FR2466494A1 - Composition a base de cristal liquide pour dispositif electro-optique - Google Patents
Composition a base de cristal liquide pour dispositif electro-optique Download PDFInfo
- Publication number
- FR2466494A1 FR2466494A1 FR8019879A FR8019879A FR2466494A1 FR 2466494 A1 FR2466494 A1 FR 2466494A1 FR 8019879 A FR8019879 A FR 8019879A FR 8019879 A FR8019879 A FR 8019879A FR 2466494 A1 FR2466494 A1 FR 2466494A1
- Authority
- FR
- France
- Prior art keywords
- anthraquinone
- group
- composition according
- dye
- diamino
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 26
- 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
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 230000003098 cholesteric effect Effects 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- YXPSFIWVUKQCQB-UHFFFAOYSA-N 2,3-diaminoanthracene-1,4-dione Chemical compound C1=CC=C2C=C(C(C(N)=C(N)C3=O)=O)C3=CC2=C1 YXPSFIWVUKQCQB-UHFFFAOYSA-N 0.000 claims 2
- LXXHEFDXGQNZGV-UHFFFAOYSA-N NC1=C(C(=C2C=C3C(C=CC(=C3C=C2C1=O)O)=O)O)N Chemical compound NC1=C(C(=C2C=C3C(C=CC(=C3C=C2C1=O)O)=O)O)N LXXHEFDXGQNZGV-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 239000000243 solution Substances 0.000 description 13
- 238000005259 measurement Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- -1 anthraquinone compounds Chemical class 0.000 description 2
- 239000000987 azo dye Substances 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
- 239000011521 glass Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQJKLTRMSHJEEN-UHFFFAOYSA-N anthracene-1,5-dione Chemical compound O=C1C=CC=C2C=C3C(=O)C=CC=C3C=C21 PQJKLTRMSHJEEN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000019571 color Nutrition 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001916 cyano esters Chemical class 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 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
- 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
- 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
- C09B1/547—Anthraquinones with aromatic ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH886379A CH642393A5 (fr) | 1979-10-02 | 1979-10-02 | Composition a base de cristal liquide pour dispositif electro-optique. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2466494A1 true FR2466494A1 (fr) | 1981-04-10 |
| FR2466494B1 FR2466494B1 (enExample) | 1984-02-03 |
Family
ID=4345612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8019879A Granted FR2466494A1 (fr) | 1979-10-02 | 1980-09-11 | Composition a base de cristal liquide pour dispositif electro-optique |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4428858A (enExample) |
| JP (1) | JPS5657872A (enExample) |
| CH (1) | CH642393A5 (enExample) |
| DE (1) | DE3036853C2 (enExample) |
| FR (1) | FR2466494A1 (enExample) |
| GB (1) | GB2062667B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075173A3 (en) * | 1981-09-18 | 1983-09-21 | Bayer Ag | Anthraquinone dyes |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4360447A (en) * | 1979-03-16 | 1982-11-23 | Mitsui Toatsu Chemicals, Inc. | Composition for liquid crystal color display elements |
| GB2065695B (en) * | 1979-10-12 | 1984-07-25 | Hitachi Ltd | Guest-host type liquid crystal composition and liquid crystal display device using the same |
| JPS5738876A (en) * | 1980-08-21 | 1982-03-03 | Mitsubishi Chem Ind Ltd | Liquid crystal composition |
| 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 |
| 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 |
| 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 |
| JPS5755984A (en) * | 1980-09-22 | 1982-04-03 | Hitachi Ltd | Liquid crystal composition |
| DE3036895C2 (de) * | 1980-09-30 | 1985-07-11 | Merck Patent Gmbh, 6100 Darmstadt | Pleochroitischer Anthrachinon-Farbstoff und Herstellungsverfahren für einen solchen Farbstoff sowie seine Verwendung in einer Flüssigkristallmischung |
| DE3036896A1 (de) * | 1980-09-30 | 1982-04-15 | Siemens AG, 1000 Berlin und 8000 München | Fluessigkristallgemisch mit einem pleochroitischen anthrachinon-farbstoff und verfahren zur herstellung eines solchen farbstoffes |
