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三嗪和吡嗪類熱致延遲熒光材料的合成及性能研究

發(fā)布時(shí)間:2018-06-07 05:02

  本文選題:有機(jī)發(fā)光二極管 + 熱致延遲熒光; 參考:《大連理工大學(xué)》2015年碩士論文


【摘要】:有機(jī)發(fā)光二極管(OLEDs, Organic light-emitting diodes)作為近幾年發(fā)展迅速并有巨大應(yīng)用前景的新型平板顯示技術(shù),是有機(jī)光電子領(lǐng)域的熱門研究方向。與傳統(tǒng)的熒光材料和磷光材料相比,熱致延遲熒光材料兼具二者的優(yōu)點(diǎn),它既能夠充分利用單重態(tài)激子發(fā)光又能充分利用三重態(tài)激子發(fā)光而使得器件內(nèi)量子效率理論上達(dá)到100%。熱致延遲熒光材料為有機(jī)小分子,化學(xué)性質(zhì)穩(wěn)定且不需要和貴重金屬配位使得器件成本大幅降低。因而,研究、開發(fā)新型的熱致延遲熒光材料具有十分重要的現(xiàn)實(shí)意義。熱致延遲熒光材料一般要求化合物具有給電子性很強(qiáng)的P型基團(tuán)和吸電子性能很強(qiáng)的N型基團(tuán),三嗪是一類性能非常好的電子傳輸功能基團(tuán),吡嗪及其衍生物由于具有較高的熒光量子產(chǎn)率,優(yōu)異的光熱穩(wěn)定性和化學(xué)穩(wěn)定性,廣泛應(yīng)用于有機(jī)光電子領(lǐng)域。通過氰基修飾的吡嗪衍生物,與吡嗪相比具有更強(qiáng)的吸電子性能,并且它們?cè)跓嶂卵舆t熒光領(lǐng)域的應(yīng)用還未見報(bào)道。咔唑是一類具有很強(qiáng)供電子性的空穴傳輸功能基團(tuán),并有較大的空間立體構(gòu)型,以它為電子給體構(gòu)建的化合物通常具有較高的空穴遷移率和較好的熱穩(wěn)定性。本文以三嗪和二氰基吡嗪為N型基團(tuán)、氮苯基咔唑?yàn)镻型基團(tuán),適當(dāng)調(diào)控分子的立體構(gòu)型,構(gòu)造出了兩大類八種目前均未見報(bào)道的新型延遲熒光分子。使用紫外-可見吸收光譜儀、熒光分光光度計(jì)、循環(huán)伏安法、瞬態(tài)吸收光譜儀等測(cè)試研究了這些化合物的光物理性質(zhì)和電化學(xué)性質(zhì)。通過理論計(jì)算了化合物的HOMO和LUMO能級(jí)分布,計(jì)算結(jié)果顯示所有化合物的HOMO與LUMO幾乎完全分離。通過測(cè)試其中二氰基吡嗪類化合物M5的納秒瞬態(tài)吸收光譜研究了它的瞬態(tài)光物理性質(zhì),研究發(fā)現(xiàn)M5在室溫條件下具有長壽命的三重態(tài)(32.2¨s),熒光壽命測(cè)試結(jié)果證實(shí)M5在波長500 nm處的熒光不僅包括短壽命(納秒級(jí))的瞬時(shí)熒光(PF),而且還包括長壽命(微秒級(jí))的延遲熒光(DF),且延遲熒光壽命在除氧甲苯中達(dá)52¨s,如此長的延遲熒光壽命比傳統(tǒng)熒光壽命高出1000倍以上。以其中三嗪類化合物M1為雙偶極主體材料,Firpic和Ir(ppy)3分別為發(fā)光客體制備了相應(yīng)的藍(lán)色和綠色磷光器件,研究了它的電致發(fā)光性質(zhì)。藍(lán)色和綠色磷光器件均具有高效的器件性能。其中,綠色磷光器件的最大效率分別為96.9 cd/A和28.7%。結(jié)果表明,M1既可以作為發(fā)光材料應(yīng)用于有機(jī)電致發(fā)光器件中,又表現(xiàn)出較好的主體材料性能。
[Abstract]:As a new flat panel display technology with rapid development and great prospect in recent years, organic light-emitting diode (OLEDs) is a hot research direction in the field of organic optoelectronics. Compared with the traditional fluorescent material and phosphorescent material, the thermally induced delayed fluorescence material has the advantages of both. It can make full use of the singlet exciton luminescence and triplet exciton luminescence, so that the quantum efficiency of the device can reach 100% theoretically. The thermally induced delayed fluorescence materials are organic small molecules, which have stable chemical properties and do not need to coordinate with precious metals, so the device cost is greatly reduced. Therefore, it is of great practical significance to study and develop new thermal delayed fluorescence materials. Thermally induced delayed fluorescence materials generally require the compounds to have strong electronic-dependent P-type groups and strong electron-absorbing N-type groups. Triazine is a class of electron transport functional groups with very good properties. Pyrazine and its derivatives have been widely used in the field of organic optoelectronics due to their high fluorescence quantum yield excellent photothermal and chemical stability. The cyanide-modified pyrazine derivatives have stronger electron absorption properties than pyrazines, and their applications in the field of thermo-induced delayed fluorescence have not been reported. Carbazole is a kind of hole transport group with strong electron supply and has a large spatial stereoscopic configuration. The compounds constructed with carbazole as electron donor usually have higher hole mobility and better thermal stability. In this paper, using triazine and dicyanopyrazine as N-type group, nitrophenyl carbazole as P-type group, and regulating the stereomorphism of the molecule properly, two kinds of eight kinds of novel delayed fluorescent molecules have been constructed, which have not been reported at present. The photophysical and electrochemical properties of these compounds were investigated by UV-Vis absorption spectrometer, fluorescence spectrophotometer, cyclic voltammetry and transient absorption spectrometer. The distributions of HOMO and LUMO energy levels of the compounds are calculated theoretically. The results show that the HOMO and LUMO of all the compounds are almost completely separated. The transient photophysical properties of dicyanopyrazines M5 were studied by nanosecond transient absorption spectra. It is found that M5 has a long lifetime triplet at room temperature. The fluorescence lifetime test shows that the fluorescence of M5 at wavelength 500nm includes not only short-lived (nanosecond) transient fluorescence, but also long-lifetime (microsecond) fluorescence. The delayed fluorescence lifetime is 52? s in deoxygenated toluene, which is more than 1000 times higher than that of the traditional fluorescence lifetime. The blue and green phosphorescence devices were prepared by using triazine M _ 1 as the bipolar host materials and Ir(ppy)3 as the luminescent object respectively. The electroluminescent properties of the devices were investigated. Both blue and green phosphors have high performance. The maximum efficiency of green phosphor is 96. 9 cd/A and 28. 7 respectively. The results show that MNO _ (1) can be used as a luminescent material in organic electroluminescent devices, and it also shows a good performance of the main material.
【學(xué)位授予單位】:大連理工大學(xué)
【學(xué)位級(jí)別】:碩士
【學(xué)位授予年份】:2015
【分類號(hào)】:TN383.1

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