Pleochroic dyes and electro-optical displays therewith
AssigneeMinnesota Mining and Manufacturing Company
InventorWilliam A. Huffman
Life of this patent
Estimating the term…
Abstract
N-substituted anthraquinones in which the substituent group is at least partially cyclic, either cyclohexyl or aromatic, and including anils of 1,4- and 1,8-diaminoanthraquinone with p-alkyl- and p-alkoxybenzaldehyde, are pleochroic and form guest-host combinations with dielectrically positive anisotropic nematic liquid crystals. These combinations are of value in electro-optical display devices.
Claims32
As a composition of matter the combination having dielectrically positive anisotropy comprising at least one nematic liquid crystalline material having dielectrically positive anisotropy and dissolved therein a pleochroic dyestuff of the general formula:
- ##STR38## wherein substituents
- (NRR') and Q may be in positions 1 through 8,
- Q is F, Cl, NO.sub.2, NH.sub.2, NH(Alk), OH,
- x is 0, 1, 2, 3,
- m is 1 or 2,
- R is H,
- R' is cyclohexyl, bicyclohexyl or --(CH.sub.2).sub.p --Ar where p is 0, 1 or 2 and Ar is aryl of 6 to 10 carbon atoms substituted in the 4 position by --NHCOCH.sub.3, CN, C.sub.b H.sub.2b+1, --OC.sub.n H.sub.2n+1, cyclohexyl, 4--(Alk)--cyclohexyl or ##STR39## where y is 0 or 1 Y is CH.sub.2, O, S, or OCH.sub.2
- Z is H, NO.sub.2, CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, F, Cl,
- and, when y is 0, Z can also be --C.sub.6 H.sub.5, and
- wherein Ar can be substituted in from 0 to 2 further
- positions by CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, NH.sub.2, or OH, provided that when p is 1 or 2 Ar can be unsubstituted aryl, and
- when m is 2, the substituent R and R' taken together with N to which R is attached can alternatively be ##STR40## where X is NO.sub.2, CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, or N(Alk).sub.2,
- n is 1 to 20,
- b is 2 to 20;
- provided that when p is 1 or 2 b can be 1 to 20, and
- Alk is alkyl of 1-8 carbon atoms.
In an electro-optical device wherein an electrical field is imposed or withdrawn from action on a cell comprising liquid crystalline material having dissolved therein a pleochroic dye between transparent electroded glass plates, the improvement wherein the liquid crystalline material has dielectrically positive anisotropy and comprises at least one nematic liquid crystalline material having dielectrically positive anisotropy and the dissolved pleochroic dyes has the general formula:
- ##STR42## wherein substituent (NRR') and Q may be in positions 1 through 8, Q is F, Cl, NO.sub.2, NH.sub.2, NH(Alk), OH,
- x is 0, 1, 2, 3,
- m is 1 or 2,
- R is H,
- R' is cyclohexyl, bicyclohexyl or --(CH.sub.2).sub.p --Ar
- where
- p is 0, 1 or 2 and Ar is aryl of 6 to 10 carbon atoms substituted in the 4 position by --NHCOCH.sub.3, CN, C.sub.b H.sub.2b+1, --OC.sub.n H.sub.2n+1, cyclohexyl, 4--(Alk)--cyclohexyl or ##STR43## where y is 0 or 1 Y is CH.sub.2, O, S, or OCH.sub.2
- Z is H, NO.sub.2, CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, F, Cl,
- and, when y is 0, X can also be --C.sub.6 H.sub.5, and
- wherein Ar can be substituted in from 0 to 2 further positions by CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, NH.sub.2, or OH, provided that when p is 1 or 2 Ar can be unsubstituted aryl, and
- when m is 2, the substituent R and R' taken together with N to which R is attached can alternatively be ##STR44## where X is NO.sub.2, CN, --C.sub.n H.sub.2n+1, --OC.sub.n H.sub.2n+1, or N(Alk).sub.2,
- n is 1 to 20,
- b is 2 to 20;
- provided that when p is 1 or 2 b can be 1 to 20, and
- Alk is alkyl of 1-8 carbon atoms.
Dependencies are inferred from the claim text.