WO1990015114A1 - Composes cycliques - Google Patents

Composes cycliques Download PDF

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Publication number
WO1990015114A1
WO1990015114A1 PCT/EP1990/000828 EP9000828W WO9015114A1 WO 1990015114 A1 WO1990015114 A1 WO 1990015114A1 EP 9000828 W EP9000828 W EP 9000828W WO 9015114 A1 WO9015114 A1 WO 9015114A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
propyl
formula
liquid crystal
cyc
Prior art date
Application number
PCT/EP1990/000828
Other languages
English (en)
Inventor
David Coates
Ian Charles Sage
Simon Greenfield
D. Baxter
Reinhard Hittich
Andreas WÄCHTLER
Original Assignee
MERCK Patent Gesellschaft mit beschränkter Haftung
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 Gesellschaft mit beschränkter Haftung filed Critical MERCK Patent Gesellschaft mit beschränkter Haftung
Publication of WO1990015114A1 publication Critical patent/WO1990015114A1/fr

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Classifications

    • 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
    • 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
    • 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
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the invention relates to ring compounds of formula I
  • n 1 or 2
  • L are each independently H or F
  • X is F, Cl, -CN, -CF 3 , -OCF 3 or -OCHF 2 or has one of the meanings given for R .
  • the compounds of the formula I can be used as components of liquid crystal media, in particular for displays which are based on the principle of the twisted nematic cell, including TN cells with a higher twist angle like_ STN, SBE, O I etc., on the guest-host effect, on the effect of deformation of orientated phases or on the effect of dynamic scattering.
  • the compounds of the formula I can also be used for two-frequency switching systems. Compounds similar to those of formula I are known from DE 3040 632. These compounds exhibit on the one hand a neutral or positive dielectric anisotropy. But on the other hand they have a rather small mesophase range and generally show smectic structures.
  • the invention was based on the object of discovering new stable liquid crystalline or mesogenic compounds which show favorable elastic properties and are especially suitable for supertwist displays without exhibiting the shortcomings of the prior art compounds.
  • the compounds of the formula I have a wide field of appli ⁇ cation. Depending on the selection of the substituents, these compounds can be used as base materials from which liquid crysta! phases are predominantly composed; however, compounds of the formula I can also be added to liquid crystal base materials from other classes of compounds, for example in order to optimize the dielectric and/or optical anisotropy of such a dielectric.
  • SUBSTITUTE SHEET The compounds of the formula I are colourless in the pure state and form liquid crystal mesophases in a temperature range which is favorably placed for electrooptical use. They are very stable towards chemicals, heat and light.
  • the invention thus relates to the compounds of the formula I and the use of these compounds as components of liquid crystal media.
  • the invention furthermore re ⁇ lates to liquid crystal media containing at least one compound of the formula I and to liquid crystal display elements, in particular electrooptical display elements, which contain media of this type.
  • the compounds of the formula I accordingly include pre ⁇ ferred species of the part formulae la to Ic:
  • R is preferably alkyl, furthermore also alkenyl or alkyl or alkenyl groups in which one CH 2 -group is replaced by oxygen.
  • R and/or X are alkyl and/or alkoxy groups, these can be straight-chain or branched. Preferably, they are straight-chain and have 2, 3, 4, 5, 6 or 7 C atoms and are accordingly preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, also methyl, octyl, nonyl, methoxy, octoxy or nonoxy.
  • R and/or X are alkenyl groups these can be straight- chain or branched. Preferably, they are straight-chain and have 2 to 8 C atoms. They are accordingly, in particular, vinyl, prop-1- or prop-2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3-, -4-, -5- or -6-enyl or oct-1-, -2.-., -3-, -4-, -5-, -6- or -7-enyl.
  • R and/or X are alkenoxy groups these can be straight chain or branched. Pre erably they are straight-chain and are given via formula II
  • r is 1 or 2 and X runs from 0 to 6.
  • Trans-isomers of both the alkenyl and the alkenoxy groups are preferred.
  • Compounds of the formula I with branched terminal groups R and/or X can be of importance because of a better solu ⁇ bility in the customary liquid crystal base materials, but in particular as chiral doping substances if they are optically active.
  • Branched groups oft this type as a rule contain not more than one chain branching.
  • formula I- includes both the optical antipodes and racemates as well as mixtures thereof.
  • X is preferably F, Cl, -CN, -CF 3 , -OCF 3 or -OCHF 2 .
  • -OCF 3 and -OCHF 2 are especially preferred.
  • m is preferably 1.
  • the compounds of the formula I are prepared by methods which are known per se, such as are described in the literature (for example in the standard works, such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry] , Georg-Thieme-Verlag, Stuttgart),
  • the starting substances can also be formed in situ, such that they are not isolated from the reaction mixture but are immediately reacted further to give the compounds of the formula I.
  • liquid crystal media according to the invention prefer- ablv contain 2-40 components and in particular 4-30 com ⁇ ponents. Liquid crystal media being composed of one or more compounds of formula I and 7-25 other components are especially preferred.
  • These additional components are preferably chosen from the nematic or nematogenic (monotropic or isotropic) substances; in particular from the classes of azoxy- benzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl cyclohexanecarboxylates, phenyl or cyclohexyl cyclo- hexylbenzoates, phenyl or cyclohexyl cyclohexylcyclo- hexanecarboxylates, cyclohexylphenylbenzoates, cyclohexyl- phenyl cyclohexanecarboxylates, cyclohexylphenylcyclo- hexylcyclohexanecarboxylates, phenylcyclohexanes, cyclohexyl
  • L and E may be equal or different from each other.
  • L and E independently from each other denote a bivalent residue selected from the group consisting of -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -G-Phe-, -G-Cyc- and their mirror images; in this compilation of residues Phe denotes un- substituted or fluorinated 1,4-phenylen, Cyc trans- 1,4- cyclohexylene or 1,4-cyclohexenylen, Pyr pyrimidine-2,5- diyl or pyridine-2,5-diyl, Dio l,3-dioxane-2,5-diyl and G 2-(t ans-l,4-cyclohexyl)-ethyl, pyrimidine-2,5-
  • One of the residues L and E is preferably Cyc, Phe. or Pyr.
  • E preferably denotes Cyc, Phe or Phe-Cyc.
  • the liquid crystal media according to the invention preferably con- tain one or more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with L and E meaning Cyc, Phe and Pyr, said liquid crystal media further containing at the same time one ore more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with one of the residues L and E denoting Cyc, Phe and Pyr and the other residue being selected from the group consisting of -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -G-Cyc-, said liquid
  • SUBSTITUTESHEET crystal media containing in addition to this optionally one or more components selected from the compounds of formulae 1, 2, 3, 4 and 5 with L and E being selected from the group consisting of -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc.
  • R 1 and R" are independent ⁇ ly from each other alkyl, alkenyl, alkoxy, alkenoxy with up to 8 carbon atoms. R' and R" differ from one another in most of these compounds, one of the residues usually being alkyl or alkenyl.
  • R" denotes -CN, -CF 3 , -F, -Cl or -NCS while R 1 has the meaning indicated in subgroup 1 and is preferably alkyl or alkenyl.
  • R 1 has the meaning indicated in subgroup 1 and is preferably alkyl or alkenyl.
  • Other variants of the envisaged substituents in the compounds of formulae 1, 2, 3, 4 and 5 are also customary. Many such substances are commercially available. All these substances are obtainable by methods which are known from the literature or by analogous methods.
  • liquid crystal media according to the invention pre ⁇ ferably contain in addition to components selected from subgroup 1 also components of subgroup 2, the percentage of these components being as follows:
  • subgroup 1 20 to 90 %, in particular 30 to 90 % subgroup 2: 10 to 50 %, in particular 10 to 50 %
  • the media according to the invention preferably contain 1 to 40 %, in particular 5 to 30 % of the compounds according to the invention. Media containing more than 40 %, in particular 45 to 90 % of the compounds accor- ding to the invention are further preferred.
  • the media contain preferably 3, 4 or 5 compounds according to the invention.
  • the media according to the invention are prepared in a manner which is customary per se.
  • the com- ponents are dissolved in one another, advantageously at elevated temperature.
  • the liquid crystal media accor ⁇ ding to the invention can be modified by suitable addi ⁇ tives so that they can be used in all the types of liquid crystal display devices. Such additives are known to the expert and are described in detail in the literature
  • pleochroic dyestuffs to prepare colored guest-host systems or substances for modifying the dielectric aniso- tropy, the viscosity and/or the orientation of the nematic phases.
  • C crystalline-solid state
  • S smectic phase (the index denoting the typ of smectic phase)
  • N nematic phase
  • Ch cholesteric phase
  • I isotropic phase. The number being embraced by 2 of these symbols denotes the tem ⁇ perature of phase change.

