Macromolecular Research, Vol.21, No.3, 257-271, March, 2013
Precision synthesis of tailor-made polythiophene-based materials and their application to organic solar cells
E-mail:
Polymer-based solar cells (PSCs) have been promising candidates as renewable energy resources, having multiple advantages of flexible, low-cost and large-area processing for their mass production. Among them, much attention has been paid to fundamental bulk-heterojunction (BHJ) devices using a blend of regioregular poly(3-hexylthiophene) (P3HT) and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the active layer. However, there are still significant limitations not only in the low power conversion efficiency (PCE), but also in the device stability. The morphological control of BHJ PSCs is one of the most important issues to improve the device performances. On the other hand, P3HT itself has received much attention in many fields, because it is the best class of balanced high-performance materials as a p-type semiconductor in terms of solubility, chemical stability, charge mobility, and commercial availability. The discovery of the quasi-living Grignard metathesis polymerization (or called catalysttransfer polycondensation) system has made it possible to synthesize a wide variety of chain-end-functional P3HT derivatives, their block copolymers and star-branched polymers. Since the competitive research areas including PSC applications have strongly demanded the accelerated developments of new materials and well-defined morphologies related to polythiophenes, the fundamental studies of P3HT have still been targeted by many research groups. In this review, the controlled synthesis of P3HT, the synthesis of P3HT-based block copolymers, their applications to PSCs, as well as the scope and potential of new thiophene-based materials are described.
Keywords:living polymerization;polycondensation;polythiophene;block copolymers;self-assembly;organic solar cells
- Krebs FC, in Polymeric Solar Cells, DEStech Pblication, Inc., PA, 2010.
- Cheng YJ, Yang SH, Hsu CS, Chem. Rev., 109(11), 5868 (2009)
- Li G, Shrotriya V, Huang JS, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4(11), 864 (2005)
- Yang XN, Loos J, Veenstra SC, Verhees WJH, Wienk MM, Kroon JM, Michels MAJ, Janssen RAJ, Nano Lett., 5, 579 (2005)
- http:// www. nrel. gov/ ncpv/ images/ efficiency_ chart. jpg in NERL home page.
- Yokoyama A, Miyakoshi R, Yokozawa T, Macromolecules, 37(4), 1169 (2004)
- Miyakoshi R, Yokoyama A, Yokozawa T, J. Am. Chem. Soc., 127(49), 17542 (2005)
- Sheina EE, Liu JS, Iovu MC, Laird DW, McCullough RD, Macromolecules, 37(10), 3526 (2004)
- Iovu MC, Sheina EE, Gil RR, McCullough RD, Macromolecules, 38(21), 8649 (2005)
- Higashihara T, Ueda M, In Complex Macromolecular Architecture, Hadhichristids N, Hirao A, Tezuka Y, Prez FD, Eds. John Wiley & Sons (Asia), Pte Ltd., Singapore, 2011.
- Di CA, Yu C, Liu YQ, Zhu DB, J. Phys. Chem. B, 111, 14083 (2000)
- Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger AJ, Science, 317, 222 (2007)
- Thompson BC, Frechet JMJ, Angew. Chem.-Int. Edit., 47, 58 (2008)
- Wei Q, Nishizawa T, Tajima K, Hashimoto K, Adv. Mater., 20, 1 (2008)
- Chen J, Cao Y, Acc. Chem. Res., 42, 1709 (2009)
