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DE3145711A1 - Insoluble compounds as colorants for liquid-crystal mixtures - Google Patents

Insoluble compounds as colorants for liquid-crystal mixtures

Info

Publication number
DE3145711A1
DE3145711A1 DE19813145711 DE3145711A DE3145711A1 DE 3145711 A1 DE3145711 A1 DE 3145711A1 DE 19813145711 DE19813145711 DE 19813145711 DE 3145711 A DE3145711 A DE 3145711A DE 3145711 A1 DE3145711 A1 DE 3145711A1
Authority
DE
Germany
Prior art keywords
insoluble compounds
colorants
liquid
compounds
insoluble
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.)
Granted
Application number
DE19813145711
Other languages
German (de)
Other versions
DE3145711C2 (en
Inventor
Walter 6900 Heidelberg Ditter
Heinz Dipl.-Chem. Dr. 6710 Frankenthal Eilingsfeld
Karl-Heinz Dipl.-Chem. Dr. 6800 Mannheim Etzbach
Fritz Dipl.-Chem. Dr. 6700 Ludwigshafen Graser
Dieter Dipl.-Chem. Dr. 6900 Heidelberg Horn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19813145711 priority Critical patent/DE3145711A1/en
Publication of DE3145711A1 publication Critical patent/DE3145711A1/en
Application granted granted Critical
Publication of DE3145711C2 publication Critical patent/DE3145711C2/de
Granted legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
    • G02F1/13725—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on guest-host interaction
    • 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

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal (AREA)

Abstract

The invention relates to the use of insoluble compounds which are optically anisotropic as colorants for electro-optical displays which contain liquid crystals and operate on the guest/host principle.

Description

Unlösliche Verbindungen als Farbgeber für Flüssigkristallmischuncren Die Erfindung betrifft die Verwendung von unlöslichen Verbindungen, die optisch anisotrop sind, als Farbgeber für Flüssigkristalle enthaltende elektrooptische Anzeigen, die nach dem Guest/Host-Prinzip arbeiten.Insoluble compounds as coloring agents for liquid-crystal mixtures The invention relates to the use of insoluble compounds that are optically are anisotropic, as color donors for electro-optical displays containing liquid crystals, which work according to the guest / host principle.

Unlöslich im Sinne der Erfindung bedeutet, daß sich die erfindungsgemäß zu verwendenden Verbindungen nicht oder nicht merklich in dem Flüssigkristallmaterial lösen, d. h.Insoluble in the context of the invention means that the invention compounds to be used are not or not noticeably in the liquid crystal material solve, d. H.

sie verhalten sich wie Pigmente.they behave like pigments.

Unter optisch anisotrop im Sinne der Erfindung werden Verbindungen verstanden, deren Lichtabsorption bezogen auf die Kristallachsen richtungsabhängig ist.For the purposes of the invention, optically anisotropic are compounds understood, their light absorption based on the crystal axes direction-dependent is.

Solche Verbindungen finden sich beispielsweise in der Azo-, Anthrachinon-,-Phthalocyanin- oder Perylenreihe sowie bei kondensierten Aromaten, die auch heterocyclische Ringe enthalten können.Such compounds can be found, for example, in the azo, anthraquinone, phthalocyanine or perylene series and in the case of condensed aromatics, which also contain heterocyclic rings may contain.

Einzelne besonders geeignete Verbindungen sind z. B. die folgenden Perylentetracarbonsäurebisimide 1 - 8. o 0 Verbindung R¾')'R Farbe o 0 1 -CH2-CH3 rot 2 -CH2-CH2-CH3 schwarz 3 -CH2-CH2-CH2-CH2 -Cli rLL 4 -CH2-Cli2-CH2 -O-CH3 schwarz 5 -CH2-CH,-CH,-O-C2H5 rot 6 -CH2-CH 4 rot CH3 7 e N=N 4 rot 8 e O-C2H5 rot Individual particularly suitable compounds are, for. B. the following perylenetetracarboxylic acid bisimides 1-8. o 0 Connection R¾ ')' R color o 0 1 -CH2-CH3 red 2 -CH2-CH2-CH3 black 3 -CH2-CH2-CH2-CH2 -Cli rLL 4 -CH2-Cli2-CH2 -O-CH3 black 5 -CH2-CH, -CH, -O-C2H5 red 6 -CH2-CH 4 red CH3 7 e N = N 4 red 8 e O-C2H5 red

Man kann die unlöslichen Verbindungen allein oder als Mischung anwenden, auch Mischungen mit löslichen pleochroitischen Farbstoffen sind möglich. Beispielsweise kann man durch Mischungen bestimmte, mit Einzelfarbstoffen nicht erreichbare Farbtöne einstellen.The insoluble compounds can be used alone or as a mixture, Mixtures with soluble pleochroic dyes are also possible. For example You can use mixtures to create certain color tones that cannot be achieved with individual dyes to adjust.

Zweckmäßigerweise werden die unlöslichen Verbindungen in feinverteilter Form verwendet, Teilchengrößen von 0,01 -0,5 Fm sind bevorzugt.Appropriately, the insoluble compounds are finely divided Shape used, particle sizes of 0.01-0.5 µm are preferred.

