Design,Synthesis And Application Of Naphthalene Monomide And Perylenediimide Acceptor Materials

Organic solar cells have attracted widespread attention due to their advantages of low cost,flexibility,and solution processing.High-performance acceptor materials are one of the major bottlenecks restricting their development.The naphthaleneimide and perylenediimide compounds have shown promising applications as acceptor materials.They have become a hot topic in the field of organic optoelectronics,but they are with low mobility,poor stability,and poor photoelectric conversion efficiency.Based on the design principles of organic semiconductors,a series of naphthalene monoimide polymers and perylenediimide acceptor molecules were designed and synthesized.Their structure characterization and optoelectronic properties were studied.1.In this study,a highly efficient four-step synthesis was developed and the key intermediate 3,6-dibromo-N-（2-octyldodecanyl）-1,8-naphthalimide was successfully obtained.Compared with the literature method,the advantage is that the intermolecular forces are regulated by different functional groups,and finally a highly pure 3,6-substituted 1,8-naphthalimide having a larger alkyl side chain modification is obtained.The naphthalene monoimide polymers were obtained for the first time using this compound as a parent.These polymers have strong absorption（at 300-600 nm）and strong electron acceptability（LUMO energy level is around-3.68 eV）.The space charge-limited current（SCLC）method tests show that these polymers are typical electron transport materials with the highest electron mobility up to 5.8 x 10^-3 cm² V^-1s^-1.2.3D distorted perylenediimide-based small molecules are excellent acceptor materials.We designed and synthesized a class of seleno twisted benzodiperylenediimides TBDPDI-Se,and TBDPDI-Se is synthesized by a six-step synthesis over an ester route in an overall yield of more than 10%.The advantage of this route is that the important intermediate phthalimide dimer anhydride TBDPDA-Se can be prepared.Starting from the key anhydride intermediates,seleno twisted benzodiperylenediimides substituted with different alkyl chains can be obtained easily.This material has a simple structure for the solar cells device and does not require additional optimization of its photoelectric conversion efficiency as high as 6.46%.