TWI300167B - Photosensitive compositions based on polycyclic polymers - Google Patents
Photosensitive compositions based on polycyclic polymers Download PDFInfo
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- TWI300167B TWI300167B TW092118096A TW92118096A TWI300167B TW I300167 B TWI300167 B TW I300167B TW 092118096 A TW092118096 A TW 092118096A TW 92118096 A TW92118096 A TW 92118096A TW I300167 B TWI300167 B TW I300167B
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- ether
- copolymer
- branched
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- 239000000203 mixture Substances 0.000 title claims abstract description 204
- 229920005567 polycyclic polymer Polymers 0.000 title description 3
- 229920001577 copolymer Polymers 0.000 claims abstract description 92
- 239000000463 material Substances 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 239000004593 Epoxy Substances 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 11
- 125000005647 linker group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- -1 dicyclopropylindenyl Chemical group 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 35
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 19
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 18
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 16
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 15
- 125000003700 epoxy group Chemical group 0.000 claims description 15
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229960000834 vinyl ether Drugs 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000002516 radical scavenger Substances 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 150000004292 cyclic ethers Chemical class 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002318 adhesion promoter Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000003849 aromatic solvent Substances 0.000 claims description 6
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- 229920001289 polyvinyl ether Polymers 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 6
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims description 4
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 claims description 4
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 claims description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002926 oxygen Chemical class 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000010665 pine oil Substances 0.000 claims description 4
- 230000009257 reactivity Effects 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 claims description 3
- QOYBXUIKQOIDQO-UHFFFAOYSA-N 1,3-bis(ethenoxy)propane Chemical compound C=COCCCOC=C QOYBXUIKQOIDQO-UHFFFAOYSA-N 0.000 claims description 3
- JOSFJABFAXRZJQ-UHFFFAOYSA-N 1,6-bis(ethenoxy)hexane Chemical compound C=COCCCCCCOC=C JOSFJABFAXRZJQ-UHFFFAOYSA-N 0.000 claims description 3
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 claims description 3
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 claims description 3
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 3
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 2
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 claims description 2
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 claims description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 206010036790 Productive cough Diseases 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 159000000014 iron salts Chemical class 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 210000003802 sputum Anatomy 0.000 claims description 2
- 208000024794 sputum Diseases 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 244000291564 Allium cepa Species 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- 229940052303 ethers for general anesthesia Drugs 0.000 claims 4
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 claims 3
- ASPUDHDPXIBNAP-UHFFFAOYSA-N 6-ethenoxyhexan-1-ol Chemical compound OCCCCCCOC=C ASPUDHDPXIBNAP-UHFFFAOYSA-N 0.000 claims 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 3
- 150000004056 anthraquinones Chemical class 0.000 claims 3
- 150000002170 ethers Chemical class 0.000 claims 3
- AAWSDNAGOTWUPV-UHFFFAOYSA-N sulfanyloxyethene Chemical compound SOC=C AAWSDNAGOTWUPV-UHFFFAOYSA-N 0.000 claims 3
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 claims 2
- IRECSNJNCXXLOR-UHFFFAOYSA-N 1,8-bis(ethenoxy)octane Chemical compound C=COCCCCCCCCOC=C IRECSNJNCXXLOR-UHFFFAOYSA-N 0.000 claims 2
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
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- 235000019239 indanthrene blue RS Nutrition 0.000 claims 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims 2
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- 239000011630 iodine Substances 0.000 claims 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims 2
- 239000003504 photosensitizing agent Substances 0.000 claims 2
- 229920000636 poly(norbornene) polymer Polymers 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 claims 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 claims 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- PSJBSUHYCGQTHZ-UHFFFAOYSA-N 3-Methoxy-1,2-propanediol Chemical compound COCC(O)CO PSJBSUHYCGQTHZ-UHFFFAOYSA-N 0.000 claims 1
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- GNPSQUCXOBDIDY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane Chemical compound C(CCCCCCC)C(C(OC)(OC)OC)CCC GNPSQUCXOBDIDY-UHFFFAOYSA-N 0.000 claims 1
- PZDQNTVFKRWKOI-UHFFFAOYSA-N 4-propan-2-yl-9H-xanthene Chemical compound C(C)(C)C1=CC=CC=2CC3=CC=CC=C3OC1=2 PZDQNTVFKRWKOI-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- RDJHNDDZKQCDPL-UHFFFAOYSA-N 8-ethenoxyoctan-1-ol Chemical compound OCCCCCCCCOC=C RDJHNDDZKQCDPL-UHFFFAOYSA-N 0.000 claims 1
- JTFLJUSQOWBZTM-UHFFFAOYSA-N C=C.C=C.Cl.Cl Chemical compound C=C.C=C.Cl.Cl JTFLJUSQOWBZTM-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 239000004386 Erythritol Substances 0.000 claims 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- DFGMFVYRMVYRRA-UHFFFAOYSA-N [O].CC Chemical compound [O].CC DFGMFVYRMVYRRA-UHFFFAOYSA-N 0.000 claims 1
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- 239000002612 dispersion medium Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NCGARFWFKHNMJK-UHFFFAOYSA-N oxiran-2-ylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CO1 NCGARFWFKHNMJK-UHFFFAOYSA-N 0.000 description 1
- RCYPXVCYMDSECE-UHFFFAOYSA-N oxiran-2-ylmethylhydrazine Chemical compound NNCC1CO1 RCYPXVCYMDSECE-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000002186 photoactivation Effects 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SWLICCIRFBHLJN-UHFFFAOYSA-N tricyclohexylphosphanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 SWLICCIRFBHLJN-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical group NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- RIUWBIIVUYSTCN-UHFFFAOYSA-N trilithium borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-] RIUWBIIVUYSTCN-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000004711 α-olefin Substances 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
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)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Materials For Photolithography (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Polymerisation Methods In General (AREA)
- Silicon Polymers (AREA)
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| US39372602P | 2002-07-03 | 2002-07-03 | |
| US10/465,511 US7022790B2 (en) | 2002-07-03 | 2003-06-19 | Photosensitive compositions based on polycyclic polymers |
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| TW200412472A TW200412472A (en) | 2004-07-16 |
| TWI300167B true TWI300167B (en) | 2008-08-21 |
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| TW092118096A TWI300167B (en) | 2002-07-03 | 2003-07-02 | Photosensitive compositions based on polycyclic polymers |
| TW097115706A TWI398459B (zh) | 2002-07-03 | 2003-07-02 | 以多環聚合物為主的光敏感性組成物（一） |
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| TW097115706A TWI398459B (zh) | 2002-07-03 | 2003-07-02 | 以多環聚合物為主的光敏感性組成物（一） |
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| EP (1) | EP1532486B1 (enExample) |
| JP (1) | JP4623419B2 (enExample) |
| KR (1) | KR100688632B1 (enExample) |
| CN (2) | CN1666150A (enExample) |
| AT (1) | ATE453135T1 (enExample) |
| AU (1) | AU2003243013A1 (enExample) |
| DE (1) | DE60330672D1 (enExample) |
| MY (1) | MY142759A (enExample) |
| TW (2) | TWI300167B (enExample) |
| WO (1) | WO2004006020A1 (enExample) |
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| US7022790B2 (en) * | 2002-07-03 | 2006-04-04 | Sumitomo Bakelite Company, Ltd. | Photosensitive compositions based on polycyclic polymers |
| US20060020068A1 (en) * | 2004-07-07 | 2006-01-26 | Edmund Elce | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
| US7501230B2 (en) * | 2002-11-04 | 2009-03-10 | Meagley Robert P | Photoactive adhesion promoter |
| US6893985B2 (en) * | 2003-03-31 | 2005-05-17 | Intel Corporation | UV-activated dielectric layer |
| ATE450813T1 (de) * | 2004-05-17 | 2009-12-15 | Fujifilm Corp | Verfahren zur erzeugung eines musters |
| JP4759311B2 (ja) * | 2004-05-17 | 2011-08-31 | 富士フイルム株式会社 | パターン形成方法 |
| JP2006096812A (ja) * | 2004-09-28 | 2006-04-13 | Sumitomo Bakelite Co Ltd | 半導体表面保護膜用樹脂組成物、及びそれを用いた半導体装置 |
| TW200628981A (en) * | 2004-09-29 | 2006-08-16 | Sumitomo Bakelite Co | Semiconductor device |
| JP2006100562A (ja) * | 2004-09-29 | 2006-04-13 | Sumitomo Bakelite Co Ltd | 半導体装置 |
| JP4556598B2 (ja) * | 2004-09-30 | 2010-10-06 | 住友ベークライト株式会社 | 半導体装置 |
| JP4170277B2 (ja) * | 2004-09-30 | 2008-10-22 | 住友ベークライト株式会社 | 感光性樹脂組成物および半導体装置 |
| JP2006098949A (ja) * | 2004-09-30 | 2006-04-13 | Sumitomo Bakelite Co Ltd | 半導体装置 |
| JP2006124648A (ja) * | 2004-10-01 | 2006-05-18 | Sumitomo Bakelite Co Ltd | 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板 |
| KR100892204B1 (ko) * | 2004-10-13 | 2009-04-07 | 스미토모 베이클리트 컴퍼니 리미티드 | 수광 장치 |
| TW200619843A (en) * | 2004-10-20 | 2006-06-16 | Sumitomo Bakelite Co | Semiconductor wafer and semiconductor device |
| KR100789247B1 (ko) * | 2005-01-05 | 2008-01-02 | 주식회사 엘지화학 | 광반응성 중합체 및 이의 제조 방법 |
| KR100655801B1 (ko) | 2005-01-18 | 2006-12-08 | 삼성전자주식회사 | 포토레지스트 조성물 및 이를 이용한 포토레지스트 패턴형성 방법 |
| EP1788434B2 (en) * | 2005-11-18 | 2019-01-02 | Agfa Nv | Method of making a lithographic printing plate |
| US8207279B2 (en) * | 2006-06-26 | 2012-06-26 | Lg Chem, Ltd. | Method for preparing norbornene monomer composition, norbornene polymer prepared therefrom, optical film comprising the norbornene polymer, and method for preparing the norbornene polymer |
| JP5040432B2 (ja) * | 2007-05-15 | 2012-10-03 | 住友ベークライト株式会社 | 感光性樹脂組成物 |
| KR101451802B1 (ko) * | 2007-07-31 | 2014-10-16 | 삼성에스디아이 주식회사 | 글리시딜 에테르계 화합물을 채용한 유기전해액 및 리튬전지 |
| US7906568B2 (en) * | 2007-09-04 | 2011-03-15 | General Electric Company | Coupling agent composition and associated method |
| US8039543B2 (en) * | 2007-09-04 | 2011-10-18 | General Electric Company | Composition comprising a coupling agent and a cycloolefin, the coupling agent comprising a reaction product of an epoxy-substituted cycloolefin and an aromatic amine |
| US8039544B2 (en) * | 2007-09-04 | 2011-10-18 | General Electric Company | Coupling agent comprising a reaction product of an epoxy-substituted cycloolefin and an aromatic amine |
| US7994238B2 (en) * | 2007-09-04 | 2011-08-09 | General Electric Company | Article and associated method |
| US9786576B2 (en) | 2007-11-12 | 2017-10-10 | Hitachi Chemical Company, Ltd | Positive-type photosensitive resin composition, method for production of resist pattern, semiconductor device, and electronic device |
| US7902279B2 (en) * | 2007-12-04 | 2011-03-08 | General Electric Company | Composition, article, and associated method |
| US7879963B2 (en) * | 2007-12-18 | 2011-02-01 | General Electric Company | Composition, article, and associated method |
| US8609574B2 (en) * | 2008-04-25 | 2013-12-17 | Promerus Llc | In situ olefin polymerization catalyst system |
| WO2010026988A1 (ja) | 2008-09-04 | 2010-03-11 | 日立化成工業株式会社 | ポジ型感光性樹脂組成物、レジストパターンの製造方法及び電子部品 |
| CN103091987B (zh) | 2008-12-26 | 2016-11-23 | 日立化成株式会社 | 正型感光性树脂组合物、抗蚀图形的制造方法、半导体装置以及电子器件 |
| JP5656413B2 (ja) * | 2009-01-30 | 2015-01-21 | 富士フイルム株式会社 | ネガ型レジストパターン形成方法、それに用いられる現像液及びネガ型化学増幅型レジスト組成物、並びにレジストパターン |
| TWI430036B (zh) * | 2009-04-20 | 2014-03-11 | Asahi Kasei E Materials Corp | Photosensitive resin laminate |
| US8753790B2 (en) * | 2009-07-01 | 2014-06-17 | Promerus, Llc | Self-imageable film forming polymer, compositions thereof and devices and structures made therefrom |
| KR101238403B1 (ko) | 2009-09-04 | 2013-02-28 | 주식회사 엘지화학 | 광 반응성기를 갖는 노보넨계 중합체를 포함하는 액정 배향용 조성물 및 이를 포함하는 광 배향 필름 |
| US8580477B2 (en) * | 2009-09-21 | 2013-11-12 | Promerus Llc | Aqueous base-developable negative-tone films based on functionalized norbornene polymers |
