DE60002312T2 - Photoaktives polymer - Google Patents
Photoaktives polymer Download PDFInfo
- Publication number
- DE60002312T2 DE60002312T2 DE60002312T DE60002312T DE60002312T2 DE 60002312 T2 DE60002312 T2 DE 60002312T2 DE 60002312 T DE60002312 T DE 60002312T DE 60002312 T DE60002312 T DE 60002312T DE 60002312 T2 DE60002312 T2 DE 60002312T2
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- halogen
- chain
- polymer according
- unsubstituted
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 87
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 90
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000006850 spacer group Chemical group 0.000 claims abstract description 20
- 230000003287 optical effect Effects 0.000 claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 15
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 238000010276 construction Methods 0.000 claims abstract description 4
- -1 pyridine-2,5-diyl Chemical group 0.000 claims description 213
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 45
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 239000011737 fluorine Substances 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
- 239000000460 chlorine Chemical group 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 229910003849 O-Si Inorganic materials 0.000 claims description 16
- 229910003872 O—Si Inorganic materials 0.000 claims description 16
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 125000005731 2,5-thiophenylene group Chemical group [H]C1=C([*:1])SC([*:2])=C1[H] 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000006358 imidation reaction Methods 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000012952 cationic photoinitiator Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 238000006349 photocyclization reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 229920000106 Liquid crystal polymer Polymers 0.000 description 15
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 229920005575 poly(amic acid) Polymers 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000005711 Benzoic acid Substances 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000003440 styrenes Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 4
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 4
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical class NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 description 4
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical class NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 description 4
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920001567 vinyl ester resin Chemical class 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 3
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- 238000006471 dimerization reaction Methods 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- NCWTXZWJQCMAGD-NHFJDJAPSA-N 11-(2-methylprop-2-enoyloxy)undecyl 5-[4-[(e)-3-methoxy-3-oxoprop-1-enyl]benzoyl]oxy-2-(4-propylbenzoyl)oxybenzoate Chemical compound C1=CC(CCC)=CC=C1C(=O)OC(C(=C1)C(=O)OCCCCCCCCCCCOC(=O)C(C)=C)=CC=C1OC(=O)C1=CC=C(\C=C\C(=O)OC)C=C1 NCWTXZWJQCMAGD-NHFJDJAPSA-N 0.000 description 2
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- UENRXLSRMCSUSN-UHFFFAOYSA-M 3,5-diaminobenzoate Chemical compound NC1=CC(N)=CC(C([O-])=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-M 0.000 description 2
