JPH0144235B2 - - Google Patents
Info
- Publication number
- JPH0144235B2 JPH0144235B2 JP57182234A JP18223482A JPH0144235B2 JP H0144235 B2 JPH0144235 B2 JP H0144235B2 JP 57182234 A JP57182234 A JP 57182234A JP 18223482 A JP18223482 A JP 18223482A JP H0144235 B2 JPH0144235 B2 JP H0144235B2
- Authority
- JP
- Japan
- Prior art keywords
- display device
- liquid crystal
- dye
- electronic display
- dichroic dye
- 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 45
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 26
- 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 claims description 22
- 235000012000 cholesterol Nutrition 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000004020 conductor Substances 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910003437 indium oxide Inorganic materials 0.000 claims description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 claims description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 37
- 239000010410 layer Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000031700 light absorption Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000005684 electric field Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 azo compound Chemical class 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- IBQDPNHVFRFCFK-UHFFFAOYSA-N 4-pentoxybenzoyl chloride Chemical compound CCCCCOC1=CC=C(C(Cl)=O)C=C1 IBQDPNHVFRFCFK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 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
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
-
- 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
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/312,678 US4401369A (en) | 1981-10-19 | 1981-10-19 | Class of dichroic dyes for use with liquid crystals |
| US312678 | 1989-02-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5879077A JPS5879077A (ja) | 1983-05-12 |
| JPH0144235B2 true JPH0144235B2 (Direct) | 1989-09-26 |
Family
ID=23212508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57182234A Granted JPS5879077A (ja) | 1981-10-19 | 1982-10-19 | エレクトロニクス表示装置 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4401369A (Direct) |
| JP (1) | JPS5879077A (Direct) |
| CH (1) | CH656889A5 (Direct) |
| DE (1) | DE3238702A1 (Direct) |
| FR (1) | FR2514774A1 (Direct) |
| GB (1) | GB2108519B (Direct) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080153B1 (en) * | 1981-11-16 | 1987-04-08 | Mitsubishi Kasei Corporation | Pleochroic azo dyes, a liquid crystal composition containing the azo dyes and a display device using the liquid crystal composition |
| JPS58138767A (ja) * | 1982-02-10 | 1983-08-17 | Hitachi Ltd | 液晶組成物及び表示素子 |
| GB2120674B (en) * | 1982-03-13 | 1986-11-19 | Nippon Kanko Shikiso Kenyusho | Dichroic dyestuffs for liquid crystals and liquid crystal compositions comprising the same |
| JPS5947261A (ja) * | 1982-09-13 | 1984-03-16 | Nippon Kanko Shikiso Kenkyusho:Kk | 液晶用アゾ色素の二色性改良法 |
| US4588517A (en) * | 1982-06-30 | 1986-05-13 | Hitachi, Ltd. | Liquid crystal composition |
| YU44866B (en) * | 1983-09-09 | 1991-04-30 | Inst Stefan Jozef | Matrix lcd with an internal reflector and a measuring net |
| US4674841A (en) * | 1985-03-08 | 1987-06-23 | Tektronix, Inc. | Color filter switchable among three state via a variable retarder |
