WO2011149056A1 - Nouveau composé et composant photo-émetteur l'employant - Google Patents

Nouveau composé et composant photo-émetteur l'employant Download PDF

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WO2011149056A1
WO2011149056A1 PCT/JP2011/062223 JP2011062223W WO2011149056A1 WO 2011149056 A1 WO2011149056 A1 WO 2011149056A1 JP 2011062223 W JP2011062223 W JP 2011062223W WO 2011149056 A1 WO2011149056 A1 WO 2011149056A1
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atom
layer
ring
light emitting
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壮太 柴原
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住友化学株式会社
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    • H—ELECTRICITY
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    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • 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 novel compound and a light emitting device using the same, and more particularly to a novel compound having excellent hole transportability and an organic electroluminescence device using the same.
  • Organic electroluminescence elements (hereinafter sometimes referred to as “organic EL elements”) are suitable for applications such as displays because they are driven at a low voltage, and have recently attracted attention.
  • the organic EL element includes an anode, a cathode, and a light emitting layer disposed between the anode and the cathode, and holes and electrons injected from the anode and the cathode are combined in the light emitting layer. To emit light.
  • an organic EL element as a transparent conductive electrode that transmits light and injects holes, indium oxide, zinc oxide, tin oxide, and their composites, indium tin oxide (ITO), indium zinc -A conductive material made of oxide or the like is used, and by providing a layer that assists the movement of holes in the light emitting layer between this electrode and the light emitting layer, the mobility of holes that are carriers is increased. It is done.
  • ITO indium tin oxide
  • ITO indium zinc -A conductive material made of oxide or the like
  • Non-Patent Document 1 has an organic layer having a film thickness of 65 nm between an anode and a light-emitting layer, and the organic layer is made of poly (3,4-ethylenedioxythiophene) and polystyrenesulfonic acid.
  • An organic EL element that is a hole transport layer containing a mixture hereinafter sometimes referred to as “PEDOT / PSS”.
  • PEDOT / PSS it is difficult to form the PEDOT / PSS in a thin layer. Therefore, when PEDOT / PSS is used as the hole transport layer, there is a problem that the organic EL element becomes thick and the manufacturing cost increases because of the large amount necessary for forming the layer.
  • an object of the present invention is to provide a novel compound having excellent hole transportability while being able to be formed in a thin layer, and a light emitting element such as an organic EL element having an organic layer containing the compound.
  • the present invention has the formula
  • C 1 ring, C 2 ring and C 3 ring represent an aromatic hydrocarbon ring or a heterocyclic ring.
  • A represents a single bond or a divalent group.
  • n 1 represents an integer of 1 to 4
  • n 2 represents an integer of 0 to 4.
  • l 1 represents an integer of 0 to 3
  • l 2 represents an integer of 0 to 4.
  • R 1 , R 2 , and R 3 are the same or different and each represents an alkoxy group, a halogen atom, a hydrogen atom, or a hydroxyl group. When there are a plurality of A, they may be the same or different. When there are a plurality of R 1 s , they may be the same or different.
  • R 2 s When there are a plurality of R 2 s , they may be the same or different. When there are a plurality of R 3 , they may be the same or different.
  • X 1 is a divalent group containing one or more atoms selected from the group consisting of boron atom, carbon atom, nitrogen atom, oxygen atom, phosphorus atom, sulfur atom and selenium atom, oxygen atom, sulfur atom or selenium atom Represents.
  • D represents an alkyl group, an alkoxy group or an aryl group. When there are a plurality of D, they may be the same or different. ] The compound represented by these is provided.
  • the present invention also provides a composition comprising at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material, and the compound.
  • the present invention also provides a solution containing the compound and a solvent.
  • the present invention also provides a thin film containing the compound.
  • the present invention also provides a light emitting device having an electrode composed of an anode and a cathode, and an organic layer containing the compound provided between the electrodes.
  • the compound of the present invention has an excellent hole transport property and functions as an organic layer such as a carrier transport layer in a light emitting device such as an organic EL device. Further, the compound of the present invention can form a thin organic layer, and when used in an organic layer in a light emitting device such as an organic EL device, a thin and inexpensive device can be produced. Therefore, the present invention is extremely useful industrially.
  • C 1 , C 2 and C 3 each independently represents an aromatic hydrocarbon ring or a heterocyclic ring.
  • C 3 may have a substituent.
  • the aromatic hydrocarbon ring has about 6 to 30 carbon atoms, preferably about 6 to 15 carbon atoms, and represents a benzene ring or a condensed aromatic hydrocarbon ring.
  • the carbon number of the aromatic hydrocarbon group does not include the carbon number of the substituent.
  • the heterocyclic ring usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms.
  • the carbon number of the heterocyclic group does not include the carbon number of the substituent.
  • the heterocyclic ring refers to a ring composed of one or more carbon atoms and one or more atoms other than carbon, such as oxygen, sulfur, nitrogen, phosphorus and boron.
  • heterocycles aromatic heterocycles are preferred. Specifically, furan ring, thiophene ring, pyrrole ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, benzofuran ring, benzothiophene ring, indole ring, quinoline ring Quinoxaline ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, acridine ring and the like.
  • the C 1 , C 2 and C 3 aromatic hydrocarbon ring or heterocyclic ring is preferably a benzene ring or a monocyclic heterocyclic ring, and more preferably a benzene ring.
  • Substituents on C 3 are halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, arylalkyl groups, arylalkoxy groups, arylalkylthio groups, alkenyl groups, alkynyl groups, disubstituted Examples include amino groups, trisubstituted silyl groups, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, substituted carboxyl groups, heteroaryloxy groups, and heteroarylthio groups.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the alkyl group may be linear, branched or cyclic, and usually has about 1 to 30 carbon atoms and preferably about 3 to 15 carbon atoms from the viewpoint of solubility in a solvent.
  • Specific examples thereof include methyl Group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group (where t- represents tert-, the same shall apply hereinafter), pentyl group, isoamyl group Group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, lauryl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group , Perfluorohexyl group, perfluoroo
  • the alkoxy group may be linear, branched or cyclic, and usually has about 1 to 30 carbon atoms and preferably about 3 to 15 carbon atoms from the viewpoint of solubility in a solvent.
  • Specific examples thereof include methoxy Group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, Nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyl group, perfluorooctyl group, methoxymethyloxy group, 2 -Methoxyethyloxy group and
  • the alkylthio group may be linear, branched or cyclic, and usually has about 1 to 30 carbon atoms and preferably about 3 to 15 carbon atoms from the viewpoint of solubility in a solvent. Specific examples thereof include methylthio group. Group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group Group, 3,7-dimethyloctylthio group, laurylthio group, trifluoromethylthio group, and the like.
  • Pentylthio, hexylthio, octylthio, 2-ethylhexylthio, decyl Thio, 3,7-dimethyloctylthio group are preferable.
