Skip to main content
Log in

Synthesis, characterization and applications of vinylsilafluorene copolymers: New host materials for electroluminescent devices

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

Abstract

Vinylsilafluorene (VSiF) was successfully synthesized and copolymerized with vinylcarbazole and methyl methacrylate via free radical copolymerization for the first time. The synthesis, photophysical properties, computational modeling studies, and organic light-emitting devices of the VSiF copolymers were presented. The good coordinated photoluminescent (PL) spectra with the absorption of blue light-emitting materials and the high energy band-gap of the VSiF copolymers were observed. Higher triplet band gap (3 E g) to host the blue phosphorescent emitters and better HOMO and LUMO than PVK for electron and hole injection and transportation of the VSiF model compounds were revealed by density functional theory (DFT) calculations. The preliminary device results in applications of these copolymers as host materials for green phosphorescent emitters demonstrate the copolymers of VSiF and vinylcarbazole have comparable device performance of polyvinylcarazole (PVK), suggesting a bright future of VSiF as building blocks for host materials.

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. Baldo MA, O’Brien DF, You Y, Shoustikov A, Sibley S, Thompson ME, Forrest SR. Highly efficient phosphorescent emission from organic electroluminescent devices. Nature, 1998, 395: 151–154

    Article  CAS  Google Scholar 

  2. Chou P-T, Chi Y. Phosphorescent dyes for organic light-emitting diodes. Chem Eur J, 2007, 13: 380–395

    Article  CAS  Google Scholar 

  3. Lee SJ, Park JS, Song M, Yoon KJ, Kim YI, Jin SH, Seo HJ. Green phosphorescent light-emitting diodes from polymer doped with iridium complex. Appl Phys Lett, 2008, 92: 193312

    Article  Google Scholar 

  4. Chen RF, Zhu R, Zheng C, Liu SJ, Fan QL, Huang W. Germafluorene conjugated copolymer — Synthesis and applications in blue-light-emitting diodes and host materials. Sci China Ser B, 2009, 52: 212–218

    Article  CAS  Google Scholar 

  5. Avilov I, Marsal P, Bredas JL, Beljonne D. Quantum-chemical design of host materials for full-color triplet emission. Adv Mater, 2004, 16: 1624–1629

    Article  CAS  Google Scholar 

  6. Tsuzuki T, Tokito S. Highly efficient, low-voltage phosphorescent organic light-emitting diodes using an iridium complex as the host material. Adv Mater, 2007, 19: 276–280

    Article  CAS  Google Scholar 

  7. Marsal P, Avilov I, da Silva DA, Bredas JL, Beljonne D. Molecular hosts for triplet emission in light emitting diodes: A quantumchemical study. Chem Phys Lett, 2004, 392: 521–528

    Article  CAS  Google Scholar 

  8. Shen JY, Yang XL, Huang TH, Lin JT, Ke TH, Chen LY, Wu CC, Yeh MC. Ambipolar conductive 2,7-carbazole derivatives for electroluminescent devices. Adv Funct Mater, 2007, 17: 983–995

    Article  CAS  Google Scholar 

  9. Li W, Qiao J, Duan L, Wang L, Qiu Y. Novel fluorene/carbazole hybrids with steric bulk as host materials for blue organic electrophosphorescent devices. Tetrahedron, 2007, 63: 10161–10168

    Article  CAS  Google Scholar 

  10. van Dijken A, Bastiaansen JJ, Kiggen NM, Langeveld BM, Rothe C, Monkman A, Bach I, Stossel P, Brunner K. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes: Polymer hosts for high-efficiency light-emitting diodes. J Am Chem Soc, 2004, 126: 7718–7727

    Article  Google Scholar 

  11. Brunner K, van Dijken A, Borner H, Bastiaansen JJ, Kiggen NM, Langeveld BM. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes: Tuning the HOMO level without influencing the triplet energy in small molecules. J Am Chem Soc, 2004, 126: 6035–6042

    Article  CAS  Google Scholar 

  12. Ge ZY, Hayakawa T, Ando S, Ueda M, Akiike T, Miyamoto H, Kajita T, Kakimoto M. Novel bipolar bathophenanthroline containing hosts for highly efficient phosphorescent OLEDs. Org Lett, 2008, 10: 421–424

    Article  CAS  Google Scholar 

  13. Pina J, de Melo JS, Burrows HD, Monkman AP, Navaratnam S. On the triplet state of poly(N-vinylcarbazole). Chem Phys Lett, 2004, 400: 441–445

    Article  CAS  Google Scholar 

  14. Wang YM, Teng F, Xu Z, Hou YB, Wang YS, Xu XR. Electroplex emission from a blend of poly(N-vinylcarbazole) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline. Eur Polym J, 2005, 41: 1020–1023

    Article  CAS  Google Scholar 

  15. Chen RF, Zheng C, Fan QL, Huang W. Structural, electronic, and optical properties of 9-heterofluorenes: A quantum chemical study. J Comput Chem, 2007, 28: 2091–2101

    Article  CAS  Google Scholar 

  16. Chen RF, Fan QL, Zheng C, Huang W. A general strategy for the facile synthesis of 2,7-dibromo-9-heterofluorenes. Org Lett, 2006, 8: 203–205

    Article  CAS  Google Scholar 

  17. Chen JW, Cao Y. Silole-containing polymers: Chemistry and optoelectronic properties. Macromol Rapid Comm 2007, 28: 1714–1742

    Article  CAS  Google Scholar 

  18. Wang E, Li C, Zhuang W, Peng J, Cao Y. High-efficiency red and green light-emitting polymers based on a novel wide bandgap poly(2,7-silafluorene). J Mat Chem, 2008, 18(7): 797–801

    Article  CAS  Google Scholar 

  19. Wang E, Li C, Peng JB, Cao Y. High-efficiency blue light-emitting polymers based on 3,6-silafluorene and 2,7-silafluorene. J Polym Sci Polym Phys, 2007, 45: 4941–4949

    CAS  Google Scholar 

  20. Mo YQ, Tian RY, Shi W, Cao Y. Ultraviolet-emitting conjugated polymer poly(9,9’-alkyl-3,6-silafluorene) with a wide band gap of 4.0 eV. Chem Commun, 2005: 4925–4926

  21. Mo YQ, Deng XY, Jiang X, Cui Q. Blue electroluminescence from 3,6-silafluorene-based copolymers. J Polym Sci Polym Chem, 2009, 47: 3286–3295

    Article  CAS  Google Scholar 

  22. Chan KL, Watkins SE, Mak CS, McKiernan MJ, Towns CR, Pascu SI, Holmes AB. Poly(9,9-dialkyl-3,6-dibenzosilole) — A high energy gap host for phosphorescent light emitting devices. Chem Commun, 2005: 5766–5768

  23. Wang E, Li C, Mo Y, Zhang Y, Ma G, Shi W, Peng J, Yang W, Cao Y. Poly(3,6-silafluorene-co-2,7-fluorene)-based high-efficiency and color-pure blue light-emitting polymers with extremely narrow band-width and high spectral stability. J Mater Chem, 2006, 16: 4133–4140

    Article  CAS  Google Scholar 

  24. Chan KL, McKiernan MJ, Towns CR, Holmes AB. Poly(2,7-dibenzosilole): A blue light-emitting polymer. J Am Chem Soc, 2005, 127: 7662–7663

    Article  CAS  Google Scholar 

  25. Chen RF, Fan QL, Liu SJ, Zhu R, Pu KY, Huang W. Fluorene and silafluorene conjugated copolymer: A new blue light-emitting polymer. Synth Met, 2006, 156: 1161–1167

    Article  CAS  Google Scholar 

  26. Agou T, Hossain MD, Kawashima T. Syntheses, optical properties, and theoretical investigation of silafluorenes and spirobisilafluorenes bearing electron-donating aminostyryl arms around a silafluorene core. Chem Eur J, 2010, 16: 368–375

    Article  CAS  Google Scholar 

  27. Wang E, Wang L, Lan L, Luo C, Zhuang W, Peng J, Cao Y. High-performance polymer heterojunction solar cells of a polysilafluorene derivative. Appl Phys Lett, 2008, 92(3): 033307/1–033307/3

    CAS  Google Scholar 

  28. Boudreault PT, Michaud A, Leclerc M. A new poly(2,7-dibenzosilole) derivative in polymer solar cells. Macromol Rapid Comm, 2007, 28: 2276–4455

    Article  Google Scholar 

  29. Zhang X, Jiang C, Mo Y, Xu Y, Shi H, Cao Y. High-efficiency blue light-emitting electrophosphorescent device with conjugated polymers as the host. Appl Phys Lett, 2006, 88: 051116/1–051116/3

    CAS  Google Scholar 

  30. Sek D, Iwan A, Jarzabek B, Kaczmarczyk B, Kasperczyk J, Mazurak Z, Domanski M, Karon K, Lapkowski M. Hole transport triphenylamine-azomethine conjugated system: Synthesis and optical, photoluminescence, and electrochemical properties. Macromolecules, 2008, 41: 6653–6663

    Article  CAS  Google Scholar 

  31. Kuo WJ, Lin SL, Chen SD, Chang CP, Lee RH, Jeng RJ. Efficient and bright non-doped blue light-emitting diodes based on glassy styrylcarbazoles. Thin Solid Films, 2008, 516: 4145–4152

    Article  CAS  Google Scholar 

  32. Ariu M, Sims M, Rahn MD, Hill J, Fox AM, Lidzey DG, Oda M, Cabanillas-Gonzalez J, Bradley DD. Exciton migration in beta-phase poly(9,9-dioctylfluorene). Phys Rev B, 2003, 67: 195333–195344

    Article  Google Scholar 

  33. Zhu R, Lin JM, Wang WZ, Zheng C, Wei W, Huang W, Xu YH, Peng JB, Cao Y. Use of the beta-phase of poly(9,9-dioctylfluorene) as a probe into the interfacial interplay for the mixed bilayer films formed by sequential spin-coating. J Phys Chem B, 2008, 112: 1611–1618

    Article  CAS  Google Scholar 

  34. Byun HY, Chung IJ, Shim HK, Kim CY. Optoelectronic and photophysical properties of polyfluorene blends as side-chain length and shape. Macromolecules, 2004, 37: 6945–6953

    Article  CAS  Google Scholar 

  35. Zeng G, Yu WL, Chua SJ, Huang W. Spectral and thermal spectral stability study for fluorene-based conjugated polymers. Macromolecules, 2002, 35: 6907–6914

    Article  CAS  Google Scholar 

  36. Wang LH, Chen ZK, Xiao Y, Kang ET, Huang W. A novel conjugated polymer containing alternating p- and n-type moieties with balanced properties of conducting holes and electrons. Macromol Rapid Commun, 2000, 21: 897–900

    Article  CAS  Google Scholar 

  37. Schwartz BJ. Conjugated polymers as molecular materials: How chain conformation and film morphology influence energy transfer and interchain interactions. Annu Rev Phys Chem, 2003, 54: 141–172

    Article  CAS  Google Scholar 

  38. Rickard D, Giordam S, Blau W, Coleman JN. Quantifying the contributions of inner-filter, re-absorption and aggregation effects in the photoluminescence of high-concentration conjugated polymer solutions. J Lumin, 2008, 128: 31–40

    Article  CAS  Google Scholar 

  39. Wong KT, Chien YY, Chen RT, Wang CF, Lin YT, Chiang HH, Hsieh PY, Wu CC, Chou CH, Su YO, Lee GH, Peng SM. Ter(9,9-diarylfluorene)s: Highly efficient blue emitter with promising electrochemical and thermal stability. J Am Chem Soc, 2002, 124: 11576–11577

    Article  CAS  Google Scholar 

  40. 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 

  41. Liu SJ, Zhao Q, Chen RF, Deng Y, Fan QL, Li FY, Wang LH, Huang CH, Huang W. Pi-conjugated chelating polymers with charged iridium complexes in the backbones: Synthesis, characterization, energy transfer, and electrochemical properties. Chem Eur J, 2006, 12: 4351–4361

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Wei Huang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, R., Zhu, R., Zheng, C. et al. Synthesis, characterization and applications of vinylsilafluorene copolymers: New host materials for electroluminescent devices. Sci. China Chem. 53, 2329–2336 (2010). https://doi.org/10.1007/s11426-010-4108-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-010-4108-7

Keywords

Navigation