6,7-DIALKOXY-2,3-DIPHENYLQUINOXALINE BASED CONJUGATED POLYMERS FOR SOLAR CELLS WITH HIGH OPEN-CIRCUIT VOLTAGE
|
摘要
6,7-Dialkoxy-2,3-diphenylquinoxaline based narrow band gap conjugated polymers, poly[2,7-(9-octyl-9H-carbazole)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PCDTQ) and poly[2,7-(9,9-dioctylfluorene)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PFDTQ), have been synthesized by Suzuki polycondensation. Their optical, electrochemical, transport and photovoltaic properties have been investigated in detail. Hole mobilities of PCDTQ and PFDTQ films spin coated from 1,2-dichlorobenzene (DCB) solutions are 1.0 × 10-4 and 4.1 × 10-4 cm2V-1s-1, respectively. Polymer solar cells were fabricated with the as-synthesized polymers as the donor and PC61BM and PC71BM as the acceptor. Devices based on PCDTQ:PC71BM (1:3) and PFDTQ:PC71BM (1:3) fabricated from DCB solutions demonstrated a power conversion efficiency (PCE) of 2.5% with a Voc of 0.95 V and a PCE of 2.5% with a Voc of 0.98 V, respectively, indicating they are promising donor materials.
6,7-Dialkoxy-2,3-diphenylquinoxaline based narrow band gap conjugated polymers, poly[2,7-(9-octyl-9H-carbazole)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PCDTQ) and poly[2,7-(9,9-dioctylfluorene)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PFDTQ), have been synthesized by Suzuki polycondensation. Their optical, electrochemical, transport and photovoltaic properties have been investigated in detail. Hole mobilities of PCDTQ and PFDTQ films spin coated from 1,2-dichlorobenzene (DCB) solutions are 1.0 × 10-4 and 4.1 × 10-4 cm2V-1s-1, respectively. Polymer solar cells were fabricated with the as-synthesized polymers as the donor and PC61BM and PC71BM as the acceptor. Devices based on PCDTQ:PC71BM (1:3) and PFDTQ:PC71BM (1:3) fabricated from DCB solutions demonstrated a power conversion efficiency (PCE) of 2.5% with a Voc of 0.95 V and a PCE of 2.5% with a Voc of 0.98 V, respectively, indicating they are promising donor materials.
6,7-Dialkoxy-2,3-diphenylquinoxaline based narrow band gap conjugated polymers, poly[2,7-(9-octyl-9H-carbazole)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PCDTQ) and poly[2,7-(9,9-dioctylfluorene)-alt-5,5-(5,8-di-2-thinenyl-(6,7-dialkoxy-2,3-diphenylquinoxaline))] (PFDTQ), have been synthesized by Suzuki polycondensation. Their optical, electrochemical, transport and photovoltaic properties have been investigated in detail. Hole mobilities of PCDTQ and PFDTQ films spin coated from 1,2-dichlorobenzene (DCB) solutions are 1.0 × 10-4 and 4.1 × 10-4 cm2V-1s-1, respectively. Polymer solar cells were fabricated with the as-synthesized polymers as the donor and PC61BM and PC71BM as the acceptor. Devices based on PCDTQ:PC71BM (1:3) and PFDTQ:PC71BM (1:3) fabricated from DCB solutions demonstrated a power conversion efficiency (PCE) of 2.5% with a Voc of 0.95 V and a PCE of 2.5% with a Voc of 0.98 V, respectively, indicating they are promising donor materials.
