WO2011016651A2 - Composition de résine photodurcissable pour lithographie d’impression et procédé de fabrication d’un moule d’impression l’utilisant - Google Patents

Composition de résine photodurcissable pour lithographie d’impression et procédé de fabrication d’un moule d’impression l’utilisant Download PDF

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WO2011016651A2
WO2011016651A2 PCT/KR2010/005035 KR2010005035W WO2011016651A2 WO 2011016651 A2 WO2011016651 A2 WO 2011016651A2 KR 2010005035 W KR2010005035 W KR 2010005035W WO 2011016651 A2 WO2011016651 A2 WO 2011016651A2
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group
acrylate
meth
resin composition
mold
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WO2011016651A9 (fr
WO2011016651A3 (fr
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김병욱
유재원
김운용
곽은진
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주식회사 동진쎄미켐
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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
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
    • B29C59/02—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
    • B29C59/022—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing characterised by the disposition or the configuration, e.g. dimensions, of the embossments or the shaping tools therefor
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • 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
    • G03F7/0017—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor for the production of embossing, cutting or similar devices; for the production of casting means
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • 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
    • G03F7/075—Silicon-containing compounds
    • G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate

Definitions

  • the present invention relates to a photocurable resin composition for imprint lithography and a method of manufacturing an imprint mold using the same for forming patterns of various sizes ranging from several nanometers to several centimeters on a substrate, wherein the resin composition has excellent adhesiveness and stain resistance, It exhibits high resilience and transmittance along with release properties, non-swelling properties and mechanical properties for organic solvents, making them useful in the manufacture of molds for imprint lithography.
  • Photolithography is widely used as a method for forming a fine pattern on a substrate.
  • the photolithography method has the advantage of uniformly and stably forming a fine pattern on a substrate, but has a disadvantage of having to go through several steps (resin coating, heat treatment, exposure, development, cleaning, etching, etc.).
  • This complex process requires expensive equipment in each step, and has a disadvantage in that it takes a lot of time to control patterns and pattern formation due to margins in each process. This, in turn, is a fundamental cause of an increase in manufacturing costs and a decrease in productivity.
  • Imprint lithography technology is one of several methods introduced to overcome the limitations of the conventional photolithography method and is recognized as a next generation lithography technology.
  • Imprint lithography technology is an economical and effective technique for producing microstructures by transferring a stamped stamp of microstructures onto a surface of a spincoated or dispensed resist onto a substrate to transfer the microstructures.
  • Technology Early imprint techniques used a method in which the surface of a resist-coated substrate was stamped with a stamp of microstructures, pressed at a high pressure at a high temperature above the glass transition temperature, and then cooled and separated. However, this method has the advantages of easy process and low equipment cost, while long process time and high pressure are required. In particular, since high temperature and high pressure are required, there is a risk of substrate damage, and separation of the mold and the substrate is not easy.
  • polydimethylsiloxane which is a polymer elastomer
  • PDMS polydimethylsiloxane
  • Molds made using polydimethylsiloxane not only have high light transmittance, but also are elastic, so that they can be uniformly contacted with the surface of the substrate to form a pattern, and the surface of the resist applied due to the low surface energy of polydimethylsiloxane
  • the adhesion force with is small and it is easy to separate from the substrate surface after pattern formation.
  • the high gas permeability due to the three-dimensional network structure has the advantage of easy absorption of the solvent.
  • the polydimethylsiloxane resin mold has low mechanical strength, so that deformation easily occurs, and stain resistance is reduced by foreign substances such as dust, and it is easily swelled by a general organic solvent so that deformation can be used for pattern formation.
  • a general organic solvent so that deformation can be used for pattern formation.
  • a fluorine resin having low surface energy and excellent light transmittance and excellent chemical resistance such as polydimethylsiloxane, or a urethane resin having a low swelling phenomenon due to an organic solvent is used.
  • the fluorine-based resin has low surface energy when forming a mold, so that high release property can be realized, but the adhesion to the supporting substrate is low, which limits the selection of a substrate to form a mold, and must process a primer on the substrate. .
