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WO2007097212A1 - Procede de fabrication d'un dispositif semi-conducteur organique et composition pour former le film isolant utilise dans celui-ci - Google Patents

Procede de fabrication d'un dispositif semi-conducteur organique et composition pour former le film isolant utilise dans celui-ci Download PDF

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Publication number
WO2007097212A1
WO2007097212A1 PCT/JP2007/052345 JP2007052345W WO2007097212A1 WO 2007097212 A1 WO2007097212 A1 WO 2007097212A1 JP 2007052345 W JP2007052345 W JP 2007052345W WO 2007097212 A1 WO2007097212 A1 WO 2007097212A1
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Prior art keywords
insulating film
forming
organic semiconductor
composition
carbon atoms
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PCT/JP2007/052345
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English (en)
Japanese (ja)
Inventor
Toshiyuki Ogata
Daisuke Kawana
Hideo Hada
Motoki Takahashi
Yutaka Ohmori
Hirotake Kajii
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Tokyo Ohka Kogyo Co Ltd
University of Osaka NUC
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Tokyo Ohka Kogyo Co Ltd
Osaka University NUC
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Publication of WO2007097212A1 publication Critical patent/WO2007097212A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
    • H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
    • H01L21/02137—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC the material comprising alkyl silsesquioxane, e.g. MSQ
    • 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

Definitions

  • the present invention relates to a method for producing an organic semiconductor element and an insulating film forming composition used therefor.
  • organic FETs organic field effect transistors
  • TFTs thin film transistors
  • Organic field effect transistors (hereinafter referred to as organic FETs) often use thin films as semiconductors and are sometimes referred to as organic thin film transistors (hereinafter referred to as organic TFTs).
  • This organic TFT consists of a substrate, an insulating film, a gate electrode layer, a source electrode, a drain electrode, and an organic semiconductor film.
  • organic TFT consists of low molecular weight compounds such as polyacenes, ⁇ -conjugated polymers such as polythiophene, and ⁇ -shared oligomers are used as materials that exhibit semiconducting properties used in organic semiconductor films.
  • low molecular weight compounds such as polyacenes, ⁇ -conjugated polymers such as polythiophene, and ⁇ -shared oligomers are used as materials that exhibit semiconducting properties used in organic semiconductor films.
  • organic TFTs Compared to amorphous silicon TFTs, organic TFTs have the same or better charge mobility, but have a very high driving voltage and threshold voltage. Therefore, in the development of organic semiconductor elements, there is a need for an organic insulator layer that can adjust the drive voltage and reduce the threshold voltage.
  • each constituent member such as an organic insulator layer and a gate insulating film has a polymer-based glass transition point in order to prevent softness and deterioration of the substrate. It must be formed at a lower temperature and avoiding a vacuum.
  • Patent Document 1 an insulating film containing a compound having a silsesquioxane structure is used. As a result, the organic insulating film can be formed at a low temperature. It is also possible to provide an organic semiconductor element that can be driven at a low voltage and has a stable driving voltage value.
  • Patent Document 1 JP 2004-304121 A
  • an object of the present invention is to provide a method for producing an organic semiconductor element that can be driven at a low voltage and has a stable driving voltage value, and a composition for forming an insulating film used therefor.
  • composition for forming an insulating film of the present invention By using the composition for forming an insulating film of the present invention, it becomes possible to form a dense insulating film.
  • the present inventors have used a coconut resin having a specific silsesquioxane skeleton.
  • the present inventors have found that it is effective in reducing intermolecular voids and has good electrical characteristics, and has completed the present invention.
  • an insulating film is formed between the gate electrode layer and the organic semiconductor film layer of the organic semiconductor element, containing the resin component (A) having a silsesquioxane skeleton.
  • X represents an alkylene group having 1 to 15 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 15 carbon atoms
  • R 1 represents a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, or a carbon number.
  • R 2 represents an alkyl group having 2 to 15 carbon atoms
  • R 2 represents an alkyl group having 1 to 4 carbon atoms
  • n is 0 or 1.
  • the second aspect of the present invention is a method of forming the insulating film by applying the composition for forming an insulating film on a substrate provided with a gate electrode layer, and an organic semiconductor on the insulating film.
  • a method for producing an organic semiconductor element comprising: forming a film; and forming a source electrode and a drain electrode on the organic semiconductor film.
  • structural unit refers to a monomer unit constituting a polymer.
  • organic semiconductor film layer hereinafter also referred to as organic semiconductor film
  • insulating film are intended to include a single thin film and a layered structure in which a plurality of thin films are laminated.
  • At least part of the side chain of the resin (A) having a silsesquioxane skeleton has a hydroxyl group and a group in which Z or a hydrogen atom of this hydroxyl group is substituted with a hydrophobic group.
  • the unit (al) it is possible to reduce the voids between molecules. As a result, a dense insulating film can be formed. As a result, it is possible to provide an organic semiconductor element that can be driven at a low voltage and has a stable driving voltage value.
  • FIG. 1 is a diagram showing a first embodiment of an organic semiconductor element according to the present invention.
  • FIG. 2 is a view showing a second embodiment of the organic semiconductor element according to the present invention.
  • FIG. 3 is a view showing a third embodiment of the organic semiconductor element according to the present invention.
  • composition for forming an insulating film according to the present invention is a resin component having a silsesquioxane skeleton.
