DE2656252C3 - Dotierungsmittel für nematische Flüssigkristalle und damit dotiertes Flüssigkristallmaterial - Google Patents
Dotierungsmittel für nematische Flüssigkristalle und damit dotiertes FlüssigkristallmaterialInfo
- Publication number
- DE2656252C3 DE2656252C3 DE2656252A DE2656252A DE2656252C3 DE 2656252 C3 DE2656252 C3 DE 2656252C3 DE 2656252 A DE2656252 A DE 2656252A DE 2656252 A DE2656252 A DE 2656252A DE 2656252 C3 DE2656252 C3 DE 2656252C3
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- dopants
- nematic liquid
- liquid crystals
- nematic
- 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
- 239000002019 doping agent Substances 0.000 title claims description 34
- 239000004988 Nematic liquid crystal Substances 0.000 title claims description 18
- 239000004973 liquid crystal related substance Substances 0.000 title description 43
- 239000000463 material Substances 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims description 31
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- -1 cyano compound Chemical class 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- VBGWOJIWYFBBBY-UHFFFAOYSA-N (4-butoxyphenyl) 4-butoxybenzoate Chemical compound C1=CC(OCCCC)=CC=C1OC(=O)C1=CC=C(OCCCC)C=C1 VBGWOJIWYFBBBY-UHFFFAOYSA-N 0.000 claims description 2
- VZMGYHUFLQDGNM-UHFFFAOYSA-N 1-butyl-4-methyl-5-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(CCCC)(C(O)=O)CC(C=2C=CC=CC=2)=C1C VZMGYHUFLQDGNM-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- CBYVEGZNJIEUJD-UHFFFAOYSA-N (4-butoxyphenyl) 4-hexoxybenzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(OCCCC)C=C1 CBYVEGZNJIEUJD-UHFFFAOYSA-N 0.000 claims 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims 1
- IALWCYFULVHLEC-UHFFFAOYSA-N 4-(octyloxy)benzoic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=C1 IALWCYFULVHLEC-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 6
- 210000002858 crystal cell Anatomy 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ASPMBYOMNHUILU-UHFFFAOYSA-N 2-hydroxy-3-(2,4,7-trinitrofluoren-9-ylidene)butanedinitrile Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1C(=C(C#N)C(C#N)O)C1=CC([N+]([O-])=O)=CC=C12 ASPMBYOMNHUILU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003487 electrochemical reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- JRRLEIPMYAOIGR-UHFFFAOYSA-N (4-butoxyphenyl) 4-octoxybenzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(OCCCC)C=C1 JRRLEIPMYAOIGR-UHFFFAOYSA-N 0.000 description 1
- WFUDBPZFGCNRDM-UHFFFAOYSA-N 1-butylcyclopenta-1,3-diene;cyclopenta-1,3-diene;iron(2+) Chemical group [Fe+2].C=1C=C[CH-]C=1.CCCCC1=CC=C[CH-]1 WFUDBPZFGCNRDM-UHFFFAOYSA-N 0.000 description 1
- BOKUDRPARARGGF-UHFFFAOYSA-N 4-butoxy-4-hexoxy-2-phenylcyclohexa-1,5-diene-1-carboxylic acid Chemical compound C1=CC(OCCCCCC)(OCCCC)CC(C=2C=CC=CC=2)=C1C(O)=O BOKUDRPARARGGF-UHFFFAOYSA-N 0.000 description 1
- FJUFINOZWSTZEZ-UHFFFAOYSA-N 5-butylcyclopenta-1,3-diene;iron(2+) Chemical group [Fe+2].CCCCC1=CC=C[CH-]1.CCCCC1=CC=C[CH-]1 FJUFINOZWSTZEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/582—Electrically active dopants, e.g. charge transfer agents
-
- 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
- C09K19/58—Dopants or charge transfer agents
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/645,155 US4066569A (en) | 1975-12-30 | 1975-12-30 | Dopants for dynamic scattering liquid crystals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2656252A1 DE2656252A1 (de) | 1977-07-14 |
| DE2656252B2 DE2656252B2 (de) | 1978-03-23 |
| DE2656252C3 true DE2656252C3 (de) | 1978-12-07 |
Family
ID=24587830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2656252A Expired DE2656252C3 (de) | 1975-12-30 | 1976-12-11 | Dotierungsmittel für nematische Flüssigkristalle und damit dotiertes Flüssigkristallmaterial |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4066569A (enExample) |
| JP (1) | JPS5285085A (enExample) |
| CH (1) | CH612513A5 (enExample) |
| DE (1) | DE2656252C3 (enExample) |
| FR (1) | FR2337188A1 (enExample) |
| GB (1) | GB1559593A (enExample) |
| SE (1) | SE441098B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128312A (en) * | 1977-10-04 | 1978-12-05 | Hughes Aircraft Company | Long life reflective liquid crystal display for dc operation |
| JPS5633360U (enExample) * | 1979-08-22 | 1981-04-01 | ||
| JPS5638378A (en) * | 1979-09-05 | 1981-04-13 | Matsushita Electric Ind Co Ltd | Dynamic scattering type liquid crystal display |
| DE3160901D1 (en) * | 1980-02-12 | 1983-10-27 | Tokyo Shibaura Electric Co | Liquid crystal display element |
| JPS56120790A (en) * | 1980-02-27 | 1981-09-22 | Toshiba Corp | Liquid crystalline display element |
| US4366080A (en) * | 1980-04-07 | 1982-12-28 | Tokyo Shibaura Denki Kabushiki Kaisha | Liquid crystal display element |
| DE3378660D1 (en) * | 1982-09-30 | 1989-01-12 | Showa Denko Kk | Electrically conductive liquid crystalline substance and polymer |
| US5283676A (en) * | 1991-05-13 | 1994-02-01 | Hughes-Jvc Technology Corporation | Liquid crystal light valve |
| WO2003018163A1 (en) | 2001-08-24 | 2003-03-06 | Dober Chemical Corporation | Controlled release of additives in fluid systems |
| WO2003088271A1 (en) * | 2002-04-08 | 2003-10-23 | The University Of Southern California | Doped organic carrier transport materials |
| TWI274082B (en) * | 2002-10-31 | 2007-02-21 | Praxair Technology Inc | Methods for making metallocene compounds |
| US7540978B2 (en) * | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
| DE602004006275T2 (de) * | 2004-10-07 | 2007-12-20 | Novaled Ag | Verfahren zur Dotierung von einem Halbleitermaterial mit Cäsium |
| EP1727221B1 (de) * | 2005-05-27 | 2010-04-14 | Novaled AG | Transparente organische Leuchtdiode |
| EP1729346A1 (de) * | 2005-06-01 | 2006-12-06 | Novaled AG | Lichtemittierendes Bauteil mit einer Elektrodenanordnung |
| EP1739765A1 (de) * | 2005-07-01 | 2007-01-03 | Novaled AG | Organische Leuchtdiode und Anordnung mit mehreren organischen Leuchtdioden |
| EP1786050B1 (de) | 2005-11-10 | 2010-06-23 | Novaled AG | Dotiertes organisches Halbleitermaterial |
| US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
| EP1837927A1 (de) * | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
| ATE394800T1 (de) | 2006-03-21 | 2008-05-15 | Novaled Ag | Heterocyclisches radikal oder diradikal, deren dimere, oligomere, polymere, dispiroverbindungen und polycyclen, deren verwendung, organisches halbleitendes material sowie elektronisches bauelement |
| DE102007012794B3 (de) * | 2007-03-16 | 2008-06-19 | Novaled Ag | Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
| DE102007018456B4 (de) * | 2007-04-19 | 2022-02-24 | Novaled Gmbh | Verwendung von Hauptgruppenelementhalogeniden und/oder -pseudohalogeniden, organisches halbleitendes Matrixmaterial, elektronische und optoelektronische Bauelemente |
