Electro-optical materials and light modulator devices containing same
AssigneeAllied-Signal Inc.
InventorsChengjiu Wu, Ajay Nahata, Michael J. McFarland, Keith Horn, James T. Yardley
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Abstract
Azo-type optically active compounds and polymers are provided based on compounds of the general structure [substituted aryl]--N.dbd.N--[substituted aryl] wherein aryl substituents are introduced which hinder or prohibit rotation around the single bonds of the --N.dbd.N-- central moiety (as well as around certain other single bonds), to provide "planarized" structures having improved optically active properties, especially electro-optically active properties. These compounds and polymers find use in optically active waveguides.
Claims24
A composition comprising a matrix of an optically clear polymer, having dispersed therein from about 1 to about 60 percent by weight of a compound of the formula:
- ##STR81## wherein:
- (a) X is selected from the group consisting of:
- (1) --NO.sub.2,
- (2) --CN,
- (3) --COOR.sup.3 wherein R.sup.3 is alkyl, straight chain, cyclic or branched having 1-20 carbon atoms,
- (4) --CH.dbd.C(CN).sub.2 and
- (5) --C(CN).dbd.C(CN).sub.2 ;
- (b) Ar is selected from the group consisting of
- (1) ##STR82## wherein Z.sup.2 is (i) --H
- (ii) --OH
- (iii) --OC--(O)--CH.dbd.CH.sub.2
- (iv) --OC--(O)--C(CH.sub.3).dbd.CH.sub.2
- (v) ##STR83## (vi) ##STR84## or (vii) --O(CH.sub.2).sub.2 --OCH.dbd.CH.sub.2 ;
- (2) ##STR85## (3) ##STR86## (c) Z.sup.1 is selected from the group consisting of --H and --OH;
- (d) R.sup.1 is selected from the group consisting of
- (1) --H,
- (2) alkyl, straight chain, branched or cyclic, having about 1-20 carbon atoms,
- (3) --C.sub.n H.sub.2n OH, wherein n is an integer of from about 1-20,
- (4) --(CH.sub.2).sub.m --CH.dbd.CH.sub.2, wherein m is an integer of from about 1-20.
- (5) ##STR87## wherein m is an integer of from about 1-20 and the --CH.dbd.CH.sub.2 substituent is in the m- or p- position,
- (6) --(CH.sub.2).sub.m --O--M wherein m is an integer of from about 1-10, and wherein M is
- (i) --CH.dbd.CH.sub.2,
- (ii) --C(O)--CH.dbd.CH.sub.2,
- (iii) --C(O)--C(CH.sub.3).dbd.CH.sub.2,
- (iv) ##STR88## or (v) ##STR89## wherein the --CH.dbd.CH.sub.2 substituent is in the m- or p-position and (7) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o- position of the aromatic ring to which the N atom is attached;
- and
- (e) R.sub.2 is selected from the group consisting of
- (1) --H,
- (2) alkyl, straight chain, branched or cyclic, having about 1-20 carbon atoms,
- (3) --C.sub.n H.sub.2n OH wherein n is an integer of from about 1-20, and
- (4) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o- position of the aromatic ring to which the N atom is attached;
- with the proviso that Z.sup.1 and Z.sup.2 may not both be H if neither one nor both of R.sup.1 and R.sup.2 represent an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to o-position of the aromatic ring to which the N atom is attached.
A homopolymer composition composed of recurring units selected from the group consisting of ##STR91## wherein R is ##STR92## wherein (a) X is selected from the group consisting of --NO.sub.2, --CN and --COOR.sup.3 wherein R.sup.3 is alkyl, straight chain, branched or cyclic, having about 1-20 carbon atoms,
- (b) Ar is selected from the group consisting of
- (1) ##STR93## wherein Z.sup.2 is --H or --OH;
- (2) ##STR94## and (3) ##STR95## (c) Z.sup.1 is selected from the group consisting of --H and --OH;
- (d) R.sup.2 is selected from the group consisting of
- (1) --H,
- (2) alkyl, straight chain, branched or cyclic, having about 1-2 carbon atoms,
- (3) --C.sub.n H.sub.2n OH, wherein n is an integer of from about 1-20, and
- (4) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o-position of the aromatic ring to which the N atom is attached;
- and
- (e) m is an integer of from about 1 to 20.
A copolymer composition of a comonomer selected from the group consisting of alkyl acrylate wherein the alkyl moiety contains from about 1 to 5 carbons;
- alkyl methacrylate wherein the alkyl moiety contains from about 1 to 5 carbons, acrylamide, methacrylamide, styrene and substituted styrene, with a comonomer having the formula ##STR99## wherein (a) X is selected from the group consisting of --NO.sub.2, --CN, --CH.dbd.C(CN).sub.2 ;
- --C(CN).dbd.C(CN).sub.2 and --COOR.sup.3 wherein R.sup.3 is alkyl, straight chain, cyclic or branched, having 1-20 carbon atoms,
- (b) Ar is selected from the group consisting of
- (1) ##STR100## wherein Z.sup.2 is --H or --OH, (2) ##STR101## and (3) ##STR102## (c) Z.sup.1 is selected from the group consisting of --H and --OH;
- (d) R.sup.1 is selected from the group consisting of
- (1) --(CH.sub.2).sub.m --CH.dbd.CH.sub.2, wherein m is an integer of from about 1-20,
- (2) ##STR103## wherein m is an integer of from about 1-20 and the --CH.dbd.CH.sub.2 substituent is in the m- or p- position,
- (3) --(CH.sub.2).sub.m --O--M wherein m is an integer of from about 1-10, and wherein M is
- (i) --CH.dbd.CH.sub.2,
- (ii) --C(O)--CH.dbd.CH.sub.2
- (iii) --C(O)--C(CH.sub.3).dbd.CH.sub.2 or
- (iv) ##STR104## wherein the --CH.dbd.CH.sub.2 substituent is in the m- or p- position;
- and
- (e) R.sup.2 is selected from the group consisting of
- (1) --H,
- (2) alkyl, straight chain, branched or cyclic, having about 1-20 carbon atoms,
- (3) --C.sub.n H.sub.2n OH wherein n is an integer of from about 1-20, and
- (4) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o- position of the aromatic ring to which the N atom is attached.
Dependencies are inferred from the claim text.