TWI825250B - 阻劑組成物、圖案形成方法及電子裝置之製造方法 - Google Patents
阻劑組成物、圖案形成方法及電子裝置之製造方法 Download PDFInfo
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- TWI825250B TWI825250B TW108146610A TW108146610A TWI825250B TW I825250 B TWI825250 B TW I825250B TW 108146610 A TW108146610 A TW 108146610A TW 108146610 A TW108146610 A TW 108146610A TW I825250 B TWI825250 B TW I825250B
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XFSBVAOIAHNAPC-WSORPINJSA-N acetylbenzoylaconine Chemical compound O([C@H]1[C@]2(O)C[C@H]3C45[C@@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)C4[C@]([C@@H](C[C@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-WSORPINJSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JXHGEIHXCLLHPI-UHFFFAOYSA-N benzene-1,3-diol;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC(O)=C1 JXHGEIHXCLLHPI-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- ORCDUNFQILYWIK-UHFFFAOYSA-N butyl 2-acetylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(C)=O ORCDUNFQILYWIK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- STMDLZXWMFBCQT-UHFFFAOYSA-N cyclohexyl 2-acetylbenzoate Chemical compound C(C)(=O)C1=C(C(=O)OC2CCCCC2)C=CC=C1 STMDLZXWMFBCQT-UHFFFAOYSA-N 0.000 description 1
- YZEBYEJFQJVWGX-UHFFFAOYSA-N cyclohexyl 4-formylbenzoate Chemical compound C1=CC(C=O)=CC=C1C(=O)OC1CCCCC1 YZEBYEJFQJVWGX-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- YCJSSCAQCRQQJT-UHFFFAOYSA-N ethyl 2-acetylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1C(C)=O YCJSSCAQCRQQJT-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZHXBADFCAMBDDB-UHFFFAOYSA-N formaldehyde;oxolane Chemical compound O=C.C1CCOC1 ZHXBADFCAMBDDB-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- GNWCSWUWMHQEMD-UHFFFAOYSA-N naphthalene-1,2-dione diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C(=O)C=CC2=C1 GNWCSWUWMHQEMD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MPRUUVCTEJZCGV-UHFFFAOYSA-N propyl 2-acetylbenzoate Chemical compound CCCOC(=O)C1=CC=CC=C1C(C)=O MPRUUVCTEJZCGV-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- HVFMAJWJJYBKCY-UHFFFAOYSA-N tert-butyl 2-acetylbenzoate Chemical compound CC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C HVFMAJWJJYBKCY-UHFFFAOYSA-N 0.000 description 1
