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Ethynylene-linked benzo[1,2-b:4,5-b']dithiophene-alt-diketopyrrolopyrrole alternating copolymer: optoelectronic properties, film morphology and photovoltaic applications

Journal Article · · Journal of Materials Chemistry. A
DOI:https://doi.org/10.1039/c5ta01004g· OSTI ID:1370264
 [1];  [2];  [2];  [3];  [3];  [2];  [2];  [2];  [4];  [5]
  1. Shanghai Univ. (China); Fudan Univ., Shanghai (China)
  2. Shanghai Univ. (China)
  3. Univ. of Massachusetts, Amherst, MA (United States)
  4. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  5. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of Massachusetts, Amherst, MA (United States)

Here, an ethynylene-linked benzo[1,2-b:4,5-b']dithiophene-alt-diketopyrrolopyrrole alternating copolymer, EDPP, was designed and synthesized to improve the open-circuit voltage of organic solar cells. The influence of the ethynylene on optoelectronic properties, energy levels, crystallinity, film morphology, and photovoltaic performance was investigated. Optical and electrochemical tests showed that introduction of ethynylene into the polymer backbone resulted in a larger bandgap, deeper HOMO energy level, and enhanced crystallinity due to the planar conformation and electron-withdrawing properties. Grazing incidence wide-angle X-ray scattering (GIWAXS) showed that the pure EDPP film preferentially adopted a face-on orientation with a π–π stacking distance of 3.65 Å. After thermal annealing the face-on and edge-on orientations coexisted and the overall degree of crystallinity increased. Blending with PC71BM did not disrupt the crystallinity of the EDPP. Resonant soft X-ray scattering (RSoXS) showed that the EDPP:PC71BM blend films contained large domains, a few hundred nanometers in size. As a result, EDPP:PC71BM photovoltaic devices exhibited a high open-circuit voltage of 0.88 V, but a low short-circuit current, with a moderate power conversion efficiency of 1.98%.

Research Organization:
Energy Frontier Research Centers (EFRC) (United States). Polymer-Based Materials for Harvesting Solar Energy (PHaSE)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC)
Grant/Contract Number:
SC0001087
OSTI ID:
1370264
Journal Information:
Journal of Materials Chemistry. A, Journal Name: Journal of Materials Chemistry. A Journal Issue: 24 Vol. 3; ISSN 2050-7488
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (59)

Bimolecular Crystals of Fullerenes in Conjugated Polymers and the Implications of Molecular Mixing for Solar Cells journal April 2009
Highly Efficient Blue Electroluminescence from Poly(phenylene ethynylene) via Energy Transfer from a Hole-Transport Matrix journal August 2005
A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells journal September 2007
Simultaneous Enhancement of Open-Circuit Voltage, Short-Circuit Current Density, and Fill Factor in Polymer Solar Cells journal September 2011
Bithiophene Imide and Benzodithiophene Copolymers for Efficient Inverted Polymer Solar Cells journal March 2012
Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications journal September 2012
A Selenium-Substituted Low-Bandgap Polymer with Versatile Photovoltaic Applications journal November 2012
The Role of Additive in Diketopyrrolopyrrole-Based Small Molecular Bulk Heterojunction Solar Cells journal August 2013
Improved Photovoltaic Performance of PPV-Based Copolymers Using Optimized Fullerene-Based Counterparts journal June 2012
Polymer–Fullerene Composite Solar Cells journal January 2008
Platinum(II)-Bis(aryleneethynylene) Complexes for Solution-Processible Molecular Bulk Heterojunction Solar Cells journal December 2011
Synthesis and optoelectronic characterization of poly(fluorenylethynylene)s containing perylene bisimide moiety in the backbone journal September 2008
On the morphology of polymer-based photovoltaics journal March 2012
Photovoltaic devices based on a novel poly(phenylene ethynylene) derivative journal February 2004
Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices journal February 1997
Low-band gap copolymers of ethynylfluorene and 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione synthesized under microwave irradiation for polymer photovoltaic cells journal June 2011
Fluorescence “turn-on” metal ion sensors based on switching of intramolecular charge transfer of donor–acceptor systems journal October 2010
A Weak Donor−Strong Acceptor Strategy to Design Ideal Polymers for Organic Solar Cells journal April 2010
Alternating Polyfluorenes Collect Solar Light in Polymer Photovoltaics journal November 2009
Use of a Folate−PPE Conjugate To Image Cancer Cells in Vitro journal May 2007
High Open-Circuit Voltage Poly(ethynylene bithienylene):Fullerene Solar Cells journal December 2006
Ambipolar Semiconducting Polymers with π- Spacer Linked Bis-Benzothiadiazole Blocks as Strong Accepting Units journal August 2014
Conformation-Insensitive Ambipolar Charge Transport in a Diketopyrrolopyrrole-Based Co-polymer Containing Acetylene Linkages journal June 2014
Cyclometalated Platinum Polymers: Synthesis, Photophysical Properties, and Photovoltaic Performance journal March 2010
Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers journal April 2007
Synthesis of Conjugated Polymers for Organic Solar Cell Applications journal November 2009
Poly(aryleneethynylene)s:  Syntheses, Properties, Structures, and Applications journal April 2000
Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties journal January 1995
Switching of Intramolecular Charge Transfer in Cruciforms:  Metal Ion Sensing journal March 2005
Synthesis of Fluorinated Polythienothiophene- co -benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties journal February 2011
Systematic Investigation of Benzodithiophene- and Diketopyrrolopyrrole-Based Low-Bandgap Polymers Designed for Single Junction and Tandem Polymer Solar Cells journal June 2012
Linear Side Chains in Benzo[1,2- b :4,5- b ′]dithiophene–Thieno[3,4- c ]pyrrole-4,6-dione Polymers Direct Self-Assembly and Solar Cell Performance journal March 2013
High Quantum Efficiencies in Polymer Solar Cells at Energy Losses below 0.6 eV journal February 2015
Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells journal May 2010
Design, synthesis, and control of conducting polymer architectures: structurally homogeneous poly(3-alkylthiophenes) journal February 1993
Alkyl Side Chain Impact on the Charge Transport and Photovoltaic Properties of Benzodithiophene and Diketopyrrolopyrrole-Based Copolymers journal August 2011
Nanostructures and Electronic Properties of a High-Efficiency Electron-Donating Polymer journal November 2013
Synthesis of Diketopyrrolopyrrole Containing Copolymers: A Study of Their Optical and Photovoltaic Properties journal March 2010
Conjugated Donor−Acceptor Copolymer Semiconductors with Large Intramolecular Charge Transfer:  Synthesis, Optical Properties, Electrochemistry, and Field Effect Carrier Mobility of Thienopyrazine-Based Copolymers journal December 2006
Benzodipyrrolidones and Their Polymers journal October 2011
New Alkylfuranyl-Substituted Benzo[1,2- b :4,5- b ′]dithiophene-Based Donor–Acceptor Polymers for Highly Efficient Solar Cells journal February 2013
Ethynylene-Linked Donor–Acceptor Alternating Copolymers journal April 2013
Simultaneous Enhancement of Solar Cell Efficiency and Photostability via Chemical Tuning of Electron Donating Units in Diketopyrrolopyrrole-Based Push–Pull Type Polymers journal September 2014
A Novel Tetrathiafulvalene- (TTF-) Fused Poly(aryleneethynylene) with an Acceptor Main Chain and Donor Side Chains: Intramolecular Charge Transfer (CT), Stacking Structure, and Photovoltaic Property journal May 2008
Porphyrin−Dithienothiophene π-Conjugated Copolymers: Synthesis and Their Applications in Field-Effect Transistors and Solar Cells journal October 2008
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 journal September 2009
New A-A-D-A-A-Type Electron Donors for Small Molecule Organic Solar Cells journal September 2011
Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells journal May 2007
Solution-processed small-molecule solar cells: breaking the 10% power conversion efficiency journal November 2013
Solution-processed bulk heterojunction solar cells based on a porphyrin small molecule with 7% power conversion efficiency journal January 2014
High performance asymmetrical push–pull small molecules end-capped with cyanophenyl for solution-processed solar cells journal January 2014
A low band-gap polymer based on unsubstituted benzo[1,2-b:4,5-b′]dithiophene for high performance organic photovoltaics journal January 2012
Copolymerization of 3,3′′′-didodecylquaterthiophene with fluorene and silole units: improving photovoltaic performance by tuning energy levels journal January 2012
Structural modification of thieno[3,4-c]pyrrole-4,6-dione: structure–property relationships and application in solution-processed small-molecule organic solar cells journal January 2013
A novel benzodipyrrolidone-based low band gap polymer for organic solar cells journal January 2013
Dihydropyrroloindoledione-based copolymers for organic electronics journal January 2013
Arenedithiocarboxyimide-containing extended π-conjugated systems with high electron affinity journal January 2013
Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions journal December 1995
Acetylene-Based Materials in Organic Photovoltaics journal April 2010

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Synthesis of fluorinated diphenyl-diketopyrrolopyrrole derivatives as new building blocks for conjugated copolymers journal January 2016
A diketopyrrolopyrrole-based fluorescent probe for investigating mitochondrial zinc ions journal January 2018
Amidinium–carboxylate salt bridge mediated proton-coupled electron transfer in a donor–acceptor supramolecular system journal January 2019
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