WO2012086959A2 - Composition de résine photodurcissable pour processus d'impression - Google Patents

Composition de résine photodurcissable pour processus d'impression Download PDF

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WO2012086959A2
WO2012086959A2 PCT/KR2011/009635 KR2011009635W WO2012086959A2 WO 2012086959 A2 WO2012086959 A2 WO 2012086959A2 KR 2011009635 W KR2011009635 W KR 2011009635W WO 2012086959 A2 WO2012086959 A2 WO 2012086959A2
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WIPO (PCT)
Prior art keywords
resin composition
printing process
photocurable resin
acrylate
polysilazane
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PCT/KR2011/009635
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English (en)
Korean (ko)
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WO2012086959A3 (fr
Inventor
송준용
신승협
최미경
이광영
Original Assignee
주식회사 동진쎄미켐
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Priority claimed from KR1020110131502A external-priority patent/KR101917156B1/ko
Application filed by 주식회사 동진쎄미켐 filed Critical 주식회사 동진쎄미켐
Publication of WO2012086959A2 publication Critical patent/WO2012086959A2/fr
Publication of WO2012086959A3 publication Critical patent/WO2012086959A3/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers

Definitions

  • the present invention relates to photocurable resin compositions for printing processes useful for the production of micropatterns and protective films used in imprint lithography and roll printing processes.
  • the circuit line width or pattern line width is determined by the wavelength of light used in the exposure process.
  • photolithography processes are difficult to form fine patterns of 50 nm or less on a substrate because of light interference.
  • the initial investment costs increase due to expensive equipment such as exposure equipment, and the price of high-resolution masks soars, resulting in a decrease in efficiency. It is also acting as another factor.
  • the process takes a long time because the exposure, the post-exposure bake, the development, the post-development bake, the etching process, the cleaning process, and the like every time the pattern is formed, the productivity is increased because the photo process must be repeated several times. The problem of deterioration was highlighted.
  • Imprint lithography and roll printing techniques have emerged as a way to solve this problem.
  • Imprint lithography is the first method invented by Stephen chou of Princeton University in order to imprint nanoscale.
  • the fine pattern is formed by painting.
  • Mold polymer mold
  • Such an imprint method is disclosed in US Patent No. 5,772,905, US Patent No. 5,259,926, and Japanese Patent Publication No. 2007-244984 (Korean Patent Publication No. 10-2009-0031274).
  • Korean Patent Application No. 2006-0005482 discloses a roll printing apparatus and a manufacturing method of a display device using the same, and roll printing using one or more rolls.
  • the method is applicable to devices such as FED (Field Emission Display), OLED (Organic Light Electroluminescent Display), PDP (Plasma Display Panel), etc., and that the manufacturing process of the device will be simplified. It is disclosed that precision will be secured.
  • the roll printing method may form a fine pattern by using a plate, a roll, a roll, and the like on a roll instead of a high-resolution mask used when forming a pattern in conventional photolithography.
  • This roll printing method improves productivity and work efficiency through a simplified process.
  • it has been proposed as an alternative that can drastically reduce the complicated process that proceeds through various processes, such as exposure or development of photolithography and the resulting process costs.
  • Japanese Patent Laid-Open No. 2005-197699 discloses an imprint composition for semiconductor microlithography in connection with such a printing technique for pattern formation that can be performed at low cost.
  • Japanese Laid-Open Patent Publication No. 2005-301289 as a member of LCD or the like also discloses the application of photocurable printing lithography to a transparent protective film material, a spacer and the like.
  • Resists such as transparent protective films, spacers, and the like, disclosed in Japanese Patent Laid-Open No. 2005-301289 are called protective films (permanent films) because, unlike etching resists, materials are finally left.
  • This protective film unlike the etching resist, is an element left in the TFT display panel.
  • a transparent protective film is formed to protect the thin film transistor.
  • the conventional protective film (permanent film) is mostly formed through a photolithography process through a photoresist material.
  • a photocurable resin is coated on the color filter, the electrode lead portion is removed by photolithography, and a thermosetting process is performed to perform the protective film (permanent film).
  • the protective film (permanent film) for the color filter reduces the step between the color filters and enables resistance to high temperature processes in forming the transparent electrode (ITO).
  • thermosetting resins such as a siloxane polymer, a silicone polyimide, an epoxy resin, and an acrylic resin
  • a transparent protective film permanent film
  • the existing protective film formed silicon nitride (SiNx) on the metal and formed a protective film (permanent film) thereon.
  • SiNx silicon nitride
  • the role of the protective film is also increased. As the SiNx) formation process can be eliminated, there are many advantages in realizing low cost.
  • a resin composition on substrates of various materials such as inorganic layers such as Cu, SiNx, Mo, and film layers such as organic layers, PET, PES, etc.
  • inorganic layers such as Cu, SiNx, Mo
  • film layers such as organic layers, PET, PES, etc.
  • the metal material when the photocurable resin composition is formed on a substrate, depending on the type of metal patterned on the substrate at the time of performing a high temperature thermal process, the metal material may be modified due to oxidation and diffusion of the metal material. .
