WO2017154883A1 - Élément luminescent - Google Patents

Élément luminescent Download PDF

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Publication number
WO2017154883A1
WO2017154883A1 PCT/JP2017/008950 JP2017008950W WO2017154883A1 WO 2017154883 A1 WO2017154883 A1 WO 2017154883A1 JP 2017008950 W JP2017008950 W JP 2017008950W WO 2017154883 A1 WO2017154883 A1 WO 2017154883A1
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group
formula
ring
atom
represented
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PCT/JP2017/008950
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English (en)
Japanese (ja)
Inventor
敏明 佐々田
大介 福島
田中　慎也
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住友化学株式会社
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Priority to JP2017518578A priority Critical patent/JP6296209B2/ja
Publication of WO2017154883A1 publication Critical patent/WO2017154883A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • the present invention relates to a light emitting element.
  • Patent Document 1 contains an organic layer containing a crosslinked material of a crosslinking material, a compound (H0-1) represented by the following formula, and a phosphorescent compound (G0-1) represented by the following formula: A light emitting element having a light emitting layer is described.
  • Patent Document 2 discloses a light emission containing an organic layer containing a crosslinked material of a crosslinking material, a compound (H0-2) represented by the following formula, and a phosphorescent compound (G0-2) represented by the following formula: A light emitting device having a layer is described.
  • the compound (H0-2) is a compound that does not have a group represented by the following formula (DA) or formula (DB).
  • an object of the present invention is to provide a light-emitting element that has an excellent luminance life.
  • the present invention provides the following [1] to [14].
  • a light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
  • the first organic layer is a layer containing a phosphorescent compound represented by formula (1) and a compound represented by formula (H);
  • the light emitting element whose 2nd organic layer is a layer containing the crosslinked body of a crosslinking material.
  • M represents a ruthenium atom, 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 is a ruthenium atom, rhodium atom or iridium atom
  • n 1 + n 2 is 3
  • M is a palladium atom or 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. When a plurality of E 1 and E 2 are present, they may be the same or different.
  • Ring L 1 represents an aromatic heterocyclic ring, and the 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 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 .
  • n H1 represents an integer of 0 or more and 5 or less.
  • n H1 When a plurality of n H1 are present, they may be the same or different.
  • n H2 represents an integer of 1 to 10.
  • Ar H1 represents a group represented by the formula (H1-1). When a plurality of Ar H1 are present, they may be the same or different.
  • L H1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR H1 ′ —, an oxygen atom or a sulfur atom, and these groups have a substituent. May be.
  • R H1 ′ 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.
  • L H1 When a plurality of L H1 are present, they may be the same or different.
  • D H1 represents a group represented by the formula (DA) or a group represented by the formula (DB). When a plurality of D H1 are present, they may be the same or different.
  • n DH1 represents an integer of 0 or more and 10 or less.
  • Ring R H1 and ring R H2 each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, 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.
  • X H1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by —N (R XH1 ) —, or a group represented by —C (R XH1 ′ ) 2 —.
  • R XH1 and R XH1 ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom. And these groups may have a substituent.
  • a plurality of R XH1 ′ 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.
  • a substituent that R XH1 and ring R H1 may have, a substituent that R XH1 and ring R H2 may have, a substituent that R XH1 ′ and ring R H1 may have, and , R XH1 ′ and the substituent which ring R H2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the group represented by the formula (H1-1) has n DH2 one D H2.
  • D H2 represents a group represented by the formula (DA) or a group represented by the formula (DB). When two or more DH2 exists, they may be the same or different.
  • n DH2 represents an integer of 0 or more and 10 or less. However, nDH1 + nDH2 is 1-20.
  • m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
  • G DA is a benzene ring, a pyridine ring, a Jiazabenzen ring or triazine ring, represent a hydrogen atom three obtained by removing group bonded directly to a carbon atom constituting the ring, these groups have a substituent Also good.
  • 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.
  • the plurality of TDAs may be the same or different. ] [Where: m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 or more.
  • G DA is a benzene ring, a pyridine ring, a Jiazabenzen ring or triazine ring, represent a hydrogen atom three obtained by removing group bonded directly to a carbon atom constituting the ring, these groups have a substituent Also good.
  • a plurality of GDAs may be the same or different.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • the plurality of TDAs may be the same or different.
  • the cross-linking material is [1] A low molecular compound having at least one crosslinking group selected from the crosslinking group A group, or a polymer compound containing a crosslinking structural unit having at least one crosslinking group selected from the crosslinking group A group. The light emitting element as described in.
  • 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
  • * 1 represents a binding position.
  • These crosslinking groups may have a substituent.
  • the cross-linking material is a polymer compound including a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group.
  • nA represents an integer of 0 to 5, and n represents 1 or 2.
  • Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may 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.
  • X represents a crosslinking group selected from the crosslinking group A group. When two or more X exists, 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 an integer of 0 or 1. When a plurality of mA are present, they may be the same or different.
  • Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
  • Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar 4 , Ar 5 and Ar 6 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 a sulfur atom to form a ring. It may be.
  • 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. 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.
  • a plurality of K A When a plurality of K A are present, they may be the same or different.
  • X ′ represents a bridging group selected from the bridging group A group, 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 a plurality of X ′ are present, they may be the same or different. However, at least one X ′ is a crosslinking group selected from the crosslinking group A group.
  • the crosslinking group possessed by the crosslinking material is represented by the formula (XL-2), formula (XL-3), formula (XL-4), formula (XL-5), formula (XL-6), formula (XL) -7), formula (XL-8), formula (XL-9), formula (XL-10), formula (XL-11), formula (XL-12), formula (XL-13), formula (XL- 14)
  • the light-emitting device according to any one of [2] to [4], which is a group represented by formula (XL-15) or formula (XL-17).
  • the group represented by the formula (H1-1) is represented by a group represented by the formula (H1-1A), a group represented by the formula (H1-1B), or a formula (H1-1C).
  • R XH2 and R XH2 ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom. And these groups may have a substituent.
  • a plurality of R XH2 ′ 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.
  • Z H1, Z H2, Z H3 , Z H4, Z H5, Z H6, Z H7, Z H8, Z H9, Z H10, Z H11 and Z H12 each independently represents a carbon atom or a nitrogen atom.
  • R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11 and R H12 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.
  • Z H1 is a nitrogen atom
  • R H2 does not exist.
  • Z H3 is a nitrogen atom
  • R H3 does not exist.
  • Z H4 is a nitrogen atom
  • Z H5 is a nitrogen atom
  • Z H6 does not exist.
  • Z H7 is a nitrogen atom
  • Z H8 does not exist.
  • Z H9 is a nitrogen atom
  • R H9 does not exist.
  • Z H10 is a nitrogen atom, R H10 does not exist.
  • R H11 When Z H11 is a nitrogen atom, R H11 does not exist.
  • Z H12 When Z H12 is a nitrogen atom, R H12 does not exist.
  • R H1 and R H2 , R H2 and R H3 , R H3 and R H4 , R H5 and R H6 , R H6 and R H7 , R H7 and R H8 , R H9 and R H10 , R H10 and R H11 , and R H11 and R H12 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • a group represented by the formula (H1-1A), a group represented by the formula (H1-1B), a group represented by the formula (H1-1C), and a group represented by the formula (H1-1D) groups respectively, having n DH2 one D H2.
  • D H2 and n DH2 represent the same meaning as described above.
  • the Ar H2 is a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, a tetraazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, A group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from a tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring (the group is substituted)
  • the light-emitting element according to any one of [1] to [6], which may have a group.
  • the group represented by the formula (DA) is represented by a group represented by the formula (D-A1), a group represented by the formula (D-A2), or a formula (D-A3).
  • R p1 , R p2 and R p4 When there are a plurality of R p1 , R p2 and R p4 , 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
  • np4 represents an integer of 0 to 4.
  • a plurality of np1 may be the same or different.
  • the group represented by the formula (DB) is represented by a group represented by the formula (D-B1), a group represented by the formula (D-B2), or a formula (D-B3).
  • 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 halogen 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.
  • a plurality of np2 may be the same or different.
  • E11B , E12B , E13B , E14B , E21B , E22B , E23B and E24B each independently represent a nitrogen atom or a carbon atom.
  • E 11B , E 12B , E 13B , E 14B , E 21B , E 22B , E 23B and E 24B they may be the same or different.
  • E 11B is a nitrogen atom
  • R 11B does not exist.
  • E 12B is a nitrogen atom
  • E 13B is a nitrogen atom
  • R 13B does not exist.
  • E 14B is a nitrogen atom, R 14B does not exist.
  • E 21B is a nitrogen atom
  • R 21B does not exist.
  • E 22B is a nitrogen atom
  • R 22B does not exist.
  • E 23B is a nitrogen atom
  • R 23B does not exist.
  • E 24B is a nitrogen atom, R 24B does not exist.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B they may be the same or different.
  • Ring L 1B represents a pyridine ring or a pyrimidine ring composed of a nitrogen atom, a carbon atom, E 11B , E 12B , E 13B and E 14B .
  • Ring L 2B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E 21B , E 22B , E 23B and E 24B .
  • the phosphorescent compound represented by the formula (1-B) is a phosphorescent compound represented by the formula (1-B1), a phosphorescent compound represented by the formula (1-B2), A phosphorescent compound represented by the formula (1-B3), a phosphorescent compound represented by the formula (1-B4) or a phosphorescent compound represented by the formula (1-B5) [10]
  • 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 ruthenium atom, rhodium atom or iridium atom, n 11 + n 12 is 3, and when M is a palladium atom or platinum atom, n 11 + n 12 is 2.
