CA1168037A - Liquid crystal materials with pleochroic dyes - Google Patents
Liquid crystal materials with pleochroic dyesInfo
- Publication number
- CA1168037A CA1168037A CA000382705A CA382705A CA1168037A CA 1168037 A CA1168037 A CA 1168037A CA 000382705 A CA000382705 A CA 000382705A CA 382705 A CA382705 A CA 382705A CA 1168037 A CA1168037 A CA 1168037A
- Authority
- CA
- Canada
- Prior art keywords
- liquid crystal
- formula
- dye
- compound
- groups
- 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
Links
- 239000000463 material Substances 0.000 title claims abstract description 129
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 74
- 239000000975 dye Substances 0.000 title claims description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 24
- -1 1,5-dihydroxy-4,8-diamino-2-(4'-hydroxyphenyl)-6-hydroxy-methylanthraquinone Chemical compound 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 230000008859 change Effects 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 239000001044 red dye Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001043 yellow dye Substances 0.000 claims description 7
- 230000003098 cholesteric effect Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 239000003989 dielectric material Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 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 5
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001045 blue dye Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 claims description 3
- ZHZMDMCKNWGPFB-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-2,6-bis(2-methylpropyl)anthracene-9,10-dione Chemical compound CC(C)CC1=CC(N)=C2C(=O)C3=C(O)C(CC(C)C)=CC(N)=C3C(=O)C2=C1O ZHZMDMCKNWGPFB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- CZJZMSRDRZJNSB-UHFFFAOYSA-N 4,5-diamino-1,8-dihydroxy-2,7-bis(2-methylpropyl)anthracene-9,10-dione Chemical compound C1=C(CC(C)C)C(O)=C2C(=O)C3=C(O)C(CC(C)C)=CC(N)=C3C(=O)C2=C1N CZJZMSRDRZJNSB-UHFFFAOYSA-N 0.000 claims description 2
- IATNWROSDJPVSJ-UHFFFAOYSA-N 4,5-diamino-1,8-dihydroxy-2,7-di(nonyl)anthracene-9,10-dione Chemical compound C1=C(CCCCCCCCC)C(O)=C2C(=O)C3=C(O)C(CCCCCCCCC)=CC(N)=C3C(=O)C2=C1N IATNWROSDJPVSJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- YUAMKDUXOKSJME-UHFFFAOYSA-N 4,5-diamino-1,8-dihydroxy-2,7-bis(2-methylpropyl)anthracene-9,10-dione;4,8-diamino-1,5-dihydroxy-2,6-bis(2-methylpropyl)anthracene-9,10-dione;4,5-diamino-1,8-dihydroxy-2,7-di(nonyl)anthracene-9,10-dione Chemical compound CC(C)CC1=CC(N)=C2C(=O)C3=C(O)C(CC(C)C)=CC(N)=C3C(=O)C2=C1O.C1=C(CC(C)C)C(O)=C2C(=O)C3=C(O)C(CC(C)C)=CC(N)=C3C(=O)C2=C1N.C1=C(CCCCCCCCC)C(O)=C2C(=O)C3=C(O)C(CCCCCCCCC)=CC(N)=C3C(=O)C2=C1N YUAMKDUXOKSJME-UHFFFAOYSA-N 0.000 claims 2
- JQJPUPWFDZQCSZ-UHFFFAOYSA-N 4,8-diamino-1,5-dihydroxy-2-(hydroxymethyl)-6-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound OC1=C2C(=O)C=3C(N)=CC(CO)=C(O)C=3C(=O)C2=C(N)C=C1C1=CC=C(O)C=C1 JQJPUPWFDZQCSZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 12
- 230000005684 electric field Effects 0.000 description 9
- 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 8
- 210000004027 cell Anatomy 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001934 cyclohexanes Chemical group 0.000 description 2
- 229960001577 dantron Drugs 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009467 reduction 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
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CUIHODIOWPLCMG-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O CUIHODIOWPLCMG-UHFFFAOYSA-N 0.000 description 1
- LSOIXWNPSSEXDZ-UHFFFAOYSA-N 1,8-dihydroxy-2,7-bis(2-methylpropyl)anthracene-9,10-dione Chemical compound C1=C(CC(C)C)C(O)=C2C(=O)C3=C(O)C(CC(C)C)=CC=C3C(=O)C2=C1 LSOIXWNPSSEXDZ-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
- JGWWBSUUFGBHCH-UHFFFAOYSA-N 2-phenylpyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2C=CC=CC=2)=N1 JGWWBSUUFGBHCH-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 244000171726 Scotch broom Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 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
- 238000000149 argon plasma sintering Methods 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 101150072047 nei1 gene Proteins 0.000 description 1
- 101150008002 nei2 gene Proteins 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method 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
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
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- 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)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8024761 | 1980-07-29 | ||
| GB8024761 | 1980-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1168037A true CA1168037A (en) | 1984-05-29 |
Family
ID=10515107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000382705A Expired CA1168037A (en) | 1980-07-29 | 1981-07-28 | Liquid crystal materials with pleochroic dyes |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4391489A (enExample) |
| EP (1) | EP0049036B1 (enExample) |
| JP (1) | JPS5773068A (enExample) |
| KR (1) | KR840001847B1 (enExample) |
| AT (1) | ATE10202T1 (enExample) |
| CA (1) | CA1168037A (enExample) |
| DD (1) | DD200090A5 (enExample) |
| DE (1) | DE3167077D1 (enExample) |
| HK (1) | HK100585A (enExample) |
| MY (1) | MY8700224A (enExample) |
| SG (1) | SG65985G (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2065695B (en) * | 1979-10-12 | 1984-07-25 | Hitachi Ltd | Guest-host type liquid crystal composition and liquid crystal display device using the same |
| 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 |
| US4391754A (en) * | 1980-07-29 | 1983-07-05 | Imperial Chemical Industries Plc | Anthraquinone compounds |
| DE3040102A1 (de) * | 1980-10-24 | 1982-06-03 | Merck Patent Gmbh, 6100 Darmstadt | Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
| JPS57126879A (en) * | 1981-01-12 | 1982-08-06 | Sumitomo Chem Co Ltd | Liquid crystal display element |
| GB2094825B (en) * | 1981-01-17 | 1984-09-12 | Mitsubishi Chem Ind | Liquid crystal compositions containing pleochroic anthraquinone dyes |
| DE3276180D1 (de) * | 1981-02-25 | 1987-06-04 | Secr Defence Brit | Liquid crystal materials comprising pleochroic dyes |
| 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 |
| JPS5825381A (ja) * | 1981-08-08 | 1983-02-15 | Nippon Kanko Shikiso Kenkyusho:Kk | 液晶組成物 |
| DE3366521D1 (en) * | 1982-04-07 | 1986-11-06 | Secr Defence Brit | Dielectric materials |
| DE3378636D1 (en) * | 1982-04-07 | 1989-01-12 | Ici Plc | Anthraquinone compounds |
| DE3216455A1 (de) * | 1982-05-03 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichtroitisches material enthaltend diese anthrachinonfarbstoffe |
| JPS5927956A (ja) * | 1982-07-17 | 1984-02-14 | バイエル・アクチエンゲゼルシヤフト | アントラキノン染料を含む二色性物質及び新規なアントラキノン染料 |
| DE3378767D1 (de) * | 1982-08-18 | 1989-02-02 | Ici Plc | Pleochroic anthraquinone dyes |
| SU1594189A1 (ru) * | 1986-10-24 | 1990-09-23 | Предприятие П/Я А-7850 | Производные 1-аминоантрахинона в качестве красител с отрицательным дихроизмом дл жидких кристаллов и жидкокристаллический материал дл электрооптических устройств на его основе |
| EP1400980A1 (en) * | 2002-09-17 | 2004-03-24 | STMicroelectronics S.r.l. | A circuit for biasing an input node of a sense amplifier with a pre-charging stage |
| TWI604527B (zh) * | 2016-11-29 | 2017-11-01 | 明基材料股份有限公司 | 液晶裝置的製造方法與由此方法所製造出之液晶裝置 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB2024844B (en) * | 1978-05-23 | 1983-03-30 | Minnesota Mining & Mfg | Pleochroic dyes and electro-optical displays therewith |
| DE2902177A1 (de) * | 1978-12-21 | 1980-07-17 | Bbc Brown Boveri & Cie | Fluessigkristallmischung |
| CH638828A5 (de) * | 1978-12-21 | 1983-10-14 | Bbc Brown Boveri & Cie | Fluessigkristallmischung. |
| CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
| US4232949A (en) * | 1979-02-23 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Liquid crystal compositions containing pleochroic dye |
| US4232950A (en) * | 1979-02-23 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Liquid crystal compositions including pleochroic dye |
| 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 |
| CH641828A5 (fr) * | 1979-08-17 | 1984-03-15 | Ebauches Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
| EP0025809A1 (de) * | 1979-09-21 | 1981-04-01 | BBC Aktiengesellschaft Brown, Boveri & Cie. | Flüssigkristallmischung |
| 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 |
| JPS56100885A (en) * | 1980-01-17 | 1981-08-13 | Mitsui Toatsu Chem Inc | Composition for liquid crystal color display |
| 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 |
| DE3014933A1 (de) * | 1980-04-18 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| GB2082196B (en) * | 1980-07-29 | 1985-01-23 | Secr Defence | Liquid crystal materials containing anthraquinone pleochroic 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 |
| US4391754A (en) * | 1980-07-29 | 1983-07-05 | Imperial Chemical Industries Plc | Anthraquinone compounds |
| EP0044893B1 (en) * | 1980-07-29 | 1984-09-19 | Imperial Chemical Industries Plc | Anthraquinone compounds and process for their preparation |
-
1981
- 1981-07-27 US US06/287,123 patent/US4391489A/en not_active Expired - Lifetime
- 1981-07-28 JP JP56118397A patent/JPS5773068A/ja active Granted
- 1981-07-28 DE DE8181303472T patent/DE3167077D1/de not_active Expired
- 1981-07-28 EP EP81303472A patent/EP0049036B1/en not_active Expired
- 1981-07-28 AT AT81303472T patent/ATE10202T1/de not_active IP Right Cessation
- 1981-07-28 CA CA000382705A patent/CA1168037A/en not_active Expired
- 1981-07-28 KR KR8102741A patent/KR840001847B1/ko not_active Expired
- 1981-07-29 DD DD81232182A patent/DD200090A5/de not_active IP Right Cessation
-
1983
- 1983-04-13 US US06/484,603 patent/US4483594A/en not_active Expired - Lifetime
-
1985
- 1985-09-09 SG SG659/85A patent/SG65985G/en unknown
- 1985-12-18 HK HK1005/85A patent/HK100585A/xx not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY224/87A patent/MY8700224A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4391489A (en) | 1983-07-05 |
| KR840001847B1 (en) | 1984-10-22 |
| ATE10202T1 (de) | 1984-11-15 |
| EP0049036A1 (en) | 1982-04-07 |
| KR830006401A (ko) | 1983-09-24 |
| MY8700224A (en) | 1987-12-31 |
| HK100585A (en) | 1985-12-27 |
| JPS5773068A (en) | 1982-05-07 |
| DD200090A5 (de) | 1983-03-16 |
| US4483594A (en) | 1984-11-20 |
| DE3167077D1 (en) | 1984-12-13 |
| EP0049036B1 (en) | 1984-11-07 |
| SG65985G (en) | 1986-11-21 |
| JPH0225949B2 (enExample) | 1990-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |