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EP0258340A1 - Phases smectiques de cristaux liquides - Google Patents

Phases smectiques de cristaux liquides

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Publication number
EP0258340A1
EP0258340A1 EP87901424A EP87901424A EP0258340A1 EP 0258340 A1 EP0258340 A1 EP 0258340A1 EP 87901424 A EP87901424 A EP 87901424A EP 87901424 A EP87901424 A EP 87901424A EP 0258340 A1 EP0258340 A1 EP 0258340A1
Authority
EP
European Patent Office
Prior art keywords
chloro
fluoro
phe
ester
coo
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Withdrawn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
EP87901424A
Other languages
German (de)
English (en)
Inventor
Joachim Krause
Volker Reiffenrath
Thomas Geelhaar
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 EP0258340A1 publication Critical patent/EP0258340A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/68—Lactic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2021—Compounds containing at least one asymmetric carbon atom
    • 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

Definitions

  • the invention relates to esters of formula I.
  • R 1 and R 2 each independently of one another R, OR, OCOR,
  • R alkyl having 1 to 15 carbon atoms, in which one or more CH 2 groups which are not adjacent and are not linked to O by -O-, -CO-, -O-CO-, -CO-O-, -CHHalogen, -CHCN- and / or -CH CH- can be replaced,
  • a 1 , A 2 and A 3 each independently of one another 1,4-phenylene or trans-1,4-cyclohexylene,
  • Z 1 and Z 2 each independently of one another -CH 2 -O-, -OCH 2 ,
  • X denotes F, Cl, Br, J or CN
  • the compounds of the formula I are suitable as components of chiral-chopped smectic phases which have ferroelectric properties.
  • Chiral-chopped smectic liquid-crystalline phases with ferroelectric properties can be produced by adding a suitable chiral dopant to base mixtures with one or more chut-smectic phases (LA Beresnev et al., Mol.Cryst.Liq.Cryst. 89, 327 (1982 HR Brand et al., J.Physigue 44 (lett.), L-771 (1983)
  • Such phases can be used as dielectrics for fast-switching displays, for example based on the principle of SSFLC technology described by Clark and Lagerwall
  • the elongated molecules are arranged in layers, the molecules having a tilt angle to the layer normal.
  • the tilt direction changes by a small angle with respect to an axis perpendicular to the layers, so that a helical structure is formed.
  • the smectic layers are arranged perpendicular to the plates of the cell. The helical arrangement of the tilt directions of the molecules is suppressed by a very small distance between the plates (approx.
  • a major disadvantage for many applications of the currently available materials with chirally-smectic phases is their low chemical, thermal and photo stability.
  • Another disadvantageous property of displays based on currently available chiral-smectic mixtures is that the spontaneous polarization has values that are too small, so that the switching time behavior of the displays is adversely affected and / or the pitch and tilt the phases do not meet the requirements of display technology.
  • the temperature range of the ferroelectric phases is usually too small and is predominantly at too high temperatures.
  • Formula I as components of chiral smutic blended mixtures can significantly reduce the disadvantages mentioned.
  • the compounds of the formula I are therefore particularly suitable as components of chiral-chopped smectic liquid-crystalline phases.
  • P is the spontaneous polarization m nC / cm 2 .
  • the compounds of formula I have a wide range of applications. Depending on the selection of the substituents, these compounds can serve as base materials from which liquid-crystalline smectic phases are predominantly composed; However, it is also possible to add compounds of the formula I to liquid-crystalline base materials from other classes of compounds, for example to improve the dielectric and / or optical anisotropy and / or the viscosity and / or the spontaneous polarization and / or the phase ranges and / or the tilt angle and / or the To vary the pitch of such a dielectric.
  • the invention thus relates to the compounds of the formula I.
  • the invention also relates to the compounds of the formula I for use in ferroelectric liquid-crystal mixtures.
  • the invention further relates to ferroelectrical liquid crystal phases containing at least one compound of the formula I and liquid crystal display elements, in particular electro-optical display elements, which contain such phases.
  • Cy in the following means a 1,4-cyclohexylene group, Phe a 1,4 phenylene group and PheX a 3-X-1,4-phenylene group.
  • the compounds of the formula I include those compounds of the sub-formulas Ia to Ie (with three rings):
  • sub-formula Ia those of sub-formula Ia, Ib, Ic, Id, If and Ij are preferred.
  • the preferred compounds of sub-formula Ia include those of sub-formulas Iaa to lad:
  • those of the sub-formulas Iaa and lab are particularly preferred.
  • sub-formula Ib include those of sub-formulas Iba to Ibd:
  • those of the sub-formulas Iba and Ibb are particularly preferred.
  • the preferred compounds of sub-formula Ic include those of sub-formulas Ica and leb:
  • the preferred compounds of sub-formula Id include those of sub-formulas Ida to Idd:
