Compositions – Liquid crystal compositions
Patent
1986-12-24
1989-05-30
Gron, Teddy S.
Compositions
Liquid crystal compositions
2522995, 25229961, 350350R, 350350S, 544233, 544238, 544239, 544240, 544241, 544242, 544294, 544295, 544296, 544315, 544316, 544298, 544318, 544333, 544334, 544224, 544335, 544336, 544357, 544405, 544406, 544408, 544409, 546255, 546257, 546258, 546261, 546263, 546264, 546265, 546267, 546268, 546275, 546276, 546278, 546280, 546285, 546286, 546287, 546288, 546290, 546298, 546299, 546300, 546301, 546302, 546303, 546314, 546315, 546318, 546321, 546322, 546323, 546326, 546330, 546339, 546340, 546341, 546342, 546
Patent
active
048349046
DESCRIPTION:
BRIEF SUMMARY
The invention relates to nitrogen-containing heterocycles of the formula I substituted alkyl group of 1-15 carbon atoms in which one or two non-adjacent CH.sub.2 groups can also be replaced by at least one member of the group --O--, --CO--, --O--CO--, --CO--O-- and --CH.dbd.CH--; F, Cl, Br, --CN, --NCS or R.sup.3 --(A.sup.3)p--Z.sup.2 --, with an asymmetric carbon atom, or substituted by one or two F atoms and/or Cl atoms and/or CH.sub.3 groups and/or CH groups, in which one or two CH groups can also be replaced by N atoms; 1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or S atoms; piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)octylene; decahydronaphthalene-2,6-diyl which is unsubstituted or substituted by CN; or 1,2,3,4-tetrahydronaphtalene-2,6-diyl, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, substituted ethylene or a single bond, atoms in which one or two non-adjacent CH.sub.2 groups can also be replaced by a member of the group --O--, --CO--, --O--CO--, --CO-O and --CH.dbd.CH--; F, Cl, Br, --NCS or --CN, and when p=2, with the proviso that when A=pyrimidine-2,5-diyl, one of the radicals R.sup.1 and R.sup.2 is an optically active organic radical and the other radical R.sup.1 or R.sup.2 is an unsubstituted or substituted alkyl group of 1-15 carbon atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by at least one member of the group --O--, --CO--, --O--CO--, --CO--O--and --CH.dbd.CH--.
For the sake of simplicity, in the following text Cy is a 1,4-cyclohexylene group, Dio is a 1,3-dioxane-2,5-diyl group, Dit is a 1,3-dithiane-2,5-diyl group, Bi is a 1,4-bicyclo(2,2,2)octylene, Phe is a 1,4-phenylene group and Pyr is a 1,4-phenylene group in which at least one CH group is replaced by N, in which these groups, in particular Cy and Phe can be unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups.
Similar compounds are known from, for example, EP-OS No. 0 131 373. However, in contrast to the above, the compounds disclosed therein do not contain nitrogen-containing heterocyclic rings.
The compounds of the formula I can be used, like similar compounds, as chiral dopants for liquid crystalline phases, in particular as components of ferroelectric liquid crystalline phases. These phases are suitable for displays, which are based on the principle of the twisted cell (TN displays), the guest-host effect, the effect of the deformation of aligned phases or the effect of dynamic scattering, in particular, however, for ferroelectric displays, for example in accordance with N. A. Clark and S. T. Lagerwall, Applied Phys. Lett. 36, 899 (1980).
The invention was based on the object of finding new stable liquid crystalline or mesogenic compounds that would be suitable as components of such phases.
It has been found that the compounds of the formula I are highly suitable as components of liquid crystalline phases. In particular, they can be used for preparing stable chiral S.sub.c phases in a temperature range favourable for electrooptical applications.
On adding compounds of the formula I to non-polar liquid crystalline phases, it was found, surprisingly, that even relatively small additions can significantly increase spontaneous polarization.
In addition, by providing the compounds of the formula I the range of liquid crystalline substances that are suitable for the preparation of ferroelectric mixtures from various points of view relating to application, has in general been substantially broadened.
The compounds of the formula I have a wide range of applications. Depending on the choice of substituents, these compounds can serve as base materials which form the predominant part of liquid crystalline phases; however, compounds of the formula I can be treated with liquid crystalline base materials from other compound classes in order to vary, for example, the dielectric and/or optical anisotropy and/or the spontaneous polarization of such a phase. Furthermore, the compounds of the formula I are suitable as in
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Bofinger Klaus
Eidenschink Rudolf
Geelhaar Thomas
Krause Joachim
Scheuble Bernhard
Gron Teddy S.
Merck Patent Gesellschaft mit beschrankter Haftung
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