Synthesis and Photovoltaic Properties of Low Band Gap π-conjugated Polymers Based on 2-pyran-4-ylidene-malononitrile Derivatives

2-pyran-4-ylidene-malononitrile을 기본으로 하는 작은 Band Gap을 가지는 공중합체의 합성 및 광전변환 특성

  • You, Hyeri (Department of Polymer Engineering, Pukyong National University) ;
  • Shin, Woong (Department of Polymer Engineering, Pukyong National University) ;
  • Park, Jeong Bae (Department of Polymer Engineering, Pukyong National University) ;
  • Park, Sang Jun (Department of Polymer Engineering, Pukyong National University) ;
  • Lim, Jun Heok (Department of Chemical Engineering, Pukyong National University) ;
  • Kim, Joo Hyun (Department of Polymer Engineering, Pukyong National University)
  • 유혜리 (부경대학교 응용화학공학부 고분자공학전공) ;
  • 신웅 (부경대학교 응용화학공학부 고분자공학전공) ;
  • 박정배 (부경대학교 응용화학공학부 고분자공학전공) ;
  • 박상준 (부경대학교 응용화학공학부 고분자공학전공) ;
  • 임준혁 (부경대학교 응용화학공학부 화학공학전공) ;
  • 김주현 (부경대학교 응용화학공학부 고분자공학전공)
  • Received : 2009.02.06
  • Accepted : 2009.03.03
  • Published : 2009.06.10

Abstract

A series of poly[2-(2,6-dimethylpyran-4-ylidene)malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PM-PPV), poly[2-{2,6-Bis-[2-(5-bromothiophen-2-yl)-vinyl]-pyran-4-ylidene}-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMT-PPV) and poly[2-[2,6-Bis-(2-{4-[(4-bromophenyl)-phenylamino]-phenyl}-vinyl)-pyran-4-ylidene]-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMTPA-PPV) were synthesized by the Heck coupling reaction. The band gap of PM-PPV, PMT-PPV and PMTPA-PPV were 2.18 eV, 1.90 eV and 2.07 eV, respectively. The LUMO energy levels of PM-PPV, PMT-PPV and PMTPA-PPV were 3.65 eV, 3.54 eV and 3.62 eV, respectively and the HOMO energy levels of those were 5.83 eV, 5.61 eV and 5.52 eV, respectively. The photovoltaic devices based on the polymers was fabricated. The efficiency of the solar cells based on PM-PPV, PMT-PPV and PMTPA-PPV were 0.028%, 0.031% and 0.11%, respectively and the open circuit voltage (Voc) was 0.59 V~0.69 V under AM 1.5 G and 1 sun condition ($100mA/cm^2$).

Heck coupling reaction을 이용해서 poly[2-(2,6-dimethylpyran-4-ylidene)malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PM-PPV), poly[2-{2,6-Bis-[2-(5-bromothiophen-2-yl)-vinyl]-pyran-4-ylidene}-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMT-PPV), poly[2-[2,6-Bis-(2-{4-[(4-bromophenyl)-phenylamino]-phenyl}-vinyl)-pyran-4-ylidene]-malononitrile-alt-1,4-bis(dodecyloxy)-2,5-divinylbenzene] (PMTPA-PPV)를 합성하였다. PM-PPV, PMT-PPV, PMTPA-PPV의 band gap은 각각 2.18 eV, 1.90 eV, 2.07 eV로 나타났다. LUMO 에너지 준위는 각각 3.65 eV, 3.54 eV, 3.62 eV로 나타났고 HOMO 에너지 준위는 각각 5.83 eV, 5.61 eV, 5.52 eV이고 소자를 제작하여 측정한 결과는 AM 1.5 G [1 sun condition ($100mA/cm^2$)]에서의 효율은 0.028%, 0.031%, 0.11%이고 open-circuit voltage (Voc)는 0.59 V~0.69 V로 나타났다.

Keywords

Acknowledgement

Supported by : 교육인적자원부, 한국 학술진흥재단

References

  1. C. W. Tang, Appl. Phys. Lett., 48, 183 (1986) https://doi.org/10.1063/1.96937
  2. J. Xue, S. Uchida, B. P. R, and, S. R. Forrest, Appl. Phys. Lett., 84, 3013 (2004) https://doi.org/10.1063/1.1713036
  3. G. Yu, J. Gao, J. C. Hummelen, F. Wudl, and A. J. Heeger, Science, 270, 1789 (1995) https://doi.org/10.1126/science.270.5243.1789
  4. C. J. Brabec, S. E. Shaheen, C. Winder, and N. S. Sariciftci, Appl. Phys. Lett., 80, 1288 (2002) https://doi.org/10.1063/1.1446988
  5. J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger, and C. G. Bazan, Nature Mater., 6, 497 (2007) https://doi.org/10.1038/nmat1928
  6. D. Muhlbacher, M. Scharber, M. Morana, Z. Zhu, D. Waller, R. Gaudiana, and C. Brabec, Adv. Mater., 18, 2884 (2006) https://doi.org/10.1002/adma.200600160
  7. Z. Zhu, D. Waller, R. Gaudiana, M. Morana, D. M$\ddot{u}$hlbacher, M. Scharber, and C. Brabec, Macromolecules, 40, 1981 (2007) https://doi.org/10.1021/ma062376o
  8. J. H. Kim, H. Nam, and H. Lee., J. Polym. Sci. Part A: Polym. Chem. Ed., 44, 3729 (2006) https://doi.org/10.1002/pola.21435
  9. J. H. Kim and H. Lee, Chem. Mater., 14, 2270 (2002) https://doi.org/10.1021/cm011553r
  10. X. Sun, Y. Liu, X. Xu, C. Yang, G. Yu, S. Chen, Z. Zhao, W. Qiu, Y. Li, and D. Zhu, J. Phys. Chem. B., 109, 10786 (2005) https://doi.org/10.1021/jp0509515
  11. C. Wu, J. C. Strum, R. A. Register, J. Tian, E. P. Dana, and M. E. Thompson, IEEE Trans. Electron Devices, 44, 1269 (1997) https://doi.org/10.1109/16.605468