JP2007526351A5 - - Google Patents
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- JP2007526351A5 JP2007526351A5 JP2006517640A JP2006517640A JP2007526351A5 JP 2007526351 A5 JP2007526351 A5 JP 2007526351A5 JP 2006517640 A JP2006517640 A JP 2006517640A JP 2006517640 A JP2006517640 A JP 2006517640A JP 2007526351 A5 JP2007526351 A5 JP 2007526351A5
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- Japan
- Prior art keywords
- group
- optionally substituted
- polymer
- substituted
- carbon atoms
- Prior art date
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- -1 alicyclic hydrocarbon Chemical class 0.000 claims description 220
- 239000000203 mixture Substances 0.000 claims description 90
- 229920000642 polymer Polymers 0.000 claims description 79
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 71
- 229920002120 photoresistant polymer Polymers 0.000 claims description 70
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 60
- 239000002952 polymeric resin Substances 0.000 claims description 46
- 125000005842 heteroatoms Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 26
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 15
- 239000000178 monomer Substances 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
- 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 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003435 aroyl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Chemical group 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000011574 phosphorus Chemical group 0.000 claims description 7
- 230000002441 reversible Effects 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 claims description 5
- 238000007342 radical addition reaction Methods 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 3
- 150000003254 radicals Chemical group 0.000 description 67
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 41
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical group [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 description 40
- 239000002253 acid Substances 0.000 description 39
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- 125000003118 aryl group Chemical group 0.000 description 28
- 239000003999 initiator Substances 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 238000003776 cleavage reaction Methods 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 125000004149 thio group Chemical group *S* 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 238000010526 radical polymerization reaction Methods 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000009792 diffusion process Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 6
- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 6
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000001459 lithography Methods 0.000 description 6
- 125000005395 methacrylic acid group Chemical group 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 230000002829 reduced Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 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
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SLAJLBDKTXRQBP-UHFFFAOYSA-N 1-naphthalen-1-yl-2-(thiolan-1-ium-1-yl)ethanone Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)C[S+]1CCCC1 SLAJLBDKTXRQBP-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-hydroxy-Succinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000001312 dry etching Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 231100000489 sensitizer Toxicity 0.000 description 5
- 125000004426 substituted alkynyl group Chemical group 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- CEZIJESLKIMKNL-UHFFFAOYSA-N 1-(4-butoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C12=CC=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 CEZIJESLKIMKNL-UHFFFAOYSA-N 0.000 description 4
- WFQNMENFJSZTGD-UHFFFAOYSA-O 2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1 WFQNMENFJSZTGD-UHFFFAOYSA-O 0.000 description 4
- 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 4
- TYXGWNTYNTZQLI-UHFFFAOYSA-O 4-(thiolan-1-ium-1-yl)naphthalen-1-ol Chemical compound C12=CC=CC=C2C(O)=CC=C1[S+]1CCCC1 TYXGWNTYNTZQLI-UHFFFAOYSA-O 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- 229940009976 Deoxycholate Drugs 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- CVGOYJZPIRCZRB-UHFFFAOYSA-N (4-cyanonaphthalen-1-yl)-diethylsulfanium Chemical compound C1=CC=C2C([S+](CC)CC)=CC=C(C#N)C2=C1 CVGOYJZPIRCZRB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GDFJRGCGROYZGS-UHFFFAOYSA-N 1-(4-butoxyphenyl)thiolan-1-ium Chemical compound C1=CC(OCCCC)=CC=C1[S+]1CCCC1 GDFJRGCGROYZGS-UHFFFAOYSA-N 0.000 description 3
- GHSQNVDGAOETGI-UHFFFAOYSA-N 1-(4-ethoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C12=CC=CC=C2C(OCC)=CC=C1[S+]1CCCC1 GHSQNVDGAOETGI-UHFFFAOYSA-N 0.000 description 3
- FUBAYNPDUBRNJU-UHFFFAOYSA-N 1-(4-methoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C12=CC=CC=C2C(OC)=CC=C1[S+]1CCCC1 FUBAYNPDUBRNJU-UHFFFAOYSA-N 0.000 description 3
- XHZFJVQQYGUCMV-UHFFFAOYSA-N 1-(4-phenylmethoxynaphthalen-1-yl)thiolan-1-ium Chemical compound C=1C=CC=CC=1COC(C1=CC=CC=C11)=CC=C1[S+]1CCCC1 XHZFJVQQYGUCMV-UHFFFAOYSA-N 0.000 description 3
- MNEFJFCBGFTMSW-UHFFFAOYSA-N 1-[4-(ethoxymethoxy)naphthalen-1-yl]thiolan-1-ium Chemical compound C12=CC=CC=C2C(OCOCC)=CC=C1[S+]1CCCC1 MNEFJFCBGFTMSW-UHFFFAOYSA-N 0.000 description 3
- LKAMDJHLFPSSAD-UHFFFAOYSA-N 1-[4-(methoxymethoxy)naphthalen-1-yl]thiolan-1-ium Chemical compound C12=CC=CC=C2C(OCOC)=CC=C1[S+]1CCCC1 LKAMDJHLFPSSAD-UHFFFAOYSA-N 0.000 description 3
- 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
- PJSNWMUSYYVXAH-UHFFFAOYSA-N 2-[4-(thiolan-1-ium-1-yl)naphthalen-1-yl]oxyoxane Chemical compound C1CCC[S+]1C(C1=CC=CC=C11)=CC=C1OC1OCCCC1 PJSNWMUSYYVXAH-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 230000036499 Half live Effects 0.000 description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive Effects 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- TUHVAFNHSRNRDK-UHFFFAOYSA-N butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate Chemical compound C12=CC=CC=C2C(OC(=O)OCCCC)=CC=C1[S+]1CCCC1 TUHVAFNHSRNRDK-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LCLLDNMEVAPSAM-UHFFFAOYSA-N diethyl(naphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](CC)CC)=CC=CC2=C1 LCLLDNMEVAPSAM-UHFFFAOYSA-N 0.000 description 3
- QUAOSAXDZIKYGO-UHFFFAOYSA-O diethyl-(4-hydroxynaphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](CC)CC)=CC=C(O)C2=C1 QUAOSAXDZIKYGO-UHFFFAOYSA-O 0.000 description 3
- MVWZJDWUSDTGDE-UHFFFAOYSA-N diethyl-(4-methylnaphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](CC)CC)=CC=C(C)C2=C1 MVWZJDWUSDTGDE-UHFFFAOYSA-N 0.000 description 3
- OGTOIEVNWNMXCG-UHFFFAOYSA-N diethyl-(4-nitronaphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](CC)CC)=CC=C([N+]([O-])=O)C2=C1 OGTOIEVNWNMXCG-UHFFFAOYSA-N 0.000 description 3
- XYWUBXNONJKKSD-UHFFFAOYSA-N dimethyl(naphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=CC2=C1 XYWUBXNONJKKSD-UHFFFAOYSA-N 0.000 description 3
- OAWHEYWQBDELJO-UHFFFAOYSA-N dimethyl-(4-methylnaphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=C(C)C2=C1 OAWHEYWQBDELJO-UHFFFAOYSA-N 0.000 description 3
- POUOKOIBKJTLBX-UHFFFAOYSA-N dimethyl-(4-nitronaphthalen-1-yl)sulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=C([N+]([O-])=O)C2=C1 POUOKOIBKJTLBX-UHFFFAOYSA-N 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- FPEMQADFSSXZSB-UHFFFAOYSA-N ethyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate Chemical compound C12=CC=CC=C2C(OC(=O)OCC)=CC=C1[S+]1CCCC1 FPEMQADFSSXZSB-UHFFFAOYSA-N 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000006606 n-butoxy group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 150000002829 nitrogen Chemical group 0.000 description 3
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RRFZHSZJDWDDES-UHFFFAOYSA-N propyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate Chemical compound C12=CC=CC=C2C(OC(=O)OCCC)=CC=C1[S+]1CCCC1 RRFZHSZJDWDDES-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004434 sulfur atoms Chemical group 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
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- GYHHZMUNWLCUAH-UHFFFAOYSA-N phenothiazine Chemical compound C1=CC=C2[N]C3=CC=CC=C3SC2=C1 GYHHZMUNWLCUAH-UHFFFAOYSA-N 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- XTANVVYNHRBVQC-UHFFFAOYSA-N piperidin-3-one;propane-1,2-diol Chemical compound CC(O)CO.O=C1CCCNC1 XTANVVYNHRBVQC-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
- 230000001376 precipitating Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 230000035484 reaction time Effects 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 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
- 239000002356 single layer Substances 0.000 description 1
- 239000001187 sodium carbonate 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
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000005469 synchrotron radiation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 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
- 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
- HXINNZFJKZMJJJ-UHFFFAOYSA-N tert-butyl N-[12-[(2-methylpropan-2-yl)oxycarbonylamino]dodecyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCCCNC(=O)OC(C)(C)C HXINNZFJKZMJJJ-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
- PDJJNHGVNMFOQO-UHFFFAOYSA-N tert-butyl N-[6-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]hexyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)CCCCCCN(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C PDJJNHGVNMFOQO-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
- 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
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical group CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 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
- 239000010409 thin film Substances 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-O thiolan-1-ium Chemical compound C1CC[SH+]C1 RAOIDOHSFRTOEL-UHFFFAOYSA-O 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US48339003P | 2003-06-26 | 2003-06-26 | |
US48331003P | 2003-06-26 | 2003-06-26 | |
PCT/US2004/020346 WO2005000923A1 (fr) | 2003-06-26 | 2004-06-25 | Polymeres de resine photosensible et compositions contenant une resine polymerique a base acrylique ou methacrylique preparee par un processus radicalaire vivant |
Publications (2)
Publication Number | Publication Date |
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JP2007526351A JP2007526351A (ja) | 2007-09-13 |
JP2007526351A5 true JP2007526351A5 (fr) | 2008-05-08 |
Family
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Family Applications (1)
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JP2006517640A Pending JP2007526351A (ja) | 2003-06-26 | 2004-06-25 | リビングフリーラジカルプロセスにより調製した、アクリル酸またはメタクリル酸ベースのポリマー樹脂を有するフォトレジストポリマーおよび組成物 |
Country Status (4)
Country | Link |
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EP (1) | EP1641849A1 (fr) |
JP (1) | JP2007526351A (fr) |
KR (1) | KR20060088478A (fr) |
WO (1) | WO2005000923A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
KR101579730B1 (ko) * | 2008-12-23 | 2015-12-24 | 주식회사 동진쎄미켐 | 감광성 고분자 및 이를 포함하는 포토레지스트 조성물 |
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 |
WO2013109878A1 (fr) | 2012-01-18 | 2013-07-25 | Iowa State University Research Foundation, Inc. | Élastomères thermoplastiques par polymérisation radicalaire par transfert d'atomes d'une huile végétale |
WO2014150700A1 (fr) | 2013-03-15 | 2014-09-25 | E. I. Du Pont De Nemours And Company | Moyen de protection dans un procédé de polymérisation |
EP2999727B1 (fr) | 2013-05-20 | 2019-07-10 | Iowa State University Research Foundation, Inc. | Élastomères thermoplastiques par l'intermédiaire d'une polymérisation réversible contrôlée par transfert de chaîne par addition-fragmentation de triglycérides (raft) |
KR102377565B1 (ko) * | 2018-12-13 | 2022-03-21 | 주식회사 엘지화학 | 아크릴계 공중합체, 이의 제조방법 및 이를 포함하는 아크릴계 공중합체 조성물 |
Family Cites Families (5)
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DE69709110T2 (de) * | 1996-07-10 | 2002-04-25 | Du Pont | Polymerisation mit "living" kennzeichen |
KR100589073B1 (ko) * | 1997-12-18 | 2006-06-13 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 리빙 특성의 중합 방법 및 이 방법으로 제조된 중합체 |
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/fr not_active Withdrawn
- 2004-06-25 JP JP2006517640A patent/JP2007526351A/ja active Pending
- 2004-06-25 KR KR1020057024718A patent/KR20060088478A/ko not_active Application Discontinuation
- 2004-06-25 WO PCT/US2004/020346 patent/WO2005000923A1/fr not_active Application Discontinuation
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