Granted Patent B2

US 9,139,770 · App. 13/803,596 · Granted Sep 22, 2015

Abstract

Claims (90)

1. A quantum dot binding-ligand comprising:

a siloxane polymer comprising a plurality of monomer repeat units;

a plurality of amine or carboxy binding groups each covalently attached to one of the monomer repeat units, thereby forming a first population of monomer repeat units; and

a plurality of solubilizing groups each covalently attached to one of the monomer repeat units, thereby forming a second population of monomer repeat units, and wherein each solubilizing group is independently selected from the group consisting of a long-chain alkyl group, a long-chain alkenyl group, a long-chain alkynyl group, a cycloalkyl and an aryl.

2. The quantum dot binding ligand of claim 1 , wherein each solubilizing group is independently selected from the group consisting of a C 8-20 long-chain alkyl group, a C 8-20 long-chain alkenyl group, a C 8-20 long-chain alkynyl group, a C 3-12 cycloalkyl and a C 6-16 aryl.

3. The quantum dot binding ligand of claim 2 , wherein each long-chain alkyl group is independently selected from the group consisting of octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, and icosane.

4. The quantum dot binding ligand of claim 3 , wherein each long-chain alkyl group is independently selected from the group consisting of hexadecane, heptadecane, octadecane, nonadecane, and icosane.

5. The quantum dot binding ligand of claim 3 , wherein each long-chain alkyl group is independently selected from the group consisting of hexadecane, octadecane, and icosane.

6. The quantum dot binding ligand of claim 3 , wherein each long-chain alkyl group is octadecane.

7. The quantum dot binding ligand of claim 1 , wherein the first population of monomer repeat units is about the same number as the second population of monomer repeat units.

8. The quantum dot binding ligand of claim 1 , wherein each monomer repeat unit is covalently linked to both the amine or carboxy binding group and the solubilizing group, such that the first and second populations of monomer repeat units are the same.

9. The quantum dot binding ligand of claim 1 , comprising the structure of formula I:

wherein

each R 1 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each L is independently selected from the group consisting of C 3-8 alkylene, C 3-8 heteroalkylene, C 3-8 alkylene-O—C 2-8 alkylene, C 3-8 alkylene-(C(O)NH—C 2-8 alkylene) q , C 3-8 heteroalkylene-(C(O)NH—C 2-8 alkylene) q , and C 3-8 alkylene-O—C 1-8 alkylene-(C(O)NH—C 2-8 alkylene) q ;

each R 2 is independently selected from the group consisting of NR 2a R 2b and C(O)OH; each of R 2a and R 2b are independently selected from the group consisting of H and C 1-6 alkyl;

each R 3 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each R 4 is a solubilizing ligand independently selected from the group consisting of C 8-20 alkyl, cycloalkyl and aryl;

each R 5 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, -L-(R 2 ) q , cycloalkyl and aryl;

subscript m is an integer from 5 to 50;

subscript n is an integer from 0 to 50; and

subscript q is an integer from 1 to 10;

wherein when subscript n is 0, then R 1 is selected from the group consisting of C 8-20 alkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl.

10. The quantum dot binding ligand of claim 9 , wherein

each R 1 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each L is independently C 3-8 alkylene;

each R 2 is independently selected from the group consisting of NR 2a R 2b and C(O)OH; each of R 2a and R 2b are independently selected from the group consisting of H and C 1-6 alkyl;

each R 3 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each R 4 is a solubilizing ligand independently selected from the group consisting of C 8-20 alkyl, cycloalkyl and aryl;

each R 5 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, -L-(R 2 ) q , cycloalkyl and aryl;

subscript m is an integer from 5 to 50;

subscript n is an integer from 0 to 50; and

subscript q is an integer from 1 to 10;

wherein when subscript n is 0, then R 1 is selected from the group consisting of C 8-20 alkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl.

11. The quantum dot binding ligand of claim 9 , wherein each L is independently selected from the group consisting of C 3-8 alkylene, C 3-8 alkylene-O—C 2-8 alkylene, C 3-8 alkylene-(C(O)NH—C 2-8 alkylene) 2 , and C 3-8 alkylene-O—C 1-8 alkylene-(C(O)NH—C 2-8 alkylene) 3 .

12. The quantum dot binding ligand of claim 9 , wherein each L is independently selected from the group consisting of propylene, butylene, pentylene, n-propylene-O-i-propylene, and pentylene-(C(O)NH-ethylene) 2 .

