Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Color Tuning of Poly(p-phenylenevinylene) Containing Terphenyl Units for Light Emitting Diodes

  • Jin, Young-Eup (Department of Chemistry and Center for Plastic Information System, Pusan National University) ;
  • Kim, Jin-Woo (Department of Chemistry and Center for Plastic Information System, Pusan National University) ;
  • Park, Sung-Heum (Department of Physics and Center for Plastic Information System, Pusan National University) ;
  • Kim, Hee-Joo (Department of Physics and Center for Plastic Information System, Pusan National University) ;
  • Lee, Kwang-Hee (Department of Physics and Center for Plastic Information System, Pusan National University) ;
  • Suh, Hong-Suk (Department of Chemistry and Center for Plastic Information System, Pusan National University)
  • Published : 2005.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

New PPV based conjugated polymers, containing terphenyl units, were prepared as the electroluminescent (EL) layer in light-emitting diodes (LEDs). The prepared polymers, poly[2,5-bis(4-(2-etylhexyloxy)phenyl)-1,4-phenylenevinylene] (BEHP-PPV), poly[2-(2-ethylhexyloxy)-5-(4-(4-(2-etylhexyloxy)phenyl)phenyl)-1,4-phenylenevinylene] (EEPP-PPV) and poly[2-(2-ethylhexyloxy)-5-(9,9-bis(2-etylhexyl)fluorenyl)-1,4 phenylenevinylene] (EHF-PPV), were soluble in common organic solvents and used as the EL layer in double layer light-emitting diodes (LEDs) (ITO/PEDOT/polymer/Al). The polymers were prepared by the Gilch reaction. The number-average molecular weight $(M_n)$, weight-average molecular weight $(M_w)$, and the polydispersities (PDI) of these polymers were in the range of 9000-58000, 27000-231000, 2.9-3.9, respectively. These polymers have quite good thermal stability with decomposition starting above 320-350. The polymers show photoluminescence (PL) with maximum peaks at around 526-562 nm (exciting wavelength, 410 nm) and blue EL with maximum peaks at around $\lambda_{max}$ = 526-552 nm. The current-voltageluminance (I-V-L) characteristics of polymers show turn-on voltages of 5 V. Even though both of EEPP-PPV and BEHP-PPV have the same terphenyl group in the repeating unit, EEPP-PPV with directly substituted alkoxy group in the back bone has longer effective conjugation length than BEHP-PPV, and exhibits red shift in the PL spectra. Both of EEPP-PPV and EHF-PPV have ter-phenyl units and directly substituted alkoxy group in back bone. EHF-PPV with fluorenyl unit attached to the PPV backbone has shorter effective conjugation length than EEPP-PPV with biphenyl unit, and exhibits blue shift in the PL spectra.

Keywords

References

  1. Tang, W. C.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913 https://doi.org/10.1063/1.98799
  2. Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332 https://doi.org/10.1126/science.267.5202.1332
  3. Dodavalapur, A.; Rotherverg, L. J.; Miller, T. M. Electron. Lett. 1994, 30, 1000 https://doi.org/10.1049/el:19940650
  4. Yan, M.; Rotherberg, L. J.; Papadimitralopoules, F.; Galvin, M. E.; Miller, T. M. Phys. Rev. Lett. 1994, 73, 744 https://doi.org/10.1103/PhysRevLett.73.744
  5. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; MacKay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990, 347, 539 https://doi.org/10.1038/347539a0
  6. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402 https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9
  7. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Santos, D. A.; Bredas, J. L.; Logdlund, M.; Salameck, W. R. Nature 1999, 397, 121 https://doi.org/10.1038/16393
  8. Jin, Y.; Kim, J.; Lee, S.; Kim, J. Y.; Park, S. H.; Lee, K.; Suh, H. Macromolecules 2004, 37, 6711 https://doi.org/10.1021/ma0493022
  9. Shim, H. K.; Jin, J. I. Adv. Polym. Sci. 2002, 158, 194
  10. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477 https://doi.org/10.1038/357477a0
  11. Hwang, D.-H.; Kim, S. T.; Shim, H.-K.; Holmes, A. B.; Moratti, S. C.; Friend, R. H. Chem. Commun. 1996, 2241
  12. Johansson, D. M.; Srdanov, G.; Yu, G.; Theander, M.; Inganas, O.; Andersson, M. R. Macromolecules 2000, 33, 2525 https://doi.org/10.1021/ma991582b
  13. Chen, Z.-K.; Lee, N. H. S.; Huang, W.; Xu, Y.-S.; Cao, Y. Macromolecules 2003, 36, 1009 https://doi.org/10.1021/ma021221n
  14. Lee, S. H.; Jang, B.-B.; Tsutsui, T. Macromolecules 2002, 35, 1356 https://doi.org/10.1021/ma010643e
  15. Sohn, B. H.; Lee, K. Y. U.S. Pat. Appl. Publ. 2002, 19
  16. Gurge, R. M.; Sarker, A.; Laht, P. M.; Hu, B.; Karasz, F. E. Macromolecules 1996, 29, 4287 https://doi.org/10.1021/ma960104n
  17. Gurge, R. M.; Sarker, A.; Laht, P. M.; Hu, B.; Karasz, F. E. Macromolecules 1997, 30, 8286 https://doi.org/10.1021/ma970693c
  18. Jin, J. I.; Kim, J. C.; Shim, H. K. Macromolecules 1992, 25, 5519 https://doi.org/10.1021/ma00046a060
  19. Lahti, P. M.; Sarker, A.; Garay, R. O.; Lenz, R. W.; Karasz, F. E. Polymer 1994, 35, 1312 https://doi.org/10.1016/0032-3861(94)90029-9
  20. Grimsdale, A. C.; Cacialli, F.; Gruner, J.; Lix, C.; Holmes, A. B.; Moratti, S. C.; Friend, R. H. Synth. Met. 1996, 76, 165 https://doi.org/10.1016/0379-6779(95)03444-O
  21. Greenham, N. C.; Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628 https://doi.org/10.1038/365628a0
  22. Gustafsson, G.; Treacy, G. M.; Cao, Y.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Synth. Met. 1993, 55-57, 4123
  23. Zhang, C.; Pakbaz, K.; Wudl, F.; Heeger, A. J. J. Electron. Mater. 1993, 22, 413 https://doi.org/10.1007/BF02661671
  24. Zhang, C.; Braun, D.; Heeger, A. J. J. Appl. Phys. 1993, 73, 5177 https://doi.org/10.1063/1.353794
  25. Jin, Y.; Ju, J.; Kim, J.; Lee, S.; Kim, J. Y.; Park, S. H.; Son, S. M.; Jin, S. H.; Lee, K.; Suh, H. Macromolecules 2003, 36, 6970 https://doi.org/10.1021/ma025862u
  26. Grem, G.; Leditzky, G.; Leising, G. Synth. Met. 1992, 51, 383 https://doi.org/10.1016/0379-6779(92)90293-R
  27. Braun, D.; Starting, E. G. J.; Demandt, R. C. J. E.; Rikken, G. L. J.; Kessener, Y. A. R. R.; Venhuizen, A. H. J. Synth. Met. 1994, 66, 75 https://doi.org/10.1016/0379-6779(94)90164-3
  28. Woo, E. P.; Inbasekaran, M.; Shiang, W. R.; Roof, G. R. Int. Pat. Appl. WO 9705184, 1997
  29. Conwell, E. Trends Polym. Sci. 1997, 5, 218
  30. Becker, H.; Spreitzer, H.; Kreuder, W.; Kluge, E.; Schenk, H.; Parker, I.; Cao, Y. Adv. Mater. 2000, 12, 42 https://doi.org/10.1002/(SICI)1521-4095(200001)12:1<42::AID-ADMA42>3.0.CO;2-F
  31. Andersson, M. R.; Berggren, M.; Inganas, O.; Gustafsson, G.; Strom, O. Macromolecules 1995, 28, 7525 https://doi.org/10.1021/ma00126a033
  32. Schrievers, T.; Brinker, U. H. Synthesis 1988, 4, 330
  33. Miyaura, N.; Yanagi, T.; Suzuki, A. Synthetic Commun. 1981, 11, 513 https://doi.org/10.1080/00397918108063618
  34. Fukazawa, Y.; Kitayama, H.; Yasuhara, K.; Yoshimura, K.; Usui, S. J. Org. Chem. 1995, 60, 1696 https://doi.org/10.1021/jo00111a030
  35. Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R. F.; Bassler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551 https://doi.org/10.1002/adma.19950070608
  36. Leeuw, D. M.; Simenon, M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53 https://doi.org/10.1016/S0379-6779(97)80097-5

Cited by

  1. Synthesis of Terphenyls vol.41, pp.5, 2009, https://doi.org/10.1080/00304940903163632
  2. -Terphenyl and Fluorene Derivatives as Efficient Dopants in Plastic Scintillators for Sensitive Nuclear Material Detection vol.23, pp.37, 2017, https://doi.org/10.1002/chem.201700877
  3. Synthesis, characterisation and intracellular imaging of PEG capped BEHP-PPV nanospheres pp.18, 2009, https://doi.org/10.1039/b903405f
  4. Synthesis and Properties of PCPP-Based Conjugated Polymers Containing Pendant Carbazole Units for LEDs vol.28, pp.12, 2005, https://doi.org/10.5012/bkcs.2007.28.12.2419
  5. Parallel Synthesis of Unsymmetrical trans-Stilbenes vol.28, pp.7, 2007, https://doi.org/10.5012/bkcs.2007.28.7.1159
  6. Blends of poly[2-(2′,5′-bis(2′-ethyl-hexyloxy)phenyl)-1,4-phenylenevinylene] and poly(3-hexylthiophene) as base materials for broad band light emission devices vol.104, pp.4, 2005, https://doi.org/10.1063/1.2973038
  7. Synthesis and properties of various PPV derivatives with phenyl substituents vol.49, pp.21, 2005, https://doi.org/10.1016/j.polymer.2008.08.037
  8. BEHP-PPV and P3HT blends for light emitting devices vol.29, pp.2, 2005, https://doi.org/10.1016/j.msec.2008.10.006
  9. Stability of the J–V characteristics of (BEHP-PPV)-co-(MEH-PPV) based light-emitting diodes vol.49, pp.12, 2005, https://doi.org/10.1016/j.microrel.2009.07.053
  10. mPW1PW91 Calculated and Experimental UV/IR Spectra of Unsymmetrical trans-Stilbenes vol.31, pp.8, 2005, https://doi.org/10.5012/bkcs.2010.31.8.2175
  11. Synthesis of Terphenyl Derivatives by Pd‐Catalyzed Suzuki‐Miyaura Reaction of Dibromobenzene Using 2N2O‐Salen as a Ligand in Aqueous Solution vol.33, pp.10, 2005, https://doi.org/10.1002/cjoc.201500446