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WO2012108326A1 - Matériau de couche d'isolation de transistor à couche mince organique réticulable par l'énergie lumineuse et thermique - Google Patents

Matériau de couche d'isolation de transistor à couche mince organique réticulable par l'énergie lumineuse et thermique Download PDF

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WO2012108326A1
WO2012108326A1 PCT/JP2012/052356 JP2012052356W WO2012108326A1 WO 2012108326 A1 WO2012108326 A1 WO 2012108326A1 JP 2012052356 W JP2012052356 W JP 2012052356W WO 2012108326 A1 WO2012108326 A1 WO 2012108326A1
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film transistor
thin film
organic thin
insulating layer
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公 矢作
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/411—Suzuki reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/92—TFT applications
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene

Definitions

  • the present invention relates to a material suitable for forming an insulating layer of an organic thin film transistor.
  • Organic thin-film transistors can be manufactured at a lower temperature than inorganic semiconductors, so plastic substrates and films can be used as their substrates, and by using such substrates, elements that are more flexible, lighter and less fragile than transistors made of inorganic semiconductors. Can be obtained.
  • an element can be manufactured by application of a solution containing an organic material or film formation using a printing method, and a large number of elements can be manufactured on a large-area substrate at low cost.
  • a voltage applied to a gate electrode acts on a semiconductor layer through a gate insulating layer to control on / off of a drain current. Therefore, a gate insulating layer is formed between the gate electrode and the semiconductor layer.
  • organic semiconductor compounds used in the manufacture of field effect organic thin film transistors are easily affected by the environment such as humidity and oxygen, and the transistor characteristics are likely to deteriorate over time due to humidity, oxygen, and the like.
  • the organic semiconductor compound is coated and protected by a gate insulating layer.
  • an insulating layer material is used to form an overcoat layer, a gate insulating layer, and the like that cover the organic semiconductor layer in the organic thin film transistor.
  • an insulating layer or an insulating film of an organic thin film transistor such as the overcoat layer and the gate insulating layer is referred to as an organic thin film transistor insulating layer.
  • a material used for forming the organic thin film transistor insulating layer is referred to as an organic thin film transistor insulating layer material.
  • the material here is a concept including an amorphous material such as a polymer compound, a composition containing the polymer compound, a resin, and a resin composition.
  • the organic thin film transistor insulating layer material is required to have excellent insulating properties and excellent dielectric breakdown strength when formed into a thin film.
  • a semiconductor layer is formed so as to overlap with a gate insulating layer. Therefore, the organic thin film transistor gate insulating layer material has an affinity with the organic semiconductor for forming an interface closely adhered to the organic semiconductor, and the organic semiconductor layer side surface of the film formed from the organic thin film transistor gate insulating layer material is flat. It is required to be.
  • Patent Document 1 describes that an epoxy resin and a silane coupling agent are used in combination as an organic thin film transistor gate insulating layer material.
  • a hydroxyl group produced during the curing reaction of an epoxy resin is reacted with a silane coupling agent. This is because the hydroxyl group enhances the hygroscopicity of the gate insulating layer material and impairs the stability of the transistor performance.
  • Non-Patent Document 1 describes that a resin obtained by thermally cross-linking polyvinylphenol and a melamine compound is used for the gate insulating layer.
  • a resin obtained by thermally cross-linking polyvinylphenol and a melamine compound is used for the gate insulating layer.
  • the hydroxyl group contained in polyvinylphenol is removed by crosslinking with a melamine compound, and at the same time the film strength is increased.
  • the pentacene TFT having this gate insulating layer has a small hysteresis and exhibits durability against gate bias stress.
  • Non-Patent Document 2 describes that polyvinyl gate and a copolymer obtained by copolymerizing vinyl phenol and methyl methacrylate are used for the gate insulating layer.
  • the hydroxyl group of vinylphenol interacts with the carbonyl group of methyl methacrylate to reduce the polarity of the entire film.
  • the pentacene TFT having this gate insulating layer has a small hysteresis and exhibits stable electrical characteristics.
  • the organic thin film transistor having the conventional gate insulating layer has a threshold voltage ( The absolute value and hysteresis of Vth) are large.
  • An object of the present invention is to provide an organic thin film transistor insulating layer material capable of producing an organic thin film transistor having a small absolute value of threshold voltage and small hysteresis.
  • the absolute value and hysteresis of the threshold voltage (Vth) of the organic thin film transistor are reduced by forming a gate insulating layer using a specific resin composition capable of forming a crosslinked structure.
  • Vth threshold voltage
  • the present invention has the formula (1)
  • R 2 represents a hydrogen atom or a methyl group.
  • R 3 and R 4 each independently represents a monovalent organic group having 1 to 20 carbon atoms. A hydrogen atom in the monovalent organic group may be substituted with a fluorine atom. The carbon atom in R 3 and the carbon atom in R 4 may be bonded to form a 5-membered ring or a 6-membered ring.
  • R bb represents a connecting part that connects the main chain and the side chain of the polymer compound and may have a fluorine atom.
  • c represents an integer of 0 or 1.
  • a second functional group containing a first functional group, and the first functional group generates a second functional group that reacts with active hydrogen by the action of electromagnetic waves or heat.
  • the present invention provides an organic thin film transistor insulating layer material containing a polymer compound (A) which is a functional group.
  • the said high molecular compound (A) is further Formula (2).
  • R 1 represents a hydrogen atom or a methyl group.
  • R represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • Rf represents a fluorine atom or a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom.
  • R aa represents a connecting portion that connects the main chain and the side chain of the polymer compound and may have a fluorine atom.
  • u represents an integer of 0 or 1
  • b represents an integer of 1 to 5.
  • u represents an integer of 0 or 1
  • b represents an integer of 1 to 5.
  • the first functional group is at least one group selected from the group consisting of an isocyanato group blocked with a blocking agent and an isothiocyanato group blocked with a blocking agent.
  • the isocyanato group blocked with the blocking agent and the isothiocyanato group blocked with the blocking agent are represented by the formula (3):
  • Xa represents an oxygen atom or a sulfur atom
  • R 5 and R 6 are the same or different and represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • It is group represented by these.
  • the isocyanato group blocked with the blocking agent and the isothiocyanato group blocked with the blocking agent are represented by the formula (4):
  • Xb represents an oxygen atom or a sulfur atom
  • R 7 to R 9 are the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • the polymer compound (A) further includes two or more structural units having one active hydrogen or a structural unit having two or more active hydrogens.
  • the present invention further includes at least one selected from the group consisting of an active hydrogen compound which is a low molecular compound containing two or more active hydrogens and an active hydrogen compound which is a polymer compound containing two or more active hydrogens.
  • the organic thin-film transistor insulating layer material containing the active hydrogen compound is provided.
  • the present invention also includes a step of applying a liquid containing the organic thin film transistor insulating layer material to a substrate to form a coating layer on the substrate; and a step of irradiating the coating layer with an electromagnetic wave or an electron beam; And a method for forming an organic thin film transistor insulating layer including the same.
  • the present invention also includes a step of applying a liquid containing the organic thin film transistor insulating layer material to a base material to form a coating layer on the base material; Irradiating the coating layer with electromagnetic waves or electron beams; and applying heat to the coating layer; And a method for forming an organic thin film transistor insulating layer including the same.
  • the electromagnetic wave is ultraviolet light.
  • the present invention also provides an organic thin film transistor having an organic thin film transistor insulating layer formed using the organic thin film transistor insulating layer material.
  • the organic thin film transistor insulating layer is a gate insulating layer.
  • the present invention also provides a display member comprising the organic thin film transistor.
  • the present invention also provides a display including the display member.
  • An organic thin film transistor having an insulating layer formed using the organic thin film transistor insulating layer material of the present invention has a small absolute value of threshold voltage and a small hysteresis.
  • polymer compound refers to a compound having a structure in which a plurality of the same structural units are repeated in the molecule, and includes a so-called dimer.
  • dimer the “low molecular compound” means a compound that does not have the same structural unit repeatedly in the molecule.
  • the organic thin film transistor insulating layer material of the present invention includes a polymer compound, and the polymer compound has a plurality of functional groups that absorb the energy of electromagnetic waves or the energy of electron beams to cause a dimerization reaction. When it acts, it has a plurality of first functional groups that generate a second functional group that reacts with active hydrogen.
