DE2024269A1 - Nematic mixtures - of low melting point, used in electronics - Google Patents

Nematic mixtures - of low melting point, used in electronics

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Publication number
DE2024269A1
DE2024269A1 DE19702024269 DE2024269A DE2024269A1 DE 2024269 A1 DE2024269 A1 DE 2024269A1 DE 19702024269 DE19702024269 DE 19702024269 DE 2024269 A DE2024269 A DE 2024269A DE 2024269 A1 DE2024269 A1 DE 2024269A1
Authority
DE
Germany
Prior art keywords
nematic
mixtures
cpds
melting
melting point
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.)
Pending
Application number
DE19702024269
Other languages
German (de)
Inventor
Ludwig Dipl Chem Dr rer nat Stemstraßer Ralf Dipl Chem Dr rer nat 6100 Darmstadt Pohl
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to DE19702024269 priority Critical patent/DE2024269A1/en
Publication of DE2024269A1 publication Critical patent/DE2024269A1/en
Pending legal-status Critical Current

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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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups

Abstract

Two or three different nematic cpds. of the general formula (I) are mixed together in the molar ratio of 2 (lowest melting cpds) to 1 (higher melting cpds.) or 1:1:1. In formula (I), A beta an azo, azoxy, azomethine or ester gp. and R and R' are straight chain alkyl, alkoxy or acyloxy gps. with up to 10 C atoms, or CN-gps., The title mixtures are used as fluid anisotropic dielectrics for electronic applications or as solvents for investigating direction-dependent molecular properties. Advantage is that the mixtures remain nematic at very low temps and possess a very wide meso phase.

Description

Verfahren zur Herstellung tiefstschmelzender Gemische nematischer Verbindungen Als flüssiges anisotropes Dielektrikum für elektronische Anwendungszwecke oder als Lösungsmittel zur Untersuchung richtungsabhängiger Moleküleigenschaften zum Beispiel in der Spektroskopie eignen sich besonders gut flüssig-kristalline nematische Systeme. Um aber ohne besonderen experimentellen Aufwand mit derartigen Verbindungen arbeiten zu können, sollten sie bereits bei möglichst niedrigen Temperaturen nematisch sein und gleichzeitig eine breite Mesophase besitzen. Process for the production of very low melting mixtures of nematic Compounds As a liquid anisotropic dielectric for electronic applications or as a solvent for the investigation of direction-dependent molecular properties For example, in spectroscopy, liquid-crystalline ones are particularly suitable nematic systems. In order to be able to work with such To be able to work connections, they should already be at the lowest possible temperatures be nematic and at the same time have a broad mesophase.

Es wurde nun gefunden, daß man bei Mischungen nematiseher p, p -disubstituierter Benzylidenaniline oder strukturell verwandter Verbindungen, z,B. Azobenzole, Azoxybenzole, Benzoesäurephenylester immer bei der gleichen Zusammensetzung von etwa 66 2/3 Mol% niedrig schmelzender Komponente und'etwa 33 1/3 Mol% höher schmelzender Komponente bei binären Systemen und von etwa 33 1/3 Mol% je Komponente bei ternären Systemen zum tiefstschmelzenden aller möglichen Gemische gelangt, das gleichzeitig auch den breitesten Mesophasenbereich aufweist. Dabei können die einzelnen Komponenten der gleichen oder auch verschiedenen Substanzklassen angehören, Gegenstand der Erfindung ist ein Verfahren zur Herstellung tiefstschmelzender Gemische nematischer Verbindungen" mit breitester Mesophase, dadurch gekennzeichnet, daß man zwei beziehungsweise drei voneinander verschiedene nematische Verbindungen der allgemeinen Formel X worin eine Zzo-, Azoxy- Azomethin-oder Estergruppe und R und R' geradkettige Alkyl-, Alkoxy-oder Zcyloxygruppen mit jeweils bis zu 10 C-Atomen oder Cyangruppen bedeuten im Molverhältnis von etwa 2 (tieferschmelzende Verbindung) zu etwa 1 (höherschmelzende Verbindung) beziehungsweise etwa 1:1:1 miteinander mischt Die Gemisch önen daduroh hergestellt werden daß man die kristallinen Bestandteile in den entsprechenden Gewichtsverhältnissen vermischt, anschließend über ihren Klärpunkt erhitzt und dabei entweder kräftig rührt oder längere Zeit tempert, um eine homogene isotrope Lösung zu erhalten und anschließend wieder abkühlt.It has now been found that mixtures of nematic p, p -disubstituted benzylidene anilines or structurally related compounds, e.g. Azobenzenes, azoxybenzenes, phenyl benzoates always have the same composition of about 66 2/3 mol% of low-melting component and about 33 1/3 mol% of higher-melting component in binary systems and about 33 1/3 mol% per component in ternary systems reaches the lowest melting point of all possible mixtures, which at the same time also has the broadest mesophase range. The individual components can belong to the same or different classes of substances. The subject matter of the invention is a process for the production of ultra-low-melting mixtures of nematic compounds "with the broadest mesophase, characterized in that two or three different nematic compounds of the general formula X wherein a zzo, azoxy, azomethine or ester group and R and R 'mean straight-chain alkyl, alkoxy or zcyloxy groups each with up to 10 carbon atoms or cyano groups in a molar ratio of about 2 (lower melting compound) to about 1 (higher melting compound) or about 1: 1: 1 mixed together cools down again.

