Solution processable nanocomposites based on silsesquioxane cores for use in organic light emitting diodes (OLEDs)
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EE14.2.1
Solution processable nanocomposites based on silsesquioxane cores for use in organic light emitting diodes (OLEDs) Alan Sellinger,*1,2 Ryo Tamaki,3,4 Richard M. Laine,4 Kazunori Ueno,5 Hiroshi Tanabe,5 Evan Williams,6 and Ghassan E. Jabbour6 1
Canon R&D Center Americas, 3300 N. First Street, San Jose, CA 95134, USA Present address: Institute of Materials Research and Engineering (IMRE), 3 Research Link 117602, Republic of Singapore 3 Present address: General Electric Company, One Research Circle, Niskayuna, NY 12309, USA 4 Macromolecular Science and Engineering, and Materials Science and Engineering, University of Michigan, Ann Arbor, MI 48109, USA 5 Canon Inc., 30-2, Shimomaruko 3-Chome, Ohta-ku, Tokyo 146-8501, Japan 6 Chemical and Materials Engineering, Arizona State University Tempe, Arizona 85287, USA * e-mail: [email protected] Abstract A new family of materials that synergistically combine the attributes of both organic and inorganic properties for use in organic light emitting diodes (OLEDs) is presented. The hybrid materials are based on 3-D inorganic cores of octavinylsilsesquioxanes (OVS). The resultant materials have high Tg’s (120-210°C), are formed from minimal step/high yield reactions and readily available starting reagents, are monodisperse (PDI85% yield. The reaction conditions were quite mild – 3 h at 70ºC, 1:1 toluene:dioxane solvent mixture, catalytic bis(tri-t-butylphosphine) palladium (0) [Pd[P(tBu)3]2] (1.0 mol %) and dicyclohexylmethylamine as base/HBr scavenger. The reactions are monitored by thin layer, size exclusion chromatography and visually by the precipitation of dicyclohexylmethylaminehydrobromide by-product. Additionally, UV light was used to qualitatively observe the appearance of intense photoluminescent emissions during the course of reaction. On completion, the reaction mixture was precipitated into methanol to produce a fine bright yellow powder that was collected by filtration. The powder was then dried and purified by column chromatography using hexanes:ethyl acetate (10:1) followed by dichloromethane.
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C244H204N12O12Si8 Mol. Wt.: 3720.99
Figure 1. Chemical structures of the hole transport functionalized nanocomposites used in this work. We refer to this material as TPD-OVS. Size exclusion chromatography in tetrahydrofuran (THF) revealed a very narrow polydispersity (
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