Enabling high-mobility, ambipolar charge-transport in a DPP-benzotriazole copolymer by side-chain engineering

In this article we discuss the synthesis of four new low band-gap co-polymers based on the diketopyrrolopyrrole (DPP) and benzotriazole (BTZ) monomer unit. We demonstrate that the BTZ unit allows for additional solubilizing side-chains on the co-monomer and show that the introduction of a linear sid...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2015-01, Vol.6 (12), p.6949-6960
Main Authors: Gruber, Mathias, Jung, Seok-Heon, Schott, Sam, Venkateshvaran, Deepak, Kronemeijer, Auke Jisk, Andreasen, Jens Wenzel, McNeill, Christopher R, Wong, Wallace W H, Shahid, Munazza, Heeney, Martin, Lee, Jin-Kyun, Sirringhaus, Henning
Format: Article
Language:English
Subjects:
Benzotriazole
Chain branching
Chain mobility
Chains
Chains (polymeric)
Chemistry
Copolymers
Design engineering
Polymers
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Summary:In this article we discuss the synthesis of four new low band-gap co-polymers based on the diketopyrrolopyrrole (DPP) and benzotriazole (BTZ) monomer unit. We demonstrate that the BTZ unit allows for additional solubilizing side-chains on the co-monomer and show that the introduction of a linear side-chain on the DPP-unit leads to an increase in thin-film order and charge-carrier mobility if a sufficiently solubilizing, branched, side chain is attached to the BTZ. We compare two different synthetic routes, direct arylation and Suzuki-polycondensation, by a direct comparison of polymers obtained the two routes and show that direct arylation produces polymers with lower electrical performance which we attribute to a higher density of chain Furthermore we demonstrate that a polymer utilizing this design motif and synthesized Suzuki-polycondensation ( ) exhibits exceptionally high and near balanced average electron and hole mobilities >2 cm V s which are among the highest, robustly extracted mobility values reported for DPP copolymers in a top-gate configuration to date. Our results demonstrate clearly that linear side chain substitution of the DPP unit together with co-monomers that allow for the use of sufficiently long or branched solubilizing side chains can be an attractive design motif for solution processable, high mobility DPP copolymers.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc01326g