  • component (A) (hereinafter also referred to as component (A)), preferably a compound (B) (hereinafter also referred to as component (B)) that generates an acid or a base by the action of light or heat.
  • component (B) preferably a compound (B) (hereinafter also referred to as component (B)) that generates an acid or a base by the action of light or heat.
  • the component (A) contains silsesquioxane succinate (A1) having a structural unit (al) represented by the following general formula (a-1).
  • X represents an alkylene group having 1 to 15 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 15 carbon atoms
  • R 1 represents a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, or a carbon number.
  • R 2 represents an alkoxyalkyl group having 2 to 15 carbon atoms
  • R 2 represents an alkylene group having 1 to 5 carbon atoms
  • n is 0 or 1.
  • X represents an alkylene group having 1 to 15 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 15 carbon atoms. Examples of the alkylene group having 1 to 15 carbon atoms include linear, branched and cyclic alkylene groups.
  • a straight-chain or branched alkylene group a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a tert-butyl group, or an isotropic hydrogen atom, preferably having 1 to 6 carbon atoms
  • Examples include groups other than individual groups.
  • a cyclic alkylene group it is preferably 4 to 15 carbon atoms, more preferably 4 to 12 carbon atoms, more preferably 5 to carbon atoms: LO is most preferable.
  • Specific examples include groups in which two or more hydrogen atoms have been removed from a polycycloalkane such as a monocycloalkane, bicycloalkane, tricycloalkane, and tetracycloalkane.
  • the divalent aromatic hydrocarbon group having 6 to 15 carbon atoms is a naphthyl group, a phenyl group, an anthracenyl group, a phenanthryl group, etc., which is a group in which one hydrogen atom is removed. I prefer a group with one hydrogen atom removed.
  • R 1 is an alkyl group having 1 to 15 carbon atoms or an alkoxyalkyl group having 2 to 15 carbon atoms.
  • alkyl group having 1 to 15 carbon atoms include linear, branched and cyclic alkyl groups.
  • the straight-chain or branched alkyl group preferably has 1 to 6 carbon atoms.
  • a cyclic alkyl group preferably has 4 to 15 carbon atoms, more preferably 4 to 12 carbon atoms, and most preferably LO.
  • Specific examples include groups in which two or more hydrogen atoms have been removed from a polycycloalkane such as a monocycloalkane, bicycloalkane, tricycloalkane, and tetracycloalkane.
  • Specific examples include monocycloalkanes such as cyclopentane and cyclohexane, and groups obtained by removing one hydrogen atom from polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane. .
  • Examples thereof include a clopentyl group, a 1-ethyl-1-cyclohexyl group, and a 1-ethyl-1-cyclopentyl group.
  • alkoxyalkyl group having 2 to 15 carbon atoms examples include 1-ethoxyethyl group, 1-ethoxymethyl group, 1-methoxyethyl group, 1-methoxymethyl group, 1-methoxypropyl group, 1-ethoxypropyl group, l Examples include —n-butoxychetyl group, 2-adamantoxymethyl group, and 1-hexoxyloxymethyl group.
  • R 2 is an alkylene group having 1 to 5 carbon atoms, and is a hydrogen atom from a methyl group, an ethyl group, an n propyl group, an i propyl group, an n butyl group, a tert-butyl, a tert-amyl group, or the like. Examples include groups other than individual groups.
  • n is 0 or 1, and is preferably 1. However, n is 0 when X is a linear or branched alkylene group.
  • the structural unit (al) is based on all the structural units that constitute the silsesquioxane O hexanes ⁇ (A1), and 10 to 95 Monore 0/0, 15 to 90 Monore 0/0 force S preferably , and most preferably 20 to 85 Monore 0/0 force S further favorable Mashigu 30 to 80 mol%. By setting it within the above range, the effect of the present invention is excellent.
  • the silsesquioxane skeleton has a siloxane unit as a main chain and a hydrocarbon group as a side chain, it can be said to be a ladder structure in which an inorganic compound and an organic compound are converted into hybrids. Since this ladder structure has fewer branches, there are fewer intermolecular voids than a resin having a normal silsesquioxane skeleton. Therefore, by having a silsesquioxane skeleton, a dense insulating film can be formed even at a low temperature. In addition, even when the film thickness is 500 nm or less, an insulating film having sufficient insulating properties can be formed.
  • the structural unit (al) represented by the general formula (a-1) when used, the group represented by R 1 in the structural unit (al) serves as a reactive site to form an insulating film. It is possible to fill the gaps between the molecules that occur during the process. As a result, it is possible to form a denser insulating film than a resin having no reaction active site.
  • the component (A) further contains a structural unit (a2) represented by the following general formula (a-2). May be.
  • R 3 represents an alkyl group having 1 to 15 carbon atoms or an aromatic hydrocarbon group having 6 to 15 carbon atoms.
  • R 3 represents an alkyl group having 1 to 15 carbon atoms or an aromatic hydrocarbon group having 6 to 15 carbon atoms.
  • alkyl group having 1 to 15 carbon atoms include linear, branched and cyclic alkyl groups.
  • the straight-chain or branched alkyl group preferably has 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and a tert-butyl group. Can be mentioned.
  • LO is most preferable.
  • Specific examples include groups in which two or more hydrogen atoms have been removed from a polycycloalkane such as a monocycloalkane, bicycloalkane, tricycloalkane, and tetracycloalkane.
  • monocycloalkanes such as cyclopentane and cyclohexane
  • groups obtained by removing one hydrogen atom from polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane.
