JP4578971B2 - フォトレジストとして有用なフッ素化ポリマーおよび微細平版印刷のための方法 - Google Patents
フォトレジストとして有用なフッ素化ポリマーおよび微細平版印刷のための方法 Download PDFInfo
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- JP4578971B2 JP4578971B2 JP2004529165A JP2004529165A JP4578971B2 JP 4578971 B2 JP4578971 B2 JP 4578971B2 JP 2004529165 A JP2004529165 A JP 2004529165A JP 2004529165 A JP2004529165 A JP 2004529165A JP 4578971 B2 JP4578971 B2 JP 4578971B2
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- Prior art keywords
- fluorine
- ethylenically unsaturated
- containing copolymer
- photoresist composition
- acid
- Prior art date
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- 229920002313 fluoropolymer Polymers 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 56
- 229920001577 copolymer Polymers 0.000 claims abstract description 42
- 239000011737 fluorine Substances 0.000 claims abstract description 41
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 26
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- 125000000217 alkyl group Chemical group 0.000 claims description 25
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- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- GQRTVVANIGOXRF-UHFFFAOYSA-N (2-methyl-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C=C)C3 GQRTVVANIGOXRF-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003833 bile salt Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- RFJVDJWCXSPUBY-UHFFFAOYSA-N 2-(difluoromethylidene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)=C1OC(F)(F)C(F)(C(F)(F)F)O1 RFJVDJWCXSPUBY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LOPXMGVYAOPZIV-UHFFFAOYSA-N 3-diazonio-4h-chromen-2-olate Chemical compound C1=CC=C2OC(=O)C(=[N+]=[N-])CC2=C1 LOPXMGVYAOPZIV-UHFFFAOYSA-N 0.000 description 3
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
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- 239000011230 binding agent Substances 0.000 description 3
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 150000002431 hydrogen Chemical group 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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Classifications
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- 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
- C08F14/00—Homopolymers and 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 halogen
- C08F14/18—Monomers containing fluorine
-
- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
-
- 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
- C08F214/00—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 halogen
- C08F214/18—Monomers containing fluorine
-
- 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
- C08F214/00—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 halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US40437402P | 2002-08-19 | 2002-08-19 | |
| PCT/US2003/026088 WO2004016664A1 (en) | 2002-08-19 | 2003-08-19 | Fluorinated polymers useful as photoresists, and processes for microlithography |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005536589A JP2005536589A (ja) | 2005-12-02 |
| JP2005536589A5 JP2005536589A5 (enExample) | 2006-09-21 |
| JP4578971B2 true JP4578971B2 (ja) | 2010-11-10 |
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| US (1) | US7312287B2 (enExample) |
| EP (1) | EP1551886B1 (enExample) |
| JP (1) | JP4578971B2 (enExample) |
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| AT (1) | ATE408173T1 (enExample) |
| AU (1) | AU2003259951A1 (enExample) |
| DE (1) | DE60323521D1 (enExample) |
| TW (1) | TW200403257A (enExample) |
| WO (1) | WO2004016664A1 (enExample) |
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| KR20050062540A (ko) * | 2002-08-19 | 2005-06-23 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 포토레지스트로서 유용한 플루오르화 중합체 및 마이크로리소그래피법 |
| JP5560854B2 (ja) * | 2010-03-31 | 2014-07-30 | Jsr株式会社 | 感放射線性樹脂組成物およびそれに用いる重合体 |
| EP2645178B1 (en) * | 2010-11-24 | 2021-06-23 | AGC Inc. | Seal ring for automobile, and seal ring and sliding member for industrial gas compressor |
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| US5229473A (en) * | 1989-07-07 | 1993-07-20 | Daikin Industries Ltd. | Fluorine-containing copolymer and method of preparing the same |
| JP4034896B2 (ja) * | 1997-11-19 | 2008-01-16 | 松下電器産業株式会社 | レジスト組成物及びこれを用いたパターン形成方法 |
| JPH11265067A (ja) * | 1998-01-16 | 1999-09-28 | Jsr Corp | 感放射線性樹脂組成物 |
| JP4327360B2 (ja) * | 1998-09-23 | 2009-09-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ホトレジスト、ポリマーおよびマイクロリソグラフィの方法 |
| AU4678100A (en) * | 1999-05-04 | 2000-11-17 | E.I. Du Pont De Nemours And Company | Fluorinated polymers, photoresists and processes for microlithography |
| KR100535149B1 (ko) * | 1999-08-17 | 2005-12-07 | 주식회사 하이닉스반도체 | 신규의 포토레지스트용 공중합체 및 이를 이용한 포토레지스트조성물 |
| JP4240786B2 (ja) * | 1999-09-17 | 2009-03-18 | Jsr株式会社 | 感放射線性樹脂組成物 |
| JP2003532765A (ja) * | 2000-05-05 | 2003-11-05 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フォトレジスト用コポリマーおよびそのための方法 |
| EP1246013A3 (en) * | 2001-03-30 | 2003-11-19 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| US6737215B2 (en) * | 2001-05-11 | 2004-05-18 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep ultraviolet lithography |
| KR20050062540A (ko) * | 2002-08-19 | 2005-06-23 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 포토레지스트로서 유용한 플루오르화 중합체 및 마이크로리소그래피법 |
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2003
- 2003-08-19 KR KR1020057002754A patent/KR20050062540A/ko not_active Withdrawn
- 2003-08-19 AT AT03788676T patent/ATE408173T1/de not_active IP Right Cessation
- 2003-08-19 WO PCT/US2003/026088 patent/WO2004016664A1/en not_active Ceased
- 2003-08-19 AU AU2003259951A patent/AU2003259951A1/en not_active Abandoned
- 2003-08-19 US US10/523,490 patent/US7312287B2/en not_active Expired - Fee Related
- 2003-08-19 DE DE60323521T patent/DE60323521D1/de not_active Expired - Lifetime
- 2003-08-19 TW TW092122760A patent/TW200403257A/zh unknown
- 2003-08-19 CN CNA038189178A patent/CN1675262A/zh active Pending
- 2003-08-19 JP JP2004529165A patent/JP4578971B2/ja not_active Expired - Fee Related
- 2003-08-19 EP EP03788676A patent/EP1551886B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004016664A1 (en) | 2004-02-26 |
| DE60323521D1 (de) | 2008-10-23 |
| JP2005536589A (ja) | 2005-12-02 |
| AU2003259951A1 (en) | 2004-03-03 |
| ATE408173T1 (de) | 2008-09-15 |
| CN1675262A (zh) | 2005-09-28 |
| US7312287B2 (en) | 2007-12-25 |
| KR20050062540A (ko) | 2005-06-23 |
| EP1551886A4 (en) | 2007-11-14 |
| EP1551886A1 (en) | 2005-07-13 |
| TW200403257A (en) | 2004-03-01 |
| US20060166129A1 (en) | 2006-07-27 |
| EP1551886B1 (en) | 2008-09-10 |
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