The Secretary of State for Defence in Her Britannic Majesty's Government

Minnesota Mining and Manufacturing Company

Exxon Research and Engineering Company

The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland

The Secretary of State for Defence in Her Brittanic Majesty's Government

The Secretary of State for Defence in Her Majesty's Government of the

Secretary of State for Defence in Her Britannic Majesty's Govt. of U.k.

Kenneth J Harrison

Edward P Raynes

George W Gray

David J Thompson

Frances C Saunders

Kenneth J Toyne

John William Goodby

Michael Hird

Sally Elizabeth Day

Alexander J Seed

Damien Gerad McDonnel

Michael J Cook

Neil Bruce McKeown

Mervyn F Daniel

Adrian J Dunn

Andrew J Thomson

David F Newton

Leo T Carlino

David Sanderson Hulme

Liquid crystal compounds of formula (I) are described, where formula (I) is given as R,&mdash;A&mdash;(X),&mdash;(B),&mdash;R,where A is selected from naphthyl, fluorinated naphthyl, brominated naphthyl, B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine. R,and R,are independently selected from alkyl, alkoxy, akynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C&equiv;C, COO and C&equiv;C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C&equiv;C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine. Also described are liquid crystal compounds suitable for inclusion in devices utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase and described by formula (II): R,&mdash;J&mdash;(Y),&mdash;(Z),&mdash;R,, where J is selected from nathhyl, fluorinated naphthyl, brominated naphthyl, Z is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R,and R,are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, Y is selected from C&boxH;C, COO and C&boxH;C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0.

Naphthyl organic compounds

##STR1## The invention describes liquid crystalline compounds or formula (I), where A, D and G are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, B and E are independently selected from a single bond C.dbd..notident.C. C.tbd.C.C00, azoxy and diazo, k and m are independently selected from 1 and 0, such that m+n is 1 or 2, and R.sub.1 and R.sub.2 are independently selected from R, R0, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R.sub.1 and R.sub.2 is selected from CN, NCS and SCN and that at least one of A, D and G is phenyl; and excluding where at least one of R.sub.1 and R.sub.2 is independently selected as CN and one of A, D or G is not thiophene, and where m is 0, A, and D are phenyl, B is a single bond and only one of R.sub.1 or R.sub.2 is NCS. Also described are compounds suitable for inclusion in a device utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase, of general formula (II) where J and Y are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, X is selected from C.dbd..notident.C. C.tbd.C.COO azoxy and diazo, k is 1 or 0 and R.sub.3 and R.sub.4 are independently selected from R, RO, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R.sub.3 and R.sub.4 is selected from CN, NCS and SCN and that at least one of J and Y is phenyl.

Anisotropic organic compounds

Substituted phthalocyanines of a formula (I) ##STR1## wherein M is a metal atom or a metal halide or oxide, or M is 2H, one H being bonded to each of the bonding N atoms (29 and 31 positions) shown, R.sub.1 to R.sub.8 are the same or different and are independently selected from C.sub.1 to C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, --X--COO--X.sup.1, --X--O--Y, .alpha., and --X--COZ where X is independently selected from a chemical bond, (--CH.sub.2).sub.n where n=0-20 or (CH.sub.2).sub.n --CH.dbd.CH (--CH.sub.2).sub.b where a and b are independently selected from 0-20 and a+b is in the range 0-20, X.sup.1 is independently selected from C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkenyl, Y is independently selected from C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl or H and Z is selected from OH or NR.sup.1 R.sup.11 where R.sup.1 and R.sup.11 are independently selected from H, C.sub.1 -C.sub.20 alkyl and C.sub.2 -C.sub.20 alkenyl, provided that where Y is alkyl and X is a chemical bond at least one of the groups R.sub.1 -R.sub.8 is selected from --X--COO--X.sup.1 and --X--COZ, and further provided that is R.sub.1 -R.sub.8 all contain more than 6 carbon atoms and are all selected from alkyl or --X--O--Y where X is --(CH.sub.2)--.sub.n and Y is alkyl then R.sub.1 -R.sub.8 are not all in the 2, 3, 9, 10, 16, 17, 23 and 24 positions indicated in formula I. These phthalocyanines may exhibit discotic liquid crystal phases, absorb infra-red radiation and make good Langmuir-Blodgett films.

