KR101392648B1 - Stripper composition for removal photoresist residue and stripping method of photoresists using the same - Google Patents
Stripper composition for removal photoresist residue and stripping method of photoresists using the same Download PDFInfo
- Publication number
- KR101392648B1 KR101392648B1 KR1020080004686A KR20080004686A KR101392648B1 KR 101392648 B1 KR101392648 B1 KR 101392648B1 KR 1020080004686 A KR1020080004686 A KR 1020080004686A KR 20080004686 A KR20080004686 A KR 20080004686A KR 101392648 B1 KR101392648 B1 KR 101392648B1
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- photoresist
- photoresist residue
- liquid composition
- compound
- Prior art date
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 99
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 45
- -1 sulfonic acid compound Chemical class 0.000 claims abstract description 34
- 239000007788 liquid Substances 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004380 ashing Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000002222 fluorine compounds Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000005530 etching Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 6
- 229940044654 phenolsulfonic acid Drugs 0.000 claims description 5
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 claims description 4
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 claims description 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 4
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 4
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 claims description 3
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 claims description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 3
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims description 2
- KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims 4
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 claims 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 229910052751 metal Inorganic materials 0.000 abstract description 20
- 239000002184 metal Substances 0.000 abstract description 20
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 239000004065 semiconductor Substances 0.000 abstract description 11
- 238000005507 spraying Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 238000000151 deposition Methods 0.000 abstract description 3
- 238000005536 corrosion prevention Methods 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 description 26
- 230000007797 corrosion Effects 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 16
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 238000001020 plasma etching Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Substances [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- IBHWREHFNDMRPR-UHFFFAOYSA-N 2,4,6-Trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 4
- 101100424834 Brugia malayi tsa-2 gene Proteins 0.000 description 4
- 229910017855 NH 4 F Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CHZLVSBMXZSPNN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1 CHZLVSBMXZSPNN-UHFFFAOYSA-N 0.000 description 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 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
- G03F7/26—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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0073—Anticorrosion compositions
-
- 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
- G03F7/06—Silver salts
- G03F7/063—Additives or means to improve the lithographic properties; Processing solutions characterised by such additives; Treatment after development or transfer, e.g. finishing, washing; Correction or deletion fluids
-
- 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
- G03F7/30—Imagewise removal using liquid means
-
- 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
-
- 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
- G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
-
- 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
- G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides
-
- C11D2111/22—
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
본 발명은 (A) 유기 술폰산 화합물, (B) 방향족 하이드록시카르복시산 화합물 및 (C) 물을 함유하는 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 이용하는 박리 방법에 관한 것이다. 본 발명에 의해, 반도체 소자 및 평판표시소자 등의 제조공정에 있어서, 에싱 공정 중 발생할 수 있는 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물의 박리를 위해, 배치 방식 또는 매엽 방식의, 침적법 또는 분무법으로 용이하게 제거할 수 있으며, 박리액 조성물에 노출되는 하부의 금속막 및 절연막에 대한 부식 방지 효과가 우수한 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 이용하는 박리 방법이 제공된다.The present invention relates to a peeling liquid composition for removing photoresist residue containing (A) an organic sulfonic acid compound, (B) an aromatic hydroxycarboxylic acid compound and (C) water, and a peeling method using the same. According to the present invention, in the manufacturing process of a semiconductor device and a flat panel display device, in order to peel off the photoresist residue including curing and / or altered photoresist that may occur during the ashing process, There is provided a peeling liquid composition for removing photoresist residues which can be easily removed by a deposition method or a spraying method and is excellent in corrosion prevention effect on a metal film and an insulating film which are exposed to the peeling liquid composition, and a peeling method using the same.
유기 술폰산 화합물, 방향족 하이드록시카르복시산 화합물, 박리 An organic sulfonic acid compound, an aromatic hydroxycarboxylic acid compound,
Description
본 발명은 반도체소자 또는 평판표시소자의 제조공정 중 에칭(etching) 및 에싱(ashing)을 거친 기판에 잔류하는 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물 등을 제거함에 있어, 박리액 조성물에 노출되는 하부 금속막 또는 절연막의 부식 없이 효과적으로 제거하는 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 이용하는 박리 방법에 관한 것이다.In removing the photoresist residues including cured and / or altered photoresist remaining on a substrate subjected to etching and ashing during the manufacturing process of a semiconductor device or a flat panel display device, To a removing liquid composition for removing photoresist residue which is effectively removed without corrosion of a lower metal film or an insulating film exposed to the liquid composition, and a peeling method using the same.
반도체소자 및 평판표시소자의 제조는, 금속막 또는 절연막을 형성하는 공정, 포토레지스트를 형성하는 공정, 포토레지스트에 마스크 패턴을 전사하는 노광 공정, 패턴을 따라 막을 에칭하는 식각 공정 및 포토레지스트를 제거하는 박리공정을 포함하여 진행된다. 상기 박리 공정에서는, 웨이퍼 또는 기판 위에 도포된 포토 레지스트를 습식 에싱 또는 건식 에싱으로 제거하고 있다. 이러한 습식 에싱 또는 건식 에싱 공정 후, 일부 변질 및/또는 경화된 포토레지스트 잔류물 등이 존재하게 된다. 상기 변질 및/또는 경화된 포토레지스트를 완전히 제거하지 않는 경 우, 포토레지스트 잔류물이 후속 공정에서의 배선의 단락, 단선의 요인으로 작용할 수 있기 때문에 생산 수율의 저하 요인이 될 수 있다.The semiconductor device and the flat panel display device are manufactured by a process including the steps of forming a metal film or an insulating film, forming a photoresist, exposing the mask pattern to a photoresist, etching the film along the pattern, Including a peeling process It proceeds. In the peeling step, the photoresist applied on the wafer or the substrate is removed by wet ashing or dry ashing. After such wet ashing or dry ashing processes, some altered and / or cured photoresist residues and the like will be present. If the modified and / or cured photoresist is not completely removed, the photoresist residue may act as a factor of shorting or breaking the wiring in the subsequent process, which may be a factor of lowering the yield of production.
이러한 문제점을 극복하기 위하여, 에싱 공정 후에 잔류하는 변질 및/또는 경화된 포토레지스트는 습식 공정을 통하여 제거되고 있다. 상기의 습식 공정에서 포토레지스트를 제거하기 위하여 사용하고 있는 박리 용액 조성물은 [아민 + 유기용매 + 부식방지제], [산 + 유기산염 또는 무기산염 + 물] 또는 [불소화합물 + 4급암모늄화합물 + 물], [불소화합물 + 4급암모늄화합물 + 유기용매 + 물]로 구성된 것들이 제안되었다. To overcome this problem, residual and / or cured photoresist remaining after the ashing process has been removed through a wet process. The removal solution composition used for removing the photoresist in the above-mentioned wet process may be a combination of [amine + organic solvent + corrosion inhibitor], [acid + organic acid salt or inorganic acid salt + water] or [fluorine compound + quaternary ammonium compound + water ], [Fluorine compound + quaternary ammonium compound + organic solvent + water].
예를 들면 미국 등록특허 제4,617,251호는, 특정 아민 화합물 [예컨대, 2-(2-아미노에톡시)에탄올, 2-(2-아미노에틸아미노)에탄올, 또는 이들의 혼합물] 및 극성 용매(예컨대, N-메틸-2-피롤리돈(NMP), 테트라히드로푸르푸릴알코올, 디메틸글루타레이트, 술포란, 감마-부티로락톤(GBL), N,N-디메틸아세트아미드 및 이들의 혼합물)을 함유하는 포지형 포토레지스트 박리제 조성물에 대해 개시하고 있다. 또한, 미국 등록특허 제5,279,771호는, 하이드록실아민, 알칸올아민 및 임의의 극성 용매를 포함하는 스트리핑 조성물을 개시하고 있다. 그러나, 상기의 아민계 박리용액은, 플라즈마 에칭, 고온 에싱 후 잔류하는 폴리머나 이온 주입 후 경화된 포토레지스트를 완전하게 제거하지 못하거나, 알루미늄과 같은 금속막을 부식시키는 등의 심각한 문제점을 안고 있다. For example, U.S. Patent No. 4,617,251 discloses a process for the preparation of a compound of formula (I) wherein a specific amine compound [such as 2- (2-aminoethoxy) ethanol, 2- (NMP), tetrahydrofurfuryl alcohol, dimethyl glutarate, sulfolane, gamma-butyrolactone (GBL), N, N-dimethylacetamide and mixtures thereof) Lt; RTI ID = 0.0 > photoresist < / RTI > Also, U.S. Patent No. 5,279,771 discloses a stripping composition comprising a hydroxylamine, an alkanolamine and optionally a polar solvent. However, the above-mentioned amine-based peeling solution has serious problems such as the plasma etching, the residual polymer after the high-temperature ashing, the complete removal of the cured photoresist after ion implantation, and the corrosion of a metal film such as aluminum.
일반적으로 상용되는 박리 용액에는, 아민 등의 성분에 의한 알루미늄과 같은 금속막의 부식을 억제하기 위한 금속 부식 방지제가 첨가되어 사용되고 있다.A metal corrosion inhibitor for suppressing corrosion of a metal film such as aluminum by a component such as amine is added to a commonly used exfoliating solution.
예를 들면 대한민국 등록특허 제10-0736800호는 수산화물, 물, 금속 부식방지제로 구성된 조성물에 금속 부식방지제로서 황 원소를 포함하는 조성물을 개시하고 있고, 대한민국 공개특허 10-2006-0045957호는 아민, 용제 및 부식방지제로 구성된 레지스트 제거용 조성물, 여기서 상기 부식방지제가 트리아졸류 화합물, 머캅토류 화합물 및 하이드록실기를 갖는 벤젠류 화합물 등에서 선택된 1종 이상인 조성물을 개시하고 있다. For example, Korean Patent Registration No. 10-0736800 discloses a composition comprising a sulfur element as a metal corrosion inhibitor in a composition composed of a hydroxide, water and a metal corrosion inhibitor. Korean Patent Laid-Open No. 10-2006-0045957 discloses a composition comprising an amine, A composition for removing a resist comprising a solvent and a corrosion inhibitor, wherein the corrosion inhibitor is at least one selected from triazole compounds, mercapto compounds and benzene compounds having a hydroxyl group.
또한, 대한민국 공개특허 제10-2004-75058호는 a)수용성 유기용매, b)술폰산 또는 그의 상응하는 염, 및 c)물로 구성된 조성물에 d)부식 억제제가 추가로 포함되는 조성물을 개시하고 있고, 대한민국 공개특허 제10-2006-98333호는, a)아세틸렌 알코올 화합물 및 유기술폰산 화합물 중 적어도 1종과 b)다가 알코올 및 그 유도체 중 적어도 1종을 함유하는 포토레지스트 박리액 조성물을 제안하고 있다. Korean Patent Laid-Open No. 10-2004-75058 discloses a composition further comprising a corrosion inhibitor in a) a water-soluble organic solvent, b) a sulfonic acid or a corresponding salt thereof, and c) water, Korean Patent Laid-Open No. 10-2006-98333 proposes a photoresist stripper composition containing at least one of a) an acetylenic alcohol compound and an organic sulfonic acid compound and b) a polyhydric alcohol and a derivative thereof.
불소화합물이 첨가된 조성물의 예로서, 일본국 특개 제2001-5200호에서 [불소화합물 + 아스코르빈산 + 극성유기용매]로 이루어진 조성물이 보고되어 있으나, 조성물의 불안전성이 문제가 되고 있다. 또한 대한민국 공개특허 제10-2006-50601호는 불소화합물과 설폰산류 및 물로 이루어진 조성물을 제안하고 있으나, 첨가되는 불소의 함유량이 높은 문제점을 갖고 있다.As an example of a composition to which a fluorine compound is added, a composition comprising [fluorine compound + ascorbic acid + polar organic solvent] has been reported in Japanese Patent Laid-Open No. 2001-5200, but the instability of the composition has been a problem. Korean Patent Laid-Open Publication No. 10-2006-50601 proposes a composition comprising a fluorine compound, a sulfonic acid group and water, but has a high content of fluorine added.
불소화합물이 포함된 조성물의 경우 조성의 불안정성과 더불어 박리 조건의 마진폭이 좁은 문제점을 갖고 있다. 또한 유기계 박리 조성물의 경우 박리 후 세정 시간이 길고 환경 처리 비용이 높은 문제점을 갖고 있을 뿐만 아니라 웨이퍼의 크기가 대구경화됨에 따라 적용되고 있는 매엽식 방식에 적용하기에는 비용면에서 문 제점이 존재한다. 따라서, 포토레지스트의 제거성이 우수함과 동시에, 금속막 및 절연막에 대한 방식효과가 우수하고, 세정처리시간을 단축시킬 수 있는 보다 효과적이고도, 저렴한 가격의 박리제가 요구되고 있다.In the case of a composition containing a fluorine compound, there is a problem that the margin of the peeling condition is narrow in addition to the instability of the composition. In addition, the organic peeling composition has a problem in that it has a long cleaning time after peeling and a high environmental treatment cost, and there is a problem in terms of cost to apply to the single-wafer method in which the size of the wafer is increased. Therefore, there is a demand for a remover which is excellent in the removability of the photoresist, excellent in the effect of the system on the metal film and the insulating film, and more effective and inexpensive to shorten the cleaning process time.
이에, 본 발명자들은 상기한 문제점을 해결하고자 예의 노력한 결과, 유기술폰산 화합물, 방향족 하이드록시카르복시산 화합물 및 물로 이루어진 본 발명의 박리액 조성물을 기판에 처리하였을 때 포토레지스트막에 대한 박리능이 탁월할 뿐만아니라, 금속막 또는 절연막의 부식성이 낮음을 확인하여 본 발명을 완성하였다.As a result, the present inventors have made extensive efforts to solve the above-mentioned problems. As a result, they have found that when the substrate is treated with the release liquid composition of the present invention comprising an organic sulfonic acid compound, an aromatic hydroxycarboxylic acid compound and water, , The corrosion resistance of the metal film or the insulating film is low, and the present invention has been completed.
따라서, 본 발명의 목적은 반도체소자 및 평판표시소자의 제조 공정에서, 에싱 후 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물을 금속막 및 절연막의 부식 없이 제거하는 박리액 조성물을 제공하는 것으로서, 특히 알루미늄 막질을 포함하는 소자의 제조 공정에 효과적인 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 이용하는 박리 방법을 제공하는 것이다.SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a peeling liquid composition for removing photoresist residues containing photoresist, which is hardened and / or altered after ashing, without corrosion of a metal film and an insulating film in a process of manufacturing semiconductor devices and flat panel display devices The present invention provides a peeling liquid composition for removing photoresist residues, which is effective for manufacturing a device including an aluminum film, and a peeling method using the same.
상기 목적의 달성을 위하여, 본 발명은 In order to achieve the above object,
(A) 유기술폰산 화합물,(A) an organic sulfonic acid compound,
(B) 하기 화학식 1로 표시되는 방향족 하이드록시카르복시산 화합물, 및 (B) an aromatic hydroxycarboxylic acid compound represented by the following formula (1), and
(C) 물을 포함하는 것을 특징으로 하는 포토레지스트 잔류물 제거용 박리액 조성물을 제공한다.(C) water. The present invention also provides a peeling liquid composition for removing photoresist residues.
[화학식 1][Chemical Formula 1]
상기 식에서, m은 1 내지 3의 정수이고, n은 1 내지 3의 정수이다.Wherein m is an integer of 1 to 3 and n is an integer of 1 to 3.
또한, 본 발명은 상기 포토레지스트 잔류물 제거용 박리액 조성물을 이용하는 것을 특징으로 하는 포토레지스트 박리 방법을 제공한다.Further, the present invention provides a photoresist stripping method using the stripper composition for removing the photoresist residue.
이하에서는 본 발명에 대해 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 반도체소자 및 평판표시소자의 제조 공정 중 하나인 포토리소그래피 공정에서 발생하는, 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트의 잔류물을 금속막 및 절연막의 부식 없이, 특히 알루미늄을 포함하는 금속의 부식 없이 효과적으로 제거할 수 있는 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 이용한 박리 방법을 제공한다.The present invention relates to a method of manufacturing a semiconductor device and a method of manufacturing a flat panel display device, in which a residue of a photoresist, which is generated in a photolithography process, which is one of the processes of manufacturing a semiconductor device and a flat panel display device, The present invention provides a peeling liquid composition for removing photoresist residues, which can be effectively removed without corrosion of metals contained therein, and a peeling method using the same.