  • a method of mixing a polymer material, an oligomer, a monomer, and the like is used to improve adhesion to the support substrate, but there is a problem in that releasability is lowered due to an increase in surface energy caused by the introduced material.
  • the urethane-based resin is not only excellent in durability, but also excellent in chemical resistance and substrate adhesion, but is widely used, but it is difficult to release mold and thermosetting or photocuring resin after patterning with high surface energy.
  • a separate surface treatment or release agent adjuvant must be additionally applied to the mold for smooth separation.
  • the present invention is not only excellent in stain resistance, but also excellent in adhesion, can be applied to various substrates such as plastic, metal, glass, etc., and shows excellent release property by adjusting surface energy of the mold surface. It is an object of the present invention to provide a photocurable resin composition for imprint lithography that has non-swelling properties, excellent mechanical properties, and high resilience and transmittance with respect to an organic solvent.
  • the present invention also provides a method for manufacturing an imprint mold using the photocurable resin composition and an imprint manufactured by the method, which can stably and easily form micropatterns necessary for various electronic device industrial processes including semiconductors, displays, and the like. It is an object to provide a mold.
  • the present invention also provides a cured polymer resin to which the pattern of the disc mold is transferred by coating and curing the photocurable resin composition on one surface of the disc mold on which the pattern is formed, and the cured polymer resin transferred to the pattern from the disc mold. It provides a method of manufacturing an imprint mold comprising the step of releasing.
  • the present invention provides an imprint mold manufactured by the manufacturing method.
  • the manufacturing time can be shortened to reduce manufacturing cost and improve productivity.
  • the photocurable resin composition according to the present invention has a non-swelling property with respect to an organic solvent, and has a large mechanical property, a high restoring force and a transmittance, so that a fine pattern necessary for various electronic device industrial processes including semiconductors and displays can be stably and easily Can be formed.
  • the photocurable resin composition according to the present invention has excellent wettability and releasability with the thermosetting or photocurable resin for pattern formation regardless of whether or not additional surface treatment, and at the same time, excellent adhesion between the mold-forming substrate and the mold. Indicates.
  • the photocurable resin composition according to the present invention includes a fluorine-based monomer, a polymer, or a mixture thereof, thereby having a significantly lower viscosity than the polymer resin compositions used in the conventional imprint mold, thereby easily forming a micropattern. Molds with completeness can be prepared.
  • FIG. 1 is a cross-sectional view schematically showing a method for producing a resin mold according to the present invention.
  • FIG. 2A is an electron microscope photograph of a pattern forming mold manufactured using a disc mold having a hole shape (spacing: 2 ⁇ m, width: 2 ⁇ m, height: 1.5 ⁇ m).
  • 2B is an electron microscope photograph of a pattern forming mold manufactured using a disc mold having a hole shape (spacing: 200 nm, width: 700 nm).
  • FIG. 2C is an electron microscope photograph of a pattern forming mold manufactured using a disc mold having a line width of 300 nm to 500 nm.
  • FIG. 2D is an electron micrograph of a pattern forming mold manufactured using a disc mold in which lines of 550 nm are formed at 100 nm intervals.
  • the photocurable resin composition Preferably the photocurable resin composition,
  • the photocurable fluorine-based polymer or oligomer (1) forms dense crosslinks upon curing of the mold to provide non-swelling properties for organic solvents and thermoset or photocurable resins, and also provides high surface energy to provide thermoset or It serves to impart releasability with the photocurable resin.
  • the photocurable fluorine-based polymer or oligomer (1) may be used a fluorine-based polymer or oligomer including a reactive functional group, preferably an aliphatic or aromatic fluorine-based polymer or oligomer containing two or more reactive functional groups Can be used.
  • photocurable fluorine-based polymer or oligomer (1) examples include urethane (meth) acrylate, ester (meth) acrylate, ether (meth) acrylate, epoxy (meth) acrylate, carbonate (meth) acrylate, and Mixtures or copolymers thereof.
