WO2009150972A1 - 絶縁膜形成用インキ組成物、該インキ組成物から形成された絶縁膜 - Google Patents
絶縁膜形成用インキ組成物、該インキ組成物から形成された絶縁膜 Download PDFInfo
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- WO2009150972A1 WO2009150972A1 PCT/JP2009/060129 JP2009060129W WO2009150972A1 WO 2009150972 A1 WO2009150972 A1 WO 2009150972A1 JP 2009060129 W JP2009060129 W JP 2009060129W WO 2009150972 A1 WO2009150972 A1 WO 2009150972A1
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- Prior art keywords
- insulating film
- ink composition
- forming
- ink
- organic solvent
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- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
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- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
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- UNDXPKDBFOOQFC-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UNDXPKDBFOOQFC-UHFFFAOYSA-N 0.000 description 1
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- 239000004925 Acrylic resin Substances 0.000 description 1
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- 229930185605 Bisphenol Natural products 0.000 description 1
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- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
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- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- HPUOAJPGWQQRNT-UHFFFAOYSA-N pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1 HPUOAJPGWQQRNT-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
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- 230000007261 regionalization Effects 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 229920002379 silicone rubber Polymers 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
Images
Classifications
-
- 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
- H01L21/02118—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 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
-
- 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
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
- H01L21/02288—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating printing, e.g. ink-jet printing
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/312—Organic layers, e.g. photoresist
-
- 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]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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 an ink composition for forming an insulating film that can be suitably used for manufacturing an electronic device, and an insulating film formed from the ink composition.
- Transistors are widely used as important electronic elements (electronic parts) that make up televisions and computer equipment, and are currently manufactured using inorganic materials such as silicon as the main material.
- an organic transistor (OFET) using an organic substance as a member of such a transistor has attracted attention (see Non-Patent Document 1).
- OFET is soft and flexible, and has the advantage that raw materials can be produced at a low price when considered per unit area, and is an essential item in the ubiquitous era, that is, a component that is indispensable for realizing flexible and low-cost terminals. It is considered.
- OFET is an electronic device having three electrodes, an insulating layer, and a semiconductor layer as essential members.
- An example of the element structure is shown in FIG.
- a wet process such as a printing method and a dry process such as vacuum deposition and sputtering.
- Patent Document 2 the wet process usually needs to undergo an overheating (firing) process after film formation.
- this overheating (firing) process is required to be performed at a lower temperature.
- PEN polyethylene naphthalate
- a baking temperature of 150 ° C. or less is required.
- the insulating film forming ink may be required to have excellent printing characteristics that can cope with fine pattern formation.
- various characteristics required for the GI itself include those related to the element manufacturing process and those related to the element electrical characteristics (FET characteristics).
- the former has a characteristic that it does not dissolve in the solvent used in the organic semiconductor layer that is the upper layer of the GI, that is, solvent resistance.
- solvent resistance In the latter, it is said that the higher the insulation in a thin film state (the smaller the leakage current) and the higher the smoothness of the surface, the better the device characteristics.
- a polyvinylphenol material (I) using a polyimide material as a curing agent is known (see Non-Patent Document 3).
- curing agent is known (refer nonpatent literature 4).
- thermoplastic resins (II) represented by polymethyl methacrylate and polystyrene are also known (see Non-Patent Document 5).
- the thermoplastic resin is inferior in solvent resistance, and it is difficult to laminate a conductive layer, a semiconductor layer, etc. on the upper layer by a printing method, and a dry process step requiring equipment such as vapor deposition is required. .
- Patent Document 6 Solid or liquid bisphenol type general-purpose epoxy resin (III) is also known (see Non-Patent Document 6).
- Patent Document 1 discloses an insulating material containing a silane coupling agent and an epoxy resin (see Patent Document 1).
- Patent Document 2 discloses a method for manufacturing a circuit element by a letterpress reverse printing method, but there is no description regarding firing at a low temperature (see Patent Document 2). Therefore, in order to form an electronic device by providing an insulating film on a flexible substrate, there is no ink technology for forming an insulating film that has sufficient firing temperature, solvent resistance, and insulating properties. Furthermore, there is currently no ink technology for forming an insulating film that has sufficient precision pattern forming ability.
- the first problem in the present invention is to provide an insulating ink composition for forming an insulating film having sufficient firing temperature, solvent resistance, and insulating properties.