引文
1 Coakley, K.M. and McGehee, M.D., Chem. Mater., 2004, 16: 4533
2 Krebs, F.C., Sol. Energy Mater. Sol. Cells., 2009, 93(4): 394
3 Yu, G., Gao, J., Hummelen, J.C., Wudl, F. and Heeger, A.J., Science, 1995, 270(5243): 1789
4 Shin, M., Kim, H., Park, J., Nam, S., Heo, K., Ree, M., Ha, C.S. and Kim, Y., Adv. Funct. Mater., 2010, 20(5): 748
5 Li, G., Shrotriya, V., Yao, Y. and Yang, Y., J. Appl. Phys., 2005, 98: 043704
6 Ma, W., Kim, J.Y., Lee, K. and Heeger, A.J., Macromol. Rapid. Commun., 2007, 28(17): 1776
7 Chen, Y.H., Huang, P.T., Lin, K.C., Huang, Y.J. and Chen, C.T., Organic Electronics, 2012, 13(2): 283
8 Li, G., Shrotriya, V., Huang, J.S., Yao, Y., Moriarty, T., Emery, K. and Yang, Y., Nat. Mater., 2005, 4(11): 864
9 Li, Y.F., Acc. Chem. Res., 2012, 45(5): 723
10 Dennler, G., Scharber, M.C., Ameri, T., Denk, P., Forberich, K., Waldauf, C. and Brabec, C.J., Adv. Mater., 2008, 20(3): 579
11 Scharber, M.C., Wuhlbacher, D., Koppe, M., Denk, P., Waldauf, C., Heeger, A.J. and Brabec, C.L., Adv. Mater., 2006, 18(6): 789
12 Chen, J.W. and Cao, Y., Acc. Chem. Res., 2009, 42(11): 1709
13 Liang, Y.Y., Xu, Z., Xia, J.B., Tsai, S.T., Wu, Y., Li, G., Ray, C. and Yu, L.P., Adv. Mater., 2010, 22(20): E135
14 Muhlbacher, D., Scharber, M., Morana, M., Zhu, Z.G., Waller, D., Gaudiana, R. and Brabec, C., Adv. Mater., 2006, 18(21): 2884
15 Huo, L.J., Zhang, S.Q., Guo, X., Xu, F., Li, Y.F. and Hou, J.H., Angew. Chem. Int. Ed., 2011, 50(41): 9697
16 Duan, C.H., Huang, F. and Cao, Y., J. Mater. Chem., 2012, 22(21): 10416
17 Winder, C. and Sariciftci, N.S., J. Mater. Chem., 2004, 14(7): 1077
18 Wang, E.G., Ma, Z.F., Zhang, Z., Vandewal, K., Henriksson, P., Inganas, O., Zhang, F.L. and Andersson, M.R., J. Am. Chem. Soc., 2011, 133(36): 14244
19 Zhang, Y., Zou, J.Y., Yip, H.L., Chen, K.S., Zeigler, D.F., Sun, Y. and Jen, A.K.Y., Chem. Mater., 2011, 23(9): 2289
20 Wang, E.G., Hou, L.T., Wang, Z.Q., Ma, Z.F., Hellstrom, S., Zhuang, W.L., Zhang, F.L., Inganas, O. and Andersson, M.R., Macromolecules, 2011, 44(7): 2067
21 Lee, Y., Nam, Y.M. and Jo, W.H., J. Mater. Chem., 2011, 21(24): 8583
22 Lee, S.K., Lee, W.H., Cho, J.M., Park, S.J., Park, J.U., Shin, W.S., Lee, J.C., Kang, I.N. and Moon, S.J., Macromolecules, 2011, 44(15): 5994
23 Lee, P.I., Hsu, S.L.C., Lee, J.F., Chuang, H.Y. and Lin, P.Y., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(3): 662
24 Lai, M.H., Chueh, C.C., Chen, W.C., Wu, J.L. and Chen, F.C., J. Polym. Sci., Part A: Polym. Chem., 2009, 47(3): 973
25 Kitazawa, D., Watanabe, N., Yamamoto, S. and Tsukamoto, J., Sol. Energy. Mater. Sol. Cells., 2012, 98: 203
26 Kitazawa, D., Watanabe, N., Yamamoto, S. and Tsukamoto, J., Appl. Phys. Lett., 2009, 95: 053701
27 Wang, M., Li, C.H., Lv, A.F., Wang, Z.H. and Bo, Z.S., Macromolecules, 2012, 45(7): 3017
28 Song, J.S., Du, C., Li, C.H. and Bo, Z.S., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(19): 4267
29 Qin, R.P., Li, W.W., Li, C.H., Du, C., Veit, C., Schleiermacher, H.F., Andersson, M., Bo, Z.S., Liu, Z.P., Inganas, O., Wuerfel, U. and Zhang, F.L., J. Am. Chem. Soc., 2009, 131(41): 14612
30 Du, C., Li, C.H., Li, W.W., Chen, X., Bo, Z.S., Veit, C., Ma, Z.F., Wuerfel, U., Zhu, H.F., Hu, W.P. and Zhang, F.L., Macromolecules, 2011, 44(19): 7617
31 Seo, J.H., Gutacker, A., Sun, Y.M., Wu, H.B., Huang, F., Cao, Y., Scherf, U., Heeger, A.J. and Bazan, G.C., J. Am. Chem. Soc., 2011, 133(22): 8416
32 Park, S.H., Roy, A., Beaupre, S., Cho, S., Coates, N., Moon, J.S., Moses, D., Leclerc, M., Lee, K. and Heeger, A.J., Nat. Photonics, 2009, 3(5): 297
33 Tolman, C.A., Seidel, W.C. and Gerlach, D.H., J. Am. Chem. Soc., 1972, 94(8): 2669
34 Liu, M.F., Chen, Y.L., Zhang, C. and Bo, Z.S., Chinese J. Polym. Sci., 2012, 30(2): 308
35 Liu, M.F., Chen, Y.L., Zhu, B., Han, Y., Huang, W.G., Du, C. and Bo, Z.S., Chinese J. Polym. Sci., 2012, 30(3): 405
36 Kaake, L.G., Welch, G.C., Moses, D., Bazan, G.C. and Heeger, A.J., J. Phys. Chem. Lett., 2012, 3(10): 1253
37 Peet, J., Kim, J.Y., Coates, N.E., Ma, W.L., Moses, D., Heeger, A.J. and Bazan, G.C., Nat. Mater., 2007, 6(7): 497
38 Campoy-Quiles, M., Ferenczi, T., Agostinelli, T., Etchegoin, P.G., Kim, Y., Anthopoulos, T.D., Stavrinou, P.N., Bradley, D.D.C. and Nelson, J., Nat. Mater., 2008, 7(2): 158
39 Chen, L.M., Hong, Z.R., Li, G. and Yang, Y., Adv. Mater., 2009, 21(14-15): 1434
40 Chirvase, D., Parisi, J., Hummelen, J.C. and Dyakonov, V., Nanotechnology, 2004, 15(9): 1317
41 Hoppe, H., Niggemann, M., Winder, C., Kraut, J., Hiesgen, R., Hinsch, A., Meissner, D. and Sariciftci, N.S., Adv. Funct. Mater., 2004, 14(10): 1005
42 Kumar, A., Li, G., Hong, Z.R. and Yang, Y., Nanotechnology, 2009, 20(16): 65202
43 Yang, X. and Loos, J., Macromolecules, 2007, 40(5): 1353
44 Yang, X.N., Loos, J., Veenstra, S.C., Verhees, W.J.H., Wienk, M.M., Kroon, J.M., Michels, M.A.J. and Janssen, R.A.J., Nano. Lett., 2005, 5(4): 579
45 Yao, Y., Hou, J.H., Xu, Z., Li, G. and Yang, Y., Adv. Funct. Mater., 2008, 18(12): 1783
2 Krebs, F.C., Sol. Energy Mater. Sol. Cells., 2009, 93(4): 394
3 Yu, G., Gao, J., Hummelen, J.C., Wudl, F. and Heeger, A.J., Science, 1995, 270(5243): 1789
4 Shin, M., Kim, H., Park, J., Nam, S., Heo, K., Ree, M., Ha, C.S. and Kim, Y., Adv. Funct. Mater., 2010, 20(5): 748
5 Li, G., Shrotriya, V., Yao, Y. and Yang, Y., J. Appl. Phys., 2005, 98: 043704
6 Ma, W., Kim, J.Y., Lee, K. and Heeger, A.J., Macromol. Rapid. Commun., 2007, 28(17): 1776
7 Chen, Y.H., Huang, P.T., Lin, K.C., Huang, Y.J. and Chen, C.T., Organic Electronics, 2012, 13(2): 283
8 Li, G., Shrotriya, V., Huang, J.S., Yao, Y., Moriarty, T., Emery, K. and Yang, Y., Nat. Mater., 2005, 4(11): 864
9 Li, Y.F., Acc. Chem. Res., 2012, 45(5): 723
10 Dennler, G., Scharber, M.C., Ameri, T., Denk, P., Forberich, K., Waldauf, C. and Brabec, C.J., Adv. Mater., 2008, 20(3): 579
11 Scharber, M.C., Wuhlbacher, D., Koppe, M., Denk, P., Waldauf, C., Heeger, A.J. and Brabec, C.L., Adv. Mater., 2006, 18(6): 789
12 Chen, J.W. and Cao, Y., Acc. Chem. Res., 2009, 42(11): 1709
13 Liang, Y.Y., Xu, Z., Xia, J.B., Tsai, S.T., Wu, Y., Li, G., Ray, C. and Yu, L.P., Adv. Mater., 2010, 22(20): E135
14 Muhlbacher, D., Scharber, M., Morana, M., Zhu, Z.G., Waller, D., Gaudiana, R. and Brabec, C., Adv. Mater., 2006, 18(21): 2884
15 Huo, L.J., Zhang, S.Q., Guo, X., Xu, F., Li, Y.F. and Hou, J.H., Angew. Chem. Int. Ed., 2011, 50(41): 9697
16 Duan, C.H., Huang, F. and Cao, Y., J. Mater. Chem., 2012, 22(21): 10416
17 Winder, C. and Sariciftci, N.S., J. Mater. Chem., 2004, 14(7): 1077
18 Wang, E.G., Ma, Z.F., Zhang, Z., Vandewal, K., Henriksson, P., Inganas, O., Zhang, F.L. and Andersson, M.R., J. Am. Chem. Soc., 2011, 133(36): 14244
19 Zhang, Y., Zou, J.Y., Yip, H.L., Chen, K.S., Zeigler, D.F., Sun, Y. and Jen, A.K.Y., Chem. Mater., 2011, 23(9): 2289
20 Wang, E.G., Hou, L.T., Wang, Z.Q., Ma, Z.F., Hellstrom, S., Zhuang, W.L., Zhang, F.L., Inganas, O. and Andersson, M.R., Macromolecules, 2011, 44(7): 2067
21 Lee, Y., Nam, Y.M. and Jo, W.H., J. Mater. Chem., 2011, 21(24): 8583
22 Lee, S.K., Lee, W.H., Cho, J.M., Park, S.J., Park, J.U., Shin, W.S., Lee, J.C., Kang, I.N. and Moon, S.J., Macromolecules, 2011, 44(15): 5994
23 Lee, P.I., Hsu, S.L.C., Lee, J.F., Chuang, H.Y. and Lin, P.Y., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(3): 662
24 Lai, M.H., Chueh, C.C., Chen, W.C., Wu, J.L. and Chen, F.C., J. Polym. Sci., Part A: Polym. Chem., 2009, 47(3): 973
25 Kitazawa, D., Watanabe, N., Yamamoto, S. and Tsukamoto, J., Sol. Energy. Mater. Sol. Cells., 2012, 98: 203
26 Kitazawa, D., Watanabe, N., Yamamoto, S. and Tsukamoto, J., Appl. Phys. Lett., 2009, 95: 053701
27 Wang, M., Li, C.H., Lv, A.F., Wang, Z.H. and Bo, Z.S., Macromolecules, 2012, 45(7): 3017
28 Song, J.S., Du, C., Li, C.H. and Bo, Z.S., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(19): 4267
29 Qin, R.P., Li, W.W., Li, C.H., Du, C., Veit, C., Schleiermacher, H.F., Andersson, M., Bo, Z.S., Liu, Z.P., Inganas, O., Wuerfel, U. and Zhang, F.L., J. Am. Chem. Soc., 2009, 131(41): 14612
30 Du, C., Li, C.H., Li, W.W., Chen, X., Bo, Z.S., Veit, C., Ma, Z.F., Wuerfel, U., Zhu, H.F., Hu, W.P. and Zhang, F.L., Macromolecules, 2011, 44(19): 7617
31 Seo, J.H., Gutacker, A., Sun, Y.M., Wu, H.B., Huang, F., Cao, Y., Scherf, U., Heeger, A.J. and Bazan, G.C., J. Am. Chem. Soc., 2011, 133(22): 8416
32 Park, S.H., Roy, A., Beaupre, S., Cho, S., Coates, N., Moon, J.S., Moses, D., Leclerc, M., Lee, K. and Heeger, A.J., Nat. Photonics, 2009, 3(5): 297
33 Tolman, C.A., Seidel, W.C. and Gerlach, D.H., J. Am. Chem. Soc., 1972, 94(8): 2669
34 Liu, M.F., Chen, Y.L., Zhang, C. and Bo, Z.S., Chinese J. Polym. Sci., 2012, 30(2): 308
35 Liu, M.F., Chen, Y.L., Zhu, B., Han, Y., Huang, W.G., Du, C. and Bo, Z.S., Chinese J. Polym. Sci., 2012, 30(3): 405
36 Kaake, L.G., Welch, G.C., Moses, D., Bazan, G.C. and Heeger, A.J., J. Phys. Chem. Lett., 2012, 3(10): 1253
37 Peet, J., Kim, J.Y., Coates, N.E., Ma, W.L., Moses, D., Heeger, A.J. and Bazan, G.C., Nat. Mater., 2007, 6(7): 497
38 Campoy-Quiles, M., Ferenczi, T., Agostinelli, T., Etchegoin, P.G., Kim, Y., Anthopoulos, T.D., Stavrinou, P.N., Bradley, D.D.C. and Nelson, J., Nat. Mater., 2008, 7(2): 158
39 Chen, L.M., Hong, Z.R., Li, G. and Yang, Y., Adv. Mater., 2009, 21(14-15): 1434
40 Chirvase, D., Parisi, J., Hummelen, J.C. and Dyakonov, V., Nanotechnology, 2004, 15(9): 1317
41 Hoppe, H., Niggemann, M., Winder, C., Kraut, J., Hiesgen, R., Hinsch, A., Meissner, D. and Sariciftci, N.S., Adv. Funct. Mater., 2004, 14(10): 1005
42 Kumar, A., Li, G., Hong, Z.R. and Yang, Y., Nanotechnology, 2009, 20(16): 65202
43 Yang, X. and Loos, J., Macromolecules, 2007, 40(5): 1353
44 Yang, X.N., Loos, J., Veenstra, S.C., Verhees, W.J.H., Wienk, M.M., Kroon, J.M., Michels, M.A.J. and Janssen, R.A.J., Nano. Lett., 2005, 5(4): 579
45 Yao, Y., Hou, J.H., Xu, Z., Li, G. and Yang, Y., Adv. Funct. Mater., 2008, 18(12): 1783