A low band-gap polymer based on unsubstituted benzo[1,2-b:4,5-b']dithiophene for high performance organic photovoltaics

Woong Jung, Jae; Woong Jo, Jea; Liu, Feng; Russell, Thomas P.; Ho Jo, Won

doi:10.1039/c2cc32985a

A low band-gap polymer based on unsubstituted benzo[1,2-b:4,5-b']dithiophene for high performance organic photovoltaics

Journal Article · Sat Dec 31 23:00:00 EST 2011 · ChemComm

DOI:https://doi.org/10.1039/c2cc32985a· OSTI ID:1382665

Woong Jung, Jae; Woong Jo, Jea; Liu, Feng; Russell, Thomas P.; Ho Jo, Won

A low band-gap conjugated polymer, PBDTDPP, composed of unsubstituted benzo[1,2-b:4,5-b']dithiophene and diketopyrrolo[3,4-c]pyrrole was synthesized. The deep HOMO level of PBDTDPP enhances the VOC of a PSC up to 0.82 V and exhibits a PCE of 5.16%, while alkoxy substituted PBDTDPP-OR yields a PCE of 2.24% with a VOC of 0.61 V.

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Polymer-Based Materials for Harvesting Solar Energy (PHaSE)

Sponsoring Organization:: USDOE SC Office of Basic Energy Sciences (SC-22)

DOE Contract Number:: SC0001087

OSTI ID:: 1382665

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 55 Vol. 48; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (39)

Development of New Semiconducting Polymers for High Performance Solar Cells Liang, Yongye; Wu, Yue; Feng, Danqin Journal of the American Chemical Society, Vol. 131, Issue 1 https://doi.org/10.1021/ja808373p	journal	January 2009
Effects of Annealing on the Nanomorphology and Performance of Poly(alkylthiophene):Fullerene Bulk-Heterojunction Solar Cells Nguyen, L. H.; Hoppe, H.; Erb, T. Advanced Functional Materials, Vol. 17, Issue 7 https://doi.org/10.1002/adfm.200601038	journal	March 2007
Alkyl Side Chain Impact on the Charge Transport and Photovoltaic Properties of Benzodithiophene and Diketopyrrolopyrrole-Based Copolymers Li, Zhao; Zhang, Yanguang; Tsang, Sai-Wing The Journal of Physical Chemistry C, Vol. 115, Issue 36 https://doi.org/10.1021/jp202996p	journal	August 2011
Efficient Polymer Solar Cells Based on the Copolymers of Benzodithiophene and Thienopyrroledione Zhang, Yong; Hau, Steven K.; Yip, Hin-Lap Chemistry of Materials, Vol. 22, Issue 9 https://doi.org/10.1021/cm100417z	journal	May 2010
A Polybenzo[1,2-b:4,5-b′]dithiophene Derivative with Deep HOMO Level and Its Application in High-Performance Polymer Solar Cells Huo, Lijun; Hou, Jianhui; Zhang, Shaoqing Angewandte Chemie International Edition, Vol. 49, Issue 8 https://doi.org/10.1002/anie.200906934	journal	January 2010
A Low-Bandgap Diketopyrrolopyrrole-Benzothiadiazole-Based Copolymer for High-Mobility Ambipolar Organic Thin-Film Transistors Sonar, Prashant; Singh, Samarendra P.; Li, Yuning Advanced Materials, Vol. 22, Issue 47, p. 5409-5413 https://doi.org/10.1002/adma.201002973	journal	October 2010
A Thieno[3,4- c ]pyrrole-4,6-dione-Based Copolymer for Efficient Solar Cells Zou, Yingping; Najari, Ahmed; Berrouard, Philippe Journal of the American Chemical Society, Vol. 132, Issue 15 https://doi.org/10.1021/ja101888b	journal	April 2010
Organic Semiconductors for Solution-Processable Field-Effect Transistors (OFETs) Allard, Sybille; Forster, Michael; Souharce, Benjamin Angewandte Chemie International Edition, Vol. 47, Issue 22 https://doi.org/10.1002/anie.200701920	journal	May 2008
Effect of Annealing Solvent Solubility on the Performance of Poly(3-hexylthiophene)/Methanofullerene Solar Cells Park, Jong Hwan; Kim, Jong Soo; Lee, Ji Hwang The Journal of Physical Chemistry C, Vol. 113, Issue 40 https://doi.org/10.1021/jp9029562	journal	September 2009
Synthesis of a Low Band Gap Polymer and Its Application in Highly Efficient Polymer Solar Cells Hou, Jianhui; Chen, Hsiang-Yu; Zhang, Shaoqing Journal of the American Chemical Society, Vol. 131, Issue 43 https://doi.org/10.1021/ja9064975	journal	November 2009
Polymer solar cells Li, Gang; Zhu, Rui; Yang, Yang Nature Photonics, Vol. 6, Issue 3 https://doi.org/10.1038/nphoton.2012.11	journal	February 2012
3,6-Di(furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and bithiophene copolymer with rather disordered chain orientation showing high mobility in organic thin film transistors Li, Yuning; Sonar, Prashant; Singh, Samarendra P. Journal of Materials Chemistry, Vol. 21, Issue 29 https://doi.org/10.1039/c1jm11290b	journal	January 2011
Small Bandgap Polymers for Organic Solar Cells (Polymer Material Development in the Last 5 Years) Kroon, Renee; Lenes, Martijn; Hummelen, Jan C. Polymer Reviews, Vol. 48, Issue 3 https://doi.org/10.1080/15583720802231833	journal	August 2008
Side-Chain Tunability of Furan-Containing Low-Band-Gap Polymers Provides Control of Structural Order in Efficient Solar Cells Yiu, Alan T.; Beaujuge, Pierre M.; Lee, Olivia P. Journal of the American Chemical Society, Vol. 134, Issue 4 https://doi.org/10.1021/ja2089662	journal	January 2012
Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics Qu, Sanyin; Tian, He Chemical Communications, Vol. 48, Issue 25 https://doi.org/10.1039/c2cc17886a	journal	January 2012
Polymer solar cells with enhanced open-circuit voltage and efficiency Chen, Hsiang-Yu; Hou, Jianhui; Zhang, Shaoqing Nature Photonics, Vol. 3, Issue 11, p. 649-653 https://doi.org/10.1038/nphoton.2009.192	journal	November 2009
Oligothiophene Derivatives Functionalized with a Diketopyrrolopyrrolo Core for Solution-Processed Field Effect Transistors: Effect of Alkyl Substituents and Thermal Annealing Tantiwiwat, Mananya; Tamayo, Arnold; Luu, Ngoc The Journal of Physical Chemistry C, Vol. 112, Issue 44 https://doi.org/10.1021/jp8068305	journal	October 2008
Charge Transport Physics of Conjugated Polymer Field-Effect Transistors Sirringhaus, Henning; Bird, Matt; Zhao, Ni Advanced Materials, Vol. 22, Issue 34 https://doi.org/10.1002/adma.200902857	journal	June 2010
Swapping field-effect transistor characteristics in polymeric diketopyrrolopyrrole semiconductors: debut of an electron dominant transporting polymer Lee, Junghoon; Cho, Shinuk; Seo, Jung Hwa J. Mater. Chem., Vol. 22, Issue 4 https://doi.org/10.1039/C1JM14549E	journal	January 2012
Small Molecule Solution-Processed Bulk Heterojunction Solar Cells ^† Walker, Bright; Kim, Chunki; Nguyen, Thuc-Quyen Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm102189g	journal	February 2011
Annealing-Free High Efficiency and Large Area Polymer Solar Cells Fabricated by a Roller Painting Process Jung, Jae Woong; Jo, Won Ho Advanced Functional Materials, Vol. 20, Issue 14 https://doi.org/10.1002/adfm.201000164	journal	June 2010
2,5-Bis(2-octyldodecyl)pyrrolo[3,4- c ]pyrrole-1,4-(2 H ,5 H )-dione-Based Donor–Acceptor Alternating Copolymer Bearing 5,5′-Di(thiophen-2-yl)-2,2′-biselenophene Exhibiting 1.5 cm ² ·V ^–1 ·s ^–1 Hole Mobility in Thin-Film Transistors Ha, Jae Seung; Kim, Kyung Hwan; Choi, Dong Hoon Journal of the American Chemical Society, Vol. 133, Issue 27, p. 10364-10367 https://doi.org/10.1021/ja203189h	journal	July 2011
Poly(diketopyrrolopyrrole‐benzothiadiazole) with Ambipolarity Approaching 100% Equivalency Cho, Shinuk; Lee, Junghoon; Tong, Minghong Advanced Functional Materials, Vol. 21, Issue 10 https://doi.org/10.1002/adfm.201002651	journal	March 2011
High-efficiency inverted dithienogermole–thienopyrrolodione-based polymer solar cells Small, Cephas E.; Chen, Song; Subbiah, Jegadesan Nature Photonics, Vol. 6, Issue 2, p. 115-120 https://doi.org/10.1038/nphoton.2011.317	journal	December 2011
Efficient Solar Cells Based on an Easily Accessible Diketopyrrolopyrrole Polymer Bijleveld, Johan C.; Gevaerts, Veronique S.; Di Nuzzo, Daniele Advanced Materials, Vol. 22, Issue 35 https://doi.org/10.1002/adma.201001449	journal	August 2010
Thieno[3,2- b ]thiophene−Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices Bronstein, Hugo; Chen, Zhuoying; Ashraf, Raja Shahid Journal of the American Chemical Society, Vol. 133, Issue 10 https://doi.org/10.1021/ja110619k	journal	March 2011
High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Li, Gang; Shrotriya, Vishal; Huang, Jinsong Nature Materials, Vol. 4, Issue 11, p. 864-868 https://doi.org/10.1038/nmat1500	journal	October 2005
Simultaneous Enhancement of Open-Circuit Voltage, Short-Circuit Current Density, and Fill Factor in Polymer Solar Cells He, Zhicai; Zhong, Chengmei; Huang, Xun Advanced Materials, Vol. 23, Issue 40, p. 4636-4643 https://doi.org/10.1002/adma.201103006	journal	September 2011
A high mobility conjugated polymer based on dithienothiophene and diketopyrrolopyrrole for organic photovoltaics Jung, Jae Woong; Liu, Feng; Russell, Thomas P. Energy & Environmental Science, Vol. 5, Issue 5 https://doi.org/10.1039/c2ee21149a	journal	January 2012
High-Efficiency Polymer Solar Cells with Water-Soluble and Self-Doped Conducting Polyaniline Graft Copolymer as Hole Transport Layer Jung, Jae Woong; Lee, Jea Uk; Jo, Won Ho The Journal of Physical Chemistry C, Vol. 114, Issue 1 https://doi.org/10.1021/jp9083844	journal	November 2009
Synthetic Control of Structural Order in N-Alkylthieno[3,4-c]pyrrole-4,6-dione-Based Polymers for Efficient Solar Cells Piliego, Claudia; Holcombe, Thomas W.; Douglas, Jessica D. Journal of the American Chemical Society, Vol. 132, Issue 22, p. 7595-7597 https://doi.org/10.1021/ja103275u	journal	June 2010
Bandgap and Molecular Level Control of the Low-Bandgap Polymers Based on 3,6-Dithiophen-2-yl-2,5-dihydropyrrolo[3,4- c ]pyrrole-1,4-dione toward Highly Efficient Polymer Solar Cells Huo, Lijun; Hou, Jianhui; Chen, Hsiang-Yu Macromolecules, Vol. 42, Issue 17 https://doi.org/10.1021/ma9012972	journal	September 2009
Enhanced Performance and Air Stability of Polymer Solar Cells by Formation of a Self-Assembled Buffer Layer from Fullerene-End-Capped Poly(ethylene glycol) Jung, Jae Woong; Jo, Jea Woong; Jo, Won Ho Advanced Materials, Vol. 23, Issue 15, p. 1782-1787 https://doi.org/10.1002/adma.201003996	journal	March 2011
Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties Liang, Yongye; Feng, Danqin; Wu, Yue Journal of the American Chemical Society, Vol. 131, Issue 22, p. 7792-7799 https://doi.org/10.1021/ja901545q	journal	June 2009
Tandem polymer solar cells featuring a spectrally matched low-bandgap polymer Dou, Letian; You, Jingbi; Yang, Jun Nature Photonics, Vol. 6, Issue 3 https://doi.org/10.1038/nphoton.2011.356	journal	February 2012
Annealing-Free High-Mobility Diketopyrrolopyrrole−Quaterthiophene Copolymer for Solution-Processed Organic Thin Film Transistors Li, Yuning; Sonar, Prashant; Singh, Samarendra P. Journal of the American Chemical Society, Vol. 133, Issue 7 https://doi.org/10.1021/ja1085996	journal	February 2011
Synthesis of Diketopyrrolopyrrole Containing Copolymers: A Study of Their Optical and Photovoltaic Properties Kanimozhi, Catherine; Balraju, P.; Sharma, G. D. The Journal of Physical Chemistry B, Vol. 114, Issue 9 https://doi.org/10.1021/jp909183x	journal	March 2010
Conjugated Polymer-Based Organic Solar Cells Günes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar Chemical Reviews, Vol. 107, Issue 4, p. 1324-1338 https://doi.org/10.1021/cr050149z	journal	April 2007
Regioregular Copolymers of 3-Alkoxythiophene and Their Photovoltaic Application Shi, Chenjun; Yao, Yan Journal of the American Chemical Society, Vol. 128, Issue 27 https://doi.org/10.1021/ja061664x	journal	July 2006

Similar Records

Influence of heteroatoms on photovoltaic performance of donor–acceptor copolymers based on 2,6-di(thiophen-2-yl)benzo[1,2-b:4,5-b']difurans and diketopyrrolopyrrole

Journal Article · Mon Dec 31 23:00:00 EST 2012 · Polymer Chemistry · OSTI ID:1382474

Chlorination of Side Chains: A Strategy for Achieving a High Open Circuit Voltage Over 1.0 V in Benzo[1,2-b:4,5-b']dithiophene-Based Non-Fullerene Solar Cells

Journal Article · Mon Apr 23 00:00:00 EDT 2018 · ACS Applied Energy Materials · OSTI ID:1440758

Temperature dependence of dc electrical conductivity of poly(benzo-[1,2-b:4,5-b{prime}]dithiophene-4,8-diyl vinylene) and poly(pyrrole)

Conference · Thu Nov 30 23:00:00 EST 1995 · OSTI ID:126949

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
materials and chemistry by design
solar (photovoltaic)' charge transport
synthesis (novel materials)
synthesis (self-assembly)

A low band-gap polymer based on unsubstituted benzo[1,2-b:4,5-b']dithiophene for high performance organic photovoltaics

Citation Formats

References (39)

Similar Records

Related Subjects