  • the functional group that absorbs electromagnetic energy or electron beam energy to cause a dimerization reaction is referred to as a “photodimerization reactive group” in this specification.
  • active hydrogen means a hydrogen atom bonded to an oxygen atom, a sulfur atom or a nitrogen atom.
  • the photodimerization reactive group is a functional group that can perform a concerted reaction when absorbing light energy or electron beam energy.
  • Functional groups that can perform a concerted reaction can be dimerized by cycloaddition with each other to form a crosslinked structure inside the insulating layer.
  • the electromagnetic wave absorbed by the photodimerization reactive group is preferably low energy, so that when the organic thin film transistor insulating layer material is formed by the photopolymerization method, the photodimerization reactive group may also react.
  • a preferable electromagnetic wave to be absorbed by the photodimerization reactive group is ultraviolet light, for example, light having a wavelength of 400 nm or less, preferably 150 to 390 nm, more preferably 280 to 380 nm.
  • “Dimerization” here means that two molecules of an organic compound are chemically bonded.
  • the molecules to be bound may be the same or different.
  • the chemical structures of the functional groups involved in dimerization in the two molecules to be dimerized may be the same or different.
  • the functional group has a structure and a combination that cause a photodimerization reaction even when a reaction aid such as a catalyst and an initiator is not used. This is because contact with the residue of the reaction aid may cause deterioration of surrounding organic materials.
  • the first functional group contained in the polymer compound does not react with active hydrogen, but when an electromagnetic wave or heat acts on the first functional group, a second functional group is generated and reacts with active hydrogen. That is, the first functional group is deprotected by electromagnetic waves or heat to generate a second functional group that reacts with active hydrogen.
  • the second functional group reacts with and binds to the active hydrogen-containing group of the active hydrogen compound (E), so that a crosslinked structure can be formed inside the insulating layer.
  • the “active hydrogen compound” means a compound having one or more active hydrogens.
  • the second functional group is protected (blocked) in the step of forming the gate insulating layer until electromagnetic waves or heat is applied, and is present in the organic thin film transistor insulating layer material as the first functional group.
  • the storage stability of the organic thin film transistor insulating layer material is improved.
  • a polymer compound containing a repeating unit having a photodimerization reactive group and a repeating unit having the first functional group corresponds to the polymer compound.
  • the repeating unit having a photodimerization reactive group is preferably a repeating unit represented by the above formula (1).
  • the polymer compound contained in the organic thin film transistor insulating layer material of the present invention is preferably a polymer compound having a repeating unit represented by the formula (1) and a repeating unit containing a first functional group. Such a polymer compound is referred to as a polymer compound (A).
  • R 2 represents a hydrogen atom or a methyl group. In some one aspect, R 2 is a methyl group.
  • R 3 and R 4 each independently represents a monovalent organic group having 1 to 20 carbon atoms.
  • a hydrogen atom in the monovalent organic group may be substituted with a fluorine atom.
  • the monovalent organic group having 1 to 20 carbon atoms may be linear, branched or cyclic, and may be saturated or unsaturated.
  • Examples of the monovalent organic group having 1 to 20 carbon atoms include a linear hydrocarbon group having 1 to 20 carbon atoms, a branched hydrocarbon group having 3 to 20 carbon atoms, and a cyclic hydrocarbon having 3 to 20 carbon atoms.
  • Group, aromatic hydrocarbon group having 6 to 20 carbon atoms preferably linear hydrocarbon group having 1 to 6 carbon atoms, branched hydrocarbon group having 3 to 6 carbon atoms, or 3 to 6 carbon atoms.
  • an aromatic hydrocarbon group having 6 to 20 carbon atoms preferably linear hydrocarbon group having 1 to 6 carbon atoms, branched hydrocarbon group having 3 to 6 carbon atoms, or 3 to 6 carbon atoms.
  • a linear hydrocarbon group having 1 to 20 carbon atoms a branched hydrocarbon group having 3 to 20 carbon atoms, and a cyclic hydrocarbon group having 3 to 20 carbon atoms
  • the hydrogen atoms contained in these groups are substituted with fluorine atoms. May be.
  • a hydrogen atom in the group may be substituted with an alkyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
  • the monovalent organic group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, tertiary butyl group, cyclopropyl group, Cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentynyl group, cyclohexynyl group, trifluoromethyl group, trifluoroethyl group, phenyl group, naphthyl group, anthryl group, tolyl group, xylyl group, dimethylphenyl group, trimethylphenyl group , Ethylphenyl group, diethylphenyl group, triethylphenyl group, propylphenyl group, butylphenyl group, methylnaphthyl group, dimethylnaphthyl group,
  • an alkyl group is preferable.
  • the carbon atom in R 3 and the carbon atom in R 4 may be bonded to form a 5-membered ring or a 6-membered ring.
  • Examples of the 5-membered ring include a cyclopentene ring.
  • Examples of the 6-membered ring include a cyclohexene ring.
  • R ⁇ 3 > and R ⁇ 4 > are the same or different, and are groups selected from the group which consists of a methyl group and an ethyl group.
  • R bb represents a linking moiety that links the main chain and the side chain and may have a fluorine atom.
  • the connecting portion may be a divalent group having a structure that does not exhibit reactivity under environmental conditions for crosslinking the organic thin film transistor insulating layer material of the present invention.
  • Specific examples of the linking moiety include a bond composed of a divalent organic group having 1 to 20 carbon atoms, an ether bond (—O—), a ketone bond (—CO—), an ester bond (—COO—, —OCO—). Amide bond (—NHCO—, —CONH—), urethane bond (—NHCOO—, —OCONH—), and a combination of these bonds.
  • c represents an integer of 0 or 1. In one certain form, c is 1.
  • the divalent organic group having 1 to 20 carbon atoms may be linear, branched or cyclic, and may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • a divalent linear aliphatic hydrocarbon group having 1 to 20 carbon atoms a divalent branched aliphatic hydrocarbon group having 3 to 20 carbon atoms, and a divalent cyclic hydrocarbon group having 3 to 20 carbon atoms
  • a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with an alkyl group or the like.
  • a divalent linear aliphatic hydrocarbon group having 1 to 6 carbon atoms a divalent linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, a divalent branched aliphatic hydrocarbon group having 3 to 6 carbon atoms, and a divalent cyclic hydrocarbon group having 3 to 6 carbon atoms.
  • a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with an alkyl group or the like is preferable.
  • divalent aliphatic hydrocarbon group and the divalent cyclic hydrocarbon group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, an isopropylene group, an isobutylene group, and dimethylpropylene.
  • cyclopropylene group, cyclobutylene group, cyclopentylene group, and cyclohexylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, an isopropylene group, an isobutylene group, and dimethylpropylene.
  • cyclopropylene group, cyclobutylene group, cyclopentylene group, and cyclohexylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pent
  • divalent aromatic hydrocarbon group having 6 to 20 carbon atoms include phenylene group, naphthylene group, anthrylene group, dimethylphenylene group, trimethylphenylene group, ethylenephenylene group, diethylenephenylene group, triethylenephenylene group, Examples include propylenephenylene group, butylenephenylene group, methylnaphthylene group, dimethylnaphthylene group, trimethylnaphthylene group, vinylnaphthylene group, ethenylnaphthylene group, methylanthrylene group, and ethylanthrylene group.
  • a preferred example of the photodimerization reactive group is a group represented by the formula (5), in which the hydrogen atom at the 3-position and the hydrogen atom at the 4-position of the maleimide group are each substituted with an alkyl group or an aryl group.
  • R ′ is preferably a propane-1,3-diyl group or a butane-1,4-diyl group.
  • R ′ represents an alkanediyl group.
  • the photodimerization reactive group is a group in which the hydrogen atom at the 3-position and the hydrogen atom at the 4-position of the maleimide group are each substituted with an alkyl group or an aryl group, or a group represented by the formula (5).
  • an ultraviolet ray or an electron beam is used.
  • a 2 + 2 cyclization reaction occurs and the organic thin film transistor insulating layer material is crosslinked.
  • preferable examples of the first functional group include an isocyanato group blocked with a blocking agent and an isothiocyanato group blocked with a blocking agent.
  • the isocyanato group blocked with the blocking agent or the isothiocyanato group blocked with the blocking agent is an isocyanate group or an isocyanate group having only one active hydrogen capable of reacting with an isocyanato group or an isothiocyanato group, or It can be produced by reacting with an isothiocyanato group.
  • the blocking agent is preferably one that dissociates at a temperature of 170 ° C. or lower even after reacting with an isocyanato group or an isothiocyanato group.
  • the blocking agent include alcohol compounds, phenol compounds, active methylene compounds, mercaptan compounds, acid amide compounds, acid imide compounds, imidazole compounds, urea compounds, and oxime compounds. , Amine compounds, imine compounds, bisulfites, pyridine compounds, and pyrazole compounds. These blocking agents may be used alone or in combination of two or more.
  • Preferable blocking agents include oxime compounds and pyrazole compounds.
  • Specific blocking agents are exemplified below.
  • alcohol compounds include methanol, ethanol, propanol, butanol, 2-ethylhexanol, methyl cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, and cyclohexanol.
  • phenolic compounds include phenol, cresol, ethylphenol, butylphenol, nonylphenol, dinonylphenol, styrenated phenol, and hydroxybenzoic acid ester.
  • active methylene compound include dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, and acetylacetone.
  • Examples of mercaptan compounds include butyl mercaptan and dodecyl mercaptan.
  • Examples of the acid amide compounds include acetanilide, acetic acid amide, ⁇ -caprolactam, ⁇ -valerolactam, and ⁇ -butyrolactam.
  • Examples of the acid imide compounds include succinimide and maleic imide.
  • Examples of the imidazole compound include imidazole and 2-methylimidazole.
  • Examples of the urea compound include urea, thiourea, and ethylene urea.
  • Examples of the amine compound include diphenylamine, aniline, and carbazole.
  • Examples of the imine compound include ethyleneimine and polyethyleneimine.
  • An example of a bisulfite is sodium bisulfite.
  • pyridine compounds include 2-hydroxypyridine and 2-hydroxyquinoline.
  • oxime compounds include formaldoxime, acetaldoxime, acetoxime, methyl ethyl ketoxime, and cyclohexanone oxime.
  • the pyrazole compound include 3,5-dimethylpyrazole and 3,5-diethylpyrazole.
  • the isocyanato group or isothiocyanato group blocked with a blocking agent that may be used in the present invention is preferably a group represented by the above formula (3) or a group represented by the above formula (4).
  • Xa represents an oxygen atom or a sulfur atom
  • Xb represents an oxygen atom or a sulfur atom
  • R 5 to R 9 are the same or different and represent a hydrogen atom or a carbon number.
  • 1 to 20 monovalent organic groups are represented. The definition and specific examples of the monovalent organic group are the same as the definition and specific examples of the monovalent organic group described above.
  • R 5 to R 9 are hydrogen atoms.
  • Examples of the isocyanato group blocked with a blocking agent include O- (methylideneamino) carboxyamino group, O- (1-ethylideneamino) carboxyamino group, O- (1-methylethylideneamino) carboxyamino group, O— [1-methylpropylideneamino] carboxyamino group, (N-3,5-dimethylpyrazolylcarbonyl) amino group, (N-3-ethyl-5-methylpyrazolylcarbonyl) amino group, (N-3,5-diethyl) And pyrazolylcarbonyl) amino group, (N-3-propyl-5-methylpyrazolylcarbonyl) amino group, and (N-3-ethyl-5-propylpyrazolylcarbonyl) amino group.
  • Examples of the isothiocyanato group blocked with a blocking agent include an O- (methylideneamino) thiocarboxyamino group, an O- (1-ethylideneamino) thiocarboxyamino group, and an O- (1-methylethylideneamino) thiocarboxyamino group.
  • the first functional group is preferably an isocyanato group blocked with a blocking agent.
  • the polymer compound (A) comprises, for example, a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (1) and a polymerizable monomer containing the first functional group as a photopolymerization initiator or heat. It can manufacture by the method of copolymerizing using a polymerization initiator.
  • Polymerization of the polymerizable monomer may be performed by a method commonly used by those skilled in the art.
  • a method for polymerizing a polymerizable monomer for example, a method in which a polymerizable monomer and a polymerization initiator are dissolved in a suitable solvent, dissolved oxygen in the resulting solution is replaced with an inert gas, and then heated or irradiated for a certain time. Is exemplified.
  • Examples of the polymerizable monomer that is a raw material for the repeating unit represented by the above formula (1) include N- (3′-methacryloyloxypropyl) -3,4-dimethylmaleimide, N- (3′-methacryloyloxypropyl). ) -1-cyclohexene-1,2-dicarboximide.
  • Examples of the polymerizable monomer containing the first functional group include a monomer having an isocyanato group blocked with a blocking agent or an isothiocyanate group blocked with a blocking agent and an unsaturated bond.
  • a monomer having an isocyanato group blocked with the blocking agent or an isothiocyanate group blocked with a blocking agent and an unsaturated bond includes an isocyanate group or a compound having an isothiocyanato group and an unsaturated bond, and a blocking agent. It can be produced by reacting. As the unsaturated bond, a double bond is preferable.
  • Examples of the compound having a double bond and an isocyanato group include 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate, and 2- (2′-methacryloyloxyethyl) oxyethyl isocyanate.
  • Examples of the compound having a double bond and an isothiocyanato group include 2-acryloyloxyethyl isothiocyanate, 2-methacryloyloxyethyl isothiocyanate, and 2- (2′-methacryloyloxyethyl) oxyethyl isothiocyanate.
  • the above blocking agent contained in the polymerizable monomer
  • the above blocking agent can be suitably used.
  • an organic solvent, a catalyst or the like can be added as necessary.
  • Examples of the monomer having an isocyanate group blocked with the blocking agent and a double bond include 2- [O- [1′-methylpropylideneamino] carboxyamino] ethyl-methacrylate, 2- [N- [ 1 ', 3'-dimethylpyrazolyl] carbonylamino] ethyl-methacrylate.
  • Examples of monomers having an isothiocyanate group and a double bond blocked with the blocking agent include 2- [O- [1′-methylpropylideneamino] thiocarboxyamino] ethyl-methacrylate, 2- [N— And [1 ′, 3′-dimethylpyrazolyl] thiocarbonylamino] ethyl-methacrylate.
  • photopolymerization initiator examples include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 4-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxy- 2-methylpropiophenone, 4,4′-bis (diethylamino) benzophenone, benzophenone, methyl (o-benzoyl) benzoate, 1-phenyl-1,2-propanedione-2- (O-ethoxycarbonyl) oxime, -Phenyl-1,2-propanedione-2- (o-benzoyl) oxime, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin octyl ether, benzyl, benzyl dimethyl
  • carbonyl compounds such as luketal, benzyl diethy
  • the wavelength of light irradiated to the polymerizable monomer is 360 nm or more, preferably 360 to 450 nm.
  • the thermal polymerization initiator may be any compound that serves as a radical polymerization initiator.
  • the polymer compound (A) used in the present invention polymerizes a polymerizable monomer other than a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (1) and a polymerizable monomer containing the first functional group. Sometimes it may be added and manufactured.
  • Additional polymerizable monomers used include, for example, acrylic acid esters and derivatives thereof, methacrylic acid esters and derivatives thereof, styrene and derivatives thereof, vinyl acetate and derivatives thereof, methacrylonitrile and derivatives thereof, acrylonitrile and derivatives thereof.
  • Examples thereof include N-vinylamide derivatives of acids, terminal unsaturated hydrocarbons and derivatives thereof, and organic germanium derivatives containing unsaturated hydrocarbon groups.
  • the type of polymerizable monomer used additionally is appropriately selected according to the characteristics required for the insulating layer. From the viewpoint of excellent durability against solvents and reducing the hysteresis of organic thin film transistors, monomers that have high molecular density and form a hard film are selected in films containing these compounds, such as styrene and styrene derivatives. . In addition, from the viewpoint of adhesion to the adjacent surface of the insulating layer such as the gate electrode or the surface of the substrate, the polymer compound (A) is made plastic such as methacrylic acid esters and derivatives thereof, acrylic acid esters and derivatives thereof. The monomer to be imparted is selected.
  • monofunctional acrylates and polyfunctional acrylates can be used although the amount of use is limited.