  • a metal material is copper.
  • a high temperature thermal process is performed during formation of a protective film (permanent film) on copper with a TFT electrode by using an imprint process, defects due to black spots and stains on the coating film are generated due to oxidation and diffusion of the copper layer. This defect is pointed out as the biggest problem in the process of forming an organic material on the copper layer.
  • the present invention can be applied to a variety of substrates such as plastic, metal, glass, such as excellent adhesiveness, durability against high temperature, high humidity and high pressure conditions, excellent permeability and heat resistance after high temperature treatment, And an object of the present invention is to provide a photocurable resin composition for a printing process with a low degree of modification of the lower film.
  • the present invention also provides a method for producing a protective film for a printing process using the photocurable resin composition and the method, which can stably and easily form fine patterns required for various electronic device industrial processes including semiconductors, displays, and the like. It is an object to provide a protective film.
  • crosslinkable monomers having at least two ethylenic double bonds
  • the present invention also provides a method for producing a protective film for a printing process comprising applying and exposing the photocurable resin composition to a substrate.
  • the present invention provides a protective film for a printing process produced by the manufacturing method.
  • the photocurable resin composition according to the present invention comprises a polysilazane compound
  • the protective film when the protective film is formed, compared with the coating film using the resin composition used in the conventional imprint lithography and roll printing process, the adhesive strength with the substrate, high transmittance even after high temperature treatment, It shows excellent performance as a protective film (permanent film) by simultaneously improving the durability, heat resistance, and prevention of underlayer film deterioration by high temperature processes in harsh conditions such as high temperature and high humidity.
  • Example 1 is an electron microscope photograph of a lower film before thermosetting a protective film prepared from the composition of Example 1 according to the present invention.
  • the photocurable resin composition for a printing process according to the present invention comprises a polysilazane compound for improving the adhesion, durability, permeability and heat resistance of the cured polymer resin, that is, the protective film, and preventing the underlayer of the composition. Characterized in that.
  • the photocurable resin composition for a printing process according to the present invention
  • the polysilazane compound used for this invention is not specifically limited, It can select arbitrarily unless the effect of this invention is impaired. These may be presented as either inorganic or organic compounds.
  • the amount of the polysilazane compound according to the present invention is preferably used in 1 to 60% by weight, preferably 10 to 40% by weight.
  • the amount of the polysilazane compound used is 1% by weight If less than, there is a tendency that the lower film denaturation prevention, adhesion and the like of the obtained thin film is lowered, and when it exceeds 60% by weight, printing characteristics may be deteriorated due to the increase in viscosity.
  • the polysilazane compound used in the present invention includes a linear structure having a structural unit represented by the following formula (1), has a molecular weight of 300 to 2,000, has 3 to 10 SiH 3 groups in one molecule, and is used for chemical analysis.
  • n is an integer.
  • the perhydropolysilazane may be prepared according to a conventional method in the art, for example, according to the method described in Japanese Patent Laid-Open No. 63-16325, and basically a chain portion in a molecule and It may be represented by the following formula (2) to include a cyclic moiety.
  • Preferred examples of the perhydropolysilazane include compounds having the structure of Formula 3 or 4 below.
  • R is One , R 2 And R 3
  • R Each independently represent a group in which a group directly connected to silicon, such as a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group or a fluoroalkyl group, is carbon, an alkylsilyl group, an alkylamino group, or an alkoxy group, n is an integer. (At this time, R One , R 2 And R 3 At least one of them is a hydrogen atom.)
  • polysilazane having a number average molecular weight of about 100 to 50,000 having a skeleton composed of the above structural units or a modified product thereof is included.
  • a method for producing polysilazane having a hydrogen atom in R 1 and R 2 and a methyl group in R 3 is described in D. Seyferth et al . Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 25.10 (1984).
  • the polysilazane obtained by this method is a chain polymer and a cyclic polymer, and both do not have a crosslinked structure.
  • the polymer in the case of the polyorgano (hydro) silazane having a hydrogen atom at R 1 and R 2 and an organic group at R 3 , the polymer has a cyclic structure having a polymerization degree of 3 to 5, or a chain in the molecule. There is one having a structure and a ring structure at the same time.
  • the organic group in the polysilazane, and R 1 and R 2 having in the general formula (4) in the R 1 an organic group to a hydrogen atom, and R 2 and R 3, and R 3 is a polymerization degree having a hydrogen atom a 3-5 degree
  • polysilazanes having a cyclic structure There are also polysilazanes having a cyclic structure.
  • organic polysilazane other than the compound having the structure of Formula 4 polyorgano (hydro) silazane having a crosslinked structure of Formula 5 below, and R1SiX3 (X: halogen) obtained by ammonia decomposition
  • Polysilazane having a structure of formula (6) obtained by co-ammonia decomposition of polysilazane, R1Si (NH) X, or R1SiX3 having a crosslinked structure (see Japanese Patent Application Laid-Open No. 49-69717) Can be.
  • R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, an alkenyl group or an aryl group, and m and n each independently represent an integer.
  • inorganic silazane copolymers or modified polysilazanes having increased molecular weight or improved hydrolysis resistance Japanese Patent Application Laid-Open No. H1-138108, H11-138107, H1-203429 and 1-203430
  • copolymerization silazane Japanese Patent Publication No. Hei 2-175726, Hei 5-86200, Hei 5-331293
  • Etc. may be included.
  • the polysilazane compounds presented above may be used alone or in combination of two or more thereof.
  • the amount of the ethylene monomer used is preferably 10 to 80% by weight, more preferably 20 to 60% by weight.
  • the amount of the ethylene-based monomer is less than 10% by weight, the obtained thin film molecular weight is not sufficient, and the strength tends to be lowered.
  • the amount of the ethylene monomer is more than 80% by weight, the unreacted material increases, which may cause shrinkage.
  • ethylene monomers are isobutyl acrylate, tert-butyl acrylate, lauryl acrylate, methyl methacrylate, alkyl acrylate, cyclohexyl acrylate, isobornyl acrylate, benzyl methacrylate, benzyl Acrylate, 2-hydroxyacrylate, trimethoxybutyl acrylate, ethylcarbidol acrylate, phenoxyethyl acrylate, 4-hydroxybutyl acrylate, phenoxypolyethylene glycol acrylate, 2-hydroxyethyl Acrylate, 2-hydroxypropyl acrylate, 2-acryloxyethyl-2-hydroxypropyl phthalate, 2-hydroxy-3-phenoxypropyl acrylate and methacrylates thereof; Acrylates including halogen compounds such as 3-fluoroethyl acrylate and 4-fluoropropyl acrylate and methacrylates thereof; Acrylates containing siloxane groups such as trifluoro
  • crosslinkable monomers having at least two ethylenic double bonds
  • the amount of the crosslinkable monomer having at least two or more ethylenic double bonds is preferably 10 to 80% by weight, more preferably 20 to 60% by weight. good.
  • the amount of the crosslinkable monomer is less than 10% by weight, the degree of curing is insufficient, which is detrimental to the pattern formation.
  • the amount of the crosslinkable monomer is greater than 80% by weight, the hardness is excessively high due to the increase of the degree of curing or rather, the unreacted substances are increased, causing the shrinkage. This can be
  • crosslinkable monomer examples include diethylene glycol monoethyl ether, dimethylol dicyclopentane diacrylate, 1,4-butanediol diacrylate, 1,3-butylene glycol diacrylate, and 1,6-hexanediol Diacrylate, aryloxy polyethylene glycol acrylate, dicyclopentenyl acrylate, hydroxy pivalate neopentyl glycol diacrylate, neopentyl glycol diacrylate, 1, 9-nonane diol diacrylate, polyethylene glycol diacryl Acrylate, sorbitol triacrylate, bisphenol A diacrylate derivative, trimethyl propane triacrylate, and methacrylates thereof, but are not limited thereto, and these may be used alone or in combination of two or more thereof.
  • EO modified glycerol triacrylate PO modified glycerol triacrylate, trimethylol propane triacrylate, pentaerythritol ethoxy tetraacrylate, dipentaerythritol hexa Acrylate, EO modified trimethylol propane triacrylate, and these methacrylates, etc. are mentioned, It is not limited to these, These can be used individually or in mixture of 2 or more types.
  • the amount of the photopolymerization initiator used is preferably from 0.1 to 12% by weight, more preferably from 0.5 to 8% by weight.
  • photopolymerization initiator examples include Irgacure 369, Igacure 907, Igacure184, Igacure 651, Igacure 819, Igacure 2959, Igacure 1800, Darocur 1173, Darocur 1116 and Darocur 1020; 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylproriophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, benzophenone, 4-chloroacetophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, 2,2'-dichloro-4-phenoxy Acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1
  • the photocurable resin composition of this invention may contain surfactant.
  • the surfactant may be used as long as it can improve the coating property of the photocurable resin composition, the amount of the surfactant used in the present invention is preferably 0.001 to 5% by weight, more preferably based on the total composition It is preferable to use 0.01 to 2% by weight. If two or more surfactants are used in combination, the total content is as indicated above.
  • the surfactant When the surfactant is contained in an amount of 0.001% by weight or less, uniform coating may be limited, and when 5% by weight or more may cause problems in mold transfer properties and formation of additional materials in a later process.
  • the said surfactant contains at least 1 type from silicone type and a fluorine type surfactant, It is also possible to mix and use 2 or more types.
  • the surfactant may include, but are not limited to, fluorine-based surfactants from Dainippon Ink Chemical Co., Ltd., 3M and Shin-Etsu Chemical Co., Ltd., and silicone-based surfactants from Dow, BK, and Evonik.
  • the photocurable resin composition of the present invention may further include a solvent.
  • a solvent is not used in the case of the photocurable resin composition for a printing process, but in the present invention, a solvent may be added for dissolution of polysilazane and compatibility with the photocurable resin composition.
  • the amount of the solvent is preferably 0 to 70% by weight, more preferably 0 to 50% by weight.
  • the solvent include acetonitrile, glycerol, dimethyl sulfoxide, nitromethane, dimethyl formamide, phenol, N-methylpyrrolidone, pyridine perfluorotributylamine, perfluoro decalin, 2-butanone, Alcohols such as methylene carbonate methanol, ethanol, ethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, propylene ethylene glycol, diethylene glycol, butanediol, benzyl alcohol and hexyl alcohol; Ethers such as propylene carbonate, tetrahydrofuran, 1,4-dioxane, 1-methoxy-2-propanol, methoxybenzene, dibutyl ether and diphenol ether; Ethyl acetate, propyl acetate, butyl acetate, ethyl propion, ethyl ester, butyl ester,
