A Fluorinated Polythiophene Derivative with Stabilized Backbone Conformation for Highly Efficient Fullerene and Non-Fullerene Polymer Solar Cells

Shaoqing Zhang, Yunpeng Qin, Mohammad Afsar Uddin, Bomee Jang, Wenchao Zhao, Delong Liu, Han Young Woo, Jianhui Hou

Research output: Contribution to journalArticle

82 Citations (Scopus)

Abstract

Here, taking a polythiophene derivative (PBDD4T) as a starting polymer, we tried to increase the rotation barrier and hence stabilize its backbone conformation by introducing fluorine into the β- and β′-position of the α-linked bithiophene segments and then synthesized a new polymer named as PBDD4T-2F. Our results demonstrate that the rotation barrier between the α-linked bithiophene significantly increases after the fluorination, so PBDD4T-2F has a more stable backbone conformation than PBDD4T. Compared to PBDD4T, PBDD4T-2F shows stronger aggregation effect in solution state and more compact π-π stacking in solid thin film and also possesses deeper HOMO level. These properties make PBDD4T-2F being an ideal donor material in PSCs. When blended with PC71BM, a fullerene acceptor, the PBDD4T-2F-based device showed a power conversion efficiency (PCE) of 9.04%, which is 38% higher than that of the PBDD4T-based device; when blended with ITIC, a non-fullerene acceptor, the PBDD4T-2F-based device showed a PCE of 8.69%, which is almost 20 times higher than that of the PBDD4T-based device. What is more, the tandem cell, in which the blend of PBDD4T-2F:PC61BM was used for making the front subcell, exhibited a high PCE of 10.12%. The photovoltaic results indicate that the fluorination is an effective method to enhance interchain π-π interaction for the polythiophene and hence to tune its photovoltaic properties in PSCs, especially for the fullerene-free device based on ITIC.

Original languageEnglish
Pages (from-to)2993-3000
Number of pages8
JournalMacromolecules
Volume49
Issue number8
DOIs
Publication statusPublished - 2016 Apr 26

Fingerprint

Fullerenes
Conversion efficiency
Conformations
Fluorination
Derivatives
Polymers
Fluorine
Agglomeration
Thin films
Polymer solar cells
polythiophene

ASJC Scopus subject areas

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

Cite this

A Fluorinated Polythiophene Derivative with Stabilized Backbone Conformation for Highly Efficient Fullerene and Non-Fullerene Polymer Solar Cells. / Zhang, Shaoqing; Qin, Yunpeng; Uddin, Mohammad Afsar; Jang, Bomee; Zhao, Wenchao; Liu, Delong; Woo, Han Young; Hou, Jianhui.

In: Macromolecules, Vol. 49, No. 8, 26.04.2016, p. 2993-3000.

Research output: Contribution to journalArticle

Zhang, Shaoqing ; Qin, Yunpeng ; Uddin, Mohammad Afsar ; Jang, Bomee ; Zhao, Wenchao ; Liu, Delong ; Woo, Han Young ; Hou, Jianhui. / A Fluorinated Polythiophene Derivative with Stabilized Backbone Conformation for Highly Efficient Fullerene and Non-Fullerene Polymer Solar Cells. In: Macromolecules. 2016 ; Vol. 49, No. 8. pp. 2993-3000.
@article{500347cc96c841019ae1b5f98a495e17,
title = "A Fluorinated Polythiophene Derivative with Stabilized Backbone Conformation for Highly Efficient Fullerene and Non-Fullerene Polymer Solar Cells",
abstract = "Here, taking a polythiophene derivative (PBDD4T) as a starting polymer, we tried to increase the rotation barrier and hence stabilize its backbone conformation by introducing fluorine into the β- and β′-position of the α-linked bithiophene segments and then synthesized a new polymer named as PBDD4T-2F. Our results demonstrate that the rotation barrier between the α-linked bithiophene significantly increases after the fluorination, so PBDD4T-2F has a more stable backbone conformation than PBDD4T. Compared to PBDD4T, PBDD4T-2F shows stronger aggregation effect in solution state and more compact π-π stacking in solid thin film and also possesses deeper HOMO level. These properties make PBDD4T-2F being an ideal donor material in PSCs. When blended with PC71BM, a fullerene acceptor, the PBDD4T-2F-based device showed a power conversion efficiency (PCE) of 9.04{\%}, which is 38{\%} higher than that of the PBDD4T-based device; when blended with ITIC, a non-fullerene acceptor, the PBDD4T-2F-based device showed a PCE of 8.69{\%}, which is almost 20 times higher than that of the PBDD4T-based device. What is more, the tandem cell, in which the blend of PBDD4T-2F:PC61BM was used for making the front subcell, exhibited a high PCE of 10.12{\%}. The photovoltaic results indicate that the fluorination is an effective method to enhance interchain π-π interaction for the polythiophene and hence to tune its photovoltaic properties in PSCs, especially for the fullerene-free device based on ITIC.",
author = "Shaoqing Zhang and Yunpeng Qin and Uddin, {Mohammad Afsar} and Bomee Jang and Wenchao Zhao and Delong Liu and Woo, {Han Young} and Jianhui Hou",
year = "2016",
month = "4",
day = "26",
doi = "10.1021/acs.macromol.6b00248",
language = "English",
volume = "49",
pages = "2993--3000",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - A Fluorinated Polythiophene Derivative with Stabilized Backbone Conformation for Highly Efficient Fullerene and Non-Fullerene Polymer Solar Cells

