EP0452444A1 - Phenylcyclohexanes et milieu mesomorphe - Google Patents

Phenylcyclohexanes et milieu mesomorphe

Info

Publication number
EP0452444A1
EP0452444A1 EP19900915456 EP90915456A EP0452444A1 EP 0452444 A1 EP0452444 A1 EP 0452444A1 EP 19900915456 EP19900915456 EP 19900915456 EP 90915456 A EP90915456 A EP 90915456A EP 0452444 A1 EP0452444 A1 EP 0452444A1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
phenylcyclohexanes
liquid
media
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.)
Withdrawn
Application number
EP19900915456
Other languages
German (de)
English (en)
Inventor
Andreas WÄCHTLER
Reinhard Hittich
Herbert Plach
David Coates
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
Publication of EP0452444A1 publication Critical patent/EP0452444A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
    • C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds

Definitions

  • the invention relates to new phenylcyclohexanes of the formula I.
  • Alkoxy each with up to 7 carbon atoms
  • Liquid crystal mixtures containing these compounds also have relatively small values for the electrical resistance and are less suitable for various applications.
  • the compounds of formula I can be prepared like similar e.g. Compounds known from DE-OS 29 07 332 are used as components of liquid-crystalline media, in particular for displays which are based on the principle of the twisted cell.
  • the substances hitherto used for this purpose all have certain disadvantages, for example melting points that are too high, clearing points that are too low, stability that is too low in relation to the action of heat, light or electrical fields, electrical resistance that is too low, temperature dependence of the threshold voltage that is too high.
  • the materials used to date have disadvantages, particularly in the case of displays of the supertwist type (STN) with twist angles of significantly more than 220 ° C. or in the case of displays with an active matrix.
  • the object of the invention was to find new liquid-crystalline compounds which are suitable as components of liquid-crystalline media, in particular for nematic media with positive dielectric anisotropy, and which do not show the disadvantages of the known compounds or only show them to a lesser extent. This object was achieved by the provision of the new compounds of the formula I.
  • the compounds of the formula I are particularly suitable as components of liquid-crystalline media.
  • liquid-crystalline media with wide nematic ranges, excellent nematogenicity to very low temperatures, excellent chemical stability, low viscosity with positive dielectric anisotropy, low temperature dependence of the threshold voltage and / or small optical anisotropy can be obtained with their help.
  • the new compounds also show good solubility for other components of such media and relatively high positive dielectric anisotropy with a favorable viscosity.
  • the compounds of the formula I enable STN displays with a very high steepness of the electro-optical characteristic as well as displays with an active matrix with excellent long-term stability.
  • the compounds of the formula I are colorless in the pure state and form liquid-crystalline mesophases in a temperature range which is favorable for electro-optical use.
  • the invention thus relates to the compounds of the formula I and to the use of the compounds of the formula I as components of liquid-crystalline media, liquid-crystalline media containing at least one compound of formula I and electro-optical displays containing such media.
  • the groups Q are preferably -CH 2 -, -CH 2 CH 2 - or a single bond.
  • X is preferably F, Cl, -CF 3 or -OCF 3 .
  • the compounds of the formula I are prepared by methods known per se, as described in the literature (for example in the standard works such as Hoitz-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart), and under reaction conditions that are known and suitable for the implementations mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • the starting materials can also be formed in situ in such a way that they are not isolated from the reaction mixture, but instead are immediately converted further into the compounds of the formula I.
  • an aldehyde of formula II Preferably an aldehyde of formula II
  • Solvents are used for the usual materials, e.g. Dimethylformamide, diethylene glycol dimethyl ether, N-methylpyrrolidone or THF.
  • the Grignard compound obtained from the corresponding bromobenzene derivative is converted to the tertiary cyclo using chlorotrialkyl orthotitanate or zirconate according to WO 87/05599 hexanol implemented.
  • the trans-cyclohexane carboxylic acid ester is obtained by customary methods. From the latter, the suitable precursors of the formula II are obtained by the customary standard method.
  • the bromobiphenyl compound can be prepared in a manner known per se by coupling metal-catalyzed coupling reactions (E. Poetsch,
  • Precursors are carried out which carry a group which can be converted into X instead of the radical X.
  • alkoxy compounds can be converted into corresponding phenols from which the
  • OCF 3 and OCF 2 H compounds can be produced by routine methods by reaction with CCl 4 / HF or CClF 2 H / NaOH.
  • the nitriles or the CF 3 compounds can be prepared from the corresponding benzoic acids or by treatment with SF 4 .
  • the iodides B can be prepared analogously or the compound of the formula is prepared from m-bromofluorobenzene in a complete analogy to Scheme 1
  • the best way to convert to alcohol is to reduce the nitrile to the aldehyde with DIBAH and then to the alcohol with LiAlH 4 .
  • liquid-crystalline media according to the invention preferably contain 2 to 40, in particular 4 to 30, components as further constituents. These media very particularly preferably contain 7 to 25 components in addition to one or more compounds according to the invention.
  • further components are preferably selected from nemati see or nematogenic (monotropic or isotropic) substances, especially substances from the classes of
  • L and E which may be the same or different, each independently represent a bivalent radical from the group consisting of -Phe-,
  • One of the radicals L and E is preferably Cyc, Phe or Pyr.
  • E is preferably Cyc, Phe or Phe-Cyc.
  • the media according to the invention preferably contain one or more components selected from the compounds of the formulas 1, 2, 3, 4 and 5, in which L and E are selected from the group Cyc, Phe and Pyr and at the same time one or more components selected from the compounds of Formulas 1, 2, 3, 4 and 5, in which one of the radicals L and E.
  • Residues L and E are selected from the group -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-.
  • R 'and R are different from one another, one of these radicals usually being alkyl or alkenyl.
  • R means -CN, -CF 3 , -OCF 3 , F, Cl or -NCS; R has the meaning given for the compounds of the partial formulas 1a to 5a and is preferably alkyl or alkenyl.
  • R " is particularly preferred, selected from the group consisting of -F, Cl, -CF 3 and -OCF 3 - but also others Variants of the proposed substituents in the compounds of the formulas 1, 2, 3, 4 and 5 are common. Many such substances or mixtures thereof are commercially available. All of these substances are based on methods known from the literature or in analogy to them
  • the media according to the invention preferably also contain components from the group of compounds 1b, 2b, 3b, 4b and 5b (group 2), the proportions of which are preferably as follows are:
  • Group 1 20 to 90%, in particular 30 to 90%,
  • Group 2 10 to 80%, in particular 10 to 50%, the sum of the proportions of the compounds according to the invention and of the compounds from groups 1 and 2 giving up to 100%.
  • the media according to the invention preferably contain
  • the media preferably contain three, four or five compounds according to the invention.
  • the media according to the invention are produced in a conventional manner.
  • the components are dissolved in one another, expediently at elevated temperature.
  • the liquid-crystalline phases according to the invention can be modified so that they can be used in all types of liquid-crystal display elements which have hitherto become known.
  • Such additives are known to the person skilled in the art and are described in detail in the literature (H. Kelker / R. Hatz,
  • pleochroic dyes can be added to produce colored guest-host systems or substances to change the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases.
  • the media according to the invention are particularly suitable for use in MLC displays.
  • K crystalline-solid state
  • S smectic phase (the index denotes the phase type)
  • N nematic state
  • Ch cholesteric phase
  • I isotropic phase.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

