TWI375122B - Positive resist compositions and patterning process - Google Patents
Positive resist compositions and patterning process Download PDFInfo
- Publication number
- TWI375122B TWI375122B TW096144172A TW96144172A TWI375122B TW I375122 B TWI375122 B TW I375122B TW 096144172 A TW096144172 A TW 096144172A TW 96144172 A TW96144172 A TW 96144172A TW I375122 B TWI375122 B TW I375122B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- sulfonate
- acid
- bis
- hydrazine
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 35
- 230000008569 process Effects 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title description 19
- 238000000059 patterning Methods 0.000 title 1
- -1 salt compound Chemical class 0.000 claims description 265
- 229920002120 photoresistant polymer Polymers 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 70
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- 229910052799 carbon Inorganic materials 0.000 claims description 66
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 239000000463 material Substances 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
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- 238000010438 heat treatment Methods 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 13
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- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 description 1
- ZPLNASMNUBJSDR-UHFFFAOYSA-N isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1.C1=CC=C2C(=O)NC(=O)C2=C1 ZPLNASMNUBJSDR-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
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- 125000000468 ketone group Chemical group 0.000 description 1
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- 125000000686 lactone group Chemical group 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
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- SXLVVVXRQLAKQK-UHFFFAOYSA-N methyl 2-[butyl-(2-methoxy-2-oxoethyl)amino]acetate Chemical compound CCCCN(CC(=O)OC)CC(=O)OC SXLVVVXRQLAKQK-UHFFFAOYSA-N 0.000 description 1
- FBGFQFGNJVSNPX-UHFFFAOYSA-N methyl 2-[hexyl-(2-methoxy-2-oxoethyl)amino]acetate Chemical compound CCCCCCN(CC(=O)OC)CC(=O)OC FBGFQFGNJVSNPX-UHFFFAOYSA-N 0.000 description 1
- DWKPPFQULDPWHX-UHFFFAOYSA-N methyl 2-aminopropanoate Chemical compound COC(=O)C(C)N DWKPPFQULDPWHX-UHFFFAOYSA-N 0.000 description 1
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- PJBQUGMIXPCWOA-UHFFFAOYSA-N methyl 3-[(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCNCCC(=O)OC PJBQUGMIXPCWOA-UHFFFAOYSA-N 0.000 description 1
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- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 description 1
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- WIURVMHVEPTKHB-UHFFFAOYSA-N tert-butyl n,n-dicyclohexylcarbamate Chemical compound C1CCCCC1N(C(=O)OC(C)(C)C)C1CCCCC1 WIURVMHVEPTKHB-UHFFFAOYSA-N 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- USMVHTQGEMDHKL-UHFFFAOYSA-M triphenylsulfanium;2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 USMVHTQGEMDHKL-UHFFFAOYSA-M 0.000 description 1
- XUECSRVFRKTFKJ-UHFFFAOYSA-N tritylhydrazine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NN)C1=CC=CC=C1 XUECSRVFRKTFKJ-UHFFFAOYSA-N 0.000 description 1
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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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- 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
- C08F224/00—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 heterocyclic ring containing oxygen
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- 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
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- G—PHYSICS
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- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
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- 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
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- 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
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- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006315315A JP4296447B2 (ja) | 2006-11-22 | 2006-11-22 | ポジ型レジスト材料及びパターン形成方法 |
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| TW200900861A TW200900861A (en) | 2009-01-01 |
| TWI375122B true TWI375122B (en) | 2012-10-21 |
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| TW096144172A TWI375122B (en) | 2006-11-22 | 2007-11-21 | Positive resist compositions and patterning process |
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| JP (1) | JP4296447B2 (ja) |
| KR (1) | KR101028646B1 (ja) |
| TW (1) | TWI375122B (ja) |
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| JP5019071B2 (ja) * | 2007-09-05 | 2012-09-05 | 信越化学工業株式会社 | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
| JP5562826B2 (ja) * | 2008-02-25 | 2014-07-30 | 株式会社ダイセル | 電子吸引性置換基及びラクトン骨格を含む単量体、高分子化合物及びフォトレジスト組成物 |
| US9046773B2 (en) | 2008-03-26 | 2015-06-02 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, pattern forming method using the same, polymerizable compound and polymer compound obtained by polymerizing the polymerizable compound |
| JP5530645B2 (ja) * | 2008-03-26 | 2014-06-25 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物及びそれを用いたパターン形成方法 |
| JP5205133B2 (ja) * | 2008-06-04 | 2013-06-05 | 東京応化工業株式会社 | 化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
| JP5469845B2 (ja) * | 2008-06-20 | 2014-04-16 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP5173642B2 (ja) * | 2008-07-18 | 2013-04-03 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP5393325B2 (ja) * | 2008-08-01 | 2014-01-22 | 富士フイルム株式会社 | ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
| JP4771101B2 (ja) * | 2008-09-05 | 2011-09-14 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| JP4655128B2 (ja) * | 2008-09-05 | 2011-03-23 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| JP5325519B2 (ja) * | 2008-10-09 | 2013-10-23 | 東京応化工業株式会社 | ポジ型レジスト組成物、高分子化合物およびレジストパターン形成方法 |
| JP5537963B2 (ja) * | 2009-01-16 | 2014-07-02 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物及びそれを用いたパターン形成方法 |
| JP5433268B2 (ja) * | 2009-03-19 | 2014-03-05 | 富士フイルム株式会社 | 感活性光線性または感放射線性樹脂組成物及びそれを用いたパターン形成方法 |
| TW201106101A (en) * | 2009-06-01 | 2011-02-16 | Fujifilm Electronic Materials | Chemically amplified positive photoresist composition |
| JP5206986B2 (ja) | 2009-06-04 | 2013-06-12 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| JP5722558B2 (ja) * | 2009-06-23 | 2015-05-20 | 住友化学株式会社 | レジスト組成物 |
| WO2015122470A1 (ja) | 2014-02-14 | 2015-08-20 | 三菱瓦斯化学株式会社 | 新規脂環式エステル化合物の製造方法、新規脂環式エステル化合物、それを重合した(メタ)アクリル共重合体、およびそれを含む感光性樹脂組成物 |
| CN105960419B (zh) | 2014-02-14 | 2018-03-16 | 三菱瓦斯化学株式会社 | (甲基)丙烯酸酯化合物及其制造方法 |
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| KR20010040187A (ko) | 1999-10-28 | 2001-05-15 | 무네유키 가코우 | 포지티브 포토레지스트 조성물 |
| KR100795109B1 (ko) * | 2001-02-23 | 2008-01-17 | 후지필름 가부시키가이샤 | 포지티브 감광성 조성물 |
| JP4117112B2 (ja) * | 2001-03-30 | 2008-07-16 | 富士フイルム株式会社 | ポジ型フォトレジスト組成物 |
| TWI332122B (en) * | 2005-04-06 | 2010-10-21 | Shinetsu Chemical Co | Novel sulfonate salts and derivatives, photoacid generators, resist compositions and patterning process |
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2007
- 2007-11-21 KR KR1020070118960A patent/KR101028646B1/ko active Active
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| KR20080046581A (ko) | 2008-05-27 |
| TW200900861A (en) | 2009-01-01 |
| JP4296447B2 (ja) | 2009-07-15 |
| KR101028646B1 (ko) | 2011-04-11 |
| JP2008129388A (ja) | 2008-06-05 |
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