Compound, electron transport material, display panel and display apparatus

Patent metadata

Field	Value
Publication number	US-12134615-B2
Application number	US-202117147085-A
Country	US
Kind code	B2
Filing date	Jan 12, 2021
Priority date	Oct 30, 2020
Publication date	Nov 5, 2024
Grant date	Nov 5, 2024

Abstract

The present disclosure provides a compound having a structure represented by Formula 1, where X 1 -X 4 are each independently selected from a carbon atom or a nitrogen atom, and at least two of X 1 -X 4 are each a nitrogen atom; R 1 -R 4 are independently absent or selected from hydrogen, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C6-C30 aryl, or C2-C30 heteroaryl; m is 1 or 2; n and q are each independently selected from 0, 1, or 2, n+q≥1, and m+n+q=3; Ar is C6-C30 aryl. The molecular structure of the compound has a nitrogen-containing multidentate ligand suitable to form complexes with metal Yb or LiQ to form a metal organic complex having multidentate bondings. When applied to an OLED device, it can effectively lower the turn-on voltage and operating voltage, improve the efficiency, and prolong lifetime of the OLED device.

First claim

What is claimed is:

1. A compound having a structure according to general formula 1:

wherein X 1 -X 4 are each independently selected from the group consisting of a carbon atom and a nitrogen atom, and at least two of X 1 -X 4 are each a nitrogen atom;
R 1 -R 4 are each independently absent or selected from the group consisting of a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 alkylamino group, a C6-C30 aryl group, and a C2-C30 heteroaryl group;
Ar is selected from the following group:

wherein R 5 and R 6 are each independently absent or selected from the group consisting of a hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 alkylamino group, a C6-C30 aryl group, and a C2-C30 heteroaryl group;
R 5 and R 6 are capable of forming a ring;
Y is selected from the group consisting of a phosphorus atom, a P—O group, a silicon atom, and a germanium atom; and
* indicates a possible bonding position;
m is an integer selected from 1 or 2; and
n and q are each integers independently selected from 0, 1 or 2, n+q≥1, and m+n+q=3.

2. The compound according to claim 1 , wherein two, three or four of X 1 -X 4 are each a nitrogen atom.

3. The compound according to claim 1 , wherein m is 1, n is 1, and q is 1.

4. The compound according to claim 1 , wherein m is 2, n is 1, and q is 0.

5. The compound according to claim 1 , wherein Ar is selected from the following groups:

wherein * indicates a possible bonding position.

6. The compound according to claim 1 , wherein Ar is selected from the following group:

wherein * indicates a possible bonding position.

7. A compound being any one of the following compounds:

8. A display panel, comprising: an organic light-emitting device, wherein the organic light-emitting device comprises:
an anode;
a cathode disposed oppositely to the anode; and
an electron transport layer and a light-emitting layer that are disposed between the anode and the cathode,
wherein the electron transport layer comprises the compound according to claim 1 and a dopant, wherein the dopant is selected from the group consisting of metal lithium, a lithium organic complex, and metal Yb.

9. The display panel according to claim 8 , wherein
the lithium organic complex is lithium 8-quinolinolate, and when lithium 8-quinolinolate is doped as the dopant, lithium 8-quinolinolate is doped in mass ratio of 30%-70%, based on a total mass of the electron transport layer;
when metal lithium is doped as the dopant, lithium is doped in mass ratio of 1.4%-3.4%, based on a total mass of the electron transport layer; and
when the metal Yb is doped as the dopant, the metal Yb is doped in a mass ratio of 0.1%-10%, based on a total mass of the electron transport layer.

10. The display panel according to claim 8 , wherein the organic light-emitting device further comprises a hole blocking layer, wherein the hole blocking layer comprises a compound according to claim 1 .

11. A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device comprises:
an anode;
a cathode;
a first lamination layer and a second lamination layer disposed between the anode and the cathode and spaced apart from each other; and
a charge generation layer between the first lamination layer and the second lamination layer and comprising a compound according to claim 1 and a dopant, wherein the dopant is selected from lithium, a lithium organic complex, or metal Yb,
wherein each of the first lamination layer and the second lamination layer comprises a light-emitting layer, wherein the light-emitting layer of the first lamination layer comprises a first light-emitting layer formed between the anode and the charge generation layer, and the light-emitting layer of the second lamination layer comprises a second light-emitting layer formed between the cathode and the charge generation layer.

12. The display panel according to claim 11 , wherein
the lithium organic complex is lithium 8-quinolinolate, and when lithium 8-quinolinolate is doped as the dopant, lithium 8-quinolinolate is doped in mass ratio of 30%-70%, based on a total mass of the charge generation layer;
when lithium is doped as the dopant, lithium is doped in mass ratio of 1.4%-3.4%, based on a total mass of the charge generation layer; and
when the metal Yb is doped as the dopant, the metal Yb is doped in a mass ratio of 0.1%-10%, based on a total mass of the charge generation layer.

13. The display panel according to claim 11 , wherein the first light-emitting layer and the second light-emitting layer are each independently selected from a mono-color light-emitting layer, or a composite light-emitting layer formed by stacking a plurality of mono-color light-emitting layers,
wherein the mono-color light-emitting layer is selected from a red light-emitting layer, a green light-emitting layer, a blue light-emitting layer, or a yellow light-emitting layer, and
wherein each mono-color light-emitting layer of the plurality of mono-color light-emitting layers is independently selected from a red light-emitting layer, a green light-emitting layer, a blue light-emitting layer, or a yellow light-emitting layer.

14. The display panel according to claim 11 , wherein the first light-emitting layer and the second light-emitting layer are each independently selected from a fluorescent light-emitting layer or a phosphorescent light-emitting layer.

15. A display apparatus, comprising the display panel according to claim 8 .

Assignees

• Wuhan Tianma Micro Electronics Co Ltd
• Wuhan Tianma Microelectronics Co Ltd Shanghai Branch

Inventors

• Gao Wei
• Zhai Lu
• Zhang Lei
• Ran Quan
• Dai Wenpeng
• Guo Yuyang
• Li Xia

Classifications

• C07D471/14 Primary

  Ortho-condensed systems · CPC title

• C07D519/00 Primary

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• H10K50/125

  specially adapted for multicolour light emission, e.g. for emitting white light · CPC title

• H10K50/131

  with spacer layers between the electroluminescent layers · CPC title

• H10K50/19

  Tandem OLEDs · CPC title