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US20180231887A1 - Method for manufacturing device, and composition - Google Patents

Method for manufacturing device, and composition Download PDF

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Publication number
US20180231887A1
US20180231887A1 US15/754,857 US201615754857A US2018231887A1 US 20180231887 A1 US20180231887 A1 US 20180231887A1 US 201615754857 A US201615754857 A US 201615754857A US 2018231887 A1 US2018231887 A1 US 2018231887A1
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film
group
composition
oxidation inhibitor
amine compound
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Inventor
Takeshi Osaki
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Toyo Gosei Co Ltd
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Toyo Gosei Co Ltd
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Assigned to TOYO GOSEI CO., LTD. reassignment TOYO GOSEI CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OSAKI, TAKESHI
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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
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/156—Heterocyclic compounds having oxygen in the ring having two oxygen atoms in the ring
    • C08K5/1575—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(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
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • 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
    • C08F2220/185—
    • C08F2220/281—

Definitions

  • One aspect of the present invention relates to a method for manufacturing a device such as an optical or electronic component, and a composition preferably used for the manufacturing method.
  • a method for manufacturing a device such as an optical or electronic component uses a nanoimprint technique for pressing a mold having a convexo-concave pattern formed thereon into a composition, performing a mechanical change, and transferring a fine pattern precisely.
  • a nanoimprint process generally includes four elements of (1) application, (2) press, (3) transfer (light or heat), and (4) release, and nano-sized processing is possible in a simple process.
  • an apparatus of the nanoimprint process is simple, and a high throughput is expected. Therefore, the nanoimprint technique is expected as a microfabrication technique capable of mass production at low cost. For these reasons, efforts to practical use in various fields such as a semiconductor device, a storage medium, biotechnology, and an optical member are progressing (see Patent Literature 1).
  • Deformation or a change in size of a cured product obtained by a nanoimprint method occurs disadvantageously due to heat and light generated in a process of manufacturing a device or heat and light generated in an operation of the device. Therefore, a composition having excellent heat resistance and/or light resistance, capable of reducing the deformation and the change in size is desired.
  • a conventional composition has problems in terms of heat resistance and light resistance.
  • One object of some aspects of the present invention is to provide a method for manufacturing a device having excellent heat resistance and/or light resistance.
  • a device manufactured using a composition containing a specific component has excellent heat resistance and/or light resistance, and has completed some aspects of the present invention.
  • One aspect of the present invention provides a method for manufacturing a device including a substrate and a second film disposed above the substrate, including:
  • first film above the substrate using a composition containing a polymerizable monomer and an oxidation inhibitor; and forming the second film by curing the first film in a state where at least one part of a mold having a convexo-concave pattern is in contact with the first film, or after at least one part of the mold is brought into contact with the first film,
  • the oxidation inhibitor is at least one of a hindered amine compound and a hindered phenol compound having a molecular weight of 700 or more, and
  • composition satisfies a relationship of (t 0(T) -t x(T) )/t 0(T) ⁇ 100 ⁇ 13.0,
  • t 0(T) is a height of a convex part of a convexo-concave part of a cured film having the convexo-concave part obtained by forming a coating film using the composition and then by curing the coating film in a state where the coating film is in contact with a convexo-concave part in which a depth of a concave part is 3 ⁇ m and a line width thereof is 5 ⁇ m, included in the mold, and
  • t x(T) is a height of the convex part after the cured film is heated from 25° C. to 260° C. over five minutes, then the temperature of the cured film is held at 260° C. for five minutes, and then the cured film is cooled to 25° C. over 30 minutes.
  • One aspect of the present invention provides a method for manufacturing a device including a substrate and a second film disposed above the substrate, including:
  • the oxidation inhibitor is a hindered amine compound and the blending amount of the hindered amine compound is 0.5% by mass or more in the composition
  • composition satisfies a relationship of (t 0(L) -t x(L) )/t 0(L) ⁇ 100 ⁇ 10.0,
  • t 0(L) is a height of a convex part of a convexo-concave part of a cured film having the convexo-concave part obtained by forming a coating film using the composition and then by curing the coating film in a state where the coating film is in contact with a convexo-concave part in which a depth of a concave part is 3 ⁇ m and a line width thereof is 5 ⁇ m, included in the mold, and
  • t x(L) is a height of the convex part after the cured film is irradiated with light at 60° C. for 60 days under a condition of 765 W/cm 2 with a xenon lamp.
  • One aspect of the present invention can provide a method for manufacturing a device having excellent heat resistance and/or light resistance.
  • FIG. 1 is a view for describing a reduction ratio of change in height of a convex part of a cured film having a pattern.
  • a method for manufacturing a device is a method for manufacturing a device including a substrate and a second film disposed above the substrate, including:
  • the second film by curing the first film in a state where at least one part of a mold having a convexo-concave pattern is in contact with the first film, or after at least one part of the mold is brought into contact with the first film.
  • composition 1 A composition (hereinafter, also referred to as “composition 1”) used in a method for manufacturing a device according to one aspect of the present invention will be described below.
  • the composition 1 is characterized in that the composition 1 contains a polymerizable monomer and an oxidation inhibitor, the oxidation inhibitor is at least one of a hindered amine compound and a hindered phenol compound having a molecular weight of 700 or more, and the composition 1 satisfies the relationship of the above formula (t 0(T) -t x(T) )/t 0(T) ⁇ 100 ⁇ 13.0.
  • Satisfaction of the relationship of (t 0(T) -t x(T) )/t 0(T) ⁇ 100 ⁇ 13.0 means that a cured film sample having a convexo-concave part obtained under the following condition using the composition 1 has a reduction ratio of 13.0% or less in a height of the convex part before and after heating.
  • a coating film is formed using the composition 1. Thereafter, the coating film of the composition 1 is cured in a state where the coating film is in contact with a convexo-concave part in which the depth of a concave part is 3 ⁇ m and a line width thereof is 5 ⁇ m, included in a mold, to manufacture a cured film sample having a convexo-concave part.
  • the cured film sample is heated from 25° C. to 260° C. over five minutes, the temperature of the cured film sample is further held at 260° C. for five minutes, and then the cured film sample is cooled to 25° C. over 30 minutes to obtain a cured film sample after heating.
  • a hindered amine compound as the oxidation inhibitor preferably has a polymerizable group in a molecule thereof. This makes the hindered amine compound incorporated into a resin component when the composition is cured. Therefore, heat resistance and/or light resistance of the cured product of the composition are improved.
  • the polymerizable group is not particularly limited as long as being polymerizable with the polymerizable monomer, but preferable examples thereof include a radically polymerizable group such as a (meth)acryloyloxy group, a vinyl group, an allyl group, or a styryl group.
  • (meth)acryloyl means inclusion of both acryloyl and methacryloyl.
  • the hindered amine compound preferably has at least one structure represented by the following formula (1) in the molecule thereof.
  • hindered amine compound has one structure represented by the above formula (1) in the molecule thereof, examples thereof include a compound having a structure represented by the following formula (2).
  • R 1 is preferably any one selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, and an alkoxy group which may have a substituent.
  • alkyl group of R 1 examples include a linear or branched alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, an n-isopropyl group, a sec-butyl group, a tert-butyl group, an n-butyl group, or a pentyl group.
  • Examples of the alkoxy group of R 1 include an alkoxy group having 1 to 15 carbon atoms, such as a methoxy group, an ethoxy group, or a propoxy group.
  • Examples of the substituent which R 1 may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, a cyano group, and an alkoxy group.
  • a total number of carbon atoms in R 1 is preferably 1 to 20, and more preferably 1 to 11 including carbon atoms of a substituent from a viewpoint of solubility with another component.
  • R 2 is a monovalent organic group
  • examples of the monovalent organic group of R 2 include an alkyl group, a hydroxy group, a carboxy group, an alkylcarbonyloxy group, an amino group, and a group containing the above polymerizable group, but are not limited thereto.
  • the alkyl group, the alkylcarbonyloxy group, the amino group, and the group containing the above polymerizable group as R 2 may have a substituent.
  • Examples of the alkyl group of R 2 include a linear or branched alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, an n-isopropyl group, a sec-butyl group, a tert-butyl group, an n-butyl group, or a pentyl group.
  • Examples of the substituent which the alkyl group may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, and an alkoxy group.
  • the group containing the above polymerizable group is not particularly limited as long as containing the above polymerizable group, and may be, for example, the polymerizable group itself or a group in which the above polymerizable group is bonded to the alkyl group, the amino group, or the like.
  • Examples of the substituent which the alkylcarbonyloxy group may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, and an alkoxy group.
  • Examples of the substituent which the amino group may have include the alkyl group having 1 to 5 carbon atoms.
  • Examples of the substituent which the group containing the polymerizable group may have include a halogen atom, an alkyl group, a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, and an alkoxy group.
  • the hindered amine compound When the hindered amine compound has two structures represented by the above formula (1), the hindered amine compound preferably has a structure represented by the following formula (3).
  • the hindered amine compound may be a high molecular weight type compound containing a unit represented by the following formula (4) or (5).
  • the hindered amine compound preferably has a weight-average molecular weight of 5000 or less in terms of polystyrene from a viewpoint of solubility.
  • Examples of X include an alkylene group, an alkylene group bonded to a structure represented by the above formula (1) through an ester bond, an alkylene group containing an aromatic hydrocarbon group or a heteroaromatic group, an alkylene group having an ether bond, an alkylene group having an acetal bond, and —O—C( ⁇ O)—O—.