  • An aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and having a condensed ring, two or more independent benzene rings or condensed rings bonded directly or through a group such as vinylene. Also included.
  • the aryl group usually has about 6 to 60 carbon atoms, preferably about 6 to 30 carbon atoms. Specific examples thereof include phenyl groups, C 1 to C 12 alkoxyphenyl groups (C 1 to C 12 are those having 1 carbon atoms).
  • C 1 -C 12 alkylphenyl group 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group
  • Examples thereof include a pentafluorophenyl group, and a C 1 to C 12 alkoxyphenyl group and a C 1 to C 12 alkylphenyl group are preferable from the viewpoints of solubility in an organic solvent, device characteristics, ease of synthesis, and the like.
  • C 1 -C 12 alkoxy examples include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, Nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy and the like are exemplified.
  • C 1 -C 12 alkylphenyl group examples include methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, t -Butylphenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, dodecylphenyl group and the like are exemplified.
  • the aryloxy group usually has about 6 to 60 carbon atoms, preferably about 6 to 30 carbon atoms. Specific examples thereof include a phenoxy group, a C 1 to C 12 alkoxyphenoxy group, a C 1 to C 12 alkylphenoxy group, Examples include 1-naphthyloxy group, 2-naphthyloxy group, pentafluorophenyloxy group and the like. From the viewpoint of solubility in organic solvents, device characteristics, ease of synthesis, etc., C 1 -C 12 alkoxyphenoxy The group C 1 -C 12 alkylphenoxy is preferred.
  • C 1 -C 12 alkoxy examples include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, Nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy and the like are exemplified.
  • C 1 -C 12 alkylphenoxy group examples include methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5-trimethylphenoxy group, methylethylphenoxy group, isopropylphenoxy group, butylphenoxy group.
  • the arylthio group usually has about 6 to 60 carbon atoms, preferably about 6 to 30 carbon atoms. Specific examples thereof include a phenylthio group, a C 1 -C 12 alkoxyphenylthio group, a C 1 -C 12 alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a pentafluorophenylthio group, and the like. From the viewpoints of solubility in a solvent, device characteristics, easiness of synthesis, etc., a C 1 -C 12 alkoxyphenylthio group and a C 1 -C 12 alkylphenylthio group are preferred.
  • the arylalkyl group usually has about 7 to 60 carbon atoms, preferably about 7 to 30 carbon atoms. Specific examples thereof include a phenyl-C 1 -C 12 alkyl group, a C 1 -C 12 alkoxyphenyl-C 1- Examples include C 12 alkyl groups, C 1 -C 12 alkylphenyl-C 1 -C 12 alkyl groups, 1-naphthyl-C 1 -C 12 alkyl groups, 2-naphthyl-C 1 -C 12 alkyl groups, and the like.
  • C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkyl group C 1 -C 12 alkylphenyl -C 1 -C 12 alkyl Groups are preferred.
  • the arylalkoxy group usually has about 7 to 60 carbon atoms, preferably about 7 to 30 carbon atoms. Specific examples thereof include a phenylmethoxy group, a phenylethoxy group, a phenylbutoxy group, a phenylpentyloxy group, a phenylhexyl group.
  • Phenyl-C 1 -C 12 alkoxy groups such as siloxy group, phenylheptyloxy group, phenyloctyloxy group, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkoxy group, C 1 -C 12 alkylphenyl-C Examples include 1 to C 12 alkoxy groups, 1-naphthyl-C 1 to C 12 alkoxy groups, and 2-naphthyl-C 1 to C 12 alkoxy groups.
  • the arylalkylthio group usually has about 7 to 60 carbon atoms, preferably about 7 to 30 carbon atoms. Specific examples thereof include a phenyl-C 1 -C 12 alkylthio group and a C 1 -C 12 alkoxyphenyl-C. Examples include 1 to C 12 alkylthio groups, C 1 to C 12 alkylphenyl-C 1 to C 12 alkylthio groups, 1-naphthyl-C 1 to C 12 alkylthio groups, and 2-naphthyl-C 1 to C 12 alkylthio groups.
  • C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkylthio groups C 1 -C 12 alkylphenyl -C 1 -C A 12 alkylthio group is preferred.
  • the alkenyl group has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms.
  • Specific examples include vinyl group, 1-propylenyl group, 2-propylenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, cyclohexenyl group, 1,3-butadienyl group, cyclohexa-1, Also included are dienyl groups and trienyl groups such as 3-dienyl group and 1,3,5-hexatrienyl group.
  • the alkynyl group has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms.
  • Specific examples include an ethynyl group, a 1-propynyl group, a 2-propylenyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a cyclohexylethynyl group, and the like, and a diynyl group such as a 1,3-butadiynyl group Is also included.
  • disubstituted amino group examples include an amino group substituted with two groups selected from an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, and the alkyl group, aryl group, arylalkyl group Alternatively, the monovalent heterocyclic group may have a substituent.
  • the carbon number of the disubstituted amino group is usually about 2 to 60, preferably about 2 to 30, not including the carbon number of the substituent.
  • Examples of the trisubstituted silyl group include a silyl group substituted with three groups selected from an alkyl group, an aryl group, an arylalkyl group, or a monovalent heterocyclic group.
  • the substituted silyl group usually has about 3 to 90 carbon atoms, preferably about 3 to 45 carbon atoms.
  • the alkyl group, aryl group, arylalkyl group or monovalent heterocyclic group may have a substituent.
  • trimethylsilyl group triethylsilyl group, tripropylsilyl group, tri-isopropylsilyl group, dimethyl-isopropylsilyl group, diethyl-isopropylsilyl group, t-butyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethyl Silyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethylsilyl group, lauryldimethylsilyl group, triphenylsilyl Group, tri-p-xylylsilyl group, tribenzylsilyl group, diphenylmethylsilyl group, t-butyldip
  • the acyl group usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms. Specific examples thereof include acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, benzoyl group, trifluoro group. Examples include an acetyl group and a pentafluorobenzoyl group.
  • the acyloxy group usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms. Specific examples thereof include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyl group. Examples thereof include an oxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
  • the imine residue has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms, and specific examples thereof include groups represented by the following structural formulas.
  • the amide group usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms. Specific examples thereof include a formamide group, an acetamide group, a propioamide group, a butyroamide group, a benzamide group, a trifluoroacetamide group, Examples include pentafluorobenzamide group, diformamide group, diacetamide group, dipropioamide group, dibutyroamide group, dibenzamide group, ditrifluoroacetamide group, dipentafluorobenzamide group, and the like.
  • the acid imide group includes a residue obtained by removing a hydrogen atom bonded to the nitrogen atom from an acid imide, and has about 4 to 30 carbon atoms, preferably about 4 to 15 carbon atoms. Specific examples include the following groups.
  • the monovalent heterocyclic group means an atomic group remaining after removing one hydrogen atom on the heterocyclic ring of the heterocyclic compound, and usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms.
  • carbon number of a substituent is not included in carbon number.
  • the heterocyclic compound is an organic compound having a cyclic structure in which the elements constituting the ring include not only carbon atoms but also hetero atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, etc. in the ring.
  • thienyl group C 1 -C 12 alkyl thienyl group, pyrrolyl group, furyl group, pyridyl group, C 1 -C 12 alkyl pyridyl group, piperidyl group, quinolyl group, isoquinolyl group and the like, and thienyl group C 1 -C 12 alkyl thienyl group, pyridyl group, and C 1 -C 12 alkyl pyridyl group are preferred.
  • substituted carboxyl group examples include a carboxyl group substituted with an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, and usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms.
  • Specific examples thereof include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, Cyclohexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, 3,7-dimethyloctyloxycarbonyl group, dodecyloxy group Carbonyl group, trifluoromethoxycarbonyl group, pentafluoroethoxycarbonyl group, perfluorobutoxycarbonyl group, perfluorohexyloxycarbonyl group, perfluorooctyloxycarbonyl group, phenoxycarbonyl group
  • the heteroaryloxy group (group represented by Q 1 —O—, Q 1 represents a monovalent heterocyclic group) usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms. In addition, although you may have a substituent on a heterocyclic group, carbon number of a substituent is not included in carbon number.
  • thienyloxy group C 1 ⁇ C 12 alkyl thienyl group, pyrrolyloxy group, furyloxy group, pyridyloxy group, C 1 ⁇ C 12 alkyl pyridyl group, imidazolyloxy group, pyrazolyloxy group, Toriazori Examples include a ruoxy group, an oxazolyloxy group, a thiazoleoxy group, and a thiadiazoleoxy group.
  • Q 1 is preferably a monovalent aromatic heterocyclic group.
  • the heteroarylthio group (group represented by Q 2 —S—, Q 2 represents a monovalent heterocyclic group) usually has about 2 to 30 carbon atoms, preferably about 2 to 15 carbon atoms. In addition, although you may have a substituent on a heterocyclic group, carbon number of a substituent is not included in carbon number.
  • Specific examples thereof include thienyl mercapto group, C 1 -C 12 alkyl thienyl mercapto group, pyrrolyl mercapto group, furyl mercapto group, pyridyl mercapto group, C 1 -C 12 alkyl pyridyl mercapto group, imidazolyl mercapto group, pyrazolyl mercapto group. , Triazolyl mercapto group, oxazolyl mercapto group, thiazole mercapto group, thiadiazole mercapto group and the like.
  • Q 2 is preferably a monovalent aromatic heterocyclic group.
  • n 1 represents an integer of 1 to 4
  • n 2 represents an integer of 0 to 4.
  • l 2 represents an integer of 0 to 4
  • l 1 represents an integer of 0 to 3.
  • n 1 is preferably 1 to 2, and more preferably 1.
  • n 2 is preferably 1 to 2, and more preferably 1.
  • R 1 , R 2 , and R 3 are the same or different and each represents an alkoxy group, a halogen atom, a hydrogen atom, or a hydroxyl group.
  • at least one of R 1 , R 2 and R 3 bonded to the same Si atom is an alkoxy group or a halogen atom, preferably the same Si atom.
  • Two or more of R 1 , R 2 and R 3 bonded to each other are an alkoxy group or a halogen atom, more preferably R 1 , R 2 and R 3 bonded to the same Si atom.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a pentyloxy group, a hexyloxy group, and a cyclohexyloxy group.
  • a methoxy group or an ethoxy group is preferable.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom is preferable from the viewpoint of use as a silane coupling agent.
  • A represents a single bond or a divalent group. When there are a plurality of A, they may be the same or different.
  • the divalent group the formula
  • B represents a single bond or an oxygen atom.
  • m 1 represents an integer of 0 to 10.
  • m 3 represents an integer of 0 to 10, and
  • m 2 represents an integer of 0 to 10.
  • E represents —CO—NH— or —CH 2 —.
  • m 1 is preferably 0 to 2, more preferably 0 to 1.
  • m 2 is preferably 0 to 1, more preferably 0.
  • m 3 is preferably 0 to 5, more preferably 0 to 3, and still more preferably 0 to 1.
  • E is preferably —CH 2 —.
  • the wavy line represents a bond bonded to the C 1 ring or the C 2 ring
  • the dotted line represents a bond bonded to the silyl atom
  • X 1 is a divalent group containing one or more atoms selected from the group consisting of a boron atom, a carbon atom, a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom and a selenium atom, an oxygen atom, Represents a sulfur atom or a selenium atom.
  • X 1 those which form a 6-membered ring or 7-membered ring with the N atom and the C 1 ring or C 2 ring are preferred, and more preferably those which form a 6-membered ring.
  • the following groups are exemplified.
  • each R is independently a hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, alkenyl group, alkynyl. Represents a group, a heteroaryloxy group or a heteroarylthio group.
  • Halogen atom represented by R alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, alkenyl group, alkynyl group, heteroaryloxy group
  • the definition and examples of the heteroarylthio group are the same as those described above for the substituent on C 3 .
  • —C (R) 2 —, —O—, —S—, —S ( ⁇ O) —, —S ( ⁇ O) 2 —, —Se— , —Se ( ⁇ O) —, —Se ( ⁇ O) 2 — are preferable, and —C (R) 2 —, —O—, and —S— are more preferable.
  • D represents an alkyl group, an alkoxy group, or an aryl group. When there are a plurality of D, they may be the same or different.
  • the definition and specific examples of the alkoxy group are the same as those of R 1 to R 3 , specific examples and the like.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, More preferably, they are a fluorine atom, a chlorine atom, and a bromine atom.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, a hexyl group, and a cyclohexyl group.
  • a methyl group, an ethyl group, and a propyl group are preferable.
  • the C 3 ring is preferably an aromatic hydrocarbon ring, and more preferably a benzene ring.
  • the group having a C 3 ring and bonded to a nitrogen atom is preferably a group represented by the following formula (3).
  • R 4 and R 5 are the same or different and are a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, Alkenyl group, alkynyl group, disubstituted amino group, trisubstituted silyl group, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, substituted carboxyl group, heteroaryloxy group or hetero Represents an arylthio group, and R 6 represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio
  • R 6 may form a ring with R 4 or R 5 when adjacent to R 4 or R 5.
  • R 4 and R 5 are preferably a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group, more preferably an alkyl group, still more preferably a methyl group. is there.
  • An alkyl group represented by R 4 , R 5 and R 6 an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an alkenyl group, an alkynyl group, Definition of 2-substituted amino group, 3-substituted silyl group, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, substituted carboxyl group, heteroaryloxy group and heteroarylthio group, Examples are the same as those described above for the substituent on C 3 .
  • n 5 represents 0, 1, 2 or 3.
  • a plurality of R 6 may be the same or different.
  • Examples of the group represented by the above formula (3) include the following groups.
