Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors

Abstract

Constructing planar, rigid, and high electronically delocalized p-conjugated molecular system is the most basic requirements of obtaining high-performance polymeric semiconductors for organic field-effect transistors (OFETs). In this regard, diarylethylene (DAE)-based polymers show great potential because many substantive progresses related to polymer field-effect transistors had been achieved from the kind of polymer materials in recent years. In the brief review, series of DAE-based polymer are highlighted, based on which several design strategies have been summarized by the way of comparative research method. These strategies have important guiding significance not only for further developing new DAEbased and other polymeric semiconductors for OFETs but also for developing specific polymeric semiconductors for other organic electronics, such as organic photovoltaics and organic light-emitting diodes. V C 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 585-603 KEYWORDS: design strategies; diarylethylene; organic fieldeffect transistors; polymeric semiconductors; synthesis INTRODUCTION Solution-processable semiconducting polymers have attracted great interest during the recent decades because of the traits of excellent film forming property, and adjustable chemical structure and property, as well as the potential to fabricate various lightweight and flexible electronic devices such as organic field-effect transistors (OFETs) via cost-effective large-area graphic printing processes.

Formation of trans-Poly(thienylenevinylene) Thin Films by Solid-State Thermal Isomerization

“…The charge carrier mobility of polymers with trans -vinylene and thiophene-derived repeating units ( trans -poly­(thienylenevinylene)­s; PTVs) has been reported to be the highest among π-conjugated polymers. − However, trans -PTVs have strong interchain π–π interactions due to their planar structure, which limits their solubility. , The more twisted configuration of the cis -vinylene units tends to result in less optimized interchain stacking and thus higher solubility . We have demonstrated that thin films of cis -poly­( p -phenylenevinylene)­s undergo cis-to-trans isomerization under UV irradiation (Figure e). − A similar isomerization of cis -vinylene may provide a direct and efficient route to the fabrication of trans -PTVs thin films (Figure f).…”

Tuning Backbone Planarity in Thiadiazolobenzotriazole–Bis(thienothiophenyl)ethylene Copolymers for Organic Field-Effect Transistors

“…In 2011, Grimsdale and co-workers substituted one of the S atoms in BBT by an N atom, allowing the introduction of a solubilizing alkyl chain and producing a new acceptor unit, [1,2,5]­thiadiazolo­[3,4- f ]­benzo­[1,2,3]­triazole (TBZ) . Since then, TBZ has been used for the design of many D–A conjugated polymers. − On the other hand, a variety of donor units have been studied, and it was shown that diarylethylene-based (DAE) donor units are suitable for high mobility polymers . This signifies the importance of the backbone planarity, which enables the formation of close π–π stacking and crystalline grains in thin films. − Examples of extensively studied DAE units are dithienyl­ethylene (DTE), − diseleno­phenylethylene (DSE), ,,− and dithieno­[3,2- b ]­thio­phenylethylene (DTTE). ,,, In particular, DTTE forms a more extended π-conjugated core in the polymer backbone compared to DTE.…”

“…36−41 On the other hand, a variety of donor units have been studied, and it was shown that diarylethylene-based (DAE) donor units are suitable for high mobility polymers. 42 This signifies the importance of the backbone planarity, which enables the formation of close π−π stacking and crystalline grains in thin films. 43−45 Examples of extensively studied DAE units are dithienylethylene (DTE), 46−51 diselenophenylethylene (DSE), 9,20,50−52 and dithieno [3,2-b]thiophenylethylene (DTTE).…”

Synthesis of a 1,2-Dithienylethene-Containing Donor-Acceptor Polymer via Palladium-Catalyzed Direct Arylation Polymerization (DArP)

“…In this study, we examined the synthesis of a D-A polymer with 1,2-dithienylethene (DTE) as donor units; poly( 1 - alt - 2 ) in Scheme 1 . DTE-based D-A polymers, such as poly( 1 - alt - 2 ), have been prepared by Migita–Kosugi–Stille cross-coupling polymerization and have proven to be competent compounds in OFETs [ 21 , 22 , 23 ]; however, their synthesis via DArP has been poorly successful [ 24 ]. This is probably due to the existence of plural C–H bonds in DTE.…”