  • Examples of Y include a nitrogen atom having a substituent, a pyrrolidione structure bonded to an alkylene group, and a trivalent group bonded to a structure represented by the above formula (1) through an ester bond.
  • Examples of the substituent of the nitrogen atom include an alkylene group and a divalent group containing an aromatic hydrocarbon group or a heteroaromatic group.
  • Z examples include an alkylene group, an alkylene group having an ester bond, an alkylene group containing an aromatic hydrocarbon group or a heteroaromatic group, an alkylene group having an ether bond, and an alkylene group having an acetal bond.
  • R 1 in the above formulas (3) to (5) include those similar to R 1 in the above formula (2).
  • TINUVIN 292 As the hindered amine compound, TINUVIN 292, TINUVIN PA144, TINUVIN 765, TINUVIN 770DF, TINUVIN 622SF, Uninul 4050FF, Uninul 5050H, CHIMASORB 2020FDL, CHIMASORB 944 FDL, and the like manufactured by BASF SE; LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, G, LA-81, LA-82, and LA-87 manufactured by ADEKA CORPORATION; and the like are easily available and can be preferably used. These compounds can be used singly or in combination thereof. Preferable examples thereof include those illustrated below, but are not limited thereto.
  • the hindered phenol compound preferably has at least one structure represented by the following formula (6) in the molecule thereof.
  • R 3 and R 4 are each independently any one selected from the group consisting of a hydrogen atom and an alkyl group
  • R 5 is any one selected from the group consisting of a hydrogen atom and an alkyl group.
  • the alkyl group serving as each of R 3 to R 5 may have a substituent.
  • alkyl group examples include a linear or branched alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, an n-isopropyl group, sec-butyl group, a tent-butyl group, an n-butyl group, or a pentyl group.
  • Examples of the substituent which the alkyl group may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, a methoxy group, and an ethoxy group.
  • R 3 to R 5 are each independently a hydrogen atom, a methyl group, or a tert-butyl group. At least one of ortho positions of a phenolic hydroxy group, that is, at least one of R 3 and R 4 is preferably a methyl group or a tert-butyl group, at least one of R 3 and R 4 is more preferably a tert-butyl group, and both of R 3 and R 4 are still more preferably tert-butyl groups.
  • hindered phenol compound has one structure represented by the above formula (6) in the molecule thereof, examples thereof include a compound having a structure represented by the following formula (7).
  • R 6 is a monovalent organic group, and examples of the monovalent organic group of R 6 include an alkyl group, a hydroxy group, a carboxy group, an alkylcarbonyloxy group, and an amino group, but are not limited thereto. Furthermore, each of the alkyl group, the alkylcarbonyloxy group, the amino group, and the like as R 6 may have a substituent.
  • R 3 to R 5 in the above formula (7) are the same as those in the above formula (6).
  • Examples of the alkyl group as R 6 in the above formula (7) include a linear or branched alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, an n-isopropyl group, a sec-butyl group, a tert-butyl group, an n-butyl group, or a pentyl group.
  • Examples of the substituent which the alkyl group may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, a methoxy group, and an ethoxy group.
  • Examples of the substituent which the alkylcarbonyloxy group may have include a hydroxy group, a sulfonyloxy group, an alkylcarbonyloxy group, an alkyloxycarbonyl group, a cyano group, a methoxy group, and an ethoxy group.
  • Examples of the substituent which the amino group may have include the alkyl group having 1 to 5 carbon atoms.
  • the hindered phenol compound When the hindered phenol compound has two or more structures represented by the above formula (6), the hindered phenol compound preferably has a structure represented by the following formula (8).
  • R 3 to R 5 in the above formula (8) are the same as those in the above formula (6).
  • R 7 is not particularly limited as long as being a divalent organic group, but examples thereof include an alkylene group and an alkylene carbonyloxyalkylene group.
  • n is 4 when W is a carbon atom.
  • n is 3 when W is a trivalent organic group.
  • n is 2 when W is any one selected from a divalent organic group, a sulfur atom, and an oxygen atom.
  • Examples of the divalent organic group for W include groups similar to those of X in the above formula (3).
  • Examples of the trivalent organic group include a benzene ring and triazinetrione.
  • the hindered phenol compound has a molecular weight of 700 or more, preferably 1000 or more. Furthermore, the molecular weight is more preferably 10000 or less. A molecular weight within the above range makes compatibility in the composition good, and improves heat resistance and/or light resistance of a cured product of the composition.
  • Irganox 1010 molecular weight 1178
  • Irganox 1330 molecular weight 775
  • Irganox 3114 molecular weight 784
  • the content of the oxidation inhibitor is preferably 0.05 to 10% by mass in the composition excluding a solvent.
  • the content is more preferably 0.1% by mass or more, still more preferably 0.2% by mass or more, particularly preferably 0.5% by mass or more, and more particularly preferably 1% by mass or more.
  • the content of the oxidation inhibitor is more preferably 9% by mass or less, and still more preferably 5% by mass or less.
  • the content of the oxidation inhibitor of 10% by mass or less is preferable because a possibility of a decrease in curability of the composition lowered or a disadvantage such as bleed-out from the cured product hardly occurs.
  • oxidation inhibitor within the above range can suppress film thickness shrinkage and a convexo-concave pattern size also due to heat generated in a process for manufacturing a device, and can suppress a decrease in transmittance. Furthermore, photopolymerization or thermal polymerization progresses efficiently, and curability can be sufficiently obtained.
  • More preferable contents are as follows depending on whether the hindered amine compound or the hindered phenol compound is used.
  • the oxidation inhibitor is a hindered amine compound having no polymerizable group
  • the content thereof is more preferably 1 to 9% by mass in the composition excluding a solvent.
  • the oxidation inhibitor is a hindered amine compound having a polymerizable group
  • the content thereof is preferably 0.2 to 9% by mass in the composition excluding a solvent.
  • the oxidation inhibitor is a hindered phenol compound
  • the content thereof is more preferably 0.1 to 10% by mass, and still more preferably 0.5 to 9% by mass in the composition excluding a solvent.
  • the oxidation inhibitor is preferably a combination of the hindered amine compound and the hindered phenol compound.
  • the content of the hindered phenol compound is preferably 1 to 100 parts by mass, and more preferably 1 to 30 parts by mass relative to 10 parts by mass of the hindered amine compound.
  • the hindered amine compound more preferably has a polymerizable group in the molecule thereof.
  • a combination of the hindered amine compound with the hindered phenol compound having a molecular weight of 1000 or more is preferable because of suppressing volatility during polymerization.
  • Examples of the polymerizable monomer according to one aspect of the present invention include a usual polymerizable monomer used for nanoimprint, microsize imprint, and millisize imprint without any particular limitation.
  • Examples thereof include a compound having at least one radically polymerizable group in one molecule thereof, a compound having an oxirane ring, a vinyl ether compound, and a fluorine atom-containing polymerizable compound.
  • Preferable examples of the radically polymerizable group include a (meth)acryloyloxy group, a vinyl group, an allyl group, and a styryl group.
  • a polymerizable monomer hardly decomposed by heat, for example, a polymerizable monomer having no heterocyclic structure is preferable from a viewpoint of heat resistance.
  • a radically polymerizable group an acryloyloxy group, a vinyl group, and the like are more preferable.
  • polymerizable monomer an appropriate combination of a polymerizable monomer having one polymerizable group in one molecule thereof, a polymerizable monomer having two polymerizable groups in one molecule thereof, a polymerizable monomer having three or more polymerizable groups in one molecule thereof, and the like is preferably used.
  • the polymerizable monomer preferably has a cyclic moiety such as an alicyclic group.
  • Content of the monofunctional monomer having one polymerizable group in one molecule thereof among the above polymerizable monomers is preferably 0.05 to 80% by mass, and more preferably 1 to 90% by mass in the composition excluding a solvent.
  • Content of the bifunctional monomer having two polymerizable groups in one molecule thereof among the above polymerizable monomers is preferably 0 to 99.5% by mass, more preferably 1 to 90% by mass, and still more preferably 10 to 80% by mass in the composition excluding a solvent.
  • Content of the polyfunctional monomer having three or more polymerizable groups in one molecule thereof among the above polymerizable monomers is preferably 0 to 99.5% by mass, more preferably 1 to 90% by mass, and still more preferably 10 to 80% by mass in the composition excluding a solvent.
  • polymerizable monomer a compound having a (meth)acryloyloxy group, an N-vinyl compound, an acrylamide compound, and the like are preferable. These monofunctional and polyfunctional compounds can be used singly or in appropriate combination thereof.
  • composition according to one aspect of the present invention preferably further contains a polymerization initiator.
  • the polymerization initiator examples include a photopolymerization initiator.
  • the photopolymerization initiator include a radical polymerization initiator which generates radicals by irradiation with light and a cationic polymerization initiator which generates an acid by irradiation with light, and the radical polymerizable initiator is preferable.
  • a usual photopolymerization initiator used in a composition for nanoimprint, microsize imprint, millisize imprint, or the like can be used.
  • Content of the photopolymerization initiator is preferably 0.01 to 20% by mass, and more preferably 0.5 to 15% by mass in the composition excluding a solvent.
  • light includes not only light having a wavelength in an ultraviolet region, a near ultraviolet region, a far ultraviolet region, a visible region, an infrared region, or the like, and an electromagnetic wave, but also a radiation.
  • thermal polymerization initiator can be also used in place of or in combination with the photopolymerization initiator.
  • the thermal polymerization initiator is only required to be an initiator usually used as a thermal polymerization initiator, and examples thereof include an azo compound and a peroxide.
