WO2023054109A1 - Composition, et élément luminescent comprenant celle-ci - Google Patents

Composition, et élément luminescent comprenant celle-ci Download PDF

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WO2023054109A1
WO2023054109A1 PCT/JP2022/035145 JP2022035145W WO2023054109A1 WO 2023054109 A1 WO2023054109 A1 WO 2023054109A1 JP 2022035145 W JP2022035145 W JP 2022035145W WO 2023054109 A1 WO2023054109 A1 WO 2023054109A1
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group
ring
compound
bonded
atom
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慎一 稲員
敏明 佐々田
浩平 浅田
太一 安倍
孝幸 飯島
孝和 斎藤
謙 吉岡
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present disclosure relates to a composition and a light-emitting device containing it.
  • a light-emitting element such as an organic electroluminescence element can be suitably used for display and lighting applications.
  • a light-emitting material used for a light-emitting layer of a light-emitting element for example, Patent Document 1 describes a composition containing a compound H1, a metal complex, and a compound B1.
  • an object of one embodiment of the present disclosure is to provide a composition useful for manufacturing a light-emitting device with excellent external quantum efficiency, and to provide a light-emitting device containing the composition.
  • the present disclosure provides the following ⁇ 1> to ⁇ 12>.
  • a composition comprising
  • M represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
  • n1 represents an integer of 1 or more
  • n2 represents an integer of 0 or more.
  • n 1 +n 2 is 3 when M is a rhodium atom or an iridium atom
  • n 1 +n 2 is 2 when M is a palladium atom or a platinum atom.
  • E 1 and E 2 each independently represent a carbon atom or a nitrogen atom. When multiple E 1 and E 2 are present, they may be the same or different.
  • Ring L 1 represents an aromatic heterocycle, and the ring may have a substituent.
  • substituents When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • rings L 1 When multiple rings L 1 are present, they may be the same or different.
  • Ring L2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. When there is more than one ring L2 , they may be the same or different.
  • the substituent that ring L 1 may have and the substituent that ring L 2 may have may be the same or different, and are bonded to each other to form a ring together with the atoms to which they are bonded. may be formed.
  • a 1 -G 1 -A 2 represents an anionic bidentate ligand.
  • a 1 and A 2 each independently represent 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 forming a bidentate ligand together with A 1 and A 2 . When multiple A 1 -G 1 -A 2 are present, they may be the same or different. ]
  • Ar H1 and Ar H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • n H1 represents an integer of 0 or more.
  • L H1 represents a divalent group, and the divalent group may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • L H1 and Ar H2 may be directly bonded or bonded via a divalent group to form a ring.
  • L H1 and Ar H1 may be directly bonded or bonded via a divalent group to form a ring.
  • L H1 and Ar H2 may be directly bonded or bonded via a divalent group to form a ring.
  • L H1 and Ar H2 may be directly bonded or bonded via a divalent group to form a ring.
  • a X1 and a X2 each independently represent an integer of 0 or more.
  • Ar 1 X1 and Ar 2 X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded; and these groups may have a substituent.
  • R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • R X2 When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • R X2 When multiple R X2 are present, they may be the same or different.
  • R X3 are present, they may be the same or different.
  • Ar Y represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded,
  • the group may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the ring L 1 is an aromatic heterocyclic ring containing a 5-membered ring or an aromatic heterocyclic ring containing a 6-membered ring, these rings may have a substituent
  • the ring L 2 is an aromatic hydrocarbon ring containing a 5- or 6-membered ring, or an aromatic heterocyclic ring containing a 5- or 6-membered ring, these rings optionally having a substituent;
  • the ring L 2 is a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring, or a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring,
  • the ring L 1 is a pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, diazole ring or triazole ring, and these rings may have a substituent
  • the ring L 2 is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these rings may have a substituent, the above ⁇ 1> to ⁇ 3>.
  • the composition according to any one of ⁇ 5> The ring L 1 is a diazole ring or a triazole ring, and these rings may have a substituent, and the ring L 2 is a benzene ring, and these rings are substituents
  • the condensed heterocyclic skeleton (b) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring.
  • composition according to any one of ⁇ 7> The composition according to any one of ⁇ 1> to ⁇ 6>, wherein the condensed heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.
  • the low-molecular-weight compound (B) is a compound represented by formula (1-1), a compound represented by formula (1-2), or a compound represented by formula (1-3).
  • Ar 1 , Ar 2 and Ar 3 each independently represent an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • Y 1 represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, an alkylene group or a cycloalkylene group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • Y 2 and Y 3 each independently represent a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, an alkylene group, It represents a cycloalkylene group, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • Ry 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 multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. When two or more Ry are present, they may be the same or different.
  • Y 1 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 1 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 2 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 2 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 3 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 3 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring.
  • Y 1 , Y 2 and Y 3 are an oxygen atom, a sulfur atom or a group represented by -N(Ry)-.
  • Y 10> The composition according to ⁇ 8> or ⁇ 9>, wherein Y 1 , Y 2 and Y 3 are groups represented by -N(Ry)-.
  • ⁇ 11> The above ⁇ 1> to ⁇ 10, further containing at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent.
  • the composition according to any one of . ⁇ 12> A light-emitting element having an anode, a cathode, and an organic layer provided between the anode and the cathode, A light-emitting device, wherein the organic layer is a layer containing the composition according to any one of ⁇ 1> to ⁇ 11>.
  • a composition useful for manufacturing a light-emitting device with excellent external quantum efficiency it is possible to provide a composition useful for manufacturing a light-emitting device with excellent external quantum efficiency. Further, according to one embodiment of the present disclosure, a light-emitting device containing the composition can be provided.
  • Room temperature means 25°C.
  • Me is a methyl group
  • Et is an ethyl group
  • Bu is a butyl group
  • i-Pr is an isopropyl group
  • t-Bu is a tert-butyl group.
  • a hydrogen atom may be a deuterium atom or a protium atom.
  • solid lines representing bonds with the central metal mean ionic bonds, covalent bonds or coordinate bonds.
  • a "low-molecular-weight compound” means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
  • a “polymer compound” means a polymer having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 or more (for example, 1 ⁇ 10 3 to 1 ⁇ 10 8 ).
  • a “structural unit” means a unit that exists at least one in a polymer compound. Two or more structural units present in a polymer compound are generally called “repeating units".
  • the polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms.
  • the terminal group of the polymer compound is preferably a stable group from the viewpoint of the light emitting properties of the light emitting device.
  • the terminal group of the polymer compound is preferably a group conjugated to the main chain of the polymer compound, for example, an aryl group or 1 valent heterocyclic groups.
  • the "alkyl group” may be either linear or branched.
  • the number of carbon atoms in the linear alkyl group is generally 1-50, preferably 1-20, more preferably 1-10, not including the number of carbon atoms in the substituents.
  • the number of carbon atoms in the branched alkyl group is usually 3-50, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
  • the alkyl group may have a substituent.
  • alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group and heptyl.
  • substituents e.g., trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl)propyl group, 3-(3,5-di-hexylphenyl)propyl group and 6-ethyloxyhexyl group).
  • the number of carbon atoms in the "cycloalkyl group” is usually 3-50, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituents.
  • a cycloalkyl group may have a substituent.
  • Cycloalkyl groups include, for example, cyclohexyl groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
  • the number of carbon atoms in the "alkylene group” is generally 1-20, preferably 1-15, more preferably 1-10, not including the number of carbon atoms in the substituents.
  • the alkylene group may have a substituent.
  • the alkylene group includes, for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, octylene group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.
  • the number of carbon atoms in the "cycloalkylene group" is usually 3 to 20, preferably 4 to 10, more preferably 5 to 7, not including the number of carbon atoms in substituents.
  • a cycloalkylene group may have a substituent.
  • the cycloalkylene group includes, for example, a cyclohexylene group and a group in which some or all of the hydrogen atoms in the group are substituted with substituents.
  • “Aromatic hydrocarbon group” means a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon.
  • a group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon is also referred to as an "aryl group”.
  • a group obtained by removing two hydrogen atoms directly bonded to carbon atoms forming a ring from an aromatic hydrocarbon is also referred to as an "arylene group”.
  • the number of carbon atoms in the aromatic hydrocarbon group is generally 6-60, preferably 6-40, more preferably 6-20, not including the number of carbon atoms in the substituents.
  • aromatic hydrocarbon group includes, for example, monocyclic aromatic hydrocarbons (e.g., benzene), or polycyclic aromatic hydrocarbons (e.g., naphthalene, indene, naphthoquinone, indenone and tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthoquinone and fluorenone; benzoanthracene, benzophenanthrene and benzofluorene.
  • monocyclic aromatic hydrocarbons e.g., benzene
  • polycyclic aromatic hydrocarbons e.g., naphthalene, indene, naphthoquinone, indenone and tetralone
  • tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone,
  • Aromatic hydrocarbon group is a monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon group in which one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed, and a plurality of groups are bonded. may be The aromatic hydrocarbon group may have a substituent.
  • alkoxy group may be either linear or branched.
  • the straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the branched alkoxy group is usually 3-40, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
  • the alkoxy group may have a substituent.
  • alkoxy groups include methoxy, ethoxy, isopropyloxy, butyloxy, hexyloxy, 2-ethylhexyloxy, 3,7-dimethyloctyloxy, lauryloxy, and hydrogen in these groups. Groups in which some or all of the atoms are substituted with substituents are included.
  • the number of carbon atoms in the "cycloalkoxy group" is usually 3-40, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituents.
  • a cycloalkoxy group may have a substituent.
  • Cycloalkoxy groups include, for example, cyclohexyloxy groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
  • the number of carbon atoms in the "aryloxy group” is generally 6-60, preferably 6-40, more preferably 6-20, not including the number of carbon atoms in the substituents.
  • the aryloxy group may have a substituent. Examples of the aryloxy group include phenoxy group, naphthyloxy group, anthracenyloxy group, pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • a “heterocyclic group” means a group obtained by removing one or more hydrogen atoms directly bonded to atoms (carbon atoms or heteroatoms) constituting a ring from a heterocyclic compound.
  • an "aromatic heterocyclic group” which is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound, is preferred.
  • a group obtained by removing p hydrogen atoms (p represents an integer of 1 or more) directly bonded to atoms constituting a ring from a heterocyclic compound is also referred to as a "p-valent heterocyclic group".
  • a group obtained by removing p hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound is also referred to as a "p-valent aromatic heterocyclic group".
  • aromatic heterocyclic compound examples include compounds in which the heterocycle itself exhibits aromaticity, such as azole, thiophene, furan, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, and carbazole, and phenoxazine. , phenothiazine, benzopyran, and the like, compounds in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity.
  • the number of carbon atoms in the heterocyclic group is generally 1-60, preferably 2-40, more preferably 3-20, not including the number of carbon atoms in the substituent.
  • the number of heteroatoms in the heterocyclic group, not including the number of heteroatoms in the substituent is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. is.
  • Heterocyclic groups include, for example, monocyclic heterocyclic compounds such as furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, tetrazole, pyridine, diazabenzene and triazine, or Polycyclic heterocyclic compounds (e.g.
  • a heterocyclic group is a group in which a plurality of groups are bonded by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic heterocyclic compound or a polycyclic heterocyclic compound, good too.
  • the heterocyclic group may have a substituent.
  • Halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the "amino group” may have a substituent, preferably a substituted amino group (that is, a secondary amino group or a tertiary amino group, more preferably a tertiary amino group).
  • Preferred substituents on the amino group are alkyl groups, cycloalkyl groups, aryl groups and monovalent heterocyclic groups, and these groups may further have substituents.
  • the amino group has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which each is bonded.
  • Substituted amino groups include, for example, dialkylamino groups, dicycloalkylamino groups, diarylamino groups, and groups in which some or all of the hydrogen atoms in these groups are further substituted with substituents.
  • substituted amino groups include dimethylamino group, diethylamino group, diphenylamino group, bis(methylphenyl)amino group, bis(3,5-di-tert-butylphenyl)amino group, and hydrogen in these groups. Groups in which some or all of the atoms are further substituted with substituents are included.
  • alkenyl group may be either linear or branched.
  • the straight-chain alkenyl group usually has 2 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the branched alkenyl group is generally 3-30, preferably 4-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
  • the number of carbon atoms in the "cycloalkenyl group” is generally 3-30, preferably 4-20, more preferably 5-10, not including the number of carbon atoms in the substituents.
  • Alkenyl groups and cycloalkenyl groups may have a substituent.
  • alkenyl groups include vinyl group, 1-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • the cycloalkenyl group includes, for example, a cyclohexenyl group, a cyclohexadienyl group, a cyclooctatrienyl group, a norbornylenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents. .
  • alkynyl group may be either linear or branched.