  • R 4 and R 5 are preferably hydrogen atoms
  • R 6 is preferably a methyl group, an ethyl group, an n-butyl group, a sec-butyl group or a tert-butyl group
  • a group represented by formula (3-2) is more preferable.
  • R 4 , R 5 and R 6 represent the same meaning as described above.
  • the wavy line represents a bond that is bonded to the N atom.
  • a preferred embodiment of the compound represented by the formula (1) is the formula
  • n 1 , n 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and A are as defined above]
  • n 1 is 1
  • n 2 is 0 or 1
  • R 1 , R 2 and R 3 are the same or different and are a methoxy group, an ethoxy group or a chlorine atom
  • R 4 and R 5 are the same or different and are a hydrogen atom, a methyl group, an ethyl group, a methoxy group or an acetyloxy group
  • R 6 is a methyl group, an ethyl group, an n-butyl group, a sec-butyl group or a tert group.
  • -Butyl group and A is a formula
  • m 3 ′ is an integer of 0 to 2 and m 3 ′′ is 0 or 1
  • Specific examples of the compound represented by the formula (1A) include the following compounds.
  • Compound (6) can be obtained by reacting Compound (4) with Compound (5).
  • a compound (4) having a group having an olefin structure in an eggplant flask is dissolved in a solvent selected from dimethylformamide, dimethylacetamide, N-methylpyrrolidone, toluene, tetrahydrofuran and the like, and the compound is dissolved in the solution.
  • A, n 1 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above, and A ′ is represented by the following formula (7- A) and (7-B).
  • composition of the present invention contains at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material, and the compound.
  • a composition containing a hole transport material and the above compound is preferable, and the composition can be used as, for example, a charge transport material.
  • the content of the compound and at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material differs depending on the application, but in general, the composition
  • the weight of the compound is preferably 1 to 80 parts by weight.
  • the weight of the compound is preferably 1 to 80 parts by weight, more preferably 100 parts by weight based on the total weight of the composition. Is 1 to 60 parts by weight.
  • the hole transport material, electron transport material, and light-emitting material contained in the composition of the present invention may be a polymer compound.
  • the polystyrene-equivalent number average molecular weight of the polymer compound is usually about 10 3 to 10 8 , preferably 10 4 to 10 6 .
  • the weight average molecular weight in terms of polystyrene is usually about 10 3 to 10 8 , and is 1 ⁇ 10 4 to 5 ⁇ 10 6 from the viewpoint of film formability and the luminous efficiency of the resulting device. preferable.
  • the average molecular weight refers to a value obtained by analyzing the polymer compound by gel permeation chromatography (GPC).
  • the solution of the present invention contains the compound of the present invention and a solvent, and the compound may be one type or two or more types. This solution is useful when forming a film by a printing method or the like.
  • the solution of the present invention includes a hole transport material, an electron transport material, a light emitting material, a stabilizer, a thickener, a low molecular weight compound for reducing viscosity, a surfactant, and an antioxidant.
  • An agent or the like may be included.
  • the thickener represents a high molecular weight compound or a poor solvent for increasing the viscosity
  • the surfactant represents a material for decreasing the surface tension.
  • the solution of the present invention may contain the composition and a solvent.
  • the ratio of the compound represented by formula (1) in the solution of the present invention is usually 1 to 99.9 parts by weight, preferably 10 to 90 parts by weight, based on 100 parts by weight of the solution.
  • the amount is preferably 20 to 80 parts by weight.
  • the viscosity of the solution of the present invention may be adjusted depending on the type of printing method. However, in the case where the solution such as an ink jet printing method passes through a discharge device, in order to prevent clogging or flight bending at the time of discharge.
  • the temperature is preferably in the range of 1 to 20 mPa ⁇ s at 25 ° C.
  • the high molecular weight compound used as the thickener is not particularly limited as long as it is soluble in the same solvent as the compound of the present invention and does not inhibit light emission or charge transport.
  • high molecular weight polystyrene, high molecular weight polymethyl Methacrylate or the like can be used.
  • These high molecular weight compounds preferably have a polystyrene equivalent weight average molecular weight of 500,000 or more, more preferably 1,000,000 or more.
  • a poor solvent can also be used as the thickener.
  • the viscosity can be increased.
  • the type and addition amount of the solvent may be selected as long as the solid content in the solution does not precipitate.
  • the amount of the poor solvent is preferably 50 parts by weight or less, and more preferably 30 parts by weight or less with respect to 100 parts by weight of the total mass of the solution.
  • the antioxidant is for improving the storage stability of the solution of the present invention.
  • the antioxidant is not particularly limited as long as it is soluble in the same solvent as the compound of the present invention and does not inhibit light emission or charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.
  • the solvent of the solution of the present invention is preferably one that can dissolve or uniformly disperse solid components in the solution.
  • the solvent include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran, dioxane and anisole, toluene and xylene.
  • Aromatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone Ketone solvents such as cyclohexanone, benzophenone and acetophenone, ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate and phenyl acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol Polyethyl alcohol, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, 1,2-hexanedi
  • solvents may be used alone or in combination of two or more.
  • aromatic hydrocarbon solvents ether solvents, aliphatic hydrocarbon solvents, ester solvents, ketones from the viewpoints of solubility of the compound of the present invention, uniformity during film formation, viscosity characteristics, etc.
  • Preferred solvents are toluene, xylene, ethylbenzene, diethylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, isobutylbenzene, sec-butylbenzene, n-hexylbenzene, cyclohexylbenzene, 1-methylnaphthalene, Tetralin, anisole, ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane, n-hexylcyclohexane, decalin, methyl benzoate, cyclohexanone, 2-propylcyclohexano , 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 2-nonanone, 2-decan
  • the solvent may be used in combination of two or more types from the viewpoint of film formability, device characteristics, etc., but it is more preferable to use only one type or a combination of two to three types.
  • one of the solvents may be in a solid state at 25 ° C.
  • one type of solvent is preferably a solvent having a boiling point of 180 ° C. or higher, and more preferably 200 ° C. or higher.
  • the solvent having the highest boiling point is 40 to 90% by weight of the total solvent weight in the solution from the viewpoint of viscosity and film formability. Preferably, it is 50 to 90% by weight, more preferably 65 to 85% by weight.
  • the compound represented by the formula (1) contained in the solution of the present invention may be one type or two or more types, and may contain a compound other than the compound as long as the device characteristics and the like are not impaired.
  • the solution of the present invention may contain water, a metal and a salt thereof as long as the device characteristics are not impaired.
  • the metal include lithium, sodium, calcium, potassium, iron, copper, nickel, aluminum, zinc, chromium, manganese, cobalt, platinum, iridium and the like.
  • the solution of the present invention may contain silicon, phosphorus, fluorine, chlorine, bromine and the like as long as the device characteristics are not impaired.
  • the thin film of the present invention contains the compound of the present invention, and examples thereof include a conductive thin film and an organic semiconductor thin film.
  • the thin film of the present invention can be produced, for example, by the following solution treatment.
  • Spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, An ink jet printing method, a capillary coating method, a nozzle coating method and the like are preferable, and a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, and more preferably an ink jet method.
  • the solution can be baked at a temperature of 100 ° C. or higher, and even when baked at a temperature of 130 ° C., the deterioration of device characteristics is small.
  • baking can be performed at a temperature of 160 ° C. or higher.
  • the conductive thin film preferably has a surface resistance of 1 K ⁇ / ⁇ or less, more preferably 100 ⁇ / ⁇ or less, and even more preferably 10 ⁇ / ⁇ or less. Electrical conductivity can be increased by doping the conductive thin film with a Lewis acid, an ionic compound or the like.
  • the higher one of the electron mobility and the hole mobility is preferably 10 ⁇ 5 cm 2 / V / second or more, and preferably 10 ⁇ 3 cm 2 / V / second or more. Is more preferably 10 ⁇ 1 cm 2 / V / second or more.
  • An organic transistor can be obtained by forming the organic semiconductor thin film on a Si substrate on which an insulating film such as SiO 2 and a gate electrode are formed, and forming a source electrode and a drain electrode with Au or the like.
  • the light emitting device of the present invention has an electrode composed of an anode and a cathode, and an organic layer containing the compound provided between the electrodes.
  • the organic layer is preferably one or more layers selected from a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and an interlayer layer, and is a hole transport layer. It is more preferable. In addition, the organic layer is preferably adjacent to the anode.
  • the light emitting layer means a layer having a function of emitting light.
  • the hole transport layer means a layer having a function of transporting holes.
  • the hole injection layer means a layer having a function of injecting holes from the anode.
  • the electron transport layer means a layer having a function of transporting electrons.
  • the electron injection layer means a layer having a function of injecting electrons from the cathode.
  • the interlayer layer is adjacent to the light emitting layer between the light emitting layer and the anode, and is a layer having a role of separating the light emitting layer and the anode or the light emitting layer from the hole injection layer or the hole transport layer. That is.
  • the electron transport layer and the hole transport layer are collectively referred to as a charge transport layer.
  • the electron injection layer and the hole injection layer are collectively referred to as a charge injection layer.
  • Each of the light emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer, and the interlayer layer may be composed of only one layer or two or more layers.
  • the ratio of the hole transport material to the total 100 parts by weight of the compound of the present invention and the hole transport material is usually 20 Is 99 parts by weight, preferably 40 to 99 parts by weight.
  • the ratio of the light emitting material to the total of 100 parts by weight of the compound of the present invention and the light emitting material is usually 20 to 99 parts by weight.
  • the organic layer contains the compound of the present invention and two or more selected from a hole transporting material, an electron transporting material, and a light emitting material
  • the ratio of the compound other than the compound of the present invention to the total of 100 parts by weight thereof Is usually 1 to 99 parts by weight, preferably 20 to 99 parts by weight.
  • a compound in which at least one of R 1 , R 2 and R 3 bonded to the same Si atom is an alkoxy group or a halogen atom is preferably used as a silane coupling agent.
  • a thin film can be formed on the electrode surface. Since a small amount of material is used for forming the organic layer, the light-emitting element can be manufactured easily and at low cost. Further, even in the case of including a plurality of light-emitting elements, crosstalk can be prevented because the film thickness is small.
  • hole transport material As the hole transport material, the electron transport material, and the light emitting material, known low molecular weight compounds, triplet light emitting complexes, or high molecular weight compounds can be used, but high molecular weight compounds are preferably used.
  • Examples of the high molecular weight compound include WO99 / 13692, WO99 / 48160, GB2340304A, WO00 / 53656, WO01 / 19834, WO00 / 55927, GB2348316, WO00 / 46321, WO00 / 06665, WO99 / 54943, WO99 / 54385, US5777070, WO98 / 06773, WO97 / 05184, WO00 / 35987, WO00 / 53655, WO01 / 34722, WO99 / 24526, WO00 / 22027, WO00 / 22026, WO98 / 27136, US573636, WO98 / 21262, US5741921, WO97 / 09394, WO96 / 29356, WO96 / 10617, EP07007020, WO95 / 07955, JP 2001-181618, JP 2001-123156, J
  • Examples of the low molecular weight compound include naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, dyes such as polymethine, xanthene, coumarin, and cyanine, metal complexes of 8-hydroxyquinoline and derivatives thereof, Examples thereof include aromatic amines, tetraphenylcyclopentadiene and derivatives thereof, tetraphenylbutadiene and derivatives thereof, and more specifically, for example, described in JP-A-57-51781 and 59-194393. And the like.
  • triplet light-emitting complex examples include Ir (ppy) 3 , Btp 2 Ir (acac) having iridium as a central metal, PtOEP having platinum as a central metal, Eu (TTA) 3 phen having a central metal as europium, etc. More specifically, for example, Nature, (1998), 395, 151, Appl. Phys. Lett. (1999), 75 (1), 4, Proc. SPIE-Int. Soc. Opt. Eng (2001), 4105 (Organic Light-Emitting Materials and Devices IV), 119, J. Am. Chem. Soc., (2001), 123, 4304, Appl. Phys. Lett., (1997), 71 (18) 2596, Adv. Mater., (1999), 11 (10), 852, Jpn. J. Appl. Phys., 34, 1883 (1995), and the like.
  • the film thickness of the light-emitting layer varies depending on the material used, and may be selected so that the drive voltage and the light emission efficiency are appropriate.
  • Examples of the method for forming the light emitting layer include a method of forming a film from a solution.
  • Examples of the method by film formation from a solution include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, and screen.
  • Coating methods such as printing method, flexographic printing method, offset printing method, ink jet printing method, capillary coating method, nozzle coating method can be used, but from the viewpoint of ease of pattern formation and multi-color coating, Printing methods such as printing methods, flexographic printing methods, offset printing methods, and ink jet printing methods are preferred.
  • the light emitting device of the present invention preferably has a maximum external quantum yield of 1% or more when a voltage of 3.5 V or more is applied between the anode and the cathode from the viewpoint of the luminance of the device. 5% or more is more preferable.
  • the light emitting device of the present invention includes a light emitting device in which an electron transport layer is provided between the cathode and the light emitting layer, a light emitting device in which a hole transport layer is provided between the anode and the light emitting layer, and a space between the cathode and the light emitting layer. And a light emitting device in which an electron transport layer is provided and a hole transport layer is provided between the anode and the light emitting layer.
  • the structure which provides an interlayer layer adjacent to a light emitting layer between a light emitting layer and an anode about each of these structures is also illustrated. That is, the structures a ′) to d ′) are exemplified.
  • the hole transport layer usually contains a hole transport material.
  • the hole transport material includes polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having aromatic amines in the side chain or main chain, pyrazoline derivatives, arylamine derivatives, stilbene. Derivatives, triphenyldiamine derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, etc.
