Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors

Yujie Zhang; Linjing Tang; Huiliang Sun; Shaohua Ling; Kun Yang; Mohammad Afsar Uddin; Han Guo; Yumin Tang; Yang Wang; Kui Feng; Yongqiang Shi; Juqing Liu; Shiming Zhang; Han Young Woo; Xugang Guo

doi:10.1002/marc.201900394

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors

Yujie Zhang, Linjing Tang, Huiliang Sun, Shaohua Ling, Kun Yang, Mohammad Afsar Uddin, Han Guo, Yumin Tang, Yang Wang, Kui Feng, Yongqiang Shi, Juqing Liu, Shiming Zhang, Han Young Woo, Xugang Guo

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conformation, well-delocalized π-system, and favorable polymer chain packing, the optimal polymer in the series shows promising n-type charge transport with an electron mobility up to 0.48 cm² V⁻¹ s⁻¹ in OTFTs, which is among the highest values for the DPP-based n-type polymers reported to date. The results demonstrate that incorporating fused bithiophene imide oligomers into polymers can serve as a promising strategy for constructing high-performance n-type polymeric semiconductors.

Original language	English
Article number	1900394
Journal	Macromolecular Rapid Communications
Volume	40
Issue number	23
DOIs	https://doi.org/10.1002/marc.201900394
Publication status	Published - 2019 Dec 1

Bibliographical note

Funding Information:
Y.Z., L.T., and H.S. contributed equally to this work. S.Z. acknowledges the financial support from the National Key R&D Program of ?Strategic Advanced Electronic Materials? (2016YFB0401100) and the National Natural Science Foundation of China (61574077), as well as the Major Program of Natural Science Foundation of the Higher Education Institutions of Jiangsu Province, China (No.19KJA460005). X.G. is grateful to the National Natural Science Foundation of China (51573076) and Shenzhen Basic Research Fund (JYJ20170817105905899). H.S. acknowledges the National Natural Science Foundation of China (21801124). The authors thank Dr. Yinhua Yang at Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for the NMR characterization. The work was also supported by Center for Computational Science and Engineering of SUSTech.

Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

bithiophene imide
diketopyrrolopyrrole
n-type polymer semiconductors
organic thin-film transistors

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1002/marc.201900394

Cite this

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title = "Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors",

abstract = "Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conformation, well-delocalized π-system, and favorable polymer chain packing, the optimal polymer in the series shows promising n-type charge transport with an electron mobility up to 0.48 cm2 V−1 s−1 in OTFTs, which is among the highest values for the DPP-based n-type polymers reported to date. The results demonstrate that incorporating fused bithiophene imide oligomers into polymers can serve as a promising strategy for constructing high-performance n-type polymeric semiconductors.",

keywords = "bithiophene imide, diketopyrrolopyrrole, n-type polymer semiconductors, organic thin-film transistors",

author = "Yujie Zhang and Linjing Tang and Huiliang Sun and Shaohua Ling and Kun Yang and Uddin, {Mohammad Afsar} and Han Guo and Yumin Tang and Yang Wang and Kui Feng and Yongqiang Shi and Juqing Liu and Shiming Zhang and Woo, {Han Young} and Xugang Guo",

note = "Funding Information: Y.Z., L.T., and H.S. contributed equally to this work. S.Z. acknowledges the financial support from the National Key R&D Program of ?Strategic Advanced Electronic Materials? (2016YFB0401100) and the National Natural Science Foundation of China (61574077), as well as the Major Program of Natural Science Foundation of the Higher Education Institutions of Jiangsu Province, China (No.19KJA460005). X.G. is grateful to the National Natural Science Foundation of China (51573076) and Shenzhen Basic Research Fund (JYJ20170817105905899). H.S. acknowledges the National Natural Science Foundation of China (21801124). The authors thank Dr. Yinhua Yang at Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for the NMR characterization. The work was also supported by Center for Computational Science and Engineering of SUSTech. Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = dec,

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doi = "10.1002/marc.201900394",

language = "English",

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T1 - Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors

AU - Zhang, Yujie

AU - Tang, Linjing

AU - Sun, Huiliang

AU - Ling, Shaohua

AU - Yang, Kun

AU - Uddin, Mohammad Afsar

AU - Guo, Han

AU - Tang, Yumin

AU - Wang, Yang

AU - Feng, Kui

AU - Shi, Yongqiang

AU - Liu, Juqing

AU - Zhang, Shiming

AU - Woo, Han Young

AU - Guo, Xugang

N1 - Funding Information: Y.Z., L.T., and H.S. contributed equally to this work. S.Z. acknowledges the financial support from the National Key R&D Program of ?Strategic Advanced Electronic Materials? (2016YFB0401100) and the National Natural Science Foundation of China (61574077), as well as the Major Program of Natural Science Foundation of the Higher Education Institutions of Jiangsu Province, China (No.19KJA460005). X.G. is grateful to the National Natural Science Foundation of China (51573076) and Shenzhen Basic Research Fund (JYJ20170817105905899). H.S. acknowledges the National Natural Science Foundation of China (21801124). The authors thank Dr. Yinhua Yang at Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for the NMR characterization. The work was also supported by Center for Computational Science and Engineering of SUSTech. Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/12/1

Y1 - 2019/12/1

N2 - Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conformation, well-delocalized π-system, and favorable polymer chain packing, the optimal polymer in the series shows promising n-type charge transport with an electron mobility up to 0.48 cm2 V−1 s−1 in OTFTs, which is among the highest values for the DPP-based n-type polymers reported to date. The results demonstrate that incorporating fused bithiophene imide oligomers into polymers can serve as a promising strategy for constructing high-performance n-type polymeric semiconductors.

AB - Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conformation, well-delocalized π-system, and favorable polymer chain packing, the optimal polymer in the series shows promising n-type charge transport with an electron mobility up to 0.48 cm2 V−1 s−1 in OTFTs, which is among the highest values for the DPP-based n-type polymers reported to date. The results demonstrate that incorporating fused bithiophene imide oligomers into polymers can serve as a promising strategy for constructing high-performance n-type polymeric semiconductors.

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DO - 10.1002/marc.201900394

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Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n-Type Thin-Film Transistors

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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