- DUNFNBQQWYQKFE-UHFFFAOYSA-N tert-butyl 4-formylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C=O)C=C1 DUNFNBQQWYQKFE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical class [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- G03F7/022—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
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/18—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
-
- 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
-
- 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
-
- 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
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
本發明關於阻劑組成物。
作為IC、LSI等半導體之製造、LCD等顯示裝置之製造、印刷原版之製造等中所用的阻劑,已知使用鹼可溶性樹脂及1,2-萘醌二疊氮化合物等的感光劑之正型光阻劑。作為前述鹼可溶性樹脂,有提案使用由間甲酚酚醛清漆樹脂及對甲酚酚醛清漆樹脂所成的混合物作為鹼可溶性樹脂之正型光阻劑組成物(例如參照專利文獻1)。
專利文獻1記載之正型光阻劑組成物係以感度等的顯影性之提升為目的而開發者,但近年來,半導體之高積體化升高,有圖案細線化之傾向,要求更優異的感度。然而,於專利文獻1記載之正型光阻劑組成物中,有得不到對應於細線化的充分感度之問題。再者,由於在半導體等之製程中施予各式各樣的熱處理,故亦要求高的耐熱性,但專利文獻1記載之正型光阻劑組成物係有不具有充分的耐熱性之問題。
又,尤其於IC、LSI等半導體製造之現場,要求更微細加工,檢討利用電子束或極紫外線(EUV)之微影術。隨著曝光源之短波長化,要求對應於其的阻劑組成物之進一步的特性提升。
[專利文獻1]日本特開平2-55359號公報
本發明所欲解決的課題在於提供一種阻劑組成物,其具有高的耐熱性,可利用於使用電子束及極紫外線之微影術。
本發明者們為了解決上述課題而進行專心致力的檢討,結果發現一種阻劑組成物,其係包含使具有特定結構之含羧酸的酚系三核體化合物與脂肪族醛反應而得之酚醛清漆型酚樹脂的金屬鹽結構者,具有高的耐熱性,可利用於使用電子束及極紫外線之微影術,而完成本發明。
即,本發明關於一種阻劑組成物,其包含以下述式(1)所示的芳香族化合物(A)與脂肪族醛(B)為必要的反應原料之酚醛清漆型酚樹脂(C)的金屬鹽。
(前述式(1)中,R1及R2各自獨立地表示氫原子、碳原子數1~9的脂肪族烴基、烷氧基、芳基、芳烷基或鹵素原子;m及n各自獨立地表示0~4之整數;
R1為複數時,複數的R1可互相相同,也可相異;R2為複數時,複數的R2可互相相同,也可相異;R3表示氫原子、碳原子數1~9的脂肪族烴基或在烴基上具有1個以上的選自烷氧基、鹵基及羥基之取代基的結構部位)。
依照本發明,可提供一種阻劑組成物,其具有高的耐熱性,可利用於使用電子束及極紫外線之微影術。
以下,說明本發明之一實施形態。本發明係不受以下的實施形態所限定,在不損害本發明的效果之範圍內可加以適宜變更而實施。
本發明之阻劑組成物包含以下述式(1)所示的芳香族化合物
(A)與脂肪族醛(B)為必要的反應原料之酚醛清漆型酚樹脂(C)的金屬鹽。
(前述式(1)中,R1及R2各自獨立地表示氫原子、碳原子數1~9的脂肪族烴基、烷氧基、芳基、芳烷基或鹵素原子;m及n各自獨立地表示0~4之整數;R1為複數時,複數的R1可互相相同,也可相異;R2為複數時,複數的R2可互相相同,也可相異;R3表示氫原子、碳原子數1~9的脂肪族烴基或在烴基上具有1個以上的選自烷氧基、鹵基及羥基之取代基的結構部位)。
阻劑組成物通常含有因酸之作用分解而極性變化之樹脂(酸分解性樹脂)及因光之照射而產生酸之化合物(光酸產生劑)。於如此的阻劑組成物中,藉由曝光而光酸產生劑產生酸,藉由所產生的酸之作用而樹脂的極性變化,形成所欲的圖案。然而,由於伴隨容易發生酸擴散不均的機構,有所形成的圖案之解析度變不足之情況。
本發明之阻劑組成物係因曝光而金屬鹽結構分解,金屬離子脫離,酚醛清漆型酚樹脂(C)的極性變化而形成所欲的圖案。於沒有伴隨容易發生酸擴散不均的機構之本發明之阻劑組成物中,可得到高的解析度。尤其於使用電子束、極紫外線等短波長的光之曝光中,解析度或圖案形狀的凹凸容易成為問題,但本發明之阻劑組成物係可消除該問題。
酚醛清漆型酚樹脂(C)的金屬鹽只要酚醛清漆型酚樹脂(C)所具有的官能基之一部分或全部變成金屬鹽結構即可。
酚醛清漆型酚樹脂(C)的金屬鹽較佳為酚醛清漆型酚樹脂(C)的羧酸金屬鹽。前述酚醛清漆型酚樹脂(C)的羧酸金屬鹽較佳為下述式(X)所示的結構。
(前述式(X)中,
R1
、R2
、R3
、m及n係與前述式(1)的R1
、R2
、R3
、m及n相同;
*係與前述式(1)的3個芳香環之任一個的鍵結點,2個*可鍵結至相同的芳香環,也可各自鍵結至不同的芳香環;
