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High-performance amorphous donor–acceptor conjugated polymers containing x-shaped anthracene-based monomer and 2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione for organic thin-film transistors

Authors

  • Joo Bin Lee,

    1. Department of Chemistry, Research Institute for Natural Sciences, Korea University, 5 Anam-dong, Sungbuk-gu, Seoul 136-701, South Korea
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  • Kyung Hwan Kim,

    1. Department of Chemistry, Research Institute for Natural Sciences, Korea University, 5 Anam-dong, Sungbuk-gu, Seoul 136-701, South Korea
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  • Chang Seop Hong,

    1. Department of Chemistry, Research Institute for Natural Sciences, Korea University, 5 Anam-dong, Sungbuk-gu, Seoul 136-701, South Korea
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  • Dong Hoon Choi

    Corresponding author
    1. Department of Chemistry, Research Institute for Natural Sciences, Korea University, 5 Anam-dong, Sungbuk-gu, Seoul 136-701, South Korea
    • Department of Chemistry, Research Institute for Natural Sciences, Korea University, 5 Anam-dong, Sungbuk-gu, Seoul 136-701, South Korea
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Abstract

New diketopyrrolopyrrole (DPP)-containing amorphous conjugated polymers, such as poly(3-(5-((9,10-bis((4-hexylphenyl)ethynyl)-6-(prop-1-ynyl)anthracen-2-yl)ethynyl) thiophen-2-yl)-5-(2-hexyldecyl)-2-(2-octyldodecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (4), and poly(3-(5-((2,6-bis((4-hexylphenyl)ethynyl)-10-(prop-1-ynyl)anthracen-9-yl)ethynyl)thiophen-2-yl)-2,5-bis(2-octyldodecyl)-6-(thio phen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (7), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7, incorporating a DPP moiety at the 9,10-position of the anthracene ring through a triple bond, showed a much lower bandgap energy (Eg = 1.81 eV) than copolymer 4 (Eg = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl-DPP from the 2,6- to the 9,10-position in the anthracene ring. Because of the donor–acceptor (D–A) interaction and the two-dimensional planar structure of the X-shaped donor monomer, the resulting polymers showed good interchain π−π stacking in the thin-film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin-film transistor, the best mobility of up to 0.12 cm2 V−1 s−1 (Ion/off = ∼ 4.4 × 106) was observed, which is one of the highest values recorded for amorphous polymer films reported to date. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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