A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors

Hung Yang Chen; Mark Nikolka; Andrew Wadsworth; Wan Yue; Ada Onwubiko; Mingfei Xiao; Andrew J.P. White; Derya Baran; Henning Sirringhaus; Iain McCulloch

doi:10.1021/acs.macromol.7b00934

A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors

Hung Yang Chen^*, Mark Nikolka, Andrew Wadsworth, Wan Yue, Ada Onwubiko, Mingfei Xiao, Andrew J.P. White, Derya Baran, Henning Sirringhaus, Iain McCulloch

^*Corresponding author for this work

Physical Sciences and Engineering

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

52 Scopus citations

Abstract

A novel fused heterocycle-flanked diketopyrrolopyrrole (DPP) monomer, thieno[2,3-b]pyridine diketopyrrolopyrrole (TPDPP), was designed and synthesized. When copolymerized with 3,4-difluorothiophene using Stille coupling polymerization, the new polymer pTPDPP-TF possesses a highly planar conjugated polymer backbone due to the fused thieno[2,3-b]pyridine flanking unit that effectively alleviates the steric hindrance with both the central DPP core and the 3,4-difluorothiophene repeat unit. This new polymer exhibits a high electron affinity (EA) of -4.1 eV and was successfully utilized as an n-type polymer semiconductor for applications in organic field-effect transistors (OFETs) and all polymer solar cells. A promising n-type charge carrier mobility of 0.1 cm² V^-1 s^-1 was obtained in bottom-contact, top-gate OFETs, and a power conversion efficiency (PCE) of 2.72% with a high open-circuit voltage (V_OC) of 1.04 V was achieved for all polymer solar cells using PTB7-Th as the polymer donor.

Original language	English (US)
Pages (from-to)	71-79
Number of pages	9
Journal	Macromolecules
Volume	51
Issue number	1
DOIs	https://doi.org/10.1021/acs.macromol.7b00934
State	Published - Jan 9 2018

Bibliographical note

Funding Information:
The authors thank KAUST for financial support and acknowledge EC FP7 Project SC2 (610115) EC H2020 (643791), and EPSRC Projects EP/G037515/1 and EP/ M005143/1. Mingfei Xiao thanks the Cambridge Overseas Trust and Chinese Scholarship Council for PhD funding.

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/acs.macromol.7b00934

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Chen, H. Y., Nikolka, M., Wadsworth, A., Yue, W., Onwubiko, A., Xiao, M., White, A. J. P., Baran, D., Sirringhaus, H., & McCulloch, I. (2018). A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors. Macromolecules, 51(1), 71-79. https://doi.org/10.1021/acs.macromol.7b00934

@article{dd47fce83ee2451c8724745013d05f03,

title = "A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors",

abstract = "A novel fused heterocycle-flanked diketopyrrolopyrrole (DPP) monomer, thieno[2,3-b]pyridine diketopyrrolopyrrole (TPDPP), was designed and synthesized. When copolymerized with 3,4-difluorothiophene using Stille coupling polymerization, the new polymer pTPDPP-TF possesses a highly planar conjugated polymer backbone due to the fused thieno[2,3-b]pyridine flanking unit that effectively alleviates the steric hindrance with both the central DPP core and the 3,4-difluorothiophene repeat unit. This new polymer exhibits a high electron affinity (EA) of -4.1 eV and was successfully utilized as an n-type polymer semiconductor for applications in organic field-effect transistors (OFETs) and all polymer solar cells. A promising n-type charge carrier mobility of 0.1 cm2 V-1 s-1 was obtained in bottom-contact, top-gate OFETs, and a power conversion efficiency (PCE) of 2.72% with a high open-circuit voltage (VOC) of 1.04 V was achieved for all polymer solar cells using PTB7-Th as the polymer donor.",

author = "Chen, {Hung Yang} and Mark Nikolka and Andrew Wadsworth and Wan Yue and Ada Onwubiko and Mingfei Xiao and White, {Andrew J.P.} and Derya Baran and Henning Sirringhaus and Iain McCulloch",