  • the aromatic hydrocarbon group is a naphthyl group, a phenyl group, an anthracenyl group, a phenanthryl group, a benzyl group or the like, and a phenyl group or a benzyl group is preferable.
  • the reactivity of the structural unit (al) can be controlled, and appropriate reactivity can be imparted to such an extent that the intermolecular voids can be reduced. Is possible.
  • silsesquioxane rosin (A1) has a structural unit (al) and a structural unit (a2) that are run. It may be a random polymer polymerized in a dam or a block polymer. Moreover, not only a binary polymer but a ternary polymer and a quaternary polymer may be sufficient. Specifically, it is preferable that the following structural formulas (A-1) to (A-7) include at least one selected from the forces.
  • the mass average molecular weight (Mw) of silsesquioxane rosin (A1) is not particularly limited!
  • the force is more than 1000 and less than 10000, more preferably more than 2000 and less than 10000. By setting it within the above range, the solubility in an organic solvent is good.
  • the present invention [component (A) component ⁇ MA, WO2004 / 055598 or ⁇ oma WO2004 / 051376 [disclosed! It can be manufactured by a method that speaks.
  • the composition for forming an insulating film according to the present invention further contains a compound ( ⁇ ) (hereinafter also referred to as ( ⁇ ⁇ ⁇ ) component) that generates an acid or a base by the action of light or heat.
  • ⁇ a compound that generates an acid or a base by the action of light or heat.
  • the "compound that generates an acid or a base by the action of heat” refers to a compound that generates an acid or a base by heating at 80 ° C or higher and 200 ° C or lower.
  • the “compound that generates an acid or a base by the action of light” refers to a compound that generates an acid or a base by irradiation with ultraviolet rays.
  • a compound that generates an acid by the action of heat is referred to as a thermal acid generator.
  • a compound that generates a base by the action of heat is a thermal base generator! / ⁇ ⁇ .
  • a compound that generates an acid by the action of light is called a photoacid generator.
  • a compound that generates a base by the action of light is a photobase generator!
  • the component (B) of the present invention preferably contains at least one selected from the group consisting of a thermal acid generator, a thermal base generator, a photoacid generator, and a photobase generator.
  • the thermal acid generator used in the present invention is a compound that generates an acid in response to heat.
  • the thermal acid generator is not particularly limited, but 2, 4, 4, 6-tetrabromocyclohexagenone, benzoin tosylate, 2-troben ditosylate, other alkyl esters of organic sulfonic acid, etc. Can be used. Specific examples include sulfo salts, iodine salts, benzothiazoum salts, ammonium salts, onium salts such as phospho- um salts, and the like. Of these, particularly preferred are ododonium salts, sulfo-salts and benzothiazol salts.
  • sulfo-um salt and the benzothiazo-um salt include, for example, 4-acetoxyphenol dimethylsulfo-hexafluoroarsenate, benzyl 4-hydroxyphenol methylsulfo-hexaflux. Oloantimonate, 4-acetoxyphenol-pentamethylsulfohexafluoroantimonate, dibenzyl-4-hydroxyphenolsulfo-hexafluoroantimonate, 4-acetoxyphenol-pentenesulfo-hexane Examples thereof include fluoroantimonate, 3-benzylbenzothiazolium hexafluoroantimonate, and a compound represented by the following chemical formula (B-1).
  • the thermal base generator used in the present invention is a compound that generates a base in response to heat.
  • the thermal base generator is not particularly limited, but 1-methyl 1- (4-biphenyl) ethyl carbamate, 1,1 dimethyl-2-cyanethyl carbamate, etc.
  • Rubamate derivatives, urea derivatives such as urea and N, N-dimethyl-N'-methylurea, dihydropyridine derivatives such as 1,4-dihydronicotinamide, quaternized ammonium salts of organic silanes and organic boranes, dicyandiamide Etc. are used.
  • the photoacid generator used in the present invention is a compound that generates an acid in response to light.
  • the photoacid generator is not particularly limited, but is a salt, diazomethane derivative, darioxime derivative, bissulfone derivative, ⁇ -ketosulfone derivative, disulfone derivative, nitrobenzyl sulfonate derivative, sulfonate ester derivative.
  • Known acid generators such as sulfonic acid ester derivatives of ⁇ -hydroxyimide compounds can be used.
  • onium salt examples include tetramethyl ammonium trifluoromethanesulfonate, tetramethyl ammonium nonafluorobutane sulfonate, and tetra ⁇ -nonafluorobutane sulfonate.
  • diazomethane derivative examples include bis (benzenesulfol) diazomethane, bis (p-toluenesulfol) diazomethane, bis (xylenesulfol) diazomethane, bis (hexylsulfol) diazomethane, bis (Cyclopentylsulfo) diazomethane, bis (n-butylsulfol) diazomethane, bis (isobutylsulfol) diazomethane, bis (sec-butylsulfol) diazomethane, bis (n-propylsulfol) diazomethane, bis (Isopropylsulfol) diazomethane, bis (tert-butylsulfol) diazomethane, bis (n-amylsulfol) diazomethane, bis (isoamylsulfonyl
  • Examples of the darioxime derivative include bis-O- (p-toluenesulfol) ⁇ -dimethyl.
  • Tildaroxime Bis-O— (p Toluenesulfol) Hiddiphenylglyoxime
  • Bis-O— Bis-O— (p Toluenesulfol) a — Dicyclohexylglyoxime
  • Bis — O— p Toluenesulfo- 3) -Pentanedione Glyoxime
  • Bis—O- (n-Butanesulfol) ⁇ -Dimethyldariooxime Bis- ⁇ - ( ⁇ -butanesulfol) ⁇ -diphenylglyoxime, bis- ⁇ - ( ⁇ -butanesulfol) ⁇ -d
  • Examples of the bissulfone derivative include bisnaphthylsulfurmethane, bistrifluoromethylsulfonylmethane, bismethylsulfonylmethane, bisethylsulfonylmethane, bispropylsulfolmethane, bisisopropylsulfurmethane, bis-l-to- olene sulfonemethane. And bisbenzenesulfurmethane.
  • Examples of the ⁇ -ketosulfone derivative include 2-cyclohexylcarbo-l- ( ⁇ -toluenesulfol) propane, 2-isopropylcarboluol-2- ( ⁇ toluenesulfol) propane, and the like.
  • disulfone derivatives examples include disulfone derivatives such as diphenyldisulfone derivatives and dicyclohexyldisulfone derivatives.
  • Examples of the -trobenzyl sulfonate derivative include ⁇ -toluenesulfonic acid 2, 6 di
  • Examples thereof include -trobenzyl sulfonate derivatives such as nitrobenzyl and p-toluenesulfonic acid 2,4 dinitrobenzil.
  • sulfonic acid ester derivatives examples include 1, 2, 3 tris (methanesulfo-loxy) benzene, 1, 2, 3 tris (trifluoromethanesulfonyloxy) benzene, 1, 2, 3-tris (P toluene) Mention may be made of sulfonic acid ester derivatives such as sulfo-loxy) benzene.
  • Examples of the sulfonic acid ester derivative of the N-hydroxyimide compound include N hydroxysuccinimide methanesulfonic acid ester, N hydroxysuccinimide trifluoromethane sulfonic acid ester, N hydroxysuccinimide ethanesulfonic acid ester, and N hydroxysuccinimide.
  • the photobase generator used in the present invention is a compound that generates a base in response to light.
  • the photobase generator is not particularly limited, and examples thereof include photoactive power rubamates such as tri-phenol methanol, benzyl carbamate and benzoin carbamate; O-power rubermoyl hydroxylamide, O— Amides such as rubamoyloxime, aromatic sulfonamide, alpha-latatatam, and N- (2-arylethyl) amide and other amides; oxime esters, (X-aminoacetophenones, cobalt complexes, etc.
  • the salt is a sodium salt or a sulfonium salt, which is represented by the above chemical formula (B-1) and the following chemical formula (B-2). Compounds are preferred.
  • the content of component (B) is preferably 0.5 to 30 parts by mass, more preferably 0.5 to 25 parts by mass, with respect to 100 parts by mass of component (A). Most preferred is 20 parts by weight.
  • the content exceeds 0.5 parts by mass, the cross-linking is sufficiently advanced and a good insulating film can be formed.
  • the content is less than 30 parts by mass, the storage stability of the composition for forming an insulating film is kept good. This makes it possible to suppress the deterioration of the formed insulating film over time.
  • the composition for forming an insulating film according to the present invention can further contain a component (C) that is a cross-linking agent component.
  • the component (C) is not particularly limited as long as it can react with the OR 1 group in the structural unit (al).
  • the hydrolysis reaction in the component (A) is promoted, and the structural units (al) and (a2) of the silsesquioxane compound are efficiently crosslinked in a ladder shape.
  • a denser insulating film can be formed than a resin having no reaction active site.
  • the component (C) is not particularly limited, and can be arbitrarily selected from known crosslinking agents.
  • an amino group-containing compound such as melamine, acetateguanamine, benzoguanamine, urea, ethylene urea, propylene urea, glycoluril, or the like is reacted with formaldehyde or formaldehyde and a lower alcohol, and the hydrogen atom of the amino group is replaced with a hydroxymethyl group or Examples thereof include compounds substituted with a lower alkoxymethyl group.
  • Component (C) is at least one selected from the group consisting of melamine-based cross-linking agents, urea-based cross-linking agents, alkylene urea-based cross-linking agents, epoxy-based cross-linking agents, oxetane-based cross-linking agents, and daricoluril-based cross-linking agents.
  • a melamine type crosslinking agent or an epoxy type crosslinking agent it is particularly preferable to use.
  • melamine-based cross-linking agent melamine and formaldehyde are reacted, a compound in which the hydrogen atom of the amino group is substituted with a hydroxymethyl group, melamine, formaldehyde and lower alcohol are reacted.
  • examples thereof include compounds in which a hydrogen atom of an amino group is substituted with a lower alkoxymethyl group.
  • Specific examples include hexamethoxymethyl melamine, hexamethoxymethyl melamine, hexapropoxymethyl melamine, hexasuboxybutyl melamine, and the like.
  • hexamethoxymethyl melamine represented by the following structural formula (C-1) It is preferable to use.
  • the urea-based cross-linking agent includes a compound in which urea and formaldehyde are reacted to replace the hydrogen atom of the amino group with a hydroxymethyl group, and urea, formaldehyde and lower alcohol are reacted to form a hydrogen in the amino group. And compounds in which the atom is substituted with a lower alkoxymethyl group. Specific examples include bismethoxymethylurea, bisethoxymethylurea, bis-propyloxymethylurea, bisbutoxymethylurea, and the like. Among them, bismethoxymethylurea is preferable.