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 2
- KAWUBNUJMFOOOE-UHFFFAOYSA-N 3-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC(Br)=C(O)C(Br)=C1 KAWUBNUJMFOOOE-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- 210000002858 crystal cell Anatomy 0.000 description 2
- 229920005565 cyclic polymer Polymers 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920001002 functional polymer Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- OFDFGWLQAKFNRX-CSKARUKUSA-N methyl (e)-3-[4-(6-hydroxyhexoxy)-3-methoxyphenyl]prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(OCCCCCCO)C(OC)=C1 OFDFGWLQAKFNRX-CSKARUKUSA-N 0.000 description 1
- OFDFGWLQAKFNRX-UHFFFAOYSA-N methyl 3-[4-(6-hydroxyhexoxy)-3-methoxyphenyl]prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(OCCCCCCO)C(OC)=C1 OFDFGWLQAKFNRX-UHFFFAOYSA-N 0.000 description 1
- 101150036770 mon2 gene Proteins 0.000 description 1
- ZFSHWYNDXCIGND-UHFFFAOYSA-N n,n-bis(5-methyl-2-propan-2-ylcyclohexyl)aniline Chemical compound CC(C)C1CCC(C)CC1N(C=1C=CC=CC=1)C1C(C(C)C)CCC(C)C1 ZFSHWYNDXCIGND-UHFFFAOYSA-N 0.000 description 1
- CLCWCGOCHZSFQE-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)cyclohexanamine Chemical compound C1OC1CN(C1CCCCC1)CC1CO1 CLCWCGOCHZSFQE-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
-
- 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
- C09K2323/02—Alignment layer characterised by chemical composition
-
- 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
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/023—Organic silicon compound, e.g. organosilicon
-
- 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
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/025—Polyamide
-
- 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
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/027—Polyimide
-
- 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
- C09K2323/02—Alignment layer characterised by chemical composition
- C09K2323/027—Polyimide
- C09K2323/0271—Polyimidfluoride
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9907801.6A GB9907801D0 (en) | 1999-04-06 | 1999-04-06 | Photoactive polymers |
| GB9907801 | 1999-04-06 | ||
| PCT/IB2000/000349 WO2000059966A1 (en) | 1999-04-06 | 2000-03-27 | Photoactive polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60002312D1 DE60002312D1 (en) | 2003-05-28 |
| DE60002312T2 true DE60002312T2 (de) | 2004-02-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60002312T Expired - Lifetime DE60002312T2 (de) | 1999-04-06 | 2000-03-27 | Photoaktives polymer |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6649230B1 (https=) |
| EP (1) | EP1171493B1 (https=) |
| JP (1) | JP4755345B2 (https=) |
| KR (1) | KR100585044B1 (https=) |
| CN (1) | CN1157425C (https=) |
| AT (1) | ATE238361T1 (https=) |
| AU (1) | AU3315400A (https=) |
| DE (1) | DE60002312T2 (https=) |
| GB (1) | GB9907801D0 (https=) |
| HK (1) | HK1039949B (https=) |
| WO (1) | WO2000059966A1 (https=) |
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| US6194481B1 (en) * | 1999-05-19 | 2001-02-27 | Board Of Regents Of The University Of Texas System | Mechanically strong and transparent or translucent composites made using zirconium oxide nanoparticles |
| EP1070731A1 (en) * | 1999-07-23 | 2001-01-24 | Rolic AG | Compound |
| KR100673265B1 (ko) * | 2000-10-04 | 2007-01-22 | 엘지.필립스 엘시디 주식회사 | 액정표시장치 |
| US7238831B2 (en) * | 2001-01-23 | 2007-07-03 | Southwest Research Institute | Mesogens |
| US20040199004A1 (en) * | 2001-01-23 | 2004-10-07 | Southwest Research Institute | Novel mesogens |
| US7147800B2 (en) * | 2001-01-23 | 2006-12-12 | Southwest Research Institute | Selective ether cleavage synthesis of liquid crystals |
| EP1229066A1 (en) * | 2001-02-05 | 2002-08-07 | Rolic AG | Photoactive polymer |
| WO2002070543A2 (en) * | 2001-03-07 | 2002-09-12 | University Of Texas System | Ultra-low shrinkage composite resins based on blended nematic liquid crystal monomers |
| EP1391476B1 (en) * | 2001-04-09 | 2015-12-09 | Sekisui Chemical Co., Ltd. | Photoreactive composition |
| US7118787B2 (en) * | 2001-06-29 | 2006-10-10 | University Of Hull | Liquid crystal alignment layer |
| US7098359B2 (en) | 2001-07-09 | 2006-08-29 | Southwest Research Institute | Mesogens and methods for their synthesis and use |
| EP1277770A1 (en) * | 2001-07-17 | 2003-01-22 | Rolic AG | Photoactive materials |
| EP1295863A1 (en) * | 2001-09-24 | 2003-03-26 | Rolic AG | Liquid crystalline "laterally polymerizable" compounds |
| EP1507161B1 (en) * | 2002-05-23 | 2006-09-20 | Nissan Chemical Industries, Ltd. | Liquid crystal aligning agent, liquid crystal aligning films and liquid crystal display devices |
| EP1386910A1 (en) | 2002-07-30 | 2004-02-04 | Rolic AG | Photoactive materials |
| AU2003278314A1 (en) * | 2002-10-17 | 2004-05-04 | Zbd Displays Ltd. | Liquid crystal alignment layer |
| KR20050084084A (ko) * | 2002-12-06 | 2005-08-26 | 롤리크 아게 | 가교성, 광활성 중합체 및 그의 용도 |
| KR100969148B1 (ko) * | 2003-05-30 | 2010-07-08 | 엘지디스플레이 주식회사 | 편광된 ｕｖ를 이용한 위상차 필름의 제조방법 |
| US7626661B2 (en) * | 2003-12-11 | 2009-12-01 | Jds Uniphase Corporation | Polarization controlling elements |
| EP1764405A1 (en) | 2005-09-20 | 2007-03-21 | Rolic AG | Functionalized photoreactive compounds |
| US7919648B2 (en) | 2005-12-08 | 2011-04-05 | Chisso Corporation | Lateral α-substituted acrylate compound and polymer thereof |
| US7785488B2 (en) | 2005-12-08 | 2010-08-31 | Chisso Corporation | Lateral oxirane compound and polymer thereof |
| CN104649916B (zh) | 2005-12-23 | 2020-12-01 | 罗利克有限公司 | 光可交联材料 |
| US7927671B2 (en) | 2006-09-21 | 2011-04-19 | Chisso Corporation | Trifunctional compound, composition and polymer thereof |
| KR101450923B1 (ko) * | 2007-03-19 | 2014-10-14 | 제이에스알 가부시끼가이샤 | 액정 배향제 및 액정 표시 소자 |
| KR101612699B1 (ko) * | 2007-05-02 | 2016-04-15 | 롤리크 아게 | 열안정성 정렬 물질 |
| CN101903494B (zh) * | 2007-12-21 | 2016-03-02 | 罗利克有限公司 | 光校准组合物 |
| EP2222740B1 (en) * | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
| JP5245118B2 (ja) * | 2008-03-07 | 2013-07-24 | 和歌山県 | 新規な重合性化合物およびその製造方法 |
| EP2138889A1 (en) * | 2008-06-26 | 2009-12-30 | Lachezar Komitov | Alignment layer for LCD |
| JP5630014B2 (ja) * | 2009-01-30 | 2014-11-26 | ソニー株式会社 | 液晶表示装置の製造方法 |
| WO2010150748A1 (ja) * | 2009-06-23 | 2010-12-29 | 日産化学工業株式会社 | 光配向性を有する熱硬化膜形成組成物 |
| JP6525590B2 (ja) | 2011-08-25 | 2019-06-05 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光反応性化合物 |
| WO2013050121A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| KR101998557B1 (ko) | 2011-10-03 | 2019-07-10 | 롤리크 아게 | 광정렬 재료 |
| EP2981591A4 (en) * | 2013-04-02 | 2016-12-21 | Empire Technology Dev Llc | LIGHT-SENSITIVE HYDROPHILIC COATING |
| US10557085B2 (en) | 2015-03-31 | 2020-02-11 | Rolic Ag | Photoalignment composition |
| US10696795B2 (en) | 2015-11-11 | 2020-06-30 | Rolic Technologies AG | Photoaligning materials |
