화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Applied Chemistry for Engineering, Vol.22, No.1, 15-20, February, 2011
Export Citation
2,3-Dimethyl-5,8-dithiophen-2-yl-quinoxaline을 기본 골격으로 한 새로운 고분자 물질의 합성 및 광전변환특성
Synthesis and Photovoltaic Properties of New π-conjugated Polymers Based on 2,3-dimethyl-5,8-dithiophen-2-yl-quinoxaline
신웅, 박정배, 박상준, 조미영, 서홍석1, 김주현†
  • 부경대학교 응용화학공학부 고분자공학과
  • 1부산대학교 화학과
Woong Shin, Jeong Bae Park, Sang Jun Park, Mi Young Jo, Hongsuk Suh1, and Joo Hyun Kim†
  • Department of Polymer Engineering, Pukyong National University, Busan 608-739, Korea
  • 1Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Korea
E-mail:
초록
2,3-Dimethyl-5,8-dithiophen-2-yl-quinoxaline을 기본 골격으로 한 poly[2,3-dimethyl-5,8-dithiophene-2-yl-quinoxaline-alt-9,9-dihexyl-9H-fluorene] (PFTQT)과 poly[2,3-dimethyl-5,8-dithiophene-2-yl-quinoxaline-alt-10-hexyl-10H-phenothiazine] (PPTTQT) 을 Suzuki coupling법을 이용하여 중합 하였다. 합성된 고분자들은 chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran(THF), toluene과 같은 유기용매에 대한 용해도가 우수하였고, PFTQT의 최대흡수파장과 밴드 갭은 각각 440 nm와 2.30 eV이고, PPTTQT의 경우는 각각 445 nm와 2.23 eV이었다. PFTQT의 HOMO 및 LUMO 에너지준위는 -6.05와 -3.75 eV이고, PPTTQT의 경우는 각각 -5.89와 -3.66 eV이었다. 합성된 고분자들과 전자 받개 물질인 (6)-1-(3-(methoxycarbonyl)-{5}-1-phenyl[5,6]-fullerene (PCBM)을 1 : 2의 중량비로 블렌딩하여 제작한 태양전지의 효율은 AM (air mass)1.5 G, 1 sun 건(100 mA/cm2)에서 PFTQT는 0.24%, PPTTQT의 경우는 0.16%로 측정되었다. 그리고 소자의 단락전류 밀도(Jsc), FF (fill factor)와 개방전압(Voc)은 PFTQT의 경우 각각 0.97 mA/cm2, 29%, 0.86 V이며, PPTTQT의 경우 각각 0.80 mA/cm2, 28%, 0.71 V이었다.
Poly[2,3-dimethyl-5,8-dithiophene-2-yl-quinoxaline-alt-9,9-dihexyl-9H-fluorene] (PFTQT) and poly[2,3-dimethyl-5,8-dithiophen-2-yl-quinoxaline-alt-10-hexyl-10H-phenothiazine (PPTTQT) based on 2,3-dimethyl-5,8-dithiophen-2-yl-quinoxaline were synthesized by Suzuki coupling reaction. All polymers were soluble in common organic solvents such as chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran (THF) and toluene. The maximum absorption wavelength and band gap of PFTQT were 440 nm and 2.30 eV, and PPTTQT were 445 nm and 2.23 eV, respectively. The HOMO and LUMO energy level of PFTQT were -6.05 and -3.75 eV, and PPTTQT were -5,89 and -3.66 eV, respectively. The organic photovoltaic devices based on the blend of polymer and PCBM (1 : 2 by weight ratio) were fabricated. Efficiencies of devices were 0.24% (PFTQT) and 0.16% (PPTTQT), respectively. The short circuit current density (Jsc), fill factor (FF), and open circuit voltage (Voc) of the device with PFTQT were 0.97 mA/cm2, 29% and 0.86 V, and the device based on PPTTQT were 0.80 mA/cm2, 28% and 0.71 V, 31% and 0.71 V, respectively, under air mass (AM) 1.5 G and 1 sun condition (100 mA/cm2).
Keywords:organic photovoltaic cells;Suzuki coupling;electron donor;quinoxaline
  1. Ju JU, Jung SO, Zhao QH, Kim YH, Je JT, Kwon SK, Bull. Korean Chem. Soc., 29, 335 (2008)
  2. Roncali J, Chem. Rev., 92, 711 (1992)
  3. Yu G, Cao J, Hummelen JC, Wudl F, Heeger AJ, Science., 270, 1789 (1996)
  4. Li G, Shrotriya V, Huang J, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4, 864 (2005)
  5. Halls JJM, Pichler K, Friend RH, Moratti SC, Holmes AB, Appl. Phys. Lett., 68, 3120 (1996)
  6. Yu G, Heeger AJ, J. Appl. Phys., 78, 4510 (1995)
  7. Brabec CJ, Sariciftci NS, Hummelen JC, Adv. Funct. Mater., 11(1), 15 (2001)
  8. Granstrom M, Petritsch K, Arias AC, Lux A, Andersson MR, Friend RH, Nature., 397, 257 (1998)
  9. Ma WL, Yang CY, Gong X, Lee K, Heeger AJ, Adv. Funct. Mater., 15(10), 1617 (2005)
  10. Hou JH, Chen HY, Zhang SQ, Chen RI, Yang Y, Wu Y, Li G, J. Am. Chem. Soc., 131(43), 15586 (2009)
  11. Kim JH, Lee H, Synth. Met., 157, 1040 (2007)
  12. Sailer M, Franz AW, Muller TJJ, Chem. Eur. J., 14, 2602 (2008)
  13. Yang RQ, Tian RY, Yan JG, Zhang Y, Yang J, Hou Q, Yang W, Zhang C, Cao Y, Macromolecules, 38(2), 244 (2005)
  14. Baek JB, Ferguson JB, Tan LS, Macromolecules, 36(12), 4385 (2003)
  15. Jung MS, Shin W, Park SJ, You HR, Park JB, Suh H, Lim Y, Yoon DY, Kim JH, Synth. Met., 159, 1928 (2009)
  16. Svensson M, Zhang FL, Veenstra SC, Verhees WJH, Hummelen JC, Kroon JM, Inganas O, Andersson MR, Adv. Mater., 15(12), 988 (2003)
  17. Beaupre S, Dumas J, Leclerc M, Chem. Mater., 18, 4011 (2006)
  18. Kong XX, Kulkarni AP, Jenekhe SA, Macromolecules, 36(24), 8992 (2003)
  19. Wu CC, Strum JC, Register RA, Tian J, Dana EP, Thompson, M. E. IEEE Trans. Electron Devices., 44, 1269 (1997)
  20. Chan SH, Chen CP, Chao TC, Ting C, Lin CS, Ko BT, Macromolecules, 41(15), 5519 (2008)
  21. Kroon JM, Wienk MM, Verhees WJH, Hummelen JC, Thin Solid Films., 403, 223 (2002)
  22. Chen CP, Chan SH, Chao TC, Ting C, Ko BT, J. Am. Chem. Soc., 130(38), 12828 (2008)