  • alkylene urea-based crosslinking agent examples include compounds represented by the following general formula (C2).
  • R and R are each independently a hydroxyl group or a lower alkoxy group, and R and R are
  • 3 4 5 6 each independently represents a hydrogen atom, a hydroxyl group or a lower alkoxy group, and p is an integer of 0-2.
  • the lower alkoxy group of R and R is preferably an alkoxy group having 1 to 4 carbon atoms.
  • This alkoxy group may be linear or branched.
  • R and R are the same
  • 3 4 may be different from each other, but are preferably the same.
  • the lower alkoxy group of R and R is preferably an alkoxy group having 1 to 4 carbon atoms.
  • This alkoxy group may be linear or branched.
  • R and R are the same
  • P is an integer of 0 to 2, preferably 0 or 1.
  • the alkylene urea crosslinking agent is particularly at least one of a compound in which p is 0 (ethylene urea crosslinking agent) or a compound in which p is 1 (propylene urea crosslinking agent). preferable.
  • the compound represented by the general formula (C2) is obtained by reacting a product obtained by condensation reaction of alkylene urea and formalin with a lower alcohol.
  • Alkylene urea crosslinking agents include mono- and Z- or dihydroxymethyl ethylene ethylene urea, mono- and Z- or dimethoxymethyl ethylene-urea, mono- and Z- or methoxymethylated ethylene urea, mono- and Z- or dipropoxy Ethyleneurea-based cross-linking agents such as methylated ethylene urea, mono and Z or dibutoxymethyl ethylene glycol; mono and Z or dihydroxymethylated propylene urea, mono and Z or dimethoxymethylated propylene urea, mono and Z or di Ethoxymethylated propylene urea, mono and Z or dipropoxymethylated propylene urea, mono and z or dibutoxymethylated propylene urea, etc. 1,3-di (methoxymethyl) 4,5-dihydroxy-2-imidazolidinone, 1,3-di (methoxymethyl) -4,5-dimethoxy-2-imidazolidinone, etc. .
  • the epoxy-based crosslinking agent is not particularly limited as long as it has an epoxy group, and can be arbitrarily selected and used. Among them, it is preferable to have two or more epoxy groups. By having two or more epoxy groups, cross-linking reactivity with the resin component (A) is improved.
  • the number of epoxy groups is preferably 2 or more, more preferably 2 to 4, and most preferably 2. The following are suitable as the epoxy-based crosslinking agent.
  • the oxetane-based crosslinking agent is not particularly limited as long as it has an oxetane skeleton and is a compound represented by the following chemical formula.
  • glycoluril-based crosslinking agent examples include glycoluril derivatives substituted with one or both of N-position S hydroxyalkyl group and C 1-4 alkoxyalkyl group.
  • a powerful glycoluril derivative is a condensation reaction between glycoluril and formalin. Obtained by reacting the product obtained by reaction with a lower alcohol.
  • Glycoluril-based crosslinking agents include mono-, di-, tri- and / or tetrahydroxymethylated glycolurils, mono-, di-, tri- and / or tetramethoxymethyl glycolurils, mono-, di- and tri- And / or tetraethoxymethylethyl glycoluril, mono, di, tri and / or tetrapropoxymethyl ethyl glycoluril, mono, di, tri and / or tetrabutoxymethyl glycol glycol.
  • the above crosslinking agents may be used alone or in combination of two or more.
  • the content of component (C) is preferably 0.5 to 30 parts by mass, more preferably 0.5 to 25 parts by mass, with respect to 100 parts by mass of component (A). Part by mass is most preferred.
  • the content exceeds 0.5 parts by mass, the cross-linking is sufficiently advanced and a good insulating film can be formed.
  • the content is less than 30 parts by mass, the storage stability of the composition for forming an insulating film can be maintained well, and deterioration of the formed insulating film over time is suppressed.
  • the composition for forming an insulating film according to the present invention further contains a component (D) that is an organic solvent.
  • the component (D) is not particularly limited as long as it can dissolve the rosin crosslinking agent such as alcohols and esters.
  • ⁇ -latatones such as petit-mouth rataton
  • ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl- ⁇ -amyl ketone, methyl isoamyl ketone, 2-heptanone;
  • Polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol;
  • Monomethino ethenore of compounds having an ester bond such as ethylene glycol monoacetate, diethylene glycol monoacetate, propylene glycol monoacetate, dipropylene glycol monoacetate, the polyhydric alcohols or the compound having an ester bond
  • polyhydric alcohols or the compound having an ester bond Derivatives of polyhydric alcohols such as compounds having an ether bond such as monoalkyl ethers or monophenyl ethers such as monoethinoreethenole, monopropinoreethenole, monobutinoleate, etc.
  • Nomethyl ether acetate (PGMEA), propylene glycol monomethyl ether ( ⁇ GME) is preferred];
  • Cyclic ethers such as dioxane, and esters such as methyl lactate, ethyl lactate (EL), methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methyl methoxypropionate, ethyl ethoxypropionate;
  • esters such as methyl lactate, ethyl lactate (EL), methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methyl methoxypropionate, ethyl ethoxypropionate;
  • organic solvents may be used alone or as a mixed solvent of two or more.
  • propylene glycol monomethyl ether acetate PGMEA
  • PGME propylene glycol monomethyl ether
  • EL EL
  • a mixed solvent in which PGMEA and a polar solvent are mixed is preferable.
