JP2016520152A - シアノスチルベン - Google Patents
シアノスチルベン Download PDFInfo
- Publication number
- JP2016520152A JP2016520152A JP2016515733A JP2016515733A JP2016520152A JP 2016520152 A JP2016520152 A JP 2016520152A JP 2016515733 A JP2016515733 A JP 2016515733A JP 2016515733 A JP2016515733 A JP 2016515733A JP 2016520152 A JP2016520152 A JP 2016520152A
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- acrylate
- polymer
- oligomer
- acid
- 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.)
- Granted
Links
- USLPZCOPYRKTGY-UHFFFAOYSA-N 2-(2-phenylethenyl)benzonitrile Chemical compound N#CC1=CC=CC=C1C=CC1=CC=CC=C1 USLPZCOPYRKTGY-UHFFFAOYSA-N 0.000 title 1
- -1 useful for alignment Chemical class 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 30
- 230000003287 optical effect Effects 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 37
- 239000000178 monomer Substances 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000000412 dendrimer Substances 0.000 claims description 18
- 229920000736 dendritic polymer Polymers 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229920001519 homopolymer Polymers 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012952 cationic photoinitiator Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 239000003504 photosensitizing agent Substances 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 46
- 239000012788 optical film Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 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 26
- 239000010410 layer Substances 0.000 description 26
- 239000000758 substrate Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000001153 fluoro group Chemical group F* 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- 229920005575 poly(amic acid) Polymers 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 229940048053 acrylate Drugs 0.000 description 13
- 125000001246 bromo group Chemical group Br* 0.000 description 13
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 101150033824 PAA1 gene Proteins 0.000 description 9
- 239000004642 Polyimide Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000010287 polarization Effects 0.000 description 9
- 229920001721 polyimide Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920000106 Liquid crystal polymer Polymers 0.000 description 8
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000001542 size-exclusion chromatography Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- YDFAJMDFCCJZSI-UHFFFAOYSA-N 8-chlorooctan-1-ol Chemical compound OCCCCCCCCCl YDFAJMDFCCJZSI-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 3
- JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 3
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 101100167427 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) paa-7 gene Proteins 0.000 description 3
- 229910003849 O-Si Inorganic materials 0.000 description 3
- 229910003872 O—Si Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 2
- AYKYOOPFBCOXSL-UHFFFAOYSA-N (4-hydroxyphenyl)acetonitrile Chemical compound OC1=CC=C(CC#N)C=C1 AYKYOOPFBCOXSL-UHFFFAOYSA-N 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
- LMVLEDTVXAGBJV-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)C(F)C(F)(F)COC(=O)C=C LMVLEDTVXAGBJV-UHFFFAOYSA-N 0.000 description 2
- JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-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
- RKYJPYDJNQXILT-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCOC(=O)C=C RKYJPYDJNQXILT-UHFFFAOYSA-N 0.000 description 2
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XLMMCMJINQVDRC-UHFFFAOYSA-N 2-[4-(8-hydroxyoctoxy)phenyl]acetonitrile Chemical compound OCCCCCCCCOC1=CC=C(CC#N)C=C1 XLMMCMJINQVDRC-UHFFFAOYSA-N 0.000 description 2
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 2
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 2
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- LSMMRJUHLKJNLR-UHFFFAOYSA-N 3-methyl-1,3-benzothiazol-2-one Chemical compound C1=CC=C2SC(=O)N(C)C2=C1 LSMMRJUHLKJNLR-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- FFKSVVOWOROQIU-UHFFFAOYSA-N 4-(2,5-dioxooxolan-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid Chemical compound C12=CC=CC=C2C(C(O)=O)C(C(=O)O)CC1C1CC(=O)OC1=O FFKSVVOWOROQIU-UHFFFAOYSA-N 0.000 description 2
- XVGDUIBDKNXCQE-UHFFFAOYSA-N 4-(8-hydroxyoctoxy)benzaldehyde Chemical compound OCCCCCCCCOC1=CC=C(C=O)C=C1 XVGDUIBDKNXCQE-UHFFFAOYSA-N 0.000 description 2
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 2
- HOOIIRHGHALACD-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(O)=O)C(C)=CC1C1C(=O)OC(=O)C1 HOOIIRHGHALACD-UHFFFAOYSA-N 0.000 description 2
- XFLZZUJRBXQEQN-LYBHJNIJSA-N 8-[4-[(Z)-1-cyano-2-[4-(trifluoromethyl)phenyl]ethenyl]phenoxy]octyl 2-methylprop-2-enoate Chemical compound CC(C(=O)OCCCCCCCCOC1=CC=C(C=C1)/C(=C/C1=CC=C(C=C1)C(F)(F)F)/C#N)=C XFLZZUJRBXQEQN-LYBHJNIJSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- FEUIEHHLVZUGPB-UHFFFAOYSA-N oxolan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCO1 FEUIEHHLVZUGPB-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
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- 230000036211 photosensitivity Effects 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229920001289 polyvinyl ether 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
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- PNOXUQIZPBURMT-UHFFFAOYSA-M potassium;3-(2-methylprop-2-enoyloxy)propane-1-sulfonate Chemical compound [K+].CC(=C)C(=O)OCCCS([O-])(=O)=O PNOXUQIZPBURMT-UHFFFAOYSA-M 0.000 description 1
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- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
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- MYGFXCLXHGITIQ-UHFFFAOYSA-N quinolin-4-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=NC2=C1 MYGFXCLXHGITIQ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
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- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
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- UBLMWQYLVOVZMT-UHFFFAOYSA-N tert-butyl n-(3-acetylphenyl)carbamate Chemical compound CC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1 UBLMWQYLVOVZMT-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
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- LPUCKLOWOWADAC-UHFFFAOYSA-M tributylstannyl 2-methylprop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C(C)=C LPUCKLOWOWADAC-UHFFFAOYSA-M 0.000 description 1
- YSUXTNDMKYYZPR-UHFFFAOYSA-M tributylstannyl prop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C=C YSUXTNDMKYYZPR-UHFFFAOYSA-M 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- VCXJEVFMVWRIQL-UHFFFAOYSA-N triethylgermyl 2-methylprop-2-enoate Chemical compound CC[Ge](CC)(CC)OC(=O)C(C)=C VCXJEVFMVWRIQL-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- VWYKMPSIISPSAM-UHFFFAOYSA-N trimethylgermylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Ge](C)(C)C VWYKMPSIISPSAM-UHFFFAOYSA-N 0.000 description 1
- PGQNYIRJCLTTOJ-UHFFFAOYSA-N trimethylsilyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[Si](C)(C)C PGQNYIRJCLTTOJ-UHFFFAOYSA-N 0.000 description 1
- OTYBJBJYBGWBHB-UHFFFAOYSA-N trimethylsilyl prop-2-enoate Chemical compound C[Si](C)(C)OC(=O)C=C OTYBJBJYBGWBHB-UHFFFAOYSA-N 0.000 description 1
- VGOXVARSERTCRY-UHFFFAOYSA-N trimethylsilylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)C VGOXVARSERTCRY-UHFFFAOYSA-N 0.000 description 1
- KRVRUAYUNOQMOV-UHFFFAOYSA-N tris(4-aminophenyl)methanol Chemical compound C1=CC(N)=CC=C1C(O)(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 KRVRUAYUNOQMOV-UHFFFAOYSA-N 0.000 description 1
