Synthesis of Fluorinated Organic and Organometallic Electroluminescent Materials: Tuning Emission in the Blue

Article Preview

Abstract:

Functionalization with fluorine atoms represents a versatile structural modification to finely tune both the emission colour and the electronic properties of organic and organometallic electroluminescent compounds. This paper reports an overview of our systematic investigation on the design and synthesis of the fluorinated version of two important classes of materials for organic light emitting diodes (OLEDs), namely poly(arylenevinylene)s and phosphorescent phenylpyridine Iridium complexes. Synthetic pathways based on organometallic methodologies affording selectively fluorinated molecular structures will be discussed together with a summary of the effect of fluorination on the optical properties of the resulting materials. In particular we will highlight the possibilities offered by the organometallic methodologies as straightforward and resourceful tools to provide a wide series of fluorinated molecular architectures with high regio- and stereoselectivity, mild experimental conditions and good yields.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

108-117

Citation:

Online since:

October 2010

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2010 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

[1] J. Liu, Q. G. Zhou, Y. X. Cheng, Y. H. Geng, L. X. Wang, D. G. Ma, X. B. Jing, F. S. Wang: Adv. Funct. Mater. Vol. 16 (2006), p.957.

Google Scholar

[2] S. Neyshtadt, M. Kalina, G. L. Frey: Adv. Mater. Vol. 20 (2008), p.2541. Y. Kim, S. Cook, S. M. Tuladhar, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, M. Giles, I. McCulloch, C. S. Ha, M. Ree: Nat. Mater. Vol. 5 (2006), p.197.

DOI: 10.1038/nmat1574

Google Scholar

[3] R. Zhang, B. Li, M. C. Iovu, M. Jeffries-El, G. Sauve`, J. Cooper, S. Jia, S. Tristram-Nagle, D. M. Smilgies, D. N. Lambeth, R. D. McCullough, T. Kowalewski: J. Am. Chem. Soc. Vol. 128 (2006), p.3480.

DOI: 10.1021/ja055192i

Google Scholar

[4] D. H. Charych, J. O. Nagy, W. Spevak, M. D. Bednarski: Science Vol. 261 (1993), p.585.

Google Scholar

[5] J. L. Bredas, A. Heeger: J Chem Phys Lett Vol. 217 (1994), p.507.

Google Scholar

[6] Reichenbacher, H. I. Suss and J. Hulliger: Chem. Soc. Rev. Vol. 34 (2005), p.22.

Google Scholar

[7] F. Babudri, G. M. Farinola, F. Naso, R. Ragni: Chem Commun (2007), p.1003. K.

Google Scholar

[8] F. Babudri, G. M. Farinola, Naso: J. Mater. Chem. Vol. 14 (2004), p.11.

Google Scholar

[9] F. Babudri, S. R. Cicco, L. Chiavarone, G. M. Farinola, L. C. Lopez, F. Naso, G. Scamarcio: J. Mater. Chem. Vol. 10 (2000), p.1573.

DOI: 10.1039/a909780e

Google Scholar

[10] G. H. Brooke, S. D. Mawson, J. Fluorine Chem., Vol. 50 (1990), p.101.

Google Scholar

[11] A. F. Renaldo, J. W. Labadie, J. K. Stille, Org. Synth., Vol. 67 (1989), p.86.

Google Scholar

[12] F. Babudri, A. Cardone, L. Chiavarone, G. Ciccarella, G. M. Farinola, F. Naso, G. Scamarcio: Chem. Commun. (2001), p. (1940).

DOI: 10.1039/b105029j

Google Scholar

[13] R. Skelton, F. Dubois, R. A. Zenobi: Anal. Chem. Vol. 72 (2000), p.1707.

Google Scholar

[14] F. Babudri, A. Cardone, G. M. Farinola, F. Naso, T. Cassano, L. Chiavarone, R. Tommasi: Macromol. Chem. Phys. Vol. 204 (2003), p.1621.

DOI: 10.1002/macp.200350021

Google Scholar

[15] Y. Jin, J. Kim, S. Lee, J. Y. Kim, S. H. Park, K. Lee, H. Suh: Macromolecules Vol. 37 (2004), p.6711.

Google Scholar

[16] D. J. Burton, Q. Liu: Org. Lett. Vol. 4 (2002), p.1483.

Google Scholar

[17] F. Babudri, A. Cardone, G. M. Farinola, C. Martinelli, R. Mendichi, F. Naso, M. Striccoli: Eur. J. Org. Chem. (2008), p. (1977).

DOI: 10.1002/ejoc.200700815

Google Scholar

[18] A. Cardone, C. Martinelli, V. Pinto, F. Babudri, M. Losurdo, G. Bruno, C. Pinalysa, F. Naso, G. M. Farinola: J. Poly. Sci.: Part A: Polym. Chem. Vol. 48 (2010), p.285.

DOI: 10.1002/pola.23782

Google Scholar

[19] Nielsen, M. W. F. Mass Spectrom Rev. Vol. 18 (1999), p.309 and references therein.

Google Scholar

[20] M. Piacenza, F. Della Sala, G.M. Farinola, C. Martinelli, G. Gigli: J. Phys. Chem. B vol. 112 (2008), p.2996.

Google Scholar

[21] M. Losurdo, M.M. Giangregorio, P. Capezzuto, A. Cardone, C. Martinelli, G.M. Farinola, F. Babudri, F. Naso, M. Büchel, G. Bruno: Adv. Mater. Vol. 21 (2009), p.1115.

DOI: 10.1002/adma.200802269

Google Scholar

[22] R. Ragni, E. A. Plummer, K. Brunner, J. W. Hofstraat, F. Babudri, G. M. Farinola, F. Naso, L. De Cola: J. Mater. Chem. Vol. 16 (2006), p.1161.

DOI: 10.1039/b512081k

Google Scholar

[23] V. V. Grushin, N. Herron, D. D. LeCloux, W. J. Marshall, V. A. Petrov, Y. Wang: Chem. Commun. (2001), p.1494.

Google Scholar

[24] S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Muy, R. Bau, M. E. Thompson: Inorg. Chem. Vol. 40 (2001), p.1704.

DOI: 10.1021/ic0008969

Google Scholar

[25] R. Ragni, E. Orselli, G. S. Kottas, O. Hassan Omar, F. Babudri, A. Pedone, F. Naso, G.M. Farinola, L. De Cola: Chem.: A Eur. J. Vol. 15 (2009), p.132.

DOI: 10.1002/chem.200801270

Google Scholar

[26] L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, F. Barigelletti: Top. Curr. Chem. Vol. 281 (2007), p.143.

Google Scholar