FI79132B - Helikromisk-smektiska vaetskekristallkompositioner och -displayceller. - Google Patents
Helikromisk-smektiska vaetskekristallkompositioner och -displayceller. Download PDFInfo
- Publication number
- FI79132B FI79132B FI833861A FI833861A FI79132B FI 79132 B FI79132 B FI 79132B FI 833861 A FI833861 A FI 833861A FI 833861 A FI833861 A FI 833861A FI 79132 B FI79132 B FI 79132B
- Authority
- FI
- Finland
- Prior art keywords
- helichromic
- composition
- liquid crystal
- mixture
- smectic
- Prior art date
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- 239000000203 mixture Substances 0.000 claims description 147
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 68
- 239000004973 liquid crystal related substance Substances 0.000 claims description 54
- -1 polyazo Chemical group 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 41
- 230000004888 barrier function Effects 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 14
- 230000007704 transition Effects 0.000 claims description 14
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 9
- ZLPCVEVCHZENMS-UHFFFAOYSA-N bis[2-(2-phenylethenyl)phenyl]diazene Chemical group C(=Cc1ccccc1N=Nc1ccccc1C=Cc1ccccc1)c1ccccc1 ZLPCVEVCHZENMS-UHFFFAOYSA-N 0.000 claims description 7
- 230000010287 polarization Effects 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 5
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 5
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 58
- 239000000047 product Substances 0.000 description 57
- 239000000975 dye Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 239000010410 layer Substances 0.000 description 39
- 238000000034 method Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 27
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- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 238000005859 coupling reaction Methods 0.000 description 20
- 230000004044 response Effects 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000011049 filling Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000006193 diazotization reaction Methods 0.000 description 14
- 230000005684 electric field Effects 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000000945 filler Substances 0.000 description 12
- PWIRSGZYRGXAQV-UHFFFAOYSA-N 4-(2-methylbutyl)aniline Chemical compound CCC(C)CC1=CC=C(N)C=C1 PWIRSGZYRGXAQV-UHFFFAOYSA-N 0.000 description 11
- 239000000654 additive Substances 0.000 description 11
- 230000003098 cholesteric effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- 238000004587 chromatography analysis Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 239000003463 adsorbent Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- XKVLZBNEPALHIO-UHFFFAOYSA-N 1-bromo-2-methylbutane Chemical compound CCC(C)CBr XKVLZBNEPALHIO-UHFFFAOYSA-N 0.000 description 6
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 6
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- IFDLFCDWOFLKEB-UHFFFAOYSA-N 2-methylbutylbenzene Chemical compound CCC(C)CC1=CC=CC=C1 IFDLFCDWOFLKEB-UHFFFAOYSA-N 0.000 description 4
- DNWPRABXFMRDEF-UHFFFAOYSA-N 4-(2-methylbutyl)benzaldehyde Chemical compound CCC(C)CC1=CC=C(C=O)C=C1 DNWPRABXFMRDEF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical group NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 4
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 3
- ISAQXIJQZLXVGM-UHFFFAOYSA-N 1,1,1-trifluoro-n-(2-methylbutyl)-n-naphthalen-1-ylmethanesulfonamide Chemical compound C1=CC=C2C(N(CC(C)CC)S(=O)(=O)C(F)(F)F)=CC=CC2=C1 ISAQXIJQZLXVGM-UHFFFAOYSA-N 0.000 description 3
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 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
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- HDXCJEJEXWIISO-UHFFFAOYSA-N n-(2-methylbutyl)naphthalen-1-amine Chemical compound C1=CC=C2C(NCC(C)CC)=CC=CC2=C1 HDXCJEJEXWIISO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000005361 soda-lime glass Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- LRVDJULRTAOFJT-UHFFFAOYSA-N 1,1,1-trifluoro-n-naphthalen-1-ylmethanesulfonamide Chemical compound C1=CC=C2C(NS(=O)(=O)C(F)(F)F)=CC=CC2=C1 LRVDJULRTAOFJT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- HXCFXWXMOAWRIT-UHFFFAOYSA-N 4-methylhexylbenzene Chemical compound CCC(C)CCCC1=CC=CC=C1 HXCFXWXMOAWRIT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- JYGSKOUHMFYYDA-UHFFFAOYSA-N CCC(C)CC(C(C)=C1)=CC(C)=C1N(N=NC1=CC=CC=C1)N=NC1=C(C)C=CC(C)=C1 Chemical compound CCC(C)CC(C(C)=C1)=CC(C)=C1N(N=NC1=CC=CC=C1)N=NC1=C(C)C=CC(C)=C1 JYGSKOUHMFYYDA-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UKRQQTUHXSUNPV-UHFFFAOYSA-N N1NNN=CC1 Chemical compound N1NNN=CC1 UKRQQTUHXSUNPV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 125000005393 dicarboximide group Chemical group 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 108010085420 helichrome Proteins 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- SYTKXVWVELMDLL-UHFFFAOYSA-N n-(4-methylhexyl)aniline Chemical compound CCC(C)CCCNC1=CC=CC=C1 SYTKXVWVELMDLL-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
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- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
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- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
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- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
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- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/16—Trisazo dyes
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- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/04—Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound
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- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2436—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
- C09B5/2445—Phtaloyl isoindoles
- C09B5/2454—5,6 phtaloyl dihydro isoindoles
- C09B5/2463—1,3 oxo or imino derivatives
- C09B5/2472—1,3 dioxo derivatives
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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- General Physics & Mathematics (AREA)
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Claims (7)
1. Komposition till användning i värmestyrbara vätskekristalldisplayer bestäende väsentligen av ett smek- 5 tiskt vätskekristallmaterial i blandning med en organisk, icke-jonisk, icke-vätskekristallin helikrom förening, vil-ken helikrom förening är löslig i det smektiska vätske-kristallmaterialet och vilken utgörs av ett cirkulärt och dikroiskt färgämne och vilken har formeln 10 Q-(Z)n i vilken Q är en azo-, azostilben-, bensotiazolyl-, poly-azo-, metin-, azometin-, merocyanin-, metinaryliden-, tet-15 razin-, oxadiazin-, karbazolazo- eller antrakinongrupp, Z är en asymmetrisk atom on n är ett heltal 1-8, känne-t e c k n a d därav, att vätskekristallmaterialet utgörs av ett smektiskt vätskekristallmaterial.
2. Komposition enligt patentkravet 1, känne-20 tecknad därav, att Z är (+)-2-metylalkyl, (+)-3-me- tylalkyl, (+)-2-metylalkoxi, (+)-3-metylalkoxi, (+)-cit-ronellyl, (+)-camfanyl, (+)-3-metylcyklohexyl, (+)-a-me-tylbensyl, ( +)-2-( metylbutyl)bifenylbenzoat, ( + )-(2-me-tylbutyl)metyl-2,3-dihydropermidin, (+)-3-metylcyklopen-25 ty1-2,3-dihydropermidin, (+)-2-metylcyklohexyl-2,3-dihyd ropermidin, (+)-2-fenetylamin eller (+)-N-(2-metylbutyl)-aminonaftalen.
3. Komposition enligt patentkravet 1, känne-tecknad därav, att den helikroma föreningen är när- 30 varande i kompositionen i en mängd tillräcklig att ästad-komma fortplantning av infallande ljus cirkulärt polari-serat sälunda att ali polarisering av det nämnda ljuset absorberas dä kompositionen används i en helikrom-smektisk vätskekristalldisplay. 35
4. Värmestyrbar vätskekristalldisplay (10) utan 94 791 32 hjälppolarisatorer, vilken display ger en högkontrastbild mot en bakgrund, och vilken omfattar ett skikt av en väts-kekristallkomposition (11) mellan en ytskiva (12) och en bottenskiva (13), vilken komposition är värmekänslig och 5 har en omvandling mellan ätminstone tvä termiska faser, varvid den övre termiska fasen är nematisk, och den nedre termiska fasen är smektisk; medel för ästadkommande av den termiska omvandlingen mellan den nedre termiska fasen och den Övre termiska fasen (r3 , r2, r3 etc.) och medel för 10 elektriskt styrande av kompositionens (11) delar (r:, r2, r3 etc. ) och (c3 , c2 , c3 etc. ), kännetecknad därav, att 1. kompositionen (11) utgörs av en komposition en-ligt patentkravet 1 och att kompositionen har tvä möjliga 15 orienteringstillständ i den smektiska fasen, varvid det första orienteringstillständet är väsentligen ljusabsorbe-rande, och det andra tillständet är väsentligen ljusgenom-släppligt och att 2. i kompositionens (11) elektriskt styrbara delar 20 utvecklas det andra 1jusgenomsläppliga tillständet dä kompositionen (11) snabbt övergär tili det nedre termiska tillständet frän det övre termiska tillständet, medan i de äterstäende, icke styrda delarna i kompositionen (11) utvecklas det första, väsentligen ljusabsorberande till-25 ständet dä kompositionen (11) snabbt övergär tili det läg-re termiska tillständet frän det övre termiska tillständet.
5. Display (10) enligt patentkravet 4, kännetecknad därav, att medlen för ästadkommande av 30 den termiska omvandlingen mellan den lägre termiska fasen och den övre termiska fasen omfattar ätminstone en värme-elektrod (r3, r2, r3 etc.) anordnad mellan bottenskivan (13) och kompositionen (11).
6. Display (10) enligt patentkravet 5, k ä n n e -35 tecknad därav, att den ytterligare omfattar ett
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US43603082 | 1982-10-22 | ||
US06/436,030 US4514045A (en) | 1981-06-22 | 1982-10-22 | Helichromic-smectic liquid crystal compositions and display cells |
Publications (4)
Publication Number | Publication Date |
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FI833861A0 FI833861A0 (fi) | 1983-10-21 |
FI833861A FI833861A (fi) | 1984-04-23 |
FI79132B true FI79132B (fi) | 1989-07-31 |
FI79132C FI79132C (sv) | 1989-11-10 |
Family
ID=23730814
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI833861A FI79132C (sv) | 1982-10-22 | 1983-10-21 | Helikromisk-smektiska vätskekristallkompositioner och -displayceller |
Country Status (8)
Country | Link |
---|---|
US (1) | US4514045A (sv) |
EP (1) | EP0107492B1 (sv) |
JP (1) | JPS5993777A (sv) |
KR (1) | KR910004825B1 (sv) |
AU (1) | AU568096B2 (sv) |
CA (1) | CA1200970A (sv) |
DE (1) | DE3380354D1 (sv) |
FI (1) | FI79132C (sv) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5887535A (ja) * | 1981-11-20 | 1983-05-25 | Sony Corp | 液晶表示装置 |
JPS6028487A (ja) * | 1983-07-27 | 1985-02-13 | Alps Electric Co Ltd | 液晶組成物 |
DE3333677A1 (de) * | 1983-09-17 | 1985-04-04 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristall-phase |
EP0153729B1 (en) * | 1984-02-27 | 1989-05-10 | TDK Corporation | Optical recording medium |
US4653866A (en) * | 1984-05-21 | 1987-03-31 | Hitachi, Ltd. | Liquid crystal compound and liquid crystal composition including the same |
GB2170214A (en) * | 1985-01-26 | 1986-07-30 | Stc Plc | Ferroelectric smectic liquid crystal mixture |
US4764619A (en) * | 1985-03-26 | 1988-08-16 | Asahi Glass Company Ltd. | Optically active compounds, smectic liquid crystal compositions containing them and smectic liquid crystal display devices |
JP2713567B2 (ja) * | 1986-04-04 | 1998-02-16 | 三井東圧化学株式会社 | 光学活性ナフタレン誘導体 |
JP2558803B2 (ja) * | 1988-04-06 | 1996-11-27 | 旭電化工業株式会社 | 光学活性ビスアリール化合物 |
JP2778670B2 (ja) * | 1989-02-17 | 1998-07-23 | 出光興産株式会社 | 液晶組成物 |
US5428137A (en) * | 1992-01-31 | 1995-06-27 | Orient Chemical Industries, Ltd. | Monoazo liquid dye and solutions thereof |
JPH05281581A (ja) * | 1992-09-28 | 1993-10-29 | Canon Inc | 液晶素子 |
EP0613720A1 (en) * | 1993-03-05 | 1994-09-07 | Duphar International Research B.V | Nickel catalyst for the cyanation of aromatic halides |
EP0613719A1 (en) * | 1993-03-05 | 1994-09-07 | Duphar International Research B.V | Nickel catalyst for the cyanation of aromatic halides |
US5854614A (en) * | 1996-11-18 | 1998-12-29 | Array Printers Ab Publ. | Display device and method for visualizing computer generated image information |
US6229514B1 (en) | 1995-11-13 | 2001-05-08 | Array Printers Publ. Ab | Display device and method for visualizing computer generated image information |
US5748277A (en) * | 1995-02-17 | 1998-05-05 | Kent State University | Dynamic drive method and apparatus for a bistable liquid crystal display |
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-
1982
- 1982-10-22 US US06/436,030 patent/US4514045A/en not_active Expired - Fee Related
-
1983
- 1983-10-04 CA CA000438342A patent/CA1200970A/en not_active Expired
- 1983-10-20 KR KR1019830004955A patent/KR910004825B1/ko not_active IP Right Cessation
- 1983-10-21 DE DE8383306409T patent/DE3380354D1/de not_active Expired
- 1983-10-21 JP JP58197488A patent/JPS5993777A/ja active Granted
- 1983-10-21 EP EP83306409A patent/EP0107492B1/en not_active Expired
- 1983-10-21 FI FI833861A patent/FI79132C/sv not_active IP Right Cessation
- 1983-10-21 AU AU20455/83A patent/AU568096B2/en not_active Expired
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FI833861A (fi) | 1984-04-23 |
AU568096B2 (en) | 1987-12-17 |
FI79132C (sv) | 1989-11-10 |
CA1200970A (en) | 1986-02-25 |
EP0107492A3 (en) | 1985-09-11 |
DE3380354D1 (en) | 1989-09-14 |
EP0107492B1 (en) | 1989-08-09 |
KR840006820A (ko) | 1984-12-03 |
KR910004825B1 (ko) | 1991-07-13 |
AU2045583A (en) | 1984-05-03 |
US4514045A (en) | 1985-04-30 |
JPS5993777A (ja) | 1984-05-30 |
JPH0410514B2 (sv) | 1992-02-25 |
FI833861A0 (fi) | 1983-10-21 |
EP0107492A2 (en) | 1984-05-02 |
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MA | Patent expired |
Owner name: MINNESOTA MINING AND MANUFACTURING COMPANY |