Efficient hybrid bulk heterojunction solar cells based on phenylenevinylene copolymer, perylene bisimide and TiO2

Solar Energy Materials and Solar Cells

Volumn 93, Issue 10, 2009, Pages 1792-1800

  Mikroyannidis, John A ^a   Stylianakis, Minas M ^a   Suresh, P ^b   Sharma, G D ^b  

^a UNIVERSITY OF PATRAS   (Greece)

^b JAI NARAIN VYAS UNIVERSITY   (India)

Author keywords

Anthracene; Copolymerization; Hybrid bulk heterojunction; Organic solar cells; Phenylenevinylene; TiO2

Indexed keywords

4-TERT-BUTYLPYRIDINE; ABSORPTION MAXIMA; AL ELECTRODE; BULK HETEROJUNCTION SOLAR CELLS; COATED GLASS; ELECTRON ACCEPTOR; EMISSION SPECTRUMS; GLASS TRANSITION TEMPERATURE; HECK COUPLING; HYBRID BULK HETEROJUNCTION; HYBRID COMPOSITES; INDIUM TIN OXIDE; INTERFACIAL AREAS; INTRAMOLECULAR ENERGY TRANSFER; LI SALT; MAIN CHAINS; ORGANIC SOLAR CELLS; PERYLENE BISIMIDES; PERYLENES; PHENYLENEVINYLENE; PHOTO-INDUCED; PHOTOACTIVE LAYERS; PHOTOVOLTAIC DEVICES; POWER CONVERSION EFFICIENCIES; THIOPHENE RING; TIO; TIO2;

ANTHRACENE; CARRIER MOBILITY; CONVERSION EFFICIENCY; COPOLYMERIZATION; ELECTRON TRANSITIONS; EMISSION SPECTROSCOPY; ENERGY TRANSFER; GLASS; GLASS TRANSITION; HETEROJUNCTIONS; INDIUM; ORGANIC POLYMERS; PHOTOVOLTAIC CELLS; PHOTOVOLTAIC EFFECTS; SOLAR CELLS; THIOPHENE; TIN;

SOLAR ENERGY;

EID: 68349097445     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2009.06.013     Document Type: Article

References (65)

1. Heeger A.J. Semiconducting and metallic polymers: the fourth generation of polymeric materials. J. Phys. Chem. B 105 (2001) 8475-8491
2. Saraciftci N.S., Smilowitz L., Heeger A.J., and Wudl F. Photoinduced electron transfer from a conducting polymer to buckminsterfullerene. Science 258 (1992) 1474-1476
3. Granström M., Petritsch K., Arias A.C., Lux A., Andersson M.R., and Friend R.H. Laminated fabrication of polymeric photovoltaic diodes. Nature (London) 395 (1998) 257-260
4. Coakley K.M., and McGehee M.D. Conjugated polymer photovoltaic cells. Chem. Mater. 16 (2004) 4533-4542
5. Brabec C.J. Organic photovoltaics: technology and market. Sol. Energy Mater. Sol. Cells 83 (2004) 273-292
6. Martens T., D'Haen J., Munters T., Beelen Z., Goris L., Manca J., D'Olieslaeger M., Vanderzande D., de Schepper L., and Andriessen R. Disclosure of the nanostructure of MDMO-PPV:PCBM bulk hetero-junction organic solar cells by a combination of SPM and TEM. Synth. Met. 138 (2003) 243-247
7. Hoppe H., Niggemann M., Winder C., Kraut J., Hiesgen R., Hinsch A., and Meissner D. N.S. Saraciftci nanoscale morphology of conjugated polymer/fullerene-based bulk-heterojunction solar cells. Adv. Funct. Mater. 14 (2004) 1005-1011
8. Zhang F.L., Johansson M., Andersson M.R., Hummelen J.C., and Inganäs O. Polymer solar cells based on MEH-PPV and PCBM. Synth. Met. 137 (2003) 1401-1402
9. Reyes-Reyes M., Kim K., Dewald J., Lopez-Sandoval R., Avadhanula A., Curran S., and Carroll D.L. Meso-structure formation for enhanced organic photovoltaic cells. Org. Lett. 7 (2005) 5749-5752
10. Kim J.Y., Lee K., Coates N.E., Moses D., Nguyen T.Q., Dante M., and Heeger A.J. Efficient tandem polymer solar cells fabricated by all-solution processing. Science 317 (2007) 222-225
11. Hoppe H., and Sariciftci N.S. Morphology of polymer/fullerene bulk heterojunction solar cells. J. Mater. Chem. 16 (2006) 45-61
12. Bundgaard E., and Krebs F.C. Low band gap polymers for organic photovoltaics. Sol. Energy Mater. Sol. Cells 91 (2007) 954-985
13. Guenes S., Neugebauer H., and Sariciftci N.S. Conjugated polymer-based organic solar cells. Chem. Rev. 107 (2007) 1324-1338
14. Boucle J., Ravirajan P., and Nelson J. Hybrid polymer-metal oxide thin films for photovoltaic applications. J. Mater. Chem. 17 (2007) 3141-3153
15. Joergensen M., Norrman K., and Krebs F.C. Stability/degradation of polymer solar cells. Sol. Energy Mater. Sol. Cells 92 (2008) 686-714
16. Thompson B.C., and Frechet J.M.J. Polymer-fullerene composite solar cells. Angew. Chem. Int. Ed. 47 (2008) 58-77
17. Kroon R., Lenes M., Hummelen J.C., Blom P.W.M., and de Boer B. Bert, small bandgap polymers for organic solar cells (polymer material development in the last 5 years). Polym. Rev. 48 (2008) 531-582
18. Krebs F.C. Fabrication and processing of polymer solar cells: a review of printing and coating techniques. Sol. Energy Mater. Sol. Cells 93 (2009) 394-412
19. Lemaur V., Steel M., Beljonne D., Bredas J.L., and Cornil J. Photoinduced charge generation and recombination dynamics in model donor/acceptor pairs for organic solar cell applications: a full quantum-chemical treatment. J. Am. Chem. Soc. 127 (2005) 6077-6086
20. Milliron D.J., Gur I., and Alivisatos A.P. Hybrid organic-nanocrystal solar cells. Mater. Res. Bull. 30 (2005) 41-44
21. Kwong C.Y., Djurišic′ A.B., Chui P.C., Cheng K.W., and Chan W.K. Influence of solvent on film morphology and device performance of poly(3-hexylthiophene):TiO2 nanocomposite solar cells. Chem. Phys. Lett. 384 (2004) 372-375
22. Beek W.J.E., Wienk M.M., and Janssen R.A. Efficient hybrid solar cells from zinc oxide nanoparticles and a conjugated polymer. J. Adv. Mater. 16 (2004) 1009-1013
23. Koster L.J.A., van Strien W.J., Beek W.J.E., and Blom P.W.M. Device operation of conjugated polymer/zinc oxide bulk heterojunction solar cells. Adv. Funct. Mater. 17 (2007) 1297-1302
24. Beek W.J.E., Wienk M.M., and Janssen R.A. Hybrid solar cells from regioregular polythiophene and ZnO nanoparticles. J. Adv. Funct. Mater. 16 (2006) 1112-1116
25. Ravirajan P., Peiró A.M., Nazeeruddin M.K., Graetzel M., Bradley D.D.C., Durrant J.R., and Nelson J. 1. Hybrid polymer/Zinc Oxide photovoltaic devices with vertically oriented ZnO nanorods and an amphiphilic molecular interface Layer. J. Phys. Chem. B 110 (2006) 7635-7639
26. Huynh W.U., Dittmer J.J., and Alivisatos A.P. Hybrid nanorod-polymer solar cells. Science 295 (2002) 2425-2427
27. Sun B., Marx E., and Greenham N.C. Photovoltaic devices using blends of branched CdSe nanoparticles and conjugated polymers. Nano Lett. 3 (2003) 961-963
28. Sun B., Snaith H.J., Dhoot A.S., and Westenhoff Sand Greenham N.C. Vertically segregated hybrid blends for photovoltaic devices with improved efficiency. J. Appl. Phys. 97 (2005) 014914/1-014914/6
29. Coakley K.M., and McGehee M.D. Photovoltaic cells made from conjugated polymers infiltrated into mesoporous titania. Appl. Phys. Lett. 83 (2003) 3380-3382
30. Coakley K.M., Liu Y., McGehee M.D., Frindell K.L., and Stucky G.D. Infiltrating semiconducting polymers into self-assembled mesoporous titania films for photovoltaic applications. Adv. Funct. Mater. 13 (2003) 301-306
31. Krebs F.C. Air stable polymer photovoltaics based on a process free from vacuum steps and fullerenes. Sol. Energy Mater. Sol. Cells 92 (2008) 715-726
32. Krebs F.C., Jorgensen M., Norrman K., Hagemann O., Alstrup J., Nielsen T.D., Fyenbo J., Larsen K., and Kristensen J. A complete process for production of flexible large area polymer solar cells entirely using screen printing-first public demonstration. Sol. Energy Mater. Sol. Cells 93 (2009) 422-441
33. Krebs F.C. Polymer solar cell modules prepared using roll-to-roll methods: knife-over-edge coating, slot-die coating and screen printing. Sol. Energy Mater. Sol. Cells 93 (2009) 465-475
34. Krebs F.C., Gevorgyan S.A., and Alstrup J. A roll-to-roll process to flexible polymer solar cells model studies, manufacture and operation stability studies. J. Mater. Chem (2009). 〈http://dx.doi.org/10.1039/B823001C〉
35. Krebs F.C. All solution roll-to-roll processed polymer solar cells free from indium-tin-oxide and vacuum coating steps. Org. Electron. (2009). 〈http://dx.doi.org/10.1016/j.orgel.2009.03.009〉
36. Park S.H., Roy A., Beaupré S., Cho S., Coates N., Moon J.S., Moses D., Leclerc M., Lee K., and Heeger A.J. Bulk heteronjuction solar cells with internal quantum efficiency approaching 100%. Nat. Photonics 3 (2009) 297-303
37. Ego C., Marsitzky D., Becker S., Zhang J., Grimsdale A.C., Müllen H., MacKenzie J.D., Silva C., and Friend R.H. Attaching perylene dyes to polyfluorene: three simple efficient methods for facile color tuning of light-emitting polymers. J. Am. Chem. Soc. 125 (2003) 437-443
38. Alibert-Fouet S., Dardel S., Bock H., Oukachmih M., Archambeau S., Seguy I., Jolinat P., and Destruel P. Electroluminescent diodes from complementary discotic benzoperylenes. Chem. Phys. Chem. 4 (2003) 983-985
39. Liu Y., Li Y., Jiang L., Gan H., Liu H., Li Y., Zhuang J., Lu F., and Zhu D. Assembly and characterization of novel hydrogen-bond-induced nanoscale rods. J. Org. Chem. 69 (2004) 9049-9054
40. Shin W.S., Jeong H.H., Kim M.K., Jin S.H., Kim M.R., Lee J.K., Lee J.W., and Gal Y.S. Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application. J. Mater. Chem. 16 (2006) 384-390
41. 'Neil M.P.O., Niemczyk M.P., Svec W.A., Gosztola D., Gaines III G.L., and Wasielewski M.R. Picosecond optical switching based on biphotonic excitation of an electron donor-acceptor-donor molecule. Science 257 (1992) 63-65
42. Zang L., Liu R., Holman M.W., Nguyen K.T., and Adams D.M. A single-molecule probe based on intramolecular electron transfer. J. Am. Chem. Soc. 124 (2002) 10640-10641
43. Schenning A.P.H.J., Herrikhuyzen J., van Jonkheijm P., Chen Z., Würthner F., and Meijer E.W. Photoinduced electron transfer in hydrogen-bonded oligo(p-phenylene vinylene)-perylene bisimide chiral assemblies. J. Am. Chem. Soc. 124 (2002) 10252-10253
44. Syamakumari A., Schenning A.P.H.J., and Meijer E.W. Synthesis, optical properties and aggregation behavior of a triad system based on perylene and oligo(p-phenylene vinylene) units. Chem. Eur. J. 8 (2002) 3353-3361
45. Valentini L., Bagnis D., Marrocchi A., Seri M., Taticchi A., and Kenny J.M. Novel anthracene-core molecule for the development of efficient PCBM-based solar cells. Chem. Mater. 20 (2008) 32-34
46. Zou Y., Wu W., Sang G., Yang Y., Liu Y., and Li Y. Polythiophene derivative with phenothiazine-vinylene conjugated side chain: synthesis and its application in field-effect transistors. Macromolecules 40 (2007) 7231-7237
47. McKean D.R., Parrinello G., Renaldo A.F., and Stille J.K. Synthesis of functionalized styrenes via palladium-catalyzed coupling of aryl bromides with vinyl tin reagents. J. Org. Chem. 52 (1987) 422-424
48. Peng Q., Li M., Tang X., Lu S., Peng J., and Cao Y. New polyphenylene- and polyphenylenevinylene-based copolymers containing triarylpyrazoline units in the main chains. J. Polym. Sci. Part A: Polym. Chem. 45 (2007) 1632-1640
49. Würthner F., Stepanenko V., Chen Z., Saha-Möller C.R., Kocher N., and Dietmar Stalke D. Preparation and characterization of regioisomerically pure 1,7-disubstituted perylene bisimide dyes. J. Org. Chem. 69 (2004) 7933-7939
50. Koyuncu S., Kus M., Demic S., Kaya E. Ozdemir I., and Icli S. Electrochemical and optical properties of novel donor-acceptor thiophene-perylene-thiophene polymers. J. Polym. Sci. Part A: Polym. Chem. 46 (2008) 1974-1989
51. Adams H., Bawa R.A., McMillan K.G., and Jones S. Asymmetric control in Diels-Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information. Tetrahedron: Asymmetry 18 (2007) 1003-1012
52. O.I. Kolodiazhnyi, Phosphorus Ylides, Wiley Interscience, New York, 1999.
53. S. Patai, F.R. Hartley, The Chemistry of organophosphorus compounds, Wiley Interscience, New York, vol. 3, 1994.
54. J.I.G. Cadogan, Organophosphorus reagents in organic synthesis, Academic press, London, 1979.
55. Ziegler Jr. C.B., and Heck R.F. Palladium-catalyzed vinylic substitution with highly activated aryl halides. Org. Chem. 43 (1978) 2941-2946
56. Amrutha S.R., and Jayakannan M. Structure control of π-conjugated polymers for enhanced solid-state luminescence: synthesis and liquid crystalline and photophysical properties of new bulky poly(p-phenylenevinylene)s and oligo(phenylenevinylene)s bearing tricyclodecane pendants. Macromolecules 40 (2007) 2380-2391
57. Zhao J., Swinnen A., Assche G.V., Manca J., Vanderzande D., and Mele B.V. Phase diagram of P3HT/PCBM blends and its implication for the stability of morphology. J. Phys. Chem. B 113 (2009) 1587-1591
58. Li X., Zhang Y., Yang R., Huang J., Yang W., and Cao Y. Novel saturated red-emitting poly(p-phenylenevinylene) copolymers with narrow-band-gap units of 2,1,3-benzothiadiazole synthesized by a palladium-catalyzed stille coupling reaction. J. Polym. Sci. Part A: Polym. Chem. 43 (2005) 2325-2336
59. Xue L.Y., Xia H., Xu B., Wen S., and Tian W. Synthesis and properties of polythiophene derivatives containing triphenylamine moiety and their photovoltaic applications. J. Polym. Sci. Part A: Polym. Chem. 46 (2008) 3970-3984
60. Hou J.H., Tan Z.A., He Y.J., Yang C.H., and Li Y.F. Branched poly(thienylene vinylene)s with absorption spectra covering the whole visible region. Macromolecules 39 (2006) 4657-4662
61. Wan J.H., Feng J.C., Wen G.A., Wei W., Fan Q.L., Wang C.M., Wang H.Y., Zhu R., Yuan X.D., Huang C.H., and Huang W. Effective tuning of HOMO and LUMO energy levels by p-n diblock and triblock oligomer approaches. J. Org. Chem. 71 (2006) 2565-2571
62. Shin W.S., Jeong H.H., Kim M.K., Jin S.H., Kim M.R., Lee J.K., Lee J.W., and Gal Y.S. Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application. J. Mater. Chem. 16 (2006) 384-390
63. Chen S.-H., Hwang S.-W., and Chen Y. Photoluminescent and electrochemical properties of novel copoly(aryl ether)s with isolated fluorophores. J. Polym. Sci. Part A: Polym. Chem. 42 (2004) 883-893
64. Kruger J., Plass R., Cevey L., Piccirelli M., Gratzel M., and Bach U. High efficiency solid-state photovoltaic device due to inhibition of interface charge recombination. Appl. Phys. Lett. 79 (2001) 2085-2087
65. Kroeze J.E., Hirata N., Schmidt-Mende L., Orizu C., Ogier S.D., Carr K., Gratzel M., and Durrant J.R. Parameters influencing charge separation in solid-state dye-sensitized solar cells using novel hole conductors. Adv. Funct. Mater. 16 (2006) 1832-1838