Nonlineaphores and polymers incorporating such nonlineaphores
AssigneeMinnesota Mining and Manufacturing Company
InventorsCecil V. Francis, Elisa M. Cross, Roberta E. Harelstad, Paul F. Korkowski, Peter C. Leung, David W. Macomber, John E. Trend
Life of this patent
Estimating the term…
Abstract
Nonlinear-optic (NLO) compositions containing functionalized merocyanine dyes, such that the molecules, comprising the NLO-active compositions have a functional group at each end of the molecule and each functional group differing in reactivity, thus permitting stepwise reaction of each functional group, and NLO-active molecules prepared from hemioxonol dyes derviatived with (meth)acrylate or (meth)acrylamide groups, and their uses in devices such as second harmonic generators or polymer integrated optics.
Claims23
An NLO-active composition having the formula:
- ##STR51## wherein:
- X is ##STR52## R and R.sup.1 are independently an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms terminated with a group having an active hydrogen, R and R.sup.1 taken together with a nitrogen atom form a heterocyclic ring containing five or six atoms in the ring, or R and R.sup.1 taken together with a nitrogen atom form a heterocyclic ring containing five or six atoms in the ring substituted with an alkyl group substituted with an active hydrogen;
- y is 0 to 2;
- M and M.sup.1 are independently an olefinic carbon atom or a nitrogen atom;
- D is carbon atoms or heteroatoms necessary to form a 5- or 6-membered ring, wherein the heteroatoms are selected from the group consisting of nitrogen, oxygen, or sulfur;
- n is 0 or 1;
- and
- Q ia the non-metallic atoms necessary to form an indandione ring, an isoxazolone ring, a 2,4,6-triketohexahydropyrimidine ring, or a 2-thio-4-thiazolidinone (rhodanine) ring.
A nonlineaphore having the formula:
- ##STR53## wherein:
- T is sulfur or oxygen;
- f is 0 or 1;
- R.sup.2 and R.sup.3 are independently an alkyl or an aromatic group having 1 to 10 carbon atoms, an alkyl or aromatic group substituted with a group having 1 to 10 carbon atoms and substituted with an active hydrogen, R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the ring, or R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the ring substituted with an alkyl group substituted with an active hydrogen;
- R.sup.4 is a substituted phenyl, fluorenyl, or stibenyl group, wherein the substituents are electron withdrawing groups;
- and
- R.sup.5 is independently an alkyl or an aromatic group, having 1 to 10 carbon atoms or an alkyl or aromatic group, having 1 to 10 carbon atoms bearing a group substituted with an active hydrogen, or R.sup.4.
A nonlineaphore having the formula:
- ##STR54## wherein:
- f is 0 or 1;
- R.sup.2 and R.sup.3 are independently an alkyl or an aromatic group having 1 to 10 carbon atoms, an alkyl or aromatic group having 1 to 10 carbon atoms and substituted with a group with an active hydrogen, R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the ring, or R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the ring substituted with an alkyl group substituted with an active hydrogen;
- and
- R.sup.9 is independently an alkyl or an aromatic group having 1 to 10 carbon atoms, an alkyl or aromatic group having 1 to 10 carbon atoms and substituted with a group with an active hydrogen, or an alkyl group having 1 to 6 carbon atoms, substituted with an ester group or an amino group.
A nonlineaphore having the formula:
- ##STR55## wherein:
- f is 0 or 1;
- R.sup.2 and R.sup.3 are independently an alkyl or an aromatic group having 1 to 10 carbon atoms, an alkyl or aromatic group having 1 to 10 carbon atoms and substituted with a group with an active hydrogen, R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the, or R.sup.2 and R.sup.3 taken together form a heterocyclic ring containing 5 or 6 atoms in the substituted with an alkyl group substituted with an active hydrogen;
- and
- R.sup.10 is a substituted alkyl, having 1 to 6 carbon atoms, or a substituted aromatic group having 5 or 6 carbon atoms, wherein the substituents are halogens or groups substituted with an active hydrogen.
A nonlineaphore derivatized from a merocyanine dye with acrylates, methacrylates, acrylamides or methacrylamides groups, said nonlineaphore having second order nonlinear susceptabilities having the formula:
- ##STR56## wherein:
- Z is --CH.sub.3 or a hydrogen atom;
- p is 1 or 2;
- Y is oxygen or nitrogen;
- R.sup.6 is a hydrogen or an alkyl having 1 to 10 carbon atoms;
- R.sup.7 and R.sup.8 are independently an alkylene having 1 to 10 carbon atoms;
- x is 0 to 2;
- m is 0 to 2;
- M and M.sup.1 are independently an olefinic carbon atom or a nitrogen atom;
- and
- A is any electron group or an indandione ring, an isoxazolone ring, a 2,4,6-triketohexahydropyrimidine ring, or a 2-thio-4-thiazolidinone (rhodanine) ring.
Dependencies are inferred from the claim text.