  • the number of carbon atoms in the alkynyl group is usually 2-30, preferably 3-10, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the branched alkynyl group is generally 4-30, preferably 4-10, not including the carbon atoms of the substituents.
  • the number of carbon atoms in the "cycloalkynyl group” is usually 4-30, preferably 4-10, not including the carbon atoms of the substituents.
  • the alkynyl group and cycloalkynyl group may have a substituent.
  • alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.
  • Cycloalkynyl groups include, for example, cyclooctynyl groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
  • a “crosslinking group” is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, or the like.
  • the cross-linking group is preferably at least one cross-linking group selected from Group A of cross-linking groups (that is, at least one group selected from groups represented by formulas (XL-1) to (XL-19)).
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • *1 represents the binding position.
  • These bridging groups may have substituents, and when there are multiple substituents, they may be the same or different, and are bonded to each other to form a ring together with the atoms to which they are bonded. may ]
  • the "substituent” includes, for example, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, Alkenyl groups, cycloalkenyl groups, alkynyl groups and cycloalkynyl groups are included.
  • a substituent may be a bridging group.
  • when multiple substituents are present they may be the same or different.
  • they may bond with each other to form a ring together with the atoms to which they are bonded, but preferably do not form a ring.
  • the divalent group may be a group in which a plurality of these groups are bonded.
  • a divalent group may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • R 0 represents a hydrogen atom or a substituent.
  • R 0 includes, for example, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom and a cyano group.
  • a hydrogen atom preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • substituents may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state (hereinafter also referred to as “ ⁇ E ST ”) is calculated by the following method. is required.
  • the ground state of the compound is structurally optimized by density functional theory at the B3LYP level.
  • 6-31G* is used as a basis function.
  • ⁇ EST of the compound is calculated by time-dependent density functional theory at the B3LYP level.
  • LANL2DZ is used for that atom.
  • Gaussian09 is used as a quantum chemical calculation program.
  • composition of the present disclosure comprises at least one compound (hereinafter also referred to as "compound (A)”) selected from the group consisting of the metal complex represented by formula (1) and the polymer compound (A).
  • compound (B) at least one compound selected from the group consisting of low-molecular compound (B) and high-molecular compound (B), and represented by formula (H-1) and a polymer compound (hereinafter referred to as "first and at least two compounds selected from the group consisting of (hereinafter also referred to as "first compound”).
  • the composition of this embodiment is a composition containing compound (A), compound (B), and two or more first compounds.
  • composition of the present disclosure can be suitably used, for example, as a composition for light-emitting elements.
  • a light-emitting device containing the composition of the present disclosure (hereinafter also referred to as a “light-emitting device of the present disclosure”) has superior external quantum efficiency.
  • composition of the present disclosure may contain only one kind of compound (A) and compound (B), or may contain two or more kinds thereof.
  • the composition of the present disclosure may contain only two types of the first compound, or may contain three or more types of the first compound.
  • the total content of the compound (A), the compound (B), and the two or more first compounds is a composition (e.g., a composition for a light-emitting device, and the same applies hereinafter) ) as long as the function is exhibited.
  • the total content of compound (A), compound (B) and two or more first compounds is, for example, 1 to 100% by mass based on the total amount of the composition. It is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, and still more preferably 50 to 100% by mass, because the external quantum efficiency of the light-emitting device of the present disclosure is better. , particularly preferably 70 to 100% by mass, particularly preferably 90 to 100% by mass.
  • the content of compound (B) may be within a range in which the function of the composition is exhibited.
  • the content of compound (B) is when the total content of compound (A), compound (B) and two or more first compounds is 100 parts by mass.
  • the content of compound (A) may be within a range in which the function of the composition is exhibited.
  • the content of compound (A) is when the total content of compound (A), compound (B) and two or more first compounds is 100 parts by mass. , For example, 0.01 to 99 parts by mass, preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, because the external quantum efficiency of the light-emitting device of the present disclosure is more excellent. , more preferably 1 to 70 parts by mass, particularly preferably 5 to 50 parts by mass, particularly preferably 10 to 30 parts by mass.
  • the content of one type of first compound may be within a range in which the function of the composition is exhibited.
  • the content of one first compound is, when the total content of two or more first compounds is 100 parts by mass, for example, 0.1 to It is 100 parts by mass, and since the external quantum efficiency of the light-emitting device of the present disclosure is more excellent, it is preferably 1 to 99 parts by mass, more preferably 10 to 90 parts by mass, and still more preferably 20 to 80 parts by mass. 30 to 70 parts by mass, particularly preferably 40 to 60 parts by mass.
  • the total content of the two first compounds may be within a range in which the function of the composition is exhibited.
  • the total content of the two first compounds is, when the total content of the two or more first compounds is 100 parts by mass, for example, 1 to It is 100 parts by mass, and since the external quantum efficiency of the light-emitting device of the present disclosure is superior, it is preferably 10 to 100 parts by mass, more preferably 30 to 100 parts by mass, and even more preferably 50 to 100 parts by mass. 70 to 100 parts by mass, particularly preferably 90 to 100 parts by mass.
  • At least one of the two or more first compounds contains the structural unit represented by formula (X) and the formula ( It is preferably a polymer compound containing at least one structural unit selected from the group consisting of structural units represented by Y), and a combination of at least two of the two or more first compounds is A compound represented by the formula (H-1) and a high molecular weight compound containing at least one structural unit selected from the group consisting of a structural unit represented by the formula (X) and a structural unit represented by the formula (Y) A combination with a molecular compound is more preferred.
  • the two or more first compounds preferably interact physically, chemically or electrically. This interaction allows, for example, the emission properties, charge transport properties, or charge injection properties of the compositions of the present disclosure to be enhanced or adjusted, resulting in better external quantum efficiencies of the light emitting devices of the present disclosure. Further, in one embodiment of the composition of the present disclosure, the interaction between two or more first compounds and/or improvement of the film quality of a layer (e.g., light-emitting layer) containing the composition of the present disclosure As a result, the composition of the present disclosure has better emission properties, charge transport properties, and/or charge injection properties, and the light emitting device of the present disclosure has better external quantum efficiency.
  • a layer e.g., light-emitting layer
  • compound (A), compound (B), and the first compound preferably interact physically, chemically, or electrically. This interaction allows, for example, the emission properties, charge transport properties, or charge injection properties of the compositions of the present disclosure to be enhanced or adjusted, resulting in better external quantum efficiencies of the light emitting devices of the present disclosure.
  • the first compound, the compound (A), and the compound (B) electrically interact, and the first compound to the compound (
  • compound (B) By efficiently transferring electric energy to A) and further efficiently transferring electric energy from compound (A) to compound (B), compound (B) can be made to emit light more efficiently, and the present disclosure , the external quantum efficiency of the light-emitting device is better.
  • the first compound has hole injection properties, hole transport properties, electron injection properties, and electron More preferably, it has at least one function selected from transportability.
  • the compound (A) has a hole injection property, a hole transport property, an electron injection property, and an electron More preferably, it has at least one function selected from transportability.
  • the compound (B) more preferably has light-emitting properties, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • the lowest excited singlet state (S 1 ) possessed by the first compound is superior in external quantum efficiency of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S 1 ) possessed by .
  • the lowest excited singlet state (S 1 ) possessed by the first compound is superior in external quantum efficiency of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S 1 ) possessed by .
  • the lowest excited singlet state (S 1 ) possessed by the compound (A) is superior in external quantum efficiency of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S 1 ) possessed by .
  • the lowest excited triplet state (T 1 ) possessed by the first compound is superior in external quantum efficiency of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T 1 ) of .
  • the lowest excited triplet state (T 1 ) possessed by the first compound is superior in external quantum efficiency of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T 1 ) of .
  • the lowest excited triplet state (T 1 ) possessed by the compound (A) is superior in the external quantum efficiency of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T 1 ) of .
  • the compound (A) preferably exhibits solubility in a solvent capable of dissolving the compound (B), since the light-emitting device of the present disclosure can be produced by a wet method.
  • the first compound preferably exhibits solubility in a solvent capable of dissolving the compound (B) and the compound (A), since the light-emitting device of the present disclosure can be produced by a wet method. .
  • the first compound is preferably a host material, an assist dopant material, or a dopant material because the light-emitting device of the present disclosure has a better external quantum efficiency. It is more preferably a dopant material, and even more preferably a host material.
  • the compound (A) is preferably a host material, an assist dopant material, or a dopant material because the light-emitting device of the present disclosure has a higher external quantum efficiency. A dopant material is more preferred, and an assist dopant material is even more preferred.
  • the compound (B) is preferably a host material, an assist dopant material, or a dopant material because the light-emitting device of the present disclosure has a higher external quantum efficiency. Dopant materials are more preferred, and dopant materials are even more preferred.
  • the host material is preferably a material that physically, chemically or electrically interacts with the assisting dopant material. In one embodiment of the composition of the present disclosure, the host material is preferably a material that physically, chemically or electrically interacts with the dopant material. In one embodiment of the composition of the present disclosure, the assisting dopant material is preferably a material that physically, chemically or electrically interacts with the dopant material. In one embodiment of the composition of the present disclosure, it is preferred that the host material, assisting dopant material and dopant material interact physically, chemically or electrically. These interactions allow, for example, the emission properties, charge transport properties, or charge injection properties of the compositions of the present disclosure to be enhanced or adjusted, resulting in better external quantum efficiencies of the light emitting devices of the present disclosure.
  • the host material, the assisting dopant material, and the dopant material electrically interact to efficiently transfer electrical energy from the host material to the assisting dopant material, and further By efficiently transferring electrical energy from the assisting dopant material to the dopant material, the dopant material can emit light more efficiently, and the light emitting device of the present disclosure has a better external quantum efficiency.
  • the light-emitting device of the present disclosure has better external quantum efficiency, so the host material has hole-injecting, hole-transporting, electron-injecting and electron-transporting properties. It is more preferable to have at least one function selected from In view of the above, in one embodiment of the composition of the present disclosure, the assist dopant material has better hole-injecting, hole-transporting, electron-injecting and electron-transporting properties, so that the light-emitting device of the present disclosure has better external quantum efficiency. It is more preferable to have at least one function selected from nature.
  • the dopant material preferably has luminescence, because the external quantum efficiency of the light emitting device of the present disclosure is superior.
  • the lowest excited singlet state (S 1 ) of the host material has the lowest external quantum efficiency of the light-emitting device of the present disclosure.
  • An energy level higher than the excited singlet state (S 1 ) is preferred.
  • the lowest excited singlet state (S 1 ) possessed by the host material is the lowest excited singlet state possessed by the dopant material, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • An energy level higher than the singlet state (S 1 ) is preferred.
  • the lowest excited singlet state (S 1 ) of the assist dopant material is the lowest excited singlet state of the dopant material, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • An energy level higher than the excited singlet state (S 1 ) is preferred.
  • the lowest excited triplet state (T 1 ) of the host material is the lowest of the assist dopant material, since the light-emitting device of the present disclosure has a higher external quantum efficiency.
  • An energy level higher than the excited triplet state (T 1 ) is preferred.
  • the lowest excited triplet state (T 1 ) of the host material is the lowest excited triplet state of the dopant material, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • An energy level higher than the triplet state (T 1 ) is preferred.
  • the lowest excited triplet state (T 1 ) possessed by the assist dopant material is the lowest excited triplet state (T 1 ) possessed by the dopant material, since the external quantum efficiency of the light emitting device of the present disclosure is superior.
  • An energy level higher than the excited triplet state (T 1 ) is preferred.
  • the total content of the host material, the assist dopant material, and the dopant material may be within a range in which the composition functions.
  • the total content of the host material, the assisting dopant material and the dopant material may be, for example, 1 to 100% by mass based on the total amount of the composition. Since the external quantum efficiency of the device is better, it is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 50 to 100% by mass, and particularly preferably 70 to 100% by mass. and particularly preferably 90 to 100% by mass.
  • the content of the dopant material may be within a range in which the function of the composition is exhibited.
  • the content of the dopant material is, for example, 0.01 to 99 parts by mass when the total content of the host material, assist dopant material and dopant material is 100 parts by mass.
  • the external quantum efficiency of the light emitting device of the present disclosure is more excellent, preferably 0.01 to 90 parts by mass, more preferably 0.05 to 70 parts by mass, still more preferably 0.1 to 50 parts by mass parts, particularly preferably 0.5 to 30 parts by mass, particularly preferably 1 to 10 parts by mass.
  • the content of the assist dopant material may be within a range in which the function of the composition is exhibited.
  • the content of the assist dopant material is, for example, 0.01 to 99 parts by mass when the total content of the host material, the assist dopant material and the dopant material is 100 parts by mass. is preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, and even more preferably 1 to 70 parts by mass, because the external quantum efficiency of the light emitting device of the present disclosure is more excellent. , particularly preferably 5 to 50 parts by mass, particularly preferably 10 to 30 parts by mass.
