TWI705079B - 負型光敏組成物 - Google Patents
負型光敏組成物 Download PDFInfo
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- TWI705079B TWI705079B TW106119645A TW106119645A TWI705079B TW I705079 B TWI705079 B TW I705079B TW 106119645 A TW106119645 A TW 106119645A TW 106119645 A TW106119645 A TW 106119645A TW I705079 B TWI705079 B TW I705079B
- Authority
- TW
- Taiwan
- Prior art keywords
- hept
- bicyclo
- group
- formula
- bis
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 131
- 229920000642 polymer Polymers 0.000 claims abstract description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000005693 optoelectronics Effects 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 13
- -1 5-Dodecylbicyclo[2.2.1]hept-2-ene 1,3-Bis(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)benzene Chemical compound 0.000 claims description 53
- 239000000758 substrate Substances 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 241000208340 Araliaceae Species 0.000 claims description 28
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 28
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 28
- 235000008434 ginseng Nutrition 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000004065 semiconductor Substances 0.000 claims description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
- 230000005855 radiation Effects 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 238000011161 development Methods 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 19
- 239000002253 acid Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 14
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 12
- NIQLOLNJWXWZHX-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1C2C(CC(O)(C(F)(F)F)C(F)(F)F)CC1C=C2 NIQLOLNJWXWZHX-UHFFFAOYSA-N 0.000 claims description 11
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- RGVBEUZSLWVYFF-UHFFFAOYSA-N 5-(5-bicyclo[2.2.1]hept-2-enylmethoxymethoxymethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCOCC1C(C=C2)CC2C1 RGVBEUZSLWVYFF-UHFFFAOYSA-N 0.000 claims description 6
- MUIADVKDDBLDLO-UHFFFAOYSA-N 5-(5-bicyclo[2.2.1]hept-2-enylmethoxymethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCC1C(C=C2)CC2C1 MUIADVKDDBLDLO-UHFFFAOYSA-N 0.000 claims description 6
- XESFUKVQVZNIIW-UHFFFAOYSA-N 5-[2-[2-(5-bicyclo[2.2.1]hept-2-enyl)ethoxy]ethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCOCCC1C(C=C2)CC2C1 XESFUKVQVZNIIW-UHFFFAOYSA-N 0.000 claims description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- QDHJPVYLXXGNTO-UHFFFAOYSA-N [4-(5-bicyclo[2.2.1]hept-2-enyl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1C(C=C2)CC2C1 QDHJPVYLXXGNTO-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- NNHGHNYBKLZWJQ-UHFFFAOYSA-N 5-[3-(5-bicyclo[2.2.1]hept-2-enyl)propyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCCC1C(C=C2)CC2C1 NNHGHNYBKLZWJQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 4
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 3
- QDIQZDCRECGYGO-UHFFFAOYSA-N 5-(4-methylphenyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1=CC(C)=CC=C1C1C(C=C2)CC2C1 QDIQZDCRECGYGO-UHFFFAOYSA-N 0.000 claims description 3
- BEECMFIGOSZCLQ-UHFFFAOYSA-N 5-[3-(5-bicyclo[2.2.1]hept-2-enylmethoxy)propoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCCCOCC1C(C=C2)CC2C1 BEECMFIGOSZCLQ-UHFFFAOYSA-N 0.000 claims description 3
- OCMPNYNPEGVYME-UHFFFAOYSA-N 5-[8-(5-bicyclo[2.2.1]hept-2-enylmethoxy)octoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCCCCCCCCOCC1C(C=C2)CC2C1 OCMPNYNPEGVYME-UHFFFAOYSA-N 0.000 claims description 3
- JFHAHWMZRTZJBL-UHFFFAOYSA-N 5-undecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCC)CC1C=C2 JFHAHWMZRTZJBL-UHFFFAOYSA-N 0.000 claims description 3
- UGUZEDRUYFOTMA-UHFFFAOYSA-N C12C(CC(C=C1)C2)C1=CC=C(C=C1)CC1=CC=C(C=C1)C1C2C=CC(C1)C2 Chemical compound C12C(CC(C=C1)C2)C1=CC=C(C=C1)CC1=CC=C(C=C1)C1C2C=CC(C1)C2 UGUZEDRUYFOTMA-UHFFFAOYSA-N 0.000 claims description 3
- VRQHZVPUKKTZLK-UHFFFAOYSA-N C12C(CC(C=C1)C2)CC(CC1C2C=CC(C1)C2)CC1C2C=CC(C1)C2 Chemical compound C12C(CC(C=C1)C2)CC(CC1C2C=CC(C1)C2)CC1C2C=CC(C1)C2 VRQHZVPUKKTZLK-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 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 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 2
- HJECNRRGJJSUKK-UHFFFAOYSA-N 2-bicyclo[2.2.2]oct-5-enylmethyl bicyclo[2.2.2]oct-5-ene-2-carboxylate Chemical compound C12C(CC(C=C1)CC2)C(=O)OCC1C2C=CC(C1)CC2 HJECNRRGJJSUKK-UHFFFAOYSA-N 0.000 claims description 2
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims description 2
- UYRZOVOOCHWSJB-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]hept-2-enyl)propanoic acid Chemical compound C1CC2C(CCC(=O)O)=CC1C2 UYRZOVOOCHWSJB-UHFFFAOYSA-N 0.000 claims description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 2
- QAUWEMDGTQKLLN-UHFFFAOYSA-N 5-[2-(5-bicyclo[2.2.1]hept-2-enylmethoxy)ethoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCCOCC1C(C=C2)CC2C1 QAUWEMDGTQKLLN-UHFFFAOYSA-N 0.000 claims description 2
- XBPHFDRIDANZMK-UHFFFAOYSA-N 5-[4-(5-bicyclo[2.2.1]hept-2-enylmethoxy)butoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCCCCOCC1C(C=C2)CC2C1 XBPHFDRIDANZMK-UHFFFAOYSA-N 0.000 claims description 2
- CEQOTRCBNBZYME-UHFFFAOYSA-N 5-[6-(5-bicyclo[2.2.1]hept-2-enylmethoxy)hexoxymethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCCCCCCOCC1C(C=C2)CC2C1 CEQOTRCBNBZYME-UHFFFAOYSA-N 0.000 claims description 2
- SOSZGLNDFITMMF-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OCC1C(C=C2)CC2C1 SOSZGLNDFITMMF-UHFFFAOYSA-N 0.000 claims description 2
- VVKPRHOUENDOED-UHFFFAOYSA-N 5-dodecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCC)CC1C=C2 VVKPRHOUENDOED-UHFFFAOYSA-N 0.000 claims description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 2
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- VXGHLZKRQOZPQK-UHFFFAOYSA-N bis(5-bicyclo[2.2.1]hept-2-enylmethyl) carbonate Chemical compound C1C(C=C2)CC2C1COC(=O)OCC1C(C=C2)CC2C1 VXGHLZKRQOZPQK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229940116333 ethyl lactate Drugs 0.000 claims description 2
- 229940117360 ethyl pyruvate Drugs 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 2
- 229940057867 methyl lactate Drugs 0.000 claims description 2
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 claims description 2
- 238000000059 patterning Methods 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 4
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 claims 1
- GBGYNUNJQGLNOK-UHFFFAOYSA-N acetic acid;pentane-2,4-diol Chemical compound CC(O)=O.CC(O)CC(C)O GBGYNUNJQGLNOK-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 abstract description 11
- 229920002125 Sokalan® Polymers 0.000 abstract description 2
- 238000004377 microelectronic Methods 0.000 abstract description 2
- 239000004584 polyacrylic acid Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 38
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 27
- 239000000463 material Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 230000018109 developmental process Effects 0.000 description 18
- 235000012431 wafers Nutrition 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 11
- 238000000879 optical micrograph Methods 0.000 description 11
- 238000003384 imaging method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000001459 lithography Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- WQVIVQDHNKQWTM-UHFFFAOYSA-N 1-tert-butyl-4-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C=C1 WQVIVQDHNKQWTM-UHFFFAOYSA-N 0.000 description 3
