Abstract

High-performance n-type organic semiconducting polymers are key components of next-generation organic electronics. Here, we designed and synthesized two electron deficient organic polymers composed of benzodifurandione-based oligo (p-phenylenevinylene) (BDOPV) and benzothiadiazole by Stille coupling polycondensation. BDOPV-benzothiadiazole-based copolymer (PBDOPV-BTT) possesses a D-A1-D-A2 type backbone with intramolecular charge–transfer interactions, while PBDOPV-BTTz is an all-acceptor polymer. The former has a higher molecular weight (Mn) of 109.7 kg∙mol−1 than the latter (Mn = 20.2 kg∙mol−1). The structural difference of these polymers was confirmed by the optical absorption spectra. PBDOPV-BTT showed a more bathochromically shifted absorption spectrum than PBDOPV-BTTz. The longer wavelength absorption of PBDOPV-BTT was due to the intramolecular charge transfer. Therefore, PBDOPV-BTT had a narrower band gap than PBDOPV-BTTz. However, this feature was not reflected by the lowest unoccupied molecular orbital (LUMO) levels. Both polymers displayed almost the same LUMO level of −3.8 eV. Accuracy of this observation was cross-verified by density functional theory (DFT) calculations. The electron-transporting properties were investigated by thin film transistors. PBDOPV-BTT showed an electron mobility (μe) of 1.02 × 10−2 cm2 V−1 s−1 under the optimized annealing conditions. PBDOPV-BTTz exhibited poorer transistor performances with the optimized μe of 9.54 × 10−6 cm2 V−1 s−1. Finally, the grazing-incidence wide angle X-ray scattering (GIWAXS) measurements of both polymer films revealed the higher crystallinity of PBDOPV-BTT with the edge-on orientation.

Highlights

  • Organic semiconducting polymers are promising candidates for the construction of low-cost and flexible electronic devices [1–11]

  • We report the synthesis of the basedoligo(p-phenylenevinylene) oligo(p-phenylenevinylene) (BDOPV) and benzothiadiazole have not yet been reported

  • We report the synthesis of the BDOPV-benzothiadiazole-basedcopolymer copolymer (PBDOPV-BTT)

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Summary

Introduction

Organic semiconducting polymers are promising candidates for the construction of low-cost and flexible electronic devices [1–11]. Ambipolar semiconducting polymers are among the most common organic semiconductors [12] As they transfer both holes and electrons in thin film electronic devices, low-power consumption complementary devices such as photovoltaics and thermoelectrics have not been achieved. Tailoring of molecular design of organic semiconductors or optimization of device architectures alleviate this problem The former is a synthetic approach, and synthetic chemists have devoted significant efforts to produce p-type semiconducting polymers with hole mobilities of over 1 cm[2] V−1 s−1. The use of common organic dyes, such as diketopyrrolopyrrole (DPP) and isoindigo (IID), is effective for producing high-mobility p-type semiconducting polymers [13–21]. In order to block hole injection and transport, behind the corresponding p-type counter polymers. Electron transporting properties and thin film all-acceptor copolymer (PBDOPV-BTTz).

Materials and Synthesis
General Measurements
Thin Film Transistors
Synthesis
Optical and Electrochemical
Thin Film Morphology
Full Text
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