AU - Zhang, Shaoqing

AU - Qin, Yunpeng

AU - Uddin, Mohammad Afsar

AU - Jang, Bomee

AU - Zhao, Wenchao

AU - Liu, Delong

AU - Woo, Han Young

AU - Hou, Jianhui

PY - 2016/4/26

Y1 - 2016/4/26

N2 - Here, taking a polythiophene derivative (PBDD4T) as a starting polymer, we tried to increase the rotation barrier and hence stabilize its backbone conformation by introducing fluorine into the β- and β′-position of the α-linked bithiophene segments and then synthesized a new polymer named as PBDD4T-2F. Our results demonstrate that the rotation barrier between the α-linked bithiophene significantly increases after the fluorination, so PBDD4T-2F has a more stable backbone conformation than PBDD4T. Compared to PBDD4T, PBDD4T-2F shows stronger aggregation effect in solution state and more compact π-π stacking in solid thin film and also possesses deeper HOMO level. These properties make PBDD4T-2F being an ideal donor material in PSCs. When blended with PC71BM, a fullerene acceptor, the PBDD4T-2F-based device showed a power conversion efficiency (PCE) of 9.04%, which is 38% higher than that of the PBDD4T-based device; when blended with ITIC, a non-fullerene acceptor, the PBDD4T-2F-based device showed a PCE of 8.69%, which is almost 20 times higher than that of the PBDD4T-based device. What is more, the tandem cell, in which the blend of PBDD4T-2F:PC61BM was used for making the front subcell, exhibited a high PCE of 10.12%. The photovoltaic results indicate that the fluorination is an effective method to enhance interchain π-π interaction for the polythiophene and hence to tune its photovoltaic properties in PSCs, especially for the fullerene-free device based on ITIC.

AB - Here, taking a polythiophene derivative (PBDD4T) as a starting polymer, we tried to increase the rotation barrier and hence stabilize its backbone conformation by introducing fluorine into the β- and β′-position of the α-linked bithiophene segments and then synthesized a new polymer named as PBDD4T-2F. Our results demonstrate that the rotation barrier between the α-linked bithiophene significantly increases after the fluorination, so PBDD4T-2F has a more stable backbone conformation than PBDD4T. Compared to PBDD4T, PBDD4T-2F shows stronger aggregation effect in solution state and more compact π-π stacking in solid thin film and also possesses deeper HOMO level. These properties make PBDD4T-2F being an ideal donor material in PSCs. When blended with PC71BM, a fullerene acceptor, the PBDD4T-2F-based device showed a power conversion efficiency (PCE) of 9.04%, which is 38% higher than that of the PBDD4T-based device; when blended with ITIC, a non-fullerene acceptor, the PBDD4T-2F-based device showed a PCE of 8.69%, which is almost 20 times higher than that of the PBDD4T-based device. What is more, the tandem cell, in which the blend of PBDD4T-2F:PC61BM was used for making the front subcell, exhibited a high PCE of 10.12%. The photovoltaic results indicate that the fluorination is an effective method to enhance interchain π-π interaction for the polythiophene and hence to tune its photovoltaic properties in PSCs, especially for the fullerene-free device based on ITIC.

UR - http://www.scopus.com/inward/record.url?scp=84967262862&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84967262862&partnerID=8YFLogxK

U2 - 10.1021/acs.macromol.6b00248

DO - 10.1021/acs.macromol.6b00248

M3 - Article

AN - SCOPUS:84967262862

VL - 49

SP - 2993

EP - 3000

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 8

ER -