  • monofunctional acrylates and polyfunctional acrylates For example, methyl acrylate, ethyl acrylate, acrylic acid-n-propyl, isopropyl acrylate, acrylic acid-n-butyl, isobutyl acrylate, acrylic acid-sec-butyl, hexyl acrylate, octyl acrylate, acrylic 2-ethylhexyl acid, decyl acrylate, isobornyl acrylate, cyclohexyl acrylate, phenyl acrylate, benzyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, Acrylic acid -Hydroxybutyl, 2-hydroxyphenylethyl acrylate, ethylene glycol diacrylate, propylene glycol diacrylate, 1,
  • methacrylic acid esters and derivatives thereof monofunctional methacrylates and polyfunctional methacrylates can be used although the amount of use is limited.
  • Such monofunctional methacrylates and Examples of the functional methacrylate include methyl methacrylate, ethyl methacrylate, methacrylic acid-n-propyl, isopropyl methacrylate, methacrylic acid-n-butyl, isobutyl methacrylate, methacrylic acid-sec.
  • styrene and its derivatives examples include styrene, 2,4-dimethyl- ⁇ -methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene.
  • organic carboxylic acid vinyl esters and derivatives thereof include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate, and divinyl adipate.
  • allyl esters of organic carboxylic acids and derivatives thereof include allyl acetate, allyl benzoate, diallyl adipate, diallyl terephthalate, diallyl isophthalate, and diallyl phthalate.
  • dialkyl esters of fumaric acid and derivatives thereof include dimethyl fumarate, diethyl fumarate, diisopropyl fumarate, di-sec-butyl fumarate, diisobutyl fumarate, di-n-butyl fumarate, di-2 fumarate -Ethylhexyl, dibenzyl fumarate.
  • dialkyl esters of maleic acid and derivatives thereof include dimethyl maleate, diethyl maleate, diisopropyl maleate, di-sec-butyl maleate, diisobutyl maleate, di-n-butyl maleate, di-2 maleate -Ethylhexyl, dibenzyl maleate.
  • dialkyl esters of itaconic acid and derivatives thereof include dimethyl itaconate, diethyl itaconate, diisopropyl itaconate, di-sec-butyl itaconate, diisobutyl itaconate, di-n-butyl itaconate, di-2 itaconate -Ethylhexyl, dibenzyl itaconate.
  • N-vinylamide derivatives of organic carboxylic acids examples include N-methyl-N-vinylacetamide.
  • terminal unsaturated hydrocarbons and derivatives thereof examples include 1-butene, 1-pentene, 1-hexene, 1-octene, vinylcyclohexane, vinyl chloride, and allyl alcohol.
  • Examples of the organic germanium derivative containing an unsaturated hydrocarbon group include allyltrimethylgermanium, allyltriethylgermanium, allyltributylgermanium, trimethylvinylgermanium, and triethylvinylgermanium.
  • acrylic acid alkyl ester methacrylic acid alkyl ester, styrene, acrylonitrile, methacrylonitrile, and allyltrimethylgermanium are preferable.
  • the charged molar ratio of the polymerizable monomer that is a raw material of the repeating unit represented by the formula (1) is 5 mol% or more and 50 mol% or less, preferably 10 mol% or more and 45 mol% in all monomers involved in the polymerization.
  • the mol% or less more preferably 20 mol% or more and 40 mol% or less.
  • the charged molar ratio of the polymerizable monomer containing the first functional group is 5% by mole or more and 50% by mole or less, preferably 10% by mole or more and 40% by mole or less, more preferably among all the monomers involved in the polymerization. Is 15 mol% or more and 30 mol% or less.
  • the polymer compound (A) has a polystyrene-equivalent weight average molecular weight of preferably 3,000 to 1,000,000, more preferably 5,000 to 500,000, and may be linear, branched or cyclic.
  • polymer compound (A) examples include poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4′-dimethylmaleimide)]-co- [2- [O- (1′- Methylpropylideneamino) carboxyamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ', 4'-dimethylmaleimide)]-co- [2- [1'- (3 ', 5'-dimethylpyrazolyl) carbonylamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3', 4'-dimethylmaleimide)]-co-acrylonitrile- Co- [2- [O- (1'-methylpropylideneamino) carboxyamino] ethyl-methacryl
  • Polymer compound (B)> Another preferable aspect of the polymer compound contained in the organic thin film transistor insulating layer material of the present invention is a polymer compound having a plurality of photodimerization reactive groups, a fluorine atom, and a plurality of the first functional groups. It is.
  • a polymer compound having a repeating unit represented by Formula (1), a repeating unit represented by Formula (2), and a repeating unit containing a first functional group is referred to as a polymer compound (B).
  • the insulating layer formed from the material has low polarity, and polarization of the insulating layer is suppressed.
  • a cross-linked structure is formed inside the insulating layer, the movement of the molecular structure is suppressed, and the polarization of the insulating layer is suppressed.
  • the polarization of the insulating layer is suppressed, for example, when used as a gate insulating layer, the hysteresis of the organic thin film transistor is lowered and the operation accuracy is improved.
  • the fluorine atom does not replace the hydrogen atom of the main chain of the polymer compound, but replaces the hydrogen atom of the side chain or side group (pendant group).
  • the fluorine atom is substituted with a side chain or a side group, the affinity for other organic materials such as an organic semiconductor is not lowered, and in the formation of a layer containing the organic material, the organic material is exposed to the exposed surface of the insulating layer. It becomes easy to form a layer in contact.
  • a polymer compound having a repeating unit having a group containing a fluorine atom, a repeating unit having a photodimerization reactive group, and a repeating unit having the first functional group corresponds to the polymer compound (B).
  • Preferred examples of the group containing a fluorine atom include an aryl group in which a hydrogen atom is substituted with fluorine, an alkylaryl group in which a hydrogen atom is substituted with fluorine, particularly a phenyl group in which a hydrogen atom is substituted with fluorine, and a hydrogen atom in fluorine.
  • Preferred examples of the photodimerization reactive group include the same groups as described above.
  • the repeating unit having a group containing a fluorine atom is preferably a repeating unit represented by the above formula (2).
  • R 1 represents a hydrogen atom or a methyl group. In one certain form, R ⁇ 1 > is a hydrogen atom.
  • Rf represents a fluorine atom or a monovalent organic group having 1 to 20 carbon atoms having a fluorine atom. In one certain form, Rf is a fluorine atom. b represents an integer of 1 to 5. In one certain form, b is 5.
  • Rf is an organic group having 1 to 20 carbon atoms having a fluorine atom
  • the monovalent organic group having 1 to 20 carbon atoms having a fluorine atom may be a trifluoromethyl group or 2,2,2-trifluoroethyl.
  • R represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • R is a monovalent organic group having 1 to 20 carbon atoms
  • the monovalent organic group does not have a fluorine atom.
  • Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R include groups having no fluorine atom among the specific examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 3. It is done.
  • R aa represents a linking moiety that links the main chain and the side chain and may have a fluorine atom.
  • the connecting portion may be a divalent group having a structure that does not exhibit reactivity under environmental conditions for crosslinking the organic thin film transistor insulating layer material of the present invention.
  • Specific examples of the linking moiety include a bond composed of a divalent organic group having 1 to 20 carbon atoms, an ether bond (—O—), a ketone bond (—CO—), an ester bond (—COO—, —OCO—). Amide bond (—NHCO—, —CONH—), urethane bond (—NHCOO—, —OCONH—), and a combination of these bonds.
  • u represents an integer of 0 or 1. In one certain form, a is 1.
  • Examples of the divalent organic group having 1 to 20 carbon atoms include the same groups as the specific examples of the divalent organic group having 1 to 20 carbon atoms represented by R bb .
  • the polymer compound (B) includes, for example, a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (1), a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (2), It can be produced by a method in which a polymerizable monomer containing a first functional group is copolymerized using a photopolymerization initiator or a thermal polymerization initiator.
  • Examples of the polymerizable monomer that is a raw material of the repeating unit represented by the above formula (2) include 2-trifluoromethylstyrene, 3-trifluoromethylstyrene, 4-trifluoromethylstyrene, 2,3,4, Examples include 5,6-pentafluorostyrene and 4-fluorostyrene.
  • the polymer compound (B) that can be used in the present invention is a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (1), and a polymerization that is a raw material of the repeating unit represented by the above formula (2).
  • a polymerizable monomer other than the polymerizable monomer and the polymerizable monomer containing the first functional group may be added during polymerization.
  • the amount of the polymerizable monomer used as the raw material of the repeating unit represented by the above formula (2) is adjusted so that the amount of fluorine atoms introduced into the polymer compound (B) becomes an appropriate amount.
