IP Library Granted Patent US 9,260,655
Granted Patent B2
US 9,260,655 · App. 14/208,084 · Granted Feb 16, 2016

Alkyl-acid ligands for nanocrystals

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Quick Facts
Patent No.
US 9,260,655
App. No.
14/208,084
Granted
Feb 16, 2016
Kind
B2
Abstract

Quantum-dot binding ligands with easy to synthesize alkyl-acids are provided. The quantum-dot binding ligands include a multiplicity of carboxy binding ligands in combination with an alkyl backbone, and optionally a solubilizing group. The ligands and coated nanostructures of the present invention are useful for close packed nanostructure compositions, which can have improved quantum confinement and/or reduced cross-talk between nanostructures.

Claims (35)

1. A composition comprising:

(a) a quantum dot binding-ligand having the formula:

wherein

each R 1a , R 1b , R 2 and R 4 is independently selected from the group consisting of H,

C 1-20 alkyl, C 1-20 heteroalkyl, C 2-20 alkenyl, C 2-20 alkynyl, and cycloalkyl; each R 3a and R 3b is independently selected from the group consisting of H and C 1-6 alkyl; subscripts m and n are each independently 0 or 1, such that m+n is 1; and subscript p is an integer of from 5 to 500; wherein

when subscript m is 0, then one of R 1a and R 1b is H, and R 2 and the other of R 1a and R 1b are selected from the group consisting of C 8-20 alkyl, C 8-20 heteroalkyl, C 8-20 alkenyl, C 8-20 alkynyl, and cycloalkyl;

when subscript m is 1, then R 1a and R 2 are both H and R 1b is selected from the group consisting of C 8-20 alkyl, C 8-20 heteroalkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl; and

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

2. The composition of claim 1 , wherein subscript p is from 70 to 80.

3. The composition of claim 1 , wherein

(a) R 2 is C 8-20 alkyl, and

(b) subscript p is from 70 to 80.

4. The composition of claim 1 , wherein R 2 is C 18 alkyl.

5. The composition of claim 1 , having the structure:

6. The composition of claim 1 , wherein

(a) at least one of R 1a , R 1b and R 2 is H; and

(b) at least one of R 1a , R 1b and R 2 is independently selected from the group consisting of C 8-20 alkyl, C 8-20 heteroalkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl.

7. The composition of claim 1 , wherein at least one of R 1a , R 1b and R 2 is C 8-20 alkyl.

8. The composition of claim 1 , wherein at least one of R 1a , R 1b and R 2 is independently selected from the group consisting of octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, and icosane.

9. The composition of claim 1 , wherein at least one of R 1a , R 1b and R 2 is independently selected from the group consisting of tetradecane, hexadecane, octadecane, and icosane.

10. The composition of claim 1 , wherein subscript p is from 10 to 100.

11. The composition of claim 1 , wherein subscript m is 0 and subscript n is 1.

12. The composition of claim 11 , having the structure:

13. The composition of claim 11 , wherein R 2 is selected from the group consisting of C 8-20 alkyl, C 8-20 heteroalkyl, C 8-20 alkenyl, C 8-20 alkynyl, and cycloalkyl.

14. The composition of claim 11 , wherein R 2 is C 8-20 alkyl.

15. The composition of claim 11 , wherein subscript p is from 25 to 100.

16. The composition of claim 1 , wherein subscript m is 1 and subscript n is 0.

17. The composition of claim 16 , having the structure:

18. The composition of claim 16 , having the structure:

19. The composition of claim 16 , wherein R 1b is selected from the group consisting of C 8-20 alkyl, C 8-20 heteroalkyl, C 8-20 alkenyl, C 8-20 alkynyl, cycloalkyl and aryl.

20. The composition of claim 16 , wherein R 1b is C 8-20 alkyl.

21. The composition of claim 16 , wherein subscript p is from 10 to 50.

22. The composition of claim 1 , wherein said InP quantum dot is a core-shell quantum dot.

23. The composition of claim 22 , wherein said core-shell quantum dot is InP/ZnS.

24. The composition of claim 1 , wherein the quantum dot binding-ligand is bound to the InP quantum dot.

Assignments (7)
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS OF THE ASSIGNEE TO BE: 2-1-1, NISHI-SHINJUKU SHINJUKU-KU TOKYO, JAPAN 163-0043 PREVIOUSLY RECORDED AT REEL: 065114 FRAME: 0769. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 9, 2023
From: NANOSYS, INC.
To: SHOEI CHEMICAL INC.
Reel/Frame 065271/0540 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2023
From: NANOSYS, INC.
To: SHOEI CHEMICAL INC.
Reel/Frame 065114/0769 →
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT RECORDED AT REEL 059569 / FRAME 0840 Recorded Sep 7, 2023
From: FORTRESS CREDIT CORP.,
To: NANOSYS, INC.
Reel/Frame 064836/0263 →
SECURITY INTEREST Recorded Apr 1, 2022
From: NANOSYS, INC.
To: FORTRESS CREDIT CORP., AS AGENT
Reel/Frame 059569/0840 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 49170/0482 Recorded Jul 1, 2021
From: OCEAN II PLO, LLC, AS AGENT
To: NANOSYS, INC.
Reel/Frame 056752/0073 →
SECURITY INTEREST Recorded Jan 17, 2019
From: NANOSYS, INC.
To: OCEAN II PLO, LLC
Reel/Frame 049170/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 1, 2014
From: FREEMAN, WILLIAM P; FURUTA, PAUL; DUBROW, ROBERT
To: NANOSYS, INC.
Reel/Frame 032576/0677 →