JP5085933B2 - コレステリック液晶コポリマーおよび添加剤 - Google Patents
コレステリック液晶コポリマーおよび添加剤 Download PDFInfo
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- JP5085933B2 JP5085933B2 JP2006524639A JP2006524639A JP5085933B2 JP 5085933 B2 JP5085933 B2 JP 5085933B2 JP 2006524639 A JP2006524639 A JP 2006524639A JP 2006524639 A JP2006524639 A JP 2006524639A JP 5085933 B2 JP5085933 B2 JP 5085933B2
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- Prior art keywords
- sub
- liquid crystal
- cholesteric liquid
- formula
- alkylene
- 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.)
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- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 title claims description 179
- 239000000654 additive Substances 0.000 title description 10
- 229920001577 copolymer Polymers 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 heterocyclylene Chemical group 0.000 claims description 75
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 27
- 125000001475 halogen functional group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000002243 precursor Substances 0.000 claims description 22
- 125000004450 alkenylene group Chemical group 0.000 claims description 21
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 20
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Chemical group 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000012948 isocyanate Chemical group 0.000 claims description 6
- 150000002513 isocyanates Chemical group 0.000 claims description 6
- 229910000077 silane Chemical group 0.000 claims description 6
- 239000010408 film Substances 0.000 description 49
- 239000004973 liquid crystal related substance Substances 0.000 description 39
- 125000001424 substituent group Chemical group 0.000 description 31
- 230000003287 optical effect Effects 0.000 description 30
- 229920000106 Liquid crystal polymer Polymers 0.000 description 21
- 230000005540 biological transmission Effects 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 238000002835 absorbance Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 14
- 239000011295 pitch Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 10
- 230000010287 polarization Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- 238000000411 transmission spectrum Methods 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RLTYIUFCZBNBSS-UHFFFAOYSA-N [4-(4-fluorobenzoyl)oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(F)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 RLTYIUFCZBNBSS-UHFFFAOYSA-N 0.000 description 3
- CSNCPNFITVRIBQ-UHFFFAOYSA-N [6-[4-[4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoyl]oxybenzoyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] 4-[4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoyl]oxybenzoate Chemical group C1=CC(OC(=O)OCCCCOC(=O)C=C)=CC=C1C(=O)OC1=CC=C(C(=O)OC2C3OCC(C3OC2)OC(=O)C=2C=CC(OC(=O)C=3C=CC(OC(=O)OCCCCOC(=O)C=C)=CC=3)=CC=2)C=C1 CSNCPNFITVRIBQ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 2
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LSALEAQKRZHRQP-UHFFFAOYSA-N [4-(4-fluorobenzoyl)oxyphenyl] 4-(2-prop-2-enoyloxyethoxy)benzoate Chemical compound C1=CC(F)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCOC(=O)C=C)C=C1 LSALEAQKRZHRQP-UHFFFAOYSA-N 0.000 description 2
- NUKCBLFKNMRSGQ-UHFFFAOYSA-N [4-[4-(2-prop-2-enoyloxyethoxy)benzoyl]oxyphenyl] 4-butoxybenzoate Chemical compound C1=CC(OCCCC)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCOC(=O)C=C)C=C1 NUKCBLFKNMRSGQ-UHFFFAOYSA-N 0.000 description 2
- FMVMXBLNCZUIFX-UHFFFAOYSA-N [4-[4-(2-prop-2-enoyloxyethoxy)benzoyl]oxyphenyl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCOC(=O)C=C)C=C1 FMVMXBLNCZUIFX-UHFFFAOYSA-N 0.000 description 2
- ANPFLCPTAOUEJX-UHFFFAOYSA-N [4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-cyanobenzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(C#N)C=C1 ANPFLCPTAOUEJX-UHFFFAOYSA-N 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FTQOIXBLZHRTFH-UHFFFAOYSA-N 1,3-dioxane-2,4-diyl Chemical group C1C[O+]=CO[CH-]1 FTQOIXBLZHRTFH-UHFFFAOYSA-N 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- LAUFPZPAKULAGB-UHFFFAOYSA-N 4-butoxybenzoic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=C1 LAUFPZPAKULAGB-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- WPQGJLSPZVTJNY-UHFFFAOYSA-N [4-(4-cyanophenyl)phenyl] 4-(2-prop-2-enoyloxyethoxy)benzoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 WPQGJLSPZVTJNY-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229920001400 block copolymer Polymers 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
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- BMFYCFSWWDXEPB-UHFFFAOYSA-N cyclohexyl(phenyl)methanone Chemical group C=1C=CC=CC=1C(=O)C1CCCCC1 BMFYCFSWWDXEPB-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- VBBRYJMZLIYUJQ-UHFFFAOYSA-N cyclopropanone Chemical compound O=C1CC1 VBBRYJMZLIYUJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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Images
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
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- G—PHYSICS
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- 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
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K2019/2035—Ph-COO-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K2019/2078—Ph-COO-Ph-COO-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K2019/3095—Cyclohexane rings in which the end group is the monoterpene menthyl
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- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/031—Polarizer or dye
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/035—Ester polymer, e.g. polycarbonate, polyacrylate or polyester
Landscapes
- Chemical & Material Sciences (AREA)
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- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Steroid Compounds (AREA)
- Polarising Elements (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US10/652,700 US7160586B2 (en) | 2003-08-29 | 2003-08-29 | Cholesteric liquid crystal copolymers and additives |
| US10/652,700 | 2003-08-29 | ||
| PCT/US2004/021610 WO2005023964A2 (en) | 2003-08-29 | 2004-07-06 | Cholesteric liquid crystal copolymers and additives |
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| JP2007504296A JP2007504296A (ja) | 2007-03-01 |
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| US7439000B2 (en) * | 2005-10-25 | 2008-10-21 | 3M Innovative Properties Company | High clarity cholesteric liquid crystal films |
| WO2007142206A1 (ja) | 2006-06-05 | 2007-12-13 | Zeon Corporation | コレステリック液晶組成物及び円偏光分離シート、並びにその用途 |
| JP2008165385A (ja) * | 2006-12-27 | 2008-07-17 | Dainippon Printing Co Ltd | 赤外線反射パターン印刷透明シート |
| US20100270058A1 (en) * | 2007-12-14 | 2010-10-28 | 3M Innovative Properties Company | Methods for making electronic devices |
| KR100940681B1 (ko) * | 2007-12-24 | 2010-02-08 | 주식회사 동부하이텍 | 반도체 회로 장치 및 코드 변환 장치 |
| JP5259501B2 (ja) * | 2009-06-11 | 2013-08-07 | 富士フイルム株式会社 | 赤外光反射板、赤外光反射性合わせガラス、並びにコレステリック液晶層を有する積層体及び合わせガラス |
| JP5718260B2 (ja) | 2011-09-08 | 2015-05-13 | 富士フイルム株式会社 | 重合性液晶化合物、重合性組成物、高分子材料、及びフィルム |
| WO2013066308A1 (en) | 2011-10-31 | 2013-05-10 | Hewlett-Packard Development Company, L.P. | Diffuse cholesteric reflector |
| JP5786000B2 (ja) * | 2012-09-25 | 2015-09-30 | 富士フイルム株式会社 | 重合性液晶化合物、液晶組成物、高分子材料の製造方法とその製造方法およびフィルム |
| WO2018020838A1 (ja) * | 2016-07-27 | 2018-02-01 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| CN107236551A (zh) * | 2017-05-16 | 2017-10-10 | 深圳市唯酷光电有限公司 | 液晶组合物、液晶手写膜和液晶手写板 |
| JP7118079B2 (ja) * | 2017-10-02 | 2022-08-15 | 富士フイルム株式会社 | 液晶組成物、反射層、反射層の製造方法、及び共重合体 |
| CN112266781A (zh) * | 2020-10-28 | 2021-01-26 | 江苏康恒化工有限公司 | 热致变色材料组合物 |
| CN116744739B (zh) * | 2023-06-20 | 2024-02-20 | 陕西晶彩明为科技有限公司 | 一种增亮膜和显示基板 |
| CN119040008B (zh) * | 2024-10-30 | 2025-02-07 | 吉林省卓材新研科技有限公司 | 一种铁电向列相液晶分子及其应用 |
| CN119846878B (zh) * | 2025-03-07 | 2025-12-30 | 南京大学 | 一种液晶结构色全息薄膜及其制备方法、彩色全息装置 |
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| DE2831909A1 (de) * | 1978-07-20 | 1980-02-07 | Basf Ag | Fluessig-kristalline polymerphase mit cholesterischer struktur, verfahren zu ihrer herstellung und ihre verwendung |
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| US4974941A (en) * | 1989-03-08 | 1990-12-04 | Hercules Incorporated | Process of aligning and realigning liquid crystal media |
| EP0525477B1 (de) * | 1991-07-26 | 1998-09-16 | Rolic AG | Orientierte Photopolymere und Verfahren zu ihrer Herstellung |
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| US5332522A (en) * | 1993-04-29 | 1994-07-26 | The University Of Rochester | Thermotropic chiral nematic liquid crystalline copolymers |
| DE4342280A1 (de) * | 1993-12-11 | 1995-06-14 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19520704A1 (de) * | 1995-06-09 | 1996-12-12 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
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-
2003
- 2003-08-29 US US10/652,700 patent/US7160586B2/en not_active Expired - Fee Related
-
2004
- 2004-07-06 EP EP04777612A patent/EP1660612B1/en not_active Expired - Lifetime
- 2004-07-06 PL PL04777612T patent/PL1660612T3/pl unknown
- 2004-07-06 WO PCT/US2004/021610 patent/WO2005023964A2/en not_active Ceased
- 2004-07-06 JP JP2006524639A patent/JP5085933B2/ja not_active Expired - Fee Related
- 2004-07-06 DE DE602004018939T patent/DE602004018939D1/de not_active Expired - Lifetime
- 2004-07-06 KR KR1020067004175A patent/KR101044151B1/ko not_active Expired - Fee Related
- 2004-07-06 CN CNB2004800244778A patent/CN100510002C/zh not_active Expired - Fee Related
- 2004-07-06 AT AT04777612T patent/ATE420148T1/de not_active IP Right Cessation
- 2004-08-11 TW TW093124092A patent/TW200523343A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005023964A2 (en) | 2005-03-17 |
| ATE420148T1 (de) | 2009-01-15 |
| JP2007504296A (ja) | 2007-03-01 |
| KR20060119900A (ko) | 2006-11-24 |
| EP1660612B1 (en) | 2009-01-07 |
| KR101044151B1 (ko) | 2011-06-24 |
| DE602004018939D1 (de) | 2009-02-26 |
| EP1660612A2 (en) | 2006-05-31 |
| US20050045854A1 (en) | 2005-03-03 |
| CN1842583A (zh) | 2006-10-04 |
| CN100510002C (zh) | 2009-07-08 |
| WO2005023964A3 (en) | 2005-06-30 |
| US7160586B2 (en) | 2007-01-09 |
| PL1660612T3 (pl) | 2009-06-30 |
| TW200523343A (en) | 2005-07-16 |
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