| WO2011105443A1 (ja) * | 2010-02-25 | 2011-09-01 | 日立化成工業株式会社 | ネガ型感光性樹脂組成物、層間絶縁膜及びその形成方法 |
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| KR101364229B1 (ko) * | 2012-12-20 | 2014-02-17 | 동우 화인켐 주식회사 | 감광성 수지 조성물 및 이로부터 제조되는 절연막 |
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| US20160311970A1 (en) * | 2013-12-13 | 2016-10-27 | Transfert Plus, Société En Commandite | Insertion polynorbornene-based thermoset resins |
| WO2015141525A1 (ja) * | 2014-03-20 | 2015-09-24 | 住友ベークライト株式会社 | 感光性樹脂組成物、および電子装置 |
| JP6459192B2 (ja) * | 2014-03-20 | 2019-01-30 | 住友ベークライト株式会社 | 感光性樹脂組成物 |
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| JP6550275B2 (ja) * | 2015-06-15 | 2019-07-24 | 東京応化工業株式会社 | ナノインプリント用組成物、硬化物、パターン形成方法及びパターンを含む物品 |
| CN109313388B (zh) * | 2016-06-14 | 2022-06-21 | 住友电木株式会社 | 负型感光性组合物 |
| JP6558479B2 (ja) * | 2018-07-18 | 2019-08-14 | 住友ベークライト株式会社 | ポリマー、および感光性樹脂組成物 |
| US12077627B2 (en) | 2022-04-26 | 2024-09-03 | Chevron Phillips Chemical Company Lp | Aqueous methods for titanating a chromium/silica catalyst with an alkali metal |
| KR102515739B1 (ko) * | 2022-12-07 | 2023-03-30 | 타코마테크놀러지 주식회사 | 감광성 수지 및 이를 포함하는 포토레지스트 조성물 |
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| US5468819A (en) | 1993-11-16 | 1995-11-21 | The B.F. Goodrich Company | Process for making polymers containing a norbornene repeating unit by addition polymerization using an organo (nickel or palladium) complex |
| DE19509173B4 (de) * | 1994-03-14 | 2005-06-16 | Nippon Zeon Co., Ltd. | Masse aus einem Epoxygruppen enthaltenden thermoplastischen Norbornenharz und ihre Verwendung |
| JP3588498B2 (ja) | 1994-03-14 | 2004-11-10 | 日本ゼオン株式会社 | エポキシ基を有する環状オレフィン系樹脂組成物および該樹脂組成物を用いた絶縁材料 |
| US6294616B1 (en) * | 1995-05-25 | 2001-09-25 | B. F. Goodrich Company | Blends and alloys of polycyclic polymers |
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| RU2194295C2 (ru) * | 1996-03-07 | 2002-12-10 | З Би. Эф. Гудрич Кампэни | Фоторезистная композиция и полимер |
| US6121340A (en) * | 1996-11-04 | 2000-09-19 | The B. F. Goodrich Company | Photodefinable dielectric compositions comprising polycyclic polymers |
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| US7022790B2 (en) | 2002-07-03 | 2006-04-04 | Sumitomo Bakelite Company, Ltd. | Photosensitive compositions based on polycyclic polymers |
-
2003
- 2003-06-19 US US10/465,511 patent/US7022790B2/en not_active Expired - Lifetime
- 2003-06-24 MY MYPI20032361A patent/MY142759A/en unknown
- 2003-07-02 KR KR1020047021566A patent/KR100688632B1/ko not_active Expired - Fee Related
- 2003-07-02 CN CN038158094A patent/CN1666150A/zh active Pending
- 2003-07-02 TW TW092118096A patent/TWI300167B/zh not_active IP Right Cessation
- 2003-07-02 JP JP2004519232A patent/JP4623419B2/ja not_active Expired - Fee Related
- 2003-07-02 TW TW097115706A patent/TWI398459B/zh not_active IP Right Cessation
- 2003-07-02 EP EP03762871A patent/EP1532486B1/en not_active Expired - Lifetime
- 2003-07-02 WO PCT/JP2003/008407 patent/WO2004006020A1/en not_active Ceased
- 2003-07-02 AT AT03762871T patent/ATE453135T1/de not_active IP Right Cessation
- 2003-07-02 AU AU2003243013A patent/AU2003243013A1/en not_active Abandoned
- 2003-07-02 DE DE60330672T patent/DE60330672D1/de not_active Expired - Lifetime
- 2003-07-02 CN CN201110146567.6A patent/CN102298265B/zh not_active Expired - Fee Related
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2006
- 2006-01-03 US US11/324,738 patent/US8114948B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MY142759A (en) | 2010-12-31 |
| DE60330672D1 (de) | 2010-02-04 |
| JP2005531680A (ja) | 2005-10-20 |
| CN1666150A (zh) | 2005-09-07 |
| KR20050033565A (ko) | 2005-04-12 |
| WO2004006020A1 (en) | 2004-01-15 |
| EP1532486B1 (en) | 2009-12-23 |
| ATE453135T1 (de) | 2010-01-15 |
| AU2003243013A1 (en) | 2004-01-23 |
| US20060167197A1 (en) | 2006-07-27 |
| US7022790B2 (en) | 2006-04-04 |
| TWI398459B (zh) | 2013-06-11 |
| CN102298265A (zh) | 2011-12-28 |
| US8114948B2 (en) | 2012-02-14 |
| KR100688632B1 (ko) | 2007-03-02 |
| TW200412472A (en) | 2004-07-16 |
| EP1532486A1 (en) | 2005-05-25 |
| CN102298265B (zh) | 2014-04-16 |
| US20040039153A1 (en) | 2004-02-26 |
| TW200835710A (en) | 2008-09-01 |
| JP4623419B2 (ja) | 2011-02-02 |
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