High-Mobility Pyrene-Based Semiconductor for Organic Thin-Film Transistors

Abstract

Numerous conjugated oligoacenes and polythiophenes are being heavily studied in the search for high-mobility organic semiconductors. Although many researchers have designed fused aromatic compounds as organic semiconductors for organic thin-film transistors (OTFTs), pyrene-based organic semiconductors with high mobilities and on-off current ratios have not yet been reported. Here, we introduce a new pyrene-based p-type organic semiconductor showing liquid crystal behavior. The thin film characteristics of this material are investigated by varying the substrate temperature during the deposition and the gate dielectric condition using the surface modification with a self-assembled monolayer, and systematically studied in correlation with the performances of transistor devices with this compound. OTFT fabricated under the optimum deposition conditions of this compound, namely, 1,6-bis(5'-octyl-2,2'-bithiophen-5-yl)pyrene (BOBTP) shows a high-performance transistor behavior with a field-effect mobility of 2.1 cm(2) V(-1) s(-1) and an on-off current ratio of 7.6 × 10(6) and enhanced long-term stability compared to the pentacene thin-film transistor.

Development of Pyrene Derivatives as Promising n‐Type Semiconductors: Synthesis, Structural and Spectral Properties

“…The most active sites are on 1‐, 3‐, 6‐ and 8‐positions and easy for electrophilic aromatic substitution reactions. Most derivatives are mono‐, 1,6‐, and 1‐, 3‐, 6‐ and 8‐position substituted, while 1,8‐position derivatives are rarely reported.…”

Diaza-analogs of benzopyrene and perylene containing thienyl and 4-(phenylamino)phenyl groups: Synthesis, characterization, optical and electrochemical properties

“…The 1 H and 13 C NMR spectra were recorded on a Bruker AV-400 spectrometer. Melting points were determined with a Kofler apparatus.…”

“…Compounds 5 -2 h). The compounds were characterized by elemental analysis, IR, 1 H NMR, 13 C NMR and mass spectrometry. Crystals of heterocycles 8b, 9b we investigated by X-ray analysis.…”

Organic Semiconductors for Field-Effect Transistors

“…Because of the nonplanar structure, the tetrasubstituted-derivatives using pyrene as core including 33 and 34 tend to afford low mobilities [90][91][92]. However, the derivatives 35 and 36 using pyrene as an end-capped group and linear pyrene derivative 37 showed high mobilities [93][94][95]. For example, thin film transistors based on derivatives 35, 36, and 37 exhibited mobilities of 0.21, 0.11, and 2.1 cm 2 V −1 s −1 , respectively.…”