- a second problem is to provide an ink composition for forming an insulating film that can form a fine insulating film pattern required for forming a highly integrated organic transistor by a printing method.
- a third problem is to provide the ink composition
- An object of the present invention is to provide an insulating film formed from the composition.
- the present invention firstly includes an organic solvent, a polyvinylphenol-based resin, an epoxy resin, and a crosslinking assistant as essential components, and an ink composition for forming an insulating film, characterized in that I will provide a.
- the present invention secondly, a further insulating film forming ink composition that allows a fine insulating film patterns formed, the organic solvent described above is, vapor pressure at 20 ° C. is 11.3 ⁇ 10 2 Pa or more And an organic solvent having a boiling point of less than 115 ° C. under atmospheric pressure, and an organic solvent having a vapor pressure of less than 11.3 ⁇ 10 2 Pa at 20 ° C. and a boiling point of 115 ° C.
- An insulating film forming ink composition is provided.
- Third, an insulating film formed from the ink composition for forming an insulating film is provided.
- the ink composition for forming an insulating film of the present invention By using the ink composition for forming an insulating film of the present invention, it is possible to obtain excellent characteristics as an insulating film at a baking temperature of 100 to 140 ° C., and an insulating film is formed on a flexible substrate such as PEN. It becomes possible. Furthermore, the formed insulating film has solvent resistance, and other layers such as a conductive layer and a semiconductor layer can be stacked thereon by a printing method. In addition, since the leakage current is small, the insulating film can be suitably used as a gate insulating film of an organic field effect transistor (OFET) or the like.
- OFET organic field effect transistor
- the ink composition for forming an insulating film of the present invention is an ink composition for forming an insulating film containing an organic solvent, a polyvinylphenol resin, an epoxy resin, and a crosslinking aid as essential components.
- any solvent can be used as long as it dissolves the polyvinylphenol resin.
- pentane, hexane, heptane, octane, decane can be used.
- Dodecane isopentane, isohexane, isooctane, cyclohexane, methylcyclohexane, cyclopentane and other aliphatic hydrocarbon organic solvents, benzene, toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, mesitylene, naphthalene, cyclohexylbenzene , Aromatic hydrocarbon solvents such as diethylbenzene, methyl formate, ethyl formate, propyl formate, methyl acetate, ethyl acetate, isopropyl acetate, n-propyl acetate, isobutyl acetate, n-butyl acetate, methyl propionate, ethyl propionate, etc.
- Polyvinylphenol resins used in the ink composition for forming an insulating film of the present invention include p-vinylphenol homopolymer, p-vinylphenol and other vinyl monomers (for example, methyl methacrylate, 2-hydroxylethyl methacrylate, Copolymer with styrene, butyl acrylate, 2-hydroxylethyl acrylate, phenylmaleimide, maleic acid, fumaric acid), bromine substituted p-vinylphenol homopolymer obtained by bromine substitution of p-vinylphenol, bromine substituted p -Copolymers of vinylphenol and other vinyl resins, homopolymers of p-vinylphenol derivatives sulfonated, t-butylated, and aminated with p-vinylphenol, p-vinylphenol derivatives and other vinyl monomers There is a copolymer of There.
- p-vinylphenol homopolymer for example, methyl me
- the polyvinylphenol-based resin is preferably contained in an amount of 10% by mass or more in the total solid content excluding the extender pigment of the insulating film forming ink composition. More preferably, it is 25 mass% or more.
- the epoxy resin used in the ink composition for forming an insulating film according to the present invention functions as a crosslinking agent for polyvinylphenol resin, and any known epoxy resin having a bifunctional or more reactive epoxy group can be used.
- any known epoxy resin having a bifunctional or more reactive epoxy group can be used.
- bisphenol A type epoxy resin, bisphenol F type epoxy resin, polyfunctional epoxy resin, flexible epoxy resin, brominated epoxy resin, glycidyl ester type epoxy resin, polymer type epoxy resin, biphenyl type There are epoxy resins, but there is no particular limitation. These may be used alone or in combination of two or more.
- a crosslinking aid is used.
- the crosslinking aid any of amine compounds, polyamide resins, imidazoles, polymercaptans, boron trifluorides, dicyandiamides, organic acid hydrazides, triphenylphosphine, and other known and commonly used crosslinking aids may be used. These crosslinking aids may be used alone or in combination of two or more. From the viewpoint of room temperature stability and low temperature curing at 150 ° C. or lower, 2-ethyl-4-methylimidazole is preferred.
