Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes

Jian Yang Cho, Benoit Domercq, Stephen Barlow, Kyrill Yu Suponitsky, Jennifer Li, Tatiana V. Timofeeva, Simon C. Jones, Lauren E. Hayden, Alpay Kimyonok, Clinton R. South, Marcus Weck, Bernard Kippelen, Seth R. Marder

Research output: Contribution to journalArticle

Abstract

A norbornene-functionalized derivative of acetylacetone has been used to synthesize a series of new polymerizable norbornene-derivatized phosphorescent platinum complexes of the form Pt(C∧N)(O∧O*) where C∧N represents a cyclometalated ligand and O∧O* represents the functionalized acetylacetonate ligand. The complexes have been fully characterized, and the structures of three examples have been determined by X-ray diffraction. Solution absorption and luminescence spectra and electrochemical data are very similar to those for analogues without these polymerizable groups. A 9,9-dialkyl-2,7-di(carbazol-9-yl)fluorene material, in which one of the alkyl groups bears a norbornene group, has been synthesized and copolymerized with the Pt(C∧N)(O∧O*) complexes using Grubbs ruthenium catalysts, resulting in copolymers with broad molecular weight distributions. The copolymers have been used as lumophores in organic light-emitting diodes, thus demonstrating that platinum phosphors can be successfully integrated into the "hybrid" approach to organic light-emitting diodes, in which molecules with transport or luminescent properties are covalently attached to electronically inert polymer backbones to give solution-processible materials. Emission from aggregate states appears to play a similar role in these copolymers to that seen in vapor-deposited devices based on small phosphor and host molecules; in particular, considerable aggregate emission is observed when a phosphor with blue solution emission is used in the devices.

Original languageEnglish (US)
Pages (from-to)4816-4829
Number of pages14
JournalOrganometallics
Volume26
Issue number19
DOIs
StatePublished - Sep 10 2007

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Cho, J. Y., Domercq, B., Barlow, S., Suponitsky, K. Y., Li, J., Timofeeva, T. V., Jones, S. C., Hayden, L. E., Kimyonok, A., South, C. R., Weck, M., Kippelen, B., & Marder, S. R. (2007). Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes. Organometallics, 26(19), 4816-4829. https://doi.org/10.1021/om700373c