Hexasubstituted cyclohexane compounds

Details Hexasubstituted cyclohexane compounds Hexasubstituted cyclohexane compounds

1987-09-11

1989-10-31

Gron, Teddy S.

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

2522995, 2522996, 25229962, 25229963, 350350R, C09K 1930, C09K 1934, C07C149273, C07C14702, C07C14714, C07D21166, C07D31906, C07D33908

Patent

active

048772208

DESCRIPTION:

BRIEF SUMMARY
The invention relates to hexasubstituted cyclohexane compounds of the formula I ##STR2## in which
Z.sup.1 is --CO--X.sup.1 --, --X.sup.1 --CO--, --CH.sub.2 --X.sup.2 --, --X.sup.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --,
Z.sup.2 has one of the meanings of Z.sup.1 or is a single bond,
Z.sup.3 is --X.sup.1 --CO-- or --X.sup.2 --CH.sub.2 --
X.sup.1 is O, S or Se,
X.sup.2 is O, S, Se, SO or SO.sub.2,
A.sup.1, A.sup.2 and A.sup.3 each are, independently of one another, a 1,4-phenylene group which is unsubstituted or mono- or poly-substituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which one or more CH groups might also be replaced by N atoms, or are a 1,4-cyclohexylene group in which one or two non-adjacent CH.sub.2 groups might also be replaced by --O-- and/or --S--, or are a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group, and A.sup.2 and A.sup.3 can also be a single bond,
p is 0 or 1,
R.sup.1 and R.sup.2 each are, independently of one another, alkyl having 1 to 20 C atoms, wherein one or more CH.sub.2 groups might also be replaced by --O--, --S--, --CHCH.sub.3 --, --CHCN--, --CHhalogen--, --CO--, --O--CO--, --CO--O-- and/or --CH.dbd.CH--, or are H, F, Cl, Br, I, OH, NH.sub.2, COOH or CN, no two heteroatoms being directly linked to one another,
m is 1, 2 or 3 and
(n+m) is 6, --X.sup.1 --CO--.
For simplicity, in the text which follows, "Cy" is a cyclohexane-1,2,3,4,5,6-hexayl group with six free valencies, Cyc is a trans-1,4-cyclohexylene group in which one or two non-adjacent CH.sub.2 groups can also be replaced by O and/or S, and Phe is a 1,4-phenylene group in which one or more CH groups can also be replaced by N. The groups Cyc and Phe can be unsubstituted or laterally substituted.
Similar compounds, namely hexaalkanoylcyclohexanes, are known (compare German Offenlegungsschrift No. 3,332,955; B. Kohne and K. Praefcke, Angew. Chem. 96 (1984), 70-71; Z. Luz, W. Poules, R. Poupko, K. Praefcke and B. Scheuble, 21st Bunsen Kolloquium, Berlin Technical University, September/October 1983; German Offenlegungsschrift No. 3,510,325).
The compounds of the formula I can, like similar compounds, be used as components of discotic liquid-crystal-line phases, in particular for displays based on the guest/host effect, the effect of the deformation of aligned phases, the effect of dynamic scattering or on a change in the elliptization of light.
It was the object of the invention to discover novel stable liquid-crystalline or mesogenic compounds which are suitable as components of discotic liquid-crystalline phases. This object has been achieved by the provision of the compounds of the formula I.
It has been found that the compounds of the formula I are outstandingly suitable as components of discotic liquid-crystalline phases. In particular, stable discotic liquid-crystalline phases with a wide mesophase temperature range in a position advantageous for electro-optical effects and very advantageous values of the dielectric anisotropy can be prepared by means of these compounds.
The compounds of the formula I are also suitable as an anisotropic, discotic matrix for spectroscopic investigations.
Other compounds having discotic properties and their use in electro-optical display elements have been described, for example, in U.S. Patent Specification No. 4,333,709. However, the discotic liquid crystals known for this field of application all have a relatively small .DELTA..epsilon. value for the dielectric anisotropy, since this anisotropy is to be attributed only to the anisotropy of the polarizability of these molecules. Although polar discotic liquid crystals of the phthalocyanine type are already known from C. Piechocki and J. Simon, J. Chem. Soc., Chem. Commun. 1085 (5), 259, the cyclohexane compounds according to the invention by contrast combine the advantages of non-polar cyclohexane compounds, known from German Offenlegungsschriften Nos. 3,332,955 and 3,510,325, with a permanent dipole character.
Surprisingly, the compounds of the formula I prove to be discotic liquid crystallin

REFERENCES:
patent: 4333709 (1982-06-01), Dubois et al.
patent: 4578210 (1986-03-01), Praefcke et al.
patent: 4702562 (1987-10-01), Scheuble et al.
patent: 4713196 (1987-12-01), Praefcke et al.
patent: 4734522 (1988-03-01), Praefcke et al.
patent: 4758373 (1988-07-01), Praefcke et al.
Angyal, S. J., et al., J. Chem. Soc., pp. 6949-6955, (1965).
Angyal, S. J., et al., J. Chem. Soc.(C)., pp. 919-992, (1967).
Kok, D. M., et al., Mol. Crystl. Lir. Cryst., vol. 129, pp. 53-60, (1985).
Angyal, S. J., et al., J. Chem. Soc.(C), pp. 919-922, (1967).
C.A., vol. 101:152229y, (1984).
C.A., vol. 76:154058f, (1972).

Affiliated with

Also associated with

Rating

Hexasubstituted cyclohexane compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Hexasubstituted cyclohexane compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hexasubstituted cyclohexane compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-621904