Naphthyl organic compounds

Details Naphthyl organic compounds Naphthyl organic compounds

1995-06-06

1998-10-13

Wu, Shean C.

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

25229962, 349182, 349186, 544299, 544303, 544334, 544335, C09K 1934, C09K 1932, G02F 1133, C07D23902

Patent

active

058207813

DESCRIPTION:

BRIEF SUMMARY
This is a continuation of U.S. application No. PCT/GB92/00411, filed Mar. 9, 1992.
This invention relates to compounds containing a naphthyl group and which have liquid crystalline properties and/or which are suitable for use as constituents of liquid crystal materials. The invention also relates to use of such compounds in liquid crystal materials.
Liquid crystal materials and devices exploit the electro-optical properties of nematic and cholesteric (N or N*), or smectic (S) with particularly useful smectic phases being chiral smectic C (S.sub.C *) or smectic A.
Liquid crystal materials which show ferroelectric S.sub.C * phase are useful in fast switching displays such as television or VDU screens as the S.sub.C * phase can be swithched in a few milliseconds or even microseconds. The principle of S.sub.C * switching is described inter alia by N. A. Clark and S. T. Lagerwall in App Phys Lett 36 (1980) p899.
Materials which show an S.sub.A liquid crystal phase may be used in display devices which exploit the electroclinic effect.
The use of liquid crystal materials to exhibit electro-optical effects in displays and other optical devices such as digital calculators, watches, meters and alphanumeric laptop computers is now well known. However, known liquid crystal materials are not ideal in all respects and a considerable amount of work is currently being carried out in the art to improve their properties.
Liquid crystal materials normally consist of specially selected mixture compositions and improved materials are often obtained by forming new mixtures having an improved combination of properties.
The composition of a liquid crystal mixture is generally selected so that the mixture shows desirable properties. In particular such properties include: (20.degree. C.)--which is as wide as possible; is as low as possible; temperature) which is as high as possible; (permittivity measured parallel to the molecular axis less that measured perpendicular to the molecular axis) which is as great as possible in order to minimise the display voltage; display switching speeds; temperatures;
Examples of further particular properties useful in specific applications include: device requirements; and
Liquid crystal materials and devices exploit the electro-optical properties of nematic or cholesteric (N and N* respectively), or smectic (S) in particular chiral smectic C (S.sub.c *) or smectic A (S.sub.a) phase. The most common type of liquid crystal materials in use are those which show a nematic phase and these are extensively used in, for example, watches, clocks, calculators, electronic displays etc.
For some applications of liquid crystal materials a high birefringence is sought, eg in so called "electrically controlled birefringence" (ECB) effect devices (see, for example, M. F. Schieckel and K. Fahrensohn Applied Physics Letters 19 p2912 1971), in thin film transistors and supertwisted nematic devices. It is rare for the requisite desirable properties to be found in a single liquid crystalline compound and generally liquid crystalline materials consist of mixtures of component compounds. Very many liquid crystalline compounds suitable for such uses are known and will be apparent to those in the art.
Some liquid crystalline compounds based on the phenyl-naphthalene system are known eg ##STR1##
For example, Bull Soc Chim Fr 11-12(2) p2521-2426 (1975) describes compounds where A is alkoxy and B is alkyl or alkoxy, and Helv Chim Acta 68(9) p1406-1426 describes those in which a is alkyl or alkoxy and B is cyano or trifluoromethyl.
It is the aim of this invention to provide novel compounds which provide improved or alternative liquid crystalline and/or monotropic characteristics.
According to this invention, liquid crystal naphthyl compounds of formula I are provided; B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R.sub.1 and R.sub.2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and

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