- crosslinking aids are contained in an amount of 0.3 to 10.0% by mass, preferably 1.0 to 5.0% by mass in the total solid content. If this content is outside this range and the amount is too small, curing will be insufficient, and if it is too large, a strong polar crosslinking aid will remain in the resulting insulating resin film, resulting in problems that hinder insulation properties. .
- constitutional component When an after-mentioned constitutional component is added, it is contained in an amount of 0.3 to 10.0% by mass, preferably 1.0 to 5.0% by mass in the total solid content excluding the constitutional component.
- the ink composition for forming an insulating film of the present invention can be used by adding various surfactants and the like as needed mainly for release agent, constitutional component, ink surface tension adjustment and leveling improvement. .
- the surfactant hydrocarbon, silicone, fluorine, and a mixture of two or more of these surfactants can be applied.
- the fluorosurfactant has excellent ink surface tension adjustment and leveling improvement effect.
- the insulating film formed from the ink added with the surfactant has a polythiophene-based crystalline organic semiconductor. It is the most suitable surfactant because it is excellent in compatibility and can be expected to improve not only ink characteristics but also transistor characteristics.
- a preferred fluorosurfactant is a nonionic fluorosurfactant having a linear perfluoroalkyl group and having a chain length of C6 or more, more preferably C8 or more.
- fuck F-482 Megafuck F-470 (R-08), Megafuck F-472SF, Megafuck R-30, Megafuck F-484, Megafuck F-486, Mega There is a fuck F-172D, a mega fuck F178RM (the trade name, manufactured by DIC), etc., but there is no particular limitation. These may be used alone or in combination of two or more.
- These surfactants are contained in the total ink composition in an amount of 0.01 to 5.0% by mass, preferably 0.05 to 1.0% by mass of the active component.
- substrates for forming electronic elements include glass woven epoxy laminates, glass nonwoven fabric epoxy laminates, paper epoxy laminates, paper phenol laminates, glass woven polyimide laminates, and the like, polyethylene naphthalate , Plastic films such as polyimide, polyethylene terephthalate, polycarbonate, etc., metal plates or foils such as copper, aluminum, stainless steel, iron coated with insulator, plate glass, alumina, zirconia, silica, etc.
- a plastic material having flexibility such as naphthalate, polyethylene terephthalate, and polycarbonate, the low temperature curability that is a feature of the present invention can be utilized.
- Various types of printing methods can be employed for forming the ink composition for forming an insulating film of the present invention into a film.
- a well-known and usual printing system can be used, and it can be manufactured by adopting a single-layer or multi-layer coating material manufacturing system.
- gravure method, offset method, letterpress method, screen method, reverse method, air doctor coater method, blade coater method, air knife coater method, squeeze coater method, impregnation coater method, transfer roll coater method, kiss coater method Examples thereof include a cast coater method, a spray coater method, a die method, a spin coater method, a bar coater method, a micro contact method, and a letterpress reverse printing method.
- the ink composition of the present invention contains an additive suitable for the printing method according to each printing method, a solvent suitable for the printing method is selected, and is prepared at a resin component concentration suitable for the printing method.
- the letterpress reverse printing method referred to here is an ink in which ink is applied to a smooth releasable surface made of polydimethylsiloxane (PDMS) and the like, and the letterpress serving as a release plate is pressed against the ink application surface, thereby contacting the letterpress.
- PDMS polydimethylsiloxane
- the ink applied to this printing method can uniformly wet the releasable surface, and the ink can be removed from the releasable surface neatly according to the relief pattern by pressing the relief, and the remaining ink pattern is released. It is required to transfer from the surface to the printing medium without remaining.
- the ink composition for forming an insulating film of the present invention suitable for such a printing method preferably contains two or more quick-drying and slow-drying solvents, a constitutional component, a surface energy adjusting agent, and a release agent in addition to the essential components. . By adding these components, the ink printing characteristics can be improved, and the fine patterning properties necessary for constituting an electronic component such as an organic transistor can be realized.
- any one or more of solvents having a vapor pressure of not less than 11.3 ⁇ 10 2 Pa (8.5 mmHg) at 20 ° C. and a boiling point of less than 115 ° C. under atmospheric pressure is used.
