5′,5″-(9,10-Bis((4-hexylphenyl)ethynyl) anthracene-2,6-diyl)bis(5-hexyl-2,2′-bithiophene) as an Organic Semiconductor and its Application to Thin Film Transistors

Abstract

New anthracene-containing conjugated molecules have been synthesized through Stille coupling reaction. 2,6-Dibromo-9,10-bis(4-hexylphenyl)ethynyl)anthracene and 2,6-dibromo-9,10-bis(phenylethynyl)anthracene were reacted with tributyl(5′-hexyl-2,2′-bithiophen-5-yl)stannane to yield 5′,5″-(9,10-bis(phenylethynyl)anthracene-2,6-diyl)bis(5-hexyl-2,2′-bithiophene), 1 and 5′,5″-(9,10-bis((4-hexylphenyl)ethynyl) anthracene-2,6-diyl)bis(5-hexyl-2,2′-bithiophene), 2. The molecule, 2 only exhibit good solubility in common organic solvents and good self-film-forming properties. The semiconducting properties of the molecule, 2 were evaluated in organic thin film transistors (OTFTs). The molecule, 2 exhibits charge carrier mobilities—as high as 5.3 × 10−3 cm2 V−1 s−1(ION/IOFF = 2.43 × 105) without thermal annealing process.