  • high molecular weight compounds include polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having an aromatic amine compound group in the side chain or main chain, polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (P-phenylene vinylene) and its derivatives, poly (2,5-thienylene vinylene) and its derivatives, etc. are preferred, polyvinyl carbazole and its derivatives, polysilane and its derivatives, poly having aromatic amine in the side chain or main chain Siloxane derivatives are more preferred.
  • low molecular weight compounds include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, and triphenyldiamine derivatives. These low molecular weight compounds are preferably used by being dispersed in a polymer binder.
  • the polymer binder is preferably one that does not extremely inhibit charge transport and does not strongly absorb visible light.
  • the polymer binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, Examples include polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.
  • Polyvinylcarbazole and its derivatives can be obtained, for example, from a vinyl monomer by cation polymerization or radical polymerization.
  • polysilanes and derivatives thereof examples include compounds described in Chem. Rev., 89, 1359 (1989), and GB 2300196 published specification. As the synthesis method, the methods described in these can be used, but the Kipping method is particularly preferably used.
  • the polysiloxane and derivatives thereof have almost no hole transporting property in the siloxane skeleton structure, those having the structure of the low molecular weight hole transporting material in the side chain or main chain are preferable, and the hole transporting aromatic group is preferable. What has an amine in a side chain or a principal chain is more preferable.
  • the method for forming the hole transport layer is not limited, but when a low molecular weight compound is used, a method by film formation from a mixed solution with a polymer binder is exemplified, and when a high molecular weight compound is used.
  • An example is a method by film formation from a solution.
  • the solvent used for film formation from a solution a solvent capable of dissolving or uniformly dispersing the hole transport material is preferable.
  • the solvent include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene and the like.
  • Aromatic hydrocarbon solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether
  • ketone solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate
  • ethylene glycol ethylene glycol monobutyl ether
  • ethylene glycol monoethyl ether ethylene glycol monomethyl ether
  • dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol,
  • a coating method such as a printing method, an offset printing method, an ink jet printing method, a capillary-coating method, or a nozzle coating method can be used.
  • the film thickness of the hole transport layer differs depending on the material used and may be selected so that the drive voltage and luminous efficiency are appropriate, but at least a thickness that does not cause pinholes is required. If the thickness is too thick, the driving voltage of the element increases, which is not preferable. Therefore, the thickness of the hole transport layer is preferably 1 to 50 nm, more preferably 5 to 35 nm.
  • the electron transport layer usually contains an electron transport material.
  • the electron transport material known materials can be used in addition to the compounds of the present invention, but oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives.
  • Tetracyanoanthraquinodimethane and derivatives thereof Fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof Derivatives, etc., JP-A-63-70257, JP-A-63-175860, JP-A-2-135359, JP-A-2-135361, JP-A-2-20988, JP-A-3-37992, 3-1. Such as those described in 2184 JP are exemplified.
  • oxadiazole derivatives benzoquinone and derivatives thereof, anthraquinone and derivatives thereof, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof are preferable. More preferred are-(4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum, and polyquinoline.
  • the method for forming the electron transport layer is not particularly limited, but when a low molecular weight compound is used, a vacuum deposition method from powder or a method by film formation from a solution or a molten state is exemplified. In the case of using a compound, a method by film formation from a solution or a molten state is exemplified. In the method using film formation from a solution or a molten state, the polymer binder may be used in combination.
  • the solvent used for film formation from a solution is preferably one that can dissolve or uniformly disperse the electron transport material and / or polymer binder.
  • the solvent include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene and the like.
  • Aromatic hydrocarbon solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether
  • ketone solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate
  • ethylene glycol ethylene glycol monobutyl ether
  • ethylene glycol monoethyl ether ethylene glycol monomethyl ether
  • dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol,
  • spin coating method For film formation from solution or molten state, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing
  • a coating method such as a method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating method can be used.
  • the film thickness of the electron transport layer varies depending on the material used, and it may be selected so that the drive voltage and the light emission efficiency are appropriate values, but at least a thickness that does not cause pinholes is required. If the thickness is too thick, the drive voltage of the element becomes high, which is not preferable.
  • the hole injection layer and the electron injection layer have a function of improving the charge injection efficiency from the electrode among the charge transport layers provided adjacent to the electrode, and have an effect of lowering the driving voltage of the element. .
  • the charge injection layer or insulating layer adjacent to the electrode (usually 0.5 to 4.0 nm in average film thickness, hereinafter the same)
  • a thin buffer layer may be inserted at the interface between the charge transport layer and the light emitting layer in order to improve the adhesion at the interface or prevent mixing.
  • the order and number of layers to be laminated and the thickness of each layer may be adjusted in consideration of the light emission efficiency and the element lifetime.
  • a light emitting device provided with a charge injection layer (electron injection layer, hole injection layer), a light emitting device provided with a charge injection layer adjacent to the cathode, and a charge injection layer provided adjacent to the anode.
  • a light emitting element is mentioned. Specific examples thereof include the structures e) to p).
  • an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode.
  • the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.
  • the charge injection layer include, in addition to the layer containing the compound of the present invention, a layer containing a conductive polymer, provided between the anode and the hole transport layer, and included in the anode material and the hole transport layer.
  • the electrical conductivity of the conductive polymer is preferably 10 ⁇ 5 to 10 3 S / cm, and the leakage current between the light emitting pixels is reduced. Therefore , 10 ⁇ 5 to 10 2 S / cm is more preferable, and 10 ⁇ 5 to 10 1 S / cm is more preferable.
  • the electrical conductivity of the conductive polymer is preferably 10 ⁇ 5 to 10 3 S / cm, and the leakage current between the light emitting pixels is reduced. Therefore , 10 ⁇ 5 to 10 2 S / cm is more preferable, and 10 ⁇ 5 to 10 1 S / cm is more preferable.
  • the conductive polymer is doped with an appropriate amount of ions.
  • the kind of ions to be doped is an anion for the hole injection layer and a cation for the electron injection layer.
  • the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, camphor sulfonate ion and the like
  • the cation include lithium ion, sodium ion, potassium ion and tetrabutylammonium ion.
  • the material used for the charge injection layer may be appropriately selected in relation to the electrode and the material of the adjacent layer.
  • Polyaniline and its derivatives, polythiophene and its derivatives, polypyrrole and its derivatives, polyphenylene vinylene and its derivatives, polythienylene Examples include vinylene and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain, metal phthalocyanine (copper phthalocyanine, etc.), carbon, etc.
  • Examples of the material for the insulating layer include metal fluorides, metal oxides, and organic insulating materials.
  • Examples of the light emitting element provided with the insulating layer include a light emitting element provided with an insulating layer adjacent to the cathode and a light emitting element provided with an insulating layer adjacent to the anode.
  • an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode.
  • the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.
