New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells

Amod Timalsina, Patrick E. Hartnett, Ferdinand S. Melkonyan, Joseph Strzalka, Vari S. Reddy, Antonio Facchetti, Michael R Wasielewski, Tobin J Marks

Research output: Contribution to journalArticle

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Abstract

The synthesis of a new tetrafluorinated semiconducting donor polymer, poly[(4,8-bis(5-(2-ethylhexyl)-4-fluorothiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethylhexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF4), and its photovoltaic performance in bulk heterojunction (BHJ) blends with the non-fullerene molecular acceptor [1,2:3,4]-bis-[N,N′-bis-1-pentylhexyl-perylenediimide-1,12-yl]-benzene (bPDI2P), are reported. PBTZF4:bPDI2P solar cells exhibit a high open circuit voltage (Voc) of 1.118 V, a short circuit current density (Jsc) of 10.02 mA cm−2, and a fill factor (FF) of 49.5%, affording a power conversion efficiency (PCE) of 5.55%. Interestingly, a lower PCE of 3.68% is obtained with the difluorinated analogue, poly[(4,8-bis(5-(2-ethylhexyl)-thiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethyl-hexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF2). Both PBTZF4:bPDI2P and PBTZF2:bPDI2P cells benefit from complementary (donor/acceptor) light absorption and very low geminate recombination, with bimolecular recombination being the dominant loss mechanism, as established by femtosecond transient absorption spectroscopy. DFT computation and physicochemical characterization data argue that the “additional” tetrafluorination planarizes the PBTZF4 backbone and enhances aggregation versusPBTZF2, affording superior charge carrier transport as assayed by field-effect mobility. In addition, fluorine-originated HOMO stabilization, −5.41 eV for PBTZF4versus −5.33 eV for PBTZF2, and a superior blend microstructure afford a higher PBTZF4:bPDI2P solar cell PCE versusPBTZF2:bPDI2P.

Original languageEnglish
Pages (from-to)5351-5361
Number of pages11
JournalJournal of Materials Chemistry A
Volume5
Issue number11
DOIs
Publication statusPublished - 2017

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Conversion efficiency
Solar cells
Polymers
Thiophenes
Fluorine
Carrier transport
Thiophene
Open circuit voltage
Benzene
Charge carriers
Absorption spectroscopy
Discrete Fourier transforms
Short circuit currents
Light absorption
Heterojunctions
Current density
Agglomeration
Stabilization
Microstructure
perylenediimide

ASJC Scopus subject areas

  • Chemistry(all)
  • Renewable Energy, Sustainability and the Environment
  • Materials Science(all)

Cite this

New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells. / Timalsina, Amod; Hartnett, Patrick E.; Melkonyan, Ferdinand S.; Strzalka, Joseph; Reddy, Vari S.; Facchetti, Antonio; Wasielewski, Michael R; Marks, Tobin J.

In: Journal of Materials Chemistry A, Vol. 5, No. 11, 2017, p. 5351-5361.

Research output: Contribution to journalArticle

Timalsina, Amod ; Hartnett, Patrick E. ; Melkonyan, Ferdinand S. ; Strzalka, Joseph ; Reddy, Vari S. ; Facchetti, Antonio ; Wasielewski, Michael R ; Marks, Tobin J. / New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells. In: Journal of Materials Chemistry A. 2017 ; Vol. 5, No. 11. pp. 5351-5361.
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abstract = "The synthesis of a new tetrafluorinated semiconducting donor polymer, poly[(4,8-bis(5-(2-ethylhexyl)-4-fluorothiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethylhexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF4), and its photovoltaic performance in bulk heterojunction (BHJ) blends with the non-fullerene molecular acceptor [1,2:3,4]-bis-[N,N′-bis-1-pentylhexyl-perylenediimide-1,12-yl]-benzene (bPDI2P), are reported. PBTZF4:bPDI2P solar cells exhibit a high open circuit voltage (Voc) of 1.118 V, a short circuit current density (Jsc) of 10.02 mA cm−2, and a fill factor (FF) of 49.5{\%}, affording a power conversion efficiency (PCE) of 5.55{\%}. Interestingly, a lower PCE of 3.68{\%} is obtained with the difluorinated analogue, poly[(4,8-bis(5-(2-ethylhexyl)-thiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethyl-hexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF2). Both PBTZF4:bPDI2P and PBTZF2:bPDI2P cells benefit from complementary (donor/acceptor) light absorption and very low geminate recombination, with bimolecular recombination being the dominant loss mechanism, as established by femtosecond transient absorption spectroscopy. DFT computation and physicochemical characterization data argue that the “additional” tetrafluorination planarizes the PBTZF4 backbone and enhances aggregation versusPBTZF2, affording superior charge carrier transport as assayed by field-effect mobility. In addition, fluorine-originated HOMO stabilization, −5.41 eV for PBTZF4versus −5.33 eV for PBTZF2, and a superior blend microstructure afford a higher PBTZF4:bPDI2P solar cell PCE versusPBTZF2:bPDI2P.",
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AU - Timalsina, Amod

AU - Hartnett, Patrick E.

AU - Melkonyan, Ferdinand S.

AU - Strzalka, Joseph

AU - Reddy, Vari S.

AU - Facchetti, Antonio

AU - Wasielewski, Michael R

AU - Marks, Tobin J

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N2 - The synthesis of a new tetrafluorinated semiconducting donor polymer, poly[(4,8-bis(5-(2-ethylhexyl)-4-fluorothiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethylhexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF4), and its photovoltaic performance in bulk heterojunction (BHJ) blends with the non-fullerene molecular acceptor [1,2:3,4]-bis-[N,N′-bis-1-pentylhexyl-perylenediimide-1,12-yl]-benzene (bPDI2P), are reported. PBTZF4:bPDI2P solar cells exhibit a high open circuit voltage (Voc) of 1.118 V, a short circuit current density (Jsc) of 10.02 mA cm−2, and a fill factor (FF) of 49.5%, affording a power conversion efficiency (PCE) of 5.55%. Interestingly, a lower PCE of 3.68% is obtained with the difluorinated analogue, poly[(4,8-bis(5-(2-ethylhexyl)-thiophene-2-yl)-benzo[1,2-b:4,5-b′]dithiophene)-alt-(5,6-difluoro-4,7-(4-(2-ethyl-hexyl)-dithien-2-yl-2,1,3-benzothiadiazole)] (PBTZF2). Both PBTZF4:bPDI2P and PBTZF2:bPDI2P cells benefit from complementary (donor/acceptor) light absorption and very low geminate recombination, with bimolecular recombination being the dominant loss mechanism, as established by femtosecond transient absorption spectroscopy. DFT computation and physicochemical characterization data argue that the “additional” tetrafluorination planarizes the PBTZF4 backbone and enhances aggregation versusPBTZF2, affording superior charge carrier transport as assayed by field-effect mobility. In addition, fluorine-originated HOMO stabilization, −5.41 eV for PBTZF4versus −5.33 eV for PBTZF2, and a superior blend microstructure afford a higher PBTZF4:bPDI2P solar cell PCE versusPBTZF2:bPDI2P.

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