DE2920730C2 - - Google Patents
Info
- Publication number
- DE2920730C2 DE2920730C2 DE2920730A DE2920730A DE2920730C2 DE 2920730 C2 DE2920730 C2 DE 2920730C2 DE 2920730 A DE2920730 A DE 2920730A DE 2920730 A DE2920730 A DE 2920730A DE 2920730 C2 DE2920730 C2 DE 2920730C2
- Authority
- DE
- Germany
- Prior art keywords
- systems according
- anthraquinone
- nematic liquid
- pleochroic dye
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000975 dye Substances 0.000 claims description 56
- 239000004973 liquid crystal related substance Substances 0.000 claims description 17
- -1 4- (n-butyl) cyclohexyl Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000005684 electric field Effects 0.000 claims description 9
- 239000002178 crystalline material Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 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 claims description 7
- 150000004056 anthraquinones Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- CELQZBPTMPTJBU-UHFFFAOYSA-N 2-heptyl-1-phenylcyclohexane-1-carbonitrile Chemical compound CCCCCCCC1CCCCC1(C#N)C1=CC=CC=C1 CELQZBPTMPTJBU-UHFFFAOYSA-N 0.000 claims description 3
- WCLNGBQPTVENHV-MKQVXYPISA-N cholesteryl nonanoate Chemical group C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCC)C1 WCLNGBQPTVENHV-MKQVXYPISA-N 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229930184652 p-Terphenyl Natural products 0.000 claims description 2
- DLTHOPXCOVTMJQ-UHFFFAOYSA-N 1,2-bis[4-(4-nitrophenyl)sulfanylanilino]anthracene-9,10-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC(C=C1)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1NC(C=C1)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1 DLTHOPXCOVTMJQ-UHFFFAOYSA-N 0.000 claims 1
- WKRWEKZGPFKMOK-UHFFFAOYSA-N 1,5-bis(n-phenylanilino)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(N(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1N(C=1C=CC=CC=1)C1=CC=CC=C1 WKRWEKZGPFKMOK-UHFFFAOYSA-N 0.000 claims 1
- IEMWRWNGMRQYAH-UHFFFAOYSA-N 1,5-bis[4-(4-pentylcyclohexyl)anilino]anthracene-9,10-dione Chemical compound C1CC(CCCCC)CCC1C(C=C1)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C=CC(=CC=3)C3CCC(CCCCC)CC3)=C1C2=O IEMWRWNGMRQYAH-UHFFFAOYSA-N 0.000 claims 1
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 20
- 239000004988 Nematic liquid crystal Substances 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910003437 indium oxide Inorganic materials 0.000 description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000374 eutectic mixture Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- HUTKUCNNEVSGLA-UHFFFAOYSA-N 1,4-bis(4-butylanilino)anthracene-9,10-dione Chemical compound C1=CC(CCCC)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(CCCC)C=C1 HUTKUCNNEVSGLA-UHFFFAOYSA-N 0.000 description 2
- FNMVOZGCURCHJU-UHFFFAOYSA-N 1,4-bis(4-ethylanilino)anthracene-9,10-dione Chemical compound C1=CC(CC)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(CC)C=C1 FNMVOZGCURCHJU-UHFFFAOYSA-N 0.000 description 2
- DDDLVWOAJHLBFW-UHFFFAOYSA-N 1,4-bis(4-phenylanilino)anthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC(C=C1)=CC=C1C1=CC=CC=C1 DDDLVWOAJHLBFW-UHFFFAOYSA-N 0.000 description 2
- YXMPVZQSOHSEJA-UHFFFAOYSA-N 1,4-dianilinoanthracene-9,10-dione Chemical compound C1=CC(NC=2C=CC=CC=2)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 YXMPVZQSOHSEJA-UHFFFAOYSA-N 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 2
- DSFSRLFEZUEQBX-UHFFFAOYSA-N 2-pentyl-1-phenylcyclohexane-1-carbonitrile Chemical compound CCCCCC1CCCCC1(C#N)C1=CC=CC=C1 DSFSRLFEZUEQBX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TXVIOHUXGGXFFY-UHFFFAOYSA-N 1,2,5,6-tetrachloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1Cl TXVIOHUXGGXFFY-UHFFFAOYSA-N 0.000 description 1
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- VXQHDXQLQLBGHS-UHFFFAOYSA-N 1,2-dianilinoanthracene-9,10-dione Chemical class C=1C=CC=CC=1NC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 VXQHDXQLQLBGHS-UHFFFAOYSA-N 0.000 description 1
