Department of Mechanical Engineering, School of Engineering , The University of Tokyo , 7-3-1 Hongo , Bunkyo-ku, Tokyo 113-8565 , Japan.
Hefei National Laboratory for Physical Sciences at the Microscale , University of Science and Technology of China , 96 Jinzhai Road , Hefei , Anhui 230026 , China.
ACS Appl Mater Interfaces. 2018 Apr 11;10(14):11810-11817. doi: 10.1021/acsami.8b00603. Epub 2018 Mar 30.
A diphenylanthracene dimethylamine derivative (9-{3,5-di( N, N-dimethylaminoethoxy)phenyl}-10-phenyl-anthracene, DPAMA) was synthesized by the Suzuki-Miyaura cross-coupling reaction. Its ammonium salt, 9-{3,5-di(trimethylammonium ethoxy)phenyl}-10-phenyl-anthracene dichloride (DPAMA-Cl), was also synthesized as a reference material. DPAMA was characterized by UV-vis and fluorescence spectroscopy, cyclic voltammetry, photoelectron yield spectroscopy, and X-ray photoelectron spectroscopy to evaluate the work function-modifying ability of DPAMA on indium tin oxide (ITO) and ZnO. The work functions of ITO and ZnO changed from 4.4 and 4.0 eV (pristine) to 3.8 and 3.9 eV, respectively. Using this surface modification effect of DPAMA, inverted organic light-emitting diodes were fabricated with device structures of ITO/DPAMA/Alq/NPD/MoO/Al (Alq = tris(8-hydroxyquinolinato)aluminum; NPD = N, N'-di-[(1-naphthyl)- N, N'-diphenyl]-1,1'-(biphenyl)-4,4'-diamine) and ITO/ZnO/DPAMA/Alq/NPD/MoO/Al. Both devices showed good performance at the range of current density, 1-300 mA/cm. The best inverted organic light-emitting diodes device showed luminance of 7720 cd/m, current efficiency of 4.51 cd/A, and external quantum efficiency of 1.45%. Also, poly(3-hexylthiophene):mixed phenyl-C and C butyric acid methyl ester-based organic solar cells using DPAMA and DPAMA-Cl as electron-transporting materials showed power conversion efficiencies of 3.3 and 3.4%, respectively.
一种二苯并蒽二甲胺衍生物（9-（3,5-二（N,N-二甲氨基乙氧基）苯基）-10-苯基蒽，DPAMA）通过 Suzuki-Miyaura 交叉偶联反应合成。它的铵盐，9-（3,5-二（三甲基铵乙氧基）苯基）-10-苯基蒽二氯化物（DPAMA-Cl），也被合成作为参考材料。DPAMA 通过紫外可见光谱和荧光光谱、循环伏安法、光电子产额光谱和 X 射线光电子能谱来评估 DPAMA 对氧化铟锡（ITO）和氧化锌的功函数修饰能力。ITO 和 ZnO 的功函数分别从 4.4 和 4.0 eV（原始）变为 3.8 和 3.9 eV。利用 DPAMA 的这种表面修饰效果，制备了具有 ITO/DPAMA/Alq/NPD/MoO/Al（Alq=三（8-羟基喹啉）铝；NPD=N，N'-二[（1-萘基）-N，N'-二苯基]-1,1'-(联苯）-4,4'-二胺）和 ITO/ZnO/DPAMA/Alq/NPD/MoO/Al 器件结构的倒置有机发光二极管。两种器件在电流密度为 1-300 mA/cm 的范围内都表现出良好的性能。最佳倒置有机发光二极管器件的亮度为 7720 cd/m，电流效率为 4.51 cd/A，外量子效率为 1.45%。此外，以 DPAMA 和 DPAMA-Cl 为电子传输材料的聚（3-己基噻吩）：混合苯基-C 和 C 丁酸甲酯有机太阳能电池的功率转换效率分别为 3.3%和 3.4%。
