Skip to main content
Log in

Phosphine oxide-functionalized polyfluorene derivatives: Synthesis, photophysics, electrochemical properties, and electroluminescence performance

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

A series of phosphine oxide-functionalized polyfluorene derivatives, PFH-PO-40-1 (P1), PFH-PO-20-1 (P2), PFH-PO-10-1 (P3), and PFH-PO-1-1 (P4), were prepared via a palladium-mediated Suzuki cross-coupling reaction. The structures and purities of all polymers were fully characterized by 1H and 13C NMR, UV-vis and photoluminescent spectroscopy, gel permeation chromatography, and TGA/DSC. Their emission features showed single broad peaks at about 445 nm in film, compared with those in dilute solutions, which might be caused by some degree of aggregation in the excited states of the backbones. The best electroluminescence (EL) performance of these polymers with configuration of ITO/PEDOT:PSS/Polymer/Alq3/LiF/Al was obtained from P1 (current efficiency was 4.2 Cd/A at 6V).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Braun D, Heeger AJ. Visible light emission from semiconducting polymer diodes. Appl Phys Lett, 1991, 58: 1982–1986

    Article  CAS  Google Scholar 

  2. Burns PL, Holmes AB, Kraft A, Bradley DDC, Brown AR, Friend RH, Gywer RW. Chemical tuning of electroluminescent copolymers to improve emission efficiencies and allow patterning. Nature, 1992, 356: 47–49

    Article  Google Scholar 

  3. Pei Q, Yu G, Zhang C, Yang Y, Heeger AJ. Polymer light-emitting electrochemical cells. Science, 1995, 269: 1086–1088

    Article  CAS  Google Scholar 

  4. Müller CD, Falcou A, Reckefuss N, Rojahn M, Wiederhirn V, Rudati P, Frohne H, Nuyken O, Becker H, Meerhotz K. Multi-colour organic light-emitting displays by solution processing. Nature, 2003, 421: 829–833

    Article  Google Scholar 

  5. Lovinger AJ, Rothverg LJ. Status of and prospects for organic electroluminescence. J Mater Res, 1996, 11: 3174–3187

    Article  Google Scholar 

  6. Bao Z, Lovinger AJ, Brown J. New air-stable n-channel organic thin film transistors. J Am Chem Soc, 1998, 120: 207–208

    Article  CAS  Google Scholar 

  7. Bao Z, Dodabalapur A, Lovinger AJ. Soluble and processable regioregular poly(3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Appl Phys Lett, 1996, 69: 4108–4110

    Article  CAS  Google Scholar 

  8. Sirringhaus H, Tessler N, Friend RH. Integrated optoelectronic devices based on conjugated polymers. Science, 1998, 280: 1741–1744

    Article  CAS  Google Scholar 

  9. Babel A, Jenekhe SA. Electron transport in thin-film transistor from an n-type conjugated polymer. Adv Mater, 2002, 14: 371–374

    Article  CAS  Google Scholar 

  10. Tang CW. Two-layer organic photovoltaic cell. Appl Phys Lett, 1986, 48: 183–185

    Article  CAS  Google Scholar 

  11. Wohrle D, Meissner D. Organic solar cell. Adv Mater, 1991, 3: 129–138

    Article  Google Scholar 

  12. Yu G, Heeger AJ. Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions. J Appl Phys, 1995, 78: 4510–4515

    Article  CAS  Google Scholar 

  13. Arias AC, MacKenzie JD, Stevenson R, Halls JJM, Inbasekaran M, Woo EP, Richards D, Friend RH. Photovoltaic performance and morphology of polyfluorene blends: A combined microscopic and photovoltaic investigation. Macromolecules, 2001, 34: 6005–6013

    Article  CAS  Google Scholar 

  14. Jenekhe SA, Yi S. Efficient photovoltaic cells from semiconducting polymer heterojunctions. Appl Phys Lett, 2000, 77: 2635–2637

    Article  CAS  Google Scholar 

  15. Bernius MT, Inbasekaran M, O’Brien J, Wu WS. Progress with light-emitting polymers. Adv Mater, 2000, 12: 1737–1750

    Article  CAS  Google Scholar 

  16. Neher D. Polyfluorene homopolymers: Conjugated liquid-crystalline polymers for bright blue emission and polarized electroluminescence. Macromol Rapid Commun, 2001, 22: 1366–1385

    Article  Google Scholar 

  17. Scherf U, List EJW. Semiconducting polyfluorenes—Towards reliable structure-property relationship. Adv Mater, 2002, 14: 477–487

    Article  CAS  Google Scholar 

  18. Klärner G, Lee JK, Davey MH, Miller RD. Exciton migration and trapping in copolymers based on dialkylfluorenes. Adv Mater, 1999, 11: 115–119

    Article  Google Scholar 

  19. Yu WL, Pei J, Huang W, Heeger AJ. Spiro-functionalized polyfluorene derivatives as blue light-emitting materials. Adv Mater, 2000, 12: 828–831

    Article  CAS  Google Scholar 

  20. Virgili T, Lidzey DG, Bradley DDC. Efficient energy transfer from blue to red in tetraphenylporphyrin-doped poly (9,9-dioctylfluorene) light-emitting diodes. Adv Mater, 2000, 12: 58–62

    Article  CAS  Google Scholar 

  21. Whitehead KS, Grell M, Bradley DDC, Jandke M, Strohriegl P. Highly polarized blue electroluminescence from homogeneously aligned films of poly(9,9-dioctylfluorene). Appl Phys Lett, 2000, 76: 2946–2948

    Article  CAS  Google Scholar 

  22. Grell M, Knoll W, Lupo D, Meisel A, Miteva T, Neher D, Nothofer HG, Scherf U, Yasuda A. Blue polarized electroluminescence from a liquid crystalline polyfluorene. Adv Mater, 1999, 11: 671–675

    Article  CAS  Google Scholar 

  23. Liu B, Bazan GC. Optimization of the molecular orbital energies of conjugated polymers for optical amplification of fluorescent sen sors. J Am Chem Soc, 2006, 128: 1188–1196

    Article  CAS  Google Scholar 

  24. Wang S, Gaylord BS, Bazan GC. Fluorescein provides a resonance gate for FRET from conjugated polymers to DNA intercalated dyes. J Am Chem Soc, 2004, 126: 5446–5451

    Article  CAS  Google Scholar 

  25. Liu B, Wang S, Bazan GC, Mikhailovsky A. Shape-adaptable water-soluble conjugated polymers. J Am Chem Soc, 2003, 125: 13306–13307

    Article  CAS  Google Scholar 

  26. Fan C, Plaxco KW, Heeger AJ, High-efficiency fluorescence quenching of conjugated polymers by proteins. J Am Chem Soc, 2002, 124: 5642–5643

    Article  CAS  Google Scholar 

  27. Zhou G, Cheng YX, Wang LX, Jing XB, Wang FS. Novel polyphenylenes containing phenol-substituted oxadiazole moieties as fluorescent chemosensors for fluoride ion. Macromolecules, 2005, 38: 2148–2153

    Article  CAS  Google Scholar 

  28. Zhou X, Yan J, Pei J. Exploiting an imidazole-functionalized polyfluorene derivative as a chemosensory material. Macromolecules, 2004, 37: 7078–7080

    Article  CAS  Google Scholar 

  29. Zhou G, Qian G, Ma L, Cheng YX, Xie ZY, Wang LX, Jing XB, Wang FS. Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials. Macromolecules, 2005, 38: 5416–5424

    Article  CAS  Google Scholar 

  30. Qin CJ, Cheng YX, Wang LX, Jing XB, Wang FS. Phosphonate-functionalized polyfluorene as a highly water-soluble iron(III) chemosensor. Macromolecules, 2008, 41: 7798–7804

    Article  CAS  Google Scholar 

  31. Qin CJ, Wu XF, Gao BX, Tong H, Wang LX. Amino acid-functionalized polyfluorene as a water-soluble Hg2+ chemosensor with high solubility and high photoluminescence quantum yield. Macromolecules, 2009, 42: 5427–5433

    Article  CAS  Google Scholar 

  32. Wu X, Xu B, Tong H, Wang LX. Phosphonate-functionalized polyfluorene film sensors for sensitive detection of iron(III) in both organic and aqueous media. Macromolecules, 2010, 43: 8917–8921

    Article  CAS  Google Scholar 

  33. Huang F, Hou L, Wu H, Wang X, Shen H, Cao W. High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors. J Am Chem Soc, 2004, 126: 9845–9853

    Article  CAS  Google Scholar 

  34. Wu H, Huang F, Mo Y, Yang W, Wang D, Peng J. Efficient electron injection from a bilayer cathode consisting of aluminum and alcohol-/water-soluble conjugated polymers. Adv Mater, 2004, 16: 1826–1830

    Article  CAS  Google Scholar 

  35. Yang R, Wu H, Cao Y, Bazan GC. Control of cationic conjugated polymer performance in light emitting diodes by choice of counterion. J Am Chem Soc, 2006, 128: 14422–14423

    Article  CAS  Google Scholar 

  36. Peng XG, Schlamp MC, Kadavanich AV, Alivisatos AP. Epitaxial growth of highly luminescent CdSe/CdS core/shell nanocrystals with photostability and electronic accessibility. J Am Chem Soc, 1997, 119: 7019–7029

    Article  CAS  Google Scholar 

  37. Skaff H, Sill K, Emrick T. Quantum dots tailored with poly(para-phenylene vinylene). J Am Chem Soc, 2004, 126: 11322–11325

    Article  CAS  Google Scholar 

  38. Scherf U, List EJW. Semiconducting polyfluorenes-Towards reliable structure-property relationships. Adv Mater, 2002, 14: 477–487

    Article  CAS  Google Scholar 

  39. Gong X, Iyer PK, Moses D, Bazan GC, Heeger AJ, Xiao SS. Stabilized blue emission from polyfluorene-based light-emitting diodes: Elimination of fluorenone defects. Adv Funct Mater, 2003, 13: 325–330

    Article  CAS  Google Scholar 

  40. Gong X, Moses D, Heeger AJ. White light electrophosphorescence from polyfluorene-based light-emitting diodes: Utilization of fluorenone defects. J Phys Chem B, 2004, 108: 8601–8605

    Article  CAS  Google Scholar 

  41. Brooks AJ, Antonio F, Micheal RW, Tobin JM. Effects of arylene diimide thin film growth conditions on n-channel OFET performance. Adv Funct Mater, 2008, 18: 1329–1339

    Article  Google Scholar 

  42. Chu B, Laser Light Scattering: Basic Principles and Practice. 2nd ed, San Diego: Academic Press, 1991

    Google Scholar 

  43. Hall J, Lehn JM, DeCian A, Fischer J. Synthesis and structure of the copper(II) complex of a chiral bis(dihydrooxazole) ligand. Helv Chim Acta, 1991, 74: 1–6

    Article  CAS  Google Scholar 

  44. Yan JC, Chen X, Zhou QL, Pei J. Chiral polyfluorene derivatives: Synthesis, chiroptical properties, and investigation of the structure-property relationships. Macromolecules, 2007, 40: 832–839

    Article  CAS  Google Scholar 

  45. Leeuw DM, Simenon MMJ, Brown AR, Einerhand REF. Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices. Synth Met, 1997, 87: 53–59

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Jian Pei, ZhangLin Zhou or Samuel S. Mao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guo, Z., Liu, D., Wang, C. et al. Phosphine oxide-functionalized polyfluorene derivatives: Synthesis, photophysics, electrochemical properties, and electroluminescence performance. Sci. China Chem. 54, 678–684 (2011). https://doi.org/10.1007/s11426-011-4249-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-011-4249-3

Keywords

Navigation