WO2017170325A1 - Élément électroluminescent - Google Patents

Élément électroluminescent Download PDF

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WO2017170325A1
WO2017170325A1 PCT/JP2017/012251 JP2017012251W WO2017170325A1 WO 2017170325 A1 WO2017170325 A1 WO 2017170325A1 JP 2017012251 W JP2017012251 W JP 2017012251W WO 2017170325 A1 WO2017170325 A1 WO 2017170325A1
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group
ring
formula
substituent
organic layer
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PCT/JP2017/012251
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English (en)
Japanese (ja)
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裕宗 朝比奈
敏明 佐々田
吉田　大泰
掌吾 山内
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住友化学株式会社
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Priority to JP2018509304A priority Critical patent/JP6982566B2/ja
Publication of WO2017170325A1 publication Critical patent/WO2017170325A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/38—Polycyclic condensed hydrocarbons containing four rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
    • C07C15/52—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed containing a group with formula
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a light emitting element.
  • Organic electroluminescence elements (hereinafter also referred to as “light-emitting elements”) can be suitably used for display and lighting applications, and in recent years, research and development of organic electroluminescence elements with a long lifetime and high luminous efficiency. Has been done.
  • Patent Document 1 in an organic electroluminescence device in which an organic thin film layer including at least a light emitting layer is sandwiched between a cathode and an anode, the light emitting layer is an organic material containing a compound having a fluoranthene structure and a condensed ring-containing compound.
  • An electroluminescent element is described (claim 1).
  • Specific examples of the compound having a fluoranthene structure include compounds (2-29) and (2-21) represented by the following formula (paragraph 0110).
  • Specific examples of the condensed ring compound include a compound (2a′-55) represented by the following formula (paragraph 0122).
  • Example 13 of Patent Document 1 an organic electroluminescence device containing a compound (2-29) and a compound (2a′-55) in a light emitting layer is described.
  • the light emitting layer is a vapor deposition layer formed by co-evaporating the compound (2-29) and the compound (2a′-55) on the hole transport layer.
  • the hole transport layer is a deposited layer formed by depositing N, N, N′N′-tetra (4-biphenylyl) benzidine on the hole injection layer (paragraph 0171).
  • Example 21 of Patent Document 1 an organic electroluminescence device containing a compound (2-21) and a compound (2a′-55) in the light emitting layer is described.
  • the light-emitting layer was formed by spin-coating a toluene solution of the compound (2-21) and the compound (2a′-55) on the hole transport layer. It is.
  • the hole transport layer is a coating layer formed by spin-coating a toluene solution of polymer 1 represented by the following formula on the hole injection layer (paragraph 0177).
  • the above-described conventional light emitting device has a driving voltage that is not sufficiently low and needs to be further reduced.
  • an object of the present invention is to provide a light emitting element having a low driving voltage.
  • the present invention provides the following [1] to [11].
  • a light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
  • the first organic layer is a layer containing a composition containing the first compound and the first light emitting material, and the maximum peak wavelength of the emission spectrum of the first light emitting material is 380 nm or more and 570 nm or less, The maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first luminescent material;
  • the first compound is a compound represented by the formula (1A)
  • the first light emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B),
  • the light emitting element whose 2nd organic layer is a layer containing the crosslinked body of a crosslinking material.
  • n 1A represents an integer of 1 or more and 10 or less.
  • n 2A represents an integer of 0 or more and 10 or less.
  • Ar 1A represents a condensed ring aromatic hydrocarbon group in which 3 to 10 benzene rings are condensed.
  • R 1A represents an aryl group of a condensed ring, and the group may have a substituent. When a plurality of R 1A are present, they may be the same or different.
  • R 2A is a halogen atom, cyano group, alkyl group, cycloalkyl group, monocyclic aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group Alternatively, it represents a cycloalkynyl group, and these groups optionally have a substituent. When a plurality of R 2A are present, they may be the same or different. ]
  • n 1B represents an integer of 0 or more and 10 or less.
  • Ar 1B represents an aromatic hydrocarbon group.
  • R 1B is a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group or cycloalkynyl. Represents a group, and these groups may have a substituent.
  • R 1B When a plurality of R 1B are present, they may be the same or different and may be bonded together to form a ring together with the carbon atoms to which they are bonded.
  • R 1B is a halogen atom, cyano group, alkyl group, cycloalkyl group, monocyclic An aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, an alkynyl group, or a cycloalkynyl group, and these groups may have a substituent. . ]
  • the cross-linking material is [1] A low molecular compound having at least one crosslinking group selected from the crosslinking group A group, or a polymer compound containing a crosslinking structural unit having at least one crosslinking group selected from the crosslinking group A group.
  • the light emitting element as described in. (Crosslinking group A group)
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • n XL represents an integer of 0 to 5.
  • * 1 represents a binding position.
  • cross-linking material is a polymer compound including a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group.
  • nA represents an integer of 0 to 5, and n represents 1 or 2.
  • Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
  • L A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good.
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • X represents a crosslinking group selected from the crosslinking group A group. When two or more X exists, they may be the same or different. ]
  • mA represents an integer of 0 to 5
  • m represents an integer of 1 to 4
  • c represents an integer of 0 or 1.
  • Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
  • Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar 4 , Ar 5 and Ar 6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be.
  • K A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good.
  • R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • X ′ represents a bridging group selected from the bridging group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of X ′ are present, they may be the same or different.
  • at least one X ′ is a crosslinking group selected from the crosslinking group A group.
  • m B1 , m B2 and m B3 each independently represent an integer of 0 or more.
  • a plurality of m B1 may be the same or different.
  • a plurality of m B3 are present, they may be the same or different.
  • Ar 7 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be. When a plurality of Ar 7 are present, they may be the same or different.
  • L B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R ′ ′′) —, an oxygen atom or a sulfur atom, and these groups are substituent groups. You may have.
  • R ′ ′′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a plurality of L B1 When a plurality of L B1 are present, they may be the same or different.
  • X ′′ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of X ′′ may be the same or different. However, at least one of a plurality of X ′′ is a crosslinking group.
  • Ar 1A is an anthracene ring, a phenanthrene ring, or one or more hydrogen atoms directly bonded to a carbon atom constituting the ring from a ring in which 1 to 7 benzene rings are condensed to these rings
  • the compound represented by the formula (1A) is represented by the formula (1A-A1), formula (1A-A2), formula (1A-A3), formula (1A-A4), formula (1A-A5) or The light-emitting device according to any one of [1] to [6], which is a compound represented by the formula (1A-A6).
  • R 1A is a naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, indene ring, fluoranthene ring, or [1] to [7], which is a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from the benzofluoranthene ring (this group may have a substituent).
  • the light emitting element in any one of.
  • the Ar 1B is a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, [1] to [8], which is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an indene ring, a fluoranthene ring, a benzofluoranthene ring, or an acenaphthofluoranthene ring.
  • the light emitting element in any one of.
  • the first organic layer is a layer containing a composition containing a first compound and a first light-emitting material;
  • the maximum peak wavelength of the emission spectrum of the first luminescent material is 380 nm or more and 570 nm or less, The maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first luminescent material;
  • the first compound is a compound represented by the formula (1A)
  • the first light emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B)
  • the second organic layer is a layer containing a crosslinked material of a crosslinking material; A step of forming a film of a crosslinking material for forming the second organic layer by a wet method;
  • a light emitting element with a low driving voltage can be provided.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • i-Pr represents an isopropyl group
  • t-Bu represents a tert-butyl group.
  • the hydrogen atom may be a deuterium atom or a light hydrogen atom.
  • the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.
  • the “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 8 .
  • Low molecular weight compound means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
  • “Structural unit” means one or more units present in a polymer compound.
  • the “alkyl group” may be linear or branched.
  • the number of carbon atoms of the straight chain alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the alkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc., for example, a trifluoromethyl group, a pentafluoroethyl group,
  • the number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.
  • Aryl group means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the number of carbon atoms of the substituent.
  • the “alkoxy group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkoxy group is usually 1 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
  • the alkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
  • a substituent for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-buty
  • the number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
  • the cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.
  • the number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
  • the aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.
  • the “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.
  • Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc.
  • a compound in which the ring itself exhibits aromaticity and a compound in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran Means.
  • the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
  • the monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.
  • Halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “amino group” may have a substituent, and a substituted amino group is preferable.