  • the amount of fluorine atoms introduced into the polymer compound (B) is preferably 1 to 80% by mass, more preferably 5 to 70% by mass, and further preferably 10 to 10% by mass with respect to the mass of the polymer compound (B). 60% by mass.
  • the amount of the fluorine base paper is less than 1% by mass, the effect of reducing the hysteresis of the field effect organic thin film transistor may be insufficient.
  • the amount exceeds 80% by mass the affinity with the organic semiconductor material is deteriorated and activated. It may be difficult to stack a layer thereon.
  • the polymer compound (B) has the number of repeating units that the polymer compound (B) has 100.
  • the amount of the repeating unit represented by the formula (2) is preferably 30 to 80.
  • the polymer compound (B) has a polystyrene-equivalent weight average molecular weight of preferably 3,000 to 1,000,000, more preferably 5,000 to 500,000, and may be linear, branched or cyclic.
  • polymer compound (B) examples include poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4′-dimethylmaleimide)]-co-pentafluorostyrene-co- [2- [ O- (1′-methylpropylideneamino) carboxyamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4′-dimethylmaleimide)]-co-penta Fluorostyrene-co- [2- [1 ′-(3 ′, 5′-dimethylpyrazolyl) carbonylamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4'-dimethylmaleimide)]-co-pentafluorostyrene-co-acrylonit
  • ⁇ Polymer compound (C)> Another preferred embodiment of the polymer compound contained in the organic thin film transistor insulating layer material of the present invention has a plurality of photodimerization reactive groups, a plurality of the first functional groups, and two active hydrogens. It is a high molecular compound contained above. Such a polymer compound is referred to as a polymer compound (C).
  • the active hydrogen may be directly bonded to the main chain constituting the polymer compound or may be bonded through a predetermined group.
  • active hydrogen may be contained in each structural unit which comprises a high molecular compound, and may be contained only in a part of structural unit. Furthermore, the active hydrogen may be bonded only to the terminal of the polymer compound.
  • polymer compound (C) examples include two structural units each having a repeating unit represented by the formula (1) and a repeating unit containing a first functional group and one active hydrogen.
  • examples thereof include a high molecular compound having the above, a high molecular compound having a repeating unit represented by the formula (1) and a repeating unit containing a first functional group and having a structural unit having two or more active hydrogens. .
  • the polymer compound (C) includes, for example, a monomer having an active hydrogen-containing group and a monomer having an unsaturated bond such as a double bond, a polymerizable monomer that is a raw material for the repeating unit represented by the above formula (1), It can be produced by copolymerizing with a polymerizable monomer containing one functional group.
  • a polymerizable monomer other than the monomer may be added during the polymerization.
  • a photopolymerization initiator or a thermal polymerization initiator may be applied.
  • the thing similar to what was mentioned above is applicable as a polymerizable monomer, a photoinitiator, and a thermal polymerization initiator.
  • Examples of the monomer having an active hydrogen-containing group and an unsaturated bond include aminostyrene, hydroxystyrene, vinyl benzyl alcohol, aminoethyl methacrylate, ethylene glycol monovinyl ether, and 4-hydroxybutyl acrylate.
  • the polymer compound (C) has a polystyrene-equivalent weight average molecular weight of preferably 3,000 to 1,000,000, more preferably 5,000 to 500,000, and may be linear, branched or cyclic.
  • the molar ratio of the polymerizable monomer containing the first functional group used in producing the polymer compound (C) to the monomer containing active hydrogen and the monomer having an unsaturated bond is preferably 60/100 to 150. / 100, more preferably 70/100 to 120/100, and still more preferably 90/100 to 110/100. If the molar ratio is less than 60/100, the active hydrogen may be excessive and the effect of reducing hysteresis may be reduced. If the molar ratio exceeds 150/100, the functional group that reacts with the active hydrogen will be excessive and the threshold voltage will be absolute. The value can be large.
  • polymer compound (C) examples include poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4′-dimethylmaleimide)]-co-aminostyrene-co- [2- [O -(1'-methylpropylideneamino) carboxyamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ', 4'-dimethylmaleimide)]-co-aminostyrene -Co- [2- [1 '-(3', 5'-dimethylpyrazolyl) carbonylamino] ethyl-methacrylate]), poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ', 4' -Dimethylmaleimide)]-co-aminostyrene-co-acrylonitrile-co- [2-
  • polymer compound (D) Another preferred embodiment of the polymer compound contained in the organic thin film transistor insulating layer material of the present invention has a plurality of photodimerization reactive groups, a fluorine atom, a plurality of the first functional groups, and A polymer compound containing two or more repeating units containing active hydrogen.
  • a polymer compound (D) Such a polymer compound is referred to as a polymer compound (D).
  • the active hydrogen may be directly bonded to the main chain constituting the polymer compound or may be bonded via a predetermined group.
  • active hydrogen may be contained in each structural unit which comprises a high molecular compound, and may be contained only in a part of structural unit. Furthermore, the active hydrogen may be bonded only to the terminal of the polymer compound.
  • polymer compound (D) examples include a repeating unit represented by the formula (1), a repeating unit represented by the formula (2), and a repeating unit containing a first functional group.
  • a polymer compound having two or more structural units having one active hydrogen, a repeating unit represented by the formula (1), a repeating unit represented by the formula (2), and a first functional group And a polymer compound having a repeating unit and a structural unit having two or more active hydrogens.
  • the polymer compound (D) includes, for example, a monomer having an active hydrogen-containing group and a monomer having an unsaturated bond such as a double bond, a polymerizable monomer serving as a raw material for the repeating unit represented by the above formula (1), It can manufacture by copolymerizing with the polymerizable monomer used as the raw material of the repeating unit represented by Formula (2), and the polymerizable monomer containing a 1st functional group.
  • the monomer which has unsaturated bonds, such as a group containing active hydrogen and a double bond the polymerizable monomer used as the raw material of the repeating unit represented by the said Formula (1), the repetition represented by the said Formula (2)
  • a polymerizable monomer other than the polymerizable monomer serving as the raw material of the unit and the polymerizable monomer containing the first functional group may be added during the polymerization.
  • a photopolymerization initiator or a thermal polymerization initiator may be applied.
  • the thing similar to what was mentioned above is applicable as a polymerizable monomer, a photoinitiator, and a thermal polymerization initiator.
  • monomers having an active hydrogen-containing group and an unsaturated bond include the monomers described above.
  • the polymer compound (D) has a polystyrene-equivalent weight average molecular weight of preferably 3,000 to 1,000,000, more preferably 5,000 to 500,000, and may be linear, branched or cyclic.
  • the molar ratio of the polymerizable monomer, which is a raw material for the first functional group used in the production of the polymer compound (D), to the active hydrogen-containing group and the monomer having an unsaturated bond is preferably 60/100 to 150/100, more preferably 70/100 to 120/100, and still more preferably 90/100 to 110/100. If the molar ratio is less than 60/100, the active hydrogen may be excessive and the effect of reducing hysteresis may be reduced. If the molar ratio exceeds 150/100, the functional group that reacts with the active hydrogen will be excessive and the threshold voltage will be reduced. The absolute value may be large.
  • polymer compound (D) examples include poly (styrene-co- [N- (3-methacryloyloxypropyl-3 ′, 4′-dimethylmaleimide)]-co-aminostyrene-co-pentafluorostyrene-co.
  • the organic thin film transistor insulating layer material of the present invention may contain an active hydrogen compound (E).
  • the active hydrogen compound (E) reacts with the second functional group generated in the polymer compounds (A) to (D) and binds to it, thereby forming a crosslinked structure inside the insulating layer. it can.
  • the active hydrogen compound (E) includes a low molecular compound containing two or more active hydrogens (hereinafter referred to as a low molecular active hydrogen compound (E-1)) and a polymer compound containing two or more active hydrogens ( Hereinafter, the polymer active hydrogen compound (E-2)) is included.
  • Examples of the active hydrogen typically include a hydrogen atom contained in an amino group, a hydroxy group, or a mercapto group.
  • active hydrogen hydrogen contained in a phenolic hydroxy group, hydrogen contained in an alcoholic hydroxy group, aromatic amino group capable of favorably producing a reaction with the above-described reactive functional groups, in particular, isocyanato groups and isothiocyanato groups. Hydrogen contained in is preferred.
  • the low molecular active hydrogen compound (E-1) include a compound having a structure in which two or more active hydrogen-containing groups are bonded to a low molecular structure.
  • this low molecular structure include an alkyl structure and a benzene ring structure.
  • Specific examples of the low molecular weight compound include amine compounds, alcohol compounds, phenol compounds, and thiol compounds.
  • the “alkyl structure” means a linear, branched, or cyclic structure composed of an aliphatic hydrocarbon.
  • the “benzene ring structure” means a linear, branched, or cyclic structure composed of an aromatic hydrocarbon.
  • amine compounds include ethylenediamine, propylenediamine, hexamethylenediamine, N, N, N ′, N ′,-tetraaminoethylethylenediamine, ortho-phenylenediamine, meta-phenylenediamine, para-phenylenediamine, N, N′-diphenyl-para-phenylenediamine, melamine, 2,4,6-triaminopyrimidine, 1,5,9-triazacyclododecane, 1,3-bis (3-aminopropyl) tetramethyldisiloxane, 1 , 4-bis (3-aminopropyldimethylsilyl) benzene, 3- (2-aminoethylaminopropyl) tris (trimethylsiloxy) silane.
  • alcohol compounds examples include ethylene glycol, 1,2-dihydroxypropane, glycerol, and 1,4-dimethanolbenzene.
  • phenolic compounds include 1,2-dihydroxybenzene, 1,3-dihydroxybenzene, 1,4-dihydroxybenzene (hydroquinone), 1,2-dihydroxynaphthalene, resorcin, fluoroglycerol, 2,3,4- Examples include trihydroxybenzaldehyde and 3,4,5-trihydroxybenzamide.
  • thiol compounds include ethylene dithiol and para-phenylene dithiol.
  • the low molecular weight compound containing two or more active hydrogens alcohol compounds, phenol compounds, and aromatic amine compounds are preferable.
  • the active hydrogen may be directly bonded to the main chain constituting the polymer compound or may be bonded through a predetermined group.
  • the active hydrogen may be contained in the structural unit constituting the polymer compound. In that case, it may be contained in each structural unit, or may be contained only in a part of the structural units. . Furthermore, the active hydrogen may be bonded only to the terminal of the polymer compound.
  • polymer active hydrogen compound (E-2) examples include a compound having a structure in which a group containing two or more active hydrogens is bonded to a polymer structure.
  • the polymer active hydrogen compound (E-2) is obtained by polymerizing a monomer having an active hydrogen-containing group and an unsaturated bond such as a double bond alone or by repeating the monomer represented by the above formula (1). Copolymerizing with a polymerizable monomer that is a raw material of the repeating unit represented by the above formula (2) or the repeating unit containing the first functional group, or by copolymerizing the monomer with another copolymerizable compound. It is obtained by forming a coalescence. The polymerization or copolymerization of these polymerizable monomers may be performed using a method usually used by those skilled in the art.
  • a photopolymerization initiator or a thermal polymerization initiator may be applied.
  • the thing similar to what was mentioned above is applicable as a polymerizable monomer, a photoinitiator, and a thermal polymerization initiator.
  • monomers having an active hydrogen-containing group and an unsaturated bond include the monomers described above.
  • monomers containing active hydrogen and monomers having unsaturated bonds monomers containing amino groups are preferred.
  • a novolak resin obtained by condensing a phenol compound and formaldehyde in the presence of an acid catalyst is also preferably used.
  • the weight average molecular weight in terms of polystyrene of the polymer compound containing two or more groups containing active hydrogen is preferably from 1,000 to 1,000,000, and more preferably from 3,000 to 500,000. Thereby, the effect that the flatness and uniformity of the insulating layer are improved can be obtained.
  • the weight average molecular weight in terms of polystyrene is measured by GPC.
  • the polymer compounds (A) to (D) are all light and heat energy crosslinkable and can be used as the organic thin film transistor insulating layer material of the present invention.
  • the polymer compounds (A) and (B) do not have active hydrogen.
  • the second functional group can react with water, and the polymer compounds (A) and (B) can also be thermally crosslinked.
  • One preferable aspect of the organic thin film transistor insulating layer material of the present invention is a composition containing the polymer compound (A) and / or (B) and the active hydrogen compound (E).
  • a composition containing the polymer compound (B) and the active hydrogen compound (E) is more preferable.
  • the mixing ratio of the polymer compound (A) and / or (B) and the active hydrogen compound (E) is determined by the second functional group that can be generated from the polymer compound (A) and / or (B) and the active hydrogen.
  • a ratio in which the molar ratio of the group containing active hydrogen in the compound (E) is 60/100 to 150/100 is preferable. The ratio is more preferably 70/100 to 120/100, and still more preferably 90/100 to 110/100. If the molar ratio is less than 60/100, the active hydrogen may be excessive and the effect of reducing hysteresis may be reduced. If the molar ratio exceeds 150/100, the functional group that reacts with the active hydrogen is excessive.
  • the absolute value of the threshold voltage may increase.
  • Another preferred embodiment of the organic thin film transistor insulating layer material of the present invention is a polymer compound (C).
  • the polymer compound (D) is more preferable. Since the polymer compound (C) and the polymer compound (D) have the first functional group and the group containing active hydrogen, they can be used alone for the organic thin film transistor insulating layer material of the present invention. .
  • the organic thin film transistor insulating layer material of the present invention contains an organic group and a functional group bonded to the polymer compounds (A) to (E).
  • the contents of the organic group and the functional group are appropriately determined by adjusting the amount of the repeating unit having the organic group and the functional group in consideration of the performance required for the organic thin film transistor insulating layer material.
  • the molar fraction of the repeating unit containing a photodimerization reactive group is 0.01 to based on the total number of repeating units of the polymer compound contained in the organic thin film transistor insulating layer material of the present invention. It is 0.7, preferably 0.05 to 0.6, more preferably 0.1 to 0.5. If the molar fraction of the repeating unit containing the photodimerization reactive group is less than 0.01, curing may be insufficient, and if it exceeds 0.7, the transistor characteristics may be adversely affected.
  • the molar fraction of the repeating unit containing the first functional group is 0.01 to 0.7, preferably 0.05 to 0.6, more preferably 0.1 to 0.5. If the molar fraction of the repeating unit containing the first functional group is less than 0.01, curing may be insufficient, and if it exceeds 0.7, transistor characteristics may be adversely affected.
  • the amount of active hydrogen is determined based on the amount that reacts with the first functional group without excess or deficiency.
  • the amount of fluorine introduced into the polymer compound is preferably 50% by mass or less, preferably 1 to 40% by mass, more preferably 5 to 35% by mass with respect to the total amount of the polymer compound.
  • the amount of fluorine exceeds 50% by mass, the affinity with the organic semiconductor material is deteriorated, and it may be difficult to stack the layer thereon.
  • the organic thin film transistor insulating layer material of the present invention includes a solvent for mixing and viscosity adjustment, a crosslinking agent used for crosslinking the polymer compounds (A) to (D), and an additive used in combination with the crosslinking agent.
  • Etc. may be included.
  • Solvents used include ether solvents such as tetrahydrofuran and diethyl ether, aliphatic hydrocarbon solvents such as hexane, alicyclic hydrocarbon solvents such as cyclohexane, unsaturated hydrocarbon solvents such as pentene, and aromatic carbonization such as xylene.
  • Examples thereof include a hydrogen solvent, a ketone solvent such as acetone, an acetate solvent such as butyl acetate, an alcohol solvent such as isopropyl alcohol, a halogen solvent such as chloroform, and a mixed solvent of these solvents.
  • the catalyst for promoting a crosslinking reaction, a leveling agent, a viscosity modifier, etc. can be used.
  • the organic thin film transistor insulating layer material of the present invention is a composition used for forming an insulating layer contained in an organic thin film transistor. Among the insulating layers of organic thin film transistors, it is preferably used for forming an overcoat layer or a gate insulating layer.
  • the organic thin film transistor insulating layer material is preferably an organic thin film transistor overcoat layer composition or an organic thin film transistor gate insulating layer composition, and more preferably an organic thin film transistor gate insulating layer material.
  • FIG. 1 is a schematic cross-sectional view showing the structure of a bottom gate top contact organic thin film transistor according to an embodiment of the present invention.
