WO2008155928A1 - 光硬化性組成物および表面に微細パターンを有する成形体の製造方法 - Google Patents

光硬化性組成物および表面に微細パターンを有する成形体の製造方法 Download PDF

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Publication number
WO2008155928A1
WO2008155928A1 PCT/JP2008/052373 JP2008052373W WO2008155928A1 WO 2008155928 A1 WO2008155928 A1 WO 2008155928A1 JP 2008052373 W JP2008052373 W JP 2008052373W WO 2008155928 A1 WO2008155928 A1 WO 2008155928A1
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WIPO (PCT)
Prior art keywords
compound
mass
photocurable composition
fine pattern
molded object
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PCT/JP2008/052373
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English (en)
French (fr)
Inventor
Yasuhide Kawaguchi
Kentaro Tsunozaki
Original Assignee
Asahi Glass Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asahi Glass Company, Limited filed Critical Asahi Glass Company, Limited
Priority to EP08711219A priority Critical patent/EP2159236B1/en
Priority to AT08711219T priority patent/ATE556098T1/de
Priority to JP2009520366A priority patent/JP5387406B2/ja
Priority to CN2008800208873A priority patent/CN101679568B/zh
Priority to KR1020097021536A priority patent/KR101431861B1/ko
Publication of WO2008155928A1 publication Critical patent/WO2008155928A1/ja
Priority to US12/542,086 priority patent/US8163813B2/en
Priority to US13/425,098 priority patent/US20120175821A1/en

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    • 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
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
    • B29C59/02—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
    • B29C59/022—Surface shaping of articles, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing characterised by the disposition or the configuration, e.g. dimensions, of the embossments or the shaping tools therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—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
    • C08F220/22—Esters containing halogen
    • 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
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/18—Diffraction gratings
    • G02B5/1847—Manufacturing methods
    • G02B5/1852—Manufacturing methods using mechanical means, e.g. ruling with diamond tool, moulding
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/18—Diffraction gratings
    • G02B5/1847—Manufacturing methods
    • G02B5/1857—Manufacturing methods using exposure or etching means, e.g. holography, photolithography, exposure to electron or ion beams
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents

Abstract

　離型性および機械的強度に優れる硬化物を得ることができる光硬化性組成物、およびモールドの反転パターンが精密に転写された微細パターンを表面に有する、耐久性に優れた成形体を製造できる方法を提供する。 　環を２つ以上有する芳香族化合物または環を２つ以上有する脂環式化合物であり、かつ（メタ）アクリロイルオキシ基を２つ有する化合物（Ａ）の１５～６０質量％と、フッ素原子を有し、かつ炭素－炭素不飽和二重結合を１つ以上有する化合物（Ｂ）（ただし化合物（Ａ）を除く。）の５～４０質量％と、（メタ）アクリロイルオキシ基を１つ有する化合物（Ｃ）（ただし化合物（Ｂ）を除く。）の１０～５５質量％と、光重合開始剤（Ｄ）の１～１２質量％とを含む（ただし（Ａ）＋（Ｂ）＋（Ｃ）＋（Ｄ）＝１００質量％である。）光硬化性組成物２０を用いる。
PCT/JP2008/052373 2007-06-20 2008-02-13 光硬化性組成物および表面に微細パターンを有する成形体の製造方法 WO2008155928A1 (ja)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP08711219A EP2159236B1 (en) 2007-06-20 2008-02-13 Photocurable composition and process for producing molded object having fine pattern in surface
AT08711219T ATE556098T1 (de) 2007-06-20 2008-02-13 Lichthärtbare zusammensetzung und verfahren zur herstellung eines formobjekts mit feiner oberflächenstruktur
JP2009520366A JP5387406B2 (ja) 2007-06-20 2008-02-13 表面に微細パターンを有する成形体の製造方法
CN2008800208873A CN101679568B (zh) 2007-06-20 2008-02-13 光固化性组合物及表面具有精细图案的成形体的制造方法
KR1020097021536A KR101431861B1 (ko) 2007-06-20 2008-02-13 광경화성 조성물 및 표면에 미세 패턴을 갖는 성형체의 제조 방법
US12/542,086 US8163813B2 (en) 2007-06-20 2009-08-17 Photocurable composition and method for producing molded product with fine pattern
US13/425,098 US20120175821A1 (en) 2007-06-20 2012-03-20 Photocurable composition and method for producing molded product with fine pattern

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007162466 2007-06-20
JP2007-162466 2007-06-20

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US12/542,086 Continuation US8163813B2 (en) 2007-06-20 2009-08-17 Photocurable composition and method for producing molded product with fine pattern

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WO2008155928A1 true WO2008155928A1 (ja) 2008-12-24

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US (2) US8163813B2 (ja)
EP (1) EP2159236B1 (ja)
JP (1) JP5387406B2 (ja)
KR (1) KR101431861B1 (ja)
CN (1) CN101679568B (ja)
AT (1) ATE556098T1 (ja)
TW (1) TWI455951B (ja)
WO (1) WO2008155928A1 (ja)