  • a substituent which an amino group has an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.
  • the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
  • the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (3,5-di-tert- Butylphenyl) amino group.
  • the “alkenyl group” may be linear or branched.
  • the number of carbon atoms of the straight-chain alkenyl group is usually 2-30, preferably 3-20, excluding the number of carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
  • the alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.
  • the “alkynyl group” may be linear or branched.
  • the number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the branched alkynyl group is usually from 4 to 30, and preferably from 4 to 20, not including the carbon atom of the substituent.
  • the number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
  • the alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.
  • the “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.
  • the arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formulas (A-1) to (A-20) are preferable.
  • the arylene group includes a group in which a plurality of these groups are bonded.
  • R and R a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
  • a plurality of R and R a may be the same or different, and R a may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Is a group represented by formula (AA-1) to formula (AA-34).
  • the divalent heterocyclic group includes a group in which a plurality of these groups
  • crosslinking group is a group capable of forming a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc.
  • “Substituent” means a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, alkenyl group. Represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group.
  • the substituent may be a crosslinking group.
  • a light-emitting element of the present invention is a light-emitting element having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.
  • the light-emitting element is a layer containing a composition including one compound and a first light-emitting material
  • the second organic layer is a layer containing a cross-linked body of a cross-linking material.
  • Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum deposition method and a wet method such as a spin coating method and an ink jet printing method, and a wet method is preferable.
  • the first organic layer is formed by a wet method, it is preferable to use a first ink described later.
  • the crosslinking material contained in the second organic layer can be crosslinked by heating or light irradiation, and the crosslinking contained in the second organic layer by heating. It is preferred to crosslink the material.
  • the crosslinked material is contained in the second organic layer in a crosslinked state (crosslinked product of the crosslinked material)
  • the second organic layer is substantially insolubilized in the solvent. Therefore, the second organic layer can be suitably used for stacking light emitting elements.
  • the heating temperature for crosslinking is usually 25 ° C to 300 ° C, preferably 50 ° C to 250 ° C, more preferably 150 ° C to 200 ° C, and further preferably 170 ° C to 190 ° C. .
  • the heating time for crosslinking is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1 to 120 minutes, and further preferably 30 to 90 minutes. .
  • the types of light used for light irradiation are, for example, ultraviolet light, near ultraviolet light, and visible light.
  • Examples of the analysis method of the components contained in the first organic layer or the second organic layer include chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
  • chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR)
  • Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
  • insoluble Component components that are substantially insoluble in the organic solvent
  • dissolved component components that dissolves in an organic solvent
  • insoluble components can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and dissolved components can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.
  • the first organic layer is a layer containing the first compound and the first light emitting material.
  • the first organic layer can be formed without being limited to the method for forming the first organic layer. Become.
  • dispersibility and compatibility between the first compound and the first light-emitting material are improved, so that it is considered that the light-emitting element has a lower driving voltage than a conventional light-emitting element.
  • the maximum peak wavelength of the emission spectrum of the first compound is preferably 300 nm or more and 550 nm or less, more preferably 340 or more and 495 nm or less, still more preferably 380 nm or more and 480 nm or less, and particularly preferably 400 nm or more and 450 nm or less. It is.
  • the maximum peak wavelength of the emission spectrum of the first light-emitting material is 380 to 570 nm, preferably 400 to 550 nm, more preferably 420 to 520 nm, and still more preferably 430 to 510 nm. Further, the maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first light emitting material.
  • the maximum peak wavelength of the emission spectrum of a compound is determined by dissolving the compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, and preparing a dilute solution (1 ⁇ 10 ⁇ 6 to 1 ⁇ 10 ⁇ 3 It can be evaluated by measuring the PL spectrum of the diluted solution at room temperature.
  • an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran
  • the first compound preferably has at least one function selected from the group consisting of light emitting property, hole injecting property, hole transporting property, electron injecting property, and electron transporting property. It is more preferable to have at least one function selected from the group consisting of properties, electron injection properties, and electron transport properties.
  • the first compound is a compound represented by the formula (1A).
  • the first light-emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B).
  • n 1A is preferably an integer of 1 to 7, and more preferably an integer of 1 to 4.
  • n 2A is preferably an integer of 0 to 7, more preferably an integer of 0 to 4, still more preferably an integer of 0 to 2, and particularly preferably 0 or 1.
  • “Aromatic hydrocarbon group of condensed ring in which 3 or more and 10 or less benzene rings are condensed” refers to a ring composed of an aromatic hydrocarbon ring in which only 3 or more and 10 or less benzene rings are condensed. A group formed by removing one or more hydrogen atoms directly bonded to a carbon atom.
  • the condensed ring aromatic hydrocarbon group in which 3 or more and 10 or less benzene rings are condensed is preferably a condensed ring aromatic hydrocarbon group in which 3 or 7 or less benzene rings are condensed, More preferably, it is a condensed ring aromatic hydrocarbon group in which 3 or more and 5 or less benzene rings are condensed, and more preferably a condensed ring aromatic hydrocarbon in which 3 or 4 benzene rings are condensed. These groups may have a substituent.
  • the condensed aromatic hydrocarbon group in which 3 to 10 benzene rings are condensed includes an anthracene ring, a phenanthrene ring, or a ring in which 1 to 7 benzene rings are condensed to these rings. And a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring, and preferably an anthracene ring, a phenanthrene ring, or one or more and three or less benzene rings in these rings.
  • the number of carbon atoms of the aryl group of the condensed ring in R 1A is usually 7 to 60, preferably 9 to 30, and more preferably 10 to 18, excluding the number of carbon atoms of the substituent.
  • Examples of the condensed aryl group in R 1A include a naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, indene A group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from a ring, a fluoranthene ring or a benzofluoranthene ring, preferably a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring , A fluorene ring, a spirobifluorene ring, a pyrene ring, a fluoranthene ring or a benzoflu
  • R 1A may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, or an alkenyl group.
  • a cycloalkenyl group more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, and still more preferably an alkyl group.
  • the number of carbon atoms of the aryl group in the substituent which R 1A may have is usually 6 to 60, preferably 6 to 40, more preferably 6 excluding the number of carbon atoms of the substituent. ⁇ 30.
  • R 1A may have, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring
  • Examples include a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from a chrysene ring, an indene ring, a fluoranthene ring and a benzofluoranthene ring, and preferably a benzene ring, a naphthalene ring or an anthracene ring , A phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spir
  • the number of carbon atoms of the monovalent heterocyclic group in the substituent that R 1A may have is usually 2 to 60, preferably 3 to 30, excluding the number of carbon atoms of the substituent. More preferably, it is 3-20.
  • Examples of the monovalent heterocyclic group in the substituent that R 1A may have include, for example, a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, Triazanaphthalene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, phenazine ring And a group formed by removing one hydrogen atom directly bonded to the carbon atom or hetero atom constituting the ring from the 5,10-dihydrophen
  • the amino group preferably has an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups are further substituted. It may have a group.
  • Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in the substituent that Ar 1 may have.
  • Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in the substituent that Ar 1 may have.
  • the substituent which R 1A may have may further have, preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group
  • Group more preferably an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, and particularly preferably an alkyl group or an aryl group, and these groups further have a substituent. May be.
  • Examples of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that the substituent which R 1A may further have may further have a preferred range and R 1A each have.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which may be the same as the preferred range are the same.
  • R 1A is preferably a group represented by the formula (1-S1) to the formula (1-S17), more preferably a formula (1-1), since the driving voltage of the light emitting device of the present invention becomes lower.
  • S1 to a group represented by formula (1-S8) or formula (1-S14) to formula (1-S17 and more preferably a group represented by formula (1-S1), formula (1-S2) or formula Groups represented by formulas (1-S5) to (1-S8), particularly preferably formula (1-S1), formula (1-S2), formula (1-S5) or formula (1-S6).
  • R 1A is preferably a group represented by the formula (1-S1) to the formula (1-S17), more preferably a formula (1-1), since the driving voltage of the light emitting device of the present invention becomes lower.
  • S1 to a group represented by formula (1-S8) or formula (1-S14) to formula (1-S17 and more preferably a group represented by formula (1-S1), formula (1-S2) or formula Groups represented by formulas (1
  • R S1 and R S2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, or an alkenyl. Represents a group or a cycloalkenyl group, and these groups optionally have a substituent.
