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Synthesis And Properties Of Perylene Bisimides Containing Benzocyclobutene Groups For Organic Light-emitting Diodes

Posted on:2011-08-29Degree:MasterType:Thesis
Country:ChinaCandidate:Y W XuFull Text:PDF
GTID:2131330338479094Subject:Analytical Chemistry
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OLED has been attracting increasing attentions and regards for its potential advantages in future display. So OLED materials have been a research hotspot. Perylene derivatives, especially perylene bisimides, have attracted intense investagation due to their high photo stability, chemical stability and thermal stability as well as high fluorescence quantum yield. However, small molecular perylene derivatives have many a shortcomings, so the researchers tend to make perylene derivatives polymerization. Hence, we want to induce benzocyclobutene which can polymerize through heating to the bay position of perylene bisimide to increase the solubility, and polymer perylene derivatives are prepared by thermal polymerization which not only posses luminescence properties, but also have good film forming ability. This process can account for the problem that is difficult to form in the solution which resulted in the cost increasing.In order to research on how to increase the solubility and the influence of performance of perylene bisimides after improving the solubility, The bromination reaction of perylene-3, 4, 9, 10-tetracarboxylic acid bisanhydride was first explored. And four soluble peyrlene bisimides [N,N'-didodecyl-1,7- dibromo-perylene-3,4,9,10-tetracar-boxylic acid diimide (d), N,N'-didodecyl- 1,6,7,12-tetrabromo-perylene-3,4,9,10-tetracarboxylic acid diimide (e), N,N'- didodecyl-1,7-di(4-t-butylphenoxy)perylene-3,4,9,10-tetra-carboxylic acid diimide (f) and N,N'-di-dodecyl-1,6,7,12- tetra(4-t-butylphenoxy)-3,4,9,10-tetra- carboxylic acid diimide (g) were synthesized. The structures were characterized by 1H NMR, FTIR and MS, and the UV-vis maximal absorption, fluorescence spectroscopy, electrochemical and thermal properties were investigated. The result indicated that the groups which were introduced into N and bay position can improve the solubility notability and can influence the performance of perylene bisimides.Subsequently, the polymerization and film forming ability of benzocyclobutene were investigated. Radical copolymerization of 4-vinyl-benzocyclobutene with styrene afforded the copolymer (4-vinylbenzocyclobutene-co-styrene) (VBCB-St). Reaction of VBCB-St and divinyl tetramethyl disiloxane-bisbenzocyclobutene (DVSBCB) gave the oligomer (VBCB-St-DVSBCB), which was subsequently subjected to the spin-coating and the cure reaction. It is found that benzocyclobutene opens the cyclobutene ring when heated to 200 oC and film forming ability is good, and the polymer resin possessed good film planarization. AFM images of polymer resin (1) shows that Ra, P-V and RMS are separately 4.473×10-1, 3.475×101 and 7.801×10-1 nm. Whereas Ra, P-V and RMS of polymer resin (2) are 7.807×10-1, 1.894×101 and 1.087 nm.Finally, two novel benzocyclobutene-peyrlene derivatives [N,N'-didodecyl-1,6,7,12-tetra(4-benzocyclobutenyloxy)perylene-3,4,9,10-tetracarboxy-lic acid diimide (h), N,N'-didodecyl-1,6,7,12-tetra- (4-benzocyclobutenyl)-3,4,9,10-tetra carboxylic acid diimide (i)] were synthesized. The structures were characterized by 1H NMR, FTIR and MS, and the UV-vis maximal absorption, fluorescence spectroscopy, thermal properties were also investigated. Meanwhile, the polymerization and film forming ability of compound i were investigated. It is found that compound h opens the cyclobutene ring to form polymers when heated to 225 oC, and UV-vis maximal absorption, fluorescence spectroscopy and electrochemical property of compound i change little after becoming oligomer i. At the same time, the film of oligomer h is received through spin-coating technique which provide the condition of achieving the large area film.
Keywords/Search Tags:perylene bisimides, benzocyclobutene, OLED, synthesis
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