New perylene diimide derivatives: stable red emission, adjustable property from ACQ to AIE, and good device performance with an EQE value of 4.93

Luyi Zong; Yanbin Gong; Yun Yu; Yujun Xie; Guohua Xie; Qian Peng; Qianqian Li; Zhen Li

doi:10.1016/j.scib.2017.10.021

New perylene diimide derivatives: stable red emission, adjustable property from ACQ to AIE, and good device performance with an EQE value of 4.93

Sci Bull (Beijing). 2018 Jan 30;63(2):108-116. doi: 10.1016/j.scib.2017.10.021. Epub 2017 Oct 27.

Authors

Luyi Zong¹, Yanbin Gong¹, Yun Yu¹, Yujun Xie¹, Guohua Xie², Qian Peng³, Qianqian Li⁴, Zhen Li⁵

Affiliations

¹ Department of Chemistry, Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, Wuhan University, Wuhan 430072, China.
² Department of Chemistry, Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, Wuhan University, Wuhan 430072, China. Electronic address: guohua.xie@whu.edu.cn.
³ Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
⁴ Department of Chemistry, Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, Wuhan University, Wuhan 430072, China. Electronic address: qianqian-alinda@163.com.
⁵ Department of Chemistry, Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, Wuhan University, Wuhan 430072, China. Electronic address: lizhen@whu.edu.cn.

PMID: 36658922
DOI: 10.1016/j.scib.2017.10.021

Abstract

Perylene diimide (PDI) derivatives, due to their special opto-electronic property, have been successfully utilized in organic field-effect transistor (OFET), solar cells, and as non-fullerene acceptor and others, while few cases in organic light-emitting diodes (OLEDs). In this work, six perylene bisimide-based red emitters, N,N'-bis(2-decyltetradecyl)-1-([1,1':3',1″-terphenyl]-5'-yl)perylene-3,4,9,10-diimide (STPH), N,N'-bis(2-decyltetradecyl)-1,7-bis([1,1':3',1″-terphenyl]-5'-yl)perylene-3,4,9,10-diimide (DTPH), N,N'-bis(2-decyltetradecyl)-1-(5'-phenyl-[1,1':3',1″-terphenyl]-4-yl)perylene-3,4,9,10-diimide (STRPH), N,N'-bis(2-decyltetradecyl)-1,7-bis(5'-phenyl-[1,1':3',1″-terphenyl]-4-yl)perylene-3,4,9,10-diimide (DTRPH), N,N'-bis(2-decyltetradecyl)-1-(4-(2,2-diphenylvinyl)phenyl)perylene-3,4,9,10-diimide (STTPE) and N,N'-bis(2-decyltetradecyl)-1,7-bis(4-(2,2-diphenylvinyl)phenyl)perylene-3,4,9,10-diimide (DTTPE), with the excellent chemical, thermal and photo-chemical stability, are synthesized through the convenient Suzuki coupling reaction, in which, the fluorescent properties can be modified easily from ACQ to AIE by just simply changing the bulky volume of the introduced aromatic substituents. After being fabricated into organic light-emitting diodes, STRPH exhibits the best performance with the maximum luminescence, power efficiency, current efficiency and external quantum efficiency of 1,948 cd m^-2, 2.04 lm W^-1, 5.85 cd A^-1, 4.93% at Commission Internationale de L'Eclairage (CIE) coordinates of (0.56, 0.34), as the result of the high efficient energy transfer and good energy match achieved in the device.

Keywords: Aggregation induced emission; Organic light-emitting diodes; PDI derivatives; Red emitters.