Article
  • Synthesis and Characterization of π-Conjugated Polymer Based on Phthalimide Derivative and its Application for Polymer Solar Cells
  • Do TT, Ha YE, Kim JH
  • 프탈이미드 유도체를 기본으로 하는 공액고분자의 합성과 특성, 그리고 태양전지의 적용
  • Do TT, 하예은, 김주현
Abstract
A new copolymer named T-TI24T (poly((5,5-(2-butyl-5,6-bisdecyloxy-4,7-di-thiophen-2-yl-isoindole-1,3-dione))-alt-(2,5-thiophene))) based on phthalimide derivative and thiophene is synthesized by the Stille-coupling reaction. The polymer shows relatively high number average molecular weight of 86500 g/mol with good solubility in common organic solvents such as chloroform, 1,2-dichlorobenzene, and toluene and is thermally stable up to 380 ℃. Besides, it possesses a relatively low highest occupied molecular orbital (HOMO) energy level of -5.33 eV, promising the high open circuit voltage (Voc) for photovoltaic applications. Active layer solution of polymer T-TI24T-as a donor and (6)-1-(3-(methoxycarbonyl)-{5}-1-phenyl[5,6]-fullerene (PCBM)-as an acceptor in different weight ratios is applied to fabricate the polymer solar cell devices. The ratio of polymer/PCBM affects the solar cell efficiency and the best performance exhibits in the device with polymer/PCBM = 1:3 (w/w), which shows a power conversion efficiency (PCE) of 0.199% and a Voc of 0.99 V, respectively. Even though the device shows the very low PCE, the Voc is higher than that of well known bulk heterojunction type solar cell based on P3HT:PC61BM (c.a. 0.5 V).

프탈이미드 유도체와 티오펜 단량체들을 이용하여 새로운 고분자인 poly((5,5-(2-butyl-5,6-bisdecyloxy-4,7-dithiophen-2-yl-isoindole-1,3-dione))-alt-(2,5-thiophene))(T-TI24T)를 Stille법을 이용하여 합성하였다. T-TI24T의 수평균 분자량은 86500 g/mol로 매우 높으며 클로로포름, 1,2-디클로로벤젠, 톨루엔과 같은 용매에 매우 잘 용해된다. 또한 380 ℃까지 매우 우수한 열적 안정성을 갖고 있다. T-TI24T는 꽤 낮은 호모에너지 준위(-5.33 eV)를 갖고 있다. 서로 다른 T-TI24T와 (6)-1-(3-(methoxycarbonyl)-{5}-1-phenyl[5,6]-fullerene(PCBM)의 무게비를 갖는 블렌드를 광활성층으로 하는 태양전지를 제작하여 특성을 살펴본 결과 고분자와 PCBM의 비율이 1:3일 때 가장 최적화된 결과를 보였으며, 이 때 광전변환 효율과 개방전압은 각각 0.199%와 0.99였다. T-TI24T 기반 태양전지들은 비록 매우 작은 광전변환 효율을 갖지만 잘 알려진 P3HT:PC61BM으로 구성된 태양전지와 비교해 큰 매우 큰 개방전압을 갖는다(약 0.5 V).

Keywords: polymer solar cells; conjugated polymer; phthalimide; stille coupling reaction.

