WO2014013922A1 - 防汚性を有する凹凸形状の表面を有する構造体及びその製造方法 - Google Patents
防汚性を有する凹凸形状の表面を有する構造体及びその製造方法 Download PDFInfo
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- WO2014013922A1 WO2014013922A1 PCT/JP2013/068876 JP2013068876W WO2014013922A1 WO 2014013922 A1 WO2014013922 A1 WO 2014013922A1 JP 2013068876 W JP2013068876 W JP 2013068876W WO 2014013922 A1 WO2014013922 A1 WO 2014013922A1
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Classifications
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- 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
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- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- B08B17/00—Methods preventing fouling
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- B08B17/06—Preventing deposition of fouling or of dust by giving articles subject to fouling a special shape or arrangement
- B08B17/065—Preventing deposition of fouling or of dust by giving articles subject to fouling a special shape or arrangement the surface having a microscopic surface pattern to achieve the same effect as a lotus flower
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- B29C59/02—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
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- B29C59/02—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
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- B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
- B29C59/16—Surface shaping of articles, e.g. embossing; Apparatus therefor by wave energy or particle radiation, e.g. infrared heating
-
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- B32B3/30—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar form; Layered products having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer characterised by a layer formed with recesses or projections, e.g. hollows, grooves, protuberances, ribs
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/6725—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing ester groups other than acrylate or alkylacrylate ester groups
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
- C08G18/8029—Masked aromatic polyisocyanates
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Definitions
- the present invention relates to a structure having a concavo-convex surface produced from an imprint material (film-forming composition for imprint) and having a Martens hardness within a predetermined range, and a method for producing the structure. More specifically, the present invention relates to a structure having the surface that can easily wipe off dirt such as fingerprints attached to the uneven surface and a method for manufacturing the structure.
- Nanoimprint lithography is a method in which a mold having an arbitrary pattern is brought into contact with a substrate on which a resin film is formed, the resin film is pressurized, and heat or light is used as an external stimulus to cure the target pattern.
- This nanoimprint lithography has an advantage that nanoscale processing can be performed easily and inexpensively as compared with optical lithography or the like in conventional semiconductor device manufacturing. Therefore, nanoimprint lithography is a technology that is expected to be applied to the manufacture of semiconductor devices, opto-devices, displays, storage media, biochips, etc., instead of optical lithography technology.
- Various reports have been made on curable compositions (Patent Documents 2 and 3).
- Electronic devices such as opto devices and displays are required to have the ability to remove fingerprints and other dirt attached to the surface.
- the electronic device can be wiped dry without using a cleaning solution such as water for handling the electronic device.
- various structures having a concavo-convex surface obtained by nanoimprint lithography have been disclosed.
- examination of removing dirt such as fingerprints attached to the structure by directly wiping with a cloth is performed. There are no reports.
- the present invention has been made based on the above circumstances, and a problem to be solved is to provide a structure having a dry wiping property against dirt such as fingerprints attached to an uneven surface, and a method for manufacturing the structure. That is.
- the present inventors have found that the hardness of a structure having a concavo-convex surface is within a specific range, so that the structure adheres to the concavo-convex surface of the structure. As a result, the inventors have found that the wiping property of the fingerprint that has been developed is expressed, and have completed the present invention.
- the present invention is produced from a composition containing at least one compound having 1 to 10 polymerizable groups per molecule and a photopolymerization initiator, and has a Martens hardness of fused quartz. There is is 3N / mm 2 or more 130N / mm 2 or less Martens hardness as measured under a condition which is 4100N / mm 2, to a structure having a corrugated surface.
- the present invention relates to the structure according to the first aspect, in which the polymerizable group is at least one group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, a vinyl group, and an allyl group.
- the composition further includes a silicone compound, and relates to the structure according to the first aspect or the second aspect, which is produced by imprinting the composition.
- the present invention relates to the structure according to the third aspect, in which the silicone compound is a compound represented by the following formula (1) or formula (2).
- R 1 represents a hydrogen atom or a methyl group
- R 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
- a plurality of R 3 s independently represent a hydrogen atom or 1 to 3 carbon atoms.
- corrugated shape is related with the structure as described in any one of the 1st viewpoint thru
- the composition containing at least one compound having 1 to 10 polymerizable groups in one molecule and a photopolymerization initiator on a substrate it has an uneven shape of a mold.
- the coating film on the substrate is pressure-bonded to a surface, and the coating film is photocured in that state to form a cured film, and the cured film on the substrate is peeled from the mold.
- the present invention relates to a method for manufacturing the structure according to any one of the above.
- the composition relates to the method for producing a structure according to the sixth aspect, further including a surfactant.
- the structure according to the sixth aspect or the seventh aspect includes a step of volatilizing the solvent by baking after applying the composition further including a solvent onto the substrate. Regarding the method.
- a film is used as the substrate, and in a test in which the cured film on the film is peeled by 90 ° from the mold, the load when the cured film on the film is peeled from the mold is set to the width of the film
- the present invention relates to the method for producing a structure according to any one of the sixth to eighth aspects, in which a release force that is a value converted per 1 cm is greater than 0 g / cm and equal to or less than 0.7 g / cm.
- a 10th viewpoint it is related with the optical member provided with the structure as described in any one of a 1st viewpoint thru
- the present invention relates to a semiconductor element including the structure according to any one of the first to fifth aspects.
- the solar cell provided with the structure as described in any one of a 1st viewpoint thru
- the present invention relates to an electronic device provided with the structure according to any one of the first to fifth aspects on a base material.
- the structure of the present invention can dry and wipe dirt such as fingerprints adhering to the uneven surface. Therefore, the structure of the present invention can be suitably used for a product using a member that is required to wipe off dirt such as fingerprints, such as a solar cell, an LED device, and a display.
- the convex portion represents a portion protruding from the reference surface
- the concave portion represents a portion recessed from the reference surface.
- the structure of the present invention may have both a concave portion and a convex portion, or may have only one of them.
- the surface of the structure is preferably a moth-eye shape.
- the moth-eye shape represents a wavy shape in which concave portions and convex portions are continuous.
- the aspect ratio is, for example, 1.0 or more and 3.0 or less, preferably 1.0 or more and 1.5 or less.
- the aspect ratio represents (average height or average depth of convex portions or concave portions from the reference surface) / (average period in at least one direction of convex portions or concave portions).
- Examples of the mold material for optical imprint used for the production of the structure of the present invention include quartz, silicon, nickel, alumina, carbonyl silane, and glassy carbon.If a desired pattern is obtained, There is no particular limitation. Further, the mold may be subjected to a mold release treatment for forming a thin film of a fluorine compound or the like on the surface thereof in order to improve the mold release property. Examples of the mold release agent used for the mold release treatment include OPTOOL (registered trademark) HD and DSX manufactured by Daikin Industries, Ltd., but are not particularly limited as long as the target pattern can be obtained.
- the pattern size of the optical imprint is on the order of nanometers, specifically according to the pattern size of less than 1 micron.
- a composition (imprint material) containing at least one compound having 1 to 10 polymerizable groups in one molecule and a photopolymerization initiator used for production of the structure of the present invention is coated on a substrate.
- known or well-known methods for example, spin coating method, dipping method, flow coating method, ink jet method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer printing method, Examples thereof include brush coating, blade coating, and air knife coating.
