Cyclohexane derivatives

Details Cyclohexane derivatives Cyclohexane derivatives

1987-10-30

1989-10-03

Gron, Teddy S.

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

350350R, 350350S, 558414, 558415, 558416, 558423, 558425, 558426, 558431, 560 59, 560 60, 560 62, 560 55, 560 8, 560102, 560116, 560129, 560188, 560255, 568329, 568367, 568631, 568642, 568659, 568661, 568664, 568816, 568743, 568744, 568745, 568746, 568747, 570129, 570130, 570182, 570188, 585 20, 585 25, C09K 1930, C07C 1328, C07C 69753, C07C12146, C07C 49313, C07C 4321, C07C 3917

Patent

active

048714704

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel cyclohexane derivatives of the formula I ##STR2## in which
R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O--or --OCO--,
A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,
X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 and
R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms, trans-1,4-cyclohexylene or fluorine-substituted 1,4-phenylene.
The compounds of the formula I can, like similar compounds, for example those known from German Offenlegungsschrift No. 2,702,598, be used as components of liquid-crystalline dielectrics, especially for displays based on the principle of the twisted cell, the guest/host effect, the effect of the deformation of aligned phases or the effect of dynamic scattering.
It was the object of the invention to discover novel stable liquid-crystalline or mesogenic compounds which are suitable as components of liquid-crystalline dielectrics.
It has been found that the compounds of the formula I are outstandingly suitable as components of liquid-crystalline dielectrics Especially, using these components, stable liquid-crystalline phases of a relatively low optical anisotropy and of a high nematic character can be prepared, which, in electro-optical display elements according to the principle of the twisted cell and/or the guest/host effect, are distinguished by a particularly advantageous angular dependence of the contrast.
Moreover, by providing the compounds of the formula I, the range of liquid-crystalline substances which are suitable under various application aspects for the preparation of nematic mixtures is in general considerably extended.
The compounds of the formula I have a wide range of applications. Depending on the selection of the substituents, these compounds can be used as base materials of which the predominant part of liquid-crystalline phases is composed, but compounds of the formula I can also be added to liquid-crystalline base materials from other classes of compounds, for example in order to influence the angular dependence of the contrast and/or the optical anisotropy of such a phase. The compounds of the formula I are also suitable as intermediates for the preparation of other substances which can be used as constituents of liquid-crystalline dielectrics.
In the pure state, the compounds of the formula I are colorless and form liquid-crystalline mesophases within a temperature range which is advantageous for electro-optical use. They are very stable chemically, thermally and towards light.
The invention thus relates to compounds of the formula I and to a process for their preparation, which is characterized in that, for preparing carbonitriles of the formula I (X=CN), the corresponding carboxylic acids (X=COOH) or one of their reactive derivatives are converted to the corresponding acid amides and the latter are dehydrated, or a corresponding acid chloride is reacted with sulfamide, or that, for preparing carboxylic acid esters of the formula I (X=--COOR.sup.1), the corresponding carboxylic acid compounds or one of their reactive derivatives are reacted with the corresponding alcohol or one of its reactive derivatives, or that, for preparing acyl compounds of the formula I (X=--COR.sup.1), the corresponding carboxylic acid compounds or one of their reactive derivatives are converted to the corresponding nitriles and the latter are reacted with the corresponding Grignard compound, or that, for preparing the alkyl compounds (X=R.sup.1), the corresponding carboxylic acid compounds or one of their reactive derivatives are converted to the corresponding keto compounds (X=--COR.sup.1) and the latter are reduced,
or that a compound which otherwise correspond

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