Zur Einstellung und Erhaltung einer ausreichenden Feinverteilung in dem Flüssigkristallmaterial ist es zweckmäßig, Mittel zur Stabilisierung zuzusetzen (siehe z. B. DE-OS 29 06 111).To set and maintain a sufficient fine distribution in It is expedient to add stabilizers to the liquid crystal material (see e.g. DE-OS 29 06 111).

Die erfindungsgemäß zu verwendenden Verbindungen werden dem Flüssigkristallmaterial in Mengen von ungefähr 0,5 -5 % zugesetzt.The compounds to be used in the present invention become the liquid crystal material added in amounts of approximately 0.5-5%.

Es ist bekannt, für elektrooptische Anzeigen lösliche Farbstoffe enthaltende Flüssigkristallmaterialien zu verwenden (siehe z. B. EP 0 025 809, EP 26 004, EP 0 002 104 und Heilmeier, G.H. et al, Molec. Cryst. and Liq. Cryst. 8, 293 - 304, 1969).It is known for electro-optical displays containing soluble dyes To use liquid crystal materials (see e.g. EP 0 025 809, EP 26 004, EP 0 002 104 and Heilmeier, G.H. et al, Molec. Cryst. and Liq. Cryst. 8, 293 - 304, 1969).

Die Farbstoffmoleküle werden hierbei von dem Flüssigkristallmaterial, in dem sie gelöst sind, entsprechend den anliegenden Feld orientiert und zeigen ae nach Orientierung eine unterschiedliche Lichtabsorption. Für die technische Verwendbarkeit ist die Löslichkeit, insbesondere bei Temperaturen CO °C, bisher die wesentliche Barriere, denn nur wenige Farbstoffe sind in ausreichendem Maße in dem Flüssigkristallmaterial löslich.The dye molecules are here from the liquid crystal material, in which they are solved, oriented and pointing according to the adjacent field ae a different light absorption after orientation. For technical usability solubility, especially at temperatures of CO ° C, has been the most important so far Barrier, because only a few dyes are in sufficient quantities in the liquid crystal material soluble.

Es war daher außerordentlich überraschend, daß auch die erfindungsgemäß zu verwendenden6 in dem Flüssigkristallmaterial unlöslichen Verbindungen, für die Verwendung in den elektrooptischen Anzeigen geeignet sind. Sie zeichnen sich weiterhin durch ein besonders hohes dichroitisches Verhältnis und hervorragende Lichtechtheiten aus.It was therefore extremely surprising that the invention Compounds insoluble in the liquid crystal material to be used6 for which Use in the electro-optical displays are suitable. You continue to stand out due to a particularly high dichroic ratio and excellent lightfastness the end.

Die unlöslichen Farbstoffe können nach bekannten Verfahren hergestellt werden.The insoluble dyes can be prepared by known methods will.

Die Messungen wurden in der nematischen Phase der Fa. Merck ZLI-1840 an einem Spektralphotometer der Fa. Hewlett Packard 8450 durchgeführt. Das dichroitische Verhältnis CR wurde durch Messung der Extinktion E parallel (E") und E senkrecht (E@) nach der Beziehung CR = Es ermittelt.The measurements were made in the nematic phase from Merck ZLI-1840 carried out on a spectrophotometer from Hewlett Packard 8450. The dichroic Ratio CR was determined by measuring the absorbance E parallel (E ") and E perpendicular (E @) determined according to the relationship CR = Es.

Hierzu wurden handelsübliche Meßzellen mit einer Schichtdicke von 10 pm eingesetzt.For this purpose, commercially available measuring cells with a layer thickness of 10 pm used.

Der Ordnungsgrad S wurde nach der bekannten Gleichung S = CR - 1 berechnet.The degree of order S was calculated according to the well-known equation S = CR - 1.

CR + 2 In der Tabelle sind für die Perylentetracarbonsäurebisimide 1 bis 8, deren Teilchengröße ca. 0,1 pm beträgt, das dichroitische Verhältnis und der Ordnungsgrad (bestimmt für X max.) zusammengestellt. CR + 2 In the table are for the perylenetetracarboxylic acid bisimides 1 to 8, the particle size of which is approx. 0.1 μm, the dichroic ratio and the degree of order (determined for X max.) is compiled.

Tabelle Farbstoff CR S 1 7,8 0,69 2 13 0,8 3 10,3 0,76 o 18,0 0,85 5 8,6 0,72 6 10,8 0,77 7 16,8 0,84 8 13,7 0,81 In den Figuren 1 und 2 sind die Absorptionsspektren in parallel und senkrecht polarisiertem Licht für die Farbstoffe 2 und 8, in Figur 3 für r-Kuprerphthalocyanin und in Figur 4 für den Bisazofarbstoff der Formel dargestellt.Tabel CR S dye 1 7.8 0.69 2 13 0.8 3 10.3 0.76 o 18.0 0.85 5 8.6 0.72 6 10.8 0.77 7 16.8 0.84 8 13.7 0.81 In FIGS. 1 and 2 the absorption spectra in parallel and perpendicularly polarized light are for the dyes 2 and 8, in FIG. 3 for r-copper phthalocyanine and in FIG. 4 for the bisazo dye of the formula shown.

Zeichn.Sign.

LeerseiteBlank page

Claims (4)

Patentansprüche 1. Verwendung von unlöslichen yerbindungen, die optisch anisotrop sindj als Farbgeber für Flüssigkristalle enthaltende elektrooptische Anzeigen, die nach dem Guest/Host-Prinzip arbeiten.Claims 1. Use of insoluble compounds which are optical are anisotropic as color donors for electro-optical displays containing liquid crystals, which work according to the guest / host principle. 2. Verwendung von Verbindungen gemäß Anspruch 1, deren Teilchengröße 0,01 bis 5 »m beträgt.2. Use of compounds according to claim 1, their particle size 0.01 to 5 »m. 3. Verwendung von Verbindungen gemäß Anspruch 1 in nedmatischen, smektischen oder cholesterischen flüssigkristallinen Phasen.3. Use of compounds according to claim 1 in nedmatic, smectic or cholesteric liquid crystalline phases. 4. Verwendung von Perylentetracarbonsäurediimiden als unlösliche Verbindungen gemäß Anspruch 14. Use of Perylenetetracarbonsäurediimiden as insoluble compounds according to claim 1
DE19813145711 1981-11-19 1981-11-19 Insoluble compounds as colorants for liquid-crystal mixtures Granted DE3145711A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19813145711 DE3145711A1 (en) 1981-11-19 1981-11-19 Insoluble compounds as colorants for liquid-crystal mixtures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19813145711 DE3145711A1 (en) 1981-11-19 1981-11-19 Insoluble compounds as colorants for liquid-crystal mixtures

Publications (2)

Publication Number Publication Date
DE3145711A1 true DE3145711A1 (en) 1983-05-26
DE3145711C2 DE3145711C2 (en) 1989-03-16

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3314654A1 (en) * 1982-04-26 1983-10-27 EPSON Corp., Suwa, Nagano LIQUID CRYSTAL DISPLAY CELL AND LIQUID CRYSTAL DISPLAY DEVICE WITH SUCH A
US4597891A (en) * 1984-06-04 1986-07-01 Polaroid Corporation Liquid crystal compositions and devices and novel compounds
US4607097A (en) * 1983-06-03 1986-08-19 Alps Electric Co., Ltd. Dichromatic coloring matter for a colored liquid crystal display element
DE3822604A1 (en) * 1987-07-17 1989-01-26 Hitachi Ltd Liquid-crystal display element
WO2005003132A1 (en) * 2003-06-25 2005-01-13 Nitto Denko Corporation Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotropic films containing the same, and methods for making the same
CN100457755C (en) * 2003-06-25 2009-02-04 日东电工株式会社 Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotr

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0002104A1 (en) * 1977-10-14 1979-05-30 BDH Chemicals Limited Pleochroic dyes suitable for use in solution with liquid crystal materials for electro-optic device applications
EP0025809A1 (en) * 1979-09-21 1981-04-01 BBC Aktiengesellschaft Brown, Boveri & Cie. Liquid crystals mixture

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0002104A1 (en) * 1977-10-14 1979-05-30 BDH Chemicals Limited Pleochroic dyes suitable for use in solution with liquid crystal materials for electro-optic device applications
EP0025809A1 (en) * 1979-09-21 1981-04-01 BBC Aktiengesellschaft Brown, Boveri & Cie. Liquid crystals mixture
EP0026004A1 (en) * 1979-09-21 1981-04-01 BBC Aktiengesellschaft Brown, Boveri & Cie. Liquid crystals mixture

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3314654A1 (en) * 1982-04-26 1983-10-27 EPSON Corp., Suwa, Nagano LIQUID CRYSTAL DISPLAY CELL AND LIQUID CRYSTAL DISPLAY DEVICE WITH SUCH A
US4607097A (en) * 1983-06-03 1986-08-19 Alps Electric Co., Ltd. Dichromatic coloring matter for a colored liquid crystal display element
US4597891A (en) * 1984-06-04 1986-07-01 Polaroid Corporation Liquid crystal compositions and devices and novel compounds
DE3822604A1 (en) * 1987-07-17 1989-01-26 Hitachi Ltd Liquid-crystal display element
WO2005003132A1 (en) * 2003-06-25 2005-01-13 Nitto Denko Corporation Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotropic films containing the same, and methods for making the same
US7025900B2 (en) 2003-06-25 2006-04-11 Nitto Denko Corporation Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotropic films containing the same, and methods for making the same
CN100457755C (en) * 2003-06-25 2009-02-04 日东电工株式会社 Perylenetetracarboxylic acid dibenzimidazole sulfoderivatives containing oxo-groups in the perylene core which form part of a para-quinoid system of bonds, lyotropic liquid crystal systems and anisotr

Also Published As

Publication number Publication date
DE3145711C2 (en) 1989-03-16

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