Polymerizable absorbers of UV and high energy visible light

1. An ophthalmic device that is a free radical reaction product of a reactive mixture comprising: one or more monomers suitable for making the ophthalmic device; and a polymerizable high energy light absorbing compound comprising a compound of formula

wherein:

m and n are independently 0, 1, 2, 3, or 4;

T is a bond, O, or NR;

X is O, S, NR, SO, or SO 2 ;

Y is a linking group;

P g is a polymerizable group;

R at each occurrence is independently H, C 1 -C 6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—P g ;

R 1 and R 2 , when present, are independently at each occurrence C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 3 R 4 , or benzyl, wherein R 3 and R 4 are independently H or C 1 -C 6 alkyl, or two adjacent R 1 or R 2 groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group.

2. The ophthalmic device of claim 1 further comprising a second polymerizable high energy light absorbing compound.

3. The ophthalmic device of claim 2 wherein the second polymerizable high energy light absorbing compound is a UV absorbing compound.

4. The ophthalmic device of claim 3 wherein the UV absorbing compound comprises a compound of formula I, a benzophenone, a benzotriazole, a triazine, a substituted acrylonitrile, a salicyclic acid derivative, a benzoic acid derivative, a cinnamic acid derivative, a chalcone derivative, a dypnone derivative, a crotonic acid derivative, or mixtures thereof.

5. The ophthalmic device of claim 1 wherein the polymerizable high energy light absorbing compound comprises a mixture of a compound of formula I wherein X is S and a compound of formula I wherein X is O.

6. The ophthalmic device of claim 1 wherein the polymerizable high energy light absorbing compound comprises a mixture of a compound of formula I wherein X is S and a benzotriazole UV absorbing compound.

7. The ophthalmic device of claim 1 wherein the monomer suitable for making the ophthalmic device comprises a hydrophilic component, a silicone-containing component, or mixtures thereof.

8. The ophthalmic device of claim 1 that is a contact lens, a corneal onlay, a corneal inlay, an intraocular lens, or an overlay lens.

9. The ophthalmic device of claim 1 that is a hydrogel contact lens.

10. The ophthalmic device of claim 1 wherein m and n are each independently 0 or 1.

11. The ophthalmic device of claim 1 wherein Y at each occurrence is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations thereof.

12. The ophthalmic device of claim 1 wherein P g comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.

13. The ophthalmic device of claim 1 wherein X is O.

14. The ophthalmic device of claim 1 wherein X is S.

15. The ophthalmic device of claim 1 wherein EWG is cyano, amide, ester, keto, or aldehyde.

16. The ophthalmic device of claim 1 wherein EWG is cyano.

17. The ophthalmic device of claim 1 wherein the compound of formula I is:

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl acrylate;

N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)methacrylamide;

N-(2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl)acrylamide;

2-(2-cyano-N-methyl-2-(9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-cyano-2-(9H-thioxanthen-9-ylidene)-N-(2-(N-vinylacetamido)ethyl)acetamide;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl acrylate;

N-(2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl)methacrylamide;

N-(2-(2-cyano-2-(9H-xanthen-9-ylidene)acetamido)ethyl)acrylamide;

2-(2-cyano-N-methyl-2-(9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-cyano-N-(2-(N-vinylacetamido)ethyl)-2-(9H-xanthen-9-ylidene)acetamide;

2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl acrylate;

N-(2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl)methacrylamide;

N-(2-(2-(acridin-9(10H)-ylidene)-2-cyanoacetamido)ethyl)acrylamide;

2-(2-(acridin-9(10H)-ylidene)-2-cyano-N-methylacetamido)ethyl methacrylate;

2-(acridin-9(10H)-ylidene)-2-cyano-N-(2-(N-vinylacetamido)ethyl)acetamide;

2-(2-cyano-2-(9H-thioxanthen-9-ylidene)acetamido)-2-methylpropyl methacrylate;

2-(2-cyano-2-(9H-xanthen-9-ylidene)acetoxy)-2-methylpropyl acrylate;

(Z)-2-(2-cyano-2-(3-hydroxyacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(10-methylacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(3,6-dihydroxyacridin-9(10H)-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-(7H-benzo[c]xanthen-7-ylidene)-2-cyanoacetamido)ethyl methacrylate;

(Z)-2-(2-cyano-2-(3-methoxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(2-cyano-2-(3,6-dihydroxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2-methyl-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(1-hydroxy-9H-xanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2,4-dichloro-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-(2-chloro-9H-thioxanthen-9-ylidene)-2-cyanoacetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(2-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

(E)-2-(2-cyano-2-(4-isopropyl-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

2-(3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(3-oxo-2-(9H-thioxanthen-9-ylidene)butanamido)ethyl methacrylate;

2-(3-methoxy-3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(3-amino-3-oxo-2-(9H-thioxanthen-9-ylidene)propanamido)ethyl methacrylate;

2-(2-cyano-2-(10,10-dioxido-9H-thioxanthen-9-ylidene)acetamido)ethyl methacrylate;

N-(2-(2-cyano-2-(10-methylacridin-9(10H)ylidene)acetamido)ethyl) methacrylamide; or

2-(2-cyano-2-(9H-thioxanthen-9-yl idene)acetoxy)ethyl methacrylate.