9,10-Bis(phenylethynyl)anthracene-based organic semiconducting molecules for annealing-free thin film transistors

• Published in: Synthetic metals Vol. 160; no. 9; pp. 1022 - 1029
• Main Authors: Bae, Suk Young, Jung, Ki Hwa, Hoang, Mai Ha, Kim, Kyung Hwan, Lee, Tae wan, Cho, Min Ju, Jin, Jung-Il, Lee, Dong Hoon, Chung, Dae Sung, Park, Chan Eon, Choi, Dong Hoon
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.05.2010; Elsevier
• Subjects: Absorption; Anthracene; Applied sciences; Design. Technologies. Operation analysis. Testing; Electronics; Exact sciences and technology; Integrated circuits; Mobility; Organic thin film transistor; Semiconductor; Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices; Transistors; X-shaped conjugated molecules; Mobility; Anthracene; Semiconductor; Absorption; Organic thin film transistor; X-shaped conjugated molecules; Charge carrier mobility; Transport process; Interconnection; Integrated circuit; Organic semiconductors; Thin film transistor; Thermal annealing; Growth from solution; Organic electronics
• ISSN: 0379-6779; 1879-3290
• DOI: 10.1016/j.synthmet.2010.02.020

New anthracene-containing conjugated molecules have been synthesized through Stille coupling reaction. 2,6-Dibromoanthracene-9,10-dione was reacted with ethynylbenzene or 1-ethynyl-4-hexylbenzene to yield 2,6-dibromo-9,10-bis(phenylethynyl)anthracene 4 and 2,6-dibromo-9,10-bis((4-hexylphenyl) ethynyl)anthracene 5. Tributyl(5-hexylthiophen-2-yl)stannane was coupled through Stille reaction to generate two anthracene-based X-shaped molecules. They exhibit good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the two molecules were evaluated in organic thin film transistors (OTFTs). Two conjugated molecules 7 and 8 exhibit fairly high charge carrier mobilities—as high as 0.010–0.014 cm 2 V −1 s −1 ( I on/ I off = 1.27 × 10 7 to 4.38 × 10 6) without thermal annealing process. The X-shaped molecules result in easy crystallization and densely cover the surface of a dielectric layer. This helps in attaining good network interconnection for the carrier transport channel, which is responsible for the relatively high carrier mobility in solution-processed OTFT.