TWI468865B - 光阻劑及其使用方法 - Google Patents
光阻劑及其使用方法 Download PDFInfo
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- TWI468865B TWI468865B TW99143922A TW99143922A TWI468865B TW I468865 B TWI468865 B TW I468865B TW 99143922 A TW99143922 A TW 99143922A TW 99143922 A TW99143922 A TW 99143922A TW I468865 B TWI468865 B TW I468865B
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- Taiwan
- Prior art keywords
- photoresist
- phenolic
- group
- resin
- component
- Prior art date
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 69
- 238000000034 method Methods 0.000 title claims description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 10
- 239000004065 semiconductor Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical group [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000005011 phenolic resin Substances 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 15
- -1 methyl adamantyl methacrylate Chemical compound 0.000 description 14
- 239000000654 additive Substances 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910001092 metal group alloy Inorganic materials 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 6
- 238000005468 ion implantation Methods 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910000679 solder Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- JWVAUCBYEDDGAD-UHFFFAOYSA-N bismuth tin Chemical compound [Sn].[Bi] JWVAUCBYEDDGAD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QCEUXSAXTBNJGO-UHFFFAOYSA-N [Ag].[Sn] Chemical compound [Ag].[Sn] QCEUXSAXTBNJGO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GQRTVVANIGOXRF-UHFFFAOYSA-N (2-methyl-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C=C)C3 GQRTVVANIGOXRF-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 206010038743 Restlessness Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- PQIJHIWFHSVPMH-UHFFFAOYSA-N [Cu].[Ag].[Sn] Chemical compound [Cu].[Ag].[Sn] PQIJHIWFHSVPMH-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- GCIYMCNGLUNWNR-UHFFFAOYSA-N (2,4-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GCIYMCNGLUNWNR-UHFFFAOYSA-N 0.000 description 1
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
