JP2005535753A5 - - Google Patents
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- Publication number
- JP2005535753A5 JP2005535753A5 JP2004527971A JP2004527971A JP2005535753A5 JP 2005535753 A5 JP2005535753 A5 JP 2005535753A5 JP 2004527971 A JP2004527971 A JP 2004527971A JP 2004527971 A JP2004527971 A JP 2004527971A JP 2005535753 A5 JP2005535753 A5 JP 2005535753A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- halogen
- photoresist composition
- ethylenically unsaturated
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 229920002120 photoresistant polymer Polymers 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- -1 Z is OH Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical class 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 238000004377 microelectronic Methods 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- YRPLSAWATHBYFB-UHFFFAOYSA-N (2-methyl-2-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C=C)C2C3 YRPLSAWATHBYFB-UHFFFAOYSA-N 0.000 description 2
- VNYGZQZFJDADCT-UHFFFAOYSA-N (3-methyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2C(C)(OC(=O)C=C)CC1C2 VNYGZQZFJDADCT-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JAIXJKPOHMMBKS-UHFFFAOYSA-N 2-chloro-1,1,3,4,4,5,6,6,6-nonafluoro-5-(trifluoromethyl)hex-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C(=C(F)F)Cl)F)(F)F)F)(F)F JAIXJKPOHMMBKS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Chemical group 0.000 description 2
- 239000011574 phosphorus Chemical group 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40235002P | 2002-08-09 | 2002-08-09 | |
| US44050403P | 2003-01-16 | 2003-01-16 | |
| PCT/US2003/025022 WO2004014964A2 (en) | 2002-08-09 | 2003-08-08 | PHOTORESISTS, FLUORINATED POLYMERS AND PROCESSES FOR 157 nm MICROLITHOGRAPHY |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005535753A JP2005535753A (ja) | 2005-11-24 |
| JP2005535753A5 true JP2005535753A5 (https=) | 2006-09-28 |
| JP4610335B2 JP4610335B2 (ja) | 2011-01-12 |
Family
ID=31720593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004527971A Expired - Fee Related JP4610335B2 (ja) | 2002-08-09 | 2003-08-08 | フォトレジストとして有用な縮合４員環状炭素を有する多環式基を有するフッ素化ポリマーおよび微細平版印刷のための方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7264914B2 (https=) |
| EP (1) | EP1546221B1 (https=) |
| JP (1) | JP4610335B2 (https=) |
| KR (1) | KR20050069979A (https=) |
| CN (1) | CN1675264A (https=) |
| AT (1) | ATE460436T1 (https=) |
| AU (1) | AU2003259727A1 (https=) |
| DE (1) | DE60331667D1 (https=) |
| TW (1) | TW200418883A (https=) |
| WO (1) | WO2004014964A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100558686C (zh) * | 2003-03-06 | 2009-11-11 | 日本电气株式会社 | 脂环族不饱和化合物、聚合物、化学增幅抗蚀剂组合物及采用所述组合物形成图案的方法 |
| EP1505439A3 (en) | 2003-07-24 | 2005-04-20 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition and method of forming resist pattern |
| KR20070119671A (ko) * | 2005-03-11 | 2007-12-20 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 광형상화가능, 열경화가능 불화 레지스트 |
| JP5225555B2 (ja) * | 2006-04-27 | 2013-07-03 | 東京応化工業株式会社 | 液浸露光用レジスト組成物およびレジストパターン形成方法 |
| JP4862033B2 (ja) * | 2007-12-19 | 2012-01-25 | 旭化成株式会社 | 光吸収性を有するモールド、該モールドを利用する感光性樹脂のパターン形成方法、及び印刷版の製造方法 |
| JP5449909B2 (ja) * | 2008-08-04 | 2014-03-19 | 東京応化工業株式会社 | ポジ型レジスト組成物及びレジストパターン形成方法 |
| JP2010106118A (ja) * | 2008-10-29 | 2010-05-13 | Sumitomo Chemical Co Ltd | 重合体及びフォトレジスト組成物 |
| JP2014509302A (ja) * | 2010-12-21 | 2014-04-17 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | フッ素化有機化合物の製造方法 |
| KR102433038B1 (ko) * | 2014-06-03 | 2022-08-18 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 광가교결합된 플루오로중합체를 포함하는 패시베이션 층 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928865A (en) * | 1957-03-25 | 1960-03-15 | Du Pont | Fluorinated tricyclononanes and tetracycloundecanes |
| US5229473A (en) * | 1989-07-07 | 1993-07-20 | Daikin Industries Ltd. | Fluorine-containing copolymer and method of preparing the same |
| EP0437619B1 (en) * | 1989-07-07 | 1995-08-30 | Daikin Industries, Limited | Fluorinated copolymer and method of producing the same |
| US6232417B1 (en) * | 1996-03-07 | 2001-05-15 | The B. F. Goodrich Company | Photoresist compositions comprising polycyclic polymers with acid labile pendant groups |
| IL141803A0 (en) * | 1998-09-23 | 2002-03-10 | Du Pont | Photoresists, polymers and processes for microlithography |
| AU2001296737A1 (en) * | 2000-10-12 | 2002-04-22 | North Carolina State University | Co2-processes photoresists, polymers, and photoactive compounds for microlithography |
| EP1326903A2 (en) * | 2000-10-18 | 2003-07-16 | E. I. du Pont de Nemours and Company | Compositions for microlithography |
| CN1498360A (zh) * | 2000-11-29 | 2004-05-19 | 纳幕尔杜邦公司 | 聚合物掺混物及其在用于微细光刻的光刻胶组合物中的应用 |
| KR20040012689A (ko) * | 2000-11-29 | 2004-02-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 포토레지스트 조성물을 함유하는 다층 엘레멘트 및 이들의미세석판인쇄에서의 용도 |
| EP1246013A3 (en) * | 2001-03-30 | 2003-11-19 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| DE60211883T2 (de) * | 2001-03-30 | 2007-06-06 | E.I. Dupont De Nemours And Co., Wilmington | Polycyclische, fluor enthaltende polymere und photoresist für mikrolithographie |
| JP2003252928A (ja) * | 2002-02-27 | 2003-09-10 | Nec Corp | フッ素含有アセタールまたはケタール構造を有する単量体、重合体、ならびに化学増幅型レジスト組成物 |
| AU2003259728A1 (en) * | 2002-08-09 | 2004-02-25 | E. I. Du Pont De Nemours And Company | Fluorinated monomers, fluorinated polymers having polycyclic groups with fused 4-membered heterocyclic rings, useful as photoresists, and processes for microlithography |
-
2003
- 2003-08-08 AT AT03785133T patent/ATE460436T1/de not_active IP Right Cessation
- 2003-08-08 JP JP2004527971A patent/JP4610335B2/ja not_active Expired - Fee Related
- 2003-08-08 AU AU2003259727A patent/AU2003259727A1/en not_active Abandoned
- 2003-08-08 US US10/523,491 patent/US7264914B2/en not_active Expired - Fee Related
- 2003-08-08 KR KR1020057002241A patent/KR20050069979A/ko not_active Withdrawn
- 2003-08-08 EP EP03785133A patent/EP1546221B1/en not_active Expired - Lifetime
- 2003-08-08 CN CNA038192993A patent/CN1675264A/zh active Pending
- 2003-08-08 DE DE60331667T patent/DE60331667D1/de not_active Expired - Lifetime
- 2003-08-08 WO PCT/US2003/025022 patent/WO2004014964A2/en not_active Ceased
- 2003-08-11 TW TW092121993A patent/TW200418883A/zh unknown
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