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Asymmetrical Fluorene[2,3‐ b ]benzo[ d ]thiophene Derivatives: Synthesis, Solid‐State Structures, and Application in Solution‐Processable Organic Light‐Emitting Diodes
Author(s) -
Du Chunyan,
Ye Shanghui,
Chen Jianming,
Guo Yunlong,
Liu Yunqi,
Lu Kun,
Liu Ying,
Qi Ting,
Gao Xike,
Shuai Zhigang,
Yu Gui
Publication year - 2009
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.200900860
Subject(s) - fluorene , thiophene , phosphorescence , substituent , quantum yield , photochemistry , oled , materials science , fluorescence , luminescence , electroluminescence , carbazole , derivative (finance) , chemistry , polymer , stereochemistry , organic chemistry , optoelectronics , nanotechnology , optics , physics , layer (electronics) , financial economics , economics , composite material
A series of novel asymmetrical fused compounds containing the backbone of fluorene[2,3‐ b ]benzo[ d ]thiophene (FBT) were effectively synthesized and fully characterized. Single‐crystal X‐ray studies demonstrated that the length of the substituent side chains greatly affects the solid‐state packing of the obtained fused compounds. DFT, photophysical, and electrochemical studies all showed that the FBTs have large band gaps, low‐lying HOMO energy levels, and therefore good stability toward oxidation. Moreover, the substituents strongly influence the fluorescence properties of the resulting FBT derivatives. The di‐ n ‐hexyl compound exhibits intense fluorescence in solution with the highest quantum yield of up to 91 %. Solution‐processed green phosphorescent organic light‐emitting diodes with the di‐ n ‐butyl derivative as the host material exhibited a maximum brightness of 14 185 cd m −2 and a luminescence efficiency of 12 cd A −1 .