Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors

Mehmet Ozdemir, Donghee Choi, Guhyun Kwon, Yunus Zorlu, Bunyemin Cosut, Hyekyoung Kim, Antonio Facchetti*, Choongik Kim, Hakan Usta

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

Electron-deficient π-conjugated small molecules can function as electron-transporting semiconductors in various optoelectronic applications. Despite their unique structural, optical, and electronic properties, the development of BODIPY-based organic semiconductors has lagged behind that of other π-deficient units. Here, we report the design and synthesis of two novel solution-proccessable BODIPY-based small molecules (BDY-3T-BDY and BDY-4T-BDY) for organic thin-film transistors (OTFTs). The new semiconductors were fully characterized by 1H/13C NMR, mass spectrometry, cyclic voltammetry, UV-vis spectroscopy, photoluminescence, differential scanning calorimetry, and thermogravimetric analysis. The single-crystal X-ray diffraction (XRD) characterization of a key intermediate reveals crucial structural properties. Solution-sheared top-contact/bottom-gate OTFTs exhibited electron mobilities up to 0.01 cm2/V·s and current on/off ratios of >108. Film microstructural and morphological characterizations indicate the formation of relatively long (∼0.1 mm) and micrometer-sized (1-2 μm) crystalline fibers for BDY-4T-BDY-based films along the shearing direction. Fiber-alignment-induced charge-transport anisotropy (μ ≈ 10) was observed, and higher mobilities were achieved when the microfibers were aligned along the conduction channel, which allows for efficient long-range charge-transport between source and drain electrodes. These OTFT performances are the highest reported to date for a BODIPY-based molecular semiconductor, and demonstrate that BODIPY is a promising building block for enabling solution-processed, electron-transporting semiconductor films.

Original languageEnglish (US)
Pages (from-to)14077-14087
Number of pages11
JournalACS Applied Materials and Interfaces
Volume8
Issue number22
DOIs
StatePublished - Jun 8 2016

Keywords

  • BODIPY
  • n-channel semiconductor
  • organic thin-film transistor
  • small molecule-based microfiber

ASJC Scopus subject areas

  • General Materials Science

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