WO2017146083A1 - Élément électroluminescent et composé polymère utilisé pour ledit élément électroluminescent - Google Patents

Élément électroluminescent et composé polymère utilisé pour ledit élément électroluminescent Download PDF

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WO2017146083A1
WO2017146083A1 PCT/JP2017/006523 JP2017006523W WO2017146083A1 WO 2017146083 A1 WO2017146083 A1 WO 2017146083A1 JP 2017006523 W JP2017006523 W JP 2017006523W WO 2017146083 A1 WO2017146083 A1 WO 2017146083A1
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group
formula
compound
substituent
ring
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PCT/JP2017/006523
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Japanese (ja)
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茉由 吉岡
星一郎 横家
元章 臼井
浩平 浅田
敦資 麻野
一栄 大内
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住友化学株式会社
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Priority to JP2018501726A priority Critical patent/JP6881430B2/ja
Publication of WO2017146083A1 publication Critical patent/WO2017146083A1/fr

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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
    • C08G61/12—Macromolecular compounds containing atoms other than carbon 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • 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

Definitions

  • the present invention relates to a light emitting element and a polymer compound used for the light emitting element.
  • Light-emitting elements can be used for display and lighting applications, and research and development are actively conducted.
  • This light-emitting element has an organic layer such as a light-emitting layer and a charge transport layer.
  • Patent Documents 1 and 2 describe, for example, a light emitting element in which a light emitting layer containing a phosphorescent compound is stacked on a light emitting layer containing a polymer compound containing an arylamine structural unit represented by the following formula. ing.
  • an object of the present invention is to provide a light-emitting element that is excellent in external quantum efficiency.
  • Another object of the present invention is to provide a polymer compound useful for producing a light emitting device having excellent external quantum efficiency.
  • the present invention provides the following [1] to [15].
  • a 2nd light emitting layer contains at least 1 sort (s) chosen from the group which consists of a high molecular compound containing the structural unit represented by Formula (1), and the crosslinked body of the said high molecular compound.
  • a 1 , a 2 and a 3 each independently represents an integer of 0 or more and 5 or less. When a plurality of a 3 are present, they may be the same or different.
  • Ring S 1 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent other than R A1 . When a plurality of the substituents are present, they may be the same or different.
  • R A1 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. It may be.
  • Ar A1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar A2 , Ar A3 and Ar A4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups May have a substituent.
  • Ar A2 , Ar A3 and Ar A4 they may be the same or different.
  • R A3 , R A4 , R A5 and R A6 each independently represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R A4 , R A5 and R A6 are present, they may be the same or different.
  • R A2 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. It may be. ] [3] The light emitting device according to [1] or [2], wherein the polymer compound containing the structural unit represented by the formula (1) or a crosslinked product of the polymer compound further contains a phosphorescent structural unit. . [4] The light emitting device according to [1] or [2], wherein the second light emitting layer further contains a phosphorescent compound.
  • L H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R H11 ) 2 ] n H11 —, and these groups optionally have a substituent. When a plurality of L H1 are present, they may be the same or different.
  • n H11 represents an integer of 1 to 10.
  • R H11 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 H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
  • L H2 represents a group represented by —N (—L H21 —R H21 ) —. When a plurality of L H2 are present, they may be the same or different.
  • L H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • R H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a polymer compound comprising the structural unit represented by the formula (1) and a phosphorescent structural unit.
  • M 1G represents a group formed by removing one hydrogen atom from a phosphorescent compound.
  • L 1 represents an oxygen atom, a sulfur atom, a group represented by —N (R A ) —, a group represented by —C (R B ) 2 —, —C (R B ) ⁇ C (R B ) —
  • R A 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 B 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 B may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • L 1 When a plurality of L 1 are present, they may be the same or different.
  • n a1 represents an integer of 0 to 10. ] [Where: M 1G has the same meaning as described above.
  • L 2 and L 3 each independently represents an oxygen atom, a sulfur atom, a group represented by —N (R A ) —, a group represented by —C (R B ) 2 —, or —C (R B ) Represents a group represented by ⁇ C (R B ) —, a group represented by —C ⁇ C—, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • R A and R B have the same meaning as described above.
  • n b1 and n c1 each independently represents an integer of 0 to 10. A plurality of n b1 may be the same or different.
  • Ar 1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
  • M 2G represents a group formed by removing two hydrogen atoms from a phosphorescent compound.
  • L 2 and n b1 have the same meaning as described above.
  • M 3G represents a group formed by removing three hydrogen atoms from a phosphorescent compound.
  • L 2 and n b1 have the same meaning as described above.
  • the polymer compound according to [9], wherein the phosphorescent compound is a compound represented by the formula (2).
  • M 2 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
  • n 3 represents an integer of 1 or more
  • n 4 represents an integer of 0 or more
  • n 3 + n 4 is 2 or 3.
  • M is a rhodium atom or an iridium atom
  • n 3 + n 4 is 3.
  • M is a palladium atom or a platinum atom
  • n 3 + n 4 is 2.
  • E 3 and E 4 each independently represents a carbon atom or a nitrogen atom. However, at least one of E 3 and E 4 is a carbon atom.
  • Ring L 1 represents an aromatic heterocyclic ring, and this ring may have a substituent.
  • substituents When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • rings L 1 When a plurality of rings L 1 are present, they may be the same or different.
  • the ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent.
  • substituents When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • rings L 2 When a plurality of rings L 2 are present, they may be the same or different.
  • a 3 -G 2 -A 4 represents an anionic bidentate ligand.
  • a 3 and A 4 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • G 2 represents a single bond or an atomic group constituting a bidentate ligand together with A 3 and A 4 .
  • n 11 and n 12 each independently represents an integer of 1 or more, and n 11 + n 12 is 2 or 3.
  • M is a rhodium atom or iridium atom
  • n 11 + n 12 is 3
  • M is a palladium atom or platinum atom
  • n 11 + n 12 is 2.
  • R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B , R 18B , R 21B , R 22B , R 23B and R 24B are each independently a hydrogen atom, an alkyl group or a cycloalkyl group Represents 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 optionally have a substituent.
  • R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B , R 18B , R 21B , R 22B , R 23B and R 24B they may be the same or different. Good.
  • R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , R 18B and R 21B , R 11B And R 21B , R 21B and R 22B , R 22B and R 23B , and R 23B and R 24B may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B, and R 24B is represented by formula (DA), formula ( The polymer compound according to [12], which is a group represented by DB) or formula (DC).
  • DA formula
  • m DA1 , m DA2 and m DA3 each independently represent an integer of 0 to 10.
  • 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 optionally have a substituent.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a plurality of TDA may be the same or different. ] [Where: m DA1, m DA2, m DA3 , G DA, Ar DA1, Ar DA2, Ar DA3 and T DA is the same as defined above.
  • m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 to 10.
  • Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 may be the same or different.
  • m DA1 , Ar DA1 and T DA have the same meaning as described above.
  • the polymer compound including the structural unit represented by the formula (1) includes a crosslinked structural unit having at least one crosslinking group selected from the crosslinking group A group. The high molecular compound in any one.
  • 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 a binding position.
  • These crosslinking groups may have a substituent.
  • the polymer compound according to [14], wherein the crosslinked structural unit is a structural unit represented by formula (3) or formula (4).
  • nA represents an integer of 0 to 5
  • n represents 1 or 2.
  • Ar 1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
  • L A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom, and these groups have a substituent. Also good.
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of LA are present, they may be the same or different.
  • X represents a crosslinking group selected from the crosslinking group A group.
  • X When two or more X exists, they may be the same or different. When a plurality of nA are present, they may be the same or different. ] [Where: mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When a plurality of mA are present, they may be the same or different.
  • Ar 3 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon group and a heterocyclic group are directly bonded, and these groups may have a substituent.
  • Ar 2 and Ar 4 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar 2 , Ar 3 and Ar 4 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or sulfur atom to form a ring.
  • K A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR ′′ —, an oxygen atom or a sulfur atom, and these groups have a substituent.
  • R ′′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • X ′ represents a bridging group selected from the bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. .
  • X ′ is a cross-linking group selected from the cross-linking group A group.
  • a light emitting device having excellent external quantum efficiency 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.
  • the “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 8 .
  • the polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or other embodiments.
  • the terminal group of the polymer compound is preferably stable because if the polymerization active group remains as it is, the light emission characteristics or external quantum efficiency may decrease when the polymer compound is used in the production of a light emitting device. It is a group.
  • the terminal group is preferably a group conjugated to the main chain, and examples thereof include a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.
  • Low molecular weight compound means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
  • “Structural unit” means one or more units present in a polymer compound.
  • the “alkyl group” may be linear or branched.
  • the number of carbon atoms of the straight chain alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the alkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc., for example, a trifluoromethyl group, a pentafluoroethyl group,
  • the number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the cycloalkyl group may have a substituent, and examples thereof 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 number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the number of carbon atoms of the substituent.
  • the “alkoxy group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkoxy group is usually 1 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the alkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
  • a substituent for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-buty
  • the number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
  • the cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.
  • the number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
  • the aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.
  • the “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.
  • Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc.
  • a compound in which the ring itself exhibits aromaticity, and a heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring Means a compound.
  • the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.
  • Halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “amino group” may have a substituent, and a substituted amino group is preferable.
  • a substituent which an amino group has an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.
  • the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
  • the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (3,5-di-tert- Butylphenyl) amino group.
  • the “alkenyl group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkenyl group is usually 2-30, preferably 3-20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.
  • the “alkynyl group” may be linear or branched.
  • the number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the branched alkynyl group is usually from 4 to 30, and preferably from 4 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
  • the alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.
  • the “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.
  • the arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formulas (A-1) to (A-20) are preferable.
  • the arylene group includes a group in which a plurality of these groups are bonded.
  • R and R a each independently represents 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 together with the atoms to which they are bonded.
  • the number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Is a group represented by formula (AA-1) to formula (AA-34).
  • the divalent heterocyclic group includes a group in which a plurality of these groups
  • crosslinking group is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc.
  • “Substituent” means 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 crosslinking group.
  • Dendrimer means a group having a regular dendritic branch structure (ie, a dendrimer structure) having an atom or ring as a branch point.
  • dendrimer examples include, for example, International Publication No. 02/066733, Japanese Patent Application Laid-Open No. 2003-231692, International Publication No. 2003/079736, International Publication No. 2006/097717 And the structure described in the literature.
  • the dendron is preferably a group represented by the formula (DA) or a group represented by the formula (DB), and more preferably a group represented by the formula (DA).
  • m DA1 to m DA7 are preferably integers of 5 or less, more preferably integers of 2 or less, and even more preferably 0 or 1.
  • m DA2 to m DA7 are preferably the same integer, and m DA1 to m DA7 are more preferably the same integer.
  • G DA is preferably a group represented by the formula (GDA-11) ⁇ (GDA -15), more preferably a group represented by the formula (GDA-11) ⁇ (GDA -14), further A group represented by formula (GDA-11) or (GDA-14) is preferred, and a group represented by formula (GDA-11) is particularly preferred.
  • 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, and these groups may further have a substituent. When there are a plurality of RDA , they may be the same or different. ]
  • R DA 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 a substituent. May be.
  • 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 carbazole-diyl group, more preferably the formula (A-1) ⁇ Formula (A-3), Formula (A-8), Formula (A-9), Formula (AA-10), Formula (AA-11), Formula (AA-33), or Formula (AA-34) And more preferably a group represented by formula (ArDA-1) to formula (ArDA-5).
  • R DA represents the same meaning as described above.
  • R DB 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 a plurality of 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, and these groups optionally have a substituent.
  • T DA is preferably a group represented by the formula (TDA-1) ⁇ (TDA -3), more preferably a group represented by the formula (TDA-1).
  • R DA and R DB represent the same meaning as described above.
  • the group represented by the formula (DA) is preferably a group represented by the formula (D-A1) to (D-A4), more preferably in the formula (D-A1) or the formula (D-A3). It is a group represented.
  • R p1 , R p2 , R p3 and R p4 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom.
  • R p1 , R p2 and R p4 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
  • np4 represents an integer of 0 to 4.
  • a plurality of np1 may be the same or different.
  • the group represented by the formula (D-B) is preferably a group represented by the formulas (D-B1) to (D-B3), more preferably a group represented by the formula (D-B1).
  • R p1 , R p2 and R p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom.
  • R p1 and R p2 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.
  • np1 and np2 may be the same or different.
  • the group represented by the formula (D-C) is preferably a group represented by the formulas (D-C1) to (D-C4), more preferably a group represented by the formula (D-C1).
  • R p4 , R p5 and R p6 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom. When there are a plurality of R p4 , R p5 and R p6 , they may be the same or different.
  • np4 represents an integer of 0 to 4
  • np5 represents an integer of 0 to 5
  • np6 represents an integer of 0 to 5.
  • Np1 is preferably 0 or 1, more preferably 1.
  • np2 is preferably 0 or 1, more preferably 0.
  • np3 is preferably 0.
  • np4 is preferably an integer of 0 to 2.
  • np5 is preferably an integer of 1 to 3.
  • np6 is preferably an integer of 0 to 2.
  • R p1 , R p2 , R p3 , R p4 , R p5 and R p6 are preferably alkyl groups or cycloalkyl groups, more preferably methyl groups, ethyl groups, isopropyl groups, tert-butyl groups, hexyl groups, 2-ethylhexyl group, cyclohexyl group, methoxy group, 2-ethylhexyloxy group, tert-octyl group or cyclohexyloxy group, more preferably methyl group, ethyl group, isopropyl group, tert-butyl group, hexyl group, 2 -Ethylhexyl group or tert-octyl group.
  • Examples of the group represented by the formula (D-A) include groups represented by the formulas (DA-1) to (DA-12).
  • R D represents 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 group. Represents a group. When two or more RD exists, they may be the same or different. ]
  • Examples of the group represented by the formula (D-B) include groups represented by the formulas (DB-1) to (DB-4).
  • R D represents the same meaning as described above.
  • Examples of the group represented by the formula (D-C) include groups represented by the formulas (DC-1) to (DC-13).
  • R D represents the same meaning as described above.
  • 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.
  • the light emitting device of the present invention is a light emitting device having an anode, a cathode, a first light emitting layer provided between the anode and the cathode, and a second light emitting layer provided between the anode and the cathode.
  • the second light-emitting layer contains at least one selected from the group consisting of a polymer compound containing the structural unit represented by the formula (1) and a crosslinked product of the polymer compound, It is.
  • the first light emitting layer is a layer containing a light emitting material.
  • a light emitting material is classified into a low molecular compound and a high molecular compound, and a low molecular compound is preferable, and these compounds may have a crosslinking group.
  • Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and phosphorescent compounds having iridium, platinum, palladium, rhodium, or europium as a central metal.
  • the light emitting material preferably contains a phosphorescent compound.
  • the first light-emitting layer preferably contains two or more phosphorescent compounds because the external quantum efficiency of the light-emitting device according to this embodiment is excellent.
  • the phosphorescent compound is a compound having phosphorescence.
  • a compound having a high emission quantum yield at room temperature for example, 25 ° C.
  • room temperature for example, 25 ° C.
  • the phosphorescent compound examples include a phosphorescent compound represented by the above formula (2) and a metal complex represented by the following formula.
  • the phosphorescent compound represented by the above formula (2) is used. It is a luminescent compound.
  • the phosphorescent compound contained in the first light emitting layer is preferably a phosphorescent compound represented by the formula (2), and among these, at least one of the phosphorescent compounds contained in the first light emitting layer. It is preferable that the phosphorescent compound represented by Formula (5) is contained as a seed.
  • M 1 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
  • n 1 represents an integer of 1 or more
  • n 2 represents an integer of 0 or more
  • n 1 + n 2 is 2 or 3.
  • M 1 is a rhodium atom or an iridium atom
  • n 1 + n 2 is 3.
  • M 1 is a palladium atom or a platinum atom
  • n 1 + n 2 is 2.
  • 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 R 1 represents a 5-membered aromatic heterocyclic ring, and this ring may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R 1 are present, they may be the same or different.
  • Ring R 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • a 1 -G 1 -A 2 represents an anionic bidentate ligand.
  • a 1 and A 2 each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • G 1 represents a single bond or an atomic group constituting a bidentate ligand together with A 1 and A 2 .
  • M 1 is preferably an iridium atom or a platinum atom, and more preferably an iridium atom.
  • E 1 and E 2 are preferably carbon atoms.
  • the ring R 1 is preferably a 5-membered aromatic heterocyclic ring having 1 to 3 nitrogen atoms as constituent atoms, more preferably an imidazole ring or a triazole ring. These rings may have a substituent.
  • ring R 2 is preferably a 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and is a benzene ring, a pyridine ring or a pyrimidine ring. More preferably, these rings may have a substituent.
  • Examples of the substituent that the ring R 1 and the ring R 2 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 halogen atom,
  • a dendron is preferable, an alkyl group, a cycloalkyl group, an aryl group, a halogen atom or a dendron is more preferable, and these groups may further have a substituent.
  • examples of the anionic bidentate ligand represented by A 1 -G 1 -A 2 include a ligand represented by the following formula. However, the anionic bidentate ligand represented by A 1 -G 1 -A 2 is different from the ligand whose number is defined by the subscript n 1 .
  • the phosphorescent compound represented by the formula (5) is preferably a phosphorescent compound represented by the formula (5-A1) to the formula (5-A4).
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A they may be the same or different.
  • R 11A and R 12A , R 12A and R 13A , R 11A and R 21A , R 21A and R 22A , R 22A and R 23A , and R 23A and R 24A are bonded to each other together with the atoms to which they are bonded.
  • a ring may be formed.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are each preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom More preferably an alkyl group or a cycloalkyl group.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A, and R 24A are an aryl group, a monovalent heterocyclic group, or a substituted amino group
  • the external quantum efficiency of the light emitting device is more excellent, so that dendron
  • a group represented by the formula (DA), formula (DB) or formula (DC) is preferable, and the group represented by the formula (DA) or formula (DC) is preferred. More preferred are the groups
  • Examples of the phosphorescent compounds represented by the formulas (5-A1) to (5-A4) include phosphorescent compounds represented by the following formulas.
  • the first light emitting layer has excellent external quantum efficiency of the light emitting device according to this embodiment, in addition to the phosphorescent compound represented by the formula (5), the following formulas (2-B1) to (2- It is preferable to contain the phosphorescent compound represented by B5).
  • Examples of the phosphorescent compound used for forming the first light-emitting layer include Japanese Unexamined Patent Publication No. 2004-530254, Japanese Unexamined Patent Application Publication No. 2008-179617, Japanese Unexamined Patent Application Publication No. 2011-105701, Japanese Unexamined Patent Publication No. 2007-504272, They can be synthesized according to the methods described in JP2013-147449A and JP2013-147450A.
  • the first light emitting layer is composed of a phosphorescent compound, a hole injecting property, a hole transporting property, an electron injecting property, and an electron transporting property.
  • a host material having at least one of the following functions.
  • the host material may be one kind alone or two or more kinds.
  • the total content of the phosphorescent compound is usually 0.
  • the amount is 1 to 50 parts by mass, preferably 5 to 40 parts by mass.
  • the lowest excited triplet state (T 1 ) of the host material has excellent external quantum efficiency of the light emitting device according to this embodiment, it is equivalent to T 1 of the phosphorescent compound used for forming the first light emitting layer. It is preferable that the energy level is higher or higher.
  • the light-emitting element according to this embodiment can be manufactured by a solution coating process, it exhibits solubility in a solvent capable of dissolving the phosphorescent compound used for forming the first light-emitting layer. It is preferable.
  • the host material is classified into a low molecular compound (hereinafter referred to as “low molecular host”) and a high molecular compound (hereinafter referred to as “polymer host”), and a low molecular host is preferable.
  • low molecular host a low molecular compound
  • polymer host a high molecular compound
  • the low molecular host is preferably a compound represented by the formula (H-1).
  • Ar H1 and Ar H2 are phenyl group, fluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, thienyl group, benzothienyl group, dibenzothienyl group, furyl group, benzofuryl Group, dibenzofuryl group, pyrrolyl group, indolyl group, azaindolyl group, carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group, phenyl group, spirobifluorenyl group, It is more preferably a pyridyl group, pyrimidinyl group, triazinyl group, dibenzothienyl group, dibenzofuryl group, carbazolyl group or azacarbazo
  • Ar H1 and Ar H2 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable.
  • Alkyl groups are more preferred, and these groups may further have a substituent.
  • n H1 is preferably 1.
  • n H2 is preferably 0.
  • n H3 is preferably an integer of 1 to 3, more preferably 1.
  • n H11 is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and still more preferably 1.
  • R H11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom or an alkyl group, and these groups have a substituent. It may be.
  • L H1 is preferably an arylene group or a divalent heterocyclic group.
  • L H1 represents formulas (A-1) to (A-3), formulas (A-8) to (A-10), formulas (AA-1) to (AA-6), formulas (AA-10) to A group represented by formula (AA-21) or formulas (AA-24) to (AA-34) is preferred, and the formula (A-1), formula (A-2), formula (AA-2), A group represented by formula (AA-4) or (AA-14) is more preferable.
  • L H1 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable, and an alkyl group, an alkoxy group, an aryl group A group or a monovalent heterocyclic group is more preferable, and these groups may further have a substituent.
  • L H21 is preferably a single bond or an arylene group, and this arylene group may have a substituent.
  • the definition and examples of the arylene group or divalent heterocyclic group represented by L H21 are the same as the definitions and examples of the arylene group or divalent heterocyclic group represented by L H1 .
  • R H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a definition of the aryl group and monovalent heterocyclic group represented by R H21 and Examples are the same as the definitions and examples of the aryl group and monovalent heterocyclic group represented by Ar H1 and Ar H2 .
  • Definition and examples of the substituent which may be R H21 optionally has are the same as definitions and examples of the substituent may have Ar H1 and Ar H2 is.
  • the compound represented by the formula (H-1) is preferably a compound represented by the formula (H-2).
  • Examples of the compound represented by the formula (H-1) include compounds represented by the formulas (H-101) to (H-118).
  • the polymer host is preferably a polymer compound containing a structural unit represented by the formula (Y).
  • Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups have a substituent. It may be.
  • Arylene group represented by Ar Y1 is more preferably the formula (A-1), formula (A-2), the formula (A-6) - (A -10), formula (A-19) or Formula ( A-20), and these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar Y1 is more preferably a formula (AA-1)-(AA-4), a formula (AA-10)-(AA-15), a formula (AA-18) -(AA-21), a group represented by formula (AA-33) or formula (AA-34), and these groups may have a substituent.
  • more preferable ranges and further preferable ranges of the arylene group and the divalent heterocyclic group are the above-mentioned Ar. This is the same as the more preferable range and further preferable range of the arylene group and divalent heterocyclic group represented by Y1 .
  • Examples of the “divalent group in which an arylene group and a divalent heterocyclic group are directly bonded” include groups represented by the following formulas, and these groups may have a substituent.
  • R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R XX is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • 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 the formula (Y) include structural units represented by the formulas (Y-1)-(Y-10).
  • 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 optionally 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 atom to which each is bonded.
  • R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • R Y1 represents the same meaning as described above.
  • X Y1 is, -C (R Y2) 2 -
  • 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 Y2 may be the same or different, and R Y2 may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]
  • R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • the combination of two R Y2 in the group represented by —C (R Y2 ) 2 — is preferably an alkyl group or a cycloalkyl group, both an aryl group, and both are monovalent complex A cyclic group, or one is an alkyl group or a cycloalkyl group, and the other is an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Two R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the group represented by —C (R Y2 ) 2 — Is preferably a group represented by the formula (Y-A1)-(Y-A5), and these groups may have a substituent.
  • the combination of two R Y2 in the group represented by —C (R Y2 ) ⁇ C (R Y2 ) — is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups optionally have a substituent.
  • R Y2 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 together with the atoms to which each is bonded. When R Y2 forms a ring, —C (R Y2 ) 2 —C (R Y2 ) 2 — The group represented is preferably a group represented by the formula (Y-B1)-(Y-B5), and these groups may have a substituent.
  • R Y2 represents the same meaning as described above.
  • R Y1 represents the same meaning as described 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 aryl group, and these groups optionally have a substituent.
  • R Y1 represents the same meaning as described 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 optionally have a substituent.
  • R Y4 is preferably an aryl group, and these groups optionally have a substituent.
  • the structural unit represented by the formula (Y) for example, a structural unit composed of an arylene group represented by the formula (Y-101)-(Y-121), a formula (Y-201)-(Y-207) A divalent group in which an arylene group represented by the formula (Y-301)-(Y-304) and a divalent heterocyclic group are directly bonded to each other.
  • the structural unit is given.
  • the structural unit represented by the formula (Y), wherein Ar Y1 is an arylene group, is excellent in external quantum efficiency, and is preferably 0.5% relative to the total amount of structural units contained in the polymer compound. It is ⁇ 80 mol%, more preferably 30 to 60 mol%.
  • the polymer host is excellent in hole transport properties, it is preferable that the polymer host further contains a structural unit represented by the following formula (X).
  • a X1 and a X2 each independently represent an integer of 0 to 2.
  • Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups are substituents You may have. When there are a plurality of Ar X2 and Ar X4 , 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. When there are a plurality of R X2 and R X3 , they may be the same or different. ]
  • a X1 is preferably 0 or 1 because of its excellent external quantum efficiency.
  • a X2 is preferably 0 because of its excellent external quantum efficiency.
  • R X1 , R X2 and R X3 are preferably aryl groups, and these groups may have a substituent.
  • the arylene group represented by Ar X1 and Ar X3 is more preferably a group represented by the formula (A-1) or the formula (A-9), and these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by the formula (AA-1), the formula (AA-2), or the formula (AA-7)-(AA-26). These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably an arylene group which may have a substituent.
  • the arylene group represented by Ar X2 and Ar X4 more preferably, the formula (A-1), the formula (A-6), the formula (A-7), the formula (A-9)-(A-11) Or it is group represented by a formula (A-19), and these groups 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 .
  • More preferred ranges and further preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group in which the arylene group represented by Ar X2 and Ar X4 and the divalent heterocyclic group are directly bonded are respectively This is the same as the more preferable range and further preferable range of the arylene group and divalent heterocyclic group represented by Ar X1 and Ar X3 .
  • Examples of the divalent group in which the arylene group represented by Ar X2 and Ar X4 and the divalent heterocyclic group are directly bonded include an arylene group represented by Ar Y1 in the formula (Y) and a divalent heterocyclic group And the same as the divalent group directly bonded to each other.
  • Ar X2 and Ar X4 are preferably an arylene group which may have a substituent.
  • the substituent which the groups represented by Ar X1 to Ar X4 and R X1 to R X3 may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups further have a substituent. You may do it.
  • the structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1)-(X-7).
  • 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 cyano. Represents a group, and these groups may have a substituent.
  • a plurality of R X4 may be the same or different.
  • a plurality of R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
  • the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably 1 to 5 mol% with respect to the total amount of the structural units contained in the polymer host. It is 40 mol%, more preferably 5 to 30 mol%.
  • Examples of the structural unit represented by the formula (X) include structural units represented by the formulas (X1-1)-(X1-11).
  • polymer host examples include polymer compounds (P-1) to (P-6) shown in Table 1.
  • the “other” structural unit means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).
  • the polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes.
  • a copolymer obtained by polymerization is preferred.
  • the polymer host can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and Suzuki reaction, Yamamoto reaction, Buchwald Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, Stille reaction, Negishi reaction, and Kumada reaction.
  • the polymerization method as a method of charging the monomer, a method of charging the entire amount of the monomer into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.
  • the transition metal catalyst include a palladium catalyst and a nickel catalyst.
  • Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination.
  • a lower alcohol such as methanol
  • filtering the deposited precipitate and then drying.
  • These methods are performed alone or in combination.
  • the purity of the polymer host is low, it can be purified by usual methods such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, and the like.
  • the first light emitting layer includes at least one light emitting material and at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, and an antioxidant. It is preferable to contain a material.
  • the content of the light emitting material is 100 parts by weight in total of the light emitting material, hole transport material, hole injection material, electron transport material and electron injection material in the first light emitting layer. Usually 0.1 to 100 parts by weight.
  • the first light-emitting layer is formed using an ink containing a light-emitting material (hereinafter also referred to as “ink used for forming the first light-emitting layer”), a spin coating method, a gravure coating method, a bar coating method, a roll coating. It can be formed by a coating method such as a method, a spray coating method, a screen printing method, a die coating method, an ink jet printing method, a capillary coating method, or a nozzle coating method.
  • a coating method such as a method, a spray coating method, a screen printing method, a die coating method, an ink jet printing method, a capillary coating method, or a nozzle coating method.
  • the viscosity of the ink used for forming the first light emitting layer may be adjusted depending on the type of printing method. However, when a solution such as an ink jet printing method is applied to a printing method via a discharge device, In order to prevent clogging and flight bending, the pressure is 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 chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene and the like.
  • Aromatic hydrocarbon solvents such as: cyclohexane, methylcyclohexane, n-hexane, n-octane, n-decane, n-dodecane, bicyclohexyl and other aliphatic hydrocarbon solvents; methyl ethyl ketone, cyclohexanone, acetophenone and other ketone solvents Ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; Alcohol solvents hexanol; sulfoxide solvents such as dimethyl sulfoxide; N- methyl-2-pyrrolidone, N, include amide solvents such as N- dimethylformamide.
  • a solvent may be used individually by 1
  • the amount of the solvent is usually 1000 to 100,000 parts by weight with respect to 100 parts by weight of the light emitting material.
  • the hole transport material is classified into a low molecular compound and a high molecular compound, and a high molecular compound is preferable, and a high molecular compound having a crosslinking group is more preferable.
  • Examples of the low molecular weight compound include triphenylamine and derivatives thereof, N, N′-di-1-naphthyl-N, N′-diphenylbenzidine, and N, N′-diphenyl-N, N′-di ( and aromatic amine compounds such as m-tolyl) benzidine.
  • polymer compound examples include polyvinyl carbazole 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. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone.
  • the content of the hole transport material is the light emitting material, hole transport material, hole injection material, electron transport material and electron injection in the first light emitting layer.
  • the amount is usually 0.1 to 99 parts by weight, preferably 0.1 to 50 parts by weight, and more preferably 0.5 to 10 parts by weight with respect to 100 parts by weight of the total material.
  • a hole transport material may be used individually by 1 type, or may use 2 or more types together.
  • Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds.
  • the electron transport material may have a crosslinking group.
  • Examples of the low molecular compound include a metal complex 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 a metal.
  • the content of the electron transport material is the same as that of the light-emitting material, hole transport material, hole injection material, electron transport material, and electron injection material in the first light-emitting layer.
  • the amount is usually 0.1 to 99 parts by weight, preferably 0.1 to 50 parts by weight, more preferably 0.5 to 10 parts by weight with respect to the total of 100 parts by weight.
  • An electron transport material may be used individually by 1 type, or may use 2 or more types together.
  • the hole injection material and the electron injection material are each classified into a low molecular compound and a high molecular compound.
  • the hole injection material and the electron injection material may have a crosslinking group.
  • low molecular weight compounds 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 compound examples include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, and polyquinoxaline, and derivatives thereof; polymers containing an aromatic amine structure in the main chain or side chain, etc.
  • the conductive polymer is mentioned.
  • the contents of the hole injecting material and the electron injecting material are the light emitting material, hole transporting material, and hole injecting in the first light emitting layer.
  • the amount is usually 0.1 to 30 parts by weight, preferably 0.1 to 10 parts by weight, more preferably 0.1 to 1 part by weight with respect to 100 parts by weight of the total of the material, the electron transport material and the electron injection material.
  • 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 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 ions to be doped is an anion for a hole injection material and a cation for an electron injection material.
  • the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion.
  • the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion. Only one kind or two or more kinds of ions may be doped.
  • the antioxidant may be a compound that does not inhibit light emission and charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.
  • the content of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the light emitting material.
  • Antioxidants may be used alone or in combination of two or more.
  • the ink used for forming the first light emitting layer may contain other components.
  • the second light emitting layer is selected from the group consisting of a polymer compound containing a structural unit represented by formula (1) and a crosslinked product of the polymer compound containing a structural unit represented by formula (1). It is a layer containing at least one kind.
  • a 1 , a 2, and a 3 are preferably 0 or 1, since the external quantum efficiency is excellent, more preferably a 1 is 1, a combination in which a 2 and a 3 are 0, and a 2 is 1. And a combination in which a 1 and a 3 are 0, or a combination in which a 1 , a 2 and a 3 are 0.
  • the aromatic hydrocarbon ring represented by the ring S 1 has usually 6 to 60, preferably 6 to 20, more preferably 6 to 14 carbon atoms constituting the ring.
  • Examples of the aromatic hydrocarbon ring represented by the ring S 1 include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, pyrene ring, perylene ring, or chrysene ring.
  • a benzene ring, a naphthalene ring, a phenanthrene ring, a dihydrophenanthrene ring or a fluorene ring, and a benzene ring is more preferable.
  • the aromatic heterocycle represented by the ring S 1 has usually 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms constituting the ring.
  • Examples of the aromatic heterocycle represented by ring S 1 include pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilole ring, phenoxazine.
  • R A1 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or an aryl group, more preferably an alkyl group, since these have higher external quantum efficiency, and these groups have a substituent. It may be.
  • the alkyl group represented by R A1 has 1 to 12 carbon atoms because the polymer compound suitably used for the light emitting device of the embodiment of the present invention has excellent solubility and facilitates the production of the light emitting device.
  • An alkyl group is preferred, an alkyl group having 2 to 12 carbon atoms is more preferred, and an alkyl group having 6 to 12 carbon atoms is still more preferred.
  • alkyl group represented by R A1 it becomes easy to synthesize a polymer compound suitably used in the light-emitting device of the embodiment of the present invention, so that a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, A hexyl group is more preferred.
  • the monocyclic or condensed arylene group represented by Ar A1 is preferably represented by the formula (A-1) to the formula (A-9), the formula (A-19), or the formula (A-20). More preferred are formulas (A-1) to (A-3), and these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar A1 is preferably a group represented by the formula (B-1) to the formula (B-4), the formula (B-10) to the formula (B-15), or the formula (B— 24) to groups represented by formula (B-26), and these groups optionally have a substituent.
  • Ar A1 is preferably an arylene group because it has a higher external quantum efficiency.
  • the arylene group represented by Ar A2 , Ar A3 and Ar A4 is preferably represented by the formula (A-1) to the formula (A-9), the formula (A-19), or the formula (A-20). These groups may have a substituent.
  • the divalent heterocyclic group represented by Ar A2 , Ar A3 and Ar A4 is preferably a group represented by formula (B-1) to formula (B-4), formula (B-10) to formula (B-15), Alternatively, groups represented by formula (B-24) to formula (B-26), and these groups may have a substituent.
  • More preferable ranges of the arylene group and the divalent heterocyclic group in the divalent group in which the arylene group represented by Ar A2 , Ar A3 and Ar A4 and the divalent heterocyclic group are directly bonded are Ar A2, is the same as the more preferred range of arylene group and divalent heterocyclic group represented by Ar A3 and Ar A4.
  • Examples of the divalent group in which the arylene group represented by Ar A2 , Ar A3 and Ar A4 and the divalent heterocyclic group are directly bonded include an arylene group represented by Ar Y1 and a divalent heterocyclic group. This is the same as the example of the divalent group directly bonded.
  • Ar A2 is preferably an arylene group, more preferably a group represented by the formula (A-7), since it has excellent external quantum efficiency, and these groups may have a substituent.
  • Ar A3 and Ar A4 are more preferably an arylene group, and more preferably a group represented by the formula (A-1), since the external quantum efficiency is excellent, and these groups have a substituent. Also good.
  • Examples of the monovalent heterocyclic group represented by R A3 , R A4 , R A5 and R A6 include a dihydrocarbazolyl group, a tetrahydrocarbazolyl group in addition to the groups mentioned in the description of the monovalent heterocyclic group. Group and hexahydrocarbazolyl group.
  • R A3 , R A4 , R A5 and R A6 are preferably groups selected from the aryl group CC group or groups selected from the monovalent heterocyclic group DD group, and are represented by the formula (CC-1), the formula (CC— 6) or a group represented by the formula (DD-14) is more preferable, and these groups may have a substituent, and when there are a plurality of R A3 , R A4 , R A5 and R A6 , They may be the same or different.
  • the group represented by Ar A1 , Ar A2 , Ar A3 , Ar A4 , R A3 , R A4 , R A5 and R A6 may have, preferably an alkyl group, a cycloalkyl group, an aryl group Alternatively, it is a monovalent heterocyclic group, and these groups may further have a substituent.
  • the content of the structural unit represented by the formula (1) is usually 0.1 mol% to 100 mol% with respect to the total content of the structural units contained in the polymer compound, and the hole transport property is Since it is excellent, it is preferably 10 mol% to 90 mol%, more preferably 30 mol% to 50 mol%, and still more preferably 40 mol% to 50 mol%.
  • Examples of the structural unit represented by the formula (1) include structural units represented by the formulas (1′-1) to (1′-18).
  • the structural unit represented by the formula (1) may be included alone or in combination of two or more.
  • the structural unit represented by the formula (1) is preferably a structural unit represented by the formula (1a) because the external quantum efficiency is more excellent.
  • the aromatic hydrocarbon ring represented by the ring S 2 has usually 6 to 60, preferably 6 to 20, more preferably 6 to 14 carbon atoms constituting the ring. Examples and preferred ranges of the aromatic hydrocarbon ring represented by ring S 2 are the same as those of the aromatic hydrocarbon ring represented by ring S 1 and preferred ranges.
  • the aromatic heterocyclic ring represented by ring S 2 has usually 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms constituting the ring. Examples and preferred ranges of the aromatic heterocycle represented by ring S 2 are the same as those of the aromatic heterocycle represented by ring S 1 and preferred ranges.
  • the preferred range of the group and atom represented by R A2 is the same as the preferred range of the group and atom represented by R A1 .
  • Examples of the structural unit represented by the formula (1a) include structural units represented by the formula (1Y-1) to the formula (1Y-13), preferably the formula (1Y-1) to the formula (1Y -3), a structural unit represented by formula (1Y-6), formula (1Y-7), formula (1Y-9), formula (1Y-10) or formula (1Y-13).
  • Examples of the structural unit represented by the formula (1) include structural units represented by the formulas (1-1) to (1-18), and preferably the formulas (1-1) to (1-6). ), Formula (1-10), formula (1-11), formula (1-13), formula (1-17) or formula (1-18).
  • the polymer compound containing the structural unit represented by the formula (1) is further a phosphorescent structural unit (in particular, a group formed by removing a hydrogen atom from the phosphorescent compound represented by the formula (2)). It is preferable that the polymer compound further contains at least one phosphorescent compound selected from the structural units represented by formula (1G), formula (2G), formula (3G), and formula (4G). More preferably, the structural unit is included.
  • R A is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent.
  • L 1 is preferably a group represented by —C (R B ) 2 — or an arylene group, and more preferably a group represented by formula (A-1) or formula (A-2). These groups may have a substituent.
  • R B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, more preferably a hydrogen atom, and these groups optionally have a substituent.
  • R A , R B and L 1 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, and a halogen atom. These groups may further have a substituent.
  • na1 is preferably an integer of 0 to 2, more preferably 0.
  • M 1G is preferably a group represented by the formula (GM-1).
  • n 111 represents 1 or 2.
  • n 112 represents 0 or 1; However, n 111 + n 112 is 1 or 2.
  • M is a rhodium atom or an iridium atom
  • n 111 + n 112 is 2
  • M is a palladium atom or a platinum atom
  • n 111 + n 112 is 1.
  • E 3 and E 4 represent the same meaning as described above.
  • Ring R 1G and ring R 1G1 each independently represent an aromatic heterocyclic ring, and these rings may have a substituent.
  • substituents When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • rings R 1G When a plurality of rings R 1G are present, they may be the same or different.
  • Ring R 2G and ring R 2G1 each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings optionally have a substituent.
  • a plurality of the substituents When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • rings R 2G When a plurality of rings R 2G are present, they may be the same or different.
  • E 4 is a carbon atom.
  • One of the ring R 1G1 and the ring R 2G1 has a bond.
  • a 3 -G 2 -A 4 represents the same meaning as described above. ]
  • n 112 is 0 or 1, and more preferably 0.
  • M is a palladium atom or a platinum atom
  • n 112 is 0.
  • Ring R 1G is preferably an aromatic heterocyclic ring having 1 to 4 nitrogen atoms as constituent atoms, more preferably a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring. May have a substituent.
  • Ring R 2G is preferably an aromatic hydrocarbon ring, more preferably a benzene ring, a naphthalene ring or a fluorene ring, and these rings may have a substituent.
  • Examples of the substituent that the ring R 1G and the ring R 2G 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, and a dendron.
  • an alkyl group, an aryl group, or a dendron is more preferable, and these groups may further have a substituent.
  • At least one ring selected from the group consisting of ring R 1G and ring R 2G has a dendron.
  • the number of dendrons contained in at least one ring selected from the group consisting of ring R 1G and ring R 2G is preferably 1 to 3, more preferably 1.
  • the dendron possessed by at least one ring selected from the group consisting of ring R 1G and ring R 2G is a group represented by the formula (DA) or (DB), and m DA1 is 1 to 10
  • Ar DA1 bonded to ring R 1G and / or ring R 2G is preferably a group represented by the formula (ArDA-1).
  • G DA bonded to R 1G and / or ring R 2G is a group represented by formula (GDA-11), formula (GDA-12), formula (GDA-14) or formula (GDA-15) are preferable, and a group represented by the formula (GDA-11) or the formula (GDA-14) is more preferable.
  • the dendron possessed by at least one of the ring R 1G and the ring R 2G is represented by the formula (D-A1), the formula (D-A3), the formula (D-B1) or the formula (D-B3). And a group represented by the formula (D-A1) or (D-A3) is more preferable.
  • GM-1 At least one of the ligands (the ligand represented by ring R 1G -ring R 2G ) whose number is defined by the subscript n 111 is represented by the formula (GM-L1 It is preferable that it is a ligand represented by.
  • R G1 and R G2 , R G2 and R G3 , and R G3 and R G4 are not bonded to form a ring.
  • R G3 and R G4 are preferably bonded to form an aromatic ring.
  • R G1 ⁇ R G8 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, cycloalkoxy group, or an aryloxy group or a dendron, and R G1 R G2 may be bonded, R G2 and R G3 may be bonded, or R G3 and R G4 may be bonded to form an aromatic ring, and these groups may have a substituent.
  • R G1 and R G2, R G2 and R G3, R G3 and R G4, R G4 and R G5, R G5 and R G6, R G6 and R G7, and, R G7 and R G8 are each bound, You may form the ring with the atom to which each couple
  • R G1 , R G4 , R G5 and R G8 are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, and these groups may have a substituent.
  • R G2 , R G3 , R G6 and R G7 are preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, and a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic ring.
  • a group or a dendron is more preferable, a hydrogen atom or a dendron is further preferable, and these groups may have a substituent.
  • At least one of R G1 to R G8 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and R G2 , R G3 , More preferably, at least one of R G6 and R G7 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group or a dendron, and these groups are substituted It may have a group.
  • R G2 , R G3 , R G6 and R G7 is preferably a dendron, and at least one of R G2 and R G6 is More preferably, it is a dendron.
  • R G2 and R G6 Is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group, and these groups optionally have a substituent. .
  • the plurality of R G1 to R G8 may be the same or different.
  • the ligand represented by the ring R 1G1 -ring R 2G1 is preferably a ligand represented by the formula (GM-L1).
  • R G1 and R G2 , R G2 and R G3 , and R G3 and R G4 are not bonded to form a ring.
  • R G3 and R G4 are preferably bonded to form an aromatic ring.
  • R G2 , R G3 , R G6 or R G7 may be a bond.
  • R G6 is a bond.
  • Exemplary and preferred embodiments of A 3 -G 2 -A 4 include those similar to the illustrative and preferred embodiments of A 3 -G 2 -A 4 in phosphorescent compound represented by the formula (2) described later .
  • L 2 is preferably a group represented by —C (R B ) 2 —, an arylene group or a divalent heterocyclic group, and represented by formula (A-1) or formula (A-2). It is more preferably a group, and these groups may have a substituent.
  • L 3 is preferably a group represented by —C (R B ) 2 — or an arylene group, and more preferably a group represented by Formula (A-1) or Formula (A-2). These groups may have a substituent.
  • n b1 and n c1 are usually integers of 0 to 10, preferably 0.
  • Ar 1M is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a carbazole ring, a phenoxazine ring, or a phenothiazine ring.
  • a group in which three hydrogen atoms directly bonded are removed is preferable, and a group in which three hydrogen atoms directly bonded to a carbon atom constituting the ring are removed from a benzene ring is more preferable. It may have a substituent.
  • M 2G is preferably a group represented by the formula (GM-2) or the formula (GM-3).
  • n113 and n114 each independently represents 0 or 1. However, n 113 + n 114 is 0 or 1. When M is a rhodium atom or an iridium atom, n 113 + n 114 is 1, and when M is a palladium atom or a platinum atom, n 113 + n 114 is 0. Ring R 1G2 represents an aromatic heterocycle, and the ring may have a substituent.
  • Ring R 2G2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and the ring may have a substituent.
  • the substituents When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • the ring R 2G2 is a 6-membered aromatic heterocyclic ring, E 4 is a carbon atom.
  • one of the ring R 1G2 and the ring R 2G2 has two bonds, or each of the ring R 1G2 and the ring R 2G2 has one bond.
  • n 114 is preferably 0.
  • the definition of ring R 1G2 is the same as the definition of ring R 1G .
  • the definition of the ring portion excluding the bond of ring R 1G2 is the same as the definition of ring R 1G .
  • the definition of ring R 2G2 is the same as the definition of ring R 2G .
  • the definition of the ring portion excluding the bond of ring R 2G2 is the same as the definition of ring R 2G .
  • the substituent that the ring R 1G2 and the ring R 2G2 may have is the same as the substituent that the ring R 1G and the ring R 2G may have.
  • Each of the ring R 1G2 and the ring R 2G2 preferably has one bond.
  • the ligand represented by ring R 1G2 -ring R 2G2 is preferably a ligand represented by the formula (GM-L1).
  • the ligand represented by the ring R 1G2 -ring R 2G2 is preferably a ligand represented by the formula (GM-L1).
  • R G2 and R G6 , R G2 and R G7 , R G3 and R G6 , or R G3 and R G7 are preferably bonds.
  • R 1G2 -ring R 2G2 is a ligand represented by the formula (GM-L1), and R G3 and R G4 are bonded to form an aromatic ring , R G2 and R G6 , or R G2 and R G7 are preferably bonds.
  • R G2 and R G3 are preferably bonded, and two of the carbon-hydrogen bonds, R G6 and R G7 have an aromatic ring formed by bonding.
  • R 1G2 -ring R 2G2 is a ligand represented by the formula (GM-L1)
  • R G1 and R G2 are combined to form an aromatic ring
  • R G6 and R G3 or R G7 and R G3 are preferably bonds.
  • M 3G is preferably a group represented by the formula (GM-4).
  • n 115 represents 0 or 1; n 116 represents 1 or 3. However, when M is a rhodium atom or an iridium atom, n 115 is 0 and n 116 is 3. When M is a palladium atom or a platinum atom, n 115 is 1 and n 116 is 1. ]
  • the phosphorescent compound is preferably a phosphorescent compound represented by the formula (2).
  • M 2 is preferably an iridium atom since the external quantum efficiency of the light-emitting device containing the composition according to this embodiment is more excellent.
  • n 3 is preferably 2 or 3, and more preferably 3.
  • M 2 is a palladium atom or a platinum atom, n 3 is preferably 2.
  • E 3 and E 4 are preferably carbon atoms.
  • the preferred range for ring L 1 is the same as the preferred range for ring R 1G .
  • Ring L 2 is preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring, and more preferably a 6-membered aromatic hydrocarbon ring. However, when the ring L 2 is a 6-membered aromatic heterocyclic ring, E 4 is a carbon atom. Ring L 2 is preferably a benzene ring, a pyridine ring or a pyrimidine ring, and more preferably a benzene ring.
  • the ring L 1 has a plurality of other substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the ring L 2 has a plurality of other substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the other substituent in the ring L 1 and the other substituent in the ring L 2 may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • anionic bidentate ligand represented by A 3 -G 2 -A 4 are the same as the anionic bidentate ligand represented by A 1 -G 1 -A 2. The However, the anionic bidentate ligand represented by A 3 -G 2 -A 4 is different from the ligand whose number is defined by the subscript n 3 .
  • the ring L 1 is a pyridine ring, pyrimidine ring, isoquinoline ring or quinoline ring, and the ring L 2 is a benzene ring, A pyridine ring or a pyrimidine ring is preferred.
  • the phosphorescent compound represented by the formula (2) is represented by the formulas (2-B1) to (2-B5). It is preferable that the phosphorescent compound be used.
  • At least one selected from the group consisting of R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B is represented by an aryl group, a monovalent heterocyclic group or a substituted amino group. These groups are preferable, and these groups may have a substituent.
  • R 11B , R 12B , R 13B and R 14B are preferably a hydrogen atom, an alkyl group or an aryl group.
  • R 11B , R 12B , R 13B and R 14B is an aryl group, a monovalent heterocyclic group or a substituted amino group
  • R 13B is an aryl group, a monovalent heterocyclic group or a substituted amino group. It is preferable.
  • These groups are preferably dendrons because the external quantum efficiency of the light emitting device is more excellent. Examples and preferred embodiments of the dendron include the same as the examples and preferred embodiments of the dendron in the phosphorescent compound represented by the formula (5-A).
  • R 21B , R 22B , R 23B and R 24B are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom, an alkyl group or an aryl group It is more preferable that R 15B , R 16B , R 17B and R 18B are preferably hydrogen atoms.
  • Examples of the phosphorescent compound represented by the formula (2) include a phosphorescent compound represented by the following formula.
  • Examples of the structural unit represented by the formula (1G) include structural units represented by the formula (1G-1) to the formula (1G-12).
  • De represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, a group represented by the formula (DA), or a formula (DB). Represents a group.
  • Examples of the structural unit represented by the formula (2G) include structural units represented by the formulas (2G-1) to (2G-12).
  • Examples of the structural unit represented by the formula (3G) include structural units represented by the formulas (3G-1) to (3G-20).
  • Examples of the structural unit represented by the formula (4G) include structural units represented by the formulas (4G-1) to (4G-7).
  • the phosphorescent light-emitting structural unit is 0 with respect to 100 mol of the total amount of the structural units contained in the polymer compound.
  • the amount is preferably from 0.01 mol to 30 mol.
  • the polymer compound containing the structural unit represented by the formula (1) since the external quantum efficiency is more excellent, phosphorescence is preferably emitted in the visible region, and the emission peak wavelength is more preferably 570 to 700 nm.
  • the polymer compound containing the structural unit represented by the formula (1) has a long wavelength of 1 to 200 nm with respect to a light emitting material having a light emission peak on the longest wavelength side among the light emitting materials contained in the first light emitting layer. It preferably has an emission peak wavelength on the side, and more preferably has an emission peak wavelength on the longer wavelength side of 50 to 160 nm.
  • the polymer compound containing the structural unit represented by the formula (1) may contain only one type of phosphorescent structural unit or two or more types.
  • the polymer compound containing the structural unit represented by the formula (1) is more excellent in external quantum efficiency, it is preferable to include a crosslinked structural unit having at least one kind of crosslinking group selected from the crosslinking group A group.
  • a structural unit represented by the formula (3) or the formula (4) is preferable.
  • nA is preferably 1 or 2 because of its excellent external quantum efficiency.
  • n is preferably 2 because the external quantum efficiency is excellent.
  • Ar 1 is preferably an aromatic hydrocarbon group which may have a substituent since it has excellent external quantum efficiency.
  • the number of carbon atoms of the aromatic hydrocarbon group represented by Ar 1 is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18, not including the number of carbon atoms of the substituent. is there.
  • the arylene moiety of the aromatic hydrocarbon group represented by Ar 1 is preferably a group represented by the formulas (A-1) to (A-20), more preferably the formula (A-1) Or a group represented by formula (A-9), and these groups each optionally have a substituent.
  • the number of carbon atoms of the divalent heterocyclic group represented by Ar 1 is usually 2 to 60, preferably 4 to 18, excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group represented by Ar 1 is preferably a group represented by the formulas (AA-1) to (AA-34).
  • the alkylene group represented by L A is not including the carbon atom number of substituent is usually 1 to 20, preferably preferably 1-10.
  • Cycloalkylene group represented by L A is not including the carbon atom number of substituent is usually 3 to 20.
  • the alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.
  • the arylene group represented by L A may have a substituent.
  • a phenylene group or a fluorenediyl group is preferable.
  • L A is preferably an arylene group or an alkylene group because it facilitates the synthesis of the polymer compound containing the structural unit represented by the formula (1) and the polymer compound of the embodiment of the present invention. These groups may have a substituent.
  • the polymer compound containing the structural unit represented by the formula (1) is excellent in crosslinkability. Therefore, the formula (XL-1), the formula (XL-3), the formula ( XL-7) to a formula (XL-10), a formula (XL-16), a formula (XL-17) or a formula (XL-20), and more preferably a formula (XL-1) ), A crosslinking group represented by formula (XL-17) or formula (XL-20).
  • the total amount of the structural units contained in the polymer compound is 100 mol. On the other hand, it is preferably 0.5 to 90 mol, more preferably 5 to 60 mol.
  • the structural unit represented by Formula (3) may be included in the polymer compound containing the structural unit represented by Formula (1), or may be included in two or more types.
  • mA is preferably 0 because the external quantum efficiency is excellent.
  • m is preferably 0 because the external quantum efficiency is excellent.
  • c is preferably 0 because it facilitates the synthesis of the polymer compound containing the structural unit represented by formula (1) and is excellent in external quantum efficiency.
  • Ar 3 is preferably an aromatic hydrocarbon group which may have a substituent since it has excellent external quantum efficiency.
  • the definition and example of the aromatic hydrocarbon group represented by Ar 3 are the same as the group obtained by removing m hydrogen atoms from the definition and example of the arylene group represented by Ar X2 in formula (X).
  • the definition and example of the heterocyclic group represented by Ar 3 are the same as the group obtained by removing m hydrogen atoms from the definition and example of the divalent heterocyclic group represented by Ar X2 in formula (X). is there.
  • the definition and examples of the group in which the aromatic hydrocarbon group represented by Ar 3 and the heterocyclic group are directly bonded are as follows: the arylene group represented by Ar X2 and the divalent heterocyclic group in the formula (X) are directly This is the same as the group formed by removing m hydrogen atoms from the definition or example of the bonded divalent group.
  • Ar 2 and Ar 4 are preferably an arylene group which may have a substituent since it has excellent external quantum efficiency.
  • the definitions and examples of the arylene group represented by Ar 2 and Ar 4 are the same as the definitions and examples of the arylene group represented by Ar X1 and Ar X3 in the formula (X).
  • the definitions and examples of the divalent heterocyclic group represented by Ar 2 and Ar 4 are the same as the definitions and examples of the divalent heterocyclic group represented by Ar X1 and Ar X3 in formula (X).
  • the definition and examples of the group and the divalent heterocyclic group are the same.
  • K A since the synthesis of the polymer compound containing a constitutional unit represented by formula (1) is facilitated, is preferably a phenylene group or methylene group, which substituent You may have.
  • crosslinking group represented by X ′ are the same as the definition and examples of the crosslinking group represented by X.
  • the structural unit represented by the formula (4) is represented by the formula (1) because the polymer compound containing the structural unit represented by the formula (1) has excellent hole transportability and crosslinkability. Is preferably 0.5 to 80 mol, more preferably 3 to 40 mol, still more preferably 5 to 20 mol, per 100 mol of the total amount of the structural units contained in the polymer compound containing the structural unit. is there.
  • the structural unit represented by Formula (4) may be included in the polymer compound containing the structural unit represented by Formula (1), or may be included in two or more types.
  • Examples of the structural unit represented by formula (3) include structural units represented by formula (3-1) to formula (3-30).
  • Examples of the structural unit represented by formula (4) include: Examples thereof include structural units represented by formulas (4-1) to (4-9).
  • the polymer compound containing the structural unit represented by the formula (1) may further contain a structural unit represented by the formula (Y) and other structural units.
  • the other structural unit may be a structural unit represented by the formula (X).
  • Examples of the polymer compound containing the structural unit represented by the formula (1) include polymer compounds PP-1 to PP-8.
  • the polymer compounds PPP-1 to PPP-8 are preferable because the external quantum efficiency of the light emitting device according to this embodiment is more excellent.
  • p, q, r, s, t, u, v, w, and x represent the molar ratio of each constituent unit.
  • p + q + r + s + t + u + v + w + x 100.
  • the other structural unit means a structural unit other than the structural units represented by Formula (1), Formula (1X), Formula (1Z), Formula (5), Formula (5 ′), and Formula (Y). . ]
  • the crosslinking group of the polymer compound containing the structural unit represented by the formula (1) described above is treated under the crosslinking conditions described later. Is obtained.
  • the second light emitting layer is composed of at least one light emitting material and at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, and an antioxidant. It is preferable to contain a material.
  • the second light-emitting layer is a phosphorescent compound in addition to at least one selected from the group consisting of a polymer compound containing the structural unit represented by the formula (1) and a crosslinked product of the polymer compound. (In particular, it may contain a phosphorescent compound represented by the formula (2)).
  • Illustrative, preferred range and content of at least one material selected from the group consisting of hole transport material, hole injection material, electron transport material, electron injection material and antioxidant, which can be contained in the second light emitting layer Etc. are the same as those of the first light-emitting layer.
  • the second light-emitting layer is spun using an ink containing a polymer compound containing the structural unit represented by the formula (1) (hereinafter also referred to as “ink used for forming the second light-emitting layer”). It can be formed by a coating method such as a coating method, a gravure coating method, a bar coating method, a roll coating method, a spray coating method, a screen printing method, a die coating method, an ink jet printing method, a capillary coating method, or a nozzle coating method.
  • a coating method such as a coating method, a gravure coating method, a bar coating method, a roll coating method, a spray coating method, a screen printing method, a die coating method, an ink jet printing method, a capillary coating method, or a nozzle coating method.
  • the preferable range of the viscosity of the ink used for forming the second light emitting layer is the same as the preferable range of the viscosity of the ink used for forming the first light emitting layer.
  • Examples and preferred ranges of the solvent contained in the ink used for forming the second light emitting layer are the same as the examples and preferred ranges of the solvent contained in the ink used for forming the first light emitting layer.
  • the polymer compound containing the structural unit represented by the formula (1) and the phosphorescent structural unit of the present invention includes, for example, a compound represented by the following formula (M-1) and a formula (M-1G) It can manufacture by carrying out condensation polymerization with the compound represented by these.
  • the compounds used for the production of the polymer compound of the present invention are sometimes collectively referred to as “raw material monomers”.
  • the polymer compound of the embodiment of the present invention may contain other structural units.
  • examples of the raw material monomer include the following formula (M-1X), formula (M-1Z), formula (M- 5), a compound represented by formula (M-5 ′) or formula (MY).
  • Z C1 to Z C10 each independently represent a group selected from the group consisting of the substituent group A and the substituent group B.
  • Z C1 and Z C2 are groups selected from the substituent group A
  • Z C3 to Z C10 select groups selected from the substituent group B
  • Z C3 to Z C10 select groups selected from the substituent group A.
  • 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, these groups may have a substituent.
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent.
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent.
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent.
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent.
  • R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substitu
  • 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); -Sn (R C3) 3 (wherein, R C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. More existing 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 atoms to which they are bonded.
  • Examples of the group represented by —B (OR C2 ) 2 include groups represented by the following formulae.
  • a compound having a group selected from Substituent Group A and a compound having a group selected from Substituent Group B are subjected to condensation polymerization by a known coupling reaction, and a group selected from Substituent Group A and Substituent Group B Carbon atoms bonded to a group 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, condensation of these compounds by condensation polymerization A polymer can be obtained.
  • the condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, but may be carried out in the presence of a phase transfer catalyst if necessary.
  • the catalyst examples include dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate and the like.
  • transition metal complexes such as palladium complexes of nickel, nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel Metal complexes; these transition metal complexes may further include complexes having ligands such as triphenylphosphine, tri-o-tolylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, etc. .
  • a catalyst may be used individually by 1 type, or may use 2 or more types together.
  • 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.
  • Examples of the base and phase transfer catalyst include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organics such as tetrabutylammonium fluoride and tetrabutylammonium hydroxide.
  • Examples of the base include phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide. Each of the base and the phase transfer catalyst may be used alone or in combination of two or more.
  • the amount of base and phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of raw material monomers.
  • the solvent examples include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
  • organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
  • a solvent may be used individually by 1 type, or may use 2 or more types together.
  • the amount of solvent used is usually 10 to 100000 parts by weight with respect to 100 parts by weight of the total amount of raw material monomers.
  • the reaction temperature of the condensation polymerization is usually -100 to 200 ° C.
  • the reaction time of the condensation polymerization is usually 1 hour or more.
  • Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are carried out alone or in combination.
  • a lower alcohol such as methanol
  • filtering the deposited precipitate and then drying.
  • these methods are carried out alone or in combination.
  • the purity of the polymer compound is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, or the like.
  • the compound represented by the formula (1m-1), which is an embodiment of the compound represented by the formula (M-1), can be synthesized, for example, by a method represented by the following formula.
  • R A1 represents the same meaning as described above.
  • Ar A11 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar A11 is a group in which at least one atom adjacent to a bromine atom or an atom that forms a bond with the group represented by —B (OR C2 ) 2 is an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group.
  • the compound represented by the formula (1m-5) is reacted with lithium bis (trimethylsilyl) amide using a palladium catalyst to induce the compound represented by the formula (1m-5).
  • the compound represented by the formula (1m-3) is reacted with the compound represented by the formula (1m-4) by the Buchwald-Hartwig reaction to obtain the compound represented by the formula (1m-3). Is synthesized.
  • the compound represented by the formula (1m-2) is reacted with the brominating agent to synthesize the compound represented by the formula (1m-2).
  • a compound represented by the formula (1m-1) can be synthesized by reacting a compound represented by the formula (1m-2) with bispinacolatodiboron using a palladium catalyst. it can.
  • the compound represented by the formula (2m-1), which is an embodiment of the compound represented by the formula (M-1), can be synthesized, for example, by the method represented by the following.
  • Ar A12 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar A12 represents a bromine atom or at least one atom adjacent to an atom that forms a bond with the group represented by —B (OR C2 ) 2 is an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group.
  • An aryl group or a monovalent heterocyclic group as a substituent, and these substituents may further have a substituent.
  • Ar A2 represents the same meaning as described above.
  • R A11 represents the same meaning as R A1 . ]
  • the compound represented by the formula (2m-7) is induced by reacting the compound represented by the formula (2m-8) with lithium bis (trimethylsilyl) amide using a palladium catalyst.
  • a compound represented by the formula (2m-5) is obtained by subjecting a compound represented by the formula (2m-7) and a compound represented by the formula (2m-6) to Buchwald-Hartwig reaction. Is synthesized.
  • the compound represented by the formula (2m-3) is reacted with the compound represented by the formula (2m-4) by a Buchwald-Hartwig reaction to thereby obtain a compound represented by the formula (2m-3). Is synthesized.
  • the compound represented by the formula (2m-2) is reacted with the brominating agent to synthesize the compound represented by the formula (2m-2).
  • the compound represented by the formula (2m-1) can be synthesized by reacting the compound represented by the formula (2m-2) with bispinacolatodiboron using a palladium catalyst. it can.
  • the light emitting device includes an anode, a cathode, and a first light emitting layer and a second light emitting layer provided therebetween.
  • the light emitting device according to this embodiment may have other layers.
  • the first light emitting layer and the second light emitting layer are preferably adjacent to each other because the external quantum efficiency is more excellent.
  • the second light emitting layer is preferably a layer provided between the anode and the first light emitting layer because the external quantum efficiency is more excellent.
  • the second light emitting layer when the second light emitting layer is a layer provided between the anode and the first light emitting layer, the external quantum efficiency is more excellent, so that the anode and the second light emitting layer It is preferable to further have at least one layer selected from the group consisting of a hole injection layer and a hole transport layer between them.
  • the second light-emitting layer is a layer provided between the anode and the first light-emitting layer, the external quantum efficiency is more excellent, so that the electron injection layer and the first light-emitting layer are provided between the cathode and the first light-emitting layer. It is preferable to further have at least one layer selected from the group consisting of electron transport layers.
  • the second light emitting layer when the second light emitting layer is a layer provided between the cathode and the first light emitting layer, the external quantum efficiency is more excellent, so that the anode and the first light emitting layer It is preferable to further have at least one layer selected from the group consisting of a hole injection layer and a hole transport layer between them.
  • the second light-emitting layer is a layer provided between the cathode and the first light-emitting layer, the external quantum efficiency is more excellent, so that the electron injection layer and the second light-emitting layer are interposed between the cathode and the second light-emitting layer. It is preferable to further have at least one layer selected from the group consisting of electron transport layers.
  • two or more anodes, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a cathode may be provided as necessary.
  • anodes, hole injection layers, hole transport layers, electron transport layers, electron injection layers, and cathodes they may be the same or different.
  • the thickness of the anode, hole injection layer, hole transport layer, first light emitting layer, second light emitting layer, electron transport layer, electron injection layer and cathode is usually 1 nm to 1 ⁇ m, preferably 5 nm to 150 nm.
  • the layer configuration of the light emitting device according to this embodiment include the layer configurations represented by the following (D1) to (D18).
  • the light emitting device according to this embodiment usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.
  • “/” means that the layers before and after are stacked adjacent to each other.
  • “second light-emitting layer / first light-emitting layer” means that the second light-emitting layer and the first light-emitting layer are stacked adjacent to each other.
  • the light emitting device may have a non-light emitting intermediate layer between a plurality of light emitting layers, and may have a multi-photon unit configuration in which the intermediate layer is a charge generation layer.
  • the charge generating layer ITO (indium tin oxide), IZO (indium zinc oxide), ZnO 2, TiN, ZrN , HfN, TiOx, VOx, CuI, InN, GaN, CuAlO 2, CuGaO 2 , conductive inorganic compound layers such as SrCu 2 O 2 , LaB 6 , RuO 2 , two-layer films such as Au / Bi 2 O 3 , SnO 2 / Ag / SnO 2 , ZnO / Ag / ZnO, Bi 2 O 3 / Au / Bi 2 O 3 , TiO 2 / TiN / TiO 2 , TiO 2 / ZrN / TiO 2 and other multilayer films, C 60 and other fullerenes
  • an insulating layer may be provided adjacent to the electrode in order to improve the adhesion between the electrode and other layers and to improve the charge injection from the electrode.
  • the hole transport layer, the electron transport layer, the first light emitting layer, or the second light emitting layer is used to improve the adhesion of the interface and prevent the mixing of two adjacent layers.
  • a thin buffer layer may be inserted at the interface of the layers. The order and number of layers to be stacked, and the thickness of each layer may be adjusted in consideration of external quantum efficiency and device lifetime.
  • the light emitting device may have a substrate on the side opposite to the light emitting layer side of the anode or on the side opposite to the light emitting layer side of the cathode.
  • the substrate forms an electrode and chemically forms an organic layer (for example, a first light emitting layer, a second light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc.).
  • an organic layer for example, a first light emitting layer, a second light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc.
  • a substrate made of glass, plastic, polymer film, metal film, silicon, or the like, and a substrate in which these are laminated are used.
  • An electron transport layer is a layer containing an electron transport material.
  • the electron transport material a polymer compound containing at least one structural unit selected from the group consisting of a structural unit represented by the formula (ET-1) and a structural unit represented by the formula (ET-2) (hereinafter referred to as “electron transport material”) And also referred to as “polymer compound of electron transport layer”).
  • nE1 represents an integer of 1 or more.
  • Ar E1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R E1 .
  • R E1 represents a group represented by the formula (ES-1). When a plurality of R E1 are present, they may be the same or different. ]
  • nE3 represents an integer of 0 or more
  • aE1 represents an integer of 1 or more
  • bE1 represents an integer of 0 or more
  • mE1 represents an integer of 1 or more.
  • nE3, aE1, and bE1 may be the same or different.
  • mE1 is 1 when R E3 is a single bond.
  • aE1 and bE1 are selected so that the charge of the group represented by the formula (ES-1) becomes zero.
  • R E3 represents a single bond, a hydrocarbon group, a heterocyclic group or —O—R E3 ′ (R E3 ′ represents a hydrocarbon group or a heterocyclic group), and these groups have a substituent. It may be.
  • Q E1 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q E1 are present, they may be the same or different.
  • Y E1 represents —CO 2 ⁇ , —SO 3 ⁇ , —SO 2 — or —PO 3 2 ⁇ . When a plurality of Y E1 are present, they may be the same or different.
  • M E1 represents an alkali metal cation, an alkaline earth metal cation or an ammonium cation, and this ammonium cation may have a substituent. When a plurality of M E1 are present, they may be the same or different.
  • Z E1 is F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E4 ) 4 ⁇ , R E4 SO 3 ⁇ , R E4 COO ⁇ , NO 3 ⁇ , SO 4 2 ⁇ , HSO 4 ⁇ . , PO 4 3 ⁇ , HPO 4 2 ⁇ , H 2 PO 4 ⁇ , BF 4 ⁇ or PF 6 ⁇ .
  • R E4 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent. When a plurality of Z E1 are present, they may be the same or different. ]
  • NE1 is usually an integer of 1 to 4, preferably 1 or 2.
  • Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar E1 include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2,6-naphthalenediyl group, 1,4 Hydrogen bonded directly to the atoms constituting the ring from a naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthenediyl group or a 2,7-carbazolediyl group
  • a group excluding one atom nE1 is preferable, and may have a substituent other than R E1 .
  • Examples of the substituent other than R E1 that Ar E1 may have include 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, and aryloxy.
  • n ′, m ′ and nx each independently represents an integer of 1 or more.
  • nE3 is preferably an integer of 0 to 2.
  • aE1 is preferably 1 or 2.
  • bE1 is preferably 0 or 1.
  • mE1 is preferably 1.
  • R E3 is —O—R E3 ′
  • the group represented by the formula (ES-1) is a group represented by the following formula. -O-R E3 '- ⁇ (Q E1 ) nE3 -Y E1 (M E1 ) aE1 (Z E1 ) bE1 ⁇ mE1
  • R E3 is preferably an aromatic hydrocarbon group. As the substituent that R E3 may have, a group represented by formula (ES-3) is preferable.
  • Q E1 is preferably an alkylene group or an oxygen atom.
  • Y E1 is preferably —CO 2 — .
  • Examples of the alkali metal cation represented by M E1 include Li + , Na + , K + , Rb + , and Cs + .
  • Examples of the alkaline earth metal cation represented by M E1 include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ .
  • M E1 is preferably an alkali metal cation or an alkaline earth metal cation.
  • Z E1 is preferably F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E4 ) 4 ⁇ , R E4 SO 3 ⁇ , R E4 COO ⁇ or NO 3 ⁇ .
  • R E4 is preferably an alkyl group.
  • Examples of the group represented by the formula (ES-1) include a group represented by the following formula.
  • M + represents Li + , Na + , K + , Cs + or N (CH 3 ) 4 + .
  • M + represents Li + , Na + , K + , Cs + or N (CH 3 ) 4 + .
  • M + may be the same or different.
  • nE2 represents an integer of 1 or more.
  • Ar E2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R E2 .
  • R E2 represents a group represented by the formula (ES-2). When a plurality of R E2 are present, they may be the same or different. ]
  • nE4 represents an integer of 0 or more
  • aE2 represents an integer of 1 or more
  • bE2 represents an integer of 0 or more
  • mE2 represents an integer of 1 or more.
  • nE4 represents an integer of 0 or more
  • aE2 represents an integer of 1 or more
  • bE2 represents an integer of 0 or more
  • mE2 represents an integer of 1 or more.
  • R E5 represents a single bond, a hydrocarbon group, a heterocyclic group or —O—R E5 ′ (R E5 ′ represents a hydrocarbon group or a heterocyclic group), and these groups have a substituent. It may be.
  • Q E2 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q E2 are present, they may be the same or different.
  • Y E2 represents -C + R E6 2 , -N + R E6 3 , -P + R E6 3 , -S + R E6 2 or -I + R E6 2 .
  • R E6 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • a plurality of R E6 may be the same or different.
  • Y E2 When a plurality of Y E2 are present, they may be the same or different.
  • M E2 represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E7 ) 4 ⁇ , R E7 SO 3 ⁇ , R E7 COO ⁇ , BF 4 ⁇ , SbCl 6 ⁇ or SbF 6 ⁇ .
  • R E7 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • M E2 represents an alkali metal cation or an alkaline earth metal cation.
  • Z E2 represents an alkali metal cation or an alkaline earth metal cation.
  • R E5 is —O—R E5 ′
  • the group represented by the formula (ES-2) is preferably a group represented by the following formula. -O-R E5 '- ⁇ (Q E1 ) nE3 -Y E1 (M E1 ) aE1 (Z E1 ) bE1 ⁇ mE1
  • Examples of the group represented by the formula (ES-2) include a group represented by the following formula.
  • X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
  • X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
  • X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
  • X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
  • Examples of the structural units represented by formula (ET-1) and formula (ET-2) include structural units represented by the following formula (ET-31) to formula (ET-38).
  • Examples of the polymer compound for the electron transport layer include, for example, JP2009-239279A, JP2012-033845A, JP2012-216281A, JP2012-216822A, and JP2012-216815A. It can be synthesized according to the method described in 1.
  • Solvents used for forming the polymer compound of the electron transport layer from a solution are water, alcohol, fluorinated alcohol, ether, ester, nitrile compound, nitro compound, alkyl halide, aryl halide, thiol, sulfide, sulfoxide.
  • a hole injection layer is a layer containing hole injection material.
  • the hole injection material which the composition of the 1st light emitting layer may contain is mentioned, for example.
  • the hole injection material may be contained singly or in combination of two or more.
  • the electron injection layer is a layer containing an electron injection material.
  • an electron injection material the electron injection material which the composition of a 1st light emitting layer may contain is mentioned, for example.
  • the electron injection material may be contained singly or in combination of two or more.
  • a hole transport layer is a layer containing hole transport material.
  • the hole transport material which the composition of the 1st light emitting layer may contain is mentioned, for example.
  • the hole transport material may be contained singly or in combination of two or more.
  • the material of the anode includes, for example, conductive metal oxides and translucent metals, and preferably conductive compounds such as indium oxide, zinc oxide, tin oxide; ITO, indium / zinc / oxide; A composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.
  • conductive metal oxides and translucent metals and preferably conductive compounds such as indium oxide, zinc oxide, tin oxide; ITO, indium / zinc / oxide; A composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.
  • Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds.
  • Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
  • At least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.
  • Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a laminating method.
  • each layer such as the first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, the electron injection layer, etc.
  • a vacuum deposition method from a powder a method by film formation from a solution or a molten state
  • a polymer compound for example, a method by film formation from a solution or a molten state can be mentioned.
  • the first light emitting layer is formed using the ink used for forming the first light emitting layer
  • the second light emitting layer is formed using the ink used for forming the second light emitting layer.
  • the hole injection layer and the electron injection layer are typified by a spin coat method and an ink jet printing method using inks containing the above-described hole transport material, electron transport material, hole injection material and electron injection material, respectively. It can be formed by a coating method.
  • the light emitting device according to this embodiment can be manufactured by sequentially laminating each layer on a substrate.
  • each of the first light-emitting layer, the second light-emitting layer, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer of the light-emitting element are manufactured for the light-emitting element.
  • Each of the hole injection layer, the hole transport layer, the second light-emitting layer, the first light-emitting layer, the electron transport layer, and the solvent used when forming the layer adjacent to the electron injection layer It is preferred to avoid dissolution of the material in the solvent.
  • a method for avoiding dissolution of the material i) a method using a material having a crosslinking group, or ii) a method of providing a difference in solubility between adjacent layers is preferable.
  • the layer after forming a layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
  • Examples of the crosslinking method of the crosslinking group include a method of crosslinking by heating or light irradiation.
  • the heating temperature for crosslinking is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 to 200 ° C.
  • Types of light used for light irradiation for crosslinking are, for example, ultraviolet light, near ultraviolet light, and visible light.
  • the second light emitting layer is formed by a coating method, it is preferable to use ink.
  • the polymer compound containing the structural unit represented by the formula (1) contained in the second light emitting layer is a polymer compound containing a crosslinked structural unit having a crosslinking group
  • the polymer compound contained in the second light emitting layer can be crosslinked.
  • the second light emitting layer is substantially insolubilized in the solvent. Therefore, the second organic layer is suitable for stacking light emitting elements.
  • the polymer compound contained in the second light emitting layer is preferably a crosslinked body.
  • the light emitting device when the second light emitting layer is a layer provided between the anode and the first light emitting layer, the light emitting device according to this embodiment forms, for example, an anode on a substrate. Then, if necessary, a hole injection layer and / or a hole transport layer is formed on the anode, a second light emitting layer is formed on the anode, the hole injection layer, or the hole transport layer, and the second A first light-emitting layer is formed on the first light-emitting layer, and an electron transport layer and / or an electron injection layer is formed on the first light-emitting layer as necessary, and the first light-emitting layer, the electron transport layer, or It can be manufactured by forming a cathode on the electron injection layer.
  • the light-emitting device when the second light-emitting layer is a layer provided between the anode and the first light-emitting layer, the light-emitting device according to this embodiment includes, for example, a cathode on a substrate. If necessary, an electron injection layer and / or an electron transport layer is formed on the cathode, a first light emitting layer is formed on the cathode, the electron injection layer, or the electron transport layer, and the first light emission is performed. A second light emitting layer is formed on the layer, and a hole transport layer and / or a hole injection layer is formed on the second light emitting layer as necessary, and the second light emitting layer and the hole transport layer are formed. Or it can manufacture by forming an anode on a positive hole injection layer.
  • the light emitting device when the second light emitting layer is a layer provided between the cathode and the first light emitting layer, the light emitting device according to this embodiment forms, for example, an anode on a substrate. Then, if necessary, a hole injection layer and / or a hole transport layer is formed on the anode, a first light emitting layer is formed on the anode, the hole injection layer, or the hole transport layer, and the first A second light-emitting layer is formed on the light-emitting layer, and an electron transport layer and / or an electron injection layer is formed on the second light-emitting layer as necessary, and the second light-emitting layer, the electron transport layer or It can be manufactured by forming a cathode on the electron injection layer.
  • the light-emitting device when the second light-emitting layer is a layer provided between the cathode and the first light-emitting layer, the light-emitting device according to this embodiment includes, for example, a cathode on a substrate. If necessary, an electron injection layer and / or an electron transport layer is formed on the cathode, a second light emitting layer is formed on the cathode, the electron injection layer, or the electron transport layer, and the second light emission A first light emitting layer is formed on the layer, and a hole transport layer and / or a hole injection layer is formed on the first light emitting layer as necessary, and the first light emitting layer and the hole transport layer are formed. Or it can manufacture by forming an anode on a positive hole injection layer.
  • planar anode and cathode may be arranged so as to overlap each other.
  • pattern-like light emission a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, a layer that is desired to be a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern.
  • a segment type display device capable of displaying numbers, characters, and the like can be obtained.
  • both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter.
  • the dot matrix display device can be driven passively, or can be driven active in combination with a TFT or the like. These display devices can be used for displays of computers, televisions, portable terminals and the like.
  • the planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can also be used as a curved light source and a display device.
  • the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp). Determined by The SEC measurement conditions are as follows. The polymer compound to be measured was dissolved in THF (tetrahydrofuran) at a concentration of 0.05% by mass, and 10 ⁇ L was injected into SEC. THF was used as the mobile phase of SEC, and flowed at a flow rate of 2.0 mL / min. As the column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.
  • THF tetrahydrofuran
  • LC-MS was measured by the following method.
  • the measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 ⁇ L was injected into LC-MS (manufactured by Agilent, trade name: 1100LCMSD).
  • the mobile phase of LC-MS was used while changing the ratio of acetonitrile and tetrahydrofuran, and was allowed to flow at a flow rate of 0.2 mL / min.
  • L-column 2 ODS 3 ⁇ m
  • TLC-MS was measured by the following method. A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran or chloroform at an arbitrary concentration, and applied on a TLC plate for DART (trade name: YSK5-100, manufactured by Techno Applications), and TLC-MS (JEOL Ltd.) (Trade name: JMS-T100TD (The AccuTOF TLC)). The helium gas temperature during measurement was adjusted in the range of 200 to 400 ° C.
  • NMR NMR was measured by the following method. About 5 to 10 mg of a measurement sample, about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethyl sulfoxide, heavy acetone, heavy N, N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol Alternatively, it was dissolved in methylene chloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).
  • HPLC high performance liquid chromatography
  • Kaseisorb LC ODS 2000 manufactured by Tokyo Chemical Industry
  • ODS column As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry) or an ODS column having equivalent performance was used.
  • the detector a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used.
  • GC gas chromatography
  • the obtained reaction solution was separated, and the obtained organic layer was washed with ion-exchanged water.
  • the obtained washing liquid was dried over anhydrous magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid.
  • Toluene and activated carbon were added to the obtained solid and stirred for 30 minutes.
  • the obtained toluene solution was filtered with a filter laid with silica gel and celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid.
  • the obtained solid was purified by silica gel column chromatography (a mixed solvent of hexane and ethyl acetate), recrystallized using isopropanol, and then dried under reduced pressure at 50 ° C.
  • reaction vessel was cooled using an ice bath, an aqueous hydrochloric acid solution (2 mol / L, 800 mL) was added, and the reaction vessel was stirred for 1.5 hours while being cooled using an ice bath. Then, it neutralized by adding sodium hydroxide aqueous solution (6 mol / L, 600 mL) there.
  • the obtained reaction solution was separated, and the obtained organic layer was washed with ion-exchanged water.
  • the obtained washing liquid was separated, and the obtained organic layer was dried over magnesium sulfate and filtered.
  • the obtained filtrate was concentrated under reduced pressure, hexane was added, and the mixture was suspended and stirred for 1 hour, followed by filtration to obtain a yellow solid.
  • the resulting reaction mixture was cooled to room temperature and then washed with ion exchange water (100 mL).
  • the obtained washing liquid was separated, and the obtained organic layer was washed with ion-exchanged water.
  • the obtained washing solution was separated, and the obtained organic layer was dried over magnesium sulfate, filtered, and the obtained filtrate was concentrated. Thereafter, toluene and activated carbon were added thereto, and the mixture was stirred at room temperature for 30 minutes, followed by filtration with a filter covered with celite, and the obtained filtrate was concentrated under reduced pressure to obtain a white solid.
  • the obtained white solid was repeatedly recrystallized using a mixed solvent of toluene and methanol, and then dried under reduced pressure at 50 ° C.
  • the reaction vessel was cooled in an ice bath, an aqueous hydrochloric acid solution (2M, 467 mL) was added, and the reaction vessel was stirred for 30 minutes while being cooled in an ice bath. After adding heptane, the organic layer was separated. The obtained aqueous layer was washed with heptane and neutralized with an aqueous sodium hydroxide solution (10%, 381 mL). Heptane was added to the obtained reaction solution, and the obtained organic layer was washed with water. The obtained organic layer was dried over magnesium sulfate, filtered, and the obtained filtrate was concentrated.
  • the obtained oil was purified by silica gel column chromatography (toluene and ethyl acetate) and dried under reduced pressure at 50 ° C. to obtain compound 9 (37.0 g, red oil).
  • the HPLC area percentage value of Compound 9 was 99.0%.
  • the obtained organic layer was washed with water, dried over magnesium sulfate, and filtered.
  • the obtained filtrate was concentrated under reduced pressure to obtain an oily substance.
  • the obtained oil was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and dried under reduced pressure at 50 ° C. to obtain compound 10 (31.9 g, oil).
  • the HPLC area percentage value of Compound 10 was 98.9%.
  • the obtained reaction liquid was cooled and toluene was added, followed by filtration with a filter containing silica gel and celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid.
  • the obtained solid was purified by silica gel column chromatography (solvent: heptane) and dried at 50 ° C. under reduced pressure.
  • the obtained solid was recrystallized using a mixed solvent of toluene and isopropyl alcohol, and then dried under reduced pressure at 50 ° C. to obtain Compound 13 (14.5 g, white solid).
  • the HPLC area percentage value of Compound 13 was 99.5% or more. By repeating this operation, the necessary amount of Compound 13 was secured.
  • the obtained oil was dissolved in heptane, activated carbon (2.6 g) was added and stirred, and then filtered through a filter pre-coated with Celite, and the resulting filtrate was concentrated to obtain a crude product.
  • the obtained crude product was purified using silica gel column chromatography (solvent: heptane) and a silica gel column modified with an octadecylsilyl group (developing solvent: ethyl acetate / acetonitrile). Then, the compound 14 (12.7g, oily substance) was obtained by making it dry under reduced pressure. The HPLC area percentage value of Compound 14 was 99.3%.
  • the obtained washing liquid was separated, and the obtained organic layer was washed with ion-exchanged water.
  • the obtained washing liquid was separated, and the obtained organic layer was dried over magnesium sulfate and filtered.
  • the obtained filtrate was concentrated, hexane and activated carbon were added, and the mixture was stirred at room temperature for 30 minutes, and then filtered through a filter with celite.
  • the obtained filtrate was concentrated under reduced pressure, hexane and activated clay were added, and the mixture was stirred at room temperature for 30 minutes, followed by filtration with a filter covered with silica gel and celite.
  • the obtained filtrate was concentrated under reduced pressure to obtain an oily substance.
  • the obtained washing liquid was separated, and the obtained organic layer was dried over magnesium sulfate, filtered, and the obtained filtrate was concentrated to obtain a white solid. Thereafter, hexane, toluene and activated carbon were added thereto, and the mixture was stirred at room temperature for 30 minutes, followed by filtration with a filter laid with celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. Hexane was added to the obtained solid, and the mixture was suspended and stirred, and then filtered. The obtained solid was recrystallized using a mixed solvent of toluene, methanol and ethanol, and then dried under reduced pressure at 50 ° C. to obtain Compound 15-b (35.0 g, white solid).
  • Compound 15-b had an HPLC area percentage value of 99.5% or more.
  • an aqueous hydrochloric acid solution (2M, 240 mL) was added, and the reaction vessel was stirred for 30 minutes while cooling using an ice bath, whereby a solid was precipitated. The precipitated solid was filtered, and the resulting residue was dissolved in a mixed solvent of toluene and hexane. Thereafter, an aqueous sodium hydroxide solution (2M, 200 mL) was added thereto for neutralization. The obtained reaction solution was separated, and the obtained organic layer was washed with ion-exchanged water. The obtained washing solution was separated, the obtained organic layer was dried over magnesium sulfate, filtered, and the obtained filtrate was concentrated.
  • the resulting reaction mixture was cooled to room temperature, and then ion exchanged water (400 mL) was added.
  • the mixture was filtered through a filter with celite, and the obtained filtrate was separated.
  • the obtained organic layer was washed with ion-exchanged water, and the obtained washing solution was separated.
  • the obtained organic layer was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated. Thereafter, hexane and activated carbon were added thereto, and the mixture was stirred at room temperature for 30 minutes, and then filtered through a filter with celite.
  • the obtained filtrate was concentrated under reduced pressure to obtain an oily substance.
  • Compound CM1 Japanese Unexamined Patent Publication No. 2011-174062
  • Compound CM2 International Publication No. 2013/199088
  • Compound CM3 Japanese Unexamined Patent Publication No. 2010-215886
  • Compound CM4 International Publication No. 2015/008851
  • Compound CM5 Japanese Unexamined Patent Publication No. 2008-106241
  • Compounds CM6 and CM9 US Patent Application Publication No. 2014/0175415
  • Compound CM7 JP 2010-189630
  • Compound CM8 International Publication No. 2015/008851
  • Compound CM10 and CM11 JP 2009/157424
  • Compound CM13 International Publication No. 2014/157016
  • Compound CM17 International Publication No.
  • compound CM25-stg0 (8.0 g) synthesized by the method described in WO2016 / 005750, bispinacolatodiboron (7.5 g), potassium acetate (7 0.0 g), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (0.6 g) and dimethoxyethane (80 mL) were added and stirred. The resulting mixture was stirred at 80 ° C. for 4 hours, cooled to room temperature, hexane (160 mL) was added, and the mixture was filtered through a filter covered with celite.
  • the obtained filtrate was concentrated, toluene and activated carbon were added, and the mixture was stirred at room temperature for 1 hour, and then filtered through a filter with celite.
  • the obtained filtrate was concentrated, ethyl acetate was added, and the mixture was filtered through a filter covered with silica gel.
  • the obtained silica gel was washed with ethyl acetate.
  • the obtained washing solution was concentrated to obtain a solid.
  • the obtained solid was recrystallized using toluene and acetonitrile, and then dried under reduced pressure at 50 ° C. to obtain Compound CM25 (7.8 g, white solid).
  • the HPLC area percentage value of Compound CM25 was 99.4%.
  • Dicyclopentadiene (40 g) and 7-bromohept-1-ene (107 g) were added to the shield tube, sealed, and then stirred at 200 ° C. for 72 hours. This operation was repeated 9 times, and the solutions obtained by 10 operations were combined. The combined solution was distilled 6 times and purified by silica gel column chromatography to obtain compound CM26-stg1 (193 g). The GC (gas chromatography) area percentage value of the compound CM26-stg1 was 94.0%.
  • the obtained washing solution was concentrated, purified by silica gel column chromatography (hexane), and then recrystallized (a mixed solvent of ethyl acetate and methanol) to repeatedly obtain Compound CM26-stg2 (58 g).
  • the HPLC area percentage value of compound CM26-stg2 was 99.4%.
  • the obtained reaction liquid was filtered with a filter covered with celite, and the obtained celite was washed with toluene (200 mL). After repeating the same operation as the above series of operations, the obtained washing solutions were combined, suspended and stirred in acetonitrile, and then filtered to obtain a solid.
  • Compound CM26 (26.5 g) was obtained by repeating the operation of recrystallizing the obtained solid (mixed solvent of toluene and acetonitrile). The HPLC area percentage value of Compound CM26 was 99.2%.
  • reaction vessel was filled with a nitrogen gas atmosphere, and then compound CM27-stg0 (25.1 g) and tetrahydrofuran (95 mL) synthesized by the method described in International Publication No. 2016/005750 were added and stirred.
  • the obtained mixture was cooled to ⁇ 70 ° C., sec-butyllithium (1M cyclohexane solution, 96 mL) was added dropwise, and the mixture was stirred for 2 hours. Thereafter, fluorenone (11.8 g) dissolved in tetrahydrofuran (24 mL) was added dropwise thereto over 1 hour, followed by stirring for 2 hours. Thereafter, methanol (12 mL) was added thereto and stirred at room temperature.
  • the reaction vessel was filled with a nitrogen gas atmosphere, and then compound CM27-stg1 (18.9 g), toluene (189 mL) and triethylsilane (24.8 g) were added and stirred. After the obtained mixture was heated to 60 ° C., methanesulfonic acid (20.5 g) was added dropwise over 1 hour and stirred for 2.5 hours. After cooling the obtained reaction liquid to room temperature, toluene (189 mL) and ion-exchange water (189 mL) were added and stirred. The obtained solution was separated, and a 5 wt% aqueous sodium hydrogen carbonate solution (95 mL) was added to the obtained organic layer for washing.
  • reaction vessel was filled with a nitrogen gas atmosphere, and then compound CM27-stg2 (13.8 g), 60 wt% sodium hydride (1.8 g) and tetrahydrofuran (74 mL) were added and stirred. Thereafter, dimethylformamide (37 mL) was added dropwise thereto over 10 minutes, and the resulting mixture was cooled to 0 ° C. Thereafter, bromochlorohexane (22.5 g) was added dropwise thereto over 40 minutes, stirred at 0 ° C. for 2.5 hours, and then stirred at room temperature. Thereafter, heptane (110 mL) and ion-exchanged water (55 mL) were added thereto and stirred.
  • the obtained solution was separated, and ion-exchanged water (55 mL) was added to the obtained organic layer for washing.
  • the obtained organic layer was dried over magnesium sulfate, filtered, and concentrated to obtain an oil.
  • the obtained oil was purified by silica gel column chromatography (a mixed solvent of hexane and chloroform), suspended and stirred in a mixed solvent of ethanol and methanol, and filtered.
  • the obtained solid was dried under reduced pressure at 50 ° C. to obtain compound CM27-stg3 (16.9 g, white solid).
  • the HPLC area percentage value of the compound CM27-stg3 was 99.5% or more.
  • the reaction vessel was filled with a nitrogen gas atmosphere, and then compound CM27-stg3 (15.7 g), sodium iodide (42.0 g) and acetone (126 mL) were added and stirred. The resulting mixture was stirred at 55 ° C. for 41 hours and then cooled to room temperature. Thereafter, toluene (126 mL) and ion-exchanged water (63 mL) were added thereto and stirred. The obtained solution was separated, and ion-exchanged water (63 mL) was added to the obtained organic layer for washing. The obtained organic layer was dried over magnesium sulfate, filtered, and concentrated to obtain a solid.
  • the reaction vessel was filled with a nitrogen gas atmosphere, 60 wt% sodium hydride (0.8 g), tetrahydrofuran (56 mL) and dimethylformamide (56 mL) were added, and the mixture was cooled to 0 ° C and stirred. Thereafter, the compound CM27-stg4 (16.1 g) was added thereto. Thereafter, compound CM27-stg5b (14.0 g, synthesized by the method described in JP-T-2014-506609) dissolved in tetrahydrofuran (56 mL) was added dropwise thereto over 1 hour and stirred for 3 hours. The resulting reaction solution was stirred at 10 ° C. for 12 hours.
  • reaction vessel was filled with an argon gas atmosphere, and then compound CM27-stg5 (22.0 g), bispinacolatodiboron (14.1 g), potassium acetate (13.1 g) and dimethoxyethane (220 mL) were added and stirred. . Thereafter, [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (0.7 g) was added thereto and stirred at 90 ° C. for 15 hours. The obtained reaction solution was cooled to room temperature, toluene (220 mL) and celite (11 g) were added, and the mixture was filtered with a filter overlaid with celite.
  • the obtained filtrate was concentrated, suspended and stirred in hexane, and filtered.
  • Toluene (218 mL) and activated carbon (14 g) were added to the obtained solid, and the mixture was stirred for 1 hour, and then filtered through a filter covered with silica gel (28 g) and celite (84 g).
  • the obtained filtrate was concentrated to obtain a solid.
  • the obtained solid was recrystallized with a mixed solvent of toluene and hexane, and the obtained solid was dried at 50 ° C. under reduced pressure to obtain Compound CM27 (18.6 g, white solid).
  • the HPLC area percentage value of Compound CM27 was 99.5% or more.
  • the obtained organic layer was concentrated under reduced pressure, and the obtained crude product was recrystallized with a mixed solution of toluene and ethanol to obtain 51.8 g of compound CM28-stg2 as a white solid.
  • the obtained compound CM28-stg2 had an HPLC area percentage value (UV254 nm) of 99.5% or more. By repeating this operation, the required amount of compound CM28-stg2 was obtained.
  • the obtained residue was recrystallized with a mixed solution of toluene and heptane to obtain 81.0 g of a compound CM28-stg3 as a white solid.
  • the obtained compound CM28-stg3 had an HPLC area percentage value (UV254 nm) of 99.5%. By repeating this operation, the required amount of compound CM28-stg3 was obtained.
  • the obtained crude product was recrystallized with a mixed solution of heptane and isopropanol to obtain 143 g of compound CM28-stg4 as a white solid.
  • the obtained compound CM28-stg4 had an HPLC area percentage value (UV254 nm) of 99.4%.
  • the obtained reaction mixture was cooled to room temperature, toluene (143 ml) was added, and the mixture was filtered through a filter packed with celite.
  • the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was dissolved in a mixed solution of toluene (173 ml) and heptane (173 ml), activated carbon (4.6 g) was added, and the mixture was filtered through a filter packed with silica gel and celite.
  • the obtained filtrate was concentrated under reduced pressure, and the operation of recrystallizing the obtained residue with a mixed solution of ethyl acetate and acetonitrile was repeated to obtain 11.2 g of Compound CM28 as a white solid.
  • Compound CM29 Japanese Patent Application Laid-Open No. 2011-105701
  • Compound CM30 Japanese Patent Application Laid-Open No. 2008-179617
  • Step 1 Synthesis of polymer compound P1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM7 (1.000412 g), Compound CM5 (0.2141 g), Compound CM12 (1.1087 g) Compound CM10 (0.0847 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (3.60 mg) and toluene (32 mL) were added, and the mixture was heated to 90 ° C. (Step 2) A 16 wt% tetrabutylammonium hydroxide aqueous solution (21.2 g) was added dropwise to the reaction solution, and the mixture was refluxed for 7 hours.
  • Step 2 A 16 wt% tetrabutylammonium hydroxide aqueous solution (21.2 g) was added dropwise to the reaction solution, and the mixture was refluxed for 7 hours.
  • Step 3 After the reaction, phenylboronic acid (98.7 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.79 mg) were added thereto and refluxed for 14.5 hours.
  • Step 4 Then, after cooling, the obtained reaction solution was washed twice with a 10 wt% aqueous hydrochloric acid solution, twice with a 3 wt% aqueous ammonia solution and twice with water, and the obtained solution was added dropwise to methanol. However, precipitation occurred.
  • the obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order.
  • the obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.30 g of polymer compound P1.
  • the polymer compound P1 had a polystyrene-equivalent number average molecular weight of 3.9 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.3 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials used for the polymer compound P1 is that the structural unit derived from the compound CM7, the structural unit derived from the compound CM5, the structural unit derived from the compound CM12, and the compound CM10
  • the derived structural unit is a copolymer having a molar ratio of 50: 10: 39.4: 1.2.
  • Step 1 Synthesis of polymer compound P2 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (0.2655 g), Compound CM2 (0.6009 g), Compound CM3 (0.1675 g) Compound CM12 (0.9919 g), Compound CM11 (0.1669 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) and toluene (31 mL) were added, and the mixture was heated to 90 ° C.
  • Step 2 A 16 wt% tetrabutylammonium hydroxide aqueous solution (20.7 g) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.
  • Step 3 After the reaction, phenylboronic acid (73.2 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) were added thereto and refluxed for 14.5 hours.
  • Step 4 Then, after cooling, the obtained reaction solution was washed twice with a 10 wt% aqueous hydrochloric acid solution, twice with a 3 wt% aqueous ammonia solution and twice with water, and the obtained solution was added dropwise to methanol.
  • the obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.27 g of the polymer compound P2.
  • the polymer compound P2 had a polystyrene-equivalent number average molecular weight of 4.7 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 2.6 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P2 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM12 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Example 3 Synthesis of polymer compound P3 (Step 1) in Example 2 was carried out as follows: "After making the inside of the reaction vessel an inert gas atmosphere, compound CM1 (0.1775 g), compound CM2 (0.4006 g), Compound CM3 (0.1116 g), Compound CM13 (1.2146 g), Compound CM11 (0.1113 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (2.64 mg) and toluene (32 mL) were added, and 90 ° C.
  • Step 2 “16 wt% tetraethylammonium hydroxide aqueous solution (21.3 g) was added dropwise to the reaction solution and refluxed for 8 hours”, (step 3). Later, there was phenylboronic acid (48.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 m). ) was added, except that it was refluxed for 14.5 hours. "By the same manner as in Example 2, to give 1.34g of the polymer compound P3. The Mn of the polymer compound P3 was 3.6 ⁇ 10 4 , and the Mw was 1.3 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials used for the polymer compound P3 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM13 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Example 4 Synthesis of polymer compound P4 (Step 1) in Example 2 was carried out by replacing "the reaction vessel with an inert gas atmosphere, then compound CM1 (0.2594 g), compound CM2 (0.6009 g), Compound CM3 (0.1675 g), Compound CM14 (0.8851 g), Compound CM11 (0.1669 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) and toluene (29 mL) were added, and 90 ° C.
  • Step 2 is the same as in Example 2 except that “16 wt% tetraethylammonium hydroxide aqueous solution (19.2 g) was added dropwise to the reaction solution and refluxed for 4 hours”. In the same manner, 1.20 g of polymer compound P4 was obtained. The Mn of the polymer compound P4 was 5.3 ⁇ 10 4 and the Mw was 4.1 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials used for the polymer compound P4 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM14 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Example 5 Synthesis of polymer compound P5 (Step 1) in Example 2 was carried out as follows: "After making the inside of the reaction vessel an inert gas atmosphere, compound CM1 (0.2252 g), compound CM2 (0.5007 g), Compound CM3 (0.1396 g), Compound CM15 (1.0202 g), Compound CM11 (0.1391 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (3.30 mg) and toluene (29 mL) were added, and 90 ° C.
  • Step 2 Heated to “ (Step 2) was changed to “16% by weight tetraethylammonium hydroxide aqueous solution (18.3 g) was added dropwise to the reaction solution and refluxed for 8 hours.”
  • Step 3 Boronic acid (61.0 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.10 mg) were added and refluxed for 14.5 hours. 1.11 g of polymer compound P5 was obtained.
  • the Mn of the polymer compound P5 was 3.1 ⁇ 10 4
  • the Mw was 9.2 ⁇ 10 4 .
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P5 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM15 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Example 6 Synthesis of polymer compound P6 (Step 1) in Example 2 was carried out as follows: "After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (0.2593 g), Compound CM2 (0.6009 g), Compound CM3 (0.1676 g), Compound CM16 (0.9438 g), Compound CM11 (0.1669 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) and toluene (30 mL) were added, and 90 ° C.
  • Step 2 was changed to “Example 2” except that “16 wt% aqueous tetraethylammonium hydroxide solution (20.0 g) was added dropwise to the reaction solution and refluxed for 4 hours”.
  • 1.22 g of the polymer compound P6 was obtained.
  • the Mn of the polymer compound P6 was 6.5 ⁇ 10 4
  • the Mw was 4.9 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials used for the polymer compound P6 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM16 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Polymer compound P7 was synthesized by Suzuki coupling reaction using Compound CM7, Compound CM5, Compound CM17, and Compound CM10 according to the method described in WO 00/0053656. Synthesized.
  • the polymer compound P7 had a polystyrene equivalent number average molecular weight of 3.5 ⁇ 10 4 and a polystyrene equivalent weight average molecular weight of 1.4 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P7 is that the structural unit derived from the compound CM7, the structural unit derived from the compound CM5, the structural unit derived from the compound CM17, and the compound CM10
  • the derived structural unit is a copolymer having a molar ratio of 50: 10: 39.4: 1.2.
  • Step 2 Heated to " (Step 2) was changed to “16% by weight tetrabutylammonium hydroxide aqueous solution (21.5 g) was added dropwise to the reaction solution and refluxed for 4 hours”. Phenylboronic acid (56.1 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.01 mg) were added and refluxed for 14.5 hours. ” Thus, 1.35 g of the polymer compound 8 was obtained. The Mn of the polymer compound 8 was 4.7 ⁇ 10 4 and the Mw was 3.2 ⁇ 10 5 .
  • the polymer compound 8 is derived from the structural unit derived from the compound CM1, the structural unit derived from the compound CM2, the structural unit derived from the compound CM3, and the compound CM17. It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • the polymer compound P9 had a polystyrene-equivalent number average molecular weight of 1.2 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.8 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material used for polymer compound P9 was 16: a structural unit derived from compound M1, a structural unit derived from compound CM6, and a structural unit derived from compound CM9. It is a copolymer formed with a molar ratio of 50:34.
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P10 is 50: a structural unit derived from the compound CM7, a structural unit derived from the compound CM4, and a structural unit derived from the compound CM8. It is a copolymer composed of a molar ratio of 26:24.
  • Step 1 Synthesis of polymer compound P12 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM18 (9.23 g), Compound CM7 (4.58 g), dichlorobis (tris-o-methoxy) Phenylphosphine) palladium (8.6 mg) and toluene (175 mL) were added and heated to 105 ° C. (Step 2) Thereafter, a 12% by weight aqueous sodium carbonate solution (40.3 mL) was added dropwise thereto and refluxed for 29 hours.
  • Step 3 phenylboronic acid (0.47 g) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (8.7 mg) were added thereto and refluxed for 14 hours.
  • Step 4 Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. When the obtained reaction solution was cooled and dropped into methanol, precipitation occurred.
  • the precipitate was collected by filtration, washed with methanol and water, and then dried, and the solid obtained was dissolved in chloroform and purified by passing through an alumina column and a silica gel column through which chloroform was passed in advance in this order. When the obtained purified solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain polymer compound P11 (7.15 g).
  • the polymer compound P11 had Mn of 3.2 ⁇ 10 4 and Mw of 6.0 ⁇ 10 4 .
  • the polymer compound P11 has a theoretical value determined from the amount of raw materials charged, and is a co-polymer composed of a structural unit derived from the compound CM18 and a structural unit derived from the compound CM7 in a molar ratio of 50:50. It is a polymer.
  • Step 5 After making the inside of the reaction vessel under an argon gas atmosphere, polymer compound P11 (3.1 g), tetrahydrofuran (130 mL), methanol (66 mL), cesium hydroxide monohydrate (2.1 g) and water (12.5 mL) was added and stirred at 60 ° C. for 3 hours. (Step 6) Then, methanol (220 mL) was added thereto and stirred for 2 hours. The obtained reaction mixture was concentrated and then added dropwise to isopropyl alcohol, followed by stirring. As a result, precipitation occurred. The precipitate was collected by filtration and dried to obtain polymer compound P12 (3.5 g). By 1 H-NMR analysis of the polymer compound P12, it was confirmed that the signal at the ethyl ester site in the polymer compound P11 disappeared and the reaction was completed.
  • the theoretical value calculated from the amount of the raw material of the polymer compound P11 is that the polymer compound P12 has a molar ratio of 50:50 between the structural unit represented by the following formula and the structural unit derived from the compound CM7. It is a copolymer formed.
  • Example 7 Synthesis of Polymer Compound P13 1.46 g of polymer compound P13 was obtained according to Example 1 using Compound CM27, Compound CM3, Compound CM12 and Compound CM11 as monomers.
  • the polymer compound P13 had a polystyrene-equivalent number average molecular weight of 5.1 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 3.3 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials used for the polymer compound P13 is that the structural unit derived from the compound CM27, the structural unit derived from the compound CM3, the structural unit derived from the compound CM12, and the compound CM11
  • the derived structural unit is a copolymer composed of a molar ratio of 40: 10: 47: 3.
  • Example 8> Synthesis of polymer compound P14 1.11 g of polymer compound P14 was obtained according to Example 1 using Compound CM1, Compound CM25, Compound CM26, Compound CM12, and Compound CM11 as monomers.
  • the number average molecular weight of polystyrene conversion of the high molecular compound P14 was 5.5 * 10 ⁇ 4 >, and the weight average molecular weight of polystyrene conversion was 4.9 * 10 ⁇ 5 >.