Met表示金屬原子;
n表示1以上之整數)。
關於前述式(X)所示的結構,例如前述金屬原子的價數為1、2、3或4時,各自成為下述式(X1)、(X2)、(X3)或(X4)所示的結構。
於本發明之阻劑組成物中,只要在酚醛清漆型酚樹脂(C)中包含金屬鹽結構即可,該金屬鹽結構之含有率係在酚醛清漆型酚樹脂(C)的全部重複單元中,例如為1~80莫耳%,較佳為10~65莫耳%,更佳為20~50莫耳%。
於本發明之阻劑組成物中,是否形成酚醛清漆型酚樹脂(C)的金屬鹽結構,可藉由實施例中記載之方法進行確認。
以下,說明本發明之阻劑組成物所含有的成分。
[酚醛清漆型酚樹脂]
酚醛清漆型酚樹脂(C)係以下述式(1)所示的芳香族化合物(A)與脂肪族醛(B)為必要的反應原料之樹脂。
(前述式(1)中,R1
及R2
各自獨立地表示氫原子、碳原子數1~9的脂肪族烴基、烷氧基、芳基、芳烷基或鹵素原子;
m及n各自獨立地表示0~4之整數;
R1
為複數時,複數的R1
可互相相同,也可相異;
R2
為複數時,複數的R2
可互相相同,也可相異;
R3
表示氫原子、碳原子數1~9的脂肪族烴基或在烴基上具有1個以上的選自烷氧基、鹵基及羥基之取代基的結構部位)。
前述式(1)中,作為R1
、R2
及R3
之碳原子數1~9的脂肪族烴基,可舉出甲基、乙基、丙基、異丙基、丁基、第三丁基、己基、環己基、庚基、辛基、壬基等之碳原子數1~9的烷基及碳原子數3~9的環烷基等。
前述式(1)中,作為R1
及R2
的烷氧基,可舉出甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、環己氧基等。
前述式(1)中,作為R1
及R2
的芳基,可舉出苯基、甲苯基、二甲苯基、萘基、蒽基等。
前述式(1)中,作為R1
及R2
的芳烷基,可舉出苄基、苯基乙基、苯基丙基、萘基甲基等。
前述式(1)中,作為R1
及R2
的鹵素原子,可舉出氟原子、氯原子、溴原子、碘原子等。
前述式(1)中,作為R3
之「在烴基上具有1個以上的選自烷氧基、鹵基及羥基之取代基的結構部位」,可舉出鹵化烷基、鹵化芳基、2-甲氧基乙氧基、2-乙氧基乙氧基等之烷氧基烷氧基、經羥基取代的烷基烷氧基等。
前述式(1)中,n及m各自較佳為2或3之整數。
n及m各自為2時,2個R1
及2個R2
各自獨立地較佳為碳原子數1~3的烷基。此時,2個R1
及2個R2
各自較佳為鍵結至酚性羥基的2, 5-位。
前述式(1)所示的芳香族化合物(A)係可單獨使用相同結構者,也可使用具有不同分子結構之複數的化合物。
前述式(1)所示的芳香族化合物(A)例如係可藉由烷基取代苯酚(a1)與具有羧基的芳香族醛(a2)之縮合反應而調製。
前述式(1)所示的芳香族化合物(A)例如係可藉由烷基取代苯酚(a1)與具有羧基的芳香族酮(a3)之縮合反應而調製。
烷基取代苯酚(a1)係烷基取代的苯酚,該烷基可舉出碳原子數1~8的烷基,較佳為甲基。
作為烷基取代苯酚(a1)之具體例,可舉出鄰甲酚、間甲酚、對甲酚、鄰乙基苯酚、間乙基苯酚、對乙基苯酚、對辛基苯酚、對第三丁基苯酚、鄰環己基苯酚、間環己基苯酚、對環己基苯酚等之單烷基苯酚;2,5-二甲苯酚、3,5-二甲苯酚、3,4-二甲苯酚、2,4-二甲苯酚、2,6-二甲苯酚等之二烷基苯酚;2,3,5-三甲基苯酚、2,3,6-三甲基苯酚等之三烷基苯酚等。於此等之中,較佳為二烷基苯酚,更佳為2,5-二甲苯酚、2,6-二甲苯酚。烷基取代苯酚(a1)係可單獨1種使用,也可併用2種以上。
具有羧基的芳香族醛(a2)可舉出在苯、萘、苯酚、間苯二酚、萘酚、二羥基萘等之芳香核上具有甲醯基的化合物、除了甲醯基之外還更具有烷基、烷氧基、鹵素原子等的化合物。
作為具有羧基的芳香族醛(a2)之具體例,可舉出4-甲醯基苯甲酸、2-甲醯基苯甲酸、3-甲醯基苯甲酸、4-甲醯基苯甲酸甲酯、4-甲醯基苯甲酸乙酯、4-甲醯基苯甲酸丙酯、4-甲醯基苯甲酸異丙酯、4-甲醯基苯甲酸丁酯、4-甲醯基苯甲酸異丁酯、4-甲醯基苯甲酸第三丁酯、4-甲醯基苯甲酸環己酯、4-甲醯基苯甲酸第三辛酯等。於此等之中,較佳為4-甲醯基苯甲酸。具有羧基的芳香族醛(a2)係可單獨1種使用,也可併用2種以上。
具有羧基的芳香族酮(a3)係在芳香環上具有至少1個羧基或其酯衍生物與羰基的化合物。
作為具有羧基的芳香族酮(a3)之具體例,例如可舉出2-乙醯基苯甲酸、3-乙醯基苯甲酸、4-乙醯基苯甲酸、及2-乙醯基苯甲酸甲酯、2-乙醯基苯甲酸乙酯、2-乙醯基苯甲酸丙酯、2-乙醯基苯甲酸異丙酯、2-乙醯基苯甲酸丁酯、2-乙醯基苯甲酸異丁酯、2-乙醯基苯甲酸第三丁酯、2-乙醯基苯甲酸環己酯、2-乙醯基苯甲酸第三辛酯等。於此等之中,較佳為2-乙醯基苯甲酸及4-乙醯基苯甲酸。
芳香族酮(a3)係可單獨1種使用,也可併用2種以上。
作為脂肪族醛(B)之具體例,可舉出甲醛、多聚甲醛、1,3,5-三烷、乙醛、丙醛、四甲醛、聚甲醛、三氯乙醛、六亞甲基四胺、糠醛、乙二醛、正丁醛、己醛、烯丙醛、巴豆醛、丙烯醛等。脂肪族醛化合物(B)係可單獨使用1種,也可併用2種以上。
脂肪族醛(B)較佳為甲醛。
作為脂肪族醛(B),使用甲醛與甲醛以外的脂肪族醛時,相對於甲醛1莫耳,前述甲醛以外的脂肪族醛之使用量較佳為0.05~1莫耳之範圍。
酚醛清漆型酚樹脂(C)之製造方法較佳為包含下述3個步驟1~3。
(步驟1)
