TWI515227B - A liquid crystal aligning agent containing a polyamic acid ester and a polyamic acid, and a liquid crystal alignment film - Google Patents
A liquid crystal aligning agent containing a polyamic acid ester and a polyamic acid, and a liquid crystal alignment film Download PDFInfo
- Publication number
- TWI515227B TWI515227B TW100108731A TW100108731A TWI515227B TW I515227 B TWI515227 B TW I515227B TW 100108731 A TW100108731 A TW 100108731A TW 100108731 A TW100108731 A TW 100108731A TW I515227 B TWI515227 B TW I515227B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- crystal alignment
- group
- added
- alignment agent
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 218
- 239000003795 chemical substances by application Substances 0.000 title claims description 108
- 229920005575 poly(amic acid) Polymers 0.000 title claims description 49
- 150000002148 esters Chemical class 0.000 title claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 238000000576 coating method Methods 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 19
- 108010039918 Polylysine Proteins 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 229920000656 polylysine Polymers 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 152
- 239000000243 solution Substances 0.000 description 142
- 230000015572 biosynthetic process Effects 0.000 description 81
- 238000003786 synthesis reaction Methods 0.000 description 80
- 239000000203 mixture Substances 0.000 description 70
- 239000000758 substrate Substances 0.000 description 47
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 46
- 238000003756 stirring Methods 0.000 description 45
- -1 diamine compound Chemical class 0.000 description 43
- 239000002253 acid Substances 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- 150000004985 diamines Chemical class 0.000 description 34
- 238000000034 method Methods 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 210000002858 crystal cell Anatomy 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 239000007822 coupling agent Substances 0.000 description 20
- 108010026466 polyproline Proteins 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 9
- XYSNGNNDJGSUMY-UHFFFAOYSA-N C(C1CO1)OCCCC(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(C1CO1)OCCCC(C(OCC)(OCC)C)CCCCCCCC XYSNGNNDJGSUMY-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 238000001816 cooling Methods 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920000954 Polyglycolide Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000004633 polyglycolic acid Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 108010094020 polyglycine Proteins 0.000 description 5
- 229920000232 polyglycine polymer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229920000037 Polyproline Polymers 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 3
- CWZQYRJRRHYJOI-UHFFFAOYSA-N 1,1,1-trimethoxydecane Chemical compound CCCCCCCCCC(OC)(OC)OC CWZQYRJRRHYJOI-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QUNAYECDJMFUKV-UHFFFAOYSA-N 2,5-bis(methoxycarbonyl)terephthalic acid Chemical compound COC(=O)C1=CC(C(O)=O)=C(C(=O)OC)C=C1C(O)=O QUNAYECDJMFUKV-UHFFFAOYSA-N 0.000 description 2
- HBLPYXIZPMDWIO-UHFFFAOYSA-N 3-(methylaminomethyl)aniline Chemical compound CNCC1=CC=CC(N)=C1 HBLPYXIZPMDWIO-UHFFFAOYSA-N 0.000 description 2
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- SLHXQWDUYXSTPA-UHFFFAOYSA-N 4-[5-(4-aminophenoxy)pentoxy]aniline Chemical compound C1=CC(N)=CC=C1OCCCCCOC1=CC=C(N)C=C1 SLHXQWDUYXSTPA-UHFFFAOYSA-N 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004954 Polyphthalamide Substances 0.000 description 2
- 229910021603 Ruthenium iodide Inorganic materials 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- NHPHHNLWGXBMKP-UHFFFAOYSA-N dimethyl cyclobutane-1,3-dicarboxylate Chemical compound COC(=O)C1CC(C(=O)OC)C1 NHPHHNLWGXBMKP-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 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
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920006375 polyphtalamide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 150000007970 thio esters Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000012463 white pigment Substances 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 1
- BWOAYXPSLWWQOR-UHFFFAOYSA-N 1,1,1-triethoxy-13-(13,13,13-triethoxytridecyldisulfanyl)tridecane Chemical compound C(C)OC(CCCCCCCCCCCCSSCCCCCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC BWOAYXPSLWWQOR-UHFFFAOYSA-N 0.000 description 1
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
- JDGFELYPUWNNGR-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene-1,3,4,6-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C2C(C(=O)O)CC(C(O)=O)C21 JDGFELYPUWNNGR-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- BWTPUFNHSVZIDT-UHFFFAOYSA-N 1,3-bis[2-(4-aminophenyl)ethyl]urea Chemical compound C1=CC(N)=CC=C1CCNC(=O)NCCC1=CC=C(N)C=C1 BWTPUFNHSVZIDT-UHFFFAOYSA-N 0.000 description 1
