高性能可溶液加工的n型有机半导体是实现低成本、所有有机和灵活的复合逻辑电路。在n型半导体材料的设计中,调整化合物的LUMO能级是一个关键点。作为一个强吸电子单元,在化学结构中引入氯原子可以增加材料的电子亲和力并降低LUMO能级。这里,6,7,8,9-四氯-4,11-双(4-((2-乙基己基)氧基)苯基)-[1,2,5]噻二唑并[3,4-b]吩嗪(O4Cl)的一系列氯取代的N-杂并苯类似物,6,7,8,9-四氯-4,11-双(4-((2-乙基己基)硫基)苯基)-[1,2,5]噻二唑并[3,4-b]吩嗪(S4Cl),已合成并表征了1,2,3,4,8,9,10,11-八氯-6,13-双(4-((2-乙基己基)氧基)苯基)喹喔啉并[2,3-b]吩嗪(8Cl)和12Cl。基于这四种化合物的溶液处理有机场效应晶体管(OFET)表现出良好的电子迁移率为0.04cm2V-1s-1,0.01cm2V-1s-1,2×10-3cm2V-1s-1和3×10-3cm2V-1s-1,分别,在环境条件下。结果表明,这些氯取代的π共轭N-杂并苯类似物在OFET应用中是有前途的n型半导体。
High performance solution processable n-type organic semiconductor is an essential element to realize low-cost, all organic and flexible composite logic circuits. In the design of n-type semiconducting materials, tuning the LUMO level of compounds is a key point. As a strong electron withdrawing unit, the introduction of chlorine atom into the chemical structure can increase the electron affinity of the material and reduce the LUMO energy level. Here, a series chlorine substituted N-heteroacene analogues of 6,7,8,9-tetrachloro-4,11-bis(4-((2-ethylhexyl)oxy)phenyl)-[1,2,5]thiadiazolo[3,4-b]phenazine (O4Cl), 6,7,8,9-tetrachloro-4,11-bis(4-((2-ethylhexyl)thio)phenyl)-[1,2,5]thiadiazolo[3,4-b]phenazine (S4Cl), 1,2,3,4,8,9,10,11-octachloro-6,13-bis(4-((2-ethylhexyl)oxy)phenyl)quinoxalino[2,3-b]phenazine (8Cl) and 12Cl have been synthesized and characterized. Solution-processed organic field-effect transistors (
OFETs) based on these four compounds exhibit good electron mobilities of 0.04 cm2 V-1 s-1 , 0.01 cm2 V-1 s-1 , 2×10-3 cm2 V-1 s-1 and 3×10-3 cm2 V-1 s-1 , respectively, under ambient conditions. The results suggest that these chlorine substituted π-conjugated N-heteroacene analogues are promising n-type semiconductors in OFET applications.