1,4-Di(3-alkoxy-2-thienyl)-2,5-difluorophenylene: A Building Block Enabling High-Performance Polymer Semiconductors with Increased Open-Circuit Voltages

Jianhua Chen, Zhenglong Yan, Linjing Tang, Mohammad Afsar Uddin, Jianwei Yu, Xin Zhou, Kun Yang, Yumin Tang, Tae Joo Shin, Han Young Woo, Xugang Guo

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A new building block, 1,4-di(3-alkoxy-2-thienyl)-2,5-difluorophenylene (DOTFP) with several desirable features such as high backbone planarity, suitably lying highest occupied molecular orbital (HOMO), and good solubility, was developed by inserting an electron-deficient difluorophenylene into the 3,3′-dialkoxy-2,2′-bithiophene (BTOR) unit. Three regioregular D-A1-D-A2 type polymers based on DOTFP and benzothiadiazole (BT) derivatives were synthesized and characterized by comparing with a D-A type BTOR-based polymer. The content of highly electron-rich alkoxythiophene is reduced by half in the DOTFP-based polymers versus that of the BTOR-based polymer analogue, which results in a deeper HOMO level and benefits high open-circuit voltage (Voc) in polymer solar cells (PSCs). Consequently, the DOTFP-ffBT-based solar cells exhibited a significantly improved power conversion efficiency (PCE) of 8.7% and an increased Voc of 0.84 V compared to the BTOR-ffBT-based solar cells with a PCE of 2.6% and a Voc of 0.49 V. Additionally, the DOTFP-based polymers showed improved charge transport properties and film morphology than the BTOR-based polymer BTOR-ffBT, resulting in simultaneous enhancement of the short-circuit current (Jsc) and fill factor (FF) in PSCs. These results demonstrate the great promise of the DOTFP building block for the construction of high-performance photovoltaic polymer semiconductors with increased Vocs.

Original languageEnglish
Pages (from-to)5352-5363
Number of pages12
JournalMacromolecules
Volume51
Issue number14
DOIs
Publication statusPublished - 2018 Jul 24

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Open circuit voltage
Polymers
Semiconductor materials
Molecular orbitals
Conversion efficiency
Solar cells
Electrons
alkoxyl radical
Short circuit currents
Transport properties
Charge transfer
Solubility
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

1,4-Di(3-alkoxy-2-thienyl)-2,5-difluorophenylene : A Building Block Enabling High-Performance Polymer Semiconductors with Increased Open-Circuit Voltages. / Chen, Jianhua; Yan, Zhenglong; Tang, Linjing; Uddin, Mohammad Afsar; Yu, Jianwei; Zhou, Xin; Yang, Kun; Tang, Yumin; Shin, Tae Joo; Woo, Han Young; Guo, Xugang.

In: Macromolecules, Vol. 51, No. 14, 24.07.2018, p. 5352-5363.

Research output: Contribution to journalArticle

Chen, Jianhua ; Yan, Zhenglong ; Tang, Linjing ; Uddin, Mohammad Afsar ; Yu, Jianwei ; Zhou, Xin ; Yang, Kun ; Tang, Yumin ; Shin, Tae Joo ; Woo, Han Young ; Guo, Xugang. / 1,4-Di(3-alkoxy-2-thienyl)-2,5-difluorophenylene : A Building Block Enabling High-Performance Polymer Semiconductors with Increased Open-Circuit Voltages. In: Macromolecules. 2018 ; Vol. 51, No. 14. pp. 5352-5363.
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abstract = "A new building block, 1,4-di(3-alkoxy-2-thienyl)-2,5-difluorophenylene (DOTFP) with several desirable features such as high backbone planarity, suitably lying highest occupied molecular orbital (HOMO), and good solubility, was developed by inserting an electron-deficient difluorophenylene into the 3,3′-dialkoxy-2,2′-bithiophene (BTOR) unit. Three regioregular D-A1-D-A2 type polymers based on DOTFP and benzothiadiazole (BT) derivatives were synthesized and characterized by comparing with a D-A type BTOR-based polymer. The content of highly electron-rich alkoxythiophene is reduced by half in the DOTFP-based polymers versus that of the BTOR-based polymer analogue, which results in a deeper HOMO level and benefits high open-circuit voltage (Voc) in polymer solar cells (PSCs). Consequently, the DOTFP-ffBT-based solar cells exhibited a significantly improved power conversion efficiency (PCE) of 8.7{\%} and an increased Voc of 0.84 V compared to the BTOR-ffBT-based solar cells with a PCE of 2.6{\%} and a Voc of 0.49 V. Additionally, the DOTFP-based polymers showed improved charge transport properties and film morphology than the BTOR-based polymer BTOR-ffBT, resulting in simultaneous enhancement of the short-circuit current (Jsc) and fill factor (FF) in PSCs. These results demonstrate the great promise of the DOTFP building block for the construction of high-performance photovoltaic polymer semiconductors with increased Vocs.",
author = "Jianhua Chen and Zhenglong Yan and Linjing Tang and Uddin, {Mohammad Afsar} and Jianwei Yu and Xin Zhou and Kun Yang and Yumin Tang and Shin, {Tae Joo} and Woo, {Han Young} and Xugang Guo",
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AU - Chen, Jianhua