| DE3529988A1 (de) * | 1985-08-22 | 1987-02-26 | Basf Ag | Trisazofarbstoffe und deren verwendung in fluessigkristallinen materialien |
| DD257889A1 (de) * | 1987-02-20 | 1988-06-29 | Werk Fernsehelektronik Veb | Verfahren zur herstellung farbiger fluessigkristallanzeigen |
| DE69016857T2 (de) * | 1989-07-03 | 1995-06-08 | Hercules Inc | Verfahren zur Herstellung von NiNi-Diakyl- 1,8-Naphthalendiamin. |
| US5097029A (en) * | 1989-07-03 | 1992-03-17 | Hercules Incorporated | Process for preparing 2,3-dihydro-1,3-dialkyl-2,3-dialkyl perimidines and N,N-'-dialkyl-1,8-naphthalene diamines |
| US5846452A (en) * | 1995-04-06 | 1998-12-08 | Alliant Techsystems Inc. | Liquid crystal optical storage medium with gray scale |
| EP2067064B1 (en) | 2006-09-13 | 2014-06-11 | Rolic AG | Volume photo-aligned retarder |
| WO2008077261A1 (en) * | 2006-12-22 | 2008-07-03 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| JP5566160B2 (ja) | 2010-03-31 | 2014-08-06 | 富士フイルム株式会社 | 液晶性化合物、液晶性組成物、光吸収異方性膜、及び液晶表示装置 |
| CN103890648B (zh) | 2011-10-03 | 2019-06-18 | 罗利克有限公司 | 具有强uv-二色性的光定向层 |
| WO2013178453A1 (en) | 2012-05-30 | 2013-12-05 | Rolic Ag | Fast generation of elements with individually patterned anisotropy |
| JP6618470B2 (ja) | 2013-08-19 | 2019-12-11 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光配向可能な物品 |
| WO2015150295A1 (en) | 2014-04-03 | 2015-10-08 | Rolic Ag | Optical devices with patterned anisotropy incorporating parallax optic |
| WO2016016156A1 (en) | 2014-07-31 | 2016-02-04 | Rolic Ag | Encapsulation structure for an oled display incorporating antireflection properties |
| KR20180082540A (ko) | 2015-11-11 | 2018-07-18 | 롤릭 테크놀로지스 아게 | 광-정렬가능 물질의 조성물 |
| WO2018019691A1 (en) | 2016-07-29 | 2018-02-01 | Rolic Ag | Method for generating alignment on top of a liquid crystal polymer material |
| US11702595B2 (en) | 2019-06-28 | 2023-07-18 | Rolic Technologies AG | Polymerizable liquid crystal |
| JP7578614B2 (ja) | 2019-06-28 | 2024-11-06 | ロリク・テクノロジーズ・アーゲー | カルバゾールコアを有する新規な重合性液晶 |
| EP3990568B1 (en) | 2019-06-28 | 2023-11-15 | Rolic Technologies AG | New polymerizable liquid crystal having a quinoxaline-hydrazone core |
| KR20220038353A (ko) | 2019-07-24 | 2022-03-28 | 롤릭 테크놀로지스 아게 | 광-정렬성 포지티브 c-플레이트 리타더 |
| CN114286852B (zh) | 2019-08-28 | 2024-06-25 | 罗利克技术有限公司 | 可聚合液晶的组合物 |
| TW202448972A (zh) | 2023-05-12 | 2024-12-16 | 瑞士商羅立克科技股份公司 | 可聚合液晶組成物 |
| WO2025247588A1 (en) | 2024-05-31 | 2025-12-04 | Rolic Technologies AG | Optical security device |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697478A (en) * | 1970-10-19 | 1972-10-10 | Monsanto Co | Polyamides from pseudo-conjugated azo-aromatic diamines |
| DE2414477C3 (de) * | 1974-03-26 | 1980-11-27 | Cassella Ag, 6000 Frankfurt | Farbstoffzubereitung und Verfahren zum Färben und Bedrucken von hochmolekularen Polyestern und Zellulosetriacetat |
| US4145114A (en) * | 1975-06-17 | 1979-03-20 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Pleochroic dyes |
| CH594897A5 (Direct) * | 1976-06-23 | 1978-01-31 | Bbc Brown Boveri & Cie | |
| US4179395A (en) * | 1976-09-09 | 1979-12-18 | General Electric Company | Dichroic dyes having a plurality of azo bonding groups |
| US4128497A (en) * | 1976-09-09 | 1978-12-05 | General Electric Company | Dichroic liquid crystal compositions |
| US4122027A (en) * | 1976-11-08 | 1978-10-24 | General Electric Company | Dichroic liquid crystal composition with 4,4-bis (substituted naphthylazo)azobenzene dichroic dyes |
| CA1077755A (en) * | 1977-02-23 | 1980-05-20 | Arnold H. Bourne | Variable lead optical tracing machine |
| CA1120478A (en) * | 1979-02-05 | 1982-03-23 | Arthur Boller | Cyclohexyl pyrimidines |
| US4350603A (en) * | 1980-06-30 | 1982-09-21 | General Electric Company | Novel tris-azo dyes and liquid crystal compositions made therewith |
| US4308163A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal composition made therewith |
| US4308161A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
| US4308164A (en) * | 1980-08-04 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal composition made therewith |
| US4308162A (en) * | 1980-12-08 | 1981-12-29 | General Electric Company | Novel yellow azo dyes and dichroic liquid crystal compositions made therewith |
| GB2090274B (en) * | 1980-12-12 | 1984-09-12 | Minnesota Mining & Mfg | Dichroic dyestuff |
| US4359398A (en) * | 1980-12-22 | 1982-11-16 | General Electric Company | Liquid crystal compositions with novel tris-azo dichroic dyes |
-
1981
- 1981-10-19 US US06/312,678 patent/US4401369A/en not_active Expired - Fee Related
-
1982
- 1982-10-15 GB GB08229524A patent/GB2108519B/en not_active Expired
- 1982-10-18 CH CH6059/82A patent/CH656889A5/fr not_active IP Right Cessation
- 1982-10-19 JP JP57182234A patent/JPS5879077A/ja active Granted
- 1982-10-19 FR FR8217495A patent/FR2514774A1/fr active Granted
- 1982-10-19 DE DE19823238702 patent/DE3238702A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2514774B1 (Direct) | 1985-05-24 |
| JPS5879077A (ja) | 1983-05-12 |
| DE3238702C2 (Direct) | 1990-03-08 |
| DE3238702A1 (de) | 1983-04-28 |
| GB2108519A (en) | 1983-05-18 |
| FR2514774A1 (fr) | 1983-04-22 |
| US4401369A (en) | 1983-08-30 |
| GB2108519B (en) | 1985-10-02 |
| CH656889A5 (fr) | 1986-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0144235B2 (Direct) | ||
| US4009934A (en) | Electro-optic display devices and methods | |
| KR850000050B1 (ko) | 다색성 염료를 함유하는 액정조성물 | |
| JPH0354140B2 (Direct) | ||
| JPS6115915B2 (Direct) | ||
| KR840001859B1 (ko) | 액정조성물 | |
| CN105824145A (zh) | 液晶显示装置及其驱动方法 | |
| US4116861A (en) | Dichroic liquid crystal compositions | |
| JPH0467169B2 (Direct) | ||
| GB1579762A (en) | Substituted biphenyl benzoic acid esters their preparation and use in liquid crystal compositions | |
| JP2715541B2 (ja) | アゾ系化合物及び該化合物を含有する液晶組成物 | |
| US6737126B2 (en) | Liquid crystal mixture and liquid crystal cell for LCDs and use of a dye with a dipole for a liquid crystal mixture | |
| EP0115136A2 (en) | Cycloalkyl-type isotropic dyes for liquid crystal display devices | |
| JP4285935B2 (ja) | 液晶ゲル組成物とそれを用いた表示媒体及び表示装置並びに表示体 | |
| KR920007662B1 (ko) | 치환된 안트라센형 등방성 염료를 포함하는 조성물 및 상기 조성물을 포함하는 액정 디스플레이 장치 | |
| JPS6124431B2 (Direct) | ||
| JPS5950713B2 (ja) | 液晶組成物 | |
| CN112433403A (zh) | 一种光调制装置 | |
| JP2719955B2 (ja) | アゾ系化合物及びそれを含有する液晶組成物 | |
| JPH03111486A (ja) | ビフェニルから誘導されるキラル液晶 | |
| JPH07138568A (ja) | 液晶組成物 | |
| JPS644557B2 (Direct) | ||
| JPS5853979A (ja) | 液晶表示素子 | |
| JP3538880B2 (ja) | 二色性色素、該色素を含む液晶組成物および液晶素子 | |
| JPS6036569A (ja) | カラ−液晶用アゾ系色素 |