note = "Funding Information: The authors thank KAUST for financial support and acknowledge EC FP7 Project SC2 (610115) EC H2020 (643791), and EPSRC Projects EP/G037515/1 and EP/ M005143/1. Mingfei Xiao thanks the Cambridge Overseas Trust and Chinese Scholarship Council for PhD funding. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2018",

month = jan,

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doi = "10.1021/acs.macromol.7b00934",

language = "English (US)",

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Chen, HY, Nikolka, M, Wadsworth, A, Yue, W, Onwubiko, A, Xiao, M, White, AJP, Baran, D, Sirringhaus, H & McCulloch, I 2018, 'A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors', Macromolecules, vol. 51, no. 1, pp. 71-79. https://doi.org/10.1021/acs.macromol.7b00934

TY - JOUR

T1 - A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors

AU - Chen, Hung Yang

AU - Nikolka, Mark

AU - Wadsworth, Andrew

AU - Yue, Wan

AU - Onwubiko, Ada

AU - Xiao, Mingfei

AU - White, Andrew J.P.

AU - Baran, Derya

AU - Sirringhaus, Henning

AU - McCulloch, Iain

N1 - Funding Information: The authors thank KAUST for financial support and acknowledge EC FP7 Project SC2 (610115) EC H2020 (643791), and EPSRC Projects EP/G037515/1 and EP/ M005143/1. Mingfei Xiao thanks the Cambridge Overseas Trust and Chinese Scholarship Council for PhD funding. Publisher Copyright: © 2017 American Chemical Society.

PY - 2018/1/9

Y1 - 2018/1/9

N2 - A novel fused heterocycle-flanked diketopyrrolopyrrole (DPP) monomer, thieno[2,3-b]pyridine diketopyrrolopyrrole (TPDPP), was designed and synthesized. When copolymerized with 3,4-difluorothiophene using Stille coupling polymerization, the new polymer pTPDPP-TF possesses a highly planar conjugated polymer backbone due to the fused thieno[2,3-b]pyridine flanking unit that effectively alleviates the steric hindrance with both the central DPP core and the 3,4-difluorothiophene repeat unit. This new polymer exhibits a high electron affinity (EA) of -4.1 eV and was successfully utilized as an n-type polymer semiconductor for applications in organic field-effect transistors (OFETs) and all polymer solar cells. A promising n-type charge carrier mobility of 0.1 cm2 V-1 s-1 was obtained in bottom-contact, top-gate OFETs, and a power conversion efficiency (PCE) of 2.72% with a high open-circuit voltage (VOC) of 1.04 V was achieved for all polymer solar cells using PTB7-Th as the polymer donor.

AB - A novel fused heterocycle-flanked diketopyrrolopyrrole (DPP) monomer, thieno[2,3-b]pyridine diketopyrrolopyrrole (TPDPP), was designed and synthesized. When copolymerized with 3,4-difluorothiophene using Stille coupling polymerization, the new polymer pTPDPP-TF possesses a highly planar conjugated polymer backbone due to the fused thieno[2,3-b]pyridine flanking unit that effectively alleviates the steric hindrance with both the central DPP core and the 3,4-difluorothiophene repeat unit. This new polymer exhibits a high electron affinity (EA) of -4.1 eV and was successfully utilized as an n-type polymer semiconductor for applications in organic field-effect transistors (OFETs) and all polymer solar cells. A promising n-type charge carrier mobility of 0.1 cm2 V-1 s-1 was obtained in bottom-contact, top-gate OFETs, and a power conversion efficiency (PCE) of 2.72% with a high open-circuit voltage (VOC) of 1.04 V was achieved for all polymer solar cells using PTB7-Th as the polymer donor.

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U2 - 10.1021/acs.macromol.7b00934

DO - 10.1021/acs.macromol.7b00934

M3 - Article

AN - SCOPUS:85040569629

SN - 0024-9297

VL - 51

SP - 71

EP - 79

JO - Macromolecules

JF - Macromolecules

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ER -

A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors

Abstract

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ASJC Scopus subject areas

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CCDC 1540600: Experimental Crystal Structure Determination : 3-bromothieno[2,3-b]pyridine-6-carbonitrile

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A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1540600: Experimental Crystal Structure Determination : 3-bromothieno[2,3-b]pyridine-6-carbonitrile

Cite this