AU - Yan, Zhenglong

AU - Tang, Linjing

AU - Uddin, Mohammad Afsar

AU - Yu, Jianwei

AU - Zhou, Xin

AU - Yang, Kun

AU - Tang, Yumin

AU - Shin, Tae Joo

AU - Woo, Han Young

AU - Guo, Xugang

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N2 - A new building block, 1,4-di(3-alkoxy-2-thienyl)-2,5-difluorophenylene (DOTFP) with several desirable features such as high backbone planarity, suitably lying highest occupied molecular orbital (HOMO), and good solubility, was developed by inserting an electron-deficient difluorophenylene into the 3,3′-dialkoxy-2,2′-bithiophene (BTOR) unit. Three regioregular D-A1-D-A2 type polymers based on DOTFP and benzothiadiazole (BT) derivatives were synthesized and characterized by comparing with a D-A type BTOR-based polymer. The content of highly electron-rich alkoxythiophene is reduced by half in the DOTFP-based polymers versus that of the BTOR-based polymer analogue, which results in a deeper HOMO level and benefits high open-circuit voltage (Voc) in polymer solar cells (PSCs). Consequently, the DOTFP-ffBT-based solar cells exhibited a significantly improved power conversion efficiency (PCE) of 8.7% and an increased Voc of 0.84 V compared to the BTOR-ffBT-based solar cells with a PCE of 2.6% and a Voc of 0.49 V. Additionally, the DOTFP-based polymers showed improved charge transport properties and film morphology than the BTOR-based polymer BTOR-ffBT, resulting in simultaneous enhancement of the short-circuit current (Jsc) and fill factor (FF) in PSCs. These results demonstrate the great promise of the DOTFP building block for the construction of high-performance photovoltaic polymer semiconductors with increased Vocs.

AB - A new building block, 1,4-di(3-alkoxy-2-thienyl)-2,5-difluorophenylene (DOTFP) with several desirable features such as high backbone planarity, suitably lying highest occupied molecular orbital (HOMO), and good solubility, was developed by inserting an electron-deficient difluorophenylene into the 3,3′-dialkoxy-2,2′-bithiophene (BTOR) unit. Three regioregular D-A1-D-A2 type polymers based on DOTFP and benzothiadiazole (BT) derivatives were synthesized and characterized by comparing with a D-A type BTOR-based polymer. The content of highly electron-rich alkoxythiophene is reduced by half in the DOTFP-based polymers versus that of the BTOR-based polymer analogue, which results in a deeper HOMO level and benefits high open-circuit voltage (Voc) in polymer solar cells (PSCs). Consequently, the DOTFP-ffBT-based solar cells exhibited a significantly improved power conversion efficiency (PCE) of 8.7% and an increased Voc of 0.84 V compared to the BTOR-ffBT-based solar cells with a PCE of 2.6% and a Voc of 0.49 V. Additionally, the DOTFP-based polymers showed improved charge transport properties and film morphology than the BTOR-based polymer BTOR-ffBT, resulting in simultaneous enhancement of the short-circuit current (Jsc) and fill factor (FF) in PSCs. These results demonstrate the great promise of the DOTFP building block for the construction of high-performance photovoltaic polymer semiconductors with increased Vocs.

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