エレクトロルミネッセント素子
WO2011105622A1 (fr) * 2010-02-25 2011-09-01 住友化学株式会社 Composé polymère de fluoranthène

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007519800A (ja) * 2004-01-30 2007-07-19 エス ケー コーポレイション ９，９−ジ（フルオレニル）−２，７−フルオレニル単位を有する有機エレクトロルミネッセント高分子およびこれを用いて製造される有機エレクトロルミネッセント素子
WO2011105622A1 (fr) * 2010-02-25 2011-09-01 住友化学株式会社 Composé polymère de fluoranthène

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