- Examples of the substrate on which the imprint material used in the manufacture of the structure of the present invention is applied include, for example, glass on which silicon and indium tin oxide (ITO) are formed (hereinafter referred to as “ITO substrate” in this specification).
- ITO substrate glass on which silicon and indium tin oxide (ITO) are formed
- SiN substrate glass formed with silicon nitride (SiN)
- IZO indium zinc oxide
- PET polyethylene terephthalate
- TAC triacetyl cellulose
- Examples include base materials made of acrylic, plastic, glass, quartz, ceramics and the like.
- flexible flexible substrates such as triacetyl cellulose, polyethylene terephthalate, polymethyl methacrylate, cycloolefin (co) polymer, polyvinyl alcohol, polycarbonate, polystyrene, polyimide, polyamide, polyolefin, polypropylene, polyethylene, polyethylene naphthalate. It is also possible to use a substrate made of phthalate, polyethersulfone, and a copolymer obtained by combining these polymers.
- the light source for curing after applying the imprint material on the substrate is not particularly limited, and examples thereof include a high pressure mercury lamp, a low pressure mercury lamp, an electrodeless lamp, a metal halide lamp, a KrF excimer laser, an ArF excimer laser, and an F 2 excimer.
- a laser, an electron beam (EB), and extreme ultraviolet (EUV) can be mentioned.
- As the wavelength generally, a 436 nm G line, a 405 nm H line, a 365 nm I line, or a GHI mixed line can be used.
- the exposure amount is preferably, 30 mJ / cm 2 to 2000 mJ / cm 2, more preferably from 30 mJ / cm 2 to 1000 mJ / cm 2.
- a baking step may be added to evaporate the solvent on at least one of the coating film before light irradiation and the cured film after light irradiation.
- the baking equipment is not particularly limited. For example, baking is performed in a suitable atmosphere, that is, in an inert gas such as air or nitrogen, or in a vacuum using a hot plate, an oven, or a furnace. Anything that can do.
- the baking temperature is not particularly limited for the purpose of evaporating the solvent, but can be performed at 40 ° C. to 200 ° C., for example.
- An apparatus for performing optical imprinting is not particularly limited as long as a target structure is obtained.
- ST50 manufactured by Toshiba Machine Co., Ltd. ST50S-LED manufactured by the same company, Sindre (registered trademark) 60 manufactured by Obducat
- Examples include commercially available devices such as NM-0801HB manufactured by Myeongchang Kiko Co., Ltd.
- coated on the base material using this apparatus are crimped
- the Martens hardness by nanoindentation is, 3N / mm 2 or more when measured under the conditions fused silica is 4100N / mm 2, preferably 8N / mm 2 or more 130N / mm 2 or less It is essential. If it is less than 8 N / mm 2 , it is difficult to form a structure by optical imprinting, and if it is greater than 130 N / mm 2 , the structure tends to be destroyed when wiping off fingerprints adhering to the uneven surface of the structure. Become.
- an ultra-fine indentation hardness tester ENT-2100 (manufactured by Elionix Co., Ltd.) is used, and the indenter is a titanium triangular indenter (manufactured by Tokyo Diamond Tool Manufacturing Co., Ltd.) having a ridge angle of 115 °. Measured.
- the 90 ° peel test for evaluating the release force generally means an adhesive (corresponding to a cured film formed by photoimprinting in the present invention) and an adherend (in the present invention, a film used as a substrate). It is a test to measure the resistance force (tension) generated when it is peeled off in a 90 ° direction at a predetermined peeling speed after a predetermined time. Usually, the measurement is an evaluation method with reference to JIS Z0237. Will be implemented. A value obtained by converting the resistance force measured here per width of the adherend can be evaluated as a release force.
- a composition containing at least one compound having 1 to 10 polymerizable groups per molecule and a photopolymerization initiator is applied on a film, and the coating film on the film is applied to the mold.
- the mold release force measured in the test to be performed that is, the value obtained by converting the load when the film on the film is completely peeled from the surface having the uneven shape of the mold per 1 cm width of the film is preferably as small as possible, For example, it is preferably greater than 0 g / cm and 0.7 g / cm or less.
- the compound having 1 to 10 polymerizable groups in one molecule may be a single compound or a combination of two or more compounds as long as the desired hardness can be obtained. Moreover, you may have an ester bond, an ether bond, or a urethane bond in a molecule
- the polymerizable group include an acryloyloxy group, a methacryloyloxy group, a vinyl group, and an allyl group.
- the acryloyloxy group may be expressed as an acryloxy group
- the methacryloyloxy group may be expressed as a methacryloxy group.
- Examples of the compound include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, Isodecyl (meth) acrylate, n-lauryl (meth) acrylate, n-stearyl (meth) acrylate, isostearyl (meth) acrylate, n-butoxyethyl (meth) acrylate), butoxydiethylene glycol (meth) acrylate, cyclohexyl (meth) Acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl
- the above-mentioned compounds can be obtained as commercial products. Specific examples thereof include light esters M, E, NB, IB, TB, EH, ID, L, S, BC, and the like. 130MA, 041MA, CH, THF (1000), BZ, PO, IB-X, HO-225 (N), HOP (N), HOA (N), HOP-A ( N), HOB (N), DM, DE, A, HOMS (N), HO-HH (N), HO-MPP (N), G, P-1M, G -101P, G-201P, EG, UA-306H, UA-306T, UA-306I, UA-510H (manufactured by Kyoeisha Chemical Co., Ltd.), NK ester AM-30G, AM-90G, AM- 130G, AM-230G, M-20G, M-40G M-90G, TM230G, AMP-10G, AMP-20GY, AMP-60G, PHE-1G,
- the photopolymerization initiator is not particularly limited as long as it has absorption in the light source used at the time of photocuring.
- tert-butylperoxy-iso-butarate 2,5-dimethyl-2, 5-bis (benzoyldioxy) hexane, 1,4-bis [ ⁇ - (tert-butyldioxy) -iso-propoxy] benzene, di-tert-butyl peroxide, 2,5-dimethyl-2,5-bis (tert -Butyldioxy) hexene hydroperoxide, ⁇ - (iso-propylphenyl) -iso-propyl hydroperoxide, tert-butyl hydroperoxide, 1,1-bis (tert-butyldioxy) -3,3,5-trimethylcyclohexane, butyl- 4,4-bis (tert-butyldioxy) valerate,
- the above-mentioned compounds can be obtained as commercial products. Specific examples thereof include IRGACURE (registered trademark) 651, 184, 500, 2959, 127, 754, 907, 369, 379, 379EG, 819, 819DW, 1800, 1870, 784, OXE01, OXE02, 250, Darocur (registered trademark) 1173, MBF, 4265, Lucirin (registered trademark) TPO (above, BASF) Japan Co., Ltd.), KAYACURE (registered trademark) DETX, MBP, DMBI, EPA, OA (above, Nippon Kayaku Co., Ltd.), VISURE-10, 55 (above, STAUFFER Co.
- IRGACURE registered trademark
- Darocur registered trademark
- ESACURE registered trademark
- KIP150, TZT 1001, KT 46, same KB1, same KL200, same KS300, same EB3, triazine-PMS, triazine A, triazine B (manufactured by Nippon Siebel Hegner), Adekaoptoma-N-1717, same N-1414, same N-1606 (stock) Company ADEKA).
