IP Library Granted Patent US 10,483,329
Granted Patent B2
US 10,483,329 · App. 15/666,923 · Granted Nov 19, 2019

Hole transporting material, hole transporting layer, OLED display panel electronic device comprising the same

Inventors: Xiangcheng Wang (Shanghai, CN); Wei He (Shanghai, CN); Ying Liu (Shanghai, CN); Jinghua Niu (Shanghai, CN); Yuji Hamada (Shanghai, CN)
Assignees: SHANGHAI TIANMA AM-OLED CO., LTD.; TIANMA MICRO-ELECTRONICS CO., LTD.
H01L27/3211C07C211/61H01L51/006H01L51/0052H01L51/0058H01L51/5056H01L51/5072H01L51/5088H01L51/5092
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Quick Facts
Patent No.
US 10,483,329
App. No.
15/666,923
Granted
Nov 19, 2019
Kind
B2
Abstract

The present disclosure relates to a hole transporting material having a structure of formula (I). The present disclosure provides a hole transporting material having at least one fluorenyl ring and having one non-hydrogen substituent on at least one benzene ring in the formula and being capable of obtaining a suitable mobility rate without occurrence of crosstalk between pixels. And the hole transporting material provided by the present disclosure is capable of satisfying the requirements on mask cleaning with solubility (in NMP solvent).

Claims (32)

1. A hole transporting material, having a structure of formula (I),

wherein L 1 is selected from the group consisting of substituted or unsubstituted fluorenylene, and substituted or unsubstituted biphenylene; wherein the two benzene rings in substituted or unsubstituted fluorenylene, are connected with the two nitrogen atoms in formula (I); wherein the two benzene rings in substituted or unsubstituted biphenylene, are connected with the two nitrogen atoms in formula (I);

L 2 , L 3 , L 4 and L 5 each is independently selected from the group consisting of substituted or unsubstituted fluorenyl, and substituted or unsubstituted biphenylyl; wherein L 2 , L 3 , L 4 and L 5 are connected with nitrogen atoms via benzene rings;

wherein L 2 , L 3 , L 4 and L 5 in the structure of formula (I) meet:

(1) L 1 is substituted or unsubstituted fluorenylene, and/or

(2) at least one of L 2 , L 3 , L 4 and L 5 is substituted or unsubstituted fluorenyl;

wherein in the structure of formula (I), at least one hydrogen atom on at least one benzene ring is substituted by a non-hydrogen group, wherein the fluorenylene or fluorenyl is not deemed as being formed by substitution of at least one hydrogen atom on at least one benzene ring therein; and

wherein the hole transporting material has a hole mobility of 9×10 −5 -5×10 −4 cm 2 /Vs, and a solubility of 10 g/L or more in NMP at 25° C.

2. The hole transporting material claimed in claim 1 , wherein L 1 is selected from the group consisting of

or a combination of at least two said groups,

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, linear chain or branched chain of alkyl groups of C1-C5, and linear chain or branched chain alkoxy group of C1-C5;

wherein L 2 , L 3 , L 4 and L 5 in formula (I) each is selected from the group consisting of

 or a combination of at least two selected;

wherein R′ 1 , R′ 2 , R′ 3 , R′ 4 , R′ 5 , R′ 6 , R′ 7 , R′ 8 , R′ 9 , R′ 10 , R′ 11 , R′ 12 , R′ 13 , R′ 14 , R′ 15 , R′ 16 , R′ 17 , and R′ 18 each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a linear chain or a branched chain alkyl group of C1-C5, and linear chain or branched chain alkoxy group of C1-C5.

3. The hole transporting material in claim 1 , wherein L 1 in formula (I) is selected from the group consisting of

L 2 , L 3 , L 4 and L 5 each independently is selected from the group comprising consisting of

 wherein at least one fluorenyl ring exists in formula (I).

4. The hole transporting material in claim 1 , wherein L 3 and L 5 are the same; and L 2 and L 4 are the same.

5. The hole transporting material in claim 1 , which is anyone of

6. A hole transport layer comprising the hole transporting material of claim 1 , wherein the hole transport layer is doped with a p-type organic material.

7. The hole transporting layer in claim 6 , having a thickness of 600-2300 Å.

8. The hole transporting layer in claim 6 , wherein the p-type organic material has a doping density of 1 to 10 wt % in the hole transporting layer.

9. An OLED display panel comprising a first electrode and a second electrode, wherein a laminate comprising a light emitting layer and a hole transporting layer is provided between the first electrode and the second electrode, and wherein the hole transporting layer comprises the hole transporting material of claim 1 .

10. The OLED display panel in claim 9 , wherein the light emitting layer comprises at least one of a blue light emitting unit, a green light emitting unit and a red light emitting unit, or a combination of at least two of said units.

11. The OLED display panel in claim 9 , wherein the light emitting layer comprises a blue light emitting unit, a green light emitting unit and a red light emitting unit, and the blue light emitting unit, the green light emitting unit and the red light emitting unit have a common hole transporting layer comprising said hole transporting material.

12. The OLED display panel in claim 11 , wherein the common hole transporting layer has a thickness of 600-2300 Å.

13. The OLED display panel in claim 10 , wherein the green light emitting unit and the red light emitting unit comprises a phosphorescent material; and wherein the blue light emitting unit comprises a fluorescent material.

14. The OLED display panel in claim 10 , wherein a red light external quantum efficiency is 16% or more, a green light external quantum efficiency is 16% or more, and a blue light external quantum efficiency is 10% or more in the OLED display panel.

15. The OLED display panel in claim 11 , wherein the laminate further comprises at least one of a hole injection layer, an electron transporting layer, and an electron injection layer, or a combination of at least two selected therefrom.

16. The OLED display panel in claim 11 , wherein the OLED display panel comprises a first electrode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, and a second electrode sequencially.

17. The OLED display panel in claim 11 , wherein the first electrode is an anode, and the second electrode is a cathode.

18. An electronic device comprising the OLED display panel in claim 17 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2022
From: SHANGHAI TIANMA AM-OLED CO.,LTD.; TIANMA MICRO-ELECTRONICS CO., LTD.
To: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD.SHANGHAI BRANCH; TIANMA MICRO-ELECTRONICS CO., LTD.
Reel/Frame 059619/0730 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2017
From: WANG, XIANGCHENG; HE, WEI; LIU, YING; NIU, JINGHUA; HAMADA, YUJI
To: SHANGHAI TIANMA AM-OLED CO., LTD.; TIANMA MICRO-ELECTRONICS CO., LTD.
Reel/Frame 043188/0147 →
Priority Claims (1)
CN 2016 1 1235778 · Dec 28, 2016 · national
Continuity (1)
Related Publication 20170330918A1 · Nov 16, 2017