  • the viscosity of the composition according to the invention is 2 mPa ⁇ s to 25 mPa ⁇ s at 25 ° C., preferably 3 mPa ⁇ s to 20 mPa ⁇ s, more preferably 5 mPa ⁇ s to 15 mPa ⁇ s to be.
  • composition viscosity of the present invention is 2 mPa ⁇ s or less, it is limited to the desired coating film thickness formation, and when the composition viscosity is 25 mPa ⁇ s or more, it may be difficult to apply the material to the substrate.
  • the present invention also provides a method for producing a protective film and a fine pattern for a printing process using the photocurable resin composition, and a protective film and a fine pattern produced by the method.
  • the method for producing a protective film for a printing process according to the present invention includes applying and exposing a photocurable composition according to the present invention to a substrate.
  • the composition after applying the composition to the substrate, by using an imprint lithography or roll printing process to form a coating film and exposed to it, it is possible to stably and easily fine patterns required for various electronic device industrial processes including semiconductors and displays Can be formed.
  • the composition is applied to a substrate (for example, silicon substrate, ceramic substrate, metal layer, polymer layer, etc.) by applying a suitable method such as spin coating, roller coating, slit, inkjet coating, etc. in a thickness of 0.5 to 10 ⁇ m It is preferable.
  • UV 190-450 nm
  • 200-400 nm area is used, and electron beam irradiation is also possible.
  • a high temperature heat treatment process may be subsequently performed to improve the use and properties of the film.
  • the protective film and the micropattern manufactured according to the present invention have excellent adhesion to a substrate, durability against high temperature, high humidity, and high pressure conditions, high permeability and heat resistance after high temperature treatment, and a low degree of modification of the lower layer, and thus include a semiconductor and a display.
  • the composition of the present invention is the imprint lithography and roll printing process using the conventional photolithography process by replacing the photolithography process for forming a fine pattern
  • the manufacturing process time can be shortened, thereby reducing manufacturing costs and improving productivity.
  • each of the photocurable compositions prepared above was applied on a degreasing-washed metal substrate with a thickness of 0.5 to 5 ⁇ m, bonded to a polymer mold and exposed using a lamp having a wavelength of 365 nm, and then formed thin film and polymer. The mold was released to form a protective film.
  • a photocurable composition and a protective film according to the present invention were prepared in the same manner as in Example 1, except that 10 parts by weight of polysilazane SN-1 having a structure of Formula 1 and a molecular weight of 500 was used.
  • a photocurable composition and a protective film were prepared in the same manner as in Example 1, except that 4-hydroxybutyl acrylate was used in an amount of 40 parts by weight without using polysilazane.
  • the protective film prepared in Examples 1 to 3, and Comparative Example 1 was measured for adhesion, durability, permeability, heat resistance, and lower film deterioration degree with respect to the substrate by the following method, and the results are shown in Table 1 below. It was.
  • the substrate on which the protective film was formed as described above was thermally cured in an oven at 230 ° C. for 30 minutes, and the adhesive strength was checked in the same manner as in the above a) to confirm 100% adhesion.
  • the substrate was treated at 120 ° C., 100% humidity, 2 atmospheres, and left for 24 hours in a device capable of high temperature, high pressure, and high humidity, and then the surface state and adhesion state of the substrate were rechecked. Evaluation was based on the same criteria.
  • the poor adhesive state means that the moisture penetrated into the coating film and the lower substrate and the lifting phenomenon occurred.
  • the substrate on which the protective film was formed was thermally cured in an oven at 230 ° C. for 150 minutes, and the substrate on which the coating film was formed was measured at 400 nm using a transmittance equipment, and evaluated according to the following criteria.
  • the weight loss was measured by a thermogravimetric analyzer (TGA) while thermally curing the substrate having the protective film formed thereon at 230 ° C. for 30 minutes in an oven, and evaluated according to the following criteria.
  • TGA thermogravimetric analyzer
  • Weight loss is more than 1% but less than 3%
  • Weight loss is more than 3% and less than 5%
  • the substrate on which the protective film was formed as described above was thermally cured in an oven at 230 ° C. for 150 minutes, and the substrate on which the coating film was formed was checked by visual inspection and SEM (Self-scanning microscope), and evaluated according to the following criteria. In addition, the SEM photograph is shown in Figs.
  • the photocurable resin composition according to the present invention comprises a polysilazane compound
  • the protective film when the protective film is formed, compared with the coating film using the resin composition used in the conventional imprint lithography and roll printing process, the adhesive strength with the substrate, high transmittance even after high temperature treatment, It shows excellent performance as a protective film (permanent film) by simultaneously improving the durability, heat resistance, and prevention of underlayer film deterioration by high temperature processes in harsh conditions such as high temperature and high humidity.

Abstract

La présente invention porte sur une composition de résine photodurcissable pour un processus d'impression, et, de façon plus spécifique, sur une composition de résine photodurcissable comprenant un composé de polysilasane. La composition selon l'invention comprend le composé de polysilasane, de façon à assurer ainsi une excellente force d'adhérence à un substrat, une excellente résistance à la chaleur, une excellente durée de vie (vis-à-vis d'une température élevée, d'une pression élevée et d'une humidité élevée) et une excellente propriété de protection de couche inférieure tout en maintenant une perméabilité élevée même après un traitement à haute température. Par conséquent, la composition de résine photodurcissable peut être utile dans la formation d'un motif fin et d'une couche protectrice.
PCT/KR2011/009635 2010-12-20 2011-12-14 Composition de résine photodurcissable pour processus d'impression WO2012086959A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2010-0130666 2010-12-20
KR20100130666 2010-12-20
KR1020110131502A KR101917156B1 (ko) 2010-12-20 2011-12-09 프린팅 프로세스용 광경화성 수지 조성물
KR10-2011-0131502 2011-12-09

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WO2012086959A2 true WO2012086959A2 (fr) 2012-06-28
WO2012086959A3 WO2012086959A3 (fr) 2012-10-18

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CN110092873A (zh) * 2019-05-16 2019-08-06 广东工业大学 一种光敏树脂陶瓷及其立体光固化制备方法

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KR20190087555A (ko) * 2016-11-25 2019-07-24 리지필드 액퀴지션 리소그래피 조성물, 레지스트 패턴의 형성 방법 및 반도체 장치의 제조 방법
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CN110092873A (zh) * 2019-05-16 2019-08-06 广东工业大学 一种光敏树脂陶瓷及其立体光固化制备方法
WO2020228054A1 (fr) * 2019-05-16 2020-11-19 广东工业大学 Céramique de résine photosensible et son procédé de préparation par stéréolithographie

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