Intraocular lenses with combinations of UV absorbers and blue light chromophores

1. An ophthalmic device material comprising:

a) a UV/Vis absorber of Formula A or Formula B shown below:

wherein:

R 1 ═H, CH 3 , CH 2 CH 3 ; or CH 2 OH;

R 2 ═C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and

R 3 ═H, CH 3 , CH 3 O, F, Cl, Br, I, or CF 3 ;

wherein:

X═C 3 -C 4 alkenyl, C 3 -C 4 alkyl, CH 2 CH 2 CH 2 SCH 2 CH 2 or CH 2 CH 2 CH 2 SCH 2 CH 2 CH 2 ;

Y=nothing if X═C 3 -C 4 alkenyl, otherwise Y═—O—C(═O)—C(R 1 )═CH 2 , —O—C(═O)NHCH 2 CH 2 OC(═O)—C(R 1 )═CH 2 , or —O—C(═O)NHC(CH 3 ) 2 (C 6 H 4 )C(CH 3 )═CH 2 ;

R 1 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH;

R 2 ═C 1 -C 4 alkyl; and

R 3 ═H, CH 3 , CH 3 O, F, Cl, Br, I, or CF 3 ; and

b) a blue light chromophore, wherein the blue light chromophore is of Formula I or Formula II as shown below:

wherein:

R 1 ═C(O)CH═CH 2 , C(O)C(CH 3 )═CH 2 , C(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 , or C(O)NHC(CH 3 ) 2 C 6 H 4 C(CH 3 )═CH 2 ;

R 2 ═H, C 1 -C 4 alkyl, OR C 1 -C 4 alkoxy;

R 3 ═H, C 1 -C 4 alkyl, F, Cl, Br, CN, NO 2 , COOR 4 ; XOC(O)CH═CH 2 , XOC(O)C(CH 3 )═CH 2 , XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 , or XOC(O)NHC(CH 3 ) 2 C 6 H 4 C(CH 3 )═CH 2 ;

R 4 ═H or C 1 -C 4 alkyl; and

X═C 1 -C 4 alkyl or C 2 -C 4 alkenyl;

wherein:

X 1 , X 2 , and X 3 independently=H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, or benzyloxy;

Y═H, F, Cl, Br, I, or C 1 -C 6 alkyl;

W=direct bond or —O—C(═O)—NH—CH 2 —CH 2 —; and

Z═H, CH 3 , C 2 H 5 , or CH 2 OH; and

c) device forming polymeric material.

2. The ophthalmics device material according to claim 1 , wherein the UV/Vis absorber includes a compound of Formula A, wherein R 1 ═H or CH 3 ; R 2 ═C 1 -C 4 alkoxy; and R 3 ═H, CH 3 , CH 3 O, F, Cl, or CF 3 .

3. The opthalmic device material according to claim 2 , wherein the compound of Formula A are selected from the group consisting of:

2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate;

3-(5-fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate;

3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate;

3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate;

2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate;

2-hydroxy-5-methoxy-3-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate; and

2-hydroxy-5-methyl-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate.

4. The opthalmic device material according to claim 3 , wherein the compound of Formula A is selected from the group consisting of 2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate and 3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate.

5. The opthalmic implant device material according to claim 1 , wherein the UV/Vis absorber includes a compound of Formula B wherein:

X═C 3 -C 4 alkenyl, C 3 -C 4 alkyl, or CH 2 CH 2 CH 2 SCH 2 CH 2 ;

Y=nothing if X═C 3 -C 4 alkenyl, otherwise Y═—O—C(═O)—C(R 1 )═CH 2 ;

R 1 ═H or CH 3 ;

R 2 ═C 1 -C 2 alkyl; and

R 3 ═CH 3 , CH 3 O, F, Cl, or CF 3 .

6. The opthalmic device material according to claim 5 , wherein the compound of Formula B is selected from the group consisting of:

2-(3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propylthio)ethyl methacrylate;

4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxyphenol;

3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propyl methacrylate (“Compound 3”);

4-allyl-2-methoxy-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenol and

3-(4-hydroxy-3-methoxy-5-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)propyl methacrylate.

7. The ophthalmic device material according to claim 1 , wherein the device material contains from 0.5 to 4% w/w of the UV/Vis absorber.

8. The ophthalmic device material according to claim 1 , wherein the UV/Vis absorber is copolymerized with one or more other ingredients selected from device-forming materials and cross-linking agents.

9. The ophthalmic device material according to claim 1 , wherein the blue light chromophore is included in the ophthalmic device material at a concentration from 0.01 to 0.08% w/w.

10. The ophthalmic device material according to claim 1 , wherein the blue light chromophore is copolymerized with one or more other ingredients selected from device-forming materials and cross-linking agents.

11. The ophthalmic device comprising the material of claim 1 , wherein the ophthalmic device is selected from the group consisting of intraocular lenses; contact lenses; keratoprostheses; and corneal rings or inlays.

12. The ophthalmic device material according to claim 1 wherein the blue light chromophore includes a compound of Formula I, wherein:

R 1 ═C(O)CH═CH 2 , C(O)C(CH 3 )═CH 2 , or C(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 2 ═H or C 1 -C 4 alkyl;

R 3 ═H, C 1 -C 4 alkyl, F, Cl, Br, CN, NO 2 , COOR 4 ; XOC(O)CH═CH 2 , XOC(O)C(CH 3 )═CH 2 , or XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 4 ═C 1 -C 4 alkyl; and

X═C 1 -C 4 alkyl.

13. The ophthalmic device material according to claim 1 wherein the blue light chromophore includes a compound of Formula I, wherein:

R 1 ═C(O)C(CH 3 )═CH 2 or C(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 2 ═H;

R 3 ═H, C 1 -C 4 alkyl, F, Cl, Br, XOC(O)C(CH 3 )═CH 2 or XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ; and

X═C 1 -C 4 alkyl.

14. The ophthalmic device material according to claim 1 wherein the blue light chromophore includes a compound of Formula I selected from (E)-4-((2-hydroxy-5-methylphenyl)diazenyl)phenethyl methacrylate and (E)-4-hydroxy-3-((4-(2-(methacryloyloxy)ethyl)phenyl)diazenyl)phenethyl methacrylate.

15. The ophthalmic device material according to claim 1 wherein the blue light chromophore includes a compound of Formula II, wherein:

X 1 , X 2 , and X 3 independently=H, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy, Y═H, C 1 or C 1 -C 4 alkyl;

W=direct bond; and

Z is H or CH 3 .

16. The ophthalmic device material according to claim 1 the blue light chromophore includes a compound of Formula II selected from 2-hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyl methacrylate; 2-hydroxy-5-methyl-3-((3,4,5-trimethoxy-phenyl)diazenyl)benzyl methacrylate; and 5-chloro-2-hydroxy-3((4-methoxyphenyl)diazenyl)benzyl methacrylate.

17. The ophthalmic device material according to claim 1 , wherein the implant device material contains from 0.5 to 4% w/w of the UV/Vis absorber.

18. An ophthalmic device material according to claim 17 , wherein the blue light chromophore is included in the ophthalmic device material at a concentration from 0.01 to 0.08% w/w.

19. The ophthalmic device material according to claim 1 , the blue light chromophore is included in the ophthalmic device material at a concentration from 0.01 to 0.08% w/w.