KR20060088478A - 리빙 자유 라디칼 방법에 의해 제조된 아크릴- 또는메타크릴-계 중합체 수지를 갖는 포토레지스트 중합체 및조성물 - Google Patents
리빙 자유 라디칼 방법에 의해 제조된 아크릴- 또는메타크릴-계 중합체 수지를 갖는 포토레지스트 중합체 및조성물 Download PDFInfo
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- KR20060088478A KR20060088478A KR1020057024718A KR20057024718A KR20060088478A KR 20060088478 A KR20060088478 A KR 20060088478A KR 1020057024718 A KR1020057024718 A KR 1020057024718A KR 20057024718 A KR20057024718 A KR 20057024718A KR 20060088478 A KR20060088478 A KR 20060088478A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 36
- 150000003254 radicals Chemical class 0.000 title claims description 77
- 239000000203 mixture Substances 0.000 title claims description 69
- 239000002952 polymeric resin Substances 0.000 title claims description 47
- 229920003002 synthetic resin Polymers 0.000 title claims description 46
- 125000005641 methacryl group Chemical group 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 75
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 43
- 239000000178 monomer Substances 0.000 claims abstract description 23
- -1 acryl Chemical group 0.000 claims description 214
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 48
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 29
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- 230000008569 process Effects 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 15
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
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- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 7
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- 239000011574 phosphorus Chemical group 0.000 claims description 7
- 230000002441 reversible effect Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 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 description 38
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
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- 125000001424 substituent group Chemical group 0.000 description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 10
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- 125000004149 thio group Chemical group *S* 0.000 description 9
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
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- 239000000654 additive Substances 0.000 description 7
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- 238000004519 manufacturing process Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
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- 239000002585 base Substances 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
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- 125000001145 hydrido group Chemical group *[H] 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000001459 lithography Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
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- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 4
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- 230000009471 action Effects 0.000 description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 238000010894 electron beam technology Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
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- 125000001188 haloalkyl group Chemical group 0.000 description 3
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- 239000012535 impurity Substances 0.000 description 3
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- WUKHZVXCZKDWMS-UHFFFAOYSA-N (4-cyanonaphthalen-1-yl)-dimethylsulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=C(C#N)C2=C1 WUKHZVXCZKDWMS-UHFFFAOYSA-N 0.000 description 2
- XLQMBODNBLKPIP-UHFFFAOYSA-O (4-hydroxynaphthalen-1-yl)-dimethylsulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=C(O)C2=C1 XLQMBODNBLKPIP-UHFFFAOYSA-O 0.000 description 2
- ZCFOLLBETMWRMU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;4-(thiolan-1-ium-1-yl)naphthalen-1-ol Chemical compound C12=CC=CC=C2C(O)=CC=C1[S+]1CCCC1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZCFOLLBETMWRMU-UHFFFAOYSA-N 0.000 description 2
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- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 2
- GYCAQKKCFIZWQQ-UHFFFAOYSA-M 1-naphthalen-1-yl-2-(thiolan-1-ium-1-yl)ethanone;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.C=1C=CC2=CC=CC=C2C=1C(=O)C[S+]1CCCC1 GYCAQKKCFIZWQQ-UHFFFAOYSA-M 0.000 description 2
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- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-M octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-M 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000005469 synchrotron radiation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- BKUKUDKXROEQFN-UHFFFAOYSA-N tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate Chemical compound C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 BKUKUDKXROEQFN-UHFFFAOYSA-N 0.000 description 1
- XTHPZPSENWSQJR-UHFFFAOYSA-M tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;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.C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 XTHPZPSENWSQJR-UHFFFAOYSA-M 0.000 description 1
- UACVJSDAGHJPNP-UHFFFAOYSA-M tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 UACVJSDAGHJPNP-UHFFFAOYSA-M 0.000 description 1
- QBOVXIMGMVOPQK-UHFFFAOYSA-N tert-butyl adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC(C)(C)C)C3 QBOVXIMGMVOPQK-UHFFFAOYSA-N 0.000 description 1
- VKUZRUNYENZANE-UHFFFAOYSA-N tert-butyl n-(1-adamantyl)-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound C1C(C2)CC3CC2CC1(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C3 VKUZRUNYENZANE-UHFFFAOYSA-N 0.000 description 1
- WFLZPBIWJSIELX-UHFFFAOYSA-N tert-butyl n-[10-[(2-methylpropan-2-yl)oxycarbonylamino]decyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCNC(=O)OC(C)(C)C WFLZPBIWJSIELX-UHFFFAOYSA-N 0.000 description 1
- VDSMPNIBLRKWEG-UHFFFAOYSA-N tert-butyl n-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCNC(=O)OC(C)(C)C VDSMPNIBLRKWEG-UHFFFAOYSA-N 0.000 description 1
- NMEQKHOJGXGOIL-UHFFFAOYSA-N tert-butyl n-[7-[(2-methylpropan-2-yl)oxycarbonylamino]heptyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCNC(=O)OC(C)(C)C NMEQKHOJGXGOIL-UHFFFAOYSA-N 0.000 description 1
- YLKUQZHLQVRJEV-UHFFFAOYSA-N tert-butyl n-[8-[(2-methylpropan-2-yl)oxycarbonylamino]octyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCNC(=O)OC(C)(C)C YLKUQZHLQVRJEV-UHFFFAOYSA-N 0.000 description 1
- XSIWKTQGPJNJBV-UHFFFAOYSA-N tert-butyl n-[9-[(2-methylpropan-2-yl)oxycarbonylamino]nonyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCNC(=O)OC(C)(C)C XSIWKTQGPJNJBV-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- MSLRPWGRFCKNIZ-UHFFFAOYSA-J tetrasodium;hydrogen peroxide;dicarbonate Chemical compound [Na+].[Na+].[Na+].[Na+].OO.OO.OO.[O-]C([O-])=O.[O-]C([O-])=O MSLRPWGRFCKNIZ-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48339003P | 2003-06-26 | 2003-06-26 | |
| US48331003P | 2003-06-26 | 2003-06-26 | |
| US60/483,390 | 2003-06-26 | ||
| US60/483,310 | 2003-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060088478A true KR20060088478A (ko) | 2006-08-04 |
Family
ID=33555604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057024718A Withdrawn KR20060088478A (ko) | 2003-06-26 | 2004-06-25 | 리빙 자유 라디칼 방법에 의해 제조된 아크릴- 또는메타크릴-계 중합체 수지를 갖는 포토레지스트 중합체 및조성물 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1641849A1 (https=) |
| JP (1) | JP2007526351A (https=) |
| KR (1) | KR20060088478A (https=) |
| WO (1) | WO2005000923A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100073588A (ko) * | 2008-12-23 | 2010-07-01 | 주식회사 동진쎄미켐 | 감광성 고분자 및 이를 포함하는 포토레지스트 조성물 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7696292B2 (en) | 2003-09-22 | 2010-04-13 | Commonwealth Scientific And Industrial Research Organisation | Low-polydispersity photoimageable acrylic polymers, photoresists and processes for microlithography |
| KR101010757B1 (ko) * | 2008-06-09 | 2011-01-25 | 주식회사 동부하이텍 | 사슬 전이제, 이를 이용한 반사방지막 수지의 제조방법 |
| US20130109816A1 (en) | 2011-10-28 | 2013-05-02 | E.I. Du Pont De Nemours And Company | Processes for removing sulfur-containing end groups from polymers |
| SG11201404228UA (en) | 2012-01-18 | 2014-10-30 | Univ Iowa State Res Found | Thermoplastic elastomers via atom transfer radical polymerization of plant oil |
| EP2970538B1 (en) | 2013-03-15 | 2021-10-20 | DuPont Electronics, Inc. | Polymerization process protection means |
| HK1220219A1 (zh) | 2013-05-20 | 2017-04-28 | 爱荷华州立大学研究基金会有限公司 | 經由甘油三酯的可逆加成-斷裂鏈轉移聚合的熱塑性彈性體 |
| KR102377565B1 (ko) * | 2018-12-13 | 2022-03-21 | 주식회사 엘지화학 | 아크릴계 공중합체, 이의 제조방법 및 이를 포함하는 아크릴계 공중합체 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2166092T3 (es) * | 1996-07-10 | 2002-04-01 | Du Pont | Polimerizacion con caracteristicas vivientes. |
| CA2309279C (en) * | 1997-12-18 | 2009-07-14 | E.I. Du Pont De Nemours And Company | Polymerization process with living characteristics and polymers made therefrom |
| US20030180662A1 (en) * | 1998-05-25 | 2003-09-25 | Daicel Chemical Industries, Ltd. | Acid-sensitive compound and resin composition for photoresist |
| JP4282185B2 (ja) * | 1999-11-02 | 2009-06-17 | 株式会社東芝 | フォトレジスト用高分子化合物及びフォトレジスト用樹脂組成物 |
| JP2004220009A (ja) * | 2002-12-28 | 2004-08-05 | Jsr Corp | 感放射線性樹脂組成物 |
-
2004
- 2004-06-25 EP EP04777056A patent/EP1641849A1/en not_active Withdrawn
- 2004-06-25 WO PCT/US2004/020346 patent/WO2005000923A1/en not_active Ceased
- 2004-06-25 JP JP2006517640A patent/JP2007526351A/ja active Pending
- 2004-06-25 KR KR1020057024718A patent/KR20060088478A/ko not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100073588A (ko) * | 2008-12-23 | 2010-07-01 | 주식회사 동진쎄미켐 | 감광성 고분자 및 이를 포함하는 포토레지스트 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005000923A1 (en) | 2005-01-06 |
| JP2007526351A (ja) | 2007-09-13 |
| EP1641849A1 (en) | 2006-04-05 |
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