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WO2018199283A1 - Composition et élément électroluminescent utilisant ladite composition - Google Patents

Composition et élément électroluminescent utilisant ladite composition Download PDF

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WO2018199283A1
WO2018199283A1 PCT/JP2018/017160 JP2018017160W WO2018199283A1 WO 2018199283 A1 WO2018199283 A1 WO 2018199283A1 JP 2018017160 W JP2018017160 W JP 2018017160W WO 2018199283 A1 WO2018199283 A1 WO 2018199283A1
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group
ring
atom
formula
compound
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PCT/JP2018/017160
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English (en)
Japanese (ja)
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元章 臼井
林　直樹
美佳 白崎
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • 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 composition and a light emitting device using the composition.
  • Organic electroluminescence elements (hereinafter also referred to as “light-emitting elements”) can be suitably used for display and lighting applications, and research and development are actively conducted.
  • This light-emitting element has an organic layer such as a light-emitting layer and a charge transport layer.
  • Patent Document 1 describes a light-emitting element having a light-emitting layer containing an iridium complex (M0) and a compound (H0).
  • the inventors of the present invention have a molecular weight higher than that of a specific compound in a light-emitting element including an organic layer containing a composition in which a specific compound and a phosphorescent compound are blended.
  • a compound having a molecular weight of 16 greatly affects the initial deterioration of the light emitting device, and further, by reducing the compound having a molecular weight of 16 larger than the specific compound to a specific amount or less, the initial deterioration of the light emitting device can be suppressed.
  • the headline and the present invention were completed. Note that Patent Document 1 does not describe that a compound having a molecular weight of 16 larger than a specific compound affects the initial deterioration of the light-emitting element.
  • the present invention provides the following [1] to [10].
  • a composition comprising a compound represented by the formula (H-1) and a phosphorescent compound, the compound represented by the formula (H-1) contained as an impurity in the composition.
  • the composition by which the content by the area percentage method using the liquid chromatography of the compound whose molecular weight is 16 larger than the compound to be made is 0.1% or less with respect to the whole quantity of the said composition.
  • Ar H1 represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar H1 are present, they may be the same or different.
  • n H1 represents an integer of 1 to 10.
  • L H1 is a group obtained by removing one or more hydrogen atoms (typically n H1 ) directly bonded to a carbon atom or a hetero atom constituting the ring from an aromatic hydrocarbon ring or heterocyclic ring, May have a substituent. ]
  • the L H1 is a heterocyclic ring having a sulfur atom, the group (base derived by removing one or more hydrogen atoms bonded directly to a carbon atom or a heteroatom constituting the ring may have a substituent
  • Ar H1 represents the same meaning as described above.
  • n H1-1 and n H1-2 each independently represent an integer of 0 or more and 10 or less. However, n H1-1 + n H1-2 is an integer of 1 or more and 10 or less.
  • Ring R 1C and ring R 2C each independently represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • X H1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by —N (R XH1 ) —, or a group represented by —C (R XH1 ′ ) 2 —.
  • R XH1 and R XH1 ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom. And these groups may have a substituent.
  • a plurality of R XH1 ′ may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]
  • [5] The composition according to any one of [1] to [4], wherein the phosphorescent compound is a compound represented by the formula (1).
  • M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
  • n 1 represents an integer of 1 or more
  • n 2 represents an integer of 0 or more
  • n 1 + n 2 is 2 or 3.
  • M is a ruthenium atom, rhodium atom or iridium atom
  • n 1 + n 2 is 3
  • M is a palladium atom or platinum atom
  • n 1 + n 2 is 2.
  • E 1 and E 2 each independently represent a carbon atom or a nitrogen atom. However, at least one of E 1 and E 2 is a carbon atom. When a plurality of E 1 and E 2 are present, they may be the same or different.
  • Ring L 1 represents an aromatic heterocycle, and the aromatic heterocycle may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L 1 are present, they may be the same or different.
  • the ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L 2 are present, they may be the same or different.
  • a 1 -G 1 -A 2 represents an anionic bidentate ligand.
  • a 1 and A 2 each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • G 1 represents a single bond or an atomic group constituting a bidentate ligand together with A 1 and A 2 .
  • a 1 -G 1 -A 2 When a plurality of A 1 -G 1 -A 2 are present, they may be the same or different.
  • E 11A When E 11A is a nitrogen atom, R 11A may or may not be present.
  • E 12A When E 12A is a nitrogen atom, R 12A may or may not be present.
  • E 13A When E 13A is a nitrogen atom, R 13A may or may not be present.
  • E 21A is a nitrogen atom, R 21A does not exist.
  • E 22A is a nitrogen atom, R 22A does not exist.
  • E 23A is a nitrogen atom
  • R 23A When E 24A is a nitrogen atom, R 24A does not exist.
  • R 11A, R 12A, R 13A , R 21A, R 22A, R 23A and R 24A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, an aryl group, an aryloxy group, An alkenyl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A they may be the same or different.
  • R 11A and R 12A , R 12A and R 13A , R 11A and R 21A , R 21A and R 22A , R 22A and R 23A , and R 23A and R 24A are bonded to each other together with the atoms to which they are bonded.
  • a ring may be formed.
  • Ring L 1A represents a triazole ring or a diazole ring.
  • Ring L 2A represents a benzene ring, a pyridine ring or a pyrimidine ring. ] [Where: M, n 1 , n 2 and A 1 -G 1 -A 2 represent the same meaning as described above.
  • E11B , E12B , E13B , E14B , E21B , E22B , E23B and E24B each independently represent a nitrogen atom or a carbon atom.
  • E 11B , E 12B , E 13B , E 14B , E 21B , E 22B , E 23B and E 24B they may be the same or different.
  • E 11B is a nitrogen atom
  • R 11B does not exist.
  • E 12B is a nitrogen atom
  • E 13B is a nitrogen atom
  • R 13B does not exist.
  • E 14B is a nitrogen atom, R 14B does not exist.
  • E 21B is a nitrogen atom
  • R 21B does not exist.
  • E 22B is a nitrogen atom
  • R 22B does not exist.
  • E 23B is a nitrogen atom
  • R 23B does not exist.
  • E 24B is a nitrogen atom, R 24B does not exist.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl It represents an oxy group, an alkenyl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B they may be the same or different.
  • Ring L 1B represents a pyridine ring or a pyrimidine ring.
  • Ring L 2B represents a benzene ring, a pyridine ring or a pyrimidine ring.
  • the compound represented by the formula (1-A) is represented by the compound represented by the formula (1-A1), the compound represented by the formula (1-A2), and the formula (1-A3). Or a composition represented by formula (1-A4).
  • [6] [Where: M, n 1 , n 2 , R 11A , R 12A , R 13A , R 21A , R 22A , R 23A , R 24A and A 1 -G 1 -A 2 represent the same meaning as described above. ]
  • a light emitting device comprising a layer containing the composition according to any one of [1] to [8].
  • a compound represented by the formula (H-1) The content by the area percentage method using liquid chromatography of a compound having a molecular weight of 16 larger than that of the compound represented by the formula (H-1) contained as an impurity is represented by the formula (H-1) including the impurity.
  • the said compound which is 0.15% or less with respect to whole quantity of the compound represented.
  • Ar H1 represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar H1 are present, they may be the same or different.
  • n H1 represents an integer of 1 to 10.
