IP Library › Granted Patent US 12,565,613

Granted Patent B2

US 12,565,613 · App. 17/859,595 · Granted Mar 3, 2026

Quantum dots with donor-acceptor ligands

Inventors: Daekyoung Kim (Santa Clara, CA); Christian Ippen (Cupertino, CA); Ruiquing Ma (Morristown, NJ); Dylan Gary (Cheney, WA); Donald Zehnder (San Carlos, CA)

Assignee: SHOEI CHEMICAL INC.

C09K11/025 C09K11/0883 C09K11/883 B82Y20/00 B82Y40/00

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Quick Facts

Patent No.: US 12,565,613
App. No.: 17/859,595
Granted: Mar 3, 2026
Kind: B2

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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.

Claims (194)

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

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:

wherein:

D 1 to D 8 independently comprise C or N;

X 11 is selected from the group consisting of O, S, NR 37 , CR 38 R 39 , and SR 40 R 41 ;

R 35 and R 36 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 37 , R 38 , R 39 , R 40 , and R 41 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(ii′) a compound of formula XIX:

wherein:

D 9 to D 16 independently comprise C or N; and

R 42 and R 45 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

(iii′) a compound of formula XX:

wherein:

D 17 to D 24 independently comprise C or N;

X 12 is selected from the group consisting of O, S, NR 48 , CR 49 R 50 , and SR 51 R 52 ;

R 46 and R 47 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 48 , R 49 , R 50 , R 51 , and R 52 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(iv′) a compound of formula XXI:

wherein:

D 25 to D 32 independently comprise C or N;

X 12 is selected from the group consisting of O, S, NR 55 , CR 56 R 57 , and SR 58 R 59 ;

R 53 and R 54 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 55 , R 56 , R 57 , R 58 , and R 59 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(v′) a compound of formula XXII:

wherein:

D 33 to D 42 independently comprise C or N; and

R 60 and R 61 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.

7 . The nanostructure composition of claim 1 , wherein D is an donor moiety that is a radical of a compound having formula XIX:

wherein:

D 9 to D 16 independently comprise C or N; and

R 42 to R 45 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.

8 . The nanostructure composition of claim 7 , wherein D 9 to D 16 are C.

9 . The nanostructure composition of claim 7 , wherein at least one of R 42 to R 45 is C 1-10 alkyl, carbazole, or diphenyl amine.

10 . An illumination device comprising the nanostructure composition of claim 1 .

11 . The illumination device of claim 10 , wherein the illumination device is a touchscreen, a monitor, a television, a cellphone, or a light emitting diode.

12 . A method of replacing a first ligand on a nanostructure with a second ligand, the method comprising:

admixing a reaction mixture comprising a population of nanostructures comprising an InP core, a ZnS shell, and a ZnSe shell, each nanostructure having the first ligand bound to the nanostructure and a donor-acceptor ligand as the second ligand, such that the second ligand displaces the first ligand and becomes bound to the nanostructure, 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 integer between 1 and 4;

d is an integer between 1 and 4; and

f is an integer between 1 and 4.

13 . The method of claim 12 , 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

(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

(iv) a compound of formula XI:

wherein:

A 23 to A 34 independently comprise C or N; and

(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 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 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 ;

(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 ;

(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 ;

14 . The method of claim 12 , wherein D is a donor moiety comprising a radical of:

(i′) a compound of formula XVIII:

wherein:

D 1 to D 8 independently comprise C or N;

X 11 is selected from the group consisting of O, S, NR 37 , CR 38 R 39 , and SR 40 R 41 ;

R 37 , R 38 , R 39 , R 40 , and R 41 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(ii′) a compound of formula XIX:

wherein:

D 9 to D 16 independently comprise C or N; and

(iii′) a compound of formula XX:

wherein:

D 17 to D 24 independently comprise C or N;

X 12 is selected from the group consisting of O, S, NR 48 , CR 49 R 50 , and SR 51 R 52 ;

R 48 , R 49 , R 50 , R 51 , and R 52 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(iv′) a compound of formula XXI:

wherein:

D 25 to D 32 independently comprise C or N;

X 12 is selected from the group consisting of O, S, NR 55 , CR 56 R 57 , and SR 58 R 59 ;

R 55 , R 56 , R 57 , R 58 , and R 59 are each independently hydrogen, C 1-10 alkyl, C 6-18 aryl, or heteroaryl; or

(v′) a compound of formula XXII:

wherein:

D 33 to D 42 independently comprise C or N; and

15 . The method of claim 12 , wherein the second ligand displaces between about 30% and about 100% on a molar basis of the first ligand on the nanostructure.

16 . The method of claim 12 , wherein the admixing is at a temperature between about 20° C. and about 100° C.

Assignments (2)

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 →