- the above photopolymerization initiators can be used alone or in combination of two or more.
- the silicone compound contributes to reducing the mold release force measured when the resin film is peeled from the mold.
- a compound having a silicone skeleton (siloxane skeleton) in the molecule is preferred, and a compound having a dimethyl silicone skeleton is preferred, and a compound represented by the formula (1) or formula (2) is particularly preferred.
- the above compounds can be obtained as commercial products, and specific examples thereof include BYK-302, BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-370, BYK-375. BYK-378, BYK-UV 3500, BYK-UV 3570 (manufactured by Big Chemie Japan Co., Ltd.), X-22-164, X-22-164AS, X-22-164A, X-22-164B, X -22-164C, X-22-164E, X-22-163, X-22-169AS, X-22-174DX, X-22-2426, X-22-9002, X-22-2475, X-22 -4952, KF-643, X-22-343, X-22-2404, X-22-2046, X-22-1602 Chemical Industry Co., Ltd.) and the like.
- the above compounds having a silicone skeleton can be used alone or in combination of two or more.
- a surfactant may be added to the imprint material for forming the structure of the present invention.
- Surfactant plays the role which adjusts the film forming property of the coating film obtained.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbionic surfact
- the above surfactants can be used alone or in combination of two or more.
- the ratio is preferably 0.01 phr to 40 phr, more preferably 0.01 phr to 10 phr with respect to the compound having 1 to 10 polymerizable groups per molecule. is there.
- An imprint material solvent for forming the structure of the present invention may be contained.
- a solvent plays the role which adjusts the film thickness of the structure obtained.
- solvent examples include toluene, p-xylene, o-xylene, styrene, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether.
- an epoxy compound As long as the imprint material for forming the structure of the present invention does not impair the effects of the present invention, an epoxy compound, a photoacid generator, a photosensitizer, an ultraviolet absorber, and an antioxidant, as necessary. Further, it may contain an adhesion aid or a mold release improver.
- epoxy compound examples include Epolide (registered trademark) GT-401, PB3600, Celoxide (registered trademark) 2021P, 2000, 3000, EHPE3150, EHPE3150CE, Cyclomer (registered trademark) M100 (above, Inc.) Daicel), EPICLON (registered trademark) 840, 840-S, N-660, N-673-80M (above, manufactured by DIC Corporation).
- photoacid generator examples include IRGACURE (registered trademark) PAG103, PAG108, PAG121, PAG203, CGI725 (above, manufactured by BASF Japan Ltd.), WPAG-145, WPAG-170, WPAG-199, WPAG-281, WPAG-336, WPAG-367 (Wako Pure Chemical Industries, Ltd.), TFE triazine, TME-triazine, MP-triazine, dimethoxytriazine, TS-91, TS-01 (Sanwa Chemical Co., Ltd.) Manufactured).
- IRGACURE registered trademark
- PAG103, PAG108, PAG121, PAG203, CGI725 above, manufactured by BASF Japan Ltd.
- WPAG-145, WPAG-170, WPAG-199, WPAG-281, WPAG-336, WPAG-367 Wako Pure Chemical Industries, Ltd.
- TFE triazine TME-triazine
- photosensitizer examples include, for example, thioxanthene series, xanthene series, ketone series, thiopyrylium salt series, base styryl series, merocyanine series, 3-substituted coumarin series, 3,4-substituted coumarin series, cyanine series, acridine series. , Thiazine, phenothiazine, anthracene, coronene, benzanthracene, perylene, ketocoumarin, coumarin, and borate.
- the above photosensitizers can be used alone or in combination of two or more.
- the absorption wavelength in the UV region can be adjusted by using the photosensitizer.
- UV absorber examples include TINUVIN (registered trademark) PS, 99-2, 109, 328, 384-2, 400, 405, 460, 477, 479, 900, 928, 1130, 111FDL, 123, 144, 152, 292, 5100, 400-DW, 477-DW, 99-DW, 123-DW, 5050, 5060, 5151 (above, BASF Japan Ltd.).
- TINUVIN registered trademark
- PS 99-2, 109, 328, 384-2
- 400 405, 460, 477, 479, 900, 928, 1130, 111FDL, 123, 144, 152, 292, 5100, 400-DW, 477-DW, 99-DW, 123-DW, 5050, 5060, 5151 (above, BASF Japan Ltd.).
- the above ultraviolet absorbers can be used alone or in combination of two or more. By using the ultraviolet absorber, it is possible to control the curing speed of the outermost surface of the film during photocuring and to improve the mold release property.
- antioxidants examples include IRGANOX (registered trademark) 1010, 1035, 1076, 1135, 1520L (above, BASF Japan Ltd.).
- the above antioxidants can be used alone or in combination of two or more. By using the antioxidant, it is possible to prevent the film from turning yellow due to oxidation.
- adhesion aid examples include 3-methacryloxypropyltrimethoxysilane and 3-acryloxypropyltrimethoxysilane.
- the content of the adhesion assistant is preferably 5 phr to 50 phr, more preferably 10 phr to 50 phr, with respect to the mass of the component (A) or the total mass of the component (A) and the component (D).
- Examples of the mold release improver include fluorine-containing compounds.
- Examples of the fluorine-containing compound include R-5410, R-1420, M-5410, M-1420, E-5444, E-7432, A-1430, and A-1630 (manufactured by Daikin Industries, Ltd.). It is done.
- the method for preparing the imprint material for forming the structure of the present invention is not particularly limited, but at least one compound having 1 to 10 polymerizable groups in one molecule, a photopolymerization initiator, and any It is only necessary that the silicone compound, surfactant, solvent, and other additives, if necessary, are mixed and the imprint material is in a uniform state. Further, the order of mixing at least one compound having 1 to 10 polymerizable groups in one molecule and a photopolymerization initiator, a silicone compound, a surfactant and a solvent, and other additives as required is as follows. If a uniform imprint material is obtained, there will be no problem and it will not specifically limit.
- Examples of the method for preparing the imprint material include a method in which a photopolymerization initiator is mixed in a predetermined ratio with at least one compound having 1 to 10 polymerizable groups in one molecule.
- a method of further mixing a silicone compound, a surfactant and a solvent to form a uniform imprint material can also be mentioned.
- a method in which other additives are further added and mixed as necessary may be mentioned.
- the semiconductor element provided with the structure of the present invention and an optical member, a solid-state imaging device, an LED device, a solar cell, a display, and an electronic device provided with the structure on a substrate are also objects of the present invention.
- Synthesis Example 2 A flask similar to that used in Synthesis Example 1 was charged with 48.2 parts by mass of toluene and 4.2 parts by mass of stearyl alcohol (NAA-46), and the temperature was raised to 40 ° C. After confirming that stearyl alcohol was completely dissolved, 25 parts by mass of isocyanurate-modified hexamethylene diisocyanate (Takenate (registered trademark) D-170N) was charged and the temperature was raised to 70 ° C. After reacting at the same temperature for 30 minutes, 0.02 part by mass of dibutyltin laurate was charged and held at the same temperature for 3 hours.
