Novel high-performance photovoltaic D-A conjugated polymers bearing 1,2-squaraine moieties as electron-deficient units

Solar Energy Materials and Solar Cells

Volumn 105, Issue , 2012, Pages 220-228

  Yang, Daobin ^a   Guan, Zhiqiang ^b   Yang, Lin ^a   Huang, Yan ^a   Wei, Qingjian ^a   Lu, Zhiyun ^a   Yu, Junsheng ^b  

^a SICHUAN UNIVERSITY   (China)

^b UNIVERSITY OF ELECTRONIC SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

1,2 squaraines; Conjugated polymers; Photovoltaic; Solar cells

Indexed keywords

1,2-SQUARAINES; BULK HETEROJUNCTION; DONOR MOIETY; ELECTRON-ACCEPTOR COMPONENTS; ELECTRON-DEFICIENT; HOMO ENERGY LEVELS; P-TYPE; PHOTOVOLTAIC; STILLE COUPLING REACTION;

HETEROJUNCTIONS; SOLAR CELLS; THIOPHENE;

CONJUGATED POLYMERS;

EID: 84863423469     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2012.06.006     Document Type: Article

References (49)

1. G. Dennler, M.C. Scharber, and C.J. Brabec Polymer-fullerene bulk-heterojunction solar cells Advanced Materials 21 2009 1323 1338
2. Y.J. Cheng, S.H. Yang, and C.S. Hsu Synthesis of conjugated polymers for organic solar cell applications Chemical Reviews 109 2009 5868 5923
3. H.Y. Chen, J. Hou, S. Zhang, Y. Liang, G. Yang, Y. Yang, L. Yu, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efficiency Nature Photonics 3 2009 649 653
4. T.Y. Chu, J. Lu, S. Beaupré, Y. Zhang, J.R. Pouliot, S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. Ding, and Y. Tao Bulk heterojunction solar cells using thieno[3,4-c]pyrrole-4,6-dione and dithieno[3,2-b:2′,3′-d] silole copolymer with a power conversion efficiency of 7.3% Journal of the American Chemical Society 133 2011 4250 4253
5. N.C. Greenham, S.C. Moratti, D.D.C. Bradley, R.H. Friend, and A.B. Holmes Efficient light-emitting diodes based on polymers with high electron affinities Nature 365 1993 628 630
6. E. Bundgaard, and F.C. Krebs Low band gap polymers for organic photovoltaics Solar Energy Materials & Solar Cells 91 2007 954 985
7. K.Y. Law Organic photoconductive materials: recent trends and developments Chemical Reviews 93 1993 449 486
8. M. Binda, T. Agostinelli, M. Caironi, D. Natali, M. Sampietro, L. Beverina, R. Ruffo, and F. Silvestri Fast and air stable near-infrared organic detector based on squaraine dyes Organic Electronics 10 2009 1314 1319
9. M. Emmelius, G. Pawlowski, and H.W. Vollmann Materials for optical data storage Angewandte Chemie-International Edition 28 1989 1445 1471
10. C.T. Chen, S.R. Marder, and L.K. Cheng Syntheses and linear and nonlinear optical properties of unsymmetrical squaraines with extended conjugation Journal of the American Chemical Society 116 1994 3117 3118
11. Q. Shi, W.G. Chen, J. Xiang, X.M. Duan, and X. Zhan A low-bandgap conjugated polymer based on squaraine with strong two-photon absorption Macromolecules 44 2011 3759 3765
12. E.C.P. Smits, S. Setayesh, T.D. Anthopoulos, M. Buechel, W. Nijssen, R. Coehoorn, P.W.M. Blom, B. de Boer, and D.M. de Leeuw Near-infrared light-emitting ambipolar organic field-effect transistors Advanced Materials 19 2007 734 738
13. L.H. Liu, K. Nakatani, R. Pansu, J.J. Vachon, P. Tauc, and E. Ishow Fluorescence patterning through photoinduced migration of squaraine- functionalized azo derivatives Advanced Materials 19 2007 433 436
14. Y. Shi, R.B.M. Hill, J.H. Yum, A. Dualeh, S. Barlow, M. Grätzel, S.R. Marder, and M.K. Nazeeruddin A high-efficiency panchromatic squaraine sensitizer for dye-sensitized solar cells Angewandte Chemie-International Edition 50 2011 6619 6621
15. V.Y. Merritt, and H.J. Hovel Organic solar cells of hydroxy squarylium Applied Physics Letters 29 1976 414 416
16. D.L. Morel, A.K. Ghosh, T. Feng, E.L. Stogryn, P.E. Purwin, R.F. Shaw, and C. Fishman High- efficiency organic solar cells Applied Physics Letters 32 1978 495 497
17. F. Silvestri, M.D. Irwin, L. Beverina, A. Facchetti, G.A. Pagani, and T.J. Marks Efficient squaraine-based solution processable bulk-heterojunction solar cells Journal of the American Chemical Society 130 2008 17640 17641
18. D. Bagnis, L. Beverina, H. Huang, F. Silvestri, Y. Yao, H. Yan, G.A. Pagani, T.J. Marks, and A. Facchetti Marked alkyl- vs alkenyl-substitutent effects on squaraine dye solid-state structure, carrier mobility, and bulk-heterojunction solar cell efficiency Journal of the American Chemical Society 132 2010 4074 4075
19. S. So, H. Choi, H.M. Ko, C. Kim, S. Paek, N. Cho, K. Song, J.K. Lee, and J. Ko Novel unsymmetrical push-pull squaraine chromophores for solution processed small molecule bulk heterojunction solar cells Solar Energy Materials & Solar Cells 98 2012 227 232
20. G. Wei, X. Xiao, S. Wang, K. Sun, K.J. Bergemann, M.E. Thompson, and S.R. Forrest Functionalized squaraine donors for nanocrystalline organic photovoltaics ACS Nano 6 2012 972 978
21. G. Chen, H. Sasabe, Z. Wang, X.F. Wang, Z. Hong, Y. Yang, and J. Kido Co-evaporated bulk heterojunction solar cells with 6.0% efficiency Advanced Materials 24 2012 2768 2773
22. 70BM (1:6) solar cells Advanced Energy Materials 1 2011 184 187
23. X. Xiao, G. Wei, S. Wang, J.D. Zimmerman, C.K. Renshaw, M.E. Thompson, and S.R. Forrest Small-molecule photovoltaics based on functionalized squaraine donor blends Advanced Materials 24 2012 1956 1960
24. S.F. Volker, S. Uemura, M. Limpinsel, M. Mingebach, C. Deibel, V. Dyakonov, and C. Lambert Polymeric squaraine dyes as electron donors in bulk heterojunction solar cells Macromolecular Chemistry and Physics 211 2010 1098 1108
25. E. Ronchi, R. Ruffo, S. Rizzato, A. Albinati, L. Beverina, and G.A. Pagani Regioselective synthesis of 1,2- vs 1,3-Squaraines Organic Letters 13 2011 3166 3169
26. C.R. Chenthamarakshan, J. Eldo, and A. Ajayaghosh Synthesis and properties of alternating acceptor-donor copolymers of squaric acid with 1-dodecyl- and 3-dodecylpyrroles Macromolecules 32 1999 251 257
27. E. Huo, Y. Zou, H. Sun, Y. Huang, Z. Lu, and Q. Jiang Synthesis and characterization of novel conjugated polymers based on 3-cyclobutene-1,2-dione moiety Chinese Chemical Letters 22 2011 1326 1330
28. H. Zhou, L. Yang, S. Stoneking, and W. You A weak donor-strong acceptor strategy to design ideal polymers for organic solar cells ACS Applied Materials & Interfaces 2 2010 1377 1383
29. J. Hou, M.H. Park, S. Zhang, Y. Yao, L.M. Chen, J.H. Li, and Y. Yang Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[1,2-b:4,5-b′] dithiophene Macromolecules 41 2008 6012 6018
30. J.Y. Lee, K.W. Song, J.R. Ku, T.H. Sung, and D.K. Moon Development of DA-type polymers with phthalimide derivatives as electron withdrawing units and a promising strategy for the enhancement of photovoltaic properties Solar Energy Materials & Solar Cells 95 2011 3377 3384
31. H. Zhou, L. Yang, S. Xiao, S. Liu, and W. You Donor-acceptor polymers incorporating alkylated dithienylbenzothiadiazole for bulk heterojunction solar cells: pronounced effect of positioning alkyl chains Macromolecules 43 2010 811 820
32. Y. Zhu, I. Heim, and B. Tieke Red emitting diphenylpyrrolopyrrole (DPP)-based polymers prepared by stille and heck coupling Macromolecular Chemistry and Physics 207 2006 2206 2214
33. M. Takahashi, K. Masui, H. Sekiguchi, N. Kobayashi, A. Mori, M. Funahashi, and N. Tamaoki Palladium-catalyzed CH homocoupling of bromothiophene derivatives and synthetic application to well-defined oligothiophenes Journal of the American Chemical Society 128 2008 10930 10933
34. M.H. Lai, C.C. Chueh, W.C. Chen, J.L. Wu, and F.C. Chen Synthesis and properties of new dialkoxyphenylene quinoxaline-based donor-acceptor conjugated polymers and their applications on thin film transistors and solar cells Journal of Polymer Science A: Polymer Chemistry 47 2009 973 985
35. B. Carsten, F. He, H.J. Son, T. Xu, and L. Yu Stille polycondensation for synthesis of functional materials Chemical Reviews 111 2011 1493 1528
36. E. Zhou, J. Cong, K. Tajima, and K. Hashimoto Synthesis and photovoltaic properties of donor- acceptor copolymers based on 5,8-dithien-2-yl-2,3- diphenylquinoxaline Chemistry Materials 22 2010 4890 4895
37. H. Zhao, W.Z. Yuan, L. Tang, J.Z. Sun, H. Xu, A. Qin, Y. Mao, J.K. Jin, and B.Z. Tang Hybrids of triphenylamine-functionalized polyacetylenes and multiwalled carbon nanotubes: high solubility, strong donor-acceptor interaction, and excellent photoconductivity Macromolecules 41 2008 8566 8574
38. J. Pommerehne, H. Vestweber, W. Guss, R.F. Mahrt, H. Bassler, M. Porsch, and J. Daub Efficient two layer LEDs on a polymer blend basis Advanced Materials 7 1995 551 554
39. J.F. Lee, S.L.C. Hsu, P.I. Lee, H.Y. Chuang, M.L. Yang, J.S. Chen, and W.Y. Chou Low bandgap carbazole copolymers containing an electron-withdrawing side chain for solar cell applications Solar Energy Materials & Solar Cells 95 2011 2795 2804
40. L. Huo, J. Hou, S. Zhang, H.Y. Chen, and Y. Yang A polybenzo[1,2-b:4,5- b′]dithiophene derivative with deep HOMO level and its application in high-performance polymer solar cells Angewandte Chemie-International Edition 49 2010 1500 1503
41. P. Peumans, V. Bulović, and S.R. Forrest Efficient photon harvesting at high optical intensities in ultrathin organic double- heterostructure photovoltaic diodes Applied Physics Letters 76 2000 2650 2652
42. 60 Solar Energy Materials & Solar Cells 94 2010 263 266
43. 61 blends Applied Physics Letters 87 2005 083506
44. K. Kim, J. Liu, M.A.G. Namboothiry, and D.L. Carrolla Roles of donor and acceptor nanodomains in 6% efficient thermally annealed polymer photovoltaics Applied Physics Letters 90 2007 163511
45. M.C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A.J. Heeger, and C.J. Brabec Design rules for donors in bulk-heterojunction solar cells-towards 10% energy-conversion efficiency Advanced Materials 18 2006 789 794
46. T. Yamanari, T. Taima, J. Sakai, and K. Saito Origin of the open-circuit voltage of organic thin-film solar cells based on conjugated polymers Solar Energy Materials & Solar Cells 93 2009 759 761
47. 60 bisadduct by device optimization Advanced Materials 22 2010 4355 4358
48. T.L. Wang, A.C. Yeh, C.H. Yang, Y.T. Shieh, W.J. Chen, and T.H. Ho Synthesis and photovoltaic properties of a low bandgap donor-acceptor alternating copolymer with benzothiadiazole unit Solar Energy Materials & Solar Cells 95 2011 3295 3302
49. Y. Li, Y. Chen, X. Liu, Z. Wang, X. Yang, Y. Tu, and X. Zhu Controlling blend film morphology by varying alkyl side chain in highly coplanar donor-acceptor copolymers for photovoltaic application Macromolecules 44 2011 6370 6381