- Cheng YJ, Yang SH, Hsu CS, Chem. Rev., 109(11), 5868 (2009)
- Green MA, Emery K, Hishikawa Y, Warta W, Prog. Photovolt: Res. Appl., 18, 144 (2010)
- McCullough RD, Lowe RD, J. Chem. Soc.-Chem. Commun., 70 (1992)
- McCullough RD, Lowe RD, Jayaraman M, Ewbank PC, Anderson DL, J. Org. Soc., 58, 904 (1993)
- Chen TA, Wu XM, Rieke RD, J. Am. Chem. Soc., 117(1), 233 (1995)
- Loewe RS, Khersonsky SM, McCullough RD, Adv. Mater., 11(3), 250 (1999)
- Loewe RS, Ewbank PC, Liu JS, Zhai L, McCullough RD, Macromolecules, 34(13), 4324 (2001)
- Amou S, Haba O, Shirato K, Hayakawa T, Ueda M, Takeuchi K, Asai M, J. Polym. Sci. A: Polym. Chem., 37(13), 1943 (1999)
- Kobayashi M, Matsumoto Y, Uchiyama M, Ohwada T, Macromolecules, 37(12), 4339 (2004)
- Higashihara T, Goto E, Ueda M, ACS Macro Lett., 1, 167 (2012)
- Wang QF, Takita R, Kikuzaki Y, Ozawa F, J. Am. Chem. Soc., 132(33), 11420 (2010)
- Tamba S, Tanaka S, Okubo Y, Meguro H, Okamoto S, Mori A, Chem. Lett., 40(4), 398 (2011)
- Tamba S, Shono K, Sugie A, Mori A, J. Am. Chem. Soc., 133(25), 9700 (2011)
- Yokozawa T, Adachi I, Miyakoshi R, Yokoyama A, High Perform. Polym., 19, 684 (2007)
- Ohshimizu K, Ueda M, Macromolecules, 41(14), 5289 (2008)
- Zhang Y, Tajima K, Hirota K, Hashimoto K, J. Am. Chem. Soc., 130(25), 7812 (2008)
- Lai YC, Ohshimizu K, Takahashi A, Hsu JC, Higashihara T, Ueda M, Chen WC, J. Polym. Sci. A: Polym. Chem., 49(12), 2577 (2011)
- Takahashi A, Lin CJ, Ohshimizu K, Higashihara T, Chen WC, Ueda M, Polym. Chem., 3, 479 (2012)
- Higashihara T, Ohshimizu K, Ryo Y, Sakurai T, Takahashi A, Nojima S, Ree M, Ued M, Polymer, 52(17), 3687 (2011)
- Hempenius MA, Langeveld-Voss BMW, van Haare JAEH, Janssen RAJ, Sheiko SS, Spatz JP, Moller M, Meijer EW, J. Am. Chem. Soc., 120(12), 2798 (1998)
- Liu J, Sheina E, Kowalewski T, McCullough RD, Angew. Chem.-Int. Edit., 41, 329 (2002)
- Iovu MC, Jeffries-El M, Sheina EE, Cooper JR, McCullough RD, Polymer, 46(19), 8582 (2005)
- Iovu MC, Craley CR, Jeffries-EL M, Krankowski AB, Zhang R, Kowalewski T, McCullough RD, Macromolecules, 40(14), 4733 (2007)
- Craley CR, Zhang R, Kowalewski T, McCullough RD, Stefan MC, Macromol. Rapid Commun., 30(1), 11 (2009)
- Zou JH, Khondaker SI, Huo Q, Zhai L, Adv. Funct. Mater., 19(3), 479 (2009)
- Urien M, Erothu H, Cloutet E, Hiorns RC, Vignau L, Cramail H, Macromolecules, 41(19), 7033 (2008)
- Radano CP, Scherman OA, Stingelin-Stutzmann N, Muller C, Breiby DW, Smith P, Janssen RAJ, Meijer EW, J. Am. Chem. Soc., 127(36), 12502 (2005)
- Dai CA, Yen WC, Lee YH, Ho CC, Su WF, J. Am. Chem. Soc., 129(36), 11036 (2007)
- Higashihara T, Ohshimizu K, Hirao A, Ueday M, Macromolecules, 41(24), 9505 (2008)
- Jeffries-El M, Sauve G, McCullough RD, Adv. Mater., 16(12), 1017 (2004)
- Jeffries-El M, Sauve G, McCullough RD, Macromolecules, 38(25), 10346 (2005)
- Higashihara T, Ueda M, React. Funct. Polym., 69(7), 457 (2009)
- Higashihara T, Ueda M, Macromolecules, 42(22), 8794 (2009)
- Lee JS, Hirao A, Nakahama S, Macromolecules, 21, 274 (1988)
- Lee JS, Hirao A, Nakahama S, Macromolecules, 22, 2602 (1989)
- Hillmyer MA, Adv. Polym. Sci., 190, 137 (2005)
- Olson DA, Chen L, Hillmyer MA, Chem. Mater., 20, 869 (2008)
- Boudouris BW, Frisbie CD, Hillmyer MA, Macromolecules, 41(1), 67 (2008)
- Botiz I, Darling SB, Macromolecules, 42(21), 8211 (2009)
