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咔唑功能化苝酰亚胺的合成及性质研究

The Synthesis and Properties Study of Carbazole-functionalized Perylene Bisimides

【作者】 冯涛

【导师】 马於光;

【作者基本信息】 吉林大学 , 物理化学, 2013, 硕士

【摘要】 苝酰亚胺衍生物是一类重要的n型有机半导体材料,具有大的共轭平面,高的荧光量子产率,优异的电子传输特性以及光、热、化学稳定性,通过在bay区和酰胺键上引入不同的取代基,可设计合成不同聚集结构和光电性能的苝酰亚胺化合物,所以近些年来受到研究者的广泛关注,其应用领域涵盖自组装功能材料,有机场效应晶体管,有机电致发光器件,有机太阳能电池等方面。咔唑具有较高的空穴迁移率;可电化学聚合,形成稳定的二聚体;具有多个咔唑基团的化合物可电化学聚合形成交联的结构,不溶解于有机溶剂。本论文设计、合成了一系列苝核上带有不同取代基的咔唑功能化的苝酰亚胺化合物,并进行了完整的结构、光学和电化学性质表征,通过控制实验条件中的氧化电位可以在不破坏苝核的情况下发生咔唑的电化学聚合,利用咔唑可以电化学聚合的性质制备了稳定的具有交联结构的苝酰亚胺化合物的薄膜。进一步,我们将咔唑功能化苝酰亚胺化合物的电化学聚合岛状超薄层用作倒置聚合物太阳能电池的电子收集层,研究了其对倒置聚合物太阳能电池器件性能的影响,结果表明,当加入一定厚度的苝酰亚胺化合物电化学聚合岛状超薄层作为电子收集层时,倒置聚合物光伏器件的效率有了一定的提高。

【Abstract】 Perylene bisimide compounds are a class of n-type materials of great importance,with large conjugate plane, high fluorescence quantum yield, excellent electrontransport properties and good light stability, thermal stability, chemical stability. Bysubstitution in different positions of perylene core and introduction of differentsubstituents to perylene core, new perylene bisimide compounds with adjustablecolors can be designed and synthesized. In recent years, perylene bisimidescompounds have been widely investigated on self-assembly functional materials,organic field-effect transistors, organic light-emitting diodes, organic solar cells andother fields.Carbazoles are commonly used as hole transport materials, which can formstable dimers through electrochemical polymerization and compounds with morecarbazole groups can form cross-linked structures by electrochemical polymerization.So we intend to introduce the electroactive carbazole to perylene bisimide in order toprepare stably cross-linked perylene bisimide films through electrochmicalpolymerization of carbazole group. We designed and synthesized a series ofcarbazole-functionalized perylene bisimides with different substituents in perylenecores. The structures of synthesized perylene bisimides were confirmed by NMR, MSand other characterization methods.We studied the optical properties and electrochemical properties ofcarbazole-functionalized perylene bisimide compounds. The compounds show the ability to form domain-like thin layer on ITO through electrochemical coupling ofperipheral carbazoles. Such domain-like ultra-thin layers are highly cross-linked inchemical structure (insoluble in any solvents), and strongly electrophilic in electronicstructure, exhibiting a potential as electron collection layers in inverted photovoltaiccells. The controlled domain-density of cross-linked particles on ITO has beenrealized through varied CV scanning cycles. Inverted polymer solar cells (PSCs)prepared by spin-coating an PCDTBT:PC71BM (90nm as active layer) on domainlayer modified ITO (as electron-collection layer) exhibit increased power conversionefficiency. Our results show that perylene bisimide derivatives are promisingcandidates for the modification of the electrodes by ECP method.

  • 【网络出版投稿人】 吉林大学
  • 【网络出版年期】2013年 09期
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