  • R S1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, more preferably a hydrogen atom, An alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, more preferably a hydrogen atom, an alkyl group, an aryl group or an alkenyl group, and particularly preferably a hydrogen atom, an alkyl group, an aryl group or An alkenyl group, particularly preferably a hydrogen atom or an aryl group, these groups optionally have a substituent.
  • R S2 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group, A cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group. And particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably an aryl group, and these groups optionally have a substituent.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R S1 and R S2 are the aryl group, monovalent heterocyclic group and R 1A in the substituent which R 1A may have, respectively.
  • Examples of the substituted amino group and the preferred range are the same.
  • Examples and preferred ranges of substituents that R S1 and R S2 may have are the same as examples and preferred ranges of substituents that R 1A may further have. is there.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that R S1 and R S2 may have are aryl in the substituent that Ar 1 may have, respectively.
  • R 2A is preferably an alkyl group, a cycloalkyl group, a monocyclic aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an alkenyl group or a cycloalkenyl group, More preferably, it is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a monocyclic aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, and more preferably an alkyl group or a cycloalkyl group.
  • a monocyclic aryl group, an alkenyl group or a cycloalkenyl group, particularly preferably an alkyl group, a monocyclic aryl group or an alkenyl group, particularly preferably a monocyclic aryl group, and these groups are Furthermore, you may have a substituent.
  • the number of carbon atoms of the monocyclic aryl group in R 2A is preferably 6, not including the number of carbon atoms of the substituent.
  • the monocyclic aryl group for R 2A is preferably a phenyl group which may have a substituent.
  • Examples and preferred ranges of the monovalent heterocyclic group and substituted amino group in R 2A are respectively examples and preferred ranges of the monovalent heterocyclic group and substituted amino group in the substituent that R 1A may have. The same.
  • Examples and preferred ranges of the substituent that R 2A may have are the same as examples and preferred ranges of the substituent that R 1A may have.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that R 2A may have are the aryl group in the substituent that R 1A may have, 1
  • the examples are the same as the examples and preferred ranges of the valent heterocyclic group and substituted amino group.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the substituent which R 2A may further have may further have a preferred range and R 1A each have the preferred range. Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which may be the same as the preferred range are the same.
  • the compound represented by the formula (1A) preferably has the formula (1A-A1), the formula (1A-A2), the formula (1) because the driving voltage of the light emitting device of the present invention becomes lower. 1A-A3), formula (1A-A4), formula (1A-A5) or compound represented by formula (1A-A6), more preferably formula (1A-A1), formula (1A-A4) A compound represented by formula (1A-A5) or formula (1A-A6), more preferably a compound represented by formula (1A-A1) or formula (1A-A5), particularly preferably A compound represented by the formula (1A-A1).
  • the compound represented by the formula (1A) preferably has the formula (1A-A1), the formula (1A-A2), the formula, because the driving voltage of the light-emitting element of the present invention becomes lower.
  • Examples of the compound represented by the formula (1A) include a compound represented by the following formula.
  • n 1B is preferably an integer of 1 to 8, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 4, and particularly preferably an integer of 2 to 4.
  • the number of carbon atoms of the aromatic hydrocarbon group in Ar 1B is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, excluding the number of carbon atoms of the substituent.
  • Examples of the aromatic hydrocarbon group in Ar 1B include benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, A group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the rylene ring, chrysene ring, indene ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring;
  • R 1B is an alkyl group, a cycloalkyl group, a monocyclic aryl group, or a monovalent heterocyclic ring.
  • An aryl group or an alkenyl group, particularly preferably an alkyl group or a monocyclic aryl group, and these groups May further have a substituent.
  • R 1B is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group Group, cycloalkoxy group, aryloxy group, halogen atom, alkenyl group or cycloalkenyl group, more preferably alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, An alkenyl group or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, and particularly preferably an aryl group or an alkenyl group. These groups are further substituted It may have a group.
  • Examples and preferred ranges of the monocyclic aryl group for R 1B are the same as those of the monocyclic aryl group for R 2A and preferred ranges.
  • Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 1B are the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which R 1A may have, respectively. The same as the examples and preferred ranges.
  • R 1B substituent which may be possessed and preferred ranges are the same as examples of the substituent which may be possessed by R 1A and preferred ranges.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that R 1B may have are the aryl group in the substituent that R 1A may have, 1
  • the examples are the same as the examples and preferred ranges of the valent heterocyclic group and substituted amino group.
  • Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the substituent which R 1B may further have may further have and R 1A each have the preferred range. Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which may be the same as the preferred range are the same.
  • R 1B s When there are a plurality of R 1B s , they 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, but the compound represented by the formula (1B) Since the maximum peak wavelength of the emission spectrum is a short wavelength, it is preferable not to form a ring.
  • the compound represented by the formula (1A) and the compound represented by the formula (1B) can be obtained from Aldrich, Luminescence Technology Corp. , AK Scientific, etc.
  • It can be synthesized according to the methods described in Japanese Patent No. 308485, Japanese Patent Application Laid-Open No. 2010-121036, Japanese Patent Application Laid-Open No. 2010-123917, Japanese Patent Application Laid-Open No. 2011-037744, and Japanese Patent Application Laid-Open No. 2011-174059.
  • the first organic layer may contain the first compound alone or two or more kinds. Further, the first organic layer may contain the first light emitting material alone or in combination of two or more kinds.
  • the content of the first light emitting material is usually 0.05 to 80 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight. Since the driving voltage of the light emitting element becomes lower, it is preferably 0.1 to 50 parts by weight, more preferably 1 to 30 parts by weight, still more preferably 5 to 15 parts by weight.
  • the first organic layer is selected from the group consisting of a first compound, a first light emitting material, a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. It may be a layer containing a composition containing at least one material (hereinafter also referred to as “first composition”). However, in the first composition, the light emitting material is different from the first light emitting material. In the first composition, the hole transport material, the hole injection material, the light-emitting material, the electron transport material, and the electron injection material are different from the first compound.
  • the hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound.
  • the hole transport material may have a crosslinking group.
  • polymer compound examples include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof.
  • the polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, and fullerene is preferable.
  • the compounding amount of the hole transport material is usually 1 to 400 parts by weight, preferably 5 when the total of the first compound and the first light emitting material is 100 parts by weight. ⁇ 150 parts by weight.
  • the hole transport material may be used alone or in combination of two or more.
  • Electron transport materials are classified into low molecular compounds and high molecular compounds.
  • the electron transport material may have a crosslinking group.
  • low molecular weight compounds include phosphorescent compounds having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene. And diphenoquinone, and derivatives thereof.
  • polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
  • the polymer compound may be doped with a metal.
  • the compounding amount of the electron transporting material is usually 1 to 400 parts by weight, preferably 5 to 5 parts when the total of the first compound and the first light emitting material is 100 parts by weight. 150 parts by weight.
  • the electron transport material may be used alone or in combination of two or more.
  • the hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively.
  • the hole injection material and the electron injection material may have a crosslinking group.
  • low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • metal phthalocyanines such as copper phthalocyanine
  • carbon such as carbon
  • metal oxides such as molybdenum and tungsten
  • metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • polymer compound examples include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.
  • the amount of the hole injecting material and the electron injecting material is usually 1 to 400 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight. Preferably, the amount is 5 to 150 parts by weight.
  • the electron injection material and the hole injection material may be used alone or in combination of two or more.
  • the electrical conductivity of the conductive polymer is preferably 1 ⁇ 10 ⁇ 5 S / cm to 1 ⁇ 10 3 S / cm.
  • the conductive polymer can be doped with an appropriate amount of ions.
  • the kind of ions to be doped is an anion for a hole injection material and a cation for an electron injection material.
  • the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion.
  • the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
  • the ions to be doped may be used alone or in combination of two or more.
  • Luminescent materials are classified into low molecular compounds and high molecular compounds.
  • the light emitting material may have a crosslinking group.
  • low molecular weight compound examples include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.
  • Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, a group represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine diyl.
  • the light emitting material preferably contains a triplet light emitting complex and / or a polymer compound.
  • triplet light-emitting complex examples include the metal complexes shown below.
  • the blending amount of the light emitting material is usually 1 to 400 parts by weight, preferably 5 to 150 parts when the total of the first compound and the first light emitting material is 100 parts by weight. Parts by weight.