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CAHGWVAXFJXDNI-UHFFFAOYSA-N 1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2Cl CAHGWVAXFJXDNI-UHFFFAOYSA-N 0.000 description 1
- UYWILBVZOSDZQT-UHFFFAOYSA-N 1,5-bis(4-cyclohexylanilino)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(NC=4C=CC(=CC=4)C4CCCCC4)=C3C(=O)C2=CC=CC=1NC(C=C1)=CC=C1C1CCCCC1 UYWILBVZOSDZQT-UHFFFAOYSA-N 0.000 description 1
- PPFJSBBANKZHFY-UHFFFAOYSA-N 1,5-bis(4-cyclohexylphenyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(C=4C=CC(=CC=4)C4CCCCC4)=C3C(=O)C2=CC=CC=1C(C=C1)=CC=C1C1CCCCC1 PPFJSBBANKZHFY-UHFFFAOYSA-N 0.000 description 1
- XHSSNROBJSYTCA-UHFFFAOYSA-N 1,5-bis(benzylamino)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(NCC=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1NCC1=CC=CC=C1 XHSSNROBJSYTCA-UHFFFAOYSA-N 0.000 description 1
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 1
- NYRPOEUUOWEMEH-UHFFFAOYSA-N 1-(butylamino)-4-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NCCCC)=CC=C1NC1=CC=C(C)C=C1 NYRPOEUUOWEMEH-UHFFFAOYSA-N 0.000 description 1
- RGGMRSFFCMWJLT-UHFFFAOYSA-N 1-(butylamino)-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2NCCCC RGGMRSFFCMWJLT-UHFFFAOYSA-N 0.000 description 1
- BSRVLAQTSIFZJL-UHFFFAOYSA-N 1-(cyclohexylamino)-4-(n-pentylanilino)anthracene-9,10-dione Chemical compound C=1C=C(NC2CCCCC2)C=2C(=O)C3=CC=CC=C3C(=O)C=2C=1N(CCCCC)C1=CC=CC=C1 BSRVLAQTSIFZJL-UHFFFAOYSA-N 0.000 description 1
- BWQIGAJDKXZJTG-UHFFFAOYSA-N 1-(cyclohexylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1CCCCC1 BWQIGAJDKXZJTG-UHFFFAOYSA-N 0.000 description 1
- MXXWVEICJNOLPM-UHFFFAOYSA-N 1-(methylamino)-4-(4-octylanilino)-2-undecylanthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC=C3C(=O)C2=C(NC)C(CCCCCCCCCCC)=CC=1NC1=CC=C(CCCCCCCC)C=C1 MXXWVEICJNOLPM-UHFFFAOYSA-N 0.000 description 1
- HXAUSOFYYXMRGT-UHFFFAOYSA-N 1-[[1-(methylamino)-4-octyl-6-undecylcyclohexa-2,4-dien-1-yl]amino]anthracene-9,10-dione Chemical compound CNC1(NC2=CC=CC=3C(C4=CC=CC=C4C(C23)=O)=O)C(C=C(C=C1)CCCCCCCC)CCCCCCCCCCC HXAUSOFYYXMRGT-UHFFFAOYSA-N 0.000 description 1
- WIMJTAGMOPIYOA-UHFFFAOYSA-N 1-bromo-4-(cyclohexylamino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Br)=CC=C1NC1CCCCC1 WIMJTAGMOPIYOA-UHFFFAOYSA-N 0.000 description 1
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 description 1
- FBODHSPJHSECGE-UHFFFAOYSA-N 1-chloro-4-(4-decylanilino)anthracene-9,10-dione Chemical compound C1=CC(CCCCCCCCCC)=CC=C1NC1=CC=C(Cl)C2=C1C(=O)C1=CC=CC=C1C2=O FBODHSPJHSECGE-UHFFFAOYSA-N 0.000 description 1
- TUZZWPYZPHNFJY-UHFFFAOYSA-N 1-chloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2O TUZZWPYZPHNFJY-UHFFFAOYSA-N 0.000 description 1
- HHHLIGOWCFIEBJ-UHFFFAOYSA-N 1-hydroxy-4-(n-pentylanilino)anthracene-9,10-dione Chemical compound C=1C=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C=1N(CCCCC)C1=CC=CC=C1 HHHLIGOWCFIEBJ-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- MMVCISHYVYMDKH-UHFFFAOYSA-N 1-phenyl-2-propylcyclohexane-1-carbonitrile Chemical compound CCCC1CCCCC1(C#N)C1=CC=CC=C1 MMVCISHYVYMDKH-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- PZNZCCLRGXLYJI-UHFFFAOYSA-N 4-butylcyclohexan-1-amine Chemical compound CCCCC1CCC(N)CC1 PZNZCCLRGXLYJI-UHFFFAOYSA-N 0.000 description 1
- WGENWPANMZLPIH-UHFFFAOYSA-N 4-decylaniline Chemical compound CCCCCCCCCCC1=CC=C(N)C=C1 WGENWPANMZLPIH-UHFFFAOYSA-N 0.000 description 1
- QNCROBVCGOMSRR-UHFFFAOYSA-N 4-n-octylbenzene-1,4-diamine Chemical compound CCCCCCCCNC1=CC=C(N)C=C1 QNCROBVCGOMSRR-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WOYOERPIKOEKAC-UHFFFAOYSA-N C(CCC)NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(CCC)NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)N(C1=CC=CC=C1)C1=CC=CC=C1 WOYOERPIKOEKAC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 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 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- NZKRSTFEUZGAMA-UHFFFAOYSA-N n-[4-[[4-(cyclohexylamino)-9,10-dioxoanthracen-1-yl]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1CCCCC1 NZKRSTFEUZGAMA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13725—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on guest-host interaction
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
- C09K19/603—Anthroquinonic
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90867178A | 1978-05-23 | 1978-05-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2920730A1 DE2920730A1 (de) | 1979-11-29 |
| DE2920730C2 true DE2920730C2 (ja) | 1990-04-12 |
Family
ID=25426093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792920730 Granted DE2920730A1 (de) | 1978-05-23 | 1979-05-22 | Fluessigkristallsysteme und elektrooptische anzeigen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54157786A (ja) |
| KR (1) | KR850000050B1 (ja) |
| CH (1) | CH640259A5 (ja) |
| DE (1) | DE2920730A1 (ja) |
| FR (1) | FR2426724B1 (ja) |
| GB (1) | GB2024844B (ja) |
| IT (1) | IT1115232B (ja) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288147A (en) * | 1978-12-20 | 1981-09-08 | Timex Corporation | Electro-optical composition of the guest-host type |
| CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
| US4304683A (en) * | 1979-03-16 | 1981-12-08 | Mitsui Toatsu Chemicals, Inc. | Composition for liquid crystal color display element |
| US4360447A (en) * | 1979-03-16 | 1982-11-23 | Mitsui Toatsu Chemicals, Inc. | Composition for liquid crystal color display elements |
| JPS56500944A (ja) * | 1979-07-27 | 1981-07-09 | ||
| CH641828A5 (fr) * | 1979-08-17 | 1984-03-15 | Ebauches Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| CH642393A5 (fr) | 1979-10-02 | 1984-04-13 | Ebauches Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| GB2065695B (en) * | 1979-10-12 | 1984-07-25 | Hitachi Ltd | Guest-host type liquid crystal composition and liquid crystal display device using the same |
| JPS56117507U (ja) * | 1980-02-12 | 1981-09-08 | ||
| DE3007198A1 (de) | 1980-02-26 | 1981-09-03 | Siemens AG, 1000 Berlin und 8000 München | Pleochroitischer anthrachinon-farbstoff, verfahren zu seiner herstellung und verwendung des farbstoffs |
| CH646452A5 (fr) * | 1980-03-14 | 1984-11-30 | Asulab Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| CH643291A5 (fr) * | 1980-03-21 | 1984-05-30 | Asulab Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| DE3014933A1 (de) * | 1980-04-18 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| US4394070A (en) * | 1980-07-16 | 1983-07-19 | Minnesota Mining And Manufacturing Company | Helichromic compounds and displays |
| US4405211A (en) * | 1980-07-29 | 1983-09-20 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compositions with pleochroic anthraquinone dyes |
| US4391489A (en) * | 1980-07-29 | 1983-07-05 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials containing pleochroic anthraquinone dyes |
| JPS5755984A (en) * | 1980-09-22 | 1982-04-03 | Hitachi Ltd | Liquid crystal composition |
| US4624532A (en) * | 1980-10-22 | 1986-11-25 | General Electric Company | Dichroic liquid crystal compositions containing anthraquinone-based dyes |
| US4356102A (en) * | 1980-10-22 | 1982-10-26 | General Electric Company | Dichroic liquid crystal compositions containing anthraquinone-based dyes |
| DE3040102A1 (de) * | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
| DE3046904A1 (de) * | 1980-12-12 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, verfahren zu ihrer herstellung ihre verwendung sowie fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| EP0056492B1 (de) * | 1981-01-10 | 1984-12-12 | BASF Aktiengesellschaft | Farbstoffe für Flüssigkristallmischungen |
| GB2094825B (en) * | 1981-01-17 | 1984-09-12 | Mitsubishi Chem Ind | Liquid crystal compositions containing pleochroic anthraquinone dyes |
| GB2091753B (en) * | 1981-01-23 | 1984-08-22 | Standard Telephones Cables Ltd | Use of 1,4-b15 (hydrocarbylamino) anthraquinos as dyes in the smetic layers of a liquid crystal cell |
| US4464282A (en) * | 1981-02-25 | 1984-08-07 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland | Organic materials |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| EP0059036B1 (en) * | 1981-02-25 | 1987-07-29 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| EP0155345B1 (en) * | 1981-02-25 | 1988-02-03 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Pleochroic anthraquinone dyes |
| US4514045A (en) * | 1981-06-22 | 1985-04-30 | Minnesota Mining And Manufacturing Company | Helichromic-smectic liquid crystal compositions and display cells |
| JPS5825381A (ja) * | 1981-08-08 | 1983-02-15 | Nippon Kanko Shikiso Kenkyusho:Kk | 液晶組成物 |
| DE3137298A1 (de) * | 1981-09-18 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe |
| JPS5857488A (ja) * | 1981-10-02 | 1983-04-05 | Mitsubishi Chem Ind Ltd | ゲスト−ホスト型液晶組成物 |
| GB2120674B (en) * | 1982-03-13 | 1986-11-19 | Nippon Kanko Shikiso Kenyusho | Dichroic dyestuffs for liquid crystals and liquid crystal compositions comprising the same |
| EP0091225B1 (en) * | 1982-04-07 | 1988-12-07 | Imperial Chemical Industries Plc | Anthraquinone compounds |
| DE3366521D1 (en) * | 1982-04-07 | 1986-11-06 | Secr Defence Brit | Dielectric materials |
| DE3380031D1 (en) * | 1982-06-30 | 1989-07-13 | Hitachi Ltd | Liquid crystal composition |
| DE3240036A1 (de) * | 1982-10-28 | 1984-05-10 | Lev Michajlovič Moskva Blinov | Anthrachinonderivate, verfahren zu ihrer herstellung und ihre verwendung in fluesigkristallmaterialien fuer elektrooptische vorrichtungen |
| US4448492A (en) * | 1982-12-23 | 1984-05-15 | Minnesota Mining And Manufacturing Company | Cycloalkyl-type isotropic dyes for liquid crystal display devices |
| US4530572A (en) * | 1982-12-30 | 1985-07-23 | Minnesota Mining And Manufacturing Company | Substituted anthraquinone-type isotropic dyes for liquid crystal display devices |
| US4452511A (en) * | 1982-12-30 | 1984-06-05 | Minnesota Mining And Manufacturing Company | Substituted anthracene-type isotropic dyes for liquid crystal display devices |
| JPS59182878A (ja) * | 1983-04-01 | 1984-10-17 | Hitachi Ltd | ゲスト― ホスト型液晶組成物 |
| JPS61276884A (ja) * | 1985-05-31 | 1986-12-06 | Mitsubishi Chem Ind Ltd | カラ−液晶の製造法 |
| JPH03128763A (ja) * | 1989-10-13 | 1991-05-31 | Mazda Motor Corp | 自動車のステアリング装置 |
| JP3537265B2 (ja) * | 1996-05-08 | 2004-06-14 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
| WO2015157983A1 (en) * | 2014-04-18 | 2015-10-22 | Dow Global Technologies Llc | Anthraquinone compound used for color filter of lcd |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5942287B2 (ja) * | 1972-12-19 | 1984-10-13 | 松下電器産業株式会社 | 色相変調表示装置 |
| US3960751A (en) * | 1973-09-19 | 1976-06-01 | Matsushita Electric Industrial Co., Ltd. | Electro-optical display element |
| DE2862064D1 (en) * | 1977-10-14 | 1982-11-25 | Bdh Chemicals Ltd | Pleochroic dyes suitable for use in solution with liquid crystal materials for electro-optic device applications |
-
1979
- 1979-05-22 DE DE19792920730 patent/DE2920730A1/de active Granted
- 1979-05-22 GB GB7917828A patent/GB2024844B/en not_active Expired
- 1979-05-22 IT IT22892/79A patent/IT1115232B/it active
- 1979-05-22 FR FR7913057A patent/FR2426724B1/fr not_active Expired
- 1979-05-22 CH CH480579A patent/CH640259A5/de not_active IP Right Cessation
- 1979-05-22 JP JP6314579A patent/JPS54157786A/ja active Granted
- 1979-05-23 KR KR7901645A patent/KR850000050B1/ko active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2024844A (en) | 1980-01-16 |
| KR850000050B1 (ko) | 1985-02-14 |
| IT7922892A0 (it) | 1979-05-22 |
| JPH0116876B2 (ja) | 1989-03-28 |
| GB2024844B (en) | 1983-03-30 |
| CH640259A5 (de) | 1983-12-30 |
| DE2920730A1 (de) | 1979-11-29 |
| JPS54157786A (en) | 1979-12-12 |
| FR2426724B1 (fr) | 1985-09-27 |
| FR2426724A1 (fr) | 1979-12-21 |
| IT1115232B (it) | 1986-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |