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Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain links: Matrix for Solution-Processable n-Channel Field-effect Transistors.

ABSTRACT: A highly soluble pyromellitic diimide-based polymer was obtained through imidization polymerization. The novel architecture features diimide subunits linked alternately at 3-6 and N,N' positions. The polymer is highly transparent in the near ultraviolet-visible regions. Smooth and uniform thin-films were obtained through spin-coating even after blending the polymer with PCBM in 1:9 polymer:PCBM weight ratio. While the polymer itself has modest electron mobility in typical bottom-gate top-contact OFETs, an electron mobility of 3 × 10(-3) cm(2)V(-1)s(-1) was achieved for the blend, which increased to 10(-2) cm(2)V(-1)s(-1) on exposure to propylamine. Thus, polyimides are demonstrated as promising binder materials for solution-processible n-channel semiconductor blends, of which very few examples are known.

SUBMITTER: Kola S

PROVIDER: S-EPMC3263818 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain links: Matrix for Solution-Processable n-Channel Field-effect Transistors.

Kola Srinivas S Tremblay Noah J NJ Yeh Ming-Ling ML Katz Howard E HE Kirschner Stuart B SB Reich Daniel H DH

ACS macro letters 20111201 1

A highly soluble pyromellitic diimide-based polymer was obtained through imidization polymerization. The novel architecture features diimide subunits linked alternately at 3-6 and N,N' positions. The polymer is highly transparent in the near ultraviolet-visible regions. Smooth and uniform thin-films were obtained through spin-coating even after blending the polymer with PCBM in 1:9 polymer:PCBM weight ratio. While the polymer itself has modest electron mobility in typical bottom-gate top-contact ...[more]

PMID: 22282725

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Project description:The development of solution-processable n-type molecular semiconductors that exhibit high electron mobility (μe ≥ 0.5 cm2/(V·s)) under ambient conditions, along with high current modulation (Ion/Ioff ≥ 106-107) and near-zero turn on voltage (Von) characteristics, has lagged behind that of other semiconductors in organic field-effect transistors (OFETs). Here, we report the design, synthesis, physicochemical and optoelectronic characterizations, and OFET performances of a library of solution-processable, low-LUMO (-4.20 eV) 2,2'-(2,8-bis(3-alkylthiophen-2-yl)indeno[1,2-b]fluorene-6,12-diylidene)dimalononitrile small molecules, β,β'-Cn-TIFDMTs, having varied alkyl chain lengths (n = 8, 12, 16). An intriguing correlation is identified between the solid-isotropic liquid transition enthalpies and the solubilities, indicating that cohesive energetics, which are tuned by alkyl chains, play a pivotal role in determining solubility. The semiconductors were spin-coated under ambient conditions on densely packed (grafting densities of 0.19-0.45 chains/nm2) ultrathin (∼3.6-6.6 nm) polystyrene-brush surfaces. It is demonstrated that, on this polymer interlayer, thermally induced dispersive interactions occurring over a large number of methylene units between flexible alkyl chains (i.e., zipper effect) are critical to achieve a favorable thin-film crystallization with a proper microstructure and morphology for efficient charge transport. While C8 and C16 chains show a minimal zipper effect upon thermal annealing, C12 chains undergo an extended interdigitation involving ∼6 methylene units. This results in the formation of large crystallites having lamellar stacking ((100) coherence length ∼30 nm) in the out-of-plane direction and highly favorable in-plane π-interactions in a slipped-stacked arrangement. Uninterrupted microstructural integrity (i.e., no face-on (010)-oriented crystallites) was found to be critical to achieving high mobilities. The excellent crystallinity of the C12-substituted semiconductor thin film was also evident in the observed crystal lattice vibrations (phonons) at 58 cm-1 in low-frequency Raman scattering. Two-dimensional micrometer-sized (∼1-3 μm), sharp-edged plate-like grains lying parallel with the substrate plane were observed. OFETs fabricated by the current small molecules showed excellent n-channel behavior in ambient with μe values reaching ∼0.9 cm2/(V·s), Ion/Ioff ∼ 107-108, and Von ≈ 0 V. Our study not only demonstrates one of the highest performing n-channel OFET devices reported under ambient conditions via solution processing but also elucidates significant relationships among chemical structures, molecular properties, self-assembly from solution into a thin film, and semiconducting thin-film properties. The design rationales presented herein may open up new avenues for the development of high-electron-mobility novel electron-deficient indenofluorene and short-axis substituted donor-acceptor π-architectures via alkyl chain engineering and interface engineering.

Dataset Information

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain links: Matrix for Solution-Processable n-Channel Field-effect Transistors.

Publications

Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain links: Matrix for Solution-Processable n-Channel Field-effect Transistors.

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