KR20060134133A - 광학 재료용 화합물 및 이의 제조 방법 - Google Patents
광학 재료용 화합물 및 이의 제조 방법 Download PDFInfo
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- KR20060134133A KR20060134133A KR1020067020103A KR20067020103A KR20060134133A KR 20060134133 A KR20060134133 A KR 20060134133A KR 1020067020103 A KR1020067020103 A KR 1020067020103A KR 20067020103 A KR20067020103 A KR 20067020103A KR 20060134133 A KR20060134133 A KR 20060134133A
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- South Korea
- Prior art keywords
- group
- monomer
- perfluorovinyl
- polymer
- electro
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 65
- 230000003287 optical effect Effects 0.000 title claims description 41
- 150000001875 compounds Chemical class 0.000 title abstract description 17
- 238000002360 preparation method Methods 0.000 title description 3
- -1 monocyclic perfluorovinyl compound Chemical class 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 76
- 229920000642 polymer Polymers 0.000 claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 32
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 30
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 24
- 229910052751 metal Inorganic materials 0.000 claims abstract description 20
- 239000002184 metal Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 230000000737 periodic effect Effects 0.000 claims abstract description 15
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 14
- 239000012788 optical film Substances 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 52
- 239000010408 film Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 23
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical compound [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004642 Polyimide Substances 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 229920001721 polyimide Polymers 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 150000002894 organic compounds Chemical group 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 239000000919 ceramic Substances 0.000 claims description 5
- 229910010272 inorganic material Inorganic materials 0.000 claims description 5
- 239000011147 inorganic material Substances 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 4
- 239000013307 optical fiber Substances 0.000 claims description 4
- 238000007655 standard test method Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- QNDHDIXRBUDLFJ-UHFFFAOYSA-N 1-(1,2,2-trifluoroethenoxy)-4-[4-(1,2,2-trifluoroethenoxy)phenyl]benzene Chemical group C1=CC(OC(F)=C(F)F)=CC=C1C1=CC=C(OC(F)=C(F)F)C=C1 QNDHDIXRBUDLFJ-UHFFFAOYSA-N 0.000 claims description 3
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 238000003618 dip coating Methods 0.000 claims description 3
- 238000001125 extrusion Methods 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
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- 238000010345 tape casting Methods 0.000 claims description 3
- BUUDSNNDBWSYIM-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,10,10-octadecafluorodeca-1,9-diene Chemical group FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=C(F)F BUUDSNNDBWSYIM-UHFFFAOYSA-N 0.000 claims description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 claims description 2
- IPDVQPDVQHNZQO-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C1=CC=C2C(=O)N(O)C(=O)C2=C1 IPDVQPDVQHNZQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 238000005253 cladding Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical group N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000002680 magnesium Chemical class 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 5
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910018557 Si O Inorganic materials 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- 125000003700 epoxy group Chemical group 0.000 description 3
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- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
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- 229920000647 polyepoxide Polymers 0.000 description 3
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- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UROHSXQUJQQUOO-UHFFFAOYSA-M (4-benzoylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].C1=CC(C[N+](C)(C)C)=CC=C1C(=O)C1=CC=CC=C1 UROHSXQUJQQUOO-UHFFFAOYSA-M 0.000 description 2
- WODNGFYRYQNMEO-UHFFFAOYSA-N (4-bromophenyl)-trichlorosilane Chemical compound Cl[Si](Cl)(Cl)C1=CC=C(Br)C=C1 WODNGFYRYQNMEO-UHFFFAOYSA-N 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- XAUHHCMRFFGRMF-UHFFFAOYSA-N 1-[1,1-bis[4-(1,2,2-trifluoroethenoxy)phenyl]ethyl]-4-(1,2,2-trifluoroethenoxy)benzene Chemical compound C=1C=C(OC(F)=C(F)F)C=CC=1C(C=1C=CC(OC(F)=C(F)F)=CC=1)(C)C1=CC=C(OC(F)=C(F)F)C=C1 XAUHHCMRFFGRMF-UHFFFAOYSA-N 0.000 description 2
- ZPYGRBTUNITHKJ-UHFFFAOYSA-N 1-bromo-1,1,2,2-tetrafluoro-2-(1,2,2-trifluoroethenoxy)ethane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)Br ZPYGRBTUNITHKJ-UHFFFAOYSA-N 0.000 description 2
- PDFSXHZXNZCKNF-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodeca-1,9-diene Chemical compound C=CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C PDFSXHZXNZCKNF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- JEZFASCUIZYYEV-UHFFFAOYSA-N chloro(triethoxy)silane Chemical compound CCO[Si](Cl)(OCC)OCC JEZFASCUIZYYEV-UHFFFAOYSA-N 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QKENRHXGDUPTEM-UHFFFAOYSA-N perfluorophenanthrene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C3(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C3(F)C(F)(F)C(F)(F)C21F QKENRHXGDUPTEM-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- GLGBZQCHVOXGRJ-UHFFFAOYSA-N trichloro-[4-(1,2,2-trifluoroethenoxy)phenyl]silane Chemical compound FC(F)=C(F)OC1=CC=C([Si](Cl)(Cl)Cl)C=C1 GLGBZQCHVOXGRJ-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- PLNNDWMRUGUSCT-UHFFFAOYSA-N (2-bromophenyl)-trichlorosilane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1Br PLNNDWMRUGUSCT-UHFFFAOYSA-N 0.000 description 1
- WHMATEBAHVQEPZ-UHFFFAOYSA-N (4-bromophenyl)-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(Br)C=C1 WHMATEBAHVQEPZ-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- KGNLXBIRBHMRHB-UHFFFAOYSA-N 1-bromo-4-(1,2,2-trifluoroethenoxy)benzene Chemical compound FC(F)=C(F)OC1=CC=C(Br)C=C1 KGNLXBIRBHMRHB-UHFFFAOYSA-N 0.000 description 1
- HPVQKOJPXRBSRI-UHFFFAOYSA-N 2-bromoethoxy-diethoxy-phenylsilane Chemical compound BrCCO[Si](OCC)(OCC)C1=CC=CC=C1 HPVQKOJPXRBSRI-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- YEMSALKQGSGSMP-UHFFFAOYSA-N triethoxy(1,2,2-trifluoroethenyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)=C(F)F YEMSALKQGSGSMP-UHFFFAOYSA-N 0.000 description 1
- 230000036266 weeks of gestation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Liquid Crystal Substances (AREA)
- Optical Integrated Circuits (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/812,191 | 2004-03-29 | ||
| US10/812,191 US7214475B2 (en) | 2004-03-29 | 2004-03-29 | Compound for optical materials and methods of fabrication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060134133A true KR20060134133A (ko) | 2006-12-27 |
Family
ID=34963875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067020103A Ceased KR20060134133A (ko) | 2004-03-29 | 2005-03-23 | 광학 재료용 화합물 및 이의 제조 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7214475B2 (enExample) |
| EP (1) | EP1732937A1 (enExample) |
| JP (1) | JP2007530682A (enExample) |
| KR (1) | KR20060134133A (enExample) |
| CN (1) | CN1938342A (enExample) |
| MY (1) | MY139112A (enExample) |
| TW (1) | TW200609240A (enExample) |
| WO (1) | WO2005097843A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12165979B2 (en) | 2019-03-07 | 2024-12-10 | Absolics Inc. | Packaging substrate and semiconductor apparatus comprising same |
| US12198994B2 (en) | 2019-03-12 | 2025-01-14 | Absolics Inc. | Packaging substrate and method for manufacturing same |
| US12456672B2 (en) | 2019-03-12 | 2025-10-28 | Absolics Inc. | Packaging substrate having element group in cavity unit and semiconductor device comprising the same |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5069570B2 (ja) * | 2005-02-16 | 2012-11-07 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | 特定のプレチルト角を持つ配列ポリマーを含んだ発光体 |
| US8529993B2 (en) * | 2006-05-01 | 2013-09-10 | Zetta Research andDevelopment LLC—RPO Series | Low volatility polymers for two-stage deposition processes |
| US7989560B2 (en) * | 2006-12-15 | 2011-08-02 | Chisso Corporation | Fluorine-containing polymer and resin composition |
| US20100304512A1 (en) * | 2007-11-30 | 2010-12-02 | University Of Toledo | System for Diagnosis and Treatment of Photovoltaic and Other Semiconductor Devices |
| US8574944B2 (en) * | 2008-03-28 | 2013-11-05 | The University Of Toledo | System for selectively filling pin holes, weak shunts and/or scribe lines in photovoltaic devices and photovoltaic cells made thereby |
| CN102382132A (zh) * | 2010-08-30 | 2012-03-21 | 珠海市吉林大学无机合成与制备化学重点实验室 | 多孔硅氧烷有机骨架材料及其制备方法 |
| US20120135165A1 (en) * | 2010-11-29 | 2012-05-31 | Yu-Hui Huang | Antiglare and antiseptic coating material and touchscreen coated with the same |
| US20120177920A1 (en) * | 2011-01-11 | 2012-07-12 | Yu-Hui Huang | Antiglare and antiseptic coating material and touchscreen coated with the same |
| US9731456B2 (en) | 2013-03-14 | 2017-08-15 | Sabic Global Technologies B.V. | Method of manufacturing a functionally graded article |
| WO2016109534A1 (en) | 2014-12-30 | 2016-07-07 | Momentive Performance Materials Inc. | Siloxane coordination polymers |
| US10294332B2 (en) | 2014-12-30 | 2019-05-21 | Momentive Performance Materials Inc. | Functionalized siloxane materials |
| WO2018079707A1 (ja) * | 2016-10-27 | 2018-05-03 | 宇部興産株式会社 | ポリイミドおよびそれを用いたフレキシブルデバイス |
| US11572454B2 (en) | 2017-02-08 | 2023-02-07 | Architectural Solutions Ip, Llc | Flame resistant material and resultant products |
| CN110734525B (zh) * | 2018-07-18 | 2022-07-01 | 浙江省化工研究院有限公司 | 一种含氟笼型倍半硅氧烷改性聚三氟氯乙烯树脂 |
| CN110606955B (zh) * | 2019-08-12 | 2021-04-27 | 武汉华星光电半导体显示技术有限公司 | 一种硬化层聚合物薄膜和制备方法 |
| WO2021229340A1 (en) * | 2020-05-14 | 2021-11-18 | 3M Innovative Properties Company | Fluorinated photoinitiators and fluorinated (co)polymer layers made using the same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292620A (en) | 1988-01-15 | 1994-03-08 | E. I. Du Pont De Nemours And Company | Optical waveguide devices, elements for making the devices and methods of making the devices and elements |
| US5023380A (en) | 1989-06-09 | 1991-06-11 | The Dow Chemical Company | Perfluorovinyl compounds |
| JPH0317088A (ja) * | 1989-06-15 | 1991-01-25 | Toshiba Silicone Co Ltd | 有機ケイ素化合物 |
| JPH0953015A (ja) * | 1995-08-11 | 1997-02-25 | Nitto Denko Corp | 紫外線感光性含フッ素シリコーン組成物 |
| JP3861966B2 (ja) * | 2000-02-16 | 2006-12-27 | 信越化学工業株式会社 | 高分子化合物、化学増幅レジスト材料及びパターン形成方法 |
| US6924384B2 (en) | 2002-01-08 | 2005-08-02 | Silecs Oy | Methods and compounds for making coatings, waveguides and other optical devices |
| US20030171607A1 (en) | 2002-01-08 | 2003-09-11 | Rantala Juha T. | Methods and compounds for making coatings, waveguides and other optical devices |
| US6803476B2 (en) | 2002-01-08 | 2004-10-12 | Silecs Oy | Methods and compounds for making coatings, waveguides and other optical devices |
| US20030176718A1 (en) | 2002-01-08 | 2003-09-18 | Rantala Juha T. | Methods and compounds for making coatings, waveguides and other optical devices |
| US6831189B2 (en) | 2002-01-08 | 2004-12-14 | Silecs Oy | Methods and compounds for making coatings, waveguides and other optical devices |
| EP1463740A2 (en) | 2002-01-08 | 2004-10-06 | Silecs, Inc. | Materials and methods for forming hybrid organic-inorganic dielectric materials |
| WO2003059990A1 (en) | 2002-01-17 | 2003-07-24 | Silecs Oy | Thin films and methods for the preparation thereof |
-
2004
- 2004-03-29 US US10/812,191 patent/US7214475B2/en not_active Expired - Fee Related
-
2005
- 2005-03-23 CN CNA2005800097171A patent/CN1938342A/zh active Pending
- 2005-03-23 KR KR1020067020103A patent/KR20060134133A/ko not_active Ceased
- 2005-03-23 EP EP05730107A patent/EP1732937A1/en not_active Withdrawn
- 2005-03-23 JP JP2007506249A patent/JP2007530682A/ja active Pending
- 2005-03-23 WO PCT/US2005/009656 patent/WO2005097843A1/en not_active Ceased
- 2005-03-28 MY MYPI20051336A patent/MY139112A/en unknown
- 2005-03-29 TW TW094109810A patent/TW200609240A/zh unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12165979B2 (en) | 2019-03-07 | 2024-12-10 | Absolics Inc. | Packaging substrate and semiconductor apparatus comprising same |
| US12198994B2 (en) | 2019-03-12 | 2025-01-14 | Absolics Inc. | Packaging substrate and method for manufacturing same |
| US12456672B2 (en) | 2019-03-12 | 2025-10-28 | Absolics Inc. | Packaging substrate having element group in cavity unit and semiconductor device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005097843A1 (en) | 2005-10-20 |
| CN1938342A (zh) | 2007-03-28 |
| EP1732937A1 (en) | 2006-12-20 |
| TW200609240A (en) | 2006-03-16 |
| MY139112A (en) | 2009-08-28 |
| JP2007530682A (ja) | 2007-11-01 |
| US20050214479A1 (en) | 2005-09-29 |
| WO2005097843A8 (en) | 2006-10-05 |
| US7214475B2 (en) | 2007-05-08 |
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