Quantum dots with donor-acceptor ligands

Patent metadata

Field	Value
Publication number	US-12565613-B2
Application number	US-202217859595-A
Country	US
Kind code	B2
Filing date	Jul 7, 2022
Priority date	Jan 8, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

The present invention provides nanostructure compositions and methods of producing nanostructure compositions. The nanostructure compositions comprise a population of nanostructures comprising donor-acceptor 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 comprising an InP core, a ZnS shell, and a ZnSe shell; and (b) at least one donor-acceptor ligand, wherein the donor-acceptor ligand comprises at least one terminal functional group, and wherein the at least one terminal functional group is bound to the surface of the nanostructures, wherein the donor-acceptor ligand has formula I or formula II:
D d -A a -FG f (I) or A a -D d -FG f   (II)

wherein: FG is —OH, —SH, —NH 2 , —CO 2 H, —P(O)(OH) 2 , —P(O)OH, or —SO 3 H; D is a donor moiety comprising a monocyclic or fused polycyclic aryl or heteroaryl comprising between 5 and 20 atoms, optionally substituted with one or more substituents; A is an acceptor moiety comprising for each occurrence independently, a monocyclic or fused polycyclic aryl or heteroaryl comprising between 5 and 20 atoms, optionally substituted with one or more substituents; a is an integer between 1 and 4; d is an integer between 1 and 4; and f is an integer between 1 and 4.

2 . The nanostructure composition of claim 1 , wherein FG is —CO 2 H.

3 . The nanostructure composition of claim 1 , wherein A is an acceptor moiety comprising a radical of:
(i) a compound of formula V:

wherein
A 1 to A 6 independently comprise C or N, and at least one of A 1 to A 6 is N; and

R 1 , R 2 , and R 3 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; or
(ii) a compound of formula IX:

wherein:
A 11 to A 14 independently comprise C or N, wherein at least one of A 11 to A 14 is N;
X 1 is O, S, or NR 12 ; R 10 and R 11 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 12 is hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or
(iii) a compound of formula X:

wherein:
A 15 to A 22 independently comprise C or N;
X 2 is O or S; and
R 13 , R 14 , and R 15 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; or
(iv) a compound of formula XI:

wherein:
A 23 to A 34 independently comprise C or N; and
R 16 , R 17 , and R 18 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; or
(v) a compound of formula XII:

wherein:
A 35 to A 38 independently comprise C or N;
X 3 is O, S, or NR 21 ;
R 19 and R 20 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 21 is hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or
(vi) a compound of formula XIII:

wherein:
A 39 and A 40 independently comprise C or N;
X 4 to X 7 independently comprise C, O, S, or NR 23 , wherein at least one of X 4 to X 7 is NR 23 ;
R 22 is hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 23 is hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or
(vii) a compound of formula XIV:

wherein:
A 41 to A 53 independently comprise C or N; or
(viii) a compound of formula XV:

wherein:
X 8 is C(O) or S(O) 2 ;
X 9 is CR 26 R 27 , C(O), or S(O) 2 ;
R 24 and R 25 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 26 and R 27 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; or
(ix) a compound of formula XVI:

wherein:
A 54 to A 61 independently comprise C or N;
X 10 is CR 30 R 31 , S, O, or S(O) 2 ;
R 28 and R 29 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 30 and R 31 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; or
(x) a compound of formula XVII:

wherein:
R 32 is —SO 2 —(C 6-18 aryl), —CN, —C(O)—(C 6-18 aryl), —C(O)—(C 6-18 aryl)-C(O)—(C 6-18 aryl), —SO 2 —(C 6-18 aryl)-SO 2 —(C 6-18 aryl), or —B—(C 6-18 aryl) 2 ;
R 33 is hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl; and
R 34 is hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl.

4 . The nanostructure composition of claim 1 , wherein A is an acceptor moiety that is a radical of a compound having formula V:

wherein:
A 1 to A 6 independently comprise C or N, and at least one of A 1 to A 6 is N; and
R 1 , R 2 , and R 3 are each independently hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 6-18 aryl, heteroaryl, C 1-10 alkoxy, C 1-10 haloalkyl, C(O)C 1-3 haloalkyl, —SO 2 H, —NO 2 , —CN, halogen, cycloalkyl, or C 6-18 haloaryl.

5 . The nanostructure composition of claim 4 , wherein at least one of R 1 , R 2 , or R 3 is —CN, methyl, phenyl, or pyridine.

6 . The nanostructure composition of claim 1 , wherein D is a donor moiety comprising a radical of:
(i′) a compound of formula XVIII:

Assignees

• Shoei Chemical Ind Co

Inventors

• Kim Daekyoung
• Ippen Christian
• Ma Ruiquing
• Gary Dylan
• Zehnder Donald

Classifications

• C09K11/883

  with zinc or cadmium · CPC title

• C09K11/0883

  Arsenides; Nitrides; Phosphides · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• B82Y20/00

  Nanooptics, e.g. quantum optics or photonic crystals · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title