JP5165274B2 - フォトレジスト組成物 - Google Patents
フォトレジスト組成物 Download PDFInfo
- Publication number
- JP5165274B2 JP5165274B2 JP2007122608A JP2007122608A JP5165274B2 JP 5165274 B2 JP5165274 B2 JP 5165274B2 JP 2007122608 A JP2007122608 A JP 2007122608A JP 2007122608 A JP2007122608 A JP 2007122608A JP 5165274 B2 JP5165274 B2 JP 5165274B2
- Authority
- JP
- Japan
- Prior art keywords
- photoresist composition
- weight
- cresol
- photoresist
- diazide
- 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.)
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 68
- 239000000203 mixture Substances 0.000 title claims description 51
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 22
- 229920003986 novolac Polymers 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 17
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 17
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 17
- 229940100630 metacresol Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 11
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 10
- 229960001755 resorcinol Drugs 0.000 claims description 10
- 230000035945 sensitivity Effects 0.000 claims description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003623 enhancer Substances 0.000 claims description 7
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims 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 claims description 3
- WFGOHWBMXOABAR-UHFFFAOYSA-N (3,4-dihydroxyphenyl)-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)C1=CC(O)=C(O)C(O)=C1O WFGOHWBMXOABAR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 claims description 2
- 101100046775 Arabidopsis thaliana TPPA gene Proteins 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229940079877 pyrogallol Drugs 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 description 20
- 206010034972 Photosensitivity reaction Diseases 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000036211 photosensitivity Effects 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance 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
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- ZYRNCIWULACSEK-UHFFFAOYSA-N 3-(4-methoxybenzoyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(=O)C(C)(C)OC1=O ZYRNCIWULACSEK-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- -1 organic acid cyclic anhydride Chemical class 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ALVGSDOIXRPZFH-UHFFFAOYSA-N [(1-diazonioimino-3,4-dioxonaphthalen-2-ylidene)hydrazinylidene]azanide Chemical compound C1=CC=C2C(=N[N+]#N)C(=NN=[N-])C(=O)C(=O)C2=C1 ALVGSDOIXRPZFH-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
-
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- 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
- G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Description
[化1]
(化学式1で、Rは水素、-OHまたは-CH3であり、nは3乃至20の整数である。)
また、本発明は前記フォトレジスト組成物を利用して製造される液晶表示装置または半導体素子を提供する。
メタ-クレゾール:パラ-クレゾール:レゾルシン及び縮合剤としてサリチルアルデヒドを使用(重量比4:4:2:2)したノボラック樹脂(重量平均分子量4,800)20g、並びに2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、さらに感度増進剤である4,4-[1-[4-[1-(1,4-ヒドロキシフェニル)-1-メチルエチル]フェニル]エチリデン]ビスフェノール2.8g、及び有機溶媒であるプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
メタ-クレゾール:パラ-クレゾール:レゾルシン及び縮合剤としてサリチルアルデヒドを使用(重量比3:4:2:2)したノボラック樹脂(重量平均分子量4,800)20g、並びに2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、さらに感度増進剤である4,4-[1-[4-[1-(1,4-ヒドロキシフェニル)-1-メチルエチル]フェニル]エチリデン]ビスフェノール2.8g、及び有機溶媒であるプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
メタ-クレゾール:パラ-クレゾール:レゾルシン及び縮合剤としてサリチルアルデヒドを使用(重量比3:3:2:2)したノボラック樹脂(重量平均分子量4,800)20g、並びに2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、さらに有機溶媒であるプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
メタ-クレゾール:パラ-クレゾール:レゾルシン及び縮合剤としてサリチルアルデヒドを使用(重量比3:3:2:2)したノボラック樹脂(重量平均分子量7,800)20g、2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、及び有機溶媒であるプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
メタ-クレゾール:パラ-クレゾールの重量比が4:6で、縮合剤としてホルムアルデヒドを使用したノボラック樹脂(重量平均分子量4,325)20g、並びに2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、さらに有機溶媒のプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
メタ-クレゾール:パラ-クレゾール:2,5-クシルレノルの重量比が4:4:2で、縮合剤としてホルムアルデヒドを使用したノボラック樹脂(重量平均分子量4,800)20g、並びに2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を50/50重量部で混合したジアジド系感光性化合物4g、さらに有機溶媒のプロピレングリコールメチルエーテルアセテート(PGMEA)60gを均一に混合してフォトレジスト組成物を製造した。
前記実施例及び比較例で製造したフォトレジスト組成物に対して下記のような実験をしてその結果は下記表1に示した。
*初期フィルム厚さ=損失厚さ+残膜の厚さ
*残膜率=(残膜の厚さ/初期フィルム厚さ)×100%
感光速度は露光エネルギーによって一定の現像条件で膜が完全に溶けていくエネルギーを測定して求め、110℃でソフトベークを行って露光及び現像した後、残膜率を測定し、その結果を示す現像前後の厚さの差を測定した。
435nm波長の紫外線に露光させた後、現像工程を経てパターンを形成してSEMによってパターンの解像度を測定した。
耐熱性はハードベークを130℃で90秒間進行した後、SEMによってパターンの流れで確認した。
モリブデン(Mo)がコーティングガラス上に形成されたパターン(微細線幅)を得た後、露出された部位のモリブデンを除去するために腐蝕溶液で処理して腐蝕溶液が露出されないモリブデンを腐蝕させた厚さを測定して接着性を実験した。
Claims (6)
- a)メタ-クレゾール(m-cresol):パラ-クレゾール(p-cresol):レゾルシン:サリチルアルデヒドを重量比2乃至5:2乃至5:0.5乃至3:0.5乃至3で混合して重合したものであり、重量平均分子量が2,000乃至10,000であるノボラック樹脂、
b)ジアジド系感光性化合物、及び
c)有機溶媒を含むことを特徴とするフォトレジスト組成物。 - a)ノボラック樹脂5乃至30重量%、
b)ジアジド系感光性化合物2乃至10重量%、及び
c)有機溶媒残部を含むことを特徴とする、請求項1に記載のフォトレジスト組成物。 - 前記b)ジアジド系感光性化合物は2,3,4-トリヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩及び2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸塩を4乃至6:6乃至4の重量比で含むことを特徴とする、請求項1に記載のフォトレジスト組成物。
- 前記c)有機溶媒はプロピレングリコールメチルエーテルアセテート(PGMEA)、乳酸エチル(EL)、2-メトキシ酢酸エチル、プロピレングリコールモノメチルエーテル(PGME)からなる群より1種以上選択されることを特徴とする、請求項1に記載のフォトレジスト組成物。
- 前記組成物は2,3,4-トリヒドロキシベンゾフェノン、2,3,4,4’-テトラヒドロキシベンゾフェノン、2,3,4,3’,4’,5-ヘキサヒドロキシベンゾフェノン、アセトン-ピロガロール縮合物、4,4’-[1-[4-[1-(4-ヒドロキシフェニル)-1-メチルエチル]フェニル]エチリデン]ビスフェノール(TPPA)及び4,4’-((2-ヒドロキシフェニル)メチレン)ビス(2,6-ジメチルフェノール)(BI26X-SA)からなる群より1種以上選択されるd)感度増進剤を0.1乃至10重量%、さらに含むことを特徴とする、請求項1に記載のフォトレジスト組成物。
- 前記フォトレジスト組成物は着色剤、染料、可塑剤、接着促進剤、速度増進剤及び界面活性剤からなる群より1種以上選択される添加剤をさらに含むことを特徴とする、請求項1に記載のフォトレジスト組成物。
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