JPS6334861B2 - - Google Patents
Info
- Publication number
- JPS6334861B2 JPS6334861B2 JP54099396A JP9939679A JPS6334861B2 JP S6334861 B2 JPS6334861 B2 JP S6334861B2 JP 54099396 A JP54099396 A JP 54099396A JP 9939679 A JP9939679 A JP 9939679A JP S6334861 B2 JPS6334861 B2 JP S6334861B2
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- liquid crystalline
- crystalline compound
- formula
- group
- 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 56
- 239000004973 liquid crystal related substance Substances 0.000 claims description 42
- 239000007788 liquid Substances 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- -1 biphenylyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 230000005684 electric field Effects 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000012071 phase Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000003098 cholesteric effect Effects 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000010287 polarization Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical class C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/321—Compounds containing a bicyclo [2,2,2] octane ring
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7832351 | 1978-08-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5524174A JPS5524174A (en) | 1980-02-21 |
| JPS6334861B2 true JPS6334861B2 (en, 2012) | 1988-07-12 |
Family
ID=10498877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9939679A Granted JPS5524174A (en) | 1978-08-04 | 1979-08-03 | Liquid crystal compound |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4261652A (en, 2012) |
| JP (1) | JPS5524174A (en, 2012) |
| CH (1) | CH646683A5 (en, 2012) |
| DE (1) | DE2931637A1 (en, 2012) |
| FR (1) | FR2432546A1 (en, 2012) |
| HK (1) | HK100785A (en, 2012) |
| MY (1) | MY8700203A (en, 2012) |
| SG (1) | SG80885G (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357078A (en) * | 1980-01-30 | 1982-11-02 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compounds containing an alicyclic ring and exhibiting a low dielectric anisotropy and liquid crystal materials and devices incorporating such compounds |
| US4400061A (en) * | 1980-01-30 | 1983-08-23 | Her Majesty's Government of the UK. | Liquid crystal ester compounds exhibiting a low or negative dielectric anisotropy and liquid crystal materials and devices incorporating such compounds |
| JPS574960A (en) * | 1980-06-09 | 1982-01-11 | Chisso Corp | 4'''-cyanobiphenyl trans-4-(trans-4'-alkylcyclohexyl)- cyclohexanecarboxylate |
| DE3022818C2 (de) * | 1980-06-19 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Flüssigkristall-Anzeigeelement |
| JPS5721359A (en) * | 1980-07-15 | 1982-02-04 | Chisso Corp | 4'''-cyano-4"-biphenylyl 4-(trans-4'-alkylcyclohexyl)benzoate |
| EP0058981B1 (en) * | 1981-02-25 | 1986-01-22 | Hitachi, Ltd. | Colorless liquid crystalline compounds |
| DE3362830D1 (en) * | 1982-02-04 | 1986-05-15 | Merck Patent Gmbh | Anisotropic compounds and liquid crystal compositions |
| JPS58140045A (ja) * | 1982-02-15 | 1983-08-19 | Kanto Kagaku Kk | 液晶化合物，液晶組成物並びに液晶表示素子 |
| DE3206269A1 (de) * | 1982-02-20 | 1983-09-01 | Merck Patent Gmbh, 6100 Darmstadt | Bicyclohexylderivate |
| DE3211601A1 (de) * | 1982-03-30 | 1983-10-06 | Merck Patent Gmbh | Hydroterphenyle |
| US4502974A (en) * | 1982-03-31 | 1985-03-05 | Chisso Corporation | High temperature liquid-crystalline ester compounds |
| US4472592A (en) * | 1982-07-09 | 1984-09-18 | Dainippon Ink And Chemicals, Inc. | Nematic liquid crystalline compounds |
| CH649988A5 (de) * | 1982-07-13 | 1985-06-28 | Merck Patent Gmbh | Nematogene verbindungen und fluessigkristallmischungen mit diesen. |
| DE3364938D1 (en) * | 1982-07-28 | 1986-09-04 | Hoffmann La Roche | Tetra- and pentacyclic monoesters |
| DE3382646D1 (de) * | 1982-08-26 | 1993-01-28 | Merck Patent Gmbh | Cyclohexanderivate und ihre verwendung als komponenten fluessigkristalliner-dielektrika. |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| CH653051A5 (de) * | 1983-01-27 | 1985-12-13 | Merck Patent Gmbh | Nematische fluessigkristallmischung mit einer negativen dielektrischen anisotropie. |
| EP0144648B1 (de) * | 1983-11-02 | 1987-10-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristalline Cyclohexylbenzol- und Cyclohexylbiphenylderivate |
| US4605510A (en) * | 1985-01-25 | 1986-08-12 | Nauchno-Issledovatelsky Institut Prikladnykh Problem Imeni A.N. Sevchenko | Liquid crystal composition for electrooptical devices for presentation of information |
| US4605520A (en) * | 1985-01-25 | 1986-08-12 | Nauchno-Issledovatelsky Institut Prikladnykh Fizicheskikh Problem Imeni A.N. Sevchenko | Liquid crystal 4-(4'-cyanodiphenyl) esters of trans-4"-N-alkylocyclohex-2-enecarboxylic acids |
