DE3703651A1 - Kristallin-fluessige gemische mit negativer dielektrischer anisotropie - Google Patents
Kristallin-fluessige gemische mit negativer dielektrischer anisotropieInfo
- Publication number
- DE3703651A1 DE3703651A1 DE19873703651 DE3703651A DE3703651A1 DE 3703651 A1 DE3703651 A1 DE 3703651A1 DE 19873703651 DE19873703651 DE 19873703651 DE 3703651 A DE3703651 A DE 3703651A DE 3703651 A1 DE3703651 A1 DE 3703651A1
- Authority
- DE
- Germany
- Prior art keywords
- crystalline
- liquid
- trans
- dielectric anisotropy
- contain
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 239000000126 substance Substances 0.000 claims abstract description 15
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- 239000000975 dye Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000005352 clarification Methods 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 4
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical class ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 4
- 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 claims 2
- 238000000034 method Methods 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 4-substituted-phenyl Chemical group 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical compound C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- GBKDCKUFKOVLBI-UHFFFAOYSA-N 4-butylcyclohexane-1-carbohydrazide Chemical compound CCCCC1CCC(C(=O)NN)CC1 GBKDCKUFKOVLBI-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- OYFBUAXJLRAPEW-UBBSCCEASA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN1)[C@@H]1CC[C@H](CC1)CCCC OYFBUAXJLRAPEW-UBBSCCEASA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OUOWCSJYDCPVDM-UHFFFAOYSA-N 4-butylbenzoyl chloride Chemical compound CCCCC1=CC=C(C(Cl)=O)C=C1 OUOWCSJYDCPVDM-UHFFFAOYSA-N 0.000 description 1
- ZHJCVLQOKPGYDJ-UHFFFAOYSA-N 4-butylcyclohexane-1-carbonyl chloride Chemical compound CCCCC1CCC(C(Cl)=O)CC1 ZHJCVLQOKPGYDJ-UHFFFAOYSA-N 0.000 description 1
- HPJDDPSWQZSHQH-UHFFFAOYSA-N 4-heptylcyclohexane-1-carbonyl chloride Chemical compound CCCCCCCC1CCC(C(Cl)=O)CC1 HPJDDPSWQZSHQH-UHFFFAOYSA-N 0.000 description 1
- WNCUHHQSGMACFL-HZCBDIJESA-N BrC=1C=C(C=CC=1OCCCCCCCCC)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound BrC=1C=C(C=CC=1OCCCCCCCCC)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCC WNCUHHQSGMACFL-HZCBDIJESA-N 0.000 description 1
- NLWNOUGZCBOKFH-AQYVVDRMSA-N C(CCC)C1=CC=C(C=C1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC Chemical compound C(CCC)C1=CC=C(C=C1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC NLWNOUGZCBOKFH-AQYVVDRMSA-N 0.000 description 1
- KLWGEWUEZXUROR-XUTJKUGGSA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC KLWGEWUEZXUROR-XUTJKUGGSA-N 0.000 description 1
- ZAPXYRNJDDXYBJ-KBQPQWKXSA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCCC ZAPXYRNJDDXYBJ-KBQPQWKXSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD28758186A DD247694A1 (de) | 1986-03-05 | 1986-03-05 | Kristallin-fluessige gemische |
| DD28759286A DD247221A1 (de) | 1986-03-05 | 1986-03-05 | Verfahren zur herstellung 2,5-disubstituierter 1,3,4-thiadiazolderivate mit trans-cyclohexanstrukturfragmenten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3703651A1 true DE3703651A1 (de) | 1987-09-10 |
Family
ID=25748035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873703651 Withdrawn DE3703651A1 (de) | 1986-03-05 | 1987-02-06 | Kristallin-fluessige gemische mit negativer dielektrischer anisotropie |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH670639A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| DE (1) | DE3703651A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008019A1 (en) * | 1987-04-16 | 1988-10-20 | MERCK Patent Gesellschaft mit beschränkter Haftung | Media containing derivatives of thiazole and thiadiazole, with smectic liquid-crystal phase |
| FR2617496A1 (fr) * | 1987-07-01 | 1989-01-06 | Werk Fernsehelektronik Veb | Cristaux liquides 1, 3, 4 - thiadiazoles disubstitues en 2,5 ayant une phase c smectique etendue |