  • R 15B , R 16B , R 17B and R 18B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group Represents a group or a halogen atom, and these groups optionally have a substituent.
  • R 15B , R 16B , R 17B and R 18B may be the same or different.
  • R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21B are bonded to each other to form a ring together with the atoms to which they are bonded. Also good.
  • the phosphorescent compound represented by the formula (1) is a phosphorescent compound represented by the formula (1-A) .
  • M, n 1 , n 2 , E 1 and A 1 -G 1 -A 2 represent the same meaning as described above.
  • E 11A , E 12A , E 13A , E 21A , E 22A , E 23A and E 24A each independently represent a nitrogen atom or a carbon atom.
  • E 11A , E 12A , E 13A , E 21A , E 22A , E 23A and E 24A they may be the same or different.
  • E 11A is a nitrogen atom
  • R 11A may or may not be present.
  • E 12A is a nitrogen atom
  • E 13A is a nitrogen atom
  • R 13A may or may not be present.
  • E 21A is a nitrogen atom, R 21A does not exist.
  • R 22A When E 22A is a nitrogen atom, R 22A does not exist.
  • E 23A When E 23A is a nitrogen atom, R 23A does not exist.
  • E 24A When E 24A is a nitrogen atom, R 24A does not exist.
  • 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.
  • Ring L 1A represents a triazole ring or a diazole ring composed of a nitrogen atom, E 1 , E 11A , E 12A and E 13A .
  • Ring L 2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E 21A , E 22A , E 23A and E 24A .
  • the second organic layer is a layer provided between the anode and the first organic layer.
  • 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 a stable group because if the polymerization active group remains as it is, there is a possibility that the light emission characteristics or the luminance life may be lowered when the polymer compound is used for the production of a light emitting device. It is.
  • 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 forming 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.
  • the light emitting device of the present invention is a light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode.
  • the first organic layer is a layer containing a phosphorescent compound represented by the formula (1) and a compound represented by the formula (H), and the second organic layer is a cross-linking of a cross-linking material.
  • a light-emitting element which is a layer containing a body.
  • Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum deposition method and a wet method such as a spin coating method and an ink jet printing method, and a wet method is preferable.
  • a dry method such as a vacuum deposition method
  • a wet method such as a spin coating method and an ink jet printing method
  • a wet method is preferable.
  • the first organic layer is formed by a wet method
  • the second organic layer is formed by a wet method, it is preferable to use a second ink described later.
  • the crosslinking material contained in the second organic layer can be crosslinked by heating or light irradiation, and the crosslinking contained in the second organic layer by heating. It is preferred to crosslink the material.
  • the crosslinked material is contained in the second organic layer in a crosslinked state (crosslinked product of the crosslinked material)
  • the second organic layer is substantially insolu
  • the heating temperature for crosslinking is usually 25 ° C to 300 ° C, preferably 50 ° C to 250 ° C, more preferably 150 ° C to 200 ° C, and further preferably 170 ° C to 190 ° C. .
  • the heating time is usually 0.1 minutes to 1000 minutes, preferably 0.5 minutes to 500 minutes, more preferably 1 minute to 120 minutes, and further preferably 30 minutes to 90 minutes.
  • the types of light used for light irradiation are, for example, ultraviolet light, near ultraviolet light, and visible light.
  • Examples of the analysis method of the components contained in the first organic layer or the second organic layer include chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
  • chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR)
  • Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
  • insoluble Component components that are substantially insoluble in the organic solvent
  • dissolved component components that dissolves in an organic solvent
  • insoluble components can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and dissolved components can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.
  • the first organic layer is a layer containing a phosphorescent compound represented by formula (1) and a compound represented by formula (H).
  • the phosphorescent compound represented by the formula (1) is usually a compound that exhibits phosphorescence at room temperature (25 ° C.), and preferably a compound that emits light from a triplet excited state at room temperature.
  • the phosphorescent compound represented by the formula (1) has M as a central metal, a ligand whose number is defined by the subscript n 1 , and its number is defined by the subscript n 2 . It consists of a ligand.
  • M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the luminance lifetime of the light emitting device of the embodiment of the present invention is excellent.
  • M is a ruthenium atom, a rhodium atom or an iridium atom, n 1 is preferably 2 or 3, and more preferably 3.
  • M is a palladium atom or a platinum atom, n 1 is preferably 2.
  • E 1 and E 2 are preferably carbon atoms.
  • Ring L 1 is preferably a 5-membered aromatic heterocyclic ring or a 6-membered aromatic heterocyclic ring, or a 5-membered aromatic heterocyclic ring having 2 to 4 nitrogen atoms as constituent atoms or one More preferably, it is a 6-membered aromatic heterocycle having 4 or less nitrogen atoms as constituent atoms, and a 5-membered aromatic heterocycle having 2 or more and 3 or less nitrogen atoms as constituent atoms or one More preferably, it is a 6-membered aromatic heterocyclic ring having 2 or less nitrogen atoms as constituent atoms, and these rings may have a substituent.
  • E 1 is preferably a carbon atom.
  • the ring L 1 include a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring and an isoquinoline ring, and a diazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring.
  • a diazole ring, a triazole ring, a pyridine ring, a quinoline ring or an isoquinoline ring is more preferable, a pyridine ring, a quinoline ring or an isoquinoline ring is further preferable, a pyridine ring is particularly preferable, and these rings may have a substituent. .
  • Ring L 2 is preferably a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocycle More preferably, it is a ring, more preferably a 6-membered aromatic hydrocarbon ring, and these rings may have a substituent.
  • E 2 is preferably a carbon atom.
  • Examples of the ring L 2 include a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, indene ring, pyridine ring, diazabenzene ring, and triazine ring, and a benzene ring, naphthalene ring, fluorene ring, pyridine ring, or pyrimidine ring is included.
  • a benzene ring, a pyridine ring or a pyrimidine ring is more preferable, and a benzene ring is more preferable, and these rings may have a substituent.
  • Examples of the substituent that the ring L 1 and the ring L 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, and a substituted amino group.
  • a halogen atom is preferable, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a fluorine atom is more preferable, and an alkyl group, a cycloalkyl group, an aryl group or a monovalent complex is preferable.
  • a cyclic group is more preferable, an aryl group or a monovalent heterocyclic group is particularly preferable, and these groups may further have a substituent.
  • the aryl group in the substituent which the ring L 1 and the ring L 2 may have is preferably a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group or a pyrenyl group.
  • a group, a naphthyl group or a fluorenyl group is more preferable, a phenyl group is more preferable, and these groups may further have a substituent.
  • Examples of the monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have include a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, A carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group is preferable, pyridyl group, pyrimidinyl group, triazinyl group, carbazolyl group, azacarbazolyl group or diazacarbazolyl group is more preferable, pyridyl group, A pyrimidinyl group or a triazinyl group is more preferable, a triazinyl group is particularly preferable, and these groups may further have a substituent.
  • the amino group preferably has an aryl group or a monovalent heterocyclic group, more preferably an aryl group, These groups may further have a substituent.
  • Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in the substituent that the ring L 1 and the ring L 2 may have.
  • Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have. It is.
  • Examples of the substituent that the ring L 1 and the ring L 2 may have further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A monovalent heterocyclic group, a substituted amino group or a halogen atom is preferable, and an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a fluorine atom is more preferable, an alkyl group, a cyclo An alkyl group, an aryl group or a monovalent heterocyclic group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, and these groups may further have a substituent.
  • the aryl group or the monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have is more excellent in the luminance lifetime of the light emitting device of the embodiment of the present invention, preferably the formula (DA ), A group represented by the formula (DB) or the formula (DC), more preferably a group represented by the formula (DA) or the formula (DB), and more preferably a group represented by the formula (DA). Group.
  • m DA1 represents an integer of 0 or more.
  • Ar DA1 represents 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.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, Preferably 0 or 1.
  • m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
  • the substituent that GDA may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, It is a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.
  • G DA is preferably a group represented by the formula (GDA-11) ⁇ formula (GDA-14), more preferably a group represented by the formula (GDA-11) ⁇ formula (GDA-14) And more preferably a group represented by the formula (GDA-11) or (GDA-14), and particularly preferably a group represented by the formula (GDA-11).
  • 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 carbazolediyl group, more preferably a formula (ArDA-1) to a formula A group represented by formula (ArDA-5), more preferably a group represented by formula (ArDA-1) to formula (ArDA-3), particularly preferably formula (ArDA-1) or formula (ArDA -2), particularly preferably a group represented by the formula (ArDA-2), and these groups may have a substituent.
  • 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 or a monovalent heterocyclic group, still more preferably an aryl group, The group may have a substituent.
  • Ar DA1, Ar DA2, Ar DA3 , Ar DA4, Ar DA5, Ar DA6 and examples and preferred ranges of the substituent which may be possessed by Ar DA7 are examples of the substituent which may be possessed by G DA and It is the same as a preferable range.
  • T DA is preferably a group represented by the formula (TDA-1) ⁇ formula (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 the formula (D-A5), more preferably the formula (D-A1) or the formula (D-A3).
  • a group represented by the formula (D-A5) more preferably a group represented by the formula (D-A1), the formula (D-A3) or the formula (D-A5), particularly preferably the formula It is a group represented by (D-A1) or formula (D-A5).
  • the group represented by the formula (DB) is preferably a group represented by the formula (D-B1) to the formula (D-B6), more preferably the formula (D-B1) to the formula (D-B3).
  • a group represented by formula (D-B5) or formula (D-B6), more preferably a group represented by formula (D-B1), formula (D-B3) or formula (D-B5) And particularly preferably a group represented by the formula (D-B1).
  • the group represented by the formula (DC) is preferably a group represented by the formulas (D-C1) to (D-C4), more preferably represented by the formulas (D-C1) to (D-C3). More preferably a group represented by the formula (D-C1) or (D-C2), and particularly 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 halogen 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 and np6 each independently represents an integer of 0 to 5.
  • Np1 is preferably an integer of 0 to 2, more preferably 0 or 1.
  • np2 is preferably 0 or 1
  • np3 is preferably 0.
  • np4 is preferably an integer of 0 to 2
  • np5 is preferably an integer of 0 to 3, more preferably 0 or 1.
  • np6 is preferably an integer of 0 to 2, more preferably 0 or 1.
  • the alkyl group or cycloalkyl group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, 2-ethylhexyl. Group, cyclohexyl group or tert-octyl group.
  • the alkoxy group or cycloalkoxy group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy group.
  • R p1 , R p2 , R p3 , R p4 , R p5 and R p6 are preferably an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and more An alkyl group which may have a substituent is preferable, and 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 is more preferable.
  • Examples of the group represented by formula (D-A) include groups represented by formula (DA-1) to formula (DA-8).
  • R D represents a hydrogen atom, 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 Represents a cyclohexyloxy group.
  • 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 formula (DB-1) to the formula (DB-7).
  • R D represents the same meaning as described above.
  • Examples of the group represented by the formula (D-C) include groups represented by the formula (DC-1) to the formula (DC-13).
  • R D represents the same meaning as described above.
  • R D is preferably a hydrogen atom, 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, and is preferably a hydrogen atom, a tert-butyl group or a tert-octyl group. More preferably, it is a group.
  • substituents that the ring L 1 may have 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.
  • substituents that the ring L 2 may have 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 substituent that the ring L 1 may have and the substituent that the ring L 2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • anionic bidentate ligand examples 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 .
  • R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
  • a plurality of R L1 may be the same or different.
  • R L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
  • R L1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a fluorine atom, more preferably a hydrogen atom or an alkyl group, and these groups optionally have a substituent. .
  • R L2 is preferably an alkyl group or an aryl group, and these groups optionally have a substituent.
  • the phosphorescent compound represented by the formula (1) has an excellent luminance life of the light emitting device of the embodiment of the present invention
  • the phosphorescent compound represented by the formula (1-A) or the formula (1-B) The phosphorescent compound represented by formula (1-B) is preferred, and the phosphorescent compound represented by formula (1-B) is more preferred.
  • ring L 1A is a diazole ring
  • an imidazole ring in which E 11A is a nitrogen atom or an imidazole ring in which E 12A is a nitrogen atom is preferable
  • an imidazole ring in which E 11A is a nitrogen atom is more preferable.
  • ring L 1A is a triazole ring
  • a triazole ring in which E 11A and E 12A are nitrogen atoms, or a triazole ring in which E 11A and E 13A are nitrogen atoms is preferable, and E 11A and E 12A are nitrogen atoms.
  • a triazole ring is more preferred.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are ring L 1 and ring L 2 , respectively.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A may have and preferred ranges thereof may have ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent may further have.
  • R 11A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
  • R 11A is 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, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
  • R 12A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
  • R 12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
  • R 13A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
  • R 13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
  • ring L 2A is a pyridine ring
  • a pyridine ring in which E 23A is a nitrogen atom is preferable
  • E 22A is a nitrogen atom
  • Ring L 2A is preferably a benzene ring.
  • R 21A , R 22A , R 23A and R 24A are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a fluorine atom, ,
  • An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group more preferably a hydrogen atom, an alkyl group or an aryl group, and particularly preferably a hydrogen atom or an aryl group. These groups may have a substituent.
  • R 22A or R 23A is preferably an aryl group or a monovalent heterocyclic group, and R 22A is an aryl group or a monovalent heterocyclic group. It is more preferable that
  • the phosphorescent compound represented by the formula (1-A) has a further excellent luminance lifetime of the light emitting device of the embodiment of the present invention
  • a phosphorescent compound represented by -A2), a phosphorescent compound represented by formula (1-A3) or a phosphorescent compound represented by formula (1-A4) is preferred. More preferably, it is a phosphorescent compound represented by -A1) or a phosphorescent compound represented by formula (1-A3), and is a phosphorescent compound represented by formula (1-A1). Is more preferable.
  • ring L 2B is a pyridine ring
  • a pyridine ring in which E 23B is a nitrogen atom is preferable
  • E 22B is a nitrogen atom
  • Ring L 2B is preferably a benzene ring.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are the ring L 1 and Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the ring L 2 may have are the same as the preferred range.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B may have and preferred ranges thereof include ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent which may be further may have.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, halogen atom, aryl group, monovalent group It is preferably a heterocyclic group or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, a hydrogen atom, an alkyl group It is more preferably a group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably a hydrogen atom, an aryl group or a monovalent heterocyclic group, and preferably a hydrogen atom or an aryl group. Particularly preferred, these groups may have a substitu
  • R 11B , R 12B or R 13B is preferably an aryl group or a monovalent heterocyclic group, and R 12B or R 13B is an aryl group or More preferably, it is a monovalent heterocyclic group, and R 13B is more preferably an aryl group or a monovalent heterocyclic group.
  • R 22B or R 23B is preferably an aryl group or a monovalent heterocyclic group, and R 22B is an aryl group or a monovalent heterocyclic group. It is more preferable that
  • the phosphorescent compound represented by the formula (1-B) has a further excellent luminance lifetime of the light emitting device of the embodiment of the present invention
  • the phosphorescent compound represented by the formula (1-B1), the formula (1) A phosphorescent compound represented by -B2), a phosphorescent compound represented by formula (1-B3), a phosphorescent compound represented by formula (1-B4), or a formula (1-B5)
  • the phosphorescent compound is preferably a phosphorescent compound represented by formula (1-B1), a phosphorescent compound represented by formula (1-B2) or a formula (1-B3).
  • the phosphorescent compound is more preferably a phosphorescent compound represented by the formula (1-B1) or a phosphorescent compound represented by the formula (1-B3).
  • a phosphorescent compound represented by (1-B1) is particularly preferable.
  • aryl groups, monovalent heterocyclic groups and substituted amino groups in R 15B , R 16B , R 17B and R 18B and preferred ranges thereof are the substituents that the ring L 1 and the ring L 2 may have, respectively.
  • R 15B , R 16B , R 17B and R 18B may have and preferred ranges thereof may be further included in the substituents which ring L 1 and ring L 2 may have. Examples of good substituents and preferred ranges are the same.
  • R 15B , R 16B , R 17B and R 18B are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, an aryl group, a monovalent heterocyclic group or a fluorine atom.
  • a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent
  • a heterocyclic group particularly preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, and these groups optionally have a substituent.
  • Examples of the phosphorescent compound represented by the formula (1) include a phosphorescent compound represented by the following formula.
  • Examples of the phosphorescent compound represented by the formula (1) include “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical, 47”. 6653 (1984) ”, Japanese translations of PCT publication No. 2004-530254, Japanese Unexamined Patent Publication No. 2008-179617, Japanese Unexamined Patent Publication No. 2011-105701, Japanese translations of PCT publication No. 2007-504272, International Publication No. 2006/121811, and Japanese Unexamined Patent Publication No. 2013-2013. It can be synthesized according to the methods described in JP-A-147450 and JP-A-2014-224101.
  • the molecular weight of the compound represented by the formula (H) is usually 1 ⁇ 10 2 to 5 ⁇ 10 4 , preferably 2 ⁇ 10 2 to 1 ⁇ 10 4 , more preferably 3 ⁇ 10 2. ⁇ a 5 ⁇ 10 3, more preferably from 4 ⁇ 10 2 ⁇ 2.5 ⁇ 10 3, particularly preferably from 5 ⁇ 10 2 ⁇ 1.5 ⁇ 10 3.
  • n H1 is preferably an integer of 0 or more, 3 or less, more preferably an integer of 0 or more, 2 or less, still more preferably 0 or 1, and particularly preferably 0 because synthesis is easy.
  • n H2 is preferably an integer of 1 or more and 7 or less, more preferably an integer of 1 or more and 5 or less, and further preferably 1 or more and 3 or less, because the luminance life of the light emitting device of the embodiment of the present invention is excellent. It is an integer, particularly preferably 1 or 2, and particularly preferably 1.
  • D H1 and D H2 are preferably a group represented by the formula (DA).
  • n DH1 is an integer of 1 or more and 7 or less, more preferably an integer of 1 or more and 5 or less, and still more preferably an integer of 1 or more and 3 or less because the luminance life of the light emitting device of the embodiment of the present invention is excellent. Yes, particularly preferably 1 or 2, particularly preferably 2.
  • nDH2 is an integer of 0 or more and 7 or less, more preferably an integer of 0 or more and 5 or less, still more preferably an integer of 0 or more and 2 or less, and particularly preferably 0 because synthesis is easy. .
  • Ar H1 is a group represented by the formula (H1-1).
  • the number of carbon atoms of the aromatic hydrocarbon ring is usually 6 to 60, preferably 6 to 30, and more preferably 6 excluding the number of carbon atoms of the substituent. ⁇ 18.
  • the aromatic hydrocarbon ring in the ring R H1 and the ring R H2 include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, indene ring, and pyrene ring.
  • Perylene ring and chrysene ring preferably benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring or spirobifluorene ring, more preferably benzene ring, naphthalene ring, fluorene.
  • a ring or a spirobifluorene ring, more preferably a benzene ring or a fluorene ring, and these rings optionally have a substituent.
  • the number of carbon atoms of the aromatic heterocyclic ring is usually 2 to 60, preferably 3 to 30, more preferably not including the number of carbon atoms of the substituent. 4-15.
  • the aromatic heterocyclic ring in the ring R H1 and the ring R H2 include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, and an indole.
  • phenazine ring preferably pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenoxazine ring, A thiazine ring, a 9,10-dihydroacridine ring or a 5,10-dihydrophenazine
  • the substituents that the ring R H1 and the ring R H2 may have are different.
  • An alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group is more preferable, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is more preferable, and an alkyl group, a cycloalkyl group or an aryl group is more preferable.
  • Particularly preferred are alkyl groups and cycloalkyl groups, and these groups may further have a substituent
  • rings R H1 and ring R H2 at least one, preferably an aromatic hydrocarbon ring, and more preferably both rings R H1 and ring R H2 is an aromatic hydrocarbon ring.
  • X H1 is preferably a single bond, an oxygen atom or a sulfur atom, and more preferably a single bond.
  • R XH1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group. These groups may have a substituent.
  • R XH1 ′ is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, still more preferably an alkyl group or A cycloalkyl group, and these groups optionally have a substituent. Examples and preferred ranges of the substituent that R XH1 and R XH1 ′ may have are examples of the substituent that the ring R H1 and the ring R H2 may further have. And the same as the preferred range.
  • the group represented by the formula (H1-1) is preferably a group represented by the formula (H1-1A), a group represented by the formula (H1-1B), or a formula (H1-1C).
  • X H2 and X H3 are preferably a single bond, a group represented by —N (R XH2 ) —, or a group represented by —C (R XH2 ′ ) 2 —, more preferably a single group.
  • At least one of X H2 and X H3 is preferably a single bond, and X H3 is more preferably a single bond.
  • X H2 and X H3 are a single bond
  • the other is an oxygen atom, a sulfur atom, a group represented by —N (R XH2 ) —, or —C (R XH2 ′ ) 2 —.
  • R XH2 and preferred ranges are the same as examples of R XH1 and preferred ranges.
  • R XH2 'examples and preferred ranges, R XH1' is the same as the examples and preferable range.
  • Examples of the substituent that R XH2 and R XH2 ′ may have and preferred ranges thereof are examples of the substituent that the ring R H1 and the ring R H2 may further have. And the same as the preferred range.
  • Z H1 , Z H2 , Z H3 , Z H4 , Z H5 , Z H6 , Z H7 , Z H8 , Z H9 , Z H10 , Z H11 and Z H12 are preferably carbon atoms.
  • R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11 and R H12 are a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, It is preferably a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group.
  • a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is more preferable, a hydrogen atom, an alkyl group or a cycloalkyl group is particularly preferable, a hydrogen atom is particularly preferable, and these groups are further substituted. It may have a group.
  • substituents that R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11, and R H12 may have are as follows.
  • the examples of the substituent which the ring R H1 and the ring R H2 may have and the substituent which the ring R H2 may further have are the same as the preferred range.
  • R H1 and R H2 , R H2 and R H3 , R H3 and R H4 , R H5 and R H6 , R H6 and R H7 , R H7 and R H8 , R H9 and R H10 , R H10 and R H11 , and R H11 and R H12 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, but it is preferable that no ring is formed.
  • L H1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group, and even more preferably an arylene group. These groups may have a substituent.
  • the arylene group represented by L H1 is preferably a phenylene group, a naphthalene diyl group, a fluorenediyl group, a phenanthrene diyl group or a dihydrophenanthrene diyl group, and more preferably a formula (A-1) to a formula ( A-9), a group represented by formula (A-19) or formula (A-20), more preferably a group represented by formula (A-1) to formula (A-3). Particularly preferred is a group represented by the formula (A-1) or (A-2), and particularly preferred is a group represented by the formula (A-2). These groups have substituents. You may have.
  • the divalent heterocyclic group represented by L H1 is preferably a group represented by the formula (AA-1) to the formula (AA-34), more preferably a formula (AA-1) to Groups represented by formula (AA-6), formula (AA-10) to formula (AA-21), or formula (AA-24) to formula (AA-34), more preferably formula (AA- 1) to groups represented by formula (AA-4), formula (AA-10) to formula (AA-15), or formula (AA-29) to formula (AA-34), particularly preferably A group represented by formula (AA-2), formula (AA-4), formula (AA-10), formula (AA-12) or formula (AA-14).
  • Examples and preferred ranges of the substituent that L H1 may have are the same as examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may have. Examples and preferred ranges of the substituent that the substituent which L H1 may have may further have a substituent which the ring R H1 and ring R H2 may have further include. Examples of the preferred substituents and the preferred ranges are the same.
  • R H1 ′ is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent. Examples and preferred ranges of the substituent that R H1 ′ may have are examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may further have. Is the same.
  • Is Ar H2 has n DH1 one D H1, has a sp 2 nitrogen atoms as ring, and, no sp 3 nitrogen atoms as ring, monocyclic or fused nitrogen-containing heterocyclic It is a cyclic group, and the group may have a substituent.
  • the number of sp 2 nitrogen atoms constituting the ring is as follows: Usually, it is 1 to 10, preferably 1 to 7, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 3.
  • the number of carbon atoms constituting the ring is usually 1 -60, preferably 2-40, more preferably 3-20, and even more preferably 3-10.
  • a monocyclic or condensed heterocyclic group having an sp 2 nitrogen atom as a ring constituent atom and no sp 3 nitrogen atom as a ring constituent atom includes an oxadiazole ring, a thiadiazole ring, a thiazole ring, Oxazole ring, isothiazole ring, isoxazole ring, benzooxadiazole ring, benzothiadiazole ring, benzothiazole ring, benzoxazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene Ring, tetraazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene
  • Ar H2 may have a substituent (a group represented by the following formula (1H ′), a group represented by the formula (DA), and a group represented by the formula (DB).
  • a substituent a group represented by the following formula (1H ′), a group represented by the formula (DA), and a group represented by the formula (DB).
  • a cycloalkyl group or an aryl group is particularly preferable, and these groups may further have a substituent. Examples of the substituent that the substituent that Ar H2 may have and the substituent that the substituent may optionally have further include the substituent that the ring R H1 and ring R H2 may further have. Examples of the preferred substituents and the preferred ranges are the same.
  • the compound represented by the formula (H) is preferably a compound represented by the formula (H′-1) to the formula (H′-11) because the luminance lifetime of the light emitting device of the embodiment of the present invention is excellent. And more preferably a compound represented by a compound represented by formula (H′-1), formula (H′-2) or formula (H′-4) to formula (H′-8), More preferred is a compound represented by the formula (H′-1), the formula (H′-2) or the formula (H′-4), and particularly preferred is a formula (H′-4).
  • R 1H is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or a formula (DA).
  • a plurality of R 1H may be the same or different. However, at least one of a plurality of R 1H is a group represented by the formula (1H ′).
  • n H2 are preferably groups represented by the formula (1H ′).
  • n DH1 is preferably a group represented by the formula (DA) or ( DB ), and n DH1 is represented by the formula (DA). More preferably, it is a group.
  • R 1H is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a group represented by the formula (DA), a formula (D— B) or a group represented by formula (1H ′), more preferably a hydrogen atom, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, formula (DA) ), A group represented by the formula (DB), or a group represented by the formula (1H ′), more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, a formula A group represented by (DA), a group represented by formula (DB), or a group represented by formula (1H ′), particularly preferably a hydrogen atom or a group represented by formula (DA).
  • Examples of the compounds represented by the formula (H′-1) to the formula (H′-11) include compounds represented by the formula (H ′′ -1) to the formula (H ′′ -22). Preferably, it is a compound represented by the formula (H ′′ -1) to the formula (H ′′ -18), more preferably the formula (H ′′ -1) to the formula (H ′′ -8). And more preferably a compound represented by the formula (H ′′ -8).
  • R 2H represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a group represented by the formula (DA), a group represented by the formula (DB), or a formula Represents a group represented by (1H ′), and these groups optionally have a substituent.
  • a plurality of R 2H may be the same or different. However, at least one of a plurality of R 2H is a group represented by the formula (1H ′).
  • n H2 are preferably groups represented by the formula (1H ′).
  • n DH1 is preferably a group represented by the formula (DA) or ( DB ), and n DH1 is represented by the formula (DA). More preferably, it is a group.
  • R 2H is preferably an aryl group, a monovalent heterocyclic group, a group represented by the formula (DA), a group represented by the formula (DB), or a formula (1H ′).
  • a group represented by (DA) or a group represented by formula (1H ′), and these groups may further have a substituent. Examples and preferred ranges of the substituent that R 2H may have include examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may further have. The same.
  • Examples of the compound represented by the formula (H) include a compound represented by the following formula.
  • Z represents a group represented by —N ⁇ or a group represented by —CH ⁇ .
  • the compound represented by the formula (H) is Aldrich, Luminescence Technologymin Corp. Etc. are available.
  • the first organic layer is a layer containing a phosphorescent compound represented by the formula (1) and a compound represented by the formula (H). Since the 1st organic layer may contain the phosphorescence-emitting compound represented by Formula (1) individually by 1 type, since the luminescent color of the light emitting element of embodiment of this invention can be adjusted. Two or more kinds may be contained. Moreover, the 1st organic layer may contain the compound represented by Formula (H) individually by 1 type, and may contain 2 or more types.
  • the content of the phosphorescent compound represented by formula (1) is the sum of the phosphorescent compound represented by formula (1) and the compound represented by formula (H).
  • it is preferably 0.1 to 80 parts by weight. More preferably, it is 65 parts by weight, even more preferably 5 to 50 parts by weight, particularly preferably 5 to 40 parts by weight, and particularly preferably 10 to 40 parts by weight.
  • the first organic layer includes a phosphorescent compound represented by the formula (1), a compound represented by the formula (H), a hole transport material, a hole injection material, an electron transport material, an electron injection material, It may be a layer containing a composition containing at least one material selected from the group consisting of a light emitting material and an antioxidant (hereinafter also referred to as “first composition”). However, in the first composition, the light emitting material is different from the phosphorescent compound represented by the formula (1). In the first composition, the hole transport material, the hole injection material, the light emitting material, the electron transport material, and the electron injection material are different from the compound represented by the formula (H).
  • the hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound.
  • the hole transport material may have a crosslinking group.
  • 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, trinitrofluorenone, and fullerene is preferable.
  • the compounding amount of the hole transport material is usually when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. 1 to 400 parts by weight, preferably 5 to 150 parts by weight.
  • 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 compounds and high molecular compounds.
  • the electron transport material may have a crosslinking group.
  • low molecular weight compounds include phosphorescent compounds 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 total amount of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight, 1 to 400 parts by weight, preferably 5 to 150 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 classified into a low molecular compound and a high molecular compound, respectively.
  • 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; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.
  • the compounding amounts of the hole injection material and the electron injection material are each 100 weights of the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H).
  • the amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight.
  • Each of the electron injection material and the hole 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. Doping ions may be used alone or in combination of two or more.
  • Luminescent materials are classified into low molecular compounds and high molecular compounds.
  • the light emitting material may have a crosslinking group.
  • low molecular weight compound examples include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.
  • Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, a group represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine diyl.
  • the light emitting material preferably comprises a triplet light emitting complex.
  • the triplet luminescent complex include the metal complexes shown below.
  • the amount of the luminescent material is usually 1 when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. Up to 400 parts by weight, preferably 5 to 150 parts by weight.
  • a luminescent material may be used individually by 1 type, or may use 2 or more types together.
  • the antioxidant may be any compound that is soluble in the same solvent as the phosphorescent compound represented by formula (1) and the compound represented by formula (H) and does not inhibit light emission and charge transport. , Phenolic antioxidants and phosphorus antioxidants.
  • the total amount of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight, 0.001 to 10 parts by weight.
  • Antioxidants may be used alone or in combination of two or more.
  • a composition containing a phosphorescent compound represented by the formula (1), a compound represented by the formula (H), and a solvent (hereinafter also referred to as “first ink”) is prepared by a spin coating method.
  • the viscosity of the first ink may be adjusted according to the type of wet method. However, when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging at the time of discharge and flight bending occur. Since it is difficult, it is preferably 1 to 20 mPa ⁇ s at 25 ° C.
  • the solvent contained in the first ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink.
  • the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone,
  • the amount of the solvent is usually 1000 to 100,000 when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. Parts by weight, preferably 2000 to 20000 parts by weight.
  • the second organic layer is a layer containing a crosslinked material of a crosslinking material.
  • a cross-linked body of the cross-linking material can be obtained by cross-linking the cross-linking material by the above-described method and conditions.
  • the cross-linking material may be a low-molecular compound or a high-molecular compound, but since the luminance life of the light-emitting device of the embodiment of the present invention is more excellent, at least one cross-linking group selected from the cross-linking group A group Or a high molecular compound (hereinafter also referred to as “low molecular compound of the second organic layer”) or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group (
  • the polymer compound is also preferably “a polymer compound of the second organic layer”), and is a polymer compound including a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. More preferred.
  • the luminance life of the light emitting device of the embodiment of the present invention is more excellent. Therefore, the formula (XL-1) to the formula (XL-4) and the formula (XL-7) are preferable.
  • the crosslinkable group selected from the crosslinkable group A is preferably a group represented by the formula (XL-2) to the formula (XL-15) or the formula (XL-17) because the crosslinkability of the crosslinkable material is more excellent. More preferably, the formula (XL-2) to the formula (XL-4), the formula (XL-7) to the formula (XL-10), the formula (XL-14), the formula (XL-15) or the formula A crosslinking group represented by (XL-17), more preferably a crosslinking group represented by formula (XL-3), formula (XL-9), formula (XL-10) or formula (XL-17) And particularly preferably a crosslinking group represented by the formula (XL-17).
  • the structural unit having at least one cross-linking group selected from the cross-linking group A group contained in the polymer compound of the second organic layer is a structural unit represented by formula (2) or formula (2 ′) described later. Although it is preferably a structural unit represented, the structural unit represented below may be sufficient.
  • nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • n is preferably 2 because the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • Ar 3 is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • the number of carbon atoms of the aromatic hydrocarbon group represented by Ar 3 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.
  • the arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar 3 is preferably a group represented by the formula (A-1) to the formula (A-20), More preferably, groups represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) And more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), This group may have a substituent.
  • the number of carbon atoms of the heterocyclic group represented by Ar 3 is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group part excluding n substituents of the heterocyclic group represented by Ar 3 is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.
  • the aromatic hydrocarbon group and heterocyclic group represented by Ar 3 may have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group.
  • Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.
  • the alkylene group represented by L A is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the number of carbon atoms of the substituent. 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.
  • Alkylene group and cycloalkylene group represented by L A may have a substituent.
  • the substituent that the alkylene group and the cycloalkylene group may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group, and these groups further have a substituent. It may be.
  • the arylene group represented by L A may have a substituent.
  • the arylene group is preferably a phenylene group or a fluorenediyl group, more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group.
  • the substituent that the arylene group 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 cyano group, or a bridging group A.
  • a crosslinking group selected from the group is preferred, and these groups may further have a substituent.
  • the divalent heterocyclic group represented by L A is preferably a group represented by formula (AA-1) to formula (AA-34).
  • L A is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group, or an alkylene group, because production of the polymer compound of the second organic layer is facilitated.
  • This group may have a substituent.
  • the crosslinking group represented by X is represented by the formula (XL-2) to the formula (XL-15) or the formula (XL-17) because the crosslinkability of the polymer compound of the second organic layer is excellent. And more preferably a formula (XL-2) to a formula (XL-4), a formula (XL-7) to a formula (XL-10), a formula (XL-14), a formula (XL-15) or A crosslinking group represented by the formula (XL-17), more preferably represented by the formula (XL-3), the formula (XL-9), the formula (XL-10) or the formula (XL-17).
  • the structural unit represented by the formula (2) is excellent in the stability and crosslinkability of the polymer compound of the second organic layer, it is based on the total amount of the structural units contained in the polymer compound of the second organic layer. Thus, it is preferably 0.5 to 80 mol%, more preferably 3 to 50 mol%, still more preferably 5 to 20 mol%.
  • One type of structural unit represented by the formula (2) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
  • mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • m is preferably 1 or 2 and more preferably 2 because the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • c is preferably 0, because the production of the polymer compound of the second organic layer is facilitated and the luminance life of the light emitting device of the embodiment of the present invention is more excellent.
  • Ar 5 is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • the definition and examples of the arylene group portion excluding m substituents of the aromatic hydrocarbon group represented by Ar 5 are the same as the definitions and examples of the arylene group represented by Ar X2 in formula (X) described later. It is.
  • the definition and examples of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar 5 are the divalent heterocyclic group represented by Ar X2 in formula (X) described later. Same as definition and example of part.
  • divalent groups excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar 5 and at least one heterocyclic ring are directly bonded are shown in the formula ( The definition and examples of the divalent group in which at least one arylene group represented by Ar X2 in X) and at least one divalent heterocyclic group are directly bonded are the same.
  • Ar 4 and Ar 6 are preferably an arylene group which may have a substituent since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • the definitions and examples of the arylene group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the arylene group represented by Ar X1 and Ar X3 in the formula (X) described later.
  • the definitions and examples of the divalent heterocyclic group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the divalent heterocyclic group represented by Ar X1 and Ar X3 in formula (X) described later. is there.
  • the groups represented by Ar 4 , Ar 5 and Ar 6 may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, Examples thereof include a halogen atom, a monovalent heterocyclic group, and a cyano group.
  • K A since production of the polymer compound of the second organic layer becomes easy, it is preferable that a phenylene group or a methylene group.
  • the definition and example of the crosslinking group represented by X ′ are the same as the definition and example of the crosslinking group represented by X described above.
  • the structural unit represented by the formula (2 ′) is excellent in the stability of the polymer compound in the second organic layer and in the crosslinking property of the polymer compound in the second organic layer.
  • the amount is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of structural units contained in the polymer compound in the layer.
  • One type of structural unit represented by the formula (2 ′) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
  • Examples of the structural unit represented by the formula (2) include structural units represented by the formula (2-1) to the formula (2-30), and the structural unit represented by the formula (2 ′) Examples include structural units represented by the formulas (2′-1) to (2′-9).
  • it is preferably a structural unit represented by the formula (2-1) to the formula (2-30), more preferably the formula (2 -1) to Formula (2-15), Formula (2-19), Formula (2-20), Formula (2-23), Formula (2-25), or Formula (2-30)
  • the second organic layer further contains a structural unit represented by the formula (X).
  • the polymer compound of the second organic layer preferably further includes a structural unit represented by the formula (Y) because the luminance life of the light emitting device of the embodiment of the present invention is more excellent.
  • the structural unit and formula represented by the formula (X) are further included. It is preferable that the structural unit represented by (Y) is included.
  • a X1 and a X2 each independently represent an integer of 0 or more.
  • Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups 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 at least one arylene group and at least one divalent heterocyclic group are directly bonded. And these groups may have a substituent.
  • Ar X2 and Ar X4 When 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 an integer of 2 or less, more preferably 1, since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • a X2 is preferably an integer of 2 or less, more preferably 0, because the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. Also good.
  • 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 more preferably a formula (A-1). These groups may have a substituent.
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably an arylene group which may have a substituent.
  • the arylene group represented by Ar X2 and Ar X4 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (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 .
  • Examples of the divalent group in which at least one arylene group represented by Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulae. These 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.
  • 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) to the formula (X-7), more preferably the formula (X-3) to the formula (X -7), more preferably structural units represented by formula (X-3) to formula (X-6).
  • R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or 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 90 mol% based on the total amount of the structural units contained in the polymer compound of the second organic layer. More preferably, it is 1 to 70 mol%, and still more preferably 10 to 50 mol%.
  • Examples of the structural unit represented by the formula (X) include structural units represented by the formula (X1-1) to the formula (X1-19), preferably the formula (X1-6) to the formula (X1 -14).
  • the structural unit represented by the formula (X) may be included alone or in combination of two or more.
  • Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent.
  • the arylene group represented by Ar Y1 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A) A-13) or a group represented by formula (A-19), more preferably in formula (A-1), formula (A-7), formula (A-9) or formula (A-19). And these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar Y1 is represented by the formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) ) Or a group represented by formula (AA-20), particularly preferably represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) These groups may have a substituent.
  • the ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar Y1 described above.
  • the divalent group in which at least one arylene group represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded to each other is at least represented by Ar X2 and Ar X4 in the formula (X). Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.
  • the substituent that the group represented by Ar Y1 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.
  • Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-1) to the formula (Y-7), and the luminance lifetime of the light emitting element according to the embodiment of the present invention. From the viewpoint, it is preferably a structural unit represented by the formula (Y-1) or the formula (Y-2), and from the viewpoint of the electron transport property of the polymer compound of the second organic layer, Y-3) or a structural unit represented by the formula (Y-4), and from the viewpoint of the hole transport property of the polymer compound of the second organic layer, preferably the formula (Y-5) to the formula (Y Y-7) is a structural unit.
  • 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.
  • the structural unit represented by the formula (Y-1) is preferably a structural unit represented by the formula (Y-1 ′).
  • R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a plurality of R Y11 may be the same or different.
  • R Y11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups 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, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. May be.
  • R Y2 in the group represented by —C (R Y2 ) 2 — in X Y1 is preferably an alkyl group or a cycloalkyl group, both are aryl groups, and both are monovalent complex
  • R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R Y2 forms a ring, the group represented by —C (R Y2 ) 2 — Is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. You may do it.
  • 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) to the formula (Y-B5), more preferably a group represented by the formula (Y-B3). It may have a substituent.
  • R Y2 represents the same meaning as described above.
  • the structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).
  • 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 alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.
  • 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 alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.
  • Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-11) to the formula (Y-56), and preferably the formula (Y-11) to the formula (Y Y-55).
  • the structural unit represented by the formula (Y), in which Ar Y1 is an arylene group, has a higher luminance life of the light-emitting element of the embodiment of the present invention.
  • the amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the structural units contained in.
  • the structural unit that is a group of the organic compound is preferably 0.5 to a total amount of the structural units contained in the polymer compound of the second organic layer because the polymer compound of the second organic layer is excellent in charge transportability. It is 40 mol%, more preferably 3 to 30 mol%.
  • One type of structural unit represented by the formula (Y) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
  • Examples of the polymer compound in the second organic layer include polymer compounds P-1 to P-8 shown in Table 1.
  • the “other structural unit” means a structural unit other than the structural units represented by Formula (2), Formula (2 ′), Formula (X), and Formula (Y).
  • the number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 to 5 ⁇ 10 5 , more preferably 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
  • the polymer compound of the second organic layer can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc. Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
  • a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
  • 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.
  • transition metal catalysts examples include palladium catalysts and nickel catalysts.
  • 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 low molecular compound of the second organic layer is preferably a low molecular compound represented by the formula (3).
  • m B1 , m B2 and m B3 each independently represent an integer of 0 or more.
  • a plurality of m B1 may be the same or different.
  • a plurality of m B3 are present, they may be the same or different.
  • Ar 7 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be. When a plurality of Ar 7 are present, they may be the same or different.
  • L B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R ′ ′′) —, an oxygen atom or a sulfur atom, and these groups are substituent groups. You may have.
  • 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.
  • a plurality of L B1 When a plurality of L B1 are present, they may be the same or different.
  • X ′′ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of X ′′ may be the same or different. However, at least one of a plurality of X ′′ is a crosslinking group.
  • m B1 is generally an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, and even more preferably 0 or 0, because synthesis of the crosslinking material is facilitated.
  • m B2 is generally an integer of 0 to 10, and is preferably an integer of 0 to 5 because the synthesis of the cross-linking material is facilitated and the luminance life of the light emitting device of the embodiment of the present invention is more excellent. More preferably, it is an integer of 0 to 3, more preferably 1 or 2, and particularly preferably 1.
  • m B3 is generally an integer of 0 to 5, and is preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and still more preferably 0 because synthesis of the cross-linking material is facilitated. is there.
  • the definition and examples of the arylene group part excluding m B3 substituents of the aromatic hydrocarbon group represented by Ar 7 are the definitions and examples of the arylene group represented by Ar X2 in the aforementioned formula (X). The same.
  • the definition and examples of the divalent heterocyclic group part excluding m B3 substituents of the heterocyclic group represented by Ar 7 are the divalent heterocyclic ring represented by Ar X2 in the above formula (X). Same as definition and example of base part.
  • the definition and examples of the divalent group excluding m B3 substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar 7 and at least one heterocycle are directly bonded are as described above.
  • the definition and example of the divalent group in which at least one kind of arylene group represented by Ar X2 and at least one kind of divalent heterocyclic group in (X) are directly bonded are the same.
  • the definition and example of the substituent that the group represented by Ar 7 may have are the same as the definition and example of the substituent that the group represented by Ar X2 in Formula (X) may have. is there.
  • Ar 7 is preferably an aromatic hydrocarbon group because the luminance lifetime of the light emitting device of the embodiment of the present invention is excellent, and this aromatic hydrocarbon group may have a substituent.
  • alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by L B1 are respectively the alkylene group, cycloalkylene group, arylene group and divalent represented by L A described above. This is the same as the definition and example of the heterocyclic group of.
  • L B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, still more preferably a phenylene group, a fluorenediyl group or An alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups optionally have a substituent.
  • X ′′ is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any one of the formulas (XL-1) to (XL-17), more preferably the formula (XL -1), a crosslinking group represented by formula (XL-3), formula (XL-7) to formula (XL-10), formula (XL-16) or formula (XL-17), or an aryl group More preferably a crosslinking group represented by the formula (XL-1), the formula (XL-16) or the formula (XL-17), a phenyl group, a naphthyl group or a fluorenyl group.
  • XL-16 or a crosslinking group represented by the formula (XL-17), a phenyl group or a naphthyl group, particularly preferably a crosslinking group represented by the formula (XL-16) or a naphthyl group, These groups may have a substituent.
  • cross-linking material examples include low molecular compounds represented by formulas (3-1) to (3-16), and preferably represented by formulas (3-1) to (3-10). Low molecular compounds, more preferably low molecular compounds represented by formulas (3-5) to (3-9).
  • the low molecular weight compound of the second organic layer is available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source. In addition, it is compoundable according to the method described in the international publication 1997/033193, the international publication 2005/035221, and the international publication 2005/049548, for example.
  • the crosslinked material of the crosslinking material may be contained singly or in combination of two or more.
  • the second organic layer includes a crosslinked material of a crosslinking material and at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. May be a layer containing a composition (hereinafter, also referred to as “second composition”).
  • Examples and preferred ranges of the hole transport material, electron transport material, hole injection material, electron injection material and luminescent material contained in the second composition are the hole transport material contained in the first composition.
  • the examples of the electron transport material, the hole injection material, the electron injection material, and the light emitting material are the same as the preferred range.
  • the compounding amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material are each usually 1 when the crosslinked material is 100 parts by weight. Up to 400 parts by weight, preferably 5 to 150 parts by weight.
  • the blending amount of the antioxidant is usually 0.001 to 10 parts by weight when the crosslinked material of the crosslinking material is 100 parts by weight.
  • the second composition containing the crosslinking material and the solvent (hereinafter also referred to as “second ink”) can be suitably used in the wet method described in the section of the first ink.
  • the preferable range of the viscosity of the second ink is the same as the preferable range of the viscosity of the first ink.
  • Examples and preferred ranges of the solvent contained in the second ink are the same as examples and preferred ranges of the solvent contained in the first ink.
  • the compounding amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight when the crosslinking material is 100 parts by weight.
  • the light emitting device of the embodiment of the present invention may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.
  • the first organic layer is usually a light emitting layer (hereinafter referred to as “first light emitting layer”).
  • the second organic layer is usually a hole transport layer, a second light emitting layer or an electron transport layer, preferably a hole transport layer or a second light emitting layer. More preferably, it is a hole transport layer.
  • the first organic layer and the second organic layer are preferably adjacent to each other because the luminance life of the light emitting device of the embodiment of the present invention is more excellent.
  • the second organic layer is a layer provided between the anode and the first organic layer because the luminance life of the light emitting device of the embodiment of the present invention is more excellent.
  • the hole transport layer or the second light-emitting layer provided between the anode and the first organic layer is more preferable, and the hole transport layer provided between the anode and the first organic layer. More preferably.
