KR20060134133A - 광학 재료용 화합물 및 이의 제조 방법 - Google Patents
광학 재료용 화합물 및 이의 제조 방법 Download PDFInfo
- Publication number
- 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
- Authority
- KR
- South Korea
- Prior art keywords
- group
- monomer
- perfluorovinyl
- polymer
- electro
- 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.)
- Ceased
Links
- 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
- 238000009472 formulation Methods 0.000 claims description 3
- 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
- 230000008859 change Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 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
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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
- 238000001816 cooling Methods 0.000 description 2
- 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
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 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
- YWGFZOBUEGEXLW-UHFFFAOYSA-N FC(Oc(cc1)ccc1-c1ccccc1)=C(F)F Chemical compound FC(Oc(cc1)ccc1-c1ccccc1)=C(F)F YWGFZOBUEGEXLW-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- PZVZTKFRZJMHEM-UHFFFAOYSA-N iodotrifluoroethylene Chemical group FC(F)=C(F)I PZVZTKFRZJMHEM-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006060 molten glass Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Liquid Crystal Substances (AREA)
- Optical Integrated Circuits (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/812,191 US7214475B2 (en) | 2004-03-29 | 2004-03-29 | Compound for optical materials and methods of fabrication |
| US10/812,191 | 2004-03-29 |
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 (https=) |
| EP (1) | EP1732937A1 (https=) |
| JP (1) | JP2007530682A (https=) |
| KR (1) | KR20060134133A (https=) |
| CN (1) | CN1938342A (https=) |
| MY (1) | MY139112A (https=) |
| TW (1) | TW200609240A (https=) |
| WO (1) | WO2005097843A1 (https=) |
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 |
|---|---|---|---|---|
| CN101840077B (zh) * | 2005-02-16 | 2015-09-02 | 皇家飞利浦电子股份有限公司 | 发光物体及其应用 |
| US8529993B2 (en) * | 2006-05-01 | 2013-09-10 | Zetta Research andDevelopment LLC—RPO Series | Low volatility polymers for two-stage deposition processes |
| ATE543846T1 (de) * | 2006-12-15 | 2012-02-15 | Jnc Corp | Fluorhaltiges polymer und harzzusammensetzung |
| 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 |
| US10287398B2 (en) | 2014-12-30 | 2019-05-14 | Momentive Performance Materials Inc. | Siloxane coordination polymers |
| EP3240807A4 (en) | 2014-12-30 | 2018-08-08 | Momentive Performance Materials Inc. | Functionalized siloxane materials |
| JP7215904B2 (ja) * | 2016-10-27 | 2023-01-31 | Ｕｂｅ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 |
| US20030176718A1 (en) | 2002-01-08 | 2003-09-18 | Rantala Juha T. | Methods and compounds for making coatings, waveguides and other optical devices |
| AU2003201736A1 (en) | 2002-01-08 | 2003-07-24 | Silecs, Inc. | Materials and methods for forming hybrid organic-inorganic dielectric materials |
| US6803476B2 (en) | 2002-01-08 | 2004-10-12 | Silecs Oy | 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 |
| US20030171607A1 (en) | 2002-01-08 | 2003-09-11 | Rantala Juha T. | Methods and compounds for making coatings, waveguides and other optical devices |
| US6924384B2 (en) | 2002-01-08 | 2005-08-02 | Silecs Oy | Methods and compounds for making coatings, waveguides and other optical devices |
| 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 WO PCT/US2005/009656 patent/WO2005097843A1/en not_active Ceased
- 2005-03-23 EP EP05730107A patent/EP1732937A1/en not_active Withdrawn
- 2005-03-23 CN CNA2005800097171A patent/CN1938342A/zh active Pending
- 2005-03-23 KR KR1020067020103A patent/KR20060134133A/ko not_active Ceased
- 2005-03-23 JP JP2007506249A patent/JP2007530682A/ja active Pending
- 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 |
| TW200609240A (en) | 2006-03-16 |
| US20050214479A1 (en) | 2005-09-29 |
| MY139112A (en) | 2009-08-28 |
| US7214475B2 (en) | 2007-05-08 |
| CN1938342A (zh) | 2007-03-28 |
| WO2005097843A8 (en) | 2006-10-05 |
| JP2007530682A (ja) | 2007-11-01 |
| EP1732937A1 (en) | 2006-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20060134133A (ko) | 광학 재료용 화합물 및 이의 제조 방법 | |
| CN103370361B (zh) | 可聚合组合物、由其得到的固化产物以及这些材料的用途 | |
| KR100553327B1 (ko) | 트리플루오로비닐에테르 기능기를 함유한 실록산 단량체와 이 단량체를 이용하여 제조된 졸-겔 하이브리드 중합체 | |
| US8513372B2 (en) | Asymmetric photo-patternable sol-gel precursors and their methods of preparation | |
| KR20090064588A (ko) | 폴리실옥산을 생산하기 위한 방법 및 그의 용도 | |
| KR102575896B1 (ko) | 실리콘-상용성 화합물 | |
| KR101890899B1 (ko) | 광도파로 형성용 조성물 | |
| KR102519935B1 (ko) | 반응성 실세스퀴옥산 화합물을 포함하는 광도파로형성용 조성물 | |
| KR102363818B1 (ko) | 실세스퀴옥산 복합 고분자 및 이의 제조방법 | |
| KR20150091318A (ko) | 실리콘-상용성 광개시제 | |
| JP5027148B2 (ja) | ケイ酸縮合生成物及びそれを使用してなる光導波路デバイス | |
| HK1105100A (en) | Compound for optical materials and methods of fabrication | |
| KR102363820B1 (ko) | 실세스퀴옥산 복합 고분자 및 이의 제조방법 | |
| Roscher et al. | Perfluoroaryl Substituted Inorganic-Organic Hybrid Materials | |
| KR101409339B1 (ko) | 아이소소바이드 유도체 화합물, 이를 포함하는 광경화성 조성물 및 투광성 복합시트 | |
| KR101005811B1 (ko) | 포스페이트 구조를 갖는 과불소화 다가 아크릴계 화합물 및이를 함유하는 광중합성 조성물 | |
| KR100226442B1 (ko) | 열 경화성 에티닐기를 갖는 불소 치환 폴리아릴렌 에테르, 그의제조방법 및 그를 이용한 광소자 | |
| JP6555499B2 (ja) | 高屈折率重合性化合物の低粘度化剤及びそれを含む重合性組成物 | |
| Karaca et al. | Preparation of the polymerizable novel high refractive index hybrid carbazole-based polysiloxane oligomers by a sol–gel condensation reaction | |
| KR100944211B1 (ko) | 실록산 함유 과불소화 다가 아크릴계 화합물 및 이의제조방법과 이를 함유하는 광중합 조성물 | |
| WO2022211070A1 (ja) | 反応性シルセスキオキサン化合物を含有した光導波路用の重合性組成物 | |
| KR20050060639A (ko) | 광도파로 소자용 에폭시 치환기를 가진 불소 스티렌단량체와 이를 이용한 고분자 화합물 | |
| JP2008031134A (ja) | フェノール誘導体及びその製造方法 | |
| JP5048984B2 (ja) | 光導波路用縮合生成物、硬化物及び光導波路デバイス | |
| HK1189611A (en) | Polymerizable compositions, cured products obtained therewith, and use of these materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20060928 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20100323 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20110906 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20120330 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20110906 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |