TWI269939B - Photoresist compositions comprising blends of photoacid generators - Google Patents
Photoresist compositions comprising blends of photoacid generators Download PDFInfo
- Publication number
- TWI269939B TWI269939B TW089102895A TW89102895A TWI269939B TW I269939 B TWI269939 B TW I269939B TW 089102895 A TW089102895 A TW 089102895A TW 89102895 A TW89102895 A TW 89102895A TW I269939 B TWI269939 B TW I269939B
- Authority
- TW
- Taiwan
- Prior art keywords
- photoacid
- photoresist composition
- acid
- generator
- compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 238
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 231
- 239000002253 acid Substances 0.000 claims abstract description 94
- 229920005989 resin Polymers 0.000 claims abstract description 44
- 239000011347 resin Substances 0.000 claims abstract description 44
- -1 fluoroalkyl sulfonic acid Chemical compound 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 36
- 238000000576 coating method Methods 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 13
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 claims description 7
- QPHBUJJTFKRYHM-UHFFFAOYSA-N adamantane-1-sulfonic acid Chemical compound C1C(C2)CC3CC2CC1(S(=O)(=O)O)C3 QPHBUJJTFKRYHM-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- QZHDEAJFRJCDMF-UHFFFAOYSA-N perfluorohexanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-N 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 4
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000004377 microelectronic Methods 0.000 claims description 4
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000052 vinegar Substances 0.000 claims description 4
- 235000021419 vinegar Nutrition 0.000 claims description 4
- 241000723346 Cinnamomum camphora Species 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 229960000846 camphor Drugs 0.000 claims description 3
- 229930008380 camphor Natural products 0.000 claims description 3
- 229920006026 co-polymeric resin Polymers 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000010432 diamond Substances 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 150000001463 antimony compounds Chemical class 0.000 claims 9
- 230000003115 biocidal effect Effects 0.000 claims 6
- 239000003139 biocide Substances 0.000 claims 6
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 claims 4
- 241000208140 Acer Species 0.000 claims 3
- 230000032683 aging Effects 0.000 claims 3
- XAQPFUUTSNMMQH-UHFFFAOYSA-N 10,10,10-trifluorodecane-1-sulfonic acid Chemical compound FC(CCCCCCCCCS(=O)(=O)O)(F)F XAQPFUUTSNMMQH-UHFFFAOYSA-N 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims 2
- 150000002506 iron compounds Chemical class 0.000 claims 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 150000003284 rhodium compounds Chemical class 0.000 claims 2
- ZWWGKYHSHZDTKG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,4-decafluorobutane sulfuric acid Chemical compound OS(O)(=O)=O.FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZWWGKYHSHZDTKG-UHFFFAOYSA-N 0.000 claims 1
- MPQOMCMWZWRHPX-UHFFFAOYSA-N 1,2,3-trifluoroanthracene Chemical compound C1=CC=C2C=C(C(F)=C(C(F)=C3)F)C3=CC2=C1 MPQOMCMWZWRHPX-UHFFFAOYSA-N 0.000 claims 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-O 4-sulfobenzenediazonium Chemical compound OS(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-O 0.000 claims 1
- 239000004925 Acrylic resin Substances 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 238000001574 biopsy Methods 0.000 claims 1
- 150000001622 bismuth compounds Chemical class 0.000 claims 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-M cyclohexanesulfonate Chemical compound [O-]S(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-M 0.000 claims 1
- 229910003460 diamond Inorganic materials 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000012954 diazonium Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 238000000059 patterning Methods 0.000 claims 1
- 229960004624 perflexane Drugs 0.000 claims 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 claims 1
- 239000011941 photocatalyst Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000003900 succinic acid esters Chemical group 0.000 claims 1
- 229960001727 tretinoin Drugs 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 239000011230 binding agent Substances 0.000 abstract description 8
- 229920000642 polymer Polymers 0.000 description 47
- 150000007513 acids Chemical class 0.000 description 15
- 239000007787 solid Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 230000002079 cooperative effect Effects 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 238000001459 lithography Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 4
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 3
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000006117 anti-reflective coating Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000005094 computer simulation Methods 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
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- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002505 iron Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical compound N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- MMIVBBGVRXGVKV-UHFFFAOYSA-N 1,2-diethoxy-9H-fluorene Chemical compound CCOC1=C(C=2CC3=CC=CC=C3C=2C=C1)OCC MMIVBBGVRXGVKV-UHFFFAOYSA-N 0.000 description 1
- IKMBXKGUMLSBOT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F IKMBXKGUMLSBOT-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—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
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/253,171 US6200728B1 (en) | 1999-02-20 | 1999-02-20 | Photoresist compositions comprising blends of photoacid generators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI269939B true TWI269939B (en) | 2007-01-01 |
Family
ID=22959171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089102895A TWI269939B (en) | 1999-02-20 | 2000-02-19 | Photoresist compositions comprising blends of photoacid generators |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US6200728B1 (enExample) |
| EP (1) | EP1030221A1 (enExample) |
| JP (3) | JP2000241965A (enExample) |
| KR (1) | KR100669183B1 (enExample) |
| TW (1) | TWI269939B (enExample) |
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| JP3955384B2 (ja) * | 1998-04-08 | 2007-08-08 | Azエレクトロニックマテリアルズ株式会社 | 化学増幅型レジスト組成物 |
| JP4272805B2 (ja) * | 1999-12-27 | 2009-06-03 | 富士フイルム株式会社 | ポジ型感放射線性組成物 |
| JP4253427B2 (ja) * | 2000-09-19 | 2009-04-15 | 富士フイルム株式会社 | ポジ型レジスト組成物 |
| EP1299774A4 (en) * | 2001-04-05 | 2005-06-08 | Arch Spec Chem Inc | PHOTOACID GENERATORS FOR USE IN PHOTORESIN COMPOSITIONS |
| JP3912767B2 (ja) * | 2001-06-21 | 2007-05-09 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| US6949329B2 (en) | 2001-06-22 | 2005-09-27 | Matsushita Electric Industrial Co., Ltd. | Pattern formation method |
| TWI300516B (enExample) * | 2001-07-24 | 2008-09-01 | Jsr Corp | |
| EP1308781A3 (en) * | 2001-10-05 | 2003-09-03 | Shipley Co. L.L.C. | Cyclic sulfonium and sulfoxonium photoacid generators and photoresists containing them |
| JP3901997B2 (ja) * | 2001-11-27 | 2007-04-04 | 富士通株式会社 | レジスト材料、レジストパターン及びその製造方法、並びに、半導体装置及びその製造方法 |
| US7214465B2 (en) * | 2002-01-10 | 2007-05-08 | Fujifilm Corporation | Positive photosensitive composition |
| US7108951B2 (en) * | 2002-02-26 | 2006-09-19 | Fuji Photo Film Co., Ltd. | Photosensitive resin composition |
| JP4410977B2 (ja) | 2002-07-09 | 2010-02-10 | 富士通株式会社 | 化学増幅レジスト材料及びそれを用いたパターニング方法 |
| US7208249B2 (en) * | 2002-09-30 | 2007-04-24 | Applied Materials, Inc. | Method of producing a patterned photoresist used to prepare high performance photomasks |
| US7314700B2 (en) * | 2002-12-05 | 2008-01-01 | International Business Machines Corporation | High sensitivity resist compositions for electron-based lithography |
| CN101118362A (zh) * | 2002-12-16 | 2008-02-06 | 伊英克公司 | 电光显示器的底板 |
| KR100561842B1 (ko) * | 2003-08-25 | 2006-03-16 | 삼성전자주식회사 | 단량체 광산발생제 조성물, 상기 조성물로 코팅된 기판,상기 단량체 광산발생제 조성물을 이용하여 기판상에서화합물을 합성하는 방법 및 상기 방법에 의하여 제조된마이크로어레이 |
| US7488565B2 (en) * | 2003-10-01 | 2009-02-10 | Chevron U.S.A. Inc. | Photoresist compositions comprising diamondoid derivatives |
| US7393627B2 (en) * | 2004-03-16 | 2008-07-01 | Cornell Research Foundation, Inc. | Environmentally friendly photoacid generators (PAGs) with no perfluorooctyl sulfonates (PFOS) |
| JP4308051B2 (ja) * | 2004-03-22 | 2009-08-05 | 富士フイルム株式会社 | 感光性組成物及びそれを用いたパターン形成方法 |
| US20050214674A1 (en) * | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
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| JP2006078760A (ja) * | 2004-09-09 | 2006-03-23 | Tokyo Ohka Kogyo Co Ltd | 電子線またはeuv(極端紫外光)用レジスト組成物及びレジストパターン形成方法 |
| EP1829942B1 (en) | 2006-02-28 | 2012-09-26 | Rohm and Haas Electronic Materials, L.L.C. | Coating compositions for use with an overcoated photoresist |
| WO2007124092A2 (en) | 2006-04-21 | 2007-11-01 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
| JP4355725B2 (ja) * | 2006-12-25 | 2009-11-04 | 信越化学工業株式会社 | ポジ型レジスト材料及びパターン形成方法 |
| US8088548B2 (en) * | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
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| US20090181319A1 (en) * | 2008-01-16 | 2009-07-16 | International Business Machines Corporation | Aromatic fluorine-free photoacid generators and photoresist compositions containing the same |
| JP5216573B2 (ja) | 2008-03-31 | 2013-06-19 | 富士フイルム株式会社 | 感活性光線または感放射線性樹脂組成物及びそれを用いたパターン形成方法 |
| US8163461B2 (en) * | 2008-04-09 | 2012-04-24 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
| JP5192277B2 (ja) * | 2008-04-14 | 2013-05-08 | シャープ株式会社 | 固体撮像装置の製造方法 |
| JP5746818B2 (ja) * | 2008-07-09 | 2015-07-08 | 富士フイルム株式会社 | 感活性光線性または感放射線性樹脂組成物及びそれを用いたパターン形成方法 |
| US8455176B2 (en) * | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
| KR101949719B1 (ko) * | 2008-12-23 | 2019-04-25 | 노보머, 인코포레이티드 | 조정 가능한 중합체 조성물 |
| EP2216683B1 (en) | 2009-02-08 | 2018-11-14 | Rohm and Haas Electronic Materials, L.L.C. | Substrates coated with an antireflective composition and a photoresist |
| JP5746824B2 (ja) | 2009-02-08 | 2015-07-08 | 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Rohm and Haas Electronic Materials LLC | 上塗りフォトレジストと共に使用するのに好適なコーティング組成物 |
| US20100203450A1 (en) * | 2009-02-11 | 2010-08-12 | International Business Machines Corporation | Photoresist compositions and methods of use |
| US8883407B2 (en) | 2009-06-12 | 2014-11-11 | Rohm And Haas Electronic Materials Llc | Coating compositions suitable for use with an overcoated photoresist |
| US8227307B2 (en) * | 2009-06-24 | 2012-07-24 | International Business Machines Corporation | Method for removing threshold voltage adjusting layer with external acid diffusion process |
| US8632948B2 (en) * | 2009-09-30 | 2014-01-21 | Az Electronic Materials Usa Corp. | Positive-working photoimageable bottom antireflective coating |
| US20110086312A1 (en) * | 2009-10-09 | 2011-04-14 | Dammel Ralph R | Positive-Working Photoimageable Bottom Antireflective Coating |
| US8460851B2 (en) * | 2010-01-14 | 2013-06-11 | Sumitomo Chemical Company, Limited | Salt and photoresist composition containing the same |
| TWI513678B (zh) | 2010-06-29 | 2015-12-21 | Sumitomo Chemical Co | 鹽、酸產生劑及光阻組成物 |
| US20120040288A1 (en) * | 2010-08-11 | 2012-02-16 | Microchem Corp. | Epoxy formulations with controllable photospeed |
| JP6049250B2 (ja) | 2010-11-30 | 2016-12-21 | 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Rohm and Haas Electronic Materials LLC | 光酸発生剤 |
| JP5906787B2 (ja) | 2011-03-08 | 2016-04-20 | 住友化学株式会社 | 塩、レジスト組成物及びレジストパターンの製造方法 |
| JP5990041B2 (ja) | 2011-07-19 | 2016-09-07 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| JP5985898B2 (ja) | 2011-07-19 | 2016-09-06 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| JP5886696B2 (ja) | 2011-07-19 | 2016-03-16 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
| JP2013174660A (ja) * | 2012-02-23 | 2013-09-05 | Fujifilm Corp | 感光性樹脂組成物、硬化膜の製造方法、硬化膜、有機el表示装置および液晶表示装置 |
| JP5856991B2 (ja) | 2012-05-21 | 2016-02-10 | 富士フイルム株式会社 | 化学増幅型レジスト組成物、ネガ型化学増幅型レジスト組成物、それを用いたレジスト膜、レジスト塗布マスクブランクス、フォトマスクの製造方法及びパターン形成方法、並びに、電子デバイスの製造方法 |
| US10248020B2 (en) * | 2012-12-28 | 2019-04-02 | Rohm And Haas Electronic Materials Llc | Acid generators and photoresists comprising same |
| JP5789705B2 (ja) * | 2014-06-16 | 2015-10-07 | 富士フイルム株式会社 | 感活性光線性または感放射線性樹脂組成物、及び該組成物を用いたパターン形成方法 |
| JP2018109701A (ja) | 2017-01-04 | 2018-07-12 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 化学増幅型ポジ型フォトレジスト組成物およびそれを用いたパターン形成方法 |
| KR102656042B1 (ko) * | 2018-03-08 | 2024-04-11 | 제이에스알 가부시끼가이샤 | 감방사선성 수지 조성물 및 그의 제조 방법 그리고 레지스트 패턴 형성 방법 |
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| JP7344108B2 (ja) | 2019-01-08 | 2023-09-13 | 信越化学工業株式会社 | レジスト組成物、及びパターン形成方法 |
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-
1999
- 1999-02-20 US US09/253,171 patent/US6200728B1/en not_active Expired - Lifetime
-
2000
- 2000-02-14 KR KR1020000006750A patent/KR100669183B1/ko not_active Expired - Lifetime
- 2000-02-15 EP EP00301138A patent/EP1030221A1/en not_active Ceased
- 2000-02-19 TW TW089102895A patent/TWI269939B/zh not_active IP Right Cessation
- 2000-02-21 JP JP2000042690A patent/JP2000241965A/ja active Pending
- 2000-04-19 US US09/552,211 patent/US6203965B1/en not_active Expired - Lifetime
-
2001
- 2001-02-17 US US09/788,106 patent/US6803169B2/en not_active Expired - Lifetime
-
2010
- 2010-04-07 JP JP2010089034A patent/JP2010186193A/ja active Pending
-
2013
- 2013-08-09 JP JP2013166405A patent/JP5810139B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6803169B2 (en) | 2004-10-12 |
| US6203965B1 (en) | 2001-03-20 |
| EP1030221A1 (en) | 2000-08-23 |
| JP2010186193A (ja) | 2010-08-26 |
| US6200728B1 (en) | 2001-03-13 |
| JP5810139B2 (ja) | 2015-11-11 |
| JP2000241965A (ja) | 2000-09-08 |
| KR100669183B1 (ko) | 2007-01-16 |
| KR20000076655A (ko) | 2000-12-26 |
| JP2013232016A (ja) | 2013-11-14 |
| US20010038970A1 (en) | 2001-11-08 |
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