Aryl-sulfur pentafluorides

Details Aryl-sulfur pentafluorides Aryl-sulfur pentafluorides

1989-12-27

1991-10-08

Stoll, Robert L.

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

25229961, 25229963, 25229966, 25229967, 25229968, 359103, 560 64, 560100, 568 74, 568 77, 544298, 558412, 558289, 558272, C09K 1932, C09K 1934, C09K 1920, G02F 113

Patent

active

050552236

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new aryl-sulfur pentafluorides of the formula I ##STR2## wherein R is H, Y or an alkyl or alkenyl radical each of which has 1-15 C atoms and is unsubstituted or substituted by at least one group Y and in which one or more non-adjacent CH.sub.2 groups can also be replaced by O and/or S atoms and/or by --E--, --CO--, --O--CO--, --CO--O--, --O--CO--O--, --S--CO-- and/or --CO--S-- groups, ##STR3## the X.sup.o s independently of one another are each Y or CH.sub.3, the Xs independently of one another are each X.sup.o or H, one another are each groups can be replaced by 0 atoms, by N, or piperidine-1,4-diyl, bicyclo-(2.2.2)octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene, it being possible for the radicals a) and b) to be monosubstituted or disubstituted by X.sup.o, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --C.tbd.C--, --OCH.sub.2 --, --CH.sub.2 O--, --CH.dbd.N--, --N.dbd.CH--, --NO.dbd.N--, --N.dbd.NO-- or a single bond,
For the sake of simplicity, in what follows Phe is a 1,4-phenylene group, Cy is a trans-1,4-cyclohexylene group, Che is a cyclohexenylene group, Bi is a bicyclo-(2.2.2)octylene group, Pyd is a pyridine-2,5-diyl group, Pyr is a pyrimidine-2,5-diyl group, Pip is a piperidine-1,4-diyl group, Dit is a 1,3-dithiane-2,5-diyl group and Dio is a 1,3-dioxane-2,5-diyl group, it being possible for these groups to be unsubstituted or substituted.
Phe X is a group of the formula ##STR4## in which X in what follows is preferably chlorine or fluorine.
The compounds of the formula I can, like similar compounds, be used as a component of liquid-crystal phases, in particular for displays based on the principle of the twisted cell, the guest-host effect, the effect of the deformation of aligned phases, the effect of dynamic scattering or the 2-frequency method.
The compounds of the formula I are also suitable for use as components of phases for use in SBE, STN or OMI displays.
The invention was based on the task of indicating a stable liquid-crystal or mesogenic compound suitable for use as a component of liquid-crystal phases.
It has been found that the aryl-sulfur pentafluorides of the formula I are excellently suitable for use as components of liquid-crystal phases. In particular, they have comparatively low viscosities and exhibit no tendency, or only a slight tendency, to form molecular associates, while, at the same time, having a pronounced positive dielectric anisotropy. It is possible with their aid to obtain stable liquid-crystal phases having a broad mesophase range, advantageous values for optical and dielectric anisotropy and favourable elastic properties.
In addition, the provision of compounds of the formula I widens considerably, in a very general manner, the range of liquid-crystal substances suitable from various aspects of technical performance for the preparation of liquid-crystal mixtures.
The compounds of the formula I possess a wide field of use. Depending on the selection of the substituents, these compounds can be used as the base materials of which liquid-crystal phases are predominantly composed; it is also possible, however, to add compounds of the formula I to liquid-crystal base materials composed of other classes of compounds in order, for example, to influence the dielectric and/or optical anisotropy of such a dielectric and/or to reduce the threshold voltage and or viscosity thereof.
In the pure state, the compounds of the formula I are colourless and they form liquid-crystal mesophases within a temperature range which is advantageously situated for electrooptical use. They are stable to chemicals, heat and light.
The invention thus relates to the aryl-sulfur pentafluorides of the formula I and to a process for their preparation which is characterized in that p-lithium-aryl- or bromomagnesium-aryl-sulfur pentafluorides are reacted with appropriate electrophiles, or corresponding 1-alkynes are coupled with p-bromoaryl-sulfur pentafluorides with transition metal catalysis, o

REFERENCES:
patent: 3102903 (1963-09-01), Coffman et al.
patent: 4481149 (1984-11-01), Misaki et al.
patent: 4696759 (1987-09-01), Isoyama et al.
patent: 4871469 (1989-10-01), Reiffenrath et al.

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