Synthesis of Cross-linkable Hole-transporting Materials Based on Diels-Alder Reaction and Their Application in Polymer Light-emitting Diodes

Jian-chao Jia; Wan-qing Cai; Sheng-jian Liu; Fei Huang; Yong Cao

doi:10.11777/j.issn1000-3304.2017.17032

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Synthesis of Cross-linkable Hole-transporting Materials Based on Diels-Alder Reaction and Their Application in Polymer Light-emitting Diodes

Research Article | 更新时间：2021-01-26

- Synthesis of Cross-linkable Hole-transporting Materials Based on Diels-Alder Reaction and Their Application in Polymer Light-emitting Diodes
  增强出版
- Acta Polymerica Sinica Issue 7, Pages: 1169-1177(2017)
- 作者机构：
  
  华南理工大学高分子光电材料及器件研究所发光材料与器件国家重点实验室广州 510640
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2017.17032
  CLC：
- Published：2017-7，
  
  Received：28 February 2017，
  
  Revised：6 April 2017，
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Jian-chao Jia, Wan-qing Cai, Sheng-jian Liu, Fei Huang, Yong Cao. Synthesis of Cross-linkable Hole-transporting Materials Based on Diels-Alder Reaction and Their Application in Polymer Light-emitting Diodes. [J]. Acta Polymerica Sinica (7):1169-1177(2017)
DOI：

Jian-chao Jia, Wan-qing Cai, Sheng-jian Liu, Fei Huang, Yong Cao. Synthesis of Cross-linkable Hole-transporting Materials Based on Diels-Alder Reaction and Their Application in Polymer Light-emitting Diodes. [J]. Acta Polymerica Sinica (7):1169-1177(2017) DOI： 10.11777/j.issn1000-3304.2017.17032.

摘要

设计合成了一种侧链含呋喃的可交联共轭聚合物空穴传输材料聚{2，7-[9，9-二（6-（2-呋喃甲氧基）己基）芴]-共-4，4'-（4″-丁基）三苯胺}（

）和侧链含马来酰亚胺的共轭小分子交联剂

，

'-二[4-（6-马来酰亚氨基己基）苯基]-

，

'-二苯基联苯二胺（

）.基于呋喃和马来酰亚胺间Diels-Alder反应，

和

共混膜可在150℃下热处理快速交联形成具有优异抗溶剂性的薄膜，同时薄膜的光电性能可以通过控制

和

的共混比例进行有效调节.器件研究结果表明，基于

交联的薄膜表现出了优异的空穴传输、电子阻挡性质，应用于聚合物发光二极管时可有效避免由传统空穴传输材料聚3，4-亚乙二氧基噻吩/聚苯乙烯磺酸（PEDOT：PSS）作为单一界面层引起的发光淬灭现象，使相应器件性能得到大幅提升.当

添加量为10%时，相关器件表现出了最佳的器件性能，器件的最大电流效率为9.0 cdA

-1

，最大亮度为35681 cd m

-2

，启亮电压为3.2 V.

Abstract

One of the most challenging tasks in the fabrication of multilayer polymer light-emitting diodes (PLEDs) by solution process is to avoid the interfacial mixing between different layers. To overcome this challenge

extensive efforts have been made in developing crosslinkable materials for PLEDs. However

considering the unfavorable effects of their harsh crosslinking conditions on device performance

it is still desirable to design crosslinkable materials with moderate cured condition to satisfy the requirements of printing device in large scale in the future. Herein

a crosslinkable conjugated polymer with hole-transporting property

poly[9

9-bis(6-furfuryloxyhexyl)-9H-fluorene-

-4

4'-(4″-butyltriphenylamine)] (

) with furan pendant side chains

and a small molecule crosslinker

'-bis[4-(6-maleimidohexyl) phenyl]-

'-di-phenylbenzidine (

) with maleimide functional group

were developed. Due to the fast Diels-Alder reaction between the maleimide in

and the furan group in

the blend films of

and

can be quickly crosslinked in extremely short time

resulting in robust hole transporting layer (HTL) films with good solvent resistance

which can overcome the interface mixing problem in solution processed multilayer PLEDs. Such a moderate cured condition (heated at 150℃ for~1 min) can decrease negative effects and the optoelectronic property of the resulting HTL film can be tuned also by changing the ratio of the small molecular crosslinker (5%-100%; maleimide/furan). The PLEDs

with the structure of ITO/poly(3

4-ethylenedioxythiophene):poly(4-styrenesulfonate) (PEDOT:PSS)/

/emmisive layer/Ba/Al

were fabricated to investigate the effects of the crosslinker ratio on device performance. The device study results indicated that the HTLs based on

exhibited excellent hole-transporting/electron blocking properties and can prevent emission quenching caused by PEDOT:PSS in the traditional PEDOT:PSS based PLEDs. When

content is below 10%

the device displayed lower

higher

max

and LE

max

and the device with HTL based on

+ 10%

exhibited the best performance with LE

max

of 9.0 cdA

-1

max

of 35681 cd m

-2

and

of 3.2 V

with a higher brightness of 5000 cd m

-2

. Our results indicated that the Diels-Alder reaction between the maleimide and the furan groups can be used to prepare optoelectronic materials for solution processed multilayer engineering of optoelectronic devices

such as PLEDs

polymer solar cells

etc

关键词

聚合物发光二极管交联空穴传输点击化学

Keywords

Polymer light-emitting diodesCrosslinkHole transportingClick reaction

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College of Chemical and Biological Engineering, Zhejiang University

Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

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