DE69313083T2 - Diaminoverbindungen, deren Herstellung sowie deren Verwendung für Flüssigkristallorientierungsschichten - Google Patents
Diaminoverbindungen, deren Herstellung sowie deren Verwendung für FlüssigkristallorientierungsschichtenInfo
- Publication number
- DE69313083T2 DE69313083T2 DE69313083T DE69313083T DE69313083T2 DE 69313083 T2 DE69313083 T2 DE 69313083T2 DE 69313083 T DE69313083 T DE 69313083T DE 69313083 T DE69313083 T DE 69313083T DE 69313083 T2 DE69313083 T2 DE 69313083T2
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- bis
- carbon atoms
- alkyl group
- group
- 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 - Fee Related
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 125
- 150000001875 compounds Chemical class 0.000 title claims description 73
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229920001721 polyimide Polymers 0.000 claims description 20
- 239000004642 Polyimide Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 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 claims description 15
- 229920005575 poly(amic acid) Polymers 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- WLHJCCUFRCTNRZ-UHFFFAOYSA-N (1-phenylcyclohexyl)benzene Chemical class C1CCCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 WLHJCCUFRCTNRZ-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical class [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 60
- 239000000758 substrate Substances 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000010408 film Substances 0.000 description 27
- 210000002858 crystal cell Anatomy 0.000 description 20
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
- 230000002688 persistence Effects 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000004697 Polyetherimide Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 229920001601 polyetherimide Polymers 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 5
- IMBDDGNKFSRAQH-UHFFFAOYSA-N 4-[[4-[1-[4-[(4-aminophenyl)methyl]phenyl]cyclohexyl]phenyl]methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=C(C2(CCCCC2)C=2C=CC(CC=3C=CC(N)=CC=3)=CC=2)C=C1 IMBDDGNKFSRAQH-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004811 liquid chromatography Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- QJPHZZUBQAASNR-UHFFFAOYSA-N 4,4-diphenylcyclohexan-1-one Chemical class C1CC(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QJPHZZUBQAASNR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- KSFBTBXTZDJOHO-UHFFFAOYSA-N diaminosilicon Chemical class N[Si]N KSFBTBXTZDJOHO-UHFFFAOYSA-N 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- JMKXDYJWNIVECB-UHFFFAOYSA-N (4-butyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 JMKXDYJWNIVECB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- -1 TeCl Chemical compound 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- OPBHPTFZYLPAFQ-UHFFFAOYSA-N (4-butyl-1-phenylcyclohex-3-en-1-yl)benzene Chemical compound C1CC(CCCC)=CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 OPBHPTFZYLPAFQ-UHFFFAOYSA-N 0.000 description 2
- SSEVIEAITQMVGE-UHFFFAOYSA-N (4-butylidene-1-phenylcyclohexyl)benzene Chemical compound C1CC(=CCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 SSEVIEAITQMVGE-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- OOTZSZHNDJGXTE-UHFFFAOYSA-N 1-[(4-nitrophenyl)methyl]-4-[1-[4-[(4-nitrophenyl)methyl]phenyl]cyclohexyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(C2(CCCCC2)C=2C=CC(CC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)C=C1 OOTZSZHNDJGXTE-UHFFFAOYSA-N 0.000 description 2
- VIBZMTQZYRPRFB-UHFFFAOYSA-N 1-[4-butyl-1-[4-[(4-nitrophenyl)methyl]phenyl]cyclohexyl]-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1CC(CCCC)CCC1(C=1C=CC(CC=2C=CC(=CC=2)[N+]([O-])=O)=CC=1)C(C=C1)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 VIBZMTQZYRPRFB-UHFFFAOYSA-N 0.000 description 2
- MEJQNPUKRTVBDA-UHFFFAOYSA-N 3-methylcyclobutane-1,1,2,2-tetracarboxylic acid Chemical compound CC1CC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O MEJQNPUKRTVBDA-UHFFFAOYSA-N 0.000 description 2
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- SIBJQHOWJFPFGC-UHFFFAOYSA-N 4-[[4-[1-[4-[(4-aminophenyl)methyl]phenyl]-4-butylcyclohexyl]phenyl]methyl]aniline Chemical compound C1CC(CCCC)CCC1(C=1C=CC(CC=2C=CC(N)=CC=2)=CC=1)C(C=C1)=CC=C1CC1=CC=C(N)C=C1 SIBJQHOWJFPFGC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- ZDZIXJZVVMSKQC-UHFFFAOYSA-N [4-[4-butyl-1-[4-(4-nitrobenzoyl)phenyl]cyclohexyl]phenyl]-(4-nitrophenyl)methanone Chemical compound C1CC(CCCC)CCC1(C=1C=CC(=CC=1)C(=O)C=1C=CC(=CC=1)[N+]([O-])=O)C1=CC=C(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C=C1 ZDZIXJZVVMSKQC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical class [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- YXNQGWHETRHZNC-UHFFFAOYSA-N (1-phenyl-4-propylcyclohexyl)benzene Chemical compound C1CC(CCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 YXNQGWHETRHZNC-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PDBXXSSFOXWAIU-UHFFFAOYSA-N (4-ethyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 PDBXXSSFOXWAIU-UHFFFAOYSA-N 0.000 description 1
- VZJYUYCOWVMAQR-UHFFFAOYSA-N (4-heptyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CCCCCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 VZJYUYCOWVMAQR-UHFFFAOYSA-N 0.000 description 1
- YCLUJEYUNKZRKN-UHFFFAOYSA-N (4-hexyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CCCCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 YCLUJEYUNKZRKN-UHFFFAOYSA-N 0.000 description 1
- ZVKVBTYICJPIPW-UHFFFAOYSA-N (4-methyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 ZVKVBTYICJPIPW-UHFFFAOYSA-N 0.000 description 1
- UOIOUSYNLFKHSL-UHFFFAOYSA-N (4-octyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CCCCCCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 UOIOUSYNLFKHSL-UHFFFAOYSA-N 0.000 description 1
- QIZBSHNUCZDJKO-UHFFFAOYSA-N (4-pentyl-1-phenylcyclohexyl)benzene Chemical compound C1CC(CCCCC)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QIZBSHNUCZDJKO-UHFFFAOYSA-N 0.000 description 1
