Carbazole-Thieno[3,4-b]thiophene Polymers: Synthesis and Photovoltaic Applications

Myung-Jin Baek; Soo-Hyoung Lee; Dong Hee Kim; Youn-Sik Lee

Macromolecular Research, Vol.20, No.2, 147-154, February, 2012

DOI10.1007/s13233-012-0019-0 Export Citation

Carbazole-Thieno[3,4-b]thiophene Polymers: Synthesis and Photovoltaic Applications

Myung-Jin Baek, Soo-Hyoung Lee , Dong Hee Kim¹, and Youn-Sik Lee^†

Division of Chemical Engineering, Nanomaterials Processing Research Center, Chonbuk National University, Jeonbuk, 561-756, Korea
¹Department of Chemistry, Kunsan National University, Jeonbuk, 573-701, Korea

E-mail:

Two novel conjugated polymers consisting of alternating thieno[3,4-b]thiophene and either carbazole (PCTT1) or carbazole with two thiophene spacers (PCTT2) were synthesized. PCTT1 (Mn 44,000) showed a bandgap of 2.14 eV but a significantly deep highest occupied molecular orbital level of -5.52 eV. PCTT1-based photovoltaic devices showed promising power conversion efficiency of 2.53% under AM 1.5 G illumination at 100 mW/cm2.

Keywords:carbazole;thieno[3,4-b]thiophene;conjugated polymer;solar cell.

[References]

Sariciftci NS, Smilowitz L, Heeger AJ, Wudl F, Science., 258, 1474 (1992)
Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ, Science, 270(5243), 1789 (1995)
Halls JJ, Walsh CA, Greenham NC, Marseglia EA, Friend RH, Moratti SC, Holmes AB, Nature, 376(6540), 498 (1995)
Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger AJ, Science., 317, 222 (2007)
Li G, Shrotriya V, Huang JS, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4(11), 864 (2005)
Ma WL, Yang CY, Gong X, Lee K, Heeger AJ, Adv. Funct. Mater., 15(10), 1617 (2005)
Kim JY, Kim SH, Lee HH, Lee K, Ma WL, Gong X, Heeger AJ, Adv. Mater., 18(5), 572 (2006)
Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP, J. Am. Chem. Soc., 131(1), 56 (2009)
Svensson M, Zhang FL, Veenstra SC, Verhees WJH, Hummelen JC, Kroon JM, Inganas O, Andersson MR, Adv. Mater., 15(12), 988 (2003)
Chen MH, Hou J, Hong Z, Yang G, Sista S, Chen LM, Yang Y, Adv. Mater., 21(42), 4238 (2009)
Wang E, Wang L, Lan L, Luo C, Zhuang W, Peng J, Cao Y, Appl. Phys. Lett., 92, 033307 (2008)
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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)
Spanggaard H, Krebs FC, Sol. Energy Mater. Sol. Cells, 83(2-3), 125 (2004)
Scharber MC, Wuhlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CL, Adv. Mater., 18(6), 789 (2006)
Liang Y, Xu Z, Xia J, Tsai ST, Wu Y, Li G, Ray C, Yu L, Adv. Mater., 22, E135-8 (2010)
Hou JH, Chen HY, Zhang SQ, Chen RI, Yang Y, Wu Y, Li G, J. Am. Chem. Soc., 131(43), 15586 (2009)
Blouin N, Michaud A, Leclerc M, Adv. Mater., 19(17), 2295 (2007)
Zou YP, Gendron D, Neagu-Plesu R, Leclerc M, Macromolecules, 42(17), 6361 (2009)
Baek MJ, Lee SH, Zong K, Lee YS, Synth. Met., 160, 1197 (2010)
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JAJ, Vreven T, Kudin KN, Tomasi J, Barone V, Mennucci B, Cossi M, Eds., Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT (2004)
Yang CJ, Jenekhe SA, Macromolecules, 28(4), 1180 (1995)
Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA, Chem. Mater., 16, 4556 (2004)
Hains AW, Ramanan C, Irwin MD, Liu J, Wasielewski MR, Marks TJ, Appl. Mater. Interfaces., 2, 175 (2010)

[Referenced By]

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[1] Sariciftci NS, Smilowitz L, Heeger AJ, Wudl F, Science., 258, 1474 (1992)

[2] Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ, Science, 270(5243), 1789 (1995)

[3] Halls JJ, Walsh CA, Greenham NC, Marseglia EA, Friend RH, Moratti SC, Holmes AB, Nature, 376(6540), 498 (1995)

[4] Kim JY, Lee K, Coates NE, Moses D, Nguyen TQ, Dante M, Heeger AJ, Science., 317, 222 (2007)

[5] Li G, Shrotriya V, Huang JS, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4(11), 864 (2005)

[6] Ma WL, Yang CY, Gong X, Lee K, Heeger AJ, Adv. Funct. Mater., 15(10), 1617 (2005)

[7] Kim JY, Kim SH, Lee HH, Lee K, Ma WL, Gong X, Heeger AJ, Adv. Mater., 18(5), 572 (2006)

[8] Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP, J. Am. Chem. Soc., 131(1), 56 (2009)

[9] Svensson M, Zhang FL, Veenstra SC, Verhees WJH, Hummelen JC, Kroon JM, Inganas O, Andersson MR, Adv. Mater., 15(12), 988 (2003)

[10] Chen MH, Hou J, Hong Z, Yang G, Sista S, Chen LM, Yang Y, Adv. Mater., 21(42), 4238 (2009)

[11] Wang E, Wang L, Lan L, Luo C, Zhuang W, Peng J, Cao Y, Appl. Phys. Lett., 92, 033307 (2008)

[12] Blouin N, Michaud A, Gendron D, Wakim S, Blair E, Neagu-Plesu R, Belletete M, Durocher G, Tao Y, Leclerc M, J. Am. Chem. Soc., 130(2), 732 (2008)

[13] 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)

[14] Spanggaard H, Krebs FC, Sol. Energy Mater. Sol. Cells, 83(2-3), 125 (2004)

[15] Scharber MC, Wuhlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CL, Adv. Mater., 18(6), 789 (2006)

[16] Liang Y, Xu Z, Xia J, Tsai ST, Wu Y, Li G, Ray C, Yu L, Adv. Mater., 22, E135-8 (2010)

[17] Hou JH, Chen HY, Zhang SQ, Chen RI, Yang Y, Wu Y, Li G, J. Am. Chem. Soc., 131(43), 15586 (2009)

[18] Blouin N, Michaud A, Leclerc M, Adv. Mater., 19(17), 2295 (2007)

[19] Zou YP, Gendron D, Neagu-Plesu R, Leclerc M, Macromolecules, 42(17), 6361 (2009)

[20] Baek MJ, Lee SH, Zong K, Lee YS, Synth. Met., 160, 1197 (2010)

[21] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JAJ, Vreven T, Kudin KN, Tomasi J, Barone V, Mennucci B, Cossi M, Eds., Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT (2004)

[22] Yang CJ, Jenekhe SA, Macromolecules, 28(4), 1180 (1995)

[23] Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA, Chem. Mater., 16, 4556 (2004)

[24] Hains AW, Ramanan C, Irwin MD, Liu J, Wasielewski MR, Marks TJ, Appl. Mater. Interfaces., 2, 175 (2010)