| EP0332024A1 (de) * | 1988-03-10 | 1989-09-13 | MERCK PATENT GmbH | Heterocyclische Derivate des 1,2-Difluorbenzols |
| DE4021811A1 (de) * | 1989-07-10 | 1991-01-17 | Canon Kk | Mesomorphe verbindung, fluessigkristallmischung, die diese enthaelt, und fluessigkristallvorrichtung, bei der diese verwendet wird |
| US5143642A (en) * | 1990-01-13 | 1992-09-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline medium for electrooptical display elements based on the ECB effect |
| US5478496A (en) * | 1987-04-16 | 1995-12-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Media containing thiazole derivatives and thiadiazole derivatives and having a smectic liquid-crystalline phase |
| US5800736A (en) * | 1994-12-29 | 1998-09-01 | Chisso Corporation | Smectic liquid crystal composition and liquid crystal device |
| DE3712995B4 (de) * | 1987-04-16 | 2004-02-05 | Qinetiq Ltd. | Thiazol- und Thiadiazol-Derivate enthaltende Medien mit smektischer flüssigkristalliner Phase und die Verwendung dieser Medien in elektrooptischen Anzeigeelementen |
-
1987
- 1987-02-06 DE DE19873703651 patent/DE3703651A1/de not_active Withdrawn
- 1987-02-12 CH CH56187A patent/CH670639A5/de not_active IP Right Cessation
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478496A (en) * | 1987-04-16 | 1995-12-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Media containing thiazole derivatives and thiadiazole derivatives and having a smectic liquid-crystalline phase |
| DE3712995B4 (de) * | 1987-04-16 | 2004-02-05 | Qinetiq Ltd. | Thiazol- und Thiadiazol-Derivate enthaltende Medien mit smektischer flüssigkristalliner Phase und die Verwendung dieser Medien in elektrooptischen Anzeigeelementen |
| JP3302356B2 (ja) | 1987-04-16 | 2002-07-15 | グレートブリテン及び北部アイルランド連合王国 | チアゾール誘導体およびチアジアゾール誘導体を含有しそしてスメクテイツク液晶相を有するメジウム |
| WO1988008019A1 (en) * | 1987-04-16 | 1988-10-20 | MERCK Patent Gesellschaft mit beschränkter Haftung | Media containing derivatives of thiazole and thiadiazole, with smectic liquid-crystal phase |
| JPS6461472A (en) * | 1987-07-01 | 1989-03-08 | Werk Fernsehelektronik Veb | Liquid crystal 2,5-disubstituted-1,3,5-thiadiazole showing smetic c-phase in broad range |
| JP2880169B2 (ja) | 1987-07-01 | 1999-04-05 | サムスング・エレクトロン・デイバイセス・カンパニー・リミテツド | 広範囲にわたつてスメチツクｃ‐相を示す液晶２，５‐二置換１，３，５‐チアジアゾール |
| DE3819972A1 (de) * | 1987-07-01 | 1989-01-12 | Werk Fernsehelektronik Veb | 2,5-disubstituierte 1,3,4-thiadiazole mit ausgedehnten smektischen c-phasen, herstellung und verwendung in ferroelektrischen, fluessig-kristallinen mischungen |
| FR2617496A1 (fr) * | 1987-07-01 | 1989-01-06 | Werk Fernsehelektronik Veb | Cristaux liquides 1, 3, 4 - thiadiazoles disubstitues en 2,5 ayant une phase c smectique etendue |
| WO1989008649A1 (en) * | 1988-03-10 | 1989-09-21 | MERCK Patent Gesellschaft mit beschränkter Haftung | Heterocyclic 1,2-difluorobenzene derivatives |
| EP0332024A1 (de) * | 1988-03-10 | 1989-09-13 | MERCK PATENT GmbH | Heterocyclische Derivate des 1,2-Difluorbenzols |
| DE4021811A1 (de) * | 1989-07-10 | 1991-01-17 | Canon Kk | Mesomorphe verbindung, fluessigkristallmischung, die diese enthaelt, und fluessigkristallvorrichtung, bei der diese verwendet wird |
| US5076961A (en) * | 1989-07-10 | 1991-12-31 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same |
| US5143642A (en) * | 1990-01-13 | 1992-09-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline medium for electrooptical display elements based on the ECB effect |
| US5800736A (en) * | 1994-12-29 | 1998-09-01 | Chisso Corporation | Smectic liquid crystal composition and liquid crystal device |
Also Published As
| Publication number | Publication date |
|---|---|
| CH670639A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee | ||
| 8180 | Miscellaneous part 1 |
Free format text: IM HEFT 7/92, SEITE 1740, SP.1: DIE VEROEFFENTLICHUNG IST ZU STREICHEN |
|
| 8130 | Withdrawal |