TWI307337B - Diamine, polymer, liquid crystal display aligned film and liquid crystal display device - Google Patents
Diamine, polymer, liquid crystal display aligned film and liquid crystal display device Download PDFInfo
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- TWI307337B TWI307337B TW094103548A TW94103548A TWI307337B TW I307337 B TWI307337 B TW I307337B TW 094103548 A TW094103548 A TW 094103548A TW 94103548 A TW94103548 A TW 94103548A TW I307337 B TWI307337 B TW I307337B
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- Prior art keywords
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- liquid crystal
- substituted
- diamine
- crystal alignment
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 227
- 150000004985 diamines Chemical class 0.000 title claims description 138
- 229920000642 polymer Polymers 0.000 title claims description 109
- -1 1,4-phenylene, naphthalene-2,6-diyl Chemical group 0.000 claims description 107
- 239000003795 chemical substances by application Substances 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 81
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
- 239000002904 solvent Substances 0.000 claims description 66
- 125000002947 alkylene group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 51
- 239000011737 fluorine Substances 0.000 claims description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 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 27
- 239000002994 raw material Substances 0.000 claims description 27
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 26
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 25
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims description 24
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 22
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 21
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 19
- 229920000768 polyamine Polymers 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 10
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920002098 polyfluorene Polymers 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
- 229910021603 Ruthenium iodide Inorganic materials 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 claims 1
- 239000010408 film Substances 0.000 description 89
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000013078 crystal Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- 239000000758 substrate Substances 0.000 description 27
- 239000012299 nitrogen atmosphere Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 125000003277 amino group Chemical group 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 125000003709 fluoroalkyl group Chemical group 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 125000000623 heterocyclic group Chemical group 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 210000002858 crystal cell Anatomy 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 108010039918 Polylysine Proteins 0.000 description 8
- 229920000656 polylysine Polymers 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 5
- 108010026466 polyproline Proteins 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- MROWFEAYAXMMRD-UHFFFAOYSA-N 4-nitro-n-propylaniline Chemical compound CCCNC1=CC=C([N+]([O-])=O)C=C1 MROWFEAYAXMMRD-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 108010094020 polyglycine Proteins 0.000 description 4
- 229920000232 polyglycine polymer Polymers 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920002312 polyamide-imide Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000004060 quinone imines Chemical class 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 2
- MYGVNBDXXZMEFG-UHFFFAOYSA-N 4-nitro-N-(4-nitrophenyl)-N-propylbenzamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(CCC)C(=O)C1=CC=C([N+]([O-])=O)C=C1 MYGVNBDXXZMEFG-UHFFFAOYSA-N 0.000 description 2
- APAZZDYJPHHFLV-UHFFFAOYSA-N 6-(4-bromophenyl)naphthalene-2-carboxylic acid Chemical compound C1=CC2=CC(C(=O)O)=CC=C2C=C1C1=CC=C(Br)C=C1 APAZZDYJPHHFLV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- MQCOPLKOLANXKP-UHFFFAOYSA-N N-heptyl-4-(4-nitrophenyl)aniline Chemical group C1=CC(NCCCCCCC)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 MQCOPLKOLANXKP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 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 2
- 150000002466 imines Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 150000003304 ruthenium compounds Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000126 substance Substances 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
- 238000005406 washing Methods 0.000 description 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- YGHWCSTYDOTTCI-UHFFFAOYSA-N 1-(1-chloropropan-2-yl)-4-nitrobenzene Chemical compound ClCC(C)C1=CC=C([N+]([O-])=O)C=C1 YGHWCSTYDOTTCI-UHFFFAOYSA-N 0.000 description 1
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 1
- LYKVCCHDBARSHV-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(Cl)C1=CC=CC=C1 LYKVCCHDBARSHV-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LVABDEFBDPWHJL-UHFFFAOYSA-N 2-(4-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=C([N+]([O-])=O)C=C1 LVABDEFBDPWHJL-UHFFFAOYSA-N 0.000 description 1
- RBSRRICSXWXMRC-UHFFFAOYSA-N 2-(4-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C([N+]([O-])=O)C=C1 RBSRRICSXWXMRC-UHFFFAOYSA-N 0.000 description 1
- PWOZSAQHUKWIHS-UHFFFAOYSA-N 2-(4-nitrophenyl)propanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=C([N+]([O-])=O)C=C1 PWOZSAQHUKWIHS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- APJHCBDHALVYQW-UHFFFAOYSA-N 2H-pyran-4-ylboronic acid Chemical compound O1CC=C(C=C1)B(O)O APJHCBDHALVYQW-UHFFFAOYSA-N 0.000 description 1
- SCJHPUGWYHCYAZ-UHFFFAOYSA-N 3,5-diethyl-2-propylpyridine Chemical compound CCCC1=NC=C(CC)C=C1CC SCJHPUGWYHCYAZ-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- SXPGQGNWEWPWQZ-UHFFFAOYSA-N 4-(triethoxymethyl)dodecan-1-amine Chemical compound NCCCC(C(OCC)(OCC)OCC)CCCCCCCC SXPGQGNWEWPWQZ-UHFFFAOYSA-N 0.000 description 1
- WTNSXWSOTDBWOR-UHFFFAOYSA-N 4-amino-2,3,5,6-tetrafluorobenzoic acid Chemical compound NC1=C(F)C(F)=C(C(O)=O)C(F)=C1F WTNSXWSOTDBWOR-UHFFFAOYSA-N 0.000 description 1
- NPMCAVBMOTZUPD-UHFFFAOYSA-N 6-bromonaphthalene-2-carboxylic acid Chemical compound C1=C(Br)C=CC2=CC(C(=O)O)=CC=C21 NPMCAVBMOTZUPD-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 description 1
- UEYMLSDWUUKDND-UHFFFAOYSA-N C(C)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C)C(C(OCC)(OCC)OCC)CCCCCCCC UEYMLSDWUUKDND-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- VPLKXGORNUYFBO-UHFFFAOYSA-N C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC VPLKXGORNUYFBO-UHFFFAOYSA-N 0.000 description 1
- GGXWDWNWNOINTP-UHFFFAOYSA-N CCCCOCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound CCCCOCCCC(C(OC)(OC)OC)CCCCCCCC GGXWDWNWNOINTP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000320892 Clerodendrum phlomidis Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- OWIYWXUEMZLIKG-UHFFFAOYSA-N N'-(4-methoxypentyl)ethane-1,2-diamine Chemical compound COC(C)CCCNCCN OWIYWXUEMZLIKG-UHFFFAOYSA-N 0.000 description 1
- XVIWLQUPISPGPS-UHFFFAOYSA-N N,2-bis(4-nitrophenyl)-N-propylpropanamide Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C(C(=O)N(CCC)C1=CC=C(C=C1)[N+](=O)[O-])C XVIWLQUPISPGPS-UHFFFAOYSA-N 0.000 description 1
- LNBCORQTMWLBNE-UHFFFAOYSA-N N-(4-nitrophenyl)-4-[4-(4-propylcyclohexyl)cyclohexyl]aniline Chemical compound C(CC)C1CCC(CC1)C1CCC(CC1)C1=CC=C(C=C1)NC1=CC=C(C=C1)[N+](=O)[O-] LNBCORQTMWLBNE-UHFFFAOYSA-N 0.000 description 1
- ZSDCMMFPXQPFIR-UHFFFAOYSA-N NC1(C=CC(C(C=C2)=CC=C2N)=CC1)[N+]([O-])=O.Cl Chemical compound NC1(C=CC(C(C=C2)=CC=C2N)=CC1)[N+]([O-])=O.Cl ZSDCMMFPXQPFIR-UHFFFAOYSA-N 0.000 description 1
- XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 102100037591 Neuroserpin Human genes 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000037429 base substitution Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid 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-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration 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
- 230000005611 electricity Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DSWNRHCOGVRDOE-UHFFFAOYSA-N n,n-dimethylmethanimidamide Chemical compound CN(C)C=N DSWNRHCOGVRDOE-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 108010080874 neuroserpin Proteins 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000004022 organic phosphonium compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N p-phenyl-aniline Natural products C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005815 pentoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/003—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor characterised by the choice of material
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0004—General aspects of dyeing
- D06P1/0012—Effecting dyeing to obtain luminescent or phosphorescent dyeings
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F13/00—Illuminated signs; Luminous advertising
- G09F13/20—Illuminated signs; Luminous advertising with luminescent surfaces or parts
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Theoretical Computer Science (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
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| JP2004035773 | 2004-02-12 | ||
| JP2005015202A JP4821118B2 (ja) | 2004-02-12 | 2005-01-24 | ジアミン、ポリマー、液晶配向膜および液晶表示素子 |
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| TW200535120A TW200535120A (en) | 2005-11-01 |
| TWI307337B true TWI307337B (en) | 2009-03-11 |
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|---|---|---|---|
| TW094103548A TWI307337B (en) | 2004-02-12 | 2005-02-04 | Diamine, polymer, liquid crystal display aligned film and liquid crystal display device |
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|---|---|
| JP (1) | JP4821118B2 (enExample) |
| KR (2) | KR100655766B1 (enExample) |
| TW (1) | TWI307337B (enExample) |
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| AU2006265835B2 (en) * | 2005-06-30 | 2012-05-03 | Amgen Inc. | Bis-aryl kinase inhibitors and their use in the treatment of inflammation, angiogenesis and cancer |
| JP2007015952A (ja) * | 2005-07-06 | 2007-01-25 | Shionogi & Co Ltd | ナフタレン誘導体 |
| US8637706B2 (en) | 2005-11-28 | 2014-01-28 | Gtx, Inc. | Nuclear receptor binding agents |
| US9409856B2 (en) | 2005-11-28 | 2016-08-09 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| US8546451B2 (en) | 2005-11-28 | 2013-10-01 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| KR100822499B1 (ko) * | 2005-12-01 | 2008-04-16 | 주식회사 엘지화학 | 신규한 폴리이미드 및 이의 제조방법 |
| KR101257437B1 (ko) * | 2006-02-22 | 2013-04-23 | 주식회사 동진쎄미켐 | 수직배향모드 액정표시소자의 배향재료 및 이의 제조방법 |
| TWI422927B (zh) | 2006-03-16 | 2014-01-11 | Jnc Corp | 光配向膜以及液晶顯示元件 |
| JP5481771B2 (ja) * | 2006-03-16 | 2014-04-23 | Ｊｎｃ株式会社 | 光配向膜及び液晶表示素子 |
| TWI477554B (zh) * | 2006-07-10 | 2015-03-21 | Jnc Corp | 液晶配向劑、液晶配向膜以及液晶顯示元件 |
| KR100710472B1 (ko) * | 2006-10-18 | 2007-04-24 | 주식회사가야건축사사무소 | 실내외 기밀성 유지를 위한 주택용 도어구조 |
| WO2008084944A1 (en) * | 2007-01-09 | 2008-07-17 | Lg Chem, Ltd. | New copolyimide, liquid crystal aligning layer comprising the same, and liquid crystal display comprising the same |
