3,6,9,12-Tetrasubstituted Chrysenes: Synthesis, Photophysical Properties, and Application as Blue Fluorescent OLED

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• 作者：Tien-Lin Wu ; Ho-Hsiu Chou ; Pei-Yun Huang ; Chien-Hong Cheng ; Rai-Shung Liu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：79
• 期：1
• 页码：267-274
• 全文大小：437K
• ISSN：1520-6904

文摘

A short synthesis of unsubstituted chrysene is described to provide a cheap source of this compound. This chrysene was used to prepare 3,6,9,12-tetrabromochrysene, which was subsequently transformed into various 3,6,9,12-tetrasubstituted chrysenes bearing four aryl, alkynyl, or amino groups by means of the Suzuki, Sonogashira, or Buchwald鈥揌artwig coupling reaction, respectively. These substituents result in large bathochromic shifts in the chrysene absorption and emission spectra. These new chrysene derivatives show blue fluorescent emission (401鈥?71 nm) with high quantum yields (0.44鈥?.87). DFT calculations on these chrysenes rationalize well the substituent effects on their HOMO and LUMO energy levels. One representative chrysene (6g) was used as a blue fluorescent emitter in an OLED device that showed an outstanding external quantum efficiency (畏 = 6.31%) with blue emission [CIE (x, y) = (0.13, 0.20)] and a low turn-on voltage (3.0 V).