  • the photocurable fluorine-based polymer or oligomer (1) is preferably included in an amount of 20-80% by weight based on the total weight of the photocurable resin composition. If the content of the photocurable fluorine-based polymer and oligomer (1) is less than 20% by weight, it is difficult to form a dense crosslink, resulting in poor mechanical strength, deterioration of chemical resistance, and swelling or breakage of organic solvents, and also fluorine. As the content decreases, the surface energy rises, which may lower the release property. In addition, when the content exceeds 80% by weight, the adhesive strength with the support is low, making the mold difficult.
  • the resin composition according to the present invention is a component (1) for improving the physical properties such as wear resistance, heat resistance, weather resistance, surface hardness, flexibility, high elasticity and bendability of the final mold Together with photocurable fluorine-based polymers or oligomers, such as polyurethane (meth) acrylate, polyester (meth) acrylate, polyether (meth) acrylate, polyepoxy (meth) acrylate and polycarbonate (meth) acrylate At least one polymer selected from the group consisting of: may further comprise 1-30% by weight based on the total weight of the component (1).
  • At least one polyfunctional free radically polymerizable compound (2) containing fluorine serves to adjust the crosslinking density by reaction with the component (1).
  • the functional group, the multifunctional free radical polymerizable group portion improves adhesion to the mold support, and the fluorine group portion is increased due to the large amount of functional groups. Offsets the surface energy of the mold to facilitate mold release with thermosetting or photocuring resins.
  • the multifunctional free radically polymerizable compound (2) of the component (2) serves as a diluent of the component (1) to facilitate the formation of a micropattern and to improve the completeness of the mold.
  • polyfunctional free radically polymerizable compound is meant herein monomers, oligomers and polymers comprising functional groups that participate in a crosslinking reaction upon exposure to a suitable source of free radicals.
  • it is a monomer having at least one multifunctional free radically polymerizable group.
  • Preferred free radically polymerizable groups are (meth) acrylic groups comprising a (meth) acrylate group or a (meth) acrylamide group optionally substituted with fluorine or sulfur, more preferably an acrylate group.
  • the at least one multifunctional free radically polymerizable compound (2) including fluorine usable in the present invention may have a different component depending on the component (1), but preferably a compound having a structure represented by the following Chemical Formula 1 have:
  • R f is a (per) fluoro group
  • T is a bonding group
  • d is an integer of 1-6
  • e is an integer of 1 or 2.
  • R f means a linear, branched or cyclic (per) fluoro group, and may be saturated or unsaturated.
  • R represents a fluorine atom, a hydrogen atom, or a methyl group here, and a fluorine atom is preferable.
  • P is an integer of 1-10 and varies depending on component (1), all of which may be linear, branched or cyclic.
  • Z is a perfluoroalkyl group, a perfluoroether group, a perfluoropolyether group, or a perfluoroalkoxy group, all of which may be linear, branched or cyclic.
  • the Z group contains 1-12 carbon atoms and may optionally include 1-4 oxygen atoms or no oxygen atoms. In such perfluoropolyether structures, different repeat units can be randomly distributed along the chain.
  • the bonding group T between the perfluoro group and the free radical polymerizable group is a divalent group selected from the group consisting of alkylene, arylene, heteroalkylene, and combinations thereof, or carbonyl, ester, amide, sulfon amide, and these And a divalent group selected from the group consisting of T may be unsubstituted or substituted with alkyl, aryl, halogen or a combination thereof.
  • T may be alkylene, alkylene substituted with aryl groups, arylene, or alkylene in combination with alkyl ether or alkyl thioether linking groups.