  • the organic thin film transistor includes a substrate 1, a gate electrode 2 formed on the substrate 1, a gate insulating layer 3 formed on the gate electrode 2, an organic semiconductor layer 4 formed on the gate insulating layer 3, A source electrode 5 and a drain electrode 6 formed on the organic semiconductor layer 4 with a channel portion interposed therebetween, and an overcoat 7 covering the entire element are provided.
  • a bottom gate top contact type organic thin film transistor includes, for example, a gate electrode formed on a substrate, a gate insulating layer formed on the gate electrode, an organic semiconductor layer formed on the gate insulating layer, and a source electrode formed on the organic semiconductor layer. It can be manufactured by forming a drain electrode and forming an overcoat.
  • the organic thin film transistor insulating layer material of the present invention is suitably used for forming a gate insulating layer as an organic thin film transistor gate insulating layer material. Moreover, it can also be used for forming an overcoat layer as an organic thin film transistor overcoat layer material.
  • FIG. 2 is a schematic cross-sectional view showing the structure of a bottom gate bottom contact type organic thin film transistor which is an embodiment of the present invention.
  • a substrate 1 a gate electrode 2 formed on the substrate 1, a gate insulating layer 3 formed on the gate electrode 2, and a channel portion on the gate insulating layer 3 are formed.
  • a bottom gate bottom contact type organic thin film transistor includes, for example, a gate electrode formed on a substrate, a gate insulating layer formed on the gate electrode, a source electrode and a drain electrode formed on the gate insulating layer, and a source electrode and a drain electrode. It can be manufactured by forming an organic semiconductor layer thereon and forming an overcoat.
  • the organic thin film transistor insulating layer material of the present invention is suitably used for forming a gate insulating layer as an organic thin film transistor gate insulating layer material. Moreover, it can also be used for forming an overcoat layer as an organic thin film transistor overcoat layer material.
  • a solvent or the like is added to prepare an insulating layer coating solution, and the insulating layer coating solution is placed under the gate insulating layer or overcoat layer. It is performed by applying to the surface of the layer located, drying and curing.
  • the organic solvent used in the insulating layer coating solution is not particularly limited as long as it dissolves the organic thin film transistor insulating layer material, but is preferably an organic solvent having a boiling point of 100 ° C. to 200 ° C. at normal pressure. .
  • organic solvent examples include 2-heptanone (boiling point 151 ° C.) and propylene glycol monomethyl ether acetate (boiling point 146 ° C.).
  • a leveling agent, a surfactant, a curing catalyst, and the like can be added to the insulating layer coating solution as necessary.
  • the organic thin film transistor insulating layer material of the present invention can also be used for forming a gate insulating layer as an organic thin film transistor gate insulating layer composition.
  • the insulating layer coating solution can be applied onto the gate electrode by a known method such as spin coating, die coater, screen printing, or ink jet.
  • the formed coating layer is dried as necessary. Drying here means removing the solvent contained in the applied resin composition.
  • the dried coating layer is then cured.
  • Curing means that the organic thin film transistor insulating layer material is crosslinked. Cross-linking of the transistor insulating layer material is performed, for example, by applying electromagnetic wave irradiation or heat to the coating layer.
  • a second functional group is generated from the first functional group of the polymer compound (A) or (B), and the second functional group reacts with the active hydrogen-containing group of the active hydrogen compound (E). Because. Alternatively, the second functional group is generated from the first functional group of the polymer compound (C) or (D), and the second functional group reacts with the active hydrogen-containing group in the molecule.
  • Crosslinking of the organic thin film transistor insulating layer material is also performed by irradiating the coating layer with electromagnetic waves or electron beams. This is because when the coating layer is irradiated with an electromagnetic wave or an electron beam, dimerization occurs due to the cyclization reaction of the photodimerization reactive groups of the polymer compounds (A) to (D).
  • the organic thin film transistor insulating layer is: Forming the coating layer on the substrate by applying a liquid containing an organic thin film transistor insulating layer material to the substrate; and irradiating the coating layer with an electromagnetic wave or an electron beam. Is preferred.
  • an organic thin film transistor insulating layer material is formed.
  • it is formed by a forming method including a step of coating a liquid containing the substrate on the substrate and forming a coating layer on the substrate; and a step of irradiating the coating layer with an electromagnetic wave or an electron beam.
  • the layer includes a step of applying a liquid containing an organic thin film transistor insulating layer material to a substrate to form a coating layer on the substrate; a step of irradiating the coating layer with an electromagnetic wave or an electron beam; and heating the coating layer. It is more preferable to form by the forming method including the step of applying.
  • the crosslink density of the insulating layer is improved by performing both the step of irradiating the coating layer with electromagnetic waves or electron beams and the step of applying heat to the coating layer.
  • the organic thin film transistor insulating layer material is used for the gate insulating layer, the absolute value and hysteresis of the threshold voltage (Vth) of the organic thin film transistor are reduced. It is considered that the polarization at the time of voltage application is further suppressed by improving the crosslinking density of the insulating layer, and the absolute value and hysteresis of the threshold voltage of the organic thin film transistor are reduced.
  • the coating layer When heat is applied to the coating layer, the coating layer is heated to a temperature of about 80 to 250 ° C., preferably about 100 to 230 ° C., and maintained for about 5 to 120 minutes, preferably about 10 to 60 minutes. If the heating temperature is too low or the heating time is too short, the insulating layer is not sufficiently crosslinked, and if the heating temperature is too high or the heating time is too long, the insulating layer may be damaged.
  • the irradiation conditions are adjusted in consideration of the degree of crosslinking and damage of the insulating layer.
  • the application condition is adjusted in consideration of the cross-linking of the insulating layer and the degree of damage.
  • the wavelength of the electromagnetic wave to be irradiated is preferably 450 nm or less, more preferably 150 to 410 nm.
  • the organic thin film transistor insulating layer material may be insufficiently crosslinked.
  • electromagnetic waves ultraviolet rays are preferable.
  • Irradiation with ultraviolet rays can be performed using, for example, an exposure apparatus used for manufacturing a semiconductor or a UV lamp used for curing a UV curable resin.
  • the electron beam irradiation can be performed using, for example, a micro electron beam irradiation tube.
  • Heating can be performed using a heater, an oven, or the like. Other irradiation conditions and heating conditions are appropriately determined according to the type and amount of the photodimerization reactive group.
  • a self-assembled monolayer may be formed on the gate insulating layer.
  • the self-assembled monolayer can be formed, for example, by treating the gate insulating layer with a solution obtained by dissolving 1 to 10% by weight of an alkylchlorosilane compound or an alkylalkoxysilane compound in an organic solvent.
  • alkylchlorosilane compound examples include methyltrichlorosilane, ethyltrichlorosilane, butyltrichlorosilane, decyltrichlorosilane, and octadecyltrichlorosilane.
  • alkylalkoxysilane compound examples include methyltrimethoxysilane, ethyltrimethoxysilane, butyltrimethoxysilane, decyltrimethoxysilane, and octadecyltrimethoxysilane.
  • the substrate 1, gate electrode 2, source electrode 5, drain electrode 6 and organic semiconductor layer 4 may be composed of commonly used materials and methods. Resin or plastic plates, films, glass plates, silicon plates, etc. are used as the material of the substrate. As the electrode material, chromium, gold, silver, aluminum, molybdenum, or the like is used, and the electrode is formed by a known method such as a vapor deposition method, a sputtering method, a printing method, or an ink jet method.
  • a ⁇ -conjugated polymer is used as the organic semiconductor compound for forming the organic semiconductor layer 4.
  • polypyrroles, polythiophenes, polyanilines, polyallylamines, fluorenes, polycarbazoles, polyindoles, poly (P -Phenylene vinylene) and the like can be used.
  • low-molecular substances having solubility in organic solvents for example, polycyclic aromatic derivatives such as pentacene, phthalocyanine derivatives, perylene derivatives, tetrathiafulvalene derivatives, tetracyanoquinodimethane derivatives, fullerenes, carbon nanotubes Etc. can be used.
  • the organic semiconductor layer can be formed, for example, by adding a solvent or the like if necessary for the organic semiconductor compound, preparing an organic semiconductor coating solution, applying the organic semiconductor coating solution on the gate insulating layer, and applying the organic semiconductor coating solution to the organic semiconductor coating solution. This is done by drying.
  • the resin constituting the gate insulating layer has a benzene ring and has an affinity for an organic semiconductor compound. Therefore, a uniform and flat interface is formed between the organic semiconductor layer and the gate insulating layer by the coating and drying method.