  • the mixing ratio may be appropriately determined in consideration of the compatibility between PGMEA and the polar solvent, but is preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2. Preferably within range! /.
  • the mass ratio of PGMEA: EL is preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2.
  • the mass ratio of PGMEA: PGME is preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2, more preferably 3: 7 to 7: Three.
  • a mixed solvent of at least one kind selected from among PGMEA and EL and ⁇ -petit-mouthed rataton is also preferable.
  • the mixing ratio of the former and the latter is preferably 70: 30-95: 5.
  • the amount of component (D) used is not particularly limited, but is a concentration that can be applied to a substrate, etc., and is appropriately set according to the coating film thickness, but in general, the solid content of the composition for forming an insulating film
  • the concentration is 2 to 20% by mass, preferably 5 to 15% by mass.
  • various components are solvents.
  • the organic semiconductor device is manufactured according to three embodiments. Hereinafter, each aspect is specifically described. explain.
  • a first aspect is a step of applying an insulating film forming composition according to the present invention on a substrate provided with a gate electrode layer to form an insulating film (hereinafter referred to as an insulating film forming step); A step of forming an organic semiconductor film on the insulating film (hereinafter referred to as an organic semiconductor film formation step), and a step of forming a source electrode and a drain electrode on the organic semiconductor film (hereinafter referred to as an electrode formation step). ) And.
  • the organic semiconductor element 1 manufactured by this process is a so-called top contact type.
  • the insulating film forming step may further include a step of forming the gate electrode layer 21 on the substrate 10.
  • the substrate 10 can be made of resin, glass, silicon or the like.
  • the material of the gate electrode layer 21 is not particularly limited as long as it can be formed on the substrate 10 at a low temperature.
  • organic materials such as polyarine and polythiophene, and raw materials such as conductive ink are used. These are formed on the substrate 10 as electrode layers.
  • the gate electrode layer 21 is made of a metal such as gold, platinum, chromium, palladium, aluminum, indium, molybdenum, nickel, an alloy using these metals, polysilicon, amorphous silicon, indium and tin. It is also possible to use inorganic materials such as oxides (ITO) and stannates. These inorganic materials can be formed as electrodes by known photolithography. The above materials may be used alone or in combination of two or more. A substrate on which a gate electrode is stacked from the beginning can also be used.
  • the insulating film 30 is formed by applying the insulating film forming composition according to the present invention to the substrate 10 on which the gate electrode layer 21 is formed.
  • the coating method of the insulating film forming composition is not particularly limited, and is not limited to the known spin coating method, dip coating method, printing method, roll coating method, cast method, spray coating method, doctor blade method, die coating method. It is performed by a wet process such as a coating method or an inkjet method. Among them, it is preferable to use a spin coating method, a date coating method, a printing method, a roll coating method, etc. in that the coating amount can be controlled to form a film with a desired film thickness.
  • the insulating film-forming composition applied on the substrate 10 is preferably dried at a predetermined temperature.
  • the drying temperature is preferably 70 ° C or higher and 200 ° C or lower, and more preferably 180 ° C or lower. When the heating temperature is in the above range, a dense insulating film can be formed, and the electrical characteristics are good.
  • the drying time is preferably 5 to 120 minutes, more preferably 5 to 100 minutes.
  • the thickness of the insulating film 30 formed through such a process is 10: LOOOnm, and preferably 10-9 OOnm, more preferably 10-800nm.
  • the organic semiconductor film forming step refers to a step of forming the organic semiconductor film 40 on the insulating film formed by the insulating film forming step.
  • the organic semiconductor film 40 it is preferable to use a ⁇ -electron conjugated aromatic compound, a chain compound, an organic pigment, an organic silicon compound, or the like. Specific examples include, but are not limited to, pentacene derivatives, tetracene, anthracene, thiophene oligomer derivatives, phenylene derivatives, phthalocyanine compounds, polyacetylene derivatives, polythiophene derivatives, cyanine dyes, and the like.
  • a known thin film forming method such as vapor deposition, coating, adhesion from a solution, or the like can be used.
  • the substrate 10 is a resin, it is more preferable. It is preferred to choose a method that can be done at low temperatures.
  • the thickness of the organic semiconductor film 40 is preferably 5 nm to 200 nm, more preferably 20 nm to 100 nm.
  • the thickness is 200 nm or more, in the case of the top contact structure, the resistance in the film thickness direction portion increases, and the transistor characteristics deteriorate. If the thickness is 5 nm or less, a thin film is not formed and an island-shaped film is formed.
  • the drain electrode 22 and the source electrode 23 are formed on the organic semiconductor film 40 formed in the organic semiconductor film forming step. These are formed in the same manner as the gate electrode layer 21. Further, the same material as that of the gate electrode layer 21 may be used, but it may be different.
  • the second aspect is a method of forming an organic semiconductor film after forming a source electrode and a drain electrode on a substrate, and applying an insulating film forming composition according to the present invention on the organic semiconductor film. Forming an insulating film, and forming a gate electrode layer on the insulating film.
  • the drain electrode 22 and the source electrode 23 are formed on the substrate 10, and the organic semiconductor film 40 and the insulating film 30 are formed thereon. Furthermore, it is a so-called bottom contact structure in which a gate electrode layer 21 is formed thereon.
  • the formation method of each structural member is performed by the method similar to a 1st aspect.
