JP2004526844A - 多環式フッ素含有ポリマーおよびマイクロリソグラフィー用フォトレジスト - Google Patents
多環式フッ素含有ポリマーおよびマイクロリソグラフィー用フォトレジスト Download PDFInfo
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- JP2004526844A JP2004526844A JP2002578302A JP2002578302A JP2004526844A JP 2004526844 A JP2004526844 A JP 2004526844A JP 2002578302 A JP2002578302 A JP 2002578302A JP 2002578302 A JP2002578302 A JP 2002578302A JP 2004526844 A JP2004526844 A JP 2004526844A
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- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JAGYXYUAYDLKNO-UHFFFAOYSA-N hepta-2,5-diene Chemical compound CC=CCC=CC JAGYXYUAYDLKNO-UHFFFAOYSA-N 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- RKBDIAMXCKXCEJ-UHFFFAOYSA-N molport-003-906-502 Chemical compound C1C2C3C(F)(F)C(F)(F)C3C1C=C2 RKBDIAMXCKXCEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012634 optical imaging Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001544 silver hexafluoroantimonate(V) Inorganic materials 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KUVYIDWVLRLCGO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate 2,2,3,3,3-pentafluoropropyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(C)(C)C.C(C(=C)C)(=O)OCC(C(F)(F)F)(F)F KUVYIDWVLRLCGO-UHFFFAOYSA-N 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28026901P | 2001-03-30 | 2001-03-30 | |
| PCT/US2002/009799 WO2002079287A1 (en) | 2001-03-30 | 2002-03-27 | Polycyclic fluorine-containing polymers and photoresists for microlithography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004526844A true JP2004526844A (ja) | 2004-09-02 |
| JP2004526844A5 JP2004526844A5 (enExample) | 2005-12-22 |
Family
ID=23072365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002578302A Pending JP2004526844A (ja) | 2001-03-30 | 2002-03-27 | 多環式フッ素含有ポリマーおよびマイクロリソグラフィー用フォトレジスト |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1383812B1 (enExample) |
| JP (1) | JP2004526844A (enExample) |
| KR (1) | KR20040018342A (enExample) |
| CN (1) | CN1215099C (enExample) |
| DE (1) | DE60211883T2 (enExample) |
| IL (1) | IL157040A0 (enExample) |
| WO (1) | WO2002079287A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1675264A (zh) * | 2002-08-09 | 2005-09-28 | E.I.内穆尔杜邦公司 | 用作光致抗蚀剂的具有带稠合4－元碳环的多环基团的氟化聚合物和用于微石印术的方法 |
| JP2005535780A (ja) * | 2002-08-09 | 2005-11-24 | 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、フルオロポリマーおよび１５７ｎｍ微細平版印刷のための方法 |
| JP4386197B2 (ja) | 2003-03-06 | 2009-12-16 | 日本電気株式会社 | 脂環式不飽和化合物、重合体、化学増幅レジスト組成物、及び該組成物を用いたパターン形成方法 |
| US7297811B2 (en) | 2003-12-04 | 2007-11-20 | International Business Machines Corporation | Precursors to fluoroalkanol-containing olefin monomers and associated methods of synthesis and use |
| US7193023B2 (en) | 2003-12-04 | 2007-03-20 | International Business Machines Corporation | Low activation energy photoresists |
| US7495135B2 (en) | 2003-12-04 | 2009-02-24 | International Business Machines Corporation | Precursors to fluoroalkanol-containing olefin monomers, and associated methods of synthesis and use |
| US7820369B2 (en) | 2003-12-04 | 2010-10-26 | International Business Machines Corporation | Method for patterning a low activation energy photoresist |
| CN1779569B (zh) * | 2004-11-22 | 2010-09-29 | 北京科华微电子材料有限公司 | 氟代环烯烃聚合物及在深紫外类光刻胶中的应用 |
| US7732547B2 (en) * | 2007-07-12 | 2010-06-08 | Industrial Technology Research Institute | Fluorinated cyclic olefinic graft polymer |
| JP6545168B2 (ja) * | 2013-11-13 | 2019-07-17 | オーソゴナル，インコーポレイテッド | 分岐型フッ素化感光性ポリマー |
| DE102014119634B4 (de) | 2014-05-05 | 2023-05-11 | Taiwan Semiconductor Manufacturing Company, Ltd. | Verfahren zum herstellen von halbleitervorrichtungen und photolitographiematerial |
| WO2021088198A1 (en) * | 2019-11-04 | 2021-05-14 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
| CN118307704A (zh) * | 2024-04-26 | 2024-07-09 | 安徽恒坤新材料科技有限公司 | 一种桥型结构光刻胶树脂和KrF光刻胶组合物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928865A (en) * | 1957-03-25 | 1960-03-15 | Du Pont | Fluorinated tricyclononanes and tetracycloundecanes |
| EP0437619B1 (en) * | 1989-07-07 | 1995-08-30 | Daikin Industries, Limited | Fluorinated copolymer and method of producing the same |
-
2002
- 2002-03-27 IL IL15704002A patent/IL157040A0/xx unknown
- 2002-03-27 WO PCT/US2002/009799 patent/WO2002079287A1/en not_active Ceased
- 2002-03-27 KR KR10-2003-7012744A patent/KR20040018342A/ko not_active Withdrawn
- 2002-03-27 DE DE60211883T patent/DE60211883T2/de not_active Expired - Lifetime
- 2002-03-27 JP JP2002578302A patent/JP2004526844A/ja active Pending
- 2002-03-27 CN CNB028077636A patent/CN1215099C/zh not_active Expired - Fee Related
- 2002-03-27 EP EP02757868A patent/EP1383812B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1066554A1 (en) | 2005-03-24 |
| WO2002079287A1 (en) | 2002-10-10 |
| CN1500099A (zh) | 2004-05-26 |
| DE60211883D1 (en) | 2006-07-06 |
| DE60211883T2 (de) | 2007-06-06 |
| EP1383812A1 (en) | 2004-01-28 |
| EP1383812B1 (en) | 2006-05-31 |
| IL157040A0 (en) | 2004-02-08 |
| KR20040018342A (ko) | 2004-03-03 |
| CN1215099C (zh) | 2005-08-17 |
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