Quantum dot ligand and method for preparing the same, light emitting device and method for preparing the same, and display device

Patent metadata

Field	Value
Publication number	US-12492335-B2
Application number	US-202117624742-A
Country	US
Kind code	B2
Filing date	Mar 3, 2021
Priority date	Mar 5, 2020
Publication date	Dec 9, 2025
Grant date	Dec 9, 2025

Abstract

The present disclosure provides a quantum dot ligand and a method for preparing the same, a light emitting device and a method for preparing the same, and a display device. The quantum dot ligand is an azobenzene compound represented by formula (I). The azobenzene compound in the quantum dot ligand of the present disclosure has at least one group on each benzene ring, and the groups on the benzene rings of the azobenzene compound can be connected to the quantum dot through a coordination bond, thereby forming a network or chain structure.

First claim

What is claimed is:

1 . A quantum dot ligand, which is an azobenzene compound represented by the following structural formula (I):

wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently —H, —(CH 2 ) n SH or —(CH 2 ) p NH 2 ; and at least one of R 1 , R 2 and R 3 is —(CH 2 ) n SH or —(CH 2 ) p NH 2 , and at least one of R 4 , R 5 and R 6 is —(CH 2 ) n SH or —(CH 2 ) p NH 2 , wherein n, m and p is independently an integer from 0 to 3.

2 . The quantum dot ligand of claim 1 , wherein at least one of R 1 , R 2 and R 3 is —SH or —NH 2 , and at least one of R 4 , R 5 and R 6 is —SH or —NH 2 .

3 . The quantum dot ligand of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are all —(CH 2 ) n SH.

4 . The quantum dot ligand of claim 2 , wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are all —SH.

5 . A method for preparing a quantum ligand, which is an azobenzene compound represented by the following structural formula (I):

wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently —H, —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 ; and at least one of R 1 , R 2 and R 3 is —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 , and at least one of R 4 , R 5 and R 6 is —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 , wherein n, m and p is independently an integer from 0 to 3,
the method comprising:
reacting halogenated nitrobenzene, nitrobenzene carboxylic acid or p-phenylenediamine, to generate mercaptoazobenzene, carboxyazobenzene, or aminoazobenzene, respectively.

6 . The method of claim 5 , wherein the method comprises:
reducing the halogenated nitrobenzene in the presence of stannous chloride and concentrated hydrochloric acid to generate halogenated phenylamine; oxidizing the halogenated phenylamine in the presence of sodium perborate and boric acid to generate a halogenated azobenzene; reacting the halogenated azobenzene with potassium thiocarboxylate or thiocarboxylic acid in the presence of CuI and 1,10-phenanthroline to generate azobenzene thioester; and reacting the azobenzene thioester in the presence of TiCl 4 and Zn to generate mercaptoazobenzene.

7 . The method of claim 5 , wherein the method comprises:
reacting the nitrobenzene carboxylic acid and its derivatives in the presence of D-glucose and sodium hydroxide to generate carboxyazobenzene.

8 . The method of claim 5 , wherein the method comprises:
reacting p-phenylenediamine and its derivatives in the presence of potassium oxide to generate the aminoazobenzene.

9 . A quantum dot material, comprising quantum dots and a quantum dot ligand, wherein at least one group on each benzene ring of one azobenzene molecule is connected to the quantum dots through the coordination bond, and groups on two different benzene rings of one azobenzene molecule are respectively connected to different quantum dots through the coordination bond,
wherein the quantum dot ligand is an azobenzene compound represented by the following structural formula (I):

wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently —H, —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 ; and at least one of R 1 , R 2 and R 3 is —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 , and at least one of R 4 , R 5 and R 6 is —(CH 2 ) n SH, —(CH 2 ) m COOH or —(CH 2 ) p NH 2 , wherein n, m and p is independently an integer from 0 to 3.

10 . A quantum dot light emitting device, comprising a light emitting layer, the light emitting layer comprising quantum dots and the quantum dot ligand of claim 1 ,
wherein at least one group on each benzene ring of one azobenzene molecule is connected to the quantum dots through the coordination bond, and groups on two different benzene rings of one azobenzene molecule are respectively connected to different quantum dots through the coordination bond.

11 . The quantum dot light emitting device of claim 10 , wherein each of the quantum dots is connected to the groups of at least two azobenzene molecules through the coordination bond.

12 . The quantum dot light emitting device of claim 11 , wherein a plurality of the quantum dots is connected with each other through a plurality of azobenzene molecules to form a network structure.

13 . The quantum dot light emitting device of claim 10 , wherein the quantum dot light emitting device further comprises an anode, a hole injection layer, a hole transport layer, an electron transport layer, and a cathode.

14 . A method for preparing a quantum dot light emitting device, comprising:
coating a solution of the quantum dot material of claim 9 ; and subjecting the coated solution of the quantum dot material to treatment to form a light emitting layer, wherein at least one group on each benzene ring of one azobenzene molecule is connected to the quantum dots through the coordination bond, and groups on two different benzene rings of one azobenzene molecule are respectively connected to different quantum dots through the coordination bond.

15 . The method of claim 14 , wherein the method further comprises:
irradiating the solution of the quantum dot material with ultraviolet light before coating the solution of the quantum dot material; and subjecting the coated solution of the quantum dot material to ultraviolet thermal annealing treatment after coating the solution of the quantum dot material to form the light emitting layer.

16 . The method of claim 14 , wherein the method further comprises:
sequentially forming an anode, a hole injection layer, and a hole transport layer, and forming the light emitting layer on the hole transport layer; and sequentially forming an electron transport layer and a cathode on the light emitting layer.

17 . The method of claim 14 , wherein the method further comprises:
sequentially forming a cathode and an electron transport layer, and forming the light emitting layer on the electron transport layer; and sequentially forming a hole transport layer, a hole injection layer and an anode on the light emitting layer.

18 . A display device comprising the quantum dot light emitting device of claim 10 .

19 . The display device of claim 18 , wherein each of the quantum dots is connected to the groups of at least two azobenzene molecules through the coordination bond.

Assignees

• Boe Technology Group Co Ltd
• Beijing Boe Technology Dev Co Ltd

Inventors

• Wang Tieshi

Classifications

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K71/40

  Thermal treatment, e.g. annealing in the presence of a solvent vapour · CPC title

• H10K71/12

  using liquid deposition, e.g. spin coating · CPC title

• H10K50/115

  comprising active inorganic nanostructures, e.g. luminescent quantum dots · CPC title

• H10K85/60

  Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence) · CPC title