본 발명은 조성물 총중량에 대하여, The present invention relates to a composition comprising,
(A) 유기술폰산 화합물 0.1 내지 20 중량%; (A) 0.1 to 20% by weight of an organic sulfonic acid compound;
(B) 하기 화학식 1로 표시되는 방향족 하이드록시카르복시산 화합물 0.1 내지 20 중량%; 및 (B) 0.1 to 20% by weight of an aromatic hydroxycarboxylic acid compound represented by the following formula (1); And
(C) 전체 조성물 총중량이 100 중량%가 되도록 하는 잔량의 물을 포함하는 것을 특징으로 하는 포토레지스트 잔류물 제거용 박리액 조성물을 제공한다.(C) a residual amount of water so that the total weight of the total composition becomes 100% by weight.
[화학식 1][Chemical Formula 1]
상기 식에서, m은 1 내지 3의 정수이고, n은 1 내지 3의 정수이다.Wherein m is an integer of 1 to 3 and n is an integer of 1 to 3.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물에 포함되는 유기술폰산 화합물은 유기술폰산 또는 이의 염 화합물로서, 수용액상에 해리될 때 해리상수, 또는 산성도가 높은 편이다. 반도체 공정에서 유기물을 제거하는 공정에는 일반적으로 황산이 널리 사용되고 있는데, 이는 황산이 산성도가 높고, 산화시키는 능력이 강하기 때문이다. 즉, 물 속에 용해되는 경우 수소 이온의 발생량이 높기 때문에 수소이온지수가 작게 표시되고 있다. 이와 같은 수소이온 즉, 산 이온은 폴리머인 소수성의 포토레지스트와 반응하여 친수성의 포토레지스트로 변화시키는 한편, 포토레지스트 내 결합을 완화시키는 작용을 할 수 있으며, 완화된 포토레지스트는 다른 작용기에 의하여 보다 쉽게 용해되는 특성을 가지게 되는 것이다. 이러한 특성으로 인하여 황산과 유사한 산 해리 상수, 즉 산성도를 가질 수 있는 유기 술폰산을 사용하는 경우, 황산과 같은 강한 산성도에 의하여 포토레지스트를 보다 쉽게 제거할 수 있게 된다. 이에 따라 종래의 박리액으로는 제거하기가 어려웠던 포토레지스트 변질층 및 측벽 보호 퇴적막을 포토레지스트와 함께 제거할 수 있 도록 하는 역할을 수행한다.The organic sulfonic acid compound contained in the stripper solution composition for removing photoresist residue of the present invention is an organic sulfonic acid or a salt thereof, and has a high dissociation constant or acidity when dissociated into an aqueous solution. Sulfuric acid is generally used in the process of removing organic substances in a semiconductor process because sulfuric acid has a high acidity and a strong oxidizing ability. That is, when dissolved in water, the amount of generated hydrogen ions is high, so that the hydrogen ion index is indicated to be small. Such a hydrogen ion, that is, an acid ion reacts with a hydrophobic photoresist as a polymer to convert it into a hydrophilic photoresist, and can act to relax the bond in the photoresist, and the relaxed photoresist can be modified by other functional groups It is easy to dissolve. Due to these properties, when an organic sulfonic acid having an acid dissociation constant similar to sulfuric acid, that is, an acidity, is used, the photoresist can be easily removed by strong acidity such as sulfuric acid. Accordingly, the photoresist modified layer and the sidewall protective deposited layer, which have been difficult to remove with conventional peeling liquid, can be removed together with the photoresist.
상기 유기술폰산 화합물은 The organic sulfonic acid compound
(a) 탄소수 1 내지 4의 알킬술폰산; (a) an alkylsulfonic acid having 1 to 4 carbon atoms;
(b) 탄소수 6 내지 8의 아릴술폰산; (b) an arylsulfonic acid having 6 to 8 carbon atoms;
(c) 탄소수 5 내지 7의 헤테로아릴술폰산;(c) a heteroarylsulfonic acid having 5 to 7 carbon atoms;
(d) 탄소수 7 내지 18의 알킬벤젠술폰산; 및 (d) an alkylbenzenesulfonic acid having 7 to 18 carbon atoms; And
(e) 이의 염을 포함하는 군으로부터 선택되는 1종 또는 2종 이상을 혼합하여 사용할 수 있다. 상기 유기술폰산 화합물은 치환기를 가질 수도 있으며, 상기 치환기는 머캅토기, 아미노기 또는 플루오로기 등이 사용될 수도 있다.(e) salts thereof, or a mixture of two or more thereof. The organic sulfonic acid compound may have a substituent, and the substituent may be a mercapto group, an amino group or a fluoro group.
상기 탄소수 1 내지 4의 알킬술폰산은 메탄술폰산, 에탄술폰산, 프로판술폰산 및 아미노메탄술폰산을 포함하는 군으로부터 선택되는 1종 또는 2종 이상을 혼합하여 사용함이 바람직하다.The alkylsulfonic acid having 1 to 4 carbon atoms is preferably a mixture of at least one member selected from the group consisting of methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and aminomethanesulfonic acid.
상기 탄소수 6 내지 8의 아릴술폰산은 벤젠술폰산 및 페놀술폰산을 포함하는 군으로부터 선택되는 1종 또는 2종 이상을 혼합하여 사용함이 바람직하다. The arylsulfonic acid having 6 to 8 carbon atoms is preferably a mixture of at least one member selected from the group consisting of benzenesulfonic acid and phenolsulfonic acid.
상기 탄소수 5 내지 7의 헤테로아릴술폰산은 피리딘술폰산인 것이 바람직하다. The heteroarylsulfonic acid having 5 to 7 carbon atoms is preferably pyridine sulfonic acid.
상기 탄소수 7 내지 18의 알킬벤젠술폰산은 도데실벤젠술폰산, 톨루엔술폰산(4-메틸벤젠술폰산), 피리디니움파라톨루엔술폰산, 크레졸술폰산(메틸페놀술폰산), 큐멘술폰산, 및 크실렌술폰산을 포함하는 군으로부터 선택되는 1종 또는 2종 이상을 혼합하여 사용함이 바람직하다.
특히, 상기 크레졸술폰산(메틸페놀술폰산)은 0-크레졸술폰산(2-메틸페놀술폰산)일 수 있으며, 상기 크실렌술폰산은 2,5-크실렌술폰산 및/또는 2,4-크실렌술폰산일 수 있다.The alkylbenzenesulfonic acid having 7 to 18 carbon atoms includes a group including dodecylbenzenesulfonic acid, toluenesulfonic acid (4-methylbenzenesulfonic acid), pyridinium p-toluenesulfonic acid, cresylsulfonic acid (methylphenolsulfonic acid), cumenesulfonic acid, and xylenesulfonic acid Or a mixture of two or more of them is preferably used.
In particular, the cresol sulfonic acid (methyl phenol sulfonic acid) may be 0-cresol sulfonic acid (2-methylphenol sulfonic acid), and the xylene sulfonic acid may be 2,5-xylene sulfonic acid and / or 2,4-xylene sulfonic acid.
그 외에 캄파술폰산(camphorsulfonic acid) 등이 사용될 수 있다.In addition, camphorsulfonic acid and the like can be used.
상기 열거한 유기술폰산 중에서는, 도데실벤젠술폰산, 톨루엔술폰산, 큐멘술폰산, 페놀술폰산, 아미노메탄술폰산, 크실렌술폰산, 캄파술폰산 및 이의 염을 포함하는 군으로부터 선택되는 1종 또는 2종 이상의 화합물을 혼합하여 사용하는 것이 더욱 바람직하다. Among the organic sulfonic acids listed above, one or more compounds selected from the group consisting of dodecylbenzenesulfonic acid, toluenesulfonic acid, cumenesulfonic acid, phenolsulfonic acid, aminomethanesulfonic acid, xylenesulfonic acid, camphorsulfonic acid and salts thereof It is more preferable to use it.
상기 유기술폰산 화합물의 배합량은 특별하게 한정하지 않으나, 제거 대상 및 제거 조건에 따라 증감이 가능하며, 바람직하게는 전체 조성물 총 중량에 대하여 0.1 내지 20 중량%, 특히 바람직하게는 0.5 내지 10중량% 포함될 수 있다. 상기 유기술폰산 화합물이 전체 조성물 총 중량에 대하여 0.1중량% 미만 포함되는 경우, 포토레지스트 잔류물의 제거가 용이치 않으며, 20중량% 초과하여 포함되는 경우, 알루미늄과 같은 금속막의 부식 원인이 될 수 있을 뿐만 아니라 제조 비용이 커지는 문제점이 있다.The amount of the organic sulfonic acid compound to be added is not particularly limited but may be increased or decreased depending on the object to be removed and the removal conditions, and is preferably 0.1 to 20% by weight, particularly preferably 0.5 to 10% by weight based on the total weight of the total composition . If the organic sulfonic acid compound is contained in an amount of less than 0.1% by weight based on the total weight of the total composition, removal of the photoresist residue is insufficient, and if it exceeds 20% by weight, it may cause corrosion of a metal film such as aluminum There is a problem that the manufacturing cost is increased.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물에 포함되고, 상기 화학식 1로 표시되는 방향족 하이드록시카르복시산(hydroxycarboxylic acid) 화합물은 포토레지스트 잔류물을 제거하는 기능도 보유하고 있으나, 금속막의 부식을 억제하는 부식방지제로서의 기능도 함께 수행한다. 상기 방향족 하이드록시카르복시산 화합물은, 화학식 1에 나타낸 바와 같이 방향족 고리, 바람직하게는 벤젠 고리에 카르복시기와 히드록시기가 결합된 화합물을 통칭하는 것으로서, 본 발명의 조성물에는 2-하이드록시벤조산, 3-하이드록시벤조산, 4-하이드록시벤조산, 3,5-디하 이드록시벤조산, 및 2,4,6-트리하이드록시벤조산 및 이의 염을 포함하는 군으로부터 선택되는 1종 또는 2종 이상의 화합물을 혼합하여 사용하는 것이 바람직하다. The aromatic hydroxycarboxylic acid compound represented by Chemical Formula 1 contained in the release liquid composition for removing the photoresist residue of the present invention has a function of removing the photoresist residue, And also functions as a corrosion inhibitor. The aromatic hydroxycarboxylic acid compound generally refers to a compound having a carboxy group and a hydroxy group bonded to an aromatic ring, preferably a benzene ring, as shown in Formula 1. The composition of the present invention includes 2-hydroxybenzoic acid, 3-hydroxy At least one compound selected from the group consisting of benzoic acid, 4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, and 2,4,6-trihydroxybenzoic acid and salts thereof is used in combination .
