Synthesis of quinoxaline-based polymers with multiple electron-withdrawing groups for polymer solar cells

Shinta Lieviana Handoko; Ho Cheol Jin; Dong Ryeol Whang; Sella Kurnia Putri; Joo Hyun Kim; Dong Wook Chang

Journal of Industrial and Engineering Chemistry, Vol.73, 192-197, May, 2019

DOI10.1016/j.jiec.2019.01.024 Export Citation

Synthesis of quinoxaline-based polymers with multiple electron-withdrawing groups for polymer solar cells

Shinta Lieviana Handoko, Ho Cheol Jin¹, Dong Ryeol Whang², Sella Kurnia Putri, Joo Hyun Kim^{1, †}, and Dong Wook Chang^†

Department of Industrial Chemistry, Pukyong National University, 48513 Busan, South Korea
¹Department of Polymer Engineering, Pukyong National University, 48513 Busan, South Korea
²Linz Institute for Organic Solar Cells (LIOS)/Institute of Physical Chemistry, Johannes Kepler University Linz, 4040, Linz, Austria

E-mail:,

Two quinoxaline-based conjugated polymers with multiple electron-withdrawing moieties were synthesized by the Stille coupling reaction for polymer solar cells (PSCs). For the construction of a typical donor-π-acceptor structure, the electron-donating indacenodithiophene (IDT) and indacenodithieno[3,2-b]thiophene (IDTT) were linked to the electron-withdrawing quinoxaline (DPQCF3F) that contained trifluoromethyl and fluorine units via a thiophene bridge to produce PIDT-Qx and PIDTT-Qx, respectively. Owing to the significant contribution of the DPQCF3F unit in the polymer backbone, Voc of the inverted-type PSCs was increased up to 0.92 V. In addition, the replacement of two thiophenes of IDT to two thieno[3,2-b] thiophene units of IDTT in the quinoxaline-based polymer backbone can efficiently improved the light absroption and charge carrier mobility of the resultant polymer. Therefore, a higher PCE of 4.54% was achieved from the device based on PIDTT-Qx with a short circuit current density of 9.30 mA/cm2, an open-circuit voltage of 0.92 V, and a fill factor of 53%, compared with the device based on PIDT-Qx (2.83%).

Keywords:Quinoxaline;Electron-withdrawing;Polymer solar cell;Indacenodithiophene;Indacenodithieno[3,2-b]thiophene

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[Referenced By]

[1] Cheng YJ, Yang SH, Hsu CS, Chem. Rev., 109(11), 5868 (2009)

[2] Li G, Zhu R, Yang Y, Nat. Photonics., 6, 153 (2012)

[3] Gunes S, Neugebauer H, Sariciftci NS, Chem. Rev., 107(4), 1324 (2007)

[4] 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)

[5] Dennler G, Scharber MC, Brabec CJ, Adv. Mater., 21(13), 1323 (2009)

[6] Blom PWM, Mihailetchi VD, Koster LJA, Markov DE, Adv. Mater., 19(12), 1551 (2007)

[7] Li SS, Ye L, Zhao WC, Zhang SQ, Mukherjee S, Ade H, Hou JH, Adv. Mater., 28(42), 9423 (2016)

[8] Zhao WC, Li SS, Yao HF, Zhang SQ, Zhang Y, Yang B, Hou JH, J. Am. Chem. Soc., 139(21), 7148 (2017)

[9] He D, Zhao F, Xin J, Rech JJ, Wei Z, Ma W, You W, Li B, Jiang L, Li Y, Wang C, Adv. Energy Mater., 8, 180205 (2018)

[10] Zhu Y, Champion RD, Jenekhe SA, Macromolecules, 39(25), 8712 (2006)

[11] Wu JS, Cheng YJ, Dubosc M, Hsieh CH, Chang CY, Hsu CS, Chem. Commun., 46, 3259 (2010)

[12] Nam SJ, Jeon SJ, Hang YW, Moon DK, J. Ind. Eng. Chem., 63, 191 (2018)

[13] Eom Y, Song CE, Shin WS, Lee SK, Lim E, J. Ind. Chem. Eng., 45, 338 (2017)

[14] Stuart AC, Tumbleston JR, Zhou HX, Li WT, Liu SB, Ade H, You W, J. Am. Chem. Soc., 135(5), 1806 (2013)

[15] Price SC, Stuart AC, Yang L, Zhou H, You W, J. Am. Chem. Soc., 133, 4625 (2011)

[16] Xu XP, Li Y, Luo MM, Peng Q, Chinese Chem. Lett., 27, 1241 (2016)

[17] Casey A, Dimitrov SD, Shakya-Tuladhar P, Fei Z, Nguyen M, Han Y, Anthopoulos TD, Durrant JR, Heeney M, Chem. Mater., 28, 5110 (2016)

[18] Huang Y, Huo L, Zhang S, Guo X, Han CC, Li Y, Hou J, Chem. Commun., 47, 8904 (2011)

[19] Shim JY, Kim T, Kim J, Kim J, Kim I, Kim JY, Suh H, Synth. Met., 205, 112 (2015)

[20] Lu Y, Xiao Z, Yuan Y, Wu H, An Z, Hou Y, Gao C, Huang J, J. Mater. Chem. C, 1, 630 (2013)

[21] Jhuo HJ, Yeh PN, Liao SH, Li YL, Cheng YS, Chen SA, J. Chinese Chem. Soc., 61, 115 (2014)

[22] Chen CP, Chen YC, Yu CY, Polym. Chem., 4, 1161 (2013)

[23] Liu DL, Zhao WC, Zhang SQ, Ye L, Zheng Z, Cui Y, Chen Y, Hou JH, Macromolecules, 48(15), 5172 (2015)

[24] Yang P, Yuan M, Zeigler DF, Watkins SE, Lee JA, Luscombe CK, J. Mater. Chem. C, 2, 3278 (2014)

[25] Putri SK, Kim YH, Whang DR, Lee MS, Kim JH, Chang DW, Org. Electron., 47, 14 (2017)

[26] Putri SK, Kim YH, Whang DR, Kim JH, Chang DW, Macromol. Rapid Commun., 39, 180026 (2018)

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

[28] Cai Y, Zhang X, Xue X, Wei D, Huo L, Sun Y, J. Mater. Chem. C, 5, 7777 (2017)

[29] Xu YX, Chueh CC, Yip HL, Ding FZ, Li YX, Li CZ, Li XS, Chen WC, Jen AKY, Adv. Mater., 24(47), 6356 (2012)

[30] Frisch MJ, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Gaussian 09, Revision A. 1, Gaussian Inc., Wallingford, CT, pp.34 2009.

[31] Yuan J, Qiu L, Zhang Z, Li Y, He Y, Jiang L, Zou Y, Chem. Commun., 52, 6881 (2016)

[32] Bagui A, Iyer SSK, Org. Electron. Phys. Mater. Appl., 15, 1387 (2014)