IP Library Granted Patent US 11,678,570
Granted Patent B2
US 11,678,570 · App. 16/755,571 · Granted Jun 13, 2023

Hole transport material, preparation method thereof, and electroluminescent device

Inventors: Jiajia Luo (Wuhan, CN); Munjae Lee (Wuhan, CN); Xianjie Li (Wuhan, CN); Xu Wang (Wuhan, CN); Kailong Wu (Wuhan, CN); Qu Zhang (Wuhan, CN)
Assignee: WUHAN CHINA STAR OPTOELECTRONICS SEMICONDUCTOR DISPLAY TECHNOLOGY CO., LTD.
H01L51/0061B01D15/426C07D307/91C07D407/12C09K11/06H01L51/006C09K2211/1018H01L51/0007H01L51/0026H01L51/0052H01L51/0056H01L51/0073H01L51/5056H01L51/56H01L2251/556
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Quick Facts
Patent No.
US 11,678,570
App. No.
16/755,571
Granted
Jun 13, 2023
Kind
B2
Abstract

The present invention provides a hole transport material, a preparation method thereof, and an electroluminescent device. Through ingenious molecular design, a xanthracene structure is combined with different electron-donating groups to synthesize a series of hole transport materials with a suitable highest occupied molecular orbital (HOMO) energy level and a suitable lowest unoccupied molecular orbital (LUMO) energy level, and a series of high-performance display devices can be manufactured using the hole transport materials provided by the present invention.

Claims (30)

1. A hole transport material, comprising a compound consisting of a donor AN and an acceptor B, the compound having a general chemical structure as shown in Formula 1:

AN-BMN  Formula 1,

wherein the donor AN is selected from any one of the following structural formulas:

and

the acceptor BMN is selected from any one of the following structural formulas:

wherein the compound AN-BMN has any one of the following structural formulas:

2. A method of preparing a hole transport material, comprising the following steps:

Step S1, adding an acceptor compound BMN-X, a donor compound AN-H, and a catalyst into an organic solvent containing an alkali under an inert gas environment to conduct a reaction for a first time period at a first temperature to obtain a first reaction solution, wherein X is halogen, the donor AN is selected from any one of the following structural formulas:

and the acceptor BMN is selected from any one of the following structural formulas:

wherein the catalyst comprises palladium acetate and tri-tert-butylphosphine tetrafluoroborate, and the compound AN-BMN has any one of the following structural formulas:

Step S2, cooling the first reaction solution to a second temperature to obtain a mixture; and

Step S3, separating the hole transport material from the mixture, the hole transport material comprising a compound having a general chemical structural formula shown in Formula 1:

AN-BMN  Formula 1.

3. The method of preparing the hole transport material according to claim 2 , wherein the first temperature ranges from 80° C. to 150° C., and the first time period ranges from 12 hours to 36 hours.

4. The method of preparing the hole transport material according to claim 2 , wherein the second temperature is room temperature.

5. The method of preparing the hole transport material according to claim 2 , wherein in the step S1, the organic solvent is toluene, the alkali is sodium tert-pentyloxylate, and the catalyst comprises a palladium catalyst and phosphine ligand catalyst.

6. The method of preparing the hole transport material according to claim 2 , wherein the step S2 further comprises: subjecting the first reaction solution to extraction, water washing, dehydration, filtration, and centrifugal drying to obtain the mixture.

7. The method of preparing the hole transport material according to claim 2 , wherein in the step S3, the separating is performed by column chromatography with an eluent of dichloromethane and n-hexane in a volume ratio of 1:3.

8. An electroluminescent device, comprising:

a substrate;

a hole injection layer disposed on the substrate;

a hole transport layer disposed on the injection layer;

an electron blocking layer disposed on the hole transport layer;

a light-emitting layer disposed on the electron blocking layer;

a hole blocking layer disposed on the light-emitting layer;

an electron transport layer disposed on the hole blocking layer;

an electron injection layer disposed on the electron transport layer;

an electrode layer disposed on the electron injection layer; and

a light-coupling output layer disposed on the electrode layer,

wherein the hole transport layer comprises the hole transport material according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2020
From: LUO, JIAJIA; LEE, MUNJAE; LI, XIANJIE; WANG, XU; WU, KAILONG; ZHANG, QU
To: WUHAN CHINA STAR OPTOELECTRONICS SEMICONDUCTOR DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 052373/0747 →
Priority Claims (1)
CN 201911163611.7 · Nov 25, 2019 · national
Continuity (1)
Related Publication 20210408389A1 · Dec 30, 2021