- the dry organic solvent is contained in the total ink composition in an amount of 5.0 to 90.0% by mass, preferably 10.0 to 60.0% by mass, and more preferably 20.0 to 40.0% by mass.
- fast-drying organic solvents are selected in consideration of the solubility of the resin and the affinity for the pigment dispersion system, and the following solvents are used as examples.
- ester solvents ethyl acetate, normal propyl acetate, isopropyl acetate, alcohol solvents as methanol, ethanol, 1-propanol, 2-propanol, hydrocarbon solvents as pentane, hexane, cyclohexane, methylcyclohexane, toluene, xylene
- ketone solvents include tetrahydrofuran and the like. These may also be a mixture of the respective systems and a plurality of systems. Of these, isopropyl acetate, ethanol and 2-propanol are preferable in view of their evaporation rate and surface tension.
- any one or more of solvents having a vapor pressure of less than 11.3 ⁇ 10 2 Pa (8.5 mmHg) at 20 ° C. and a boiling point of 115 ° C. or more at atmospheric pressure is used.
- the dry organic solvent is contained in the total ink composition in an amount of 5.0 to 90.0% by mass, preferably 30.0 to 70.0% by mass, and more preferably 40.0 to 60.0% by mass.
- These solvents are selected in consideration of the solubility of the resin and the affinity for the pigment dispersion system. For example, the following solvents are used.
- propylene glycol monomethyl ether acetate 3-methoxy-3-methyl-butyl acetate, ethoxyethyl propionate, and Diadol 135 are preferable in view of their evaporation rate and surface tension.
- the mold release agent one or two or more known and commonly used silicone compounds are used. Specific examples include dimethyl silicone oil, dimethyl silicone rubber, silicone resin, organically modified silicone, methylphenyl silicone oil, long chain alkyl modified silicone oil, mixture of fluorine compound and silicone polymer, fluorine modified silicone, etc. There is no particular limitation. These may be used alone or in combination of two or more. Among these, KF-96L series (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) is preferable from the viewpoint of releasability and compatibility with PVP resin. These release agents are contained in the total ink composition in an amount of 0.0 to 5.0% by mass, preferably 0.0 to 1.0% by mass. If the content is outside this range, an excessive amount is not preferable because not only the printing characteristics are deteriorated, but also a problem of inhibiting the insulating film characteristics occurs.
- a known and commonly used color pigment simple substance, fine particle powder simple substance, and a pigment dispersion in which these color pigment simple substance and fine particle powder alone are previously dispersed in a dispersant or an organic solvent are used.
- EXCEDIC BLUE0565, EXCEDIC RED 0759, EXCEDIC YELLOW 0599, EXCEDIC GREEN0358, EXCEDIC YELLOW0648 (trade name made by DIC), Aerosil series (trade name made by Evonik Co., Ltd.), Silicia, Silo Pure, Thylosphere, Silo Mask, Silwell, Fuji Balloon (trade name, manufactured by Fuji Silysia), PMA-ST, IPA-ST (trade name: Nissan Chemical), NANOBIC 3600 series, NANOBIC 3800 series (trade name, manufactured by Big Chemie)
- these may be used alone or in combination of two or more.
- the average particle size of the constitutional component added to the ink is preferably 1 to 150 nm, and more preferably 5 to 50 nm.
- the average particle diameter of the constitutional component can be easily measured by, for example, a dynamic light scattering method.
- These constitutional components are contained in the total solid content of 20 to 90% by mass, preferably 40 to 70% by mass. If the content is outside this range and the amount is too large, the insulating film becomes brittle, which is not preferable. On the other hand, if the amount is too small, the fine patterning characteristics of the ink are insufficient, which is not preferable.
- the ink suitable for the letterpress reverse printing method has the above-mentioned composition, but its physical properties are also an important factor.
- the physical properties first, the ink viscosity at a temperature of 25 ° C. is in the range of 0.5 mPa ⁇ s to 30.0 mPa ⁇ s. Of these, 1.0 to 5.0 mPa ⁇ s is more preferable.
- the surface energy of the ink composition is also an important factor.
- the surface energy of the ink composition is preferably 17 mN / m to 30 mN / m, but the surface energy is preferably lower than 22 mN / m.
- Example 1 As a polyvinylphenol resin, 2.3 g of Marcalinker M (manufactured by Maruzen Petroleum), 3.3 g of epoxy resin Epicron 850CPR (manufactured by DIC) as a crosslinking agent, and 2-ethyl-4-methylimidazole as a crosslinking aid
- Example 1 ink was prepared by mixing 0.14 g and 22.0 g of isopropyl acetate (hereinafter referred to as IPAc) as a solvent.
- IPAc isopropyl acetate
- Example 2 As a polyvinylphenol resin, 2.3 g of poly (4-vinylphenol-co-methyl methacrylate) (manufactured by Aldrich), 3.3 g of epoxy resin Epicron 850CPR (manufactured by DIC) as a crosslinking agent, Ink of Example 2 was prepared by mixing 0.06 g of 2-ethyl-4-methylimidazole, 22.0 g of cyclohexanone as a solvent, and 0.5 g of F-482 as a fluorosurfactant.
- Example 3 As a polyvinylphenol resin, 2.3 g of Marcalinker M (manufactured by Maruzen Petroleum), 3.3 g of epoxy resin Epicron 850CPR (manufactured by DIC) as a crosslinking agent, and 2-ethyl-4-methylimidazole as a crosslinking aid 0.15 g, 15 g of IPAc as solvent, 29 g of propylene glycol monomethyl ether, 6.0 g of propylene carbonate, 2.0 g of KF96L-1cs (manufactured by Shin-Etsu Chemical) as a release agent,
- Example 3 ink was prepared by mixing 1.0 g of F-482 (manufactured by DIC) and 0.3 g of MCF-350SF (manufactured by DIC), 25 g of PMA-ST (manufactured by Nissan Chemical) as a constitutional component, and mixing the above. did.
- Comparative Example 1 Comparative Example 1 in which 20.0 g of polymethyl methacrylate (PMMA) (manufactured by Aldrich: Mw 120,000) as an acrylic resin was mixed with 80.0 g of a solvent cyclohexanone instead of polyvinyl phenol resin and epoxy resin as a resin component. An ink was prepared.
- PMMA polymethyl methacrylate
- Mw 120,000 a solvent cyclohexanone
- Comparative Example 2 ink was prepared by mixing 20.0 g of a polystyrene resin (manufactured by Aldrich: Mw 44,000) with 80.0 g of a solvent cyclohexanone instead of polyvinylphenol resin and epoxy resin as a resin component.
- Comparative Example 4 1.9 g of phenol novolak resin (Phenolite TD-2090-60M: MEK solution with a solid content of 60%) and 2.0 g of epoxy resin Epicron 850CPR (manufactured by DIC), 2-ethyl-4-methylimidazole as a crosslinking aid Ink of Comparative Example 4 was prepared by mixing 4.0 g of isopropyl acetate (hereinafter referred to as IPAc) and 3.8 g of methyl ethyl ketone as a solvent.
- IPAc isopropyl acetate
- the ink of Comparative Example 3 was prepared from the above Example 1 ink on a glass plate having a thickness of 1.5 mm by a spin coater printing method so as to have a dry film thickness of 1 ⁇ m. Then, it baked for 30 minutes at 140 degreeC, and formed the solvent-resistant evaluation sample. The solvent resistance evaluation was performed by immersing the thin film produced as described above in butyl carbitol acetate for 20 hours together with the glass plate, and evaluating whether the thin film remained. The results are shown in Tables 1 and 2.
- each ink composition is printed on a glass plate with ITO having a thickness of 1.5 mm and baked at 140 ° C. for 30 minutes to obtain an insulating film having a dry film thickness of about 1 ⁇ m.
- a silver electrode was formed on the insulating film by a vacuum deposition method, and the current value when 150 V was applied to the insulating film was measured.
- the unit is mAcm- 2 .
- a transistor characteristic measuring element having a bottom gate bottom contact (BGBC) structure shown in FIG. 1 was prepared.
- BGBC bottom gate bottom contact
- a source / drain electrode pattern having a channel length of 50 ⁇ m and a channel width of 4 mm is formed on the previously formed gate insulating film by using a printing plate reverse printing using a conductive ink for reverse printing. The silver electrode was formed by baking for 40 minutes at 170 degreeC in oven.
- a P3HT thin film was formed on the insulating film, source and drain electrodes by spin coating using a 0.5 wt% solution of organic semiconductor (P3HT) Poly (3-hexylthiophene) in xylene.
- the prepared device was heat-treated in a glow box at 150 ° C. for about 5 minutes, and then the Id-Vg and Id-Vd characteristics were measured using a semiconductor parameter measuring apparatus (Keithley 4200).
- the field effect mobility and ON / OFF were determined by known methods.
- the unit of mobility is cm 2 / Vs.
- the ink composition for forming an insulating film of the present invention can be fired at a low temperature, and can be suitably applied to the production of an electronic device using a flexible film as a substrate.
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Abstract
Description
ポリビニルフェノール系樹脂として、マルカリンカーM(丸善石油製)を2.3g、架橋剤として、エポキシ樹脂エピクロン850CPR(DIC製)を3.3g、架橋助剤として、2-エチル-4-メチルイミダゾールを0.14gに、溶剤として、イソプロピルアセテート(以下IPAc)を22.0g、混合して実施例1インキを調製した。
ポリビニルフェノール系樹脂として、ポリ(4-ビニルフェノール-co-メチルメタアクリレート)(アルドリッチ製)を2.3g、架橋剤として、エポキシ樹脂エピクロン850CPR(DIC製)を3.3g、架橋助剤として、2-エチル-4-メチルイミダゾールを0.06gに、溶剤として、シクロヘキサノンを22.0g、フッ素系界面活性剤としてF-482を0.5g混合して実施例2インキを調製した。
ポリビニルフェノール系樹脂として、マルカリンカーM(丸善石油製)を2.3g、架橋剤として、エポキシ樹脂エピクロン850CPR(DIC製)を3.3g、架橋助剤として、2-エチル-4-メチルイミダゾールを0.15g、溶剤として、IPAcを15g、プロピレングリコールモノメチルエーテルを29g、プロピレンカーボネートを6.0g、離型剤として、KF96L-1cs(信越化学製)を2.0g、フッ素系界面活性剤として、F-482(DIC製)を1.0gおよび、MCF-350SF(DIC製)0.3g、体質成分として、PMA-ST(日産化学製)を25g、以上を混合して実施例3インキを調製した。
樹脂成分としてポリビニルフェノール系樹脂、エポキシ樹脂の代わりに、アクリル樹脂であるポリメチルメタクリレート(PMMA)(アルドリッチ社製:Mw120,000)20.0gを、溶剤シクロヘキサノン80.0gと混合して比較例1インキを調製した。
樹脂成分としてポリビニルフェノール系樹脂、エポキシ樹脂の代わりに、ポリスチレン樹脂(アルドリッチ社製:Mw44,000)20.0gを、溶剤シクロヘキサノン80.0gと混合して比較例2インキを調製した。
ポリビニルフェノール系樹脂であるマルカリンカーM(丸善石油化学社製)20.0g、架橋剤としてエポキシ樹脂に代えて、サイメル303(日本サイテック製)8.0g、溶剤シクロヘキサノン100.0gを混合して比較例3インキを調製した。
フェノールノボラック樹脂(フェノライトTD-2090-60M:固形分60%MEK溶液)1.9g、とエポキシ樹脂エピクロン850CPR(DIC製)を2.0g、架橋助剤として、2-エチル-4-メチルイミダゾールを0.1gに、溶剤として、イソプロピルアセテート(以下IPAc)を4.0g、メチルエチルケトンを3.8g混合して比較例4のインキを調製した。
上記の実施例1インキから比較例3インキを、厚さ1.5mmのガラス板上に、スピンコーター印刷方式で、乾燥膜厚1μmの厚さに調製した。その後、140℃で30分焼成し、耐溶剤性評価サンプルを形成した。耐溶剤性評価は、上記のようにして作製した薄膜をガラス板ごと酢酸ブチルカルビトールに20時間浸漬し、薄膜が残留しているかどうかで評価した。結果を表1、2に示す。
前記の耐溶剤性評価サンプルと同様に、厚さ1.5mmのITO付きガラス板上に、前記各インキ組成物を印刷し、140℃で30分焼成して、乾燥膜厚約1μmの絶縁膜を得た。該絶縁膜上部に銀電極を真空蒸着法により形成し、絶縁膜に150V印加したときの電流値を測定した。単位はmAcm-2である。
実施例3のインキを用いて、ブランケットのPDMS表面に絶縁性インキ塗膜を形成し、この塗膜に抜き版となる凸版ガラス版を押圧、余分なインクを除去して線幅20μmの格子状のパターンをブランケット上に形成した後、これを被印刷基材であるガラス板に転写し画像を形成した。このガラス板上に形成された画像品質を光学顕微鏡で観察し、上記凸版のパターンが正確に再現されているかどうかを評価した。結果を表1に示す。
