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Synthesis and Properties of Perylene Bisimides Containing Benzocyclobutene Groups for Organic Light-emitting Diodes

Author: XuYeWei
Tutor: ZhangLin
School: Southwest University of Science and Technology
Course: Analytical Chemistry
Keywords: Perylenediim Benzocyclobutene Synthesis Electroluminescent Characterization
CLC: O621.25
Type: Master's thesis
Year: 2010
Downloads: 91
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Abstract


Organic EL (OLED) display technology with the future development trend causing more and more concern and attention, and therefore become the hot research field of organic electroluminescent light emitting materials. Perylene compounds, especially compounds of the perylene diimide, because of its advantage of having excellent light stability, thermal stability, chemical stability, and a high fluorescence quantum efficiency and widespread concern. The perylene small organic molecules, there are many drawbacks, however, researchers tend to perylene macromolecularized. This article was first proposed reactive benzocyclobutene groups polymerizable introduced the perylene diimide BAY bit (1,6,7,12-bit), to increase its solubility at the same time, through the thermal polymerization reaction crosslinked polymer, the resulting polymer is not only having a good light-emitting properties, and has a good film-forming properties, in order to resolve small molecules difficult due to poor solubility with the film formation of the solution method, ultimately increased the cost of the production costs of the device problems. In order to understand how to increase the solubility of the perylene diimide and the impact on the the perylene diimide performance the increased solubility after we first explore perylene dianhydride bromination process, while synthetic four Soluble perylene diimide: N, N'-bis (dodecyl) -1 , 7 - dibromo--3,4,9,10 - perylene imide (d), N, N'-bis (dodecyl) -1 , 6,7,12 - tetrabromo -3,4,9,10 - perylene imide (e), N, N'-bis (dodecyl) -1 , 7 - di (tert-butyl-phenoxy) -3,4,9,10 - perylene diimide (f) and N , N'-bis (dodecyl) -1 , 6,7,12 - tetra (t-butyl-phenoxy) -3,4,9,10 - perylene diimide (g). Means of 1H NMR, FTIR, and MS identified four product structure, but also to study its UV - visible absorption, fluorescence, cyclic voltammetry, and thermal performance. Experimental results show that: the introduction of the group in the imide nitrogen position and bay location can significantly improve the perylene imide solubility, also have a certain impact on the performance of its various aspects. Then, the benzocyclobutene polymerization and film-forming properties were studied. 4 - vinyl benzocyclobutene (VBCB) first and styrene (St) radical polymerization reaction, and the product with divinylsiloxane the - double the benzocyclobutene (DVSBCB) thermal polymerization reaction generates a pre mers (VBCB-St-DVSBCB), then the prepolymer was dissolved in toluene is spin-coating, and finally curing reaction. The experimental found, benzocyclobutene derivative of the four-membered ring at about 200 ℃ easy ring-opening polymerization reaction, while its film-forming performance is very good, and a high degree of film formation, the Polymer RESIN film (1), Ra, PV and RMS were 4.473 × 10 -1 , 3.475 × 101 and 7.801 × 10 -1 nm, and the polymer resin film (2), Ra, PV and RMS were 7.807 × 10 -1 , 1.894 × 101 and 1.087 nm. Finally, the combination of the first two chapters of the target product was synthesized the two novel benzocyclobutene - perylene imide compound: N, N'-di (dodecyl) -1 , of 6,7,12 - the tetrakis (benzocyclobutene yloxy) -3,4,9,10 - perylene diimide (h) and, N, N'-bis (dodecyl) -1 , 6,7,12 - tetrakis (benzo ring butenyl) -3,4,9,10 - perylene diimide (i), and using a variety of analytical tools to determine The structure of the product, but also UV - visible absorption, fluorescence, and its thermal performance of the product. The same time, the thermal polymerization and film-forming properties of the product h. It was found that the four-membered ring of the product h at about 225 ℃ easy open loop cross-linking reaction occurs. Generated H prepolymer after its UV-visible absorption, fluorescence, and cyclic voltammetry characteristic respect to the product of h changes, the same time, the prepolymer h can be spin coating, laid the foundation for the realization of large area deposition.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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