IP Library Granted Patent US 11,920,069
Granted Patent B2
US 11,920,069 · App. 17/438,238 · Granted Mar 5, 2024

Compositions containing semiconducting nanoparticles, and polymer or composite layers formed therefrom, and optical devices

Inventor: Artyom Semyonov (Rehovot, IL)
Assignee: MERCK PATENT GMBH
C09K11/025C09K11/70C09K11/883
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Quick Facts
Patent No.
US 11,920,069
App. No.
17/438,238
Granted
Mar 5, 2024
Kind
B2
Abstract

Compositions containing at least one sort of semiconducting nanoparticle, at least one antioxidant, a polymerizable component, a liquid organic compound and an organic additive of formula (II) wherein M is a divalent metal ion; and R 1 and R 2 are, each independently, a straight chain alkyl group having 1 to 16 carbons atoms, or a straight chain alkenyl group having 2 to 15 carbon atoms or branched chain alkyl or alkenyl group having 3 to 15 carbon atoms, and polymer or composite layers formed therefrom, optical devices containing the layers and their preparation and method of use, as well as a method to improve at least one feature of a quantum material or a quantum material layer.

Claims (52)

1. A composition comprising at least these components:

i) at least one sort of semiconducting nanoparticle;

ii) at least one antioxidant, which is 2-tert-Butylhydrochinone; 4-tert-Butylcatechol; 6-tert-Butyl-2, 4-xylenol; 3,5-Di-tert-butyl-4-hydroxytoluene; 2,6-Di-tert-butylphenol; or a combination of two or more thereof;

iii) a polymerizable component; and

iv) a liquid organic compound; and

v) an organic additive of formula (II)

wherein

M is a divalent metal ion; and

R 1 and R 2 are, each independently, a straight chain alkyl group having 1 to 16 carbons atoms, or a straight chain alkenyl group having 2 to 15 carbon atoms or a branched chain alkyl or alkenyl group having 3 to 15 carbon atoms.

2. The composition of claim 1 , wherein the polymerizable component is selected from the group consisting of UV curable monomers and thermal-curable monomers.

3. The composition according to claim 1 , wherein the composition comprises 20 to 1,000 parts of the at least one antioxidant based on 100 parts of the semiconducting nanoparticles in the composition.

4. The composition according to claim 1 , wherein M is Zn, Mg or Cd.

5. The composition according to claim 1 , wherein the at least one sort of semiconducting nanoparticle comprises In and P.

6. The composition according to claim 1 , wherein the liquid organic compound is selected from the group consisting of monoalkyl ethers, diethylene glycol dialkyl ethers, alkylene glycol ether acetates, ethylene glycol alkyl ether acetates, propylene glycol alkyl ether acetates, aromatic hydrocarbons, ketones, alcohols esters, ethylene carbonate, and combinations of two or more thereof.

7. The composition according to claim 1 , wherein the quantum yield of the composition after 16 hours from said composition having been prepared is at least 90%, with respect to the composition at the time of preparation.

8. The composition according to claim 1 , wherein the composition comprises 50 to 400 parts of the polymerizable component based on 100 parts of the semiconducting nanoparticles in the composition.

9. The composition of claim 1 , wherein said antioxidants is 2-tert-Butylhydrochinone; 4-tert-Butylcatechol; 6-tert-Butyl-2,4-xylenol; 2,6-Di-tert-butylphenol; or a combination of two or more thereof.

10. A method of manufacturing the composition according to claim 1 , comprising at least these steps:

(i) providing the quantum material;

(ii) providing the at least one antioxidant, which is 2-tert-Butylhydrochinone; 4-tert-Butylcatechol; 6-tert-Butyl-2,4-xylenol; 3,5-Di-tert-butyl-4-hydroxytoluene; 2,6-Di-tert-butylphenol; or a combination of two or more thereof;

(iii) providing the liquid organic component;

(iv) providing the polymerizable component;

(v) providing the organic additive of formula (II); and mixing the components of steps (i)-(v).

11. The method of claim 10 , wherein the composition is subjected to irradiation with light of a wavelength of 300 to 600 nm having an intensity of a wavelength of 300 to 600 nm having an intensity of 0.025 to 1 W/cm 2 .

12. A method of manufacturing a polymer layer comprising at least these steps:

(a) providing a substrate;

(b) providing the composition of claim 1 ;

(c) applying the composition to the substrate to form a layer; and

(d) polymerizing the composition.

13. An optical device comprising a layered composite obtained by a method according to claim 12 .

14. A layered composite comprising at least:

aa) a layer comprising at least

(A) a quantum material comprising a plurality of at least one kind of semiconducting nanoparticle,

(B) a matrix polymer,

(C) at least one antioxidant, which is 2-tert-Butylhydrochinone; 4-tert-Butylcatechol; 6-tert-Butyl-2,4-xylenol; 3,5-Di-tert-butyl-4-hydroxytoluene; 2,6-Di-tert-butylphenol; or a combination of two or more thereof, and

(D) an organic additive of formula (II)

wherein

M is a divalent metal ion; and

R 1 and R 2 are, each independently, a straight chain alkyl group having 1 to 16 carbons atoms, or a straight chain alkenyl group having 2 to 15 carbon atoms or a branched chain alkyl or alkenyl group having 3 to 15 carbon atoms and

bb) a substrate.

15. The layered composite according to claim 14 , wherein said antioxidant is 3,5-Di-tert-butyl-4-hydroxytoluene.

16. The layered composite according to claim 14 , wherein M is Zn, Mg or Cd.

17. An optical device comprising a layered composite according to claim 14 .

18. A composition comprising at least these components:

i) at least one sort of semiconducting nanoparticle;

ii) at least one antioxidant, which includes 3,5-di-tert-butyl-4-hydroxytoluene;

iii) a polymerizable component;

iv) a liquid organic compound; and

v) an organic additive of formula (II)

wherein

M is divalent metal ion; and

R 1 and R 2 are, each independently, a straight chain alkyl group having 1 to 16 carbons atoms, or a straight chain alkenyl group having 2 to 15 carbon atoms or a branched chain alkyl or alkenyl group having 3 to 15 carbon atoms.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2025
From: MERCK PATENT GMBH
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 071620/0512 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2022
From: SEMYONOV, ARTYOM
To: QLIGHT NANOTECH LTD.,
Reel/Frame 061345/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2022
From: QLIGHT NANOTECH LTD.,
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 061345/0448 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2022
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 061345/0525 →
Priority Claims (1)
EP 19162358 · Mar 12, 2019 · regional
Continuity (1)
Related Publication 20220186113A1 · Jun 16, 2022
Cited By (1)
US 12,552,979