Substituted phthalocyanines

Phthalocyanine of formula (I), wherein M is a metal or is 2H, bonded at 29 and 31 positions shown, R.sub.1 to R.sub.8 are the same or different and are independently selected from C.sub.1 to C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, --X--COO--X.sup.1, --X--O--Y, a, and --X--COZ where X is independently selected from a chemical bond, (CH.sub.2).sub.n where n-0-20 or (CH.sub.2).sub.a CH--CH (CH.sub.2).sub.b where a and b are independently selected from 0-20 and a+b is in the range 0-20, X.sup.1 is independently selected from C.sub.1 -C.sub.20 alkyl or C.sub.2 -C.sub.20 alkenyl, Y is independently selected from C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl or H and Z is selected from OH or NR.sup.1 R.sup.11 are independently selected from H, C.sub.1 -C.sub.20 alkyl and C.sub.2 -C.sub.20 alkenyl. These phthalocyanines may exhibit discotic liquid crystal phases, absorb infra-red radiation and make good Langmuir-Blodgett films.

Liquid crystal compounds of formula (I) are described, where formula (I) is given as R.sub.1 --A--(X.sub.m --(B).sub.n --R.sub.2 where A is selected from nathyl, flourinated naphthyl, brominated naphthyl, 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 hydrogen, X is selected from C.tbd.C, COO and C.tbd.C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C.tbd.C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine. Also described are liquid crystal compounds suitable for inclusion in devices utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase and described by formula (II): R.sub.3 --J--(Y).sub.p --(Z).sub.q --R.sub. 4, where J is selected from nathyl, fluorinated naphthyl, brominated naphthyl, Z 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 hydrogen, Y is selected from C.dbd.C, COO and C.dbd.C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0.

A material suitable for a guest-host liquid crystal device comprises a solution of a liquid crystal material and a pleochroic dye characterized in that the dye comprises at least one anthraquinone compound free from water-solubilizing and ionic substituents and having the formula: ##STR1## wherein each of R and R.sup.1 independently represents an n-alkyl group having from 4 to 7 carbon atoms inclusive and wherein each of R.sup.2 and R.sup.3 is independently selected from hydrogen and alkyl groups having from 1 to 4 carbon atoms inclusive.

Liquid crystal materials containing pleochroic anthraquinone dyes

A material suitable for a guest-host liquid crystal device comprises a soion of a liquid crystal material and a pleochroic dye where in the pleochroic dye comprises at least one anthrquinone compound free from water solubilizing and ionic substituents and having the formula: ##STR1## wherein Q is NH.sub.2, OH, alkyl, aryl, NO.sub.2 or halo;

Liquid crystal compositions with pleochroic anthraquines dyes

A material suitable for a guest-host liquid crystal device comprises a solution of a liquid crystal material and a pleochroic dye wherein the pleochroic dye comprises at least one compound having a formula: ##STR1## wherein one of X and Y is OH and the other is NHR wherein R is H or lower alkyl; each of R.sub.1 and R.sub.2 independently represents alkyl, aryl, aralkyl, alkoxy or --NR.sub.3 R.sub.4 wherein each of R.sub.3 and R.sub.4 is independently H or lower alkyl, provided that R.sub.2 is always adjacent to an OH group.

A material suitable for a guest-host liquid crystal device comprises a solution of a liquid crystal material and a pleochroic dye wherein the pleochroic dye comprises at least one anthraquinone compound free from water solubilizing and ionic substituents and having the formula: ##STR1## wherein P is OH or NH.sub.2 ; each group X.sup.A is independently selected from OH, NO.sub.2, SR and NZ.sub.1 Z.sub.2 provided that one group X.sup.A is SR and the other group X.sup.A is OH, NO.sub.2 or NZ.sub.1 Z.sub.2 is 1 or 2; each group Q.sub.1 is independently alkyl having from 1 to 20 carbon atoms; each group R is independently selected from alkyl having from 1 to 20 carbon atoms, aryl having up to 15 carbon atoms and cycloalkyl having from 4 to 8 carbon atoms.

Organic materials

A material suitable for a guest-host liquid crystal device comprises a solution of a liquid crystal material and a pleochroic dye wherein the pleochroic dye comprises at least one compound having a formula: ##STR1## wherein: R represents a group selected from optionally substituted alkyl and optionally substituted monocyclic aryl;

Liquid crystal compositions with pleochroic anthraquinone dyes

In accordance with the invention, a liquid crystal composition for multiplexed twisted nematic displays which exists in a nematic mesophase from at least about -20.degree. C. to 50.degree. C., comprises:

Liquid crystal compositions for multiplexed displays

In accordance with the invention, a liquid crystal composition for multiplexed twisted neumatic displays which exists in a nematic mesophase from at least about -20.degree. C. to 50.degree. C. comprises:

A range of eutectic mixtures containing at least three compounds having the formula ##SPC1## Where X.sup.1 is an alkyl group, an alkoxy group or a substituted phenyl group ##SPC2## Where R is an alkyl or alkoxy group, are described. The eutectic mixtures extend the temperature ranges over which their constituent compounds exhibit liquid crystal properties and are thus useful in liquid crystal devices operating in those temperature ranges.

Growing community of inventors

Malvern Link, United Kingdom

Kenneth J Harrison