  • composition according to one aspect of the present invention may contain another additive such as a silane coupling agent, a surfactant, a release agent, an adhesion promoter, a solvent, a polymer component, a filler, a polymerization inhibitor, a colorant, a plasticizer, a photo acid generator, a photobase generator, and the like within a range not impairing an effect of the present invention.
  • a silane coupling agent such as a silane coupling agent, a surfactant, a release agent, an adhesion promoter, a solvent, a polymer component, a filler, a polymerization inhibitor, a colorant, a plasticizer, a photo acid generator, a photobase generator, and the like.
  • composition 1 according to one aspect of the present invention is characterized in that a reduction ratio in height of the convex part of a cured film sample having the convexo-concave part obtained under the above condition before and after heating is 13.0% or less.
  • a mold used for obtaining the cured film sample is a quartz mold (product name: NIM-PH3000, manufactured by NTT Advanced Technology Co., Ltd.). Curing is performed in a nitrogen atmosphere by exposure with a Hg—Xe lamp at 20 mW/cm 2 (wavelength 365 nm) for 50 seconds.
  • the obtained cured film sample is released from the quartz mold, and the pattern height of the cured film sample is measured with a confocal laser microscope (OLS 3100, manufactured by Olympus Corporation).
  • OLS 3100 confocal laser microscope
  • the pattern height measurement is performed at a position of a line and a space where the height of a convex part is 3 ⁇ m and the line width thereof is 5 ⁇ m.
  • t 0(T) and t x(T) are used as the height before heating and the height after heating, respectively, as illustrated in FIG. 1 .
  • the composition 1 satisfies the relationship of the following formula (t 0(T) -t x(T) )/t 0(T) ⁇ 100 ⁇ 13.0.
  • the composition 1 In order for the composition 1 to satisfy the above physical property, the composition 1 only needs to contain the above components appropriately. Possession of the above physical property by the composition 1 makes it possible to obtain a cured film having a small change in shape of a convexo-concave pattern due to excellent heat resistance and having excellent transmittance.
  • composition 2 A composition (hereinafter, also referred to as “composition 2”) used in a method for manufacturing a device according to one aspect of the present invention will be described below.
  • the composition 2 is characterized in that the composition 2 contains a polymerizable monomer and an oxidation inhibitor, the oxidation inhibitor is the hindered amine compound, the blending amount of the hindered amine compound is 0.5% by mass or more in the composition, and the composition 2 satisfies a relationship of (t 0(L) -t x(L) )/t 0(L) ⁇ 100 ⁇ 10.0.
  • Satisfaction of the relationship of (t 0(L) -t x(L) )/t 0(L) ⁇ 100 ⁇ 10.0 means that a cured film sample having a convexo-concave part obtained under the following condition using the above composition 2 has a reduction ratio of 10% or less in height of the convex part before and after irradiation with light.
  • the above hindered phenol compound may be also used as the oxidation inhibitor in a similar manner to the above composition 1.
  • the other components are similar to those of the composition 1.
  • a coating film is formed using the composition. Thereafter, the composition is cured in a state where the coating film is in contact with a convexo-concave part in which a depth of a concave part is 3 ⁇ m and a line width thereof is 5 ⁇ m, included in a mold, to manufacture a cured film sample having a convexo-concave part.
  • the cured film sample is irradiated with light at 60° C. for 60 days under a condition of 765 W/cm 2 with a xenon lamp to obtain a cured film sample after irradiation with light.
  • the mold used for obtaining the sample, the curing condition, and the method for measuring a reduction ratio in height of the convex part are similar to those of the composition 1.
  • composition 2 In order for the composition 2 to satisfy the above physical property, the composition 2 only needs to contain the above components appropriately.
  • a method for manufacturing a device according to one aspect of the present invention includes:
  • a second film by curing the first film in a state where at least one part of a mold having a convexo-concave pattern is in contact with the first film, or after at least one part of the mold is brought into contact with the first film, and a device including the substrate and the second film as a cured layer disposed above the substrate is thereby obtained.
  • the process used for the method for manufacturing a device can be a similar process to a usual process.
  • a device pattern refers to pattern transfer of several nm to several mm size, and can be applied to pattern transfer of nano order, micro order, milli order, or the like.
  • the methods for manufacturing a device according to some aspects of the present invention are particularly effective for fine pattern transfer of nano order and micro order.
  • a preferable size of a pattern which exhibits an optical function on an optical device has a relationship to a wavelength (( ⁇ )nm) of light which passes through the optical device or reflects on the optical device.
  • a repetition period of the pattern is preferably 0.1 ⁇ nm to 100 ⁇ nm
  • the line width is preferably 0.05 ⁇ nm to 100 ⁇ nm
  • the height is preferably 0.01 ⁇ nm to 200 ⁇ nm.