  • the assist dopant material is preferably soluble in a solvent capable of dissolving the dopant material, since the light-emitting device of the present disclosure can be produced by a wet method.
  • the host material preferably exhibits solubility in a solvent capable of dissolving the assist dopant material and the dopant material, since the light-emitting device of the present disclosure can be produced by a wet method.
  • the compound (B) is at least one selected from the group consisting of low-molecular-weight compounds (B) and high-molecular-weight compounds (B).
  • the low - molecular-weight compound (B) is a condensed heterocyclic skeleton (b ) is a low-molecular-weight compound.
  • the condensed heterocyclic skeleton (b) contains a nitrogen atom
  • at least one of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) is a nitrogen that does not form a double bond. It is preferably an atom, and more preferably all of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) are nitrogen atoms that do not form double bonds.
  • the low-molecular-weight compound (B) is preferably a low-molecular-weight compound containing no transition metal element (that is, a low-molecular-weight compound composed only of typical elements).
  • the number of carbon atoms in the condensed heterocyclic skeleton (b) is generally 1 to 60, preferably 5 to 40, more preferably 10 to 25, not including the number of carbon atoms of substituents.
  • the number of heteroatoms in the condensed heterocyclic skeleton (b) is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, more preferably 2 to 10, not including the number of heteroatoms in the substituents. is 2 to 5, particularly preferably 2 or 3.
  • the number of boron atoms in the condensed heterocyclic skeleton (b) is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 3, not including the number of boron atoms in the substituents. is 1.
  • the total number of oxygen atoms, sulfur atoms, selenium atoms, sp3 carbon atoms and nitrogen atoms in the condensed heterocyclic skeleton (b) is usually 1 to 20, preferably 1 to 20, not including the number of substituent atoms. 10, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 2.
  • the condensed heterocyclic skeleton (b) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring, since the light-emitting device of the present disclosure has a superior external quantum efficiency. It is more preferable to contain a boron atom and a nitrogen atom in the ring, and it is even more preferable to contain a nitrogen atom that does not form a double bond with the boron atom in the ring.
  • the condensed heterocyclic skeleton (b) is preferably a 3- to 12-ring condensed heterocyclic skeleton, more preferably a 3- to 6-ring condensed heterocyclic skeleton, because the light-emitting device of the present disclosure has a superior external quantum efficiency. and more preferably a pentacyclic condensed heterocyclic skeleton.
  • the condensed heterocyclic skeleton (b) can also be said to be a compound having a heterocyclic group (b') containing the condensed heterocyclic skeleton (b).
  • the heterocyclic group (b') is a polycyclic heterocyclic group containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an sp3 carbon atom and a nitrogen atom in the ring. It may be a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a cyclic compound, and the group may have a substituent.
  • a polycyclic heterocyclic compound preferably consists of boron atoms, oxygen atoms, sulfur atoms and nitrogen atoms, because the external quantum efficiency of the light-emitting device of the present disclosure is superior.
  • a polycyclic heterocyclic compound containing in the ring at least one selected from the group, more preferably a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom in the ring More preferably, it is a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom not forming a double bond in the ring.
  • the polycyclic heterocyclic compound is preferably a 3- to 12-ring heterocyclic compound, more preferably a heterocyclic compound, since the light-emitting device of the present disclosure has superior external quantum efficiency. is a 3- to 6-ring heterocyclic compound, more preferably a pentacyclic heterocyclic compound.
  • heterocyclic group (b′) may have include halogen atoms, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryloxy groups, aryl groups, monovalent heterocyclic groups.
  • a cyclic group or a substituted amino group is preferable, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group, a cycloalkyl group, an aryl group, A monovalent heterocyclic group or a substituted amino group is more preferred, and an alkyl group, cycloalkyl group or aryl group is particularly preferred, and these groups may further have a substituent.
  • the aryl group in the substituent optionally possessed by the heterocyclic group (b′) is preferably a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon to an atom constituting the ring.
  • the group may have a substituent.
  • the monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound, A group in which one hydrogen atom directly bonded to a constituent atom is removed, and one hydrogen atom directly bonded to a ring-constituting atom is removed from a monocyclic, bicyclic or tricyclic heterocyclic compound.
  • pyridine diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, excluding one hydrogen atom directly bonded to a ring-constituting atom and particularly preferably a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene or triazine, and these groups may have a substituent.
  • the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group.
  • the group may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituents of the amino group are, respectively, the aryl group and the monovalent heterocyclic ring in the substituents that the heterocyclic group (b') may have It is the same as the example and preferred range of the group.
  • Substituents which the heterocyclic group (b′) may further have include halogen atoms, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl An oxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is preferred, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group or An aryl group is more preferred, and an alkyl group or a cycloalkyl group is particularly preferred.
  • These groups may further have a substituent, but preferably have no further substituent.
  • Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent that the heterocyclic group (b′) may further have are The same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the ring group (b') may have.
  • a “nitrogen atom that does not form a double bond” means a nitrogen atom that is bonded to three other atoms via single bonds. "Containing a nitrogen atom that does not form a double bond in the ring” means -N(-R N )- (wherein R N represents a hydrogen atom or a substituent) or the formula:
  • the low-molecular-weight compound (B) is preferably a thermally activated delayed fluorescence (TADF) compound, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • the heat-activated delayed fluorescence compound is a compound having heat-activated delayed fluorescence.
  • ⁇ EST of the low-molecular-weight compound (B) may be 2.0 eV or less, 1.5 eV or less, 1.0 eV or less, or 0.80 eV or less. However, it is preferably 0.60 eV or less, more preferably 0.55 eV or less, and even more preferably 0.50 eV or less, because the external quantum efficiency of the light-emitting device of the present disclosure is superior.
  • ⁇ EST of the low-molecular-weight compound (B) may be 0.001 eV or more, 0.01 eV or more, 0.10 eV or more, or 0.20 eV or more. may be 0.30 eV or more, or 0.40 eV or more.
  • the molecular weight of the low molecular weight compound (B) is preferably 1 ⁇ 10 2 to 5 ⁇ 10 3 , more preferably 2 ⁇ 10 2 to 3 ⁇ 10 3 , still more preferably 3 ⁇ 10 2 to 1.5. ⁇ 10 3 , particularly preferably 4 ⁇ 10 2 to 1 ⁇ 10 3 .
  • the low-molecular-weight compound (B) is a compound represented by formula (1-1), formula (1-2), or formula (1-3) because the light-emitting device of the present disclosure has superior external quantum efficiency. is preferred, a compound represented by formula (1-2) or formula (1-3) is more preferred, and a compound represented by formula (1-2) is even more preferred.
  • Ar 1 , Ar 2 and Ar 3 are preferably monocyclic or bicyclic to hexacyclic aromatic hydrocarbons, or monocyclic or A group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a bicyclic to hexacyclic heterocyclic compound, more preferably monocyclic, bicyclic or tricyclic A group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from an aromatic hydrocarbon or a monocyclic, bicyclic or tricyclic heterocyclic compound, more preferably , a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic aromatic hydrocarbon or a monocyclic heterocyclic compound, particularly preferably benzene, pyridine or diazabenzene is a group obtained by removing one or more hydrogen atoms directly bonded to ring-constituting atoms from benzene, and particularly preferably
  • Y 1 is preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group, more preferably an oxygen atom, since the light-emitting device of the present disclosure has a superior external quantum efficiency.
  • a sulfur atom or a group represented by -N(Ry)-, more preferably a group represented by -N(Ry)-, and these groups may have a substituent.
  • Y 2 and Y 3 are preferably a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, -B A group represented by (Ry)-, an alkylene group or a cycloalkylene group, more preferably a single bond, an oxygen atom, a sulfur atom, a group represented by -N(Ry)-, or -B(Ry)- A group or an alkylene group represented by, more preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group, particularly preferably an oxygen atom, a sulfur atom or -N It is a group represented by (Ry)-, particularly preferably a group represented by -N(Ry)-, and these groups may have a substituent.
  • the arylene group for Y 2 and Y 3 is preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon. and more preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene from which two hydrogen atoms directly bonded to carbon atoms constituting a ring are removed; particularly preferably, benzene, naphthalene or fluorene constitutes a ring; It is a group excluding two hydrogen atoms directly bonded to a carbon atom, particularly preferably a phenylene group, and these groups may have a substituent.
  • the divalent heterocyclic group for Y 2 and Y 3 is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound directly bonded to a ring-constituting atom (preferably a carbon atom).
  • a group with two atoms removed more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-
  • all of Y 1 , Y 2 and Y 3 are preferably an oxygen atom, a sulfur atom or a group represented by -N(Ry)-, and Y All of 1 , Y 2 and Y 3 are more preferably groups represented by -N(Ry)-.
  • Examples and preferred ranges of substituents that Y 1 , Y 2 and Y 3 may have are the same as examples and preferred ranges of substituents that the heterocyclic group (b′) may have.
  • Ry is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group; A group may have a substituent.
  • Examples and preferred ranges of the aryl group and monovalent heterocyclic group in Ry are respectively examples and preferred examples of the aryl group and monovalent heterocyclic group in the substituent that the heterocyclic group (b′) may have Same as range.
  • Examples and preferred ranges of substituents that Ry may have are the same as examples and preferred ranges of substituents that the heterocyclic group (b') may have.
  • Y 1 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • the divalent group is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent hetero a cyclic group, a group represented by -N(R 0 )-, a group represented by -B(R 0 )-, a group represented by -O-, a group represented by -S- or -Se- and more preferably an alkylene group, a cycloalkylene group, a group represented by -N(R 0 )-, a group represented by -B(R 0 )-, and a group represented by -O- a group represented by -S- or a group represented by -Se-, more preferably an alkylene group, a group represented by -N(R 0 )-, a group represented by -B(R 0 )-
  • examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in the divalent group are They are the same as the examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group for Y2 and Y3 , respectively.
  • examples and preferred ranges of substituents that the divalent group may have include Y 2 and Y It is the same as the examples and preferred range of the substituent that 3 may have.
  • examples and preferred ranges of R 0 in the divalent group are the same as examples and preferred ranges of Ry .
  • Y 1 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • Examples and preferred ranges of the divalent group when Y 1 and Ar 2 are bonded via a divalent group to form a ring are Y 1 and Ar 1 via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Y 2 and Ar 1 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • Examples and preferred ranges of the divalent group when Y 2 and Ar 1 are bonded via a divalent group to form a ring are Y 1 and Ar 1 via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Y 2 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • Examples and preferred ranges of the divalent group when Y 2 and Ar 3 are bonded via a divalent group to form a ring are Y 1 and Ar 1 via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Y 3 and Ar 2 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • Examples and preferred ranges of the divalent group when Y 3 and Ar 2 are bonded via a divalent group to form a ring are Y 1 and Ar 1 via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Y 3 and Ar 3 may be directly bonded or bonded via a divalent group to form a ring. preferably not.
  • Examples and preferred ranges of the divalent group when Y 3 and Ar 3 are bonded via a divalent group to form a ring are Y 1 and Ar 1 via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Examples of the low-molecular-weight compound (B) include compounds represented by the following formula and compound B1 described later.
  • Z 1 represents an oxygen atom or a sulfur atom. When multiple Z 1 are present, they may be the same or different.
  • the maximum peak wavelength of the emission spectrum of the low-molecular-weight compound (B) at 25° C. is preferably 380 nm or longer, more preferably 400 nm or longer, even more preferably 420 nm or longer, and particularly preferably 440 nm or longer.
  • the maximum peak wavelength of the emission spectrum of the low-molecular-weight compound (B) at 25° C. is preferably 750 nm or less, more preferably 620 nm or less, even more preferably 570 nm or less, particularly preferably 495 nm or less. It is preferably 480 nm or less.
  • the maximum peak wavelength of the emission spectrum of the compound at room temperature can be determined by dissolving the compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, etc., and preparing a dilute solution (1 ⁇ 10 ⁇ 6 mass % to 1 ⁇ 10 ⁇ 3 mass %). %), which can be evaluated by measuring the PL spectrum of the dilute solution at room temperature.
  • Xylene is preferred as the organic solvent for dissolving the compound.
  • the polymer compound (B) is a polymer compound containing a structural unit (hereinafter also referred to as “structural unit (B)”) having a group obtained by removing one or more hydrogen atoms from the low molecular weight compound (B).
  • the structural unit (B) is preferably a structural unit having a group obtained by removing 1 or more and 5 or less hydrogen atoms from the low-molecular-weight compound (B), and more preferably, because the synthesis of the polymer compound (B) is easy.
  • the structural unit (B) is preferably represented by the formula (BP-1) or the formula (BP- 2) or a structural unit represented by formula (BP-3), more preferably a structural unit represented by formula (BP-1) or formula (BP-2).
  • MBP1 represents a group obtained by removing one hydrogen atom from the low-molecular-weight compound (B).