  • the preferred compounds of sub-formula Ie include those of sub-formulas Iea to Ied:
  • R 1 -Phe-Z 1 -PheX-COO-Phe-R 2 Iea R 1 -Cy-Z 1 -PheX-COO-Phe-R 2 live
  • the preferred compounds of the sub-formula include those of the sub-formulas Ifa to Ifd:
  • the preferred compounds of the sub-formula Ig include those of the sub-formulas Iga to Igd:
  • R 1 -Phe-Z Z -PheX-COO-Cy-Cy-R 2 Igd The preferred compounds of sub-formula Ih include those of sub-formulas Iha to Ihd:
  • the preferred compounds of sub-formula Ii include those of sub-formulas Iia to Iid:
  • the preferred compounds of sub-formula Ij include those of sub-formulas Ija to Ijd:
  • the preferred compounds of the sub-formula Ik include those of the sub-formulas Ika to Ikd:
  • the preferred compounds of the sub-formula Im include those of the sub-formulas Ima to Imd:
  • the preferred compounds of sub-formula In include those of sub-formulas Ina and Inb:
  • R 1 and R 2 are preferably R or OR, furthermore OCOR,
  • R is preferably alkyl, furthermore oxaalkyl.
  • Compounds of the formula I in which one of the radicals R 1 and R 2 is R or OR and the other radical is OR, OCOR, COOR or -OCOOR are particularly preferred
  • Z 1 and Z 2 independently of one another represent -CH 2 O-, -OCH 2 -,
  • n, n and o each represent 0 or 1 and m + n + o is 0.1 or 2.
  • X is preferably F, Cl or CN, furthermore also Br or J, fluorine is particularly preferred.
  • 1,4-phenylene group F and Z 2 means a single bond.
  • Halogen is preferably F or Cl.
  • the alkyl radicals R in the groups R 1 and / or R 2 can be straight-chain or branched. They are preferably straight-chain, have 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and accordingly preferably mean pentyl, hexyl, heptyl,
  • R 1 and R 2 together preferably have 12-20 C atoms, in particular 12-16 C atoms. If R is an alkyl radical in which one ("alkoxy” or “oxaalkyl”) or two (“alkoxyalkoxy” or “dioxaalkyl”) CH 2 groups have been replaced by O atoms, it can be straight-chain or branched.
  • It is preferably straight-chain, has 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and accordingly preferably means pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7- Oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl, 1 , 3-dioxabutyl ( methoxy-methoxy), 1,3-, 1,4- or 2,4-dioxapentyl, 1,3-, 1,4- 1,5-, 2,4-, 2,5- or 3,5-dioxahexyl, 1,3-, 1,4
  • 1,4-dioxadecyl also tridecoxy, tetradecoxy, pentadecoxy, methoxy, ethoxy, propoxy or butoxy.
  • the branched wing groups R 1 or R 2 can be an optically active organic radical with an asymmetric carbon atom.
  • the asymmetric carbon atom is preferably linked to two differently substituted carbon atoms, an hydrogen atom and a substituent selected from the group consisting of halogen (in particular F, Cl or Br), alkyl or alkoxy, each having 1 to 5 carbon atoms and CN.
  • the optically active organic radical R * preferably has the formula
  • Y CN halogen, methyl or methoxy
  • Q is preferably -CH 2 -, -CH-CH 2 - or a single bond, particularly preferably a single bond.
  • Y is preferably CH 3 , -CN or Cl, particularly preferably -CN.
  • R is preferably straight-chain alkyl having 1 to 10, in particular having 1 to 7, carbon atoms.
  • Formula I are those whose wing groups R 1 and R 2
  • R 2 are straight-chain.
  • a preferred group of compounds of the formula I are the compounds in which the laterally substituted ring is external, m then being 0.
  • R 2 contain the group -OCOR, in which R denotes an alkyl group which is preferably branched and in which a CH 2 group is replaced by -CH-halogen-, halogen is preferably chlorine, or also by -CHCN- very particularly preferred are the residues -OCOCH (Cl) -CH (CH 3 ) 2 , (2-chloro-3-methylbutyryloxy), -OCOCH (Cl) -CH (CH 3 ) -C 2 H 5 , (2-chloro-3 -methylvaleryloxy) or -OCOCH (Cl) -CH 2 -CH (CH 3 ) 2 (2-chloro-4-methylvaleryloxy).
  • R denotes an alkyl group which is preferably branched and in which a CH 2 group is replaced by -CH-halogen-, halogen is preferably chlorine, or also by -CHCN- very particularly preferred are the residues -OCOCH (Cl) -CH (CH 3
  • R 1 or R 2 then preferably denotes R or OR.
  • the lateral substituent on the ring is preferably fluorine or chlorine.
  • These compounds are preferably 2- or 3-core.
  • RO-PheCl-COO-Phe-Cy-R I 6 R-PheCN-COO-Phe-Cy-R I 7 RO-Phe-OCH 2 -PheX-COO-Phe-Phe-R I 8
  • RO-PheX-COO-Phe-Phe-R 2 * I 37 R 2 * means an optically active organic radical as described for R 1 and R 2 .
  • optically active compounds of the formula I are also suitable as components of ferroelectric liquid crystal phases according to the invention.
  • Optically active compounds of the formula I are also suitable as components of nematic liquid-crystalline phases, for example to avoid reverse twist.
  • 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 reacted further to give the compounds of the formula I.
  • the compounds of the formula I can be prepared by reducing a compound which otherwise corresponds to the formula I but contains one or more reducible groups and / or CC bonds instead of H atoms.
  • reducible groups are preferably carbonyl groups, in particular keto groups, furthermore, for example, free or esterified hydroxyl groups or aromatically bound halogen atoms.
  • any CN group which may be present remains intact, expediently by catalytic hydrogenation at temperatures between 0 ° and about 100 ° and pressures between 1 and 200 bar in an inert solvent, for example an alcohol such as methanol, ethanol or isopropanol, an ether such as tetrahydrofuran (THF) or dioxane, an ester such as ethyl acetate, a carboxylic acid such as acetic acid or a hydrocarbon such as cyclohexane.
  • an inert solvent for example an alcohol such as methanol, ethanol or isopropanol, an ether such as tetrahydrofuran (THF) or dioxane, an ester such as ethyl acetate, a carboxylic acid such as acetic acid or a hydrocarbon such as cyclohexane.
  • an inert solvent for example an alcohol such as methanol, ethanol or isopropanol, an ether
  • Suitable catalysts are suitably noble metals such as Pt or Pd, which can be used in the form of oxides (for example PtO 2 , PdO), on a support (for example Pd on carbon, calcium carbonate or strontium carbonate) or in finely divided form.
  • Pt or Pd which can be used in the form of oxides (for example PtO 2 , PdO), on a support (for example Pd on carbon, calcium carbonate or strontium carbonate) or in finely divided form.
  • the compounds of the formula I can also be prepared, for example, by esterifying a corresponding carboxylic acid or one of its reactive derivatives with a corresponding alcohol or phenol or one of its reactive derivatives.
  • Suitable reactive derivatives of the carboxylic acids mentioned are, in particular, the acid halides, especially the chlorides and bromides, furthermore anhydrides, azides or esters, in particular alkyl esters with 1-4 C atoms in the alkyl group.
  • Suitable reactive derivatives of the alcohols or phenols mentioned are in particular the corresponding metal alcoholates or phenolates, in which the metal is preferably an alkali metal such as Na or K.
  • the esterification is advantageously carried out in the presence of an inert solvent.
  • ethers such as diethyl ether, di-n-butyl ether, THF, dioxane or anisole, ketones such as acetone, butanone or cyclohexanone, amides such as DMF or phosphoric acid hexamethyltriamide, hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as carbon tetrachloride or tetrachlorethylene and sulfoxides such as Dirnethyl sulfoxide or sulfolane.
  • Solvents immiscible with water can at the same time advantageously be used for azeotropically distilling off the water formed during the esterification.
  • an excess of an organic base for example pyridine, quinoline or triethylamine, can also be used as a solvent for the esterification.
  • the esterification can also be carried out in the absence of a solvent, for example by simply heating the components in the presence of sodium acetate.
  • the reaction temperature is usually between -50 ° and + 250 °, preferably between -20 ° and + 80 °. At these temperatures, the esterification reactions are usually complete after 15 minutes to 48 hours.
  • reaction conditions for the esterification largely depend on the nature of the starting materials used.
  • a free carboxylic acid is usually reacted with a free alcohol or phenol in the presence of a strong acid, for example a mineral acid such as hydrochloric acid or sulfuric acid.
  • a preferred reaction mode is the reaction of an acid anhydride or, in particular, an acid chloride with an alcohol, preferably in a basic environment, alkali metal hydroxides such as sodium or potassium hydroxide and alkali metal carbonates being used as bases or hydrogen carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate or potassium hydrogen carbonate, alkali metal acetates such as sodium or potassium acetate, alkaline earth metal hydroxides such as calcium hydroxide or organic bases such as triethylamine, pryridine, lutidine, collidine or quinoline are important.
  • alkali metal hydroxides such as sodium or potassium hydroxide and alkali metal carbonates being used as bases or hydrogen carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate or potassium hydrogen carbonate
  • alkali metal acetates such as sodium or potassium acetate
  • alkaline earth metal hydroxides such as calcium hydroxide or organic bases such as triethylamine, pryridine, lutidine, coll
  • a further preferred embodiment of the esterification is that the alcohol or the phenol is first converted into the sodium or potassium alcoholate or phenolate, for example by treatment with ethanol or sodium hydroxide solution, and this is isolated and together with sodium hydrogen carbonate or potassium carbonate suspended in acetone or diethyl ether with stirring and this suspension with a solution of the acid chloride or anhydride in diethyl ether, acetone or
  • DMF offset expedient at temperatures between approximately -25 ° and + 20 °.
  • the phases according to the invention preferably contain at least three, in particular at least five, compounds of the formula I.
  • Particular preference is given to chiral-tipped smectic liquid-crystalline phases, the achiral base mixture of which, in addition to compounds of the formula I, contains at least one other component with a negative or small positive dielectric anisotropy.
  • These further component (s) of the achiral base mixture can make up I to 50%, preferably 10 to 25%, of the base mixture.
  • compounds of the partial form in IIa to IIIp are suitable:
  • R 4 and R 5 are each preferably straight-chain alkyl
  • X " is O or S, preferably O.
  • n is 0 or 1.
