Ring substituents mediate the morphology of PBDTTPD-PCBM bulk-heterojunction solar cells

Julien Warnan; Abdulrahman El Labban; Clement Cabanetos; Eric T. Hoke; Pradeep Kumar Shukla; Chad Risko; Jean Luc Brédas; Michael D. McGehee; Pierre Beaujuge

doi:10.1021/cm500172w

Ring substituents mediate the morphology of PBDTTPD-PCBM bulk-heterojunction solar cells

Julien Warnan, Abdulrahman El Labban, Clement Cabanetos, Eric T. Hoke, Pradeep Kumar Shukla, Chad Risko, Jean Luc Brédas, Michael D. McGehee, Pierre Beaujuge

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

121 Scopus citations

Abstract

Among π-conjugated polymer donors for efficient bulk-heterojunction (BHJ) solar cell applications, poly(benzo[1,2-b:4,5-b′]dithiophene- thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers yield some of the highest open-circuit voltages (VOC, ca. 0.9 V) and fill-factors (FF, ca. 70%) in conventional (single-cell) BHJ devices with PCBM acceptors. In PBDTTPD, side chains of varying size and branching affect polymer self-assembly, nanostructural order, and impact material performance. However, the role of the polymer side-chain pattern in the intimate mixing between polymer donors and PCBM acceptors, and on the development of the BHJ morphology is in general less understood. In this contribution, we show that ring substituents such as furan (F), thiophene (T) and selenophene (S)-incorporated into the side chains of PBDTTPD polymers-can induce significant and, of importance, very different morphological effects in BHJs with PCBM. A combination of experimental and theoretical (via density functional theory) characterizations sheds light on how varying the heteroatom of the ring substituents impacts (i) the preferred side-chain configurations and (ii) the ionization, electronic, and optical properties of the PBDTTPD polymers. In parallel, we find that the PBDT(X)TPD analogs (with X = F, T, or S) span a broad range of power conversion efficiencies (PCEs, 3-6.5%) in optimized devices with improved thin-film morphologies via the use of 1,8-diiodooctane (DIO), and discuss that persistent morphological impediments at the nanoscale can be at the origin of the spread in PCE across optimized PBDT(X)TPD-based devices. With their high VOC ∼1 V, PBDT(X)TPD polymers are promising candidates for use in the high-band gap cell of tandem solar cells. © 2014 American Chemical Society.

Original language	English (US)
Pages (from-to)	2299-2306
Number of pages	8
Journal	Chemistry of Materials
Volume	26
Issue number	7
DOIs	https://doi.org/10.1021/cm500172w
State	Published - Mar 28 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-C1-015-21
Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). E.H., CR., J.L.B., and M.D.M.c.G. acknowledge financial support by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by KAUST. The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements and elemental analyses, and Sandra Seywald (MPIP-Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. P.K.S. is grateful to the University Grants Commission, New Delhi, India for a research fellowship.

ASJC Scopus subject areas

Materials Chemistry
General Chemical Engineering
General Chemistry

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10.1021/cm500172w

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@article{92ef07afdeeb42a589a8e3f3a0badab1,

title = "Ring substituents mediate the morphology of PBDTTPD-PCBM bulk-heterojunction solar cells",

abstract = "Among π-conjugated polymer donors for efficient bulk-heterojunction (BHJ) solar cell applications, poly(benzo[1,2-b:4,5-b′]dithiophene- thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers yield some of the highest open-circuit voltages (VOC, ca. 0.9 V) and fill-factors (FF, ca. 70%) in conventional (single-cell) BHJ devices with PCBM acceptors. In PBDTTPD, side chains of varying size and branching affect polymer self-assembly, nanostructural order, and impact material performance. However, the role of the polymer side-chain pattern in the intimate mixing between polymer donors and PCBM acceptors, and on the development of the BHJ morphology is in general less understood. In this contribution, we show that ring substituents such as furan (F), thiophene (T) and selenophene (S)-incorporated into the side chains of PBDTTPD polymers-can induce significant and, of importance, very different morphological effects in BHJs with PCBM. A combination of experimental and theoretical (via density functional theory) characterizations sheds light on how varying the heteroatom of the ring substituents impacts (i) the preferred side-chain configurations and (ii) the ionization, electronic, and optical properties of the PBDTTPD polymers. In parallel, we find that the PBDT(X)TPD analogs (with X = F, T, or S) span a broad range of power conversion efficiencies (PCEs, 3-6.5%) in optimized devices with improved thin-film morphologies via the use of 1,8-diiodooctane (DIO), and discuss that persistent morphological impediments at the nanoscale can be at the origin of the spread in PCE across optimized PBDT(X)TPD-based devices. With their high VOC ∼1 V, PBDT(X)TPD polymers are promising candidates for use in the high-band gap cell of tandem solar cells. {\textcopyright} 2014 American Chemical Society.",

author = "Julien Warnan and {El Labban}, Abdulrahman and Clement Cabanetos and Hoke, {Eric T.} and Shukla, {Pradeep Kumar} and Chad Risko and Br{\'e}das, {Jean Luc} and McGehee, {Michael D.} and Pierre Beaujuge",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). E.H., CR., J.L.B., and M.D.M.c.G. acknowledge financial support by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by KAUST. The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements and elemental analyses, and Sandra Seywald (MPIP-Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. P.K.S. is grateful to the University Grants Commission, New Delhi, India for a research fellowship.",

year = "2014",

month = mar,

day = "28",

doi = "10.1021/cm500172w",

language = "English (US)",

volume = "26",

pages = "2299--2306",

journal = "Chemistry of Materials",

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T1 - Ring substituents mediate the morphology of PBDTTPD-PCBM bulk-heterojunction solar cells

AU - Warnan, Julien

AU - El Labban, Abdulrahman

AU - Cabanetos, Clement

AU - Hoke, Eric T.

AU - Shukla, Pradeep Kumar

AU - Risko, Chad

AU - Brédas, Jean Luc

AU - McGehee, Michael D.

AU - Beaujuge, Pierre

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). E.H., CR., J.L.B., and M.D.M.c.G. acknowledge financial support by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by KAUST. The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements and elemental analyses, and Sandra Seywald (MPIP-Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. P.K.S. is grateful to the University Grants Commission, New Delhi, India for a research fellowship.

PY - 2014/3/28

Y1 - 2014/3/28

N2 - Among π-conjugated polymer donors for efficient bulk-heterojunction (BHJ) solar cell applications, poly(benzo[1,2-b:4,5-b′]dithiophene- thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers yield some of the highest open-circuit voltages (VOC, ca. 0.9 V) and fill-factors (FF, ca. 70%) in conventional (single-cell) BHJ devices with PCBM acceptors. In PBDTTPD, side chains of varying size and branching affect polymer self-assembly, nanostructural order, and impact material performance. However, the role of the polymer side-chain pattern in the intimate mixing between polymer donors and PCBM acceptors, and on the development of the BHJ morphology is in general less understood. In this contribution, we show that ring substituents such as furan (F), thiophene (T) and selenophene (S)-incorporated into the side chains of PBDTTPD polymers-can induce significant and, of importance, very different morphological effects in BHJs with PCBM. A combination of experimental and theoretical (via density functional theory) characterizations sheds light on how varying the heteroatom of the ring substituents impacts (i) the preferred side-chain configurations and (ii) the ionization, electronic, and optical properties of the PBDTTPD polymers. In parallel, we find that the PBDT(X)TPD analogs (with X = F, T, or S) span a broad range of power conversion efficiencies (PCEs, 3-6.5%) in optimized devices with improved thin-film morphologies via the use of 1,8-diiodooctane (DIO), and discuss that persistent morphological impediments at the nanoscale can be at the origin of the spread in PCE across optimized PBDT(X)TPD-based devices. With their high VOC ∼1 V, PBDT(X)TPD polymers are promising candidates for use in the high-band gap cell of tandem solar cells. © 2014 American Chemical Society.

AB - Among π-conjugated polymer donors for efficient bulk-heterojunction (BHJ) solar cell applications, poly(benzo[1,2-b:4,5-b′]dithiophene- thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers yield some of the highest open-circuit voltages (VOC, ca. 0.9 V) and fill-factors (FF, ca. 70%) in conventional (single-cell) BHJ devices with PCBM acceptors. In PBDTTPD, side chains of varying size and branching affect polymer self-assembly, nanostructural order, and impact material performance. However, the role of the polymer side-chain pattern in the intimate mixing between polymer donors and PCBM acceptors, and on the development of the BHJ morphology is in general less understood. In this contribution, we show that ring substituents such as furan (F), thiophene (T) and selenophene (S)-incorporated into the side chains of PBDTTPD polymers-can induce significant and, of importance, very different morphological effects in BHJs with PCBM. A combination of experimental and theoretical (via density functional theory) characterizations sheds light on how varying the heteroatom of the ring substituents impacts (i) the preferred side-chain configurations and (ii) the ionization, electronic, and optical properties of the PBDTTPD polymers. In parallel, we find that the PBDT(X)TPD analogs (with X = F, T, or S) span a broad range of power conversion efficiencies (PCEs, 3-6.5%) in optimized devices with improved thin-film morphologies via the use of 1,8-diiodooctane (DIO), and discuss that persistent morphological impediments at the nanoscale can be at the origin of the spread in PCE across optimized PBDT(X)TPD-based devices. With their high VOC ∼1 V, PBDT(X)TPD polymers are promising candidates for use in the high-band gap cell of tandem solar cells. © 2014 American Chemical Society.

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UR - https://pubs.acs.org/doi/10.1021/cm500172w

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U2 - 10.1021/cm500172w

DO - 10.1021/cm500172w

M3 - Article

SN - 0897-4756

VL - 26

SP - 2299

EP - 2306

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 7

ER -

Ring substituents mediate the morphology of PBDTTPD-PCBM bulk-heterojunction solar cells

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