JPH0144186B2 - - Google Patents
Info
- Publication number
- JPH0144186B2 JPH0144186B2 JP59190378A JP19037884A JPH0144186B2 JP H0144186 B2 JPH0144186 B2 JP H0144186B2 JP 59190378 A JP59190378 A JP 59190378A JP 19037884 A JP19037884 A JP 19037884A JP H0144186 B2 JPH0144186 B2 JP H0144186B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- picolinic acid
- crystal composition
- fluoro
- cyanophenyl ester
- 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 22
- 239000000203 mixture Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 12
- -1 5-substituted-2-picolinic acid Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- GDNCVJFXNPGRSC-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-butylpyridine-2-carboxylate Chemical compound N1=CC(CCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 GDNCVJFXNPGRSC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JTAKAVLZTSUJLM-UHFFFAOYSA-N (3-chloro-4-cyanophenyl) 5-butoxypyridine-2-carboxylate Chemical compound N1=CC(OCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(Cl)=C1 JTAKAVLZTSUJLM-UHFFFAOYSA-N 0.000 description 1
- ITQSTGXJFNAEIU-UHFFFAOYSA-N (3-chloro-4-cyanophenyl) 5-ethylpyridine-2-carboxylate Chemical compound N1=CC(CC)=CC=C1C(=O)OC1=CC=C(C#N)C(Cl)=C1 ITQSTGXJFNAEIU-UHFFFAOYSA-N 0.000 description 1
- ODKRBRABGIMQFS-UHFFFAOYSA-N (3-chloro-4-cyanophenyl) 5-propoxypyridine-2-carboxylate Chemical compound N1=CC(OCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(Cl)=C1 ODKRBRABGIMQFS-UHFFFAOYSA-N 0.000 description 1
- TZVYOBMWQIBLTO-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-butoxypyridine-2-carboxylate Chemical compound N1=CC(OCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 TZVYOBMWQIBLTO-UHFFFAOYSA-N 0.000 description 1
- IQFJCJSSHOOMPG-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-ethylpyridine-2-carboxylate Chemical compound N1=CC(CC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 IQFJCJSSHOOMPG-UHFFFAOYSA-N 0.000 description 1
- SLHPXHZZHCGECL-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-pentoxypyridine-2-carboxylate Chemical compound N1=CC(OCCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 SLHPXHZZHCGECL-UHFFFAOYSA-N 0.000 description 1
- WEHZWOFVYJTMEW-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-pentylpyridine-2-carboxylate Chemical compound N1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 WEHZWOFVYJTMEW-UHFFFAOYSA-N 0.000 description 1
- ZFOPAHRPZVIDBN-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-propoxypyridine-2-carboxylate Chemical compound N1=CC(OCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 ZFOPAHRPZVIDBN-UHFFFAOYSA-N 0.000 description 1
- NAOITHNWWDORSF-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 5-propylpyridine-2-carboxylate Chemical compound N1=CC(CCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 NAOITHNWWDORSF-UHFFFAOYSA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
-
- 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
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pyridine Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59190378A JPS6168467A (ja) | 1984-09-11 | 1984-09-11 | 正の誘電異方性を有するエステル誘導体 |
| US06/774,945 US4659500A (en) | 1984-09-11 | 1985-09-11 | Ester derivative having a positive dielectric anisotropy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59190378A JPS6168467A (ja) | 1984-09-11 | 1984-09-11 | 正の誘電異方性を有するエステル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6168467A JPS6168467A (ja) | 1986-04-08 |
| JPH0144186B2 true JPH0144186B2 (en]) | 1989-09-26 |
Family
ID=16257174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59190378A Granted JPS6168467A (ja) | 1984-09-11 | 1984-09-11 | 正の誘電異方性を有するエステル誘導体 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4659500A (en]) |
| JP (1) | JPS6168467A (en]) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD227441A1 (de) * | 1984-04-09 | 1985-09-18 | Luther Uni Halle M | Anwendung fluessiger kristalle |
| DE3524489A1 (de) * | 1984-07-12 | 1986-01-23 | Kabushiki Kaisha Suwa Seikosha, Tokio/Tokyo | 2-phenylpyridinderivate und verfahren zu ihrer herstellung |
| DE3518734A1 (de) * | 1985-05-24 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Smektische fluessigkristalline phasen |
| DE3600052A1 (de) * | 1986-01-03 | 1987-07-09 | Merck Patent Gmbh | Heterocyclische verbindungen |
| DE3606787A1 (de) * | 1986-03-01 | 1987-09-03 | Merck Patent Gmbh | Elektrooptisches anzeigeelement |
| JPS62234066A (ja) * | 1986-04-01 | 1987-10-14 | Chisso Corp | フエニルピリジン誘導体 |
| JP2516014B2 (ja) * | 1986-05-24 | 1996-07-10 | チッソ株式会社 | ２−（アルキルオキシカルボニルオキシフエニル）−５−アルキルピリジン及び組成物 |
| CA2042603A1 (en) * | 1989-10-02 | 1991-04-03 | David Coates | Electrooptical liquid crystal system |
| JP6166176B2 (ja) | 2010-04-28 | 2017-07-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体を含む光学的スイッチ素子 |
| JP6166656B2 (ja) | 2010-05-19 | 2017-07-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体を含む光学的スイッチ素子 |
| GB201009488D0 (en) * | 2010-06-07 | 2010-07-21 | Merck Patent Gmbh | Switch element comprising a liquid-crystaline medium |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5490144A (en) * | 1977-11-18 | 1979-07-17 | Dainippon Ink & Chem Inc | 4-n-alkylbenzoxy-3'-chloro-4'-cyanobenzen |
| JPS6055058B2 (ja) * | 1981-11-11 | 1985-12-03 | 大日本インキ化学工業株式会社 | ４−ｎ−アルキルベンゾイルオキシ−３’−フロロ−４’−シアノベンゼン |
| SU1069413A1 (ru) * | 1982-04-11 | 1985-04-23 | Предприятие П/Я А-7850 | Жидкокристаллический материал дл электрооптических устройств |
| SU1063101A1 (ru) * | 1982-04-22 | 1985-06-30 | Предприятие П/Я А-7850 | Жидкокристаллический материал дл электрооптических устройств |
| US4490276A (en) * | 1982-09-20 | 1984-12-25 | Merck Patent Gmbh | Liquid crystal admixtures including chloro-cyanophenyl substituted benzoates |
| DE3315295A1 (de) * | 1983-04-27 | 1984-10-31 | Merck Patent Gmbh, 6100 Darmstadt | Fluorhaltige pyrimidinderivate |
| JPS60149564A (ja) * | 1983-12-20 | 1985-08-07 | Chisso Corp | ２−（β−置換エチル）−５−置換ピリジン |
| JPS60163865A (ja) * | 1984-02-03 | 1985-08-26 | Chisso Corp | ２−置換エチル−５−置換ピリジン |
| DD227441A1 (de) * | 1984-04-09 | 1985-09-18 | Luther Uni Halle M | Anwendung fluessiger kristalle |
| DE3524489A1 (de) * | 1984-07-12 | 1986-01-23 | Kabushiki Kaisha Suwa Seikosha, Tokio/Tokyo | 2-phenylpyridinderivate und verfahren zu ihrer herstellung |
-
1984
- 1984-09-11 JP JP59190378A patent/JPS6168467A/ja active Granted
-
1985
- 1985-09-11 US US06/774,945 patent/US4659500A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6168467A (ja) | 1986-04-08 |
| US4659500A (en) | 1987-04-21 |
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