Synthesis of conjugated polymers bearing indacenodithiophene and cyclometalated platinum(II) units and their application in organic photovoltaics

Solar Energy Materials and Solar Cells

Volumn 109, Issue , 2013, Pages 111-119

  Liao, Chuang Yi ^a   Chen, Chih Ping ^b   Chang, Ching Chih ^a   Hwang, Gue Wuu ^c   Chou, Ho Hsiu ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b MING CHI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^c INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE   (Taiwan)

Author keywords

Cyclometalated polymers; Organic photovoltaics; Platinum

Indexed keywords

FILL FACTOR; METHYL ESTERS; ORGANIC PHOTOVOLTAICS; PHOTOVOLTAIC PROPERTY; POWER CONVERSION EFFICIENCIES; RED-SHIFTED; SPACE CHARGE LIMITED CURRENTS; WEIGHT RATIOS;

CONVERSION EFFICIENCY; DENSITY FUNCTIONAL THEORY; OPEN CIRCUIT VOLTAGE; ORGANOMETALLICS; PLATINUM; THIOPHENE;

CONJUGATED POLYMERS;

EID: 84869128536     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2012.09.033     Document Type: Article

References (43)

1. B.C. Thompson, and J.M.J. Fréchet Polymer-Fullerene composite solar cells Angewandte Chemie International Edition 47 2007 58 77
2. P. Heremans, D. Cheyns, and B.P. Rand Strategies for increasing the efficiency of heterojunction organic solar cells: material selection and device architecture Accounts of Chemical Research 42 2009 1740 1747
3. M. Helgesen, R. Sondergaard, and F.C. Krebs Advanced materials and processes for polymer solar cell devices Journal of Materials Chemistry 20 2010 36 60
4. F.C. Krebs Polymer solar cell modules prepared using roll-to-roll methods: knife-over-edge coating, slot-die coating and screen printing Solar Energy Materials and Solar Cells 93 2009 465 475
5. F.C. Krebs, J. Fyenbo, D.M. Tanenbaum, S.A. Gevorgyan, R. Andriessen, B. van Remoortere, Y. Galagan, and M. Jorgensen The OE-A OPV demonstrator anno domini 2011 Energy Environmental Science 4 2011 4116 4123
6. M. Jorgensen, K. Norrman, S.A. Gevorgyan, T. Tromholt, B. Andreasen, and F.C. Krebs Stability of polymer solar cell Advanced Materials 24 2012 580 612
7. G. Dennler, M.C. Scharber, and C.J. Brabec Polymer-Fullerene bulk-heterojunction solar cell Advanced Materials 21 2009 1323 1338
8. J. Lu, F. Liang, N. Drolet, J. Ding, Y. Tao, and R. Movileanu Crystalline low band-gap alternating indolocarbazole and benzothiadiazole-cored oligothiophene copolymer for organic solar cell applications Chemical Communications 2008 5315 5317
9. A. Köhler, H.F. Wittmann, R.H. Friend, M.S. Khan, and J. Lewis Enhanced photocurrent response in photocells made with platinum-poly-yne/C60 blends by photoinduced electron transfer Synthetic Metal 77 1996 147 150
10. Y. Shao, and Y. Yang Efficient organic heterojunction photovoltaic cells based on triplet materials Advanced Materials 17 2005 2841 2844
11. F. Guo, Y.-G. Kim, J.R. Reynolds, and K.S. Schanze Platinum-acetylide polymer based solar cells: involvement of the triplet state for energy conversion Chemical Communications 2006 1887 1889
12. F. Guo, K. Ogawa, Y.-G. Kim, E.O. Danilov, F.N. Castellano, J.R. Reynolds, and K.S. Schanze A fulleropyrrolidine end-capped platinum-acetylide triad: the mechanism of photoinduced charge transfer in organometallic photovoltaic cell Physical Chemistry Chemical Physics 9 2007 2724 2734
13. K.Y.K. Man, H.L. Wong, and W.K. Chan Use of a ruthenium-containing conjugated polymer as a photosensitizer in photovoltaic devices fabricated by a layer-by-layer deposition process Langmuir 22 2006 3368 3375
14. K.W. Cheng, C.S.C. Mak, W.K. Chan, A.M.C. Ng, and A.B. Djurišic Synthesis of conjugated polymers with pendant ruthenium terpyridine trithiocyanato complexes and their applications in heterojunction photovoltaic cells Journal of Polymer Science Part A: Polymer Chemistry 46 2008 1305 1317
15. G.L. Schulz, and S. Holdcroft Conjugated polymers bearing iridium complexes for triplet photovoltaic devices Chemistry of Materials 20 2008 5351 5355
16. W.-Y. Wong Metallopolyyne polymers as new functional materials for photovoltaic and solar cell applications Macromolecular Chemistry and Physics 209 2008 14 24
17. W.-Y. Wong, X.-Z. Wang, Z. He, K.-K. Chan, A.B. Djurišic, K.-Y. Cheung, C.-T. Yip, A.M.C. Ng, Y.Y. Xi, C.S.K. Mak, and W.-K. Chan Tuning the absorption, charge transport properties, and solar cell efficiency with the number of thienyl rings in platinum-containing poly(aryleneethynylene)s Journal of the American Chemical Society 129 2007 14372 14380
18. P.-T. Wu, T. Bull, F.S. Kim, C.K. Luscombe, and S.A. Jenekhe Organometallic donor-acceptor conjugated polymer semiconductors: tunable optical, electrochemical, charge transport, and photovoltaic properties Macromolecules 42 2009 671 681
19. J. Mei, K. Ogawa, Y.-G. Kim, N.C. Heston, D.J. Arenas, Z. Nasrollahi, T.D. McCarley, D.B. Tanner, J.R. Reynolds, and K.S. Schanze Low-band-gap platinum acetylide polymers as active materials for organic solar cells ACS Applied Materials Interfaces 1 2009 150 161
20. L. Sudha Devi, M.K. Al-Suti, N. Zhang, S.J. Teat, L. Male, H.A. Sparkes, P.R. Raithby, M.S. Khan, and A. Köhler Synthesis and comparison of the optical properties of platinum(II) poly-ynes with fused and non-fused oligothiophenes Macromolecules 42 2009 1131 1141
21. N.S. Baek, S.K. Hau, H.-L. Yip, O. Acton, K.-S. Chen, and A.K.-Y. Jen High performance amorphous metallated π-conjugated polymers for field-effect transistors and polymer solar cells Chemistry of Materials 20 2008 5734 5736
22. X.-Z. Wang, W.-Y. Wong, K.-Y. Cheung, M.-K. Fung, A.B. Djurišic, and W.-K. Chan Polymer solar cells based on very narrow-bandgap polyplatinynes with photocurrents extended into the near-infrared region Dalton Transactions 2008 5484 5494
23. T.A. Clem, D.F.J. Kavulak, E.J. Westling, and J.M.J. Fréchet Cyclometalated platinum polymers: synthesis, photophysical properties, and photovoltaic performance Chemistry of Materials 22 2010 1977 1987
24. W.-Y. Wong, X.-Z. Wang, Z. He, A.B. Djurišic, C.-T. Yip, K.-Y. Cheung, H. Wang, C.S.-K. Mak, and W.-K. Chan Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells Nature Materials 6 2007 521 527
25. A.A. Rachford, S. Goeb, and F.N. Castellano Accessing the triplet excited state in perylenediimides Journal of the American Chemical Society 130 2008 2766 2767
26. J. Brooks, Y. Babayan, S. Lamansky, P.I. Djurovich, I. Tsyba, R. Bau, and M.E. Thompson Synthesis and characterization of phosphorescent cyclometalated platinum complexes Inorganic Chemistry 41 2002 3055 3066
27. C.-P. Chen, S.-H. Chan, T.-C. Chao, C. Ting, and B.-T. Ko Low-band gap poly(thiophene-phenylene-thiophene) derivatives with broaden absorption spectra for use in high-performance bulk-heterojunction polymer solar cells Journal of the American Chemical Society 130 2008 12828 12833
28. C.-P. Chen, Y.-D. Chen, and S.-C. Chuang High-performance and highly durable inverted organic photovoltaics embedding solution-processable vanadium oxides as an interfacial hole-transporting layer Advanced Materials 23 2011 3859 3863
29. C.-Y. Yu, C.-P. Chen, S.-H. Chan, G.-W. Hwang, and C. Ting Thiophene/phenylene/thiophene-based low-bandgap conjugated polymers for efficient near-infrared photovoltaic applications Chemistry of Materials 21 2009 3262 3269
30. Y.-C. Chen, C.-Y. Yu, Y.-L. Fan, L.-I. Hung, C.-P. Chen, and C. Ting Low-bandgap conjugated polymer for high efficient photovoltaic applications Chemical Communications 46 2010 6503 6505
31. K.T. Wong, T.-C. Chao, L.-C. Chi, Y.-Y. Chu, A. Balaiah, S.-F. Chiu, Y.-H. Liu, and Y. Wang Syntheses and structures of novel heteroarene-fused coplanar π-conjugated chromophores Organic Letters 8 2006 5033 5036
32. T. Yamamoto, T. Maruyama, Z.-H. Zhou, T. Ito, T. Fukuda, Y. Yoneda, F. Begum, T. Ikeda, S. Sasaki, H. Takezoe, A. Fukuda, and K. Kubota π-conjugated poly(pyridine-2,5-diyl), poly(2,2′-bipyridine-5,5′-diyl), and their alkyl derivatives. Preparation, linear structure, function as a ligand to form their transition metal complexes, catalytic reactions, n-type electrically conducting properties, optical properties, and alignment on substrates Journal of the American Chemical Society 116 1994 4832 4845
33. K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, and S. Yamaguchi Silole derivatives as efficient electron transporting materials Journal of the American Chemical Society 118 1996 11974 11975
34. M. Klein, P. Sandner, R. Frey, B. Riedl, O. Christensen, Compounds for treating pulmonary hypertension, WO2007118602.
35. S.-H. Chan, C.-P. Chen, T.-C. Chao, C. Ting, C.-S. Lin, and B.T. Ko Synthesis, characterization, and photovoltaic properties of novel semiconducting polymers with thiophene-phenylene-thiophene (TPT) as coplanar units Macromolecules 41 2008 5519 5526
36. K.-T. Wong, T.-H. Hung, T.-C. Chao, and T.-I. Ho Synthesis, properties, and electrogenerated chemiluminescence (ECL) of a novel carbazole-based chromophore Tetrahedron Letters 46 2005 855 858
37. S.W. Thomas III, S. Yagi, and T.M. Swager Towards chemosensing phosphorescent conjugated polymers: cyclometalated platinum(II) poly(phenylene)s Journal of Materials Chemistry 15 2005 2829 2835
38. D.N. Kozhevnikov, V.N. Kozhevnikov, M.Z. Shafikov, A.M. Prokhorov, D.W. Bruce, and J.A.G. Williams Phosphorescence vs fluorescence in cyclometalated platinum(II) and iridium(III) complexes of (oligo)thienylpyridines Inorganic Chemistry 50 2011 3804 3815
39. J.S. Wilson, N. Chawdhury, M.R.A. Al-Mandhary, M. Younus, M.S. Khan, P.R. Raithby, A. Köhler, and R.H. Friend The energy gap law for triplet states in Pt-containing conjugated polymers and monomers Journal of the American Chemical Society 123 2001 9412 9417
40. Q. Zheng, B.J. Jung, J. Sun, and H.E. Katz Ladder-type oligo-p-phenylene-containing copolymers with high open-circuit voltage and ambient photovoltaic activity Journal of the American Chemical Society 132 2010 5394 5404
41. N. Chawdhury, A. Köhler, R.H. Friend, W.-Y. Wong, J. Lewis, M. Younus, P.R. Raithby, T.C. Corcoran, M.R.A. Al-Mandhary, and M.S. Khan Evolution of lowest singlet and triplet excited states with number of thienyl rings in platinum poly-ynes Journal of Chemical Physics 110 1999 4963 4970
42. J.S. Wilson, A. Köhler, R.H. Friend, M.K. Al-Suti, M.R.A. Al-Mandhary, M.S. Khan, and P.R. Raithby Triplet states in a series of Pt-containing ethynylenes Journal of Chemical Physics 113 2000 7627 7634
43. G. Kim, H.R. Yeom, S. Cho, J.H. Seo, J.Y. Kim, and C. Yang Easily attainable phenothiazine-based polymers for polymer solar cells: advantage of S,S-dioxides into its polymer for inverted structure solar cells Macromolecules 45 2012 1847 1857