Synthesis and Optical Properties of Fluoranthene Derivatives for Organic Light Emitting Diodes

• Main Authors: Chun-Ming Chen, 陳均銘
• Other Authors: Pei-Hua Ho
• Format: Others
• Language: zh-TW
• Published: 2007
• Online Access: http://ndltd.ncl.edu.tw/handle/96849161650618455568

碩士 === 靜宜大學 === 應用化學研究所 === 95 === The thesis is aimed at synthesis and optical properties of 7,14-diphenylacenaphtho[1,2-k]fluoranthene derivatives for organic light emitting diodes. It has been demonstrated that resonance in conjugated double bonds of the fluoranthene derivatives resulted in better optical properties. Accordingly, we further designed a series of 7,14-diphenyl- acenaphtho[1,2-k]fluoranthene derivatives in which substituted acetyl and diphenylamino groups with different functional groups were introduced onto the 3- and 10-position to expect better luminescence properties. Acenaphthenequinone (1) and 1,3-diphenylpropan-2-one (2) underwent condensation under the base condition to give 7,9-diphenyl-8H-cyclopenta- [1]acenaphthylen-8-one (3) which reacted with acenaphthylene (4) under a nitrogen atmosphene and oxidated by KMnO4 to afford 7,14-diphenyl- acenaphtho[1,2-k]fluoranthene (5). After brominetion, nucleophilic addi- tion was proceeded to introduce acetyl and diphenylamino groups at 3- and 10-position. All compounds were measured by UV-visible, photo- luminescence spectra and lifetime. We found that the spectra are red shift, if the functional groups were electron donating groups (11a ~ 11e). This was attributed to an effective increase in the electronic density and delocalization of π electrons in the molecules due to substitution. The emission maxima(λmax) was from 560 nm shift to 610 nm. When the functional groups is electron withdrawing (12), the emission maxima(λmax) was 541 nm. Further, compound 11b possessed the best in lifetime (τ) 46.34 ns. In the thermochemistry, the decompose temperature of compound 11a was highest, 562 °C. The next was compound 11c, 547 °C. Afer all compounds were measured by Differentail Scanning Calorimeter, the compound 11a was best, 98 °C. In the electrochemical, Although all compounds were had oxidation and reduction potential, compound 5 and 11a were only reversible. The other were irreversible.