本文選題：合成 + 咔唑　； 參考：《長春工業(yè)大學(xué)》2017年碩士論文

【摘要】：咔唑具有穩(wěn)定的平面共軛剛性結(jié)構(gòu),結(jié)構(gòu)中氮原子含孤對電子是一種稠環(huán)結(jié)構(gòu)的化合物,同時咔唑基團(tuán)是一種具有優(yōu)良光電性能的基團(tuán)。其不僅光熱穩(wěn)定性良好,還能進(jìn)行多位點的化學(xué)反應(yīng)。將咔唑設(shè)計于光電功能材料中,不僅能保證其具有良好的光電性能,也可擴展科研人員對化合物的設(shè)計思路。當(dāng)前對于咔唑基團(tuán)的研究與利用是通過共軛的方式引入到主鏈中,或以不同的聚合方式將咔唑引入聚合物鏈中形成高分子聚合材料等。將咔唑以烷基鏈的方式結(jié)合到目標(biāo)化合物中研究的則比較少。由于烷基鏈連接的咔唑基團(tuán)具有給電子的特性,其中咔唑本身又具有光電性質(zhì)和電荷傳輸性能,使得這類材料在光電材料領(lǐng)域應(yīng)用潛力巨大。溶解度在有機發(fā)光材料中是一個很重要的條件,在化合物中引入烷基鏈可以有效的提高溶解度還可以促進(jìn)高質(zhì)量的薄膜沉積。光電器件的穩(wěn)定性和壽命關(guān)鍵在于化合物的熱穩(wěn)定性。咔唑衍生物是一類強的藍(lán)色光發(fā)射、高Tg溫度和熱穩(wěn)定性效應(yīng)的化合物,使它們成為OLED設(shè)計有吸引力的候選者。本文設(shè)計合成三種含有不同長度烷基鏈具有較強的藍(lán)色發(fā)光性和高穩(wěn)定性的咔唑衍生物。并利用DSC、TGA研究了其熱化學(xué)性能;利用紫外光譜、熒光光譜研究了其光化學(xué)性能;還利用循環(huán)伏安對其電化學(xué)性能進(jìn)行了研究,探尋了其在光和電轉(zhuǎn)化方面的應(yīng)用潛力。通過測定三種目標(biāo)化合物的熱化學(xué)性能及熒光量子效率,表明咔唑基團(tuán)能提高目標(biāo)化合物的熱穩(wěn)定性,同時咔唑基團(tuán)可提高目標(biāo)化合物的液態(tài)熒光量子效率。其中目標(biāo)化合物在DMF、THF、DMSO等溶液中的溶液熒光量子效率更是高達(dá)70%以上。通過積分球測試目標(biāo)化合物的絕對熒光量子產(chǎn)率發(fā)現(xiàn),目標(biāo)化合物的固態(tài)熒光量子效率隨著碳原子數(shù)目的增加而增加,液態(tài)熒光量子產(chǎn)率隨著碳原子數(shù)的增加而減少,且液態(tài)熒光量子效率明顯比固態(tài)熒光量子效率大。通過熒光壽命的測試可知含有兩個碳烷基鏈接的目標(biāo)化合物在THF中的平均壽命8.24納秒,含有四個碳烷基鏈接的目標(biāo)化合物在THF溶液中的平均壽命為8.02納秒,含有兩個碳烷基鏈接目標(biāo)化合物固態(tài)平均壽命為1.04納秒,含有四個碳烷基鏈接的目標(biāo)化合物固態(tài)平均壽命為1.17納秒。熒光壽命均在納秒數(shù)量級,這正是典型的π-π*躍遷的壽命,通過測試發(fā)現(xiàn)化合物的熒光壽命正好與單線態(tài)激子的壽命相當(dāng),表明了該化合物發(fā)光主要為單線態(tài)激子發(fā)光。從電化學(xué)分析可知目標(biāo)化合物的HOMO能級為-5.31 eV~-5.33eV,目標(biāo)化合物的LUMO能級為-1.84 eV~-1.83 eV。對目標(biāo)化合物的熱穩(wěn)定性研究可知,目標(biāo)化合物的熱分解溫度分別為425℃,415℃,356℃,可知目標(biāo)化合物具有熱穩(wěn)定性。從電化學(xué)和理論計算可知該目標(biāo)化合物存在分子內(nèi)電荷轉(zhuǎn)移性能。
[Abstract]:Carbazole has a stable planar conjugate rigid structure in which nitrogen atoms have solitary pairs of electrons which are a dense ring structure and carbazole groups have excellent photoelectric properties. It not only has good photothermal stability, but also can carry out multiple chemical reactions. The design of carbazole in optoelectronic functional materials can not only guarantee its good optoelectronic properties, but also extend the design ideas of compounds. At present, carbazole groups are introduced into the main chain by conjugation, or carbazole is introduced into the polymer chain in different ways to form polymeric materials. Less research has been done on carbazole in the form of alkyl chains in the target compounds. Because the carbazole group connected with alkyl chain has the characteristics of electron giving, and carbazole itself has photoelectric property and charge transport property, this kind of material has great application potential in the field of optoelectronic materials. Solubility is a very important condition in organic luminescent materials. The introduction of alkyl chain in compounds can effectively improve the solubility and promote the deposition of high quality thin films. The stability and lifetime of optoelectronic devices depend on the thermal stability of compounds. Carbazole derivatives are a class of compounds with strong blue light emission, high TG temperature and thermal stability, which make them attractive candidates for OLED design. In this paper, three carbazole derivatives with different length alkyl chains are designed and synthesized with strong blue luminescence and high stability. Its thermochemical properties were studied by DSC-TGA, its photochemical properties were studied by UV spectra and fluorescence spectra, and its electrochemical properties were studied by cyclic voltammetry to explore its application potential in photo-electric conversion. By measuring the thermochemical properties and fluorescence quantum efficiency of the three target compounds, it is shown that the carbazole group can improve the thermal stability of the target compound and the carbazole group can improve the liquid fluorescence quantum efficiency of the target compound. The fluorescence quantum efficiency of the target compounds in DMFU THF DMSO solution is more than 70%. By measuring the absolute fluorescence quantum yield of the target compound with the integration sphere, it is found that the quantum efficiency of solid state fluorescence increases with the increase of the number of carbon atoms, and the quantum yield of liquid fluorescence decreases with the increase of the number of carbon atoms. The quantum efficiency of liquid fluorescence is higher than that of solid state fluorescence. The average lifetime of target compounds with two alkyl links in THF was 8.24 nanoseconds, and that of target compounds with four alkyl links in THF solution was 8.02 nanoseconds. The average solid-state life of target compounds containing two alkyl chains is 1.04 nanoseconds, and that of target compounds with four alkyl links is 1.17 nanoseconds. The fluorescence lifetime is in the order of nanosecond, which is exactly the lifetime of the typical 蟺-蟺 * transition. It is found that the fluorescence lifetime of the compound is exactly the same as that of the singlet exciton, which indicates that the luminescence of the compound is mainly a singlet exciton. Electrochemical analysis shows that the HOMO energy level of the target compound is -5.31 EV ~ (-5.33) EV, and the LUMO energy level of the target compound is -1.84 eV~-1.83 EV. The thermal stability of the target compound is studied. The thermal decomposition temperature of the target compound is 425 鈩，

本文編號：1828697