TW554250B - Resist with high resolution to i ray and process for forming pattern - Google Patents
Resist with high resolution to i ray and process for forming pattern Download PDFInfo
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- TW554250B TW554250B TW090128011A TW90128011A TW554250B TW 554250 B TW554250 B TW 554250B TW 090128011 A TW090128011 A TW 090128011A TW 90128011 A TW90128011 A TW 90128011A TW 554250 B TW554250 B TW 554250B
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- Prior art keywords
- resin composition
- photosensitive resin
- resin
- exposure
- weight
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 47
- 239000011347 resin Substances 0.000 claims abstract description 47
- 239000011342 resin composition Substances 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000003504 photosensitizing agent Substances 0.000 claims description 17
- 239000004922 lacquer Substances 0.000 claims description 16
- 239000004793 Polystyrene Substances 0.000 claims description 14
- 229920002223 polystyrene Polymers 0.000 claims description 14
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 claims description 12
- 229920000058 polyacrylate Polymers 0.000 claims description 9
- 229920000193 polymethacrylate Polymers 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000005011 phenolic resin Substances 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical group OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 claims 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000007261 regionalization Effects 0.000 claims 1
- -1 polyethylene Polymers 0.000 abstract description 27
- 239000003513 alkali Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 229920002125 Sokalan® Polymers 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229920003986 novolac Polymers 0.000 abstract 1
- 239000004584 polyacrylic acid Substances 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 150000003440 styrenes Chemical class 0.000 description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 9
- 229920002120 photoresistant polymer Polymers 0.000 description 9
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 4
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical class COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- WWGUMAYGTYQSGA-UHFFFAOYSA-N 2,3-dimethylnaphthalene Chemical compound C1=CC=C2C=C(C)C(C)=CC2=C1 WWGUMAYGTYQSGA-UHFFFAOYSA-N 0.000 description 2
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 238000001459 lithography Methods 0.000 description 2
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
554250 五、發明說明(1) 【技術領域】 本發明係有關一種製造半導體裝置、平面顯示板顯示器 (FPD)等時藉由適當的i線曝光之圖樣形成方法及其所使用 的感光性樹脂組成物。 【先前技術】 以LSI等半導體積體電路、或FPD之顯示製造、熱針頭 等之電路基板製造等爲始的廣泛領域中,爲進行微細元件 之形成或微細加工時自古以來即使用微影術。於微影術 中,爲形成光阻劑圖樣時使用正型或負型感光性樹脂組成 物。此等感光性樹脂組成物中,正型感光性樹脂組成物廣 泛使用含有鹼可溶性樹脂與作爲感光劑之醒二物 之組成物。該組成物例如日本特開昭54-23570號公報(美 國專利第3,666,473號說明書)、特開昭56- 30850號公報 (美國專利第4,115,128號說明書)、特開昭5 5 - 7 3 045號公 報' 特開昭61 - 205933號公報等多數文獻中記載的各種組 成者作爲「酚醛淸漆樹脂/醌二疊氮化合物」。此等含有酚 醛淸漆樹脂與醌二疊氮化合物之組成物,直至目前就酚醛 淸漆樹脂及感光劑兩面而言進行硏究開發。就酚醛淸漆樹 脂而言,當然是開發新的樹脂,惟可藉由改善習知樹脂之 物性等,製得具有優異特性之感光性樹脂組成物。例如於 特開昭60 - 1 40235號公報、特開平1 - 1 05243號公報中揭 示,藉由在酚醛淸漆樹脂中具有特有的分子量分布,以及 特開昭60- 97347號公報、特開昭60· 1 897 39號公報、專利 554250 五、發明說明(2) 第2590342號公報中揭示藉由使用分別除去低分子量成分 之酚醛淸漆樹脂,可提供具有優異特性之感光性樹脂組成 物。 然而,半導體構件中積體電路的積體度逐年提高,於半 導體構件等製造中要求半微米以下線寬之圖樣加工,係爲 習知技術所無法充分對應者。而且,於製造液晶顯示器 (LCD)等顯示面時,爲形成光阻劑圖樣時以往藉由使用g線 或g + h線作爲光源之曝光裝置以進行曝光,爲形成微細元 件時開始檢討以i線作爲曝光光源之製造工程,企求對應 於i線曝光、具有高解像力之感光性樹脂組成物。 爲使對應於i線之感光性樹脂組成物高解像力化時,直 至目前爲止提案有作爲使用感光劑之1,1,1-參(4-羥基-3, 5-二甲基苯基)丁烷之1,2-萘醌-2-二疊氮基-5-磺酸酯 的技術(特開平6-3321 67號公報)、使用由特定苯酚化合物 衍生的酚醛淸漆樹脂與感光劑之技術(特開平5 - 88364號公 報、特開平10-20503號公報、特開2000- 1 37324號公 報)、使用含有特定比例的三羥基二苯甲酮之萘醌二疊氮基 磺酸酯與三羥基二苯甲酮之感光成份的技術(特開平8-82926號公報)、使用特定酯化率之2,3,4-三羥基二苯甲酮 的1,2-萘醌二疊氮基-5-磺酸酯與2, 3,4,4’-四羥基二苯甲 酮之1,2-萘醌二疊氮基-5-磺酸酯之混合物作爲感光劑之 技術(特開平2 - 1 0905 1號公報)、使用以特定聚羥基化合物 之1,2-萘醌二疊氮基-5-及/或-4-磺酸酯規定四酯成分之 554250 五、發明說明(3 ) 量的感光劑技術(特開平9-1 5853號)、2,3,4,4,-四羥基二 苯甲酮之1,2-萘醋二疊氮基-5-磺酸酯及1,2-萘醌二疊氮 基-4-磺酸酯以特定混合比混合者作爲感光劑之技術(特開 平9-15853號公報)等。然而,以往所提案者就解像力及所 形成光阻劑圖樣產生邊緣突出情形等圖樣形狀而言會有問 題’故企求具有高解像力、所得圖樣形狀良好的對應於i 線曝光光源之感光性樹脂組成物及用它之圖樣形成方法。 有鑑於上述情形,本發明之目的係提供一種可以高解像 力、形成不會有邊緣突出情形等良好圖樣的i線曝光用感 光性樹脂組成物以及用它之圖樣形成方法。 本發明人等再三深入硏究的結果,發現以i線作爲曝光 光源之圖樣形成方法中,含有鹼可溶性樹脂與含醌二疊氮 基之感光劑、且該鹼可溶性樹脂爲酚醛淸漆樹脂與一種或 二種以上選自於(i)聚丙烯酸酯、(ii)聚甲基丙烯酸酯、 (iii)聚苯乙烯衍生物、及(iv)丙烯酸酯、甲基丙烯酸酯及 苯乙烯衍生物之單體單位所成共聚物的樹脂之混合物所成 者,可達成上述目的遂而完成本發明。 【發明之揭示】 換言之,本發明係有關一種圖樣形成方法,其係於以i 線作爲曝光光源之圖樣形成方法中,其特徵爲感光性樹脂 組成物爲含有鹼可溶性樹脂與含醌二疊氮基之感光劑、且 該鹼可溶性樹脂爲酚醛淸漆樹脂與一種或二種以上選自於 (i)聚丙烯酸酯、(ii)聚甲基丙烯酸酯、(iii)聚苯乙烯衍 554250 五、發明說明(4 ) 生物、及(iv)丙烯酸酯、甲基丙烯酸酯及苯乙烯衍生物之 單體單位所成共聚物的樹脂之混合物所成。 而且,本發明係有關一種i線曝光用感光性樹脂組成 物,其係於含有鹼可溶性樹脂與含醌二疊氮基之感光劑的 i線曝光用感光性樹脂組成物中,其特徵爲鹼可溶性樹脂 爲酚醛淸漆樹脂與一種或二種以上選自於(i)聚丙烯酸酯、 (ii)聚甲基丙烯酸酯、(iii)聚苯乙烯衍生物、及(iv)丙烯 酸酯、甲基丙烯酸酯及苯乙烯衍生物之單體單位所成共聚 物的樹脂之混合物所成。 於下述中,更詳細說明本發明。 本發明之圖樣形成方法中,使用i線作爲曝光光源、且 感光性樹脂組成物使用含有鹼可溶性樹脂與含醌二疊氮基 之感光劑、且該鹼可溶性樹脂爲酚醛淸漆樹脂與一種或二 種以上選自於(i)聚丙烯酸酯、(ii)聚甲基丙烯酸酯、(iii) 聚苯乙烯衍生物、及(iv)丙烯酸酯、甲基丙烯酸酯及苯乙 烯衍生物之單體單位所成共聚物的樹脂之混合物所成。使 用本發明感光性樹脂組成物進行i線曝光時之曝光量視感 光性樹脂組成物之組成而定予以適當選擇,惟實用上沒有 邊緣突出情形之圖樣形成時最適曝光量爲50〜5 OOnJ/cm2。 而且,適合FPD時以50〜200mJ/cm2較佳。 本發明之i線曝光用感光性樹脂組成物所使用的酚醛淸 漆樹脂可以爲習知含有鹼可溶性樹脂與含醌二疊氮基之感 光劑之感光性樹脂組成物所使用的酚醛淸漆樹脂,沒有特 554250 五、發明說明(5 ) 別的限制。