In den nachstehenden Beispielen sind in Klammern die nematischen Bereiche zwischen Schmelzpunkt (erste Temperaturangabe) und Klärpunkt (zweite Temperaturangabe) genannt.In the examples below, the nematic ranges are in brackets between melting point (first temperature specification) and clearing point (second temperature specification) called.

Beispiel Man mischt 2 Mol N-(p-n-Butoxybenzyliden)-p-butyryloxy-anilin (52-110°) mit 1 Mol N-(p-n-Butoxybenzyliden)-p-capronyloxyanilin (80 - 1140), erhitzt unter Rühren bis zur völligen Klärung, kühlt ab und erhält ein eutektisches Gemisch (4-101°).Example 2 moles of N- (p-n-butoxybenzylidene) -p-butyryloxy-aniline are mixed (52-110 °) with 1 mol of N- (p-n-butoxybenzylidene) -p-capronyloxyaniline (80-1140), heated while stirring until it is completely clear, it cools and becomes a eutectic mixture (4-101 °).

Analog erheilt man: aus 2 Mol p-n-Butoxycarbonyloxy-benzoesäure-(p-äthoxyphenylester) (54-67°) und 1 Mol N-(p-Methoxybenzyliden)-p-acetoxyanilin (82-109°): ein eutektisches Gemisch (27-78°); aus 2-Mol p-n-Butyl-p'-methoxy-azoxybenzol (16-76o) und 1 Mol p-n-Butyl-p'-hexyloxy-azoxybenzol (28-92°): ein eutektisches Gemisch (-15 bis +85°); aus je 1 Mol N-(p-n-Hexyloxybenzyliden)-p-cyan-anilin (55-100°), N-(p-Heptanoyloxybenzyliden)-p-cyan-anilin (54-94°) und N-(p-Octanoyloxy-benzyliden)-p-cyan-anilin(52-93°) ein eutektisches Gemisch (26-88°).The following is obtained analogously: from 2 moles of p-n-butoxycarbonyloxy-benzoic acid (p-ethoxyphenyl ester) (54-67 °) and 1 mole of N- (p-methoxybenzylidene) -p-acetoxyaniline (82-109 °): a eutectic Mixture (27-78 °); from 2 moles of p-n-butyl-p'-methoxy-azoxybenzene (16-76o) and 1 mole p-n-Butyl-p'-hexyloxy-azoxybenzene (28-92 °): a eutectic mixture (-15 to + 85 °); from 1 mole each of N- (p-n-hexyloxybenzylidene) -p-cyano-aniline (55-100 °), N- (p-heptanoyloxybenzylidene) -p-cyano-aniline (54-94 °) and N- (p-octanoyloxy-benzylidene) -p-cyano-aniline (52-93 °) a eutectic Mixture (26-88 °).

Claims (1)

Patentanspruch Claim Verfahren zur Herstellung tiefstschmelzender Gemische nematischer Verbindungen mit breitester Mesophase, dadurch gekennzeichnet, daß man zwei beziehungsweise drei voneinander verschiedene nematische Verbindungen der allgemeinen Formel 1 worin A eine Azo-, A,zoxy-, Azomethin-oder Estergruppe und R und R' geradkettige Alkyl- Alkoxy oder Acyloxygruppen mit jeweils bis zu 10 C-Atomen oder Cyangruppen bedeaten im Molverhältnis von etwa 2 (tieferschmelzende Verbindung) zu etwa 1 (höherschmelzende Verbindung) beziehungsweise etwa 1:1:1 miteinander mischt.Process for the preparation of extremely low-melting mixtures of nematic compounds with the broadest mesophase, characterized in that two or three different nematic compounds of the general formula 1 in A is an azo, A, zoxy, azomethine or ester group and R and R 'are straight-chain alkyl, alkoxy or acyloxy groups, each with up to 10 carbon atoms or cyano groups, in a molar ratio of about 2 (lower melting compound) to about 1 (higher melting compound) Compound) or about 1: 1: 1 mixes with each other.
DE19702024269 1970-05-19 1970-05-19 Nematic mixtures - of low melting point, used in electronics Pending DE2024269A1 (en)

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Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2173165A1 (en) * 1972-02-23 1973-10-05 Hoffmann La Roche
FR2195617A1 (en) * 1971-08-07 1974-03-08 Merck Patent Gmbh
US3954653A (en) * 1973-07-06 1976-05-04 Kabushiki Kaisha Suwa Seikosha Liquid crystal composition having high dielectric anisotropy and display device incorporating same
US3956167A (en) * 1973-05-17 1976-05-11 Beckman Instruments, Inc. Liquid crystal compositions and devices
US3960748A (en) * 1972-10-24 1976-06-01 Eastman Kodak Company Nematic liquid crystal compositions
US3960752A (en) * 1972-10-24 1976-06-01 Eastman Kodak Company Liquid crystal compositions
US3974087A (en) * 1973-10-17 1976-08-10 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Liquid crystal compositions
US3975286A (en) * 1974-09-03 1976-08-17 Beckman Instruments, Inc. Low voltage actuated field effect liquid crystals compositions and method of synthesis
US3976591A (en) * 1972-05-19 1976-08-24 Thomson-Csf Novel chemical substance presenting a nematic liquid phase
US3981817A (en) * 1973-04-04 1976-09-21 Hoffmann-La Roche Inc. Mixtures of liquid crystals
US3983049A (en) * 1974-05-02 1976-09-28 General Electric Company Liquid crystal compositions with positive dielectric anisotropy
US3984344A (en) * 1975-04-30 1976-10-05 General Electric Company Positive dielectric anisotropy liquid crystal compositions
US3984392A (en) * 1973-12-13 1976-10-05 U.S. Philips Corporation Liquid crystalline azobenzene compounds
US3997242A (en) * 1973-03-02 1976-12-14 Hoffmann-La Roche Inc. Electro-optical cell containing dielectric isonitriles
US4000084A (en) * 1973-12-17 1976-12-28 Hughes Aircraft Company Liquid crystal mixtures for electro-optical display devices
US4001137A (en) * 1971-08-07 1977-01-04 Merck Patent Gesellschaft Mit Beschrankter Haftung Nematic compounds and mixtures
US4004848A (en) * 1973-03-13 1977-01-25 Kabushiki Kaisha Suwa Seikosha Liquid crystal display device
US4009938A (en) * 1972-12-06 1977-03-01 Kabushiki Kaisha Suwa Seikosha Liquid crystal display device
US4011173A (en) * 1972-08-03 1977-03-08 Merck Patent Gesellschaft Mit Beschrankter Haftung Modified nematic mixtures with positive dielectric anisotropy
US4014811A (en) * 1974-12-28 1977-03-29 Dai Nippon Toryo Kabushiki Kaisha Nematic liquid crystal compositions
US4027950A (en) * 1973-08-20 1977-06-07 Matsushita Electric Industrial Co., Ltd. Electro-optical display device
US4031028A (en) * 1976-06-18 1977-06-21 Motorola, Inc. Nematic liquid crystal composition
US4038200A (en) * 1972-08-07 1977-07-26 Texas Instruments Incorporated Lyotropic nematic liquid crystals for use in electro-optical display devices
US4043935A (en) * 1973-07-06 1977-08-23 Kabushiki Kaisha Suwa Seikosha Liquid crystal composition having high dielectric anisotropy and display device incorporating same
US4046708A (en) * 1973-11-28 1977-09-06 Thomson-Csf Mixture of nematic liquid crystals exhibiting a positive dielectric anisotropy and a wide temperature range
US4047803A (en) * 1973-04-24 1977-09-13 Dai Nippon Toryo Kabushiki Kaisha Nematic liquid crystal compositions
US4048089A (en) * 1975-07-31 1977-09-13 Dainippon Ink & Chemicals, Inc. Nematic liquid crystal composition
US4058478A (en) * 1972-02-23 1977-11-15 Hoffmann-La Roche Inc. Liquid crystal esters
US4058476A (en) * 1973-03-02 1977-11-15 Hoffmann-La Roche Inc. Liquid crystalline isonitriles
US4058477A (en) * 1972-02-23 1977-11-15 Hoffmann-La Roche Inc. Liquid crystal Schiffs bases
US4086002A (en) * 1972-02-03 1978-04-25 Haffmann-La Roche Inc. Field effect light shutter employing low temperature nematic liquid crystals
US4089588A (en) * 1975-09-25 1978-05-16 U.S. Philips Corporation Nematic liquid crystalline mixture of α-cyanostilbenes and application thereof in image display devices
US4097120A (en) * 1973-12-13 1978-06-27 U.S. Philips Corporation Liquid crystalline compounds and mixtures
US4134888A (en) * 1975-12-22 1979-01-16 Rca Corporation Cholesteryl carbonates and carbamates of azo dyes
US4137192A (en) * 1974-01-25 1979-01-30 Canon Kabushiki Kaisha Liquid crystalline composition
US4147651A (en) * 1974-09-03 1979-04-03 Beckman Instruments, Inc. Biphenyl based liquid crystal compositions
US4222636A (en) * 1972-10-10 1980-09-16 Thomson-Csf Liquid crystal mixture and its application to optical modulation
WO1980002462A1 (en) * 1979-05-08 1980-11-13 Rockwell International Corp Electrochromic display using rare-earth diphthalocyanines and a low-freezing-point electrolyte
US4371236A (en) * 1976-12-20 1983-02-01 Rockwell International Corporation Electrochromic display using rare-earth diphthalocyanines and a low freezing-point electrolyte
FR2525626A1 (en) * 1982-04-22 1983-10-28 Asulab Sa LUBRICANT BASED ON LIQUID CRYSTALS
US4533483A (en) * 1973-07-02 1985-08-06 American Hospital Supply Corporation Heat source providing a substantially constant temperature
US4979805A (en) * 1984-07-23 1990-12-25 Canon Kabushiki Kaisha Ferroelectric liquid crystal device containing optically active azo or azoxy benzene type mesomorphic compound with extended life

