Quantum dots with charge-transporting ligands

Patent metadata

Field	Value
Publication number	US-2020067006-A1
Application number	US-201916546486-A
Country	US
Kind code	A1
Filing date	Aug 21, 2019
Priority date	Aug 21, 2018
Publication date	Feb 27, 2020
Grant date	—

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

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 an aromatic or heteroaromatic ring system having 5-60 ring atoms, which in each case may be unsubstituted or substituted and which may be linked to the aromatic or heteroaromatic ring system via any desired position;
R 3 is hydrogen or an aromatic or heteroaromatic ring system having 5-60 ring atoms, which in each case may be unsubstituted or substituted and which may be linked to the aromatic or heteroaromatic ring system via any desired position; or
R 2 and R 3 form together with the carbon atoms to which they are bonded, a 5- or 6-membered ring which may contain an aromatic or heteroaromatic ring system having 5-60 ring atoms, which in each case may be unsubstituted or substituted and which may be linked to the aromatic or heteroaromatic ring system via any desired position;
or
(ii) an electron-transporting ligand of formula (X)

wherein:
R 11 is an aromatic or heteroaromatic ring system having 5-60 ring atoms, which in each case may be unsubstituted or substituted and which may be linked to the aromatic or heteroaromatic ring system via any desired position;
R 12 is hydrogen or an aromatic or heteroaromatic ring system having 5-60 ring atoms, which in each case may be unsubstituted or substituted and which may be linked to the aromatic or heteroaromatic ring system via any desired position; or
(iii) a combination thereof.

2 .- 3 . (canceled)

4 . 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.

5 .- 8 . (canceled)

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

10 . The nanostructure composition of claim 1 , wherein in the hole-transporting ligand of formula I,
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, C 1-10 haloalkyl, halogen, C 1-10 alkylamino, or cycloalkyl; and
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:

11 . 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.

12 . (canceled)

13 . The nanostructure composition of claim 11 , 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.

14 . 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.

15 .- 16 . (canceled)

17 . 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.

18 .- 19 . (canceled)

20 . 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.

21 . (canceled)

22 . 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.

23 .- 24 . (canceled)

25 . 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.

26 . (canceled

Assignees

• Nanosys Inc

Inventors

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

Classifications

• C09K11/70

  containing phosphorus · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• H01L51/502 Primary

  Electricity · mapped topic