JPS6152141B2 - - Google Patents
Info
- Publication number
- JPS6152141B2 JPS6152141B2 JP4432983A JP4432983A JPS6152141B2 JP S6152141 B2 JPS6152141 B2 JP S6152141B2 JP 4432983 A JP4432983 A JP 4432983A JP 4432983 A JP4432983 A JP 4432983A JP S6152141 B2 JPS6152141 B2 JP S6152141B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- threshold voltage
- substituted
- 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
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- -1 For example Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- DPSSSDFTLVUJDH-UHFFFAOYSA-N 3-fluoro-4-hydroxybenzonitrile Chemical class OC1=CC=C(C#N)C=C1F DPSSSDFTLVUJDH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4432983A JPS59170056A (ja) | 1983-03-18 | 1983-03-18 | 新規ネマチツク液晶化合物 |
| GB08328731A GB2132192B (en) | 1982-10-30 | 1983-10-27 | Nematic liquid crystalline 3-fluro-4-cyanophenol derivatives |
| US06/546,534 US4551280A (en) | 1982-10-30 | 1983-10-28 | Nematic liquid crystalline compounds |
| DE3339216A DE3339216C2 (de) | 1982-10-30 | 1983-10-28 | 3-Fluor-4-cyanophenol-Derivate und deren Verwendung |
| CH5883/83A CH654829A5 (de) | 1982-10-30 | 1983-10-31 | 3-fluor-4-cyanophenol-derivate. |
| US06/744,978 US4673756A (en) | 1982-10-30 | 1985-06-17 | Nematic liquid crystalline compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4432983A JPS59170056A (ja) | 1983-03-18 | 1983-03-18 | 新規ネマチツク液晶化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59170056A JPS59170056A (ja) | 1984-09-26 |
| JPS6152141B2 true JPS6152141B2 (US20080094685A1-20080424-C00004.png) | 1986-11-12 |
Family
ID=12688462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4432983A Granted JPS59170056A (ja) | 1982-10-30 | 1983-03-18 | 新規ネマチツク液晶化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59170056A (US20080094685A1-20080424-C00004.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6425648U (US20080094685A1-20080424-C00004.png) * | 1987-08-05 | 1989-02-13 | ||
| JPS6425647U (US20080094685A1-20080424-C00004.png) * | 1987-08-05 | 1989-02-13 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8314077D0 (en) * | 1983-05-20 | 1983-06-29 | Secr Defence | Disubstituted ethanes |
| DE10116400A1 (de) * | 2000-04-28 | 2001-12-06 | Merck Patent Gmbh | Elektrooptische Anzeige und darin enthaltenes Flüssigkristallmedium |
-
1983
- 1983-03-18 JP JP4432983A patent/JPS59170056A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6425648U (US20080094685A1-20080424-C00004.png) * | 1987-08-05 | 1989-02-13 | ||
| JPS6425647U (US20080094685A1-20080424-C00004.png) * | 1987-08-05 | 1989-02-13 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59170056A (ja) | 1984-09-26 |