상기 방향족 하이드록시카르복시산 화합물의 배합량은 특별하게 한정하지 않으나, 제거 대상 및 제거 조건에 따라 증감이 가능하며, 바람직하게는 전체 조성물 총중량에 대하여 0.1 내지 20중량%, 특히 바람직하게는 0.1 내지 10중량% 포함될 수 있다. 상기 방향족 하이드록시카르복시산이 전체 조성물 총 중량에 대하여 0.1중량% 미만 포함되는 경우, 알루미늄과 같은 금속막의 부식 원인이 되고, 20중량% 초과하여 포함되는 경우, 유기 술폰산의 활동도 저하의 원인을 제공하여 포토레지스트 잔류물의 제거가 용이치 않은 문제점이 있다.The amount of the aromatic hydroxycarboxylic acid compound to be added is not particularly limited but may be increased or decreased depending on the object to be removed and the condition of removal, and is preferably 0.1 to 20% by weight, particularly preferably 0.1 to 10% . When the aromatic hydroxycarboxylic acid is contained in an amount of less than 0.1% by weight based on the total weight of the composition, it becomes a cause of corrosion of a metal film such as aluminum. When the aromatic hydroxycarboxylic acid is contained in an amount exceeding 20% by weight, There is a problem that removal of the photoresist residue is inadequate.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물에 포함되는 물은 특별히 한정되는 것은 아니나 반도체 공정용의 물로서, 비저항값이 18MΩ/㎝ 이상인 탈이온수를 사용하는 것이 바람직하다. 상기 물의 함량은 다른 구성성분의 함량에 따라 조정될 수 있다.Water contained in the stripper solution composition for removing photoresist residue of the present invention is not particularly limited, but it is preferable to use deionized water having a specific resistance value of 18 M? / Cm or more as water for semiconductor processing. The water content can be adjusted according to the content of the other constituents.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 추가로 불소화합물을 더 포함할 수 있다. 상기 불소화합물은 기판 상에 잔류하는 경화, 변질된 포토레지스트의 제거를 촉진하는 역할을 한다. 또한, 기판 상의 오염물질, 즉 미세 먼지 등을 제거시켜 주는 역할을 한다. The release liquid composition for removing the photoresist residue of the present invention may further contain a fluorine compound. The fluorine compound plays a role in promoting the removal of the hardened and deteriorated photoresist remaining on the substrate. It also serves to remove contaminants, such as fine dust, on the substrate.
상기 불소화합물은 특별히 한정하지 않으나, 불산, 불화암모늄, 중불화암모늄 및 불화붕소산으로 이루어진 군에서 선택되는 1종 또는 2종 이상을 혼합하여 사용함이 바람직하다.The fluorine compound is not particularly limited, but is preferably a mixture of at least one member selected from the group consisting of hydrofluoric acid, ammonium fluoride, ammonium fluoride, and boron fluoride.
상기 불소화합물의 배합량은 특별하게 한정하지 않으나, 제거 대상 및 제거 조건에 따라 증감이 가능하며, 바람직하게는 전체 조성물 총중량에 대하여 0.0001중량% 내지 5중량%가 포함될 수 있다. 상기 불소화합물이 전체 조성물 총 중량에 대하여 0.0001중량% 미만 포함되는 경우, 포토레지스트 잔류물의 제거가 용이치 않으며, 5중량% 초과하여 포함될 경우, 알루미늄과 같은 금속막, SiO2 또는 SiNx와 같은 절연막의 부식 원인이 될 수 있다.The blending amount of the fluorine compound is not particularly limited, but may be increased or decreased depending on the object to be removed and the removal conditions, and preferably 0.0001 to 5% by weight based on the total weight of the entire composition. When the fluorine compound is contained in an amount of less than 0.0001 wt% based on the total weight of the entire composition, removal of the photoresist residue is unreasonable, and if it exceeds 5 wt%, a metal film such as aluminum, an insulating film such as SiO 2 or SiN x It may cause corrosion.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 상기에서 언급한 화합물을 일정량으로 유리하게 혼합하여 제조될 수 있으며, 혼합 방법은 특별히 제한되지 않으며 여러 가지 공지 방법을 적용할 수 있다. The removing solution composition for removing the photoresist residue of the present invention may be prepared by mixing the above-mentioned compounds in an appropriate amount, and the mixing method is not particularly limited and various known methods can be applied.
본 발명에 의해 제조된 포토레지스트 잔류물 제거용 박리액 조성물의 pH는 1 내지 7로 조정됨이 바람직하다. 포토레지스트 잔류물 제거용 박리액 조성물이 pH 1 미만일 경우, 알루미늄과 같은 금속막질의 부식 현상이 심화되고, pH 7 초과인 경우, 포토레지스트 잔류물의 제거 효과가 현저히 떨어진다.The pH of the peeling liquid composition for removing photoresist residue produced by the present invention is preferably adjusted to 1 to 7. When the stripper composition for removing the photoresist residue is less than pH 1, corrosion of metallic film such as aluminum is intensified, and when the pH is more than 7, the photoresist residue removal effect is significantly reduced.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 반도체소자 혹은 평판표시소자의 제조 공정에서 하드 베이킹(hard baking), 플라즈마 에칭, 고온 에싱 후 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물을 효과적으로 제거하는 박리 공정에 사용할 수 있다. The peeling liquid composition for removing the photoresist residue of the present invention can be used as a photoresist residue containing a photoresist hard baking, plasma etching, curing after high temperature ashing and / or altered photoresist in the manufacturing process of a semiconductor device or a flat panel display device It can be used in a peeling process for effectively removing water.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 수계형(water system type)으로 조성물 내의 화합물의 활동도를 증가시켜 포토레지스트 잔류물을 제거할 수 있을 뿐만 아니라, 가격적으로도 유기계 박리제보다 유리하다. 또한 유기계 박리액과 비교하여, 점도가 물과 비슷하게 낮아 분무가 가능한 조성물이므로 매엽 방식에 적용 가능하다. 따라서, 본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 여러장의 웨이퍼를 한번에 박리하는 배치(batch) 방식, 또는 한번에 한장씩 박리하는 매엽(single wafer processor) 방식 모두에 적용할 수 있다.The detachment liquid composition for removing photoresist residues of the present invention is a water system type which can increase the activity of a compound in a composition to remove photoresist residues and is more cost effective than an organic release agent Do. Compared with the organic peeling liquid, since the composition is low in viscosity similar to water and can be sprayed, it is applicable to a sheet-like method. Therefore, the peeling liquid composition for removing photoresist residue of the present invention can be applied to both a batch method for peeling a plurality of wafers at a time or a single wafer processor for peeling a wafer at a time.
본 발명은 또한, 본 발명의 박리액 조성물을 사용하는 것을 특징으로 하고, 하드 베이킹, 플라즈마 에칭, 고온 에싱 후 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물을 효과적으로 제거할 수 있는 포토레지스트 박리 방법을 제공한다.The present invention is also characterized by the use of the release liquid composition of the present invention and is a photoresist material that can effectively remove photoresist residues including hard baking, plasma etching, curing after hot etching and / A resist stripping method is provided.
상기의 포토레지스트 박리 방법은, In the photoresist stripping method,
(Ⅰ) 기판 상에 포토레지스트막을 형성하는 단계;(I) forming a photoresist film on a substrate;
(Ⅱ) 상기 포토레지스트막을 선택적으로 노광하는 단계;(II) selectively exposing the photoresist film;
(Ⅲ) 상기 노광 후의 포토레지스트막을 현상하여 포토레지스트 패턴을 형성하는 단계;(III) developing the exposed photoresist film to form a photoresist pattern;
(Ⅳ) 상기 포토레지스트 패턴을 마스크로 하여 상기 기판을 식각하는 단계; 및(IV) etching the substrate using the photoresist pattern as a mask; And
(Ⅴ) 상기 포토레지스트 패턴을 에싱하는 단계; 및(V) subjecting the photoresist pattern to ashing; And
(Ⅵ) 상기 에싱 후의 포토레지스트 잔류물을, 본 발명의 포토레지스트 잔류물 제거용 박리액 조성물을 사용하여 기판으로부터 박리하는 단계를 포함하는 것을 특징으로 한다.(VI) peeling the photoresist residue after the ashing from the substrate using the peeling liquid composition for removing the photoresist residue of the present invention.
또한, 본 발명의 박리 방법은, 마스크를 이용한 포토레지스트 패턴 형성 공정을 진행하지 않고, 에치백 (etchback) 공정과 같은 건식 식각 공정 또는 CMP(Chemical Mechanical Polishing) 공정을 수행한 다음, 노출된 포토레지스트막을 본 발명의 박리액 조성물로 박리하는 방법도 포함할 수 있다.In addition, in the removing method of the present invention, a dry etching process such as an etchback process or a CMP (Chemical Mechanical Polishing) process is performed without performing a photoresist pattern forming process using a mask, And a method of peeling the film with the release liquid composition of the present invention.
상기 박리 방법 중의, 포토레지스트막의 형성, 노광, 현상, 식각 및 에싱 공정은 당업계에 통상적으로 알려진 방법에 의하여 수행할 수 있고 특별히 한정되는 것이 아니며, 경화되거나 폴리머로 변질된 포토레지스트를 포함하는 포토레지스트 잔류물이 존재하는 기판과 박리액 조성물이 접촉할 수 있는 방법이면 양호한 박리 결과를 얻을 수 있다. The photoresist film formation, exposure, development, etching, and ashing processes in the peeling method can be performed by a method commonly known in the art, and are not particularly limited. A photoresist film containing a photoresist that is hardened or modified with a polymer If the substrate on which the resist residues are present and the peeling liquid composition can be brought into contact with each other, good peeling results can be obtained.
상기 박리 방법에는 침적법, 분무법 또는 침적 및 분무법를 이용할 수 있다. 침적, 분무 또는 침적 및 분무에 의하여 박리하는 경우, 박리 조건으로서 온도는 대개 10~100℃, 바람직하게는 20~80℃이고, 침적, 분무, 또는 침적 및 분무 시간은 대개 30초 내지 40분, 바람직하게는 1분 내지 20분이지만, 본 발명에 있어서 엄밀하게 적용되지는 않으며, 당업자에 의해 용이한 그리고 적합한 조건으로 수정될 수 있다.The peeling method may be a deposition method, a spraying method, or a deposition and spraying method. In the case of peeling by immersion, spraying or immersion and spraying, the temperature for peeling is usually from 10 to 100 캜, preferably from 20 to 80 캜, and the immersion, spraying or immersion and spraying time is usually from 30 seconds to 40 minutes, Preferably 1 minute to 20 minutes, but is not strictly applied in the present invention, and can be modified in a condition that is easy and suitable for a person skilled in the art.
또한, 상기 본 발명의 포토레지스트 잔류물 제거용 박리액 조성물 및 이를 사용하는 박리 방법은, 반도체소자 및 평판표시소자의 제조에 사용하여 알루미늄과 같은 금속 배선 및 SiO2 또는 SiNx와 같은 절연막에 대한 방식성이 뛰어난 장점이 있다.The stripping liquid composition for removing the photoresist residue and the stripping method using the same according to the present invention can be used for manufacturing semiconductor devices and flat panel display devices and can be used for metal wiring such as aluminum and a method for insulating films such as SiO 2 or SiN x There is an advantage of goodness.