  • a step of forming an organic semiconductor film on a substrate, and after forming a source electrode and a drain electrode on the organic semiconductor film, the composition for forming an insulating film according to the present invention is applied to form an insulating film And a step of forming a gate electrode layer on the insulating film.
  • the organic semiconductor film 40 is formed on the substrate 10, the drain electrode 22 and the source electrode 23 are formed thereon, and further, the insulating This is a so-called bottom contact structure in which the film 30 and the gate electrode layer 21 are formed.
  • the formation method of each structural member is performed by the method similar to a 1st aspect.
  • a P-type organic thin film transistor having a top contact structure as shown in Fig. 1 was manufactured as an organic semiconductor element. This was designated as Sample 1.
  • composition for forming an insulating film includes 100 parts by mass of a resin represented by the following structural formula (A-1a)
  • ⁇ , ⁇ -dihexylosexithiophene (a, ⁇ -dih exylsexithiophen: trade name DH-6T: manufactured by Starck Vitec) was used.
  • substrate a commercially available polished indium stannate glass substrate (a glass substrate) was used.
  • the gate electrode layer was formed by patterning this glass substrate by etching.
  • the above-mentioned composition for forming an insulating film is applied onto a gate electrode layer formed on a glass substrate by a spin coating method to form a film, and then in the atmosphere at 200 ° C for 20 minutes. An insulating film was formed by heating. The thickness of the insulating film at this time was 360 nm.
  • the organic semiconductor film composition was formed to a thickness of 30 nm at a deposition rate of lA / min by the organic molecular beam deposition method to form an organic semiconductor film.
  • a gold electrode was formed as a source drain electrode by vapor deposition, and the P-type organic thin film transistor having the top contact structure shown in FIG. 1 was manufactured.
  • the channel length was 100 m
  • the channel width was 2 mm
  • the film thickness was 30 nm.
  • V Gate voltage threshold (V)
  • Example 1 the mobility was 0 ⁇ 10 cm 2 ZVs, and V was 6.6V.
  • Example except using 100 parts by mass A P-type organic thin film transistor was manufactured in the same manner as in 1. This was designated as Sample 2. The film thickness of the insulating film at this time was 310 nm. Further, the mobility of the transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • a p-type organic thin film transistor was produced in the same manner as in Example 1 except that a crosslinking agent represented by the following structural formula (C1) was used as the composition for forming an insulating film. This was designated as Sample 3.
  • the addition amount of this crosslinking agent was 10 parts by mass with respect to 100 parts by mass of the resin. Note that the thickness of the insulating film at this time was 290 nm. Further, the mobility of the transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • a p-type organic thin film transistor was produced in the same manner as in Example 3 except that the thermal acid generator represented by the following structural formula (B-2) was used as the composition for forming an insulating film. This was designated as sample 4. Note that the thickness of the insulating film at this time was 310 nm. At this time, the addition amount of the crosslinking agent and the thermal acid generator was 10 parts by mass of the crosslinking agent and 2 parts by mass of the thermal acid generator with respect to 100 parts by mass of the resin, respectively.
  • Example 1 The composition described in Example 1 was used as the composition for forming an insulating film.
  • PCBM polyphenyl C61-butylic acid methyl ester
  • E-1 the organic semiconductor film forming material. It was.
  • Example 1 As in Example 1, ⁇ , ⁇ -dihexyl-sexithiophene was used as the organic semiconductor film forming material, and a commercially available indium stannate glass substrate (substrate glass) was used as the substrate. Substrate). As the gate electrode layer, this glass substrate was patterned by etching to form an electrode layer.
  • the composition for forming an insulating film is applied onto a gate electrode layer formed on a glass substrate by a spin coating method to form a film, and then, for 20 minutes at 200 ° C in the atmosphere. An insulating film was formed by heating. The thickness of the insulating film at this time was 360 nm.
  • the organic semiconductor film forming material was formed into a thickness of 30 nm by spin coating to form an organic semiconductor film.
  • gold electrodes were formed as the source and drain electrodes by vapor deposition, and the n-type organic thin film transistor having the top contact structure shown in FIG. 1 was manufactured.
  • the channel length was 100 m
  • the channel width was 2 mm
  • the film thickness was 30 nm. This was designated as Sample 5.
  • the mobility of transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • composition for forming an insulating film the resin described in Example 1, the crosslinking agent (C3) represented by the following structural formula, and the thermal acid represented by the following structural formula (B-1) A generator was used.
  • the addition amount of the crosslinking agent and thermal acid generator is 10 parts by weight for each 100 parts by weight of the resin.
  • the mass part and the thermal acid generator were 3 parts by mass.
  • This composition for forming an insulating film was applied onto a silicon substrate by a spin coating method, and formed into a thickness of 30 nm to form an organic semiconductor film.
  • a p-type organic thin film transistor was produced in the same manner as in Example 7 except that a crosslinking agent represented by the following structural formula (C-4) was used as the composition for forming an insulating film. This was designated as Sample 8. The addition amount of this crosslinking agent was 10 parts by mass with respect to 100 parts by mass of the resin. At this time, the thickness of the insulating film was 380 nm. Further, the mobility of the transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • a P-type organic thin film transistor was manufactured in the same manner as in Example 1 except that 100 parts by mass was used and an insulating film having a thickness of 390 nm was formed. This was designated as comparative sample 1. Further, the mobility of transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • the composition for forming an insulating film in addition to 100 parts by mass of the resin represented by the structural formula (A-8) described in Comparative Example 1, the crosslinking represented by the structural formula (C 1) described in Example 3 is used.