- Sivanandan K, Chatterjee T, Treat N, Kramer EJ, Hawker CJ, Macromolecules, 43, 233 (2009)
- Higashihara T, Takahashi A, Tajima S, Jin S, Rho Y, Ree M, Ueda M, Polym. J., 42, 43 (2010)
- Takahashi A, Ryo Y, Higashihara T, Ahn B, Ree M, Ueda M, Macromolecules, 44, 4843 (2010)
- Schilinsky P, Asawapirom U, Sherf U, Biele M, Brabec CJ, Chem. Mater., 17, 2175 (2005)
- Ma W, Kim JY, Lee K, Heeger AJ, Macromol. Rapid Commun., 28(17), 1776 (2007)
- Kim Y, Cook S, Tuladhar SM, Choulis SA, Nelson J, Durrant JR, Bradley DDC, Giles M, Mcculloch I, Ha CS, Ree M, Nat. Mater., 5(3), 197 (2006)
- Kim JB, Allen K, Oh SJ, Ree S, Tony MF, Kim YS, Kagan CR, Nuckolls C, Loo YL, Chem. Mater., 22, 5762 (2010)
- Richard F, Brochon C, Leclerc N, Eckhardt D, Heiser T, Hadziioannou G, Macromol. Rapid Commun., 29(11), 885 (2008)
- Lee JU, Cirpan A, Emrick T, Russell TP, Jo WH, J. Mater. Chem., 19, 1483 (2009)
- Yang C, Lee JK, Heeger AJ, Wudl F, J. Mater. Chem., 19, 5416 (2009)
- Sommer M, Lang AS, Thelakkat M, Angew. Chem.-Int. Edit., 47, 7901 (2008)
- Zhang QL, Cirpan A, Russell TP, Emrick T, Macromolecules, 42(4), 1079 (2009)
- Tao Y, McCulloch B, Kim S, Segalman RA, Soft Matter, 5, 4219 (2009)
- Tsai JH, Lai YC, Higashihara T, Lin CJ, Ueda M, Chen WC, Macromolecules, 43(14), 6085 (2010)
- Lai YC, Higashihara T, Hsu JC, Ueda M, Chen WC, Sol. Energy Mater. Sol. Cells, 97, 164 (2012)
- Hou JH, Tan ZA, Yan Y, He YJ, Yang CH, Li YF, J. Am. Chem. Soc., 128(14), 4911 (2006)
- Scharber MC, Wuhlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CL, Adv. Mater., 18(6), 789 (2006)
- Liang YY, Xu Z, Xia JB, Tsai ST, Wu Y, Li G, Ray C, Yu LP, Adv. Mater., 22(20), E135 (2010)
- Chu TY, Lu J, Beaupre S, Zhang Y, Pouliot JR, Wakim S, Zhou J, Leclerc M, Li Z, Ding J, Tao Y, J. Am. Chem. Soc., 133, 4250 (2011)
- Zhou H, Yang L, Stuart AC, Price SC, Liu S, You W, Angew. Chem.-Int. Edit., 50, 2995 (2011)
- Amb CM, Chen S, Graham KR, Subbiah J, Small CE, So F, Reynolds JR, J. Am. Chem. Soc., 133(26), 10062 (2011)
- He ZC, Zhong CM, Huang X, Wong WY, Wu HB, Chen LW, Su SJ, Cao Y, Adv. Mater., 23(40), 4636 (2011)
- Service RF, Science, 332(6027), 293 (2011)
- Muhlbacher D, Scharber M, Morana M, Zhu ZG, Waller D, Gaudiana R, Brabec C, Adv. Mater., 18(21), 2884 (2006)
- Coffin RC, Peet J, Rogers J, Bazan GC, Nat. Chem., 1, 657 (2009)
- Park SH, Roy A, Beaupre S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ, Nat. Photonics, 3, 297 (2009)
- Ong KH, Lim SL, Tan HS, Wong HK, Li J, Ma Z, Moh LCH, Lim SH, De Mello JC, Chen ZK, Adv. Mater., 23(11), 1409 (2011)
- Zhang M, Guo X, Wang X, Wang H, Li Y, Chem. Mater., 23, 4264 (2011)
- Du C, Li CH, Li WW, Chen X, Bo ZS, Veit C, Ma ZF, Wuerfel U, Zhu HF, Hu WP, Zhang FL, Macromolecules, 44(19), 7617 (2011)
- Umeyama T, Douvogianni E, Imahori H, Chem. Lett., 41(4), 354 (2012)
- Patil PS, Haram NS, Pal RR, Periasamy N, Wadgaonkar PP, Salunkhe MM, J. Appl. Polym. Sci., 125(3), 1882 (2012)
- Higashihara T, Wu HC, Mizobe T, Lu C, Ueda M, Chen WC, Macromolecules, 45(22), 9046 (2012)
- Ko SW, Hoke ET, Pandey L, Hong SH, Mondal R, Risko C, Yi YP, Noriega R, McGehee MD, Bredas JL, Salleo A, Bao ZA, J. Am. Chem. Soc., 134(11), 5222 (2012)
- Peet J, Heeger AJ, Bazan GC, Acc. Chem. Res., 42, 1700 (2009)