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- KRLHYNPADOCLAJ-UHFFFAOYSA-N undecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C(C)=C KRLHYNPADOCLAJ-UHFFFAOYSA-N 0.000 description 1
- RRLMGCBZYFFRED-UHFFFAOYSA-N undecyl prop-2-enoate Chemical compound CCCCCCCCCCCOC(=O)C=C RRLMGCBZYFFRED-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
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- 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
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/124—Unsaturated polyimide precursors the unsaturated precursors containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
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- 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
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- G—PHYSICS
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Abstract
Description
好ましくは、(Ia):
に係る化合物に関し、式中、
Ar1及びAr2は、互いに独立して、4〜40個の原子の環系であり、ここで、各環系は、式(I)に示される二重結合に電子共役(π−π結合)を介して直接連結された少なくとも1つの不飽和を含み、
ここで、環系は、非置換であるか、又は
ハロゲン原子及び/又はヒドロキシ、ニトロ、ニトリル、−CF3のような極性基によって;あるいはカルボキシ基、及び/又は1〜30個の炭素原子を有する環式の直鎖若しくは分岐アルキル残基(非置換であるか、メチル、フッ素及び/又は塩素によって単又は多置換されており、ここで、1つ以上の、好ましくは隣接していない−CH2−基は、独立して、−O−、−CO−、−CO−O−、−O−CO−、−NR1’−、−NR1’−CO−、−CO−NR1’−、−NR1’−CO−O−、−O−CO−NR1’−、−NR1’−CO−NR1’−、−CH=CH−、−C≡C−、−O−CO−O−及び−Si(CH3)2−O−Si(CH3)2−から選択される基、芳香族又は脂環式基によって置き換わっていてよく、ここで、R1’は、水素原子又は低級アルキルである);及び/又は1〜20個の炭素原子を有する、好ましくは1〜10個の炭素原子を有する、アクリロイルオキシ、アルコキシ、アルキルカルボニルオキシ、アルキルオキソカルボニルオキシ、メタクリロイルオキシ、ビニル、アリル、ビニルオキシ及び/又はアリルオキシ基によって単若しくは多置換されており;好ましくは、環系は、非置換であるか又はアルコキシ基によって置換されており;そして、式中;
Xが水素であり、そしてYがCNである場合、
R1、R2又はR3は、互いに独立して、水素、ハロゲン又は−CF3であるが、但し、R1、R2又はR3は、同時に水素ではなく;
XがCNであり、そしてYが水素である場合;
R1、R2又はR3は、互いに独立して、水素、ハロゲン又は−CF3であり;
Mは、単一の共有結合又はスペーサー単位であり;
Y1、Y2は、互いに独立して、架橋基であり、
nは、0、1、2又は3;好ましくは0であり、
Pは、水素原子、場合により置換されているアルキル、又は重合性基である。
Ar1は、式(II):
で表される環系であり、そして
Ar2は、式(IIa):
で表される環系であり、式中:
C1、C2は、各々独立して、好ましくは架橋基Z1及びZ2を介して反対の位置で互いに連結されている、5〜14個の原子の非芳香族又は芳香族の場合により置換されている炭素環式又は複素環式基であり、
Z1、Z2は、各々独立して、単結合、又は好ましくは−CH(OH)−、−O−、−CH2(CO)−、−SO−、−CH2(SO)−、−SO2−、−CH2(SO2)−、−COO−、−OCO−、−COF2−、−CF2CO−、−S−CO−、−CO−S−、−SOO−、−OSO−、−CH2−CH2−、−O−CH2−、−CH2O−、−CH=CH−、−C≡S−、−SH=CH−COO−、−OCO−CH=CH−、−CH=N−、−C(CH3)=N−、−O−CO−O−、−N=N−から選択される架橋基、又は1〜6個の炭素原子、好ましくは1〜3個の炭素原子の短鎖アルキルスペーサーであり、
aは、0、1、2又は3であり、
但し、二重結合に直接連結されているC2は、不飽和でありかつ二重結合と共役している。
式中、
Lは、ハロゲン、ヒドロキシル、及び/又は極性基、例えばニトロ、シアノ若しくはカルボキシ、及び/又はアクリロイルオキシ、アルコキシ、例えばメトキシ、エトキシ、プロポキシ、アルキルカルボニルオキシ、アルキルオキソカルボニルオキシ、メタクリロイルオキシ、ビニル、ビニルオキシ、アリル、アリルオキシ、及び/又は環式の直鎖若しくは分岐アルキル残基(非置換であるか又はフッ素及び/若しくは塩素によって単若しくは多置換されている)、及び/又はシラン基、及び/又はシロキサン基であり、ここで、アルキル残基は、1〜20個のC原子を有し、ここで、1つ以上の、好ましくは隣接していない−CH2−基は、独立して、好ましくは−O−、−CO−、−COO−、−OCO−、−C=C−、−C≡C−、−Si(CH3)2−、−Si(CH3)2−O−Si(CH3)2−から選択される基によって置き換わっていてよく、好ましくは、Lは、メトキシであり、
u1は、0、1、2、3又は4、好ましくは0又は1であり、
u2は、0、1、2又は3、好ましくは0又は1であり、そして
u3は、0、1又は2、好ましくは0又は1であり、
但し、二重結合に直接連結されているC2は、不飽和でありかつ二重結合と共役している。
Ar1が、式(II):
で表される環系であり、そして
Ar2が、式(IIa):
で表される環系であり、式中、
C1、C2は、各々独立して、好ましくは架橋基Z1及びZ2を介して反対の位置で互いに連結されている、5〜14個の原子の非芳香族又は芳香族の場合により置換されている炭素環式又は複素環式基であり、
Z1、Z2は、各々独立して、単結合、又は好ましくは−CH(OH)−、−O−、−CH2(CO)−、−SO−、−CH2(SO)−、−SO2−、−CH2(SO2)−、−COO−、−OCO−、−COF2−、−CF2CO−、−S−CO−、−CO−S−、−SOO−、−OSO−、−CH2−CH2−、−O−CH2−、−CH2O−、−CH=CH−、−C≡S−、−SH=CH−COO−、−OCO−CH=CH−、−CH=N−、−C(CH3)=N−、−O−CO−O−、−N=N−から選択される架橋基、又は1〜6個の炭素原子、好ましくは1〜3個の炭素原子の短鎖アルキルスペーサーであり、
aは、0、1、2又は3であり、好ましくは、aは、0又は1、より好ましくは0であり、
但し、二重結合に直接連結されているC2は、不飽和でありかつ二重結合と共役している、化合物であるか、
又はより好ましいのは、
Xが水素であり、そしてYがCNである場合、
R1、R2又はR3が、互いに独立して、水素、ハロゲン又は−CF3であるが、但し、R1、R2又はR3が、同時に水素ではなく;
又は好ましくは、Xが水素であり、そしてYがCNである場合、
R1が、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R2及びR3が、水素であるか;又は
R1及びR2が、互いに独立して、フルオロ、クロロ、ブロモ又は−CF3であり、そしてR3が、水素であるか;又は
R1、R2又はR3が、同時にフルオロ、クロロ又はブロモであるか;
又は
XがCNであり、そしてYが水素である場合;
R1が、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R2及びR3が、水素であるか;又は
R1及びR2が、互いに独立して、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R3が、水素であるか;又は
R1、R2又はR3が、同時に水素、フルオロ、クロロ又はブロモであり;
Mが、単結合、又は1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23若しくは24個、好ましくは1、2、3、4、5、6、7、8、9、10、11、12、13、14、15若しくは16個、より好ましくは6、7、8、9、10、11若しくは12、最も好ましくは8、9、10若しくは11個の炭素原子を有する直鎖若しくは分岐アルキレン残基であり、ここで、1つ以上の−CH2−基が、独立して、−O−、−CO−、−COO−、−OCO−、−C=C−、−C≡C−から選択される基によって置き換わっていてよく;
Pが、水素原子、場合により置換されているアルキル、又は重合性基である、式(Ia)の化合物である。
Ar1が、式(II):
で表される環系であり、そして
Ar2が、式(IIa):
で表される環系であり、式中、
C1、C2は、各々独立して、フェニル又はフェニレンであり;
Z1、Z2は、各々独立して、単結合又は−O−、−CH2(CO)−、−COO−、−OCO−、−CH2−CH2−、−OCO−CH=CH−、−N=N−、又は1〜3個の炭素原子の短鎖アルキルスペーサーであり、
aは、0又は1、好ましくは0である、式(I)に係る化合物であるか、
又は最も好ましいのは、
Xが水素であり、そしてYがCNである場合、
R1、R2又はR3が、互いに独立して、水素、ハロゲン又は−CF3であるが、但し、R1、R2又はR3が、同時に水素ではなく;
又は好ましくは、Xが水素であり、そしてYがCNである場合、
R1が、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R2及びR3が、水素であるか;又は
R1及びR2が、互いに独立して、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R3が、水素であるか;又は
R1、R2又はR3が、同時にフルオロ、クロロ又はブロモであり;
又は
XがCNであり、そしてYが水素である場合;
R1が、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R2及びR3が、水素であるか;又は
R1及びR2が、互いに独立して、フルオロ、クロロ、ブロモ又は−CF3であり、そして、R3が、水素であるか;又は
R1、R2又はR3が、水素、フルオロ、クロロ又はブロモであり;
Mが、単結合、又は1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23若しくは24個、好ましくは1、2、3、4、5、6、7、8、9、10、11、12、13、14、15若しくは16個、より好ましくは6、7、8、9、10、11若しくは12、最も好ましくは8、9、10若しくは11個の炭素原子を有する直鎖又は分岐アルキレン残基であり、ここで、1つ以上の−CH2−基が、独立して、−O−、−COO−、−OCO−、−C=C−から選択される基によって置き換わっていてよく;
Pは、水素原子、場合により置換されているアルキル、又はアクリラート、メタクリラート、ビニルエーテル及びエステル、エポキシ、シロキサン、シラン、ジアミン、イミドモノマー、アミド酸モノマー及びそれらのエステル、並びにそれらの混合物、若しくはそれらの対応するホモ−及びコポリマーから選択される重合性基である、式(Ia)の化合物である。
ンデシルメタクリラート、2−フルオロエチルメタクリラート、1h,1h,2h,2h−ペルフルオロデシルメタクリラート、2,2,3,4,4,4−ヘキサフルオロブチルメタクリラート、ペンタフルオロベンジルメタクリラート、ペンタフルオロフェニルメタクリラート、2,2,3,3−テトラフルオロプロピルメタクリラート、2−ブロモエチルメタクリラート、メタクリラトクロム酸クロリド、2−クロロエチルメタクリラート、シクロペンチルメタクリラート、1,4−シクロヘキサンジメチル1,4−ジメタクリラート,2−シアノエチルメタクリラート、メタクリル酸バリウム、メタクリル酸カリウム、メタクリル酸マグネシウム、メタクリル酸ナトリウム、メタクリル酸亜鉛、フルフリルメタクリラート、フェニルメタクリラート、ネオペンチルグリコールジメタクリラート、メタアリルメタクリラート、2−メトキシエチルメタクリラート、プロパルギルメタクリラート、3−メトキシブチルメタクリラート、tert−ブチルメタクリラート、イソプロピルメタクリラート、イソ−アミルメタクリラート、n−デシルメタクリラート、sec−ブチルメタクリラート、2−エチルブチルメタクリラート、n−プロピルメタクリラート、2−n−ブトキシエチルメタクリラート、ヒドロキシプロピルメタクリラート、メタクリルオキシプロピルメチルジクロロシラン、ベンジルメタクリラート、2−フェノキシエチルメタクリラート、メタクリルオキシプロピルトリス(メトキシエトキシ)シラン、3−メタクリルオキシプロピルペンタメチルジシロキサン、イソ−デシルメタクリラート、メタクリルオキシトリ−n−ブチルスズ、n−アミルメタクリラート、n−オクチルメタクリラート、トリメチルシリルメタクリラート、2−(トリメチルシロキシ)エチルメタクリラート、メタクリルオキシプロピルビス(トリメチルシロキシ)メチルシラン、メタクリルオキシプロピルトリス(トリメチルシロキシ)シラン、メタクリルオキシプロピルジメチルエトキシシラン、3−メタクリルオキシプロピルメチルジエトキシシラン、3−メタクリルオキシプロピルジメチルクロロシラン、2−メタクリルオキシエチルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロリド、アセトアセトキシエチルメタクリラート、メタクリルオキシプロピルトリクロロシラン、3−メタクリルオキシプロピルトリス(ビニルジメチルシロキシ)シラン、トリメチルシリルメチルメタクリラート、(メタクリルオキシメチル)フェニルジメチルシラン、メタクリルオキシプロペニルトリメトキシシラン、メタクリル酸カルシウム、トリデシルメタクリラート、ビニルメタクリラート、メトキシエトキシエチルメタクリラート、[2−(メタクリロイルオキシ)エチル]トリメチルアンモニウムクロリド、モノ−(2−(メタクリロイルオキシ)−エチル)フタラート、2−ヒドロキシ−3−フェノキシプロピルメタクリラート、メタクリルオキシプロピルトリエトキシシラン、2−ジイソプロピルアミノエチルメタクリラート、1h,1h,2h,2h−ペルフルオロオクチルメタクリラート、2−アミノエチルメタクリラート塩酸塩、2−トリメチルアンモニウムエチルメタクリラートメトスルファート、トリチルメタクリラート、ペルフルオロオクチルメタクリラート、2,4,6−トリブロモフェニルメタクリラート、4−ヒドロキシブチルメタクリラート、ヘキサデシルメタクリラート、ウンデシルメタクリラート、n−ノニルメタクリラート、2−アリルオキシエトキシエチルメタクリラート、3,3,5−トリメチルシクロヘキシルメタクリラート、2,3−ジブロモプロピルメタクリラート、シンナミルメタクリラート、クロチルメタクリラート、1h,1h,9h−ヘキサデカフルオロノニルメタクリラート、n−ヘプチルメタクリラート、2−アリルオキシエチルメタクリラート、アリルオキシプロピルメタクリラート、ネオ−ペンチルメタクリラート、2−(1−アジリジニル)−エチルメタクリラート、ベヘニルメタクリラート、5−ノルボルネン−2−メタノールメタクリラート、1,3−ビス(4−ベンゾイル−3−ヒドロキシフェノキシ)−2−プロピルメタクリラート、エトキシエトキシエチルメタクリラート、p−クロロフェノキシエチルメタクリラート、4−クミルフェニルメタクリラート、ジブチルスズメタクリラート、n,n−ジエチルアミノエチルメタクリラートq−塩メトスルファート、ジエチレングリコールモノ−メタクリラート、2,3−ジヒドロキシプロピルメタクリラート、3,3−ジメチルブタノール−2メタクリラート、エチルトリグリコールメタクリラート、エチリデンジメタクリラート、エチルチオエチルメタクリラート、ヘキソキシエチルメタクリラート、2−(1−イミダゾロイル)エチルメタクリラート、3−ヨードベンジルメタクリラート、イソシアナトエチルメタクリラート、d−メンチルメタクリラート、l−メンチルメタクリラート、メタクリル酸アルミニウム、n−(メタクリルオキシエチル)フタルイミド、n−(メタクリルオキシエチル)スクシンイミド、4−メタクリルオキシエチルトリメリット酸無水物、4−メタクリルオキシ−2−ヒドロキシベンゾフェノン、モノ−(2−(メタクリロイルオキシ)−エチル)マレアート、2−メタクリロイルオキシメチル−2,3−ジヒドロ−4h−ピラン、メトキシプロピルメタクリラート、3−メチルブタノール−2メタクリラート、3−メチルブテン−2−イル−メタクリラート、2−メチルブチルメタクリラート、3−(4−メチルフェノキシ)−2−ヒドロキシプロピルメタクリラート、2−n−モルホリノエチルメタクリラート、α−ナフチルメタクリラート、2−ナフチルメタクリラート、2−(1−ナフチルオキシ)−エチルメタクリラート、2−(2−ナフチルオキシ)−エチルメタクリラート、2−ニトロエチルメタクリラート、p−ニトロフェニルメタクリラート、ノニルフェニルメタクリラート、ノルボルニルメタクリラート、イソ−オクチルメタクリラート、ペンタブロモフェニルメタクリラート、ペンタクロロフェニルメタクリラート、ペルフルオロシクロヘキシルメチルメタクリラート、フェニルプロピルメタクリラート、1−ピペリジンエチルメタクリラート、ソルビトールメタクリラート、2−スルホエチルメタクリラート、トリブロモネオペンチルメタクリラート、トリクロロエチルメタクリラート、1h,1h,7h−ドデカフルオロヘプチルメタクリラート、3,5,5−トリメチルヘキシルメタクリラート,メタクリルオキシエトキシトリス(トリメチルシロキシ)シラン、ビニルベンジルメタクリラート、2−(n−エチルペルフルオロオクタンスルファミド)エチルメタクリラート、3−(トリフルオロメチル)ベンジルメタクリラート、イソボルニルメタクリラート、ポリ(エチレングリコール)メタクリラート、ヒドロキシプロピルメタクリラート、メタクリル酸鉛2−エチルヘキサノアート、2−メタクリルオキシエチルグルコシド、ビス(2,3−ジブロモプロピル)2−(メタクリロイルオキシ)−エチルホスファート、3−メチル−2−ベンゾチアゾリノン、4−(2−(me−アクリロイル−o)eto)−m−アニスアルデヒドを含むアジン、2−(メタクリロイルオキシ)エチルn−(3−ブロモフェニル)カルバマート、2−(メタクリロイルオキシ)エチルn−(n−(3,5−ジクロロフェニル)カルバモイル)カルバマート、2−(メタクリロイルオキシ)エチルn−(4−イソプロピルフェニル)カルバマート、エチレングリコールメタクリラートホスファート、トリメチロールプロパンジアリルエーテルモノ−メタクリラート、アビトールメタクリラート、イソシアナトエチルメタクリラートブチルウレタン、イソシアナトエチルメタクリラートオクチルウレタン、イソシアナトエチルメタクリラートカプロラクタム付加体、イソシアナトエチルメタクリラートピロリドン付加体、メタクリル酸ヒドロキシプロピルエステル、メタクリル酸カルシウム水和物、2−ヒドロキシ−4−[2−ヒドロキシ−3−(メタクリロイルオキシ)−プロポキシ]ベンゾフェン、メタクリルオキシジフェニルアンチモン、(2−メタクリルオキシエトキシ)トリイソプロポキシチタナート、(メタクリルオキシメチル)ビス(トリメチルシロキシ)メチルシラン、(メタクリルオキシメチル)ジメチルエトキシシラン、メタクリルオキシメチルトリエトキシシラン、メタクリルオキシメチルトリメトキシシラン、メタクリルオキシメチルトリメチルゲルマン、メタクリルオキシメチルトリス(トリメチルシロキシ)シラン、メタクリルオキシプロピルジメチルメトキシシラン、メタクリルオキシプロピルメチルジメトキシシラン、メタクリルオキシプロピルシラトラン、メタクリルオキシトリエチルゲルマン、チタンメタクリラートトリイソプロポキシド、ジシクロペンテニルメタクリラート、テトラヒドロピラニルメタクリラート、カプロラクトン2−(メタクリロイルオキシ)エチルエステル、2−メチル−2−ニトロプロピルメタクリラート、2−(2−オキソ−1−イミダゾリジニル)エチルメタクリラート、テトラキス(2−メタクリルオキシエトキシ)シラン、2−(メチルチオ)エチルメタクリラート、2−[3−(2h−ベンゾトリアゾール−2−イル)−4−ヒドロキシフェニル]エチルメタクリラート、ジシクロペンテニルオキシエチルメタクリラート、2−メチル−アクリル酸4−ヒドロキシ−フェニルエステル、2−(ペルフルオロブチル)エチルメタクリラート、2−(ペルフルオロデシル)エチルメタクリラート、2−(ペルフルオロ−3−メチルブチル)エチルメタクリラート、3−(ペルフルオロ−3−メチルブチル)−2−ヒドロキシプロピルメタクリラート、2−(ペルフルオロ−5−メチルヘキシル)エチルメタクリラート、3−(ペルフルオロ−5−メチルヘキシル)−2−ヒドロキシプロピルメタクリラート、2−(ペルフルオロ−7−メチルオクチル)エチルメタクリラート、3−(ペルフルオロ−7−メチルオクチル)−2−ヒドロキシプロピルメタクリラート、2−(ペルフルオロ−9−メチルデシル)エチルメタクリラート、3−(ペルフルオロ−8−メチルデシル)−2−ヒドロキシプロピルメタクリラート、(9−アントリル)メタクリラート、(9−フェナントリル)メチルメタクリラート、n−(3−メタクリルオキシ−2−ヒドロキシプロピル)−3−アミノプロピルトリエトキシシラン、4−(メタクリロイルオキシ)カルコン、モノ−2−(メタクリロイルオキシ)エチルスクシナート、2−(スルホオキシ)エチルメタクリラートアンモニウム塩、エチレンメタクリラートホスファート、2−me−アクリル酸2−(4−(1,3−ジオキソ−1,3−ジヒドロ−イソインドール−2−イル)−フェニル)−エチルエステル、2−(2’−メタクリルオキシ−5’−メチルフェニル)ベンゾトリアゾール、2−me−アクリル酸3(3,5−ジオキソ−4−アザ−トリシクロ(5.2.1.0(2,6))デカ−8−エン−4−イル)phエステル、2−me−アクリル酸4−(4−ニトロ−1,3−ジオキソ−1,3−ジヒドロ−イソインドール−2−イル)−フェニルエステル、rcl r35,715−4,9−アントラセニルメチルメタクリラート、1−ピレニルメチルメタクリラート、2−メチル−アクリル酸3−(1−オキソ−1,3−ジヒドロ−イソインドール−2−イル)−フェニルエステル、2−me−アクリル酸3−(4−ニトロ−1,3−ジオキソ−1,3−ジヒドロ−イソインドール−2−イル)−フェニルエステル、2−メチル−アクリル酸3−(2,5−ジオキソ−ピロリジン−1−イル)−フェニルエステル、2−メチル−アクリル酸4−(2,5−ジオキソ−ピロリジン−1−イル)−フェニルエステル、rcl r35,836−3,2−メチル−アクリル酸4−アセチルアミノ−フェニルエステル、(1−ピレン)メチルメタクリラート、2−ヒドロキシプロピル2−(メタクリロイルオキシ)エチルフタラート、pegモノメタクリラート、3−メチルブテン−2−イル−l−メタクリラート、(メタクリルオキシメチル)ビス(トリメチルシロキシ
)−(メチルシロキシ)メチルシラン、(r)−2−ヒドロキシ−2’−メタクリルオキシ−1,1’−ビ−2−ナフトール、4−[[6−(メタクリロイルオキシ)ヘキシル]オキシ]ベンゼンカルボン酸、イソシアナトエチルメタクリラートのヘキサフルオロイソプロピルウレタン、ジシクロペンテニル−2−メタクリラート、(r)−(−)−イソボルニルメタクリラート、3−ペルフルオロヘキシル−2−ヒドロキシプロピルメタクリラート、3−ペルフルオロオクチル−2−ヒドロキシプロピルメタクリラート、(1−ナフチル)エチルメタクリラート、(1−ナフチル)メチルメタクリラート、o−メタクリロイルヘキスト33258、o−(メタクリルオキシエチル)−n−(トリエトキシシリルプロピル)ウレタン、4−[3−(メタクリロイルオキシ)プロポキシ]ベンゼンカルボン酸、4−[4−(メタクリロイルオキシ)ブトキシ]ベンゼンカルボン酸、ヘキサフルオロイソプロピルウレタン−n−エチルメタクリラート、2−メチル−アクリル酸2−(4−(4,5−ジヒドロ−オキサゾール−2−イル)−フェノキシ)−エチルエステル、3−メタクリルオキシプロピルトリス(ペンタメチルジシロキシ)シラン、ジ(プロピレングリコール)アリルエーテルメタクリラート、トリアセトンアミノイルメタクリラート、1h,1h−ペルフルオロ−n−デシルメタクリラート、3−(ペルフルオロブチル)−2−ヒドロキシプロピルメタクリラート、2−メチル−アクリル酸4−(3−フェニル−アクリロイル)−フェニルエステル、3−(5−ニトロ−1,3−ジオキソ−1,3−ジヒドロ−2h−イソインドール−2−イル)フェニル2−メチルアクリラート、n−(2−ヒドロキシ−3((2−メチル−1−オキソ−2−プロペニル)オキシ)プロピル)−n−(4−メチルフェニル)−グリシン又はそれらの混合物。
[式中:
T1は、四価の有機ラジカルを表す]
で表される1つ以上のテトラカルボン酸無水物との反応によって得られ得るか又は得ることが可能である。
1,1,4,4−ブタンテトラカルボン酸二無水物、
エチレンマレイン酸二無水物、
1,2,3,4−シクロブタンテトラカルボン酸二無水物、
1,2,3,4−シクロペンタンテトラカルボン酸二無水物、
2,3,5−トリカルボキシシクロペンチル酢酸二無水物、
3,5,6−トリカルボキシノルボルニル酢酸二無水物、
2,3,4,5−テトラヒドロフランテトラカルボン酸二無水物、