將烷基取代苯酚(a1)與具有羧基的芳香族醛(a2)在酸觸媒存在下,視需要地使用溶劑,在60~140℃之範圍中加熱,藉由聚縮合而得到芳香族化合物(A)。
(步驟2)
從反應溶液中單離出步驟1所得之芳香族化合物(A)。
(步驟3)
將步驟2所單離的芳香族化合物(A)與脂肪族醛(B)在酸觸媒存在下,視需要地使用溶劑,在60~140℃之範圍中加熱,藉由聚縮合而得到酚醛清漆型酚樹脂(C)。
作為上述步驟1及步驟3所用之酸觸媒,例如可舉出乙酸、草酸、硫酸、鹽酸、苯酚磺酸、對甲苯磺酸、乙酸鋅、乙酸錳等。此等之酸觸媒係可僅使用1種,也可併用2種以上。又,於此等之酸觸媒之中,從活性優異之點來看,在步驟1中較佳為硫酸、對甲苯磺酸,在步驟3中較佳為硫酸、草酸、乙酸鋅。還有,酸觸媒係可在反應前添加,也可在反應途中添加。
作為上述步驟1及步驟3中視需要使用的溶劑,例如可舉出甲醇、乙醇、丙醇等之一元醇;乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、三亞甲基二醇、二乙二醇、聚乙二醇、丙三醇等之多元醇;2-乙氧基乙醇、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、乙二醇單戊基醚、乙二醇二甲基醚、乙二醇乙基甲基醚、乙二醇單苯基醚等之二醇醚;1,3-二烷、1,4-二烷等之環狀醚;乙二醇乙酸酯等之二醇酯;丙酮、甲基乙基酮、甲基異丁基酮等之酮;甲苯、二甲苯等之芳香族烴等。此等之溶劑係可僅使用1種,也併用2種以上。又,於此等之溶劑之中,從所得之化合物的溶解性優異之點來看,較佳為2-乙氧基乙醇。
步驟1中的烷基取代苯酚(a1)與具有羧基的芳香族醛(a2)之加入比率[(a1)/(a2)],從未反應的烷基取代苯酚(a1)之去除性、生成物的產率及反應生成物的純度優異來看,莫耳比較佳為1/0.2~1/0.5之範圍,更佳為1/0.25~1/0.45之範圍。
步驟3中的芳香族化合物(A)與脂肪族醛(B)之加入比率[(A)/(B)],從可抑制過度的高分子量化(凝膠化),得到阻劑用酚樹脂的適當分子量來看,莫耳比較佳為1/0.5~1/1.2之範圍,更佳為1/0.6~1/0.9之範圍。
作為步驟2中的芳香族化合物(A)從反應溶液中單離之方法,例如可舉出將反應溶液投入反應生成物不溶或難溶的不良溶劑(S1)中,將所得之沈澱物過濾分離後,溶解反應生成物,溶解於與不良溶劑(S1)亦混合的溶劑(S2)中,再度投入不良溶劑(S1)中,過濾分離所產生的沈澱物之方法。
作為此時所用的前述不良溶劑(S1),例如可舉出水;甲醇、乙醇、丙醇等之一元醇;正己烷、正庚烷、正辛烷、環己烷等之脂肪族烴;甲苯、二甲苯等之芳香族烴。於此等之不良溶劑(S1)之中,從高效率地亦同時進行酸觸媒的去除來看,較佳為水、甲醇。另一方面,作為前述溶劑(S2),例如可舉出甲醇、乙醇、丙醇等之一元醇;乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、三亞甲基二醇、二乙二醇、聚乙二醇、丙三醇等之多元醇;2-乙氧基乙醇、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、乙二醇單戊基醚、乙二醇二甲基醚、乙二醇乙基甲基醚、乙二醇單苯基醚等之二醇醚;1,3-二烷、1,4-二烷等之環狀醚;乙二醇乙酸酯等之二醇酯;丙酮、甲基乙基酮、甲基異丁基酮等之酮等。又,使用水作為前述不良溶劑(S1)時,前述(S2)較佳為丙酮。還有,前述不良溶劑(S1)及溶劑(S2)係可各自僅1種使用,也可併用2種以上。
於上述步驟1及步驟3中作為溶劑,使用甲苯、二甲苯等之芳香族烴時,若在80℃以上加熱,則因反應而生成的前述芳香族化合物(A)係溶解於溶劑中,故直接冷卻,由於前述芳香族化合物(A)之結晶析出,藉由過濾分離其,可單離出前述芳香族化合物(A)。此時,亦可不使用前述不良溶劑(S1)及溶劑(S2)。
藉由上述步驟2之單離方法,可得到前述式(1)所示的芳香族化合物(A)。芳香族化合物(A)之純度係從凝膠滲透層析(GPC)圖所算出的純度,較佳為90%以上,更佳為94%以上,特佳為98%以上。芳香族化合物(A)之純度係可從GPC圖的面積比求出,為於後述之測定條件下測定者。
酚醛清漆型酚樹脂(C)之重量平均分子量(Mw)較佳為2,000~35,000之範圍,更佳為2,000~25,000之範圍。酚醛清漆型酚樹脂(C)之重量平均分子量(Mw)係使用凝膠滲透層析儀(以下簡稱「GPC」),於下述之測定條件下測定者。
(GPC之測定條件)
測定裝置:東曹股份有限公司製「HLC-8220 GPC」
管柱:昭和電工股份有限公司製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工股份有限公司製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工股份有限公司製「Shodex KF803」(8.0mmФ×300mm)
+昭和電工股份有限公司製「Shodex KF804」(8.0mmФ×300mm)
管柱溫度:40℃
檢測器:RI(示差折射計)
數據處理:東曹股份有限公司製「GPC-8020型號II版本4.30」
展開溶劑:四氫呋喃
流速:1.0mL/分鐘
試料:以微濾器過濾樹脂固體成分換算為0.5質量%的四氫呋喃溶液者(100μl)
標準試料:下述單分散聚苯乙烯
(標準試料:單分散聚苯乙烯)
東曹股份有限公司製「A-500」
東曹股份有限公司製「A-2500」
東曹股份有限公司製「A-5000」
東曹股份有限公司製「F-1」
東曹股份有限公司製「F-2」
東曹股份有限公司製「F-4」
東曹股份有限公司製「F-10」
東曹股份有限公司製「F-20」
[形成金屬鹽之金屬原子]
作為與酚醛清漆型酚樹脂(C)形成金屬鹽的金屬原子,可舉出鈣、鋅、銅、鐵、鋁、鋯、鉿、鈦、銦、錫等。於此等之中,較佳為鈣、鋅、銅、鐵、鋯、鉿及錫。前述金屬原子係可單獨1種使用,也可併用2種以上。
酚醛清漆型酚樹脂(C)的金屬鹽係可藉由一邊加熱包含酚醛清漆型酚樹脂(C)的組成物,一邊添加金屬原子的鹽酸鹽、硝酸鹽、硫酸鹽等的金屬鹽及或金屬氧化物而形成。於此等之中,較佳為硝酸鹽及或金屬氧化物。
相對於酚醛清漆型酚樹脂(C)100質量份,前述金屬鹽及或金屬氧化物之添加量例如為1~100質量份,較佳為10~50質量份。
[鹼可溶性樹脂]
於本發明之阻劑組成物中,酚醛清漆型酚樹脂(C)係鹼可溶性樹脂,但亦可包含酚醛清漆型酚樹脂(C)以外的鹼可溶性樹脂(D)。
鹼可溶性樹脂(D)只要是可溶於鹼水溶液中的樹脂即可,較佳為甲酚酚醛清漆樹脂。前述甲酚酚醛清漆樹脂係以酚系化合物及醛化合物為反應原料,使此等縮合而成之酚醛清漆型酚樹脂,較佳為以選自由鄰甲酚、間甲酚及對甲酚所組成之群組的1種以上之酚系化合物為必要的反應原料之樹脂。
作為成為前述甲酚酚醛清漆樹脂的反應原料之酚系化合物,亦可併用甲酚以外的苯酚或苯酚衍生物。作為甲酚以外的酚系化合物,例如可舉出苯酚;2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚等之二甲苯酚;鄰乙基苯酚、間乙基苯酚、對乙基苯酚等之乙基苯酚;異丙基苯酚、丁基苯酚、對第三丁基苯酚等之丁基苯酚;對戊基苯酚、對辛基苯酚、對壬基苯酚、對異丙苯基苯酚等的烷基苯酚;氟酚、氯酚、溴酚、碘酚等之鹵化苯酚;對苯基苯酚、胺基苯酚、硝基苯酚、二硝基苯酚、三硝基苯酚等之1取代苯酚;1-萘酚、2-萘酚等之縮合多環式苯酚;間苯二酚、烷基間苯二酚、五倍子酚、兒茶酚、烷基兒茶酚、氫醌、烷基氫醌、根皮三酚、雙酚A、雙酚F、雙酚S、二羥基萘等之多元酚等。前述甲酚以外的酚系化合物係可單獨1種使用,也可併用2種以上。
於鹼可溶性樹脂(D)之調製中以甲酚與甲酚以外的酚系化合物為反應原料時,相對於甲酚1.0莫耳,前述甲酚以外的酚系化合物之使用量較佳為0.05~1.0莫耳之範圍。
作為成為前述甲酚酚醛清漆樹脂的原料之醛化合物,例如可舉出甲醛、多聚甲醛、三烷、乙醛、丙醛、聚甲醛、三氯乙醛、六亞甲基四胺、糠醛、乙二醛、正丁醛、己醛、烯丙醛、苯甲醛、巴豆醛、丙烯醛、四甲醛、苯基乙醛、鄰甲苯甲醛、水楊醛等。於此等之中,較佳為甲醛。前述醛化合物係可單獨1種使用,也可併用2種以上。
作為成為前述甲酚酚醛清漆樹脂的原料之醛化合物,使用甲醛時,亦可使用甲醛以外的醛化合物。於前述甲酚酚醛清漆樹脂之調製中以甲醛與甲醛以外的醛化合物為反應原料時,相對於前述甲醛1.0莫耳,前述甲醛以外的醛化合物之使用量較佳為0.05~1.0莫耳之範圍。
前述酚系化合物及醛化合物之縮合反應較佳為在酸觸媒存在下進行。作為前述酸觸媒,例如可舉出草酸、硫酸、鹽酸、苯酚磺酸、對甲苯磺酸、乙酸鋅、乙酸錳等。於此等之中,從催化活性優異來看,較佳為草酸。前述酸觸媒係可單獨1種使用,也可併用2種以上。酸觸媒係可在反應前加入,也可在反應途中加入,任一者皆可。
調製前述甲酚酚醛清漆樹脂時的酚系化合物與醛化合物之加入比(莫耳比),較佳將醛化合物/酚系化合物設為0.3~1.6之範圍,更佳設為0.5~1.3之範圍。
作為調製前述甲酚酚醛清漆樹脂時的酚系化合物與醛化合物之反應之具體例,可舉出將酚系化合物與醛化合物在酸觸媒存在下加熱至60~140℃,使聚縮合反應進行,接著在減壓條件下進行脫水、脫單體之方法。
本發明之阻劑組成物可包含感光劑(E),也可不含。作為感光劑(E),可使用具有醌二疊氮基的化合物。作為該具有醌二疊氮基的化合物,例如可舉出2,3,4-三羥基二苯基酮、2,4,4’-三羥基二苯基酮、2,4,6-三羥基二苯基酮、2,3,6-三羥基二苯基酮、2,3,4-三羥基-2’-甲基二苯基酮、2,3,4,4’-四羥基二苯基酮、2,2’,4,4’-四羥基二苯基酮、2,3’,4,4’,6-五羥基二苯基酮、2,2’,3,4,4’-五羥基二苯基酮、2,2’,3,4,5-五羥基二苯基酮、2,3’,4,4’,5’,6-六羥基二苯基酮、2,3,3’,4,4’,5’-六羥基二苯基酮等之多羥基二苯基酮系化合物;雙(2,4-二羥基苯基)甲烷、雙(2,3,4-三羥基苯基)甲烷、2-(4-羥基苯基)-2-(4’-羥基苯基)丙烷、2-(2,4-二羥基苯基)-2-(2’,4’-二羥基苯基)丙烷、2-(2,3,4-三羥基苯基)-2-(2’,3’,4’-三羥基苯基)丙烷、4,4’-{1-[4-[2-(4-羥基苯基)-2-丙基]苯基]亞乙基}雙酚,3,3’-二甲基-{1-[4-[2-(3-甲基-4-羥基苯基)-2-丙基]苯基]亞乙基}雙酚等之雙[(聚)羥基苯基]烷系化合物;參(4-羥基苯基)甲烷、雙(4-羥基-3,5-二甲基苯基)-4-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-4-羥基苯基甲烷、雙(4-羥基-3,5-二甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-3,4-二羥基苯基甲烷、雙(4-羥基-3,5-二甲基苯基)-3,4-二羥基苯基甲烷等之參(羥基苯基)甲烷類或其甲基取代物;雙(3-環己基-4-羥基苯基)-3-羥基苯基甲烷、雙(3-環己基-4-羥基苯基)-2-羥基苯基甲烷、雙(3-環己基-4-羥基苯基)-4-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-2-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-3-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-4-羥基苯基甲烷、雙(3-環己基-2-羥基苯基)-3-羥基苯基甲烷、雙(5-環己基-4-羥基-3-甲基苯基)-4-羥基苯基甲烷、雙(5-環己基-4-羥基-3-甲基苯基)-3-羥基苯基甲烷、雙(5-環己基-4-羥基-3-甲基苯基)-2-羥基苯基甲烷、雙(3-環己基-2-羥基苯基)-4-羥基苯基甲烷、雙(3-環己基-2-羥基苯基)-2-羥基苯基甲烷、雙(5-環己基-2-羥基-4-甲基苯基)-2-羥基苯基甲烷、雙(5-環己基-2-羥基-4-甲基苯基)-4-羥基苯基甲烷等之雙(環己基羥基苯基)(羥基苯基)甲烷類或其甲基取代物等與萘醌-1,2-二疊氮-5-磺酸或萘醌-1,2-二疊氮-4-磺酸、鄰蒽醌二疊氮磺酸等之具有醌二疊氮基的磺酸之完全酯化合物、部分酯化合物、醯胺化物或部分醯胺化物等。此等之感光劑(E)係可僅1種使用,也可併用2種以上。
本發明之阻劑組成物的感光劑(E)之含量,從得到良好的感度,得到所欲的圖案來看,相對於酚醛清漆型酚樹脂(C)及鹼可溶性樹脂(D)之合計100質量份,較佳為3~50質量份之範圍,更佳為5~30質量份之範圍。
本發明之阻劑組成物較佳為包含溶劑(F)。作為前述溶劑(F),例如可舉出乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚等之乙二醇烷基醚;二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚等之二乙二醇二烷基醚;甲基賽珞蘇乙酸酯、乙基賽珞蘇乙酸酯等之乙二醇烷基醚乙酸酯;丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯等之丙二醇烷基醚乙酸酯;丙酮、甲基乙基酮、環己酮、甲基戊基酮等之酮;二烷等的環式醚;2-羥基丙酸甲酯、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、甲酸乙酯、乙酸乙酯、乙酸丁酯、乙醯乙酸甲酯、乙醯乙酸乙酯等之酯等。此等之溶劑(F)係可僅1種使用,也可併用2種以上。
本發明之阻劑組成物中的溶劑(F)之含量,從組成物的流動性、藉由旋塗法等塗布法得到均勻的塗膜來看,較佳為使本發明之阻劑組成物中的固體成分濃度成為15~65質量%之量。
本發明之阻劑組成物只要包含酚醛清漆型酚樹脂(C)的金屬鹽以及任意包含的鹼可溶性樹脂(D)、感光劑(E)及溶劑(F)即可,也可包含酚醛清漆型酚樹脂(C)的金屬鹽以及任意包含的鹼可溶性樹脂(D)、感光劑(E)、溶劑(F)及成分(C)~(F)以外之成分(例如由填充材、顏料、調平劑等之界面活性劑、密著性提升劑、溶解促進劑所選出的1種以上),也可在不損害本發明效果之範圍內包含不可避免的雜質。
本發明之阻劑組成物例如係溶劑(F)以外的固體成分之80質量%以上、90質量%以上、95質量%以上、98質量%以上或100質量%,但亦可包含酚醛清漆型酚樹脂(C)的金屬鹽以及任意包含的鹼可溶性樹脂(D)、感光劑(E)及成分(C)~(F)以外之成分。
本發明之阻劑組成物係可藉由通常的方法,攪拌混合酚醛清漆型酚樹脂(C)、金屬鹽、任意配合的其它鹼可溶性樹脂(D)、感光劑(E)及溶劑(F)、更視需要添加的各種添加劑,成為均勻的液體而調製。
於本發明之阻劑組成物中摻合填充材、顏料等之固體者時,較佳為使用溶解器、均質機、三輥硏磨機等之分散裝置進行分散、混合。又,為了去除粗粒或雜質,亦可使用篩網過濾器、薄膜過濾器等來過濾該組成物。
[圖案形成方法]
本發明之阻劑組成物係可作為負型光阻劑組成物使用,也可作為正型光阻劑使用。使用本發明之阻劑組成物的圖案之製造方法包含:使用本發明之阻劑組成物來形成阻劑膜之步驟,將前述阻劑膜曝光之步驟,及使用顯影液,將前述經曝光的阻劑膜顯影而形成圖案之步驟。
阻劑膜之形成、阻劑膜之曝光及經曝光的阻劑膜之顯影係可藉由眾所周知的方法實施。作為將本發明之阻劑組成物曝光的光源,例如可舉出紅外光、可見光、紫外光、遠紫外光、X射線、電子束等。於此等之光源之中,較佳為紫外光,宜為高壓水銀燈的g線(波長436nm)、i線(波長365nm)、EUV雷射(波長13.5nm)。
作為曝光後之顯影中使用的鹼顯影液,例如可使用氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、氨水等之無機鹼性物質;乙胺、正丙胺等之一級胺類;二乙胺、二正丁胺等之二級胺類;三乙胺、甲基二乙基胺等之三級胺類;二甲基乙醇胺、三乙醇胺等之醇胺;氫氧化四甲銨、氫氧化四乙銨等之四級銨鹽;吡咯、哌啶等的環狀胺等之鹼性水溶液。於此等之鹼顯影液中,視需要亦可適宜添加醇、界面活性劑等而使用。鹼顯影液之鹼濃度通常較佳為2~5質量%之範圍,一般使用2.38質量%氫氧化四甲銨水溶液。