  • L H1 is a group obtained by removing one or more hydrogen atoms (typically n H1 ) directly bonded to a carbon atom or a hetero atom constituting the ring from an aromatic hydrocarbon ring or heterocyclic ring, May have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
  • the present invention it is possible to provide a composition and a compound useful for producing a light emitting device in which initial deterioration is sufficiently suppressed.
  • a light emitting device in which initial deterioration is sufficiently suppressed it is possible to provide a light emitting device in which initial deterioration is sufficiently suppressed.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • i-Pr represents an isopropyl group
  • t-Bu represents a tert-butyl group.
  • the hydrogen atom may be a deuterium atom or a light hydrogen atom.
  • the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.
  • the “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 8 .
  • the polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or other embodiments.
  • the terminal group of the polymer compound is preferably a stable group because if the polymerization active group remains as it is, there is a possibility that the light emission characteristics or the luminance life may be lowered when the polymer compound is used for the production of a light emitting device. It is.
  • the terminal group is preferably a group conjugated to the main chain, and examples thereof include a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.
  • Low molecular weight compound means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
  • “Structural unit” means one or more units present in a polymer compound.
  • the “alkyl group” may be linear or branched.
  • the number of carbon atoms of the straight chain alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the alkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl
  • 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, a pentafluoroethyl group,
  • the number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.
  • the “alkoxy group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkoxy group is usually 1 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the alkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
  • a substituent for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-buty
  • the number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
  • the cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.
  • Aryl group means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the number of carbon atoms of the substituent.
  • the number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
  • the aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.
  • the “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.
  • Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc.
  • a compound in which the ring itself exhibits aromaticity, and a heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring Means a compound.
  • the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.
  • the “amino group” may have a substituent, and a substituted amino group is preferable.
  • a substituent which an amino group has an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.
  • the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
  • the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (3,5-di-tert- Butylphenyl) amino group.
  • “Halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “alkenyl group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkenyl group is usually 2-30, preferably 3-20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.
  • the “alkynyl group” may be linear or branched.
  • the number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the branched alkynyl group is usually from 4 to 30, and preferably from 4 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
  • the alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.
  • the “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.
  • the arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formulas (A-1) to (A-20) are preferred.
  • the arylene group includes a group in which a plurality of these groups are bonded.
  • R and R a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
  • a plurality of R and R a may be the same or different, and R a may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Are groups 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.
  • the “substituent” is a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group. Represents an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl group.
  • the substituent may be a crosslinking group.
  • the “functional group” having a substituent a hydrogen atom and a halogen are excluded.
  • the compound represented by the formula (H-1) is preferably a host material.
  • the host material preferably has at least one function selected from the group consisting of light emitting property, hole injecting property, hole transporting property, electron injecting property, and electron transporting property, hole injecting property, hole transporting property, It is more preferable to have at least one function selected from the group consisting of electron injecting properties and electron transporting properties.
  • the lowest excited triplet state (T 1 ) of the compound represented by the formula (H-1) is a light emitting device (hereinafter referred to as “present”) having a layer containing the composition of the present invention. It is also referred to as “light-emitting element of the invention”.), So that it has an energy level equivalent to or higher than T 1 of the phosphorescent compound contained in the composition of the present invention. It is preferable.
  • the molecular weight of the compound represented by the formula (H-1) is usually 1 ⁇ 10 2 to 1 ⁇ 10 4 , preferably 4 ⁇ 10 2 to 2.5 ⁇ 10 3 , more preferably 4 ⁇ 10 2 to 1.5 ⁇ 10 3 .
  • the aryl group in Ar H1 is preferably a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a pyrenyl group, a chrycenyl group, or a triphenylenyl group.
  • a phenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrenyl group or a dihydrophenanthrenyl group still more preferably a phenyl group, a fluorenyl group or a spirobifluorenyl group, This group may have a substituent.
  • the monovalent heterocyclic group in Ar H1 is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, thienyl group, benzothienyl group, dibenzothienyl group, furyl group, benzofuryl group, dibenzofuryl group Pyrrolyl group, indolyl group, azaindolyl group, carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group, more preferably a dibenzothienyl group, a dibenzofuryl group or a carbazolyl group, A carbazolyl group is preferred, and these groups may have a substituent.
  • Ar H1 is more preferably inhibited from initial deterioration of the light emitting device of the present invention, and is preferably a phenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a dibenzothienyl group, a dibenzofuryl group.
  • the substituent that Ar H1 may have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, More preferably, they are an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.
  • Ar H1 When there are a plurality of substituents that Ar H1 may have, it is preferable that they are bonded to each other and do not form a ring together with the atoms to which they are bonded.
  • substituents which Ar H1 may have may further have, preferably, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent It is a heterocyclic group or a substituted amino group.
  • n H1 is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and still more preferably 2.
  • the number of carbon atoms of the aromatic hydrocarbon ring in L H1 is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, excluding the number of carbon atoms of the substituent.
  • the aromatic hydrocarbon ring in L H1 include a benzene ring, naphthalene ring, anthracene ring, fluorene ring, spirobifluorene ring, phenanthrene ring, dihydrophenanthrene ring, pyrene ring, chrysene ring and triphenylene ring.
  • L H1 is preferably a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or heteroatom from the heterocyclic ring, and a carbon atom constituting the ring from the heterocyclic ring having a sulfur atom. Or it is more preferable that it is the group except one or more hydrogen atoms couple
  • the number of carbon atoms of the heterocyclic ring in L H1 is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, excluding the number of carbon atoms of the substituent.
  • heterocyclic ring having a sulfur atom in L H1 examples include a thiophene ring, a thiadiazole ring, a thiazole ring, a benzothiophene ring, an azabenzothiophene ring, a diazabenzothiophene ring, a benzothiadiazole ring, a benzothiazole ring, and a dibenzothiophene ring.
  • heterocycle other than the heterocycle having a sulfur atom in L H1 examples include a pyrrole ring, a furan ring, an oxadiazole ring, an oxazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring, an isoquinoline ring, and a quinazoline ring.
  • L H1 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a substituent is preferable. It is an amino group, more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.
  • L H1 When there are a plurality of substituents (substituents other than an aryl group and a monovalent heterocyclic group) that L H1 may have, it is preferable that they are bonded to each other and do not form a ring with the atoms to which they are bonded. .
  • Examples and preferred ranges of the substituent that the substituent that L H1 may further have may further include the substituent that the substituent that Ar H1 may further have. Same as example and preferred range.
  • the compound represented by the formula (H-1) is preferably a compound represented by the formula (A) because initial deterioration of the light emitting device of the present invention is further suppressed.
  • the number of carbon atoms of the aromatic hydrocarbon ring is usually 6 to 60, preferably 6 to 30, and more preferably 6 excluding the number of carbon atoms of the substituent. ⁇ 18.
  • Examples of the aromatic hydrocarbon ring in ring R 1C and ring R 2C include, for example, a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, indene ring, pyrene ring, perylene ring and chrysene.
  • a ring is mentioned, Preferably, they are a benzene ring, a naphthalene ring, or a fluorene ring, More preferably, it is a benzene ring, These rings may have a substituent.
  • the number of carbon atoms of the aromatic heterocyclic ring is usually 2 to 60, preferably 3 to 30, more preferably not including the number of carbon atoms of the substituent. 4-15.
  • Examples of the aromatic heterocycle in the ring R 1C and the ring R 2C include, for example, a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, and an indole.
  • phenazine ring preferably pyridine ring, diazabenzene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, phenazine ring and 5,10-dihydro And phenazine ring, preferably pyridine ring, diazabenzene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacrylate.
  • substituents that the ring R 1C and ring R 2C may have (substituents other than an aryl group and a monovalent heterocyclic group) and preferred ranges thereof are the substituents that L H1 may have ( Examples and preferred ranges of the substituents other than the aryl group and the monovalent heterocyclic group are the same.
  • At least one is preferably an aromatic hydrocarbon ring, more preferably both the ring R 1C and the ring R 2C are aromatic hydrocarbon rings, More preferably, both H1 and ring R H2 are benzene rings.
  • X H1 is preferably a single bond, an oxygen atom or a sulfur atom, and more preferably a single bond.
  • R XH1 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • R XH1 ′ is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R XH1 and R XH1 ′ may have are the same as examples and preferred ranges of substituents that L H1 may further have. It is.
  • n H1-1 and n H1-2 are each independently preferably an integer of 0 or more and 4 or less, more preferably an integer of 0 or more and 2 or less, and even more preferably 1.
  • n H1-1 + n H1-2 which is the sum of n H1 and n H1-2 , is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and still more preferably 2.
  • the compound represented by the formula (A) is preferably a compound represented by the formula (A-1) because initial deterioration of the light emitting device of the present invention is further suppressed.
  • R H1 to R H8 are each independently preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a group represented by the formula (AR-1), a substituted amino group, or a halogen atom. More preferably a hydrogen atom, an alkyl group, a cycloalkyl group or a group represented by the formula (AR-1), still more preferably a hydrogen atom or a group represented by the formula (AR-1). These groups may have a substituent.
  • At least one of R H1 , R H2 , R H4 , R H5 , R H7 and R H8 is a group represented by the formula (AR-1). It is preferable that at least one of R H2 , R H4 , R H5 and R H7 is a group represented by the formula (AR-1), and among R H2 and R H7 , More preferably, at least one is a group represented by the formula (AR-1), and R H2 and R H7 are particularly preferably a group represented by the formula (AR-1).
  • Examples and preferred ranges of substituents that R H1 to R H8 may have are the same as examples and preferred ranges of substituents that L H1 may further have. is there.
  • Examples of the compound represented by the formula (H-1) include compounds represented by the following formulas (H-101) to (H-127), and are represented by the formulas (H-113), (H-117), Compounds represented by formula (H-119) to formula (H-122), formula (H-124) and formula (H-127) are preferred.
  • the compound represented by the formula (H-1) can be obtained from Aldrich, Luminescence Technology Corp. Etc. are available.
  • the compound represented by the formula (H-1) can be produced, for example, using the reaction represented by the following Reaction Scheme 1: (In the above reaction scheme 1, Ar H1 , n H1 and L H1 are as described above. R 25 represents halogen or the like.) Mixing ratio of each raw material in the reaction of the compound represented by the formula (H-1) a and the compound represented by the formula (H-1) b; solvent, catalyst type, amount used; reaction temperature; reaction time Etc. can be appropriately set with reference to the examples described later and the methods described in the above-mentioned documents.
  • Impurities contained in the composition of the present invention are typically represented by the reaction represented by the above reaction formula 1 (for example, reaction by heating under reflux). )
  • the reaction represented by the above reaction formula 1 for example, reaction by heating under reflux.
  • the content of the compound having a molecular weight of 16 larger than that of the compound represented by the formula (H-1) is within the desired range. can do.
  • the formula (H-1) expression as impurity of the compound represented by (H-1) molecular weight than the compounds represented by the 16 large compound (hereinafter, also referred to as O H) is Since the initial deterioration of the light emitting device of the present invention is suppressed, the content by the area percentage method using liquid chromatography is preferably based on the total amount of the compound represented by the formula (H-1) including the impurity. 0.1% or less, more preferably 0.04% or less, further preferably 0.01% or less, particularly preferably 0.001% or less, and particularly preferably less than 0.001%. is there.
  • the amount of a compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1) can be measured by an area percentage method using high performance liquid chromatography (HPLC). That is, the “amount of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1)” refers to the compound represented by the formula (H-1) measured by the area percentage method using HPLC. It means a value measured by an area percentage method using HPLC of a compound having a large molecular weight of 16. The detection limit value is 0.001%, and “the amount of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1)” is “0.001% or less”. When measured by the percentage method, it means that it is below the detection limit value measured by the area percentage method using HPLC of a compound having a molecular weight of 16 larger than the compound represented by the formula (H-1).
  • HPLC high performance liquid chromatography
  • the present inventors have surprisingly found that there is a correlation between the amount of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1) and the initial deterioration of the light emitting device of the present invention. It is presumed that the compound having a molecular weight of 16 larger than the compound represented by the formula (H-1) is a compound in which one oxygen atom is added to the compound represented by the formula (H-1).
  • the compound having a molecular weight of 16 larger than the compound represented by the formula (H-1) is, for example, one hydrogen atom bonded to the sp 2 carbon atom or the sp 3 carbon atom in the compound represented by the formula (H-1).
  • the present inventors presume that in a compound in which one oxygen atom is added to the compound represented by the formula (H-1), the oxygen source is oxygen in the air.
  • the above structure of the compound having a molecular weight of 16 larger than that of the compound represented by the formula (H-1) is an estimate, but even if the above assumption is not followed, the compound having the molecular weight as long as the requirement defined in the present invention is satisfied. It is included in the technical scope of the invention.
  • HM-N when the total amount of the compound consisting essentially of the compound represented by -1) and the phosphorescent compound is 100 (%), respectively Y HM-1, Y HM- 2,
  • ⁇ Y HM-N the content of O H to the compound the total amount of the formula (H-1) (%) is the following formula Is calculated by The specific method for calculating the O H with Example D1 and Example D2 described later, it will be described.
  • Example D1 since the amount of molecular weight from Compound HM-1 as measured by the area percentage method using HPLC is 16 larger compound is below the detection limit, O H is measured to 0.001%.
  • Example D2 the amount of the compound having a molecular weight of 16 larger than that of the compound HM-1 and the amount of the compound having a molecular weight of 16 larger than that of the compound HM-2 measured by the area percentage method using HPLC are each below the detection limit ( That is, 0.001%) and 0.229%.
  • O H may be determined from the amount and the amount of their charge of molecular weight from Compound HM-1 is 16 larger compounds and molecular weight from the compound HM-2 is 16 larger compound, is determined as follows.
  • the compound represented by the formula (H-1) of the present invention is essentially composed of the compound represented by the formula (H-1), that is, the compound represented by the formula (H-1) and the formula When considered as a composition consisting only of impurities generated during the synthesis of the compound represented by (H-1), preferably, the compound represented by formula (H-1) as an impurity of the compound represented by formula (H-1)
  • the content of the compound having a molecular weight of 16 larger than that of the compound represented by the area percentage method using liquid chromatography is 0.15 based on the total amount of the compound represented by the formula (H-1) including the impurities. % Or less. In this case, it is possible to provide a compound and a composition useful for manufacturing a light-emitting device in which initial deterioration is sufficiently suppressed.
  • the total amount of the compound represented by the formula (H-1) including impurities is expressed by the molecular weight of the compound represented by the formula (H-1) and the compound represented by the formula (H-1). May be approximated as the total amount of compounds with a 16 greater.
  • the content of a compound having a molecular weight of 16 larger than the compound represented by the formula (H-1) as an impurity of the compound represented by the formula (H-1) by the area percentage method using liquid chromatography is represented by the formula (H-1). It is preferably 0.15% or less based on the total amount of the compound represented by -1) and the compound having a molecular weight of 16 larger than that of the compound represented by Formula (H-1).
  • Method of reducing O H is, for example, the processing method by purification.
  • Examples of purification include sublimation, extraction, reprecipitation, recrystallization, chromatography, and adsorption, and recrystallization is preferable.
  • Purification may be performed once but may be performed twice or more. When the purification is performed twice or more, these methods may be the same or different.
  • the degree of vacuum and the sublimation temperature may be appropriately set according to the material to be sublimated.
  • the degree of vacuum is preferably 1 ⁇ 10 ⁇ 10 to 1 ⁇ 10 5 Pa, more preferably 1 ⁇ 10 ⁇ 4 to 1 ⁇ 10 ⁇ 2 Pa.
  • the sublimation temperature is preferably ⁇ 100 ° C. to 1000 ° C., more preferably 200 ° C. to 350 ° C.
  • the extraction is preferably liquid separation or solid-liquid extraction using a Soxhlet extractor, and more preferably liquid separation.
  • solvent used for extraction examples include alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, 2-ethoxyethanol; diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, diglyme.
  • alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, 2-ethoxyethanol; diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, diglyme.
  • Ether solvents such as methylene chloride and chloroform; nitrile solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene and mesitylene; N, N-dimethylformamide, N Amide solvents such as N, dimethylacetamide; ester solvents such as ethyl acetate and butyl acetate; acetone, dimethyl sulfoxide and water. Ethyl acetate, ester solvents such as butyl acetate are preferred because it can more effectively reduce the O H.
  • a solvent may be used individually by 1 type, or may use 2 or more types together.
  • the solvent used for reprecipitation is preferably a solvent containing an ether solvent, a halogen solvent, an amide solvent, a hydrocarbon solvent or an ester solvent, and is a mixed solvent of a hydrocarbon solvent and an ester solvent. Is more preferable.
  • the solvent used for reprecipitation may be used alone or in combination of two or more.
  • the solvent used for recrystallization is preferably a solvent containing an ether solvent, a halogen solvent, an amide solvent, a hydrocarbon solvent or an ester solvent, and is a mixed solvent of a hydrocarbon solvent and an ester solvent. Is more preferable.
  • the solvent used for recrystallization may be used individually by 1 type, or may use 2 or more types together.
  • Reduction of O H from the viewpoint of the balance between the yield of the compound represented by the formula (H-1), the solvent used for the recrystallization, it is preferred to use two or ⁇ 10 species, two or three Is more preferable, and it is particularly preferable to use two types in combination.
  • recrystallization is preferably carried out below 10 times more than once, it is carried out following 5 or more times 3 times More preferred.
  • the chromatography is preferably column chromatography.
  • a filler used for column chromatography silica gel or alumina is preferable.
  • the example of the solvent used for chromatography is the same as the example of the solvent used for the extraction described above.
  • the adsorbent is preferably activated carbon, silica gel, alumina or celite.
  • the treatment with the adsorbent is usually performed in a solvent.
  • the solvent used for the treatment with the adsorbent are the same as the examples of the solvent used for the extraction described above.
  • 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 compounds represented by the formula (H-1).
  • the phosphorescent compound is usually a compound that exhibits phosphorescence at room temperature (25 ° C.), and preferably a compound that emits light from a triplet excited state at room temperature (25 ° C.).
  • the phosphorescent compound is preferably a compound represented by the formula (1) because initial deterioration of the light emitting device of the present invention is suppressed.
  • the compound represented by the formula (1) includes M as a central metal, a ligand whose number is defined by the subscript n 1 , and a ligand whose number is defined by the subscript n 2 It consists of and.
  • M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, since initial deterioration of the light emitting device of the present invention is suppressed.
  • M is a ruthenium atom, a rhodium atom or an iridium atom
  • n 1 is preferably 2 or 3, and more preferably 3.
  • n 1 is preferably 2.
  • E 1 and E 2 are preferably carbon atoms.
  • Ring L 1 is preferably a 5- to 10-membered aromatic heterocycle, more preferably a 5-membered or 6-membered aromatic heterocycle, and 2 to 4 nitrogen atoms as constituent atoms. More preferably, it is a 5-membered aromatic heterocyclic ring or a 6-membered aromatic heterocyclic ring having 1 or more and 4 or less nitrogen atoms as constituent atoms, and 2 or more and 3 or less nitrogen atoms as constituent atoms.
  • the 5-membered aromatic heterocyclic ring or a 6-membered aromatic heterocyclic ring having one or more and two or less nitrogen atoms as constituent atoms is particularly preferred, and these rings may have a substituent.
  • E 1 is preferably a carbon atom.
  • Examples of the ring L 1 include a diazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, a diazabenzene ring, a triazine ring, a quinoline ring and an isoquinoline ring, and a diazole ring, a triazole ring, a pyridine ring or a pyrimidine ring is preferable.
  • a ring or a triazole ring is more preferable, a diazole ring is more preferable, and these rings may have a substituent.
  • Ring L 2 is preferably a 5- to 14-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocyclic ring, or a 5-membered or 6-membered aromatic hydrocarbon ring, or 5-membered or More preferably, it is a 6-membered aromatic heterocyclic ring, more preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocyclic ring, and particularly preferably a 6-membered aromatic hydrocarbon ring. Preferably, these rings may have a substituent.
  • E 2 is preferably a carbon atom.
  • Examples of the ring L 2 include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an indene ring, a pyridine ring, a pyrimidine ring, a diazabenzene ring, and a triazine ring, and a benzene ring, a pyridine ring, or a pyrimidine ring is preferable. Rings are more preferable, and these rings may have a substituent.
  • Examples of the substituent that the ring L 1 and the ring L 2 may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, and a substituted amino group.
  • a halogen atom is preferable, an aryl group or a monovalent heterocyclic group is more preferable, an aryl group is further preferable, and these groups may further have a substituent.
  • a phenyl group in the substituent that the ring L 1 and the ring L 2 may have, a phenyl group, a naphthyl group, an anthracenyl group, a fentrenyl group, a dihydrofentrenyl group, a fluorenyl group, or a pyrenyl group is preferable.
  • a naphthyl group or a fluorenyl group is more preferable, a phenyl group is further preferable, and these groups may further have a substituent.
  • Examples of the monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have include a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, A carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group or a phenothiazinyl group is preferred, a triazinyl group is more preferred, and these groups may further have a substituent.
  • the amino group in the substituted amino group in the substituent that the ring L 1 and the ring L 2 may have, the amino group preferably has an aryl group or a monovalent heterocyclic group, and these groups are further substituted. You may have. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent that the amino group has are the aryl group and monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have. Same as example and preferred range.
  • Examples of the substituent that the ring L 1 and the ring L 2 may have further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A monovalent heterocyclic group, a substituted amino group or a halogen atom is preferred, an alkyl group, a cycloalkyl group or an aryl group is more preferred, and these groups may further have a substituent.
  • the aryl group, monovalent heterocyclic group, or substituted amino group in the substituent that the ring L 1 and the ring L 2 may have is more preferable because initial deterioration of the light emitting device of the present invention is further suppressed.
  • m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
  • GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent.
  • Ar DA1 , Ar DA2 and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • the plurality of TDAs may be the same or different.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 or more.
  • GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent.
  • a plurality of GDAs may be the same or different.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • the plurality of TDAs may be the same or different.
  • m DA1 represents an integer of 0 or more.
  • Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • m DA1, m DA2, m DA3 , m DA4, m DA5, m DA6 and m DA7 is usually 10 or less integer is preferably 5 or less integer, more preferably 2 or less an integer, further Preferably 0 or 1.
