Ethyne derivatives

Details Ethyne derivatives Ethyne derivatives

1988-11-25

1992-11-17

Stoll, Robert L.

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

25229963, 25229966, 25229967, 25229901, 570129, 544298, 546340, C09K 1934, C09K 1930, C07D23902, C07C 1908

Patent

active

051641143

DESCRIPTION:

BRIEF SUMMARY
The invention relates to ethyne derivatives of the formula I --A.sup.2).sub.n --R.sup.2 I unsubstituted, monosubstituted by --CN or at least monosubstituted by halogen, it also being possible for one or more CH.sub.2 groups in these radicals in each case independently of one another to be replaced by --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O-- or --C.tbd.C-- such that heteroatoms are not linked directly to one another, H, halogen, --CN or --NCS, replaced by N, CH.sub.2 groups can also be replaced by --O-- and/or --S--, 1,4-cyclohexadienylene or 1,4-bicyclo-(2.2.2)-octylene, more than once by halogen, cyano and/or CH.sub.3, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or a single bond, can also be replaced by N, 1,4-cyclohexadienylene or 1,4-bicyclo(2.2.2)octylene, more than once by halogen, cyano and/or CH.sub.3, least one CH group is replaced by N and/or at least one of the groups A.sup.3 and A.sup.4 is trans-1,4-cyclohexylene or 1,4-bicyclo(2.2.2)octylene and/or at least one of the groups A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is 1,4-cyclohexenylene or 1,4-cyclohexadienylene.
For simplicity, in the following text Phe is an unsubstituted 1,4-phenylene group, PheX is a substituted 1,4-phenylene group (where X is halogen, CN and/or CH.sub.3), Cyc is a 1,4-cyclohexylene group, Che is a 1,4-cyclohexenylene group, Cha is a 1,4-cyclohexadienylene group, Dio is a 1,3-dioxane-2,5-diyl group, Dit is a 1,3-dithiane-2,5-diyl group, Pyd is a pyridine-2,5-diyl group, Pyr is a pyrimidine-2,5-diyl group, Pyz is a pyrazine-2,5-diyl group, Pyn is a pyridazine-3,6-diyl group, Bco is a 1,4-bicyclo(2.2.2)octylene group and Biphe is a 4,4'-biphenylyl group, wherein one or more CH groups can also be replaced by N.
The compounds of the formula I can be used as components of liquid crystal phases, in particular for displays based on the principle of the twisted cell, on the guest-host effect, on the effect of deformation of orientated phases or on the effect of dynamic scattering.
Similar compounds are known, for example, from European Patent 111,695-A, for displays which operate by the two-frequency method.
The invention was based on the object of discovering new stable liquid crystal or mesogenic compounds which are suitable as components of liquid crystal phases. This object was achieved by providing the compounds of the formula I.
It has been found that the compounds of the formula I are outstandingly suitable as components of liquid crystal phases In particular, these compounds are distinguished by a positive dielectric anisotropy and a high birefringence.
The compounds of the formula I are thus preferably suitable for use as components of liquid crystal phases for SBE or OMI applications.
Surprisingly, it has been found that the addition of compounds of the formula I gives liquid crystal phases with wide nematic ranges.
By providing the compounds of the formula I, the range of liquid crystal substances which are suitable from various technological aspects for the preparation of nematic mixtures is also quite generally widened considerably.
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 the base materials from which liquid crystal phases are predominantly composed; however, it is also possible to add compounds of the formula I to liquid crystal base materials from other classes of compounds, for example in order to optimize the dielectric and/or optical anisotropy of such a dielectric.
The compounds of the formula I are furthermore suitable as intermediates for the preparation of other substances which can be used as constituents of liquid crystal phases.
The compounds of the formula I are colorless in the pure state and form liquid crystal mesophases in a temperature range which is favorably placed for electro-optical use. They are very stable towards chemicals, heat and light.
The invention thus relates to the compounds of the formula I and the use of these compounds as c

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