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WO2019004247A1 - Élément luminescent, et composé polymère avantageux pour la fabrication de celui-ci - Google Patents

Élément luminescent, et composé polymère avantageux pour la fabrication de celui-ci Download PDF

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Publication number
WO2019004247A1
WO2019004247A1 PCT/JP2018/024288 JP2018024288W WO2019004247A1 WO 2019004247 A1 WO2019004247 A1 WO 2019004247A1 JP 2018024288 W JP2018024288 W JP 2018024288W WO 2019004247 A1 WO2019004247 A1 WO 2019004247A1
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group
formula
represented
substituent
ring
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Japanese (ja)
Inventor
孝和 斎藤
龍二 松本
吉田　大泰
大介 福島
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a light emitting device and a polymer compound useful for the production thereof.
  • Patent Document 1 discloses a light emitting device having an organic layer containing a polymer compound (HT-1) and a light emitting layer containing a polymer compound containing a constitutional unit represented by the formula (C-1). Is described.
  • an object of this invention is to provide the light emitting element which is excellent in an external quantum efficiency.
  • 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 polymer compound (TP)
  • the second organic layer is a layer containing a crosslinked body of a crosslinked material, From the low molecular weight compound (T) in which the high molecular compound (TP) has an absolute value of 0.5 eV or less of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state Containing a constitutional unit containing a group excluding the above hydrogen atom,
  • the crosslinkable material is a low molecular weight compound having at least one crosslinkable group selected from crosslinkable group A, or a polymer compound including a crosslinkable structural unit having at least one crosslinkable group selected from crosslinkable group A group
  • the light emitting element is.
  • 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 bonding position.
  • the crosslinkable material is a polymer compound including a crosslinkable structural unit having at least one crosslinkable group selected from the crosslinkable group A group, and the crosslinkable structural unit is represented by the formula (2) [1], which is a structural unit represented by the formula or a structural unit represented by the formula (2 ′): [In the formula, nA represents an integer of 0 to 5, and n represents 1 or 2. When a plurality of nA are present, they may be the same or different.
  • Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
  • L A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N (R ') -, a group represented by an oxygen atom or a sulfur atom, chromatic these groups the substituent It may be done.
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L A is plurally present, they may be the same or different.
  • X represents a crosslinking group selected from the aforementioned crosslinking group A group. When two or more X exist, they may be same or different.
  • mA represents an integer of 0 to 5
  • m represents an integer of 1 to 4
  • c represents 0 or 1.
  • Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent.
  • Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
  • Ar 4 , Ar 5 and Ar 6 each form a ring by being directly bonded or bonded via an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded It may be done.
  • K A 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 have a substituent It may be done.
  • R ' represents the same meaning as described above. If K A there are a plurality, they may be the same or different.
  • X ' represents a bridging group selected from the above bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent .
  • a plurality of X 'are present they may be the same or different.
  • at least one X ′ is a crosslinking group selected from the aforementioned crosslinking group A group.
  • the crosslinking material is a low molecular weight compound having at least one type of crosslinking group selected from the crosslinking group A group, and the low molecular weight compound is a low molecular weight compound represented by Formula (3) , The light emitting element as described in [1].
  • Each of m B1 and m B2 independently represents an integer of 0 or more and 10 or less.
  • m B3 represents an integer of 0 or more and 5 or less.
  • Plural m B1 may be the same or different. When 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 an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent. 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 substituents May be included.
  • R ′ ′ ′ 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.
  • X ′ ′ represents a bridging group selected from the above bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent Good.
  • Plural X ′ ′ may be the same or different.
  • a constitutional unit containing a group formed by removing one or more hydrogen atoms from the low molecular weight compound (T) is a constitutional unit represented by the formula (1C), a constitutional unit represented by the formula (2C), The light emitting device according to any one of [1] to [3], which is a structural unit represented by the formula (3C) or a structural unit represented by the formula (4C).
  • T 1C represents a group obtained by removing one hydrogen atom from the low molecular weight compound (T).
  • R A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • R B represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Plural R.sup.B's may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are attached. When a plurality of L C exist, they may be the same or different.
  • n c1 represents an integer of 0 or more and 10 or less. ] [In the formula, T 1C represents the same meaning as described above.
  • R A and R B represent the same meaning as described above.
  • n d1 and n e1 each independently represent an integer of 0 or more and 10 or less. Plural n d1 may be the same or different.
  • Ar 1 M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
  • L d and n d1 represent the same meaning as described above.
  • T 2C represents a group obtained by removing two hydrogen atoms from the low molecular weight compound (T).
  • L d and n d1 represent the same meaning as described above.
  • T 3 C represents a group formed by removing three hydrogen atoms from the low molecular weight compound (T).
  • the light emitting device according to any one of [1] to [4], wherein the polymer compound (TP) further contains a constitutional unit represented by the formula (Y).
  • Ar Y1 represents an arylene group which may have a substituent.
  • the structural unit represented by the formula (Y) is described in [5], which is a structural unit represented by the formula (Y-1), the formula (Y-2) or the formula (Y-3) Light emitting element.
  • R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent.
  • Plural R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • R Y1 is not a hydrogen atom.
  • R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl 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 atoms to which they are bonded. However, at least one R Y1 is not a hydrogen atom.
  • R Y1 and X Y1 have the same meaning as described above. However, at least one R Y1 is not a hydrogen atom.
  • [7] The light emitting device according to any one of [1] to [6], wherein the oscillator strength of the low molecular compound (T) is 0.0001 or more and 1 or less.
  • n T1 represents an integer of 0 or more and 5 or less. When there are a plurality of n T1 's , they may be the same or different.
  • Ar T1 represents a substituted amino group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar T1 are present, they may be the same or different, and may be directly bonded or may be bonded via a divalent group to form a ring.
  • R ZT1 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.
  • L T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R T1 ′) —, an oxygen atom or a sulfur atom, and these groups each have a substituent You may have.
  • R T1 ′ 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.
  • L T1 When a plurality of L T1 are present, they may be the same or different, and may be directly bonded or may be bonded via a divalent group to form a ring.
  • n T2 represents an integer of 1 or more and 15 or less.
  • n T2 is 3.
  • Ar T1 and L T1 may be directly bonded or may be bonded via a divalent group to form a ring.
  • Ar T2 and L T1 may be directly bonded or may be bonded via a divalent group to form a ring.
  • Ar T1 and Ar T2 may be directly bonded, or may be bonded via a divalent group to form a ring.
  • the first organic layer further contains at least one selected from the group consisting of a host material, a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material and an antioxidant.
  • the light-emitting device according to any one of [1] to [8].
  • R D1 , R D2 , R D3 , R D4 , R D5 , R D6 , R D7 and R D8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent.
  • R D1 , R D2 , R D3 , R D4 , R D5 , R D6 , R D7 and R D8 may be the same or different.
  • a D2 represents an anionic bidentate ligand
  • a D1 and A D2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom, and these The atom of may be an atom constituting a ring.
  • n D1 represents 1, 2 or 3
  • n D2 represents 1 or 2; ] [11]
  • k represents 0 or 1; Plural k may be the same or different.
  • m DA1 represents an integer of 0 or more and 10 or less. When a plurality of m DA1 are present, they may be the same or different.
  • n d1 represents an integer of 0 or more and 10 or less. Plural n d1 may be the same or different.
  • n T1 represents 1 or 2;
  • Ar DA1 represents an arylene group which may have a substituent. When a plurality of Ar DA1 are present, they may be the same or different.
  • Ar L1 represents a group obtained by removing one hydrogen atom from the group represented by T DA . When a plurality of Ar L1 are present, they may be the same or different.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Ar TW represents a constitutional unit represented by the formula (Y-1), the formula (Y-2) or the formula (Y-3). Plural Ar TWs may be the same or different.
  • R A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • R B represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Plural R.sup.B's may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are attached.
  • L T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R T1 ′) —, an oxygen atom or a sulfur atom, and these groups each have a substituent You may have.
  • R T1 ′ 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.
  • a plurality of L T1 When a plurality of L T1 are present, they may be the same or different, and may be directly bonded or may be bonded via a divalent group to form a ring.
  • the formula (P) Represents a heterocyclic ring which does not contain the group represented by 1 in the ring, and these rings may have a substituent.
  • R ZT1 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.
  • X T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R XT1 )-, or a group represented by -C (R XT1 ') 2- .
  • R XT1 and R XT1 ′ are each independently 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 cyano group is represented, and these groups may have a substituent.
  • a plurality of R XT1 ' may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • the light emitting element which is excellent in an external quantum efficiency, and the high molecular compound useful to its manufacture can be provided.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • i-Pr represents an isopropyl group
  • t-Bu represents a tert-butyl group.
  • the hydrogen atom may be a deuterium atom or a light hydrogen atom.
  • the solid line representing the bond to 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 may be another embodiment.
  • the end group of the polymer compound is preferably a stable group because the light emission characteristics or the luminance life may be reduced when the polymer compound is used for the preparation of a light emitting device if the polymerization active group remains as it is. It is.
  • the terminal group include a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.
  • the “low molecular weight compound” means a compound having no molecular weight distribution and having a molecular weight of 1 ⁇ 10 4 or less.
  • the "constituent unit” means a unit which is present one or more in the polymer compound.
  • the “alkyl group” may be linear or branched.
  • the carbon atom number of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent.
  • the carbon atom number of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent.
  • the alkyl group may have a substituent, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group and an 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 or the like (for example, a trifluoromethyl 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, not including 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.
  • the “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 carbon atom number of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the carbon atom number of the substituent.
  • the aryl group may have a substituent, and examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-pyrenyl, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atom in these groups Are groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like.
  • the "alkoxy group” may be linear or branched.
  • the carbon atom number of the linear alkoxy group is usually 1 to 40, preferably 4 to 10, not including the carbon atom number of the substituent.
  • the carbon atom number of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the carbon atom number of the substituent.
  • the alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, And heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3, 7-dimethyloctyloxy group, lauryloxy group, and a hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, Examples thereof include groups substituted with a cycloalkoxy group, an aryl group, a fluorine atom and the like.
  • the carbon atom number of the "cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the carbon atom number 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, and examples thereof include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Pyrenyloxy groups and groups 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 can be mentioned.
  • the “p-valent heterocyclic group” (p represents an integer of 1 or more) means p out of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from the heterocyclic compound. Means the remaining atomic groups excluding the hydrogen atom of Among p-valent heterocyclic groups, carbon atoms constituting the ring or the remaining atomic groups obtained by removing p hydrogen atoms from hydrogen atoms directly bonded to a hetero atom from an aromatic heterocyclic compound "P-valent aromatic heterocyclic group” is preferred.
  • the “aromatic heterocyclic compound” is a complex such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole etc.
  • Compounds in which the ring itself exhibits aromaticity, and heterocycles such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran and the like themselves do not show aromaticity, but an aromatic hydrocarbon ring is condensed to the heterocycle.
  • the carbon atom number of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the carbon atom number of the substituent.
  • the monovalent heterocyclic group may have a substituent, and examples thereof include thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and the like Groups in which a hydrogen atom in any of the groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or the like.
  • halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the "amino group” may have a substituent and is preferably a substituted amino group.
  • 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 dialkylamino group, dicycloalkylamino group and diarylamino group.
  • the amino group include dimethylamino, diethylamino, diphenylamino, bis (4-methylphenyl) amino, bis (4-tert-butylphenyl) amino, and bis (3,5-di-tert-). And butylphenyl) amino.
  • the "arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon.
  • the carbon atom number of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the carbon atom number of the substituent.
  • the arylene group may have a substituent, and examples thereof include phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrendiyl group, dihydrophenanthrendiyl group, naphthacene diyl group, fluorenediyl group, pyrene diyl group, perylene diyl group, There may be mentioned a chrysendiyl group and a group in which these groups have a substituent, and preferably a group represented by the formula (A-1) to the formula (A-20).
  • the arylene group includes a group in which a plurality of these groups are bonded.
  • R and R a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
  • Plural R and R a may be the same as or different from each other, and R a may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • the carbon atom number of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15, not including the carbon atom number of the substituent.
  • the divalent heterocyclic group may have a substituent, and examples thereof include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, and the like.
  • dihydroacridines furans, thiophenes, azoles, diazoles and triazoles
  • divalent groups in which two hydrogen atoms of hydrogen atoms directly bonded to ring carbon atoms or hetero atoms are removed, 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 are bonded.
  • crosslinking group is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction and the like, preferably a crosslinking group. It is a crosslinking group represented by formulas (XL-1) to (XL-17) of group A.
  • the “substituent” represents a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group or a substituted amino 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 polymer compound (TP)
  • the second organic layer is a layer containing a crosslinked body of a crosslinked material
  • the polymer compound (TP) has an absolute value (hereinafter also referred to as “ ⁇ E ST ”) of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less
  • the crosslinkable material is a low molecular weight compound having at least one crosslinkable group selected from crosslinkable group A, or a polymer compound including a crosslinkable structural unit having at least one crosslinkable group selected from crosslinkable group A group It is the said light emitting element.
  • a dry method such as a vacuum evaporation method and a wet method such as a spin coating method and an inkjet method can be mentioned, and a wet method is preferable.
  • the first organic layer is formed by a wet method, it is preferable to use a first ink described later.
  • the crosslinking material contained in the second organic layer can be crosslinked by heating or light irradiation, and by heating, the crosslinking contained in the second organic layer It is preferred to crosslink the material.
  • the crosslinked material is contained in the second organic layer in a crosslinked state (crosslinked body of the crosslinked material)
  • the second organic layer is substantially insolubilized in the solvent. Therefore, the second organic layer can be suitably used for laminating light emitting elements.
  • the heating temperature for crosslinking is usually 25 ° C. to 300 ° C., preferably 50 ° C. to 260 ° C., more preferably 130 ° C. to 230 ° C., still more preferably 180 ° C. to 210 ° C. .
  • the heating time is usually 0.1 minute to 1000 minutes.
  • the type of light used for light irradiation is, for example, ultraviolet light, near ultraviolet light, or visible light.
  • chemical separation analysis such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis method and instrumental analysis method can be mentioned.
  • IR infrared spectroscopy
  • NMR nuclear magnetic resonance spectroscopy
  • MS mass spectrometry
  • a component substantially insoluble in the organic solvent insoluble It is possible to separate into components (components) and components (soluble components) that dissolve in organic solvents.
  • the insoluble component can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and the dissolved component can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.
  • the polymer compound (TP) contained in the first organic layer is a structural unit (C) comprising a group formed by removing one or more hydrogen atoms from a low molecular compound (T) having a ⁇ E ST of 0.5 eV or less. )including.
  • the low molecular weight compound (T) is preferably a thermally activated delayed fluorescence (TADF) material.
  • the ⁇ E ST of the low molecular weight compound (T) is preferably 0.0001 eV or more and 0.45 eV or less, more preferably 0.001 eV or more and 0.20 eV or less because the external quantum efficiency of the light emitting device of the present invention is excellent. More preferably, it is 0.01 eV or more and 0.11 eV or less.
  • the oscillator strength of the low molecular weight compound (T) is preferably 0.005 or more and 1 or less, and more preferably 0.01 or more and 0.3 or less because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • Gaussian 09 which is a quantum chemistry calculation program
  • ⁇ E ST and oscillator strength can be calculated by using time dependent density functional theory at the B 3 LYP level.
  • a basis function usually, 6-31 G * is used, but when an atom which can not use 6-31 G * is included in the compound, LANL2DZ can be used for the atom.
  • the low molecular weight compound (T) is preferably a low molecular weight compound represented by the formula (T-1) because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • n T1 is preferably 1 or 2, and more preferably 1, because the external quantum efficiency of the light-emitting element of the present invention is excellent.
  • n T2 is preferably an integer of 1 or more and 3 or less, more preferably 1, because n T2 is excellent in the external quantum efficiency of the light-emitting element of the present invention.
  • Examples of the monovalent heterocyclic group represented by Ar T1 include a monovalent donor-type heterocyclic group described later and a monovalent heterocyclic group other than a monovalent donor-type heterocyclic group described below.
  • a monovalent donor-type heterocyclic group described later a monovalent donor-type heterocyclic group described below.
  • carbazolyl group, 1,2,3,4-tetrahydrocarbazolyl group, dibenzofuryl group or dibenzothienyl group more preferably carbazolyl group, and these groups have a substituent It is also good.
  • an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable, and an aryl group is more preferable, and these groups are further It may have a substituent.
  • Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent group possessed by the amino group are the examples and preferred examples of aryl group and monovalent heterocyclic group in the substituent which may be possessed by Ar T1 described below. It is the same as the range.
  • nitrogen atom having no double bond means a nitrogen atom having only a single bond between the nitrogen atom and all atoms bonded to the nitrogen atom.
  • “Containing a nitrogen atom having no double bond in the ring” means —N (—R N ) — (wherein, R N represents a hydrogen atom or a substituent), or
  • the number of nitrogen atoms having no double bond constituting the ring is usually 1 to 10.
  • the carbon atom number of the monovalent donor heterocyclic group is usually 2 to 60, not including the carbon atom number of the substituent.
  • Examples of the monovalent donor heterocyclic group include pyrrolyl group, indolyl group, isoindolyl group, carbazolyl group, 1,2,3,4-tetrahydrocarbazolyl group, 9,10-dihydroacridinyl group, 5 , 10-dihydrophenazinyl group, acridinyl group, phenoxazinyl group or phenothiazinyl group, preferably pyrrolyl group, indolyl group, carbazolyl group, 1,2,3,4-tetrahydrocarbazolyl group, 9, 10-dihydroacridinyl group, phenoxazinyl group or phenothiazinyl group, these groups may have a substituent.
  • the number of carbon atoms of the monovalent heterocyclic group other than the monovalent donor heterocyclic group is usually 2 to 60, not including the number of carbon atoms of the substituent.
  • monovalent heterocyclic groups other than monovalent donor type heterocyclic groups include diazolyl, triazolyl, furyl, thienyl, oxadiazolyl, thiadiazolyl, pyridinyl, diazaphenyl, triazinyl and azanaphthyl groups.
  • the monovalent donor group and the monovalent heterocyclic group other than the donor type heterocyclic group are preferably groups excluding one hydrogen atom directly bonded to a hetero atom constituting the heterocyclic ring.
  • Examples of the substituent which Ar T1 may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or cyano.
  • Group is preferable, an alkyl group, an aryl group, a substituted amino group or a monovalent heterocyclic group is more preferable, an aryl group or a monovalent heterocyclic group is more preferable, and these groups may further have a substituent Good.
  • Ar T1 may have, for example, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, naphthacenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group And a perylenyl group, a chrysenyl group, or a group formed by condensing these groups, preferably a phenyl group, and these groups may have a substituent.
  • Examples of the monovalent heterocyclic group and substituted amino group Ar T1 is a substituent which may have and preferred ranges, respectively, examples of the monovalent heterocyclic group and substituted amino group represented by Ar T1 And the same as the preferred range.
  • Ar T1 preferably has a monovalent heterocyclic group as a substituent because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • Preferred examples of the substituent which the substituent which Ar T1 may have may further have preferably include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent group.
  • a heterocyclic group, a substituted amino group, a halogen atom or a cyano group more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group Or an aryl group, which may further have a substituent.
  • Examples and preferred ranges of the aryl group which is a substituent which the substituent which Ar T1 may optionally have further have, a monovalent heterocyclic group, and a substituted amino group are respectively possessed by Ar T1.
  • Examples and preferred ranges of the optionally substituted aryl group, monovalent heterocyclic group and substituted amino group are the same.
  • At least one of Ar T1 is preferably a group represented by the formula (T1-1) described later because the external quantum efficiency of the light emitting device of the present invention is excellent, and these groups have a substituent. May be
  • Ar T1 is preferably a monovalent donor-type heterocyclic group, and more preferably a group represented by Formula (T1-1) described below, because the external quantum efficiency of the light-emitting element of the present invention is excellent. These groups may have a substituent.
  • Ar T1 When a plurality of Ar T1 are present, they may be the same or different, and may be directly bonded or may be bonded via a divalent group to form a ring.
  • R ArT1 and R ArT1 ′ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or A cyano group is represented, and these groups may have a substituent.
  • Examples and preferred ranges of the divalent alkylene group and cycloalkylene group is a group are the same as examples and preferred ranges of the alkylene group and cycloalkylene group represented by the below-mentioned L A.
  • Examples and preferred ranges of divalent and arylene group is a divalent heterocyclic group are the same as examples and preferred ranges of the arylene group and divalent heterocyclic group represented by the below-mentioned L T1.
  • R ArT1 and R ArT1 ′ are the same as the examples and preferred ranges of R XT1 and R XT1 ′ described below, respectively.
  • Examples and preferred ranges of the substituent that the divalent group may have and the substituent that the substituent may further have are the substituent that the Ar T1 may have and the substituent The same as the examples and the preferred ranges of the substituents which may further be possessed.
  • the formula (P) Represents a heterocyclic ring which does not contain the group represented by 1 in the ring, and these rings may have a substituent.
  • Z T1 represents the same meaning as described above.
  • X T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R XT1 )-, or a group represented by -C (R XT1 ') 2- .
  • R XT1 and R XT1 ′ are each independently 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 cyano group is represented, and these groups may have a substituent.
  • Plural R XT1 's may be the same or different. ]
  • the chrysene ring and the ring which these rings condensed are mentioned, Preferably, it is a benzene ring, These rings may have a substituent.
  • the carbon atom number of the heterocyclic group which does not contain the group represented by the above-mentioned formula (P) in the ring is usually 2 to 60, not including the carbon atom number of the substituent.
  • heterocyclic groups which do not contain the group represented by the above-mentioned formula (P) in the ring include, for example, pyrrole ring, furan ring, thiophene ring, silole ring and phosphole ring, and these rings May have a substituent.
  • the ring RT1 has a monovalent heterocyclic group or a substituted amino group as a substituent, or the ring RT2 is a monovalent heterocyclic group or a substituent. It is preferable to have a substituted amino group, and it is more preferable that the ring R T1 has a monovalent heterocyclic group as a substituent, or the ring R T2 has a monovalent heterocyclic group as a substituent, the ring R It is further preferred that only one of T1 and ring RT2 has a monovalent heterocyclic group as a substituent.
  • Examples and preferred ranges of the substituent which may be possessed by the ring RT1 and the ring RT2 and the substituent which the substituent may further have are the substituent which the Ar T1 may optionally have and Examples and preferred ranges of the substituent which the substituent may further have are the same.
  • X T1 is preferably a single bond, an oxygen atom or a group represented by —C (R XT1 ′) 2 —, more preferably a single bond.
  • R XT1 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.
  • R XT1 ′ is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of R XT1 ' may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R XT1 and R XT1 ′ are, respectively, an aryl group which is a substituent which Ar T1 may have, a monovalent group And the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
  • the group represented by the formula (T1-1) is preferably a group represented by the formula (T1-1A).
  • X T1 represents the same meaning as described above.
  • R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 and R T8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent.
  • R T1 , R T2 , R T3 , R T4 , R T5 , R T6 , R T7 and R T8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent hetero
  • R T1 to R T8 are preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may further have a substituent.
  • R T1 , R T2 , R T4 , R T5 , R T7 and R T8 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom, and these groups further have a substituent May be
  • R T3 and R T6 at least one, since the external quantum efficiency of the light-emitting device of the present invention is excellent, an alkyl group, an aryl group, preferably a monovalent heterocyclic group or a substituted amino group, an aryl group It is more preferably a monovalent heterocyclic group or a substituted amino group, further preferably a monovalent heterocyclic group, and these groups may further have a substituent.
  • R T3 and R T6 are alkyl group, an aryl group, preferably a monovalent heterocyclic group or a substituted amino group, an aryl group, It is more preferably a monovalent heterocyclic group or a substituted amino group, and further preferably a monovalent heterocyclic group, and these groups may further have a substituent.
  • Examples and preferable ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R T1 to R T8 are respectively an aryl group in a substituent which may be possessed by Ar T1 and a monovalent complex
  • Examples and preferred ranges of the cyclic group and the substituted amino group are the same.
  • L T1 is preferably an arylene group or a divalent heterocyclic group, more preferably an arylene group, and these groups may have a substituent.
  • the arylene group represented by L T1 is preferably a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenyl group or a dihydrophenanthrendiyl group, and more preferably a group represented by formula (A-1) to a group It is a group represented by A-3), more preferably a group represented by formula (A-1), and these groups may have a substituent.
  • the divalent heterocyclic group represented by L T1 is preferably a group represented by Formula (AA-1) to Formula (AA-34).
  • Examples and preferred ranges of the substituent which may be possessed by L T1 and the substituent which may further be possessed by the substituent are those which Ar T1 may optionally have and the substituent The same as the examples and the preferred ranges of the substituents which may further be possessed.
  • R T1 ′ is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituent represented by R T1 ′ are respectively an aryl group in a substituent which may be possessed by Ar T1 , a monovalent heterocyclic group and It is the same as the example and the preferred range of the substituent.
  • a group represented by the above formula (P), an aromatic hydrocarbon group having an electron withdrawing group, a heterocyclic group containing a boron atom in the ring, or a group represented by N- in the ring
  • These groups are a heterocyclic group containing in the ring thereof, and these groups may have a substituent.
  • Z T1 is preferably an oxygen atom.
  • R ZT1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituent represented by R ZT1 are respectively the aryl group, monovalent heterocyclic group and substituent in the substituent which Ar T1 may have. It is the same as the example and the preferred range of the group.
  • the carbon atom number of the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 18, not including the carbon atom number of the substituent. .
  • the aromatic hydrocarbon group in the aromatic hydrocarbon group having an electron-withdrawing group is, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, Indene ring, pyrene ring, perylene ring, chrysene ring, and a group formed by removing a part or all of hydrogen atoms from a ring formed by direct bonding of these rings, preferably a part or all of a benzene ring
  • These groups may have a substituent, except for hydrogen atoms of these groups.
  • the alkyl group which has a fluorine atom as a substituent, a fluorine atom, a cyano group, and a nitro group are mentioned, for example.
  • the alkyl group having a fluorine atom as a substituent is preferably a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group or a perfluorooctyl group.
  • the number of electron withdrawing groups that the aromatic hydrocarbon group has is usually 1 to 10, and preferably 1 or 2.
  • the number of carbon atoms constituting the ring is usually 1 to 60, preferably 12 to 18.
  • the heterocyclic group containing a boron atom in the ring includes, for example, a borol ring, a benzoborol ring, a dibenzoborol ring group, a borin ring, a benzoborin ring, a dibenzoborin ring, a phenazaborin ring, a phenoxaborin ring, a phenothiaborine ring, phenosena Borin ring, formula (DB):
  • a group formed by removing a part or all of hydrogen atoms from a ring formed by condensation of these rings preferably a phenazaborin ring or a ring represented by the formula (DB) It is a group formed by removing some or all hydrogen atoms, and these groups may have a substituent.
  • the number of nitrogen atoms having a double bond constituting the ring is usually 1 to 10, preferably 3.
  • the number of carbon atoms constituting the ring is usually 1 to 60, preferably 3 to 5.
  • Ar T2 has at least one group represented by Formula (1T ′) as a substituent.
  • Ar T2 may have n T3 groups represented by Formula (DC) as a substituent, and preferably has at least one group represented by Formula (DC).
  • n T3 represents an integer of 0 or more and 15 or less, preferably an integer of 0 or more and 5 or less, and more preferably 1 or 2.
  • m DA1 represents an integer of 0 or more and 10 or less.
  • Ar DA1 represents an arylene group which may have a substituent. When a plurality of Ar DA1 are present, they may be the same or different.
  • T DA represents an aryl group which may have a substituent.
  • m DA1 is preferably 0 or 1, more preferably 0.
  • Ar DA1 is preferably a phenylene group or a fluorenidyl group, more preferably a group represented by the formulas (ArDA-1) to (ArDA-4), and these groups have a substituent May be When two or more Ar DA1 are present, they are preferably identical.
  • R DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may further have a substituent. When there are a plurality of RDAs , they may be the same or different.
  • R DB represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. When there are multiple R DBs , 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
  • R DB is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an aryl group, and these groups may have a substituent.
  • the substituent which Ar DA1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these Groups may have a substituent.
  • T DA is preferably a group represented by Formula (TDA-1) or Formula (TDA-2), and more preferably a group represented by Formula (TDA-1).
  • R DA and R DB represent the same meaning as described above.
  • the group represented by Formula (DC) is preferably a group represented by Formula (D-C1) to Formula (D-C4), and more preferably a group represented by Formula (D-C1) .
  • R p4 , R p5 and R p6 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom, and these groups may have a substituent. When a plurality of R p4 , R p5 and R p6 are present, they may be the same or different.
  • np4 represents an integer of 0 to 4.
  • np5 and np6 each independently represent an integer of 0 to 5.
  • Np4 is preferably an integer of 0 to 2, more preferably 0.
  • np5 is preferably an integer of 0 to 3, more preferably 0.
  • np6 is preferably an integer of 0 to 2, more preferably 0.
  • R p4 to R p6 are preferably an alkyl group which may have a substituent, and more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or It is a tert-octyl group.
  • Examples of the substituent which Ar T2 may have (different from the group represented by the formula (1T ′) and the group represented by the formula (DC). The same applies to the following.
  • An alkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group is preferable, an alkyl group or a cycloalkyl group is more preferable, and these groups may have a substituent.
  • the example and the preferable range of the substituent which the substituent which Ar T2 may have may further have are the substituents of the substituent which Ar T1 may have may further have. Same as example and preferred range.
  • the compound represented by the formula (T-1) when Ar T2 is an aromatic hydrocarbon group having an electron-withdrawing group, the compound represented by the formula (T-1) is a light-emitting device of the present invention
  • the compound is preferably a compound represented by the formula (T'-15) to the formula (T'-18) described later, and more preferably a compound represented by the formula (T'-15).
  • Preferred are compounds represented by the following formulas (T'-19) to (T'-22), and more preferred are compounds represented by formula (T'-21).
  • the compound represented by the formula (T-1) when Ar T2 is a heterocyclic group containing a boron atom in the ring, the compound represented by the formula (T-1) is an external compound of the light emitting device of the present invention
  • Preferred are compounds represented by Formula (T'-23) or Formula (T'-24) described later, and more preferably compounds represented by Formula (T'-24), because the quantum efficiency is excellent. It is.
  • the compound represented by Formula (T-1) is preferably selected from Formula (T′-1) to Formula (T′-4) or Formula (T′ ⁇ ) because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • R 1T represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, a cyano group, a group represented by formula (1T ′) or a group represented by formula (DC), These groups may have a substituent.
  • Plural R 1T 's may be the same or different, and may be directly bonded or may be bonded via a divalent group to form a ring. However, among the R 1T presence of a plurality of, at least one is a group represented by the formula (1T ').
  • R 1T ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron withdrawing group, a group represented by the formula (1T ′), or a group represented by the formula (DC) These groups may have a substituent.
  • Plural R 1T 's may be the same or different, and may be directly linked or linked via a divalent group to form a ring. However, among the plurality of R 1T 's, at least one is a group represented by formula (1T'), and at least one is an electron-withdrawing group. ]
  • n T3 are each preferably a group represented by formula (DC), and at least one is a group represented by formula (DC) More preferable.
  • 1 to 5 are preferably electron withdrawing groups, and more preferably 1 or 2 are electron withdrawing groups.
  • R 1T is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, a cyano group, a group represented by formula (1T ′) or a group represented by formula (DC) And more preferably a hydrogen atom, a group represented by the formula (1T ′) or a group represented by the formula (DC), and these groups may have a substituent.
  • R 1T ′ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron-withdrawing group, a group represented by the formula (1T ′) or a formula (DC)
  • R 1T and R 1T ′ are not a group represented by the formula (1T ′) or a group represented by the formula (DC), respectively, of the substituents that R 1T and R 1T ′ may have
  • the example and the preferable range are the same as the example and the preferable range of the substituent which the substituent which Ar T2 may have may further have.
  • T As a low molecular weight compound (T), the compound represented by a following formula is mentioned, for example.
  • Z 2 represents an oxygen atom or a sulfur atom.
  • Plural Z 1 and Z 2 may be the same or different.
  • Z 2 is preferably an oxygen atom.
  • T Low molecular weight compounds
  • International Publication No. 2007/063754 International Publication No. 2008/056746, International Publication No. 2011/02686, International Publication No. 2012/096263, Japanese Patent Publication 2009-227663, Japanese Patent Publication 2010-226663. No. 275,255, Advanced Materials, 26: 7931-7958, 2014.
  • the polymer compound (TP) in the first organic layer, may be contained singly or in combination of two or more.
  • the structural unit (C) contained in the polymer compound (TP) is preferably a low molecular weight compound because the external quantum efficiency of the light emitting device of the present invention is excellent and the production of the polymer compound (TP) is easy. It is a constituent unit containing a group formed by removing one or more and five or less hydrogen atoms from (T), more preferably a constituent unit represented by formula (1C) to formula (4C), and still more preferably It is a structural unit represented by Formula (3C).
  • arylene group and divalent heterocyclic group represented by the structural unit L C represented by the formula (1C) are respectively an arylene group and divalent hetero ring represented by Ar Y 1 described later The same as the examples and the preferred range of the cyclic group.
  • L C is preferably an oxygen atom, —C (R B ) 2 — or an arylene group.
  • n c1 is preferably an integer of 1 or more and 4 or less.
  • arylene group and divalent heterocyclic group represented by the structural unit L d and L e represented by the formula (2C) are respectively an arylene group and 2 represented by Ar Y 1 described below Examples and preferred ranges of the valent heterocyclic groups are the same.
  • L d and L e are preferably an oxygen atom, —C (R B ) 2 — or an arylene group, and more preferably an arylene group.
  • n d1 is preferably 0 because the external quantum efficiency of the light-emitting element of the present invention is excellent.
  • n e1 is preferably an integer of 1 or more and 4 or less.
  • Ar 1 M is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, dihydrophenanthrene ring, pyridine ring, diazabenzene ring, triazine ring, carbazole ring, phenoxazine ring or phenothiazine ring, to a carbon atom or hetero atom constituting the ring It is preferable that it is a group which remove
  • Examples and preferred ranges of the substituent which L d , L e and Ar 1M may have are the examples and preferred ranges of the substituent which the group represented by Ar Y 1 described below may have, and It is the same.
  • the structural unit T 2C represented by the formula (3C) is preferably a group represented by the formulas (T-2C-1) to (T-2C-5), and the formula (T-2C-2) Or a group represented by the formula (T-2C-5) is more preferable, and a group represented by the formula (T-2C-2) is more preferable.
  • m DA1 , n T1 , n T2 , n T3 , Ar DA1 , Ar T1 , L T1 and T DA have the same meanings as described above.
  • Ar T2 ′ represents a group formed by removing one hydrogen atom from Ar T2 .
  • Ar T2 ′ ′ represents a group obtained by removing two hydrogen atoms from Ar T2 .
  • An aromatic hydrocarbon group having the formula, a heterocyclic group containing a boron atom in the ring, or a heterocyclic group containing the group represented by N- in the ring, and these groups have a substituent May be Z T1 represents the same meaning as described above.
  • Ar L1 represents a group formed by removing one hydrogen atom from T DA .
  • Plural Ar L1 may be the same or different.
  • Ar L2 represents a group formed by removing two hydrogen atoms from T DA .
  • Ar K1 represents a group formed by removing one hydrogen atom from Ar T1 .
  • Plural Ar K1 may be the same or different.
  • Ar K2 represents a group formed by removing two hydrogen atoms from Ar T1 . ]
  • the aromatic hydrocarbon group having the following, the heterocyclic group containing a boron atom in the ring, and the heterocyclic group containing the group represented by N- in the ring.
  • Examples and preferred ranges of m DA1 , n T1 , n T2 , n T3 , Ar DA1 and L T1 in formulas (T-2C-1) to (T-2C-5) are respectively low molecular weight compounds (T).
  • T low molecular weight compounds
  • the groups represented by T 1C , T 2C and T 3C are low molecular weight compounds (T-1) It is preferable that it is a group formed by removing one or more hydrogen atoms from Ar T1 , Ar T2 or T DA, and it is more preferable that it is a group formed by removing one or more hydrogen atoms from Ar T1 or T DA. preferably, it is more preferably a group formed by eliminating one or more hydrogen atoms from T DA.
  • the structural unit represented by Formula (3C) is preferably a structural unit represented by Formula (3C-1) to Formula (3C-3).
  • Ring R T1, ring R T2, m DA1, n d1 , n T1, Ar DA1, Ar L1, L d, L T1, R 1T and X T1 are as defined above.
  • k represents 0 or 1; When there are a plurality of k, they may be the same or different.
  • the definition of the ring R T1 or ring R T2 examples and preferable ranges, the definition of the ring R T1 or ring R T2 in a low molecular weight compound (T), examples and preferred It is the same as the range.
  • the definition, the example and the preferred range of the moiety of the ring RT1 or the ring RT2 excluding-(L d ) n d1- are The same as the definition, the example and the preferred range of the ring RT1 or the ring RT2 in the low molecular weight compound (T).
  • Examples and preferable ranges of m DA1 , n T1 , Ar DA1 , L T1 , R 1 T and X T1 in the structural units represented by formulas (3C-1) to (3C-3) are low molecular weight compounds ( Examples and preferred ranges of m DA1 , n T1 , Ar DA1 , L T1 , R 1 T and X T1 in T) are the same.
  • n d1 and L d in the structural units represented by the formulas (3C-1) to (3C-3) are n d1 and L in the structural units represented by the formula (3C), respectively. Same as example and preferred range.
  • K is preferably 1, and when there are a plurality of k, they are preferably identical.
  • R TS represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups May further have a substituent.
  • a plurality of R TS may be the same or different.
  • J is preferably 0, and when there are a plurality of j, they are preferably the same.
  • R TS 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 substituted amino group or a cyano group, and a hydrogen atom, an alkyl group or 1 It is more preferable that it is a divalent heterocyclic group.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R TS are respectively an aryl group in a substituent which may be possessed by Ar T1 , a monovalent heterocyclic group and Examples and preferred ranges of the substituted amino group are the same.
  • the example and the preferable range of the substituent which R TS may have are respectively the same as the example and the preferable range of the substituent which the substituent which Ar T1 may have may further have. .
  • the total amount of structural units (C) is preferably 0.01 to the total amount of structural units contained in the polymer compound (TP) because the external quantum efficiency of the present invention is excellent. It is 50 mol%, more preferably 0.1 to 30 mol%, still more preferably 1 to 20 mol%, and particularly preferably 6 to 15 mol%.
  • the polymer compound (TP) preferably further includes the structural unit represented by the above formula (Y) because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • Ar Y 1 is preferably represented by the formula (A-1), the formula (A-2), the formula (A-6) -the formula (A-10), the formula (A-19) or the formula (A-20) These groups may have a substituent.
  • Groups represented by Ar Y1 is preferably has a substituent, the substituent which may be be included in the group represented by Ar Y1 is preferably an alkyl group, a cycloalkyl group or an aryl group, more Preferably, it is an alkyl group or a cycloalkyl group, and these groups may further have a substituent.
  • the structural unit represented by the formula (Y) since the external quantum efficiency of the light emitting device of the present invention is excellent, it is represented by the formula (Y-1), the formula (Y-2) or the formula (Y-3) It is preferably a constituent unit, more preferably a constituent unit represented by formula (Y-1) or formula (Y-2), and a constituent unit represented by formula (Y-1) More preferable.
  • R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.
  • the constitutional unit represented by the formula (Y-1) is preferably a constitutional unit represented by the formula (Y-1 ′).
  • R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent.
  • Plural 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 may have a substituent.
  • R Y2 is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.
  • the combination of two R Y2 in the group represented by —C (R Y2 ) 2 — is preferably both an alkyl group or a cycloalkyl group, both an aryl group, or one of which is an alkyl group. Or a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.
  • R Y2 's may be bonded to each other to form a ring together with the atoms to which each is attached, and when R Y2 forms a ring, a group represented by —C (R Y2 ) 2 — Is preferably a group represented by formula (Y-A1) -formula (Y-A5), and these groups may have a substituent.
  • R Y2 in the group represented by —C (R Y2 ) 2 —C (R Y2 ) 2 — in X Y1 is an alkyl group or a cycloalkyl group which may have a substituent. It is. More than one R Y2 may be bonded to each other to form a ring with the atoms to which each is attached, and in the case where R Y2 forms a ring, -C (R Y2 ) 2 -C (R Y2 ) 2-
  • the group represented is preferably a group represented by the formula (Y-B1)-(Y-B5), and these groups may have a substituent.
  • R Y2 represents the same meaning as described above.
  • the structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′), and a structural unit represented by the formula (Y-2 ′ ′) Is more preferred.
  • R Y2 and R Y11 represent the same meaning as described above.
  • the constitutional unit represented by the formula (Y-3) is preferably a constitutional unit represented by the formula (Y-3 ′).
  • Examples of the structural unit represented by the formula (Y) include a structural unit represented by the formula (Y-101) -formula (Y-108).
  • the total amount of structural units represented by the formula (Y) is preferably 0.5 to the total amount of structural units contained in the polymer compound (TP) because the external quantum efficiency of the light emitting device of the present invention is excellent. It is 80 mol%, more preferably 30 to 60 mol%.
  • the polymer compound (TP) may further contain a constituent unit represented by the formula (X) described later.
  • a constituent unit represented by the formula (X) described later An example and a preferred range of the structural unit represented by the formula (X) which may be contained in the polymer compound (TP) are represented by the formula (X) which the second polymer compound described later may contain. It is the same as the example and the preferred range of the structural unit represented by).
  • the constitutional unit represented by the formula (X) and the constitutional unit represented by the formula (Y) may be contained alone or in combination of two or more. Good.
  • the polymer compound (TP) is a structural chain represented by any one of Formula (S-1) to Formula (S-3) It is preferable to have the structural chain represented by formula (S-2).
  • Ar TW is at least one structural unit selected from the group consisting of the structural units represented by the formulas (Y-1) to (Y-3). When there are a plurality of Ar TWs , they may be the same or different.
  • L S1 is a structural unit represented by the above formula (1C).
  • L S2 is a constitutional unit represented by the formula (2C) or a constitutional unit represented by the formula (3C).
  • L S3 is a structural unit represented by the above formula (4C).
  • Ar TWs When a plurality of Ar TWs exist in the constituent chain represented by Formula (S-1) to Formula (S-3), they may be the same or different, but are preferably the same.
  • Examples and preferred ranges of Ar TW in formulas (S-1) to (S-3) are the examples and preferred ranges of the structural units represented by formulas (Y-1) to (Y-3), respectively. Is the same as
  • the example and the preferred range of the structural unit represented by L S1 are the same as the example and the preferred range of the structural unit represented by the formula (1C), respectively, and the example and the preferred range of the structural unit represented by L S2 Is the same as an example and a preferred range of the structural unit represented by the formula (2C) and the structural unit represented by the formula (3C), and an example and a preferred range of the structural unit represented by L S3 are They are respectively the same as the examples and the preferred ranges of the constituent units represented by the formula (4C).
  • the constituent unit represented by L S2 is preferably a constituent unit represented by formula (3C).
  • the constituent chain represented by formula (S-2) is preferably a constituent chain represented by formula (S2-1) to formula (S2-3), and the structure represented by formula (S2-1) More preferably, it is a chain.
  • Ring R T1, ring R T2, k, m DA1, n d1, n T1, Ar DA1, Ar L1, Ar TW, L d, L T1, R 1T, X T1 and Z 3 are as defined above.
  • rings R T1 , rings R T2 , rings R DA2 , m DA1 , n T1 , Ar DA1 , Ar L1 , L d , L T1 , R 1 T , X T1 and Z 3 are present, they are identical or different from each other It is also good.
  • Plural n d1 and Ar TW may be the same or different.
  • the ranges are the same as the examples and preferred ranges of the ring RT1 , the ring RT2 , the ring RT2 , m DA1 , n T1 , Ar DA1 , L T1 , R 1 T and X T1 in the low molecular weight compound (T), respectively.
  • rings R T1 , rings R T2 , m DA1 , n T1 , Ar DA1 , L T1 , R 1T and X T1 are present, they are preferably identical to each other.
  • Examples and preferred ranges of k, n d1 , Ar L1 , L d and Z 3 in the constituent chains represented by formulas (S2-1) to (S2-3) are each represented by formula (3C)
  • Examples and preferred ranges of k, n d1 , Ar L1 , L d and Z 3 in the structural units are the same.
  • a plurality of k, Ar L1 , L d and Z 3 are present, they are preferably identical to each other. It is preferable that a plurality of n d1 be identical.
  • An example and a preferred range of Ar TW in the constituent chain represented by Formula (S2-1) to Formula (S2-3) are an example and a preferred range of Ar TW in the constituent chain represented by Formula (S-2) Is the same as When there are a plurality of Ar TWs , they are preferably identical.
  • Examples of constituent chains represented by formulas (S-1) to (S-3) include constituent chains represented by the following formulas.
  • the definitions, examples and preferred ranges of k, n e1 , L e , R 1 T , R TS , R Y 2 , R Y 4 , R Y 11 , Z 2 and Z 3 are the same as above, and they are plural When they exist, they may be the same or different.
  • the bond to the group represented by and the bond to the group represented by Ar TW and the group represented by L S3 are each preferably a carbon-carbon bond.
  • the dihedral angle between the group represented by Ar TW and the group represented by L S1 is represented by ⁇ 1
  • the smallest dihedral angle is ⁇ 2
  • ⁇ 1 , ⁇ 2 and ⁇ 3 are each preferably 45 ° or more, more preferably 50 ° or more, 55 More preferably, it is at least °°.
  • Gaussian 09 which is a quantum chemistry calculation program
  • a semi-empirical molecular orbital method AM1 is a method of By optimizing the ground state of the compound, ⁇ 1 , ⁇ 2 and ⁇ 3 can be calculated.
  • the constituent chains represented by formulas (S-1) to (S-3) may each be contained singly or in combination of two or more. It is preferable that only one kind is contained.
  • the total amount of constituent chains represented by the formulas (S-1) to (S-3) is excellent in the external quantum efficiency of the light emitting device of the present invention, and thus the structural unit (C) contained in the polymer compound (TP) It is preferably 20 to 100 mol%, more preferably 50 to 100 mol%, still more preferably 80 to 100 mol%, particularly preferably 100 mol%, based on the total amount of (a).
  • polymer compound (TP) examples include polymer compound A and polymer compounds TP-A to TP-G.
  • the “other” structural unit means a structural unit other than the structural unit represented by the structural unit (C), the formula (X), and the formula (Y).
  • the polymer compound (TP) may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may have other embodiments, but a plurality of raw materials It is preferable that it is a copolymer formed by copolymerizing a monomer.
  • the polystyrene equivalent number average molecular weight of the polymer compound (TP) is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , and more preferably 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
  • the polymer compound (TP) may be, for example, a compound represented by formula (M-1), a compound represented by formula (MT-1) to formula (MT-4), and other compounds (eg, It can be produced by condensation polymerization of (M-2) to a compound represented by formula (M-4).
  • M-1 a compound represented by formula
  • MT-1 a compound represented by formula (MT-1) to formula (MT-4)
  • other compounds eg, It can be produced by condensation polymerization of (M-2) to a compound represented by formula (M-4).
  • the compounds used for producing the polymer compound (TP) of the present invention may be collectively referred to as "raw material monomers".
  • Z C1 to Z C16 each independently represent a group selected from the group consisting of Substituent Group A and Substituent Group B.
  • Z C1 and Z C2 are a group selected from Substituent Group A
  • Z C3 to Z C16 respectively select a group selected from Substituent Group B.
  • Z C1 and Z C2 are a group selected from Substituent Group B
  • Z C3 to Z C16 each select a group selected from Substituent Group A.
  • ⁇ Substituent group A> Chlorine atom, bromine atom, iodine atom, —O—S ( O) 2 R C1 (wherein, R C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent)
  • R C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent
  • a group represented by —BF 3 Q ′ (wherein, Q ′ represents Li, Na, K, Rb or Cs); A group represented by the formula -MgY '(wherein Y' represents a chlorine atom, a bromine atom or an iodine atom); A group represented by —ZnY ′ ′ (wherein Y ′ ′ represents a chlorine atom, a bromine atom or an iodine atom); -Sn (R C3) 3 (wherein, R C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. More existing R C3 is And groups which may be the same or different and may be linked to each other to form a ring structure together with the tin atoms to which they are attached.
  • Examples of the group represented by —B (OR C2 ) 2 include groups represented by the following formulae.
  • the compound having a group selected from the substituent group A and the compound having a group selected from the substituent group B are condensation-polymerized by a known coupling reaction to form a group selected from the substituent group A and the substituent group B And a carbon atom bonded to a group selected from Therefore, if a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B are subjected to a known coupling reaction, condensation polymerization results in condensation of these compounds. Polymers can be obtained.
  • the condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, but if necessary, it may be carried out in the coexistence of a phase transfer catalyst.
  • a catalyst for example, bis (triphenylphosphine) palladium (II) dichloride, bis (tris-o-methoxyphenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) And palladium complexes such as palladium acetate, palladium acetate, etc., tetrakis (triphenylphosphine) nickel (0), [1,3-bis (diphenylphosphino) propane) nickel (II) dichloride, bis (1,4) Transition metal complexes such as nickel complexes such as cyclooctadiene) nickel (0); these transition metal complexes further include triphenylphosphine, tri (o-tolyl) phosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine,
  • the amount of the catalyst used is usually 0.00001 to 3 molar equivalents as the amount of transition metal based on the total number of moles of the raw material monomer.
  • a base and a phase transfer catalyst for example, inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate and the like; tetrabutyl ammonium fluoride, tetraethyl ammonium hydroxide, tetra hydroxide hydroxide Organic bases such as butyl ammonium; phase transfer catalysts such as tetrabutyl ammonium chloride and tetrabutyl ammonium bromide.
  • the base and the phase transfer catalyst may be used alone or in combination of two or more.
  • the amount of the base and phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of the raw material monomers.
  • the solvent examples include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
  • organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
  • the solvents may be used alone or in combination of two or more.
  • the amount of the solvent used is usually 10 to 100,000 parts by mass with respect to 100 parts by mass in total of the raw material monomers.
  • the reaction temperature of the condensation polymerization is usually ⁇ 100 to 200 ° C.
  • the reaction time of the condensation polymerization is usually 1 hour or more.
  • Post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, adding a reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate and drying it.
  • the method of making it etc. is carried out alone or in combination.
  • the purity of the polymer compound is low, it can be purified by a usual method such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography and the like.
  • the first organic layer is at least one selected from the group consisting of a polymer compound (TP), a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material, and an antioxidant. And a layer containing a composition (hereinafter, also referred to as a "first composition").
  • TP polymer compound
  • the hole transport material, the hole injection material, the electron transport material, the electron injection material, the light emitting material, and the polymer compound (TP) are different.
  • the external quantum efficiency of the light emitting device of the present invention is excellent, so the hole transport material, the hole injection material ,
  • the electron transport material and the electron injection material each have an energy level higher than the lowest excited triplet state of the polymer compound (TP), and more than the lowest excited singlet state of the polymer compound (TP) It is preferable to have a high energy level.
  • Hole transport materials are classified into low molecular weight compounds and high molecular weight compounds.
  • polymer compound examples include polyvinylcarbazole and derivatives thereof; polyarylenes having an aromatic amine structure in the side chain or main chain and derivatives thereof.
  • the macromolecular compound may be a compound having an electron accepting moiety bound thereto. Examples of the electron accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, with preference given to fullerene.
  • the amount of the hole transport material in the first composition is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound (TP).
  • the hole transport material may be used alone or in combination of two or more.
  • Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds.
  • low molecular weight compound for example, metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone And as well as their derivatives.
  • polyphenylene, polyfluorene, and these derivatives are mentioned, for example.
  • the polymer compound may be doped with metal.
  • the amount of the electron transport material in the first composition is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound (TP).
  • the electron transporting material may be used alone or in combination of two or more.
  • the hole injecting material and the electron injecting material are classified into low molecular weight compounds and high molecular weight compounds, respectively.
  • metal phthalocyanines such as copper phthalocyanine; Carbon; Metal oxides, such as molybdenum and tungsten; Metal fluorides, such as lithium fluoride, sodium fluoride, cesium fluoride, potassium fluoride, etc. are mentioned, for example.
  • polyaniline polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof
  • conductive materials such as polymers containing an aromatic amine structure in the main chain or side chain Polymers are included.
  • the amount of the hole injection material and the electron injection material in the first composition is usually 1 to 400 parts by mass, preferably 5 to 400 parts by mass, based on 100 parts by mass of the polymer compound (TP). 150 parts by mass.
  • Each of the electron injecting material and the hole injecting material may be used alone or in combination of two or more.
  • the 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 in order to bring the conductivity of the conductive polymer into such a range.
  • the type of ion to be doped is an anion if it is a hole injecting material, and a cation if it is an electron injecting material.
  • the anion include polystyrene sulfonate ion, alkyl benzene sulfonate ion and camphor sulfonate ion.
  • the cation include lithium ion, sodium ion, potassium ion and tetrabutyl ammonium ion.
  • the ions to be doped may be used alone or in combination of two or more.
  • the light emitting material is classified into a low molecular weight compound and a high molecular weight compound, and the light emitting material is preferably a low molecular weight compound because the external quantum efficiency of the light emitting element of the present invention is excellent.
  • low molecular weight compounds examples include naphthalene and derivatives thereof, anthracene and derivatives thereof, fluorescent compounds represented by perylene and derivatives thereof, and phosphorescent compounds 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 phenanthrendiyl group, a dihydrophenanthrendiyl group, a group represented by the formula (X) described later, a carbazole diyl group, a phenoxazine diyl group, A high molecular compound containing a phenothiazine diyl group, an anthracene diyl group, a pyrene diyl group, etc. is mentioned.
  • the phosphorescent compounds represented by the formulas Ir-1 to Ir-5 are preferable, and the phosphorescent compounds represented by the formula Ir-1 are preferable. More preferable.
  • R D11 to R D20 , R D21 to R D26 and R D31 to R D37 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent group It represents a heterocyclic group or a halogen atom, and these groups may have a substituent.
  • R D11 to R D20 , R D21 to R D26 and R D31 to R D37 may be the same or different.
  • -A D1 --- A D2- , n D1 , n D2 and R D1 to R D8 have the same meanings as described above. ]
  • Examples of the anionic bidentate ligand represented by -A D1 --- A D2- include a ligand represented by the following formula.
  • the phosphorescence compound shown below is mentioned, for example.
  • the polymer compound (TP) When the first composition contains a light emitting material, the polymer compound (TP) has an energy level higher than the lowest excitation triplet state of the light emitting material because the external quantum efficiency of the light emitting element of the present invention is excellent. And, it is preferable to have an energy level higher than the lowest excited singlet state of the light emitting material.
  • the content of the light emitting material is usually 0.1 to 50 parts by weight, based on 100 parts by weight of the total of the polymer compound (TP) and the light emitting material.
  • the light emitting materials may be used alone or in combination of two or more.
  • the antioxidant may be a compound which is soluble in the same solvent as the polymer compound (TP) and does not inhibit light emission and charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.
  • the blending amount of the antioxidant is usually 0.001 to 10 parts by mass based on 100 parts by mass of the polymer compound (TP).
  • the antioxidant may be used alone or in combination of two or more.
  • first ink The composition containing the polymer compound (TP) and a solvent (hereinafter, also referred to as “first ink”) can be suitably used in a wet method such as a spin coating method or an inkjet method.
  • the viscosity of the first ink may be adjusted according to the type of wet method, but when a solution such as an ink jet method is applied to a printing method via a discharge device, clogging and flying bending at the time of discharge are difficult to occur Therefore, 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 for example, chlorinated solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc .; ether solvents such as tetrahydrofuran, dioxane, anisole, 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane and
  • the blending amount of the solvent is usually 1000 to 100000 parts by mass, based on 100 parts by mass of the polymer compound (TP).
  • the crosslinked body of the crosslinked material is obtained by bringing the crosslinked material into a crosslinked state by the method and conditions described above.
  • the crosslinking material is selected from a low molecular weight compound having at least one kind of crosslinking group selected from the crosslinking group A group (hereinafter, also referred to as "a low molecular weight compound of the second organic layer”), or a crosslinking group A group Since it is a polymer compound (hereinafter, also referred to as “polymer compound of second organic layer”) containing a crosslinking structural unit having at least one type of crosslinking group, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable that it is a high molecular compound containing the crosslinking structural unit which has at least 1 sort (s) of crosslinking group chosen from crosslinking group A group.
  • the external quantum efficiency of the light emitting device of the present invention is excellent, and preferably, the formula (XL-1) to the formula (XL-4) and the formula (XL-7) to the formula (XL-10) or a crosslinking group represented by the formula (XL-14) to the formula (XL-17), more preferably a crosslink represented by the formula (XL-1) or the formula (XL-17) And more preferably a crosslinking group represented by formula (XL-17).
  • the structural unit having at least one cross-linking group selected from the cross-linking group A, which is contained in the polymer compound of the second organic layer, is a structural unit represented by the formula (2) or the formula (2 ′)
  • the constituent unit is preferably a constituent unit, but may be a constituent unit represented by the following formula.
  • the polymer compound of the second organic layer contains two or more structural units having at least one crosslinking group selected from the crosslinking group A group, it has at least one crosslinking group selected from the crosslinking group A group It is preferred that at least two of the constituent units have mutually different crosslinking groups.
  • Examples of combinations of crosslinking groups which are different from one another include formula (XL-1), formula (XL-2), formula (XL-5) to formula (XL-8) or formula (XL-14) to formula (XL-16)
  • a combination of a crosslinking group represented by the formula (XL-3), a formula (XL-4), a formula (XL-13) or a formula (XL-17) is preferable, and the formula (XL) -1) or a combination of a crosslinking group represented by the formula (XL-16) and a crosslinking group represented by the formula (XL-17) is more preferable, and a crosslinking group represented by the formula (XL-1) And the combination with the crosslinking group represented by formula (XL-17) is more preferable.
  • the structural unit nA represented by the formula (2) is preferably an integer of 0 to 3, more preferably 1, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • N is preferably 2, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • Ar 3 is preferably an aromatic hydrocarbon group which may have a substituent, because the external quantum efficiency of the light emitting device of the present invention is 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, not including the number of carbon atoms of the substituent. is there.
  • the arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by Ar 3 is preferably a group represented by Formula (A-1) to Formula (A-20), More preferably, it is a group represented by Formula (A-1), Formula (A-2), Formula (A-7), Formula (A-9) or Formula (A-19), and these groups are It may have a substituent.
  • the carbon atom number of the heterocyclic group represented by Ar 3 is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, not including the carbon atom number of the substituent.
  • the divalent heterocyclic group moiety excluding the n substituents of the heterocyclic group represented by Ar 3 is preferably a group represented by Formula (AA-1) to Formula (AA-34) is there.
  • the aromatic hydrocarbon group and the heterocyclic group represented by Ar 3 may have a substituent, and as the substituent, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group can be mentioned Preferred is a group, a halogen atom, a monovalent heterocyclic group or a cyano group.
  • L A number of carbon atoms of the alkylene group represented by the not including the carbon atom number of substituent is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10.
  • the number of carbon atoms a 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 which the alkylene group and the cycloalkylene group may have an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group is preferable, and these groups further have a substituent It may be
  • 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 which the arylene group may have, 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 crosslinking group
  • a crosslinking group selected from Group A is preferable, and these groups may further have a substituent.
  • the divalent heterocyclic group represented by L A is preferably a group represented by the formula (AA-1) ⁇ formula (AA-34).
  • L A is preferably an arylene group or an alkylene group, and more preferably a phenylene group, a fluorenicyl group or an alkylene group, since it facilitates the production of the polymer compound of the second organic layer. Groups may have a substituent.
  • the external quantum efficiency of the light-emitting element of the present invention is excellent, and therefore preferably, formulas (XL-1) to (XL-4) and formulas (XL-7) to (XL) -10) or a crosslinking group represented by the formula (XL-14) to the formula (XL-17), more preferably a crosslinking group represented by the formula (XL-1) or the formula (XL-17) And more preferably a crosslinking group represented by formula (XL-17).
  • the total amount of the constituent units represented by the formula (2) is excellent in the stability and the crosslinkability of the polymer compound in the second organic layer, and therefore, the total of the constituent units contained in the polymer compound in the second organic layer.
  • the amount is preferably 0.5 to 80% by mole, more preferably 3 to 65% by mole, still more preferably 5 to 50% by mole, relative to the amount.
  • the constituent unit represented by the formula (2) may be contained singly or in combination of two or more in the polymer compound of the second organic layer.
  • the polymer compound of the second organic layer contains two or more structural units represented by the formula (2)
  • at least two of the structural units represented by the formula (2) are cross-linked represented by X
  • the groups are different from one another.
  • the preferred range of the combination of crosslinking groups represented by different X's is the same as the preferred range of the aforementioned combination of different crosslinking groups.
  • the structural unit mA represented by the formula (2 ′) is preferably an integer of 0 to 3, and more preferably 0, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • M is preferably 1 or 2, and more preferably 2, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • C is preferably 0 because the production of the polymer compound of the second organic layer is facilitated, and the external quantum efficiency of the light emitting device of the present invention is excellent.
  • Ar 5 is preferably an aromatic hydrocarbon group which may have a substituent, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • the definition and examples of the divalent heterocyclic group moiety excluding the m substituents of the heterocyclic group represented by Ar 5 are the divalent heterocyclic group represented by Ar X2 in the formula (X) described later The same as the definition and example of the part.
  • the definition and examples of the divalent group excluding “m” substituents of “a group in which an aromatic hydrocarbon ring and a heterocycle are directly bonded” represented by Ar 5 are the same as Ar X2 in Formula (X) described later The same as the definition and the example of a divalent group in which at least one arylene group represented by and at least one divalent heterocyclic group are directly bonded.
  • Ar 4 and Ar 6 each are preferably an arylene group which may have a substituent, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • arylene group and divalent heterocyclic group represented by Ar 4 and Ar 6 are the same as those of the arylene group and divalent heterocyclic group represented by Ar X1 and Ar X3 in the formula (X) described later. Same as definition and example.
  • the group represented by Ar 4 , Ar 5 and Ar 6 may have a substituent, and as the substituent, 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 and a cyano group are preferred.
  • alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by K A are respectively the alkylene group, cycloalkylene group, arylene group and divalent hetero group represented by L A The same as the definition and examples of the ring group.
  • K A is preferably a phenylene group or a methylene group because this facilitates the production of the polymer compound of the second organic layer.
  • the total amount of the constituent units represented by the formula (2 ′) is excellent in the stability of the polymer compound of the second organic layer and the crosslinkability of the polymer compound of the second organic layer, so 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 the structural units contained in the polymer compound of the second organic layer. is there.
  • the structural unit represented by the formula (2 ′) may be contained alone or in combination of two or more in the polymer compound of the second organic layer.
  • the polymer compound of the second organic layer contains two or more structural units represented by the formula (2 ′), at least two of the structural units represented by the formula (2 ′) are represented by X ′
  • the crosslinking groups used are different from one another.
  • the preferred range of the combination of crosslinking groups represented by different X's is the same as the preferred range of the combination of different crosslinking groups described above.
  • the structural unit represented by the formula (2) is represented by, for example, the formulas (2-1) to (2-13) Structural units are listed.
  • Examples of the structural unit represented by the formula (2 ′) include structural units represented by the formulas (2′-1) to (2′-4). Among these, since the crosslinkability of the polymer compound of the second organic layer is excellent, the structural units represented by formulas (2-1) to (2-13) are preferable, and more preferably formula (2) -1) to (2-6) or (2-13).
  • the polymer compound of the second organic layer preferably has a structural unit represented by Formula (X) since it has excellent hole transportability. Further, since the polymer compound of the second organic layer is excellent in the external quantum efficiency of the light-emitting element of the present invention, it is preferable that the polymer compound further include a structural unit represented by the formula (Y).
  • Each of a X1 and a X2 independently represents an integer of 0 or more and 10 or less.
  • Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
  • Ar X2 and Ar X4 are each independently 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 These groups may have a substituent.
  • Ar X2 and Ar X4 When a plurality of Ar X2 and Ar X4 exist, they may be the same or different.
  • R X1 , R X2 and R X3 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • R X2 and R X3 may be the same or different.
  • a X1 is preferably an integer of 2 or less, more preferably 1, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • a X2 is preferably an integer of 2 or less, more preferably 0, because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • the arylene group represented by Ar X1 and Ar X3 is more preferably a group represented by Formula (A-1) or Formula (A-9), and these groups may have a substituent .
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by Formula (AA-1), Formula (AA-2) or Formula (AA-7) -Formula (AA-26). These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably arylene groups which may have a substituent.
  • the arylene group represented by Ar X2 and Ar X4 is more preferably a group represented by the formula (A-1), a formula (A-6), a formula (A-7) or a formula (A-9) -formula (A-11) Or a group represented by 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 “a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded” represented by Ar X2 and Ar X4 include, for example, a group represented by the following formula: 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 may have a substituent.
  • R XX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.
  • Ar X2 and Ar X4 are preferably arylene groups which may have a substituent.
  • the substituent which the group 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 have.
  • the constitutional unit represented by formula (X) is preferably a constitutional unit represented by formula (X-1) -formula (X-7).
  • R X4 and R X5 are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, halogen atom, 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.
  • Plural R X5 s may be the same or different, and adjacent R X5 s may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • Examples of the structural unit represented by the formula (X) include a structural unit represented by the formula (X1-1) -the formula (X1-11).
  • the polymer compound of the second organic layer is excellent in the hole transportability and excellent in the external quantum efficiency of the light emitting device of the present invention, so that the structural unit represented by the formula (X) and the formula (Y) It is preferable that the structural unit represented by these is included.
  • the definition and the example of the constitutional unit represented by the formula (Y) which the polymer compound of the second organic layer may contain is represented by the formula (Y) which the above-mentioned polymer compound (TP) may contain It is the same as the definition and example of the constitutional unit represented.
  • the structural unit represented by the formula (X) may be contained alone or in combination of two or more in the polymer compound of the second organic layer.
  • the structural unit represented by the formula (Y) may be contained singly or in combination of two or more in the polymer compound of the second organic layer.
  • the total amount of the constitutional units represented by the formula (X) is excellent in the hole transportability, so that the second The amount is preferably 0.1 to 90 mol%, more preferably 35 to 70 mol%, still more preferably 45 to 50 mol%, based on the total amount of the structural units contained in the polymer compound of the organic layer.
  • the total amount of the constitutional units represented by the formula (Y) is excellent in the external quantum efficiency of the light emitting device of the present invention Therefore, it is preferably 0.5 to 90 mol%, more preferably 30 to 60 mol%, with respect to the total amount of structural units contained in the polymer compound of the second organic layer.
  • polymer compound of the second organic layer examples include polymer compounds IP-A to IP-H.
  • the "other structural unit” means a structural unit other than the structural units represented by the formula (2), the formula (2 '), the formula (X) and the formula (Y).
  • p ′, q ′, r ′, s ′ and t ′ each represent a molar ratio of each constituent unit.
  • p ′ + q ′ + r ′ + s ′ + t ′ 100 and 70 ⁇ p ′ + q ′ + r ′ + s ′ ⁇ 100.
  • the polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, and may be other embodiments, but plural It is preferable that it is the copolymer which copolymerized the raw material monomer of seed
  • the polystyrene equivalent number average molecular weight of the polymer compound of the second organic layer is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
  • the polymer compound of the second organic layer can be produced by the same method as the method for producing the polymer compound (TP) described above.
  • the low molecular weight compound of the second organic layer is preferably a low molecular weight compound represented by Formula (3).
  • m B1 is preferably an integer of 0 to 5, and more preferably 0 because this facilitates the synthesis of the crosslinked material.
  • m B2 is preferably an integer of 0 to 5, and more preferably 1, because it facilitates the synthesis of the crosslinked material and has excellent external quantum efficiency of the light emitting device of the present invention.
  • m B3 is preferably an integer of 0 to 4, and more preferably 0 because this facilitates the synthesis of the crosslinked material.
  • the definition and examples of the divalent heterocyclic group moiety excluding the m 3 B 3 substituents of the heterocyclic group represented by Ar 7 are the same as the divalent heterocyclic ring represented by Ar X 2 in the above-mentioned formula (X) It is the same as the definition and example of the base moiety.
  • divalent groups other than m B3 substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar 7 and at least one hetero ring are directly bonded are the same as the aforementioned formulas
  • 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 to each other are the same as the definition and the example.
  • Ar 7 is preferably an aromatic hydrocarbon group because the external quantum efficiency of the light emitting device of the present invention is excellent, and the aromatic hydrocarbon group may have a substituent.
  • alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by L B1 are respectively the above-mentioned alkylene group, cycloalkylene group, arylene group and divalent group represented by L A are the same as the definition and the example of the heterocyclic group of
  • L B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably a phenylene group or an alkylene group, because these facilitate the synthesis of the cross-linking material, and these groups have a substituent. It is also good.
  • X ′ ′ is preferably a bridging group represented by any one of formulas (XL-1) to (XL-17), an aryl group or a monovalent heterocyclic group, and more preferably a formula (XL) A bridging group represented by -16) or a naphthyl group, and these groups may have a substituent.
  • Examples of the low molecular weight compound of the second organic layer include low molecular weight compounds represented by Formula (3-1) to Formula (3-16).
  • Low molecular weight compounds of the second organic layer are available, for example, from Aldrich, Luminescence Technology Corp., American Dye Source, and the like.
  • the low molecular weight compound in the second organic layer may be synthesized, for example, according to the methods described in, for example, WO 1997/033193, WO 2005/035221, WO 2005/049548. Can.
  • the crosslinked body of the crosslinked material may be contained singly or in combination of two or more.
  • the second organic layer is a crosslinked body of a crosslinked material, and at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant.
  • a layer containing a composition hereinafter also referred to as “second composition”) containing
  • Examples and preferred ranges of the hole transporting material, the electron transporting material, the hole injecting material and the electron injecting material contained in the second composition are the hole transporting material and the electron transporting material contained in the first composition. , The same as the examples and preferred ranges of the hole injection material and the electron injection material.
  • a fluorescent compound which may be contained in the first composition for example, a fluorescent compound which may be contained in the first composition, and a phosphorescent compound having iridium, platinum or europium as a central metal are exemplified. It can be mentioned.
  • the light emitting materials may be used alone or in combination of two or more.
  • the compounding amount of the hole transporting material, the electron transporting material, the hole injecting material, the electron injecting material and the light emitting material is generally 1 when the crosslinked body of the crosslinking material is 100 parts by mass -400 parts by mass.
  • the example and the preferable range of the antioxidant contained in a 2nd composition are the same as the example and a preferable range of the antioxidant contained in a 1st composition.
  • the blending amount of the antioxidant is usually 0.001 to 10 parts by mass, based on 100 parts by mass of the crosslinked material of the crosslinking material.
  • a composition containing a crosslinking material and a 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 preferred range of the viscosity of the second ink is the same as the preferred 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 blending amount of the solvent is usually 1000 to 100000 parts by mass, based on 100 parts by mass of the crosslinking material.
  • the light emitting device 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 also referred to as “first light emitting layer”).
  • the second organic layer is usually a hole transporting layer, a second light emitting layer or an electron transporting layer, preferably a hole transporting layer or a second light emitting layer, more preferably Is a hole transport layer.
  • the first organic layer and the second organic layer are preferably adjacent to each other because the external quantum efficiency of the light emitting device of the present invention is excellent.
  • the second organic layer is preferably a layer provided between the anode and the first organic layer, because the external quantum efficiency of the light emitting device of the present invention is excellent. More preferably, it is a hole transporting layer or a second light emitting layer provided between one organic layer, and still more preferably, it is a hole transporting layer provided between an anode and a first organic layer. .
  • the polymer compound (TP) may be contained singly or in combination of two or more.
  • the crosslinked material of the crosslinking material may be contained singly or in combination of two or more.
  • the second organic layer is a hole transport layer provided between the anode and the first organic layer
  • the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further have a hole injection layer between the two organic layers.
  • the second organic layer is a hole transport layer provided between the anode and the first organic layer
  • the external quantum efficiency of the light emitting device of the present invention is excellent, so the distance between the cathode and the first organic layer is
  • at least one of the electron injection layer and the electron transport layer is further included.
  • the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further include at least one layer of a hole injection layer and a hole transport layer between the second organic layer and the second organic layer. When the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further include at least one of the electron injection layer and the electron transport layer in between.
  • the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further include at least one layer of a hole injection layer and a hole transport layer between the first organic layer and the first organic layer. When the second organic layer is the second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further include at least one of the electron injection layer and the electron transport layer in between.
  • the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the organic layer of When the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent, so that it is between the cathode and the second organic layer. It is preferable to further have an electron injection layer.
  • the layer configuration of the light emitting device of the present invention include the layer configurations represented by (D1) to (D15).
  • the light emitting device of the present invention generally has a substrate, but may be laminated from the anode on the substrate or may be laminated from the cathode on the substrate.
  • “/” means that the layers before and after that are stacked adjacent to each other.
  • “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” refers to the second light emitting layer (second organic layer) and the first light emitting layer It means that the light emitting layer (first organic layer) is stacked adjacent to one another.
  • 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 each provided in two or more layers as necessary. It is also good.
  • a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers and cathodes are present, they may be the same or different.
  • the thickness of the anode, the hole injection layer, the hole transport layer, the first light emitting layer, the second light emitting layer, the electron transport layer, the electron injection layer and the cathode is usually 1 nm to 1 ⁇ m.
  • the order, the number, and the thickness of the layers to be stacked may be adjusted in consideration of the external quantum efficiency, driving voltage and luminance life of the light emitting element.
  • the second light emitting layer is usually a second organic layer or a layer containing a light emitting material, preferably a layer containing 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 a light emitting material which may be contained in the above-mentioned second composition.
  • the light emitting materials 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 organic layer Is preferred.
  • the hole transport layer is usually a second organic layer or a layer containing a hole transport material, preferably a second organic layer.
  • the hole transport layer is a layer containing a hole transport material
  • examples of the hole transport material include a hole transport material which 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 transporting layer is the second organic layer. Is preferred.
  • the electron transport layer is usually a second organic layer or a layer containing an electron transport material, 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 an electron transport material which may be contained in the above-mentioned first composition. .
  • the electron transporting material contained in the electron transporting layer may be contained singly or in combination of two or more.
  • the electron transporting layer is the second organic layer Is preferred.
  • 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 injecting material contained in the electron injecting 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 an electrode and does not change chemically when forming an organic layer, and is, for example, a substrate made of a material such as glass, plastic, or silicon.
  • Examples of the material of the anode include conductive metal oxides and semitransparent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc. Conductive compounds; complexes of silver, palladium and copper (APC); NESA, gold, platinum, silver, copper.
  • the material of the cathode includes, for example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc and indium; alloys of two or more of them; one of them And alloys thereof with one or more species of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds.
  • the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminium alloy, indium-silver alloy, lithium-aluminium alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminium alloy.
  • At least one of the anode and the cathode is usually transparent or translucent.
  • Examples of the method for forming the anode and the cathode include dry methods such as vacuum evaporation.
  • a low molecular weight compound is used as a method of forming each of 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 and the like.
  • a dry method and a wet method can be mentioned, and in the case of using a polymer compound, for example, a wet method can be mentioned.
  • the first light emitting layer, the second light emitting layer, the hole transporting layer, the electron transporting layer, the hole injecting layer and the electron injecting layer include the first ink, the second ink, and the light emitting material described above, the holes It can be formed by a wet method using an ink containing each of a transport material, an electron transport material, a hole injection material and an electron injection material.
  • a planar anode and a cathode may be arranged to overlap.
  • a method of installing a mask provided with a pattern-like window on the surface of a planar light-emitting element is used.
  • both the anode and the cathode may be formed in stripes and arranged orthogonal to each other.
  • Partial color display and multi-color display can be performed by a method of separately coating a plurality of types of polymer compounds different in emission color and a method of using a color filter or a fluorescence conversion filter.
  • the dot matrix display device can be driven passively, or can be driven active in combination with a TFT or the like.
  • These display devices can be used as displays of computers, televisions, portable terminals, and the like.
  • a planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar light source for illumination. If a flexible substrate is used, it can also be used as a curved light source and display device.
  • the polystyrene equivalent number average molecular weight (Mn) of the polymer compound and the polystyrene equivalent weight average molecular weight (Mw) were determined by size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase.
  • SEC size exclusion chromatography
  • the polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 ⁇ L was injected into SEC.
  • the mobile phase flowed 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.
  • LC-MS was measured by the following method.
  • the measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 ⁇ L was injected into LC-MS (manufactured by Agilent, trade name: 1100 L CMSD).
  • the mobile phase of LC-MS was used while changing the ratio of acetonitrile and tetrahydrofuran, and flowed at a flow rate of 0.2 mL / min.
  • L-column 2 ODS 3 ⁇ m
  • NMR NMR was measured by the following method. About 5 to 10 mg of a measurement sample is added to about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethyl sulfoxide, heavy acetone, heavy N, N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol or It was dissolved in methylene dichloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA 300 or MERCURY 400 VX).
  • HPLC high performance liquid chromatography
  • an ODS column having Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or the like was used.
  • a detector a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used.
  • ⁇ E ST of the compound For the calculation of ⁇ E ST of the compound, oscillator strength, ⁇ 1 , ⁇ 2 and ⁇ 3 , Gaussian 09, which is a quantum chemistry calculation program, was used. After optimizing the structure of the ground state of the compound using the density functional theory at the B3LYP level, ⁇ E ST and the oscillator strength were calculated by using the time-dependent density functional theory at the B3LYP level.
  • the polymer compound contains a constituent chain represented by the above-mentioned formula (S-1) to formula (S-3), a semi-empirical molecule is obtained for a compound in which each bond in the constituent chain is replaced by a hydrogen atom.
  • ⁇ 1 , ⁇ 2 and ⁇ 3 were calculated.
  • the resulting mixture was cooled to room temperature and heptane (510 mL) and Celite 545 (Aldrich, 72 g) were added.
  • the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was purified using a silica gel column (developing solvent: hexane / toluene) to obtain 56.4 g of a compound T2-1 as a pale yellow oil.
  • the resulting mixture was cooled to room temperature, the aqueous layer was separated, and the resulting organic layer was further washed with water. Magnesium sulfate was added to the obtained organic layer.
  • the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product was purified using a silica gel column (developing solvent: hexane / toluene) to obtain 12.8 g of compound T2-2 as a pale yellow solid.
  • the HPLC area percentage value was 96.1%.
  • the obtained crude product was purified using a silica gel column (developing solvent: hexane / toluene) to obtain 7.2 g of compound T2-5 as a white solid.
  • the HPLC area percentage value was 98.9%.
  • the necessary amount of compound T2-5 was obtained by repeating this operation.
  • the resulting mixture was cooled to room temperature, heptane (83 mL) was added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to give a crude product.
  • the obtained crude product was purified using a silica gel column (developing solvent: hexane / toluene) to obtain 8.8 g of compound T2-6 as a white solid.
  • the HPLC area percentage value was 94.9%.
  • the resulting mixture was cooled to room temperature, then toluene (85 mL) and Celite 545 (manufactured by Aldrich, 7 g) were added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to give a crude product .
  • the obtained crude product was purified using a silica gel column (developing solvent: hexane / toluene) to obtain 6.1 g of a compound T2-7 as a white solid.
  • the HPLC area percentage value was 99.0%.
  • the resulting mixture was cooled to room temperature, the aqueous layer was separated, and the resulting organic layer was further washed with water. Magnesium sulfate was added to the obtained organic layer, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product is purified using an alumina column (developing solvent: hexane / toluene), and then purified using a silica gel column (developing solvent: hexane / toluene) to obtain Compound T2 4.6 as a pale yellow solid. g got.
  • the HPLC area percentage value was 99.5% or more.
  • the obtained oil was purified using silica gel column chromatography (a mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried to give compound T3-1 (29.6 g, colorless oil).
  • the HPLC area percentage value of compound T3-1 was 99.2%.
  • the obtained oil was purified using silica gel column chromatography (a mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried to give compound T3-2 (14.9 g, colorless oil).
  • the HPLC area percentage value of compound T3-2 was 99.0%.
  • reaction vessel was changed to a nitrogen gas atmosphere, compound T3-3 (7.5 g) and tert-butylbenzene (56 mL) were added, and after cooling to 0 ° C., t-BuLi ⁇ pentane solution (while maintaining 0 ° C. 1.5 M, 9.6 mL) was added slowly. The resulting mixture was stirred at 60 ° C. for 3 hours, and then pentane was distilled off under reduced pressure. The resulting mixture was cooled to ⁇ 50 ° C., BBr 3 (4.5 g) was added, and the mixture was stirred at ⁇ 50 ° C. for 0.5 hour. The resulting mixture was heated to 120 ° C. and allowed to react at 120 ° C. for 3 hours.
  • the resulting mixture was cooled to room temperature, aqueous sodium acetate solution and ethyl acetate were added, and the obtained organic layer was washed with ion-exchanged water.
  • the obtained organic layer was concentrated under reduced pressure to obtain a yellow oil.
  • the obtained oil was purified by silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried to obtain a yellow solid.
  • the obtained solid was dispersed in acetonitrile and then filtered to give compound T3-H (1.1 g, yellow solid).
  • the HPLC area percentage value of compound T3-H was 99.4%.
  • the obtained oil was purified by silica gel column chromatography (developing solvent: mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried to obtain compound T4-1 (5.4 g, pale yellow solid).
  • the HPLC area percentage value of compound T4-1 was 96.1%.
  • reaction vessel was changed to an argon gas atmosphere, then compound T4-1 (4.44 g), chloroform (58 mL) and trifluoroacetic acid (8.9 mL) were charged and ice-cooled.
  • N-iodosuccinimide (3.39 g) was added in two portions to the resulting mixture, the mixture was stirred for 1 hour while being kept warm.
  • To the resulting mixture was added 10% by mass aqueous sodium sulfite solution (20 mL), then water (58 mL) and hexane (115 mL) were added, and then separated, and the obtained organic layer was washed with water (58 mL) .
  • reaction vessel was changed to an argon gas atmosphere, and then compound T4-3 (4.00 g), a palladium catalyst ((2-Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropyl-1,1′-biphenyl) [2- ( 2'-amino-1,1'-biphenyl)] palladium (II) methanesulfonate, X phos Pd G3, from Aldrich) (0.21 g), bispinacolate diboron (6.28 g), potassium acetate (3.17 g) and cyclopentyl methyl Ether (48 mL) was added and warmed to reflux temperature and stirred at reflux temperature for 1 hour.
  • a palladium catalyst ((2-Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropyl-1,1′-biphenyl) [2- ( 2'-amino-1,1'-b
  • reaction vessel was changed to an argon gas atmosphere, and then Compound T4-4 (4.33 g), Compound T2-8 (4.79 g), toluene (153 mL) and ethanol (31 mL) were added.
  • the resulting mixture is bubbled with argon gas for 5 minutes while stirring, then tetrakis (triphenylphosphine) palladium (0) (0.87 g) is added, and then 20% by mass tetraethylammonium hydroxide (24.9 g) and water ( After the mixture with 53 mL) was added, it heated up to 50 degreeC and stirred at 50 degreeC for 1 hour.
  • the resulting mixture was cooled to room temperature and then diluted with toluene, the aqueous layer was separated, and the resulting organic layer was washed with water.
  • Magnesium sulfate was added to the obtained organic layer, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
  • the obtained crude product is purified using an alumina column (developing solvent: hexane / toluene), and then purified using a silica gel column (developing solvent: hexane / toluene) to obtain compound T4 (4.0 as a light yellow solid). g, pale yellow solid).
  • the HPLC area percentage value was 99.5% or more.
  • Synthesis Examples MC1 and MC2 Synthesis of Phosphorescent Compounds MC-1 and MC-2
  • the phosphorescent compound MC-1 was synthesized according to the method described in WO 2009/131255.
  • the phosphorescent compound MC-2 was synthesized according to the method described in JP-A-2008-179617.
  • Compound M11 was synthesized according to the method described in JP-A-2010-189630.
  • the compound M12 utilized the commercial item.
  • Compound M13 was synthesized according to the method described in WO 2012/086671.
  • Compound M14 was synthesized according to the method described in WO 2013/191086.
  • the polymer compound TP-1 has a structural unit derived from the compound M11, a structural unit derived from the compound M6, and a structural unit derived from the compound T1 in the theoretical value determined from the amount of the feed material. It is a copolymer comprised by the molar ratio of 50:40:10.
  • the ⁇ E ST and the oscillator strength of the compound T1-H were 0.16 eV and 0.0001, respectively.
  • the polymer compound TP-1 contained a constituent chain represented by the following formula, and ⁇ 2 of the constituent chain was 57 °.
  • Example TP2 Synthesis of polymer compound TP-2 After the reaction container was changed to an inert gas atmosphere, compound M11 (825 mg), compound M6 (772 mg), compound T2 (547 mg), dichlorobis (tris-o-methoxy) Phenylphosphine) palladium (1.5 mg) and toluene (35 mL) were added and heated to 105.degree. To the resulting reaction solution, a 20% by mass aqueous tetraethylammonium hydroxide solution (26 mL) was dropped, and the mixture was refluxed for 5.5 hours.
  • the resulting solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.1 g of a polymer compound TP-2.
  • the Mn of the polymer compound TP-2 was 5.7 ⁇ 10 4 and the Mw was 1.2 ⁇ 10 5 .
  • the polymer compound TP-2 has a structural unit derived from the compound M11, a structural unit derived from the compound M6, and a structural unit derived from the compound T2 in the theoretical values determined from the amounts of the raw materials charged. It is a copolymer comprised by the molar ratio of 50:40:10.
  • the ⁇ E ST and the oscillator strength of the compound T2-H were 0.06 eV and 0.0922, respectively.
  • the polymer compound TP-2 contains a constituent chain represented by the following formula, and ⁇ 2 of the constituent chain is 57 °.
  • Example TP3 Synthesis of polymer compound TP-3 Compound T3 (0.104 g), compound M12 (0.502 g), compound M13 (0.628 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.86 mg) and Toluene (27 mL) was mixed and heated to 105.degree. Then, 10 mass% tetraethylammonium hydroxide aqueous solution (18 mL) was dripped there, and it was made to reflux for 4 hours.
  • the resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed.
  • the resulting precipitate was collected by filtration and dried to obtain 0.68 g of a polymer compound TP-3.
  • the Mn of the polymer compound TP-3 was 4.5 ⁇ 10 4
  • the Mw was 1.1 ⁇ 10 5 .
  • the constitutional unit derived from the compound M12, the constitutional unit derived from the compound T3, and the constitutional unit derived from the compound M13 are It is a copolymer comprised by the molar ratio of 45: 5: 50.
  • the ⁇ E ST and the oscillator strength of the compound T3-H were 0.44 eV and 0.3782, respectively.
  • Example TP4 Synthesis of polymer compound TP-4 Compound M11 (0.643 g), compound M14 (0.613 g), compound T2 (0.427 g), dichlorobis (tri-o-methoxyphenylphosphine) palladium (1.22 mg) and Toluene (24.2 g) was mixed and heated to 80.degree. Then, 10 mass% tetraethylammonium hydroxide aqueous solution (20 mL) was dripped there, and it was made to reflux for 12 hours.
  • phenylboronic acid (64.7 mg) and dichlorobis (tri-o-methoxyphenylphosphine) palladium (0.12 mg) were added thereto, and the mixture was refluxed for 11 hours.
  • the resulting reaction mixture was cooled, and then washed once with water, twice with a 10% by mass aqueous hydrochloric acid solution, twice with a 3% by mass aqueous ammonia solution, and twice with water.
  • the water was removed by distillation of the resulting mixture under reduced pressure.
  • the resulting solution was purified by passing it through a column packed with a mixture of alumina and silica gel.
  • the resulting solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 0.76 g of a polymer compound TP-4.
  • the Mn of the polymer compound TP-4 was 5.3 ⁇ 10 4
  • the Mw was 1.1 ⁇ 10 5 .
  • the structural unit derived from the compound M11, the structural unit derived from the compound M14, and the structural unit derived from the compound T2 are It is a copolymer comprised by the molar ratio of 50:40:10.
  • the polymer compound TP-4 contains the same constituent chain as the polymer compound TP-2.
  • Example TP5 Synthesis of polymer compound TP-5 Compound M11 (0.626 g), compound M15 (0.629 g), compound T2 (0.414 g), dichlorobis (tri-o-methoxyphenylphosphine) palladium (1.28 mg) and Toluene (24.5 g) was mixed and heated to 80.degree. Then, 10 mass% tetraethylammonium hydroxide aqueous solution (20 mL) was dripped there, and it was made to reflux for 7 hours.
  • phenylboronic acid (62.9 mg) and dichlorobis (tri-o-methoxyphenylphosphine) palladium (0.12 mg) were added thereto, and the mixture was refluxed for 10 hours.
  • the resulting reaction mixture was cooled, and then washed once with water, twice with a 10% by mass aqueous hydrochloric acid solution, twice with a 3% by mass aqueous ammonia solution, and twice with water.
  • the water was removed by distillation of the resulting mixture under reduced pressure.
  • the resulting solution was purified by passing it through a column packed with a mixture of alumina and silica gel.
  • the obtained solution was added dropwise to methanol and stirred, and then the obtained precipitate was collected by filtration and dried to obtain 0.98 g of a polymer compound TP-5.
  • the Mn of the polymer compound TP-5 was 5.2 ⁇ 10 4 and the Mw was 1.1 ⁇ 10 5 .
  • the structural unit derived from the compound M11, the structural unit derived from the compound M15, and the structural unit derived from the compound T2 are It is a copolymer comprised by the molar ratio of 50:40:10.
  • the polymer compound TP-5 contains the same constituent chain as the polymer compound TP-2.
  • Example TP6 Synthesis of polymer compound TP-6 Compound M11 (0.798 g), compound M6 (0.730 g), compound T4 (0.280 g), dichlorobis (tri-o-methoxyphenylphosphine) palladium (1.48 mg) and Toluene (24.2 g) was mixed and heated to 80.degree. Then, 20 mass% tetraethylammonium hydroxide aqueous solution (20 mL) was dripped there, and it was made to reflux for 2.5 hours.
  • phenylboronic acid (81.2 mg) and dichlorobis (tri-o-methoxyphenylphosphine) palladium (1.47 mg) were added thereto, and the mixture was refluxed for 6 hours.
  • the resulting reaction mixture was cooled, and then washed once with water, twice with a 10% by mass aqueous hydrochloric acid solution, twice with a 3% by mass aqueous ammonia solution, and twice with water.
  • the water was removed by distillation of the resulting mixture under reduced pressure.
  • the resulting solution was purified by passing it through a column packed with a mixture of alumina and silica gel.
  • the resulting solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 0.71 g of a polymer compound TP-6.
  • the Mn of the polymer compound TP-6 was 9.5 ⁇ 10 4 , and the Mw was 2.2 ⁇ 10 5 .
  • the constitutional unit derived from the compound M11, the constitutional unit derived from the compound M6, and the constitutional unit derived from the compound T4 are It is a copolymer comprised by the molar ratio of 50:40:10.
  • the ⁇ E ST and the oscillator strength of the compound T4-H were 0.06 eV and 0.0781, respectively.
  • the polymer compound TP-6 contains a constituent chain represented by the following formula, and ⁇ 2 of the constituent chain is 57 °.
  • 2-ethylphenylboronic acid (60.0 mg), 20% by mass aqueous tetraethylammonium hydroxide solution (8.7 mL) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) are added thereto, and the reaction is continued for 16 hours. It was allowed to reflux. Thereafter, an aqueous solution of sodium diethyldithiacarbamate was added thereto, and the mixture was stirred at 80 ° C. for 2 hours.
  • the obtained reaction solution was cooled, washed twice with 3.6% by mass hydrochloric acid, twice with 2.5% by mass aqueous ammonia solution, and 6 times with water, and the obtained solution was added dropwise to methanol, whereby a precipitate was generated.
  • the obtained precipitate was dissolved in toluene, and purified by passing through an alumina column and a silica gel column in this order.
  • the resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed.
  • the resulting precipitate was collected by filtration and dried to obtain 1.14 g of a polymer compound IP-4.
  • the Mn of the polymer compound IP-4 was 3.6 ⁇ 10 4
  • the Mw was 2.0 ⁇ 10 5 .
  • the constitutional unit derived from the compound M8 in terms of theoretical values determined from the amount of the raw materials charged, the constitutional unit derived from the compound M8, the constitutional unit derived from the compound M9, and the constitutional unit derived from the compound M2 are It is a copolymer comprised by the molar ratio of 40:10:50.
  • the resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed. The resulting precipitate was collected by filtration and dried to obtain 3.00 g of a polymer compound IP-6.
  • the Mn of the polymer compound IP-6 was 4.5 ⁇ 10 4 , and the Mw was 1.5 ⁇ 10 5 .
  • the structural unit derived from the compound M11 and the structural unit derived from the compound M5 are configured at a molar ratio of 50:50 in the theoretical value determined from the amount of the raw materials charged Copolymer.
  • phenylboronic acid 97.5 mg
  • 20% by mass aqueous tetraethylammonium hydroxide solution 28 mL
  • dichlorobis tris-o-methoxyphenylphosphine
  • palladium 7. mg
  • the resulting reaction mixture was cooled, and then washed twice with water, twice with a 10% by mass aqueous hydrochloric acid solution, twice with a 3% by mass aqueous ammonia solution, and twice with water.
  • the resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed.
  • the obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed. The resulting precipitate was collected by filtration and dried to obtain 6.65 g of a polymer compound IP-7.
  • the Mn of the polymer compound IP-7 was 2.6 ⁇ 10 4
  • the Mw was 1.4 ⁇ 10 5 .
  • the structural unit derived from the compound M11, the structural unit derived from the compound M5, and the structural unit derived from the compound M7 are It is a copolymer comprised by the molar ratio of 50: 42.5: 7.5.
  • the polymer compound IP-1 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film is formed to a thickness of 20 nm by spin coating on the hole injection layer, and the film is heated at 180 ° C. for 60 minutes on a hot plate under a nitrogen gas atmosphere. Form an organic layer.
  • xylene solution Using the obtained xylene solution, a film is formed on the second organic layer to a thickness of 80 nm by spin coating, and the first organic layer is heated at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. Formed.
  • Example D1 Production and Evaluation of Light-Emitting Element D1 (Formation of Anode and Hole Injection Layer)
  • An anode was formed by depositing an ITO film with a thickness of 45 nm on a glass substrate by sputtering.
  • AQ-1200 manufactured by Plectronics
  • the hole injection layer was formed by heating at 170 ° C. for 15 minutes on a hot plate under an air atmosphere.
  • the polymer compound IP-2 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film is formed to a thickness of 20 nm by spin coating on the hole injection layer, and the film is heated at 180 ° C. for 60 minutes on a hot plate under a nitrogen gas atmosphere. Form an organic layer. By this heating, the polymer compound IP-2 became a crosslinked body.
  • xylene solution Using the obtained xylene solution, a film is formed on the second organic layer to a thickness of 80 nm by spin coating, and the first organic layer is heated at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. Formed.
  • Example D1 the first organic layer Light-emitting elements D2 to D16, D4 ′, D14 ′ and D15 ′ were produced in the same manner as in Example D1 except that the second organic layer was as shown in Table 3, and the EQE was measured.
  • a light emitting device CD2 was produced in the same manner as in Comparative Example CD1 except that the first organic layer and the second organic layer in Comparative Example CD1 were as shown in Table 3, and the EQE was measured. The results are shown in Table 3.
  • the light emitting element which is excellent in an external quantum efficiency, and the high molecular compound useful to its manufacture can be provided.

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Abstract

L'invention fournit un élément luminescent dont l'efficacité quantique externe est excellente. Plus précisément, l'invention concerne un élément luminescent qui 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 à poids moléculaire élevé (TP), et la seconde couche organique comprend un corps réticulé d'un matériau de réticulation. Le composé à poids moléculaire élevé (TP) contient une unité structurale qui contient une base constituée par élimination d'au moins un atome d'hydrogène d'un composé à bas poids moléculaire (T) tel que la valeur absolue de la différence entre un niveau d'énergie dans l'état excité triplet minimal et un niveau d'énergie dans l'état singulet minimal est inférieure ou égale à 0,5eV. Le matériau de réticulation consiste en un composé à bas poids moléculaire qui possède un groupe de réticulation spécifique, ou un composé à poids moléculaire élevé qui contient une unité constitutive de réticulation possédant un groupe de réticulation spécifique.
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