DD219498A5 - Fluessigkristallzusammensetzungen fuer guest-host-fluessigkristallanzeigevorrichtungen - Google Patents

Fluessigkristallzusammensetzungen fuer guest-host-fluessigkristallanzeigevorrichtungen Download PDF

Info

Publication number: DD219498A5
Authority: DD; German Democratic Republic
Prior art keywords: liquid crystal; compositions according; crystal compositions; formula; dye
Prior art date: 1982-08-18

Application number

DD83254028A

Other languages

German (de)

English (en)

Inventor

Kenneth J Harrison

Adward P Raynes

Frances C Saunders

David J Thompson

Original Assignee

Secr Defence Brit

Priority date (The priority date 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 date listed.)

1982-08-18

Filing date

1983-08-17

Publication date

1985-03-06

1983-08-17 Application filed by Secr Defence Brit filed Critical Secr Defence Brit

1985-03-06 Publication of DD219498A5 publication Critical patent/DD219498A5/de

Links

239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 134
239000000203 mixture Substances 0.000 title claims abstract description 82
239000000463 material Substances 0.000 claims abstract description 103
-1 anthraquinone compound Chemical class 0.000 claims abstract description 30
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 abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 13
125000001424 substituent group Chemical group 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
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 abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
239000000975 dye Substances 0.000 claims description 101
150000001875 compounds Chemical class 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 15
230000008033 biological extinction Effects 0.000 claims description 11
239000004988 Nematic liquid crystal Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
239000001043 yellow dye Substances 0.000 claims description 5
239000001045 blue dye Substances 0.000 claims description 4
230000003098 cholesteric effect Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 3
239000001044 red dye Substances 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 2
239000001048 orange dye Substances 0.000 claims description 2
150000004056 anthraquinones Chemical class 0.000 claims 2
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
125000002877 alkyl aryl group Chemical group 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
239000001047 purple dye Substances 0.000 claims 1
239000000047 product Substances 0.000 description 33
239000000758 substrate Substances 0.000 description 29
230000000694 effects Effects 0.000 description 28
238000002360 preparation method Methods 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
230000005684 electric field Effects 0.000 description 14
238000000034 method Methods 0.000 description 13
210000004027 cell Anatomy 0.000 description 11
230000008859 change Effects 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000004949 mass spectrometry Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000005540 biological transmission Effects 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
AOJKIHFUPFIDNE-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitro-2,6-di(nonyl)anthracene-9,10-dione Chemical compound CCCCCCCCCC1=CC([N+]([O-])=O)=C2C(=O)C3=C(O)C(CCCCCCCCC)=CC([N+]([O-])=O)=C3C(=O)C2=C1O AOJKIHFUPFIDNE-UHFFFAOYSA-N 0.000 description 3
239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
239000004990 Smectic liquid crystal Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000576 coating method Methods 0.000 description 3
229960001577 dantron Drugs 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
230000008569 process Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
230000007704 transition Effects 0.000 description 3
CYSHZLYMRMVDBC-UHFFFAOYSA-N 1,5-dihydroxy-4-nitro-2,6-di(nonyl)-8-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=C(O)C(CCCCCCCCC)=CC([N+]([O-])=O)=C3C(=O)C2=C(O)C(CCCCCCCCC)=CC=1SC1=CC=CC=C1 CYSHZLYMRMVDBC-UHFFFAOYSA-N 0.000 description 2
GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 2
244000007853 Sarothamnus scoparius Species 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
210000002858 crystal cell Anatomy 0.000 description 2
239000003989 dielectric material Substances 0.000 description 2
HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
230000000802 nitrating effect Effects 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000004381 surface treatment Methods 0.000 description 2
ICQYRMKYGAVTCP-UHFFFAOYSA-N 1-(4-tert-butylphenyl)sulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC=CC=3)=C1C2=O ICQYRMKYGAVTCP-UHFFFAOYSA-N 0.000 description 1
XIRMKOCIWUOAOL-UHFFFAOYSA-N 1-amino-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1SC1=CC=CC=C1 XIRMKOCIWUOAOL-UHFFFAOYSA-N 0.000 description 1
AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
NQSWABRDUWHNMW-UHFFFAOYSA-N 2,6-bis(2,4-dimethylpentyl)-1,5-dihydroxy-4-nitro-8-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=C(O)C(CC(C)CC(C)C)=CC([N+]([O-])=O)=C3C(=O)C2=C(O)C(CC(C)CC(C)C)=CC=1SC1=CC=CC=C1 NQSWABRDUWHNMW-UHFFFAOYSA-N 0.000 description 1
XYJKFJNFDJZAJY-UHFFFAOYSA-N 2-(4-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XYJKFJNFDJZAJY-UHFFFAOYSA-N 0.000 description 1
HFAYALSSUIQQGG-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfanyl-2,6-bis(2,4-dimethylpentyl)-1,5-dihydroxy-8-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=C(O)C(CC(C)CC(C)C)=CC(SC=4C=CC(=CC=4)C(C)(C)C)=C3C(=O)C2=C(O)C(CC(C)CC(C)C)=CC=1SC1=CC=CC=C1 HFAYALSSUIQQGG-UHFFFAOYSA-N 0.000 description 1
BRBGROGKVKVCEC-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfanyl-2,7-didodecyl-1,8-dihydroxy-5-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC(=CC=4)C(C)(C)C)C=C(CCCCCCCCCCCC)C(O)=C3C(=O)C2=C(O)C(CCCCCCCCCCCC)=CC=1SC1=CC=CC=C1 BRBGROGKVKVCEC-UHFFFAOYSA-N 0.000 description 1
UDXUDPUMJHAHSG-UHFFFAOYSA-N 4-amino-1,8-dihydroxy-5-phenylsulfanyl-2,7-bis(3,5,5-trimethylhexyl)anthracene-9,10-dione Chemical compound C1=C(CCC(C)CC(C)(C)C)C(O)=C2C(=O)C3=C(O)C(CCC(C)CC(C)(C)C)=CC(N)=C3C(=O)C2=C1SC1=CC=CC=C1 UDXUDPUMJHAHSG-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
JKKLDPWAUGKESB-UHFFFAOYSA-N C1=C(CCCCCCCCCCCC)C(O)=C2C(=O)C3=C(O)C(CCCCCCCCCCCC)=CC([N+]([O-])=O)=C3C(=O)C2=C1[N+]([O-])=O Chemical compound C1=C(CCCCCCCCCCCC)C(O)=C2C(=O)C3=C(O)C(CCCCCCCCCCCC)=CC([N+]([O-])=O)=C3C(=O)C2=C1[N+]([O-])=O JKKLDPWAUGKESB-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KCBIWSFMIQVENA-UHFFFAOYSA-N OC1=C(C=C(C=2C(C3C(C(=CC=C3C(C12)=O)CCCCCCCCC)(SC1=C(C=CC=C1)C(C)(C)C)O)=O)SC1=CC=CC=C1)CCCCCCCCC Chemical compound OC1=C(C=C(C=2C(C3C(C(=CC=C3C(C12)=O)CCCCCCCCC)(SC1=C(C=CC=C1)C(C)(C)C)O)=O)SC1=CC=CC=C1)CCCCCCCCC KCBIWSFMIQVENA-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000005352 clarification Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000002019 doping agent Substances 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
229910001635 magnesium fluoride Inorganic materials 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000005693 optoelectronics Effects 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000001259 photo etching Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000010287 polarization Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000001429 visible spectrum Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- 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

Landscapes

Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Physics & Mathematics (AREA)
Organic Chemistry (AREA)
Nonlinear Science (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Liquid Crystal (AREA)
Liquid Crystal Substances (AREA)

DD83254028A 1982-08-18 1983-08-17 Fluessigkristallzusammensetzungen fuer guest-host-fluessigkristallanzeigevorrichtungen DD219498A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8223855		1982-08-18

Publications (1)

Publication Number	Publication Date
DD219498A5 true DD219498A5 (de)	1985-03-06

Family

ID=10532393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83254028A DD219498A5 (de)	1982-08-18	1983-08-17	Fluessigkristallzusammensetzungen fuer guest-host-fluessigkristallanzeigevorrichtungen

Country Status (6)

Country	Link
EP (1)	EP0108472B1 (fr)
JP (1)	JPS5953575A (fr)
KR (1)	KR920002649B1 (fr)
CA (1)	CA1200376A (fr)
DD (1)	DD219498A5 (fr)
DE (1)	DE3380962D1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0103952B1 (fr) *	1982-08-18	1988-12-28	Imperial Chemical Industries Plc	Colorants anthraquinoniques pléochroiques
JP2002327176A (ja)	2001-03-01	2002-11-15	Toshiba Corp	ゲスト−ホスト液晶組成物および液晶表示素子
GB0116788D0 (en)	2001-07-10	2001-08-29	Koninkl Philips Electronics Nv	Colour liquid crystal display devices
JP4169692B2 (ja) *	2001-08-02	2008-10-22	富士フイルム株式会社	アントラキノン化合物、液晶組成物、セル及びそれを用いた表示素子
CN119432401A (zh) *	2024-11-06	2025-02-14	北京八亿时空液晶科技股份有限公司	一种染料pdlc组合物及pdlc调光膜

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
GB2082196B (en) *	1980-07-29	1985-01-23	Secr Defence	Liquid crystal materials containing anthraquinone pleochroic dyes
EP0142617B1 (fr) *	1981-02-25	1987-07-22	Imperial Chemical Industries Plc	Colorants anthraquinoniques pléochroiques
GB2094822B (en) *	1981-02-25	1986-03-05	Ici Plc	Anthraquinone dyes
DE3244815A1 (de) *	1982-12-03	1984-06-07	Bayer Ag, 5090 Leverkusen	Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichroitisches material enthaltend anthrachinonfarbstoffe

1983
- 1983-08-08 EP EP83304569A patent/EP0108472B1/fr not_active Expired
- 1983-08-08 DE DE8383304569T patent/DE3380962D1/de not_active Expired - Lifetime
- 1983-08-16 CA CA000434692A patent/CA1200376A/fr not_active Expired
- 1983-08-17 DD DD83254028A patent/DD219498A5/de not_active IP Right Cessation
- 1983-08-17 JP JP58150115A patent/JPS5953575A/ja active Pending
- 1983-08-18 KR KR1019830003869A patent/KR920002649B1/ko not_active Expired

Also Published As

Publication number	Publication date
EP0108472A2 (fr)	1984-05-16
EP0108472A3 (en)	1986-05-14
EP0108472B1 (fr)	1989-12-13
KR920002649B1 (ko)	1992-03-31
KR840005838A (ko)	1984-11-19
CA1200376A (fr)	1986-02-11
DE3380962D1 (de)	1990-01-18
JPS5953575A (ja)	1984-03-28

Legal Events

Date	Code	Title	Description
1999-04-15	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3009940C2 (fr)	1988-04-14
DE3009974C2 (fr)	1989-06-29
DE2920730C2 (fr)	1990-04-12
DE2356085C2 (de)	1982-10-21	Flüssigkristalline 4'-substituierte 4-Cyanodiphenyle und flüssigkristalline 4"-substituierte 4-Cyanoterphenyle, daraus bestehende flüssigkristalline Materialien und Flüssigkristallgemische und ihre Verwendung
DD200091A5 (de)	1983-03-16	Fluessigkristallzusammensetzungen und ihre verwendung in anzeigevorrichtungen
EP0069257B1 (fr)	1984-09-26	Diélectrique à base de cristaux liquides et dispositif d'affichage électrooptique
CH642345A5 (de)	1984-04-13	2,3-dicyano-hydrochinon derivate.
DE3040102A1 (de)	1982-06-03	Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement
DE2639838A1 (de)	1977-03-17	Optisch aktive cyanodiphenylverbindungen, fluessigkristallmaterialien und fluessigkristallvorrichtungen
DE2617593A1 (de)	1976-11-11	Diphenylderivate und ihre verwendung
EP0047027A1 (fr)	1982-03-10	Mélange de cristaux liquides
EP0093367B1 (fr)	1989-09-13	Colorants anthraquinoniques, leur préparation et utilisation et matériau dichroique contenant ces colorants anthraquinoniques
DD204100A5 (de)	1983-11-16	Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika
DD200090A5 (de)	1983-03-16	Fluessigkristallzusammensetzungen und ihre verwendung in anzeigevorrichtungen
EP0158252B1 (fr)	1988-12-21	Phase liquide cristalline
DE3101290C2 (fr)	1988-02-04
CH645916A5 (de)	1984-10-31	Pleochroitische farbstoffe enthaltende fluessigkristallmassen.
DE3141309C2 (fr)	1991-05-02
DE3510733A1 (de)	1986-09-25	Fluessigkristallphase
DD219498A5 (de)	1985-03-06	Fluessigkristallzusammensetzungen fuer guest-host-fluessigkristallanzeigevorrichtungen
DE3880012T2 (de)	1993-07-15	Fluessigkristallzusammensetzung, die eine verbindung des pleochroic-azo-typs enthaelt.
DE3416515A1 (de)	1984-11-08	Dichroitischer farbstoff fuer fluessigkristall
DE2841245C2 (de)	1986-04-30	Nematische kristallin-flüssige Substanzen
DD209643A5 (de)	1984-05-16	Dielektrische materialien
DE3152228C1 (de)	1985-07-18	2,2'-Azoimidazolderivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung eines fluessigkristallinen Materials