Skip to main content
SpringerLink
Log in

Polyfluorenes containing pyrazine units: Synthesis, photophysics and electroluminescence

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

Abstract

A series of conjugated copolymers of 9,9-dioctylfluorene and symmetrical pyrazine unit (BY) were synthesized by Suzuki copolymerization and were used as novel light-emitting materials in PLEDs. Efficient energy transfer was observed in both thin film and solution. Compared with the lowest occupied molecular orbital (LUMO) energy level of the polyfluorenes homopolymer (PFO), the lower LUMO energy levels of copolymers indicated that the introduction of the BY unit would be benefit to electron injection. The turn-on voltages of their single-layer electroluminescent (EL) devices (ITO/PEDOT/polymer/LiF/Al) were at 6.1–4.0 V, which were much lower than that of PFO (7.0 V). The maximum brightness, current efficiency, and external quantum efficiency of all PFBY copolymers were higher than those of the PFO homopolymer. The single-layer device of PFBY5 was the best one in the copolymers, with a maximum brightness of 485 cd/m2, a current efficiency of 0.29 cd/A, and an external quantum efficiency of 0.10%. The introduction of PVK and TPBI for the multilayer device of PFBY5 increased the device efficiencies, which showed a maximum brightness of 3012 cd/m2, a maximum current efficiency of 1.81 cd/A, and an external quantum efficiency of 0.66%.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB. Light-emitting-diodes based on conjugated polymers. Nature, 1990, 347: 539–541

    Article  CAS  Google Scholar 

  2. Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos DA, Bredas JL, Logdlund M, Salaneck WR. Electroluminescence in conjugated polymers. Nature, 1999, 397: 121–128

    Article  CAS  Google Scholar 

  3. Jin Y, Song S, Park SH, Park JA, Kim J, Woo HY, Lee K, Suh H. Synthesis and properties of various PPV derivatives with phenyl substituents. Polymer, 2008, 49: 4559–4568

    Article  CAS  Google Scholar 

  4. Chen Q, Liu N, Ying L, Yang W, Wu H, Xu W, Cao Y. Novel white-light-emitting polyfluorenes with benzothiadiazole and Ir complex on the backbone. Polymer, 2009, 50: 1430–1437

    Article  CAS  Google Scholar 

  5. Yu W L, 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 

  6. Park JW, Park SJ, Kim YH, Shin DC, You H, Kwon SK. Pure color and stable blue-light emission-alternating copolymer based on fluorene and dialkoxynaphthalene. Polymer, 2009, 50: 102–106

    Article  CAS  Google Scholar 

  7. Zhu Y, Gibbons KM, Kulkarni AP, Jenekhe SA. Polyfluorenes containing dibenzo[a,c]phenazine segments: Synthesis and efficient blue electroluminescence from intramolecular charge transfer states. Macromolecules, 2007, 40: 804–813

    Article  CAS  Google Scholar 

  8. Herguch P, Jiang XZ, Liu MS, Jen AKY. Highly efficient fluorene- and benzothiadiazole-based conjugated copolymers for polymer light-emitting diodes. Macromolecules, 2002, 35: 6094–6100

    Article  Google Scholar 

  9. Qiao Z, Peng JB, Jin Y, Liu QL, Weng JEN, He ZC, Han SH, Cao DR. Synthesis and electroluminescence properties of fluorene-co-diketopyrrolopyrrole-co-phenothiazine polymers. Polymer, 2000, 51: 1016–1023

    Article  Google Scholar 

  10. Yang J, Jiang CY, Zhang Y, Yang RQ, Yang W, Hou Q, Cao Y. High-efficiency saturated red emitting polymers derived from fluorene and naphthoselenadiazole. Macromolecules, 2004, 37: 1211–1218

    Article  CAS  Google Scholar 

  11. Wang M, Tong H, Cheng YX, Xie ZY, Wang LX, Jing XB, Wang FS. Synthesis and characterization of polyfluorenes containing bisphenazine units. J Polym Sci Polym Chem, 2010, 48: 1990–1999

    Article  CAS  Google Scholar 

  12. Li YY, Wu HB, Zou JH, Ying L, Yang W, Cao Y. Enhancement of spectral stability and efficiency on blue light-emitters via introducing dibenzothiophene-S,S-dioxide isomers into polyfluorene backbone. Org Electron, 2009, 10: 901–909

    Article  CAS  Google Scholar 

  13. Gao BX, Wang M, Cheng YX, Wang LX, Jing XB, Wang FS. Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings. J Am Chem Soc, 2008, 130: 8297–8306

    Article  CAS  Google Scholar 

  14. Hu J, Zhang D, Harris FW. Ruthenium(III) chloride catalyzed oxidation of pyrene and 2,7-disubstitued pyrenes: An efficient, one-step synthesis of pyrene-4,5-diones and pyrene-4,5,9,10-tetraones. J Org Chem, 2005, 70: 707–708

    Article  CAS  Google Scholar 

  15. Li SB, Zhao P, Huang YQ, Li TC, Tang C, Zhu R, Zhao L, Fan QL, Huang SQ, Xu ZS, Huang W. Poly-(p-phenylene vinylenes) with pendent 2,4-difluorophenyl and fluorenyl moieties: Synthesis, characterization, and device performance. J Polym Sci Polym Chem, 2009, 47: 2500–2508

    Article  CAS  Google Scholar 

  16. Xin Y, Wen GA, Zeng WJ, Zhao L, Zhu XR, Fan QL, Feng JC, Wang LH, Wei W, Peng B, Cao Y Huang, W. Hyperbranched oxadiazole-containing polyfluorenes: Toward stable blue light PLEDs. Macromolecules, 2005, 38: 6755–6758

    Article  CAS  Google Scholar 

  17. Lee DC, Jang K, McGrath KK, Uy R, Robins KA, Hatchett DW. Self-assembling asymmetric bisphenazines with tunable electronic properties. Chem Mater, 2008, 20: 3688–3695

    Article  CAS  Google Scholar 

  18. Jin Y, Kim Y, Kim SH, Song S, Woo HY, Lee K, Suh H. Novel green-light-emitting polymers based on cyclopenta[def]phenanthrene. Macromolecules, 2008, 41: 5548–5554

    Article  CAS  Google Scholar 

  19. Smith AA, Kannan K, Manavalan R, Rajendiran N. Spectral characteristics of bicalutamide drug in different solvents and beta-cyclodextrin. J Inclusion Phenom Macrocyclic Chem, 2007, 58: 161–167

    Article  CAS  Google Scholar 

  20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR. Gaussian 03 R C. Wallingford: Gaussian Inc, 2004

    Google Scholar 

  21. Jiang ZQ, Zhang WJ, Yao HQ, Yang CL, Cao Y, Qin JG, Yu G, Liu YQ. Copolyfluorenes containing bridged triphenylamine or triphenylamine: Synthesis, characterization, and optoelectronic properties. J Polym Sci Polym Chem, 2009, 47: 3651–3661

    Article  CAS  Google Scholar 

  22. Wang P, Jin H, Yang Q, Liu WL, Shen ZH, Chen XF, Fan XH, Zou DC, Zhou QF. Synthesis, characterization, and electroluminescence of novel copolyfluorenes and their applications in white light emission. J Polym Sci Polym Chem, 2009, 47: 4555–4565

    Article  CAS  Google Scholar 

  23. Liu J, Chen L, Shao SY, Xie ZY, Cheng YX, Geng YH, Wang LX, Jing XB, Wang FS. Three-color white electroluminescence from a single polymer system with blue, green and red dopant units as individual emissive species and polyfluorene as individual polymer host. Adv Mater. 2007, 19: 4224–4228

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory of Polymer Physics and Chemistry; Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China

    Ming Wang, Ying Li, ZhiYuan Xie & LiXiang Wang

Authors
  1. Ming Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ying Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. ZhiYuan Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. LiXiang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to LiXiang Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, M., Li, Y., Xie, Z. et al. Polyfluorenes containing pyrazine units: Synthesis, photophysics and electroluminescence. Sci. China Chem. 54, 656–665 (2011). https://doi.org/10.1007/s11426-011-4238-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-011-4238-6

Keywords

Search

Navigation