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- UUNHRGSUOBTBKW-UHFFFAOYSA-M 2-hydroxypropanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC(O)C([O-])=O UUNHRGSUOBTBKW-UHFFFAOYSA-M 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
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- 244000291564 Allium cepa Species 0.000 description 1
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- 241000208340 Araliaceae Species 0.000 description 1
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- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
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- 238000000059 patterning Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
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- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/26—Bombardment with radiation
- H01L21/263—Bombardment with radiation with high-energy radiation
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- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- 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
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/02—Semiconductor bodies ; Multistep manufacturing processes therefor
- H01L29/36—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by the concentration or distribution of impurities in the bulk material
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Description
本項發明係關於新穎光阻劑,其包含酚系(phenolic)成分,且其特別適用於離子植入微影應用。本發明光阻劑可顯現增加之聚焦深度(曝光寬容度(exposure latitude))。
光阻劑是用於將影像轉到基板的感光膜。於基板表面上形成一層光阻劑塗層,然後經光罩暴露於活化輻射源下。
離子植入技術業已用於摻雜半導體晶圓。藉由此方法,離子束植入器於抽真空(低壓)艙中產生離子束,且該離子被導向並「植入」至晶圓。
但使用目前的離子植入方法遇到嚴重問題。具體來說,可能難以獲得可接受之聚焦深度(depth of focus,DOF),特別是在高解析度應用中以及稠密特徵與分隔(isolated)特徵將被同時成像處。若是經顯影阻劑線或其他特徵與其最鄰近阻劑特徵相距等於兩倍或更多倍線寬之距離,則一般將其視為“分隔”的。因此,舉例來說,若一線被印刷成0.25μm寬,且下一個相鄰阻劑特徵與該線相距至少約0.5μm,則視該線為分隔(而非稠密)。
所欲為擁有提供良好解析度(包括良好聚焦深度)之新穎光阻劑系統。
我們現提供用於短波長成像(例如193 nm)之新穎化學放大型光阻劑組成物,其除了包含含光酸不安定基之樹脂及一種或多種光酸產生劑化合物外,還包含酚系成分。意外發現添加酚系成分(例如酚系樹脂)可顯著增加光阻劑之聚焦深度(曝光寬容度)。本發明之光阻劑特別適用於離子植入微影方案。
酚系成分適當為酚系樹脂,例如,多羥基苯乙烯,其可以相對較少量存在,例如少於光阻劑組成物之總固體(除溶劑載劑以外的所有成分)之10、8、6、5、4或2或甚至1重量%。
本發明之較佳阻劑可於短波長成像,包括低於300 nm與低於200 nm,例如248 nm、193 nm及EUV。
本發明之特佳光阻劑係含有如本文所述之酚系成分;成像有效量之一種或多種光酸產生劑化合物(PAG);以及選自下述所組成群組之樹脂:
