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Received May 26, 2014
Accepted July 30, 2014
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This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits
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Molecular structure-device performance relationship in polymer solar cells based on indene-C60 bis-adduct derivatives
Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea 1Department of Chemical Engineering, Pohang University of Science and Technology (POSTECH), Pohang, Gyeongbuk 790-784, Korea
bumjoonkim@kaist.ac.kr
Korean Journal of Chemical Engineering, February 2015, 32(2), 261-267(7), 10.1007/s11814-014-0220-2
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Abstract
Interfacial tension between two materials is a key parameter in determining their miscibility and, thus, their morphological behavior in blend films. In bulk heterojunction (BHJ)-type polymer solar cells (PSCs), control of the interfacial tension between the electron donor and the electron acceptor is critically important in order to increase miscibility and achieve optimized BHJ morphology for producing efficient exciton dissociation and charge transport. Herein, we report the synthesis of a series of indene-C60 bis-adducts (ICBA) derivatives by modifying their end-groups with fluorine (FICBA), methoxy (MICBA) and bromine (BICBA) functional units. We systematically studied the effects of their structural changes on the blend morphology with poly(3-hexylthiophene) (P3HT) and their performance in the PSCs. The end-group modification of ICBA derivatives induced a dramatic change in their interfacial tensions with P3HT (i.e., from 4.9 to 8.3mN m-1), resulting in large variations in the power conversion efficiency (PCE) of the PSCs,_x000D_
ranging from 2.9 to 5.2%.
Keywords
References
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Thompson BC, Frechet JMJ, Angew. Chem., Int. Ed., 47, 58 (2008)
Hauch JA, Schilinsky P, Choulis SA, Childers R, Biele M, Brabec CJ, Sol. Energy Mater. Sol. Cells, 92(7), 727 (2008)
Ma WL, Yang CY, Gong X, Lee K, Heeger AJ, Adv. Funct. Mater., 15(10), 1617 (2005)
Kozub DR, Vakhshouri K, Orme LM, Wang C, Hexemer A, Gomez ED, Macromolecules, 44(14), 5722 (2011)
Li G, Yao Y, Yang H, Shrotriya V, Yang G, Yang Y, Adv. Funct. Mater., 17(10), 1636 (2007)
Yao Y, Hou JH, Xu Z, Li G, Yang Y, Adv. Funct. Mater., 18(12), 1783 (2008)
Peet J, Senatore ML, Heeger AJ, Bazan GC, Adv. Mater., 21(14-15), 1521 (2009)
Lee JK, Ma WL, Brabec CJ, Yuen J, Moon JS, Kim JY, Lee K, Bazan GC, Heeger AJ, J. Am. Chem. Soc., 130(11), 3619 (2008)
Lou SJ, Szarko JM, Xu T, Yu LP, Marks TJ, Chen LX, J. Am. Chem. Soc., 133(51), 20661 (2011)
Cho CH, Kang H, Kang TE, Cho HH, Yoon SC, Jeon MK, Kim BJ, Chem. Commun., 47, 3577 (2011)
Ko SW, Verploegen E, Hong S, Mondal R, Hoke ET, Toney MF, McGehee MD, Bao ZN, J. Am. Chem. Soc., 133(42), 16722 (2011)
Cheng YJ, Chen CH, Lin YS, Chang CY, Hsu CS, Chem. Mater., 23, 5068 (2011)
Son HJ, Wang W, Xu T, Liang YY, Wu YE, Li G, Yu LP, J. Am. Chem. Soc., 133(6), 1885 (2011)
Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K, J. Am. Chem. Soc., 134(7), 3498 (2012)
Kang TE, Cho HH, Kim HJ, Lee W, Kang H, Kim BJ, Macromolecules, 46, 6806 (2013)
Cho HH, Kang TE, Kim KH, Kang H, Kim HJ, Kim BJ, Macromolecules, 45(16), 6415 (2012)
Szarko JM, Guo JC, Liang YY, Lee B, Rolczynski BS, Strzalka J, Xu T, Loser S, Marks TJ, Yu LP, Chen LX, Adv. Mater., 22(48), 5468 (2010)
Kim JS, Lee Y, Lee JH, Park JH, Kim JK, Cho K, Adv. Mater., 22(12), 1355 (2010)
