JP2008532067A5 - - Google Patents
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- Publication number
- JP2008532067A5 JP2008532067A5 JP2007556415A JP2007556415A JP2008532067A5 JP 2008532067 A5 JP2008532067 A5 JP 2008532067A5 JP 2007556415 A JP2007556415 A JP 2007556415A JP 2007556415 A JP2007556415 A JP 2007556415A JP 2008532067 A5 JP2008532067 A5 JP 2008532067A5
- Authority
- JP
- Japan
- Prior art keywords
- topcoat material
- polymer
- topcoat
- layer
- methacrylate
- 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
Links
- 239000000463 material Substances 0.000 claims 35
- 229920002120 photoresistant polymer Polymers 0.000 claims 13
- 229920000642 polymer Polymers 0.000 claims 11
- 239000000758 substrate Substances 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 230000005855 radiation Effects 0.000 claims 7
- 125000002723 alicyclic group Chemical group 0.000 claims 6
- 238000003384 imaging method Methods 0.000 claims 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- -1 hydrocarbon alcohols Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 150000002734 metacrylic acid derivatives Chemical group 0.000 claims 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- 229920002818 (Hydroxyethyl)methacrylate Chemical group 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical group COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical group OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims 1
- 239000000919 ceramic Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000000151 deposition Methods 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 claims 1
- 0 CC(CN)(*N)C(OC(CC(C1)C(C(F)(F)F)(C(F)(F)F)O)CC1C(C(F)(F)F)(C(F)(F)F)O)=O Chemical compound CC(CN)(*N)C(OC(CC(C1)C(C(F)(F)F)(C(F)(F)F)O)CC1C(C(F)(F)F)(C(F)(F)F)O)=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/063,940 | 2005-02-23 | ||
| US11/063,940 US7288362B2 (en) | 2005-02-23 | 2005-02-23 | Immersion topcoat materials with improved performance |
| PCT/US2006/006225 WO2006091648A2 (en) | 2005-02-23 | 2006-02-22 | Immersion topcoat materials with improved performance |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008532067A JP2008532067A (ja) | 2008-08-14 |
| JP2008532067A5 true JP2008532067A5 (enExample) | 2009-02-12 |
| JP5046236B2 JP5046236B2 (ja) | 2012-10-10 |
Family
ID=36913114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007556415A Expired - Fee Related JP5046236B2 (ja) | 2005-02-23 | 2006-02-22 | 改善された性能を有する液浸トップコート材料 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7288362B2 (enExample) |
| EP (1) | EP1851589B1 (enExample) |
| JP (1) | JP5046236B2 (enExample) |
| CN (1) | CN101164013B (enExample) |
| AT (1) | ATE474249T1 (enExample) |
| DE (1) | DE602006015428D1 (enExample) |
| TW (1) | TWI397773B (enExample) |
| WO (1) | WO2006091648A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI297809B (enExample) * | 2001-10-24 | 2008-06-11 | Toyo Boseki | |
| US7473512B2 (en) * | 2004-03-09 | 2009-01-06 | Az Electronic Materials Usa Corp. | Process of imaging a deep ultraviolet photoresist with a top coating and materials thereof |
| JP4355944B2 (ja) * | 2004-04-16 | 2009-11-04 | 信越化学工業株式会社 | パターン形成方法及びこれに用いるレジスト上層膜材料 |
| JP4697406B2 (ja) * | 2004-08-05 | 2011-06-08 | 信越化学工業株式会社 | 高分子化合物，レジスト保護膜材料及びパターン形成方法 |
| JP4621451B2 (ja) * | 2004-08-11 | 2011-01-26 | 富士フイルム株式会社 | 液浸露光用保護膜形成組成物及びそれを用いたパターン形成方法 |
| US7358035B2 (en) * | 2005-06-23 | 2008-04-15 | International Business Machines Corporation | Topcoat compositions and methods of use thereof |
| JP5055743B2 (ja) * | 2005-11-04 | 2012-10-24 | セントラル硝子株式会社 | 含フッ素高分子コーティング用組成物、該コーティング用組成物を用いた含フッ素高分子膜の形成方法、ならびにフォトレジストまたはリソグラフィーパターンの形成方法。 |
| US20070117040A1 (en) * | 2005-11-21 | 2007-05-24 | International Business Machines Corporation | Water castable-water strippable top coats for 193 nm immersion lithography |
| JP5151038B2 (ja) * | 2006-02-16 | 2013-02-27 | 富士通株式会社 | レジストカバー膜形成材料、レジストパターンの形成方法、半導体装置及びその製造方法 |
| US7951524B2 (en) * | 2006-04-28 | 2011-05-31 | International Business Machines Corporation | Self-topcoating photoresist for photolithography |
| US8945808B2 (en) * | 2006-04-28 | 2015-02-03 | International Business Machines Corporation | Self-topcoating resist for photolithography |
| US8034532B2 (en) | 2006-04-28 | 2011-10-11 | International Business Machines Corporation | High contact angle topcoat material and use thereof in lithography process |
| US7521172B2 (en) * | 2006-04-28 | 2009-04-21 | International Business Machines Corporation | Topcoat material and use thereof in immersion lithography processes |
| US20080311530A1 (en) * | 2007-06-15 | 2008-12-18 | Allen Robert D | Graded topcoat materials for immersion lithography |
| JP5075516B2 (ja) * | 2007-07-25 | 2012-11-21 | 株式会社ダイセル | レジスト保護膜用重合体溶液の製造方法 |
| US8003309B2 (en) * | 2008-01-16 | 2011-08-23 | International Business Machines Corporation | Photoresist compositions and methods of use in high index immersion lithography |
| JP5010569B2 (ja) * | 2008-01-31 | 2012-08-29 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
| US8084193B2 (en) * | 2008-07-12 | 2011-12-27 | International Business Machines Corporation | Self-segregating multilayer imaging stack with built-in antireflective properties |
| US8541523B2 (en) * | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| KR101099506B1 (ko) | 2010-11-17 | 2011-12-27 | 주식회사 동진쎄미켐 | 고분자 화합물 및 이를 포함하는 액침 노광 프로세스용 레지스트 보호막 조성물 |
| US8476004B2 (en) | 2011-06-27 | 2013-07-02 | United Microelectronics Corp. | Method for forming photoresist patterns |
| US8701052B1 (en) | 2013-01-23 | 2014-04-15 | United Microelectronics Corp. | Method of optical proximity correction in combination with double patterning technique |
| WO2014115843A1 (ja) | 2013-01-24 | 2014-07-31 | 日産化学工業株式会社 | リソグラフィー用レジスト上層膜形成組成物及びそれを用いた半導体装置の製造方法 |
| US8627242B1 (en) | 2013-01-30 | 2014-01-07 | United Microelectronics Corp. | Method for making photomask layout |
| US9230812B2 (en) | 2013-05-22 | 2016-01-05 | United Microelectronics Corp. | Method for forming semiconductor structure having opening |
| KR102312211B1 (ko) | 2014-02-26 | 2021-10-14 | 닛산 가가쿠 가부시키가이샤 | 레지스트 상층막 형성 조성물 및 이것을 이용한 반도체장치의 제조방법 |
| WO2017062822A1 (en) * | 2015-10-09 | 2017-04-13 | Illinois Tool Works Inc. | Surface appearance simulation system and method |
| US11993091B2 (en) * | 2021-03-12 | 2024-05-28 | Darin A. Grassman | Methods and apparatus for hand printing designs and patterns |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59211045A (ja) * | 1983-05-17 | 1984-11-29 | Toshiba Corp | ポジ型フォトレジストの露光方法 |
| US5240812A (en) | 1990-09-18 | 1993-08-31 | International Business Machines Corporation | Top coat for acid catalyzed resists |
| JP2643056B2 (ja) | 1991-06-28 | 1997-08-20 | インターナショナル・ビジネス・マシーンズ・コーポレイション | 表面反射防止コーティング形成組成物及びその使用 |
| US5330883A (en) | 1992-06-29 | 1994-07-19 | Lsi Logic Corporation | Techniques for uniformizing photoresist thickness and critical dimension of underlying features |
| US5506090A (en) | 1994-09-23 | 1996-04-09 | Minnesota Mining And Manufacturing Company | Process for making shoot and run printing plates |
| JPH0936017A (ja) * | 1995-07-20 | 1997-02-07 | Hitachi Ltd | パタン形成方法及びそれを用いた半導体素子の製造方法 |
| US5879853A (en) | 1996-01-18 | 1999-03-09 | Kabushiki Kaisha Toshiba | Top antireflective coating material and its process for DUV and VUV lithography systems |
| JP3691897B2 (ja) | 1996-03-07 | 2005-09-07 | 富士通株式会社 | レジスト材料及びレジストパターンの形成方法 |
| US6274295B1 (en) * | 1997-03-06 | 2001-08-14 | Clariant Finance (Bvi) Limited | Light-absorbing antireflective layers with improved performance due to refractive index optimization |
| JPH1115150A (ja) * | 1997-06-20 | 1999-01-22 | Toppan Printing Co Ltd | 多層構造を有するドライフィルムレジスト |
| EP1476788A2 (en) | 2002-02-21 | 2004-11-17 | Honeywell International Inc. | Fluorinated molecules and methods of making and using same |
| JP2003345026A (ja) | 2002-05-24 | 2003-12-03 | Tokyo Ohka Kogyo Co Ltd | 反射防止膜形成用塗布液組成物およびこれを用いたホトレジスト積層体、並びにホトレジストパターンの形成方法 |
| JP3851594B2 (ja) | 2002-07-04 | 2006-11-29 | Ａｚエレクトロニックマテリアルズ株式会社 | 反射防止コーティング用組成物およびパターン形成方法 |
| JP4410508B2 (ja) * | 2002-08-07 | 2010-02-03 | セントラル硝子株式会社 | 含フッ素化合物とその高分子化合物 |
| US20040091813A1 (en) | 2002-11-05 | 2004-05-13 | Honeywell International Inc. | Fluorinated polymers |
| KR100620672B1 (ko) * | 2002-12-14 | 2006-09-13 | 주식회사 하이닉스반도체 | 포토레지스트 조성물 |
| WO2004108769A2 (en) * | 2003-06-06 | 2004-12-16 | Georgia Tech Research Corporation | Composition and method of use thereof |
| JP2005045083A (ja) * | 2003-07-24 | 2005-02-17 | Sony Corp | 露光方法 |
| JP4376718B2 (ja) * | 2003-07-28 | 2009-12-02 | エーエスエムエル ネザーランズ ビー．ブイ． | リソグラフィ装置、デバイス製造方法、及び基板 |
| CN100555083C (zh) * | 2003-12-23 | 2009-10-28 | 皇家飞利浦电子股份有限公司 | 用于浸入式光刻的可除去薄膜 |
| US20050202351A1 (en) * | 2004-03-09 | 2005-09-15 | Houlihan Francis M. | Process of imaging a deep ultraviolet photoresist with a top coating and materials thereof |
| JP4484603B2 (ja) * | 2004-03-31 | 2010-06-16 | セントラル硝子株式会社 | トップコート組成物 |
| JP4355944B2 (ja) * | 2004-04-16 | 2009-11-04 | 信越化学工業株式会社 | パターン形成方法及びこれに用いるレジスト上層膜材料 |
| JP4697406B2 (ja) * | 2004-08-05 | 2011-06-08 | 信越化学工業株式会社 | 高分子化合物，レジスト保護膜材料及びパターン形成方法 |
-
2005
- 2005-02-23 US US11/063,940 patent/US7288362B2/en not_active Expired - Fee Related
-
2006
- 2006-02-17 TW TW095105386A patent/TWI397773B/zh not_active IP Right Cessation
- 2006-02-22 DE DE602006015428T patent/DE602006015428D1/de active Active
- 2006-02-22 CN CN2006800047266A patent/CN101164013B/zh not_active Expired - Fee Related
- 2006-02-22 JP JP2007556415A patent/JP5046236B2/ja not_active Expired - Fee Related
- 2006-02-22 EP EP06735757A patent/EP1851589B1/en not_active Not-in-force
- 2006-02-22 WO PCT/US2006/006225 patent/WO2006091648A2/en not_active Ceased
- 2006-02-22 AT AT06735757T patent/ATE474249T1/de not_active IP Right Cessation
-
2007
- 2007-10-05 US US11/868,320 patent/US7855045B2/en not_active Expired - Fee Related
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