1)含有可提供特別適合於248 nm成像之化學放大型正阻劑的酸不安定基之酚系樹脂。此類樹脂之特佳者包括:i)含有乙烯基酚及丙烯酸烷基酯之聚合單元的聚合物,其中該經聚合之丙烯酸烷基酯單元可於光酸存在下進行去封阻反應(deblocking reaction)。可進行光酸誘導之去封阻反應的例示性丙烯酸烷基酯包括例如丙烯酸第三丁酯、甲基丙烯酸第三丁酯、丙烯酸甲基金剛烷基酯、甲基丙烯酸甲基金剛烷基酯、以及其他可進行光酸誘導反應之丙烯酸非環狀烷基酯及丙烯酸脂環族酯;例如美國專利案第6,042,997號及第5,492,793號之聚合物,該等案併入本文作為參考文獻;ii)含有下列聚合單元之聚合物(如美國專利案第6,042,997號所揭示之聚合物,其併入本文作為參考文獻):乙烯基酚;環上不含羥基或羧基取代基之視需要經取代之乙烯基苯基(如苯乙烯);以及丙烯酸烷基酯,如彼等揭示於上述聚合物i)之去封阻基;以及iii)含有下列重複單元之聚合物:包含將與光酸反應之縮醛或縮酮部分之重複單元,以及視需要之芳香族重複單元(如苯基或酚系基);
2)可提供特別適合在低於200 nm波長(如193 nm)成像之化學放大型正光阻的實質上或完全不含苯基或其他芳香族基之樹脂。此類樹脂的特佳者包括:i)含有非芳香族環狀烯烴(內環雙鍵)之聚合單元(如視需要經取代之降莰烯)的聚合物,如美國專利案第5,843,624號所揭示之聚合物(其係併入本文作為參考文獻);ii)含有丙烯酸烷基酯單元(如丙烯酸第三丁酯、甲基丙烯酸第三丁酯、丙烯酸甲基金剛烷基酯、甲基丙烯酸甲基金剛烷基酯以及其他丙烯酸非環狀烷基酯及丙烯酸脂環族酯)之聚合物,該等聚合物係揭示於美國專利案第6,057,083號。
本發明之阻劑也可包含分開(distinct)之PAG的混合物,典型為2種或3種不同PAG的混合物,更典型為由總共2種不同PAG所構成的混合物。
本發明也提供本用於形成本發明光阻劑之浮雕影像的方法,包含用於形成低於四分之一微米直徑或更低(如低於0.2或0.1微米)之高度解析的經圖案化光阻劑影像(如,具有實質上垂直側壁的圖案化線)之方法。
本項發明進一步包括包含基板之製造件,如其上塗佈有本發明之光阻劑及浮雕影像的微電子晶圓。本發明也包括製造微電子晶圓和其他物件的方法。
此外,如前述,於一較佳態樣中,所提供之本發明告知(informed)離子植入加工。此製程可包含將摻雜劑離子(第III族及/或第V族離子,如硼、砷、磷等)植入至基板(如半導體晶圓)表面,於該基板表面上係有做為遮罩之前述有機光阻劑。被阻劑遮罩之基板可置於反應腔室中,該反應腔室可提供減壓及來自可離子化源之離子電漿。這些離子包含前述摻雜劑離子,當其被植入基板時為電活性者。可對反應腔室施加電壓(如透過導電的腔室牆),以選擇性植入摻雜劑離子。
本發明的其他態樣將於下文中揭示。
如前述,我們現提供新穎光阻劑組成物,其適當地包含1)樹脂成分,其可適當地含有光酸不安定基;2)一或多種光酸產生劑化合物;以及3)酚系成分,其可為聚合物或非聚合物。較佳地,該等成分1)、2)及3)係分開的,亦即,該等成分不共價鏈結,且各自為不同材料。本發明的較佳光阻劑為正作用阻劑,特別是化學放大型阻劑。本發明也包括負作用光阻劑,其中該阻劑可包含樹脂、交聯官能和本文所述之酚系成分。
特別地,本發明光阻劑將包含分開之成份:1)樹脂成分;2)一或多種光酸產生劑化合物;以及3)酚系成分,其可為聚合物或非聚合物;其中該樹脂成分1)不包含或至少實質上不含(少於5重量%)苯基或酚系基,且較佳地,該樹脂之所有重複單元的50%為非芳香族者,更較佳為少於該樹脂1)之40或35所有重複單元為非芳香族者。於許多較佳具體實施例中,樹脂1)可為實質上不含任何芳香族重複單元,其中該樹脂之所有重複單元中,少於15、10、5、3、2或1%為芳香族。
特佳酚系成分包括酚系樹脂,其可為包含酚系基之重複單元的均聚物,例如聚(羥基苯乙烯)均聚物,或可為包含具有其他經聚合基團之酚系重複單元的共聚物。
本發明阻劑之酚系成分中,也可包含各式其他基團,例如鹵素、氰基、烷氧基、醚、視需要經取代之C1-20
烷基。
如前述,該酚系成分可為非聚合物,亦即,不含多個重複單元。然而,於許多較佳態樣中,該酚系成分為聚合物。於該類本發明態樣中,該酚系成分添加劑視需要地可具有相對較高之分子量,例如超過1000、2000、5000、10000、15000、20000重量平均分子量之分子量。
較佳地,該酚系成分於光組劑組成物中係安定,且不會干擾阻劑之微影式加工。亦即,較佳地,該酚系成分不會促進過早的阻劑降解(亦即,降低之貨架期),或是不會必然需使用交替微影式加工條件。
典型地,該酚系成分將是除其他阻劑成分(例如光酸不安定或去封阻樹脂、光酸產生劑、鹼性添加劑、表面活性劑/流平劑、塑化劑及/或溶劑)以外之進一步分開的阻劑成分。因此,於至少某些態樣中,阻劑中所用之酚系成分將不會含有光酸不安定部分(例如於光阻劑曝光步驟後會進行去封阻反應之光酸不安定酯基或光酸不安定縮醛基)。
然而,該酚系成分可將其他功能提供給阻劑組成物,例如提供或增加固體成分的溶解力。然而,與其他揮發性溶劑不同,於任何曝光前熱處理後,酚系成分添加劑仍將以有效量留在阻劑層中,例如較佳地,於任何曝光前熱處理後,至少約10、20、30、40或50莫耳%量之調配於液體阻劑組成物中的酚系成分將留在阻劑組成物中。典型地,於任何熱處理後,僅須小量之酚系成分添加劑仍留在阻劑塗層中來達到有效結果,例如,酚系成分添加劑可適當地以揮發性溶劑移除後該組劑層總材料之自約0.05或1重量%至約5重量%之量存在。
如本文所述,阻劑成分的各式取代基可視需要地經取代。經取代之部分係視需要地於一個或是多個可行位置經例如下述基取代:鹵素(例如F、Cl、Br及/或I)、硝基、氰基、磺酸基(sulfono)、烷基(包括C1-16
烷基,以C1-8
