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C−H Direct Arylated 6 H ‐Indolo[2,3‐ b ]quinoxaline Derivative as a Thickness‐Dependent Hole‐Injection Layer
Author(s) -
Dong Dai,
Fang Da,
Li Hairong,
Zhu Caixia,
Zhao Xianghua,
Li Jiewei,
Jin Lingzhi,
Xie Linghai,
Chen Lin,
Zhao Jianfeng,
Zhang Hongmei,
Huang Wei
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700112
Subject(s) - quinoxaline , oled , electroluminescence , photoluminescence , cyclic voltammetry , analytical chemistry (journal) , materials science , spectroscopy , derivative (finance) , luminescence , layer (electronics) , ionization , ionization energy , chemistry , optoelectronics , electrode , ion , nanotechnology , organic chemistry , electrochemistry , physics , financial economics , economics , quantum mechanics
A novel perfluoro‐1,4‐phenylenyl 6 H ‐indolo[2,3‐ b ]quinoxaline derivative ( TFBIQ ) was designed and synthesized by using a C−H direct arylation method. The optoelectrical properties of the obtained TFBIQ were fully characterized by UV/Vis spectroscopy, photoluminescence spectroscopy, cyclic voltammetry, and a group of Alq 3 ‐based green organic light‐emitting diodes (OLEDs). Device A, which used 0.5 nm‐thick TFBIQ as the interfacial modification layer, exhibited the five best advantages of device performance including a minimum turn‐on voltage as low as 3.1 V, a maximum luminescence intensity as high as 26564 cd m −2 , a highest current density value of 348.9 mA cm −2 at a voltage of 11 V, the smallest efficiency roll‐off, as well as the greatest power efficiency of 1.46 lm W −1 relative to all of the other tested devices with thicker TFBIQ and also 10 nm‐thick MoO 3 as hole‐injection layers (HILs). As a promising candidate for an organic HIL material, the as‐prepared TFBIQ exhibited a strong thickness effect on the performance of corresponding OLEDs. Furthermore, the theoretical calculated vertical ionization potential of the fluorinated TFBIQ suggests better anti‐oxidation stability than that of the non‐fluorinated structure.