| EP3457451B1 (de) | 2007-04-30 | 2019-07-17 | Novaled GmbH | Die verwendung von oxokohlenstoff-, pseudooxokohlenstoff- und radialenverbindungen |
| EP1990847B1 (de) * | 2007-05-10 | 2018-06-20 | Novaled GmbH | Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials |
| DE102007031220B4 (de) * | 2007-07-04 | 2022-04-28 | Novaled Gmbh | Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen |
| US20090205538A1 (en) * | 2008-01-24 | 2009-08-20 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
| US20090203917A1 (en) * | 2008-01-24 | 2009-08-13 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
| US20090203928A1 (en) * | 2008-01-24 | 2009-08-13 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
| US20090209777A1 (en) * | 2008-01-24 | 2009-08-20 | Thompson David M | Organometallic compounds, processes for the preparation thereof and methods of use thereof |
| US8057712B2 (en) * | 2008-04-29 | 2011-11-15 | Novaled Ag | Radialene compounds and their use |
| US8848158B2 (en) | 2008-07-01 | 2014-09-30 | Gentex Corporation | Liquid crystal display device and associated liquid crystal media for use in the same |
| US7803285B2 (en) * | 2008-07-01 | 2010-09-28 | Gentex Corporation | Liquid crystal display device and associated liquid crystal media for use in the same |
| CN109370615B (zh) * | 2018-11-26 | 2020-09-15 | 深圳市国华光电科技有限公司 | 两性离子掺杂剂在制备基于动态散射模式的液晶材料中的应用 |
| CN116042236B (zh) * | 2023-02-20 | 2023-09-05 | 哈尔滨工业大学 | 一种应用于多响应模式智能窗的液晶材料及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162641A (en) * | 1962-07-23 | 1964-12-22 | Du Pont | Charge-transfer compounds of 7, 7, 8, 8-tetracyano-p-quinodimethan and chydrocarbylsubstituted 7, 7, 8, 8-tetracyano-p-quinodimethans with lewis bases |
| US3838059A (en) * | 1972-02-22 | 1974-09-24 | Hughes Aircraft Co | Liquid crystal composition |
| US3923857A (en) * | 1972-02-23 | 1975-12-02 | Hoffmann La Roche | Liquid crystal esters |
| US3876286A (en) * | 1972-06-14 | 1975-04-08 | Werk Fernsehelektronik Veb | Use of nematic liquid crystalline substances |
| US3814700A (en) * | 1972-08-03 | 1974-06-04 | Ibm | Method for controllably varying the electrical properties of nematic liquids and dopants therefor |
| US3975285A (en) * | 1972-10-30 | 1976-08-17 | Hodogaya Chemical Co., Ltd. | Liquid crystal composition |
| JPS5347795B2 (enExample) * | 1973-01-19 | 1978-12-23 | ||
| US3932298A (en) * | 1973-07-19 | 1976-01-13 | Temple University | Nematic liquid crystals with charge-transfer acceptors as dopants |
| FR2266541B1 (enExample) * | 1974-04-05 | 1979-10-19 | Anvar |
-
1975
- 1975-12-30 US US05/645,155 patent/US4066569A/en not_active Expired - Lifetime
-
1976
- 1976-11-30 GB GB49839/76A patent/GB1559593A/en not_active Expired
- 1976-12-11 DE DE2656252A patent/DE2656252C3/de not_active Expired
- 1976-12-14 CH CH1572576A patent/CH612513A5/xx not_active IP Right Cessation
- 1976-12-20 FR FR7638354A patent/FR2337188A1/fr active Granted
- 1976-12-28 SE SE7614628A patent/SE441098B/xx not_active IP Right Cessation
- 1976-12-28 JP JP15766376A patent/JPS5285085A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1559593A (en) | 1980-01-23 |
| DE2656252B2 (de) | 1978-03-23 |
| SE7614628L (sv) | 1977-07-01 |
| JPS5285085A (en) | 1977-07-15 |
| US4066569A (en) | 1978-01-03 |
| FR2337188B1 (enExample) | 1980-08-01 |
| FR2337188A1 (fr) | 1977-07-29 |
| SE441098B (sv) | 1985-09-09 |
| DE2656252A1 (de) | 1977-07-14 |
| CH612513A5 (enExample) | 1979-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |