화학공학소재연구정보센터
Macromolecular Research, Vol.23, No.2, 214-222, February, 2015
2,2-dimethyl-2H-benzimidazole based small molecules for organic solar cells
E-mail:
We report the small molecules utilizing new electron-deficient unit, 2,2-dimethyl-2H-benzimidazole (MBI) and phenanthro[9,10-c][1,2,5]thiadiazole (PT), for the photovoltaic application. Donor-acceptor-donor (D-A-D) types of conjugated small molecules containing benzo[1,2-b;3,4-b′]dithiophene (BDT) as electron rich unit and MBI and PT as electron deficient units (SM1 and SM2) were synthesized. D-A-D type of small molecules has the abilities of increasing intramolecular charge transfer (ICT) inducing long wavelength absorption and lowering the HOMO level for the improvement of open-circuit voltage (V OC ). SM1 was synthesized by coupling BDT and PT units by Stille coupling reaction with Pd(0)-catalyst. By using same type of Pd(0)-catalized reaction, BDT unit and MBI unit linked with two thiophenes were coupled to provide SM2. The spectrum of SM2 in the solid thin film shows absorption band with maximum peak at 601 nm and the absorption onset at 756 nm, corresponding to band gap of 1.64 eV. The device comprising SM2 with PCBM (3:7) showed a V OC of 0.62 V, a J SC of 1.69 mA/cm2, and a fill factor (FF) of 0.27, giving a power conversion efficiency of 0.28%.
  1. Dou LT, Chen CC, Yoshimura K, Ohya K, Chang WH, Gao J, Liu YS, Richard E, Yang Y, Macromolecules, 46(9), 3384 (2013)
  2. Seri M, Bolognesi M, Chen ZH, Lu SF, Koopman W, Facchetti A, Muccini M, Macromolecules, 46(16), 6419 (2013)
  3. Shi Q, Cheng P, Li Y, Zhan X, Adv. Energy Mater., 2, 63 (2012)
  4. Lu Z, Li C, Fang T, Lia G, Bo Z, J. Mater. Chem. A, 1, 7657 (2013)
  5. Tang A, Li L, Lu Z, Huang J, Jia H, Zhan C, Tan Z, Lib Y, Yao J, J. Mater. Chem. A, 1, 5747 (2013)
  6. Roquet S, Cravino A, Leriche P, Aleveque O, Frere P, Roncali J, J. Am. Chem. Soc., 128(10), 3459 (2006)
  7. Shang H, Fan H, Liu Y, Hu W, Li Y, Zhan X, J. Mater. Chem., 21, 9667 (2011)
  8. Tamayo AB, Dang XD, Walker B, Seo J, Kent T, Nguyen TQ, Appl. Phys. Lett., 94, 103301 (2009)
  9. Walker B, Tomayo AB, Dang XD, Zalar P, Seo JH, Garcia A, Tantiwiwat M, Nguyen TQ, Adv. Funct. Mater., 19(19), 3063 (2009)
  10. Zhang J, Yang Y, He C, He YJ, Zhao GJ, Li YF, Macromolecules, 42(20), 7619 (2009)
  11. Shang HX, Fan HJ, Liu Y, Hu WP, Li YF, Zhan XW, Adv. Mater., 23(13), 1554 (2011)
  12. Ying W, Zhang X, Li X, Wu W, Guo F, Li J, Agren H, Hua J, Tetrahedron, 70, 3901 (2014)
  13. Min J, Zhang ZG, Zhang SY, Zhang MJ, Zhang J, Li YF, Macromolecules, 44(19), 7632 (2011)
  14. Song S, Park SH, Jin Y, Park J, Shim JY, Kim I, Lee H, Lee K, Suh H, J. Polym. Sci. A: Polym. Chem., 48(20), 4567 (2010)
  15. Song S, Park SH, Jin Y, Kim I, Lee K, Suh H, Polymer, 51(23), 5385 (2010)
  16. Zhang WM, Smith J, Watkins SE, Gysel R, McGehee M, Salleo A, Kirkpatrick J, Ashraf S, Anthopoulos T, Heeney M, McCulloch I, J. Am. Chem. Soc., 132(33), 11437 (2010)
  17. Tsao HN, Cho D, Andreasen JW, Rouhanipour A, Breiby DW, Pisula W, Mullen K, Adv. Mater., 21(2), 209 (2009)
  18. Carle JE, Andreasen JW, Jorgensen M, Krebs FC, Sol. Energy Mater. Sol. Cells, 94(5), 774 (2010)
  19. Song S, Park S, Kwon S, Lee BH, Shim JY, Lee J, Park SH, Jin Y, Kim I, Lee K, Suh H, Sol. Energy Mater. Sol. Cells, 105, 229 (2012)
  20. Lee TH, Wu KY, Lin TY, Wu JS, Wang CL, Hsu CS, Macromolecules, 46(19), 7687 (2013)
  21. Kim JH, Song CE, Kim BS, Kang IN, Shin WS, Hwang DH, Chem. Mater., 26, 1234 (2014)
  22. Frisch MJ, Gaussian 03, Revision E.01. Gaussian Inc., Wallingford (2004)
  23. Mei CY, Liang L, Zhao FG, Wang JT, Yu LF, Li YX, Li WS, Macromolecules, 46(19), 7920 (2013)
  24. Robert CC, Christopher MMN, Eric DP, Jeremy WW, Jack WO, Claire AML, Gregory MS, Ronald EN, Oana DJ, J. Nanotechnol., 572329, 10 (2011)
  25. Keshtov ML, Marochkin DV, Kochurov VS, Khokhlov AR, Koukaras EN, Sharma GD, J. Mater. Chem. A, 2, 155 (2014)
  26. Wang XC, Jiang P, Chen Y, Luo H, Zhang ZG, Wang HQ, Li XY, Yu G, Li YF, Macromolecules, 46(12), 4805 (2013)
  27. Keshtov ML, Marochkin DV, Kochurov VS, Khokhlov AR, Koukaras EN, Sharma GD, Polym. Chem., 4, 4033 (2013)
  28. Li YW, Chen LW, Chen YJ, Li C, Zhang P, Gao LF, Yang XM, Tu YF, Zhu XL, Sol. Energy Mater. Sol. Cells, 108, 136 (2013)