References
  • 1. Yang X, Loos J, Macromolecules., 5, 1353 (2007)
  •  
  • 2. Liang YY, Wu Y, Feng DQ, Tsai ST, Son HJ, Li G, Yu LP, J. Am. Chem. Soc., 131(1), 56 (2009)
  •  
  • 3. Cai WZ, Gong X, Cao Y, Sol. Energy Mater. Sol. Cells, 94(2), 114 (2010)
  •  
  • 4. Guo XG, Xin H, Kim FS, Liyanage ADT, Jenekhe SA, Watson MD, Macromolecules, 44(2), 269 (2011)
  •  
  • 5. Wang EG, Hou LT, Wang ZQ, Ma ZF, Hellstrom S, Zhuang WL, Zhang FL, Inganas O, Andersson MR, Macromolecules, 44(7), 2067 (2011)
  •  
  • 6. Jin EQ, Du C, Wang M, Li WW, Li CH, Wei HD, Bo ZS, Macromolecules, 45(19), 7843 (2012)
  •  
  • 7. Zhang ZG, Wang J, J. Mater. Chem., 22, 4178 (2012)
  •  
  • 8. Jo MY, Park SJ, Park T, Won YS, Kim JH, Org. Electron., 13, 2185 (2012)
  •  
  • 9. Price SC, Stuart AC, Yang L, Zhou H, You W, J. Am.Chem. Soc., 133, 4625 (2011)
  •  
  • 10. Chu TY, Lu J, Beaupre S, Zhang Y, Pouliot J, Wakim S, Zhou J, Leclerc M, Li Z, Ding J, Tao Y, J. Am. Chem. Soc, 133, 4250 (2011)
  •  
  • 11. Amb CM, Chen S, Graham KR, Subbiah J, Small CE, So F, Reynolds JR, J. Am. Chem. Soc., 133(26), 10062 (2011)
  •  
  • 12. You JB, Chen CC, Dou LT, Murase S, Duan HS, Hawks SA, Xu T, Son HJ, Yu LP, Li G, Yang Y, Adv. Mater., 24(38), 5267 (2012)
  •  
  • 13. Huo LJ, Ye L, Wu Y, Li ZJ, Guo X, Zhang MJ, Zhang SQ, Hou JH, Macromolecules, 45(17), 6923 (2012)
  •  
  • 14. Lee JW, Choi YS, Jo WH, Org. Electron., 13, 3060 (2012)
  •  
  • 15. Ding P, Zhong C, Zou Y, Pan C, Wu H, Cao Y, J. Phys.Chem. C., 115, 16211 (2011)
  •  
  • 16. Jiang JM, Yang PA, Hsieh TH, Wei KH, Macromolecules, 44(23), 9155 (2011)
  •  
  • 17. Wang M, Li CH, Lv AF, Wang ZH, Bo ZS, Macromolecules, 45(7), 3017 (2012)
  •  
  • 18. Weitz RT, Amsharov K, Zschieschang U, Villas EB, Goswami DK, Burghard M, Dosch H, Jansen M, Kern K, Klauk H, J. Am. Chem. Soc., 130(14), 4637 (2008)
  •  
  • 19. Gundlach DJ, Pernstich KP, Wilckens G, Gruter M, Haas S, Batlogg B, J. Appl. Phys.064502/1, 98 (2005)
  •  
  • 20. Tatemichi S, Ichikawa M, Koyama T, Taniguchi Y, Appl.Phys. Lett., 89, 112108 (2006)
  •  
  • 21. Xin H, Guo X, Ren G, Watson MD, Jenekhe SA, Adv.Energ. Mater., 2, 575 (2012)
  •  
  • 22. Zhang MJ, Guo X, Zhang ZG, Li YF, Polymer, 52(24), 5464 (2011)
  •  
  • 23. Lee JY, Song KW, Ku JR, Sung TH, Moon DK, Sol. Energy Mater. Sol. Cells, 95(12), 3377 (2011)
  •  
  • 24. Lee JY, Lee SM, Song KW, Moon DK, Eur. Polym.J., 48, 532 (2012)
  •  
  • 25. Babudri F, Cicco SR, Chiavarone L, Farinola GM, Lopez LC, Naso F, Scamarcio G, J. Mater. Chem., 10, 1573 (2000)
  •  
  • 26. Sleven J, Walrand CG, Binnemans K, Mater. Sci. Eng. C., 18, 229 (2001)
  •  
  • 27. Topacli C, Topach A, Civan M, Ercan F, Durmus M, Ahsen V, Thin Solid Films, 516(23), 8299 (2008)
  •  
  • 28. Wintgens V, Amiel C, J. Photochem. Photobiol. A., 168, 217 (2004)
  •  
  • 29. Najari A, Beaupre S, Berrouard P, Zou YP, Pouliot JR, Lepage-Perusse C, Leclerc M, Adv. Funct. Mater., 21(4), 718 (2011)
  •  
  • 30. Helgesen M, Gevorgyan SA, Krebs FC, Janssen RAJ, Chem. Mater., 21, 4669 (2009)
  •  
  • 31. Lee JF, Hsu SLC, Lee PI, Chuang HY, Chen JS, Chou WY, J. Polym. Sci. A: Polym. Chem., 49(21), 4618 (2011)
  •  
  • 32. Wakim S, Beaupre S, Blouin N, Aich BR, Rodman S, Gaudiana R, Tao Y, Leclerc M, J. Mater. Chem., 19, 5351 (2009)
  •  
  • 33. Coffin RC, Peet J, Rogers J, Bazan GC, Nat. Chem., 1, 657 (2009)
  •  
  • 34. 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)
  •  
  • 35. Baran D, Balan A, Stubhan T, Ameri T, Toppare L, Brabec CJ, Synth. Met., 162, 2047 (2012)
  •  
  • 36. Patil AV, Lee WH, Kim K, Park H, Kang IN, Lee SH, Polym. Chem., 2, 2907 (2011)
  •  
  • 37. Xin H, Guo X, Kim FS, Ren G, Watson MD, Jenekhe SA, J. Mater. Chem., 19, 5303 (2009)
  •  
  • 38. Zhang G, Fu Y, Zhang Q, Xie Z, Macromol. Chem. Phys., 211, 2596 (2010)
  •  
  • 39. Zhang Y, Hau SK, Yip HL, Sun Y, Acton A, Jen AKY, Chem. Mater., 22, 2696 (2010)
  •  
  • 40. Chen GY, Cheng YH, Chou YJ, Su MS, Chen CM, Wei KH, Chem. Commun., 47, 5064 (2011)
  •  
  • 41. von Hauff E, Parisi J, Dyakonov V, Thin Solid Films, 511(-), 506 (2006)
  •  
  • 42. Nakamura J, Murata K, Takahashi K, Appl. Phys. Lett., 87, 132105 (2005)
  •  
  • 43. Liu J, Shi YJ, Yang Y, Adv. Funct. Mater., 11(6), 420 (2001)
  •  
  • 44. Berton N, Ottone C, Labet V, Bettignies R, Bailly S, Grand A, Morell C, Sadki S, Chandezon F, Macromol. Chem. Phys., 212, 2127 (2011)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2023 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2013; 37(6): 694-701

    Published online Nov 25, 2013

  • Received on May 17, 2013
  • Accepted on Sep 6, 2013