Conjugated polymer consisting of benzothiadiazole and phenazine as donor materials for organic photovoltaics

Ho Jun Song; Munju Goh; Kyung Ho Choi; Sangkug Lee; Doo Kyung Moon; Gyo Jic Shin

Journal of Industrial and Engineering Chemistry, Vol.23, 338-343, March, 2015

DOI10.1016/j.jiec.2014.08.037 Export Citation

Conjugated polymer consisting of benzothiadiazole and phenazine as donor materials for organic photovoltaics

Ho Jun Song, Munju Goh¹, Kyung Ho Choi, Sangkug Lee, Doo Kyung Moon², and Gyo Jic Shin^†

Cungcheong Regional Division IT convergence material R&D Group, Korea Institute of Industrial Technology, 89 Yangdaegiro-gil, Ipjang-myeon, Seobuk-gu, Cheonan-si 331-822, Chungcheongnam-do, Republic of Korea
¹Carbon Convergence Materials Research Center, Korea Institute of Science and Technology, Eunhari san 101, Bongdong-eup, Jeonbuk 565-905, Wanju-gun, Republic of Korea
²Department of Materials Chemistry and Engineering, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143-701, Republic of Korea

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Two new polymers, poly(thiophene-benzothiadiazole) (PThBT) and poly(thiophene-dibenzophenazine) (PThFQ), were successfully polymerized through a Stille coupling reaction. PThBT exhibited the formation of an ordered lamellar structure with conventional edge-on π-stacking. In contrast, the PThFQ backbones were oriented face-on relative to the substrate. For solar cells using a 1:6 ratio of PThFQ to PC71BM, the resulting Voc, Jsc, FF and PCE were 0.73 V, 3.4 mA/cm2, 30.5% and 0.76%, respectively. The value of the FF for PThFQ increased by 22% compared to PThBT due to the effects of the backbone planarity of the polymers and the face-on orientation.

Keywords:Benzothiadiazole;Phenazine;OPVs;Conjugated polymer

[References]

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Lu W, Kuwabara J, Kanbara T, Macromolecules, 44(6), 1252 (2011)
Song HJ, Lee JY, Song IS, Moon DK, Haw JR, J. Ind. Eng. Chem., 17(2), 352 (2011)
Song HJ, Kim DH, Lee EJ, Heo SW, Lee JY, Moon DK, Macromolecules, 45(19), 7815 (2012)
Iwan A, Palewicz M, Chuchmała A, Gorecki L, Sikora A, Mazurek B, Synth. Met., 162, 143 (2012)
Lee JY, Song HJ, Lee SM, Lee JH, Moon DK, Eur. Polym. J., 47, 1686 (2011)
Xiang N, Liu Y, Zhou W, Huang H, Guo X, Tan Z, Zhao B, Shen P, Tan S, Eur. Polym. J., 46, 1084 (2010)
Zhang JE, Cai WZ, Huang F, Wang EG, Zhong CM, Liu SJ, Wang M, Duan CH, Yang TB, Cao Y, Macromolecules, 44(4), 894 (2011)
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Manceau M, Angmo D, Jorgensen M, Krebs FC, Org. Electron., 4, 566 (2011)
Lee JY, Aleshin AN, Kim DW, Lee HJ, Kim YS, Wegner G, Enkelmann V, Roth S, Park YW, Synth. Met., 152, 169 (2005)
Yamamoto T, Kokubo H, Kobashi M, Sakai Y, Chem. Mater., 23, 4616 (2004)
Yasuda T, Sakai Y, Aramaki S, Yamamoto T, Chem. Mater., 24, 6060 (2005)
Lee Y, Nam YM, Jo WH, J. Mater. Chem., 24, 8583 (2011)
Blouin N, Michaud A, Gendron D, Wakim S, Blair E, Neagu-Plesu R, J. Am. Chem. Soc., 130, 732 (2007)
Zhang Y, Zou J, Yip HL, Chen KS, Zeigler DF, Sun Y, Jen AKY, Chem. Mater., 23, 2289 (2011)
Song HJ, Lee TH, Han MH, Lee JY, Moon DK, Polymer, 54(3), 1072 (2013)
Li YX, Zou JY, Yip HL, Li CZ, Zhang Y, Chueh CC, Intemann J, Xu YX, Liang PW, Chen Y, Jen AKY, Macromolecules, 46(14), 5497 (2013)
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Jiang JM, Yang PA, Hsieh TH, Wei KH, Macromolecules, 23, 9155 (2011)

[Referenced By]

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[1] Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos DA, Bredas JL, Logdlund M, Salaneck WR, Nature, 397(6715), 121 (1999)

[2] Lu W, Kuwabara J, Kanbara T, Macromolecules, 44(6), 1252 (2011)

[3] Song HJ, Lee JY, Song IS, Moon DK, Haw JR, J. Ind. Eng. Chem., 17(2), 352 (2011)

[4] Song HJ, Kim DH, Lee EJ, Heo SW, Lee JY, Moon DK, Macromolecules, 45(19), 7815 (2012)

[5] Iwan A, Palewicz M, Chuchmała A, Gorecki L, Sikora A, Mazurek B, Synth. Met., 162, 143 (2012)

[6] Lee JY, Song HJ, Lee SM, Lee JH, Moon DK, Eur. Polym. J., 47, 1686 (2011)

[7] Xiang N, Liu Y, Zhou W, Huang H, Guo X, Tan Z, Zhao B, Shen P, Tan S, Eur. Polym. J., 46, 1084 (2010)

[8] Zhang JE, Cai WZ, Huang F, Wang EG, Zhong CM, Liu SJ, Wang M, Duan CH, Yang TB, Cao Y, Macromolecules, 44(4), 894 (2011)

[9] Subramaniyan S, Xin H, Kim FS, Shoaee S, Durrant JR, Jenekhe SA, Adv. Eng. Mater., 5, 854 (2011)

[10] Manceau M, Angmo D, Jorgensen M, Krebs FC, Org. Electron., 4, 566 (2011)

[11] Lee JY, Aleshin AN, Kim DW, Lee HJ, Kim YS, Wegner G, Enkelmann V, Roth S, Park YW, Synth. Met., 152, 169 (2005)

[12] Yamamoto T, Kokubo H, Kobashi M, Sakai Y, Chem. Mater., 23, 4616 (2004)

[13] Yasuda T, Sakai Y, Aramaki S, Yamamoto T, Chem. Mater., 24, 6060 (2005)

[14] Lee Y, Nam YM, Jo WH, J. Mater. Chem., 24, 8583 (2011)

[15] Blouin N, Michaud A, Gendron D, Wakim S, Blair E, Neagu-Plesu R, J. Am. Chem. Soc., 130, 732 (2007)

[16] Zhang Y, Zou J, Yip HL, Chen KS, Zeigler DF, Sun Y, Jen AKY, Chem. Mater., 23, 2289 (2011)

[17] Song HJ, Lee TH, Han MH, Lee JY, Moon DK, Polymer, 54(3), 1072 (2013)

[18] Li YX, Zou JY, Yip HL, Li CZ, Zhang Y, Chueh CC, Intemann J, Xu YX, Liang PW, Chen Y, Jen AKY, Macromolecules, 46(14), 5497 (2013)

[19] Hou J, Chen TL, Zhang S, Huo L, Sista S, Yang Y, Macromolecules, 23, 9217 (2009)

[20] Jiang JM, Yang PA, Hsieh TH, Wei KH, Macromolecules, 23, 9155 (2011)