13. The quantum dot binding ligand of claim 9 , wherein each L-(R 2 ) q group is independently selected from the group consisting of C 3-8 alkylene-C(O)OH, C 3-8 alkylene-(C(O)OH) 2 , C 3-8 alkylene-NR 2a R 2b , C 3-8 alkylene-O—C 2-8 alkylene-(C(O)OH) 3 , and C 3-8 alkylene-(C(O)NH—C 2-8 alkylene-NR 2a R b2 ) 2 .

14. The quantum dot binding ligand of claim 9 , wherein each L-(R 2 ) q group is independently selected from the group consisting of C 3-8 alkylene-C(O)OH, C 3-8 alkylene-(C(O)OH) 2 , and C 3-8 alkylene-NR 2a R 2b .

15. The quantum dot binding ligand of claim 9 , wherein each -L-(R 2 ) q group is independently selected from the group consisting of:

16. The quantum dot binding ligand of claim 9 , wherein at least one of R 1 and R 4 is C 8-20 alkyl.

17. The quantum dot binding ligand of claim 9 , wherein at least one of R 1 and R 4 is selected from the group consisting of C 16 alkyl, C 18 alkyl, and C 20 alkyl.

18. The quantum dot binding ligand of claim 9 , wherein

each R 5 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

subscript in is an integer from 5 to 50; and

subscript n is an integer from 1 to 50.

19. The quantum dot binding ligand of claim 18 , wherein the ratio of subscript m to subscript n is about 2:1.

20. The quantum dot binding ligand of claim 18 , wherein the ratio of subscript in to subscript n is about 1:1.

21. The quantum dot binding ligand of claim 18 , wherein the ratio of subscript m to subscript n is about 1:2.

22. The quantum dot binding ligand of claim 18 , wherein

R 1 and R 3 are each independently C 1-3 alkyl;

each R 1a is independently C 1-6 alkyl;

each R 4 is independently C 8-20 alkyl;

each R 5 is independently C 1-3 alkyl; and

subscript q is an integer from 1 to 3.

23. The quantum dot binding ligand of claim 22 , having the structure:

wherein subscripts m and n are each an integer from 10 to 14.

24. The quantum dot binding ligand of claim 18 , having the structure selected from the group consisting of:

wherein

subscripts in and n are each an integer from 10 to 14.

25. The quantum dot binding ligand of claim 9 , wherein

each R 5 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl, wherein the alkyl group is optionally substituted with one —Si(R 1a ) 3 group;

subscript m is an integer from 5 to 50; and

subscript n is 0.

26. The quantum dot binding ligand of claim 25 , wherein

each R 1 is independently C 8-20 alkyl;

each R 5 is independently C 1-3 alkyl; and

subscript q is an integer from 1 to 3.

27. The quantum dot binding ligand of claim 26 , having the structure:

28. The quantum dot binding ligand of claim 27 , wherein R 1 is C 8-20 alkyl.

29. The quantum dot binding ligand of claim 25 , having the structure selected from the group consisting of:

wherein subscript m is an integer from 5 to 50.

30. A composition comprising:

(a) a quantum dot binding-ligand of claim 1 ; and

(b) a first population of light emitting quantum dots (QDs).

31. The composition of claim 30 , wherein the quantum dot binding-ligand comprises the structure of formula I:

wherein

each R 1 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each L is independently selected from the group consisting of C 3-8 alkylene, C 3-8 heteroalkylene, C 3-8 alkylene-O—C 2-8 alkylene, C 3-8 alkylene-(C(O)NH—C 2-8 alkylene) q , C 3-8 heteroalkylene-(C(O)NH—C 2-8 alkylene) q , and C 3-8 alkylene-O—C 1-8 alkylene-(C(O)NH—C 2-8 alkylene) q ;

each R 2 is independently selected from the group consisting of NR 2a R 2b and C(O)OH; each of R 2a and R 2b are independently selected from the group consisting of H and C 1-6 alkyl;

each R 3 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, cycloalkyl and aryl;

each R 4 is a solubilizing ligand independently selected from the group consisting of C 8-20 alkyl, cycloalkyl and aryl;

each R 5 is independently selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl, C 2-10 alkynyl cycloalkyl and aryl;

subscript m is an integer from 5 to 50;

subscript n is an integer from 0 to 50; and

subscript q is an integer from 1 to 10;

wherein when subscript n is 0, then R 1 is selected from the group consisting of C 8-20 alkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl.

32. The composition of claim 31 , wherein the quantum dot binding-ligand comprises the structure of formula I:

wherein subscripts m and n are each an integer from 10 to 14.

33. The composition of claim 31 , wherein the quantum dot binding-ligand comprises the structure:

34. The composition of claim 31 , wherein each -L-(R 2 ) q group is independently selected from the group consisting of:

Assignments (7)