JPS6346120B2 - - Google Patents
Info
- Publication number
- JPS6346120B2 JPS6346120B2 JP55135339A JP13533980A JPS6346120B2 JP S6346120 B2 JPS6346120 B2 JP S6346120B2 JP 55135339 A JP55135339 A JP 55135339A JP 13533980 A JP13533980 A JP 13533980A JP S6346120 B2 JPS6346120 B2 JP S6346120B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- anthraquinone
- composition according
- formula
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 28
- 239000000975 dye Substances 0.000 claims description 17
- -1 anthraquinone compound Chemical class 0.000 claims description 10
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000001000 anthraquinone dye Substances 0.000 claims description 6
- 150000004056 anthraquinones Chemical group 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical group 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 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 3
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 claims 2
- HSYLKWSCFRLSKB-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(O)=C2C(=O)C2=C1C(O)=CC=C2N HSYLKWSCFRLSKB-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- HNRGOVGFMBHMNW-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonitrile Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1C#N HNRGOVGFMBHMNW-UHFFFAOYSA-N 0.000 claims 1
- 239000004988 Nematic liquid crystal Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- 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 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 description 1
- RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 description 1
- DNJQGRFZQMOYGM-UHFFFAOYSA-N 4-[4-(2-methylbutyl)phenyl]benzonitrile Chemical compound C1=CC(CC(C)CC)=CC=C1C1=CC=C(C#N)C=C1 DNJQGRFZQMOYGM-UHFFFAOYSA-N 0.000 description 1
- GQJHPVOLXNKXKB-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 GQJHPVOLXNKXKB-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 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 |
|---|---|
| JPS5657872A JPS5657872A (en) | 1981-05-20 |
| JPS6346120B2 true JPS6346120B2 (enExample) | 1988-09-13 |
Family
ID=4345612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13533980A Granted JPS5657872A (en) | 1979-10-02 | 1980-09-30 | Liquid crystal composition for electrooptical device |
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) |
Families Citing this family (22)
| 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 |
| DE3137298A1 (de) * | 1981-09-18 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226177A (en) | 1961-12-02 | 1965-12-28 | Mitsui Kagaku Kogyo Kabushiki | Process for the dyeing of polyolefin fibrous materials |
| BE627438A (enExample) * | 1962-01-24 | 1900-01-01 | ||
| DE1930777A1 (de) * | 1969-06-18 | 1971-02-04 | Bayer Ag | Verfahren zum kontinuierlichen Faerben synthetischer Fasermaterialien |
| 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
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 |
| FR2466494A1 (fr) | 1981-04-10 |
| JPS5657872A (en) | 1981-05-20 |
| US4428858A (en) | 1984-01-31 |
| GB2062667B (en) | 1984-08-30 |
| GB2062667A (en) | 1981-05-28 |
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