本發明之圖案形成方法係可適用於電子裝置之製程。作為上述電子裝置,可舉出家庭用電氣機器、辦公室自動化機器、媒體相關機器、光學用機器、通訊機器等。
以下,藉由實施例與比較例,具體地說明本發明。
合成例1含羧酸的酚性三核體化合物之合成
於設有冷卻管的2000ml之4口燒瓶中,加入293.2g(2.4mol)的2,5-二甲苯酚、150g(1mol)的4-甲醯基苯甲酸,溶解於500ml的乙酸中。在冰浴中邊冷卻邊添加5ml的硫酸後,以加熱包加熱到100℃為止,邊攪拌2小時邊使其反應。於反應結束後,在所得之溶液中加入水,而使粗生成物再沈澱。將粗生成物再溶解於丙酮中,更以水使其再沈澱後,過濾分離沈澱物,進行真空乾燥,得到283g的淺桃色結晶的前驅物化合物(A-1)。
對於所得之前驅物化合物(A-1),進行13
C-NMR測定,結果確認為下述結構式所示的化合物。又,由GPC圖所算出的純度(GPC純度)為95.3%。圖1中顯示前驅物化合物(A-1)之GPC圖,圖2中顯示13
C-NMR圖。
合成例2 酚性三核體化合物之合成
於設有冷卻管的2000ml之4口燒瓶中,加入293.2g(2.4mol)的2,5-二甲苯酚、122g(1mol)的2-羥基苯甲醛,溶解於500ml的2-乙氧基乙醇中。在冰浴中邊冷卻邊添加10ml的硫酸後,以加熱包加熱到100℃為止,邊攪拌2小時邊使其反應。於反應結束後,在所得之溶液中加入水,而使粗生成物再沈澱。將粗生成物再溶解於丙酮中,更以水使其再沈澱後,過濾分離沈澱物,進行真空乾燥,得到283g的白色結晶的前驅物化合物(A’-2)。
對於所得之前驅物化合物(A’-2),進行13
C-NMR測定,結果確認為下述結構式所示的化合物。又,由GPC圖所算出的純度(GPC純度)為98.2%。圖3中顯示前驅物化合物(A’-2)之GPC圖,圖4中顯示13
C-NMR圖。
製造例1 含羧酸的酚醛清漆型酚樹脂之合成
於設有冷卻管的1000ml之4口燒瓶,加入188g的前驅物化合物(A-1)、16g的92%多聚甲醛後,溶解於500ml的乙酸中。在冰浴中邊冷卻邊添加10ml的硫酸後,在油浴中加熱到80℃為止,邊攪拌4小時邊使其反應。於反應結束後,在所得之溶液中加入水,而使粗生成物再沈澱。將粗生成物再溶解於丙酮中,更以水使其再沈澱後,過濾分離沈澱物,進行真空乾燥,得到182g的橙色粉末的酚醛清漆型酚樹脂(C-1)。所得之酚醛清漆型酚樹脂(C-1)的數量平均分子量(Mn)為3946,重量平均分子量(Mw)為8504,多分散度(Mw/Mn)為2.16。圖5中顯示酚醛清漆型酚樹脂(C-1)之GPC圖。
製造例2 含羧酸的酚醛清漆型酚樹脂之合成
除了代替前驅物化合物(A-1),使用9.4g(0.025mol)的前驅物化合物(A-1)及8.7g(0.025mol)的前驅物化合物(A’-2)以外,與製造例1同樣地,得到16.8g的淺紅色粉末的酚醛清漆型酚樹脂(C-2)。所得之酚醛清漆型酚樹脂(C-2)的數量平均分子量(Mn)為3331,重量平均分子量(Mw)為6738,多分散度(Mw/Mn)為2.02。圖6中顯示酚醛清漆型酚樹脂(C-2)之GPC圖。
製造例3 酚醛清漆樹脂之合成
於具備攪拌機、溫度計的2L之4口燒瓶中,加入552g(4mol)的2-羥基苯甲酸、498g(3mol)的1,4-雙(甲氧基甲基)苯、2.5g的對甲苯磺酸、500g的甲苯,升溫到120℃為止,進行脫甲醇反應。於減壓下升溫、蒸餾,進行230℃、6小時減壓餾去,得到882g的淡黃色固體的酚醛清漆樹脂(C’-3)。酚醛清漆樹脂(C’-3)的數量平均分子量(Mn)為1016,重量平均分子量(Mw)為2782,多分散度(Mw/Mn)為2.74。圖7中顯示酚醛清漆樹脂(C’-3)之GPC圖。
製造例4 酚醛清漆樹脂之合成
於具備攪拌機、溫度計的2L之4口燒瓶中,加入648g(6mol)的間甲酚、432g(4mol)的對甲酚、2.5g(0.2mol)的草酸、492g的42%甲醛,升溫到100℃為止而使其反應。於常壓下脫水、蒸餾到200℃為止,進行230℃、6小時減壓蒸餾,得到736g的淡黃色固體的酚醛清漆樹脂(C’-4)。
酚醛清漆樹脂(C’-4)的GPC為數量平均分子量(Mn)為1450,重量平均分子量(Mw)為10316,多分散度(Mw/Mn)為7.116。圖8中顯示酚醛清漆樹脂(C’-4)之GPC圖。
實施例1
[樹脂溶液之調製]
將製造例1所調製之酚醛清漆型酚樹脂(C-1)與丙二醇單甲基醚乙酸酯(PGMEA),以酚醛清漆型酚樹脂(C-1):PGMEA=20:80之質量比進行混合,成為酚醛清漆型酚樹脂(C-1)的PGMEA溶液,對於此溶液,以0.1μm的聚四氟乙烯製盤濾機進行精密過濾,調製樹脂溶液。
[複合化評價]
於30ml的耐熱管中加入5g的所得之樹脂溶液與各0.2g作為金屬硝酸鹽水合物的Ca(NO3
)2
・4H2
O、Zn(NO3
)2
・6H2
O、Cu(NO3
)2
・3H2
O及Fe(NO3
)3
・9H2
O,一邊振盪處理,一邊加熱到100℃為止。用下述基準評價加熱後的樹脂溶液與金屬硝酸鹽水合物之混合物的狀態。表1中顯示凝膠化評價之結果。
○:不動凝膠化
△:黏稠液體化
×:無黏度變化