  • the at least one multifunctional free radically polymerizable compound (2) containing fluorine include perfluorobutyl ethylene, perfluorohexyl ethylene, perfluorooctyl ethylene, perfluorodecyl ethylene, 2,2, 2-trifluoroethyl (meth) acrylate, 2,2,3,3,3, -pentafluoropropyl (meth) acrylate, 2-perfluorobutylethyl (meth) acrylate, 3-perflow Orobutyl-2-hydroxypropyl (meth) acrylate, 2-perfluorohexylethyl (meth) acrylate, 3-perfluorohexyl-2-hydroxypropyl (meth) acrylate, 2-perfluoro Octylethyl (meth) acrylate, 3-perfluorooctyl-2-hydroxypropyl (meth) acrylate, 2-perfluorodecylethyl (meth)
  • At least one polyfunctional free radically polymerizable compound (2) including fluorine also includes reaction products of the polymerizable compounds and even mixtures thereof.
  • the at least one polyfunctional free radically polymerizable compound (2) containing fluorine preferably has a weight average molecular weight of 3,000 or more, and a weight average of 3,000-20,000 in consideration of the difficulty in forming a micropattern due to a decrease in chemical resistance and high viscosity. It is more preferable to have a molecular weight.
  • the at least one multifunctional free radically polymerizable compound (2) containing fluorine is preferably included in an amount of 20-80 wt% based on the total weight of the photocurable resin composition. If the content of the component (2) is less than 20% by weight, the adhesive strength with the support of the mold is lowered, and the high viscosity of the resin composition is not preferable for forming a micropattern, and if it is more than 80% by weight, the surface energy is reduced as the fluorine content decreases. Rises and the releasability decreases, which is not preferable.
  • the component (3) not only functions as a diluent, but also increases crosslinking density to prevent swelling and breakage caused by an organic solvent and to increase release property when forming a fine pattern.
  • a compound having a polyester structure having a weight average molecular weight of 150 or more, preferably 150-50,000 and containing at least one reactive functional group together with a carboxy group is preferable.
  • the reactive functional group include photo-curable (meth) acryl groups, -SH, allyl groups, and vinyl groups, and these may be fluorinated.
  • olefinically unsaturated compound examples include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, 2-propylheptyl acrylate, sec-butyl methacrylate, tert-butyl methacrylate, methyl Acrylate, isopropyl acrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, dicyclopentenyl acrylate, dicyclopentanyl acrylate, dicyclopentenyl methacrylate, dicyclopentanyl methacrylate , 1-adamantyl acrylate, 1-adamantyl methacrylate, dicyclopentanyloxyethyl methacrylate, isoboroyl methacrylate, dicyclohexyl acrylate, 2-methylcyclohexyl acrylate, di Cyclopentanyloxyethyl acrylate, isoboroyl methacrylate, di
  • the a) olefinically unsaturated compound may be included in an amount of 70 parts by weight or less, preferably 5-70 parts by weight, even more preferably 5-50 parts by weight, based on 100 parts by weight of the total amount of the components (1) and (2). have.
  • the olefinically unsaturated compound is included in the content range, the adhesion to the mold support is excellent, and at the same time it can significantly reduce the breakage phenomenon when exposed to organic solvents for a long time.
  • it exceeds 70 parts by weight the surface energy is increased, there is a fear that the releasability between the mold and the resin is reduced.
  • the unsaturated compound containing the epoxy group of b) may include a phenyl epoxy (meth) acrylate oligomer having at least one reactive functional group, a bisphenol A epoxy di (meth) acrylate oligomer, an aliphatic alkyl epoxy di (meth) acrylate oligomer, And a compound selected from the group consisting of aliphatic alkyl epoxy tri (meth) acrylate oligomers.
  • the said reactive functional group means the (meth) acryl group, -SH, allyl group, or vinyl group which can be photocured.
  • the unsaturated compound containing the epoxy group of b) are glycidyl acrylate, glycidyl methacrylate, glycidyl ⁇ -ethyl acrylate, glycidyl ⁇ -propyl acrylate, ⁇ -n-butyl acrylic acid Glycidyl, acrylic acid-beta -methyl glycidyl, methacrylic acid-beta -methyl glycidyl, acrylic acid-beta -ethylglycidyl, methacrylic acid-beta -ethylglycidyl, acrylic acid -3,4- Epoxybutyl, methacrylic acid-3,4-epoxybutyl, acrylic acid-6,7-epoxyheptyl, methacrylic acid-6,7-epoxyheptyl, ⁇ -ethylacrylic acid-6,7-epoxyheptyl, acrylic acid-3, 4-epoxy cyclo
  • the unsaturated compound containing the epoxy group of b) is 70 parts by weight or less, preferably 5-70 parts by weight, even more preferably 5-50 parts by weight based on 100 parts by weight of the total amount of the components (1) and (2). It may be included in parts by weight.
  • the swelling phenomenon due to the organic solvent can be reduced, but also surface hardness, wear resistance, heat resistance, and the like can be improved.
  • the surface energy is increased to reduce the mold release properties of the mold and the resin, and the surface hardness is increased to reduce the surface properties such as the restoring force after stamping the mold.
  • the unsaturated compound containing the ether group or glycol group of c) is 70 parts by weight or less, preferably 5-70 parts by weight, and even more preferably, based on 100 parts by weight of the total amount of the components (1) and (2). It may be included in 5-50 parts by weight.
  • the swelling phenomenon due to the organic solvent can be reduced but also surface hardness, wear resistance, heat resistance, and the like can be improved.
  • the surface energy is high, and the mold and the resin are not easily released.
  • severe shrinkage that occurs during photoreaction results in undesirable mold patterns.
  • a silicone compound containing an epoxy group, an amine group, or a fluorine group, or an unsaturated silicone compound can be used.
  • Specific examples include (3-glycidoxypropyl) trimethoxy silane, (3-glycidoxyoxy) triethoxysilane, (3-glycidoxypropyl) methyldimethoxysilane, (3-glycidoxyoxy) ) Trimethoxysilane, (3-glycidoxypropyl) dimethylethoxysilane, (3-glycidoxyoxy) dimethylethoxysilane, 3- (methacryloxy) propyltrimethoxysilane, 3,4 -Epoxybutyl trimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethyltrie
  • the d) silicone compound may be included in an amount of 70 parts by weight or less, preferably 5-70 parts by weight, even more preferably 5-50 parts by weight, based on 100 parts by weight of the total amount of the components (1) and (2). .
  • the diluent by increasing the crosslinking density to prevent swelling and breakage phenomenon by the organic solvent, to mitigate the shrinkage of the polymer due to the photoreaction, it can increase the releasability when forming a fine pattern.
  • Component (3) as described above may include a mixture of two or more selected from one or more selected from each group, even when used in combination of two or more of the total weight of the components (1) and (2) It is preferable that it is 5-70 weight part with respect to 100 weight part of total sum total, More preferably, it is 5-50 weight part. When the content of the component (3) exceeds 70 parts by weight, there is a fear that the mechanical strength and flexibility are lowered.
  • Irgacure 369 (hereinafter referred to as Shiva Specialty Chemical Co., Ltd.), Irgacure 651, Irgacure 907, Irgacure 819, diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, methylbenzoyl formate, ethyl (2) , 4,6-trimethylbenzoyl) phenylphosphinate, 2,4-bistrichloromethyl-6-p-methoxystyryl-s-triazine, 2-p-methoxystyryl-4,6-bis Trichloromethyl-s-triazine, 2,4-trichloromethyl-6-triazine, 2,4-trichloromethyl-4-methylnaphthyl-6-triazine, benzophenone, p- (diethylamino ) Benzophenone, 2,2-dichloro-4-phenoxyacetophen
  • the photoinitiator (4) is preferably included in an amount of 0.1-10 parts by weight based on 100 parts by weight of the total amount of the components (1), (2), and (3). Permeability and storage stability can be satisfied at the same time.
  • the photocurable resin composition according to the present invention comprising the above components may further include a surfactant in order to improve applicability and to further improve releasability when removing the original mold and stripping.
  • surfactant examples include polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, F171 (hereinafter referred to as Nippon Ink Co., Ltd.), F172, F173 FC430 (hereinafter referred to as Sumitomo Trim Corporation), FC431, KP341 (Shin-Etsu Chemical Co., Ltd. And the like, and the content thereof is preferably contained in an amount of 0.01-2 parts by weight based on 100 parts by weight of the total amount of the components (1), (2) and (3).
