摘要
通过Suzuki偶联反应合成了三种多支化p-n结构窄带隙材料P1,P2和P3.通过1H NMR,13C NMR,GC-MS/MALDI-TOF等表征了其化学结构,并研究了其光物理性质、热力学性质、电化学性质及其电子结构与光电性能等.结果表明这三种星型分子具有溶解性好、能隙窄、吸收光谱宽及热稳定性高等特点.
Well-defined π conjugated molecules have attracted much attention in the field of organic electronics, due to their promising optoelectronic properties, good monodispersity, high purity, excellent reproducibility and facile functionalization. Here, a series of starburst molecules (P1, P2 and P3) with truxene as the core, thiophene unit as p-type electron donating segments, and benzothiadiazole chromophore as the n-type electron accepting segments, have been designed and synthesized. The aim of the systematic investigation of these structural variations was to provide insight into the relationship between the effective conjugation length and the photophysical properties, the intramolecular energy transfer process, which would shed light for the rational design of novel optoelectronic materials for organic electronic devices. The resulting molecules, P1, P2, and P3, possess a series of advantages, including high solubility, broad absorption, low band gap and good thermal stability, etc. The chemical structures of the intermediates and resulting molecules were confirmed by 1H NMR, 13C NMR, GC-MS/MALDI-TOF. P1, P2, and P3 exhibited good thermal stability according to thermogravimetric analysis (TGA) and low-lying HOMO and LUMO energy levels as well as narrow band gaps according to cyclic voltammetry (CV). P1 and P3 possessed amorphous properties, while P2 exhibited crystalline properties as revealed by differential scanning calorimetry (DSC). The electronic properties have also been investigated by DFT calculation. The HOMO/LUMO energy levels and band gaps could be fine tuned by varying the content of p and/or n type moieties. Compared to P1 and P2, the maximum absorption and emission of P3 were obviously red-shifted due to increased effective conjugation with introducing additional thiophene units into the p-n branches and modulating the substituted position of the alkyl group. To investigate the primarily optoelectronic properties of these molecules, OLEDs were fabricated using the following configuration: ITO/PEDOT: PSS (50 nm)/EML (74 nm)/TPBi (30 nm)/LiF (1.3 nm)/Al (80 nm). Maximum luminance of 2908, 4683, 1085 and 4730 cd/m2 were demonstrated with maximum current efficiency of 1.18, 0.50, 0.16 and 2.50 cd/A, respectively.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2013年第9期1248-1256,共9页
Acta Chimica Sinica
基金
国家重大基础研究发展计划项目(No.2009CB930601)
国家自然科学基金(Nos.20904024,51173081,61136003,61106036,61204048)
江苏省自然科学基金(No.BK2011760)
南京邮电大学攀登计划(Nos.NY210016,NY212072)
江苏高校优势学科建设工程资助项目
江苏省“青蓝工程”项目
江苏省普通高校研究生科研创新计划项目(No.CXLX11_0399)资助~~
关键词
共轭分子
噻吩衍生物
星型多支化分子
窄带隙
有机电致发光
conjugated molecules
thiophene
star-shaped molecules
narrow band gap
organic light-emitting diodes