  • Fluorescent materials may be used alone or in combination of two or more.
  • the antioxidant may be any compound that is soluble in the same solvent as the first compound and the first light-emitting material and does not inhibit light emission and charge transport.
  • a phenol-based antioxidant and a phosphorus-based antioxidant Is mentioned.
  • the blending amount of the antioxidant is usually 0.001 to 10 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight.
  • Antioxidants may be used alone or in combination of two or more.
  • First ink A composition containing a first compound, a first light emitting material, and a solvent (hereinafter, also referred to as “first ink”) is formed by spin coating, casting, micro gravure coating, or gravure coating.
  • first ink Bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc.
  • Bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. Can be suitably used.
  • the viscosity of the first ink may be adjusted according to the type of wet method. However, when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging at the time of discharge and flight bending occur. Since it is difficult, it is preferably 1 to 20 mPa ⁇ s at 25 ° C.
  • the solvent contained in the first ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink.
  • the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone,
  • the blending amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight. It is.
  • the second organic layer is a layer containing a crosslinked material of a crosslinking material. Since the crosslinking material is contained in the second organic layer in a crosslinked state, the second organic layer is substantially insolubilized in the solvent. Therefore, when the organic layer is formed on the second organic layer by a wet method, the second organic layer is hardly eroded by the solvent, and the original function is sufficiently exhibited. Moreover, the film formability of the organic layer formed on the second organic layer is improved, and an organic layer having excellent thickness uniformity and excellent surface smoothness is formed.
  • a cross-linked body of the cross-linking material can be obtained by cross-linking the cross-linking material by the above-described method and conditions.
  • the cross-linking material may be a low-molecular compound or a high-molecular compound, but it has at least one cross-linking group selected from the cross-linking group A group because the driving voltage of the light emitting device of the present invention becomes lower.
  • a low molecular compound (hereinafter, also referred to as “second organic layer low molecular compound”), or a high molecular compound (hereinafter, referred to as a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group) It is also preferably a “polymer compound of the second organic layer”), and more preferably a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. .
  • the bridging group selected from the bridging group A group since the driving voltage of the light emitting device of the present invention is lower, preferably the formulas (XL-1) to (XL-4) and (XL-7) to A crosslinking group represented by formula (XL-10) or formula (XL-14) to formula (XL-17), more preferably formula (XL-1), formula (XL-3), formula (XL) -9), a crosslinking group represented by formula (XL-10), formula (XL-16) or formula (XL-17), more preferably formula (XL-1) or formula (XL-16) Or a crosslinking group represented by the formula (XL-17), particularly preferably a crosslinking group represented by the formula (XL-1) or the formula (XL-17), particularly preferably a formula (XL- It is a crosslinking group represented by 17).
  • the structural unit having at least one cross-linking group selected from the cross-linking group A group contained in the polymer compound of the second organic layer is a structural unit represented by formula (2) or formula (2 ′) described later. Although it is preferably a structural unit represented, the structural unit represented below may be sufficient.
  • nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 1 or 2 because the driving voltage of the light emitting device of the present invention becomes lower.
  • N is preferably 2 because the driving voltage of the light emitting device of the present invention is lower.
  • Ar 3 is preferably an aromatic hydrocarbon group which may have a substituent since the driving voltage of the light-emitting element of the present invention becomes lower.
  • the number of carbon atoms of the aromatic hydrocarbon group represented by Ar 3 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.
  • the arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar 3 is preferably a group represented by the formula (A-1) to the formula (A-20), More preferably, groups represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) And more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), This group may have a substituent.
  • the number of carbon atoms of the heterocyclic group represented by Ar 3 is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, excluding the number of carbon atoms of the substituent.
  • the divalent heterocyclic group part excluding n substituents of the heterocyclic group represented by Ar 3 is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.
  • the aromatic hydrocarbon group and heterocyclic group represented by Ar 3 may have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group.
  • Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.
  • the alkylene group represented by L A is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the number of carbon atoms of the substituent. Cycloalkylene group represented by L A is not including the carbon atom number of substituent is usually 3 to 20.
  • the alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.
  • Alkylene group and cycloalkylene group represented by L A may have a substituent.
  • the substituent that the alkylene group and the cycloalkylene group may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group, and these groups further have a substituent. It may be.
  • the arylene group represented by L A may have a substituent.
  • the arylene group is preferably a phenylene group or a fluorenediyl group, more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group.
  • the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, or a bridging group A.
  • a crosslinking group selected from the group is preferred, and these groups may further have a substituent.
  • the divalent heterocyclic group represented by L A is preferably a group represented by formula (AA-1) to formula (AA-34).
  • L A is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group, or an alkylene group, because production of the polymer compound of the second organic layer is facilitated.
  • This group may have a substituent.
  • the driving voltage of the light emitting device of the present invention is lower, preferably the formula (XL-1) to the formula (XL-4), the formula (XL-7) to the formula ( XL-10) or a crosslinking group represented by formula (XL-14) to formula (XL-17), more preferably formula (XL-1), formula (XL-3), formula (XL-9) ), A formula (XL-10), a formula (XL-16) or a formula (XL-17), more preferably a formula (XL-1), a formula (XL-16) or a formula A crosslinking group represented by (XL-17), particularly preferably a crosslinking group represented by formula (XL-1) or formula (XL-17), and particularly preferably a formula (XL-17). It is a crosslinking group represented by these.
  • the structural unit represented by the formula (2) is excellent in the stability and crosslinkability of the polymer compound of the second organic layer, it is based on the total amount of the structural units contained in the polymer compound of the second organic layer. Thus, it is preferably 0.5 to 90 mol%, more preferably 3 to 75 mol%, still more preferably 5 to 60 mol%.
  • the structural unit represented by the formula (2) may be contained in the polymer compound of the second organic layer only in one kind, or in two or more kinds.
  • mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably, because the driving voltage of the light emitting device of the present invention becomes lower. 0.
  • M is preferably 1 or 2 and more preferably 2 because the driving voltage of the light emitting device of the present invention is lower.
  • C is preferably 0 because it facilitates the production of the polymer compound of the second organic layer and lowers the driving voltage of the light emitting device of the present invention.
  • Ar 5 is preferably an aromatic hydrocarbon group which may have a substituent since the driving voltage of the light-emitting element of the present invention becomes lower.
  • the definition and examples of the arylene group portion excluding m substituents of the aromatic hydrocarbon group represented by Ar 5 are the same as the definitions and examples of the arylene group represented by Ar X2 in formula (X) described later. It is.
  • divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar 5 are the divalent heterocyclic group represented by Ar X2 in formula (X) described later. Same as definition and example of part.
  • divalent groups excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar 5 and at least one heterocyclic ring are directly bonded are shown in the formula ( The definition and examples of the divalent group in which at least one arylene group represented by Ar X2 in X) and at least one divalent heterocyclic group are directly bonded are the same.
  • Ar 4 and Ar 6 are preferably an arylene group which may have a substituent since the driving voltage of the light-emitting element of the present invention becomes lower.
  • the definitions and examples of the arylene group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the arylene group represented by Ar X1 and Ar X3 in the formula (X) described later.
  • the definitions and examples of the divalent heterocyclic group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the divalent heterocyclic group represented by Ar X1 and Ar X3 in formula (X) described later. is there.
  • the groups represented by Ar 4 , Ar 5 and Ar 6 may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A halogen atom, a monovalent heterocyclic group and a cyano group are preferred.
  • L A the alkylene group represented by L A
  • a cycloalkylene group an arylene group
  • a divalent heterocyclic The definition and examples of the ring group are the same.
  • crosslinking group represented by X ′ are the same as the definition and example of the crosslinking group represented by X described above.
  • the structural unit represented by the formula (2 ′) is excellent in the stability of the polymer compound in the second organic layer and in the crosslinking property of the polymer compound in the second organic layer.
  • the amount is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of structural units contained in the polymer compound in the layer.
  • the structural unit represented by the formula (2 ′) may be included alone or in combination of two or more in the polymer compound of the second organic layer.
  • Examples of the structural unit represented by the formula (2) include structural units represented by the formula (2-1) to the formula (2-30), and the structural unit represented by the formula (2 ′) Examples include structural units represented by the formulas (2′-1) to (2′-9).