- Synthesis Example 3 A flask similar to that used in Synthesis Example 1 was charged with 44.8 parts by mass of toluene and 4.6 parts by mass of stearyl alcohol (NAA-46), and the temperature was raised to 40 ° C. Thereafter, it was confirmed that stearyl alcohol was completely dissolved, and trimethylolpropane adduct modified type of xylylene diisocyanate (Takenate (registered trademark) D-110N; manufactured by Mitsui Chemicals, Inc., solid content: 75%, NCO%: 11. 5) 50 parts by mass were charged and the temperature was raised to 70 ° C.
- Synthesis Example 4 A flask similar to that used in Synthesis Example 1 was charged with 61.3 parts by mass of toluene and 9.7 parts by mass of behenyl alcohol (NAA-422; manufactured by NOF Corporation, hydroxyl value: 180), and the temperature was raised to 40 ° C. . Thereafter, it was confirmed that the behenyl alcohol was completely dissolved, and 50 parts by mass of isocyanurate modified type of hexamethylene diisocyanate (Takenate (registered trademark) D-170N) was charged and the temperature was raised to 70 ° C. After reacting at the same temperature for 30 minutes, 0.02 part by mass of dibutyltin laurate was charged and held at the same temperature for 3 hours.
- NAA-422 isocyanurate modified type of hexamethylene diisocyanate
- urethane acrylate (I) prepared in Synthesis Example 1 5 g was added to Lucirin (registered trademark) TPO (manufactured by BASF Japan Ltd.) (hereinafter abbreviated as “Lucirin TPO”) 0.125 g (in weight of urethane acrylate (I)). 2.5 phr was added to prepare an imprint material PNI-1.
- Lucirin TPO registered trademark
- Preparation Example 6 Imprint as in Preparation Example 1 except that the urethane acrylate (I) in Preparation Example 1 was changed to NK Economer A-1000PER (hereinafter abbreviated as “A-1000PER”) (manufactured by Shin-Nakamura Chemical Co., Ltd.). Material PNI-6 was prepared.
- A-1000PER NK Economer A-1000PER
- Preparation Example 7 An imprint material PNI-7 was prepared in the same manner as in Preparation Example 1, except that the urethane acrylate (I) in Preparation Example 1 was changed to X-22-1602 (manufactured by Shin-Etsu Chemical Co., Ltd.).
- Preparation Example 9 Imprinting as in Preparation Example 1 except that the urethane acrylate (I) in Preparation Example 1 was changed to NK ester APG-700 (hereinafter abbreviated as “APG-700”) (manufactured by Shin-Nakamura Chemical Co., Ltd.). Material PNI-9 was prepared.
- APG-700 NK ester APG-700
- Preparation Example 11 An imprint material PNI-11 was prepared in the same manner as in Preparation Example 1, except that the urethane acrylate (I) in Preparation Example 1 was changed to NK ester A-TMPT-9EO (manufactured by Shin-Nakamura Chemical Co., Ltd.).
- Preparation Example 12 An imprint material PNI-12 was prepared in the same manner as in Preparation Example 1, except that the urethane acrylate (I) in Preparation Example 1 was changed to tetraethylene glycol diacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.).
- Preparation Example 13 Preparation Example, except that urethane acrylate (I) in Preparation Example 1 was changed to KAYARAD (registered trademark) DPEA-12 (hereinafter abbreviated as “DPEA-12” in this specification) (manufactured by Nippon Kayaku Co., Ltd.) Imprint material PNI-13 was prepared in the same manner as in Example 1.
- KAYARAD registered trademark
- DPEA-12 registered trademark of DPEA-12
- Imprint material PNI-13 was prepared in the same manner as in Example 1.
- NK ester AM-90G (hereinafter abbreviated as “AM-90G”) (made by Shin-Nakamura Chemical Co., Ltd.) 2.5 g and NK ester A-TMPT (hereinafter abbreviated as “A-TMPT” in this specification) (Mixed with Shin-Nakamura Chemical Co., Ltd.) 2.5 g, add 0.125 g of Lucirin TPO (2.5 phr to the total mass of AM-90G and A-TMPT) to the mixture, and imprint Material PNI-16 was prepared.
- AM-90G NK ester AM-90G
- A-TMPT NK ester A-TMPT
- KAYARAD registered trademark
- DPHA DPHA
- A-1000PER 2.5 g
- Lucirin TPO 0.125 g, based on the total mass of DPHA and A1000PER
- Imprint material PNI-23 was prepared by mixing 3.0 g of DPHA and 2.0 g of A-1000PER and adding 0.125 g of Lucirin TPO (2.5 phr based on the total mass of DPHA and A1000PER) to the mixture.
- NK Ester A1000 (hereinafter abbreviated as “A1000”) (manufactured by Shin-Nakamura Chemical Co., Ltd.) 5 g, Lucirin TPO 0.125 g (2.5 phr with respect to the mass of A1000), methyl ethyl ketone (hereinafter “MEK”) Abbreviated. ) 5.125 g was mixed to prepare imprint material PNI-29.
- A1000 NK Ester A1000
- MEK methyl ethyl ketone
- ⁇ Preparation Example 31> Mix UA-306H 2.0g, 3.0g X-22-1602, Lucirin TPO 0.125g (UAphr-306H, 2.5phr relative to the total mass of X-22-1602), MEK 5.125g, imprint Material PNI-31 was prepared.
- Imprint material PNI-33 was prepared by mixing 5 g of A-TMPT and 0.125 g of Lucirin TPO (2.5 phr with respect to the mass of A-TMPT).
- PET30 KAYARAD PET30
- Lucirin TPO 2.5 phr with respect to the mass of PET30
- ⁇ Preparation Example 35 5 g of UA-510 (manufactured by Kyoeisha Chemical Co., Ltd.) and 0.125 g of Lucirin TPO (2.5 phr with respect to the mass of UA-510) were mixed to prepare imprint material PNI-35.
- Imprint material PNI-36 was prepared by mixing 3.25 g of DPHA, 1.75 g of A-1000PER and 0.125 g of Lucirin TPO (2.5 phr with respect to the total mass of DPHA, A-1000PER).
- Imprint material PNI-37 was prepared by mixing 3.5 g of DPHA, 1.5 g of A-1000PER, and 0.125 g of Lucirin TPO (2.5 phr with respect to the total mass of DPHA, A-1000PER).
- Each of the imprint materials obtained in Preparation Examples 1 to 37 is a triacetyl cellulose film having a thickness of 80 ⁇ m (using Fujitac (registered trademark) manufactured by FUJIFILM Corporation) (hereinafter abbreviated as “TAC film”). ) was coated using a bar coater (fully automatic film applicator KT-AB3120 manufactured by Co-Tech Co., Ltd.), and the coating film on the TAC film was roller-bonded to the moth-eye pattern mold subjected to the above-described release treatment.
- TAC film Triacetyl cellulose film having a thickness of 80 ⁇ m (using Fujitac (registered trademark) manufactured by FUJIFILM Corporation) (hereinafter abbreviated as “TAC film”). ) was coated using a bar coater (fully automatic film applicator KT-AB3120 manufactured by Co-Tech Co., Ltd.), and the coating film on the TAC film was roller-bonded to the moth-eye pattern mold subjected
- the coating film was exposed to light of 350 mJ / cm 2 from the TAC film side with an electrodeless uniform irradiation device (QRE-4016A, manufactured by Oak Manufacturing Co., Ltd.), and photocured. Then, a 90 ° peel test was performed with reference to JIS Z0237, and the cured film formed on the TAC film adhered to the surface having the uneven shape of the mold was completely peeled from the surface having the uneven shape of the mold. The load was measured. The load per 1 cm width of the film was calculated and used as the release force (g / cm). The results are shown in Tables 1 and 2.