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

L'invention concerne des composés cycliques de formule (I), dans laquelle R1 représente un reste d'alkyle contenant jusqu'à 12 atomes de carbone, dans lequel un ou deux groupes CH¿2? peuvent également être remplacés par -O- et/ou -CH=CH-, m représente 1 ou 2, L?1, L2 et L3¿ représentent chacun indépendamment H ou F, et X représente F, Cl, -CN, -CF¿3?, -OCF3 ou -OCHF2 ou a une des définitions données pour R?1¿, lesdits composés étant adaptés en tant que constituants de milieux à cristaux liquides.
PCT/EP1990/000828 1989-06-08 1990-05-23 Composes cycliques WO1990015114A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898913205A GB8913205D0 (en) 1989-06-08 1989-06-08 Ring compounds
GB8913205.4 1989-06-08

Publications (1)

Publication Number Publication Date
WO1990015114A1 true WO1990015114A1 (fr) 1990-12-13

Family

ID=10658118

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/000828 WO1990015114A1 (fr) 1989-06-08 1990-05-23 Composes cycliques

Country Status (4)

Country Link
EP (1) EP0427837A1 (fr)
JP (1) JPH04500214A (fr)
GB (1) GB8913205D0 (fr)
WO (1) WO1990015114A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0475254A1 (fr) * 1990-09-10 1992-03-18 F. Hoffmann-La Roche Ag Composés de chlorophényl alkoxyalkyl

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3237367A1 (de) * 1981-10-14 1983-04-28 F. Hoffmann-La Roche & Co AG, 4002 Basel Phenylaethane
EP0129177A2 (fr) * 1983-06-17 1984-12-27 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Bentonitriles nématiques
EP0149208A2 (fr) * 1984-01-17 1985-07-24 MERCK PATENT GmbH Dérivés d'éthane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3237367A1 (de) * 1981-10-14 1983-04-28 F. Hoffmann-La Roche & Co AG, 4002 Basel Phenylaethane
EP0129177A2 (fr) * 1983-06-17 1984-12-27 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Bentonitriles nématiques
EP0149208A2 (fr) * 1984-01-17 1985-07-24 MERCK PATENT GmbH Dérivés d'éthane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0475254A1 (fr) * 1990-09-10 1992-03-18 F. Hoffmann-La Roche Ag Composés de chlorophényl alkoxyalkyl
US5399689A (en) * 1990-09-10 1995-03-21 Hoffmann-La Roche Inc. Chlorophenylalkoxyalkyl compounds

Also Published As

Publication number Publication date
JPH04500214A (ja) 1992-01-16
GB8913205D0 (en) 1989-07-26
EP0427837A1 (fr) 1991-05-22

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