図1に示すボトムゲートボトムコンタクト(BGBC)構造を有するトランジスタ特性測定用素子を作成した。
(1)ゲート電極の形成:厚さ約125μmのハードコード付PENフィルムを所定の大きさにカットし、ナノ粒子銀を均一に分散させた導電インキをスピンコートによりフィルム上に均一に塗布し、クリーンオーブン中で150℃、40分焼成した。
(2)絶縁膜の形成:前記導電インキにより形成したゲート電極上に、本発明の絶縁膜形成用インキを用いてスピンコートにより塗布し、クリーンオーブン中で140℃約1時間熱処理し膜厚約1μmのゲート絶縁膜を形成した。
(3)ソース、ドレイン電極の形成:反転印刷用の導電インキを用い凸版反転印刷により、先に形成したゲート絶縁膜上にチャネル長50μm、チャネル幅4mmのソース、ドレイン電極パターンを形成し、クリーンオーブン中で、170℃で40分焼成し、銀電極を形成した。
(4)有機半導体層の形成:有機半導体(P3HT)Poly(3-hexylthiophene)のキシレン0.5重量%溶液を用いスピンコート法により、絶縁膜、ソース、ドレイン電極上にP3HT薄膜を形成した。
(5)作成した素子はグローボックス中で150℃、約5分の熱処理を行った後にId-Vg、Id-Vd特性を、半導体パラメター測定装置(ケースレー社4200)を用いて測定した。電界効果移動度およびON/OFFは周知の方法より求めた。移動度の単位はcm2/Vsである。
2.ゲート電極
3.絶縁膜
4.有機半導体層
5.ソース、ドレイン電極
Claims (4)
- 有機溶剤、ポリビニルフェノール系樹脂、エポキシ樹脂、及び、架橋助剤を含有することを特徴とする絶縁膜形成用インキ組成物
- フッ素系界面活性剤を含有する請求項1に記載の絶縁膜形成用インキ組成物。
- 前記した有機溶剤が、20℃における蒸気圧が11.3×102Pa以上かつ大気圧下における沸点が115℃未満の有機溶剤、及び、20℃における蒸気圧が11.3×102Pa未満かつ大気圧下における沸点が115℃以上の有機溶剤を含む溶剤であって、体積平均粒径が1~150nmの体質成分およびシリコーン系離型性分を含有し、25℃におけるインキの表面張力が17~30mN/mであり、インキの粘度が0.5~30mPa・sである請求項1又は2に記載の絶縁膜形成用インキ組成物。
- 請求項1~3の何れかに記載の絶縁膜形成用インキ組成物より形成されることを特徴とする絶縁膜。
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EP09762402.7A EP2292707B1 (en) | 2008-06-13 | 2009-06-03 | Ink composition for forming an insulating film and an insulating film formed from said ink composition |
US12/737,145 US8791173B2 (en) | 2008-06-13 | 2009-06-03 | Ink composition for forming insulating film and insulating film formed from the ink composition |
JP2010501307A JP4626837B2 (ja) | 2008-06-13 | 2009-06-03 | 絶縁膜形成用インキ組成物、該インキ組成物から形成された絶縁膜 |
CN200980121884.3A CN102057000B (zh) | 2008-06-13 | 2009-06-03 | 绝缘膜形成用油墨组合物、由该油墨组合物形成的绝缘膜 |
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Also Published As
Publication number | Publication date |
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EP2292707B1 (en) | 2017-03-08 |
KR101615398B1 (ko) | 2016-04-25 |
US8791173B2 (en) | 2014-07-29 |
KR20110019367A (ko) | 2011-02-25 |
CN102057000B (zh) | 2014-05-07 |
EP2292707A4 (en) | 2012-11-28 |
JP4626837B2 (ja) | 2011-02-09 |
EP2292707A1 (en) | 2011-03-09 |
JPWO2009150972A1 (ja) | 2011-11-17 |
CN102057000A (zh) | 2011-05-11 |
US20110086946A1 (en) | 2011-04-14 |
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