- a fingerprint wiping test was performed by reciprocating 50 times at a load of 570 g / cm 2 , and the fingerprint wiping property was confirmed visually.
- the wipe performed in the test is a dry wipe. Tables 1 and 2 show the results of evaluating the case where the fingerprint could be wiped off after the wiping test, and the case where the fingerprint could not be wiped off, that is, the case where the fingerprint remained as x.
- the measurement device uses an ultra-fine indentation hardness tester ENT-2100 (manufactured by Elionix Co., Ltd.), and the indenter melts using a titanium triangular indenter (manufactured by Tokyo Diamond Tool Mfg. Co., Ltd.) with a ridge angle of 115 °.
- the measurement was performed under the condition that the Martens hardness of quartz was 4100 N / mm 2 .
- the obtained results are shown in Tables 1 and 2.
- the structure of the present invention can be suitably used for the surface of a display, a solar cell, or an LED device, for example, because it can wipe off the fingerprint attached to the uneven surface.
Abstract
Description
したがって、ナノインプリントリソグラフィは、光リソグラフィ技術に代わり、半導体デバイス、オプトデバイス、ディスプレイ、記憶媒体、バイオチップ等の製造への適用が期待されている技術であることから、ナノインプリントリソグラフィに用いる光ナノインプリントリソグラフィ用硬化性組成物について様々な報告がなされている(特許文献2、特許文献3)。
第2観点として、前記重合性基がアクリロイルオキシ基、メタアクリロイルオキシ基、ビニル基及びアリル基からなる群から選ばれる少なくとも1種の基である、第1観点に記載の構造体に関する。
第3観点として、前記組成物はシリコーン化合物をさらに含み、該組成物をインプリントすることによって作製される、第1観点又は第2観点に記載の構造体に関する。
第4観点として、前記シリコーン化合物が下記式(1)又は式(2)で表される化合物である第3観点に記載の構造体に関する。
第5観点として、前記凹凸形状はモスアイ構造である第1観点乃至第4観点のいずれか一つに記載の構造体に関する。
第6観点として、重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤を含有する前記組成物を基材上に塗布した後、モールドの凹凸形状を有する面に前記基材上の塗膜を圧着し、その状態で前記塗膜を光硬化させて硬化膜とし、前記基材上の硬化膜を前記モールドから剥離する、第1観点乃至第5観点のいずれか一つに記載の構造体の製造方法に関する。
第7観点として、前記組成物は界面活性剤をさらに含む第6観点に記載の構造体の製造方法に関する。
第8観点として、溶剤をさらに含む前記組成物を前記基材上に塗布した後、ベークをすることにより前記溶剤を揮発させる工程を含む、第6観点又は第7観点に記載の構造体の製造方法に関する。
第9観点として、前記基材としてフィルムを用い、前記フィルム上の硬化膜を前記モールドから90°剥離する試験において、前記フィルム上の硬化膜を前記モールドから剥離したときの荷重を前記フィルムの幅1cmあたりに換算した値である離型力が0g/cmより大きく0.7g/cm以下である、第6観点乃至第8観点のいずれか一つに記載の構造体の製造方法に関する。
第10観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えた光学部材に関する。
第11観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えた固体撮像装置に関する。
第12観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えたLEDデバイスに関する。
第13観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を備えた半導体素子に関する。
第14観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えた太陽電池に関する。
第15観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えたディスプレイに関する。
第16観点として、第1観点乃至第5観点のいずれか一つに記載の構造体を基材上に備えた電子デバイスに関する。
本発明の構造体において、凸部とは基準となる面よりも突出している部分を表し、凹部とは基準となる面よりも凹んでいる部分を表す。本発明の構造体は、凹部及び凸部を両方有していても、どちらか一方のみを有していてもよい。また、本発明の構造体をデバイスの反射防止膜として使用する場合は、その構造体の表面はモスアイ形状が好ましい。ここで、モスアイ形状とは凹部と凸部が連続し、波打った形状を表す。
本発明の構造体は、ナノインデンテーションによるマルテンス硬さが、溶融石英が4100N/mm2となる条件で測定したときに3N/mm2以上、好ましくは8N/mm2以上130N/mm2以下であることが必須である。8N/mm2よりも小さいと光インプリントによる構造体の形成が困難となり、130N/mm2よりも大きいと構造体の凹凸形状の表面に付着した指紋の拭き取り時において構造体の破壊が起こりやすくなる。測定装置としては、超微小押し込み硬さ試験機 ENT-2100(株式会社エリオニクス製)を使用し、圧子は稜間角115°のチタン製三角圧子(株式会社東京ダイヤモンド工具製作所製)を用いて測定される。
本明細書における離型力を評価する90°剥離試験とは、一般に接着物(本発明では光インプリントにより形成された硬化膜に相当する)を被着物(本発明では基材として使用するフィルムに相当する)に貼付けし、所定時間後に所定の剥離速度で90°方向に引き剥がす際に生じる抵抗力(張力)を測定する試験であり、通常、測定は、JIS Z0237を参考にした評価法にて実施される。ここで測定された抵抗力を被着物の幅あたりに換算した値を離型力として評価することができる。本発明においては、重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤を含有する組成物をフィルム上に塗布し、そのフィルム上の塗膜をモールドの凹凸形状を有する面に接着させ、続いて当該塗膜を、モールドの凹凸形状を有する面を接着させたまま光硬化させ、その後フィルム上の硬化被膜をモールドの凹凸形状を有する面から90°剥離する試験において計測された離型力、すなわち、当該フィルム上の被膜をモールドの凹凸形状を有する面から完全に剥離したときの荷重を当該フィルムの横幅1cmあたりに換算した値は、小さいほど好ましく、例えば0g/cmより大きく0.7g/cm以下であることが好ましい。
以下に、本発明の構造体を形成するためのインプリント材料(組成物)について詳述する。
重合性基を1分子中に1個乃至10個有する化合物は、所望の硬度を得ることができれば単独でも2種以上の組み合わせでもよい。また、分子中にエステル結合、エーテル結合又はウレタン結合を有していてもよい。前記重合性基としては、例えば、アクリロイルオキシ基、メタアクリロイルオキシ基、ビニル基、アリル基が挙げられる。ここで、アクリロイルオキシ基はアクリロキシ基と、メタアクリロイルオキシ基はメタアクリロキシ基と表現されることがある。
光重合開始剤としては、光硬化時に使用する光源に吸収をもつものであれば、特に限定されるものではないが、例えば、tert-ブチルペルオキシ-iso-ブタレート、2,5-ジメチル-2,5-ビス(ベンゾイルジオキシ)ヘキサン、1,4-ビス[α-(tert-ブチルジオキシ)-iso-プロポキシ]ベンゼン、ジ-tert-ブチルペルオキシド、2,5-ジメチル-2,5-ビス(tert-ブチルジオキシ)ヘキセンヒドロペルオキシド、α-(iso-プロピルフェニル)-iso-プロピルヒドロペルオキシド、tert-ブチルヒドロペルオキシド、1,1-ビス(tert-ブチルジオキシ)-3,3,5-トリメチルシクロヘキサン、ブチル-4,4-ビス(tert-ブチルジオキシ)バレレート、シクロヘキサノンペルオキシド、2,2’,5,5’-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-ブチルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-アミルペルオキシカルボニル)ベンゾフェノン、3,3’,4,4’-テトラ(tert-ヘキシルペルオキシカルボニル)ベンゾフェノン、3,3’-ビス(tert-ブチルペルオキシカルボニル)-4,4’-ジカルボキシベンゾフェノン、tert-ブチルペルオキシベンゾエート、ジ-tert-ブチルジペルオキシイソフタレート等の有機過酸化物;9,10-アントラキノン、1-クロロアントラキノン、2-クロロアントラキノン、オクタメチルアントラキノン、1,2-ベンズアントラキノン等のキノン類;ベンゾインメチル、ベンゾインエチルエーテル、α-メチルベンゾイン、α-フェニルベンゾイン等のベンゾイン誘導体;2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン、1-ヒドロキシ-シクロヘキシル-フェニル-ケトン、2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン、1-[4-(2-ヒドロキシエトキシ)-フェニル]-2-ヒドロキシ-2-メチル-1-プロパン-1-オン、2-ヒドロキシ-1-[4-{4-(2-ヒドロキシ-2-メチル-プロピオニル)ベンジル}-フェニル]-2-メチル-プロパン-1-オン、フェニルグリオキシリックアシッドメチルエステル、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-ブタノン-1、2-ジメチルアミノ-2-(4-メチル-ベンジル)-1-(4-モリホリン-4-イル-フェニル)-ブタン-1-オン等のアルキルフェノン系化合物;ビス(2,4,6-トリメチルベンゾイル)-フェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイル-ジフェニル-ホスフィンオキサイド等のアシルホスフィンオキサイド系化合物;1,2-オクタンジオン,1-[4-(フェニルチオ)-,2-(O-ベンゾイルオキシム)]、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)等のオキシムエステル系化合物が挙げられる。
シリコーン化合物は、樹脂膜をモールドから剥離した際に計測される離型力を低下させることに寄与する。分子内にシリコーン骨格(シロキサン骨格)を有する化合物を表し、ジメチルシリコーン骨格を有するものが好ましく、前記式(1)又は式(2)で表される化合物が特に好ましい。
本発明の構造体を形成するためのインプリント材料は、界面活性剤が添加されていてもよい。界面活性剤は、得られる塗膜の製膜性を調整する役割を果たす。
上記界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンノニルフェニルエーテル等のポリオキシエチレンアルキルアリールエーテル類、ポリオキシエチレン・ポリオキシプロピレンブロックコポリマー類、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤;商品名エフトップ(登録商標)EF301、同EF303、同EF352(三菱マテリアル電子化成株式会社(旧株式会社ジェムコ製))、商品名メガファック(登録商標)F171、同F553、同F554、同F477、同F173、同R-08、同R-30(DIC株式会社製)、フロラードFC430、同FC431(住友スリーエム株式会社製)、商品名アサヒガード(登録商標)AG710、サーフロン(登録商標)S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(旭硝子株式会社製)等のフッ素系界面活性剤;及びオルガノシロキサンポリマーKP341(信越化学工業株式会社製)を挙げることができる。
本発明の構造体を形成するためのインプリント材料溶剤を含有してもよい。溶剤は、得られる構造体の膜厚を調整する役割を果たす。
本発明の構造体を形成するためのインプリント材料は、本発明の効果を損なわない限りにおいて、必要に応じて、エポキシ化合物、光酸発生剤、光増感剤、紫外線吸収剤、酸化防止剤、密着補助剤又は離型性向上剤を含有することもできる。
本発明の構造体を形成するためのインプリント材料の調製方法は、特に限定されないが、重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤、並びに任意成分であるシリコーン化合物、界面活性剤及び溶剤並びに所望によりその他添加剤を混合し、インプリント材料が均一な状態となっていればよい。
また、重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤、シリコーン化合物、界面活性剤及び溶剤、並びに所望によりその他添加剤を混合する際の順序は、均一なインプリント材料が得られるなら問題なく、特に限定されない。当該インプリント材料の調製方法としては、例えば、重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物に光重合開始剤を所定の割合で混合する方法が挙げられる。また、これに更にシリコーン化合物、界面活性剤及び溶剤を混合し、均一なインプリント材料とする方法も挙げられる。さらに、この調製方法の適当な段階において、必要に応じて、その他の添加剤を更に添加して混合する方法が挙げられる。
攪拌機、温度計及びコンデンサーを備えた500ml容のフラスコにトルエン60.8質量部、ステアリルアルコール(NAA-46;日本油脂株式会社製、水酸基価:207)8.4質量部を仕込み、40℃まで昇温した。その後ステアリルアルコールが完全に溶解したのを確認し、ヘキサメチレンジイソシアネートのイソシアヌレート変性タイプ(タケネート(登録商標)D-170N;三井化学株式会社製、NCO%:20.9)50質量部を仕込み70℃まで昇温させた。同温度で30分反応後、ジブチル錫ラウレートを0.02質量部仕込み、同温度で3時間保持した。その後、ポリカプロラクトン変性ヒドロキシエチルアクリレート(プラクセル(登録商標)FA2D;株式会社ダイセル製、水酸基価:163)83.5質量部、ジブチル錫ラウレート0.02質量部、ハイドロキノンモノメチルエーテル0.02質量部を仕込み、70℃で3時間保持して反応を終了した後、エバポレーターでトルエンを除去し、固形分100質量%のウレタンアクリレート(I)を得た。
合成例1で用いたのと同様のフラスコにトルエン48.2質量部、ステアリルアルコール(NAA-46)4.2質量部を仕込み、40℃まで昇温した。その後ステアリルアルコールが完全に溶解したのを確認し、ヘキサメチレンジイソシアネートのイソシアヌレート変性タイプ(タケネート(登録商標)D-170N)25質量部を仕込み70℃まで昇温させた。同温度で30分反応後、ジブチル錫ラウレートを0.02質量部仕込み、同温度で3時間保持した。その後、ポリカプロラクトン変性ヒドロキシエチルアクリレート(プラクセル(登録商標)FA5;株式会社ダイセル製、水酸基価:81.8)83.3質量部、ジブチル錫ラウレート0.02質量部、ハイドロキノンモノメチルエーテル0.02質量部を仕込み、70℃で3時間保持して反応を終了した後、エバポレーターでトルエンを除去し、固形分100質量%のウレタンアクリレート(II)を得た。
合成例1で用いたのと同様のフラスコにトルエン44.8質量部、ステアリルアルコール(NAA-46)4.6質量部を仕込み、40℃まで昇温した。その後ステアリルアルコールが完全に溶解したのを確認し、キシリレンジイソシアネートのトリメチロールプロパンアダクト変性タイプ(タケネート(登録商標)D-110N;三井化学株式会社製、固形分:75%、NCO%:11.5)50質量部を仕込み70℃まで昇温させた。同温度で30分反応後、ジブチル錫ラウレートを0.02質量部仕込み、同温度で3時間保持した。その後、ポリカプロラクトン変性ヒドロキシエチルアクリレート(プラクセル(登録商標)FA5)91.7質量部、ジブチル錫ラウレート0.02質量部、ハイドロキノンモノメチルエーテル0.02質量部を仕込み、70℃で3時間保持して反応を終了した後、エバポレーターでトルエンを除去し、固形分100質量%のウレタンアクリレート(III)を得た。
