KR20040030511A - 신규 코폴리머 및 포토레지스트 조성물 - Google Patents
신규 코폴리머 및 포토레지스트 조성물 Download PDFInfo
- Publication number
- KR20040030511A KR20040030511A KR10-2003-7011140A KR20037011140A KR20040030511A KR 20040030511 A KR20040030511 A KR 20040030511A KR 20037011140 A KR20037011140 A KR 20037011140A KR 20040030511 A KR20040030511 A KR 20040030511A
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- KR
- South Korea
- Prior art keywords
- photoresist
- resin
- group
- photoacid
- polymer
- 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.)
- Ceased
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 63
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 229920001577 copolymer Polymers 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 56
- 229920005989 resin Polymers 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 29
- -1 hydroxyadamantyl functional groups Chemical group 0.000 claims abstract description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000004185 ester group Chemical group 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 12
- 239000011247 coating layer Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229920001897 terpolymer Polymers 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 239000010410 layer Substances 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 6
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- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229920006029 tetra-polymer Polymers 0.000 claims description 3
- 238000004377 microelectronic Methods 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004989 dicarbonyl group Chemical group 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
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- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 8
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- 238000003384 imaging method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
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- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 125000002015 acyclic group Chemical group 0.000 description 2
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- 238000010511 deprotection reaction Methods 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 108010001861 pregnancy-associated glycoprotein 1 Proteins 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZEFPSJCRLPUDJQ-UHFFFAOYSA-N (2-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(O)C2(OC(=O)C=C)C3 ZEFPSJCRLPUDJQ-UHFFFAOYSA-N 0.000 description 1
- AATKCDPVYREEEG-UHFFFAOYSA-N (2-methyl-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C(C)=C)C3 AATKCDPVYREEEG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- MNEXVZFQQPKDHC-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-nonadecafluorononane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MNEXVZFQQPKDHC-UHFFFAOYSA-M 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- WQNHWIYLCRZRLR-UHFFFAOYSA-N 2-(3-hydroxy-2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1(O)CC(=O)OC1=O WQNHWIYLCRZRLR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 description 1
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- ZUHAKVLHBJLXGV-UHFFFAOYSA-N tert-butyl 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOC(C)(C)C ZUHAKVLHBJLXGV-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- G03F7/0397—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 an alicyclic moiety in a side chain
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27140401P | 2001-02-25 | 2001-02-25 | |
| US60/271,404 | 2001-02-25 | ||
| PCT/US2002/005627 WO2002069044A2 (en) | 2001-02-25 | 2002-02-25 | Polymers and photoresist compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040030511A true KR20040030511A (ko) | 2004-04-09 |
Family
ID=23035399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7011140A Ceased KR20040030511A (ko) | 2001-02-25 | 2002-02-25 | 신규 코폴리머 및 포토레지스트 조성물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20020187420A1 (enExample) |
| JP (1) | JP2004524565A (enExample) |
| KR (1) | KR20040030511A (enExample) |
| CN (1) | CN1310090C (enExample) |
| AU (1) | AU2002255598A1 (enExample) |
| TW (1) | TWI293402B (enExample) |
| WO (1) | WO2002069044A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3890989B2 (ja) * | 2002-01-25 | 2007-03-07 | 住友化学株式会社 | レジスト組成物 |
| US7488565B2 (en) | 2003-10-01 | 2009-02-10 | Chevron U.S.A. Inc. | Photoresist compositions comprising diamondoid derivatives |
| US7208334B2 (en) * | 2004-03-31 | 2007-04-24 | Kabushiki Kaisha Toshiba | Method of manufacturing semiconductor device, acid etching resistance material and copolymer |
| JP4279237B2 (ja) * | 2004-05-28 | 2009-06-17 | 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 |
| US20060172223A1 (en) * | 2004-11-24 | 2006-08-03 | Rohm And Haas Electronic Materials Llc | Photoresist compositions |
| JP5031310B2 (ja) * | 2006-01-13 | 2012-09-19 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
| JP5782283B2 (ja) * | 2010-03-31 | 2015-09-24 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 新規のポリマーおよびフォトレジスト組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100245410B1 (ko) * | 1997-12-02 | 2000-03-02 | 윤종용 | 감광성 폴리머 및 그것을 이용한 화학증폭형 레지스트 조성물 |
| US6103445A (en) * | 1997-03-07 | 2000-08-15 | Board Of Regents, The University Of Texas System | Photoresist compositions comprising norbornene derivative polymers with acid labile groups |
| CN1190706C (zh) * | 1998-08-26 | 2005-02-23 | 住友化学工业株式会社 | 一种化学增强型正光刻胶组合物 |
| TWI263866B (en) * | 1999-01-18 | 2006-10-11 | Sumitomo Chemical Co | Chemical amplification type positive resist composition |
| JP3353292B2 (ja) * | 1999-03-29 | 2002-12-03 | 日本電気株式会社 | 化学増幅系レジスト |
| JP4061801B2 (ja) * | 2000-01-24 | 2008-03-19 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
| US6610465B2 (en) * | 2001-04-11 | 2003-08-26 | Clariant Finance (Bvi) Limited | Process for producing film forming resins for photoresist compositions |
-
2002
- 2002-02-25 AU AU2002255598A patent/AU2002255598A1/en not_active Abandoned
- 2002-02-25 TW TW091103266A patent/TWI293402B/zh active
- 2002-02-25 KR KR10-2003-7011140A patent/KR20040030511A/ko not_active Ceased
- 2002-02-25 US US10/082,769 patent/US20020187420A1/en not_active Abandoned
- 2002-02-25 JP JP2002568102A patent/JP2004524565A/ja active Pending
- 2002-02-25 CN CNB028069366A patent/CN1310090C/zh not_active Expired - Fee Related
- 2002-02-25 WO PCT/US2002/005627 patent/WO2002069044A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20020187420A1 (en) | 2002-12-12 |
| CN1310090C (zh) | 2007-04-11 |
| AU2002255598A1 (en) | 2002-09-12 |
| TWI293402B (en) | 2008-02-11 |
| WO2002069044A3 (en) | 2003-02-27 |
| CN1498361A (zh) | 2004-05-19 |
| JP2004524565A (ja) | 2004-08-12 |
| WO2002069044A2 (en) | 2002-09-06 |
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