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001137A (en) * 1971-08-07 1977-01-04 Merck Patent Gesellschaft Mit Beschrankter Haftung Nematic compounds and mixtures
FR2195617A1 (en) * 1971-08-07 1974-03-08 Merck Patent Gmbh
US4086002A (en) * 1972-02-03 1978-04-25 Haffmann-La Roche Inc. Field effect light shutter employing low temperature nematic liquid crystals
FR2173165A1 (en) * 1972-02-23 1973-10-05 Hoffmann La Roche
US4058478A (en) * 1972-02-23 1977-11-15 Hoffmann-La Roche Inc. Liquid crystal esters
US4058477A (en) * 1972-02-23 1977-11-15 Hoffmann-La Roche Inc. Liquid crystal Schiffs bases
US3976591A (en) * 1972-05-19 1976-08-24 Thomson-Csf Novel chemical substance presenting a nematic liquid phase
US4011173A (en) * 1972-08-03 1977-03-08 Merck Patent Gesellschaft Mit Beschrankter Haftung Modified nematic mixtures with positive dielectric anisotropy
US4038200A (en) * 1972-08-07 1977-07-26 Texas Instruments Incorporated Lyotropic nematic liquid crystals for use in electro-optical display devices
US4222636A (en) * 1972-10-10 1980-09-16 Thomson-Csf Liquid crystal mixture and its application to optical modulation
US3960752A (en) * 1972-10-24 1976-06-01 Eastman Kodak Company Liquid crystal compositions
US3960748A (en) * 1972-10-24 1976-06-01 Eastman Kodak Company Nematic liquid crystal compositions
US4009938A (en) * 1972-12-06 1977-03-01 Kabushiki Kaisha Suwa Seikosha Liquid crystal display device
US4058476A (en) * 1973-03-02 1977-11-15 Hoffmann-La Roche Inc. Liquid crystalline isonitriles
US3997242A (en) * 1973-03-02 1976-12-14 Hoffmann-La Roche Inc. Electro-optical cell containing dielectric isonitriles
US4004848A (en) * 1973-03-13 1977-01-25 Kabushiki Kaisha Suwa Seikosha Liquid crystal display device
US3981817A (en) * 1973-04-04 1976-09-21 Hoffmann-La Roche Inc. Mixtures of liquid crystals
US4047803A (en) * 1973-04-24 1977-09-13 Dai Nippon Toryo Kabushiki Kaisha Nematic liquid crystal compositions
US3956167A (en) * 1973-05-17 1976-05-11 Beckman Instruments, Inc. Liquid crystal compositions and devices
US4533483A (en) * 1973-07-02 1985-08-06 American Hospital Supply Corporation Heat source providing a substantially constant temperature
US3954653A (en) * 1973-07-06 1976-05-04 Kabushiki Kaisha Suwa Seikosha Liquid crystal composition having high dielectric anisotropy and display device incorporating same
US4043935A (en) * 1973-07-06 1977-08-23 Kabushiki Kaisha Suwa Seikosha Liquid crystal composition having high dielectric anisotropy and display device incorporating same
US4027950A (en) * 1973-08-20 1977-06-07 Matsushita Electric Industrial Co., Ltd. Electro-optical display device
US3974087A (en) * 1973-10-17 1976-08-10 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Liquid crystal compositions
US4046708A (en) * 1973-11-28 1977-09-06 Thomson-Csf Mixture of nematic liquid crystals exhibiting a positive dielectric anisotropy and a wide temperature range
US3984392A (en) * 1973-12-13 1976-10-05 U.S. Philips Corporation Liquid crystalline azobenzene compounds
US4097120A (en) * 1973-12-13 1978-06-27 U.S. Philips Corporation Liquid crystalline compounds and mixtures
US4000084A (en) * 1973-12-17 1976-12-28 Hughes Aircraft Company Liquid crystal mixtures for electro-optical display devices
US4137192A (en) * 1974-01-25 1979-01-30 Canon Kabushiki Kaisha Liquid crystalline composition
US3983049A (en) * 1974-05-02 1976-09-28 General Electric Company Liquid crystal compositions with positive dielectric anisotropy
US4147651A (en) * 1974-09-03 1979-04-03 Beckman Instruments, Inc. Biphenyl based liquid crystal compositions
US3975286A (en) * 1974-09-03 1976-08-17 Beckman Instruments, Inc. Low voltage actuated field effect liquid crystals compositions and method of synthesis
US4014811A (en) * 1974-12-28 1977-03-29 Dai Nippon Toryo Kabushiki Kaisha Nematic liquid crystal compositions
US3984344A (en) * 1975-04-30 1976-10-05 General Electric Company Positive dielectric anisotropy liquid crystal compositions
US4048089A (en) * 1975-07-31 1977-09-13 Dainippon Ink & Chemicals, Inc. Nematic liquid crystal composition
US4089588A (en) * 1975-09-25 1978-05-16 U.S. Philips Corporation Nematic liquid crystalline mixture of α-cyanostilbenes and application thereof in image display devices
US4134888A (en) * 1975-12-22 1979-01-16 Rca Corporation Cholesteryl carbonates and carbamates of azo dyes
US4031028A (en) * 1976-06-18 1977-06-21 Motorola, Inc. Nematic liquid crystal composition
US4371236A (en) * 1976-12-20 1983-02-01 Rockwell International Corporation Electrochromic display using rare-earth diphthalocyanines and a low freezing-point electrolyte
WO1980002462A1 (en) * 1979-05-08 1980-11-13 Rockwell International Corp Electrochromic display using rare-earth diphthalocyanines and a low-freezing-point electrolyte
FR2525626A1 (en) * 1982-04-22 1983-10-28 Asulab Sa LUBRICANT BASED ON LIQUID CRYSTALS
EP0092682A1 (en) * 1982-04-22 1983-11-02 Asulab S.A. Lubricant
US4979805A (en) * 1984-07-23 1990-12-25 Canon Kabushiki Kaisha Ferroelectric liquid crystal device containing optically active azo or azoxy benzene type mesomorphic compound with extended life

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