Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells

Huiliang Sun; Bin Liu; Chang Woo Koh; Yujie Zhang; Jianhua Chen; Yang Wang; Peng Chen; Bao Tu; Maoyao Su; Hang Wang; Yumin Tang; Yongqiang Shi; Han Young Woo; Xugang Guo

doi:10.1002/adfm.201903970

Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells

Huiliang Sun, Bin Liu, Chang Woo Koh, Yujie Zhang, Jianhua Chen, Yang Wang, Peng Chen, Bao Tu, Maoyao Su, Hang Wang, Yumin Tang, Yongqiang Shi, Han Young Woo, Xugang Guo

Department of Chemistry

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

51 Citations (Scopus)

Abstract

The aggregation/crystallinity of classic n-type terpolymers based on naphthalene diimide and perylene diimide is challenging to tune due to their rigid and extended cores, leading to suboptimal film morphology. A new strategy for developing high-performance n-type terpolymers by incorporating imide-functionalized heteroarenes is reported here to balance crystallinity and miscibility without sacrificing charge carrier mobilities. The introduction of thienopyrroledione (TPD) into the copolymer f-BTI2-FT results in a series of terpolymers BTI2-xTPD having distinct TPD content. The irregular backbone reduces crystallinity, yielding improved miscibility with the polymer donor. More importantly, TPD triggers noncovalent S⋯O interactions, increasing backbone planarity and in-chain charge transport. Such interactions also promote face-on polymer packing. As a result, all-polymer solar cells (all-PSCs) based on BTI2-30TPD achieve an optimal power conversion efficiency (PCE) of 8.28% with a small energy loss (0.53 eV). This efficiency is substantially higher than that of TPD (4.4%) or a BTI2-based copolymer (6.8%) and is also the highest for additive-free all-PSCs based on a terpolymer acceptor. Moreover, the BTI2-30TPD cell exhibits excellent stability with the PCE retaining 90% of its initial value after 400 h of aging. The results demonstrate that random polymerization using imide-functionalized heteroarenes is a powerful approach to develop terpolymer acceptors toward efficient and stable all-polymer solar cell PSCs.

Original language	English
Article number	1903970
Journal	Advanced Functional Materials
Volume	29
Issue number	42
DOIs	https://doi.org/10.1002/adfm.201903970
Publication status	Published - 2019 Oct 1

Bibliographical note

Funding Information:
H.S. and B.L. contributed equally to this work. The authors thank NSFC (21774055, 51573076, and 21801124), Shenzhen Basic Research Fund ((JCYJ20170817105905899), and Shenzhen Peacock Plan Project (KQTD20140630110339343). H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911 and 2019R1A6A1A11044070). The authors thank Dr. Yinhua Yang at the Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for NMR measurement. Our work was also supported by Center for Computational Science and Engineering of SUSTech.

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

Keywords

all-polymer solar cells
imide-functionalized heteroarenes
n-type polymers
organic electronics
random terpolymers

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Chemistry(all)
Materials Science(all)
Electrochemistry
Biomaterials

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10.1002/adfm.201903970

Cite this

Sun, H., Liu, B., Koh, C. W., Zhang, Y., Chen, J., Wang, Y., Chen, P., Tu, B., Su, M., Wang, H., Tang, Y., Shi, Y., Woo, H. Y., & Guo, X. (2019). Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells. Advanced Functional Materials, 29(42), Article 1903970. https://doi.org/10.1002/adfm.201903970

Sun, H, Liu, B, Koh, CW, Zhang, Y, Chen, J, Wang, Y, Chen, P, Tu, B, Su, M, Wang, H, Tang, Y, Shi, Y, Woo, HY & Guo, X 2019, 'Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells', Advanced Functional Materials, vol. 29, no. 42, 1903970. https://doi.org/10.1002/adfm.201903970

@article{89e88c3d9a0f4a14b1538a0e22aee642,

title = "Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells",

abstract = "The aggregation/crystallinity of classic n-type terpolymers based on naphthalene diimide and perylene diimide is challenging to tune due to their rigid and extended cores, leading to suboptimal film morphology. A new strategy for developing high-performance n-type terpolymers by incorporating imide-functionalized heteroarenes is reported here to balance crystallinity and miscibility without sacrificing charge carrier mobilities. The introduction of thienopyrroledione (TPD) into the copolymer f-BTI2-FT results in a series of terpolymers BTI2-xTPD having distinct TPD content. The irregular backbone reduces crystallinity, yielding improved miscibility with the polymer donor. More importantly, TPD triggers noncovalent S⋯O interactions, increasing backbone planarity and in-chain charge transport. Such interactions also promote face-on polymer packing. As a result, all-polymer solar cells (all-PSCs) based on BTI2-30TPD achieve an optimal power conversion efficiency (PCE) of 8.28% with a small energy loss (0.53 eV). This efficiency is substantially higher than that of TPD (4.4%) or a BTI2-based copolymer (6.8%) and is also the highest for additive-free all-PSCs based on a terpolymer acceptor. Moreover, the BTI2-30TPD cell exhibits excellent stability with the PCE retaining 90% of its initial value after 400 h of aging. The results demonstrate that random polymerization using imide-functionalized heteroarenes is a powerful approach to develop terpolymer acceptors toward efficient and stable all-polymer solar cell PSCs.",

keywords = "all-polymer solar cells, imide-functionalized heteroarenes, n-type polymers, organic electronics, random terpolymers",

author = "Huiliang Sun and Bin Liu and Koh, {Chang Woo} and Yujie Zhang and Jianhua Chen and Yang Wang and Peng Chen and Bao Tu and Maoyao Su and Hang Wang and Yumin Tang and Yongqiang Shi and Woo, {Han Young} and Xugang Guo",

note = "Funding Information: H.S. and B.L. contributed equally to this work. The authors thank NSFC (21774055, 51573076, and 21801124), Shenzhen Basic Research Fund ((JCYJ20170817105905899), and Shenzhen Peacock Plan Project (KQTD20140630110339343). H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911 and 2019R1A6A1A11044070). The authors thank Dr. Yinhua Yang at the Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for NMR measurement. Our 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 = oct,

day = "1",

doi = "10.1002/adfm.201903970",

language = "English",

volume = "29",

journal = "Advanced Functional Materials",

issn = "1616-301X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells

AU - Sun, Huiliang

AU - Liu, Bin

AU - Koh, Chang Woo

AU - Zhang, Yujie

AU - Chen, Jianhua

AU - Wang, Yang

AU - Chen, Peng

AU - Tu, Bao

AU - Su, Maoyao

AU - Wang, Hang

AU - Tang, Yumin

AU - Shi, Yongqiang

AU - Woo, Han Young

AU - Guo, Xugang

N1 - Funding Information: H.S. and B.L. contributed equally to this work. The authors thank NSFC (21774055, 51573076, and 21801124), Shenzhen Basic Research Fund ((JCYJ20170817105905899), and Shenzhen Peacock Plan Project (KQTD20140630110339343). H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911 and 2019R1A6A1A11044070). The authors thank Dr. Yinhua Yang at the Materials Characterization and Preparation Center, Southern University of Science and Technology (SUSTech) for NMR measurement. Our work was also supported by Center for Computational Science and Engineering of SUSTech. Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/10/1

Y1 - 2019/10/1

N2 - The aggregation/crystallinity of classic n-type terpolymers based on naphthalene diimide and perylene diimide is challenging to tune due to their rigid and extended cores, leading to suboptimal film morphology. A new strategy for developing high-performance n-type terpolymers by incorporating imide-functionalized heteroarenes is reported here to balance crystallinity and miscibility without sacrificing charge carrier mobilities. The introduction of thienopyrroledione (TPD) into the copolymer f-BTI2-FT results in a series of terpolymers BTI2-xTPD having distinct TPD content. The irregular backbone reduces crystallinity, yielding improved miscibility with the polymer donor. More importantly, TPD triggers noncovalent S⋯O interactions, increasing backbone planarity and in-chain charge transport. Such interactions also promote face-on polymer packing. As a result, all-polymer solar cells (all-PSCs) based on BTI2-30TPD achieve an optimal power conversion efficiency (PCE) of 8.28% with a small energy loss (0.53 eV). This efficiency is substantially higher than that of TPD (4.4%) or a BTI2-based copolymer (6.8%) and is also the highest for additive-free all-PSCs based on a terpolymer acceptor. Moreover, the BTI2-30TPD cell exhibits excellent stability with the PCE retaining 90% of its initial value after 400 h of aging. The results demonstrate that random polymerization using imide-functionalized heteroarenes is a powerful approach to develop terpolymer acceptors toward efficient and stable all-polymer solar cell PSCs.

AB - The aggregation/crystallinity of classic n-type terpolymers based on naphthalene diimide and perylene diimide is challenging to tune due to their rigid and extended cores, leading to suboptimal film morphology. A new strategy for developing high-performance n-type terpolymers by incorporating imide-functionalized heteroarenes is reported here to balance crystallinity and miscibility without sacrificing charge carrier mobilities. The introduction of thienopyrroledione (TPD) into the copolymer f-BTI2-FT results in a series of terpolymers BTI2-xTPD having distinct TPD content. The irregular backbone reduces crystallinity, yielding improved miscibility with the polymer donor. More importantly, TPD triggers noncovalent S⋯O interactions, increasing backbone planarity and in-chain charge transport. Such interactions also promote face-on polymer packing. As a result, all-polymer solar cells (all-PSCs) based on BTI2-30TPD achieve an optimal power conversion efficiency (PCE) of 8.28% with a small energy loss (0.53 eV). This efficiency is substantially higher than that of TPD (4.4%) or a BTI2-based copolymer (6.8%) and is also the highest for additive-free all-PSCs based on a terpolymer acceptor. Moreover, the BTI2-30TPD cell exhibits excellent stability with the PCE retaining 90% of its initial value after 400 h of aging. The results demonstrate that random polymerization using imide-functionalized heteroarenes is a powerful approach to develop terpolymer acceptors toward efficient and stable all-polymer solar cell PSCs.

KW - all-polymer solar cells

KW - imide-functionalized heteroarenes

KW - n-type polymers

KW - organic electronics

KW - random terpolymers

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U2 - 10.1002/adfm.201903970

DO - 10.1002/adfm.201903970

M3 - Article

AN - SCOPUS:85070763992

SN - 1616-301X

VL - 29

JO - Advanced Functional Materials

JF - Advanced Functional Materials

IS - 42

M1 - 1903970

ER -

Imide-Functionalized Heteroarene-Based n-Type Terpolymers Incorporating Intramolecular Noncovalent Sulfur∙∙∙Oxygen Interactions for Additive-Free All-Polymer Solar Cells

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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