| CN109804306A (zh) * | 2016-10-11 | 2019-05-24 | 罗利克技术有限公司 | 光配向共聚物材料 |
| US11827727B2 (en) * | 2021-11-29 | 2023-11-28 | Fujifilm Corporation | Photo-alignment polymer, binder composition, binder layer, optical laminate, optical laminate manufacturing method, and image display device |
| EP4493638A1 (en) | 2022-03-16 | 2025-01-22 | Rolic Technologies AG | Photoaligning materials |
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|---|---|---|---|---|
| JP2761781B2 (ja) * | 1988-12-30 | 1998-06-04 | キヤノン株式会社 | 高分子液晶化合物、モノマー性の液晶化合物、それらの液晶組成物及びそれらの液晶素子 |
| DE4115415A1 (de) * | 1991-05-10 | 1992-11-12 | Basf Ag | Fluessigkristalline polymere mit nahezu einheitlichem molekulargewicht |
| DE59408097D1 (de) | 1993-02-17 | 1999-05-20 | Rolic Ag | Orientierungsschicht für Flüssigkristalle |
| SG50569A1 (en) | 1993-02-17 | 2001-02-20 | Rolic Ag | Optical component |
| CN1082061C (zh) * | 1994-09-29 | 2002-04-03 | 罗列克股份公司 | 用于生产液晶取向层的香豆素及喹啉酮衍生物 |
| US6107427A (en) | 1995-09-15 | 2000-08-22 | Rolic Ag | Cross-linkable, photoactive polymer materials |
| DE59707681D1 (de) * | 1996-10-28 | 2002-08-14 | Rolic Ag Zug | Vernetzbare, photoaktive Silanderivate |
| DE59814236D1 (de) * | 1997-02-24 | 2008-07-17 | Rolic Ag | Photovernetzbare Polymere |
| EP0860455B1 (de) | 1997-02-24 | 2008-06-04 | Rolic AG | Photovernetzbare Polymere |
| US6084057A (en) * | 1997-05-20 | 2000-07-04 | Elsicon, Inc. | Polarizable amines and polyimides for optical alignment of liquid crystals |
| WO1999015576A1 (en) * | 1997-09-25 | 1999-04-01 | Rolic Ag | Photocrosslinkable polyimides |
| JP4207233B2 (ja) * | 1997-11-18 | 2009-01-14 | Ｄｉｃ株式会社 | 液晶組成物及びこれを用いた光学異方体 |
| US6103322A (en) * | 1998-12-23 | 2000-08-15 | Elsicon Inc. | Materials for inducing alignment of liquid crystals and liquid crystal optical elements |
-
1999
- 1999-04-06 GB GBGB9907801.6A patent/GB9907801D0/en not_active Ceased
-
2000
- 2000-03-27 DE DE60002312T patent/DE60002312T2/de not_active Expired - Lifetime
- 2000-03-27 KR KR1020017012704A patent/KR100585044B1/ko not_active Expired - Fee Related
- 2000-03-27 WO PCT/IB2000/000349 patent/WO2000059966A1/en not_active Ceased
- 2000-03-27 CN CNB008056498A patent/CN1157425C/zh not_active Expired - Lifetime
- 2000-03-27 US US09/958,043 patent/US6649230B1/en not_active Expired - Lifetime
- 2000-03-27 HK HK02100918.7A patent/HK1039949B/en not_active IP Right Cessation
- 2000-03-27 AU AU33154/00A patent/AU3315400A/en not_active Abandoned
- 2000-03-27 JP JP2000609472A patent/JP4755345B2/ja not_active Expired - Lifetime
- 2000-03-27 EP EP00911160A patent/EP1171493B1/en not_active Expired - Lifetime
- 2000-03-27 AT AT00911160T patent/ATE238361T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6649230B1 (en) | 2003-11-18 |
| WO2000059966A1 (en) | 2000-10-12 |
| HK1039949B (en) | 2003-08-22 |
| HK1039949A1 (en) | 2002-05-17 |
| DE60002312D1 (en) | 2003-05-28 |
| AU3315400A (en) | 2000-10-23 |
| ATE238361T1 (de) | 2003-05-15 |
| KR100585044B1 (ko) | 2006-06-01 |
| CN1345342A (zh) | 2002-04-17 |
| CN1157425C (zh) | 2004-07-14 |
| EP1171493B1 (en) | 2003-04-23 |
| JP4755345B2 (ja) | 2011-08-24 |
| GB9907801D0 (en) | 1999-06-02 |
| JP2002541277A (ja) | 2002-12-03 |
| EP1171493A1 (en) | 2002-01-16 |
| KR20010108454A (ko) | 2001-12-07 |
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| 8364 | No opposition during term of opposition |