合成例1で用いたのと同様のフラスコにトルエン61.3質量部、ベヘニルアルコール(NAA-422;日本油脂株式会社製、水酸基価:180)9.7質量部を仕込み、40℃まで昇温した。その後ベヘニルアルコールが完全に溶解したのを確認し、ヘキサメチレンジイソシアネートのイソシアヌレート変性タイプ(タケネート(登録商標)D-170N)50質量部を仕込み70℃まで昇温させた。同温度で30分反応後、ジブチル錫ラウレートを0.02質量部仕込み、同温度で3時間保持した。その後、ポリカプロラクトン変性ヒドロキシエチルアクリレート(プラクセル(登録商標)FA2D)83.4質量部、ジブチル錫ラウレート0.02質量部、ハイドロキノンモノメチルエーテル0.02質量部を仕込み、70℃で3時間保持して反応を終了した後、エバポレーターでトルエンを除去し、固形分100質量%のウレタンアクリレート(IV)を得た。
<調製例1>
合成例1で作製したウレタンアクリレート(I)5gにLucirin(登録商標)TPO(BASFジャパン株式会社製)(以下、「Lucirin TPO」と略称する。)0.125g(ウレタンアクリレート(I)の質量に対して2.5phr)を加え、インプリント材料PNI-1を調製した。
調整例1のウレタンアクリレート(I)を合成例2で得たウレタンアクリレート(II)へ変更した以外は調製例1と同様にインプリント材料PNI-2を調製した。
調整例1のウレタンアクリレート(I)を合成例3で得たウレタンアクリレート(III)へ変更した以外は調製例1と同様にインプリント材料PNI-3を調製した。
調整例1のウレタンアクリレート(I)を合成例4で得たウレタンアクリレート(IV)へ変更した以外は調製例1と同様にインプリント材料PNI-4を調製した。
調整例1のウレタンアクリレート(I)をUA-7100(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-5を調製した。
調整例1のウレタンアクリレート(I)をNKエコノマー A-1000PER(以下、「A-1000PER」と略称する。)(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-6を調製した。
調整例1のウレタンアクリレート(I)をX-22-1602(信越化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-7を調製した。
調整例1のウレタンアクリレート(I)をファンクリル(登録商標)FA-023M(日立化成工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-8を調製した。
調整例1のウレタンアクリレート(I)をNKエステル APG-700(以下、「APG-700」と略称する。)(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-9を調製した。
調整例1のウレタンアクリレート(I)をNKエステル ATM-35E(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-10を調製した。
調整例1のウレタンアクリレート(I)をNKエステル A-TMPT-9EO(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-11を調製した。
調整例1のウレタンアクリレート(I)をテトラエチレングリコールジアクリレート(東京化成工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-12を調製した。
調整例1のウレタンアクリレート(I)をKAYARAD(登録商標)DPEA-12(以下、本明細書では「DPEA-12」と略称する。)(日本化薬株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-13を調製した。
調整例1のウレタンアクリレート(I)をNKエステル A-TMPT-3EO(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-14を調製した。
調整例1のウレタンアクリレート(I)をNKエステル A-DCP(新中村化学工業株式会社製)へ変更した以外は調製例1と同様にインプリント材料PNI-15を調製した。
NKエステル AM-90G(以下、「AM-90G」と略称する。)(新中村化学工業株式会社製)2.5gとNKエステル A-TMPT(以下、本明細書では「A-TMPT」と略称する。)(新中村化学工業株式会社製)2.5gとを混合し、その混合物にLucirin TPO0.125g(AM-90GとA-TMPTの総質量に対して2.5phr)を加え、インプリント材料PNI-16を調製した。
2.5gのDPEA-12と合成例1で得たウレタンアクリレート(I)2.5gとを混合し、その混合物にLucirin TPO0.125g(DPEA-12とウレタンアクリレート(I)の総質量に対して2.5phr)を加え、インプリント材料PNI-17を調製した。
調製例17のウレタンアクリレート(I)を合成例2で得たウレタンアクリレート(II)へ変更した以外は、調製例17と同様にインプリント材料PNI-18を調製した。
調製例17のウレタンアクリレート(I)を合成例3で得たウレタンアクリレート(III)へ変更した以外は、調製例17と同様にインプリント材料PNI-19を調製した。
調製例17のウレタンアクリレート(I)を合成例4で得たウレタンアクリレート(IV)へ変更した以外は、調製例17と同様にインプリント材料PNI-20を調製した。
KAYARAD(登録商標)DPHA(以下、「DPHA」と略称する。)2.5gとA-1000PER2.5gとを混合し、その混合物にLucirin TPO0.125g(DPHAとA1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-21を調製した。
DPHA2.75gとA-1000PER2.25gとを混合し、その混合物にLucirin TPO0.125g(DPHAとA1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-22を調製した。
DPHA3.0gとA-1000PER2.0gとを混合し、その混合物にLucirin TPO0.125g(DPHAとA1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-23を調製した。
DPHA0.25g、UA-306H(共栄社化学株式会社製)1.75g、A-1000PER3.0gを混合し、その混合物にLucirin TPO0.125g(DPHA、UA-306H、A1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-24を調製した。
0.5gのDPEA-12、A-TMPT2.0g、A-1000PER2.5gを混合し、その混合物にLucirin TPO0.125g(DPEA-12、A-TMPT、A1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-25を調製した。
0.5gのDPEA-12、UA-306H2.0g、A-1000PER2.5g、BYK-333(ビックケミー・ジャパン株式会社製)0.05g(DPEA-12、UA-306H、A1000PERの総質量に対して1phr)を混合し、その混合物にLucirin TPO0.125g(DPEA-12、UA-306H、A1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-26を調製した。
0.5gのDPEA-12、UA-306H2.0g、2.5gのAPG-700を混合し、その混合物にLucirin TPO0.125g(DPEA-12、UA-306H、APG-700の総質量に対して2.5phr)を加え、インプリント材料PNI-27を調製した。
0.5gのDPEA-12、DPHA2.0g、A-1000PER2.5gを混合し、その混合物にLucirin TPO0.125g(DPEA-12、DPHA、A-1000PERの総質量に対して2.5phr)を加え、インプリント材料PNI-28を調製した。
NKエステル A1000(以下、「A1000」と略称する。)(新中村化学工業株式会社製)5g、Lucirin TPO0.125g(A1000の質量に対して2.5phr)、メチルエチルケトン(以下、「MEK」と)略称する。)5.125gを混合し、インプリント材料PNI-29を調製した。
UA-306H1.75g、3.25gのX-22-1602、Lucirin TPO0.125g(UA-306H、X-22-1602の総質量に対して2.5phr)、MEK5.125gを混合し、インプリント材料PNI-30を調製した。
UA-306H2.0g、3.0gのX-22-1602、Lucirin TPO0.125g(UA-306H、X-22-1602の総質量に対して2.5phr)、MEK5.125gを混合し、インプリント材料PNI-31を調製した。
UA-306H2.25g、2.75gのX-22-1602、メガファック(登録商標)F477(DIC株式会社製)0.0025g(UA-306H、X-22-1602の総質量に対して0.05phr)、Lucirin TPO0.125g(UA-306H、X-22-1602の総質量に対して2.5phr)、MEK5.125gを混合し、インプリント材料PNI-32を調製した。
A-TMPT5g、Lucirin TPO0.125g(A-TMPTの質量に対して2.5phr)を混合し、インプリント材料PNI-33を調製した。
KAYARAD PET30(以下、「PET30」と略称する。)(日本化薬株式会社製)を5g、Lucirin TPO0.125g(PET30の質量に対して2.5phr)を混合し、インプリント材料PNI-34を調製した。
UA-510(共栄社化学株式会社製)5g、Lucirin TPO0.125g(UA-510の質量に対して2.5phr)を混合し、インプリント材料PNI-35を調製した。
DPHA3.25g、A-1000PER1.75g、Lucirin TPO0.125g(DPHA、A-1000PERの総質量に対して2.5phr)を混合し、インプリント材料PNI-36を調製した。
DPHA3.5g、A-1000PER1.5g、Lucirin TPO0.125g(DPHA、A-1000PERの総質量に対して2.5phr)を混合し、インプリント材料PNI-37を調製した。
ニッケル製の、周期250nm、高さ250nmのモスアイパターンモールド(株式会社イノックス製)及びシリコンウエハを、オプツール(登録商標)DSX(ダイキン工業株式会社製)をノベック(登録商標)HFE-7100(ハイドロフルオロエーテル、住友スリーエム株式会社)(以下、本明細書では「ノベックHFE-7100」と略称する。)で0.1質量%に希釈した溶液へ浸漬し、温度が90℃、湿度が90RH%の高温高湿装置を用いて1時間処理し、ノベックHFE-7100でリンス後、エアーで乾燥させた。
調製例1乃至調製例37で得られた各インプリント材料を、厚さ80μmのトリアセチルセルロースフィルム(富士フイルム株式会社製 フジタック(登録商標)を使用)(以下、「TACフィルム」と略称する。)上にバーコーター(全自動フィルムアプリケーター KT-AB3120 コーテック株式会社製)を用いて塗布し、そのTACフィルム上の塗膜を前述の離型処理を施したモスアイパターンモールドへローラー圧着させた。続いて、前記塗膜に対し、TACフィルム側から無電極均一照射装置(QRE-4016A、株式会社オーク製作所製)にて、350mJ/cm2の露光を施し、光硬化を行った。そしてJIS Z0237を参考にして90°剥離試験を行い、モールドの凹凸形状を有する面と接着しているTACフィルム上に形成された硬化膜がモールドの凹凸形状を有する面から完全に剥がれたときの荷重を測定した。そしてフィルムの幅1cm当たりの荷重を算出し、離型力(g/cm)とした。結果を表1及び表2に示す。
上記離型力試験後に、凹凸形状としてモスアイパターンが転写された構造体がTACフィルム上に得られた。そのTACフィルムにおいて、モスアイパターンが転写された構造体が得られた面とは反対の面をスーパーラッカースプレー(アサヒペン株式会社製)にて黒色に塗装した。そして、TACフィルム上に得られた構造体のモスアイパターン上に人工指紋液(TDK株式会社製)を付着させ、大栄精機(有)製試験機にベンコット(登録商標)M-1(旭化成せんい株式会社製)を取り付け、570g/cm2の荷重にて50往復させる指紋の拭き取り試験を行い、目視にて指紋の拭き取り性を確認した。当該試験で行われる拭き取りは乾拭きである。拭き取り試験後、指紋の拭き取りができた場合を○、指紋の拭き取りができなかった即ち指紋が残存していた場合を×と評価した結果を、表1及び表2に示す。
調製例1乃至調製例37で得られた各インプリント材料を、石英基板上にバーコーター(全自動フィルムアプリケーター KT-AB3120 コーテック株式会社製)を用いて塗布し、その石英基板上の塗膜を前述の離型処理を施したシリコンウエハへローラー圧着させた。続いて、前記塗膜に対し、石英基板側から無電極均一照射装置(QRE-4016A、株式会社オーク製作所製)にて、350mJ/cm2の露光を施して光硬化を行った。そして前記石英基板からシリコンウエハを剥がし、得られた硬化膜に対してマルテンス硬さ測定を行った。測定装置は超微小押し込み硬さ試験機 ENT-2100(株式会社エリオニクス製)を使用し、圧子は稜間角115°のチタン製三角圧子(株式会社東京ダイヤモンド工具製作所製)を用いて、溶融石英のマルテンス硬さが4100N/mm2となる条件で測定した。得られた結果を表1及び表2に示す。
Claims (16)
- 重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤を含有する組成物から作製され、溶融石英のマルテンス硬さが4100N/mm2である条件で測定したときのマルテンス硬さが3N/mm2以上130N/mm2以下である、凹凸形状の表面を有する構造体。
- 前記重合性基がアクリロイルオキシ基、メタアクリロイルオキシ基、ビニル基及びアリル基からなる群から選ばれる少なくとも1種の基である、請求項1に記載の構造体。
- 前記組成物はシリコーン化合物をさらに含み、該組成物をインプリントすることによって作製される、請求項1又は請求項2に記載の構造体。
- 前記凹凸形状はモスアイ構造である請求項1乃至請求項4のいずれか一項に記載の構造体。
- 重合性基を1分子中に1個乃至10個有する少なくとも1種の化合物及び光重合開始剤を含有する前記組成物を基材上に塗布した後、モールドの凹凸形状を有する面に前記基材上の塗膜を圧着し、その状態で前記塗膜を光硬化させて硬化膜とし、前記基材上の硬化膜を前記モールドから剥離する、請求項1乃至請求項5のいずれか一項に記載の構造体の製造方法。
- 前記組成物は界面活性剤をさらに含む請求項6に記載の構造体の製造方法。
- 溶剤をさらに含む前記組成物を前記基材上に塗布した後、ベークをすることにより前記溶剤を揮発させる工程を含む、請求項6又は請求項7に記載の構造体の製造方法。
- 前記基材としてフィルムを用い、前記フィルム上の硬化膜を前記モールドから90°剥離する試験において、前記フィルム上の硬化膜を前記モールドから剥離したときの荷重を前記フィルムの幅1cmあたりに換算した値である離型力が0g/cmより大きく0.7g/cm以下である、請求項6乃至請求項8のいずれか一項に記載の構造体の製造方法。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えた光学部材。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えた固体撮像装置。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えたLEDデバイス。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を備えた半導体素子。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えた太陽電池。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えたディスプレイ。
- 請求項1乃至請求項5のいずれか一項に記載の構造体を基材上に備えた電子デバイス。
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TW201420318A (zh) | 2014-06-01 |
US20170107343A1 (en) | 2017-04-20 |
KR20150038094A (ko) | 2015-04-08 |
TWI648147B (zh) | 2019-01-21 |
US20150239022A1 (en) | 2015-08-27 |
CN104487179A (zh) | 2015-04-01 |
JPWO2014013922A1 (ja) | 2016-06-30 |
KR102121762B1 (ko) | 2020-06-11 |
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