  • it is preferably a structural unit represented by the formula (2-1) to the formula (2-30), more preferably the formula (2 -1) to Formula (2-15), Formula (2-19), Formula (2-20), Formula (2-23), Formula (2-25), or Formula (2-30) More preferably a structural unit represented by formula (2-1) to formula (2-9), formula (2-20), formula (2-22) or formula (2-30).
  • the second organic layer further contains a structural unit represented by the formula (X).
  • the polymer compound of the second organic layer preferably further includes a structural unit represented by the formula (Y) because the driving voltage of the light-emitting element of the present invention becomes lower.
  • the structural unit represented by the formula (X) and the formula (Y) It is preferable that the structural unit represented by this is included.
  • a X1 and a X2 each independently represent an integer of 0 or more.
  • Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
  • Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. And these groups may have a substituent.
  • Ar X2 and Ar X4 When there are a plurality of Ar X2 and Ar X4 , they may be the same or different.
  • R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of R X2 and R X3 , they may be the same or different. ]
  • a X1 is preferably an integer of 2 or less, more preferably 1, since the driving voltage of the light emitting device of the present invention is lower.
  • a X2 is preferably an integer of 2 or less, more preferably 0, because the driving voltage of the light emitting device of the present invention becomes lower.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. Also good.
  • the arylene group represented by Ar X1 and Ar X3 is more preferably a group represented by the formula (A-1) or the formula (A-9), and more preferably a formula (A-1). These groups may have a substituent.
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably an arylene group which may have a substituent.
  • the arylene group represented by Ar X2 and Ar X4 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11). Or it is group represented by a formula (A-19), and these groups may have a substituent.
  • the more preferable range of the divalent heterocyclic group represented by Ar X2 and Ar X4 is the same as the more preferable range of the divalent heterocyclic group represented by Ar X1 and Ar X3 .
  • Examples of the divalent group in which at least one arylene group represented by Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulae. These may have a substituent.
  • R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R XX is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • Ar X2 and Ar X4 are preferably an arylene group which may have a substituent.
  • the substituent which the groups represented by Ar X1 to Ar X4 and R X1 to R X3 may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups further have a substituent. You may do it.
  • the structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1) to the formula (X-7), more preferably the formula (X-3) to the formula (X -7), more preferably structural units represented by formula (X-3) to formula (X-6).
  • R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or cyano. Represents a group, and these groups may have a substituent.
  • a plurality of R X4 may be the same or different.
  • a plurality of R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
  • the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 90 mol% based on the total amount of the structural units contained in the polymer compound of the second organic layer. More preferably, it is 1 to 70 mol%, and still more preferably 10 to 50 mol%.
  • Examples of the structural unit represented by the formula (X) include structural units represented by the formula (X1-1) to the formula (X1-19), preferably the formula (X1-6) to the formula (X1 -14).
  • the structural unit represented by the formula (X) may be included alone or in combination of two or more.
  • Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent.
  • the arylene group represented by Ar Y1 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A) A-13) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9) formula (A-11) or formula A group represented by (A-19), and these groups optionally have a substituent;
  • the divalent heterocyclic group represented by Ar Y1 is represented by the formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) ) Or a group represented by formula (AA-20), particularly preferably represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) These groups may have a substituent.
  • the ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar Y1 described above.
  • the divalent group in which at least one arylene group represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded to each other is at least represented by Ar X2 and Ar X4 in the formula (X). Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.
  • the substituent that the group represented by Ar Y1 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.
  • Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-1) to the formula (Y-7), and from the viewpoint of the driving voltage of the light emitting element of the present invention.
  • a structural unit represented by the formula (Y-1) or (Y-2) and from the viewpoint of electron transport properties of the polymer compound of the second organic layer, preferably the formula (Y-3 ) Or a structural unit represented by formula (Y-4), and preferably from formula (Y-5) to formula (Y-7) from the viewpoint of hole transport properties of the polymer compound of the second organic layer.
  • a structural unit represented by the formula (Y-1) or (Y-2) Preferably a structural unit represented by the formula (Y-3 ) Or a structural unit represented by formula (Y-4), and preferably from formula (Y-5) to formula (Y-7) from the viewpoint of hole transport properties of the polymer compound of the second organic layer.
  • R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a plurality of R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
  • R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
  • the structural unit represented by the formula (Y-1) is preferably a structural unit represented by the formula (Y-1 ′).
  • R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a plurality of R Y11 may be the same or different.
  • R Y11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.
  • R Y1 represents the same meaning as described above.
  • X Y1 is, -C (R Y2) 2 -
  • R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of R Y2 may be the same or different, and R Y2 may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]
  • R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. May be.
  • R Y2 in the group represented by —C (R Y2 ) 2 — in X Y1 is preferably an alkyl group or a cycloalkyl group, both are aryl groups, and both are monovalent complex A cyclic group, or one is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group. May have a substituent.
  • Two R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • R Y2 forms a ring
  • the group represented by —C (R Y2 ) 2 — Is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. You may do it.
  • the combination of two R Y2 in the group represented by —C (R Y2 ) ⁇ C (R Y2 ) — is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups optionally have a substituent.
  • R Y2 in the group represented by —C (R Y2 ) 2 —C (R Y2 ) 2 — are preferably an alkyl group or a substituent which may have a substituent. It is a cycloalkyl group that may have.
  • a plurality of R Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded.
  • R Y2 forms a ring —C (R Y2 ) 2 —C (R Y2 ) 2 —
  • the group represented is preferably a group represented by the formula (Y-B1) to the formula (Y-B5), more preferably a group represented by the formula (Y-B3). It may have a substituent.
  • R Y2 represents the same meaning as described above.
  • the structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).
  • R Y1 represents the same meaning as described above.
  • R Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • R Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.
  • R Y1 represents the same meaning as described above.
  • R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.
  • Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-11) to the formula (Y-56), and preferably the formula (Y-11) to the formula (Y Y-55).
  • the structural unit represented by the formula (Y), in which Ar Y1 is an arylene group, is included in the polymer compound of the second organic layer because the driving voltage of the light-emitting element of the present invention is lower.
  • the amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the structural units.
  • the structural unit that is a group of the organic compound is preferably 0.5 to a total amount of the structural units contained in the polymer compound of the second organic layer because the polymer compound of the second organic layer is excellent in charge transportability. It is 40 mol%, more preferably 3 to 30 mol%.
  • the structural unit represented by the formula (Y) may be contained in the high molecular compound of the second organic layer, or may be contained in two or more types.
  • Examples of the polymer compound in the second organic layer include polymer compounds P-1 to P-8 shown in Table 1.
  • the “other structural unit” means a structural unit other than the structural units represented by Formula (2), Formula (2 ′), Formula (X), and Formula (Y).
  • the polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes.
  • a copolymer obtained by copolymerizing seed raw material monomers is preferable.
  • the number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 to 5 ⁇ 10 5 , more preferably 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
  • the polymer compound of the second organic layer can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc. Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
  • a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
  • a method of charging the monomer a method of charging the entire amount of the monomer into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.
  • transition metal catalysts examples include palladium catalysts and nickel catalysts.
  • Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination.
  • a lower alcohol such as methanol
  • filtering the deposited precipitate and then drying.
  • These methods are performed alone or in combination.
  • the purity of the polymer compound in the second organic layer is low, it can be purified by a usual method such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, or the like.
  • the low molecular compound of the second organic layer is preferably a low molecular compound represented by the formula (3).
  • m B1 is generally an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, and even more preferably 0 or 0, because synthesis of the crosslinking material is facilitated. 1, particularly preferably 0.
  • m B2 is usually an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably, since it facilitates the synthesis of the cross-linking material and lowers the driving voltage of the light emitting device of the present invention. Is an integer of 0 to 3, more preferably 1 or 2, and particularly preferably 1.
  • m B3 is generally an integer of 0 to 5, and is preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and still more preferably 0 because synthesis of the cross-linking material is facilitated. is there.
  • the definition and examples of the arylene group part excluding m B3 substituents of the aromatic hydrocarbon group represented by Ar 7 are the definitions and examples of the arylene group represented by Ar X2 in the aforementioned formula (X). The same.
  • divalent heterocyclic group part excluding m B3 substituents of the heterocyclic group represented by Ar 7 are the divalent heterocyclic ring represented by Ar X2 in the above formula (X). Same as definition and example of base part.
  • the definition and examples of the divalent group excluding m B3 substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar 7 and at least one heterocycle are directly bonded are as described above.
  • the definition and example of the divalent group in which at least one kind of arylene group represented by Ar X2 and at least one kind of divalent heterocyclic group in (X) are directly bonded are the same.
  • Ar 7 is preferably an aromatic hydrocarbon group because the driving voltage of the light-emitting element of the present invention is low, and this aromatic hydrocarbon group may have a substituent.
  • alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by L B1 are respectively the alkylene group, cycloalkylene group, arylene group and divalent represented by L A described above. This is the same as the definition and example of the heterocyclic group of.
  • L B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, still more preferably a phenylene group, a fluorenediyl group or An alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups optionally have a substituent.
  • X ′′ is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any one of the formulas (XL-1) to (XL-17), more preferably the formula (XL -1), a crosslinking group represented by formula (XL-3), formula (XL-7) to formula (XL-10), formula (XL-16) or formula (XL-17), or an aryl group More preferably a crosslinking group represented by the formula (XL-1), the formula (XL-16) or the formula (XL-17), a phenyl group, a naphthyl group or a fluorenyl group.
  • XL-16 or a crosslinking group represented by the formula (XL-17), a phenyl group or a naphthyl group, particularly preferably a crosslinking group represented by the formula (XL-16) or a naphthyl group, These groups may have a substituent.
  • cross-linking material examples include low molecular compounds represented by formulas (3-1) to (3-16), and preferably represented by formulas (3-1) to (3-10). Low molecular compounds, more preferably low molecular compounds represented by formulas (3-5) to (3-9).
  • the low molecular weight compound of the second organic layer is available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source. In addition, it is compoundable according to the method described in the international publication 1997/033193, the international publication 2005/035221, and the international publication 2005/049548, for example.
  • the crosslinked material of the crosslinking material may be contained singly or in combination of two or more.
  • the second organic layer includes a crosslinked material of a crosslinking material and at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. May be a layer containing a composition (hereinafter, also referred to as “second composition”).
  • Examples and preferred ranges of the hole transport material, electron transport material, hole injection material, electron injection material and luminescent material contained in the second composition are the hole transport material contained in the first composition.
  • the examples of the electron transport material, the hole injection material, the electron injection material, and the light emitting material are the same as the preferred range.
  • the compounding amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material are each usually 1 when the crosslinked material is 100 parts by weight. Up to 400 parts by weight, preferably 5 to 150 parts by weight.
  • the blending amount of the antioxidant is usually 0.001 to 10 parts by weight when the crosslinked material of the crosslinking material is 100 parts by weight.
  • the second composition containing the crosslinking material and the solvent (hereinafter also referred to as “second ink”) can be suitably used in the wet method described in the section of the first ink.
  • the preferable range of the viscosity of the second ink is the same as the preferable range of the viscosity of the first ink.
  • Examples and preferred ranges of the solvent contained in the second ink are the same as examples and preferred ranges of the solvent contained in the first ink.
  • the compounding amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight when the crosslinking material is 100 parts by weight.
  • the light emitting element of the present invention may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.
  • the first organic layer is usually a light emitting layer (hereinafter referred to as “first light emitting layer”).
  • the second organic layer is usually a hole transport layer, a second light emitting layer or an electron transport layer, preferably a hole transport layer or a second light emitting layer, more preferably. Is a hole transport layer.
  • the first organic layer and the second organic layer are preferably adjacent to each other because the driving voltage of the light emitting device of the present invention becomes lower.
  • the second organic layer is preferably a layer provided between the anode and the first organic layer because the driving voltage of the light emitting device of the present invention is lower. More preferably, it is a hole transport layer or a second light emitting layer provided between the first organic layers, and it is further a hole transport layer provided between the anode and the first organic layer. preferable.
  • the driving voltage of the light emitting device of the present invention when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the driving voltage of the light emitting device of the present invention is lower, It is preferable to further have a hole injection layer between the second organic layer.
  • the driving voltage of the light-emitting element of the present invention becomes lower, so the cathode and the first organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer.
  • the driving voltage of the light emitting device of the present invention becomes lower, so the anode It is preferable to further include at least one of a hole injection layer and a hole transport layer between the first organic layer and the second organic layer.
  • the driving voltage of the light emitting element of the present invention becomes lower, so the cathode and the first organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer between the layers.
  • the driving voltage of the light emitting device of the present invention becomes lower, so that the anode
  • at least one of a hole injection layer and a hole transport layer is further provided between the first organic layer and the first organic layer.
  • the driving voltage of the light emitting element of the present invention becomes lower, so the cathode and the second organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer between the layers.
  • the driving voltage of the light emitting device of the present invention when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light emitting device of the present invention is lower, It is preferable to further include at least one of a hole injection layer and a hole transport layer between one organic layer.
  • the driving voltage of the light-emitting element of the present invention when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light-emitting element of the present invention is lower, so the cathode, the second organic layer, It is preferable to further have an electron injection layer in between.
  • the layer structure of the light emitting device of the present invention include the layer structures represented by the following (d1) to (d15).
  • the light-emitting element of the present invention usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.
  • “/” means that the layers before and after are adjacently stacked.
  • “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” means the second light emitting layer (second organic layer) and the first light emitting layer (second organic layer). The light emitting layer (first organic layer) is adjacently laminated.
  • the layer configuration represented by (d3) to (d12) is preferable, and the layer configuration represented by (d7) to (d10) is more preferable.
  • the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are each provided in two or more layers as necessary. Also good.
  • anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers, and cathodes they may be the same or different.
  • the thickness of the anode, hole injection layer, hole transport layer, first light emitting layer, second light emitting layer, electron transport layer, electron injection layer and cathode is usually 1 nm to 1 ⁇ m, preferably 2 nm to It is 500 nm, more preferably 5 nm to 150 nm.
  • the order, number, and thickness of the layers to be stacked may be adjusted in consideration of the driving voltage of the light emitting element and the element life.
  • the second light emitting layer is usually a layer containing a second organic layer or a light emitting material.
  • the second light emitting layer is a layer containing a light emitting material
  • examples of the light emitting material contained in the second light emitting layer include the light emitting material that may be contained in the first composition. It is done.
  • the light emitting material contained in the second light emitting layer may be contained singly or in combination of two or more.
  • the second light-emitting layer is the second organic layer. It is preferable that
  • the hole transport layer is usually a layer containing a second organic layer or a hole transport material.
  • the hole transport layer is a layer containing a hole transport material
  • examples of the hole transport material include a hole transport material that may be contained in the first composition described above.
  • the hole transport material contained in the hole transport layer may be contained singly or in combination of two or more.
  • the hole-transport layer is the second organic layer. Preferably there is.
  • the electron transport layer is usually the second organic layer or a layer containing an electron transport material, and preferably a layer containing an electron transport material.
  • the electron transport layer is a layer containing an electron transport material
  • examples of the electron transport material contained in the electron transport layer include the electron transport material that may be contained in the first composition described above. .
  • the electron transport material contained in the electron transport layer may be contained singly or in combination of two or more.
  • the hole injection layer is a layer containing a hole injection material.
  • a hole injection material contained in a hole injection layer the hole injection material which the above-mentioned 1st composition may contain is mentioned, for example.
  • the hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.
  • the electron injection layer is a layer containing an electron injection material.
  • an electron injection material contained in an electron injection layer the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example.
  • the electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.
  • the substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed.
  • the substrate is made of a material such as glass, plastic, or silicon.
  • the electrode farthest from the substrate is transparent or translucent.
  • Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • conductive metal oxides and translucent metals preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
  • ITO indium tin oxide
  • Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds.
  • Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
  • At least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.
  • Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a laminating method.
  • a low molecular compound is used as a method for forming each of the first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, the electron injection layer, and the like.
  • a vacuum deposition method from a powder a method by film formation from a solution or a molten state can be mentioned, and when a polymer compound is used, for example, a method by film formation from a solution or a molten state can be mentioned.
  • the first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer are the first ink, the second ink, and the above-described light-emitting material and hole. It can be formed by a wet method such as a spin coating method or an ink jet printing method using inks each containing a transport material, an electron transport material, a hole injection material, and an electron injection material.
