Low band gap copolymers consisting of porphyrins, thiophenes, and 2,1,3‐benzothiadiazole moieties for bulk heterojunction solar cells

Two novel low band gap conjugated copolymers containing porphyrins, thiophenes, and 2,1,3-benzothiadiazole (BTZ) moieties were synthesized and applied in bulk heterojunction solar cells. The thermal, optical, electrochemical, and photovoltaic properties of the two copolymers were examined to investigate the effect of the introduction of BTZ moiety in the backbone of the porphyrin polymers. The copolymers exhibited good thermal stability and film-forming ability. The absorption spectra indicated that the BTZ moiety has significant influence on the UV―visible region spectra of the copolymers: with increasing the molar amount of BTZ moieties in conjugated main chain, the absorption in the range of 450― 700 nm is largely broadened and red-shifted compared to the similar polymers without BTZ moiety, and the optical band gaps of copolymers were narrowed to ∼1.50 eV. The photoluminescence spectra showed that there is effective charge transfer in the whole conjugated main chain. Cyclic voltammetry displayed that the band gaps were reduced effectively by the introduction of the BTZ moieties. The bulk heterojunction solar cells were fabricated based on the blend of the copolymers and [6,6]-phenyl-C 61 -butyric acid methyl ester (PC 61 BM) in a 1:2 weight ratio. The maximum power conversion efficiency of 0.91% was obtained by using P2 as the electron donor under the illumination of AM 1.5, 100 mW/cm 2 .

[1]  Martijn Lenes,et al.  Small Bandgap Polymers for Organic Solar Cells (Polymer Material Development in the Last 5 Years) , 2008 .

[2]  Christoph J. Brabec,et al.  Design Rules for Donors in Bulk‐Heterojunction Solar Cells—Towards 10 % Energy‐Conversion Efficiency , 2006 .

[3]  René A. J. Janssen,et al.  Synthesis and photovoltaic performance of a series of small band gap polymers , 2009 .

[4]  Fei Huang,et al.  Development of new conjugated polymers with donor-pi-bridge-acceptor side chains for high performance solar cells. , 2009, Journal of the American Chemical Society.

[5]  A. Jen,et al.  High Performance Amorphous Metallated π-Conjugated Polymers for Field-Effect Transistors and Polymer Solar Cells , 2008 .

[6]  A. Heeger,et al.  Flexible light-emitting diodes made from soluble conducting polymers , 1992, Nature.

[7]  Bin Zhao,et al.  Synthesis and photovoltaic properties of polythiophene stars with porphyrin core , 2010 .

[8]  Yang Yang,et al.  Synthesis, characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole. , 2008, Journal of the American Chemical Society.

[9]  J. Fréchet,et al.  Polymer-fullerene composite solar cells. , 2008, Angewandte Chemie.

[10]  D. D. de Leeuw,et al.  Poly(diketopyrrolopyrrole-terthiophene) for ambipolar logic and photovoltaics. , 2009, Journal of the American Chemical Society.

[11]  Bin Zhao,et al.  Synthesis and characterization of porphyrin-terthiophene and oligothiophene π-conjugated copolymers for polymer solar cells , 2010 .

[12]  A. Bard,et al.  Effect of Structural Variation on Photocurrent Efficiency in Alkyl-Substituted Porphyrin Solid-State Thin Layer Photocells , 1998 .

[13]  J. Brédas,et al.  Molecular understanding of organic solar cells: the challenges. , 2009, Accounts of chemical research.

[14]  O. Inganäs,et al.  Polymer Photovoltaics with Alternating Copolymer/Fullerene Blends and Novel Device Architectures , 2010, Advanced materials.

[15]  Yang Yang,et al.  A polybenzo[1,2-b:4,5-b']dithiophene derivative with deep HOMO level and its application in high-performance polymer solar cells. , 2010, Angewandte Chemie.

[16]  Ye Tao,et al.  A thieno[3,4-c]pyrrole-4,6-dione-based copolymer for efficient solar cells. , 2010, Journal of the American Chemical Society.

[18]  J. Reynolds,et al.  Spectral Broadening in MEH-PPV:PCBM-Based Photovoltaic Devices via Blending with a Narrow Band Gap Cyanovinylene−Dioxythiophene Polymer , 2005 .

[19]  R. N. Marks,et al.  Light-emitting diodes based on conjugated polymers , 1990, Nature.

[20]  Yunlong Guo,et al.  Porphyrin−Dithienothiophene π-Conjugated Copolymers: Synthesis and Their Applications in Field-Effect Transistors and Solar Cells , 2008 .

[21]  Alex K.-Y. Jen,et al.  Efficient Polymer Solar Cells Based on the Copolymers of Benzodithiophene and Thienopyrroledione , 2010 .

[22]  Yong Cao,et al.  Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. , 2009, Accounts of chemical research.

[23]  K. Schanze,et al.  Donor–acceptor copolymers for red‐ and near‐infrared‐emitting polymer light‐emitting diodes , 2005 .

[24]  Nelson E. Coates,et al.  Bulk heterojunction solar cells with internal quantum efficiency approaching 100 , 2009 .

[25]  M. Andersson,et al.  A planar copolymer for high efficiency polymer solar cells. , 2009, Journal of the American Chemical Society.

[26]  Chain‐Shu Hsu,et al.  Synthesis of conjugated polymers for organic solar cell applications. , 2009, Chemical reviews.

[27]  Jianhui Hou,et al.  Synthesis and Photovoltaic Properties of Two Benzo[1,2-b:3,4-b′]dithiophene-Based Conjugated Polymers , 2009 .

[28]  N. E. Coates,et al.  Efficient Tandem Polymer Solar Cells Fabricated by All-Solution Processing , 2007, Science.