JP5359029B2 - 酸二無水物、液晶配向膜および液晶表示素子 - Google Patents
酸二無水物、液晶配向膜および液晶表示素子 Download PDFInfo
- Publication number
- JP5359029B2 JP5359029B2 JP2008139079A JP2008139079A JP5359029B2 JP 5359029 B2 JP5359029 B2 JP 5359029B2 JP 2008139079 A JP2008139079 A JP 2008139079A JP 2008139079 A JP2008139079 A JP 2008139079A JP 5359029 B2 JP5359029 B2 JP 5359029B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- liquid crystal
- formula
- represented
- diamine
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 84
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 61
- 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 title claims abstract description 54
- 239000004642 Polyimide Substances 0.000 claims abstract description 42
- 229920001721 polyimide Polymers 0.000 claims abstract description 42
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000004985 diamines Chemical class 0.000 claims description 25
- 239000004952 Polyamide Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 229920002647 polyamide Polymers 0.000 claims description 23
- 239000004962 Polyamide-imide Substances 0.000 claims description 18
- 229920002312 polyamide-imide Polymers 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000006159 dianhydride group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 43
- 238000000034 method Methods 0.000 description 26
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002966 varnish Substances 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- -1 dicarboxylic acid chlorides Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000006358 imidation reaction Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- UHNUHZHQLCGZDA-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCC1=CC=C(N)C=C1 UHNUHZHQLCGZDA-UHFFFAOYSA-N 0.000 description 1
- ODXNOGQHTZSYFY-UHFFFAOYSA-N 4-ethenylphthalic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1C(O)=O ODXNOGQHTZSYFY-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- AYWIQBRNNVPNQL-UHFFFAOYSA-N C(C)OC(C=1C(C(=O)OCC)=C(C=CC1)CCCO)=O Chemical compound C(C)OC(C=1C(C(=O)OCC)=C(C=CC1)CCCO)=O AYWIQBRNNVPNQL-UHFFFAOYSA-N 0.000 description 1
- GSHMOJHOYDXOMS-UHFFFAOYSA-N CCOC(=O)C1=CC=CC(=C1C(=O)OCC)C#CCO Chemical compound CCOC(=O)C1=CC=CC(=C1C(=O)OCC)C#CCO GSHMOJHOYDXOMS-UHFFFAOYSA-N 0.000 description 1
- KZPOSCZRBUIVMC-UHFFFAOYSA-N CCOC(=O)C1=CC=CC(=C1C(=O)OCC)CCCOS(=O)(=O)C2=CC=C(C=C2)C Chemical compound CCOC(=O)C1=CC=CC(=C1C(=O)OCC)CCCOS(=O)(=O)C2=CC=C(C=C2)C KZPOSCZRBUIVMC-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910000661 Mercury cadmium telluride Inorganic materials 0.000 description 1
- WLPFVIZPFXMGPR-UHFFFAOYSA-N O=C(c1c2cc(CCCCCCCCCCOc(cc3)cc(C(O4)=O)c3C4=O)cc1)OC2=O Chemical compound O=C(c1c2cc(CCCCCCCCCCOc(cc3)cc(C(O4)=O)c3C4=O)cc1)OC2=O WLPFVIZPFXMGPR-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- MCMSPRNYOJJPIZ-UHFFFAOYSA-N cadmium;mercury;tellurium Chemical compound [Cd]=[Te]=[Hg] MCMSPRNYOJJPIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MNNWYBSNAIKTLH-UHFFFAOYSA-N diethyl 3-bromobenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(Br)=C1C(=O)OCC MNNWYBSNAIKTLH-UHFFFAOYSA-N 0.000 description 1
- JPVQDAGVARKAFY-UHFFFAOYSA-N diethyl 3-hydroxybenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(O)=C1C(=O)OCC JPVQDAGVARKAFY-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- SFMGRZPVYXQKIZ-UHFFFAOYSA-N dimethyl 4-(hydroxymethyl)benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(CO)C=C1C(=O)OC SFMGRZPVYXQKIZ-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Liquid Crystal (AREA)
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008139079A JP5359029B2 (ja) | 2007-06-06 | 2008-05-28 | 酸二無水物、液晶配向膜および液晶表示素子 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007149991 | 2007-06-06 | ||
| JP2007149991 | 2007-06-06 | ||
| JP2008139079A JP5359029B2 (ja) | 2007-06-06 | 2008-05-28 | 酸二無水物、液晶配向膜および液晶表示素子 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009013165A JP2009013165A (ja) | 2009-01-22 |
| JP2009013165A5 JP2009013165A5 (enExample) | 2011-01-06 |
| JP5359029B2 true JP5359029B2 (ja) | 2013-12-04 |
Family
ID=40354488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008139079A Expired - Fee Related JP5359029B2 (ja) | 2007-06-06 | 2008-05-28 | 酸二無水物、液晶配向膜および液晶表示素子 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5359029B2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5625384B2 (ja) * | 2010-02-25 | 2014-11-19 | Jnc株式会社 | 液晶配向剤、液晶配向膜および液晶表示素子 |
| WO2015111982A1 (ko) * | 2014-01-27 | 2015-07-30 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
| KR101574016B1 (ko) | 2014-01-27 | 2015-12-02 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
| WO2015125734A1 (ja) * | 2014-02-24 | 2015-08-27 | マナック株式会社 | ハロヘキサヒドロフタル酸誘導体 |
| KR101615431B1 (ko) * | 2014-05-15 | 2016-04-25 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
| WO2015182894A1 (ko) * | 2014-05-30 | 2015-12-03 | 주식회사 동진쎄미켐 | 광반응성 다이아민 단량체 합성 및 이를 이용한 lcd용 배향막 |
| JP7084710B2 (ja) * | 2017-01-20 | 2022-06-15 | 住友化学株式会社 | ポリアミドイミド樹脂および該ポリアミドイミド樹脂を含んでなる光学部材 |
| KR101952823B1 (ko) * | 2017-01-20 | 2019-02-27 | 스미또모 가가꾸 가부시키가이샤 | 필름, 수지 조성물 및 폴리아미드이미드 수지의 제조 방법 |
| WO2018135431A1 (ja) * | 2017-01-20 | 2018-07-26 | 住友化学株式会社 | ポリアミドイミド樹脂及び該ポリアミドイミド樹脂を含んでなる光学部材 |
| TW202104360A (zh) * | 2019-02-27 | 2021-02-01 | 日商日產化學股份有限公司 | 薄膜及其製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000298279A (ja) * | 1999-02-12 | 2000-10-24 | Hitachi Chem Co Ltd | 樹脂組成物、液晶配向膜用樹脂組成物、液晶配向膜、液晶挟持基板及び液晶表示装置 |
| JP2001131285A (ja) * | 1999-10-29 | 2001-05-15 | Hitachi Chemical Dupont Microsystems Ltd | ポリアミド酸、ポリイミド液晶配向膜用組成物、液晶配向膜、液晶挟持基板及び液晶表示素子 |
| DE10129335A1 (de) * | 2001-06-19 | 2003-01-02 | Merck Patent Gmbh | Polyimide mit CF¶2¶O-Strukturelementen |
| JP4415566B2 (ja) * | 2002-07-04 | 2010-02-17 | チッソ株式会社 | 非対称な構造を有する酸無水物、液晶配向膜および液晶表示素子 |
| JP5245329B2 (ja) * | 2006-09-15 | 2013-07-24 | Ｊｎｃ株式会社 | 液晶配向剤、液晶配向膜および液晶表示素子 |
-
2008
- 2008-05-28 JP JP2008139079A patent/JP5359029B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009013165A (ja) | 2009-01-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5359029B2 (ja) | 酸二無水物、液晶配向膜および液晶表示素子 | |
| JP5120580B1 (ja) | 液晶配向剤 | |
| KR101905897B1 (ko) | 디아민, 액정 배향제, 액정 배향막 및 액정 표시 소자 | |
| CN101724410B (zh) | 液晶配向剂、液晶配向膜以及液晶显示元件 | |
| JP5481771B2 (ja) | 光配向膜及び液晶表示素子 | |
| JP5293943B2 (ja) | 液晶配向剤、液晶配向膜および液晶表示素子 | |
| JP2014024846A (ja) | 光配向膜及び液晶表示素子 | |
| WO2008126978A1 (en) | 3,4-dicarboxy-1,2,3,4-tetrahydro-6-t-butyl-1-naphthalene succinic dianhydride and liquid crystal aligning agent comprising polyimide resin prepared from the dianhydride | |
| JP6064997B2 (ja) | ポリイミド系の液晶配向処理剤、液晶配向膜、及び液晶表示素子 | |
| JP4779339B2 (ja) | 液晶配向剤およびそれを用いた液晶表示素子 | |
| JP4595417B2 (ja) | フェニレンジアミン、それを用いて形成される配向膜、および該配向膜を含む液晶表示素子 | |
| JP4461909B2 (ja) | 酸二無水物、配向膜、および液晶表示素子 | |
| WO2005033248A1 (en) | Diamine compound having dendron side chain and liquid crystal alignment material produced using the same | |
| JP7102536B2 (ja) | 液晶配向剤組成物、これを用いた液晶配向膜の製造方法、これを用いた液晶配向膜および液晶表示素子 | |
| JP5919411B2 (ja) | シロキサン含有三無水物、ポリマー、液晶配向剤、液晶配向膜、および液晶表示装置 | |
| JP4992893B2 (ja) | 非対称な構造を有する酸無水物、液晶配向膜および液晶表示素子 | |
| JP5012067B2 (ja) | 側鎖にナフタレン環を有するポリアミック酸もしくはポリイミドを含有する液晶配向剤 | |
| JP4271173B2 (ja) | デンドロン構造の側鎖を有するジアミン化合物及びこれを用いた液晶配向剤 | |
| WO2015080185A1 (ja) | 液晶配向剤及びそれを用いた液晶表示素子 | |
| JP4415566B2 (ja) | 非対称な構造を有する酸無水物、液晶配向膜および液晶表示素子 | |
| JP2004075944A (ja) | 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 | |
| JP5092382B2 (ja) | 液晶類似構造を有するジアミン | |
| JP5034411B2 (ja) | テトラカルボン酸二無水物、液晶配向剤および液晶表示素子 | |
| CN111936600B (zh) | 液晶取向组合物、使用其制备液晶取向膜的方法及使用其的液晶取向膜、液晶显示器 | |
| JP4026327B2 (ja) | ビスアニリン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101112 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20101112 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20110331 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130115 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130122 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130325 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130328 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130419 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130806 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130819 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5359029 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |