TY - JOUR
T1 - Stretchable Semiconducting Polymers with Hydrogen-Bonding-Capable Conjugation Breakers
T2 - Synthesis and Application in Organic Thin-Film Transistors
AU - Kim, Aesun
AU - Ahn, Yooseong
AU - Li, Wenhao
AU - Park, Su Hong
AU - Cho, Min Ju
AU - Choi, Dong Hoon
AU - Yang, Hoichang
N1 - Publisher Copyright:
© 2023 American Chemical Society
PY - 2023/12/20
Y1 - 2023/12/20
N2 - Diketopyrrolopyrrole (DPP)-based conjugated copolymers are important organic semiconductors for applications in high-efficiency organic thin-film transistors (OTFTs). However, the direct application of these polymers with rigid backbones in stretchable devices has limitations. In this study, we designed and synthesized three kinds of DPPBT-based copolymers, DPPBT-A1, DPPBT-A3, and DPPBT-A5, which have amide-coupled alkylene conjugation breakers capable of hydrogen bonding. Linkers with different segment lengths were copolymerized with DPP and bithiophene (BT) backbone units. A DPP-based copolymer with alternating BT moieties, DPPBT, was synthesized as a reference fully conjugated copolymer. The synthesized polymers with freely rotational backbone linkers have sufficient flexibility to develop ordered phase domains, even in thin films, in comparison to the reference copolymer. However, the introduction of the conjugation breakers, which disconnect the intramolecular π-π overlapping, tends to decrease the hole mobility (μ) from 0.76 to 0.20 cm2 V-1 s-1 in the corresponding OTFT devices. The TFT fabricated using DPPBT-A3 showed a mobility of 0.50 cm2 V-1 s-1, and the mobility value did not show a significant change even when elongated by more than 50%. Therefore, the molecular design strategy of introducing amide-coupled alkylene conjugation breakers into conjugated polymer chains can contribute significantly to the development of high-mobility stretchable conjugated polymers in future.
AB - Diketopyrrolopyrrole (DPP)-based conjugated copolymers are important organic semiconductors for applications in high-efficiency organic thin-film transistors (OTFTs). However, the direct application of these polymers with rigid backbones in stretchable devices has limitations. In this study, we designed and synthesized three kinds of DPPBT-based copolymers, DPPBT-A1, DPPBT-A3, and DPPBT-A5, which have amide-coupled alkylene conjugation breakers capable of hydrogen bonding. Linkers with different segment lengths were copolymerized with DPP and bithiophene (BT) backbone units. A DPP-based copolymer with alternating BT moieties, DPPBT, was synthesized as a reference fully conjugated copolymer. The synthesized polymers with freely rotational backbone linkers have sufficient flexibility to develop ordered phase domains, even in thin films, in comparison to the reference copolymer. However, the introduction of the conjugation breakers, which disconnect the intramolecular π-π overlapping, tends to decrease the hole mobility (μ) from 0.76 to 0.20 cm2 V-1 s-1 in the corresponding OTFT devices. The TFT fabricated using DPPBT-A3 showed a mobility of 0.50 cm2 V-1 s-1, and the mobility value did not show a significant change even when elongated by more than 50%. Therefore, the molecular design strategy of introducing amide-coupled alkylene conjugation breakers into conjugated polymer chains can contribute significantly to the development of high-mobility stretchable conjugated polymers in future.
KW - conjugation breaker
KW - hydrogen bonding
KW - organic thin film transistor
KW - semiconducting polymer
KW - stretchability
UR - http://www.scopus.com/inward/record.url?scp=85180104877&partnerID=8YFLogxK
U2 - 10.1021/acsami.3c12057
DO - 10.1021/acsami.3c12057
M3 - Article
C2 - 38064280
AN - SCOPUS:85180104877
SN - 1944-8244
VL - 15
SP - 58663
EP - 58672
JO - ACS applied materials & interfaces
JF - ACS applied materials & interfaces
IS - 50
ER -