Design and synthesis of side-chain functionalized regioregular poly(3-hexylthiophene)-based copolymers and application in polymer: Fullerene bulk heterojunction solar cells

Proceedings of SPIE - The International Society for Optical Engineering

Volumn 7416, Issue , 2009, Pages

  Campo, B ^a   Oosterbaan, W D ^a   Gilot, J ^c   Cleij, T J ^a   Lutsen, L ^b   Janssen, R A J ^c   Vanderzande, D ^a,b  

^a HASSELT UNIVERSITY   (Belgium)

^b HASSELT UNIVERSITY   (Belgium)

^c EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Bulk heterojunction solar cells; Functionalized polythiophenes; Morphology; Post polymerization functionalization; Stability

Indexed keywords

ACID GROUPS; ALKYL SIDE CHAINS; BULK HETEROJUNCTION SOLAR CELLS; BUTYRIC ACIDS; DEVICE PERFORMANCE; ELECTRON ACCEPTOR; ESTER FUNCTIONS; FUNCTIONALIZATION REACTIONS; FUNCTIONALIZED; LAYER MORPHOLOGY; METHYL ESTERS; POLY (3-HEXYLTHIOPHENE); POLYTHIOPHENES; POST-POLYMERIZATION; POST-POLYMERIZATION FUNCTIONALIZATION; RANDOM COPOLYMER; REGIO-REGULAR; SIDE CHAINS; SIDE-CHAIN; SIDE-CHAIN FUNCTIONALITIES;

ALKYLATION; CARRIER MOBILITY; CONJUGATED POLYMERS; COPOLYMERIZATION; COPOLYMERS; ESTERIFICATION; ESTERS; FATTY ACIDS; FLUORINE CONTAINING POLYMERS; FULLERENES; HETEROJUNCTIONS; MORPHOLOGY; ORGANIC POLYMERS; PHOTOVOLTAIC EFFECTS; PLASTIC PRODUCTS; POLYMERS; SOLAR CELLS; SYNTHESIS (CHEMICAL); THIOPHENE;

FUNCTIONAL POLYMERS;

EID: 70449644811     PISSN: 0277786X     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.825881     Document Type: Conference Paper

References (60)

1. Sariciftci, N. S., Smilowitz, L., Heeger, A. J. and Wudl, F., "Photoinduced electron transfer from a conducting polymer to buckminsterfullerene", science 258, 1474-1476 (1992)
2. Halls, J. J. M., C. A., W., Greenham, N. C., Marseglia, E. A., Friend, R. H., Moratti, S. C. and Holmes, A. B., "Efficient photodiodes from interpenetrating networks", Nature 376, 498-500 (1995)
3. Yu, G., Gao, J., Hummelen, J. C., Wudl, F. and Heeger, A. J., "Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions", science 270, 1789-1791 (1995)
4. 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(5835), 222-225 (2007) (Pubitemid 47076192)
5. Li, G., Shrotriya, V., Huang, J. S., Yao, Y., Moriarty, T., Emery, K. and Yang, Y., "High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends", Nature Materials 4(11), 864-868 (2005)
6. Ma, W., Yang, C., Gong, X., Lee, K. and Heeger, A. J., "Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology", Advanced functional materials 15, 1617-1622 (2005)
7. Reyes-Reyes, M., Kim, K. and Carroll, D. L., "High-efficiency photovoltaic devices on annealed poly(3- hexylthiophene) and 1-(3-methoxycarbonyl)-propyl-1-phenyl-(6, 6)C61 blends", Applied physics letters 87(083506), (2005)
8. Scharber, M. C., Wuhlbacher, D., Koppe, M., Denk, P., Waldauf, C., Heeger, A. J. and Brabec, C. L., "Design rules for donors in bulk-heterojunction solar cells - Towards 10 % energy-conversion efficiency", Advanced materials 18(6), 789 (2006)
9. Thompson, B. C. and Frechet, J. M. J., "Organic photovoltaics - Polymer-fullerene composite solar cells", Angewandte chemie international edition 47(1), 58-77 (2008)
10. Lee, K., Kim, J. Y., Ma, W. and Heeger, A. J., "New architecture for thermally stable high efficiency polymer solar cells", Proceedings of SPIE 5938, 59380B1-12 (2005)
11. Kim, J. Y., Kim, S. H., Lee, H. H., Lee, K., Ma, W. L., Gong, X. and Heeger, A. J., "New architecture for highefficiency polymer photovoltaic cells using solution-based titanium oxide as an optical spacer", Advanced materials 18(5), 572-+(2006)
12. Peet, J., Kim, J. Y., Coates, N. E., Ma, W. L., Moses, D., Heeger, A. J. and Bazan, G. C., "Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols", Nature Materials 6, 497-500 (2007)
13. Brabec, C. J., Shaheen, S. E., Winder, C., Sariciftci, N. S. and Denk, P., "Effect of LiF/metal electrodes on the performance of plastic solar cells", Applied physics letters 80(7), 1288-1290 (2002)
14. Moulé, A. J., Bonekamp, J. B., Ruhl, A., Klesper, H. and Meerholz, K., "The effect of active layer thickness on the efficiency of Polymer solar cells", Proceedings of SPIE 5938, 593808 1-7 (2005)
15. Hadipour, A., de Boer, B. and Blom, P. W. M., "Organic tandem and multi-junction solar cells", Advanced functional materials 18(2), 169-181 (2008)
16. Gilot, J., Barbu, I., Wienk, M. M. and Janssen, R. A. J., "The use of ZnO as optical spacer in polymer solar cells: Theoretical and experimental study", Applied physics letters 91(11), - (2007)
17. Jorgensen, M., Norrman, K. and Krebs, F. C., "Stability/degradation of polymer solar cells", Solar energy materials and solar cells 92(7), 686-714 (2008)
18. Dennler, G., Scharber, M. C. and Brabec, C. J., "Polymer-Fullerene Bulk-Heterojunction Solar Cells", Advanced materials 21(13), 1323-1338 (2009)
19. Yang, X., Loos, J., Veenstra, S. C., Verhees, W. J. H., Wienk, M. M., Kroon, J. M., Michels, M. A. J. and Janssen, R. A. J., "Nanoscale morphology of high-performance polymer solar cells", Nanoletters 5(4), 579-583 (2005) (Pubitemid 40609723)
20. Yao, Y., Hou, J. H., Xu, Z., Li, G. and Yang, Y., "Effect of solvent mixture on the nanoscale phase separation in polymer solar cells", Advanced functional materials 18(12), 1783-1789 (2008)
21. Shaheen, S. E., Brabec, C. J., Sariciftci, N. S., Padinger, F., Fromherz, T. and Hummelen, J. C., "2.5% efficient organic plastic solar cells", Applied physics letters 78(6), 841-843 (2001)
22. Vanlaeke, P., Vanhoyland, G., Aernouts, T., Cheyns, D., Deibel, C., Manca, J., Heremans, P. and Poortmans, J., "Polythiophene based bulk heterojunction solar cells: morphology and its implications", Thin solid films 511-512, 358-361(2006)
23. Padinger, F., Rittberger, R. S. and Sariciftci, N. S., "Effects of postproduction treatment on plastic solar cells", Advanced functional materials 13(1), 85-88 (2003)
24. Li, G., Yao, Y., Yang, H., Shrotriya, V., Yang, G. and Yang, Y., ""Solvent annealing" effect in polymer solar cells based on poly(3-hexylthiophene) and methanofullerenes", Advanced functional materials 17(10), 1636-1644 (2007)
25. Swinnen, A., Haeldermans, I., vande Ven, M., D'Haen, J., Vanhoyland, G., Aresu, S., D'Olieslaeger, M. and Manca, J., "Tuning the dimensions of C-60-based needlelike crystals in blended thin films", Advanced functional materials 16(6), 760-765 (2006)
26. Krebs, F. C., "Air stable polymer photovoltaics based on a process free from vacuum steps and fullerenes", Solar energy materials and solar cells 92(7), 715-726 (2008)
27. Zhu, Z., Hadjikyriacou, S., Waller, D. and Gaudiana, R., "Stabilization of film morphology in polymer-fullerene heterojunction solar cells", Journal of macromolecular science: part A: pure and applied chemistry 41(12), 1467-1487 (2004)
28. Drees, M., Hoppe, H., Winder, C., Neugebauer, H., Sariciftci, N. S., Schwinger, W., Schaffler, F., Topf, C., Scharber, M. C., Zhu, Z. G. and Gaudiana, R., "Stabilization of the nanomorphology of polymer-fullerene "bulk heterojunction'' blends using a novel polymerizable fullerene derivative", journal of materials chemistry 15(48), 5158-5163 (2005)
29. Zhou, Z. Y., Chen, X. W. and Holdcroft, S., "Stabilizing bicontinuous nanophase segregation in pi CP-C-60 donoracceptor blends", Journal of the American chemical society 130(35), 11711-11718 (2008)
30. Miyanishi, S., Tajima, K. and Hashimoto, K., "Morphological Stabilization of Polymer Photovoltaic Cells by Using Cross-Linkable Poly(3-(5-hexenyl)thiophene)", macromolecules 42(5), 1610-1618 (2009)
31. Nierengarten, J. F. and Setayesh, S., "Towards polymerizable fullerene derivatives to stabilize the initially formed phases in bulk-heterojunction solar cells", New journal of chemistry 30, 313-316 (2006)
32. Björstrom, C. M., Magnusson, K. O. and Moons, E., "Control of phase separation in blends of polyfluorene (co)polymers and the C60-derivative PCBM", Synthetic Metals 152, 109-112 (2005)
33. Rajaram, S., Armstrong, P. B., Kim, B. J. and Frechet, J. M. J., "Effect of Addition of a Diblock Copolymer on Blend Morphology and Performance of Poly(3-hexylthiophene):Perylene Diimide Solar Cells", Chemistry of materials 21(9), 1775-1777 (2009)
34. Sivula, K., Ball, Z. T., Watanabe, N. and Frechet, J. M. J., "Amphiphilic diblock copolymer compatibilizers and their effect on the morphology and performance of polythiophene: Fullerene solar cells", Advanced materials 18(2), 206- + (2006)
35. Woo, C. H., Thompson, B. C., Kim, B. J., Toney, M. F. and Fréchet, J. M., "The influence of Poly(3- hexylthiophene) regioregularity on fullerene-composite solar cell performance", Journal of the American chemical society 130(48), 16324-16329 (2008)
36. Sivula, K., Luscombe, C. K., Thompson, B. C. and Fréchet, J. M. J., "Enhancing the Thermal Stability of Polythiophene:Fullerene Solar Cells by Decreasing Effective Polymer Regioregularity", Journal of the American chemical society 128, 13988-13989 (2006)
37. Bertho, S., Haeldermans, I., Swinnen, A., Moons, W., Martens, T., Lutsen, L., Vanderzande, D., Manca, J., Senes, A. and Bonfiglio, A., "Influence of thermal ageing on the stability of polymer bulk heterojunction solar cells", Solar energy materials and solar cells 91(5), 385-389 (2007)
38. Kim, B. J., Miyamoto, Y., Ma, B. and Fréchet, J. M. J., "Photocrosslinkable pholythiophenes for efficient, thermally stable, organic photovoltaics", Advanced functional materials 19, 1-9 (2009)
39. Osaka, I. and McCullough, R. D., "Advances in molecular design and synthesis of regioregular polythiophenes", Accounts of Chemical Research 41(9), 1202-1214 (2008)
40. Loewe, R. S., Khersonsky, S. M. and McCullough, R. D., "A simple method to prepare head-to-tail coupled, regioregular poly(3-alkylthiophenes) using grignard metathesis", Advanced materials 11(3), 250-+ (1999)
41. Liu, J. and McCullough, R. D., "End group modification of regioregular polythiophene through postpolymerization functionalization", macromolecules 35, 9882-9889 (2002)
42. Zhai, L., Laird, D. W. and McCullough, R. D., "Soft-lithography patterning of functionalized regioregular polythiophenes", Langmuir 19(16), 6492-6497 (2003)
43. Mccullough, R. D., Lowe, R. D., Jayaraman, M. and Anderson, D. L., "Design, Synthesis, and Control of Conducting Polymer Architectures - Structurally Homogeneous Poly(3-Alkylthiophenes)", Journal of organic chemistry 58(4), 904-912 (1993)
44. Zhai, L., Pilston, R. L., Zaiger, K. L., Stokes, K. K. and McCullough, R. D., "A simple method to generate sicechain derivatives of regioregular polythiophene via the GRIM methathesis and post-polymerization functionalization", macromolecules 36, 61-64 (2003)
45. Dai, C. A., Yen, W. C., Lee, Y. H., Ho, C. C. and Su, W. F., "Facile synthesis of well-defined block copolymers containing regioregular poly(3-hexyl thiophene) via anionic macroinitiation method and their self-assembly behavior", Journal of the American chemical society 129(36), 11036-+ (2007)
46. Sheina, E. E., Khersonsky, S. M., Jones, E. G. and McCullough, R. D., "Highly conductive, regioregular alkoxyfunctionalized polythiophenes: A new class of stable, low band gap materials", Chemistry of materials 17(13), 3317-3319 (2005)
47. Jeffries-El, M., Sauve, G. and McCullough, R. D., "In-situ end-group functionalization of regioregular poly(3- alkylthiophene) using the Grignard metathesis polymerization method", Advanced materials 16(12), 1017-+ (2004)
48. Stokes, K. K., Heuze, K. and McCullough, R. D., "New phosphonic acid functionalized, regioregular polythiophenes", macromolecules 36(19), 7114-7118 (2003)
49. Chen, T. A., Wu, X. M. and Rieke, R. D., "Regiocontrolled Synthesis of Poly(3-Alkylthiophenes) Mediated by Rieke Zinc - Their Characterization and Solid-State Properties", Journal of the American chemical society 117(1), 233-244 (1995)
50. Oosterbaan, W. D., Vrindts, V., Berson, S., Guillerez, S., Douhéret, O., Ruttens, B., D'Haen, J., Adriaensens, P., Manca, J., Lutsen, L. and Vanderzande, D., "Efficient formation, isolation and characterization of poly(3-alkylthiophene) nanofibres: probing order as a function of side-chain length", journal of materials chemistry DOI: 10.1039/b900670b,(2009)
51. Zhu, L., Wehmeyer, R. M. and Rieke, R. D., "The Direct Formation of Functionalized Alkyl(Aryl)Zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid-Chlorides, Alpha, Beta- Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides", Journal of organic chemistry 56(4), 1445-1453 (1991)
52. Kato, M., Hirayama, T., Matsuda, H., Minami, N., Okada, S. and Nakanishi, H., "Photocrosslinkable Azo-Dye Polymers for 2nd-Order Nonlinear Optics", Macromolecular Rapid Communications 15(9), 741-750 (1994)
53. Bauerle, P., Pfau, F., Schlupp, H., Wurthner, F., Gaudl, K. U., Caro, M. B. and Fischer, P., "Synthesis and Structural Characterization of Alkyl Oligothiophenes - the 1st Isomerically Pure Dialkylsexithiophene", Journal of the Chemical Society-Perkin Transactions 2 (3), 489-494 (1993)
54. Tamao, K., Kodama, S., Nakajima, I., Kumada, M., Minato, A. and Suzuki, K., "Nickel-Phosphine Complex- Catalyzed Grignard Coupling.2. Grignard Coupling of Heterocyclic-Compounds", Tetrahedron 38(22), 3347-3354 (1982)
55. Lowe, J. and Holdcroft, S., "Synthesis and polylithography of polymers and copolymers based on Poly(3-(2- (methacryloyloxy)ethyl)thiophene) ", macromolecules 28, 4608-4616 (1995)
56. Dai, J., Sellers, J. L. and Noftle, R. E., "An efficient method for the synthesis of 3-alkylthiophenes bearing groups on the side chain: imides and amides", Synthetic Metals 139, 81-88 (2003)
57. Kock, T. J. J. M. and de Ruiter, B., "A radiation-crosslinkable thiophene copolymer", Synthetic Metals 79, 215-218 (1996)
58. Spano, F. C., "Modeling disorder in polymer aggregates: the optical spectroscopy of regioregular poly(3- hexylthiophene) thin films", The Journal of Chemical Physics 122, 234701 (2005)
59. Spano, F. C., "Absorption in regio-regular poly(3-hexylthiophene) thin films: Fermi resonances, interband coupling and disorder", Chemical Physics 325, 22-35 (2006)
60. Zhokhavets, U., Erb, T., Gobsch, G., Al-Ibrahim, M. and Ambacher, O., "Relation between absorption and crystallinity of poly(3-hexylthiophene)/ fullerene films for plastic solar cells", Chemical Physics Letters 418(4-6), 347-350 (2006)