Quantum dots with charge-transporting ligands

Patent metadata

Field	Value
Publication number	US-11637256-B2
Application number	US-201916546486-A
Country	US
Kind code	B2
Filing date	Aug 21, 2019
Priority date	Aug 21, 2018
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The present invention provides nanostructure compositions and methods of producing nanostructure compositions. The nanostructure compositions comprise a population of nanostructures comprising charge-transporting ligands. The present invention also provides nanostructure films comprising the nanostructure compositions and methods of making nanostructure films using the nanostructure compositions.

First claim

What is claimed is:

1. A nanostructure composition comprising:
(a) at least one population of nanostructures; and
(b) at least one charge-transporting ligand bound to the surface of the nanostructures, the charge-transporting ligand comprising:
(i) a hole-transporting ligand of formula (I)

wherein:
R 1 is hydrogen or carboxy;
R 2 is

R 3 is hydrogen;
X 1 -X 8 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
X 9 -X 13 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 4 is an unsubstituted or substituted aryl or heteroaryl group;
X 14 -X 17 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 5 is an unsubstituted or substituted aryl or heteroaryl group;
R 6 is hydrogen; or
R 5 and R 6 together form:

X 18 -X 22 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 7 is an unsubstituted or substituted aryl or heteroaryl group; or
R 2 and R 3 together form:

X 23 -X 26 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 8 is an unsubstituted or substituted aryl or heteroaryl group;
R 9 is an unsubstituted or substituted aryl or heteroaryl group;
R 10 is hydrogen or an unsubstituted or substituted aryl or heteroaryl group; or
R 9 and R 10 together form:

or
(ii) an electron-transporting ligand of formula (X)

wherein:
R 11 is

R 12 is hydrogen or is

R 13 and R 17 independently are a substituted or unsubstituted aryl or heteroaryl group;
R 14 and R 18 independently are hydrogen, or

R 15 and R 19 independently are a substituted or unsubstituted aryl or heteroaryl group;
R 16 and R 20 independently are a substituted or unsubstituted aryl or heteroaryl group;
R 21 is a substituted or unsubstituted aryl or heteroaryl group;
R 22 is a substituted or unsubstituted aryl or heteroaryl group;
R 23 is H or a substituted or unsubstituted aryl or heteroaryl group; and
R 24 is H or a substituted or unsubstituted aryl or heteroaryl group;
or
(iii) a combination thereof.

2. The nanostructure composition of claim 1 , wherein the nanostructures comprise a core selected from the group consisting of InP, InZnP, InGaP, CdSe, CdS, CdSSe, CdZnSe, CdZnS, ZnSe, ZnTe, ZnSeTe, ZnS, ZnSSe, InAs, InGaAs, and InAsP.

3. The nanostructure composition of claim 1 , wherein the nanostructures comprises an InP core, a ZnSe shell, and a ZnS shell.

4. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has formula II:

wherein:
X 1 -X 8 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl; and
R 1 is hydrogen or carboxy.

5. The nanostructure composition of claim 4 , wherein X 1 , X 2 , X 4 , X 5 , X 7 , and X 8 are hydrogen, X 3 and X 6 independently are hydrogen, methyl, tert-butyl, methoxy, dimethylamino, or trifluoromethyl, and R 1 is hydrogen.

6. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula III:

wherein:
X 9 -X 13 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 1 is hydrogen or carboxy; and
R 4 is an unsubstituted or substituted aryl or heteroaryl group.

7. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula IV:

wherein:
X 14 -X 17 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 1 is hydrogen or carboxy;
R 5 is an unsubstituted or substituted aryl or heteroaryl group; and
R 6 is hydrogen.

8. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula V:

wherein:
X 14 -X 17 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl; and
R 1 is hydrogen or carboxy.

9. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula VI:

wherein:
X 18 -X 22 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 1 is hydrogen or carboxy; and
R 7 is an unsubstituted or substituted aryl or heteroaryl group.

10. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula VII:

wherein:
X 23 -X 26 independently are hydrogen, carboxy, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl;
R 1 is hydrogen or carboxy; and
R 8 is an unsubstituted or substituted aryl or heteroaryl group.

11. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula VIII:

wherein:
R 1 is hydrogen or carboxy; and
R 9 is an unsubstituted or substituted aryl or heteroaryl group; and
R 10 is an unsubstituted or substituted aryl or heteroaryl group.

12. The nanostructure composition of claim 1 , wherein the hole-transporting ligand has the structure of formula IX:

wherein:
R 1 is hydrogen or carboxy.

13. The nanostructure composition of claim 1 , wherein the electron-transporting ligand has the structure of formula XII:

Assignees

• Nanosys Inc

Inventors

• Ippen Christian
• Kim Daekyoung
• Dohner Emma Rose
• Manders Jesse
• Olmeijer David
• Ma Ruiqing

Classifications

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• C09K11/70

  containing phosphorus · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title