- VORHCVGDBFIAAQ-UHFFFAOYSA-N 1-[4-butyl-1-(2-ethylphenyl)cyclohexyl]-2-ethylbenzene Chemical compound C1CC(CCCC)CCC1(C=1C(=CC=CC=1)CC)C1=CC=CC=C1CC VORHCVGDBFIAAQ-UHFFFAOYSA-N 0.000 description 1
- BVBBHDFPBCKXAL-UHFFFAOYSA-N 1-[4-butyl-1-(2-fluorophenyl)cyclohexyl]-2-fluorobenzene Chemical compound C1CC(CCCC)CCC1(C=1C(=CC=CC=1)F)C1=CC=CC=C1F BVBBHDFPBCKXAL-UHFFFAOYSA-N 0.000 description 1
- IXRXDPFBEGDZJH-UHFFFAOYSA-N 1-[4-butyl-1-(2-methylphenyl)cyclohexyl]-2-methylbenzene Chemical compound C1CC(CCCC)CCC1(C=1C(=CC=CC=1)C)C1=CC=CC=C1C IXRXDPFBEGDZJH-UHFFFAOYSA-N 0.000 description 1
- RWGMVGPKCBLBPN-UHFFFAOYSA-N 1-[4-butyl-1-(2-propylphenyl)cyclohexyl]-2-propylbenzene Chemical compound C1CC(CCCC)CCC1(C=1C(=CC=CC=1)CCC)C1=CC=CC=C1CCC RWGMVGPKCBLBPN-UHFFFAOYSA-N 0.000 description 1
- ZMOJUUQOGDEQGG-UHFFFAOYSA-N 1-[4-butyl-1-(3-fluorophenyl)cyclohexyl]-3-fluorobenzene Chemical compound C1CC(CCCC)CCC1(C=1C=C(F)C=CC=1)C1=CC=CC(F)=C1 ZMOJUUQOGDEQGG-UHFFFAOYSA-N 0.000 description 1
- DZNBXWXIPFVHEP-UHFFFAOYSA-N 1-[4-butyl-1-(3-methylphenyl)cyclohexyl]-3-methylbenzene Chemical compound C1CC(CCCC)CCC1(C=1C=C(C)C=CC=1)C1=CC=CC(C)=C1 DZNBXWXIPFVHEP-UHFFFAOYSA-N 0.000 description 1
- UYNOUICHKMPJMT-UHFFFAOYSA-N 1-[4-butyl-1-(3-propylphenyl)cyclohexyl]-3-propylbenzene Chemical compound C1CC(CCCC)CCC1(C=1C=C(CCC)C=CC=1)C1=CC=CC(CCC)=C1 UYNOUICHKMPJMT-UHFFFAOYSA-N 0.000 description 1
- JTKLVACMABHMQB-UHFFFAOYSA-N 1-[4-ethyl-1-(2-fluorophenyl)cyclohexyl]-2-fluorobenzene Chemical compound C1CC(CC)CCC1(C=1C(=CC=CC=1)F)C1=CC=CC=C1F JTKLVACMABHMQB-UHFFFAOYSA-N 0.000 description 1
- MAVYZKURTFFWLJ-UHFFFAOYSA-N 1-[4-ethyl-1-(2-methylphenyl)cyclohexyl]-2-methylbenzene Chemical compound C1CC(CC)CCC1(C=1C(=CC=CC=1)C)C1=CC=CC=C1C MAVYZKURTFFWLJ-UHFFFAOYSA-N 0.000 description 1
- FUDLWTYSXOAVBV-UHFFFAOYSA-N 1-[4-ethyl-1-(2-propylphenyl)cyclohexyl]-2-propylbenzene Chemical compound CCCC1=CC=CC=C1C1(C=2C(=CC=CC=2)CCC)CCC(CC)CC1 FUDLWTYSXOAVBV-UHFFFAOYSA-N 0.000 description 1
- DCEZAQDGGGGDNQ-UHFFFAOYSA-N 1-[4-ethyl-1-(3-fluorophenyl)cyclohexyl]-3-fluorobenzene Chemical compound C1CC(CC)CCC1(C=1C=C(F)C=CC=1)C1=CC=CC(F)=C1 DCEZAQDGGGGDNQ-UHFFFAOYSA-N 0.000 description 1
- VGRJVRWUKHTZMU-UHFFFAOYSA-N 1-[4-ethyl-1-(3-methylphenyl)cyclohexyl]-3-methylbenzene Chemical compound C1CC(CC)CCC1(C=1C=C(C)C=CC=1)C1=CC=CC(C)=C1 VGRJVRWUKHTZMU-UHFFFAOYSA-N 0.000 description 1
- KKXRGZIILDRDQP-UHFFFAOYSA-N 1-[4-ethyl-1-(3-propylphenyl)cyclohexyl]-3-propylbenzene Chemical compound CCCC1=CC=CC(C2(CCC(CC)CC2)C=2C=C(CCC)C=CC=2)=C1 KKXRGZIILDRDQP-UHFFFAOYSA-N 0.000 description 1
- SUAKMXVULYLWRX-UHFFFAOYSA-N 1-[4-heptyl-1-(2-methylphenyl)cyclohexyl]-2-methylbenzene Chemical compound C1CC(CCCCCCC)CCC1(C=1C(=CC=CC=1)C)C1=CC=CC=C1C SUAKMXVULYLWRX-UHFFFAOYSA-N 0.000 description 1
- UYKJOROUTGUITH-UHFFFAOYSA-N 1-[4-heptyl-1-(2-propylphenyl)cyclohexyl]-2-propylbenzene Chemical compound C1CC(CCCCCCC)CCC1(C=1C(=CC=CC=1)CCC)C1=CC=CC=C1CCC UYKJOROUTGUITH-UHFFFAOYSA-N 0.000 description 1