  • MBP2 represents a group obtained by removing two hydrogen atoms from the low-molecular-weight compound (B).
  • MBP3 represents a group obtained by removing three hydrogen atoms from the low-molecular-weight compound (B).
  • L BP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R BP1 )-, an oxygen atom or a sulfur atom, and these groups are It may have a substituent.
  • RBP1 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.
  • substituents they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • LBP1 When multiple LBP1 are present, they may be the same or different.
  • nBP1 represents an integer of 0 or more and 10 or less.
  • Ar BP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
  • L BP1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an alkylene group or an arylene group, still more preferably an arylene group, these groups may have a substituent.
  • Examples and preferred ranges of the arylene group and divalent heterocyclic group in LBP1 are the same as those of the arylene group and divalent heterocyclic group in Ar Y1 described below.
  • the alkylene group in LBP1 is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
  • Examples and preferred ranges of R BP1 are the same as examples and preferred ranges of R X1 to R X3 described later.
  • nBP1 is preferably an integer of 0-5, preferably an integer of 0-3, more preferably 0 or 1, still more preferably 0.
  • the hydrocarbon group for Ar BP1 includes an optionally substituted aromatic hydrocarbon group and an optionally substituted aliphatic hydrocarbon group.
  • the hydrocarbon group in Ar BP1 includes groups in which multiple of these groups are bonded.
  • the aliphatic hydrocarbon group includes a group obtained by removing one hydrogen atom nBP from an alkylene group or a cycloalkylene group, preferably a group obtained by removing one hydrogen atom nBP from an alkylene group, These groups may have a substituent. Examples and preferred range of this alkylene group include the examples and preferred range of the alkylene group in L H1 described later.
  • the aromatic hydrocarbon group includes a group obtained by removing one hydrogen atom n BP from an arylene group, and this group may have a substituent.
  • Examples and preferred ranges of the arylene group include the examples and preferred ranges of the arylene group in Ar Y1 described later.
  • the heterocyclic group for Ar BP1 includes a group obtained by removing one hydrogen atom n BP from a divalent heterocyclic group, and this group may have a substituent.
  • Examples and preferred ranges of the divalent heterocyclic group include the examples and preferred ranges of the divalent heterocyclic group in Ar Y1 described later.
  • Examples and preferred examples of substituents that L BP1 and Ar 2 BP1 may have are the same as examples and preferred ranges of substituents that the group represented by Ar Y1 may have, which will be described later.
  • Examples of structural units (B) include structural units represented by the following formula.
  • RTS is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may further have a substituent. Multiple RTSs may be the same or different.
  • Examples and preferred ranges of the aryl group , monovalent heterocyclic group and substituted amino group in R TS are, respectively, the aryl group, monovalent heterocyclic It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.
  • Examples and preferred ranges of substituents that R TS may have include examples and preferred ranges of substituents that the group represented by Ar Y1 described later may further have. are the same.
  • the content of the structural unit (B) contained in the polymer compound (B) may be within a range where the function of the polymer compound (B) is achieved.
  • the content of the structural unit (B) contained in the polymer compound (B) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (B). , preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, because the external quantum efficiency of the light-emitting device of the present disclosure is better. , particularly preferably 0.5 to 30 mol %, particularly preferably 1 to 10 mol %. Only one type of structural unit (B) may be contained in the polymer compound (B), or two or more types thereof may be contained.
  • the polymer compound (B) is superior in external quantum efficiency of the light-emitting device of the present disclosure, it is a group consisting of a structural unit represented by the formula (X) described later and a structural unit represented by the formula (Y) described later. It is preferable to further contain at least one structural unit selected from the above. That is, the polymer compound (B) contains at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later; It is preferably a polymer compound containing the unit (B).
  • the polymer compound (B) comprises at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later, and a structural unit ( B), the structural unit (B) is preferably different from the structural unit represented by the formula (X) described later and the structural unit represented by the formula (Y) described later.
  • the polymer compound (B) preferably further contains a structural unit represented by the below-described formula (Y), since the light-emitting device of the present disclosure has a more excellent external quantum efficiency. Since the polymer compound (B) has excellent hole-transport properties and the external quantum efficiency of the light-emitting device of the present disclosure is superior, the polymer compound (B) is a structural unit represented by the formula (X) described later.
  • the polymer compound (B) has excellent hole-transport properties and the light-emitting device of the present disclosure has a further excellent external quantum efficiency
  • the polymer compound (B) is a structural unit represented by the formula (X) described below. and preferably further contains a structural unit represented by formula (Y) described later.
  • the content of the structural unit represented by the below-described formula (X) is such that the polymer compound (B) functions as It can be any range as long as it can be played.
  • the content of the structural unit represented by the below-described formula (X) is the constitution contained in the polymer compound (B).
  • the hole transport property of the polymer compound (B) is excellent, and the external quantum efficiency of the light emitting device of the present disclosure is Since it is more excellent, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0.5 to 30 mol %, particularly preferably 1 to 10 mol %.
  • the structural unit represented by formula (X) may be contained in the polymer compound (B) singly or in combination of two or more.
  • the content of the structural unit represented by the formula (Y) is within the range in which the polymer compound (B) functions. If it is When the polymer compound (B) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is the total of the structural units contained in the polymer compound (B).
  • the content it is, for example, 1 to 99.99 mol%, and since the external quantum efficiency of the light-emitting device of the present disclosure is superior, it is preferably 10 to 99.95 mol%, more preferably 30 to 99 0.9 mol %, more preferably 50 to 99.8 mol %, particularly preferably 70 to 99.5 mol %, particularly preferably 90 to 99 mol %.
  • the structural unit represented by formula (Y) may be contained in the polymer compound (B) singly or in combination of two or more.
  • the polymer compound (B) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (B), it is represented by the formula (X)
  • the total content of the structural unit represented by the formula (Y) and the structural unit (B) may be within a range in which the function of the polymer compound (B) can be exhibited.
  • the polymer compound (B) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (B), it is represented by the formula (X)
  • the total content of the structural unit represented by the formula (Y) and the structural unit (B) is, for example, 1 It is preferably 10 to 100 mol%, more preferably 10 to 100 mol%, because the hole transport property of the polymer compound (B) is excellent and the external quantum efficiency of the light emitting device of the present disclosure is more excellent. It is 30 to 100 mol %, more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.
  • polymer compound (B) examples include polymer compounds BP-1 to BP-4.
  • “other” means a structural unit other than the structural unit (B), the structural unit represented by formula (X), and the structural unit represented by formula (Y).
  • p b , q b , r b and s b represent the molar ratio (mol %) of each structural unit.
  • p b +q b +r b +s b 100 and 70 ⁇ p b +q b +r b ⁇ 100.
  • the polymer compound (B) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other modes. It is preferably a copolymer obtained by copolymerizing monomers.
  • the example and preferred range of the polystyrene-equivalent number average molecular weight of the polymer compound (B) are the same as the example and preferred range of the polystyrene-equivalent number average molecular weight of the first polymer compound described below.
  • the example and preferred range of the polystyrene-equivalent weight average molecular weight of the polymer compound (B) are the same as the example and preferred range of the polystyrene-equivalent weight average molecular weight of the first polymer compound described below.
  • the polymer compound (B) can be produced by the same method as the method for producing the first polymer compound described below.
  • the compound (A) is at least one selected from the group consisting of the metal complex represented by Formula (1) and the polymer compound (A).
  • the metal complex represented by Formula (1) is preferably a low-molecular-weight compound.
  • the molecular weight of the metal complex represented by formula (1) is preferably 3 ⁇ 10 2 to 1 ⁇ 10 4 , more preferably 4 ⁇ 10 2 to 7 ⁇ 10 3 , still more preferably 5 ⁇ 10 2 to 7 ⁇ 10 3 .
  • 10 2 to 5 ⁇ 10 3 particularly preferably 6 ⁇ 10 2 to 3 ⁇ 10 3 , particularly preferably 7 ⁇ 10 2 to 2 ⁇ 10 3 .
  • M is preferably an iridium atom or a platinum atom, more preferably an iridium atom, since the light-emitting device of the present disclosure has a better external quantum efficiency.
  • n1 is preferably 2 or 3, more preferably 3.
  • n1 is preferably 2 when M is a palladium atom or a platinum atom.
  • At least one of E 1 and E 2 is preferably a carbon atom, more preferably E 1 and E 2 are carbon atoms.
  • E 1 and E 2 are preferably the same because the metal complex represented by formula (1) can be easily synthesized. Further, since the metal complex represented by formula (1) can be easily synthesized, when there are a plurality of E 1 's, it is preferable that at least two of the plurality of E 1 's are the same. are all the same. In addition, since the metal complex represented by formula (1) can be easily synthesized, when there are a plurality of E 2 s, it is preferable that at least two of the plurality of E 2s are the same. are all the same.
  • the number of carbon atoms in the aromatic heterocyclic ring in ring L 1 is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 10, not including the number of carbon atoms in substituents. , particularly preferably 1 to 5, particularly preferably 1 to 3.
  • the number of heteroatoms in the aromatic heterocyclic ring in ring L 1 is preferably 1 to 30, more preferably 1 to 10, still more preferably 1 to 5, not including the number of heteroatoms in the substituents. , particularly preferably 1 to 3.
  • Examples of the ring L 1 include aromatic heterocycles containing one or more nitrogen atoms in the ring among the aromatic heterocycles exemplified in the section of the heterocyclic group described above, and the aromatic heterocycle may have a substituent.
  • the ring L 1 is preferably an aromatic heterocyclic ring containing a 5-membered ring or an aromatic heterocyclic ring containing a 6-membered ring, more preferably , an aromatic heterocycle containing a 5-membered ring containing 2 or more and 4 or less nitrogen atoms in the ring, or an aromatic heterocycle containing a 6-membered ring containing 1 or more and 4 or less nitrogen atoms in the ring and more preferably an aromatic heterocyclic ring containing a 5-membered ring containing 2 or 3 nitrogen atoms in the ring, or an aromatic containing a 6-membered ring containing 1 or 2 nitrogen atoms in the ring It is a heterocyclic ring, particularly preferably an aromatic heterocyclic ring containing a 5-membered ring containing 2 or 3 nitrogen atoms in the ring, and these rings may have a substituent.
  • Ring L 1 is a 6-membered aromatic heterocycle
  • E 1 is preferably a carbon atom.
  • Ring L 1 is preferably a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring, more preferably a pyridine ring or a diazabenzene ring, since the light-emitting device of the present disclosure has a superior external quantum efficiency.
  • an azanaphthalene ring, a diazanaphthalene ring, a diazole ring or a triazole ring more preferably a pyridine ring, an azanaphthalene ring, a diazole ring or a triazole ring, particularly preferably a diazole ring or a triazole ring, especially A triazole ring is preferred, and these rings may have a substituent. Since the metal complex represented by formula (1) can be easily synthesized, when a plurality of ring L 1 are present, it is preferable that at least two of the plurality of ring L 1 are the same. 1 are more preferably the same.
  • the number of carbon atoms in the aromatic hydrocarbon ring in ring L 2 is preferably 6 to 60, more preferably 6 to 40, still more preferably 6 to 20, not including the number of carbon atoms in substituents.
  • Examples of the aromatic hydrocarbon ring in the ring L 2 include the aromatic hydrocarbon rings exemplified in the section of the aromatic hydrocarbon group above, preferably an aromatic hydrocarbon ring containing a 5- or 6-membered ring. It is a hydrogen ring, and these aromatic hydrocarbon rings may have a substituent.
  • the aromatic hydrocarbon ring in the ring L 2 is preferably a monocyclic or bicyclic a cyclic or tricyclic aromatic hydrocarbon ring (preferably an aromatic hydrocarbon ring containing a 5- or 6-membered ring), more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring or a dihydrophenanthrene It is a ring, more preferably a benzene ring or a fluorene ring, particularly preferably a benzene ring, and these rings may have a substituent.
  • the number of carbon atoms in the aromatic heterocyclic ring in ring L 2 is preferably 1 to 60, more preferably 2 to 40, still more preferably 3 to 20, not including the number of carbon atoms in substituents. .
  • the number of heteroatoms in the aromatic heterocyclic ring in ring L 2 is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, not including the number of heteroatoms in substituents.
  • Examples of the aromatic heterocyclic ring in the ring L 2 include the aromatic heterocyclic rings exemplified in the section of the heterocyclic group described above, preferably an aromatic heterocyclic ring containing a 5- or 6-membered ring, These aromatic heterocycles may have a substituent.
  • the aromatic heterocyclic ring in the ring L 2 is preferably monocyclic, bicyclic or tricyclic, as exemplified in the section of the heterocyclic group above, because the external quantum efficiency of the light-emitting device of the present disclosure is superior.
  • cyclic aromatic heterocycle (preferably aromatic heterocycle containing 5- or 6-membered ring), more preferably pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, indole ring, benzofuran ring, benzothiophene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring or dibenzothiophene ring, more preferably pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring;
  • a pyridine ring or a diazabenzene ring is particularly preferred, and these rings may have a substituent.