  • the interlayer layer is provided between the anode and the light emitting layer, and the anode, the hole injection layer or the hole transport layer, and the light emitting layer. It is preferably composed of a material having an ionization potential intermediate to that of the polymer compound constituting
  • materials used for the interlayer layer include polyvinyl carbazole and derivatives thereof, polyarylene derivatives having aromatic amines in the side chain or main chain, arylamine derivatives, triphenyldiamine derivatives, and other aromatic amines.
  • polyvinyl carbazole and derivatives thereof polyarylene derivatives having aromatic amines in the side chain or main chain
  • arylamine derivatives arylamine derivatives
  • triphenyldiamine derivatives and other aromatic amines.
  • the method for forming the interlayer layer is not particularly limited.
  • a method by film formation from a solution is exemplified.
  • the solvent used for film formation from a solution a solvent that can dissolve or uniformly disperse the material used for the interlayer layer is preferable.
  • the solvent include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene and the like.
  • Aromatic hydrocarbon solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether
  • ketone solvents such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate
  • ethylene glycol ethylene glycol monobutyl ether
  • ethylene glycol monoethyl ether ethylene glycol monomethyl ether
  • dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol,
  • a coating method such as a printing method, an offset printing method, an ink jet printing method, a capillary-coating method, or a nozzle coating method can be used.
  • the film thickness of the interlayer layer varies depending on the material used and may be selected so that the drive voltage and the light emission efficiency are appropriate.
  • the materials of the two layers may be mixed to adversely affect the characteristics of the device. is there.
  • the light emitting layer is formed by the coating method after the interlayer layer is formed by the coating method, as a method for reducing the mixing of the materials of the two layers, the interlayer layer is formed by the coating method, and the interlayer layer is A method of forming a light emitting layer after heating to insolubilize in an organic solvent used for preparing the light emitting layer is mentioned.
  • the heating temperature is usually about 150 to 300 ° C.
  • the heating time is usually about 1 minute to 1 hour.
  • the interlayer layer may be rinsed with a solvent used for forming the light emitting layer after heating and before forming the light emitting layer.
  • a solvent used for forming the light emitting layer When the solvent is insolubilized sufficiently by heating, the rinsing can be omitted.
  • the number of polymerizable groups is preferably 5% or more with respect to the number of structural units in the molecule.
  • the substrate on which the light emitting element of the present invention is formed may be any material that does not change chemically when an electrode is formed and an organic layer is formed.
  • the substrate is made of a material such as glass, plastic, a polymer film, or silicon. This is exemplified.
  • the opposite electrode is preferably transparent or translucent.
  • At least one of the anode and the cathode included in the light emitting device of the present invention is usually transparent or translucent, but the anode side is preferably transparent or translucent.
  • Examples of the material of the anode include a conductive metal oxide film, a translucent metal thin film, and the like. Specifically, indium oxide, zinc oxide, tin oxide, and a composite thereof such as indium / tin / Films (NESA, etc.) made using conductive materials made of oxide (ITO), indium, zinc, oxide, etc., gold, platinum, silver, copper, etc. are used, ITO, indium, zinc, oxide, tin oxide Is preferred. Examples of the production method include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like. As the anode, an organic transparent conductive film such as polyaniline and a derivative thereof, polythiophene and a derivative thereof may be used. The anode may have a laminated structure of two or more layers.
  • the film thickness of the anode can be appropriately selected in consideration of light transmittance and electrical conductivity, and is, for example, 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, more preferably 50 to 500 nm. is there.
  • a layer made of a phthalocyanine derivative, a conductive polymer, carbon or the like; an insulating layer made of a metal oxide, a metal fluoride, an organic insulating material or the like may be provided.
  • the material for the cathode is preferably a material having a low work function.
  • metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, or the like
  • Two or more alloys, or one or more of them and one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, and graphite and graphite intercalation compounds Etc. are used.
  • the cathode may have a laminated structure of two or more layers.
  • the film thickness of the cathode may be appropriately adjusted in consideration of electric conductivity and durability, and is usually 10 nm to 10 ⁇ m, preferably 20 nm to 1 ⁇ m, more preferably 50 to 500 nm.
  • a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression bonded, or the like is used.
  • a layer made of a conductive polymer or a layer made of a metal oxide, a metal fluoride, an organic insulating material or the like having an average film thickness of 2 nm or less may be provided between the cathode and the organic material layer.
  • a protective layer for protecting the polymer light emitting device may be attached. In order to stably use the polymer light emitting device for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the device from the outside.
  • the protective layer high molecular weight compounds, metal oxides, metal fluorides, metal borides and the like can be used.
  • the protective cover is bonded to the element substrate with a thermosetting resin or a photocurable resin and sealed. The method is preferably used. If a space is maintained using a spacer, it is easy to prevent damage to the element. If an inert gas such as nitrogen or argon is enclosed in the space, oxidation of the cathode can be prevented, and further, moisture adsorbed in the manufacturing process can be obtained by installing a desiccant such as barium oxide in the space. Or it becomes easy to suppress that the trace amount water
  • the light emitting device of the present invention can be used as a planar light source, a segment display device, a dot matrix display device, a backlight of a liquid crystal display device, and the like.
  • the planar anode and cathode may be arranged so as to overlap each other.
  • both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by a method of separately coating a plurality of types of polymer phosphors having different emission colors or a method using a color filter or a fluorescence conversion filter.
  • the dot matrix element can be driven passively, or may be actively driven in combination with a TFT or the like.
  • planar light emitting element is self-luminous and thin, and can be suitably used as a planar light source for a 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 or display device.
  • NMR measurement was performed using INOVA300 (manufactured by Varian) after dissolving the compound in deuterated chloroform at a concentration of 0.5 wt%.
  • Measurement of FT-IR was performed using FT / IR-460 plus (manufactured by JASCO).
  • the polystyrene-equivalent number average molecular weight and weight average molecular weight were determined by gel permeation chromatography (GPC, manufactured by Shimadzu Corporation, trade name: LC-10Avp).
  • the polymer compound to be measured was dissolved in tetrahydrofuran to a concentration of about 0.5% by weight, and 30 ⁇ L was injected into GPC. Tetrahydrofuran was used for the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
  • TSKgel SuperHM-H manufactured by Tosoh
  • TSKgel SuperH2000 manufactured by Tosoh
  • a differential refractive index detector (manufactured by Shimadzu Corporation, trade name: RID-10A) was used as the detector.
  • the polymer compound “F8TFB” had a polystyrene equivalent number average molecular weight of 1.3 ⁇ 10 5 and a polystyrene equivalent weight average molecular weight of 3.0 ⁇ 10 5 .
  • the polymer compound “F8TFB” is a random copolymer having the following repeating units at a composition ratio of 90:10.
  • Example 1 Synthesis of Compound 1 A 3 L 4-neck round bottom flask was equipped with a mechanical stirrer and a condenser. The reaction vessel was purged with nitrogen, and 1.10 g of palladium (II) acetate, 1.51 g of tris (o-tolyl) phosphine and 368 ml of toluene were added, and the mixture was stirred at room temperature for 30 minutes.
