Photovoltaic Properties of Polymer with Fluorene and Imine Groups in the Main Chain

이민기와 플루오렌기를 주쇄에 함유하는 고분자의 광기전 성질

  • Kim, Hyung-Jun (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University) ;
  • Lee, Jung-Hyo (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University) ;
  • Kwak, Chan-Kyu (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University) ;
  • Jin, Sung-Ho (Department of Chemistry Education and Interdisciplinary Program of Advanced Information and Display Materials, Pusan National University) ;
  • Lee, Taek-Seung (Organic and Optoelectronic Materials Laboratory, Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University)
  • 김형준 (충남대학교 공과대학 바이오응용화학부) ;
  • 이정효 (충남대학교 공과대학 바이오응용화학부) ;
  • 곽찬규 (충남대학교 공과대학 바이오응용화학부) ;
  • 진성호 (부산대학교 화학교육과) ;
  • 이택승 (충남대학교 공과대학 바이오응용화학부)
  • Published : 2008.02.29

Abstract

New polyimine derivative containing fluorene group in the main chain was synthesized via Suzuki cross-coupling polymerization, reduction, and imine formation reaction, consecutively. The synthesized polymer was characterized and explored as organic photovoltaic cell device. The imine polymer P3 in diluted chloroform solution emitted red light (582 nm), whereas its precursor polymers P1 and P2 showed green (about 530 nm) and blue fluorescence (477 nm), respectively. Bulk heterojunction photovoltaic cells fabricated by blending P3 with the fullerene derivative PCBM was found to have a power conversion efficiency of upto 0.0005%, while cells from blending P3 with MEH-PPV yielded 0.0008% of power conversion efficiency.

Keywords

References

  1. S.-S. Sun and N. S. Saricftci, 'Organic Photovoltaics', Taylor & Francis, Boca Raton, 2005
  2. M. B. Schubert and J. H. Werner, 'Flexible Solar Cells for Clothing', Mater Today, 2006, 9, 42-50
  3. M. Halik, H. Klauk, U. Zschieschang, G. Schmid, W. Radlik, and W. Weber, 'Polymer Gate Dielectrics and Conducting-polymer Contacts for High-performance Organic Thin-film Transistors', Adv Mater, 2002, 14, 1717-1722 https://doi.org/10.1002/1521-4095(20021203)14:23<1717::AID-ADMA1717>3.0.CO;2-G
  4. Z. Bao, A. Dodabalapur, and A. J. Lovinger, 'Soluble and Processable Regioregular Poly(3-hexylthiophene) for Thin Film Field-effect Transistor Applications with High Mobility', Appl Phys Lett, 1996, 69, 4108-4110 https://doi.org/10.1063/1.117834
  5. C. J. Brabec, N. S. Sariciftci, and J. C. Hummelen, 'Plastic Solar Cells', Adv Funct Mater, 2001, 11, 15-26 https://doi.org/10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO;2-A
  6. F. Padinger, R. Rittberger, and N. S. Sariciftci, 'Effects of Postproduction Treatment on Plastic Solar Cells', Adv Funct Mater, 2003, 13, 85-88 https://doi.org/10.1002/adfm.200390011
  7. B. R. Hsieh, Y. Yu, E. W. Forsythe, G. M. Schaaf, and W.A. Feld, 'A New Family of Highly Emissive Soluble Poly(p-phenylene vinylene) Derivatives: A Step Toward Fully Conjugated Blue-emitting Poly(p-phenylene vinylenes)', J Am Chem Soc, 1998, 120, 231-232 https://doi.org/10.1021/ja973553r
  8. S. H. Lee, B. B. Jang, and T. Tsutsui, 'Sterically Hindered Fluorenyl-substituted Poly(p-phenylenevinylenes) for Lightemitting Diodes', Macromolecules, 2002, 35, 1356-1364 https://doi.org/10.1021/ma010643e
  9. L. S. Roman, W. Mammo, L. A. A. Petterson, M. R. Andersson, and O. Inganas, 'High Quantum Efficiency Polythiophene', Adv Mater, 1998, 10, 774-777 https://doi.org/10.1002/(SICI)1521-4095(199807)10:10<774::AID-ADMA774>3.0.CO;2-J
  10. H. J. Kim, J. H. Lee, C. K. Kwak, W. K. Son, W. H. Park, and T. S. Lee, 'Fluorogenic Patterning Based on Fluorescence Quenching of $pi$-Conjugated Polymers: Fluorescence Patterning on Films and on Flexible Electrospun Fibrous Mats', Text Sci Eng, 2006, 43, 228
  11. H. J. Kim, J. H. Lee, T. H. Kim, W. S. Lyoo, D. W. Kim, C. Lee, and T. S. Lee, 'Synthesis of Chromo- and Fluorogenic Poly(ortho-diaminophenylene) Chemosensors for Fluoride Anion', J Polym Sci, Part A: Polym Chem, 2007, 45, 1546 https://doi.org/10.1002/pola.21923
  12. K. Pilgram, M. Zupan, and R. Skiles, 'Bromination of 2,1,3- Benzothiadiazole', J Heterocycl Chem, 1970, 7, 629-633 https://doi.org/10.1002/jhet.5570070324
  13. J. C. Hummelen, B. W. Knight, F. LePeq, and F. Wudl, 'Preparation and Characterization of Fulleroid and Methanofullerene Derivatives', J Org Chem, 1995, 60, 532-538 https://doi.org/10.1021/jo00108a012
  14. S. E. Shaheen, C. J. Brabec, N. S. Sariciftci, F. Padinger, T. Fromherz, and J. C. Hummelen, '2.5% Efficient Organic Plastic Solar Cells', Appl Phys Lett, 2001, 78, 841-843.1 https://doi.org/10.1063/1.1345834