| JPS61233635A (ja) * | 1985-03-22 | 1986-10-17 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ビシクロオクタン誘導体 |
| US4680137A (en) * | 1985-06-10 | 1987-07-14 | Chisso Corporation | Liquid crystal ester compound |
| CA1294954C (en) * | 1986-12-26 | 1992-01-28 | Masakatsu Nakatsuka | Optically active naphthalene derivatives |
| TW472081B (en) * | 1996-09-17 | 2002-01-11 | Merck Patent Gmbh | Optical retardation film |
| GB9620108D0 (en) * | 1996-09-26 | 1996-11-13 | Secr Defence | Liquid crystal alkenyl bicyclo[2 2 2]octanes and mixtures and devices containing such compounds |
| JP5422898B2 (ja) * | 2007-03-08 | 2014-02-19 | Ｊｎｃ株式会社 | ハロゲン化アルキル基と結合した２，２，２−ビシクロオクタンを有する新規な化合物およびこれを用いた液晶組成物 |
| JP2010215523A (ja) * | 2009-03-13 | 2010-09-30 | Fujifilm Corp | フルオロビシクロ［２．２．２］−２−オクテン化合物、その製造方法、及びその用途 |
| JP2010215524A (ja) * | 2009-03-13 | 2010-09-30 | Fujifilm Corp | フルオロビシクロ［２．２．２］オクタン化合物、その製造方法、及びその用途 |
| CN102892862B (zh) * | 2010-05-19 | 2015-05-13 | 默克专利股份有限公司 | 包含液晶介质的光开关元件 |
| GB201009488D0 (en) | 2010-06-07 | 2010-07-21 | Merck Patent Gmbh | Switch element comprising a liquid-crystaline medium |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787198A (fr) * | 1971-08-07 | 1973-02-05 | Merck Patent Gmbh | Composes et melanges nematiques |
| US4058478A (en) * | 1972-02-23 | 1977-11-15 | Hoffmann-La Roche Inc. | Liquid crystal esters |
| US3876286A (en) * | 1972-06-14 | 1975-04-08 | Werk Fernsehelektronik Veb | Use of nematic liquid crystalline substances |
| DD105701A1 (en, 2012) * | 1973-07-02 | 1974-05-05 | ||
| US4017416A (en) * | 1974-10-11 | 1977-04-12 | Chisso Corporation | P-cyanophenyl 4-alkyl-4'-biphenylcarboxylate, method for preparing same and liquid crystal compositions using same |
| FR2288732A1 (fr) * | 1974-10-22 | 1976-05-21 | Merck Patent Gmbh | Nouveaux esters biphenyliques, procede pour leur preparation et application comme constituants de cristaux liquides |
| FR2297201A1 (fr) * | 1975-01-10 | 1976-08-06 | Thomson Csf | Produits mesogenes pour cellules a cristal liquide, et procede de fabrication desdits produits |
| US4113647A (en) * | 1976-08-13 | 1978-09-12 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystalline materials |
| GB1592161A (en) * | 1976-08-13 | 1981-07-01 | Secr Defence | Biphenyl carboxylic esters and their use as liquid crystal materials |
| GB1587819A (en) * | 1976-08-13 | 1981-04-08 | Secr Defence | Aromatic diester liquid crystal materials |
| DE2636684C3 (de) * | 1976-08-14 | 1980-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika |
| GB1596012A (en) * | 1976-08-16 | 1981-08-19 | Secr Defence | Optically active liquid crystal materials and liquid crystal devices containing them |
| DE2701591C3 (de) * | 1977-01-15 | 1979-12-20 | Merck Patent Gmbh, 6100 Darmstadt | Hexahydroterphenylderivate und deren Verwendung in flüssigkristallinen Dielektrika |
| DD132591A1 (de) * | 1977-08-31 | 1978-10-11 | Dietrich Demus | Nematische fluessig-kristalline gemische |
| GB2009219B (en) * | 1977-11-02 | 1982-04-28 | Secr Defence | Liquid ctystal material mixtures and devices incorporating such mixtures |
| JPS5483694A (en) * | 1977-12-16 | 1979-07-03 | Hitachi Ltd | Nematic liquid crystal body for display device |
| DE2800553A1 (de) * | 1978-01-07 | 1979-07-12 | Merck Patent Gmbh | Cyclohexanderivate |
| GB2027027B (en) * | 1978-08-04 | 1982-12-15 | Gray G W | Alkyl bicyclo (2,2,2)octyl-phenyl-or-polyphenyl-nitriles their use as liquid crystal compounds and materials and devices containing them |
| GB2017742B (en) * | 1979-02-21 | 1982-08-18 | Suwa Seikosha Kk | Liquid crystal materials |
-
1979
- 1979-08-01 US US06/062,623 patent/US4261652A/en not_active Expired - Lifetime
- 1979-08-03 CH CH715979A patent/CH646683A5/de not_active IP Right Cessation
- 1979-08-03 DE DE19792931637 patent/DE2931637A1/de active Granted
- 1979-08-03 JP JP9939679A patent/JPS5524174A/ja active Granted
- 1979-08-03 FR FR7920011A patent/FR2432546A1/fr active Granted
-
1985
- 1985-10-25 SG SG808/85A patent/SG80885G/en unknown
- 1985-12-18 HK HK1007/85A patent/HK100785A/xx not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY203/87A patent/MY8700203A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY8700203A (en) | 1987-12-31 |
| SG80885G (en) | 1986-07-18 |
| JPS5524174A (en) | 1980-02-21 |
| CH646683A5 (de) | 1984-12-14 |
| DE2931637A1 (de) | 1980-02-28 |
| HK100785A (en) | 1985-12-27 |
| DE2931637C2 (en, 2012) | 1988-12-01 |
| US4261652A (en) | 1981-04-14 |
| FR2432546B1 (en, 2012) | 1983-02-04 |
| FR2432546A1 (fr) | 1980-02-29 |
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