  • the solvent used in the organic semiconductor coating solution is not particularly limited as long as it dissolves or disperses the organic semiconductor, but is preferably a solvent having a boiling point of 50 ° C. to 200 ° C. at normal pressure.
  • the solvent include chloroform, toluene, anisole, 2-heptanone, and propylene glycol monomethyl ether acetate.
  • the organic semiconductor coating liquid can be applied onto the gate insulating layer by a known method such as spin coating, die coater, screen printing, and ink jet as in the case of the insulating layer coating liquid.
  • the organic thin film transistor of the present invention may be coated with an overcoat material for the purpose of protecting the organic thin film transistor and improving the smoothness of the surface.
  • the insulating layer manufactured using the organic thin film transistor insulating layer material of the present invention can be laminated with a flat film or the like, and a laminated structure can be easily formed. Moreover, an organic electroluminescent element can be suitably mounted on the insulating layer.
  • a display member having an organic thin film transistor can be suitably produced using the organic thin film transistor insulating layer material of the present invention.
  • a display provided with a display member can be manufactured using the display member having the organic thin film transistor.
  • the organic thin film transistor insulating layer material of the present invention can also be used for forming a layer included in a transistor other than an insulating layer and a layer included in an organic electroluminescence element.
  • Synthesis example 1 (Synthesis of Compound 1) In a 500 ml eggplant flask containing a water trap and stirrer, 25 g of 1-cyclohexene-1,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry), 12 g of 3-aminopropanol, and 200 ml of toluene are placed in an oil bath. The reaction was carried out at 140 ° C. for 4 hours. After completion of the reaction, the reaction mixture was concentrated with a rotary evaporator, and 100 ml of diethyl ether (manufactured by Wako Pure Chemical Industries) was added.
  • the obtained diethyl ether solution was transferred to a separatory funnel, washed with an aqueous sodium carbonate solution, and then washed with water until the aqueous layer became neutral and separated. After the organic layer was dried over anhydrous magnesium sulfate, the solid was filtered off and the filtrate was concentrated with a rotary evaporator to obtain Compound 1 as a tan viscous liquid.
  • the high molecular compound 3 has the following repeating unit.
  • the numbers in parentheses indicate the mole fraction of repeating units.
  • Synthesis example 2 (Synthesis of polymer compound 4) 1.88 g of 2,1,3-benzothiadiazole-4,7-di (ethylene boronate) and 2,6-dibromo- (4,4-bis-hexadecanyl-4H-cyclopenta [2,1-b; In toluene (80 mL) containing 3.81 g of 3,4-b ′]-dithiophene, under nitrogen, 0.75 g of tetrakis (triphenylphosphine) palladium, methyltrioctylammonium chloride (manufactured by Aldrich, trade name “Aliquat”) 336 "(R)) and 24 mL of 2M aqueous sodium carbonate solution were added.
  • Polymer compound 4 which has the following repeating unit represents the number of repeating units.
  • Example 1 (Production of organic thin film transistor insulating layer material and field effect organic thin film transistor) Into a 10 ml sample bottle, 2.00 g of the propylene glycol monomethyl ether acetate solution of the polymer compound 3 obtained in Synthesis Example 1 and 2.00 g of propylene glycol monomethyl ether acetate are added and dissolved while stirring. A uniform coating solution 1 as a material was prepared.
  • the obtained coating solution was filtered using a membrane filter having a pore diameter of 0.2 ⁇ m, spin-coated on a glass substrate with a chromium electrode, and then dried on a hot plate at 100 ° C. for 1 minute. Then, after irradiating UV light (wavelength 365 nm) of 1600 mJ / cm 2 using an aligner (manufactured by Canon; PLA-521), the gate insulating layer is obtained by baking at 200 ° C. for 30 minutes on a hot plate in nitrogen. It was.
  • the polymer compound 4 was dissolved in xylene as a solvent to prepare a solution (organic semiconductor composition) having a concentration of 0.5% by weight, and this was filtered through a membrane filter to prepare a coating solution. .
  • the obtained coating solution is applied on the gate insulating layer by a spin coating method to form an active layer having a thickness of about 30 nm, and then, on the active layer by a vacuum deposition method using a metal mask,
  • a field effect organic thin film transistor was manufactured by forming a source electrode and a drain electrode (having a laminated structure in the order of molybdenum oxide and gold from the active layer side) having a channel length of 20 ⁇ m and a channel width of 2 mm.
  • the field effect organic thin film transistor thus fabricated has the transistor characteristics of a vacuum probe (BCT22MDC-5-5) under the condition that the gate voltage Vg is changed to 20 to -40V and the source-drain voltage Vsd is changed to 0 to -40V.
  • the hysteresis of the field effect organic thin film transistor is that the source-drain voltage Vsd is ⁇ 40 V, and the threshold voltage Vth1 and the gate voltage Vg are changed from ⁇ 40 V to 20 V when the gate voltage Vg is changed from 20 V to ⁇ 40 V. It was expressed as a voltage difference from the threshold voltage Vth2.
  • Comparative Example 1 Manufacture of field-effect organic thin-film transistors
  • a field effect organic thin film transistor was produced in the same manner as in Example 1 except that the coating solution 2 was used in place of the coating solution 1 and UV irradiation was not performed when forming the gate insulating layer. When the transistor characteristics were measured and evaluated, it did not operate as a transistor in the region where the gate voltage Vg was 20V to -40V.

Landscapes

  • Thin Film Transistor (AREA)
  • Electroluminescent Light Sources (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Le problème résolu par la présente invention est la description d'un matériau de couche d'isolation de transistor à couche mince organique capable de produire un transistor à couche mince organique ayant une faible hystérésis et ayant une tension de seuil avec une faible valeur absolue. Le problème est résolu par un matériau de couche d'isolation de transistor à couche mince organique contenant un composé polymère (A) qui a un motif de répétition ayant un groupe maléimide substitué et a une unité de répétition contenant un premier groupe fonctionnel, ledit premier groupe fonctionnel étant un groupe fonctionnel qui génère un deuxième groupe fonctionnel qui réagit avec un hydrogène actif par l'intermédiaire de l'action d'un rayonnement électromagnétique ou de la chaleur.
PCT/JP2012/052356 2011-02-07 2012-02-02 Matériau de couche d'isolation de transistor à couche mince organique réticulable par l'énergie lumineuse et thermique Ceased WO2012108326A1 (fr)

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JP2011-023926 2011-02-07
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2908608A4 (fr) * 2012-10-15 2016-06-29 Sumitomo Chemical Co Procédé permettant de fabriquer un dispositif électronique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007111168A1 (fr) * 2006-03-29 2007-10-04 Sumitomo Bakelite Company, Ltd. Composition de résine, vernis, film de résine et dispositif à semi-conducteur utilisant le film de résine
JP2007301551A (ja) * 2006-04-12 2007-11-22 Sumitomo Bakelite Co Ltd 樹脂膜の製造方法、樹脂膜及び半導体装置
WO2008016110A1 (fr) * 2006-08-04 2008-02-07 Mitsubishi Chemical Corporation Couche isolante, dispositif électronique, transistor à effet de champ, et polyvinylthiophénol
WO2010024238A1 (fr) * 2008-08-28 2010-03-04 住友化学株式会社 Composition de résine, couche d’isolation de grille et transistor à couches minces organiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007111168A1 (fr) * 2006-03-29 2007-10-04 Sumitomo Bakelite Company, Ltd. Composition de résine, vernis, film de résine et dispositif à semi-conducteur utilisant le film de résine
JP2007301551A (ja) * 2006-04-12 2007-11-22 Sumitomo Bakelite Co Ltd 樹脂膜の製造方法、樹脂膜及び半導体装置
WO2008016110A1 (fr) * 2006-08-04 2008-02-07 Mitsubishi Chemical Corporation Couche isolante, dispositif électronique, transistor à effet de champ, et polyvinylthiophénol
WO2010024238A1 (fr) * 2008-08-28 2010-03-04 住友化学株式会社 Composition de résine, couche d’isolation de grille et transistor à couches minces organiques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2908608A4 (fr) * 2012-10-15 2016-06-29 Sumitomo Chemical Co Procédé permettant de fabriquer un dispositif électronique
US9437821B2 (en) 2012-10-15 2016-09-06 Sumitomo Chemical Company, Limited Method for manufacturing electronic device

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