依照上述評價,確認不動凝膠化或黏稠液體化後,更添加1g的鹽酸水溶液後,在室溫下進行3小時振盪處理。用下述基準評價振盪處理後之含有金屬硝酸鹽水合物的樹脂溶液之狀態,確認有無形成金屬鹽結構。表1中顯示溶膠化評價之結果。
○:低黏度液體化
△:黏稠液體化
×:無狀態變化
由表1之結果可確認,因添加金屬硝酸鹽水合物而不動凝膠化或黏稠液體化,且因更添加鹽酸水溶液而低黏度液體化之製造例1的酚醛清漆型酚樹脂(C-1),係藉由添加金屬硝酸鹽水合物而形成金屬鹽結構。
因於添加金屬硝酸鹽水合物而不動凝膠化或黏稠液體化,且因更添加鹽酸水溶液而低黏度液體化者,係由於顯示以下的行為:金屬-酚醛清漆間的配位鍵結所致的交聯結構之形成,與其解離所致的交聯結構之分解為可逆的,故表示已形成羧酸的金屬鹽。
對於所調製的樹脂溶液,另外進行下述評價。表1中顯示結果。
[鹼顯影性評價]
以在5吋矽晶圓上成為約1μm之厚度的方式,用旋塗機塗布所得之樹脂溶液,在110℃的熱板上乾燥60秒,而在矽晶圓上形成樹脂膜。將所得之晶圓浸漬於顯影液(2.38%氫氧化四甲銨水溶液)中60秒後,在110℃的熱板上乾燥60秒。測定顯影液浸漬前後的膜厚,將其差量除以60後之值當作鹼顯影性(ADR1(Å/s))。
於所得之樹脂溶液中,以成為酚醛清漆型酚樹脂/P-200/PGMEA=20/5/75(質量比)之方式,加入感光劑P-200(東洋合成工業股份有限公司製;1莫耳的4,4’-[1-[4-[1-(4-羥基苯基)-1甲基乙基]苯基]亞乙基]雙酚與2莫耳的1,2-萘醌-2-二疊氮-5-磺醯氯之縮合物),以在5吋矽晶圓上成為約1μm之厚度的方式,用旋塗機塗布此樹脂組成物,在110℃的熱板上乾燥60秒,而在矽晶圓上形成樹脂膜。將所得之晶圓浸漬於顯影液(2.38%氫氧化四甲銨水溶液)中60秒後,在110℃的熱板上乾燥60秒。測定顯影液浸漬前後的膜厚,將其差量除以60後之值當作鹼顯影性(ADR2(Å/s))。
[耐熱性評價]
以在5吋矽晶圓上成為約1μm之厚度的方式,用旋塗機塗布所得之樹脂溶液,在110℃的熱板上乾燥60秒,而在矽晶圓上形成樹脂膜。刮取此樹脂膜,測定玻璃轉移點溫度(以下簡稱「Tg」),用下述基準進行評價。
○:Tg為150℃以上
×:Tg為150℃以下
還有,Tg之測定係使用示差熱掃描熱量計(TA Instruments股份有限公司製「示差熱掃描熱量計(DSC)Q100」),於氮氣環境下、溫度範圍-100~200℃、升溫速度10℃/分鐘之條件下進行。
實施例2及比較例1-2
除了代替酚醛清漆型酚樹脂(C-1),使用表1中所示的樹脂以外,與實施例1同樣地調製樹脂溶液,進行評價。表1中顯示結果。還有,關於酚醛清漆樹脂(C’-3)及酚醛清漆樹脂(C’-4)之樹脂溶液,在凝膠化評價中無黏度變化時,不進行溶膠化之評價。
[表1]
實施例1 | 實施例2 | 比較例1 | 比較例2 | |||
樹脂 | C-1 | C-2 | C'-3 | C'-4 | ||
鹼顯 影性 | ADR1 [Å/s] | 15000 | 10000 | 3500 | 110 | |
ADR2 [Å/s] | 80 | 56 | 2900 | 15 | ||
耐熱性 | Tg [℃] | 270 | 220 | 52 | 110 | |
判定 | ○ | ○ | × | × | ||
複合化 | Ca(NO3 )2 ・4H2 O | 凝膠化 | △ | △ | × | × |
溶膠化 | ○ | ○ | - | - | ||
Zn(NO3 )2 ・6H2 O | 凝膠化 | △ | △ | × | × | |
溶膠化 | ○ | ○ | - | - | ||
Cu(NO3 )2 ・3H2 O | 凝膠化 | ○ | ○ | △ | × | |
溶膠化 | ○ | ○ | × | - | ||
Fe(NO3 )3 ・9H2 O | 凝膠化 | ○ | ○ | △ | × | |
溶膠化 | ○ | ○ | △ | - |
無。
圖1係合成例1所得之前驅物化合物的GPC圖。
圖2係合成例1所得之前驅物化合物的13C-NMR圖。
圖3係合成例2所得之前驅物化合物的GPC圖。
圖4係合成例2所得之前驅物化合物的13C-NMR圖。
圖5係製造例1所得之酚醛清漆型酚樹脂的GPC圖。
圖6係製造例2所得之酚醛清漆型酚樹脂的GPC圖。
圖7係製造例3所得之酚醛清漆樹脂的GPC圖。
圖8係製造例4所得之酚醛清漆樹脂的GPC圖。
無。
Claims (9)
- 如請求項1之阻劑組成物,其中該金屬鹽係羧酸金屬鹽。
- 如請求項1或2之阻劑組成物,其中該金屬鹽的金屬原子係選自鈣原子、鋅原子、銅原子及鐵原子之1個以上。
- 如請求項1或2之阻劑組成物,其中該芳香族化合物(A)係苯酚化合物與具有羧基或羧基酯基的芳香族醛及/或 具有羧基或羧基酯基的芳香族酮之聚縮合物。
- 如請求項4之阻劑組成物,其中該具有羧基的芳香族醛係甲醯基苯甲酸。
- 如請求項1或2之阻劑組成物,其中該脂肪族醛(B)係甲醛及/或多聚甲醛。
- 一種圖案形成方法,其包含:使用如請求項1至6中任一項之阻劑組成物來形成阻劑膜之步驟,將該阻劑膜曝光之步驟,及使用顯影液,將該經曝光的阻劑膜顯影而形成圖案之步驟。
- 如請求項7之圖案形成方法,其中該曝光係藉由電子束或極紫外線所致的曝光。
- 一種電子裝置之製造方法,其包含如請求項7或8之圖案形成方法。
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