Synthesis, characterization, and physical properties of a conjugated heteroacene: 2-methyl-1,4,6,7,8,9-hexaphenylbenz(g)isoquinolin-3(2H)-one (BIQ)

• Main Authors: Duong, Hieu M., Zhang, Qichun, Xiao, Jinchong, Yin, Zongyou, Qiao, Fen, Hu, Xiao, Zhang, Hua, Wudl, Fred, Boey, Freddy Yin Chiang
• Other Authors: School of Materials Science & Engineering
• Format: Article
• Language: English
• Published: 2012
• Subjects: DRNTU::Engineering::Materials::Microelectronics and semiconductor materials
• Online Access: https://hdl.handle.net/10356/94500; http://hdl.handle.net/10220/8685
• Institution: Nanyang Technological University

We report the synthesis and characterization of a novel, stable and blue heteroacene, 2-methyl-1,4,6,7,8,9-hexaphenylbenz(g)isoquinolin-3(2H)-one (BIQ 3). BIQ 3, with its relatively small π framework, has an absorption λmax at 620 nm, which is larger than that of pentacene (λmax=582 nm), but BIQ 3 is more stable. The solutions of BIQ 3 are observed without any noticeable photobleaching on the order of days. In the solid state, it is very stable at ambient conditions and can be stored indefinitely. Owing to its pyridone end unit, BIQ 3 can display different resonance structures in different solvents (aprotic and protic) or Lewis acids to give different colors. The attractive stability exhibited by BIQ 3 is very desirable in organic semiconductor devices. Herein, we investigated a simple heterojunction photovoltaic device based on BIQ 3 as an electron donor and [6,6]-phenyl-C61 butyric methyl ester as an electron acceptor. Our results show that this type of heteroacene could be a good candidate as a charge-transport material in organic semiconductor devices.