| US9624161B2 (en) | 2009-02-23 | 2017-04-18 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| US9427418B2 (en) | 2009-02-23 | 2016-08-30 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| KR101582157B1 (ko) | 2009-08-05 | 2016-01-05 | 삼성디스플레이 주식회사 | 액정표시패널 및 이의 제조방법 |
| JP5416282B2 (ja) * | 2009-10-23 | 2014-02-12 | 中国科学院上海有机化学研究所 | 硫黄含有複素環が縮合したナフタレンテトラカルボン酸ジイミド誘導体及びその製造方法と応用 |
| JP5856147B2 (ja) | 2010-04-23 | 2016-02-09 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光配向材料 |
| JP6318467B2 (ja) * | 2013-04-18 | 2018-05-09 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法及び重合体 |
| JPWO2014185413A1 (ja) * | 2013-05-13 | 2017-02-23 | 日産化学工業株式会社 | 横電界駆動型液晶表示素子用液晶配向膜を有する基板の製造方法 |
| JP6492564B2 (ja) * | 2014-02-13 | 2019-04-03 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法、重合体及び化合物 |
| KR102212324B1 (ko) | 2014-02-21 | 2021-02-04 | 삼성디스플레이 주식회사 | 광배향제 및 이를 포함하는 액정 표시 장치 |
| JP6243862B2 (ja) * | 2015-02-17 | 2017-12-06 | 富士フイルム株式会社 | 液晶配向膜の製造方法、液晶表示装置の製造方法および液晶表示装置 |
| KR102605000B1 (ko) * | 2015-03-24 | 2023-11-22 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| KR101989587B1 (ko) | 2016-03-28 | 2019-06-14 | 주식회사 엘지화학 | 액정 배향제, 이를 포함하는 액정배향막 및 액정배향막의 제조 방법 |
| DE112017003977T5 (de) * | 2016-08-11 | 2019-07-04 | Merck Patent Gmbh | Organische halbleiterverbindungen umfassend einen tetraazapyren-kern |
| KR102089122B1 (ko) * | 2016-08-25 | 2020-03-13 | 주식회사 엘지화학 | 디아민 화합물 및 이를 이용하여 제조된 플렉시블 소자용 기판 |
| KR102782854B1 (ko) | 2019-06-04 | 2025-03-14 | 삼성전자주식회사 | 폴리(아미드-이미드) 코폴리머, 폴리(아미드-이미드) 코폴리머 제조용 조성물, 폴리(아미드-이미드) 코폴리머를 포함하는 성형품 및 표시 장치 |
| JP2022142780A (ja) * | 2021-03-16 | 2022-09-30 | 東ソー株式会社 | 光反応性ポリマー、モノマー、光学フィルム |
| JP2023053917A (ja) * | 2021-10-01 | 2023-04-13 | エスケー イノベーション カンパニー リミテッド | 新規なジアミン、それにより製造された重合体およびフィルム |
| JP2023081407A (ja) * | 2021-12-01 | 2023-06-13 | 東ソー株式会社 | 光反応性ポリマーを含む樹脂組成物、光学薄膜 |
| CN115784923B (zh) * | 2022-12-12 | 2024-06-14 | 宁波博雅聚力新材料科技有限公司 | 制备聚酰亚胺薄膜用二胺单体及制备方法和聚酰亚胺薄膜 |
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| US3282897A (en) * | 1963-09-25 | 1966-11-01 | Du Pont | Process for preparing a polyamide-ester |
| US3926922A (en) * | 1974-03-14 | 1975-12-16 | Polaroid Corp | Polyurethane elastomers prepared from diamine curing agents |
| FR2279822A1 (fr) * | 1974-07-24 | 1976-02-20 | Ugine Kuhlmann | Nouveaux colorants disazoiques hydrosolubles et nouvelles matieres premieres utilisables pour leur preparation |
| JPS6317933A (ja) * | 1986-07-09 | 1988-01-25 | Toray Ind Inc | 熱硬化性アミドイミド樹脂およびその製造法 |
| US4742150A (en) * | 1986-09-25 | 1988-05-03 | General Electric Company | Solvent resistant polyetheramideimide containing benzanilide units |
| JPH07152037A (ja) * | 1993-11-26 | 1995-06-16 | Chisso Corp | 液晶配向膜及び液晶表示素子 |
| KR100645616B1 (ko) * | 1998-08-26 | 2006-11-13 | 닛산 가가쿠 고교 가부시키 가이샤 | 액정배향 처리제 및 그것을 사용한 액정소자와 액정의배향방법 |
| KR100565739B1 (ko) * | 2000-10-28 | 2006-03-29 | 엘지.필립스 엘시디 주식회사 | 광배향성 물질 및 이를 이용한 액정표시소자 |
| JP2003073471A (ja) * | 2001-08-31 | 2003-03-12 | Jsr Corp | 垂直配向型液晶配向剤およびそれを用いた液晶表示素子 |
| JP2003255349A (ja) * | 2002-03-05 | 2003-09-10 | Jsr Corp | 液晶配向膜、液晶配向膜の製造方法、および液晶表示素子 |
-
2005
- 2005-01-24 JP JP2005015202A patent/JP4821118B2/ja not_active Expired - Fee Related
- 2005-02-04 TW TW094103548A patent/TWI307337B/zh not_active IP Right Cessation
- 2005-02-07 KR KR1020050011449A patent/KR100655766B1/ko not_active Expired - Fee Related
-
2006
- 2006-09-01 KR KR1020060084237A patent/KR100775012B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100775012B1 (ko) | 2007-11-08 |
| TW200535120A (en) | 2005-11-01 |
| JP4821118B2 (ja) | 2011-11-24 |
| KR100655766B1 (ko) | 2006-12-08 |
| KR20060101411A (ko) | 2006-09-22 |
| KR20060041851A (ko) | 2006-05-12 |
| JP2005255981A (ja) | 2005-09-22 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |