DE60205555T2 - Fluorinierte cycloolefinpolymere und verfahren zu deren herstellung, sowie deren verwendung - Google Patents
Fluorinierte cycloolefinpolymere und verfahren zu deren herstellung, sowie deren verwendung Download PDFInfo
- Publication number
- DE60205555T2 DE60205555T2 DE60205555T DE60205555T DE60205555T2 DE 60205555 T2 DE60205555 T2 DE 60205555T2 DE 60205555 T DE60205555 T DE 60205555T DE 60205555 T DE60205555 T DE 60205555T DE 60205555 T2 DE60205555 T2 DE 60205555T2
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- carbon atoms
- group
- alkyl group
- containing alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 137
- 238000000034 method Methods 0.000 title claims description 64
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 490
- 239000011737 fluorine Substances 0.000 claims description 476
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 475
- 125000004432 carbon atom Chemical group C* 0.000 claims description 301
- 229920000642 polymer Polymers 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 229
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 155
- -1 hydroxycarbonyl group Chemical group 0.000 claims description 139
- 238000005984 hydrogenation reaction Methods 0.000 claims description 79
- 239000000178 monomer Substances 0.000 claims description 50
- 239000000460 chlorine Substances 0.000 claims description 49
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
- 150000001925 cycloalkenes Chemical class 0.000 claims description 46
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 43
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 41
- 238000010521 absorption reaction Methods 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 36
- 238000000576 coating method Methods 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- 239000010409 thin film Substances 0.000 claims description 34
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229920002120 photoresistant polymer Polymers 0.000 claims description 33
- 229910052710 silicon Inorganic materials 0.000 claims description 33
- 239000010703 silicon Substances 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 238000005227 gel permeation chromatography Methods 0.000 claims description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 229910052740 iodine Inorganic materials 0.000 claims description 26
- 239000011630 iodine Substances 0.000 claims description 25
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
- 125000004185 ester group Chemical group 0.000 claims description 24
- 125000001033 ether group Chemical group 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000001459 lithography Methods 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 238000004776 molecular orbital Methods 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000758 substrate Substances 0.000 description 62
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 53
- 229920000728 polyester Polymers 0.000 description 53
- 239000010408 film Substances 0.000 description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000003054 catalyst Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 40
- 239000000843 powder Substances 0.000 description 37
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 36
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- 239000012528 membrane Substances 0.000 description 29
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 28
- 238000003756 stirring Methods 0.000 description 25
- UCCWJJZPOSPPIC-UHFFFAOYSA-N COOCF Chemical compound COOCF UCCWJJZPOSPPIC-UHFFFAOYSA-N 0.000 description 24
- 229910004261 CaF 2 Inorganic materials 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910052760 oxygen Inorganic materials 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229910052723 transition metal Inorganic materials 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 230000035699 permeability Effects 0.000 description 13
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- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000003624 transition metals Chemical class 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 125000002524 organometallic group Chemical group 0.000 description 11
- 239000010948 rhodium Substances 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000002834 transmittance Methods 0.000 description 9
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ICGUZQMJLPIVHP-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,2,2,2-pentafluoroethyl)-3-(trifluoromethyl)bicyclo[2.2.1]hept-5-ene Chemical compound C1C2C=CC1C(C(F)(F)C(F)(F)F)(F)C2(F)C(F)(F)F ICGUZQMJLPIVHP-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
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 5
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- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 5
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000007154 radical cyclization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 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
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- GHPHCACQRYSXSS-UHFFFAOYSA-N ruthenium;tricyclohexylphosphane Chemical compound [Ru].C1CCCCC1P(C1CCCCC1)C1CCCCC1 GHPHCACQRYSXSS-UHFFFAOYSA-N 0.000 description 1
- IQRJQJHIBJHUIP-UHFFFAOYSA-N ruthenium;triethylphosphane Chemical compound [Ru].CCP(CC)CC IQRJQJHIBJHUIP-UHFFFAOYSA-N 0.000 description 1
- XNBYBQSCHAFTIY-UHFFFAOYSA-N ruthenium;tris(2-methylphenyl)phosphane Chemical compound [Ru].CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C XNBYBQSCHAFTIY-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 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
- 239000007790 solid phase Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(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
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 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
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- SMAVBLSQIQGWLU-UHFFFAOYSA-M trioctylstannanylium;iodide Chemical compound CCCCCCCC[Sn](I)(CCCCCCCC)CCCCCCCC SMAVBLSQIQGWLU-UHFFFAOYSA-M 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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-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
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
-
- 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)
- 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001132434 | 2001-04-27 | ||
| JP2001132434 | 2001-04-27 | ||
| JP2002064653 | 2002-03-11 | ||
| JP2002064653 | 2002-03-11 | ||
| PCT/JP2002/004140 WO2002088216A1 (fr) | 2001-04-27 | 2002-04-25 | Polymeres cycloolefiniques fluores, procedes de preparation de monomeres cycloolefiniques fluores et polymeres associes, et leur application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60205555D1 DE60205555D1 (de) | 2005-09-22 |
| DE60205555T2 true DE60205555T2 (de) | 2006-03-30 |
Family
ID=26614474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60205555T Expired - Lifetime DE60205555T2 (de) | 2001-04-27 | 2002-04-25 | Fluorinierte cycloolefinpolymere und verfahren zu deren herstellung, sowie deren verwendung |
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) |
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| JP4236935B2 (ja) * | 2001-04-27 | 2009-03-11 | 三井化学株式会社 | フッ素含有環状オレフィンポリマー、その環状オレフィン系単量体、ポリマーの製造方法およびその用途 |
| US7316869B2 (en) * | 2003-08-26 | 2008-01-08 | Intel Corporation | Mounting a pellicle to a frame |
| US7264853B2 (en) * | 2003-08-26 | 2007-09-04 | Intel Corporation | Attaching a pellicle frame to a reticle |
| CA2539560A1 (en) * | 2003-09-25 | 2005-03-31 | Dario Lazzari | Romp with fluorinated groups |
| 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 |
| US20060008731A1 (en) * | 2004-07-09 | 2006-01-12 | Michael Van Der Puy | Novel photoresist monomers and polymers |
| US20060008730A1 (en) * | 2004-07-09 | 2006-01-12 | Puy Michael V D | Monomers for photoresists bearing acid-labile groups of reduced optical density |
| 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 |
| EP1827674B1 (en) | 2005-11-08 | 2012-09-12 | 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 |
| WO2009154879A2 (en) * | 2008-06-20 | 2009-12-23 | 3M Innovative Properties Company | Polymeric molds and articles made therefrom |
| CN102066456A (zh) * | 2008-06-20 | 2011-05-18 | 3M创新有限公司 | 模制微结构化制品及其制备方法 |
| JP2010113315A (ja) * | 2008-10-10 | 2010-05-20 | Jsr Corp | フォトマスク |
| US20110301313A1 (en) * | 2009-02-27 | 2011-12-08 | Mitsui Chemicals, Inc. | Imprint product and method for producing the same |
| 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 |
| WO2011024421A1 (ja) * | 2009-08-26 | 2011-03-03 | 三井化学株式会社 | フッ素含有環状オレフィンポリマー組成物、該組成物から得られた転写体およびその製造方法 |
| 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 |
| EP2555052B1 (en) * | 2010-04-02 | 2024-10-16 | Shin-Etsu Chemical Co., Ltd. | Photomask unit and method of manufacturing same |
| CN103201396B (zh) * | 2010-11-11 | 2014-12-03 | 克拉里安特国际有限公司 | 非金属鞣制 |
| BR112013011268B1 (pt) * | 2010-11-11 | 2020-02-27 | Stahl International B.V. | Processo para a produção de couro, peles ou pelicas curtidos por curtimento não metálico, uso da composição de curtimento (T1), couro, peles ou pelicas curtidos e seu uso |
| KR101845691B1 (ko) * | 2010-11-12 | 2018-04-05 | 스탈 인터내셔날 비.브이. | 비금속 태닝 |
| KR101699635B1 (ko) * | 2012-08-02 | 2017-01-24 | 미쓰이 가가쿠 가부시키가이샤 | 펠리클 |
| 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 |
| 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 |
| EP3257885A4 (en) * | 2015-02-09 | 2018-05-09 | Asahi Glass Company, Limited | Method for producing fluorine-containing polymer |
| CN107407059B (zh) * | 2015-03-26 | 2019-05-17 | 三井化学株式会社 | 铁路轨道用轨道垫片用组合物及铁路轨道用轨道垫片 |
| JP6840844B2 (ja) | 2017-05-31 | 2021-03-10 | 三井化学株式会社 | 下層膜形成用材料、レジスト下層膜、レジスト下層膜の製造方法および積層体 |
| 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 |
| JP2024132551A (ja) * | 2023-03-17 | 2024-10-01 | 日本ゼオン株式会社 | 含フッ素開環重合体 |
| CN121343135B (zh) * | 2025-12-17 | 2026-06-09 | 拓烯科技(衢州)有限公司 | 一种环烯烃聚合物、有色环烯烃聚合物薄膜及其制备方法与应用 |
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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 |
| 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 |
| JP2581182B2 (ja) | 1987-08-14 | 1997-02-12 | 旭硝子株式会社 | 環化重合方法 |
| 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 |
| JPH04104155A (ja) | 1990-08-23 | 1992-04-06 | Shin Etsu Chem Co Ltd | リソグラフィー用ペリクル |
| JPH06199997A (ja) * | 1993-01-06 | 1994-07-19 | Japan Synthetic Rubber Co Ltd | 重合体の製造法 |
| JPH06206985A (ja) * | 1993-01-08 | 1994-07-26 | Japan Synthetic Rubber Co Ltd | （水添）ノルボルネン系重合体 |
| JPH06256477A (ja) * | 1993-03-02 | 1994-09-13 | Japan Synthetic Rubber Co Ltd | 重合体の製造法 |
| AU7692294A (en) * | 1993-09-10 | 1995-03-27 | Ciba-Geigy 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 |
| WO1998020394A1 (en) | 1996-11-04 | 1998-05-14 | The B.F. Goodrich Company | Photodefinable dielectric compositions |
| EP0907106A4 (en) | 1997-02-13 | 2000-04-05 | Mitsui Chemicals Inc | FILM MEMBRANE FOR ULTRAVIOLET RAYS AND FILM |
| WO2000017712A1 (en) * | 1998-09-23 | 2000-03-30 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| DE60044493D1 (de) | 1999-05-04 | 2010-07-15 | Du Pont | Fluorierte photoresists und verfahren für die mikrolithographie |
| 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 |
| JP4236935B2 (ja) * | 2001-04-27 | 2009-03-11 | 三井化学株式会社 | フッ素含有環状オレフィンポリマー、その環状オレフィン系単量体、ポリマーの製造方法およびその用途 |
-
2002
- 2002-04-25 JP JP2002585513A patent/JP4236935B2/ja not_active Expired - Fee Related
- 2002-04-25 WO PCT/JP2002/004140 patent/WO2002088216A1/ja not_active Ceased
- 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 DE DE60205555T patent/DE60205555T2/de not_active Expired - Lifetime
- 2002-04-25 US US10/312,506 patent/US6875819B2/en not_active Expired - Lifetime
- 2002-04-25 CN CNB028014243A patent/CN1233685C/zh 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
Also Published As
| Publication number | Publication date |
|---|---|
| US20030187168A1 (en) | 2003-10-02 |
| JP2008239995A (ja) | 2008-10-09 |
| EP1298156A1 (en) | 2003-04-02 |
| WO2002088216A1 (fr) | 2002-11-07 |
| DE60205555D1 (de) | 2005-09-22 |
| TW575596B (en) | 2004-02-11 |
| EP1298156A4 (en) | 2003-09-10 |
| KR20040002398A (ko) | 2004-01-07 |
| US6875819B2 (en) | 2005-04-05 |
| JPWO2002088216A1 (ja) | 2004-08-19 |
| KR100583297B1 (ko) | 2006-05-24 |
| EP1298156B1 (en) | 2005-08-17 |
| CN1233685C (zh) | 2005-12-28 |
| JP4236935B2 (ja) | 2009-03-11 |
| CN1462286A (zh) | 2003-12-17 |
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