| 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 |
| JPS57126879A (en) * | 1981-01-12 | 1982-08-06 | Sumitomo Chem Co Ltd | Liquid crystal display element |
| JPS57117581A (en) * | 1981-01-12 | 1982-07-22 | Sumitomo Chem Co Ltd | Liquid crystal display element |
| DE3201120A1 (de) | 1981-01-17 | 1982-10-21 | Hitachi, Ltd., Tokyo | Fluessigkristall-zusammensetzung |
| JPS5876482A (ja) * | 1981-10-30 | 1983-05-09 | Alps Electric Co Ltd | 液晶混合物 |
| DE3202761A1 (de) * | 1982-01-28 | 1983-08-04 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristallines dielektrikum, neue farbstoffe, verfahren zu ihrer herstellung und elektrooptisches anzeigeelement |
| DE3216455A1 (de) * | 1982-05-03 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichtroitisches material enthaltend diese anthrachinonfarbstoffe |
| EP0120463B1 (en) * | 1983-03-23 | 1991-11-06 | Hitachi, Ltd. | Anthraquinone dyes and liquid crystal compositions including the same |
| US7235258B1 (en) | 1999-10-19 | 2007-06-26 | Nps Pharmaceuticals, Inc. | Sustained-release formulations for treating CNS-mediated disorders |
| KR101654019B1 (ko) * | 2011-08-31 | 2016-09-05 | 제이에스알 가부시끼가이샤 | 액정 표시 소자의 제조 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1345397A (fr) * | 1962-01-24 | 1963-12-06 | Ciba Geigy | Colorants anthraquinoniques et procédé pour leur préparation et utilisation |
| GB973262A (en) * | 1961-12-02 | 1964-10-21 | Mitsui Kagaku Kogyo Kabushiki | Improvements in or relating to the dyeing of polyolefin fibrous materials with anthraquinone dyestuffs |
| FR2049197A1 (enExample) * | 1969-06-18 | 1971-03-26 | Bayer Ag |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960751A (en) | 1973-09-19 | 1976-06-01 | Matsushita Electric Industrial Co., Ltd. | Electro-optical display element |
| GB1507030A (en) | 1974-10-21 | 1978-04-12 | Secr Defence | Liquid crystal display devices |
| JPS53126033A (en) | 1977-04-11 | 1978-11-02 | Minnesota Mining & Mfg | Multiicolored dyestuff and electrooptical device |
| FR2426724B1 (fr) | 1978-05-23 | 1985-09-27 | Minnesota Mining & Mfg | Composition a base de colorants anthraquinoniques pleochroiques et son application a des dispositifs electro-optiques d'affichage |
| CH638828A5 (de) | 1978-12-21 | 1983-10-14 | Bbc Brown Boveri & Cie | Fluessigkristallmischung. |
| DE2902177A1 (de) | 1978-12-21 | 1980-07-17 | 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. |
| GB2065695B (en) | 1979-10-12 | 1984-07-25 | Hitachi Ltd | Guest-host type liquid crystal composition and liquid crystal display device using the same |
| 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 |
-
1979
- 1979-10-02 CH CH886379A patent/CH642393A5/fr not_active IP Right Cessation
-
1980
- 1980-09-11 US US06/186,138 patent/US4428858A/en not_active Expired - Lifetime
- 1980-09-11 FR FR8019879A patent/FR2466494A1/fr active Granted
- 1980-09-18 GB GB8030150A patent/GB2062667B/en not_active Expired
- 1980-09-30 JP JP13533980A patent/JPS5657872A/ja active Granted
- 1980-09-30 DE DE3036853A patent/DE3036853C2/de not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB973262A (en) * | 1961-12-02 | 1964-10-21 | Mitsui Kagaku Kogyo Kabushiki | Improvements in or relating to the dyeing of polyolefin fibrous materials with anthraquinone dyestuffs |
| FR1345397A (fr) * | 1962-01-24 | 1963-12-06 | Ciba Geigy | Colorants anthraquinoniques et procédé pour leur préparation et utilisation |
| FR2049197A1 (enExample) * | 1969-06-18 | 1971-03-26 | Bayer Ag |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/76 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075173A3 (en) * | 1981-09-18 | 1983-09-21 | Bayer Ag | Anthraquinone dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| CH642393A5 (fr) | 1984-04-13 |
| DE3036853C2 (de) | 1986-07-31 |
| FR2466494B1 (enExample) | 1984-02-03 |
| DE3036853A1 (de) | 1981-04-09 |
| JPS6346120B2 (enExample) | 1988-09-13 |
| JPS5657872A (en) | 1981-05-20 |
| US4428858A (en) | 1984-01-31 |
| GB2062667B (en) | 1984-08-30 |
| GB2062667A (en) | 1981-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property | ||
| ST | Notification of lapse |