화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Clean Technology, Vol.20, No.4, 415-424, December, 2014
Export Citation
Rigid한 Phenothiazine-Quinoxaline D/A 공액 고분자 구조의 용해성 향상 연구 및 유기박막태양전지로의 특성 분석
Improved Solubility and Characterization of Photovoltaic Properties D/A Copolymers based on Rigid Structure of Phenothiazine-Quinoxaline
성기호, 윤대희, 박용성†
  • 상명대학교 공업화학과, 110-743 서울특별시 종로구 홍지문2길 20
Ki-Ho Seong, Dae-Hee Yun, and Yong-Sung Park†
  • Department of Industrial Chemistry, Sangmyung University, 20, Hongjimun 2-gil, Jongno-gu, Seoul 110-743, Korea
E-mail:
초록
본 연구는 전자주개 물질인 phenothiazine 유도체와 전자받개 물질로 quinoxaline 유도체를 Suzuki coupling reaction으로 push-pull 구조의 고분자(PPQX-2hdPTZ (P1), POPQX-2hdPTZ (P2))를 합성하였다. 용해도 향상을 위해 기본 골격에 alkoxy 사슬을 도입하였고, 반응시간을 단축시키고 중합도를 높이기 위해 마이크로웨이브 합성 반응기를 이용하여 중합시켰다. 합성된 고분자는 물리적, 열적, 광학적 및 전기화학적 특성을 확인하였다. 두 고분자의 초기분해온도는 323-328 ℃로서 열 안정성이 우수함을 확인하였고, 추가로 alkoxy 사슬을 도입한 P2의 중합도가 더 높았다. 전기화학적 특성을 분석한 결과 두 고분자의 HOMO에너지 레벨은 유사하였다. 합성된 고분자는 ITO/PEDOT:PSS/active layer/BaF2/Al 구조로 소자를 제작하여 유기박막태양전지로의 특성을 확인하였다. 각 소자는 박막의 두께를 다르게 하여 이에 따른 효율의 변화를 확인하였고, 박막의 두께가 얇아질수록 높은 효율을 나타내었다(PCEmax: P1 = 1.0%, P2 = 1.1%).
In this study, two kinds of polymer (PPQX-2hdPTZ (P1), POPQX-2hdPTZ (P2)) were synthesised by Suzuki coupling reaction based on phenothiazine derivative as electron-donor and quinoxaline derivative as electron-acceptor. Microwave synthesis workstation was used to shorten the polymerization time and increase the degree of polymerization. The physical, thermal stability, optical and electrochemical properties of the synthesized polymer were confirmed. The thermal stability of two polymers was outstanding as the initial decomposition temperature was 323-328℃. And additional substituted alkoxy chain on P2 showed higher degree of polymerization. An analysis of electrochemical properties, all polymer had similar HOMO energy level values. Device was fabricated by ITO/PEDOT:PSS/active layer/BaF2/Al structure and photovoltaic properties were confirmed. Each device has a different film thickness and the resulting change in PCE was confirmed. As a result the thinner thickness of the film showed a high efficiency (PCEmax: P1 = 1.0%, P2 = 1.1%).
Keywords:Quinoxaline;Phenothiazine;Conjugated polymer;Rigid structure
  1. Hong YR, Ng JY, Wong HK, Moh LCH, Yip YJ, Chen ZK, Norsten TB, Sol. Energy Mater. Sol. Cells, 102, 58 (2012)
  2. Mondal R, Ko SW, Norton JE, Miyaki N, Becerril HA, Verploegen E, Toney MF, Breadas JL, McGehee MM, Bao Z, J. Mater. Chem., 19, 7195 (2009)
  3. Lee SK, Lee WH, Cho JM, Park SJ, Park JU, Shin WS, Lee JC, Kang IN, Moon SJ, Macromolecules, 44(15), 5994 (2011)
  4. Yiu AT, Beaujuge PM, Lee OP, Woo CH, Toney MF, Frechet JMJ, J. Am. Chem. Soc., 134(4), 2180 (2012)
  5. Tan Z, Imae I, Ooyama Y, Komaguchi K, Ohshita J, Harima Y, Eur. Polym. J., 49, 1634 (2013)
  6. Heo SW, Song KW, Choi MH, Oh HS, Moon DK, Sol. Energy Mater. Sol. Cells, 114, 82 (2013)
  7. Li S, He ZC, Yu J, Chen SA, Zhong AS, Wu HB, Zhong C, Qin JG, Li Z, J. Polym. Sci. A: Polym. Chem., 50(14), 2819 (2012)
  8. Burkhart B, Khlyabich PP, Canak TC, LaJoie TW, Thompson BC, Macromolecules, 44(6), 1242 (2011)
  9. Burkhart B, Khlyabich PP, Thompson BC, Macromolecules, 45(9), 3740 (2012)
  10. Biniek L, Fall S, Chochos CL, Anokhin DV, Ivanov DA, Leclerc N, Leveque P, Heiser T, Macromolecules, 43(23), 9779 (2010)
  11. Xu XF, Cai P, Lu Y, Choon NS, Chen JW, Hu X, Ong BS, J. Polym. Sci. A: Polym. Chem., 51(2), 424 (2013)
  12. Kim G, Yeom HR, Cho S, Seo JH, Kim JY, Yang C, Macromolecules, 45(4), 1847 (2012)
  13. Biniek L, Chochos CL, Leclerc N, Boyron O, Fall S, Leveque P, Heiser T, J. Polym. Sci. A: Polym. Chem., 50(9), 1861 (2012)
  14. Lee JY, Shin WS, Haw JR, Moon DK, J. Mater. Chem., 19, 4938 (2009)
  15. Aaron SH, Chandra BKC, Navaneetha KS, Paul AK, Francis D, Appl. Mater. Interfaces, 4, 5183 (2012)
  16. Petran A, Bogdan E, Terec A, Grosu I, Rev. Roum. Chim., 57, 345 (2012)
  17. Iqbal Z, Wu WQ, Zhang H, Han L, Fang X, Wang L, Kuang DB, Meier H, Cao D, Organic Electronics, 14, 2662 (2013)
  18. Kim SH, Sakong C, Chang JB, Kim B, Ko MJ, Kim DH, Hong KS, Kim JP, Dyes Pigment, 97, 262 (2013)
  19. Lapkowski M, Plewa S, Stolarczyk A, Doskocz J, Soloducho J, Cabaj J, Bartoszek M, Sulkowski WW, Electrochim. Acta, 53(5), 2545 (2008)
  20. Pan DH, Phillips DL, J. Phys. Chem. A, 103(24), 4737 (1999)
  21. Jang W, Lyu F, Park H, Meng QB, Lee SH, Lee YS, Chem. Phys. Lett., 584, 119 (2013)
  22. Seo YH, Lee WH, Park JH, Bae C, Hong Y, Park JW, Kang IN, J. Polym. Sci. A: Polym. Chem., 50(4), 649 (2012)
  23. Iqbal Z, Wu WQ, Kuang DB, Wang L, Meier H, Cao D, Dyes Pigment, 96, 722 (2013)
  24. Zhang MJ, Fan HJ, Guo X, Yang Y, Wang SS, Zhang ZG, Zhang J, Zhan XW, Li YF, J. Polym. Sci. A: Polym. Chem., 49(12), 2746 (2011)
  25. Guo X, Zhang MJ, Huo LJ, Cui CH, Wu Y, Hou JH, Li YF, Macromolecules, 45(17), 6930 (2012)
  26. Huo LJ, Tan ZA, Wang X, Zhou Y, Han MF, Li YF, J. Polym. Sci. A: Polym. Chem., 46(12), 4038 (2008)
  27. Peng Q, Xu J, Zheng WX, J. Polym. Sci. A: Polym. Chem., 47(13), 3399 (2009)
  28. He YJ, Wu WP, Zhao GJ, Liu YQ, Li YF, Macromolecules, 41(24), 9760 (2008)
  29. Seong, Yun DH, Woo JW, Appl. Chem. Eng., 24(5), 537 (2013)
  30. Yun DH, Yoo HS, Heo SW, Song HJ, Moon DK, Woo JW, Park YS, J. Ind. Eng. Chem., 19(2), 421 (2013)
  31. Price SC, Stuart AC, You W, Macromolecules, 43(10), 4609 (2010)
  32. Tan Z, Imae I, Ooyama Y, Komaguchi K, Ohshita J, Harima Y, Eur. Polym. J., 49, 1634 (2013)
  33. Morvillo P, Parenti F, Diana R, Fontanesi C, Mucci A, Tassinari F, Schenetti L, Sol. Energy Mater. Sol. Cells, 104, 45 (2012)
  34. Peng Q, Liu X, Qin Y, Xu J, Li M, Dai L, J. Mater. Chem., 21, 7714 (2011)
  35. Wu FY, Zha DJ, Chen L, Chen YW, J. Polym. Sci. A: Polym. Chem., 51(7), 1506 (2013)
  36. Yang P, Yuan M, Zeigler DF, Watkins SE, Lee JA, Luscombe CK, J. Mater. Chem. C, 41, 1754 (2012)
  37. Zhang JE, Cai WZ, Huang F, Wang EG, Zhong CM, Liu SJ, Wang M, Duan CH, Yang TB, Cao Y, Macromolecules, 44(4), 894 (2011)
  38. Zhou EJ, Cong JZ, Yamakawa S, Wei QS, Nakamura M, Tajima K, Yang CH, Hashimoto K, Macromolecules, 43(6), 2873 (2010)
  39. Li YW, Chen YJ, Liu X, Wang Z, Yang XM, Tu YF, Zhu XL, Macromolecules, 44(16), 6370 (2011)
  40. Zhang Z, Peng Q, Yang D, Chen Y, Huang Y, Pu X, Lu Z, Jiang Q, Liu Y, Synth. Met., 175, 21 (2013)
  41. Yoo HS, Park YS, Appl. Chem. Eng., 24(1), 93 (2013)
  42. Zhang GB, Fu YY, Zhang Q, Xie ZY, Polymer, 51(11), 2313 (2010)
  43. Colladet K, Fourier S, Cleij TJ, Lutsen L, Gelan J, Vanderzande D, Nguyen LH, Neugebauer H, Sariciftci S, Aguirre A, Janssen G, Goovaerts E, Macromolecules, 40(1), 65 (2007)