  • Ring L 2 is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring (preferably a 5- or 6-membered ring (an aromatic hydrocarbon ring containing is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, more preferably a benzene ring, a pyridine ring or a diazabenzene ring, particularly preferably a benzene ring, These rings may have a substituent. Since the metal complex represented by formula (1) can be easily synthesized, when there are a plurality of ring L 2 , it is preferable that at least two of the plurality of ring L 2 are the same. 2 are more preferably the same.
  • the ring L 1 is an aromatic heterocyclic ring containing a 5-membered ring (preferably a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring) or an aromatic heterocycle containing a 6-membered ring (preferably a monocyclic, bicyclic or tricyclic aromatic heterocycle), and ring L 2 is an aromatic containing a 5- or 6-membered ring aromatic hydrocarbon ring (preferably monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring), or an aromatic heterocyclic ring containing a 5- or 6-membered ring (preferably monocyclic, bicyclic or tricyclic aromatic heterocycle), ring L 1 is pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, diazole ring or triazole ring, and ring L 2 is more preferably a benzene ring, fluorene ring,
  • ring L 2 is more preferably a benzene ring, pyridine ring or diazabenzene ring
  • ring L 1 is a pyridine ring, azanaphthalene ring, diazole ring or triazole ring
  • ring L 2 is particularly preferably a benzene ring, particularly preferably ring L 1 is a diazole ring or triazole ring
  • ring L 2 is a benzene ring
  • ring L 1 is a triazole ring
  • Ring L2 is particularly preferably a benzene ring, and these rings may have a substituent.
  • Preferred substituents that the ring L 1 and ring L 2 may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group and an aryl group.
  • an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups are further substituted (hereinafter referred to as "secondary substituted Also referred to as "group").
  • At least one of ring L 1 and ring L 2 preferably has a primary substituent because the external quantum efficiency of the light-emitting device of the present disclosure is better.
  • a plurality of ring L 1 and ring L 2 are present
  • At least one ring out of ring L 1 and ring L 2 may have a primary substituent, but since the light-emitting device of the present disclosure has superior external quantum efficiency, multiple ring L 1 and ring L
  • At least two of 2 preferably have a primary substituent, and more preferably at least three of the plurality of ring L 1 and ring L 2 have a primary substituent.
  • the present since the external quantum efficiency of the disclosed light-emitting device is superior, at least two of the multiple rings L 1 have a primary substituent, or at least two of the multiple rings L 2 have a primary substituent. More preferably, all of the plurality of ring L 1 have a primary substituent, or all of the plurality of ring L 2 have a primary substituent, and all of the plurality of ring L 1 more preferably has a primary substituent.
  • the metal complex represented by formula (1) when at least one of ring L 1 and ring L 2 has a primary substituent, at least one of ring L 1 and ring L 2 has a primary substituent
  • the number is usually 1 to 10, and preferably 1 to 5 because the metal complex represented by formula (1) can be easily synthesized and the external quantum efficiency of the light emitting device of the present disclosure is superior. , more preferably 1 to 3, still more preferably 1 or 2.
  • ring L 1 and ring L 2 when at least one of ring L 1 and ring L 2 has a primary substituent and M is a rhodium atom or an iridium atom, ring L 1 and ring
  • the total number of primary substituents that L 2 has is usually 1 to 30, the metal complex represented by formula (1) can be easily synthesized, and the external quantum efficiency of the light emitting device of the present disclosure is more excellent, the number is preferably 1 to 18, more preferably 2 to 12, still more preferably 3 to 6.
  • the metal complex represented by formula (1) when at least one of ring L 1 and ring L 2 has a primary substituent and M is a palladium atom or a platinum atom, ring L 1 and ring
  • the total number of primary substituents that L 2 has is usually 1 to 20, the metal complex represented by formula (1) can be easily synthesized, and the external quantum efficiency of the light emitting device of the present disclosure is more excellent, the number is preferably 1 to 12, more preferably 1 to 8, even more preferably 2 to 4.
  • the aryl group in the primary substituent is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, A phenyl group, a naphthyl group or a fluorenyl group is more preferred, and a phenyl group is even more preferred, and these groups may have a substituent.
  • the monovalent heterocyclic group in the primary substituent preferably, one hydrogen atom directly bonded to a carbon atom or heteroatom constituting a ring from a monocyclic, bicyclic or tricyclic heterocyclic compound and more preferably a pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring directly to a carbon atom or heteroatom constituting the ring.
  • a group in which one hydrogen atom is removed more preferably a group in which one hydrogen atom directly bonded to a ring-constituting carbon atom is removed from a pyridine ring, a diazabenzene ring or a triazine ring, and these groups may have a substituent.
  • the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. . Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the same as those of the aryl group and monovalent heterocyclic group in the primary substituent.
  • Examples and preferred ranges of the secondary substituents are the same as the examples and preferred ranges of the primary substituents.
  • the secondary substituent may further have a substituent (hereinafter also referred to as "tertiary substituent").
  • Examples and preferred ranges of tertiary substituents are the same as examples and preferred ranges of primary substituents.
  • the tertiary substituent may further have a substituent (hereinafter also referred to as "quaternary substituent").
  • the quaternary substituent (substituent that the tertiary substituent may further have) is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent a cyclic group, a substituted amino group or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group or An aryl group, particularly preferably an alkyl group or a cycloalkyl group, which may further have a substituent, because the metal complex represented by the formula (1) can be easily synthesized.
  • aryl group, monovalent heterocyclic group and substituted amino group in the secondary substituent, tertiary substituent and quaternary substituent are, respectively, the aryl group in the primary substituent, the monovalent heterocyclic group and It is the same as the example and preferred range of the substituted amino group.
  • anionic bidentate ligand examples include ligands represented by the following formulae. 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 .
  • Examples of the metal complex represented by formula (1) include the metal complexes shown below.
  • the polymer compound (A) is a polymer containing a structural unit (hereinafter also referred to as "structural unit (A)") having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (1). is a compound.
  • Structural unit (A) is preferably a structural unit having a group obtained by removing 1 or more and 5 or less hydrogen atoms from the metal complex represented by formula (1), since synthesis of polymer compound (A) is easy.
  • the structural unit (A) is preferably represented by the formula (AP-1) or the formula (AP- 2) or a structural unit represented by formula (AP-3), more preferably a structural unit represented by formula (AP-1) or formula (AP-2), still more preferably a structural unit represented by formula ( It is a structural unit represented by AP-1).
  • MAP1 represents a group obtained by removing one hydrogen atom from the metal complex represented by formula (1).
  • MAP2 represents a group obtained by removing two hydrogen atoms from the metal complex represented by formula (1).
  • MAP3 represents a group obtained by removing three hydrogen atoms from the metal complex represented by formula (1).
  • L AP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R AP1 )-, an oxygen atom or a sulfur atom, and these groups are It may have a substituent.
  • RAP1 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.
  • substituents they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • LAP1 When multiple LAP1 are present, they may be the same or different.
  • n AP1 represents an integer of 0 or more and 10 or less.
  • Ar AP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
  • L AP1 are the same as the examples and preferred ranges of L BP1 .
  • RAP1 are the same as the examples and preferred ranges of RBP1 .
  • nAP1 are the same as the examples and preferred ranges of nBP1 .
  • Ar AP1 are the same as the examples and preferred ranges of Ar BP1 .
  • Examples of structural units (A) include structural units represented by the following formula.
  • RA represents a hydrogen atom or a primary substituent. When multiple RAs are present, they may be the same or different.
  • the content of the structural unit (A) contained in the polymer compound (A) may be within a range in which the function of the polymer compound (A) is exhibited.
  • the content of the structural unit (A) contained in the polymer compound (A) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (A). , preferably 0.1 to 99 mol%, more preferably 0.5 to 90 mol%, still more preferably 1 to 70 mol%, because the external quantum efficiency of the light-emitting device of the present disclosure is better. , particularly preferably 5 to 50 mol %, particularly preferably 10 to 30 mol %.
  • 1 type of structural units (A) may be contained in the polymer compound (A), and 2 or more types may be contained.
  • the polymer compound (A) is superior in external quantum efficiency of the light-emitting device of the present disclosure, it is a group consisting of a structural unit represented by the formula (X) described later and a structural unit represented by the formula (Y) described later. It is preferable to further contain at least one structural unit selected from the above. That is, the polymer compound (A) includes at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later; It is preferably a polymer compound containing the unit (A).
  • the polymer compound (A) comprises at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later, and a structural unit ( A), the structural unit (A) is preferably different from the structural unit represented by the formula (X) described later and the structural unit represented by the formula (Y) described later.
  • the polymer compound (A) preferably further contains a structural unit represented by the below-described formula (Y) because the light-emitting device of the present disclosure has a more excellent external quantum efficiency.
  • the polymer compound (A) Since the polymer compound (A) has excellent hole-transport properties and the external quantum efficiency of the light-emitting device of the present disclosure is superior, the polymer compound (A) is a structural unit represented by the below-described formula (X). It is preferable to further include Since the polymer compound (A) has excellent hole-transport properties and the external quantum efficiency of the light-emitting device of the present disclosure is superior, the polymer compound (A) is a structural unit represented by the below-described formula (X). and preferably further contains a structural unit represented by formula (Y) described later.
  • the content of the structural unit represented by the below-described formula (X) is such that the polymer compound (A) functions as It is acceptable as long as it is within the range where it can be played.
  • the content of the structural unit represented by the formula (X) described below is the constitution contained in the polymer compound (A).
  • the hole transport property of the polymer compound (B) is excellent, and the external quantum efficiency of the light emitting device of the present disclosure is Since it is more excellent, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0.5 to 30 mol %, particularly preferably 1 to 10 mol %.
  • the structural unit represented by formula (X) may be contained in the polymer compound (A) singly or in combination of two or more.
  • the content of the structural unit represented by the formula (Y) is within the range in which the polymer compound (A) functions. If it is When the polymer compound (A) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is the total of the structural units contained in the polymer compound (A).
  • the content for example, it is 0.1 to 99.99 mol%, and since the external quantum efficiency of the light emitting device of the present disclosure is superior, it is preferably 1 to 99.9 mol%, more preferably 10 99.5 mol %, more preferably 30 to 99 mol %, particularly preferably 50 to 95 mol %, particularly preferably 70 to 90 mol %.
  • the structural unit represented by formula (Y) may be contained in the polymer compound (A) singly or in combination of two or more.
  • the polymer compound (A) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (A), it is represented by the formula (X)
  • the total content of the structural unit represented by the formula (Y), the structural unit represented by the formula (Y), and the structural unit (A) may be within a range in which the function of the polymer compound (A) can be exhibited.
  • the polymer compound (A) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (A), it is represented by the formula (X)
  • the total content of the structural unit represented by the formula (Y) and the structural unit (A) is, for example, 1 It is preferably 10 to 100 mol%, more preferably 10 to 100 mol%, because the hole transport property of the polymer compound (A) is excellent and the external quantum efficiency of the light emitting device of the present disclosure is more excellent. It is 30 to 100 mol %, more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.
  • polymer compound (A) examples include polymer compounds AP-1 to AP-4.
  • “other” means a structural unit other than the structural unit (A), the structural unit represented by formula (X), and the structural unit represented by formula (Y).
  • p a , q a , r a and sa represent the molar ratio (mol %) of each structural unit.
  • p a +q a + ra +s a 100 and 70 ⁇ pa +q a + ra ⁇ 100.
  • the polymer compound (A) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may be in other forms. It is preferably a copolymer obtained by copolymerizing monomers.
  • the example and preferred range of the polystyrene-equivalent number average molecular weight of the polymer compound (A) are the same as the example and preferred range of the polystyrene-equivalent number average molecular weight of the first polymer compound described below.
  • the example and preferred range of the polystyrene-equivalent weight average molecular weight of the polymer compound (A) are the same as the example and preferred range of the polystyrene-equivalent weight average molecular weight of the first polymer compound described below.
  • the polymer compound (A) can be produced by the same method as the method for producing the first polymer compound described below.
  • the first compound is at least two selected from the group consisting of the compound represented by formula (H-1) and the first polymer compound.
  • At least one of the two or more first compounds is preferably the first polymer compound.
  • a combination of at least two of the above first compounds is a combination of two first polymer compounds, or a combination of a first polymer compound and a compound represented by Formula (H-1).
  • a combination is more preferable, and at least two of the two or more first compounds are a combination of the first polymer compound and the compound represented by formula (H-1). is more preferred.
  • the total content of the first polymer compound and the compound represented by formula (H-1) may be within a range in which the composition functions.
  • the total content of the first polymer compound and the compound represented by formula (H-1) is 100 parts by mass of the total content of two or more first compounds.
  • it is, for example, it is 1 to 100 parts by mass, and the external quantum efficiency of the light emitting device of the present disclosure is more excellent, so it is preferably 10 to 100 parts by mass, more preferably 30 to 100 parts by mass, and still more preferably. is 50 to 100 parts by weight, particularly preferably 70 to 100 parts by weight, and most preferably 90 to 100 parts by weight.
  • the content of the first polymer compound is It is acceptable as long as it is within the range of In the composition of the present disclosure, when at least one of the two or more first compounds is the first polymer compound, the content of the first polymer compound is When the total content of the compounds is 100 parts by mass, for example, it is 0.1 to 100 parts by mass, and the external quantum efficiency of the light emitting device of the present disclosure is more excellent, so it is preferably 1 to 99 parts by mass, More preferably 10 to 90 parts by mass, still more preferably 20 to 80 parts by mass, particularly preferably 30 to 70 parts by mass, particularly preferably 40 to 60 parts by mass.
  • the amount when at least one of the two or more first compounds is a compound represented by formula (H-1), containing the compound represented by formula (H-1) The amount may be within a range in which the function of the composition is exhibited. In the composition of the present disclosure, when at least one of the two or more first compounds is a compound represented by formula (H-1), containing the compound represented by formula (H-1) The amount is, for example, 0.1 to 100 parts by mass when the total content of the two or more first compounds is 100 parts by mass. Preferably 1 to 99 parts by mass, more preferably 10 to 90 parts by mass, still more preferably 20 to 80 parts by mass, particularly preferably 30 to 70 parts by mass, particularly preferably 40 to 60 parts by mass Department.
  • the compound represented by formula (H-1) is preferably a low-molecular-weight compound. Since the external quantum efficiency of the light-emitting device of the present disclosure is superior, the molecular weight of the compound represented by formula (H-1) is preferably 1 ⁇ 10 2 to 5 ⁇ 10 3 , more preferably 2 ⁇ 10 2 . 3 ⁇ 10 3 to 3 ⁇ 10 3 , more preferably 3 ⁇ 10 2 to 1.5 ⁇ 10 3 , particularly preferably 4 ⁇ 10 2 to 1 ⁇ 10 3 .
  • the compound represented by formula (H-1) is preferably a compound different from compound (B), and more preferably a compound that does not have a condensed heterocyclic skeleton (b).
  • the aryl groups in Ar H1 and Ar H2 are preferably monocyclic or 2- to 7-ring aromatic hydrocarbons directly bonded to atoms constituting a ring, because the light-emitting device of the present disclosure has superior external quantum efficiency.
  • the aryl groups in Ar H1 and Ar H2 are preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene, benzofluorene, dibenzo a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from anthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene or benzofluoranthene, more preferably benzene, naphthalene, anthracene, phenanthrene, A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene or benzofluorene, more preferably benzene, naphthalene, anthracene,
  • the monovalent heterocyclic group in Ar H1 and Ar H2 is a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from a heterocyclic compound that does not contain a condensed heterocyclic skeleton (b). is preferred, and this group may have a substituent.
  • the heterocyclic compound that does not contain a condensed heterocyclic skeleton (b) includes, for example, among the heterocyclic compounds described in the section on the heterocyclic group above, , a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an sp3 carbon atom and a nitrogen atom in the ring.
  • the monovalent heterocyclic groups in Ar H1 and Ar H2 are preferably monocyclic or bi- to seven-ring heterocyclic compounds (preferably condensed A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or 2- to 7-ring heterocyclic compound containing no heterocyclic skeleton (b)), more preferably Atoms constituting a ring from a monocyclic or bi- to pentacyclic heterocyclic compound (preferably a monocyclic or bi- to pentacyclic heterocyclic compound containing no condensed heterocyclic skeleton (b)) is a group excluding one hydrogen atom directly bonded to the (monocyclic, bicyclic or tricyclic heterocyclic compound) by removing one hydrogen atom directly bonded to an atom constituting the ring, particularly preferably tricyclic heterocyclic compound (Preferably, a tricyclic heterocyclic compound that does not contain a condensed heterocyclic skeleton (b))
  • the monovalent heterocyclic groups in Ar 1 H1 and Ar 2 H2 are preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, pyridine, diazabenzene, because the external quantum efficiency of the light-emitting device of the present disclosure is further excellent.
  • pyridine diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10- dihydrophenazine, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole or di A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from zaindenocarbazole, more preferably pyridine, diazabenzen
  • the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. good too.
  • Examples and preferred ranges of the aryl group, which is a substituent of the amino group are the same as the examples and preferred ranges of the aryl group in Ar H1 and Ar H2 .
  • Examples and preferred ranges of the monovalent heterocyclic group which is a substituent of the amino group are the same as the examples and preferred range of the monovalent heterocyclic group in Ar 1 H1 and Ar 2 H2 .
  • Ar H1 and Ar H2 is preferably an aryl group or a monovalent heterocyclic group, and both Ar H1 and Ar H2 are aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • the aryl group and monovalent heterocyclic group in Ar H1 and Ar H2 are monocyclic, bicyclic or tricyclic aromatic hydrocarbons, or , a monocyclic, bicyclic or tricyclic heterocyclic compound (preferably a monocyclic, bicyclic or tricyclic heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)) , is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring is removed, and a ring is preferably formed from benzene, naphthalene, fluorene, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothi
  • a group in which one hydrogen atom directly bonded to a constituent atom is removed is more preferable, and a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzothienyl group or a dibenzofuryl group is more preferable, and a phenyl group, a naphthyl group or a carbazolyl group. is particularly preferred, and these groups may have a substituent.
  • Preferred substituents that Ar H1 and Ar H2 may have are a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, and a monovalent A heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group , a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, even if these groups further have a substituent good.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that Ar H1 and Ar H2 may have are the aryl group and monovalent heterocyclic group in Ar H1 and Ar H2 , respectively. It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.
  • Preferred substituents that the substituents Ar H1 and Ar H2 may further have include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably , an alkyl group, a cycloalkyl group or an aryl group, particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but should not have a further substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents which the substituents which Ar H1 and Ar H2 may further have are respectively Ar H1 and The same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in Ar H2 .
  • the divalent group for L H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, —N(R 0 ), since the light-emitting device of the present disclosure has better external quantum efficiency.
  • At least one of the divalent groups in L H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, since the light-emitting device of the present disclosure has superior external quantum efficiency, and more An arylene group or a divalent heterocyclic group is preferable, and these groups may have a substituent.
  • the arylene group is preferably a monocyclic or bi- to seven-cyclic aromatic hydrocarbon ring-constituting atom, since the light-emitting device of the present disclosure has superior external quantum efficiency.
  • a group in which two hydrogen atoms directly bonded to are removed more preferably a monocyclic or 2- to 5-cyclic aromatic hydrocarbon in which two hydrogen atoms directly bonded to the atoms constituting the ring are removed group, more preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, and these groups are substituted
  • You may have a group.
  • arylene groups are preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzoanthracene, benzophenanthrene, benzo a group obtained by removing two hydrogen atoms directly bonded to ring-constituting atoms from fluorene, dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene or benzofluoranthene, more preferably benzene, naphthalene or anthracene , phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene or benzofluorene, from which two hydrogen atoms directly bonded to atoms constituting the ring are removed, more preferably benzene, naphthalene, anthracene, phen
  • the divalent heterocyclic group is a hydrogen atom directly bonded to a ring-constituting atom (preferably a carbon atom) from a heterocyclic compound that does not contain a condensed heterocyclic skeleton (b). It is preferably a group excluding two, and this group may have a substituent.
  • the heterocyclic compound that does not contain a condensed heterocyclic skeleton (b) in the divalent heterocyclic group includes the heterocyclic compounds described in the section on the heterocyclic group above.
  • the divalent heterocyclic group is preferably a monocyclic or bi- to seven-ring heterocyclic compound (preferably is a monocyclic or 2- to 7-ring heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)), except for two hydrogen atoms directly bonded to the atoms (preferably carbon atoms) constituting the ring more preferably a monocyclic or bi- to pentacyclic heterocyclic compound (preferably a monocyclic or bi- to pentacyclic heterocyclic ring that does not contain a condensed heterocyclic skeleton (b) A group obtained by removing two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting a ring from the formula compound),
  • a divalent heterocyclic group preferably includes furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole , phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracen
  • the alkylene group is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
  • Examples and preferred ranges of substituents that L H1 may have are the same as examples and preferred ranges of substituents that Ar H1 and Ar H2 may have.
  • R 0 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, An aryl group is more preferable, and these groups may have a substituent.
  • Examples and preferred ranges of the aryl group and monovalent heterocyclic group for R 0 in the divalent group for L H1 are the examples and preferred ranges for the aryl group and monovalent heterocyclic group for Ar H1 and Ar H2 , respectively. is the same as In the divalent group L H1 , examples and preferred ranges of substituents R 0 may have are the same as examples and preferred ranges of substituents Ar H1 and Ar H2 may have. .
  • n H1 is usually an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 7 or less, more preferably an integer of 1 or more and 5 or less, and still more preferably an integer of 1 or more and 3 or less, 1 or 2 is particularly preferred.
  • Ar H1 and Ar H2 may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easy to synthesize. Therefore, it is preferred not to form a ring.
  • examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in the divalent group are They are the same as the examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in L H1 , respectively.
  • examples and preferred ranges of R 0 in the divalent group are R 0 in the divalent group of L H1 is the same as the example and preferred range of
  • examples and preferred ranges of substituents that the divalent group may have include Ar H1 and Ar It is the same as the example and preferred range of the substituent that H2 may have.
  • L 1 H1 and Ar 1 H1 may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easy to synthesize. Therefore, it is preferred not to form a ring.
  • Examples and preferred ranges of the divalent group in the case where L H1 and Ar H1 are bonded via a divalent group to form a ring are: are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • L H1 and Ar H2 may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easily synthesized. Therefore, it is preferred not to form a ring.
  • Examples and preferred ranges of the divalent group in the case where L H1 and Ar H2 are bonded via a divalent group to form a ring are: are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
  • Examples of compounds represented by formula (H-1) include compounds represented by the following formula.
  • the first polymer compound is a polymer compound containing at least one structural unit selected from the group consisting of structural units represented by formula (X) and structural units represented by formula (Y).
  • the first polymer compound is preferably a polymer compound different from the polymer compound (A) and the polymer compound (B), and is a polymer compound that does not contain the structural unit (A) and the structural unit (B). is more preferable.
  • the first polymer compound preferably contains a structural unit represented by formula (Y) because the light-emitting device of the present disclosure has a superior external quantum efficiency.
  • the content of the structural unit represented by formula (Y) contained in the first polymer compound is Any range is acceptable as long as it functions as a molecular compound.
  • the content of the structural unit represented by formula (Y) contained in the first polymer compound is For example, it is 1 to 100 mol% with respect to the total content of structural units contained in the molecular compound, and is preferably 10 to 100 mol% because the external quantum efficiency of the light emitting device of the present disclosure is superior, More preferably 30 to 100 mol %, still more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.
  • the structural unit represented by the formula (Y) may be contained in one kind, or may be contained in two or more kinds.
  • the first polymer compound includes a structural unit represented by formula (X) because the first polymer compound has excellent hole-transport properties and the external quantum efficiency of the light-emitting device of the present disclosure is superior. is preferred.
  • the content of the structural unit represented by formula (X) contained in the first polymer compound is Any range is acceptable as long as it functions as a molecular compound.
  • the content of the structural unit represented by formula (X) contained in the first polymer compound is For example, it is 0.01 to 100 mol% with respect to the total content of the structural units contained in the molecular compound, the hole transport property of the first polymer compound is excellent, and the light emitting device of the present disclosure is obtained. Since the external quantum efficiency is better, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0 .5 to 30 mol %, particularly preferably 1 to 10 mol %.
  • the structural unit represented by the formula (X) may be contained in one kind, or may be contained in two or more kinds.
  • the structural unit represented by formula (Y) and the formula It preferably contains a structural unit represented by (X).
  • the first polymer compound contains a structural unit represented by the formula (Y) and a structural unit represented by the formula (X)
  • it is represented by the formula (Y) contained in the first polymer compound
  • the total content of the structural units and the structural units represented by formula (X) may be within a range in which the function as the first polymer compound can be exhibited.
  • the first polymer compound contains a structural unit represented by the formula (Y) and a structural unit represented by the formula (X), it is represented by the formula (Y) contained in the first polymer compound
  • the total content of the structural units and the structural units represented by the formula (X) is, for example, 1 to 100 mol%, the hole transport property of the first polymer compound is excellent, and the light emission of the present disclosure Since the external quantum efficiency of the device is further improved, it is preferably 10 to 100 mol%, more preferably 30 to 100 mol%, even more preferably 50 to 100 mol%, and particularly preferably 70 to 100 mol%. and particularly preferably 90 to 100 mol %.
