Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/imide-based acceptors

Jason T. Bloking; Xu Han; Andrew T. Higgs; John P. Kastrop; Laxman Pandey; Joseph E. Norton; Chad Risko; Cynthia E. Chen; Jean-Luc Bredas; Michael D. McGehee; Alan Sellinger

doi:10.1021/cm203111k

Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/imide-based acceptors

Jason T. Bloking, Xu Han, Andrew T. Higgs, John P. Kastrop, Laxman Pandey, Joseph E. Norton, Chad Risko, Cynthia E. Chen, Jean-Luc Bredas, Michael D. McGehee, Alan Sellinger^*

^*Corresponding author for this work

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

236 Scopus citations

Abstract

A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexyl-naphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency.

Original language	English (US)
Pages (from-to)	5484-5490
Number of pages	7
Journal	Chemistry of Materials
Volume	23
Issue number	24
DOIs	https://doi.org/10.1021/cm203111k
State	Published - Dec 27 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-C1-015-21
Acknowledgements: This project was funded by the Center for Advanced Molecular Photovoltaics (CAMP), Award No. KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST), and by the Global Climate and Energy Project (GCEP), Award No. 1138721. We also thank Dr. Peng Wei for the TGA measurement.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

Keywords

electron acceptors
n-type materials
organic electronics
photovoltaic devices
solar cells

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/cm203111k

Cite this

@article{cae589953d3340f09f757b409fc4b0d0,

title = "Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/imide-based acceptors",

abstract = "A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexyl-naphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency.",

keywords = "electron acceptors, n-type materials, organic electronics, photovoltaic devices, solar cells",

author = "Bloking, {Jason T.} and Xu Han and Higgs, {Andrew T.} and Kastrop, {John P.} and Laxman Pandey and Norton, {Joseph E.} and Chad Risko and Chen, {Cynthia E.} and Jean-Luc Bredas and McGehee, {Michael D.} and Alan Sellinger",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: This project was funded by the Center for Advanced Molecular Photovoltaics (CAMP), Award No. KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST), and by the Global Climate and Energy Project (GCEP), Award No. 1138721. We also thank Dr. Peng Wei for the TGA measurement. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2011",

month = dec,

day = "27",

doi = "10.1021/cm203111k",

language = "English (US)",

volume = "23",

pages = "5484--5490",

journal = "Chemistry of Materials",

issn = "0897-4756",

publisher = "AMER CHEMICAL SOC",

number = "24",

}

TY - JOUR

T1 - Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/imide-based acceptors

AU - Bloking, Jason T.

AU - Han, Xu

AU - Higgs, Andrew T.

AU - Kastrop, John P.

AU - Pandey, Laxman

AU - Norton, Joseph E.

AU - Risko, Chad

AU - Chen, Cynthia E.

AU - Bredas, Jean-Luc

AU - McGehee, Michael D.

AU - Sellinger, Alan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: This project was funded by the Center for Advanced Molecular Photovoltaics (CAMP), Award No. KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST), and by the Global Climate and Energy Project (GCEP), Award No. 1138721. We also thank Dr. Peng Wei for the TGA measurement. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2011/12/27

Y1 - 2011/12/27

N2 - A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexyl-naphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency.

AB - A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexyl-naphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency.

KW - electron acceptors

KW - n-type materials

KW - organic electronics

KW - photovoltaic devices

KW - solar cells

UR - http://www.scopus.com/inward/record.url?scp=84055192620&partnerID=8YFLogxK

U2 - 10.1021/cm203111k

DO - 10.1021/cm203111k

M3 - Article

AN - SCOPUS:84055192620

SN - 0897-4756

VL - 23

SP - 5484

EP - 5490

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 24

ER -

Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/imide-based acceptors

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this