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∥/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 language||English (US)|
|Number of pages||11|
|Journal||ACS Applied Materials and Interfaces|
|State||Published - Jun 8 2016|
- n-channel semiconductor
- organic thin-film transistor
- small molecule-based microfiber
ASJC Scopus subject areas
- Materials Science(all)
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CCDC 1435038: Experimental Crystal Structure Determination
Ozdemir, M. (Contributor), Choi, D. (Contributor), Kwon, G. (Contributor), Zorlu, Y. (Contributor), Cosut, B. (Contributor), Kim, H. (Contributor), Facchetti, A. F. (Contributor), Kim, C. (Contributor) & Usta, H. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc1k58kk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1k58kk&sid=DataCite