Synthesis of Anthracene Derivatives with Azaacene-Containing Iptycene Wings and the Utilization as a Dopant for Solution-Processed Organic Light-Emitting Diodes

Hironobu Hayashi, Yuki Kato, Akinobu Matsumoto, So Shikita, Naoya Aizawa, Mitsuharu Suzuki, Naoki Aratani, Takuma Yasuda, Hiroko Yamada

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)15565-15571
Number of pages7
JournalChemistry - A European Journal
Volume25
Issue number68
DOIs
Publication statusPublished - Dec 5 2019

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Anthracene
Organic light emitting diodes (OLED)
Doping (additives)
Derivatives
Fluorescence
Molecules
Condensation reactions
X ray analysis
Electroluminescence
Organic solvents
Elongation
Luminance
Energy dissipation
Optical properties
Solubility
Single crystals
Fabrication
anthracene
Air

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of Anthracene Derivatives with Azaacene-Containing Iptycene Wings and the Utilization as a Dopant for Solution-Processed Organic Light-Emitting Diodes. / Hayashi, Hironobu; Kato, Yuki; Matsumoto, Akinobu; Shikita, So; Aizawa, Naoya; Suzuki, Mitsuharu; Aratani, Naoki; Yasuda, Takuma; Yamada, Hiroko.

In: Chemistry - A European Journal, Vol. 25, No. 68, 05.12.2019, p. 15565-15571.

Research output: Contribution to journalArticle

Hayashi, Hironobu ; Kato, Yuki ; Matsumoto, Akinobu ; Shikita, So ; Aizawa, Naoya ; Suzuki, Mitsuharu ; Aratani, Naoki ; Yasuda, Takuma ; Yamada, Hiroko. / Synthesis of Anthracene Derivatives with Azaacene-Containing Iptycene Wings and the Utilization as a Dopant for Solution-Processed Organic Light-Emitting Diodes. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 68. pp. 15565-15571.
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