De nouveaux phénylcyclohexanes de formule (I) où Q est alkylène avec jusqu'à 5 atomes de carbone ou une liaison simple, A est (a), (b), (c), (d), (e), (f), (g), -CH2CH2CH2CH2-, -CH2CH2- ou une liaison simple, X représente F, Cl, -CF3, -CN, -OCF3, -OCHF2, alkyle ou alkoxy avec respectivement jusqu'à 7 atomes de C, et Y et Z représentent indépendamment H ou F, à condition que si X = CN et Y = Z = H, A soit différent de la liaison simple, peuvent être utilisés comme constituants de milieux mésomorphes.
EP19900915456 1989-11-03 1990-10-30 Phenylcyclohexanes et milieu mesomorphe Withdrawn EP0452444A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3936615 1989-11-03
DE3936615 1989-11-03
DE4006337 1990-03-01
DE4006337 1990-03-01

Publications (1)

Publication Number Publication Date
EP0452444A1 true EP0452444A1 (fr) 1991-10-23

Family

ID=25886719

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900915456 Withdrawn EP0452444A1 (fr) 1989-11-03 1990-10-30 Phenylcyclohexanes et milieu mesomorphe

Country Status (3)

Country Link
EP (1) EP0452444A1 (fr)
JP (1) JPH04502627A (fr)
WO (1) WO1991006522A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4217248B4 (de) * 1991-06-05 2005-06-16 Merck Patent Gmbh Vinylverbindungen
ATE179204T1 (de) * 1993-10-08 1999-05-15 Chisso Corp Cyclohexanderivat
WO1998008791A1 (fr) 1996-08-26 1998-03-05 Chisso Corporation Compose a base de derives de fluorovinyl, composition de cristal liquide et afficheur a cristaux liquides
AU4222497A (en) 1996-09-27 1998-04-17 Chisso Corporation Compound having alkadienyl group as side chain, and liquid crystal composition using same
JP2001328975A (ja) * 2000-05-22 2001-11-27 Chisso Corp フッ素置換アルケニル化合物、液晶組成物および液晶表示素子

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1336441C (fr) * 1987-12-28 1995-07-25 Manabu Uchida Composition de cristal liquide
JPH01216967A (ja) * 1988-02-26 1989-08-30 Chisso Corp 液晶化合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9106522A2 *

Also Published As

Publication number Publication date
JPH04502627A (ja) 1992-05-14
WO1991006522A3 (fr) 1991-10-03
WO1991006522A2 (fr) 1991-05-16

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