  • the present invention provides a method for producing a mold using the photocurable resin composition and a mold prepared by the method.
  • the method of manufacturing a mold according to the present invention comprises applying a cured photocurable resin composition to one surface of a disk mold on which a pattern is formed and preparing a cured polymer resin to which the pattern of the disk mold is transferred, and the cured polymer resin to which the pattern is transferred. Releasing from the disc mold.
  • FIG. 1 is a cross-sectional view schematically showing a method for manufacturing a mold according to the present invention.
  • step S1 the pattern of the disc mold 101 to be manufactured is turned upward, and then the photocurable resin composition 102a according to the present invention is applied (step S1).
  • the coating process may be carried out by a method such as spin coating, slit coating, it is preferable to apply the photocurable resin composition 102a to a thickness of 5-60 ⁇ m on the original mold.
  • the photocurable resin composition 102a is cured by irradiating with light in an atmosphere of nitrogen or air (step S2).
  • the back support 103 is a transparent glass plate (bare glass), ITO (indium tin oxide) substrate, COC (cyclic olefin copolymer), PAc (polyacrylate), PC ( polycarbonate, PE (polyethylene), PEEK (polyetheretherketone), PEI (polyetherimide), PEN (polyethylenenaphthalate), PES (polyethersulfone), PET (polyethyleneterephtalate), PI (polyimide), PO (polyolefin), PMMA (polymethylmethacrylate), PSF ( polysulfone, polyvinylalcohol (PVA), polyvinylcinnamate (PVC), triacetylcellulose (TAC), polysilicone (polysilicone), polyurethane (polyurethane), epoxy resin (epoxy Resin) and the like can be used.
  • the transmittance is 97-99.9% in the light source of 500 nm wavelength.
  • step S3 the cured polymer resin 102b to which the pattern of the disc mold 101 transferred to the back support 103 is transferred is released from the disc mold 101.
  • a pattern transferred from the disc mold 101 is formed on one surface of the release cured polymer resin 102b.
  • the molding mold 104 is completed by aging the mold having the patterned cured polymer resin 102b (step S4).
  • aging means that the surface of the cured polymer resin mold on which the pattern is formed is excessively exposed to ultraviolet rays to improve the hardness of the mold and to completely extinguish the remaining reactors against ultraviolet rays or to extinguish the remaining reactors through heat treatment and at the same time, the surface flatness. And it means a process for further improving the adhesion with the support.
  • the aging step is preferably a process of improving the hardness of the mold by excessively exposing the surface of the mold to ultraviolet rays, may be carried out by selecting one of the exposure and heat treatment, or both may be carried out step by step.
  • a mold having a high degree of completeness can be produced by the method according to the present invention.
  • the imprint lithography process using the mold replaces the conventional photolithography process for forming a fine pattern, thereby simplifying various steps such as exposure, development, and cleaning of the existing photolithography process, as well as manufacturing time (tact time). ), The manufacturing cost can be reduced and the productivity can be improved.
  • oligomer of 40% by weight of the photocurable fluorine-based urethane acrylate 40% by weight of 2-perfluorooctylethyl methacrylate and 20% by weight of 3-perfluorobutyl-2-hydroxypropyl (meth) acrylate
  • 40 parts by weight of a mixture of 10 parts by weight of phenylepoxy acrylate, 20 parts by weight of diethylene glycol dimethacrylate and 30 parts by weight of methacrylate propyltrimethoxysilane, and ethyl (2,4,6-trimethyl as a photoinitiator 40 parts by weight of a mixture of 10 parts by weight of phenylepoxy acrylate, 20 parts by weight of diethylene glycol dimethacrylate and 30 parts by weight of methacrylate propyltrimethoxysilane, and ethyl (2,4,6-trimethyl as a photoinitiator.
  • the pattern of the disc mold 101 was turned upward, and the photocurable resin composition 102a prepared above was slit-coated so that the thickness was 30 micrometers.
  • the back support 103 is bonded onto the disc mold to which the photocurable resin composition is applied, and then irradiated with ultraviolet rays in a nitrogen atmosphere to cure, and the back support on which the cured polymer resin 102b to which the pattern of the disc mold 101 is transferred is attached. (103) was released from the disc mold (101). Ultraviolet rays were irradiated for complete curing of the adhesive cured polymer resin 102b.
  • Polymer resin was carried out in the same manner as in Example 1, except that 60% by weight of 2-perfluorooctylethyl methacrylate was used as the multifunctional free radically polymerizable compound of component (2) in Example 1 Mold was prepared.
  • Example 1 30 wt% of EGC-1700 (Fluorochemical acrylate polymer, manufactured by 3M), a fluorine acrylate polymer, and 30 wt% of 2-perfluorooctylethyl methacrylate as the multifunctional free-radically polymerizable compound of component (2) in Example 1
  • EGC-1700 Fluorochemical acrylate polymer, manufactured by 3M
  • fluorine acrylate polymer a fluorine acrylate polymer
  • 2-perfluorooctylethyl methacrylate 2-perfluorooctylethyl methacrylate
  • a polymer resin mold was prepared in the same manner as in Example 1, except that 30 parts by weight and 50 parts by weight of phenylepoxy acrylate and diethylene glycol dimethacrylate were used in Example 1, respectively.
  • a polymer resin mold was prepared in the same manner as in Example 1, except that 20 parts by weight of methacrylate propyltrimethoxysilane and 20 parts by weight of trifluoropropyl trimethoxysilane were used as the silicon compound in Example 1. Prepared.
  • a polymer resin mold was prepared in the same manner as in Example 1, except that the photocurable resin composition was manufactured by using 100 wt% of fluorine-based urethane acrylate alone in Example 1.
  • a polymer resin mold was prepared in the same manner as in Example 1, except that 100 wt% of the fluorine-based urethane acrylate was used in Example 1, and the polyfunctional free radical polymerizable compound of Component (2) was not used. Prepared.
  • PDMS Density Polymer
  • sylgard (R) 184 silicone elastomer kit which is a material of a conventional polymer resin mold, was prepared in the same manner as in Example 1 101) was applied to a thickness of 100 ⁇ m and cured by baking in an oven at 60 ° C. for 180 minutes, and then the cured resin was released from the disc mold to prepare a polymer resin mold.
  • Adhesive force The coating film surfaces of the final polymer resin molds prepared in Examples 1 to 5 and Comparative Examples 1 to 3 were divided into 100 cells at regular intervals, and then slowly peeled off after attaching 3M 610 tape. When counting the remaining cells, expressed as%.
  • the average of the force constantly applied is less than 70 mN, it is represented by ⁇ , 70-100 mN, ⁇ , X is greater than 100 mN.
  • a polymer resin mold was prepared in the same manner as in Example 1, except that a disc mold having various shapes was used. The prepared mold was observed using a scanning electron microscope, and the results are shown in FIGS. 2A-2D.
  • FIG. 2A is an electron microscope photograph of a dot-shaped pattern mold manufactured using a hole-shaped disk mold having a thickness of 2 ⁇ m, a width of 2 ⁇ m, and a height of 1.5 ⁇ m.
  • 2B is an electron microscope photograph of a dot-shaped pattern mold manufactured using a hole-shaped disk mold having a gap of 200 nm and a width of 700 nm.
  • FIG. 2C is an electron micrograph of a pattern forming mold manufactured using a disc mold having various nanometer sizes having a line width of 300 nm to 500 nm and irregular shapes different from each other.
  • FIG. 2D is an electron micrograph of a pattern forming mold manufactured using a disc mold in which 550 nm lines are formed at 100 nm intervals.
  • the photocurable resin composition for imprint lithography according to the present invention exhibits low surface energy and low viscosity due to the addition of fluorine-based compounds, it was possible to manufacture molds for pattern formation of various shapes and sizes. It can be seen that the nanometer level micropattern can be easily formed.
  • the manufacturing time can be shortened to reduce manufacturing cost and improve productivity.
  • the photocurable resin composition according to the present invention has a non-swelling property with respect to an organic solvent, and has a large mechanical property, a high restoring force and a transmittance, so that a fine pattern necessary for various electronic device industrial processes including semiconductors and displays can be stably and easily Can be formed.
  • the photocurable resin composition according to the present invention has excellent wettability and releasability with the thermosetting or photocuring resin for pattern formation, regardless of whether or not additional surface treatment, and at the same time provides excellent adhesion between the mold-forming substrate and the mold. Indicates.
  • the photocurable resin composition according to the present invention includes a fluorine-based monomer, a polymer, or a mixture thereof, thereby having a significantly lower viscosity than the polymer resin compositions used in the conventional imprint mold, thereby easily forming a micropattern. Molds with completeness can be prepared.

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  • Manufacturing & Machinery (AREA)
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  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Shaping Of Tube Ends By Bending Or Straightening (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Moulds For Moulding Plastics Or The Like (AREA)

Abstract

La présente invention concerne une composition de résine photodurcissable pour lithographie d’impression pour former des motifs de diverses tailles sur un substrat, et un procédé de fabrication d’un moule d’impression l’utilisant. La composition de résine photodurcissable a des propriétés adhésives supérieures, et peut ainsi être appliquée sur divers matériaux tels que du plastique, du métal, du verre, etc. La composition de résine photodurcissable présente non seulement une excellente résistance à la contamination, mais régule également l’énergie de surface d’un moule pour présenter des propriétés de démoulage supérieures afin de permettre de détacher facilement le moule du substrat. La composition de résine photodurcissable de la présente invention présente une excellente réticulabilité, et présente ainsi des propriétés de non-gonflement lorsqu’elle est exposée à un solvant organique. La composition de résine photodurcissable de la présente invention présente des propriétés mécaniques supérieures, et une force de rappel et une perméabilité élevées, et peut ainsi être utilisée efficacement pour la fabrication d’un moule pour la lithographie d’impression.
PCT/KR2010/005035 2009-08-07 2010-07-30 Composition de résine photodurcissable pour lithographie d’impression et procédé de fabrication d’un moule d’impression l’utilisant WO2011016651A2 (fr)

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CN105103329A (zh) * 2013-09-30 2015-11-25 株式会社Lg化学 制备有机电子器件的方法
US9619741B1 (en) 2011-11-21 2017-04-11 Dynamics Inc. Systems and methods for synchronization mechanisms for magnetic cards and devices
EP4160312A1 (fr) * 2021-10-04 2023-04-05 Joanneum Research Forschungsgesellschaft mbH Laque de gaufrage élastique à haute dispersion optique

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JP5794387B2 (ja) 2012-04-10 2015-10-14 ダイキン工業株式会社 インプリント用樹脂モールド材料組成物
EP2825359B1 (fr) 2012-04-13 2017-02-01 Nanogriptech, LLC Procédé permettant de mouler des éléments simples ou complexes à micromotifs et/ou nanomotifs à la fois sur des objets moulés plans ou non plans et des surfaces planes ou non planes et objets moulés produits à l'aide de ce dernier
CN104932197B (zh) * 2015-05-26 2020-01-17 南方科技大学 一种纳米压印用膨胀聚合压印胶
KR102206859B1 (ko) * 2015-09-23 2021-01-22 코오롱인더스트리 주식회사 유기발광다이오드용 오버코트층 형성용 조성물 및 이를 포함하는 유기발광다이오드
KR20180014287A (ko) 2016-07-28 2018-02-08 삼성디스플레이 주식회사 패터닝된 경화물의 제조 방법 및 패터닝된 경화물

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CN105103329A (zh) * 2013-09-30 2015-11-25 株式会社Lg化学 制备有机电子器件的方法
EP4160312A1 (fr) * 2021-10-04 2023-04-05 Joanneum Research Forschungsgesellschaft mbH Laque de gaufrage élastique à haute dispersion optique

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