烷基較佳)、鹵烷基(如氟烷基,例如三氟甲基;及全氟烷基,例如全氟C1-4
烷基)、烷氧基(包括具有一個或多個氧連結之C1-16
烷氧基,以C1-8
烷氧基較佳)、烯基(包括C2-12
烯基,以C2-8
烯基較佳)、炔基(包括C2-12
炔基,以C2-8
炔基較佳)、芳基(例如苯基或萘基)、及經取代之芳基(例如經鹵基、烷氧基、烯基、炔基及/或烷基取代之芳基,該等取代基較佳具有上述相應基團之碳數)。較佳的經取代之芳基包括經取代之苯基、經取代之蔥基及經取代之萘基。
本發明之光阻劑典型包含樹脂黏合劑及光活性成分及酚系成分。於許多具體實施例中,較佳為化學放大型正作用阻劑。已有多種此類阻劑組成物被揭露於,例如,美國專利案第4,968,581號、4,883,740號4,810,613及4,491,628號,及加拿大專利申請案2,001,384號中。
用於本發明之光阻劑亦包含光活性成分,特別是一種或是多種光酸產生劑化合物(亦即PAG),該PAG係以足以在曝光於活化輻射後於該阻劑之塗層中產生潛像之量使用。用於在193 nm及248 nm成像之較佳PAG係包括醯亞胺基磺酸酯(imidosulfonate),如下式之化合物:
其中R為樟腦基、金剛烷基、烷基(如C1-12
烷基)及氟烷基(如氟(C1-18
烷基));例如RCF2
-,其中R為視需要經取代之金剛烷基。
其他已知之PAG亦可用於本發明之阻劑中。尤其對於在193 nm成像而言,為了提供增加之透明度,通常較佳者為不含有芳香族基之PAG,如上揭之醯亞胺基磺酸酯。
其他適用於本發明之光阻劑的光酸產生劑係包括,舉例而言:鎓鹽,如三氟甲烷磺酸三苯基硫鎓、三氟甲烷磺酸(對第三丁氧基苯基)二苯基硫鎓、三氟甲烷磺酸參(對第三丁氧基苯基)硫鎓、對甲苯磺酸三苯基硫鎓;硝基苄基衍生物,如對甲苯磺酸2-硝基苄基酯、對甲苯磺酸2,6-二硝基苄基酯及對甲苯磺酸2,4-二硝基苄基酯;磺酸酯,如1,2,3-參(甲烷磺醯氧基)苯、1,2,3-參(三氟甲烷磺醯氧基)苯及1,2,3-參(對甲苯磺醯氧基)苯;重氮甲烷衍生物,如雙(苯磺醯基)重氮甲烷、雙(對甲苯磺醯基)重氮甲烷;乙二醛二肟(glyoxime)衍生物,如雙-O-(對甲苯磺醯基)-α-二甲基乙二醛二肟及雙-O-(正丁烷磺醯基)-α-二甲基乙二醛二肟;N-羥基醯亞胺化合物之磺酸酯衍生物,如N-羥基琥珀醯亞胺甲烷磺酸酯、N-羥基琥珀醯亞胺三氟甲烷磺酸酯;以及含鹵素之三化合物,如2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-1,3,5-三及2-(4-甲氧基萘基)-4,6-雙(三氯甲基)-1,3,5-三。可使用一種或多種此等PAG。
根據本發明使用之該阻劑之視需要的添加劑較佳為添加鹼(added base),尤其是氫氧化四甲基銨(TBAH)或乳酸四甲基銨,其可增加經顯影之阻劑浮雕影像的解析度。對於在193 nm成像之阻劑而言,較佳之添加鹼典型為氫氧化四甲基銨之乳酸鹽以及多種其他胺類如三異丙醇胺、二氮雜雙環十一烯或二氮雜雙環壬烯。該添加鹼係適宜地以相對較小量使用,如相對於總固體為約0.03至5重量%。
根據本發明使用之光阻劑亦可含有其他視需要之材料。舉例而言,其他視需要之添加劑包括抗條紋劑、塑化劑及加速劑等。除了填料及染料可以相對較大濃度(例如,為阻劑乾燥成分之總重量的約5至30重量%)存在外,此等視需要之添加劑典型將以較小濃度存在於光阻劑組成物中。
根據本發明使用之光阻劑通常係藉由下列已知方法製備。舉例而言,本發明之阻劑可藉由將光阻劑之成分溶解於適宜溶劑中而製備為塗佈組成物,該溶劑為諸如二醇醚如2-甲氧基乙基醚(二乙二醇單甲醚)、乙二醇單甲醚、丙二醇單甲醚;丙二醇單甲醚乙酸酯;乳酸酯如乳酸乙酯或乳酸甲酯,其中乳酸乙酯為較佳者;丙酸酯,尤其是丙酸甲酯、丙酸乙酯及乙氧基丙酸乙酯;賽路蘇酯(Cellosolve ester)如甲基賽路蘇乙酸酯;芳香族烴如甲苯或二甲苯;或酮如甲基乙基酮、環己酮及2-庚酮。該光阻劑之固體含量典型係於該光阻劑組成物之總重量的5至35重量%間變化。此等溶劑之摻合物亦為適宜者。
液體光阻劑組成物可藉由諸如旋塗、浸塗、輥塗或其他傳統塗佈技術施加至基板。當旋塗時,可基於所使用之具體旋塗設備、溶液之黏度、旋塗器之速度以及允許旋塗之時間量來調整該塗佈溶液之固體含量,以提供所欲之膜厚度。
根據本發明使用之光阻劑組成物係適合施加於與塗佈光阻劑有關之製程所習用的基板。舉例而言,該組成物可施加於用以生產微處理器及其他積體電路組件之矽晶圓或塗佈有二氧化矽之矽晶圓上。亦可適宜地使用鋁-氧化鋁、砷化鎵、陶瓷、石英、銅、玻璃基板等。光阻劑亦可適宜地施加於抗反射層上,尤其是有機抗反射層。
將該光阻劑塗佈於表面後,其可藉由加熱移除溶劑而予以乾燥,較佳係加熱至該光阻劑塗層無黏性為止。
之後,以將該光阻劑層曝光於成像輻射。可使用浸潤式微影製程。本文所稱“浸潤曝光”或其他類似術語意指曝光係以插置於曝光工具與該經塗佈之光阻劑組成物層之間的流體層(如水或具有添加劑之水)進行。
該光阻劑組成物層係適當地圖案化曝光於活化輻射,且曝光能量係取決於該曝光工具及該光阻劑組成物之成分,典型介於約1至100 mJ/cm2
之範圍內。本文所稱將光阻劑組成物曝光於活化該光阻劑之輻射係意指該輻射可藉由諸如引發該光活性成分之反應(如由光酸產生劑化合物產生光酸)而於該光阻劑中形成潛像。
如上所述,光阻劑組成物可藉由短曝光波長(尤其是低於400 nm,低於300 nm及低於200 nm之曝光波長)予以光活化,其中,I線(365 nm),248 nm與193 nm以及EUV為特佳之曝光波長。
曝光之後,該組成物之膜層較佳係於約70℃至160℃之溫度範圍烘烤。之後,較佳係藉由使用水性鹼性顯影劑來處理而使該膜顯影,該水性鹼性顯影劑係諸如四級銨氫氧化物溶液如氫氧化四烷基銨溶液;各式胺溶液,較佳係0.26 N氫氧化四甲基銨,如乙胺、正丙胺、二乙胺、二正丙胺、三乙胺或甲基二乙基胺;醇胺如二乙醇胺或三乙醇胺;以及環狀胺如吡咯、吡啶等。通常,係依照該技術領域所熟知之方法進行顯影。
本發明之光阻劑及方法可使用於廣範圍的應用中,包括,例如於薄膜頭(如約3至5μm)、磁碟、CD罩以及後端植入的製造中。
本發明之光阻劑亦可適用於在半導體晶圓上形成金屬凸塊。此加工可包括:a)將本發明之光阻劑置於半導體晶圓上,較佳提供厚膜塗層,例如50μm或更厚之乾燥後阻劑塗層;c)將該光阻劑組成物層成像式曝光於光化輻射,包括低於300 nm或低於200 nm輻射,尤其是248 nm及193 nm;d)顯影該經曝光光阻劑組成物層以提供經圖案化區域;e)沈積金屬於經圖案化區域中;以及f)移除該經曝光光阻劑組成物層以提供具金屬凸塊之半導體晶圓。
於此凸塊形成方法中,係將光阻劑層成像而得以於感光層中形成穴,例如孔(via)。於此製程中,感光層係置於電子裝置上的導電層上。感光組成物的曝光與後續顯影於該感光組成成物中提供了經定義之洞(孔),並暴露出下方導電層。因此,該製程的下一個步驟為使用該經定義之洞(孔)沈積金屬或金屬合金凸塊。此金屬沈積可能藉由無電或電解式沈積製程。電解式金屬沈積為較佳者。於電解式金屬沈積製程中,電子裝置基板(亦即,半導體基板)係作為陰極。
於沈積金屬或金屬合金前,諸如適合作為焊料、導電層,例如銅或鎳,可藉由濺鍍、無電沈積等沈積,以形成凸塊下金屬。此凸塊下金屬層典型為自1000至50000厚,並作為後續鍍覆之焊料凸塊的可濕潤基礎。
有廣泛種類的金屬可無電式地沈積,包括但不限於銅、錫-鉛、鎳、金、銀、鈀等。可無電式沈積之適當金屬及金屬合金包括但不限於銅、錫、錫-鉛、鎳、金、銀、錫-銻、錫-銅、錫-鉍、錫-銦、錫-銀、鈀等。此金屬鍍覆浴為技術領域中具有通常知識者已知,並已可由各種來源取得,例如自羅門哈斯(Rohm and Haas)。
於一具體實施例中,於半導體晶圓上之金屬沈積物有用於作為焊料凸塊。因此,較佳地,該金屬凸塊為可焊性金屬及金屬合金,例如錫、錫-鉛、錫-銅、錫-銀、錫-鉍、錫-銅-鉍、錫-銅-銀等。焊料凸塊之適當金屬及金屬合金的形成方法係揭露於美國專利案第5,186,383、5,902,472、5,990,564、6,099,713及6,013,572號中以及歐洲專利申請案第EP 1 148 548號(Cheung et al.)中,所有該等案藉此併入參考。例示性金屬及金屬合金包括但不限於錫;具有少於2重量%銅(較佳約0.7重量%銅)之錫-銅合金;具有少於20重量%銀(較佳約自3.5至10重量%銀)之錫-銀合金;具有自5至25重量%鉍(較佳約20重量%鉍)之錫-鉍合金;具有少於5重量%銀(較佳約3.5重量%銀)、少於2重量%銅(較佳約0.7重量%銅)以及餘量錫之錫-銀-銅合金。於一具體實施例中,用於銲錫凸塊之金屬合金係不含鉛,亦即,其含有10 ppm鉛。
通常,適當之電解金屬鍍覆浴為酸性,且含有酸、該一種或多種待沈積金屬之水可溶形式、及視需要之一種或多種有機添加劑,例如亮光劑(加速劑)、載劑(抑制劑)、流平劑、延性增加劑、濕潤劑、浴安定劑(特別適用於含錫浴)、細粒劑等。各視需要成份的存在與否、種類及含量係依所使用之具體金屬鍍覆浴而變化。此金屬鍍覆浴通常為商業上可購得者,例如購自希普列公司(Shipley Company)。
於此製程中,阻劑組成物作為不被鍍覆區域之保護層。金屬沉積後,將剩餘阻劑組成物剝除,例如藉由於約40至69℃之溫度使用商業上可購得之N-甲基吡咯啶酮(NMP)系剝除劑。適當之剝除劑可購自各式來源,例如Shipley-SVC(加州金山灣區)。
所有本文中提及之檔案於此併入本文參考。下述非限制性實施例係例示性說明本發明。
實施例1:阻劑之製備
藉由混合下述成分(下述1至5)而製備了光阻劑,其中含量係以阻劑總重的重量%表示。
1.樹脂。光阻劑之樹脂係甲基丙烯酸2-甲基-2-金剛烷基酯/甲基丙烯酸β-羥基-γ-丁內酯/甲基丙烯酸氰基-降莰酯之三元共聚物,基於流體光阻劑總重計,存在量為10.80重量%。
2.光酸產生劑化合物(PAG)。PAG為全氟丁烷磺酸第三丁基苯基四亞甲基硫鎓,基於流體光阻劑總重計,存在量為2.5重量%。
3.鹼性添加劑。鹼性添加劑為N-烷基己內醯胺,基於光阻劑組成物的總重計,其量為0.017重量%。
4.酚系成分。酚系成分為聚(羥基苯乙烯)樹脂(重量平均分子量為約10000),基於光阻劑的總重計,其量為3.5重量%。
5.溶劑。溶劑為乳酸乙酯,以阻劑餘量提供。
實施例2:微影加工
實施例1中配製之阻劑組成物係旋塗於SiON晶圓表面,並藉由真空熱板於90℃軟烤60秒。阻劑塗層係透過光罩於193 nm曝光,接著該經曝光塗層係於110℃經曝光後烘烤。接著將經塗覆晶圓以0.26N氫氧化四丁基銨水溶液處理,以顯影成像後阻劑層。
於光阻劑浮雕影像形成後,基板(連同阻劑遮罩)係曝光於高能量(>20 eV,減壓環境)磷離子植入加工。
Claims (8)
- 一種提供經離子植入之半導體基板的方法,包含:提供其上塗覆有化學放大型正作用光阻劑組成物之浮雕影像之半導體基板;其中該光阻劑包含樹脂、光活性成分及酚系成分,其中該酚系成分包含選自由下列所組成群組中之至少一基團:氰基、烷氧基及醚;以及施加離子至該基板。
- 如申請專利範圍第1項所述之方法,其中該酚系成分係酚系樹脂。
- 如申請專利範圍第1項所述之方法,其中該光阻劑為化學放大型正光阻劑,且該樹脂成分包含含有少於50重量%芳香族基之樹脂。
- 一種經塗覆基板,包含:其上塗覆有化學放大型正作用光阻劑組成物之浮雕影像之半導體晶圓,該光阻劑組成物包含分開之成份:1)樹脂、2)光活性成分及3)酚系成分,其中該酚系成分包含選自由下列所組成群組中之至少一基團:氰基、烷氧基及醚;以及該晶圓具經施加之摻雜劑離子。
- 一種形成光阻劑浮雕影像之方法,包含:(a)將包含樹脂、光活性成分及酚系成分之光阻劑施加至基板,其中該酚系成分包含選自由下列所組成群組中之至少一基團:氰基、烷氧基及醚;以及 (b)將該光阻劑塗層曝光至經圖案化之活化輻射。
- 如申請專利範圍第1至3及5項中任一項所述之方法,其中該輻射為193nm。
- 如申請專利範圍第1至3及5項中任一項所述之方法,其中該光阻劑組成物係施加至無機表面。
- 一種光阻劑組成物,包含非酚系樹脂、光活性成分及酚系成分,其中該酚系成分包含選自由下列所組成群組中之至少一基團:氰基、烷氧基及醚。
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JP5776580B2 (ja) * | 2011-02-25 | 2015-09-09 | 信越化学工業株式会社 | ポジ型レジスト材料及びこれを用いたパターン形成方法 |
US9704724B2 (en) * | 2011-12-26 | 2017-07-11 | Toray Industries, Inc. | Photosensitive resin composition and method for producing semiconductor device |
KR102248976B1 (ko) * | 2013-12-26 | 2021-05-06 | 아사히 가세이 가부시키가이샤 | 감광성 수지 조성물 및 감광성 수지 적층체 |
US10365322B2 (en) | 2016-04-19 | 2019-07-30 | Analog Devices Global | Wear-out monitor device |
US10677822B2 (en) | 2016-09-27 | 2020-06-09 | Analog Devices Global Unlimited Company | Electrical overstress detection device |
US11112436B2 (en) | 2018-03-26 | 2021-09-07 | Analog Devices International Unlimited Company | Spark gap structures for detection and protection against electrical overstress events |
CN109164685B (zh) * | 2018-09-26 | 2022-06-28 | 珠海雅天科技有限公司 | 一种euv光刻胶及其制备方法与应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007072183A (ja) * | 2005-09-07 | 2007-03-22 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物およびレジストパターン形成方法 |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4491628A (en) | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
US4564575A (en) * | 1984-01-30 | 1986-01-14 | International Business Machines Corporation | Tailoring of novolak and diazoquinone positive resists by acylation of novolak |
US4968581A (en) | 1986-02-24 | 1990-11-06 | Hoechst Celanese Corporation | High resolution photoresist of imide containing polymers |
US4810613A (en) | 1987-05-22 | 1989-03-07 | Hoechst Celanese Corporation | Blocked monomer and polymers therefrom for use as photoresists |
DE3721741A1 (de) | 1987-07-01 | 1989-01-12 | Basf Ag | Strahlungsempfindliches gemisch fuer lichtempfindliche beschichtungsmaterialien |
DE68926019T2 (de) | 1988-10-28 | 1996-10-02 | Ibm | Positiv arbeitende hochempfindliche Photolack-Zusammensetzung |
DE4112970A1 (de) | 1991-04-20 | 1992-10-22 | Hoechst Ag | Saeurespaltbare strahlungsempfindliche verbindungen, diese enthaltendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial |
US5186383A (en) | 1991-10-02 | 1993-02-16 | Motorola, Inc. | Method for forming solder bump interconnections to a solder-plated circuit trace |
DE69322946T2 (de) | 1992-11-03 | 1999-08-12 | Ibm | Photolackzusammensetzung |
EP0818563A1 (en) | 1996-01-30 | 1998-01-14 | Naganoken | Aqueous solution for forming metal complexes, tin-silver alloy plating bath, and process for producing plated object using the plating bath |
US5843624A (en) | 1996-03-08 | 1998-12-01 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
US5861231A (en) | 1996-06-11 | 1999-01-19 | Shipley Company, L.L.C. | Copolymers and photoresist compositions comprising copolymer resin binder component |
US6099713A (en) | 1996-11-25 | 2000-08-08 | C. Uyemura & Co., Ltd. | Tin-silver alloy electroplating bath and tin-silver alloy electroplating process |
JPH10254137A (ja) * | 1997-03-11 | 1998-09-25 | Nec Corp | 化学増幅系レジスト |
KR100219806B1 (ko) | 1997-05-27 | 1999-09-01 | 윤종용 | 반도체장치의 플립 칩 실장형 솔더 범프의 제조방법, 이에 따라 제조되는 솔더범프 및 그 분석방법 |
US5990564A (en) | 1997-05-30 | 1999-11-23 | Lucent Technologies Inc. | Flip chip packaging of memory chips |
US6057083A (en) | 1997-11-04 | 2000-05-02 | Shipley Company, L.L.C. | Polymers and photoresist compositions |
US6365321B1 (en) * | 1999-04-13 | 2002-04-02 | International Business Machines Corporation | Blends of hydroxystyrene polymers for use in chemically amplified positive resist formulations |
US6890448B2 (en) * | 1999-06-11 | 2005-05-10 | Shipley Company, L.L.C. | Antireflective hard mask compositions |
US6638847B1 (en) | 2000-04-19 | 2003-10-28 | Advanced Interconnect Technology Ltd. | Method of forming lead-free bump interconnections |
US6593182B2 (en) * | 2001-03-19 | 2003-07-15 | Macronix International Co., Ltd. | Method for forming multiple gate oxide layer with the plasma oxygen doping |