- FEHSMAYCLKFEBU-UHFFFAOYSA-N 5-[[3-(5-bicyclo[2.2.1]hept-2-enylmethoxy)phenoxy]methyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1=CC(OCC2C3CC(C=C3)C2)=CC(OCC2C3CC(C=C3)C2)=C1 FEHSMAYCLKFEBU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
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| JP7434853B2 (ja) * | 2019-12-03 | 2024-02-21 | 住友ベークライト株式会社 | 架橋剤、感光性樹脂組成物、硬化膜、および電子装置 |
| TWI850509B (zh) * | 2019-12-30 | 2024-08-01 | 日商住友電木股份有限公司 | 催化多環烯烴組成物的uv活性衍生物 |
| TWI850512B (zh) * | 2019-12-30 | 2024-08-01 | 日商住友電木股份有限公司 | 作為光學材料之uv活性鈀催化多環烯烴聚合物組成物 |
| TWI834019B (zh) * | 2020-01-09 | 2024-03-01 | 日商住友電木股份有限公司 | 作為3d列印材料之穩定本體聚合型多環烯烴組成物及其製備方法 |
| US20220413386A1 (en) * | 2021-06-09 | 2022-12-29 | Jeremy Golden | Improved Transparency in Negative Epoxy Photoresist |
| KR20250107860A (ko) * | 2022-11-14 | 2025-07-14 | 가부시끼가이샤 레조낙 | 중합성 조성물 |
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| US5910394A (en) * | 1997-06-18 | 1999-06-08 | Shipley Company, L.L.C. | I-line photoresist compositions |
| TW201033167A (en) * | 2008-10-20 | 2010-09-16 | Basf Se | Sulfonium derivatives and the use therof as latent acids |
| JP2011107170A (ja) * | 2009-09-21 | 2011-06-02 | Promerus Llc | 水性ベースの現像可能な官能化したノルボルネンポリマーをベースとしたネガ型フィルム |
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| US4898916A (en) | 1987-03-05 | 1990-02-06 | Hoechst Celanese Corporation | Process for the preparation of poly(vinylphenol) from poly(acetoxystyrene) by acid catalyzed transesterification |
| US4877843A (en) | 1987-09-11 | 1989-10-31 | Hoechst Celanese Corporation | Selective hydrolysis of copolymers of para-acetoxy styrene and allyl esters of ethylenically unsaturated acids |
| US4857601A (en) | 1987-09-11 | 1989-08-15 | Hoechst Celanese Corp. | Selective hydrolysis of copolymers of para-acetoxy styrene and dialkyl muconates or alkyl sorbates |
| US7022790B2 (en) * | 2002-07-03 | 2006-04-04 | Sumitomo Bakelite Company, Ltd. | Photosensitive compositions based on polycyclic polymers |
| US7160669B2 (en) * | 2002-10-16 | 2007-01-09 | Sumitomo Chemical Company, Limited | Chemical amplification type resist composition |
| JP4084710B2 (ja) * | 2003-06-12 | 2008-04-30 | 松下電器産業株式会社 | パターン形成方法 |
| TW200707106A (en) * | 2005-05-17 | 2007-02-16 | Kyowa Hakko Chemical Co Ltd | Photoresist composition |
| GB2457497B (en) * | 2008-02-15 | 2012-08-08 | Pilot Drilling Control Ltd | Flow stop valve |
| US8808959B2 (en) * | 2008-11-13 | 2014-08-19 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, novel compound, and acid generator |
| US8753790B2 (en) * | 2009-07-01 | 2014-06-17 | Promerus, Llc | Self-imageable film forming polymer, compositions thereof and devices and structures made therefrom |
| JP5728762B2 (ja) | 2010-11-24 | 2015-06-03 | 住友ベークライト株式会社 | 自己画像形成性フィルム形成ポリマー、その組成物、並びにそれから製造されるデバイス及び構造物 |
| CN103649220B (zh) | 2011-07-14 | 2015-09-09 | 住友电木株式会社 | 在成像式曝光于光化辐射下之后形成构图层的聚合物及其组合物 |
| CN104221176B (zh) * | 2012-01-16 | 2017-03-01 | 住友电木株式会社 | 用于微电子和光电子器件及其组件的热氧化稳定的、侧链聚醚官能化的聚降冰片烯 |
| KR101659940B1 (ko) | 2013-04-26 | 2016-09-27 | 스미토모 베이클리트 컴퍼니 리미티드 | 감광성 조성물 및 이의 적용 |
| WO2015038412A2 (en) * | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5910394A (en) * | 1997-06-18 | 1999-06-08 | Shipley Company, L.L.C. | I-line photoresist compositions |
| TW201033167A (en) * | 2008-10-20 | 2010-09-16 | Basf Se | Sulfonium derivatives and the use therof as latent acids |
| JP2011107170A (ja) * | 2009-09-21 | 2011-06-02 | Promerus Llc | 水性ベースの現像可能な官能化したノルボルネンポリマーをベースとしたネガ型フィルム |
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