본 발명의 포토레지스트 잔류물 제거용 박리액 조성물은 반도체소자 및 평판표시소자의 제조 공정 중 하드 베이킹, 플라즈마 에칭, 고온 에싱에 의해 경화 및/또는 변질된 포토레지스트를 포함하는 포토레지스트 잔류물을 효과적으로 제거할 수 있으며, 또한 금속막 및 절연막의 부식을 방지할 수 있는 효과가 있다. 특히 본 발명의 박리액 조성물은 알루미늄 배선 및 알루미늄 비아홀 등의 제조공정에 적합하며, 탈이온수 세정이 용이하여 세정시간의 단축이 가능하다.The stripper composition for removing photoresist residue of the present invention can effectively remove photoresist residues containing photoresist hardened and / or altered by hard baking, plasma etching, hot ashing during the manufacturing process of semiconductor devices and flat panel display devices And the corrosion of the metal film and the insulating film can be prevented. Particularly, the release liquid composition of the present invention is suitable for a production process of an aluminum wiring and an aluminum via hole and the like, and deionized water cleaning is easy, and the cleaning time can be shortened.
이하, 본 발명을 실시예 및 비교예를 이용하여 더욱 상세하게 설명한다. 그러나 하기 실시예 및 비교예는 본 발명을 예시하기 위한 것으로서 본 발명은 하기 실시예 및 비교예에 의해 한정되지 않고 다양하게 수정 및 변경될 수 있다. Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the following examples and comparative examples are provided for illustrating the present invention, and the present invention is not limited by the following examples and comparative examples, and various modifications and changes may be made.
실시예Example 1 내지 8 및 1 to 8 and 비교예Comparative Example 1 내지 5 1 to 5
하기 표 1과 같은 조성과 함량으로 혼합하여 실시예 1~8 및 비교예 1~5의 포토레지스트 박리액 조성물을 제조하였다.The photoresist stripping solution compositions of Examples 1 to 8 and Comparative Examples 1 to 5 were prepared by mixing the components as shown in Table 1 below.
(중량%)Sulfonic acid compound
(weight%)
화합물
(중량%)Aromatic hydroxycarboxylic acid
compound
(weight%)
(중량%)Fluorine compound
(weight%)
(중량%)etc
(weight%)
(중량%)water
(weight%)
주) DBSA : 도데실벤젠술폰산Note) DBSA: Dodecylbenzenesulfonic acid
TSA : 톨루엔술폰산TSA: toluenesulfonic acid
PSA : 페놀술폰산PSA: phenolsulfonic acid
HBA-1 : 2-하이드록시벤조산HBA-1: 2-hydroxybenzoic acid
HBA-2 : 4-하이드록시벤조산HBA-2: 4-hydroxybenzoic acid
HBA-3 : 2,4,6-트리하이드록시벤조산HBA-3: 2,4,6-trihydroxybenzoic acid
FBA : 불화붕소산 FBA: fluoroboric acid
TMAH : 테트라메틸암모늄하이드록사이드TMAH: tetramethylammonium hydroxide
시험예Test Example : : 박리성Peelability 및 And 방식성Improvisation 시험 exam
SiO2 절연막에 Al 금속 배선을 가지며, 플라즈마 에칭 또는 고온 에싱 후 발생한 변질된 포토레지스트 잔류물 및 폴리머 잔사물이 상기의 금속막 및 절연막에 부착된 시편을 온도 40℃의 박리액(상기 실시예 및 비교예) 각각에 20분간 침적시킨 후 박리액으로부터 시편을 꺼내고 초순수로 1분간 린스한 후 질소 가스를 이용하여 건조시켰다. 그리고 주사전자현미경을 이용하여 건식 식각 또는 고온 에싱 후 잔류하는 포토레지스트 잔류물 및 폴리머의 제거성과, 약액에 노출된 금속막 및 절연막의 방식성을 평가하였다. 박리성 및 방식성 평가는 하기와 같은 기준에 의거 평가하였으며, 그 결과는 하기의 표 2에 나타내었다.A specimen having an Al metal wiring in an SiO 2 insulating film and adhered to the metal film and the insulating film with deteriorated photoresist residue and polymer residue generated after plasma etching or high temperature ashing was applied to a peeling liquid Comparative Example) After each sample was immersed for 20 minutes, the specimen was taken out from the peeling solution, rinsed with ultrapure water for 1 minute, and dried using nitrogen gas. The removal of residual photoresist and polymer after dry or high temperature ashing using a scanning electron microscope and the corrosion resistance of the metal film and insulating film exposed to the chemical solution were evaluated. The peelability and corrosion resistance were evaluated according to the following criteria, and the results are shown in Table 2 below.
[박리성 평가 기준][Evaluation criteria for peelability]
◎: 매우 양호, ○: 양호, △: 일부 잔류물 존재, X: 잔류물 제거 불가⊚: very good, ∘: good, △: presence of some residues, X: impossible to remove residues
[Al 방식성 평가 기준][Evaluation Criteria for Aluminum Anchoring Properties]
◎: 부식 없음, ○: 부식 거의 없음, △: 일부 부식, 표면 거칠기 변화, X: 에칭 발생?: No corrosion,?: Almost no corrosion,?: Partial corrosion, Change in surface roughness, X: Etching
상기 표 2에 나타난 결과와 같이, 본 발명의 유기 술폰산, 방향족 하이드록시카르복시산 화합물 및 물을 포함하는 조성물인 실시예 1 내지 8의 포토레지스트 잔류물 박리능 및 알루미늄에 대한 방식성이 좋은 것을 확인하였다.As shown in Table 2, it was confirmed that the photoresist residue peelability and the corrosion resistance to aluminum of Examples 1 to 8, which are compositions containing the organic sulfonic acid, aromatic hydroxycarboxylic acid compound and water of the present invention, are good .
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