  • a range of A is preferably a range of ultraviolet light to infrared light, and is preferably 100 nm to 10000 nm.
  • the above composition is preferably used in a method for manufacturing a device having a pattern size within the above range. This makes it possible to obtain a cured film having excellent heat resistance and light resistance, and to manufacture a device having a cured film with a small change in pattern shape and excellent transmittance.
  • Composition samples 1 to 37 are prepared by blending components as indicated in Tables 1 and 2. Components A to N described in Tables 1 to 4 are specifically indicated below. In Tables, the blending ratio is based on mass.
  • composition samples are subjected to a heat resistance test and a light resistance test as follows.
  • a heat resistance test is performed by placing an appropriate amount of a composition on a 2 cm 2 alkali-free glass (thickness 360 ⁇ m), placing a quartz mold (product name: NIM-PH3000, manufactured by NTT Advanced Technology Co., Ltd.) thereon, filling the composition into a pattern of the quartz mold, and exposing the composition to light in a nitrogen atmosphere with a Hg—Xe lamp at 20 mW/cm 2 (wavelength 365 nm) for 50 seconds.
  • a quartz mold product name: NIM-PH3000, manufactured by NTT Advanced Technology Co., Ltd.
  • the obtained cured product is released from the quartz mold, and a pattern height of the cured product is measured with a confocal laser microscope (product name: OLS 3100, manufactured by Olympus Corporation).
  • the pattern height measurement is performed at a position of a line and a space where a height of a convex part is 3 ⁇ m and a line width is 5 ⁇ m.
  • the obtained cured product is put in a desktop reflow oven (product name: STR-3000RC, manufactured by Shin Apex Co., Ltd.), the cured product is heated from room temperature to 260° C. over five minutes in an air atmosphere, the temperature of the cured product is held at 260° C. for five minutes, and then the cured product is cooled to room temperature over 30 minutes.
  • a pattern height of the resin molded product after heating is measured in a similar manner to that before heating, and the reduction ratio is determined from the pattern heights of the resin molded product before and after heating. Tables 1 to 3 indicate results thereof.
  • a heat resistance test is performed by placing an appropriate amount of a composition on a 3 cm 2 alkali-free glass (thickness 700 ⁇ m), placing a quartz mold (mold having a thickness of 6.35 mm, an area of 25 mm ⁇ , and a pattern of a line and a space where a depth of a concave part is 200 nm and a line width of the concave part is 500 nm, manufactured by Toppan Printing Co., Ltd.) thereon, filling the composition into a pattern of the quartz mold, and exposing the composition to light in a nitrogen atmosphere with a Hg—Xe lamp at 20 mW/cm 2 (wavelength 365 nm) for 50 seconds.
  • the obtained cured product is released from the quartz mold, and a pattern height of the cured product is measured with an atomic force microscope (product name: NANOPICS 1000, manufactured by Seiko Instruments Inc.).
  • the pattern height measurement is performed at a position of a line and a space where the height of a convex part is 200 nm and a line width is 500 nm.
  • the obtained cured product is put in the desktop reflow oven used in the above (heat resistance test: pattern with a height of 3 ⁇ m), the cured product is heated from room temperature to 260° C. over five minutes in an air atmosphere, the temperature of the cured product is held at 260° C. for five minutes, and then the cured product is cooled to room temperature over 30 minutes.
  • a pattern height of the resin molded product after heating is measured in a similar manner to that before heating, and the reduction ratio is determined from the pattern heights of the resin molded product before and after heating. Tables 1 to 3 indicate results thereof.
  • the cured product manufactured in the above (heat resistance test: pattern with a height of 3 ⁇ m) is put in a light resistance tester (product name: SUSTEST CPS+, manufactured by ATLAS), and is irradiated with light for 60 days under the following condition.
  • the light resistance tester is set such that an optical filter is special window glass, black standard temperature is 60° C., and illuminance is 765 W/m 2 (300 to 800 nm) with a xenon lamp.
  • Pattern heights of the cured product before and after irradiation with light are measured with a confocal laser microscope (product name: OLS 3100, manufactured by Olympus Corporation). Table 4 indicates results thereof.
  • the cured product manufactured in the above (heat resistance test: pattern with a height of 200 nm) is put in a light resistance tester (product name: SUSTEST CPS+, manufactured by ATLAS), and is irradiated with light for 60 days under the following condition.
  • the light resistance tester is set such that an optical filter is special window glass, black standard temperature is 60° C., and illuminance is 765 W/m 2 (300 to 800 nm) with a xenon lamp.
  • Pattern heights of the cured product before and after irradiation with light are measured with an atomic force microscope (product name: NANOPICS 1000, manufactured by Seiko Instruments Inc.). Table 4 indicates results thereof.
  • Transmittances before and after heating are determined by measuring transmittances at a wavelength of 450 nm of the cured product with a convexo-concave pattern before and after heated at 260° C. for five minutes.
