TW575596B - Fluorine-containing cyclic olefin polymer, its cyclic olefinic monomer, process for producing the polymer and use thereof - Google Patents
Fluorine-containing cyclic olefin polymer, its cyclic olefinic monomer, process for producing the polymer and use thereof Download PDFInfo
- Publication number
- TW575596B TW575596B TW091108668A TW91108668A TW575596B TW 575596 B TW575596 B TW 575596B TW 091108668 A TW091108668 A TW 091108668A TW 91108668 A TW91108668 A TW 91108668A TW 575596 B TW575596 B TW 575596B
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- Prior art keywords
- fluorine
- group
- carbon atoms
- alkyl group
- containing alkyl
- Prior art date
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 367
- 239000011737 fluorine Substances 0.000 title claims abstract description 363
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 347
- 229920000642 polymer Polymers 0.000 title claims abstract description 207
- 238000000034 method Methods 0.000 title claims abstract description 55
- 239000000178 monomer Substances 0.000 title claims abstract description 55
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 121
- 125000004122 cyclic group Chemical group 0.000 title claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 204
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 191
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 238000010521 absorption reaction Methods 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 23
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 10
- -1 cyclic olefin Chemical class 0.000 claims description 191
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 142
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 109
- 229910052799 carbon Inorganic materials 0.000 claims description 102
- 238000005984 hydrogenation reaction Methods 0.000 claims description 97
- 239000010408 film Substances 0.000 claims description 81
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 56
- 229920002120 photoresistant polymer Polymers 0.000 claims description 51
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 31
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052710 silicon Inorganic materials 0.000 claims description 30
- 239000010703 silicon Substances 0.000 claims description 30
- 239000002313 adhesive film Substances 0.000 claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 238000005227 gel permeation chromatography Methods 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 229910052740 iodine Inorganic materials 0.000 claims description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 239000011630 iodine Substances 0.000 claims description 23
- 230000003287 optical effect Effects 0.000 claims description 22
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000004185 ester group Chemical group 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000010409 thin film Substances 0.000 claims description 13
- 125000001033 ether group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000001459 lithography Methods 0.000 claims description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004776 molecular orbital Methods 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000004576 sand Substances 0.000 claims description 2
- 239000000779 smoke Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 74
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 53
- 239000003054 catalyst Substances 0.000 description 44
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 37
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 37
- 239000000843 powder Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000000758 substrate Substances 0.000 description 35
- 238000001228 spectrum Methods 0.000 description 32
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 24
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 23
- 229910001634 calcium fluoride Inorganic materials 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 21
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical group CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 18
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 16
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 15
- 229910052723 transition metal Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 14
- 238000005649 metathesis reaction Methods 0.000 description 14
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 13
- 150000001993 dienes Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 239000010948 rhodium Substances 0.000 description 11
- 229910052707 ruthenium Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000002524 organometallic group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000002170 ethers Chemical group 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229920002313 fluoropolymer Polymers 0.000 description 8
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 8
- 150000003624 transition metals Chemical class 0.000 description 8
- 235000012431 wafers Nutrition 0.000 description 8
- 239000004811 fluoropolymer Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 5
- 150000002902 organometallic compounds Chemical class 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229960004624 perflexane Drugs 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910000314 transition metal oxide Inorganic materials 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
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- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 208000018459 dissociative disease Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
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- JAGYXYUAYDLKNO-UHFFFAOYSA-N hepta-2,5-diene Chemical compound CC=CCC=CC JAGYXYUAYDLKNO-UHFFFAOYSA-N 0.000 description 4
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- 230000007062 hydrolysis Effects 0.000 description 4
- 150000002576 ketones Chemical group 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
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- 241000208340 Araliaceae Species 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 150000001723 carbon free-radicals Chemical class 0.000 description 3
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 3
- 150000001735 carboxylic acids Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
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- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007154 radical cyclization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001055 reflectance spectroscopy Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- RIECPYZYOLVSJK-UHFFFAOYSA-N tert-butyl 2-dimethylsilyl-5-methylindole-1-carboxylate Chemical compound C[SiH](C)c1cc2cc(C)ccc2n1C(=O)OC(C)(C)C RIECPYZYOLVSJK-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical class C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- JTGNPNLBCGBCMP-UHFFFAOYSA-N tetraoctylstannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTGNPNLBCGBCMP-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AKQHUJRZKBYZLC-UHFFFAOYSA-N tri(propan-2-yl)-prop-2-enylsilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)CC=C AKQHUJRZKBYZLC-UHFFFAOYSA-N 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- BYQWEYFCJKJRHO-UHFFFAOYSA-K tribromo(butyl)stannane Chemical compound CCCC[Sn](Br)(Br)Br BYQWEYFCJKJRHO-UHFFFAOYSA-K 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- SVGQCVJXVAMCPM-UHFFFAOYSA-N triethyl(prop-2-enyl)silane Chemical compound CC[Si](CC)(CC)CC=C SVGQCVJXVAMCPM-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- ULAQISQDFQAUCH-UHFFFAOYSA-N trifluoromethanesulfonic acid hydroiodide Chemical compound I.OS(=O)(=O)C(F)(F)F ULAQISQDFQAUCH-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- BYVAUQCHMDRWFV-UHFFFAOYSA-M trioctylstannanylium;bromide Chemical compound CCCCCCCC[Sn](Br)(CCCCCCCC)CCCCCCCC BYVAUQCHMDRWFV-UHFFFAOYSA-M 0.000 description 1
- XMHKTINRBAKEDS-UHFFFAOYSA-N trioctyltin Chemical compound CCCCCCCC[Sn](CCCCCCCC)CCCCCCCC XMHKTINRBAKEDS-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G61/08—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 of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001132434 | 2001-04-27 | ||
| JP2002064653 | 2002-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW575596B true TW575596B (en) | 2004-02-11 |
Family
ID=26614474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091108668A TW575596B (en) | 2001-04-27 | 2002-04-26 | Fluorine-containing cyclic olefin polymer, its cyclic olefinic monomer, process for producing the polymer and use thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6875819B2 (enExample) |
| EP (1) | EP1298156B1 (enExample) |
| JP (2) | JP4236935B2 (enExample) |
| KR (1) | KR100583297B1 (enExample) |
| CN (1) | CN1233685C (enExample) |
| DE (1) | DE60205555T2 (enExample) |
| TW (1) | TW575596B (enExample) |
| WO (1) | WO2002088216A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI477530B (zh) * | 2009-08-26 | 2015-03-21 | Mitsui Chemicals Inc | 含氟環狀烯烴聚合物組成物、由該組成物得到的壓印體及其製造方法 |
| US11886119B2 (en) | 2017-05-31 | 2024-01-30 | Mitsui Chemicals, Inc. | Material for forming underlayer film, resist underlayer film, method of producing resist underlayer film, and laminate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875819B2 (en) * | 2001-04-27 | 2005-04-05 | Mitsui Chemicals, Inc. | Fluorinated cycloolefin polymers, processes for preparation of fluorinated cycloofefin monomers and polymers thereof, and use of the same |
| US7264853B2 (en) * | 2003-08-26 | 2007-09-04 | Intel Corporation | Attaching a pellicle frame to a reticle |
| US7316869B2 (en) * | 2003-08-26 | 2008-01-08 | Intel Corporation | Mounting a pellicle to a frame |
| JP2007506828A (ja) * | 2003-09-25 | 2007-03-22 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 弗素化された基を用いる開環メタセシス重合 |
| US7314667B2 (en) * | 2004-03-12 | 2008-01-01 | Intel Corporation | Process to optimize properties of polymer pellicles and resist for lithography applications |
| US20050202252A1 (en) * | 2004-03-12 | 2005-09-15 | Alexander Tregub | Use of alternative polymer materials for "soft" polymer pellicles |
| US20060008730A1 (en) * | 2004-07-09 | 2006-01-12 | Puy Michael V D | Monomers for photoresists bearing acid-labile groups of reduced optical density |
| US20060008731A1 (en) * | 2004-07-09 | 2006-01-12 | Michael Van Der Puy | Novel photoresist monomers and polymers |
| WO2007032048A1 (ja) * | 2005-09-12 | 2007-03-22 | Tadahiro Ohmi | 透明部材の製造方法およびプラスチック部材 |
| WO2007055489A1 (en) | 2005-11-08 | 2007-05-18 | Lg Chem, Ltd. | Colloidal photonic crystals using colloidal nanoparticles and method for preparation thereof |
| JP4866086B2 (ja) * | 2005-12-27 | 2012-02-01 | 三井化学株式会社 | 組み合わせレンズ、色収差の補正方法 |
| JP5475761B2 (ja) * | 2008-06-20 | 2014-04-16 | スリーエム イノベイティブ プロパティズ カンパニー | ポリマー鋳型 |
| JP5563567B2 (ja) * | 2008-06-20 | 2014-07-30 | スリーエム イノベイティブ プロパティズ カンパニー | 成型された微細構造物品及びその製造方法 |
| JP2010113315A (ja) * | 2008-10-10 | 2010-05-20 | Jsr Corp | フォトマスク |
| CN102334177B (zh) * | 2009-02-27 | 2014-01-08 | 三井化学株式会社 | 转印体及其制造方法 |
| JP2010210974A (ja) * | 2009-03-11 | 2010-09-24 | Shin-Etsu Chemical Co Ltd | ペリクルの製造方法及びペリクル |
| JP5366740B2 (ja) * | 2009-09-28 | 2013-12-11 | 富士フイルム株式会社 | 含エーテル環状構造含有ポリマー、光学材料用樹脂組成物、並びにその成形体、光学部品及びレンズ |
| KR20130024878A (ko) * | 2010-04-02 | 2013-03-08 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 포토 마스크 유닛 및 그 제조 방법 |
| AU2011328555B2 (en) * | 2010-11-11 | 2016-10-20 | Stahl International Bv | Non metal tanning |
| WO2012062411A1 (en) * | 2010-11-11 | 2012-05-18 | Clariant International Ltd | Non metal tanning |
| WO2012062413A1 (en) * | 2010-11-12 | 2012-05-18 | Clariant International Ltd | Non metal tanning |
| EP2881792B1 (en) * | 2012-08-02 | 2017-04-26 | Mitsui Chemicals, Inc. | Pellicle |
| KR101805280B1 (ko) | 2013-04-03 | 2017-12-05 | 미쓰이 가가쿠 가부시키가이샤 | 광학 필름 |
| JP2016105131A (ja) * | 2014-12-01 | 2016-06-09 | ウシオ電機株式会社 | 表面が改質された基板の製造方法、パターン形成体、基板表面の改質方法、および光照射装置 |
| CN107207708A (zh) * | 2015-02-09 | 2017-09-26 | 旭硝子株式会社 | 含氟聚合物的制造方法 |
| JP6593351B2 (ja) * | 2015-02-09 | 2019-10-23 | Ａｇｃ株式会社 | 含フッ素重合体の製造方法 |
| JP6448768B2 (ja) * | 2015-03-26 | 2019-01-09 | 三井化学株式会社 | 鉄道レール用軌道パッド用組成物及び鉄道レール用軌道パッド |
| CN107216444B (zh) * | 2017-07-20 | 2019-06-21 | 中国科学院长春应用化学研究所 | 一种透明、高耐热环烯烃共聚物及其制备方法 |
| JP7253340B2 (ja) * | 2018-09-04 | 2023-04-06 | アークレイ株式会社 | 光学素子及び光学素子の製造方法 |
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| JPS63238111A (ja) | 1987-03-27 | 1988-10-04 | Asahi Glass Co Ltd | 環状構造を有する含フツ素重合体の製造方法 |
| JP2581182B2 (ja) | 1987-08-14 | 1997-02-12 | 旭硝子株式会社 | 環化重合方法 |
| JP2526641B2 (ja) | 1987-08-14 | 1996-08-21 | 旭硝子株式会社 | 新規含フッ素環状重合体 |
| JPH024722A (ja) * | 1988-06-23 | 1990-01-09 | Mitsui Petrochem Ind Ltd | 弗素含有環状オレフィン化合物及びその製法 |
| JP2951337B2 (ja) | 1989-04-17 | 1999-09-20 | 古河電気工業株式会社 | ペリクル |
| JP2952962B2 (ja) | 1989-05-31 | 1999-09-27 | 旭硝子株式会社 | 汚染防止保護器具 |
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| JPH06199997A (ja) * | 1993-01-06 | 1994-07-19 | Japan Synthetic Rubber Co Ltd | 重合体の製造法 |
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| JPH06256477A (ja) * | 1993-03-02 | 1994-09-13 | Japan Synthetic Rubber Co Ltd | 重合体の製造法 |
| EP0722468A1 (en) * | 1993-09-10 | 1996-07-24 | Ciba SC Holding AG | Process for the polymerization of cyclic olefins and a polymerizable composition |
| US5677405A (en) * | 1995-05-24 | 1997-10-14 | The B.F. Goodrich Company | Homopolymers and copolymers of cationically polymerizable monomers and method of their preparation |
| US6121340A (en) * | 1996-11-04 | 2000-09-19 | The B. F. Goodrich Company | Photodefinable dielectric compositions comprising polycyclic polymers |
| WO1998036324A1 (en) | 1997-02-13 | 1998-08-20 | Mitsui Chemicals, Inc. | Pellicle membrane for ultraviolet rays and pellicle |
| WO2000017712A1 (en) * | 1998-09-23 | 2000-03-30 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| EP1183571B1 (en) | 1999-05-04 | 2010-06-02 | E.I. Du Pont De Nemours And Company | Fluorinated photoresists and processes for microlithography |
| JP3901401B2 (ja) * | 1999-07-13 | 2007-04-04 | 三井化学株式会社 | ポジ型フォトレジスト組成物およびパターン形成方法 |
| JP2001226467A (ja) * | 2000-02-17 | 2001-08-21 | Hitachi Chem Co Ltd | フッ素含有ノルボルネン系重合体およびその製造方法 |
| JP2001328964A (ja) * | 2000-05-19 | 2001-11-27 | Tokyo Ohka Kogyo Co Ltd | 新規多環式不飽和炭化水素誘導体及びその製造方法 |
| US6875819B2 (en) * | 2001-04-27 | 2005-04-05 | Mitsui Chemicals, Inc. | Fluorinated cycloolefin polymers, processes for preparation of fluorinated cycloofefin monomers and polymers thereof, and use of the same |
-
2002
- 2002-04-25 US US10/312,506 patent/US6875819B2/en not_active Expired - Lifetime
- 2002-04-25 JP JP2002585513A patent/JP4236935B2/ja not_active Expired - Fee Related
- 2002-04-25 CN CNB028014243A patent/CN1233685C/zh not_active Expired - Lifetime
- 2002-04-25 EP EP02722782A patent/EP1298156B1/en not_active Expired - Lifetime
- 2002-04-25 KR KR1020027017694A patent/KR100583297B1/ko not_active Expired - Lifetime
- 2002-04-25 WO PCT/JP2002/004140 patent/WO2002088216A1/ja not_active Ceased
- 2002-04-25 DE DE60205555T patent/DE60205555T2/de not_active Expired - Lifetime
- 2002-04-26 TW TW091108668A patent/TW575596B/zh not_active IP Right Cessation
-
2008
- 2008-05-19 JP JP2008130940A patent/JP2008239995A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI477530B (zh) * | 2009-08-26 | 2015-03-21 | Mitsui Chemicals Inc | 含氟環狀烯烴聚合物組成物、由該組成物得到的壓印體及其製造方法 |
| US11886119B2 (en) | 2017-05-31 | 2024-01-30 | Mitsui Chemicals, Inc. | Material for forming underlayer film, resist underlayer film, method of producing resist underlayer film, and laminate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1233685C (zh) | 2005-12-28 |
| EP1298156A1 (en) | 2003-04-02 |
| WO2002088216A1 (fr) | 2002-11-07 |
| KR20040002398A (ko) | 2004-01-07 |
| US20030187168A1 (en) | 2003-10-02 |
| JP2008239995A (ja) | 2008-10-09 |
| US6875819B2 (en) | 2005-04-05 |
| EP1298156A4 (en) | 2003-09-10 |
| JP4236935B2 (ja) | 2009-03-11 |
| EP1298156B1 (en) | 2005-08-17 |
| DE60205555T2 (de) | 2006-03-30 |
| DE60205555D1 (de) | 2005-09-22 |
| JPWO2002088216A1 (ja) | 2004-08-19 |
| CN1462286A (zh) | 2003-12-17 |
| KR100583297B1 (ko) | 2006-05-24 |
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