rel−[1S,5R,6R]−3−オキサビシクロ[3.2.1]オクタン−2,4−ジオン−6−スピロ−3’−(テトラヒドロフラン2’,5’−ジオン),4−(2,5−ジオキソテトラヒドロフラン−3−イル)テトラヒドロナフタレン−1,2−ジカルボン酸二無水物、5−(2,5−ジオキソテトラヒドロフラン−3−イル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸二無水物、ビシクロ[2.2.2]オクタ−7−エン−2,3,5,6−テトラカルボン酸二無水物、ビシクロ[2.2.2]オクタン−2,3,5,6−テトラカルボン酸二無水物、1,8−ジメチルビシクロ[2.2.2]オクタ−7−エン−2,3,5,6−テトラカルボン酸二無水物など。
ピロメリト酸二無水物、
3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物、
4,4’−オキシジフタル酸二無水物、
3,3’,4,4’−ジフェニルスルホンテトラカルボン酸二無水物、
1,4,5,8−ナフタレンテトラカルボン酸二無水物、
2,3,6,7−ナフタレンテトラカルボン酸二無水物、
3,3’,4,4’−ジメチルジフェニルシランテトラカルボン酸二無水物、
3,3’,4,4’−テトラフェニルシランテトラカルボン酸二無水物、
1,2,3,4−フランテトラカルボン酸二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルスルフィド二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルスルホン二無水物、
4,4’−ビス(3,4−ジカルボキシフェノキシ)ジフェニルプロパン二無水物、
3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、
エチレングリコールビス(トリメリット酸)二無水物、
4,4’−(1,4−フェニレン)ビス(フタル酸)二無水物、
4,4’−(1,3−フェニレン)ビス(フタル酸)二無水物、
4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物、
4,4’−オキシジ(1,4−フェニレン)ビス(フタル酸)二無水物、
4,4’−メチレンジ(1,4−フェニレン)ビス(フタル酸)二無水物など。
1,2,3,4−シクロブタンテトラカルボン酸二無水物、
1,2,3,4−シクロペンタンテトラカルボン酸二無水物、
2,3,5−トリカルボキシシクロペンチル酢酸二無水物、
5−(2,5−ジオキソテトラヒドロフラン−3−イル)−3−メチル−3−シクロヘキセン−1,2−ジカルボン酸二無水物、
4−(2,5−ジオキソテトラヒドロフラン−3−イル)テトラヒドロナフタレン−1,2−ジカルボン酸二無水物、
4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物、及び
ビシクロ[2.2.2]オクタ−7−エン−2,3,5,6−テトラカルボン酸二無水物。
4−アミノ−2,3,5,6−テトラフルオロ安息香酸
4−アミノ−3,5−ジヨード安息香酸、3,4−ジアミノ安息香酸、
4−アミノ−3−メチル安息香酸、
4−アミノ−2−クロロ安息香酸
4−アミノサリチル酸
4−アミノ安息香酸
4−アミノフタル酸
1−(4−アミノフェニル)エタノール
4−アミノベンジルアルコール
4−アミノ−3−メトキシ安息香酸
4−アミノフェニルエチルカルビノール
4−アミノ−3−ニトロ安息香酸
4−アミノ−3,5−ジニトロ安息香酸
4−アミノ−3,5−ジクロロ安息香酸
4−アミノ−3−ヒドロキシ安息香酸
4−アミノベンジルアルコール塩酸塩
4−アミノ安息香酸塩酸塩
パラローザニリン塩基
4−アミノ−5−クロロ−2−メトキシ安息香酸
4−(ヘキサフルオロ−2−ヒドロキシイソプロピル)アニリン
ピペラジン−p−アミノベンゾアート
4−アミノ−3,5−ジブロモ安息香酸
イソニコチン酸ヒドラジドp−アミノサリチル酸塩
4−アミノ−3,5−ジヨードサリチル酸
4−アミノ−2−メトキシ安息香酸
2−[2−(4−アミノフェニル)−2−ヒドロキシ−1−(ヒドロキシメチル)エチル]イソインドリン−1,3−ジオン
4−アミノ−2−ニトロ安息香酸
2,4−ジアミノ安息香酸
p−アミノ安息香酸、
[3,5−3h]−4−アミノ−2−メトキシ安息香酸
L−(+)−トレオ−2−アミノ−1−(4−アミノフェニル)−1,3−プロパンジオール
L−(+)−トレオ−2−(N,N−ジメチルアミノ)−1−(4−アミノフェニル)−1,3−プロパンジオール
2−(4−アミノフェニル)−3,3,3−トリフルオロ−2−ヒドロキシプロパン酸エチル
2−(4−アミノ−3−メチルフェニル)−3,3,3−トリフルオロ−2−ヒドロキシプロパン酸エチル
2−(4−アミノ−3−メトキシフェニル)−3,3,3−トリフルオロ−2−ヒドロキシプロパン酸エチル
3,4−ジアミノベンジルアルコール二塩酸塩
4−アミノナフタレン−1,8−ジカルボン酸
4−アミノ−3−クロロ−5−メチル安息香酸
4−アミノ−2,6−ジメチル安息香酸
4−アミノ−3−フルオロ安息香酸
4−アミノ−5−ブロモ−2−メトキシベンゼンカルボン酸
2,7−ジアミノフルオレン
4,4’−ジアミノオクタフルオロビフェニル
3,3’−ジアミノベンジジン
3,3’,5,5’−テトラメチルベンジジン
3,3’−ジメトキシベンジジン
o−トリジン
3,3’−ジニトロベンジジン
2−ニトロベンジジン
3,3’−ジヒドロキシベンジジン
o−トリジンスルホン
ベンジジン、
3,3’−ジクロロベンジジン
2,2’,5,5’−テトラクロロベンジジン、
ベンジジン−3,3’−ジカルボン酸
4,4’−ジアミノ−1,1’−ビナフチル
4,4’−ジアミノジフェニル−3,3’−ジグリコール酸
ジヒドロエチジウム
o−ジアニシジン
2,2’−ジクロロ−5,5’−ジメトキシベンジジン
3−メトキシベンジジン
3,3’−ジクロロベンジジン(ジフェニル−d6)、
2,7−ジアミノ−9−フルオレノン
3,5,3’,5’−テトラブロモ−ビフェニル−4,4’−ジアミン
2,2’−ビス(トリフルオロメチル)ベンジジン
2,2’−ジクロロ[1,1’−ビフェニル]−4,4’−ジアミン
3,9−ジアミノ−1,11−ジメチル−5,7−ジヒドロ−ジベンゾ(a,c)シクロヘプテン−6−オン
3,3’−ビス(トリフルオロメチル)ベンジジン
ジベンゾ(1,2)ジチイン−3,8−ジアミン
3,3’−トリジン−5−スルホン酸
3,3’−ジクロロベンジジン−d6
テトラメチルベンジジン
3,3’−ジアミノベンゾフェノン、3,3’−ジアミノジフェニルメタン、
4,4−ビス−(3−アミノ−4−ヒドロキシフェニル)−バレリアン酸
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン
2,2−ビス(3−アミノ−4−メチルフェニル)ヘキサフルオロプロパン
テトラブロモメチレンジアニリン
2,7−ジアミノ−9−フルオレノン
2,2−ビス(3−アミノフェニル)ヘキサフルオロプロパン
ビス−(3−アミノ−4−クロロ−フェニル)−メタノン
ビス−(3−アミノ−4−ジメチルアミノ−フェニル)−メタノン
3−[3−アミノ−5−(トリフルオロメチル)ベンジル]−5−(トリフルオロメチル)アニリン
1,5−ジアミノナフタレン
又はそれらの誘導体から製造されるか又は選択される(但しこの場合も、列挙される化合物で2つのアミノ基を保持しないものは、少なくとも1つの追加のアミノ基を有する誘導体として考慮される)。
エチレンジアミン、1,3−プロピレンジアミン、1,4−ブチレンジアミン、1,5−ペンチレンジアミン、1,6−ヘキシレンジアミン、1,7−ヘプチレンジアミン、1,8−オクチレンジアミン、1,9−ノニレンジアミン、1,10−デシレンジアミン、1,11−ウンデシレンジアミン、1,12−ドデシレンジアミン、α,α’−ジアミノ−m−キシレン、α,α’−ジアミノ−p−キシレン、(5−アミノ−2,2,4−トリメチルシクロペンチル)メチルアミン、1,2−ジアミノシクロヘキサン、4,4’−ジアミノジシクロヘキシルメタン、1,3−ビス(メチルアミノ)シクロヘキサン、4,9−ジオキサドデカン−1,12−ジアミン、3,5−ジアミノ安息香酸メチルエステル、3,5−ジアミノ安息香酸ヘキシルエステル、3,5−ジアミノ安息香酸ドデシルエステル、3,5−ジアミノ安息香酸イソプロピルエステル、4,4’−メチレンジアニリン、4,4’−エチレンジアニリン、4,4’−ジアミノ−3,3’−ジメチルジフェニルメタン、3,3’,5,5’−テトラメチルベンジジン、4,4’−ジアミノジフェニルスルホン、4,4’−ジアミノジフェニルエーテル、1,5−ジアミノナフタレン、3,3’−ジメチル−4,4’−ジアミノビフェニル、3,4’−ジアミノジフェニルエーテル、3,3’−ジアミノベンゾフェノン、4,4’−ジアミノベンゾフェノン、4,4’−ジアミノ−2,2’−ジメチルビベンジル、ビス[4−(4−アミノフェノキシ)フェニル]スルホン、1,4−ビス(4−アミノフェノキシ)ベンゼン、1,3−ビス(4−アミノフェノキシ)ベンゼン、1,3−ビス(3−アミノフェノキシ)ベンゼン、2,7−ジアミノフルオレン、9,9−ビス(4−アミノフェニル)フルオレン、4,4’−メチレン−ビス(2−クロロアニリン)、4,4’−ビス(4−アミノフェノキシ)ビフェニル、2,2’,5,5’−テトラクロロ−4,4’−ジアミノビフェニル、2,2’−ジクロロ−4,4’−ジアミノ−5,5’−ジメトキシビフェニル、3,3’−ジメトキシ−4,4’−ジアミノビフェニル、4,4’−(1,4−フェニレンイソプロピリデン)ビスアニリン、4,4’−(1,3−フェニレンイソプロピリデン)ビスアニリン、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、2,2−ビス[3−(4−アミノフェノキシ)フェニル]ヘキサフルオロプロパン、2,2−ビス[3−アミノ−4−メチルフェニル]ヘキサフルオロプロパン、2,2−ビス(4−アミノフェニル)ヘキサフルオロプロパン、2,2’−ビス[4−(4−アミノ−2−トリフルオロメチルフェノキシ)フェニル]ヘキサフルオロプロパン、4,4’−ジアミノ−2,2’−ビス(トリフルオロメチル)ビフェニル、及び4,4’−ビス[(4−アミノ−2−トリフルオロメチル)フェノキシ]−2,3,5,6,2’,3’,5’,6’−オクタフルオロビフェニル。
実施例において使用される定義:
LC/MS:液体クロマトグラフィー/質量分析
[M+Na]=分子質量プラスナトリウム
[M+H]=分子質量プラスプロトン
[M+NH4]=分子質量プラスアンモニウム
1H NMR=1H核磁気共鳴分光法
DMSO−d6=重水素化ジメチルスルホキシド
THF−d8=重水素化テトラヒドロフラン
300MHz=300メガヘルツ
m=マルチプレット
d=ダブレット
dd=ダブルダブレット
t=トリプレット
s=シングレット
q=クインテット
br=ブロード
δ=化学シフト
HCl=塩化水素
MeOH:メタノール
EtOAc:酢酸エチル
NMP:N−メチル−2−ピロリドン
THF:テトラヒドロフラン
TBME:tert.ブチルメチルエーテル
DMF:N,N−ジメチルホルムアミド
RT:室温、通常18℃〜28℃の範囲
[η]:粘度
v.t.%:体積百分率
MLC7067:Merck KGAから市販されている、誘電異方性10.3、光学異方性0.1025及び回転粘度81m.Pa.sの液晶の混合物。
実施例10A 2.00g(4.1mmol)を脱気したシクロヘキサノン10mLに溶解する。溶液をアルゴンでパージし、60℃に加熱する。シクロヘキサノン2mL中の2,2’−アゾビス(2−メチルプロピオニトリル)20.0mg(0.14mmol)の溶液を滴下する。60℃で36時間後、反応混合物を室温まで冷まし、テトラヒドロフラン5mLで希釈し、冷メタノール200mL中に沈殿させる。沈殿物を濾別し、メタノールで洗浄し、30℃で一晩乾燥させる。実施例11A 1.50gが白色の固体として得られる(収率75%)。
サイズ排除クロマトグラフィー(PS換算値):Mw 60,800。
サイズ排除クロマトグラフィー(PS換算値)、Mw 53,100。
サイズ排除クロマトグラフィー(PS換算値) Mw 75,400。
サイズ排除クロマトグラフィー(PS換算値) Mw 78,900。
実施例22A 4.8g(5.55mmol)をDMF63mlと水7mlの混合物に溶解する。塩化第二鉄六水和物13.8g(51.3mmol)を加える。亜鉛末5.58g(85.5mmol)を30分以内に少しずつ加える。混合物を2時間反応させる。次いで、反応混合物を酢酸エチルと水で分液し、濾過する。有機相を水で繰り返し洗浄し、硫酸ナトリウムで乾燥させ、濾過し、回転蒸発によって濃縮する。溶離剤としてトルエン:酢酸エチル(1:3)を使用してシリカゲル上で残渣を濾過し、実施例23A 3.56g(99%)が白色の粉状物として得られる。
1,2,3,4−シクロブタンテトラカルボン酸469mg(2.4mmol)を、NMP6.6g中の実施例23A 1200mg(2.4mmol)の溶液に加える。次いで、0℃で2時間撹拌を行う。その後、混合物を室温で21時間反応させる。ポリマー混合物をNMP4.4mLで希釈し、水150mL中に沈殿させて、40℃の真空下で乾燥させた後、PAA−1 1700mgが白色の粉状物の形態で得られる。η=0.38dL/g
PAA−1(実施例24)の調製と同様にして、PAA−2〜PAA−7は、2,3,5−トリカルボキシシクロペンチル酢酸−1,2:3,4−二無水物を用いて、ジアミン(以下の表を参照のこと)から調製される。分析データを以下の表に提供する。
29.1wt%のLCM1、0.3wt%の光開始剤IRGACURE(商標)369(Ciba SC社)、0.3wt%のTinuvine 123、及び0.3wt%のBHTの溶液を、溶媒としてアニソールを使用して調製する。溶液を室温で30分間撹拌し、0.20μmのPTFE hi-capで濾過する。
光反応性ポリマーの材料の2%重量の溶液S1を、シクロペンタノン中に調製する。溶液を室温で30分間撹拌し、0.20μmのPTFE hi-capで濾過する。溶液を2000rpmでガラス基板上にスピンコーティングし、次いで、これを180℃で5分間乾燥させる。その後、高圧水銀ランプからの偏光UVA光を基板に照射し、入射方向は基板表面と垂直にする。偏光には、Moxtec偏光子を使用する。Moxtec偏光子を使用して偏光UVAの曝露エネルギーを0.2〜250mJ.cm-2で変更した。製剤S2(実施例26)を直線偏光で曝露した基板上に800rpmでスピンコーティングし、次いで、これを50℃で30秒間乾燥させる。その後、得られた基板を窒素雰囲気で30秒間パージし、次いで、窒素雰囲気下にて1J.cm-2の等方性UV光で曝露する。交差偏光子を備えたLeitz顕微鏡下に調製するデバイスを置き、顕微鏡に接続された光電子増倍管によって明状態及び暗状態で光強度を別々に測定し、その結果をデジタル電圧計に送る。コントラスト比を以下の方程式から計算する:
コントラスト=[I45−Ioffset]/[I0°−Ioffset]、式中:
I0°(V)は、最小光強度、すなわち暗状態であり、
I45°(V)は、最大光強度、すなわち明状態であり、
Ioffset(V)は、S2溶液のコーティングなしで測定された光強度である。
実施例11O、実施例11N、実施例11F、実施例11E、実施例11M由来の実施例27において調製したデバイスの、150mJ.cm-2の偏光UVAの曝露エネルギーに対するハイコントラストを測定し、以下の表に示す。
液晶セル1を調製する。ここでは、液晶が光反応性ポリアミド酸PAA−1によってアラインされ、電界がセルギャップの各側上の2つの平面電極間に適用される。
コントラスト比=Tmax/Tmin
実施例12〜実施例17由来の材料を使用し、その後、基板を偏光UVB及びUVAで照射する以外は、実施例27と同様にアライメント層を調製する。LCPフィルム中に欠陥のない良好なアライメント品質を得るために必要な最小エネルギーを各化合物について決定する。また、方位安定性を実施例29と同様に測定する。結果を以下の表に提供する。
Claims (12)
- 一般式(I):
[式中、
Ar1及びAr2は、互いに独立して、4〜40個の原子の環系であり、ここで、各環系は、式(I)に示される二重結合に電子共役(π−π結合)を介して直接連結された少なくとも1つの不飽和を含み、
ここで、環系は、非置換であるか、又は
ハロゲン原子及び/又はヒドロキシ、ニトロ、ニトリル、−CF3のような極性基によって;あるいはカルボキシ基、及び/又は1〜30個の炭素原子を有する環式の直鎖若しくは分岐アルキル残基(非置換であるか、メチル、フッ素及び/又は塩素によって単又は多置換されており、ここで、1つ以上の、好ましくは隣接していない−CH2−基は、独立して、−O−、−CO−、−CO−O−、−O−CO−、−NR1’−、−NR1’−CO−、−CO−NR1’−、−NR1’−CO−O−、−O−CO−NR1’−、−NR1’−CO−NR1’−、−CH=CH−、−C≡C−、−O−CO−O−及び−Si(CH3)2−O−Si(CH3)2−から選択される基、芳香族又は脂環式基によって置き換わっていてよく、ここで、R1’は、水素原子又は低級アルキルである);及び/又は1〜20個の炭素原子を有する、好ましくは1〜10個の炭素原子を有する、アクリロイルオキシ、アルコキシ、アルキルカルボニルオキシ、アルキルオキソカルボニルオキシ、メタクリロイルオキシ、ビニル、アリル、ビニルオキシ及び/又はアリルオキシ基によって単若しくは多置換されており;好ましくは、環系は、非置換であるか又はアルコキシ基によって置換されており;そして、式中;
Xが水素であり、そしてYがCNである場合、
R1、R2又はR3は、互いに独立して、水素、ハロゲン又は−CF3であるが、但し、R1、R2又はR3は、同時に水素ではなく;
XがCNであり、そしてYが水素である場合;
R1、R2又はR3は、互いに独立して、水素、ハロゲン又は−CF3であり;
Mは、単一の共有結合又はスペーサー単位であり;
Y1、Y2は、互いに独立して、架橋基であり、
Pは、水素原子、場合により置換されているアルキル、又は重合性基である]
に係る化合物。 - 請求項1に記載の少なくとも1つの化合物をモノマー単位として含む、オリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)。
- ゲル又はネットワークの形態の請求項2に記載のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)。
- シラン含有化合物、アクリラート−若しくはエポキシ含有架橋剤、光増感剤、光ラジカル発生剤及び/又はカチオン光開始剤などの添加剤をさらに含む、請求項2に記載のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)。
- 他のポリマー、オリゴマー、モノマー、光活性ポリマー、光活性オリゴマー及び/又は光活性モノマーを混合物でさらに含む、請求項2に記載のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)。
- 支持体に適用され、アライニング光を照射することによって架橋される、請求項2に記載のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)。
- 請求項2〜6に記載のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)を含む、組成物。
- 液晶用のアライメント層としての、請求項2に記載の1つ以上のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)の使用。
- 請求項2に記載の1つ以上のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)を含むアライメント層。
- 異なるアライメント方向のパターンを有する請求項9に記載のアライメント層。
- 請求項9に記載のアライメント層の調製のための方法であって、請求項2に記載の1つ以上のオリゴマー、デンドリマー又はポリマー(ポリマーは、とりわけ、コポリマー又はホモポリマーである)が、好ましくは溶液で、場合により電極を備えた支持体に、場合により先のイミド化後に適用され、前記の適用されたオリゴマー、デンドリマー又はポリマーがアライニング光を照射することによって架橋される、方法。
- 請求項9に記載の少なくとも1つのアライメント層を含む、光学及び電気光学的な非構造化又は構造化構成素子、好ましくは液晶ディスプレイセル、多層及びハイブリッド層素子。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13169419 | 2013-05-28 | ||
EP13169419.2 | 2013-05-28 | ||
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KR20180082540A (ko) * | 2015-11-11 | 2018-07-18 | 롤릭 테크놀로지스 아게 | 광-정렬가능 물질의 조성물 |
US11181674B2 (en) | 2016-07-29 | 2021-11-23 | Rolic Technologies AG | Method for generating alignment on top of a liquid crystal polymer material |
US20220163853A1 (en) | 2019-07-24 | 2022-05-26 | Rolic Technologies AG | Photo-alignable positive c-plate retarder |
CN113862000B (zh) * | 2021-11-09 | 2023-07-11 | 西北工业大学 | 一种荧光颜色连续可调液晶聚合物及制备方法 |
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JPH0211542A (ja) * | 1988-04-25 | 1990-01-16 | Eli Lilly & Co | プロパンアミン誘導体 |
JP2009511431A (ja) * | 2005-09-20 | 2009-03-19 | ロリク アーゲー | 官能化された光反応性化合物 |
WO2013026691A1 (en) * | 2011-08-25 | 2013-02-28 | Rolic Ag | Photoreactive compounds |
WO2013050121A1 (en) * | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
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US6107427A (en) | 1995-09-15 | 2000-08-22 | Rolic Ag | Cross-linkable, photoactive polymer materials |
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JPS57154157A (en) * | 1981-03-16 | 1982-09-22 | Chisso Corp | 2-(4-fluorophenyl)-3c-(4-substituted phenyl)-acrylonitrile |
JPH0211542A (ja) * | 1988-04-25 | 1990-01-16 | Eli Lilly & Co | プロパンアミン誘導体 |
JP2009511431A (ja) * | 2005-09-20 | 2009-03-19 | ロリク アーゲー | 官能化された光反応性化合物 |
WO2013026691A1 (en) * | 2011-08-25 | 2013-02-28 | Rolic Ag | Photoreactive compounds |
WO2013050121A1 (en) * | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
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JP2019204071A (ja) * | 2017-10-31 | 2019-11-28 | Jnc株式会社 | 光配向用液晶配向剤、液晶配向膜およびこれを用いた液晶表示素子、並びに、ジアミンおよびポリマー |
JP7247511B2 (ja) | 2017-10-31 | 2023-03-29 | Jnc株式会社 | 光配向用液晶配向剤、液晶配向膜およびこれを用いた液晶表示素子、並びに、ジアミンおよびポリマー |
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CN105377811A (zh) | 2016-03-02 |
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EP3004050B1 (en) | 2020-09-02 |
US10329486B2 (en) | 2019-06-25 |
US20160083655A1 (en) | 2016-03-24 |
CN111533668A (zh) | 2020-08-14 |
KR102250929B1 (ko) | 2021-05-13 |
KR20160013178A (ko) | 2016-02-03 |
JP2019039012A (ja) | 2019-03-14 |
TWI662075B (zh) | 2019-06-11 |
HK1218744A1 (zh) | 2017-03-10 |
JP6644676B2 (ja) | 2020-02-12 |
WO2014191292A1 (en) | 2014-12-04 |
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