  • m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
  • G DA is preferably a group represented by the formula (GDA-11) ⁇ formula (GDA-15).
  • R DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of RDA , they may be the same or different. ]
  • R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, and these groups may have a substituent.
  • Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 are preferably groups represented by the formulas (ArDA-1) to (ArDA-5), more preferably the formula (ArDA -1) to a group represented by formula (ArDA-3), more preferably a group represented by formula (ArDA-1) or formula (ArDA-2), and particularly preferably a group represented by formula (ArDA-1). ), And these groups may have a substituent.
  • R DA represents the same meaning as described above.
  • R DB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of RDBs , they may be the same or different. ]
  • R DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • T DA is preferably a group represented by the formula (TDA-1) ⁇ formula (TDA-3), more preferably a group represented by the formula (TDA-1).
  • R DA and R DB represent the same meaning as described above.
  • the group represented by the formula (D-A) is preferably a group represented by the formula (D-A1) to the formula (D-A4).
  • R p1 , R p2 , R p3 and R p4 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom.
  • R p1 , R p2 and R p4 may be the same or different.
  • np1 represents an integer of 0 to 5
  • np2 represents an integer of 0 to 3
  • np3 represents 0 or 1
  • np4 represents an integer of 0 to 4.
  • a plurality of np1 may be the same or different.
  • the group represented by the formula (D-B) is preferably a group represented by the formula (D-B1) to the formula (D-B3).
  • R p1 , R p2 and R p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom.
  • R p1 and R p2 they may be the same or different.
  • np1 represents an integer of 0 to 5
  • np2 represents an integer of 0 to 3
  • np3 represents 0 or 1.
  • np1 and np2 may be the same or different.
  • the group represented by the formula (DC) is preferably a group represented by the formula (D-C1) to the formula (D-C4), more preferably the formula (D-C1) to the formula (D-C3). More preferably a group represented by the formula (D-C1) or the formula (D-C2), and particularly preferably a group represented by the formula (D-C2).
  • R p4 , R p5 and R p6 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R p4 , R p5 and R p6 , they may be the same or different.
  • np4 represents an integer of 0 to 4
  • np5 represents an integer of 0 to 5
  • np6 represents an integer of 0 to 5.
  • Np1 is preferably 0 or 1, more preferably 1.
  • np2 is preferably 0 or 1, more preferably 0.
  • np3 is preferably 0.
  • np4 is preferably an integer of 0 to 2, and preferably 2.
  • np5 is preferably an integer of 1 to 3, and preferably 1.
  • np6 is preferably an integer of 0 to 2, preferably 0.
  • the alkyl group or cycloalkyl group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, 2-ethylhexyl.
  • the alkoxy group or cycloalkoxy group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy group.
  • R p1 , R p2 , R p3 , R p4 , R p5 and R p6 are preferably an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and more An alkyl group which may have a substituent is preferable, and a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group is more preferable. Particularly preferred is an isopropyl group.
  • Examples of the group represented by the formula (D-A) include groups represented by the formula (D-A-1) to the formula (D-A-12).
  • R D represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or Represents a cyclohexyloxy group.
  • two or more RD exists, they may be the same or different.
  • Examples of the group represented by the formula (D-B) include groups represented by the formula (D-B-1) to the formula (D-B-7).
  • R D represents the same meaning as described above.
  • Examples of the group represented by the formula (D-C) include groups represented by the formula (D-C-1) to the formula (D-C-13).
  • R D represents the same meaning as described above.
  • R D is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group.
  • the ring L 1 When there are a plurality of substituents that the ring L 1 may have, they are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.
  • substituents that the ring L 2 When there are a plurality of substituents that the ring L 2 may have, they are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.
  • the substituent that the ring L 1 may have and the substituent that the ring L 2 may have are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.
  • anionic bidentate ligand examples include a ligand represented by the following formula. However, the anionic bidentate ligand represented by A 1 -G 1 -A 2 is different from the ligand whose number is defined by the subscript n 1 .
  • R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
  • a plurality of R L1 may be the same or different.
  • R L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
  • R L1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a fluorine atom, and these groups may have a substituent.
  • R L2 is preferably an alkyl group or an aryl group, and these groups optionally have a substituent.
  • the compound represented by the formula (1) is a compound represented by the formula (1-A) or the compound represented by the formula (1-B) because the initial deterioration of the light emitting device of the present invention is further suppressed.
  • it is a compound represented by the formula (1-A).
  • ring L 1A is a triazole ring
  • a triazole ring in which E 11A and E 12A are nitrogen atoms, or a triazole ring in which E 11A and E 13A are nitrogen atoms is preferable, and E 11A and E 12A are nitrogen atoms.
  • a triazole ring is more preferred.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are ring L 1 and ring L 2 , respectively.
  • R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A may have and preferred ranges thereof may have ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent may further have.
  • R 11A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
  • R 11A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups have a substituent. It may be.
  • R 12A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. You may do it.
  • R 12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, These groups may have a substituent.
  • R 13A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. You may do it.
  • R 13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, These groups may have a substituent.
  • the solid line “-” connecting C and E 21A , E 21A and E 22A , E 22A and E 23A , E 23A and E 24A , E 24A and C, and C and C in ring L 2A is independently a single bond Or a double bond is shown.
  • ring L 2A is a pyridine ring
  • a pyridine ring in which E 21A is a nitrogen atom a pyridine ring in which E 22A is a nitrogen atom, or a pyridine ring in which E 23A is a nitrogen atom is preferable.
  • the ring L 2A is a pyrimidine ring
  • a pyrimidine ring in which E 22A and E 24A are nitrogen atoms is preferable.
  • Ring L 2A is preferably a benzene ring.
  • R 21A , R 22A , R 23A and R 24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, fluorine atom or substituted amino group Are more preferable, and a hydrogen atom or a group represented by the formula (DA) is more preferable, and these groups may have a substituent.
  • R 22A or R 23A is an aryl group, a monovalent heterocyclic group or a substituted amino group.
  • R 11A and R 12A , R 12A and R 13A , R 11A and R 21A , R 21A and R 22A , R 22A and R 23A , and R 23A and R 24A are bonded to each other together with the atoms to which they are bonded. It is preferable not to form a ring.
  • the compound represented by the formula (1-A) can further suppress the initial deterioration of the light-emitting element of the present invention
  • the compound represented by the formula (1-A1) and the compound represented by the formula (1-A2) Preferably, the compound is a compound represented by the formula (1-A3) or a compound represented by the formula (1-A4), and a compound represented by the formula (1-A1) or the formula (1-A3)
  • the compound represented by formula (1-A3) is more preferred.
  • the solid line “-” connecting C and E 21B , E 21B and E 22B , E 22B and E 23B , E 23B and E 24B , E 24B and C, and C and C in the ring L 2B is independently a single bond Or a double bond is shown.
  • a pyridine ring in which E 21B is a nitrogen atom
  • E 23B is a nitrogen atom
  • Ring L 2B is preferably a benzene ring.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are the ring L 1 and Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the ring L 2 may have are the same as the preferred range.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B may have and preferred ranges thereof include ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent which may be further may have.
  • R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, fluorine atom, aryl A monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom or a group represented by the formula (DA), and these groups have a substituent. It may be.
  • R 11B and R 12B , R 12B and R 13B , and R 13B and R 14B are bonded to form a ring together with the atoms to which they are bonded
  • R 11B and R 12B , R 12B and R 13B , R 13B and R 14B are preferably bonded to each other to form an aromatic hydrocarbon ring or an aromatic heterocycle together with the atoms to which they are bonded.
  • Examples of the aromatic hydrocarbon ring and aromatic heterocycle formed include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an indene ring, a pyridine ring, a diazabenzene ring, and a triazine ring, and a benzene ring is preferable. These rings may have a substituent.
  • R 11B and R 21B , R 21B and R 22B , R 22B and R 23B , and R 23B and R 24B are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.
  • R 11B , R 12B or R 13B is preferably an aryl group, monovalent heterocyclic group or substituted amino group.
  • R 22B or R 23B is preferably an aryl group, a monovalent heterocyclic group or a substituted amino group.
  • the compound represented by the formula (1-B) is further represented by the compound represented by the formula (1-B1) and the formula (1-B2) because the initial deterioration of the light emitting device of the present invention is further suppressed.
  • the compound is a compound represented by the formula (1-B3), a compound represented by the formula (1-B4), or a compound represented by the formula (1-B5).
  • n 11 and n 12 each independently represents an integer of 1 or more, and n 11 + n 12 is 2 or 3.
  • M is a ruthenium atom, rhodium atom or iridium atom, n 11 + n 12 is 3, and when M is a palladium atom or platinum atom, n 11 + n 12 is 2.
  • R 15B , R 16B , R 17B and R 18B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group Represents a group or a halogen atom, and these groups optionally have a substituent.
  • R 15B , R 16B , R 17B and R 18B may be the same or different.
  • R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21B are bonded to each other to form a ring together with the atoms to which they are bonded. Also good. ]
  • aryl groups, monovalent heterocyclic groups and substituted amino groups in R 15B , R 16B , R 17B and R 18B and preferred ranges thereof are the substituents that the ring L 1 and the ring L 2 may have, respectively.
  • R 15B , R 16B , R 17B and R 18B may have and preferred ranges thereof may be further included in the substituents which ring L 1 and ring L 2 may have. Examples of good substituents and preferred ranges are the same.
  • R 15B , R 16B , R 17B and R 18B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, fluorine atom, aryl group, monovalent heterocyclic group or substituted amino group It is preferable that these groups may have a substituent.
  • R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21B may be bonded to each other and do not form a ring with the atoms to which they are bonded. preferable.
  • R 11B and R 12B , R 12B and R 13B , and R 13B and R 14B are bonded to each other and are bonded to each other. It is preferred not to form a ring with the atoms.
  • Examples of the phosphorescent compound include compounds represented by the following formula.
  • Examples of the phosphorescent compound include “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical Society, Vol. 2004-530254, JP-A-2008-179617, JP-A-2011-105701, JP-T-2007-504272, International Publication No. 2006/121811, JP-A-2013-147450, JP-A-2014-14 It can be synthesized according to the method described in Japanese Patent No. 224101.
  • the phosphorescent compound does not include a compound having a molecular weight of 16 larger than that of the compound represented by the formula (H-1) as an impurity
  • the phosphorescent compound measured by an area percentage method using HPLC has an impurity as an impurity.
  • the amount (O 1 ) of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1) contained is not more than the detection limit value, that is, not more than 0.001% with respect to the total amount of the composition.
  • O 1 is 0.001%.
  • the composition of the present invention is a composition containing a compound represented by the formula (H-1) and a phosphorescent compound.
  • the content of the compound having a molecular weight of 16 larger than the compound represented by the formula (H-1) contained as an impurity in the composition by an area percentage method using liquid chromatography is based on the total amount of the composition. , Preferably 0.07% or less, more preferably 0.03% or less, still more preferably 0.01% or less, particularly preferably 0.001% or less, and particularly preferably 0.001. %.
  • the compound represented by the formula (H-1) may be blended singly or in combination of two or more.
  • the phosphorescent compound may be blended alone or in combination of two or more.
  • the compound having a molecular weight of 16 larger than that of the compound represented by formula (H-1) is usually an area percentage method using liquid chromatography with respect to the total solid content blended in the composition. Is preferably 0.1% or less, more preferably 0.07% or less, still more preferably 0.03% or less, particularly preferably 0.001% or less, and particularly preferably Is less than 0.001%.
  • the solid content blended in the composition of the present invention consists essentially of a compound represented by the formula (H-1) and a phosphorescent compound, and a compound represented by the formula (H-1) as an impurity
  • a compound having a larger molecular weight of 16 is included, the total amount of the compound having a molecular weight of 16 larger than that of the compound represented by the formula (H-1) is the difference between the compound represented by the formula (H-1) and the phosphorescent compound.
  • the ratio of the mass of the compound represented by the formula (H-1) to the total mass is W H , and the ratio of the phosphorescent compound to the total mass of the compound represented by the formula (H-1) and the phosphorescent compound
  • W 1 the ratio of the phosphorescent compound to the total mass of the compound represented by the formula (H-1) and the phosphorescent compound
  • W 1 is usually 0.0001 to 0.90, and is preferably 0.01 to 0.60, because initial deterioration of the light emitting device of the present invention is further suppressed, and preferably 0.10 to 0.00. More preferably, it is 40.
  • the specific calculation method of W 1 can be obtained in the same manner as the specific calculation method of WH .
  • WH is usually 0.1 to 0.9999, and is preferably 0.40 to 0.99, since initial deterioration of the light emitting device of the present invention is further suppressed, and is preferably 0.60 to 0.00. More preferably, it is 90.
  • O H W H + O 1 W 1 will be described using Examples D1 to D5 and Comparative Example CD1 described later. Note that O 1 in Examples D1 to D5 and Comparative Example CD1 is not more than the detection limit value, that is, 0.001%.
  • O H W H + O 1 W 1 in the embodiment D1 is determined as follows.
  • O H W H + O 1 W 1 in the embodiment D2 is determined as follows.
  • O H W H + O 1 W 1 in the embodiment D3 is calculated as follows.
  • O H W H + O 1 W 1 in the embodiment D4 is determined as follows.
  • O H W H + O 1 W 1 in the embodiment D5 is determined as follows.
  • O H W H + O 1 W 1 in Comparative Example CD1 is determined as follows.
  • O H W H + O 1 W 1 is preferably 0.1% or less, more preferably 0.07% or less, still more preferably 0.03% or less, and particularly preferably 0.01% or less. And particularly preferably 0.001%.
  • composition of the present invention further satisfies the formula (2 ′).
  • O 1 and O H are as defined above.
  • Formula (2 ′) is preferably Formula (2′-1), more preferably Formula (2′-2), still more preferably Formula (2′-3), and particularly preferably Formula (2′-3). 2′-4).
  • the total amount of impurities contained in the composition of the present invention (typically, the total amount of impurities derived from the production of the compound represented by the formula (H-1) and the phosphorescent compound)
  • the content by the area percentage method using liquid chromatography is preferably less than 0.777%, more preferably 0.56% or less, based on the total amount of solids contained in the composition. 0.42% or less, still more preferably 0.38% or less, particularly preferably 0.34% or less, particularly preferably 0.33% or less.
  • the compounding amount of the compound represented by the formula (H-1) in the composition of the present invention is not particularly limited, but may be 10 to 99.99% by mass on the basis of the total solid content blended in the composition. 40 to 99% by mass, and more preferably 60 to 90% by mass.
  • the blending amount of the phosphorescent compound in the composition of the present invention is not particularly limited, but may be 0.01 to 90% by mass based on the total solid content blended in the composition, and may be 1 to 60% by mass. It is preferably 10 to 40% by mass.
  • the composition of the present invention is at least selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from a phosphorescent compound), an antioxidant, and a solvent.
  • a hole transport material a hole injection material
  • an electron transport material an electron injection material
  • a light emitting material different from a phosphorescent compound
  • an antioxidant an antioxidant
  • a solvent a solvent
  • One kind of material may be further contained.
  • the hole transport material, the hole injection material, the electron transport material, the electron injection material, and the light emitting material are different from the compound represented by the formula (H-1).
  • composition of the present invention further contains at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant, these material is a reduction method similar to the method of O H, it is preferable to reduce impurities.
  • the hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound.
  • the hole transport material may have a crosslinking group.
  • polymer compound examples include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof.
  • the polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like.
  • the compounding amount of the hole transport material is usually 1 to 400 parts by mass when the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 parts by mass.
  • the amount is 5 to 150 parts by mass.
  • the hole transport material may be used alone or in combination of two or more.
  • Electron transport materials are classified into low molecular compounds and high molecular compounds.
  • the electron transport material may have a crosslinking group.
  • low molecular weight compound examples include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone. As well as these derivatives.
  • polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
  • the polymer compound may be doped with a metal.
  • the amount of the electron transporting material is usually 1 to 400 parts by mass when the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 parts by mass. Yes, preferably 5 to 150 parts by mass.
  • the electron transport material may be used alone or in combination of two or more.
  • the hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively.
  • the hole injection material and the electron injection material may have a crosslinking group.
  • low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • metal phthalocyanines such as copper phthalocyanine
  • carbon such as carbon
  • metal oxides such as molybdenum and tungsten
  • metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • polymer compound examples include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.
  • the compounding amounts of the hole injecting material and the electron injecting material are usually in the case where the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 parts by mass. 1 to 400 parts by mass, preferably 5 to 150 parts by mass.
  • the electron injection material and the hole injection material may be used alone or in combination of two or more.
  • the electrical conductivity of the conductive polymer is preferably 1 ⁇ 10 ⁇ 5 S / cm to 1 ⁇ 10 3 S / cm.
  • the conductive polymer can be doped with an appropriate amount of ions.
  • the kind of ions to be doped is an anion for a hole injection material and a cation for an electron injection material.
  • the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion.
  • the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
  • the ions to be doped may be used alone or in combination of two or more.
  • Luminescent material Luminescent materials (different from phosphorescent compounds) are classified into low molecular compounds and high molecular compounds.
  • the light emitting material may have a crosslinking group.
  • Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, and perylene and derivatives thereof.
  • polymer compound examples include arylene groups such as a phenylene group, naphthalenediyl group, fluorenediyl group, phenanthrene diyl group, dihydrophenanthrene diyl group, anthracenediyl group, and pyrenediyl group;
  • arylene groups such as a phenylene group, naphthalenediyl group, fluorenediyl group, phenanthrene diyl group, dihydrophenanthrene diyl group, anthracenediyl group, and pyrenediyl group
  • aromatic amine residues such as groups to be removed
  • polymer compounds containing divalent heterocyclic groups such as carbazolediyl group, phenoxazinediyl group, and phenothiazinediyl group.
  • the amount of the luminescent material is usually 0.1 to 400 parts by mass when the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 parts by mass. It is preferably 1 to 150 parts by mass.
  • Fluorescent materials may be used alone or in combination of two or more.
  • the antioxidant may be any compound that is soluble in the same solvent as the compound represented by the formula (H-1) and the phosphorescent compound and does not inhibit light emission and charge transport.
  • a phenolic antioxidant And phosphorus antioxidants for example, a phenolic antioxidant And phosphorus antioxidants.
  • the blending amount of the antioxidant is usually 0.001 to 10 mass when the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 mass parts. Part.
  • Antioxidants may be used alone or in combination of two or more.
  • [ink] A composition (hereinafter also referred to as “ink”) containing a compound represented by the formula (H-1), a phosphorescent compound, and a solvent is prepared by spin coating, casting, microgravure coating, Gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. It can be suitably used for the coating method.
  • the viscosity of the ink may be adjusted depending on the type of coating method, but when a solution such as an inkjet printing method is applied to a printing method that passes through a discharge device, clogging and flight bending at the time of discharge are less likely to occur.
  • the pressure is preferably 1 to 20 mPa ⁇ s at 25 ° C.
  • the solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink.
  • the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone,
  • the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 100 parts by mass when the total of the compound represented by the formula (H-1) and the phosphorescent compound is 100 parts by mass. It is 20000 parts by mass.
  • the membrane contains the composition of the present invention.
  • the film is suitable as a layer in a light emitting element, particularly as a light emitting layer.
  • the film can be produced by using, for example, the coating method using ink.
  • the thickness of the film is usually 1 nm to 10 ⁇ m.
  • the light emitting device of the present invention is a light emitting device comprising a layer containing the composition of the present invention.
  • a structure of the light emitting element of this invention it has the electrode which consists of an anode and a cathode, for example, and the layer containing the composition of this invention provided between this electrode.
  • the layer containing the composition of the present invention is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and is preferably a light emitting layer.
  • Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material.
  • Each of these layers is the same as the above-described film production, in which a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material are dissolved in the above-described solvent and ink is prepared and used. It can be formed using a method.
  • the light emitting element has a light emitting layer between the anode and the cathode.
  • the light emitting device of the present invention preferably has at least one of a hole injection layer and a hole transport layer between the anode and the light emitting layer from the viewpoint of hole injection and hole transport. From the viewpoint of injection property and electron transport property, it is preferable to have at least one of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.
  • Examples of the material of the hole transport layer, the electron transport layer, the light emitting layer, the hole injection layer, and the electron injection layer include, for example, the above-described hole transport material, electron transport material, and light emitting material, in addition to the composition of the present invention. , Hole injection materials and electron injection materials.
  • the material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are used as solvents used in forming the layer adjacent to the hole transport layer, the electron transport layer, and the light emitting layer, respectively, in the production of the light emitting element.
  • the material When dissolved, the material preferably has a cross-linking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
  • each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer
  • a low molecular compound for example, vacuum deposition from powder
  • a method using film formation from a solution or a molten state may be used.
  • the order, number and thickness of the layers to be laminated are adjusted in consideration of the external quantum efficiency and the luminance lifetime.
  • the substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed.
  • the substrate is made of a material such as glass, plastic, or silicon.
  • the electrode farthest from the substrate is preferably transparent or translucent.
  • Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • conductive metal oxides and translucent metals preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds.
  • Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
  • Each of the anode and the cathode may be a single layer or a stacked structure of two or more layers.
  • the planar anode and the cathode may be arranged so as to overlap each other.
  • a method of forming an anode or a cathode, or both electrodes in a pattern is a method.
  • a segment type display device capable of displaying numbers, characters, and the like can be obtained.
  • both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter.
  • the dot matrix display device can be driven passively, or can be driven active in combination with a TFT or the like.
  • These display devices can be used for displays of computers, televisions, portable terminals and the like.
  • the planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source and display device.
  • the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by the following size exclusion chromatography (SEC) using tetrahydrofuran as the moving bed. .
  • 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 was run at a flow rate of 2.0 mL / min.
  • PLgel MIXED-B manufactured by Polymer Laboratories
  • a UV-VIS detector manufactured by Shimadzu Corporation, trade name: SPD-10Avp was used as the detector.
  • 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 names: 1290 Infinity LC and 6230 TOF LC / MS. LC-MS migration).
  • the phase was flowed at a flow rate of 1.0 mL / min while changing the ratio of acetonitrile and tetrahydrofuran, and the column was SUMPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Center, inner diameter: 4.6 mm, length: 250 mm, particle size 3 ⁇ m) was used.
  • TLC-MS was measured by the following method. A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran or chloroform at an arbitrary concentration, and applied on a TLC plate for DART (trade name: YSK5-100, manufactured by Techno Applications), and TLC-MS (JEOL Ltd.) (Trade name: JMS-T100TD (The AccuTOF TLC)). The helium gas temperature during measurement was adjusted in the range of 200 to 400 ° C.
  • NMR NMR was measured by the following method. About 5 to 10 mg of a measurement sample, about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethyl sulfoxide, heavy acetone, heavy N, N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol Alternatively, it was dissolved in methylene chloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).
  • the HPLC area percentage value was used as an indicator of the purity of the compound. Unless otherwise specified, this value is a value at 254 nm by HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured is dissolved in an ink solvent so as to have a concentration of 0.01 to 1.0% by mass, preferably 0.01 to 0.2% by mass, and is analyzed by HPLC according to the concentration. 10 ⁇ L was injected. Sample preparation for HPLC was performed within 30 minutes, stored in the dark, and measured within 10 hours after sample preparation.
  • SUMPAX ODS Z-CLUE manufactured by Sumika Chemical Analysis Center
  • ODS column having equivalent performance was used.
  • the detector a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used.
  • the amount of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1) was measured by HPLC. Confirmation of the compound having a molecular weight of 16 larger than that of the compound was performed by LC-MS.
  • Step 1 After setting the inside of the reaction vessel to an inert gas atmosphere, Compound M1 (0.923 g), Compound M2 (0.0496 g), Compound M3 (0.917 g), dichlorobis (tris-o-methoxyphenylphosphine) Palladium (1.76 mg) and toluene (34 mL) were added and heated to 105 ° C.
  • Step 2 A 20 mass% tetraethylammonium hydroxide aqueous solution (6.7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.
  • Step 3 After the reaction, phenylboronic acid (48.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 mg) were added thereto and refluxed for 14.5 hours.
  • Step 4 Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the resulting reaction solution was washed twice with water, twice with a 3% by mass aqueous acetic acid solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred.
  • the obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order.
  • the obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.23 g of a polymer compound HTL-1.
  • the polymer compound HTL-1 had a polystyrene-equivalent number average molecular weight of 2.3 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.2 ⁇ 10 5 .
  • the theoretical value obtained from the amount of charged raw materials for polymer compound HTL-1 is that the structural unit derived from compound M1, the structural unit derived from compound M2, and the structural unit derived from compound M3 are: It is a copolymer formed by a molar ratio of 45: 5: 50.
  • reaction vessel was filled with a nitrogen gas atmosphere, then compound HM-1a (324 g), compound HM-1b (300 g), xylene (12 L), palladium (II) acetate (11.5 g), tri-tert-butylphosphonium tetra Fluoroborate (29.8 g) and sodium tert-butoxide (555 g) were added, and the mixture was stirred with heating under reflux for 40 hours. Then, the obtained reaction liquid was filtered with a filter coated with silica gel and celite, and the filter coated with silica gel and celite was washed with toluene (10 L).
  • the obtained filtrate was washed 5 times with ion-exchanged water (4 L), and then the obtained organic layer was dried over anhydrous sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was recrystallized from toluene and dried under reduced pressure at 50 ° C. to obtain Compound HM-2 (361 g). The HPLC area percentage value of Compound HM-2 was 99.1%.
  • the obtained compound HM-2 (140 g) was recrystallized twice each with butyl acetate and toluene, and then dried under reduced pressure at 50 ° C. to obtain compound HM-1 (100 g).
  • the HPLC area percentage value of Compound HM-1 was 99.7% or more.
  • the amount of the compound having a molecular weight 16 larger than that of Compound HM-2 contained in Compound HM-2 was 0.229%.
  • the amount of the compound having a molecular weight 16 larger than that of Compound HM-1 contained in Compound HM-1 was below the detection limit (0.001%).
  • Compound HM-1 and Compound HM-2 were subjected to HPLC analysis under the following conditions. The sample was analyzed by diluting the ink with dichloromethane so that the concentrations of HM-1 and Compound HM-2 were 0.2 mass% to 0.3 mass%.
  • the obtained filtrate was extracted with toluene and 10% saline to obtain an organic layer.
  • the obtained organic layer was dried over anhydrous magnesium sulfate and then filtered with a filter coated with amino silica gel.
  • the obtained filtrate was concentrated under reduced pressure to obtain a solid.
  • the obtained solid was recrystallized with a mixed solvent of toluene and acetonitrile, and then filtered to obtain a residue.
  • the obtained residue was dried under reduced pressure at 50 ° C. to obtain phosphorescent compound MC2 (125 g).
  • the HPLC area percentage value of the phosphorescent compound MC2 was 99.5% or more.
  • the residue contained in the phosphorescent compound MC2 was dehalogenated. Specifically, after the light-shielded reaction vessel was filled with an argon gas atmosphere, phosphorescent compound MC2 (40.0 g), phenylboronic acid (3.67 g), (di-tert-butyl (4-dimethylaminophenyl) ) Phosphine) dichloropalladium (II) (0.64 g) and toluene (210 mL) were added and heated to 90.degree. 40 mass% tetrabutylammonium hydroxide aqueous solution (97 mL) was added there, and it stirred at 90 degreeC for 120 hours.
  • the HPLC area percentage value of phosphorescent compound MC3 was 99.59%. Further, the amount of the compound having a molecular weight 16 larger than that of the compound represented by the formula (H-1) contained as an impurity in the phosphorescent compound MC3 was below the detection limit (0.001%).
  • Example D1 Fabrication and evaluation of light-emitting element D1 (production of light-emitting element D1) (Formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries
  • a hole injection layer was formed by heating on a hot plate at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
  • the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.
  • Example D2 Fabrication and evaluation of light-emitting element D2 (production of light-emitting element D2) A light-emitting element D2 was produced in the same manner as in Example D1, except that (Formation D1 of light-emitting layer) in Example D1 was changed to (Formation D2 of light-emitting layer) described below.
  • Example D3 Fabrication and evaluation of light-emitting element D3 (production of light-emitting element D3) A light emitting device D3 was produced in the same manner as in Example D1, except that (Formation D1 of light emitting layer) in Example D1 was changed to (Formation D3 of light emitting layer) described below.
  • Example D4 Fabrication and evaluation of light-emitting element D4 (production of light-emitting element D4) A light-emitting element D4 was produced in the same manner as in Example D1, except that (Formation of light-emitting layer D1) in Example D1 was changed to (Formation of light-emitting layer D4) described below.
  • Example D5 Fabrication and evaluation of light-emitting element D5 (production of light-emitting element D5) A light-emitting element D5 was produced in the same manner as in Example D1, except that (Light-emitting layer formation D1) in Example D1 was changed to the following (Light-emitting layer formation D5).

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une composition contenant un composé représenté par la formule (H-1) et un composé phosphorescent, la quantité d'un composé qui est contenu comme impureté dans ladite composition, et qui présente un poids moléculaire qui est supérieur de 16 à celui du composé représenté par la formule (H-1), étant inférieure ou égale à 0,1 % par rapport à la quantité totale de la composition, ladite quantité étant déterminée par une technique de pourcentage de surface faisant appel à la chromatographie liquide.
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