JPS6121274B2 - - Google Patents
Info
- Publication number
- JPS6121274B2 JPS6121274B2 JP13144578A JP13144578A JPS6121274B2 JP S6121274 B2 JPS6121274 B2 JP S6121274B2 JP 13144578 A JP13144578 A JP 13144578A JP 13144578 A JP13144578 A JP 13144578A JP S6121274 B2 JPS6121274 B2 JP S6121274B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- nematic liquid
- crystal material
- layer
- electrodes
- 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
- 239000000463 material Substances 0.000 claims description 17
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 14
- 239000004973 liquid crystal related substance Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000005684 electric field Effects 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- -1 3-(4-butoxyphenyl)-6-n-pentyl-1,2,4,5-tetrazine Chemical compound 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000001429 visible spectrum Methods 0.000 description 2
- JRNQQLWJXYJSRU-UHFFFAOYSA-N (4-cyanophenyl) 4-pentylcyclohexane-1-carboxylate Chemical compound C1CC(CCCCC)CCC1C(=O)OC1=CC=C(C#N)C=C1 JRNQQLWJXYJSRU-UHFFFAOYSA-N 0.000 description 1
- OYUKHSSBYCYPKP-UHFFFAOYSA-N 3,6-bis(4-octoxyphenyl)-1,2,4,5-tetrazine Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=NN=C(C=2C=CC(OCCCCCCCC)=CC=2)N=N1 OYUKHSSBYCYPKP-UHFFFAOYSA-N 0.000 description 1
- XBDKJRQWPQJHRE-UHFFFAOYSA-N 3-(4-butoxyphenyl)-6-hexyl-1,2,4,5-tetrazine Chemical compound N1=NC(CCCCCC)=NN=C1C1=CC=C(OCCCC)C=C1 XBDKJRQWPQJHRE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FYZWMCWAXFXKLK-UHFFFAOYSA-N 4-nonylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CCCCCCCCCC1=CC=C(C(N)=N)C=C1 FYZWMCWAXFXKLK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMKBLBDMQOYLGP-UHFFFAOYSA-N N1NN=CC=N1 Chemical compound N1NN=CC=N1 PMKBLBDMQOYLGP-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/08—Six-membered rings
-
- 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
- C09K19/3475—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 at least three nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD20336178A DD137117B1 (de) | 1978-01-23 | 1978-01-23 | Nematische kristallin-fluessige substanzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54110185A JPS54110185A (en) | 1979-08-29 |
| JPS6121274B2 true JPS6121274B2 (hu) | 1986-05-26 |
Family
ID=5511327
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13144578A Granted JPS54110185A (en) | 1978-01-23 | 1978-10-25 | Nematic liquid crystal substance |
| JP21114383A Granted JPS59112974A (ja) | 1978-01-23 | 1983-11-11 | 新規のテトラジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21114383A Granted JPS59112974A (ja) | 1978-01-23 | 1983-11-11 | 新規のテトラジン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS54110185A (hu) |
| CH (1) | CH640257A5 (hu) |
| DD (1) | DD137117B1 (hu) |
| DE (1) | DE2841245C2 (hu) |
| FR (1) | FR2422707A1 (hu) |
| GB (1) | GB2014130B (hu) |
| HU (1) | HU186345B (hu) |
| SU (1) | SU956536A1 (hu) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD137118B1 (de) * | 1978-02-06 | 1980-10-01 | Hermann Schubert | Elektrooptische anordnung zur lichtmodulation oder symbolanzeige |
| DD137242B1 (de) * | 1978-06-16 | 1980-10-29 | Dietrich Demus | Nematische kristallin-fluessige mischungen |
| US4358589A (en) * | 1979-02-02 | 1982-11-09 | Veb Werk Fur Fernsehelektronik Im Veb Kombinat Mikroelektronik | Nematic liquid crystal compounds |
| CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
| CH645102A5 (de) * | 1980-10-14 | 1984-09-14 | Hoffmann La Roche | Disubstituierte pyrimidine. |
| FR3085912B1 (fr) | 2018-09-19 | 2020-11-27 | Psa Automobiles Sa | Vehicule comprenant un systeme de repartition d’efforts monte sur le dispositif de pare-chocs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3863010A (en) * | 1973-09-28 | 1975-01-28 | American Cyanamid Co | Compositions of matter and method of use of phenyl and substituted phenyl tetrazines |
| SU498300A1 (ru) * | 1973-11-27 | 1976-01-05 | Институт Органической Химии Ан Украинской Сср | Способ получени производных 3,6-диарил-симм-тетразина |
-
1978
- 1978-01-23 DD DD20336178A patent/DD137117B1/de not_active IP Right Cessation
- 1978-09-22 DE DE19782841245 patent/DE2841245C2/de not_active Expired
- 1978-10-23 FR FR7830116A patent/FR2422707A1/fr active Granted
- 1978-10-25 JP JP13144578A patent/JPS54110185A/ja active Granted
- 1978-10-27 GB GB7842260A patent/GB2014130B/en not_active Expired
- 1978-12-06 HU HUFE001033 patent/HU186345B/hu not_active IP Right Cessation
- 1978-12-19 SU SU787770395A patent/SU956536A1/ru active
-
1979
- 1979-01-16 CH CH39379A patent/CH640257A5/de not_active IP Right Cessation
-
1983
- 1983-11-11 JP JP21114383A patent/JPS59112974A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2841245C2 (de) | 1986-04-30 |
| DE2841245A1 (de) | 1979-07-26 |
| HU186345B (en) | 1985-07-29 |
| GB2014130A (en) | 1979-08-22 |
| DD137117B1 (de) | 1980-10-01 |
| GB2014130B (en) | 1982-07-28 |
| FR2422707B1 (hu) | 1984-02-03 |
| SU956536A1 (ru) | 1982-09-07 |
| FR2422707A1 (fr) | 1979-11-09 |
| CH640257A5 (de) | 1983-12-30 |
| JPS59112974A (ja) | 1984-06-29 |
| DD137117A1 (de) | 1979-08-15 |
| JPS54110185A (en) | 1979-08-29 |
| JPS6133824B2 (hu) | 1986-08-04 |
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