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Synthesis of Anthracene Derivatives with Azaacene‐Containing Iptycene Wings and the Utilization as a Dopant for Solution‐Processed Organic Light‐Emitting Diodes
Author(s) -
Hayashi Hironobu,
Kato Yuki,
Matsumoto Akinobu,
Shikita So,
Aizawa Naoya,
Suzuki Mitsuharu,
Aratani Naoki,
Yasuda Takuma,
Yamada Hiroko
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903476
Subject(s) - anthracene , oled , dopant , electroluminescence , materials science , tetracene , photochemistry , acene , fluorescence , diphenylamine , molecule , doping , optoelectronics , chemistry , organic chemistry , nanotechnology , optics , physics , layer (electronics) , metallurgy
Substituted acene derivatives are regarded as promising materials for organic electronic devices such as organic light‐emitting diodes (OLEDs). In particular, anthracene derivatives are known to exhibit good fluorescence property, with the air stability and solubility in common organic solvents expected to give advantages for solution‐processed device fabrication. In this study, a series of bistriisopropylsilyl(TIPS)ethynyl anthracene derivatives with azaacene‐containing iptycene wings have been synthesized by using condensation reactions. Effects of size of azaacenes on optical properties and packing structures were investigated. UV/Vis absorption and fluorescence spectra indicate that the π‐elongation of iptycene units has small effects on the overall π‐system, which is also supported by electrochemical measurements. Secondly, single‐crystal X‐ray analysis implies that the molecules likely have interactions with the iptycene units of adjacent molecules, while the iptycene wings and TIPSethynyl groups can prevent the central anthracene unit from undesirable non‐radiative energy loss. Finally, the most emissive derivative was used as a dopant for solution‐processed OLEDs, showing obvious electroluminescence with a luminance of over 920 cd m −2 .