Park JK, Jo J, Seo JH, Moon JS, Park YD, Lee K, Heeger AJ, Bazan GC, Adv. Mater., 23(21), 2430 (2011)
Cho CH, Kim HJ, Kang H, Shin TJ, Kim BJ, J. Mater. Chem., 22, 14236 (2012)
Piliego C, Holcombe TW, Douglas JD, Woo CH, Beaujuge PM, Frechet JMJ, J. Am. Chem. Soc., 132(22), 7595 (2010)
Kim HJ, Han AR, Cho CH, Kang H, Cho HH, Lee MY, Frechet JMJ, Oh JH, Kim BJ, Chem. Mater., 24, 215 (2011)
Cheng YJ, Hsieh CH, Li PJ, Hsu CS, Adv. Funct. Mater., 21(9), 1723 (2011)
Yang XN, van Duren JKJ, Janssen RAJ, Michels MAJ, Loos J, Macromolecules, 37(6), 2151 (2004)
Swinnen A, Haeldermans I, vande Ven M, D'Haen J, Vanhoyland G, Aresu S, D'Olieslaeger M, Manca J, Adv. Funct. Mater., 16(6), 760 (2006)
Kim KH, Kang H, Nam SY, Jung J, Kim PS, Cho CH, Lee C, Yoon SC, Kim BJ, Chem. Mater., 23, 5090 (2011)
Kang H, Cho CH, Cho HH, Kang TE, Kim HJ, Kim KH, Yoon SC, Kim BJ, ACS Appl. Mater. Interfaces, 4, 110 (2011)
Liu C, Xiao S, Shu X, Li Y, Xu L, Liu T, Yu Y, Zhang L, Liu H, Li Y, ACS Appl. Mater. Interfaces, 4, 1065 (2012)
Varotto A, Treat ND, Jo J, Shuttle CG, Batara NA, Brunetti FG, Seo JH, Chabinyc ML, Hawker CJ, Heeger AJ, Wudl F, Angew. Chem., Int. Ed., 50, 5166 (2011)
Backer SA, Sivula K, Kavulak DF, Frechet JMJ, Chem. Mater., 19, 2927 (2007)
Zhao GJ, He YJ, Li YF, Adv. Mater., 22(39), 4355 (2010)
Lenes M, Wetzelaer GJAH, Kooistra FB, Veenstra SC, Hummelen JC, Blom PWM, Adv. Mater., 20(11), 2116 (2008)
He YJ, Chen HY, Hou JH, Li YF, J. Am. Chem. Soc., 132(4), 1377 (2010)
Treat ND, Varotto A, Takacs CJ, Batara N, Al-Hashimi M, Heeney MJ, Heeger AJ, Wudl F, Hawker CJ, Chabinyc ML, J. Am. Chem. Soc., 134(38), 15869 (2012)
Collins BA, Gann E, Guignard L, He X, McNeill CR, Ade H, J. Phys. Chem. Lett., 1, 3160 (2010)
Kim KH, Kang H, Kim HJ, Kim PS, Yoon SC, Kim BJ, Chem. Mater., 24, 2373 (2012)
Mayorova JY, Nikitenko SL, Troshin PA, Peregudova SM, Peregudov AS, Kaplunov MG, Lyubovskaya RN, Mendeleev Commun., 17, 175 (2007)
He Y, Chen C, Richard E, Dou L, Wu Y, Li G, Yang Y, J. Mater. Chem., 22, 13391 (2012)
Zhao H, Guo X, Tian H, Li C, Xie Z, Geng Y, Wang F, J. Mater. Chem., 20, 3092 (2010)
Kang H, Kim KH, Kang TE, Cho CH, Park S, Yoon SC, Kim BJ, ACS Appl. Mater. Interfaces, 5, 4401 (2013)
Puplovskis A, Kacens J, Neilands O, Tetrahedron Lett., 38, 285 (1997)
Brabec CJ, Cravino A, Meissner D, Sariciftci NS, Fromherz T, Rispens MT, Sanchez L, Hummelen JC, Adv. Funct. Mater., 11(5), 374 (2001)
Chang YT, Hsu SL, Chen GY, Su MH, Singh TA, Diau EWG, Wei KH, Adv. Funct. Mater., 18(16), 2356 (2008)
Kooistra FB, Knol J, Kastenberg F, Popescu LM, Verhees WJH, Kroon JM, Hummelen JC, Org. Lett., 9, 551 (2007)
Comyn J, Int. J. Adhes. Adhes, 12, 145 (1992)
Wu S, J. Polym. Sci., Part C: Polym. Symp., 34, 19 (1971)
Kim JB, Allen K, Oh SJ, Lee S, Toney MF, Kim YS, Kagan CR, Nuckolls C, Loo YL, Chem. Mater., 22, 5762 (2010)
Oh JY, Jang WS, Lee TI, Myoung JM, Baik HK, Appl. Phys. Lett., 98, 023303 (2011)
Campoy-Quiles M, Ferenczi T, Agostinelli T, Etchegoin PG, Kim Y, Anthopoulos TD, Stavrinou PN, Bradley DDC, Nelson J, Nat. Mater., 7(2), 158 (2008)
Rosen MJ, Surfactants and interfacial phenomena, John Wiley & Sons, Inc., New York, i (2004)
Wu JL, Chen FC, Hsiao YS, Chien FC, Chen P, Kuo CH, Huang MH, Hsu CS, ACS Nano, 5, 959 (2011)
Alam MM, Jenekhe SA, Chem. Mater., 16, 4647 (2004)
Dittmer JJ, Marseglia EA, Friend RH, Adv. Mater., 12(17), 1270 (2000)
Wang PS, Yao K, Chen L, Chen YW, Li F, Wang HM, Yu SX, Sol. Energy Mater. Sol. Cells, 97, 34 (2012)
Matsuo Y, Sato Y, Niinomi T, Soga I, Tanaka H, Nakamura E, J. Am. Chem. Soc., 131(44), 16048 (2009)
Chen L, Yao K, Chen Y, J. Mater. Chem., 22, 18768 (2012)