  • the method for producing a light-emitting device of the present invention includes a step of forming a second organic layer between an anode and a cathode by a wet method, a step of crosslinking the formed second organic layer, The method includes a step of forming an organic layer on the crosslinked second organic layer by a wet method.
  • the second organic layer is formed on an organic layer such as an anode or a hole transport layer and a hole injection layer, for example.
  • the organic layer formed on the second organic layer may be the first organic layer, and may be an organic layer such as an electron transport layer, a hole injection layer, and a second light emitting layer.
  • planar anode and the cathode may be arranged so as to overlap each other.
  • pattern-like light emission a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, a layer that is desired to be a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern.
  • a segment type display device capable of displaying numbers, characters, and the like can be obtained.
  • both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter.
  • the dot matrix display device can be driven passively or can be driven actively in combination with TFTs. These display devices can be used for displays of computers, televisions, portable terminals and the like.
  • the planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source and display device.
  • the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound are either one of the following size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. Determined by The SEC measurement conditions are as follows.
  • the polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 ⁇ L was injected into SEC. The mobile phase was run at a flow rate of 2.0 mL / min.
  • PLgel MIXED-B manufactured by Polymer Laboratories
  • a UV-VIS detector manufactured by Shimadzu Corporation, trade name: SPD-10Avp was used as the detector.
  • LC-MS was measured by the following method.
  • the measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 ⁇ L was injected into LC-MS (manufactured by Agilent, trade name: 1100LCMSD).
  • the mobile phase of LC-MS was used while changing the ratio of acetonitrile and tetrahydrofuran, and was allowed to flow at a flow rate of 0.2 mL / min.
  • L-column 2 ODS 3 ⁇ m
  • TLC-MS was measured by the following method. A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran or chloroform at an arbitrary concentration, and applied on a TLC plate for DART (trade name: YSK5-100, manufactured by Techno Applications), and TLC-MS (JEOL Ltd.) (Trade name: JMS-T100TD (The AccuTOF TLC)). The helium gas temperature during measurement was adjusted in the range of 200 to 400 ° C.
  • NMR NMR was measured by the following method. About 5 to 10 mg of a measurement sample, about 0.5 mL of heavy chloroform (CDCl 3 ), heavy tetrahydrofuran, heavy dimethyl sulfoxide, heavy acetone, heavy N, N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol Alternatively, it was dissolved in methylene chloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).
  • HPLC high performance liquid chromatography
  • Kaseisorb LC ODS 2000 manufactured by Tokyo Chemical Industry
  • ODS column As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry) or an ODS column having equivalent performance was used.
  • the detector a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used.
  • the maximum peak wavelength of the emission spectrum of the compound was measured with a spectrophotometer (manufactured by JASCO Corporation, FP-6500) at room temperature.
  • a toluene solution in which the compound was dissolved in xylene at a concentration of about 0.8 ⁇ 10 ⁇ 4 mass% was used as a sample.
  • excitation light UV light having a wavelength of 325 nm was used.
  • HM1 Synthesis of Compounds HM-1 to HM-6, and Obtained Compound HM-1 was synthesized according to the method described in JP2011-174059A.
  • Compound HM-2 was purchased from AK Scientific.
  • Compound HM-3 was synthesized according to the method described in International Publication No. 2011/137922.
  • Compound HM-4 and Compound HM-5 were synthesized according to the methods described in JP2011-10000942 and International Publication No. 2011-137922.
  • Compound HM-6 was synthesized according to the method described in International Publication No. 2011/098030.
  • the maximum peak wavelength of the emission spectrum of Compound HM-1 was 426 nm.
  • the maximum peak wavelength of the emission spectrum of Compound HM-2 was 425 nm.
  • the maximum peak wavelength of the emission spectrum of compound HM-3 was 430 nm.
  • the maximum peak wavelength of the emission spectrum of Compound HM-4 was 430 nm.
  • the maximum peak wavelength of the emission spectrum of Compound HM-5 was 415 nm.
  • the maximum peak wavelength of the emission spectrum of compound HM-6 was 431 nm.
  • Compound EM-7 was synthesized according to the method described in International Publication No. 2005/033051.
  • Compound EM-8 was synthesized according to the method described in JP-A-2007-142171.
  • Compound EM-A1 was synthesized according to the method described in JP2011-105643A.
  • the obtained solid was dissolved in toluene and washed with ion exchange water, and then the aqueous layer was removed.
  • the obtained organic layer was filtered with a filter coated with silica gel, and the obtained filtrate was concentrated under reduced pressure.
  • the obtained concentrate was crystallized using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure to obtain Compound EM-9 (3.5 g).
  • Compound EM-9 had an HPLC area percentage value of 99.5% or more.
  • the maximum peak wavelength of the emission spectrum of Compound EM-1 was 439 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-2 was 441 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-3 was 460 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-4 was 446 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-5 was 446 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-6 was 453 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-7 was 453 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-8 was 502 nm.
  • the maximum peak wavelength of the emission spectrum of Compound EM-9 was 440 nm.
  • the maximum peak wavelength of the emission spectrum of compound EM-A1 was 454 nm.
  • the polymer compound HTL-1 has a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound M6 and the structural unit derived from the compound M7 are configured in a molar ratio of 50:50. It is a copolymer.
  • Polymer compound HTL-2 was synthesized according to the method described in International Publication No. 2015/194448 using Compound M5 and Compound M9.
  • the theoretical value obtained from the amount of charged raw materials for polymer compound HTL-2 was that the structural unit derived from compound M5 and the structural unit derived from compound M9 were composed at a molar ratio of 50:50. It is a copolymer.
  • the theoretical value obtained from the amount of charged raw material for polymer compound HTL-3 is that the structural unit derived from compound M6, the structural unit derived from compound M7, and the structural unit derived from compound M8 are: A copolymer composed of a molar ratio of 50: 42.5: 7.5.
  • the theoretical value obtained from the amount of the raw material used for polymer compound HTL-4 is that the structural unit derived from compound M3, the structural unit derived from compound M4, and the structural unit derived from compound M5 are: It is a copolymer composed of 45: 5: 50 molar ratio.
  • the low molecular weight compound HTM-1 was purchased from Luminesense Technology.
  • Example D1 Fabrication and evaluation of light-emitting element D1 (formation of anode and hole injection layer)
  • An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by sputtering.
  • a hole injection material ND-3202 manufactured by Nissan Chemical Industries
  • the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
  • the polymer compound HTL-4 was dissolved in xylene at a concentration of 0.6% by weight. Using the obtained xylene solution, a second film was formed on the hole injection layer by spin coating to a thickness of 20 nm, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. An organic layer of was formed. By this heating, the polymer compound HTL-4 became a crosslinked product.
  • the substrate on which the first organic layer is formed is depressurized to 1 ⁇ 10 ⁇ 4 Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the first organic layer, and then fluorinated. About 80 nm of aluminum was deposited on the sodium layer. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.
  • Example D2 Fabrication and Evaluation of Light-Emitting Element D2
  • a light-emitting element D2 was fabricated in the same manner as in Example D1, except that Compound EM-1 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D2.
  • the driving voltage at 400 cd / m 2 was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).
  • Example D3 Production and evaluation of light-emitting device D3 A light-emitting device D3 was produced in the same manner as in Example D1, except that Compound EM-3 was used instead of Compound EM-2 in Example D1.
  • Example D4 Production and evaluation of light-emitting device D4 A light-emitting device D4 was produced in the same manner as in Example D1, except that Compound EM-4 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D4.
  • the driving voltage at 400 cd / m 2 was 6.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).
  • Example D5 Production and evaluation of light-emitting device D5 A light-emitting device D5 was produced in the same manner as in Example D1, except that Compound EM-5 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D5.
  • the driving voltage at 400 cd / m 2 was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).
  • Example D6 Fabrication and Evaluation of Light-Emitting Element D6 A light-emitting element D6 was fabricated in the same manner as in Example D1, except that Compound EM-6 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D6.
  • the driving voltage at 400 cd / m 2 was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.18).
  • Example D7 Production and evaluation of light-emitting device D7 A light-emitting device D7 was produced in the same manner as in Example D1, except that Compound EM-7 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D7.
  • the driving voltage at 400 cd / m 2 was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.24).
  • Example D8 Production and evaluation of light-emitting device D8 A light-emitting device D8 was produced in the same manner as in Example D1, except that Compound EM-8 was used instead of Compound EM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D8.
