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Materials 2013, 6(3), 1061-1071; doi:10.3390/ma6031061

Quinacridone-Diketopyrrolopyrrole-Based Polymers for Organic Field-Effect Transistors

1,2,*  and 1,2
1 Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan 2 RIKEN Center for Emergent Matter Science, Wako, Saitama 351-0198, Japan
* Author to whom correspondence should be addressed.
Received: 29 January 2013 / Revised: 7 March 2013 / Accepted: 8 March 2013 / Published: 18 March 2013
(This article belongs to the Special Issue Conjugated Polymers)
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Incorporation of pigment or dye molecules as building units is of great interest in the development of semiconducting polymers, due to their strong intermolecular interactions arising from the strong local dipoles in the unit structure, which would facilitate the charge transport property. In this paper, semiconducting polymers based on well-known pigments, namely, quinacridone and diketopyrrolopyrrole, are synthesized and characterized. The π-stacking distances are found to be 3.5–3.8 Å, which is fairly narrow for semiconducting polymers, indicating that they possess strong intermolecular interactions. Interestingly, polymer orientation is influenced by the composition of alkyl side chains. While the edge-on orientation is observed when the linear alkyl groups are introduced for all the side chains, the face-on orientation is observed when the branched alkyl groups are introduced either in the quinacridone or diketopyrrolopyrrole unit. It is found that the electronic structure of the present polymers is mostly affected by that of the diketopyrrolopyrrole unit, as evidenced by the absorption spectra and computation. Although the field-effect mobility of the polymers is modest, i.e., in the order of 10−4–10−3 cm2/Vs, these findings could be important information for the development of semiconducting polymers.
Keywords: semiconducting polymers; pigment; quinacridone; diketopyrrolopyrrole; organic field-effect transistors semiconducting polymers; pigment; quinacridone; diketopyrrolopyrrole; organic field-effect transistors
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Akita, M.; Osaka, I.; Takimiya, K. Quinacridone-Diketopyrrolopyrrole-Based Polymers for Organic Field-Effect Transistors. Materials 2013, 6, 1061-1071.

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