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US 5,186,865 AGranted
Electro-optical materials and light modulator devices containing same
AssigneeAllied-Signal Inc.
InventorsChengjiu Wu, Ajay Nahata, Michael J. McFarland, Keith Horn, James T. Yardley
Life of this patent
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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.-- 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.
Claims5
A compound of the formula:
- ##STR75## 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 ##STR76## 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 ##STR77## (vii) --O(CH.sub.2).sub.2 --OCH.dbd.CH.sub.2 ;
- ##STR78## (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, ##STR79## 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, ##STR80## 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 at least one of R.sup.1 and R.sup.2 is an alkylene bridging group having from 2 to 4 carbon atoms connecting the N atom to o- position of the aromatic ring to which the N atom is attached.
25 more elements
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 ##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 ##STR83## (vii) --O(CH.sub.2).sub.2 --OCH.dbd.CH.sub.2 ;
- ##STR84## (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 ##STR85## 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, ##STR86## 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;
- with the proviso that Z.sup.1 and Z.sup.2 may not both be H unless either one or 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.
20 more elements
A compound of formula:
- ##STR87## 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) Z is H or OH:
- (c) 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, and
- (4) --(CH.sub.2).sub.m --CH.dbd.CH.sub.2, wherein m is an integer of from about 1-20, ##STR88## 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, ##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
- (d) 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,
- wherein at least one of R.sup.1 and R.sup.2 is an alkylene bridging group having from 2 to 4 carbon atoms connecting the N atom to o- position of the aromatic ring to which the N atom is attached.
21 more elements
Dependencies are inferred from the claim text.