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JP2010258421A (ja) * 2009-03-26 2010-11-11 Fujifilm Corp レジスト組成物、レジスト層、インプリント方法、パターン形成体、磁気記録媒体の製造方法、及び磁気記録媒体
JP2010264370A (ja) * 2009-05-14 2010-11-25 Tokyo Metropolitan Univ マイクロリアクターおよびマイクロリアクターの製造方法
JP2011021113A (ja) * 2009-07-16 2011-02-03 Fujifilm Corp インプリント用硬化性組成物、硬化物およびパターン形成方法
JP2011181704A (ja) * 2010-03-01 2011-09-15 Osaka Prefecture Univ 溶剤溶解型光硬化性組成物を用いた微細構造体の製造方法
WO2011125800A1 (ja) * 2010-03-31 2011-10-13 Jsr株式会社 ナノインプリント用硬化性組成物、半導体素子及びナノインプリント方法
JP2012519224A (ja) * 2009-02-26 2012-08-23 コーニング インコーポレイテッド 電気的絶縁性高分子組成物
JP2012224793A (ja) * 2011-04-21 2012-11-15 Maruzen Petrochem Co Ltd 金属不純物量の少ない半導体リソグラフィー用共重合体の製造方法及び該共重合体を製造するための重合開始剤の精製方法
JPWO2011024421A1 (ja) * 2009-08-26 2013-01-24 三井化学株式会社 フッ素含有環状オレフィンポリマー組成物、該組成物から得られた転写体およびその製造方法
WO2013047136A1 (ja) * 2011-09-27 2013-04-04 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
WO2013118791A1 (en) 2012-02-09 2013-08-15 Canon Kabushiki Kaisha Photocured product and method for producing the same
KR20130103484A (ko) * 2010-08-04 2013-09-23 아사히 가라스 가부시키가이샤 광 경화성 조성물 및 표면에 미세 패턴을 갖는 성형체의 제조 방법
WO2013157496A1 (ja) * 2012-04-16 2013-10-24 日産化学工業株式会社 含フッ素高分岐ポリマー及びそれを含むポリカーボネート樹脂組成物
JP5617632B2 (ja) * 2008-05-29 2014-11-05 旭硝子株式会社 光硬化性組成物および表面に微細パターンを有する成形体の製造方法
WO2015076309A1 (ja) * 2013-11-21 2015-05-28 旭硝子株式会社 硬化性組成物、硬化物、カメラモジュール、および撮像装置の製造方法
WO2016104670A1 (ja) * 2014-12-25 2016-06-30 富士フイルム株式会社 インプリント用光硬化性組成物、パターン形成方法およびデバイスの製造方法
JP2016199617A (ja) * 2015-04-07 2016-12-01 日本合成化学工業株式会社 光硬化性組成物
KR20170118156A (ko) 2015-03-20 2017-10-24 후지필름 가부시키가이샤 임프린트용 경화성 조성물, 경화물, 패턴 형성 방법, 리소그래피 방법, 패턴 및 리소그래피용 마스크
US9978479B2 (en) 2009-02-26 2018-05-22 Corning Incorporated Electrically isolating polymer composition
WO2018173930A1 (ja) * 2017-03-23 2018-09-27 Ａｇｃ株式会社 インプリント用硬化性組成物、レプリカモールドおよびその製造方法
WO2023018224A3 (ja) * 2021-08-12 2023-04-06 ニッカ コリア カンパニー リミテッド フッ素系ポリマー、表面処理剤、繊維製品の製造方法、及び、繊維製品

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JP5413195B2 (ja) * 2007-09-28 2014-02-12 旭硝子株式会社 微細パターン形成体、微細パターン形成体の製造方法、光学素子および光硬化性組成物
JP2009215179A (ja) * 2008-03-07 2009-09-24 Fujifilm Corp （メタ）アクリレート化合物、これを用いた硬化性組成物、光ナノインプリント用組成物、並びにこれらの硬化性組成物の硬化物およびその製造方法
KR20110002008A (ko) * 2008-04-03 2011-01-06 아사히 가라스 가부시키가이샤 와이어 그리드형 편광자 및 그 제조 방법
WO2009125751A1 (ja) * 2008-04-08 2009-10-15 旭硝子株式会社 ワイヤグリッド型偏光子の製造方法
KR20110031440A (ko) * 2008-07-10 2011-03-28 아사히 가라스 가부시키가이샤 와이어 그리드형 편광자 및 그 제조 방법
EP2357205A4 (en) * 2008-12-05 2013-11-20 Asahi Glass Co Ltd LIGHT-CURING COMPOSITION AND METHOD OF MANUFACTURING A SHAPE WITH A FINE PATTERN ON THE SURFACE
JP5671302B2 (ja) 2009-11-10 2015-02-18 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
JP5693925B2 (ja) * 2010-02-04 2015-04-01 丸善石油化学株式会社 樹脂型、成形体、及び成形体の製造方法
TWI480324B (zh) * 2010-08-04 2015-04-11 Asahi Glass Co Ltd A photohardenable composition, and a molded article having a fine pattern on its surface
US9504987B2 (en) * 2011-07-18 2016-11-29 New Jersey Institute Of Technology System and method for superabsorbent material
CN104220224B (zh) * 2012-04-10 2016-11-09 大金工业株式会社 压印用树脂模具材料组合物
US11294278B1 (en) 2018-12-11 2022-04-05 Facebook Technologies, Llc Reducing adhesive failure during nanoimprint lithography demolding
US11262650B1 (en) * 2018-12-11 2022-03-01 Facebook Technologies, Llc Reducing adhesive failure during nanoimprint lithography demolding

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