JPH058706B2 - - Google Patents
Info
- Publication number
- JPH058706B2 JPH058706B2 JP59250171A JP25017184A JPH058706B2 JP H058706 B2 JPH058706 B2 JP H058706B2 JP 59250171 A JP59250171 A JP 59250171A JP 25017184 A JP25017184 A JP 25017184A JP H058706 B2 JPH058706 B2 JP H058706B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- phase
- optically active
- pyrimidine
- 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 - Lifetime
Links
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 21
- -1 pyrimidine compound Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 54
- 239000004973 liquid crystal related substance Substances 0.000 description 49
- 239000012071 phase Substances 0.000 description 30
- 230000004044 response Effects 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 230000007704 transition Effects 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000005684 electric field Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004781 supercooling Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 101150078024 CRY2 gene Proteins 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59250171A JPS61129169A (ja) | 1984-11-27 | 1984-11-27 | 液晶化合物 |
| US06/830,530 US4725688A (en) | 1984-06-07 | 1985-05-30 | Liquid crystal compound |
| PCT/JP1985/000302 WO1986000087A1 (en) | 1984-06-07 | 1985-05-30 | Liquid crystal compound |
| EP85902658A EP0191860B1 (de) | 1984-06-07 | 1985-05-30 | Flüssigkristallverbindung |
| DE8585902658T DE3577211D1 (de) | 1984-06-07 | 1985-05-30 | Fluessigkristallverbindung. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59250171A JPS61129169A (ja) | 1984-11-27 | 1984-11-27 | 液晶化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61129169A JPS61129169A (ja) | 1986-06-17 |
| JPH058706B2 true JPH058706B2 (de) | 1993-02-02 |
Family
ID=17203872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59250171A Granted JPS61129169A (ja) | 1984-06-07 | 1984-11-27 | 液晶化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61129169A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3515373A1 (de) * | 1985-04-27 | 1986-11-06 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| DE3518734A1 (de) * | 1985-05-24 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Smektische fluessigkristalline phasen |
| EP0225195B1 (de) * | 1985-12-04 | 1993-11-24 | Ajinomoto Co., Inc. | Verbindungen auf der Basis der Phenylpyrimidine und sie enthaltende flüssigkristalline Zusammensetzungen |
| JP2691405B2 (ja) * | 1987-11-06 | 1997-12-17 | チッソ株式会社 | 強誘電性液晶組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6084232A (ja) * | 1983-09-10 | 1985-05-13 | 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 | 異方性化合物および液晶混合物 |
-
1984
- 1984-11-27 JP JP59250171A patent/JPS61129169A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6084232A (ja) * | 1983-09-10 | 1985-05-13 | 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 | 異方性化合物および液晶混合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61129169A (ja) | 1986-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0533943B2 (de) | ||
| JPH0623135B2 (ja) | 液晶物質及び液晶組成物 | |
| CA2093945C (en) | Carboxylic acid ester compound, liquid crystal material, liquid crystal composition and liquid crystal element | |
| JPS6330300B2 (de) | ||
| JPH058706B2 (de) | ||
| EP0445037A2 (de) | Flüssigkristallverbindung | |
| JPH0425951B2 (de) | ||
| JP3255965B2 (ja) | 反強誘電性液晶化合物 | |
| JPS63165370A (ja) | ピリミジン化合物 | |
| JPH0521106B2 (de) | ||
| JPH0420422B2 (de) | ||
| JPH0420432B2 (de) | ||
| JP2989324B2 (ja) | 新規なナフチルピリジン化合物、これを含む液晶組成物および光スイッチング素子 | |
| JP2663171B2 (ja) | 光学活性化合物及びその用途 | |
| JP2770373B2 (ja) | 液 晶 | |
| JP3101984B2 (ja) | ピラジン誘導体とそれを含む強誘電性液晶組成物 | |
| JP2575782B2 (ja) | 新規な光学活性エステル化合物 | |
| JPH0764828B2 (ja) | 液晶化合物 | |
| JP3249602B2 (ja) | 反強誘電性液晶化合物 | |
| JP3095435B2 (ja) | 液晶化合物 | |
| JPH08253441A (ja) | 五員環中に不斉炭素をもつ液晶化合物およびそれを含む液晶組成物 | |
| JPS61229844A (ja) | ニトロ基を有する化合物および液晶組成物 | |
| JPH03181470A (ja) | ピラジン誘導体 | |
| JPH04368370A (ja) | 新規なフェニルキノリン化合物、これを含む液晶組成物および光スイッチング素子 | |
| JPH06135894A (ja) | 新規なエステル化合物、光学活性体、液晶組成物および光スイッチング素子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term |