  • a heat resistance test is performed by placing about 0.05 g of a composition on a Ni mold (product name: AR mold 2 (special product) 2200055088 made of Ni, manufactured by Kyodo International, Inc., having a thickness of 0.3 mm, an area of 3 cm ⁇ 3 cm, a conical shaped concave part, and a pattern having a pattern pitch of 250 nm and a depth of 250 nm), placing 5 cm ⁇ 5 cm alkali-free glass (thickness 700 ⁇ m) thereon, filling the composition into the pattern of the Ni mold, and exposing the composition to light in a nitrogen atmosphere with a Hg—Xe lamp at 10 mW/cm 2 (wavelength 365 nm) for 100 seconds.
  • a Ni mold product name: AR mold 2 (special product) 2200055088 made of Ni, manufactured by Kyodo International, Inc., having a thickness of 0.3 mm, an area of 3 cm ⁇ 3 cm, a conical shaped concave part, and a pattern
  • an obtained cured product is released from the Ni mold to obtain a cured product having a convexo-concave pattern on the alkali-free glass.
  • a transmittance of the obtained alkali-free glass and cured product at a wavelength of 450 nm is measured with a spectrophotometer (ultraviolet visible spectrophotometer, product name: V-550, manufactured by JASCO Corporation) to obtain a transmittance before heating.
  • a spectrophotometer ultraviolet visible spectrophotometer, product name: V-550, manufactured by JASCO Corporation
  • the obtained alkali-free glass and cured product are placed on a hot plate (hot plate, product name: HT-900, manufactured by AS ONE Corporation) set at 260° C. for five minutes. After five minutes, the obtained alkali-free glass and cured product are removed from the hot plate, and cooled to room temperature over 10 minutes. After the cooling to room temperature, a transmittance of the alkali-free glass and cured product after heating is measured with a spectrophotometer at a wavelength of 450 nm to obtain a transmittance after heating. Tables 1 to 3 indicate measurement results of the transmittances at a wavelength of 450 nm before and after heating.
  • Light Resistance Test Transmittances Before and After Light Resistance Test
  • Transmittances before and after a light resistance test are determined by measuring the transmittances at a wavelength of 450 nm of a cured product with a convexo-concave pattern before and after irradiated with light.
  • the cured product manufactured in the above (heat resistance test: transmittances before and after heating) is subjected to a light resistance test as described below, and transmittances before and after irradiation with light are measured.
  • a transmittance of the obtained alkali-free glass and cured product at a wavelength of 450 nm is measured with a spectrophotometer (ultraviolet visible spectrophotometer, product name: V-550, manufactured by JASCO Corporation) to obtain a transmittance before irradiation with light.
  • a spectrophotometer ultraviolet visible spectrophotometer, product name: V-550, manufactured by JASCO Corporation
  • the obtained alkali-free glass and cured product are put in a light resistance tester (product name: SUSTEST CPS+, manufactured by ATLAS), and are irradiated with light for 60 days under the following condition.
  • the light resistance tester is set such that an optical filter is special window glass, black standard temperature is 60° C., and illuminance is 765 W/m 2 (300 to 800 nm) with a xenon lamp.
  • a transmittance of the alkali-free glass and cured product after irradiation with light at a wavelength of 450 nm is measured with a spectrophotometer to obtain a transmittance after irradiation with light.
  • Table 4 indicates measurement results of the transmittances at a wavelength of 450 nm before and after the light resistance test.
  • Pattern with 4.1% 2.8% 2.1% 5.3% 2.4% 4.7% height of 200 nm Appearance of cured film after heating over five ⁇ ⁇ ⁇ ⁇ ⁇ minutes at 260° C. Transmittance of cured product Before heating 94.7% 94.7% 94.7% 94.7% 94.7% 94.7% 94.6% having convexo-concave pattern After heating 94.5% 94.5% 94.3% 94.6% 94.5% 94.2% at wavelength of 450 nm before and after heating over five minutes at 260° C.
  • Composition Samples 2 to 11, 13 to 23, 25 to 27, and 31 containing at least one of the hindered amine compound and the hindered phenol compound having a molecular weight of 700 or more as the oxidation inhibitor have excellent heat resistance and can suppress the pattern reduction ratio.
  • Tables indicate that there is a preferable content in the presence or absence of the polymerizable group of the hindered amine compound and in the hindered phenol compound.
  • Samples 11 and 31 using a combination of the hindered amine compound and the hindered phenol compound having a molecular weight of 700 or more have better heat resistance than a sample containing either one of the oxidation inhibitors and that the pattern reduction ratio of Samples 11 and 31 can be suppressed.
  • Samples 1, 12, 24, and 28 to 30 containing neither the hindered amine compound nor the hindered phenol compound having a molecular weight of 700 or more as the oxidation inhibitor have a large pattern reduction ratio and have poor heat resistance.
  • Composition Samples 33 to 37 containing an appropriate amount of a hindered amine compound as the oxidation inhibitor have excellent light resistance and can suppress the pattern reduction ratio. Meanwhile, it is indicated that Sample 32 containing no hindered amine compound as the oxidation inhibitor has a large pattern reduction ratio and poor light resistance. In addition, it is indicated that Sample 33 having a small blending amount of hindered amine compound has insufficient light resistance. It is found that Sample 37 using a combination of the hindered amine compound and the hindered phenol compound having a molecular weight of 700 or more has better light resistance than a sample containing either one of the oxidation inhibitors and that the pattern reduction ratio of Sample 37 can be suppressed.
  • One aspect of the present invention can provide a method for manufacturing a device having excellent heat resistance and/or light resistance.

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Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2394645A1 (en) 1999-06-11 2000-12-21 Sydney Hyman Image making medium
JP2004020702A (ja) 2002-06-13 2004-01-22 Sumitomo Electric Ind Ltd 光ケーブル接続函
JP5065209B2 (ja) * 2007-11-02 2012-10-31 富士フイルム株式会社 ナノインプリント用硬化性組成物、硬化物およびその製造方法
JP2009167317A (ja) * 2008-01-17 2009-07-30 Nippon Zeon Co Ltd 光学用成形体
CN102026795B (zh) 2008-05-13 2013-08-07 三菱瓦斯化学株式会社 可弯曲加工的聚碳酸酯树脂层压体和透光型电磁波屏蔽层压体以及它们的制造方法
JP5306903B2 (ja) * 2008-07-02 2013-10-02 富士フイルム株式会社 インプリント用硬化性組成物、これを用いた硬化物およびその製造方法、並びに、液晶表示装置用部材
JP2010087165A (ja) * 2008-09-30 2010-04-15 Fujifilm Corp ナノインプリント用硬化性組成物、これを用いた硬化物およびその製造方法、ならびに液晶表示装置用部材
JP5968933B2 (ja) * 2008-12-03 2016-08-10 富士フイルム株式会社 インプリント用硬化性組成物、パターン形成方法およびパターン
JP2010186979A (ja) * 2008-12-03 2010-08-26 Fujifilm Corp インプリント用硬化性組成物、パターン形成方法およびパターン
JP5479141B2 (ja) 2010-02-12 2014-04-23 株式会社日本触媒 硬化性樹脂組成物、カラーフィルタ用着色硬化性樹脂組成物およびカラーフィルタ
JP2011222732A (ja) * 2010-04-09 2011-11-04 Fujifilm Corp パターン形成方法及びパターン基板製造方法
US20130303649A1 (en) * 2010-12-02 2013-11-14 Kaneka Corporation Active energy ray-curable composition for optical material, cured product, and production method
US9157000B2 (en) 2011-03-29 2015-10-13 Toyo Ink Sc Holdings Co., Ltd. Active energy beam-curable inkjet ink composition
BR112014001160A2 (pt) * 2011-07-19 2017-02-21 3M Innovative Properties Co filme dupla face de redirecionamento de luz do dia
JP5643163B2 (ja) 2011-07-22 2014-12-17 株式会社日本触媒 活性エネルギー線硬化性組成物及びその硬化物
JP5710553B2 (ja) * 2011-08-25 2015-04-30 富士フイルム株式会社 インプリント用硬化性組成物、パターン形成方法およびパターン
EP2760969B1 (en) * 2011-09-30 2018-05-16 Switch Materials, Inc. Diarylethene compounds and uses thereof
CN104159940B (zh) 2012-03-07 2016-11-23 Dic株式会社 氨基甲酸酯(甲基)丙烯酸酯树脂组合物及被覆材料
JP2014093385A (ja) 2012-11-02 2014-05-19 Fujifilm Corp インプリント用密着膜の製造方法およびパターン形成方法
CN105377543B (zh) * 2013-03-29 2017-08-01 三菱化学株式会社 表面具备微细凹凸结构层的物品
JP6065733B2 (ja) 2013-04-25 2017-01-25 東洋インキＳｃホールディングス株式会社 インクジェット用インキ
US9884973B2 (en) 2013-10-23 2018-02-06 Toyo Ink Sc Holdings Co., Ltd. Active energy ray-curable inkjet ink and ink set
JP5776129B1 (ja) 2014-03-26 2015-09-09 東洋インキＳｃホールディングス株式会社 活性エネルギー線硬化型インクジェットインキ組成物
JP6797529B2 (ja) 2015-01-21 2020-12-09 東洋合成工業株式会社 光学部材の製造方法及びそれに用いられる組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220373889A1 (en) * 2021-04-28 2022-11-24 Tokyo Ohka Kogyo Co., Ltd. Pattern forming method

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