  • the theoretical value obtained from the amount of charged raw materials for polymer compound P14 is that the structural unit derived from compound CM1, the structural unit derived from compound CM25, the structural unit derived from compound CM26, and the compound CM12 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • Example 9 Synthesis of polymer compound P15 According to Example 1, 1.09 g of polymer compound P15 was obtained using Compound CM28, Compound CM3, Compound CM12, and Compound CM29 as monomers.
  • the polymer compound P15 had a polystyrene-equivalent number average molecular weight of 4.3 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 3.5 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P15 is that the structural unit derived from the compound CM28, the structural unit derived from the compound CM3, the structural unit derived from the compound CM12, and the compound CM29
  • the derived structural unit is a copolymer composed of a molar ratio of 40: 10: 47: 3.
  • Example 10 Synthesis of polymer compound P16 According to Example 1, 5.2 g of polymer compound P16 was obtained using Compound CM28, Compound CM3, Compound CM12, and Compound CM11 as monomers.
  • the polymer compound P16 had a polystyrene-equivalent number average molecular weight of 5.3 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 3.1 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P16 is that the structural unit derived from the compound CM28, the structural unit derived from the compound CM3, the structural unit derived from the compound CM12, and the compound CM11
  • the derived structural unit is a copolymer composed of a molar ratio of 40: 10: 47: 3.
  • Example 18 Synthesis of Polymer Compound P17 According to Example 1, 1.22 g of polymer compound P17 was obtained using Compound CM28, Compound CM3, and Compound CM12 as monomers.
  • the polymer compound P17 had a polystyrene-equivalent number average molecular weight of 6.7 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 4.4 ⁇ 10 5 .
  • the theoretical value obtained from the amount of the raw material for the polymer compound P17 is 40: a structural unit derived from the compound CM28, a structural unit derived from the compound CM3, and a structural unit derived from the compound CM12. It is a copolymer formed with a molar ratio of 10:50.
  • the theoretical value obtained from the amount of the raw material used for the polymer compound P18 is that the structural unit derived from the compound CM27, the structural unit derived from the compound CM3, the structural unit derived from the compound CM17, and the compound CM11
  • the derived structural unit is a copolymer composed of a molar ratio of 40: 10: 47: 3.
  • Example 20 Synthesis of Polymer Compound P19 According to Example 1, 63.8 g of polymer compound P19 was obtained using Compound CM1, Compound CM25, Compound CM26, Compound CM17, and Compound CM11 as monomers.
  • the polymer compound P19 had a polystyrene-equivalent number average molecular weight of 5.1 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 4.0 ⁇ 10 5 .
  • the theoretical value obtained from the amount of charged raw material for polymer compound P19 is that the structural unit derived from compound CM1, the structural unit derived from compound CM25, the structural unit derived from compound CM26, and the compound CM17 It is a copolymer in which the structural unit derived and the structural unit derived from the compound CM11 are configured in a molar ratio of 10: 30: 10: 47: 3.
  • the theoretical value obtained from the amount of the raw material used for polymer compound P20 is that the structural unit derived from compound CM28, the structural unit derived from compound CM3, the structural unit derived from compound CM17, and the compound CM29
  • the derived structural unit is a copolymer composed of a molar ratio of 40: 10: 47: 3.
  • Example 22 Synthesis of Polymer Compound P21 According to Example 1, 2.56 g of polymer compound P21 was obtained using Compound CM28, Compound CM3, and Compound CM17 as monomers.
  • the polymer compound P21 had a polystyrene-equivalent number average molecular weight of 4.5 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 3.1 ⁇ 10 5 .
  • the theoretical value obtained from the amount of raw materials for the polymer compound P21 is 40: a structural unit derived from the compound CM28, a structural unit derived from the compound CM3, and a structural unit derived from the compound CM17. It is a copolymer formed with a molar ratio of 10:50.
  • Example D1 Fabrication and evaluation of light-emitting element D1 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P1 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the substrate on which the first light emitting layer is formed is depressurized to 1.0 ⁇ 10 ⁇ 4 Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the electron transport layer, and then sodium fluoride. About 80 nm of aluminum was deposited on the layer. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.
  • Example D2 Production and Evaluation of Light-Emitting Element D2
  • the ratio of polymer compound P9, compound CM19, and compound CM20 was such that polymer compound P9 / compound CM19 / compound.
  • CM20 64% by mass / 35% by mass / 1% by mass
  • a light emitting device D2 was produced in the same manner as in Example D1, and EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 15.8%. The results are shown in Table 4.
  • Example D3 Production and evaluation of light-emitting device D3
  • Example D1 formation of the first light-emitting layer
  • polymer compound P10 was used instead of polymer compound P9
  • the same procedure as in Example D1 was performed.
  • a light emitting element D3 was manufactured, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 15.4%.
  • the results are shown in Table 4.
  • Example D4 Production and evaluation of light-emitting element D4
  • Example D2 formation of the first light-emitting layer
  • polymer compound P10 was used instead of polymer compound P9
  • a light emitting element D4 was manufactured, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 16.5%. The results are shown in Table 4.
  • Example D5 Production and Evaluation of Light-Emitting Element D5
  • a light-emitting element was produced in the same manner as in Example D1, except that Compound CM22 was used instead of Compound CM19 in Example D1 (Formation of First Light-Emitting Layer).
  • EL emission was observed by producing D5 and applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 16.3%. The results are shown in Table 4.
  • Example CD1 Production and Evaluation of Light-Emitting Element CD1
  • Example D1 formation of the second light-emitting layer
  • the polymer compound P7 instead of the polymer compound P1, the polymer compound P7 was used.
  • a light emitting device CD1 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 13.3%. The results are shown in Table 4.
  • Example D2 formation of second light-emitting layer
  • polymer compound P7 was used instead of polymer compound P1
  • a light emitting device CD2 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 13.9%. The results are shown in Table 4.
  • Example D6 Fabrication and evaluation of light-emitting element D6 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P1 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D7 Fabrication and evaluation of light-emitting element D7
  • Example D6 formation of the second light-emitting layer
  • polymer compound P2 was used instead of polymer compound P1.
  • a light emitting element D7 was produced, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 18.8%. The results are shown in Table 5.
  • Example D8 Fabrication and evaluation of light-emitting element D8
  • Example D6 formation of the second light-emitting layer
  • polymer compound P3 was used instead of polymer compound P1
  • a light emitting element D8 was manufactured, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 15.7%. The results are shown in Table 5.
  • Example D9 Fabrication and evaluation of light-emitting element D9
  • Example D6 formation of the second light-emitting layer
  • polymer compound P4 was used instead of polymer compound P1.
  • a light emitting device D9 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 14.5%. The results are shown in Table 5.
  • Example D10 Production and evaluation of light-emitting element D10
  • Example D6 formation of the second light-emitting layer
  • polymer compound P5 was used instead of polymer compound P1.
  • a light emitting element D10 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 17.3%. The results are shown in Table 5.
  • Example D11 Production and evaluation of light-emitting element D11
  • Example D6 formation of the second light-emitting layer
  • polymer compound P6 was used instead of polymer compound P1.
  • a light emitting element D11 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 16.1%. The results are shown in Table 5.
  • Example D6 formation of the second light-emitting layer
  • the polymer compound P7 was used.
  • a light emitting device CD3 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 13.4%. The results are shown in Table 5.
  • Example CD4 Production and Evaluation of Light-Emitting Element CD4 Same as Example D6, except that in Example D6 (Formation of Second Light-Emitting Layer), Polymer Compound P8 was Used instead of Polymer Compound P1. Then, a light emitting device CD4 was manufactured, and EL light emission was observed by applying a voltage. The external quantum efficiency at 1000 cd / m 2 was 10.4%. The results are shown in Table 5.
  • Example D12 Fabrication and evaluation of light-emitting element D12 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • ND-3202 Nisan Chemical Industry Co., Ltd.
  • ND-3202 which is a hole injection material
  • the hole injection layer was formed by heating at 230 ° C. for 15 minutes on a hot plate.
  • Polymer compound P2 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D12 formation of second light-emitting layer
  • polymer compound P8 polymer compound P8 was used.
  • a light emitting device CD5 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 2.45%. The results are shown in Table 6.
  • Example D13 Fabrication and evaluation of light-emitting element D13 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P1 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D13 Formation of Second Light-Emitting Layer
  • Polymer Compound P7 was used instead of Polymer Compound P1.
  • a light emitting device CD6 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 7.02%. The results are shown in Table 7.
  • Example D14 Fabrication and evaluation of light-emitting element D14 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • ND-3202 was formed to a thickness of 35 nm by a spin coating method, and was heated on a hot plate at 50 ° C. for 3 minutes. The solvent was evaporated by heating, and then the hole injection layer was formed by heating at 230 ° C. for 15 minutes on a hot plate.
  • Polymer compound P1 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D14 formation of second light-emitting layer
  • polymer compound P2 was used instead of polymer compound P1
  • a light emitting device CD7 was fabricated, and EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 13.3%. The results are shown in Table 8.
  • Example D15 Fabrication and evaluation of light-emitting element D15 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P2 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D16 Fabrication and evaluation of light-emitting element D16
  • Example D15 formation of second light-emitting layer
  • polymer compound P3 was used instead of polymer compound P2
  • a light emitting element D16 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 19.8%.
  • the results are shown in Table 9.
  • Example D17 Production and evaluation of light-emitting element D17
  • Example D15 formation of the second light-emitting layer
  • polymer compound P4 was used instead of polymer compound P2
  • a light emitting element D17 was fabricated, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 16.8%.
  • the results are shown in Table 9.
  • Example D15 Formation of Second Light-Emitting Layer
  • Polymer Compound P8 was used instead of Polymer Compound P2
  • a light emitting device CD8 was fabricated, and EL light emission was observed by applying a voltage.
  • External quantum efficiency at 1000 cd / m 2 was 15.0%. The results are shown in Table 9.
  • Example D18 Fabrication and evaluation of light-emitting element D18 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P13 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D19 Production and evaluation of light-emitting device D19
  • polymer compound P14 was used instead of polymer compound P13, except that polymer compound P14 was used.
  • a light emitting device D19 was manufactured, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 16.1%. The results are shown in Table 10.
  • Example D18 Formation of Second Light-Emitting Layer
  • Polymer Compound P18 was used instead of Polymer Compound P13.
  • a light emitting device CD9 was manufactured, and EL light emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 9.9%. The results are shown in Table 10.
  • Example CD10 Production and Evaluation of Light-Emitting Element CD10
  • Example D20 Fabrication and evaluation of light-emitting element D20 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P15 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example CD11 Production and Evaluation of Light-Emitting Element CD11 Same as Example D20 except that in Example D18 (Formation of Second Light-Emitting Layer), instead of Polymer Compound P15, Polymer Compound P20 was used. Then, a light emitting device CD11 was fabricated, and EL light emission was observed by applying a voltage. The external quantum efficiency at 1000 cd / m 2 was 11.4%. The results are shown in Table 11.
  • Example D21 Fabrication and evaluation of light-emitting element D21 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P16 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D22 Production and evaluation of light-emitting element D22
  • polymer compound P17 and compound CM30 90 mass% / 10 mass%) Except that was used, a light-emitting element D22 was produced in the same manner as in Example D21, and EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 10.1%. The results are shown in Table 12.
  • Example D21 Formation of Second Light-Emitting Layer
  • Polymer Compound P21 and Compound CM30 Polymer Compound P21 / Compound CM30
  • Polymer Compound P16 90 mass% / 10 mass%)
  • a light-emitting element CD12 was produced in the same manner as in Example D21, and EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 7.3%. The results are shown in Table 12.
  • Example D23 Fabrication and evaluation of light-emitting element D23 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • the hole injection layer was formed by volatilizing and subsequently heating on a hot plate at 230 ° C. for 15 minutes.
  • Polymer compound P16 was dissolved in xylene at a concentration of 0.7 mass%.
  • the obtained xylene solution was used to form a film having a thickness of 20 nm on the hole injection layer by spin coating, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere.
  • the light emitting layer was formed.
  • the polymer compound P12 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm is formed on the first light-emitting layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.
  • Example D24 Production and Evaluation of Light-Emitting Element D24
  • Example D21 Formation of Second Light-Emitting Layer
  • Polymer Compound P17 and Compound CM30 Polymer Compound P17 / Compound CM30
  • Polymer Compound P16 90 mass% / 10 mass%)
  • a light emitting device D24 was produced in the same manner as in Example D23 except that EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 5.9%. The results are shown in Table 13.
  • Example D23 Formation of Second Light-Emitting Layer
  • Polymer Compound P21 and Compound CM30 Polymer Compound P21 / Compound CM30
  • Polymer Compound P16 90 mass% / 10 mass%)
  • a light emitting device CD13 was fabricated in the same manner as in Example D23 except that EL emission was observed by applying a voltage.
  • the external quantum efficiency at 1000 cd / m 2 was 2.4%. The results are shown in Table 13.
  • a light emitting device having excellent external quantum efficiency can be provided.

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Abstract

L'invention concerne un élément électroluminescent ou analogue présentant un excellent rendement quantique externe. Cet élément électroluminescent comprend une anode, une cathode, une première couche électroluminescente disposée entre l'anode et la cathode, et une seconde couche électroluminescente disposée entre l'anode et la cathode. La seconde couche électroluminescente contient au moins un élément choisi dans le groupe constitué par un composé polymère contenant un motif constitutif représenté par la formule (1), et un produit réticulé du composé polymère. (Dans la formule, a1, a2 et a3 représentent des entiers compris entre 0 et 5, inclus. Le cycle S1 représente un cycle hydrocarboné aromatique ou analogue. RA1 représente un groupe alkyle ou analogue. ArA1 représente un groupe arylène ou analogue. ArA2, ArA3 et ArA4 représentent un groupe arylène ou analogue. RA3, RA4, RA5 et RA6 représentent un groupe aryle ou analogue.)
PCT/JP2017/006523 2016-02-25 2017-02-22 Élément électroluminescent et composé polymère utilisé pour ledit élément électroluminescent WO2017146083A1 (fr)

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WO2019049225A1 (fr) 2017-09-06 2019-03-14 住友化学株式会社 Élément électroluminescent
WO2019065389A1 (fr) * 2017-09-29 2019-04-04 住友化学株式会社 Dispositif émetteur de lumière
CN109956977A (zh) * 2017-12-25 2019-07-02 北京夏禾科技有限公司 含杂环取代配体的金属络合物，以及包含该络合物的电致发光器件和化合物配方
WO2021166921A1 (fr) * 2020-02-20 2021-08-26 保土谷化学工業株式会社 Composé à poids moléculaire élevé et diode électroluminescente comprenant ledit composé à poids moléculaire élevé
US11917899B2 (en) 2020-03-05 2024-02-27 Samsung Electronics Co., Ltd. Arylamine-fluorene alternating copolymer, electroluminescence device material, and electroluminescence device using the polymer

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WO2019065389A1 (fr) * 2017-09-29 2019-04-04 住友化学株式会社 Dispositif émetteur de lumière
CN109956977A (zh) * 2017-12-25 2019-07-02 北京夏禾科技有限公司 含杂环取代配体的金属络合物，以及包含该络合物的电致发光器件和化合物配方
WO2021166921A1 (fr) * 2020-02-20 2021-08-26 保土谷化学工業株式会社 Composé à poids moléculaire élevé et diode électroluminescente comprenant ledit composé à poids moléculaire élevé
US11917899B2 (en) 2020-03-05 2024-02-27 Samsung Electronics Co., Ltd. Arylamine-fluorene alternating copolymer, electroluminescence device material, and electroluminescence device using the polymer

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