IP Library Granted Patent US 12,134,615
Granted Patent B2
US 12,134,615 · App. 17/147,085 · Granted Nov 5, 2024

Compound, electron transport material, display panel and display apparatus

Inventors: Wei Gao (Shanghai, CN); Lu Zhai (Shanghai, CN); Lei Zhang (Shanghai, CN); Quan Ran (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Yuyang Guo (Shanghai, CN); Xia Li (Shanghai, CN)
Assignee: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.
C07D471/14C07D519/00H10K50/125H10K50/131H10K85/40H10K85/615H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/165H10K50/171H10K50/18H10K50/19
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Quick Facts
Patent No.
US 12,134,615
App. No.
17/147,085
Granted
Nov 5, 2024
Kind
B2
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.

Claims (43)

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 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2022
From: SHANGHAI TIANMA AM-OLED CO.,LTD.
To: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
Reel/Frame 059498/0307 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2021
From: GAO, WEI; ZHAI, LU; ZHANG, LEI; RAN, QUAN; DAI, WENPENG; GUO, YUYANG; LI, XIA
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 054894/0813 →
Priority Claims (1)
CN 202011193784.6 · Oct 30, 2020 · national
Continuity (1)
Related Publication 20210130355A1 · May 6, 2021