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

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.

Authors:
 [1];  [1]; ORCiD logo [1];  [2];  [1];  [3]; ORCiD logo [1]; ORCiD logo [1]
  1. Northwestern Univ., Evanston, IL (United States)
  2. Argonne National Lab. (ANL), Argonne, IL (United States)
  3. Northwestern Univ., Evanston, IL (United States); Polyera Corp., Slokie, IL (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1376900
Alternate Identifier(s):
OSTI ID: 1388126
Grant/Contract Number:  
AC02-06CH11357; SC0001059
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Materials Chemistry. A
Additional Journal Information:
Journal Volume: 5; Journal Issue: 11; Journal ID: ISSN 2050-7488
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous), catalysis (heterogeneous), solar (photovoltaic), solar (fuels), photosynthesis (natural and artificial), bio-inspired, hydrogen and fuel cells, electrodes - solar, defects, charge transport, spin dynamics, membrane, materials and chemistry by design, optics, synthesis (novel materials), synthesis (self-assembly)

Citation Formats

Timalsina, Amod, Hartnett, Patrick E., Melkonyan, Ferdinand S., Strzalka, Joseph, Reddy, Vari S., Facchetti, Antonio, Wasielewski, Michael R., and Marks, Tobin J. New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells. United States: N. p., 2017. Web. doi:10.1039/c7ta00063d.
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. United States. doi:10.1039/c7ta00063d.
Timalsina, Amod, Hartnett, Patrick E., Melkonyan, Ferdinand S., Strzalka, Joseph, Reddy, Vari S., Facchetti, Antonio, Wasielewski, Michael R., and Marks, Tobin J. Thu . "New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells". United States. doi:10.1039/c7ta00063d. https://www.osti.gov/servlets/purl/1376900.
@article{osti_1376900,
title = {New donor polymer with tetrafluorinated blocks for enhanced performance in perylenediimide-based solar cells},
author = {Timalsina, Amod and Hartnett, Patrick E. and Melkonyan, Ferdinand S. and Strzalka, Joseph and Reddy, Vari S. and Facchetti, Antonio and Wasielewski, Michael R. and Marks, Tobin J.},
abstractNote = {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.},
doi = {10.1039/c7ta00063d},
journal = {Journal of Materials Chemistry. A},
number = 11,
volume = 5,
place = {United States},
year = {2017},
month = {2}
}

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Figures / Tables:

Figure 1 Figure 1: Structures of the donor polymers PBTZF4 and PBTZF2, and acceptor bPDI2P, studied in this contribution (R 1 = CH2CH(C2H5)C4H9, R = $n$-C5H11). The geometry optimized DFT structures of the polymers (top and side views) and the acceptor (side view only, adapted from ref. 51) are also shown, andmore » important dihedral angles are highlighted.« less

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    Works referencing / citing this record:

    Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[ j , l ]fluoranthenes via palladium-catalysed C–H bond functionalisation
    journal, January 2018

    • Shi, Xinzhe; Roisnel, Thierry; Soulé, Jean-François
    • Organic Chemistry Frontiers, Vol. 5, Issue 3
    • DOI: 10.1039/c7qo00799j

    Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[ j , l ]fluoranthenes via palladium-catalysed C–H bond functionalisation
    journal, January 2018

    • Shi, Xinzhe; Roisnel, Thierry; Soulé, Jean-François
    • Organic Chemistry Frontiers, Vol. 5, Issue 3
    • DOI: 10.1039/c7qo00799j

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