KR100393230B1 (ko) * | 2001-08-16 | 2003-07-31 | 삼성전자주식회사 | 잔막율을 조절할 수 있는 포토레지스트 패턴의 형성방법 |
WO2004092831A2 (en) * | 2003-04-09 | 2004-10-28 | Rohm And Haas, Electronic Materials, L.L.C. | Photoresists and methods for use thereof |
JP4570910B2 (ja) * | 2004-06-08 | 2010-10-27 | 東京応化工業株式会社 | 重合体およびポジ型レジスト組成物 |
US7433004B2 (en) * | 2004-06-11 | 2008-10-07 | Sharp Kabushiki Kaisha | Color filter substrate, method of making the color filter substrate and display device including the color filter substrate |
EP1662320A1 (en) * | 2004-11-24 | 2006-05-31 | Rohm and Haas Electronic Materials, L.L.C. | Photoresist compositions |
JP4789599B2 (ja) * | 2004-12-06 | 2011-10-12 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | フォトレジスト組成物 |
US7081327B2 (en) | 2004-12-29 | 2006-07-25 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive photoresist composition for thick film, thick-film photoresist laminated product, manufacturing method for thick-film resist pattern, and manufacturing method for connection terminal |
JP4533756B2 (ja) * | 2005-01-07 | 2010-09-01 | 富士フイルム株式会社 | イオン注入工程用ポジ型レジスト組成物及びそれを用いたイオン注入方法 |
JP5047502B2 (ja) * | 2005-01-19 | 2012-10-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | 樹脂混合物を含むフォトレジスト組成物 |
JP4905811B2 (ja) * | 2006-08-24 | 2012-03-28 | Jsr株式会社 | イオンインプランテーション方法及びそれに用いる感放射線性樹脂組成物 |
JP4798027B2 (ja) * | 2007-01-18 | 2011-10-19 | Jsr株式会社 | イオンインプランテーション用感放射線性樹脂組成物、及びイオンインプランテーション用パターン形成方法 |
JP5260094B2 (ja) * | 2007-03-12 | 2013-08-14 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | フェノール系ポリマー及びこれを含有するフォトレジスト |
JP5032362B2 (ja) * | 2007-03-12 | 2012-09-26 | ローム アンド ハース カンパニー | ヒドロキシフェニルアクリレート系モノマーおよびポリマー |
JP2009063823A (ja) * | 2007-09-06 | 2009-03-26 | Tokyo Ohka Kogyo Co Ltd | ポジ型ホトレジスト組成物、積層体およびパターン形成方法 |
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2336827B1 (en) | 2015-09-16 |
CN102201333B (zh) | 2014-04-30 |
JP5753681B2 (ja) | 2015-07-22 |
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US8815754B2 (en) | 2014-08-26 |
JP6121464B2 (ja) | 2017-04-26 |
KR20110068936A (ko) | 2011-06-22 |
KR101877360B1 (ko) | 2018-07-11 |
US9502254B2 (en) | 2016-11-22 |
JP2011227448A (ja) | 2011-11-10 |
US20140361415A1 (en) | 2014-12-11 |
JP2015135983A (ja) | 2015-07-27 |
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