本發明中較佳的酚醛淸漆樹脂可使各種苯酚類 單獨或此等數種之混合物以甲醛水等之醛類聚縮合所得。 構成該酚醛淸漆樹脂之苯酚類例如苯酚、對-甲酚、間-甲酚、鄰-甲酚、2,3 -二甲基苯酚、2,4 -二甲基苯酚、2,5-二甲基苯酚、2,6-二甲基苯酚、3,4-二甲基苯酚、3,5-二 甲基苯酚、2,3,4-三甲基苯酚、2,3,5-三甲基苯酚、 3,4,5 -三甲基苯酚、2,4,5 -三甲基苯酚、伸甲基雙苯酚、 伸甲基雙對-甲酚、間苯二酚、兒茶酚、2 -甲基間苯二酚、 4 -甲基間苯二酚、鄰-氯化苯酚、2,3 -二氯化苯酚、間-甲 氧基苯酚、對-甲氧基苯酚、對-丁氧基苯酚、鄰-乙基苯 酚、間-乙基苯酚、對-乙基苯酚、2,3-二乙基苯酚、2,5-二乙基苯酚、對-異丙基苯酚、α-萘酚、/3-萘酚等,此等 可單獨使用或數種之混合物。 而且,醛類例如甲醛、對甲醛、乙醛、苯甲醛、羥基苯 甲醛、氯化乙醛等’此等可單獨使用或數種之混合物使 用。 因此,本發明之感光性樹脂組成物所使用的酚醛淸漆樹 脂之重量平均分子量,以聚苯乙烯換算2,000〜50,000較 佳、更佳者以聚苯乙烯換算3,000〜40,000。 另外,例如與本發明之i線曝光用感光性樹脂組成物所 使用的構成(i)聚丙烯酸酯、(ii)聚甲基丙烯酸酯、(iii) 聚苯乙烯衍生物、及(iv)由二種以上選自於丙烯酸酯、甲 基丙烯酸酯及苯乙烯衍生物之單體單位所成的共聚物之單 554250 五、發明說明(6 ) 體例如下述所示丙烯酸酯、甲基丙烯酸酯、聚苯乙烯衍生 物較佳。 丙烯酸酯: 丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丙酯、丙烯酸正丁 酯、丙烯酸正己酯、丙烯酸異丙酯、丙烯酸異丁酯、丙烯 酸第3 -丁酯、丙烯酸環己酯、丙烯酸苯甲酯、2 -氯化乙基 丙烯酸酯、甲基-α -氯化丙烯酸酯、苯基-溴化丙烯酸 酯等。 甲基丙烯酸酯: 甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丙酯、 甲基丙烯酸正丁酯、甲基丙烯酸正己酯、甲基丙烯酸異丙 酯、甲基丙烯酸異丁酯、甲基丙烯酸第3-丁酯、甲基丙烯 酸環己酯、甲基丙烯酸苯甲酯、甲基丙烯酸苯酯、甲基丙 烯酸1-苯基乙酯、甲基丙烯酸2-苯基乙酯、甲基丙烯酸糠 酯、甲基丙烯酸二苯基甲酯、甲基丙烯酸五氯化苯酯、甲 基丙烯酸萘酯、甲基丙烯酸異冰片酯、甲基丙烯酸苯甲酯 等。 苯乙烯衍生物: 4-氟化苯乙烯、2,5-二氟化苯乙烯、2,4-二氟化苯乙烯、 對-異丙基苯乙烯、苯乙烯、鄰-氯化苯乙烯、4 -乙醯基苯 乙烯、4 -苯甲醯基苯乙烯、4·溴化苯乙烯、4 -丁氧基羰基 苯乙烯、4-丁氧基甲基苯乙烯、4-丁基苯乙烯、4-乙基苯 乙烯、4-己基苯乙烯、4-甲氧基苯乙烯、4-甲基苯乙烯、 554250 五、發明說明(7 ) 2,4-二甲基苯乙烯、2,5-二甲基苯乙烯、2,4,5-三甲基苯 乙烯、心苯基苯乙烯、4-丙氧基苯乙烯等。 另外,上述各聚合物中視其所需可使用有機酸單體作爲 共聚合成分。有機酸單體之較佳者例如下所示者。 有機酸單體: 丙烯酸、甲基丙烯酸、衣康酸、馬來酸酐、2-丙烯醯基氫 化酞酸酯、2-丙烯醯氧基丙基氫化酞酸酯等。 使用有機酸單體作爲共聚合成分時,共聚物中之丙烯酸 酯、甲基丙烯酸酯及苯乙烯衍生物部分對感光性樹脂組成 物而言具有鹼溶解抑制效果,有機酸單體部分具有提高鹼 可溶性效果。而且,藉由有機酸單體之量而定可使感光性 樹脂組成物在曝光範圍中對顯像液之溶解阻止效果與溶解 性提高效果平衡。 而且,此等聚丙烯酸酯、聚甲基丙烯酸酯、聚苯乙烯衍 生物或二種以上選自於丙烯酸酯、甲基丙烯酸酯及苯乙烯 衍生物之單體單位所成共聚物的重量平均分子量,以聚苯 乙烯換算較佳者爲2,000〜80,000、更佳者爲5,000〜 40,000。此等聚丙烯酸酯、聚甲基丙烯酸酯聚苯乙烯衍生 物、兩種以上選自於丙烯酸酯、甲基丙烯酸酯及苯乙烯衍 生物之單體單位所成共聚物的感光性樹脂組成物之含量, 對100重量份酚醛淸漆樹脂而言以0.1〜10.0重量份較 ^佳、更佳者爲0.5〜5.0重量份。 本發明i線曝光用感光性樹脂組成物中所使用的含醌二 554250 五、發明說明(8 ) 疊氮基之感光劑可使用習知含醌二疊氮基之感光劑中任一 種,惟以藉由使如含醌二疊氮基磺酸氯化物或苯并醌二疊 氮基磺酸氯化物之醒二疊氮基磺酸鹵化物與具有可與該酸 鹵化物縮合反應的官能基之低分子化合物或高分子化合物 反應所得者較佳。此處,可與酸鹵化物縮合的官能基例如 羥基、胺基等,尤以羥基爲宜。含羥基之低分子化合物例 如氫醌、間苯二酚、2,4-二羥基二苯甲酮、2,3,4-三羥基 二苯甲酮、2,4,6-三羥基二苯甲酮、2,4,4,-三羥基二苯甲 酮、2,3,4,4’-四羥基二苯甲酮、2,2,,4,4,-四羥基二苯甲 酮、2,2’,3,4,6’-六羥基二苯甲酮等,含羥基之高分子化 合物例如酚醛淸漆樹脂、聚羥基苯乙烯等。此等含醌二疊 氮基之感光劑的含量,於本發明中對100重量份感光性樹 脂組成物中之樹脂成分而言以10〜3 0重量份較佳、更佳者 爲15〜25重量份。若小於10重量份時,會有殘膜率降低 的傾向 '且在顯像時間相關性等之工程範圍內會極端惡 化。另外,若大於30重量份時低感度過低、會有感光劑析 出的情形,故在實用上會有問題。 於本發明中,另以在感光性樹脂組成物中含有下述一般
10- 554250 五、發明說明(9 ) (其中,1、R2、R3、R4、R5、R6及R7係各表示獨立的Η、 〇1〜(:4之烷基、(:1〜(:4之烷氧基、環己基、或式:
所示之基,R8係表示Η、C4之烷基、(^〜C4之烷氧基、 環己基,m及η係各爲0、1或2,a、b、c、d、e、f、g 及 h 係爲可滿足 a+bS5、c+dS5、e+f$5、g+h$5 之 0或1〜5之整數,i係表示0、1或2) 上述一般式(I)所示聚苯酚性羥基之低分子化合物,由 於本發明之感光性樹脂組成物一般作爲溶解促進劑以調整 溶解速度、或爲提高感光性樹脂組成物之感度或調整感度 時使用。 上述一般式(I)所示具苯酚性羥基之低分子化合物例如 有鄰·甲酚、對-甲酚、間-甲酚、2,4 -二甲苯酚、2,5 -二甲 苯酚、2,6-二甲苯酚、雙酚八、雙酚人、:8、(:、只、?及0、 4,4’,4”·次甲基參苯酚、2,6-雙[(2-羥基-5-甲基苯基)甲 基]-4-甲基苯酚、4,4’-[1-[4-[1-(4-羥基苯基)-1-甲基乙 基]苯基]次乙基]雙酚、4,4’,4”·次乙基參苯酚、4-[雙(4-羥基苯基)甲基]-2-乙氧基苯酚、4,4’-[(2-羥基苯基)伸甲 基]雙[2,3-二甲基苯酚]、4,4’-[(3_羥基苯基)伸甲基]雙 [2,6-二甲基苯酚]、4,4’-[(4-羥基苯基)伸甲基]雙[2,6-二甲基苯酚]、2,2’-[(2-羥基苯基)伸甲基]雙[3,5-二甲基 -11- 554250 五、發明說明(1〇) 苯酚]、2,2’-[(4-羥基苯基)伸甲基]雙[3,5-二甲基苯 酚1、4,4’-[(3,4-二羥基苯基)伸甲基]雙[2,3,6-二甲基苯 酚]、4-[雙(3-環己基-4-羥基·6-甲基苯基)甲基]-1,2-苯 二醇、4,6-雙[(3,5-二甲基-4-羥基苯基)甲基]-1,2,3-苯 三醇、4,4,-[(2-羥基苯基)伸甲基]雙[3-甲基苯酚]、 4,4’,4”-(3-甲基-1-丙基-3-鳶尾甘)參苯酚、 4,4’,4”,4’”-(1,4-伸苯基二次甲基)肆苯酚、2,4,6-參 「(3, 5-二甲基-4-羥基苯基)甲基」-1,3-苯二醇、2,4,6-參「(3, 5-二甲基-2-羥基苯基)甲基」-1,3-苯二醇、4,4,-[1-[4-[1-[4-羥基- 3,-5-雙[(羥基-3-甲基苯基)甲基]苯 基]-卜甲基乙基]苯基]次乙基]雙[2,6-雙(羥基-3-甲基苯 基)甲基]苯酚等。此等具苯酚性羥基之低分子化合物,對 100重量份酚醛淸漆樹脂而言通常爲1〜20重量份、較佳 者爲3〜1 5重量份。 於本發明之感光性樹脂組成物中可添加含有螢光物質。 本發明之感光性樹·脂組成物中可使用的螢光物質例如有萘 及1-羥基萘、1·甲基萘、2,3-二甲基萘、1-胺基萘、2-氟 化萘、2-氯化萘、1,7 -二苯基萘等之萘衍生物、蒽及9 -甲 基蒽、9, 10 -二甲基蒽、9·氰基蒽、1-胺基蒽、9 -苯基蒽、 9, 10-二苯基蒽、9-乙烯基蒽、9-(對-乙烯基苯基)-10-苯 基蒽等之蒽衍生物、菲及3,4,-苯并菲、2-苯基菲等之菲 衍生物、芘及1,3,6,8 -四苯基芘、二芘、鄰-伸苯基芘等 之芘衍生物、茈及苯并茈等之茈衍生物、芴及1-甲基芴、 -12- 554250 五、發明說明(11) 1,2 -苯幷芴等之芴衍生物、咔唑及N_甲基咔唑、甲基苯 幷味哩、N -苯基咔唑、N -乙烯基咔室等之咔唑衍生物、聯 苯及4 -甲基苯基聯苯、3,3,_二甲基聯苯、仁甲氧基聯 苯、4,4,-二甲氧基聯苯、4,4,_二羥基聯苯、4-苯甲基聯 苯、4 -乙烯基聯苯、八甲基聯苯等聯苯衍生物、對-三聯苯 及4 -甲基參聯苯、2 -甲基參聯苯、2 -甲基-對-參聯苯、 3,3”-二甲基參聯苯、4_(3,3-二甲基丁氧基卜對-參聯苯、 2,2’-伸甲基-對-參聯苯等之對-參聯苯、對聯四苯及 3, 3’”-二甲基-對聯四苯、四甲基-對聯四苯、4_(3 -乙基丁 氧基)-對聯四苯等之對聯四苯衍生物、吲哚及2 -苯基吲 哚、1-甲基-2-苯基吲哚、1-N_ 丁基-聯苯基吲哚、 二苯基吲哚、i _聯苯基-2 ·吲哚等之吲哚衍生物、吖啶及其 衍生物、丁省及其衍生物、紅縈烯及其衍生物、苯并菲及 其衍生物等。此等以考慮所使用的感光劑之吸收波長範圍 予以選擇較佳,而且,此等單獨使用或2種以上組合使 用。添加量對100重量份感光性物質而言爲0.001〜1 .0重 量份、較佳者爲0.000 5〜0.5重量份。藉由添加感光劑可 提高感度。 本發明之鹼可溶性樹脂、感光劑及使上述一般式(I )所 示溶解促進劑溶解的溶劑例如乙二醇單甲醚、乙二醇單乙 醚等乙二醇單烷醚類、乙二醇單甲醚乙酸酯、乙二醇單乙 醚乙酸酯等乙二醇單烷醚乙酸酯類、丙二醇單甲醚、丙二 醇單乙醚等丙二醇單烷醚類、丙二醇單甲醚乙酸酯、丙二 -13- 554250 五、發明說明(12 ) 醇單乙醚乙酸酯等丙二醇單烷醚乙酸酯類、乳酸甲酯、乳 酸乙酯等之乳酸酯類、甲苯、二甲苯等之芳香族烴類、甲 基乙酮、2-庚酮、環己烷等之酮類、N,N-二甲基乙烯醯 胺、N-甲基吡咯烷酮等之醯胺類、7-丁內酯等內酯類。此 等溶劑可單獨使用或2種以上混合使用。 本發明之感光性樹脂組成物中,視其所需可配合染料、 黏合助劑及界面活性劑。染料例如甲基藍、水晶紫、雲母 綠等,黏合助劑例如烷基咪唑啉、丁酸、烷酸、聚羥基苯 乙烯、聚乙烯基甲醚,界面活性劑例如非離子系界面活性 劑、例如聚醇類與其衍生物、即聚丙二醇或環氧乙烷月桂 醚、含氟界面活性劑、例如氟龍拉頓(商品名、住友斯里 耶姆公司製)、梅卡法克(商品名、大日本油墨化學工業 公司製)、史魯氟龍(商品名、旭玻璃公司製)、或有機聚 矽氧烷界面活性劑、例如KP341(商品名、信越化學工業公 司製)。 而且,光阻劑感度係不爲一義所決定的性質者,光阻劑 感度係對工程條件而言非常敏感,使不確定性原理之工程 條件決定爲某種條件時,首先決定感度之値。本發明記載 的最適曝光量係爲下述工程條件時所得之値。首先,基板 係使用4吋矽晶圓或玻璃晶圓。塗覆條件藉由旋轉條件、 預烘烤爲100°C、90秒時使光阻膜厚爲1.5//m之回轉數塗 覆光阻劑。另外,曝光係使用日立製作所公司製分檔曝光 器(光源i線·波長365nm、NA=0.50)作爲曝光機。曝 -14- 554250 五、發明說明(13) 光後之顯像條件係使用2.38重量%ΤΜΑΗ(氫氧化四甲銨)水 溶液作爲顯像液,在23 °C下進行攪拌方式顯像60秒後, 在純水中洗淨60秒、且使基板乾燥。上述爲求取本發明記 載的最適曝光量時之工程條件,變更該工程條件時,最適 曝光量爲不同之値。 於下述中藉由實施例更具體地說明本發明,惟本發明之 形態不受此等實施例所限制。 實施例1 對100重量份重量平均分子量以聚苯乙烯換算爲8,000 之酚醛淸漆樹脂而言,使2重量份聚(甲基丙烯酸甲酯- co-正-甲基丙烯酸丁酯)、21重量份平均酯化率爲75%之 2,3,4,4’-四羥基二苯甲酮與1,2-萘醌二疊氮基-5-磺醯基 氯化物之酯化物、5重量份4,4’-[1-[4-[1-(4 -羥基苯基)-1-甲基乙基]苯基]次乙基]雙酚溶解於3 90重量份丙二醇單 甲醚乙酸酯,另對全部固成分而言添加300ppm氟系界面活 性劑、梅卡法克(大日本油墨化學工業公司製)予以攪拌 後,以0 · 2 // m過濾器過濾,調製本發明感光性樹脂組成 物。將該組成物回轉塗覆於4吋矽晶圓及4吋玻璃晶圓 上,在100°C下、於熱板上烘烤後,製得1.5/z m厚之光阻 膜。在該光阻膜上以日立製作所公司製i線分檔曝光器 (ΝΑ = 0·5)曝光,以2.38重量%TMAH水溶液、在23°C下顯像 60秒。然後,藉由掃描型電子顯微鏡進行觀察最適曝光 量、臨界解樣力及圖樣形狀時,最適曝光量爲80mJ/cm2、 -15- 554250 五、發明說明(14) 臨界解像力爲0.5//m、圖樣形狀爲矩形之最佳者。 實施例2 除使用平均酯化率爲87.5%之2,3,4,4’-四羥基二苯甲 酮與1,2-萘醌二疊氮基-5-磺醯基氯化物之酯化物及平均 酯化率爲75.0%之2,3,4,4’-四羥基二苯甲酮與1,2-萘醌 二疊氮基-5-磺醯基氯化物之酯化物的混合物(混合比50: 50)外,與實施例1相同地製得最適曝光量爲85nJ/cm2、臨 界解像力爲〇.5//m、圖樣形狀爲矩形之最佳者。 實施例3 除加入2.1 Χ1(Γ5重量份(對感光劑而言0.0001重量份) 螢光物質之蒽外,與實施例1相同地製得最適曝光量爲 75m;i/cm2、臨界解像力爲0.5/ΖΠ1、圖樣形狀爲矩形之最佳 者。 實施例4 除加入1 .05 X 10_3重量份(對感光劑而言0.005重量份) 螢光物質之蒽外,與實施例1相同地製得最適曝光量爲 71m;T/Cm2、臨界解像力爲〇.5em、圖樣形狀爲矩形之最佳 者。 實施例5 除加入2.1X10·2重量份(對感光劑而言0.1重量份)螢 光物質之蒽外,與實施例1相同地製得最適曝光量爲 74m J/cm2、臨界解像力爲0.5// m、圖樣形狀爲矩形之最佳 者。 -16- 554250 五、發明說明(15) 比較例1 除使用平均酯化率爲75.0%之2,3,4,4’-四羥基二苯甲 酮與1,2-萘醌二疊氮基-5-磺醯基氯化物之酯化物爲25重 量份、且沒有使用聚(甲基丙醯酸甲酯- co-正-甲基丙烯酸 丁酯)外,與實施例1相同地製得最適曝光量爲80mJ/cm2、 臨界解像力爲〇.75/zm、圖樣形狀產生邊緣突出情形,與 實施例相比爲垂直性不佳的圖樣形狀。 【發明之效果】 如上所述,藉由本發明可形成以i線曝光形成高解像力 之圖樣形狀良好的圖樣。 -17-
Claims (1)
- 554250 --------- ι_公·告本 六、申請專利範圍 修正 (¾2¾ f辱翁茫修正:) 第901 2801 1號「對應i線之高解像光阻劑及圖樣形成 方法」專利案 六申請專利範圍 1 . 一種圖樣形成方法,其係於以i線作爲曝光光源之圖樣 形成方法中,其特徵爲感光性樹脂組成物爲含有鹼可溶 性樹脂與含醌二疊氮基之感光劑、且該鹼可溶性樹脂爲 酚醛淸漆樹脂與一種或二種以上選自於(i )聚丙烯酸 酯、(i i )聚甲基丙烯酸酯、(i i i )聚苯艺烯衍生物、及 (iv)丙烯酸酯、甲基丙烯酸酯及苯乙烯衍生物之單體單 位所成共聚物的樹脂之混合物。 2 . —種i線曝光用感光性樹脂組成物,其係於含有鹼可溶 性樹脂與含醌二疊氮基之感光劑的i線曝光用感光性樹 脂組成物中,其特徵爲鹼可溶性樹脂爲酚醛淸漆樹脂與 一種或二種以上選自於(1)聚丙烯酸酯、(ii)聚甲基丙 烯酸酯、(i i i )聚苯乙烯衍生物、及(i v )丙烯酸酯、甲 基丙烯酸酯及苯乙烯衍生物之單體單位所成共聚物的樹 脂之混合物;該感光性樹脂組成物中相對於樹脂成分爲 1 0 0重量份,所含有的醌二疊氮基爲1 〇〜3 0重量份。 3 .如申請專利範圍第2項之i線曝光用感光性樹脂組成 物,其中含醌二疊氮基之感光劑係爲四羥基二苯甲酮與 1,2 -萘醌二疊氮基磺酸之酯化物。 4 .如申請專利範圍第2或3項之i線曝光用感光性樹脂組 554250 六、申請專利範圍 成物,其中含醌二疊氮基之感光劑係爲四羥基二苯甲酮 與1,2 -萘醌二疊氮基磺酸之酯化物的混合物。 5 .如申請專利範圍第2或3項之i線曝光用感光性樹脂 組成物,其中對1 〇〇重量份含醌二疊氮基之感光劑而 言含有0.0001〜1.0重量份。
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JP3633179B2 (ja) | 1997-01-27 | 2005-03-30 | Jsr株式会社 | ポジ型フォトレジスト組成物 |
EP1087260A4 (en) * | 1999-02-15 | 2002-01-16 | Clariant Finance Bvi Ltd | PHOTOSENSITIVE RESIN COMPOSITION |
US6737212B1 (en) * | 1999-10-07 | 2004-05-18 | Clariant Finance (Bvi) Limited | Photosensitive composition |
-
2001
- 2001-11-12 TW TW090128011A patent/TW554250B/zh not_active IP Right Cessation
- 2001-12-11 JP JP2002550442A patent/JP3842736B2/ja not_active Expired - Fee Related
- 2001-12-11 WO PCT/JP2001/010857 patent/WO2002048793A1/ja not_active Application Discontinuation
- 2001-12-11 KR KR1020027010475A patent/KR100857042B1/ko not_active IP Right Cessation
- 2001-12-11 US US10/203,359 patent/US6806019B2/en not_active Expired - Fee Related
- 2001-12-11 EP EP01270806A patent/EP1345081A1/en not_active Withdrawn
- 2001-12-11 CN CNB018048307A patent/CN1208687C/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPWO2002048793A1 (ja) | 2004-04-15 |
US20030022093A1 (en) | 2003-01-30 |
US6806019B2 (en) | 2004-10-19 |
KR20030034042A (ko) | 2003-05-01 |
KR100857042B1 (ko) | 2008-09-05 |
WO2002048793A1 (fr) | 2002-06-20 |
CN1401096A (zh) | 2003-03-05 |
JP3842736B2 (ja) | 2006-11-08 |
EP1345081A1 (en) | 2003-09-17 |
CN1208687C (zh) | 2005-06-29 |
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