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Synthesis of Bio-based Block Copolymers with Conjugated Segments and Their Applications in Electronic Devices

徐, 立哲 北海道大学

2021.09.24

概要

In this dissertation, bio-based and stretchable semiconducting polymers through elegant design of conjugated block copolymers (BCPs) with linear and branched soft segments of poly(δ-decanolactone) (PDL) were developed. PDL was chose as the green and soft building block in the target BCPs since it is a bio-based soft polymer with a metal-free and living ring-opening polymerization process. Conjugated-insulating BCPs were prepared through Cu-catalyzed azido–alkyne click reaction (CuAAC) between azido-functionalized PDLs and typical conjugated polymers with alkyne functional group including poly(3-hexylthiophene) (P3HT) and poly(9,9-di-n-hexyl-2,7-fluorene) (PF). Thermal, mechanical and electronic properties were systematically studied for the stretchable electronic applications. In chapter 2, I propose soft-hard-soft type triblock BCPs with poly(3-hexylthiophene) (P3HT) and branched PDL segments to enhance stretchability of BCP without sacrificing charge mobility. The BCPs with AB, AB2, B2AB2 and B3AB3 structure (A: P3HT, B: PDL) exhibit competitive hole mobility of 0.088, 0.085, 0.089 and 0.045 cm2 V-1 s-1, respectively. Interestingly, stretchability of the BCPs increases by introducing soft-hard-soft structure and the branched soft segments, as investigated by optical microscopy (OM) and amplitude modulation-frequency modulation atomic force microscopy (AM-FM AFM). This can be attributed to more random phase separation and smaller P3HT crystallites of the branched triblock BCPs. Finally, OFETs with the stretched and transferred semiconducting layer of the BCPs were fabricated and the B3AB3 device shows the highest mobility retention among all the synthesized BCPs (72%-75%) under 100% strain, and 71-75% mobility retention after 500 stretch-release cycles at 50% strain. In chapter 3, poly(9,9-di-n-hexyl-2,7-fluorene)-block-poly(δ-decanolactone)s (PF-b-PDLs) with AB, AB2 and AB3 structure (A: PF, B: PDL) were designed as stretchable charge-storage layer of organic field-effect transistor (OFET) memory. The BCP thin films exhibit extraordinary stretchability with no cracks observed by optical microscopy (OM) under up to 100% strain owing to the incorporated PDL soft segments. Meanwhile, the trapping density of the electret film of the branched polymers is boosted by the tailored phase separation and higher crystallinity of the BCPs. Quantitative analysis of the polymer thin films on the atomic force microscopic (AFM) images was performed to correlate thin film morphology with memory device performance. As a result, PF-b-PDL3 device exhibits the largest memory window (102 V) and the highest memory ratio (3.5 × 104). OFET memories made by the stretched and transferred BCPs can retain their memory performance under up to 100% strain, and the PF-b-PDL3 device can endure 500 stretch-release cycles at 50% strain with 84% memory window retention. These results highlight the importance of architecture design on modulating electronic properties and stretchability of conjugated BCP using bio-based and soft polymer as building blocks.

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