- SBHHKGFHJWTZJN-UHFFFAOYSA-N 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C)(C(O)=O)C1C(O)=O SBHHKGFHJWTZJN-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- VPQDCNLNZYGLNT-UHFFFAOYSA-N 2,4-bis(methoxycarbonyl)cyclobutane-1,3-dicarboxylic acid Chemical compound COC(=O)C1C(C(O)=O)C(C(=O)OC)C1C(O)=O VPQDCNLNZYGLNT-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010058554 | 2010-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201200541A TW201200541A (en) | 2012-01-01 |
| TWI515227B true TWI515227B (zh) | 2016-01-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100108731A TWI515227B (zh) | 2010-03-15 | 2011-03-15 | A liquid crystal aligning agent containing a polyamic acid ester and a polyamic acid, and a liquid crystal alignment film |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6048143B2 (ja) |
| KR (1) | KR101818788B1 (ja) |
| CN (1) | CN102893208B (ja) |
| TW (1) | TWI515227B (ja) |
| WO (1) | WO2011115078A1 (ja) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI485489B (zh) * | 2011-07-27 | 2015-05-21 | Nissan Chemical Ind Ltd | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
| KR101973226B1 (ko) * | 2011-10-12 | 2019-04-26 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| JP5939614B2 (ja) * | 2012-02-01 | 2016-06-22 | 株式会社ジャパンディスプレイ | 配向膜およびそれを用いた液晶表示装置 |
| WO2014157143A1 (ja) * | 2013-03-25 | 2014-10-02 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| JP6400284B2 (ja) * | 2013-10-22 | 2018-10-03 | 株式会社ジャパンディスプレイ | 液晶表示装置 |
| KR102331107B1 (ko) * | 2014-02-05 | 2021-11-24 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막, 및 그것을 사용한 액정 표시 소자 |
| KR102346494B1 (ko) * | 2014-04-03 | 2021-12-31 | 닛산 가가쿠 가부시키가이샤 | 폴리아믹산에스테르-폴리아믹산 공중합체를 함유하는 액정 배향제, 및 그것을 사용한 액정 배향막 |
| JP6350045B2 (ja) | 2014-07-07 | 2018-07-04 | Jsr株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| JP6805475B2 (ja) * | 2014-09-09 | 2020-12-23 | Jsr株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| CN115746874A (zh) * | 2014-10-28 | 2023-03-07 | 日产化学工业株式会社 | 液晶取向剂、液晶取向膜和液晶表示元件 |
| JP6447304B2 (ja) * | 2015-03-27 | 2019-01-09 | Jsr株式会社 | 液晶配向剤、液晶配向膜及びその製造方法、液晶表示素子、位相差フィルム及びその製造方法、重合体並びに化合物 |
| KR102710874B1 (ko) * | 2015-12-03 | 2024-09-26 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막 및 그것을 사용한 액정 표시 소자 |
| JP6174194B2 (ja) * | 2016-05-12 | 2017-08-02 | 株式会社ジャパンディスプレイ | 配向膜およびそれを用いた液晶表示装置 |
| US20180373099A1 (en) * | 2016-11-28 | 2018-12-27 | Lg Chem, Ltd. | Liquid crystal alignment film, method for preparing the same and liquid crystal display device using the same |
| JP7006033B2 (ja) | 2017-09-01 | 2022-02-10 | 富士フイルムビジネスイノベーション株式会社 | ポリイミド前駆体溶液、及びポリイミド成形体 |
| KR102065718B1 (ko) * | 2017-10-17 | 2020-02-11 | 주식회사 엘지화학 | 액정 배향막 및 이를 이용한 액정표시소자 |
| CN109942817A (zh) * | 2019-03-21 | 2019-06-28 | 深圳先进技术研究院 | 一种聚酰亚胺前体、制备方法以及树脂组合物及其应用 |
| WO2021049255A1 (ja) * | 2019-09-09 | 2021-03-18 | Jsr株式会社 | 液晶配向剤、液晶配向膜及び液晶素子 |
| JP2022054005A (ja) | 2020-09-25 | 2022-04-06 | 株式会社ジャパンディスプレイ | 液晶表示装置 |
| CN114479077B (zh) * | 2022-01-19 | 2024-03-29 | 波米科技有限公司 | 一种聚酰胺酸酯及其在液晶取向剂、液晶取向膜和液晶单元中的应用 |
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| JP4665333B2 (ja) * | 2000-11-27 | 2011-04-06 | 東レ株式会社 | ポジ型感光性樹脂前駆体組成物 |
| JP2003026918A (ja) | 2001-07-13 | 2003-01-29 | Hitachi Ltd | 液晶配向膜用材料、液晶表示素子、その製造方法及び液晶表示装置 |
| JP2004075944A (ja) * | 2002-08-22 | 2004-03-11 | Chisso Corp | 方向が規制されたポリイミド、これを用いた液晶配向膜、および液晶表示素子 |
| JP4159838B2 (ja) * | 2002-09-20 | 2008-10-01 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物及び半導体装置 |
| JP2008176304A (ja) * | 2006-12-22 | 2008-07-31 | Jsr Corp | 液晶配向剤、液晶配向膜、液晶表示素子および光学部材 |
| CN101663348B (zh) * | 2007-04-25 | 2012-06-06 | 日产化学工业株式会社 | 聚酰亚胺前体和聚酰亚胺以及形成图像的下层膜涂布液 |
| JP5382346B2 (ja) * | 2007-06-15 | 2014-01-08 | 日産化学工業株式会社 | 熱硬化膜形成用樹脂組成物 |
| CN101373296B (zh) * | 2007-08-24 | 2012-07-04 | 株式会社日立显示器 | 液晶显示装置及其制造方法 |
| CN101614912B (zh) * | 2008-06-26 | 2011-01-05 | 奇美实业股份有限公司 | 液晶定向剂及其所形成液晶定向膜的制造方法 |
| JP5355970B2 (ja) * | 2008-09-16 | 2013-11-27 | 株式会社ジャパンディスプレイ | 液晶表示装置 |
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- 2011-03-14 WO PCT/JP2011/055973 patent/WO2011115078A1/ja not_active Ceased
- 2011-03-14 KR KR1020127026739A patent/KR101818788B1/ko active Active
- 2011-03-14 JP JP2012505685A patent/JP6048143B2/ja active Active
- 2011-03-15 TW TW100108731A patent/TWI515227B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| TW201200541A (en) | 2012-01-01 |
| KR101818788B1 (ko) | 2018-01-15 |
| JP6048143B2 (ja) | 2016-12-21 |
| KR20130016275A (ko) | 2013-02-14 |
| WO2011115078A1 (ja) | 2011-09-22 |
| CN102893208A (zh) | 2013-01-23 |
| CN102893208B (zh) | 2015-07-08 |
| JPWO2011115078A1 (ja) | 2013-06-27 |
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