  • the arylene group represented by the structural unit Ar Y1 represented by the formula (Y) is preferably monocyclic or bicyclic to hexacyclic because the light-emitting device of the present disclosure has superior external quantum efficiency.
  • a group in which two hydrogen atoms directly bonded to the constituent atoms are removed more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, and two hydrogen atoms directly bonded to the ring-constituting atoms are removed.
  • the divalent heterocyclic group represented by Ar Y1 is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound, because the light-emitting device of the present disclosure has a superior external quantum efficiency.
  • a group excluding two hydrogen atoms that are directly bonded to the atoms that constitute a group with two hydrogen atoms removed more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10 -
  • the preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, It is the same as the preferred range of the arylene group and divalent heterocyclic group represented by Ar Y1 .
  • the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded” includes, for example, groups represented by the following formulae, The group may have a substituent.
  • Ar Y1 is preferably an optionally substituted arylene group because the light-emitting device of the present disclosure has a more excellent external quantum efficiency.
  • the substituent that the group represented by Ar Y1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a bridging group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a bridging group, more preferably , an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a bridging group, particularly preferably an alkyl group, a cycloalkyl group, an aryl group or a bridging group, and these groups are Furthermore, it may have a substituent.
  • the aryl group in the substituent that the group represented by Ar Y1 may have is preferably a monocyclic or bicyclic to hexacyclic aromatic group because the light-emitting device of the present disclosure has superior external quantum efficiency.
  • the monovalent heterocyclic group in the substituent that the group represented by Ar Y1 may have is preferably monocyclic or bicyclic to 6 A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from a cyclic heterocyclic compound, more preferably a monocyclic, bicyclic or tricyclic heterocyclic compound , a group in which one hydrogen atom directly bonded to a ring-constituting atom is removed, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine, excluding one hydrogen atom directly bonded to an atom (preferably a carbon atom or a nitrogen atom) constituting a ring, particularly preferably pyridine, diazabenz
  • the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group.
  • the group may further have a substituent.
  • Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the aryl group and monovalent heterocyclic group in the substituent that the group represented by Ar Y1 may have, respectively. is the same as the example and preferred range of
  • the substituents that the group represented by Ar Y1 may further have include: preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a bridging group, more preferably an alkyl group, A cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a bridging group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a bridging group, particularly preferably an alkyl group or a cyclo It is an alkyl group or a bridging group, and these groups may further have a substituent, but preferably have no further substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by Ar Y1 may further have are Ar Y1 are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the group may have.
  • the structural unit represented by formula (Y) is preferably a structural unit represented by formula (Y-1) or formula (Y-2), since the light-emitting device of the present disclosure has superior external quantum efficiency. .
  • R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a bridging group; may have a substituent. When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. A plurality of R Y1 may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom or a bridging group; may have a substituent.
  • substituents When there are multiple such substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • a plurality of RY2 may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
  • R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a bridging group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, It is an aryl group or a bridging group, more preferably a hydrogen atom, an alkyl group or a bridging group, and these groups may have a substituent.
  • R 1 Y1 is preferably an alkyl group, a cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, fluorine atom or bridging group, more preferably alkyl group, cycloalkyl group, aryl group, 1 a valent heterocyclic group, a substituted amino group or a bridging group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a bridging group, An alkyl group or a cross-linking group is particularly preferred, and these groups may have a substituent.
  • R Y2 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a bridge because the light-emitting device of the present disclosure has a superior external quantum efficiency.
  • a group more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a bridging group, still more preferably an alkyl group, a cycloalkyl group, an aryl group or a bridging group,
  • the group may have a substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group for R Y1 and R Y2 are, respectively, the aryl group and the monovalent It is the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
  • Examples and preferred ranges of substituents that R Y1 and R Y2 may have are the same as examples and preferred ranges of substituents that the group represented by Ar Y1 may have.
  • X Y1 is preferably a group represented by -C(R Y2 ) 2 - or -C(R Y2 ) 2 -C(R Y2 ) 2 -, since the light-emitting device of the present disclosure has superior external quantum efficiency. and more preferably a group represented by —C(R Y2 ) 2 —.
  • Examples of structural units represented by formula (Y) include structural units represented by the following formula.
  • X1 and a X2 represented by formula (X) are usually integers of 0 to 10, and are preferably integers of 0 to 5 because the external quantum efficiency of the light emitting device of the present disclosure is superior. , more preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, because the light-emitting device of the present disclosure has superior external quantum efficiency. or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.
  • Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in R X1 , R X2 and R X3 are, respectively, the aryl group and the monovalent heterocyclic group in the substituent that the group represented by Ar Y1 may have. It is the same as the example and preferred range of the cyclic group.
  • Ar X1 , Ar X2 , Ar X3 and Ar X4 are preferably arylene groups optionally having substituents, since the light-emitting device of the present disclosure has a higher external quantum efficiency.
  • Examples and preferred ranges of the arylene group and divalent heterocyclic group for Ar X1 , Ar X2 , Ar X3 and Ar X4 are the same as the examples and preferred ranges of the arylene group and divalent heterocyclic group for Ar Y1 respectively. be.
  • Examples and preferred arylene groups and divalent heterocyclic groups in the divalent group in which at least one arylene group and at least one divalent heterocyclic group represented by Ar X2 and Ar X4 are directly bonded The ranges are the same as the examples and preferred ranges of the arylene group and the divalent heterocyclic group in Ar Y1 , respectively.
  • the divalent group in which at least one arylene group and at least one divalent heterocyclic group in Ar X2 and Ar X4 are directly bonded includes at least one arylene group and at least one divalent heterocyclic group in Ar Y1 . Examples thereof include the same divalent groups to which a valent heterocyclic group is directly bonded.
  • Examples and preferred ranges of the substituents that the groups represented by Ar X1 to Ar X4 and R X1 to R X3 may have are the examples and preferred ranges of the substituents that the group represented by Ar Y1 may have. Same as range.
  • Examples of structural units represented by formula (X) include structural units represented by the following formula.
  • Examples of the first polymer compound include polymer compounds HP-1 to HP-3.
  • Other structural units mean structural units other than the structural units represented by the formula (Y) and the structural units represented by the formula (X). ]
  • the first polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, or a graft copolymer. It is preferably a copolymer obtained by copolymerizing monomers. Since the external quantum efficiency of the light-emitting device of the present disclosure is superior, the polystyrene-equivalent number-average molecular weight of the first polymer compound is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 . to 5 ⁇ 10 5 , more preferably 2 ⁇ 10 4 to 2 ⁇ 10 5 .
  • the polystyrene-equivalent weight-average molecular weight of the first polymer compound is preferably 1 ⁇ 10 4 to 2 ⁇ 10 6 , more preferably 2 ⁇ 10 4 . to 1 ⁇ 10 6 , more preferably 5 ⁇ 10 4 to 9 ⁇ 10 5 .
  • the first polymer compound can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), Suzuki reaction, Yamamoto , Buchwald reaction, Stille reaction, Negishi reaction, Kumada reaction, and other coupling reactions using a transition metal catalyst.
  • the method of charging the monomers includes a method of charging the entire amount of the monomers into the reaction system at once, a method of charging a part of the monomers and reacting them, and then charging the remaining monomers all at once. Examples thereof include a method of continuously or dividedly charging, a method of continuously or dividingly charging a monomer, and the like.
  • transition metal catalysts include palladium catalysts and nickel catalysts.
  • the post-treatment of the polymerization reaction is performed by a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., is performed singly or in combination.
  • a method of removing water-soluble impurities by liquid separation adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., is performed singly or in combination.
  • the purity of the first polymer compound is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.
  • the composition of the present disclosure comprises a compound (A), a compound (B), two or more first compounds, a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, A composition containing at least one selected from the group consisting of an antioxidant and a solvent may also be used.
  • the hole-transporting material, hole-injecting material, electron-transporting material, electron-injecting material, and light-emitting material are different from the compound (A), the compound (B), and the first compound.
  • a composition containing compound (A), compound (B), two or more first compounds, and a solvent (hereinafter referred to as "ink”) can be prepared by, for example, spin coating, casting, Micro gravure coating method, 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 It is suitable for fabricating a light-emitting device using a wet method such as a nozzle coating method.
  • the viscosity of the ink may be adjusted depending on the type of printing method, but when applying to a printing method such as an inkjet printing method in which a solution passes through an ejection device, it is necessary to prevent clogging and flight deflection during ejection. , preferably 1 mPa ⁇ s to 20 mPa ⁇ s at 25°C.
  • the solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink.
  • solvents include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; 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
  • polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , and N-dimethylformamide.
  • a solvent may be used individually by 1 type, or may use 2 or more types together.
  • the content of the solvent is usually 1000 parts by mass to 1000000 parts by mass when the total content of the compound (A), the compound (B) and the two or more first compounds is 100 parts by mass. is.
  • Hole-transporting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.
  • the hole-transporting material may have a cross-linking group.
  • low-molecular-weight compounds include triphenylamine and its derivatives, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine ( ⁇ -NPD), and N,N'-diphenyl-N, Aromatic amine compounds such as N'-di(m-tolyl)benzidine (TPD) can be mentioned.
  • Polymer compounds include, for example, polyvinylcarbazole and derivatives thereof; polyarylenes and derivatives thereof having aromatic amine structures in side chains or main chains.
  • the polymer compound may be a compound having electron-accepting moieties such as fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene and trinitrofluorenone bound thereto.
  • the content of the hole-transporting material is the total content of compound (A), compound (B), and two or more first compounds. When 100 parts by mass, it is usually 1 to 1000 parts by mass.
  • the hole transport materials may be used singly or in combination of two or more.
  • Electron transport materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.
  • the electron transport material may have a cross-linking group.
  • Examples of low-molecular-weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone. , as well as derivatives thereof.
  • Polymer compounds include, for example, polyphenylene, polyfluorene, and derivatives thereof.
  • the polymeric compounds may be doped with metals.
  • the content of the electron-transporting material is the total content of the compound (A), the compound (B), and the two or more first compounds, which is 100 mass When expressed as parts, it is usually 1 to 1000 parts by mass.
  • the electron transport materials may be used singly or in combination of two or more.
  • Hole-injecting materials and electron-injecting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds, respectively.
  • the hole-injecting material and the electron-injecting material may have cross-linking groups.
  • Examples of low-molecular 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.
  • Polymer compounds include, for example, 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; and a flexible polymer.
  • the content of the hole-injection material and the electron-injection material is, respectively, compound (A) and compound (B)
  • the total content of the and two or more first compounds is 100 parts by mass, it is usually 1 to 1000 parts by mass.
  • Each of the hole injection material and the electron injection material may be used alone or in combination of two or more.
  • the hole-injecting material or the electron-injecting material may be doped with ions.
  • the electrical conductivity of the conductive polymer is preferably between 1 ⁇ 10 ⁇ 5 S/cm and 1 ⁇ 10 3 S/cm.
  • the conductive polymer can be doped with an appropriate amount of ions in order to set the electrical conductivity of the conductive polymer within this range.
  • the type of ions to be doped into the hole injection material or the electron injection material is, for example, an anion for the hole injection material, and a cation for the electron injection material.
  • Anions include, for example, polystyrene sulfonate, alkylbenzene sulfonate, and camphor sulfonate.
  • Cations include, for example, lithium ion, sodium ion, potassium ion and tetrabutylammonium ion. Ions for doping may be used alone or in combination of two or more.
  • Luminous material Light-emitting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.
  • the luminescent material may have a cross-linking group.
  • low-molecular-weight compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and phosphorescent compounds having iridium, platinum, or europium as a central metal.
  • polymer compounds include polymer compounds containing structural units represented by formula (Y) and/or structural units represented by formula (X).
  • Examples of phosphorescent compounds include metal complexes shown below.
  • the content of the light-emitting material is the total content of the compound (A), the compound (B), and the two or more first compounds.
  • 100 parts by mass it is usually 1 to 1000 parts by mass.
  • a luminescent material may be used individually by 1 type, or may use 2 or more types together.
  • the antioxidant may be a compound that is soluble in the same solvent as the compound (A), the compound (B), and the first compound and does not inhibit light emission and charge transport. system antioxidants.
  • the content of the antioxidant is the total content of compound (A), compound (B), and two or more first compounds When the amount is 100 parts by mass, it is usually 0.001 to 10 parts by mass.
  • Antioxidants may be used singly or in combination of two or more.
  • the membranes of the present disclosure contain the compositions of the present disclosure described above.
  • the film of the present disclosure is suitable as a light-emitting layer in a light-emitting device.
  • the membranes of the present disclosure can be made by wet methods, using inks, for example.
  • the film of the present disclosure can be produced, for example, by a dry method such as a vacuum deposition method. Methods for producing the film of the present disclosure by a dry method include, for example, a method of vapor-depositing the composition described above, and a method of co-depositing compound (A), compound (B), and two or more first compounds. is mentioned.