- LKTLHKCZMSRFQI-UHFFFAOYSA-N 1-[4-heptyl-1-(3-methylphenyl)cyclohexyl]-3-methylbenzene Chemical compound C1CC(CCCCCCC)CCC1(C=1C=C(C)C=CC=1)C1=CC=CC(C)=C1 LKTLHKCZMSRFQI-UHFFFAOYSA-N 0.000 description 1
- OTURKNXPHRECLR-UHFFFAOYSA-N 1-[4-heptyl-1-(3-propylphenyl)cyclohexyl]-3-propylbenzene Chemical compound C1CC(CCCCCCC)CCC1(C=1C=C(CCC)C=CC=1)C1=CC=CC(CCC)=C1 OTURKNXPHRECLR-UHFFFAOYSA-N 0.000 description 1
- OLCURMZSZDRZDG-UHFFFAOYSA-N 1-[4-hexyl-1-(2-methylphenyl)cyclohexyl]-2-methylbenzene Chemical compound C1CC(CCCCCC)CCC1(C=1C(=CC=CC=1)C)C1=CC=CC=C1C OLCURMZSZDRZDG-UHFFFAOYSA-N 0.000 description 1
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- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- RWQDJQYCVZRHFV-UHFFFAOYSA-N CCO[SiH](OCC)CC1=CC=CC(N)=C1 Chemical compound CCO[SiH](OCC)CC1=CC=CC(N)=C1 RWQDJQYCVZRHFV-UHFFFAOYSA-N 0.000 description 1
- RNNIAGFHOPUZCZ-UHFFFAOYSA-N CO[SiH](OC)CC1=CC=CC(N)=C1 Chemical compound CO[SiH](OC)CC1=CC=CC(N)=C1 RNNIAGFHOPUZCZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- UJAAQCCNKHQCKD-UHFFFAOYSA-N [4-[1-[4-(4-nitrobenzoyl)phenyl]cyclohexyl]phenyl]-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C(C2(CCCCC2)C=2C=CC(=CC=2)C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C=C1 UJAAQCCNKHQCKD-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical group C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- UJTGYJODGVUOGO-UHFFFAOYSA-N diethoxy-methyl-propylsilane Chemical compound CCC[Si](C)(OCC)OCC UJTGYJODGVUOGO-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- 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
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Liquid Crystal (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35134092 | 1992-12-07 | ||
| JP35134192 | 1992-12-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69313083D1 DE69313083D1 (de) | 1997-09-18 |
| DE69313083T2 true DE69313083T2 (de) | 1997-12-11 |
Family
ID=26579375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69313083T Expired - Fee Related DE69313083T2 (de) | 1992-12-07 | 1993-12-06 | Diaminoverbindungen, deren Herstellung sowie deren Verwendung für Flüssigkristallorientierungsschichten |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5382688A (enExample) |
| EP (1) | EP0601813B1 (enExample) |
| KR (2) | KR0123896B1 (enExample) |
| DE (1) | DE69313083T2 (enExample) |
| SG (1) | SG54126A1 (enExample) |
| TW (1) | TW321681B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW320629B (enExample) * | 1994-10-20 | 1997-11-21 | Chisso Corp | |
| JPH08146422A (ja) * | 1994-11-15 | 1996-06-07 | Sony Corp | 液晶表示装置および製造方法 |
| US5700860A (en) * | 1995-03-27 | 1997-12-23 | Japan Synthetic Rubber Co., Ltd. | Liquid crystal orienting agent |
| JP3731229B2 (ja) * | 1995-10-20 | 2006-01-05 | チッソ株式会社 | ポリアミド酸、ポリイミド膜及びこれを用いた液晶配向膜、液晶表示素子 |
| JP4029452B2 (ja) * | 1997-12-29 | 2008-01-09 | チッソ株式会社 | ポリアミド酸組成物、液晶配向膜及び液晶表示素子 |
| JP3978754B2 (ja) | 1997-12-29 | 2007-09-19 | チッソ株式会社 | ポリアミド酸組成物、液晶配向膜、及び液晶表示素子 |