  • a p-type organic thin film transistor was produced in the same manner as in Comparative Example 1 except that 10 parts by mass of the agent was added to 100 parts by mass of the resin to form an insulating film having a thickness of 410 nm. This was designated as comparative sample 2. Further, the mobility of transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • n-type organic thin film transistor was manufactured using the composition for forming an insulating film described in Comparative Example 1 as the composition for forming an insulating film. This was designated as Comparative Sample 3. Further, the mobility of transistor characteristics was calculated in the same manner as in Example 1. The results are shown in Table 1.
  • Vth V
  • nm cm 2 / V s
  • composition for forming an insulating film can provide an organic semiconductor element that can be driven at a low voltage and has a stable driving voltage value.

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Abstract

La présente invention concerne une composition destinée à la formation d'un film isolant, pouvant réduire les espaces entre les molécules, formant ainsi un film isolant dense. L'invention concerne également un film isolant et un dispositif semi-conducteur organique qui peut être commandé à une faible tension tout en ayant une tension de commande stable en utilisant un tel film isolant. L'invention concerne en particulier une composition pour la formation d'un film isolant entre une couche d'électrode de grille et une couche de film semi-conducteur organique dans un dispositif semi-conducteur organique, laquelle composition contient un composant résineux (A) ayant une structure de silsesquioxane. Le composant résineux (A) est composé d'une résine (A1) ayant un motif structural (a1) représenté par la formule générale (a-1) ci-dessous. (a-1) (Dans la formule, X représente un groupe alkylène comportant 1 à 15 atomes de carbone ou un groupe hydrocarbure aromatique divalent comportant 6 à 15 atomes de carbone ; R1 représente un atome d'hydrogène, un groupe alkyle comportant 1 à 15 atomes de carbone ou un groupe alcoxyalkyle comportant 2 à 15 atomes de carbone ; R2 représente un groupe alkyle comportant 1 à 4 atomes de carbone ; et n représente 0 ou 1.)
PCT/JP2007/052345 2006-02-22 2007-02-09 Procede de fabrication d'un dispositif semi-conducteur organique et composition pour former le film isolant utilise dans celui-ci Ceased WO2007097212A1 (fr)

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WO2009075233A1 (fr) * 2007-12-10 2009-06-18 Kaneka Corporation Composition durcissable développable par un alcali, film mince isolant utilisant celle-ci et transistor à film mince
JP2012119679A (ja) * 2010-12-01 2012-06-21 Xerox Corp 薄膜トランジスタのための誘電性組成物
US8809414B2 (en) 2008-10-02 2014-08-19 Kaneka Corporation Photocurable composition and cured product

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JP2007254677A (ja) * 2006-03-24 2007-10-04 Tokyo Ohka Kogyo Co Ltd シリカ系被膜形成用組成物およびシリカ系被膜
JP4962714B2 (ja) * 2007-03-15 2012-06-27 Ｊｓｒ株式会社 二酸化ケイ素膜およびトレンチアイソレーションの形成方法ならびにそのための組成物
JP5407860B2 (ja) 2008-03-18 2014-02-05 東レ株式会社 ゲート絶縁材料、ゲート絶縁膜、および有機電界効果型トランジスタ
JP2011040634A (ja) * 2009-08-13 2011-02-24 Ulvac Japan Ltd 多孔質膜の前駆体組成物、多孔質膜及びその作製方法、並びに半導体装置
JP2012109538A (ja) 2010-10-29 2012-06-07 Tokyo Ohka Kogyo Co Ltd 積層体、およびその積層体の分離方法
JP5756334B2 (ja) 2010-10-29 2015-07-29 東京応化工業株式会社 積層体、およびその積層体の分離方法
JP5802106B2 (ja) 2010-11-15 2015-10-28 東京応化工業株式会社 積層体、および分離方法
KR101746270B1 (ko) 2011-10-31 2017-06-12 도오꾜오까고오교 가부시끼가이샤 웨이퍼와 당해 웨이퍼의 지지체를 접착하기 위한 접착제 조성물, 및 그 이용
JP6826361B2 (ja) * 2015-05-13 2021-02-03 東京応化工業株式会社 絶縁膜形成用感光性組成物、及び絶縁膜パターンの形成方法
WO2024034385A1 (fr) * 2022-08-08 2024-02-15 ダウ・東レ株式会社 Procédé de fabrication d'organopolysiloxane ramifié à teneur en groupe hydroxyle phénolique

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JP2005520354A (ja) * 2002-07-11 2005-07-07 インターナショナル・ビジネス・マシーンズ・コーポレーション ハードマスク層としてのシリコン含有反射防止組成物
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WO2009075233A1 (fr) * 2007-12-10 2009-06-18 Kaneka Corporation Composition durcissable développable par un alcali, film mince isolant utilisant celle-ci et transistor à film mince
CN101896537B (zh) * 2007-12-10 2012-10-24 株式会社钟化 具有碱显影性的固化性组合物、使用该组合物的绝缘性薄膜以及薄膜晶体管
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US8809414B2 (en) 2008-10-02 2014-08-19 Kaneka Corporation Photocurable composition and cured product
JP2012119679A (ja) * 2010-12-01 2012-06-21 Xerox Corp 薄膜トランジスタのための誘電性組成物

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