Compositions – Liquid crystal compositions – Containing nonsteryl liquid crystalline compound of...
Patent
1987-08-11
1989-08-01
Gron, Teddy S.
Compositions
Liquid crystal compositions
Containing nonsteryl liquid crystalline compound of...
2522995, 25229963, 350350R, 544179, 544182, 544230, 546 15, 549 20, 549 21, 549 22, 549 13, 549 14, 549 28, 549330, 558 17, 558265, 558266, 558267, 558268, 558269, 558270, 558271, 558273, 558275, 558276, 558384, 560 20, 560 21, 560 59, 560 60, 560 64, 560 73, 560102, 560104, 560105, 560106, 560107, 560108, 560116, 560 8, 560138, 560141, 560 1, 560174, 560183, 560187, 560188, 560220, 560221, 560255, 560256, 568326, 568329, 568367, 568368, 568585, 568583, 568631, 568632, 568634, 568642, 568659, 568661, 5686
Patent
active
048531510
DESCRIPTION:
BRIEF SUMMARY
The invention relates to dispirotetradecanes of the formula I ##STR2## wherein
R.sup.1 and R.sup.2 are each independently of the other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --0--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,
A.sup.1 and A.sup.2 are each independently of the other trans1,4-cyclohexylene wherein one or two nonadjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,
Z.sup.1 and Z.sup.2 are each independently of the other --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,
m and n are each 0, 1 or 2,
(m+n) 0, 1 or 2,
N.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each independently of the other H, F, Cl or Cn, and one or both of the groups CX.sup.1 X.sup.2 and CX.sup.3 X.sup.4 may also be C.dbd.O, with the proviso that (m+n) is 1 or 2 if both groups CX.sup.1 X.sup.2 and CX.sup.3 X.sup.4 are C.dbd.O.
For the sake of simplicity, in what follows 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 and Phe is a 1,4-phenylene group.
Similar compounds are known, for example, from German Offenlegungsschrift No. 3,426,035 and German Offenlegungsschrift No. 3,407,013. However, in contrast to the present compounds, the compounds specified there always contain cyclohexane rings linked via a single bond while the novel compounds always have the dispirotetradecane structure.
The compounds of the formula I can be used like similar compounds as components of liquid-crystalline phases, in particular for displays which are based on the principle of the twisted cell (TN displays), the guest-host effect, the aligned phase deformation effect, the dynamic scattering effect or the SSFLC principle.
The invention was based on the object of finding novel stable liquid-crysalline or mesogenic compounds which are suitable as components of liquid-crystalline phases.
It has now been found that the compounds of the formula I are eminently suitable as components of liquid-crystalline phases. In particular, they are suitable for wide-range mixtures with particularly low optical anisotropy.
In addition, the provision of the compounds of the formula I substantially widens, quite generally, the range of liquid-crystalline substances which are suitable for producing liquid-crystalline mixtures from various application points of view.
The compounds of the formula I have a wide field of application. Depending on the choice of substituents, these compounds can act as base materials of which liquid-crystalline phases are predominantly composed; however, compounds of the formula I may also be added to liquid-crystalline base materials from other compound categories in order, for example, to optimize the dielectric and/or optical anisotropy or other parameters of such a dielectric. The compounds of formula I for furthermore suitable as intermediate products for preparing other substances which can be used as constituents of liquid-crystalline phases. In the pure state, the compounds of the formula I are colorless and form liquid-crystalline mesophases in a temperature range which is favorably situated for electrooptical use. They are very stable chemically, thermally and towards light.
The subject of the invention is therefore formed by the compounds of the formula I and also by a method for producing them, wherein suitably substituted cyclohexanecarboxylic acid halides are converted into the ketenes by dehydrohalogenation and the latter are dimerized to the dispirotetradecanedione system, or wherein one or both C.dbd.O groups in a compound which otherwise corresponds to the formula I but contains two C.dbd.O groups in the 7,14 position are treated with a red
REFERENCES:
Calaminus, W., et al., Z. Naturforsch, vol. 416, pp. 1011-1014 (1986).
Franke, V., et al., Angew. Makromol. Chemie., vol. 21, pp. 195-205 (1972).
Farina, M., et al., Tetrahedron Letters, No. 3, pp. 183-186 (1975).
Calaminus Wolfgang
Vogtle Fritz
Gron Teddy S.
Merck Patent Gesellschaft Mit Beschrankfter Haftung
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