| US6080832A (en) * | 1998-09-10 | 2000-06-27 | Industrial Technology Research Institute | Low-pretilt alignment layer material |
| US7074344B2 (en) * | 2001-10-03 | 2006-07-11 | Jsr Corporation | Liquid crystal aligning agent and liquid crystal display element |
| CN101039987A (zh) * | 2004-10-19 | 2007-09-19 | 日立电线株式会社 | 聚酰亚胺树脂组合物及用其的液晶定向膜及用该膜的液晶显示元件 |
| JP2006243637A (ja) * | 2005-03-07 | 2006-09-14 | Sharp Corp | 液晶表示装置及びその製造方法 |
| KR101148400B1 (ko) * | 2005-06-29 | 2012-05-23 | 엘지디스플레이 주식회사 | Ips 모드 액정표시소자 |
| JP4995693B2 (ja) * | 2006-11-08 | 2012-08-08 | エルジー・ケム・リミテッド | 液晶配向用組成物、それによって製造された液晶配向膜、およびそれを含む液晶ディスプレイ |
| EP1931167B1 (en) | 2006-12-07 | 2012-08-29 | 3M Innovative Properties Company | A switch module in a distribution point in the field of telecommunications and assemblies including as well as methods of using same |
| US7967849B2 (en) * | 2007-04-06 | 2011-06-28 | Warsaw Orthopedic, Inc. | Adjustable multi-axial spinal coupling assemblies |
| TWI545104B (zh) * | 2011-12-22 | 2016-08-11 | Diphenylamine-based compound, a polyamic acid composition, a polyimide composition and a liquid crystal aligning agent |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1851391A (en) * | 1928-03-02 | 1932-03-29 | Korten Ernst | Process for producing amino derivatives of hexahydrodiphenyl |
| US2883365A (en) * | 1955-03-01 | 1959-04-21 | Goodrich Co B F | Sulfur vulcanizable rubber and 1,1-bis(4-hydroxy phenyl) cycloalkane |
| US3247199A (en) * | 1961-01-27 | 1966-04-19 | Ciba Geigy Corp | Diphenyl-methanes |
| JP2720053B2 (ja) * | 1988-11-09 | 1998-02-25 | チッソ株式会社 | 新規なジアミノ化合物、ジニトロ化合物、ジオール化合物および製造方法 |
| US5152918A (en) * | 1989-02-09 | 1992-10-06 | Chisso Corporation | Liquid crystal-aligning coating and a liquid crystal display element |
| DE4014847A1 (de) * | 1990-05-09 | 1991-11-14 | Bayer Ag | Neue diaminodiphenylcycloalkane, ihre herstellung und verwendung |
-
1993
- 1993-12-04 KR KR1019930026449A patent/KR0123896B1/ko not_active Expired - Lifetime
- 1993-12-06 DE DE69313083T patent/DE69313083T2/de not_active Expired - Fee Related
- 1993-12-06 SG SG1996001545A patent/SG54126A1/en unknown
- 1993-12-06 EP EP19930309737 patent/EP0601813B1/en not_active Expired - Lifetime
- 1993-12-07 US US08/162,318 patent/US5382688A/en not_active Expired - Fee Related
- 1993-12-24 TW TW82110987A patent/TW321681B/zh not_active IP Right Cessation
-
1994
- 1994-08-25 US US08/295,457 patent/US5501884A/en not_active Expired - Fee Related
-
1997
- 1997-05-08 KR KR1019970017661A patent/KR0136940B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1001838A1 (en) | 1998-07-10 |
| SG54126A1 (en) | 1998-11-16 |
| EP0601813B1 (en) | 1997-08-13 |
| KR0136940B1 (ko) | 1998-04-25 |
| KR940014298A (ko) | 1994-07-18 |
| TW321681B (enExample) | 1997-12-01 |
| EP0601813A1 (en) | 1994-06-15 |
| KR0123896B1 (ko) | 1997-11-24 |
| US5501884A (en) | 1996-03-26 |
| DE69313083D1 (de) | 1997-09-18 |
| US5382688A (en) | 1995-01-17 |
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