  • the film thickness is typically between 1 nm and 10 ⁇ m
  • the light-emitting device of the present disclosure contains the composition described above.
  • a light-emitting device of the present disclosure may comprise, for example, an anode, a cathode, and an organic layer containing the composition described above provided between the anode and the cathode.
  • the layer containing the composition of the present disclosure is usually one or more layers selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer and an electron-injecting layer, preferably This is the light-emitting layer.
  • These layers each contain a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material.
  • Each of these layers can be formed from a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material using the same method as for the above-described films.
  • a light-emitting element has a light-emitting layer between an anode and a cathode.
  • the light emitting device of the present disclosure preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer.
  • Materials for the hole-transporting layer, electron-transporting layer, light-emitting layer, hole-injecting layer, and electron-injecting layer include, in addition to the composition of the present disclosure, the hole-transporting material, electron-transporting material, light-emitting material, and electron-injecting layer described above, respectively. Examples include hole-injecting materials and electron-injecting materials.
  • the materials for the hole-transporting layer, the electron-transporting layer, and the light-emitting layer are selected from the solvents used in forming the layers adjacent to the hole-transporting layer, the electron-transporting layer, and the light-emitting layer, respectively, in the manufacture of the light-emitting device.
  • the material has cross-linking groups to avoid dissolving the material in the solvent. After forming each layer using a material having a cross-linking group, the layer can be made insoluble by cross-linking the cross-linking group.
  • each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, when using a low-molecular compound
  • vacuum deposition from powder Dry methods such as methods
  • wet methods such as methods by film formation from a solution or a molten state
  • wet methods such as methods by film formation from a solution or a molten state, for example, when using a polymer compound.
  • the order, number and thickness of the layers to be laminated are adjusted in consideration of, for example, the external quantum efficiency.
  • the substrate in the light emitting device may be a substrate on which an electrode can be formed and which does not change chemically when the organic layer is formed.
  • the electrodes furthest from the substrate be transparent or translucent.
  • materials 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 compounds of; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, copper.
  • cathode materials include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of them; alloys of one or more species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, tin; and graphite and graphite intercalation compounds.
  • alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.
  • Each of the anode and the cathode may have a laminated structure of two or more layers.
  • the light-emitting element of the present disclosure is suitable as a light source for backlight of a liquid crystal display device, a light source for illumination, organic EL lighting, a display device such as a computer, a television, and a mobile terminal (e.g., an organic EL display and an organic EL television). can be used.
  • the polystyrene-equivalent number-average molecular weight (Mn) and polystyrene-equivalent weight-average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase.
  • SEC size exclusion chromatography
  • each measurement condition of SEC is as follows. A polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 ⁇ L of the solution was injected into SEC. Mobile phase was run at a flow rate of 2.0 mL/min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as a detector.
  • NMR NMR was measured by the following method. 5 to 10 mg of a measurement sample was added to about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethylsulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol. Alternatively, it was dissolved in methylene dichloride and measured using an NMR device (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).
  • Calculation of the ⁇ EST value of the compound was performed as follows. First, the ground state of the compound was structurally optimized by density functional theory at the B3LYP level. At that time, 6-31G* was used as a basis function. Then, using the obtained optimized structure, ⁇ EST of the compound was calculated by time-dependent density functional theory at the B3LYP level. The calculation was performed using Gaussian09 as a quantum chemical calculation program.
  • the maximum peak wavelength of the emission spectrum of the compound at room temperature was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, FP-6500).
  • a xylene solution in which a compound was dissolved in xylene at a concentration of about 8 ⁇ 10 ⁇ 4 mass % was used as a sample.
  • Ultraviolet (UV) light with a wavelength of 325 nm was used as excitation light.
  • the ⁇ EST of compound B1 was 0.49 eV.
  • the maximum peak wavelength of the emission spectrum of compound B1 at room temperature was 452 nm.
  • the maximum peak half width of the emission spectrum of compound B1 at room temperature was 22 nm.
  • Compound M1 was synthesized according to the method described in WO2015/145871.
  • Compound M2 was synthesized according to the method described in WO2013/146806.
  • Compound M3 was synthesized according to the method described in WO2005/049546.
  • Compound M4 was synthesized according to the method described in JP-A-2010-189630.
  • Compound M5 was synthesized according to the method described in WO2013/146806.
  • the compound M6 used was manufactured by Aldrich.
  • Compound M7 was synthesized according to the method described in WO2009/131255. A commercially available product was used as compound M8.
  • Compound M9 was synthesized according to the method described in WO2016/031639.
  • Compound M10 was synthesized according to the method described in International Publication No. 2013/191088.
  • Compound M11 was synthesized according to the method described in WO2015/145871.
  • Metal complex MC2 was synthesized according to the method described in JP-A-2015-144260.
  • Compound B2 was synthesized according to the method described in WO2019/004248.
  • Polymer compound HTL-1 was synthesized using compound M1, compound M2 and compound M3 according to the method described in WO 2015/145871.
  • the Mn of the polymer compound HTL-1 was 2.3 ⁇ 10 4 and the Mw was 1.2 ⁇ 10 5 .
  • the theoretical values obtained from the amounts of the raw materials charged are the structural units derived from the compound M1, the structural units derived from the compound M2, and the structural units derived from the compound M3. It is a copolymer composed of a molar ratio of 45:5:50.
  • the polymer compound ET1a is a compound ET1-1 synthesized according to the method described in JP-A-2012-33845, and a compound ET1-2 synthesized according to the method described in JP-A-2012-33845. It was synthesized according to the method described in JP-A-2012-33845.
  • Mn of the polymer compound ET1a was 5.2 ⁇ 10 4 .
  • the polymer compound ET1a is composed of structural units derived from the compound ET1-1 and structural units derived from the compound ET1-2 at a molar ratio of 50:50, according to the theoretical value obtained from the amount of the raw materials. It is a copolymer that has been
  • polymer compound BP1 (Synthesis of polymer compound BP1) Polymer compound BP1 was synthesized using compound M8, compound M9, compound M7 and compound B2 according to the method described in WO2019/004248. Mn of the polymer compound BP1 was 4.5 ⁇ 10 4 and Mw was 1.1 ⁇ 10 5 . According to the theoretical values obtained from the amounts of the starting materials, the polymer compound BP1 has a structural unit derived from the compound M8, a structural unit derived from the compound M9, a structural unit derived from the compound M7, and a structural unit derived from the compound B2. The derived structural units are copolymers made up in a molar ratio of 45:5:49:1.
  • Polymer compound HP1 was synthesized using compound M4, compound M5, compound M2 and compound M6 according to the method described in JP-A-2015-144260.
  • the Mn of the polymer compound HP1 was 6.6 ⁇ 10 4 and the Mw was 7.5 ⁇ 10 5 .
  • the polymer compound HP1 has a structural unit derived from the compound M4, a structural unit derived from the compound M6, a structural unit derived from the compound M5, and a structural unit derived from the compound M2.
  • the derived structural units are copolymers made up in a molar ratio of 30:10:10:50.
  • polymer compound HP2 (Synthesis of polymer compound HP2) Polymer compound HP2 was synthesized according to the method described in JP-A-2015-144260 using compound M4, compound M5, compound M2, compound M6 and metal complex MC2.
  • the polymer compound HP2 had Mn of 5.5 ⁇ 10 4 and Mw of 1.4 ⁇ 10 5 .
  • the polymer compound HP1 has a structural unit derived from the compound M4, a structural unit derived from the compound M5, a structural unit derived from the compound M2, and a structural unit derived from the compound M6. It is a copolymer composed of structural units derived from the metal complex MC2 and structural units derived from the metal complex MC2 at a molar ratio of 30:10:10:35.5:14.5.
  • Example D1 Production and evaluation of light emitting device D1 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method.
  • ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • a spin coating method was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film.
  • the substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.
  • a polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.
  • the polymer compound ET1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.4% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 20 nm was formed on the light-emitting layer by spin coating. An electron transport layer was formed by heating at 130° C. for 10 minutes in a gas atmosphere.
  • Example CD1 Production and evaluation of light-emitting element CD1 A light-emitting element CD1 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer CD1) below. bottom.
  • Example CD2 Production and Evaluation of Light-Emitting Element CD2
  • a light-emitting element CD2 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer CD2) below. bottom.
  • Table 4 shows the results of Example D1 and Comparative Examples CD1 and CD2.
  • the relative values of the external quantum efficiencies of the light-emitting elements D1 and CD1 are shown when the external quantum efficiency of the light-emitting element CD2 is set to 1.00.
  • Example D2 Production and evaluation of light-emitting element D2
  • Light-emitting element D2 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer D2) below. bottom.
  • Example CD3 Production and evaluation of light-emitting element CD3 A light-emitting element CD3 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer CD3) below. bottom.
  • Table 5 shows the results of Example D2 and Comparative Example CD3. The relative value of the external quantum efficiency of the light-emitting element D2 is shown when the external quantum efficiency of the light-emitting element CD3 is set to 1.00.
  • Example D3 Production and evaluation of light-emitting element D3
  • Light-emitting element D3 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer D3) below. bottom.
  • Example D4 Production and evaluation of light-emitting element D4
  • Light-emitting element D4 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer D4) below. bottom.
  • Example D5 Production and evaluation of light-emitting element D5
  • Light-emitting element D5 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer D5) below. bottom.
  • Example D6 Preparation and evaluation of light-emitting element D6
  • Light-emitting element D6 was prepared in the same manner as in Example D1 except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer D-6) below. was made.
  • Table 6 shows the results of Examples D3 to D6 and Comparative Example CD4. The relative values of the external quantum efficiencies of the light-emitting elements D3 to D6 are shown when the external quantum efficiency of the light-emitting element CD4 is set to 1.00.
  • Example D7 Production and evaluation of light emitting device D7 (formation of anode and hole injection layer) An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.
  • ND-3202 manufactured by Nissan Chemical Industries, Ltd.
  • a polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.
  • Example CD5 Production and evaluation of light-emitting element CD5 A light-emitting element CD5 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer CD1). .
  • Example CD6 Production and Evaluation of Light-Emitting Element CD6
  • a light-emitting element CD6 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to the following (formation of light-emitting layer CD6). made.
  • Table 7 shows the results of Example D7 and Comparative Examples CD5 to CD6.
  • the relative values of the external quantum efficiencies of the light-emitting element D7 and the comparative example CD6 are shown when the external quantum efficiency of the light-emitting element CD5 is set to 1.00.
  • Example D8 Production and evaluation of light-emitting element D8 Light-emitting element D8 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer D8) below. bottom.
  • Example D9 Production and Evaluation of Light-Emitting Device D9
  • a light-emitting device D9 was produced in the same manner as in Example D7, except that (Formation of light-emitting layer) of Example D7 was the same as (Formation of light-emitting layer D4).
  • Example D10 Production and evaluation of light-emitting element D10
  • Light-emitting element D10 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer D10) below. bottom.
  • Example D11 Production and evaluation of light-emitting element D11 Light-emitting element D11 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer D5). .
  • Example D12 Production and evaluation of light-emitting element D12 Light-emitting element D12 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer D6). .
  • Example CD7 Production and evaluation of light-emitting element CD7 A light-emitting element CD7 was produced in the same manner as in Example D7, except that (formation of light-emitting layer) of Example D7 was changed to (formation of light-emitting layer CD4). .
  • Table 8 shows the results of Examples D8 to D12 and Comparative Example CD7.
  • the relative values of the external quantum efficiencies of the light-emitting elements D8 to D12 are shown when the external quantum efficiency of the light-emitting element CD7 is set to 1.00.
  • composition useful for manufacturing a light-emitting device with excellent external quantum efficiency it is possible to provide a composition useful for manufacturing a light-emitting device with excellent external quantum efficiency, and a light-emitting device containing the composition.

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Abstract

L'invention fournit une composition avantageuse dans la fabrication d'un élément luminescent d'une excellente efficacité quantique externe, et fournit également un élément luminescent comprenant cette composition.　Plus précisément, l'invention concerne une composition qui comprend : au moins une sorte de composé choisie dans un groupe constitué d'un complexe métallique représenté par la formule (1) et d'un composé à haut poids moléculaire (A) ; au moins une sorte de composé choisie dans un groupe constitué d'un composé à faible poids moléculaire (B) et d'un composé à haut poids moléculaire (B) ; et d'au moins deux sortes de composé choisies dans un groupe constitué d'un composé représenté par la formule (H-1), et d'un composé à haut poids moléculaire contenant au moins une sorte d'unité structurale choisie parmi une unité structurale représentée par la formule (X) et une unité structurale représentée par la formule (Y).
PCT/JP2022/035145 2021-09-29 2022-09-21 Composition, et élément luminescent comprenant celle-ci WO2023054109A1 (fr)

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