WO1991015450A1 - Phenylcyclohexanes et milieu de cristaux liquides - Google Patents

Phenylcyclohexanes et milieu de cristaux liquides Download PDF

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Publication number
WO1991015450A1
WO1991015450A1 PCT/EP1991/000603 EP9100603W WO9115450A1 WO 1991015450 A1 WO1991015450 A1 WO 1991015450A1 EP 9100603 W EP9100603 W EP 9100603W WO 9115450 A1 WO9115450 A1 WO 9115450A1
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WO
WIPO (PCT)
Prior art keywords
compounds
formula
phenylene
trans
liquid
Prior art date
Application number
PCT/EP1991/000603
Other languages
German (de)
English (en)
Inventor
Eike Poetsch
Volker Meyer
Ulrich Finkenzeller
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 WO1991015450A1 publication Critical patent/WO1991015450A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/192—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • 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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • 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 new phenylcyclohexanes of the formula I
  • RR alkyl or alkenyl with up to 12 carbon atoms E -A-, -CH 2 CH 2 -, -CH 2 CH 2 -A- or -A-CH 2 CH 2 -,
  • 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 poor with respect 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.
  • STN Supertwist type
  • Twist angles of significantly more than 220 ° C or in displays with an active matrix have disadvantages in the materials used to date.
  • 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 groups Q are preferably -O-.
  • X is preferably F, Cl, -OCHF 2 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 Houben-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.
  • a cyclohexanol of the formula II is preferably
  • the bromobiphenyl compound can be produced in a manner known per se by coupling reactions catalyzed by noble metals (E. Poetsch, Contacts, Merck, Darmstadt 1988, 15).
  • the 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.
  • These further constituents are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular substances from the classes of the biphenyls, ter phenyls, phenyl or cyclohexyl benzoates, cyclohexane-carboxylic acid phenyl- or cyclohexyl ester, phenyl or cyclohexyl esters of cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl of benzoic acid, of cyclohexanecarboxylic acid, or of cyclohexylic acid, or of cycl
  • R '-LC ⁇ CER "5 In formulas 1, 2, 3, 4 and 5, L and E, which may be the same or different, each independently represent a bivalent radical from the group consisting of -Phe-, -Cyc-, -Phe-Phe-, -Phe- Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -G-Phe- and -G-Cyc- as well as their mirror images formed group, whereby Phe unsubstituted or substituted by fluorine-substituted 1,4-phenylene, Cyc- 1,4-cyclohexylene or 1,4-cyclohexenylene, pyr pyrimidine-2,5-diyl or pyridine-2,5-diyl, dio 1,3-dioxane-2,5-diyl and G 2- (trans-1, 4-Cyclohexyl) ethyl, pyrimidine-2,
  • 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 is selected from the group Cyc, Phe and Pyr and the other radical is selected from the group -Phe-Phe-, -Phe-Cyc-, - Cyc-Cyc-, -G-Phe- and -G-Cyc-, and optionally one or more components selected from the compounds of the formulas 1, 2, 3, 4 and 5, in which the radicals L and E are selected from the group -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-C
  • R 'and R each independently represent alkyl, alkenyl, alkoxy, alkenyloxy or alkanoyloxy having up to 8 carbon atoms. In most of these compounds, R' and R" are different from one another different, one of these radicals is usually alkyl or alkenyl.
  • Sub-formulas Ib, 2b, 3b, 4b and 5b mean R "-CN, -CF 3 , -OCF 3 , F, Cl or -NCS; R has the meaning given for the compounds of sub-formulas Ia to 5a and is preferably alkyl or Alkenyl. Particularly preferred is R ", selected from the group consisting of F, Cl, -CF 3 and
  • the media according to the invention preferably also contain components from the group of compounds 1a, 2a, 3a, 4a and 5a (group 1), the media according to the invention preferably also contain components from the group of
  • 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 1 to 40%, particularly preferably 5 to 30%, of compounds according to the invention. Also preferred are media containing more than 40%, in particular 45 to 90%, of compounds according to the invention.
  • 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, advantageously 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
  • pleochroic dyes for producing colored guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases can be added.
  • the media according to the invention are particularly suitable for use in MLC displays.
  • mp. Melting point, cp. - Clarification point.
  • Foreland below percentages mean percentages by weight; all temperatures are given in degrees Celsius.
  • Conventional work-up means: water is added, the mixture is extracted with methylene chloride, the mixture is separated off, the organic phase is dried, evaporated and the product is purified by crystallization and / or chromatography.
  • K crystalline-solid state
  • S smectic phase (the index denotes the phase type)
  • N nematic state
  • Ch cholesteric phase
  • I isotropic phase. The number between two symbols indicates the transition temperature in degrees Celsius.

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 -O- ou bien -CO-O-, R est alkyle ou alkényle avec jusqu'à 12 atomes de carbone, E est -A-, -CH2-CH2-, -CH2CH2-A- ou bien -A-CH2CH2-, A est trans-1,4-cyclohexylène, 1,4-phénylène, 3-fluor-1,4-phénylène, 3,5-difluor-1,4-phénylène ou bien une liaison simple, X est F, Cl, -CF3, -OCF3 ou bien -OCHF2, et Y et Z sont indépendamment H ou F, à condition que si E = trans-1,4-cyclohexylène et qu'en même temps Q = -CO-O-, X soit Cl, -CF3, -OCF3 ou bien -OCHF2 et/ou Y = Z = F, s'utilisent comme constituants de milieu de cristaux liquides.
PCT/EP1991/000603 1990-04-04 1991-03-28 Phenylcyclohexanes et milieu de cristaux liquides WO1991015450A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4010917 1990-04-04
DEP4010917.8 1990-04-04

Publications (1)

Publication Number Publication Date
WO1991015450A1 true WO1991015450A1 (fr) 1991-10-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/000603 WO1991015450A1 (fr) 1990-04-04 1991-03-28 Phenylcyclohexanes et milieu de cristaux liquides

Country Status (3)

Country Link
EP (1) EP0476103A1 (fr)
JP (1) JPH04506361A (fr)
WO (1) WO1991015450A1 (fr)

Cited By (5)

* 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
WO1993002153A1 (fr) * 1991-07-16 1993-02-04 MERCK Patent Gesellschaft mit beschränkter Haftung Milieu a cristaux liquides
EP0595144A1 (fr) * 1992-10-30 1994-05-04 F. Hoffmann-La Roche Ag Alcènoates de cyclohexyles comme constituants de mélanges de cristaux liquides
US5520846A (en) * 1991-07-16 1996-05-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid-crystalline medium
EP0478739B1 (fr) * 1990-04-13 1996-09-11 MERCK PATENT GmbH Milieu de cristaux liquides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998032722A1 (fr) 1997-01-29 1998-07-30 Chisso Corporation Composes de cristaux liquides contenant des groupes alkyles fluores, composition de cristaux liquides, et dispositif d'affichage a cristaux liquides
JP4742210B2 (ja) * 2001-05-16 2011-08-10 Ｊｎｃ株式会社 酸フッ化物誘導体およびそれを含む液晶組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3136624A1 (de) * 1981-09-15 1983-03-31 Merck Patent Gmbh, 6100 Darmstadt Fluessigkristalline halogenverbindungen, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DE3508425A1 (de) * 1984-03-23 1986-09-11 Merck Patent Gmbh, 6100 Darmstadt Cyclohexanderivate
DE3714043A1 (de) * 1987-04-28 1988-11-17 Merck Patent Gmbh Elektrooptisches fluessigkristallanzeigeelement
DE3732284A1 (de) * 1987-09-25 1989-04-13 Merck Patent Gmbh Substituierte phenyltrifluormethylether
DE3807872A1 (de) * 1988-03-10 1989-09-21 Merck Patent Gmbh Difluorbenzolderivate
DE3904817A1 (de) * 1989-02-17 1990-09-20 Nematel Dr Rudolf Eidenschink Difluormethyl-verbindungen

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3136624A1 (de) * 1981-09-15 1983-03-31 Merck Patent Gmbh, 6100 Darmstadt Fluessigkristalline halogenverbindungen, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DE3508425A1 (de) * 1984-03-23 1986-09-11 Merck Patent Gmbh, 6100 Darmstadt Cyclohexanderivate
DE3714043A1 (de) * 1987-04-28 1988-11-17 Merck Patent Gmbh Elektrooptisches fluessigkristallanzeigeelement
DE3732284A1 (de) * 1987-09-25 1989-04-13 Merck Patent Gmbh Substituierte phenyltrifluormethylether
DE3807872A1 (de) * 1988-03-10 1989-09-21 Merck Patent Gmbh Difluorbenzolderivate
DE3904817A1 (de) * 1989-02-17 1990-09-20 Nematel Dr Rudolf Eidenschink Difluormethyl-verbindungen

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0478739B1 (fr) * 1990-04-13 1996-09-11 MERCK PATENT GmbH Milieu de cristaux liquides
EP0521420A1 (fr) * 1991-07-04 1993-01-07 MERCK PATENT GmbH Dérivés fluorés du cyclohexyle
WO1993002153A1 (fr) * 1991-07-16 1993-02-04 MERCK Patent Gesellschaft mit beschränkter Haftung Milieu a cristaux liquides
US5520846A (en) * 1991-07-16 1996-05-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid-crystalline medium
EP0595144A1 (fr) * 1992-10-30 1994-05-04 F. Hoffmann-La Roche Ag Alcènoates de cyclohexyles comme constituants de mélanges de cristaux liquides
US5380462A (en) * 1992-10-30 1995-01-10 Hoffmann-La Roche Inc. Cyclohexyl alkenoate compounds

Also Published As

Publication number Publication date
EP0476103A1 (fr) 1992-03-25
JPH04506361A (ja) 1992-11-05

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