  • R 4 and R 5 each preferably denotes straight-chain alkyl or alkoxy each having 5 to 10 C atoms.
  • the compounds of the subforms IIIc, IIIh and IIli are suitable as additives for lowering the melting point and are normally added to the base mixtures in an amount of not more than 5%, preferably 1 to 3%.
  • R 4 and R 5 in the compounds of the sub-formulas IIIc, Illh and IIli are preferably straight-chain alkyl having 2 to 7, preferably 3 to 5, carbon atoms.
  • Another class of compounds suitable for lowering the melting point in the phases according to the invention is that of the formula
  • R 4 and R 5 have the preferred meaning given for IIIc, Illh and IIli.
  • Compounds containing the structural element A, B or C are also suitable as further components with negative dielectric anisotropy.
  • Preferred compounds of this type correspond to the formulas IVa, IVb and IVc:
  • R 'and R' 'each preferably represent straight-chain
  • Alkyl or alkoxy groups each with 2 to 10 carbon atoms.
  • Q 1 and Q 2 each represent 1,4 phenylene, trans-1,4-cyclohexylene, 4,4'-biphenylyl, 4- (trans-4-cyclohexyl) phenyl, trans, trans -4, 4 'bicyclohexyl or one of the groups Q 1 and Q 2 is also a single bond.
  • Q 3 and Q 4 each represent 1,4-phenylene, 4,4'-biphenylyl or trans-1,4-cyclohexylene.
  • One of the groups Q 3 and Q 4 can also mean 1,4-phenylene, in which at least one CH group has been replaced by N.
  • R ''' is an optically active residue with an asymmetric carbon atom the structure or Particularly preferred compounds of the formula IVc are those of the formula IVc ':
  • A is 1,4-phenylene or trans-1,4-cyclohexylene and n is 0 or 1.
  • Compounds of the formula I are also suitable as components of nematic liquid-crystalline phases. These liquid-crystalline phases according to the invention consist of 2 to 15, preferably 3 to 12 components, including at least one compound of the formula I.
  • the other constituents are preferably selected from the nematic or nematogenic substances, in particular the known substances from the classes of azoxybenzenes, benzylidene anilines and biphenyls , Terphenyls, phenyl- or cyclohexylbenzoates, cyclohexanecarboxylic acid phenyl- or -cyclohexyl esters, phenylcyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, cyclohexylnaphthalenes, 1, 3-bis-cyclohexylbenzenes, 4,4'-bis-cyclohexyl- or cyclylhexylylphen
  • L and E each have a carbocyclic or heterocyclic ring system consisting of 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3-dioxane rings , 2,6-disubstituted naphthalene, di- and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline,
  • Y halogen preferably chlorine, or CN
  • R 6 and R 7 are different from one another, one of these radicals usually being an alkyl or alkoxy group.
  • other variants of the proposed substituents are also common. Many such substances or mixtures thereof are commercially available. All of these substances can be produced by methods known from the literature.
  • the phases according to the invention contain about 0.1 to 99%, preferably 10 to 95%, of one or more compounds of the formula I.
  • dielectrics according to the invention containing 0.1 to 40, preferably 0.5 to 30%, one or more compounds of the formula I.
  • the dielectrics according to the invention are produced in a conventional manner. As a rule, the components are dissolved in one another, expediently at elevated temperature.
  • liquid-crystalline dielectrics according to the invention can be modified such that they can be used in all types of liquid-crystal display elements which have hitherto become known.
  • conductive salts preferably ethyl-dimethyl-dodecyl-ammonium-4-hexyloxybenzoate, tetrabutylammonium-tetraphenylboranate or complex salts of crown ethers (cf. e.g. I. Haller et al., Mol.Cryst.Liq.Cryst. Volume 24, pages 249-258
  • dichroic dyes for the production of colored guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases are added.
  • dichroic dyes for the production of colored guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases are added.
  • Such substances are e.g. B. in DE-OS 22 09 127, 22 40 854, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 and 29 02 177 described.
  • Mp. Melting point
  • Kp. Clearing point. Percentages above and below mean percentages by weight; all temperatures are given in degrees Celsius. It also means:
  • K crystalline solid state
  • S smectic phase (the index indicates the phase type)
  • N nematic state
  • Ch cholesteric phase
  • I isotropic phase. The number between two symbols indicates the transition temperature in degrees Celsius.
  • optically active connections are made analogously:
  • optically active connections are made analogously:
  • a liquid crystalline phase consisting of
  • a liquid crystalline phase consisting of
  • a liquid crystalline mixture consisting of
  • a liquid crystalline phase consisting of
  • trans-4-pentyl-4'-methoxycyclohexylcyclohexane 8% trans, trans-4-pentyl-4'-ethoxycyclohexylcyclohexane, 4% trans, trans-4-propylcyclohexylcyclohexane-4'-carboxylic acid trans -4-propylcyclohexyl ester, 4% trans, trans-4-propylcyclohexyl-cyclohexane 4'-carboxylic acid trans-4-pentylcyclohexyl ester, 4% trans, trans-4-butylcyclohexyl-cyclohexane-4'-carboxylic acid trans-4-propylcyclohexyl ester ,
  • a liquid crystalline phase consisting of
  • a liquid crystalline phase consisting of

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

Abstract

Des composés ont la formule (I) dans laquelle: R1, R2 représentent indépendamment l'un de l'autre R, OR, OCOR, COOR ou OCOOR, R représente un groupe alkyle à 1-15 atomes de C, où un ou plusieurs groupes CH2 non adjacents et non liés à O peuvent être substitutés par -O-, -CO-, -O-CO-, -CO-O-, -CHhalogène, -CHCN- et/ou -CH=CH-; A1, A2 et A3 représentent indépendamment les uns des autres 1,4-phénylène ou trans-1,4-cyclohexylène; m, n et o sont égaux à 0 ou 1; m+n+o égal à 0, 1 ou 2; Z1 et Z2 représentent indépendamment l'un de l'autre -CH2-O-, -OCH2-, -CH2CH2- ou une liaison simple; et X représente F, Cl, Br, J ou CN. Dans les conditions décrites dans la première revendication, ces composés peuvent être utilisés comme composants de phases de cristaux liquides ferro-électriques.
EP87901424A 1986-02-13 1987-02-05 Phases smectiques de cristaux liquides Withdrawn EP0258340A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3604462 1986-02-13
DE19863604462 DE3604462A1 (de) 1986-02-13 1986-02-13 Smektische fluessigkristalline phasen

Publications (1)

Publication Number Publication Date
EP0258340A1 true EP0258340A1 (fr) 1988-03-09

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US (1) US4871472A (fr)
EP (1) EP0258340A1 (fr)
JP (1) JP2545254B2 (fr)
KR (1) KR880700785A (fr)
DE (1) DE3604462A1 (fr)
WO (1) WO1987005013A2 (fr)

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DE3604462A1 (de) 1987-08-20
JPS63502589A (ja) 1988-09-29
JP2545254B2 (ja) 1996-10-16
US4871472A (en) 1989-10-03
WO1987005013A3 (fr) 1988-01-14
WO1987005013A2 (fr) 1987-08-27
KR880700785A (ko) 1988-04-12

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