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WO1995013999A1 - 3,5-difluorobenzenes et leur utilisation dans des melanges de cristaux liquides - Google Patents

3,5-difluorobenzenes et leur utilisation dans des melanges de cristaux liquides Download PDF

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Publication number
WO1995013999A1
WO1995013999A1 PCT/EP1994/003533 EP9403533W WO9513999A1 WO 1995013999 A1 WO1995013999 A1 WO 1995013999A1 EP 9403533 W EP9403533 W EP 9403533W WO 9513999 A1 WO9513999 A1 WO 9513999A1
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Prior art keywords
diyl
liquid crystal
trans
atoms
difluorobenzenes
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English (en)
Inventor
Hubert Schlosser
Dietmar Jungbauer
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Hoechst AG
Merck Patent GmbH
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Hoechst AG
Merck Patent GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • 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
    • 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
    • C09K19/06—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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • 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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • 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
    • 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone

Definitions

  • Optical effects can be achieved, for example, with the help of birefringence, the incorporation of dichroic dye molecules (guest host mode) or light scattering.
  • thermodynamic and electro-optical variables such as phase sequence and electro-optical variables
  • Phase temperature range refractive index, birefringence and dielectric anisotropy, switching time, threshold voltage, steepness of the electro-optical
  • electromagnetic radiation as well as to the materials with which they are associated during and after the manufacturing process (e.g.
  • Liquid crystal mixtures known see: DE-A 41 16 158,
  • Liquid crystal mixtures are suitable.
  • the present invention therefore relates to new 3,5-difluorobenzenes of the general formula (I), ⁇
  • a 1 , A 2 , A 3 are identical or different 1, 4-phenylene, pyrazine-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, in which one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, (1,3,4) thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, Bicyclo [2.2.2] octane-1,4-diyl or 1,3-dioxaborinane-2,5-diyl;
  • k, l, m, n, o are zero or one, provided that the sum k + m + o is greater than zero; with the following provisos: for k + m + o equal to one is X
  • -CH 2 CH 2 -, -CH CH-, -C ⁇ C-, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 -O-,
  • -CH 2 CH 2 -, -CH CH-, -C ⁇ C-, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 -O-,
  • R 1 is a straight-chain alkyl having 1 to 15 carbon atoms
  • a 1 , A 2 , A 3 are identical or different 1, 4-phenylene, in which one or two H atoms can be replaced by F, or trans-1, 4-cyclohexylene;
  • M 1 , M 2 are the same or different -CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -,
  • k, I, m, n, o are zero or one, provided that the sum k + m + o is greater than zero; with the following provisos: for k + m + o equal to one is X
  • Particularly preferred compounds of the formula (I) are the 3,5-difluorobenzenes of the formulas (11) to (125) listed below:
  • R 1 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl.
  • the compounds according to the invention can generally be prepared without problems by methods known per se from literature and to the person skilled in the art.
  • 3,5-difluorophenol (II) can be obtained by esterification with carboxylic acids or
  • 3,5-difluorobenzoic acid (III) gives compounds (I) according to the invention by esterification with alcohols of Z 2 (see: Tetrahedron 1980, 36, 2409).
  • bromo-3,5-difluorobenzene (IV) with organometallic derivatives of Z 2 , for example Grignard, lithium and zinc derivatives, and boronic acids of Z 2 using transition metal catalysts, for example dichloro [1, 3-bis (diphenylphosphino) propane] nickel (II), tetrakis (triphenylphosphine) palladium and [1, 1 'bis (diphenylphosphino) ferrocene] palladium (II) chloride
  • the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • EP-A O3 91 203 for compounds with pyridine-2,5-diyl groups
  • Disubstituted pyrimidines can also be found, for example, in the corresponding volumes of the series "The Chemistry of Heterocyclic Compounds" by
  • Dioxane derivatives are useful by reacting an appropriate aldehyde (or one of its reactive derivatives) with one
  • Sulfuric acid, benzene or p-toluenesulfonic acid at temperatures between about 20 ° C and about 150 ° C, preferably between 80 ° C and 120 ° C.
  • Acetals are primarily suitable as reactive derivatives of the starting materials.
  • the aldehydes can be obtained by oxidation of corresponding alcohols or by reduction of nitriles or corresponding carboxylic acids or their derivatives, and the diols can be obtained by reducing corresponding diesters.
  • Esters of the formula (I) can also be correspondingly esterified
  • Carboxylic acids (or their reactive derivatives) with alcohols or
  • the acid halides especially the chlorides and bromides
  • the anhydrides e.g. also mixed anhydrides, azides or esters, in particular alkyl esters with 1 to 4 carbon atoms in the alkyl group.
  • Reactive derivatives of the alcohols or phenols mentioned include, in particular, the corresponding metal alcoholates or phenolates,
  • an alkali metal such as sodium or potassium.
  • esterification is advantageously carried out in the presence of an inert solvent.
  • an inert solvent particularly suitable are ethers, such as diethyl ether,
  • Hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as carbon tetrachloride, dichloromethane or tetrachlorethylene and sulfoxides such as dimethyl sulfoxide or sulfolane.
  • Ethers of the formula (I) are more appropriate by etherification
  • Hydroxy compounds preferably corresponding phenols, are available, the hydroxyl compound expediently first in a corresponding
  • Metal derivative for example by treatment with NaH, NaNH 2 , NaOH, KOH, Na 2 CO 3 or K 2 CO 3 is converted into the corresponding alkali metal alcoholate or alkali metal phenolate.
  • This can then be reacted with the corresponding alkyl halide, sulfonate or dialkyl sulfate, advantageously in an inert solvent such as acetone, 1, 2-dimethoxyethane, DMF or dimethyl sulfoxide, or with an excess of aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 20 and 100 ° C.
  • Light modulators elements for image processing, signal processing or generally in the field of nonlinear optics are suitable. This also applies to compounds that have no liquid-crystalline phases as the pure substance.
  • the compounds of formula (I) are for introduction or
  • the invention therefore also relates to the use of compounds of the formula (I) in liquid-crystal mixtures.
  • the invention further relates to liquid crystal mixtures which contain one or more compounds of the formula (I).
  • the liquid crystal mixtures according to the invention generally consist of 2 to 20, preferably 2 to 15 components, including at least one, preferably 1 to 5, particularly preferably 1 to 3, compounds of the formula (I).
  • the LC mixtures according to the invention can be nematic or chiral nematic, for example.
  • the liquid crystal mixtures generally contain 0.1 to 70 mol%, preferably 0.5 to 50 mol%, in particular 1 to 25 mol%, of the compound (s) of the formula (I) according to the invention.
  • constituents of the mixtures according to the invention are preferably selected from the known compounds with nematic or
  • cholesteric phases include, for example, biphenyls, terphenyls, phenylcyclohexanes, bicyclohexanes, cyclohexylbiphenyls, mono-, di- and Trifluorophenyls.
  • the commercially available liquid crystal mixtures already exist as mixtures of various components, at least one of which is mesogenic, before the addition of the compound (s) according to the invention.
  • Nematic liquid crystal mixtures are examples
  • Phenylcyclohexanes as described for example in DE-A 4 108 448.
  • Liquid-crystalline mixtures which contain compounds of the general formula (I) are particularly suitable for use in electro-optical switching and display devices (displays). Such switching and
  • Display devices generally have, inter alia, the following
  • a liquid-crystalline medium e.g. made of glass or plastic
  • carrier plates e.g. made of glass or plastic
  • transparent electrodes at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • adhesive frames at least one orientation layer
  • spacers spacers
  • polarizers polarizers
  • thin color filter layers for color displays.
  • Other possible components are anti-reflective, passivation, compensation and barrier layers as well as electrical nonlinear elements such as thin film transistors (TFT) and metal-insulator-metal (MIM) elements.
  • TFT thin film transistors
  • MIM metal-insulator-metal
  • phase transition temperatures are determined with the help of a polarizing microscope on the basis of the texture changes.
  • the melting point is determined with a DSC device
  • Glass transition (Tg) takes place in ° C and the values are between the phase names in the phase sequence.
  • the values for the optical and dielectric anisotropy and the electro-optical characteristic are recorded at a temperature of 20 ° C.
  • Liquid crystals which do not have a nematic phase at 20 ° C. are mixed in 10% by weight in ZLI-1565 and / or in 20% by weight in ZLI-4792 (commercial nematic liquid crystal mixtures from E. Merck, Darmstadt) and the values are extrapolated from the results of the mixture.
  • Electro-optical characteristics are determined on the basis of the transmission of a measuring cell.
  • the cell is positioned between crossed polarizers in front of a light source.
  • There is a light detector behind the cell the sensitivity of which is optimized by filters for the visible area of the light. Analogous to the gradual increase in the voltage applied to the cell, the change in transmission is recorded. Values such as threshold voltage and slope are determined from this.
  • the optical anisotropy is determined using an Abb ⁇ refractometer (from Zeiss). To orient the liquid crystal, a
  • Orientation layer obtained from a 1% by weight lecithin-methanol solution.
  • Measuring cell attached to the turntable of a polarizing microscope between crossed analyzer and polarizer. To determine the contrast, the measuring cell is positioned by turning it so that a photodiode indicates minimal light transmission (dark state). The microscope illumination is controlled so that the photodiode shows the same light intensity for all cells. After a switching operation, the light intensity (bright state) changes, and the contrast is calculated from the ratio of the light intensity of these states.
  • triphenylphosphine are at 0 ° C in 40 ml
  • Example 11 the substance according to the invention from Example 11 is compared with a reference substance from WO 92/13928 as the pure substance and in a mixture with a commercially available TFT-TN mixture ZLI-4792 (E. Merck, Darmstadt).
  • the substance according to the invention is characterized by a lower melting point (heating), higher nematic-isotropic transition and significantly wider

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

Abstract

3,5-difluorobenzènes de formule générale (I) dans laquelle les symboles et les indices ont les significations suivantes: R1 est un H, un alkyle à chaîne droite ou ramifiée (avec, ou sans atome de carbone asymétrique) ayant de 1 à 15 atomes de C, où un ou deux groupes CH¿2? non voisins peuvent être remplacés par -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O-, -CH=CH-, -C C-, cyclopropane-1,2-diyle ou -Si(CH3)2- et où un ou plusieurs atomes H du reste alkyle peuvent être remplacés par F, Cl ou CN; A?1, A2, A3¿, qui peuvent être identiques ou différents, représentent les restes suivants: 1,4-phénylène, pyrazine-2,5-diyle, ou pyridine-2,5-diyle, dans lesquels un ou deux atomes H peuvent être remplacés par F, trans-1,4-cyclohexylène, (1,3,4)-thiadiazole-2,5-diyle, 1,3-dioxanne-2,5-diyle, naphtaline-2,6-diyle, bicyclo[2.2.2]octane-1,4-diyle ou 1,3-dioxaborinane-2,5-diyle; M1 et M2, qui peuvent être identiques ou différents, représentent -CH¿2?CH2-, -CH=CH-, -C C-, -CH2CH2CH2CH2-, -CH2CH2CH2-O-, -O-CH2CH2CH2-, -CH2CH2CO-O-, -O-CO-CH2CH2-, -CH2-O-, -O-CH2-, -CO-O- ou -O-CO-; k, l, m, n et o sont égaux à zéro ou à un, pour autant que la somme k+m+o soit supérieure à zéro; avec les conditions suivantes: lorsque k+m+o est égal à un, X désigne -CH2-CH2-, -CH=CH-, -C C-, -CH2CH2CH2CH2-, -CH2CH2CH2-O-, -O-CH2CH2CH2-, -CH2CH2CO-O-, -O-CO-CH2CH2-, -CH2-O-, -O-CH2-, -CO-O- ou -O-CO; et lorsque k+m+o est supérieur à un, X désigne -CH2CH2-, -CH=CH-, -C C-, -CH2CH2CH2CH2-, -CH2CH2CH2-O-, -O-CH2CH2CH2-, -CH2CH2-CO-O-, -O-CO-CH2CH2-, -CH2-O-, -O-CH2-, -CO-O-, -O-CO- ou une simple liaison. Les composés selon l'invention sont des composants utiles pour des mélanges de cristaux liquides nématiques.
PCT/EP1994/003533 1993-11-10 1994-10-27 3,5-difluorobenzenes et leur utilisation dans des melanges de cristaux liquides Ceased WO1995013999A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4338266A DE4338266A1 (de) 1993-11-10 1993-11-10 3,5-Difluorbenzole und ihre Verwendung in Flüssigkristallmischungen
DEP4338266.5 1993-11-10

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WO1995013999A1 true WO1995013999A1 (fr) 1995-05-26

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1352886A1 (fr) * 2002-04-09 2003-10-15 Chisso Corporation Composé crystal liquide ayant un atome d'hydrogène comme groupe terminal, composition contenant le composé et dispositif d'affichage à crystaux liquides contenant la composition

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Publication number Priority date Publication date Assignee Title
JPH01131144A (ja) * 1987-11-16 1989-05-24 Chisso Corp シクロヘキサン誘導体
JPH03130253A (ja) * 1989-10-16 1991-06-04 Chisso Corp ジフルオロベンゾニトリル誘導体
JPH04169574A (ja) * 1990-11-01 1992-06-17 Seiko Epson Corp ピリミジン誘導体及びそれを含有する液晶組成物及びそれを用いた液晶表示素子
WO1992013928A1 (fr) * 1991-02-12 1992-08-20 MERCK Patent Gesellschaft mit beschränkter Haftung Composes de cristaux liquides
WO1993003113A1 (fr) * 1991-08-03 1993-02-18 MERCK Patent Gesellschaft mit beschränkter Haftung Composes a cristaux liquides
JPH05310618A (ja) * 1992-04-28 1993-11-22 Dainippon Ink & Chem Inc ３，５−ジフルオロベンゼン誘導体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01131144A (ja) * 1987-11-16 1989-05-24 Chisso Corp シクロヘキサン誘導体
JPH03130253A (ja) * 1989-10-16 1991-06-04 Chisso Corp ジフルオロベンゾニトリル誘導体
JPH04169574A (ja) * 1990-11-01 1992-06-17 Seiko Epson Corp ピリミジン誘導体及びそれを含有する液晶組成物及びそれを用いた液晶表示素子
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EP1352886A1 (fr) * 2002-04-09 2003-10-15 Chisso Corporation Composé crystal liquide ayant un atome d'hydrogène comme groupe terminal, composition contenant le composé et dispositif d'affichage à crystaux liquides contenant la composition
US7125589B1 (en) 2002-04-09 2006-10-24 Chisso Corporation Liquid crystal compound having hydrogen as a terminal group, composition comprising the compound, and liquid crystal display element comprising the composition

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