  • Example 2 Mixture 4 was added to xylene in an amount of 0.1% by weight, and stirred for 4 hours using a magnetic stirrer. Thereafter, the solution was filtered through a filter having a pore diameter of 0.1 micron to prepare a solution containing the mixture 4.
  • an ITO film having a thickness of 45 nm was formed as an anode by sputtering. The surface of the ITO film was irradiated with ultraviolet rays having a wavelength of 185 nm and ultraviolet rays having a wavelength of 254 nm in an oxygen atmosphere for 10 minutes to clean the surface.
  • the solution containing the mixture 4 is applied onto the ITO film by spin coating at a rotational speed of 2000 rpm, and the glass substrate is dried at 130 ° C. for 10 minutes using a hot plate in a nitrogen atmosphere, thereby containing the mixture 4.
  • An organic layer was formed.
  • the film thickness of the organic layer was approximately 30 nm.
  • FIG. 1 is a schematic cross-sectional view showing the structure of an organic EL element according to an embodiment of the present invention.
  • an ITO film having a thickness of 45 nm was formed as the anode 2 by sputtering.
  • the surface of the ITO film was cleaned by irradiating ultraviolet rays with a wavelength of 185 nm and ultraviolet rays with a wavelength of 254 nm for 10 minutes in an oxygen atmosphere. Thereafter, the solution containing the mixture 4 is applied onto the ITO film by spin coating at a rotational speed of 3000 rpm, and the glass substrate is dried at 130 ° C. for 10 minutes using a hot plate in a nitrogen atmosphere, thereby containing the mixture 4.
  • a hole transport layer 3 was formed.
  • a 1.3 wt% xylene solution of “F8TFB” was applied onto the hole transport layer by spin coating, and a film having a thickness of about 80 nm was formed to form the light emitting layer 4.
  • the glass substrate was dried at 130 ° C. for 10 minutes using a hot plate in a nitrogen atmosphere, and then barium 5 was deposited to a thickness of about 5 nm as a cathode 7, and then aluminum 6 was deposited to a thickness of about 80 nm.
  • an organic EL element was produced.
  • metal deposition was started after the degree of vacuum reached 1 ⁇ 10 ⁇ 4 Pa or less.
  • the organic EL element was sealed using a sealing material and a glass plate in a nitrogen atmosphere, and the characteristics of the element were evaluated in the air.
  • PEDOT / PSS manufactured by HC Stark, trade name: CLEVIOS P AI4083
  • a hole transport layer that is an organic layer containing PEDOT / PSS.
  • the film thickness of the hole transport layer was 65 nm.
  • a 1.3 wt% xylene solution of “F8TFB” was applied onto the hole transport layer by spin coating, and a film having a thickness of about 80 nm was formed to form a light emitting layer.
  • barium was vapor-deposited with a thickness of about 5 nm as a cathode, and then aluminum was vapor-deposited with a thickness of about 80 nm.
  • metal deposition was started after the degree of vacuum reached 1 ⁇ 10 ⁇ 4 Pa or less.
  • the organic EL element was sealed using a sealing material and a glass plate in a nitrogen atmosphere, and the characteristics of the element were evaluated in the air.
  • the organic EL device obtained in Example 2 was thin and could be manufactured at low cost because the film thickness of the hole transport layer 3 between the anode and the light emitting layer was 15 to 30 nm. Moreover, compared with the organic EL element whose film thickness of the positive hole transport layer containing PEDOT / PSS obtained by the comparative example 1 is 65 nm, when 8.0V was applied, the same current density was shown.

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé pouvant être mis en forme sous l'aspect d'une couche mince et qui présente une excellente capacité de transport des trous, ainsi qu'un composant photo-émetteur tel qu'un composant électroluminescent organique présentant une couche organique qui contient le composé susmentionné. La présente invention concerne spécifiquement un composé de formule. [Dans la formule, les cycles C1, C2 et C3 représentent un cycle hydrocarbure aromatique ou un cycle complexe. A représente une liaison simple ou un groupement divalent. n1 représente un entier compris entre 1 et 4, et n2 représente un entier compris entre 0 et 4. l1 représente un entier compris entre 0 et 3, et l2 représente un entier compris entre 0 et 4. Chacun des radicaux R1 à R3 est identique ou différent et représente un groupement alcoxy, un atome d'halogène, un atome d'hydrogène ou un groupement hydroxyle. X1 représente un atome d'oxygène, un atome de soufre, un atome de sélénium ou un groupement divalent contenant au moins un atome choisi parmi le bore, le carbone, l'azote, l'oxygène, le phosphore, le soufre et le sélénium. D représente un atome d'hydrogène ou un groupement alkyle, un groupement alcoxy ou un groupement aryle.]
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Cited By (2)

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WO2016203773A1 (fr) * 2015-06-19 2016-12-22 Ricoh Company, Ltd. Composé électrochromique, composition électrochromique et élément d'affichage électrochromique
CN107683320A (zh) * 2015-06-19 2018-02-09 株式会社理光 电致变色化合物、电致变色组合物和电致变色显示元件

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JPH05323634A (ja) * 1992-05-26 1993-12-07 Konica Corp 電子写真感光体
WO2009069523A1 (fr) * 2007-11-30 2009-06-04 Sumitomo Chemical Company, Limited Composé polymérique de type amine et élément émettant de la lumière le comportant

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Publication number Priority date Publication date Assignee Title
JPH05323634A (ja) * 1992-05-26 1993-12-07 Konica Corp 電子写真感光体
WO2009069523A1 (fr) * 2007-11-30 2009-06-04 Sumitomo Chemical Company, Limited Composé polymérique de type amine et élément émettant de la lumière le comportant

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016203773A1 (fr) * 2015-06-19 2016-12-22 Ricoh Company, Ltd. Composé électrochromique, composition électrochromique et élément d'affichage électrochromique
CN107683320A (zh) * 2015-06-19 2018-02-09 株式会社理光 电致变色化合物、电致变色组合物和电致变色显示元件
US10534236B2 (en) 2015-06-19 2020-01-14 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic display element
EP3660123A1 (fr) * 2015-06-19 2020-06-03 Ricoh Company, Ltd. Composé électrochromique, composition électrochromique et élément d'affichage électrochromique
CN107683320B (zh) * 2015-06-19 2020-06-16 株式会社理光 电致变色化合物、电致变色组合物和电致变色显示元件
CN111548318A (zh) * 2015-06-19 2020-08-18 株式会社理光 电致变色化合物和电致变色组合物
JP2021006911A (ja) * 2015-06-19 2021-01-21 株式会社リコー エレクトロクロミック表示素子
US10935862B2 (en) 2015-06-19 2021-03-02 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic display element
JP7036175B2 (ja) 2015-06-19 2022-03-15 株式会社リコー エレクトロクロミック表示素子

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