  • the driving voltage at 400 cd / m 2 was 5.5 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.50).
  • Example D9 Production and evaluation of light-emitting device D9 A light-emitting device D9 was produced in the same manner as in Example D1, except that compound HM-3 was used instead of compound HM-2 in Example D1.
  • Example D10 Production and evaluation of light-emitting device D10 A light-emitting device D10 was produced in the same manner as in Example D1, except that compound HM-4 was used instead of compound HM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D10.
  • the driving voltage at 400 cd / m 2 was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).
  • Example D11 Production and evaluation of light-emitting device D11 A light-emitting device D11 was produced in the same manner as in Example D1, except that compound HM-5 was used instead of compound HM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D11.
  • the driving voltage at 400 cd / m 2 was 5.2 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).
  • Example D12 Production and evaluation of light-emitting device D12 A light-emitting device D12 was produced in the same manner as in Example D1, except that Compound EM-9 was used instead of Compound EM-2 in Example D1.
  • Example D13 Production and evaluation of light-emitting device D13 A light-emitting device D13 was produced in the same manner as in Example D1, except that compound HM-6 was used instead of compound HM-2 in Example D1.
  • EL light emission was observed by applying a voltage to the light emitting element D13.
  • the driving voltage at 400 cd / m 2 was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.18).
  • Example D14 Production and evaluation of light-emitting device D14 A light-emitting device D14 was produced in the same manner as in Example D13, except that Compound EM-8 was used instead of Compound EM-2 in Example D13.
  • EL light emission was observed by applying a voltage to the light emitting element D14.
  • the driving voltage at 400 cd / m 2 was 6.6 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.46).
  • Example D15 Production and Evaluation of Light-Emitting Element D15
  • “High molecular compound HTL-4 was dissolved in xylene at a concentration of 0.6% by weight”.
  • a light-emitting device D15 was produced in the same manner as in Example D1, except that “Compound HTM-1 was dissolved in chlorobenzene at a concentration of 0.9% by weight”.
  • EL light emission was observed by applying a voltage to the light emitting element D15.
  • the driving voltage at 400 cd / m 2 was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).
  • Example D16 Production and evaluation of light-emitting device D16 A light-emitting device D16 was produced in the same manner as in Example D15 except that Compound EM-3 was used instead of Compound EM-2 in Example D15.
  • EL light emission was observed by applying a voltage to the light emitting element D16.
  • the driving voltage at 400 cd / m 2 was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.12).
  • Example D17 Production and evaluation of light-emitting device D17 A light-emitting device D17 was produced in the same manner as in Example D15 except that Compound EM-9 was used instead of Compound EM-2 in Example D15.
  • EL light emission was observed by applying a voltage to the light emitting element D17.
  • the driving voltage at 400 cd / m 2 was 6.4 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).
  • EL light emission was observed by applying a voltage to the light emitting device CD1.
  • the driving voltage at 400 cd / m 2 was 7.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).
  • Example D18 Production and evaluation of light-emitting device D18 Light-emitting device D18 was prepared in the same manner as in Example D1, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D1. Produced.
  • EL light emission was observed by applying a voltage to the light emitting element D18.
  • the driving voltage at 3000 cd / m 2 was 8.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).
  • the drive voltage at 5000 cd / m 2 was 9.3 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).
  • Example D19 Production and evaluation of light-emitting device D19 Light-emitting device D19 was prepared in the same manner as in Example D2, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D2. Produced.
  • the driving voltage at 3000 cd / m 2 was 8.1 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).
  • the drive voltage at 5000 cd / m 2 was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).
  • Example D20 Production and evaluation of light-emitting device D20 Light-emitting device D20 was prepared in the same manner as in Example D2, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D8. Produced.
  • EL light emission was observed by applying a voltage to the light emitting element D20.
  • the driving voltage at 3000 cd / m 2 was 7.0 V, and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).
  • the drive voltage at 5000 cd / m 2 was 7.9 V, and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).
  • Example D21 Production and evaluation of light-emitting device D21 A light-emitting device D21 was prepared in the same manner as in Example D17, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D17. Produced.
  • the driving voltage at 3000 cd / m 2 was 8.5 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.12).
  • the drive voltage at 5000 cd / m 2 was 10.1 V, and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).
  • Example D22 Production and evaluation of light-emitting device D22 A light-emitting device D22 was fabricated in the same manner as in Example D13, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D13. Produced.
  • the driving voltage at 3000 cd / m 2 was 8.2 V, and the CIE chromaticity coordinates (x, y) were (0.21, 0.43).
  • the drive voltage at 5000 cd / m 2 was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).
  • the driving voltage at 3000 cd / m 2 was 9.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.13).
  • the drive voltage at 5000 cd / m 2 was 11.1 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.13).
  • Example CD3 Production and Evaluation of Light Emitting Element CD3
  • the light emitting element CD3 was fabricated in the same manner as in Example D1, except that the polymer compound HTL-1 was used instead of the polymer compound HTL-4 in Example D1. Produced.
  • Example D23 Production and evaluation of light-emitting device D23 A light-emitting device D23 was prepared in the same manner as in Example D2, except that polymer compound HTL-3 was used instead of polymer compound HTL-4 in Example D2. Produced.
  • the driving voltage at 100 cd / m 2 was 4.6 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).
  • the driving voltage at 200 cd / m 2 was 5.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).
  • EL light emission was observed by applying a voltage to the light emitting device CD4.
  • the driving voltage at 100 cd / m 2 was 10.6 V, and the CIE chromaticity coordinates (x, y) were (0.19, 0.17). Further, although the voltage was applied up to 12 V, it did not reach 200 cd / m 2 .

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

La présente invention aborde le problème de la production d'un élément électroluminescent ayant une faible tension d'attaque. L'invention résout ce problème en réalisant un élément électroluminescent comprenant une anode, une cathode ainsi qu'une première couche organique et une deuxième couche organique disposées entre l'anode et la cathode, la première couche organique contenant une composition qui contient un premier composé et un premier matériau électroluminescent, le premier composé étant le composé représenté par la formule (1A), le premier matériau électroluminescent étant le composé représenté par la formule (1a) ou le composé représenté par la formule (1B), et la deuxième couche organique contenant un corps de réticulation comprenant un matériau de réticulation. [Dans la formule, Ar1A représente un groupe hydrocarboné aromatique à noyaux condensés dans lequel les noyaux benzéniques 3 à 10 sont condensés. R1A représente un groupe aryle à noyaux condensés. R2A représente un groupe aryle, etc.] [Dans la formule, Ar1B représente un groupe hydrocarboné aromatique. R1B représente un groupe alkyle, etc.]
PCT/JP2017/012251 2016-03-29 2017-03-27 Élément électroluminescent WO2017170325A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008059713A1 (fr) * 2006-11-15 2008-05-22 Idemitsu Kosan Co., Ltd. Composé de fluoranthène, dispositif électroluminescent organique utilisant le composé de fluoranthène et solution contenant un matériau électroluminescent organique
JP2010183010A (ja) * 2009-02-09 2010-08-19 Mitsubishi Chemicals Corp 有機電界発光素子用組成物、有機薄膜、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2010185008A (ja) * 2009-02-12 2010-08-26 Mitsubishi Chemicals Corp 有機電界発光素子用組成物、有機薄膜、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2011108792A (ja) * 2009-11-16 2011-06-02 Mitsubishi Chemicals Corp 有機電界発光素子の製造方法、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008059713A1 (fr) * 2006-11-15 2008-05-22 Idemitsu Kosan Co., Ltd. Composé de fluoranthène, dispositif électroluminescent organique utilisant le composé de fluoranthène et solution contenant un matériau électroluminescent organique
JP2010183010A (ja) * 2009-02-09 2010-08-19 Mitsubishi Chemicals Corp 有機電界発光素子用組成物、有機薄膜、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2010185008A (ja) * 2009-02-12 2010-08-26 Mitsubishi Chemicals Corp 有機電界発光素子用組成物、有機薄膜、有機電界発光素子、有機ｅｌ表示装置および有機ｅｌ照明
JP2011108792A (ja) * 2009-11-16 2011-06-02 Mitsubishi Chemicals Corp 有機電界発光素子の製造方法、有機電界発光素子、有機ｅｌ表示装置及び有機ｅｌ照明

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