  • the luminance life of the light emitting device of the embodiment of the present invention is further improved. Since it is excellent, it is preferable to further have a hole injection layer between the anode and the second organic layer. In addition, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the luminance life of the light emitting device of the embodiment of the present invention is more excellent. It is preferable to further include at least one of an electron injection layer and an electron transport layer between the organic layer.
  • the luminance lifetime of the light emitting device of the embodiment of the present invention is Since it is more excellent, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the second organic layer.
  • the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the luminance life of the light emitting device of the embodiment of the present invention is more excellent, and therefore the cathode and the first It is preferable to further include at least one of an electron injection layer and an electron transport layer between the organic layer and the organic layer.
  • the luminance life of the light emitting device of the embodiment of the present invention is Since it is more excellent, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the first organic layer.
  • the second organic layer is a second light emitting layer provided between the cathode and the first organic layer
  • the luminance life of the light emitting device of the embodiment of the present invention is more excellent, and therefore, the cathode and the second organic layer.
  • the luminance life of the light emitting device of the embodiment of the present invention is more excellent. Therefore, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the first organic layer. In addition, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the luminance life of the light emitting device of the embodiment of the present invention is more excellent. It is preferable to further have an electron injection layer between the layers.
  • the layer structure of the light emitting device according to the embodiment of the present invention include layer structures represented by the following (D1) to (D15).
  • the light emitting device of the embodiment of the present invention usually has a substrate, but may be laminated on the substrate from the anode, or may be laminated on the substrate from the cathode.
  • “/” means that the previous and subsequent layers are adjacently stacked.
  • “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” means the second light emitting layer (second organic layer) and the first light emitting layer (second organic layer).
  • the light emitting layer (first organic layer) is adjacently laminated. Since the luminance lifetime of the light emitting device of the embodiment of the present invention is more excellent, the layer configuration represented by (D3) to (D12) is preferable, and the layer configuration represented by (D7) to (D10) is more preferable.
  • the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are provided in two or more layers as necessary. It may be done. When there are a plurality of anodes, hole injection layers, hole transport layers, second light emitting 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 2 nm to It is 500 nm, more preferably 5 nm to 150 nm.
  • the order, the number, and the thickness of the layers to be stacked may be adjusted in consideration of the light emission efficiency and the element life of the light emitting element.
  • the second light emitting layer is usually a layer containing a second organic layer or a light emitting material.
  • the second light emitting layer is a layer containing a light emitting material
  • examples of the light emitting material contained in the second light emitting layer include the light emitting material that may be contained in the first composition. It is done.
  • the light emitting material contained in the second light emitting layer may be contained singly or in combination of two or more.
  • the second light-emitting layer is the second light-emitting layer.
  • the organic layer is preferable.
  • the hole transport layer is usually a layer containing a second organic layer or a hole transport material.
  • the hole transport layer is a layer containing a hole transport material
  • examples of the hole transport material include a hole transport material that may be contained in the first composition described above.
  • the hole transport material contained in the hole transport layer may be contained singly or in combination of two or more.
  • the hole transport layer is the second transport layer.
  • An organic layer is preferred.
  • the electron transport layer is usually the second organic layer or a layer containing an electron transport material, and preferably a layer containing an electron transport material.
  • the electron transport layer is a layer containing an electron transport material
  • examples of the electron transport material contained in the electron transport layer include the electron transport material that may be contained in the first composition described above. .
  • the electron transport material contained in the electron transport layer is represented by the formula (ET-1).
  • a polymer compound containing at least one structural unit selected from the group consisting of the structural unit represented by formula (ET-2) hereinafter also referred to as “polymer compound of electron transport layer”. It is preferable that
  • 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 usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.
  • aE1 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.
  • bE1 is generally an integer of 0 to 10, preferably an integer of 0 to 4, more preferably 0 or 1.
  • mE1 is usually an integer of 1 to 5, preferably 1 or 2, and more 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 a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.
  • R E3 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3).
  • the group represented by 3) is preferred.
  • Q E1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an oxygen atom.
  • Y E1 is preferably CO 2 ⁇ , SO 2 ⁇ or PO 3 2 ⁇ , more preferably CO 2 ⁇ .
  • Examples of the alkali metal cation represented by M E1 include Li + , Na + , K + , Rb + , and Cs + . K + , Rb +, and Cs + are preferable, and Cs + is more preferable.
  • Examples of the alkaline earth metal cation represented by M E1 include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ , and Mg 2+ , Ca 2+ and Sr 2+. Or Ba ⁇ 2+> is preferable and Ba ⁇ 2+> is more preferable.
  • M E1 is preferably an alkali metal cation or alkaline earth metal cation, more preferably an alkali 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 ⁇ , and F ⁇ , Cl ⁇ . , Br -, I -, OH -, R E4 SO 3 - or R E4 COO - is more preferable.
  • 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.
  • NE2 is usually an integer of 1 to 4, preferably 1 or 2.
  • Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar E2 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 n2 atoms is preferable, and may have a substituent other than R E2 .
  • the substituent group other than Ar E2 is may have R E2, is the same as the substituent other than optionally Ar E1 is have R E1.
  • nE4 is generally an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.
  • aE2 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.
  • bE2 is usually an integer of 0 to 10, preferably an integer of 0 to 4, more preferably 0 or 1.
  • mE2 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 1.
  • R E5 is —O—R E5 ′
  • the group represented by the formula (ES-2) is a group represented by the following formula. -O-R E5 '- ⁇ (Q E1 ) nE3 -Y E1 (M E1 ) aE1 (Z E1 ) bE1 ⁇ mE1
  • R E5 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.
  • R E5 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3).
  • the group represented by 3) is preferred.
  • Q E2 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an oxygen atom.
  • R E6 is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group.
  • M E2 is preferably F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (R E7 ) 4 ⁇ , R E7 SO 3 ⁇ , R E7 COO ⁇ , BF 4 ⁇ or SbF 6 ⁇ , and Br ⁇ , I -, B (R E7) 4 -, R E7 COO - or SbF 6- is more preferable.
  • R E7 is preferably an alkyl group.
  • Examples of the alkali metal cation represented by Z E2 include Li + , Na + , K + , Rb + and Cs + , and Li + , Na + or K + is preferable.
  • Examples of the alkaline earth metal cation represented by Z E2 include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ , with Mg 2+ or Ca 2+ being preferred.
  • Z E2 is preferably an alkali metal cation.
  • 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.
  • a material used for forming a hole injection layer a material used for forming a hole transport layer, a material used for forming a first light emitting layer, a material used for forming a second light emitting layer, and a material for forming an electron transport layer.
  • the materials used and the materials used to form the electron injection layer are a hole injection layer, a hole transport layer, a first light emitting layer, a second light emitting layer, an electron transport layer, and an electron, respectively, in manufacturing a light emitting element.
  • 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.
  • the electron-emitting layer when an electron transport layer is stacked on a first light-emitting layer or a second light-emitting layer using a difference in solubility, the electron-emitting layer is soluble in the first light-emitting layer or the second light-emitting layer.
  • the electron transport layer can be stacked by using a low solution.
  • a solvent used when an electron transport layer is laminated on the first light-emitting layer or the second light-emitting layer using a difference in solubility water, alcohol, ether, ester, nitrile compound, nitro compound, Fluorinated alcohol, thiol, sulfide, sulfoxide, thioketone, amide, carboxylic acid and the like are preferable.
  • the solvent examples include methanol, ethanol, 2-propanol, 1-butanol, tert-butyl alcohol, acetonitrile, 1,2-ethanediol, N, N-dimethylformamide, dimethyl sulfoxide, acetic acid, nitromethane, propylene carbonate , Pyridine, carbon disulfide, and a mixed solvent of these solvents.
  • a mixed solvent one or more solvents selected from water, alcohols, ethers, esters, nitrile compounds, nitro compounds, fluorinated alcohols, thiols, sulfides, sulfoxides, thioketones, amides, carboxylic acids, and the like, and chlorinated solvents Further, it may be a mixed solvent with one or more of an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, and a ketone solvent.
  • the hole injection layer is a layer containing a hole injection material.
  • a hole injection material contained in a hole injection layer the hole injection material which the above-mentioned 1st composition may contain is mentioned, for example.
  • the hole injection material contained in the hole injection layer 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 contained in an electron injection layer the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example.
  • the electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.
  • the substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed.
  • the substrate is made of a material such as glass, plastic, or silicon.
  • the electrode farthest from the substrate is transparent or translucent.
  • Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • conductive metal oxides and translucent metals preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • ITO indium tin oxide
  • 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 transporting layer, the electron transporting layer, the hole injecting layer, the electron injecting layer, the electron injecting layer,
  • a method for forming each layer such as the first light emitting layer, the second light emitting layer, the hole transporting layer, the electron transporting layer, the hole injecting layer, the electron injecting layer,
  • a compound for example, a vacuum deposition method from a powder, a method by film formation from a solution or a molten state can be mentioned. .
  • the first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer are the first ink, the second ink, and the above-described light-emitting material and hole. It can be formed by a wet method such as a spin coating method or an ink jet printing method using inks each containing a transport material, an electron transport material, a hole injection material, and an electron injection material.
  • planar anode and the 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 actively in combination with TFTs. 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 be used as a curved light source and display device.
  • the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound are either one of the following size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. Determined by The SEC measurement conditions are as follows.
  • the polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 ⁇ L was injected into SEC. The mobile phase was run at a flow rate of 2.0 mL / min.
  • PLgel MIXED-B manufactured by Polymer Laboratories
  • a UV-VIS detector manufactured by Shimadzu Corporation, trade name: SPD-10Avp was used as the detector.
  • the phosphorescent compound G1 was synthesized according to the method described in JP2013-237789A.
  • the phosphorescent compound G2 was synthesized according to the method described in International Publication No. 2004/026886.
  • the phosphorescent compound G3 was synthesized according to the method described in International Publication No. 2009/131255.
  • the phosphorescent compound G4 was synthesized according to the method described in JP 2014-224101 A.
  • the phosphorescent compound G5 was synthesized according to the method described in JP 2014-224101 A.
  • the phosphorescent compound G6 was synthesized according to the method described in International Publication No. 2011/032626.
  • the phosphorescent compound R1 was synthesized according to the method described in International Publication No. WO 2002/044189.
  • the phosphorescent compound R2 was synthesized according to the method described in JP-A-2006-188673.
  • the phosphorescent compound R3 was synthesized according to the method described in JP-A-2008-179617.
  • the phosphorescent compound R4 was synthesized according to the method described in JP2011-105701A.
  • the theoretical value obtained from the amount of charged raw materials for polymer compound HTL-1 is that the structural unit derived from compound M5, the structural unit derived from compound M3, and the structural unit derived from compound M6 are: It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.
  • phenylboronic acid 36.8 mg
  • dichlorobis triphenylphosphine
  • a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours.
  • the resulting reaction solution was washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation.
  • 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 3.12 g of a polymer compound HTL-2.
  • the polymer compound HTL-2 had an Mn of 7.8 ⁇ 10 4 and an Mw of 2.6 ⁇ 10 5 .
  • the polymer compound HTL-2 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M1, a structural unit derived from the compound M2, a structural unit derived from the compound M3, and a compound.
  • the structural unit derived from M4 is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.
  • 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.
  • AQ-1200 manufactured by Plextronics
  • the hole injection layer was formed by heating for 15 minutes.
  • the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. An organic layer of was formed. By this heating, the polymer compound HTL-1 became a crosslinked product.
  • the substrate on which the first organic 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 first organic layer. About 80 nm of aluminum was deposited on the sodium hydride layer. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.
  • Example D3 Production and Evaluation of Light-Emitting Element D3
  • a light emitting device D3 was manufactured.
  • Example D1 Formation of second organic layer“ 0.6 wt% of polymer compound HTL-1 in xylene ” Instead of “dissolved at a concentration of 5%”, light was emitted in the same manner as in Example D1, except that “polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by weight”. Element CD1 was produced.
  • Example D1 Formation of First Organic Layer
  • the compound H4 and phosphorescent compound G2 70 wt% in chlorobenzene.
  • 30 wt%) was dissolved at a concentration of 2 wt% ”in
  • Example D1 Formation of the second organic layer
  • “Polmer compound HTL-1 in xylene was 0.6 wt%.
  • a light emitting device CD3 was prepared in the same manner as in Example D1, except that “the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7 wt%”.
  • the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7 wt%”.
  • Table 2 shows the results obtained in Examples D1 to D3 and Comparative Examples CD1 to CD4.
  • Example D4 Production and Evaluation of Light-Emitting Element D4
  • polymer compound HTL-1 in (formation of second organic layer) in example D1
  • polymer compound HTL-2 was used.
  • Example D1 Formation of first organic layer
  • Example D5 Production and Evaluation of Light-Emitting Element D5 “Polymer Compound HTL-3” was used in place of “Polymer Compound HTL-2” in (Formation of Second Organic Layer) in Example D4 Except for the above, a light-emitting element D5 was produced in the same manner as in Example D4.
  • Table 3 shows the results obtained in Examples D4 to D5 and Comparative Example CD5.
  • 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.
  • AQ-1200 manufactured by Plextronics
  • the hole injection layer was formed by heating for 15 minutes.
  • the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. An organic layer of was formed. By this heating, the polymer compound HTL-1 became a crosslinked product.
  • the substrate on which the first organic 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 first organic layer. About 80 nm of aluminum was deposited on the sodium hydride layer. After vapor deposition, the light emitting element D6 was produced by sealing using a glass substrate.
  • Example D7 Production and Evaluation of Light-Emitting Element D7
  • Example D6 Formation of First Organic Layer
  • a light emitting device D7 was manufactured.
  • Example D8 Production and Evaluation of Light-Emitting Element D8
  • 10 wt% was dissolved at a concentration of 3.3 wt%, and a light emitting device D8 was fabricated in the same manner as in Example D6.
  • Example D9 Production and Evaluation of Light-Emitting Element D9
  • / 10 wt%) was dissolved at a concentration of 3.3 wt%.
  • a light emitting device D9 was produced in the same manner as in Example D6, except that the content was dissolved.
  • Example D10 Fabrication and Evaluation of Light-Emitting Element D10 “Polymer Compound HTL-2” was used instead of “Polymer Compound HTL-1” in (Formation of Second Organic Layer) in Example D6 Except for the above, a light-emitting element D10 was produced in the same manner as in Example D6.
  • Example D6 Production and Evaluation of Light-Emitting Element CD6
  • a light emitting device CD6 was produced.
  • Table 4 shows the results obtained in Examples D6 to D10.

Abstract

L'invention fournit un élément luminescent dont la durée de vie de luminance est excellente. Cet élément luminescent possède une anode, une cathode, et une première ainsi qu'une seconde couche organique agencées entre l'anode et la cathode. La première couche organique comprend un composé luminescent phosphorescent représenté par la formule (1), et un composé représenté par la formule (H). La seconde couche organique comprend un corps réticulé d'un corps réticulable. [Dans la formule (1), M représente un atome d'iridium, ou similaire. ｎ1 représente un nombre entier supérieur ou égal à 1, et ｎ2 représente un nombre entier supérieur ou égal à 0. Ｅ1 et Ｅ2 représentent un atome de carbone, ou similaire. Le cycle Ｌ1 représente un hétérocycle aromatique. Le cycle Ｌ2 représente un cycle hydrocarbure aromatique, ou similaire. Ａ1－Ｇ1－Ａ2 représente un ligand bidentate.] [Dans la formule (H), ｎH1 représente un nombre entier compris entre 0 et 5. ｎH2 représente un nombre entier compris entre 1 et 10. ＡｒH1 représente un groupe hétérocyclique monovalent spécifique. ＬH1 représente un groupe alkylène, un groupe arylène, ou similaire. ＡｒH2 représente un groupe hétérocyclique azoté possédant un atome d'azote ｓｐ2 en tant qu'atome constitutif de cycle. ＡｒH1 et/ou ＡｒH2 possède un dendron.]
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018062276A1 (fr) * 2016-09-29 2018-04-05 住友化学株式会社 Élément électroluminescent

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012096263A1 (fr) * 2011-01-11 2012-07-19 三菱化学株式会社 Composition pour élément électroluminescent organique, élément électroluminesecent organique, dispositif d'affichage et dispositif d'éclairage
WO2013146806A1 (fr) * 2012-03-27 2013-10-03 住友化学株式会社 Composé polymère et élément d'émission de lumière utilisant celui-ci
WO2015020217A1 (fr) * 2013-08-09 2015-02-12 出光興産株式会社 Composition pour électroluminescence organique, matériau pour élément électroluminescent organique, solution de matériau pour élément électroluminescent organique, et élément électroluminescent organique
JP2015110751A (ja) * 2013-10-31 2015-06-18 住友化学株式会社 組成物およびそれを用いた発光素子
WO2016000803A1 (fr) * 2014-06-30 2016-01-07 Merck Patent Gmbh Complexes métalliques
WO2016015815A1 (fr) * 2014-07-28 2016-02-04 Merck Patent Gmbh Complexes métalliques
JP2016506399A (ja) * 2012-12-21 2016-03-03 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセント素子のための材料
US20160181535A1 (en) * 2014-12-18 2016-06-23 Samsung Electronics Co., Ltd. Material for organic light-emitting device and organic light-emitting device including the same
WO2016184540A1 (fr) * 2015-05-18 2016-11-24 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016119340A (ja) * 2014-12-18 2016-06-30 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機電界発光素子用材料

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012096263A1 (fr) * 2011-01-11 2012-07-19 三菱化学株式会社 Composition pour élément électroluminescent organique, élément électroluminesecent organique, dispositif d'affichage et dispositif d'éclairage
WO2013146806A1 (fr) * 2012-03-27 2013-10-03 住友化学株式会社 Composé polymère et élément d'émission de lumière utilisant celui-ci
JP2016506399A (ja) * 2012-12-21 2016-03-03 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセント素子のための材料
WO2015020217A1 (fr) * 2013-08-09 2015-02-12 出光興産株式会社 Composition pour électroluminescence organique, matériau pour élément électroluminescent organique, solution de matériau pour élément électroluminescent organique, et élément électroluminescent organique
JP2015110751A (ja) * 2013-10-31 2015-06-18 住友化学株式会社 組成物およびそれを用いた発光素子
WO2016000803A1 (fr) * 2014-06-30 2016-01-07 Merck Patent Gmbh Complexes métalliques
WO2016015815A1 (fr) * 2014-07-28 2016-02-04 Merck Patent Gmbh Complexes métalliques
US20160181535A1 (en) * 2014-12-18 2016-06-23 Samsung Electronics Co., Ltd. Material for organic light-emitting device and organic light-emitting device including the same
WO2016184540A1 (fr) * 2015-05-18 2016-11-24 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018062276A1 (fr) * 2016-09-29 2018-04-05 住友化学株式会社 Élément électroluminescent
JPWO2018062276A1 (ja) * 2016-09-29 2019-07-11 住友化学株式会社 発光素子
JP7020420B2 (ja) 2016-09-29 2022-02-16 住友化学株式会社 発光素子

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