WO1990014406A1 - Derives de cyclohexyle fluores - Google Patents

Derives de cyclohexyle fluores Download PDF

Info

Publication number
WO1990014406A1
WO1990014406A1 PCT/EP1990/000741 EP9000741W WO9014406A1 WO 1990014406 A1 WO1990014406 A1 WO 1990014406A1 EP 9000741 W EP9000741 W EP 9000741W WO 9014406 A1 WO9014406 A1 WO 9014406A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
cyclohexyl
denotes
cyc
formula
Prior art date
Application number
PCT/EP1990/000741
Other languages
English (en)
Inventor
David Coates
Ian Charles Sage
Simon Greenfield
Dieter Dorsch
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 WO1990014406A1 publication Critical patent/WO1990014406A1/fr

Links

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
    • C09K19/30—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
    • 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
    • C07C43/225—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
    • 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 fluorinated cyclohexyl deri ⁇ vatives of formula I
  • n 0 or 1
  • X is F, -CF, -OCF 3 or -OCHF 2
  • liquid crystalline media being a mixture of at least 2 compounds, characterized in that at least one compound is a fluorinated cyclohexyl derivative accord ⁇ ing to formula I.
  • the invention was based on the object of discovering new stable liquid crystal or mesogenic compounds which are suitable as components of liquid crystalline media and, in particular, have advantageous values for optical and dielectric anisotropy combined with low viscosity and high nematcgenity. Similar bicyclohexyl derivatives are described in Euro ⁇ pean Patent 0 125 563 :
  • fluorinated cyclohexyls of formula I are highly suitable as components of liquid crystalline media.
  • they have especially advantageous values of optical and dielectric anisotropy ( ⁇ , ⁇ j_ and ⁇ character). It is also possible to obtain stable liquid crystal phases with a broad ne atic mesophase range including a good deep temperature behaviour and a comparatively low viscosity with the aid of these compounds.
  • the compounds of the formula I can be used as the base materials from which liquid crystal media are predominantly composed; however, it is also possible for compounds of the formula I to be added to liquid crystal base materials of other classes of compounds, for example in order to influence the dielectric and/or optical anisotropy and/or the viscosity and/or the nematic mesophase range of such a dielectric.
  • the compounds of the formula I are colourless in the pure state and are liquid crystalline in a temperature range which is favourably placed for electrooptical use. They are very stable towards chemicals, heat and light.
  • the invention thus relates to the fluorinated cyclohexyl derivatives of the formula I, to liquid crystalline media with at least two liquid crystalline components, wherein at least on component is a compound of the formula I and to liquid crystal display devices containing such media.
  • R is preferably alkyl, alkoxy, oxaalkyl, alkanoyloxy or alkenyl and can exhibit a straight-chain or branched structure.
  • Alkyl or alkoxy preferably are straight-chain and have 2 , 3, 4, 5, 6 or 7 C atoms. Accordingly they are prefer- ably ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, also methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetra- decyl,. pentadecyl, methoxy, octoxy, nonoxy, decoxy, un- decoxy, dodecoxy, tridecoxy or tetradecoxy.
  • Alkenyl is preferably straight-chain and has 2 or 10 C atoms. It is accordingly, in particular, vinyl, prop-1- or prop-2- enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5- -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl or dec-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.
  • Branched groups of this type as a rule contain not more than one chain branching.
  • formula I includes both the optical antipodes and race ates as well as mixtures thereof.
  • n is preferably 1.
  • X is preferably -OCF 3 or -OCHF 2 and furthermore preferably -CF 3 .
  • 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, ethoden der Organischen Chemie [Methods of Organic Chemistry], Georg Thieme Verlag, Stuttgart), and in particular under reaction conditions which are known and suitable for the reactions mentioned. Variants which are known per ⁇ e and are not mentioned in more detail here can also be used in this connection.
  • the starting materials can also be formed t in situ, such that they are not isolated from the reac ⁇ tion mixture but are immediately reacted further to give the compounds of the formula I.
  • the liquid crystal media according to the invention prefer ⁇ ably 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 cyclohexyl- benzoates, phenyl or cyclohexyl cyclohexylcyclohexane- carboxylates, cyclohexylphenylbenzoates, cyclohexyl- phenyl cyclohexanecarboxylates, cyclohexylphenyl cyclo ⁇ hexylcyclohexanecarboxylates, phenylcyclohexanes, cyclohexylbi
  • the 1,4-phenylene groups of these compounds may be fluorinated.
  • the most important compounds which are possible consti ⁇ tuents of liquid crystal media according to the invention can be characterized by the formalae 1, 2, 3, 4 and 5:
  • L and U may be equal or different from each other.
  • L and U 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-(trans-l,4-cyclohexyl)-ethyl, pyrimidine-2,5-di
  • One of the residues L and U is preferably Cyc, Phe or ⁇ r.
  • U 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 ⁇ 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 U 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 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 ⁇ being selected from the group consisting of -Phe-Cyc-, -Cyc-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 percentages of the com ⁇ pounds according to the invention and the compounds of sub ⁇ group 1 and 2 may add up to give 100 %.
  • 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 it is possible to add 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.
  • a liquid crystalline medium consisting of

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 se rapporte à des dérivés de cyclohexyle fluorés représentés par la formule (I), où R1 représente un résidu alkyle comportant jusqu'à 12 atomes de carbone, dans lequel un ou deux groupes CH¿2?- non adjacents peuvent également être remplacés par -O-, -O-CO-, -CO-O- et/ou -CH=CH-, m est égal à 0 ou à 1, et X représente F, -CF3, -OCF3 ou -OCHF2.
PCT/EP1990/000741 1989-05-16 1990-05-08 Derives de cyclohexyle fluores WO1990014406A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8911217.1 1989-05-16
GB898911217A GB8911217D0 (en) 1989-05-16 1989-05-16 Fluorinated cyclohexyl derivatives

Publications (1)

Publication Number Publication Date
WO1990014406A1 true WO1990014406A1 (fr) 1990-11-29

Family

ID=10656817

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/000741 WO1990014406A1 (fr) 1989-05-16 1990-05-08 Derives de cyclohexyle fluores

Country Status (5)

Country Link
EP (1) EP0425624A1 (fr)
JP (1) JPH03506038A (fr)
CA (1) CA2033087A1 (fr)
GB (1) GB8911217D0 (fr)
WO (1) WO1990014406A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0521420A1 (fr) * 1991-07-04 1993-01-07 MERCK PATENT GmbH Dérivés fluorés du cyclohexyle

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0125563A2 (fr) * 1983-05-14 1984-11-21 MERCK PATENT GmbH Bicyclohexyléthanes
WO1987006602A1 (fr) * 1986-05-02 1987-11-05 MERCK Patent Gesellschaft mit beschränkter Haftung Phases smectiques de cristaux liquides
DE3732284A1 (de) * 1987-09-25 1989-04-13 Merck Patent Gmbh Substituierte phenyltrifluormethylether
EP0315014A2 (fr) * 1987-11-06 1989-05-10 F. Hoffmann-La Roche Ag Dérivés halogénés du benzène
DE3736489A1 (de) * 1987-10-28 1989-05-11 Merck Patent Gmbh Kreuzkopplung von titanorganylen

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0125563A2 (fr) * 1983-05-14 1984-11-21 MERCK PATENT GmbH Bicyclohexyléthanes
WO1987006602A1 (fr) * 1986-05-02 1987-11-05 MERCK Patent Gesellschaft mit beschränkter Haftung Phases smectiques de cristaux liquides
DE3732284A1 (de) * 1987-09-25 1989-04-13 Merck Patent Gmbh Substituierte phenyltrifluormethylether
DE3736489A1 (de) * 1987-10-28 1989-05-11 Merck Patent Gmbh Kreuzkopplung von titanorganylen
EP0315014A2 (fr) * 1987-11-06 1989-05-10 F. Hoffmann-La Roche Ag Dérivés halogénés du benzène

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0521420A1 (fr) * 1991-07-04 1993-01-07 MERCK PATENT GmbH Dérivés fluorés du cyclohexyle

Also Published As

Publication number Publication date
CA2033087A1 (fr) 1990-11-17
GB8911217D0 (en) 1989-07-05
EP0425624A1 (fr) 1991-05-08
JPH03506038A (ja) 1991-12-26

Similar Documents

Publication Publication Date Title
EP0413785B1 (fr) Milieux cristallins liquides contenant des oligophenyles fluores
US5356562A (en) Fluoro tolans and liquid crystalline media
US4897216A (en) 2,3-difluorophenol derivatives
US5194178A (en) Chloro tolanes
US6200654B1 (en) 1,4-disubstituted 2,6-difluorobenzene compounds, and a liquid-crystalline medium
WO1992005230A2 (fr) Derives de fluorobenzene
EP0445248B1 (fr) Derives de pyridine
US5190692A (en) Four ring esters and ethers
EP0426815B1 (fr) Derives de byphenyles fluorures
EP0423520B1 (fr) Composition liquide cristalline pour utilisation dans une cellule nématique torsadée
US5637257A (en) Fluoro-chloro-benzene derivatives
EP0437595B1 (fr) Derives de fluoro-chloro-benzene
EP0428666B1 (fr) Derives de fluoro-chloro-benzene
US5389294A (en) Chlorobenzene derivatives
WO1990014406A1 (fr) Derives de cyclohexyle fluores
EP0394906B1 (fr) Composition liquide cristalline
EP0446911A1 (fr) Dérivés de fluorobenzène
GB2266714A (en) Liquid-crystalline alkoxymethylene compounds
WO1990015114A1 (fr) Composes cycliques
EP0521420A1 (fr) Dérivés fluorés du cyclohexyle
GB2235197A (en) Liquid crystalline p-chlorobenzene derivatives with a lateral fluorine substituent
GB2272216A (en) Liquid crystalline di-, tri- and tetra-fluorinated phenylpyrazines
GB2271563A (en) Liquid crystalline (2-(cyclylcarboxy)-5-pyrazyl)benzenes
WO1991009016A1 (fr) Derives heterocycliques substitues par halophenyle

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1990906983

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2033087

Country of ref document: CA

WWP Wipo information: published in national office

Ref document number: 1990906983

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1990906983

Country of ref document: EP