Amide and imide groups have been widely used in the design of organic semiconductors, and the development of new structure semiconductors based on these functional groups is of great interest to further improve the performance of organic electronic devices. Herein, we designed and synthesized two novel 5,10-dihydrodithieno[3,2-c:3′,2′-h][2,6]naphthyridine-4,9-dione (TVTDA) based quinoidal molecules with different side chains, TVTDA-CN-EH and TVTDA-CN-OD. Both molecules showed the deep lowest unoccupied molecular orbital (LUMO) and the deep highest occupied molecular orbital (HOMO) energy levels and strong absorption in the long wavelength region. Organic field-effect transistors (OFETs) based on TVTDA-CN-EH and TVTDA-CN-OD exhibited unipolar n-type electron transport behavior with mobilities of 0.04 and 0.0064 cm²·V⁻¹·s⁻¹, respectively. TVTDA-CN-EH with shorter alkyl side chains demonstrated better electron transport properties, which is attributed to the larger grain size in the film to facilitate charge transport. Furthermore, organic phototransistors (OPTs) based on TVTDA-CN-EH film showed good photo detection property from red light to near infrared region. Our work provides a new idea for the design and synthesis of organic semiconductors, especially for n-type organic semiconductors with photoresponse in the long wavelength.

酰胺和酰亚胺基团已广泛应用于有机半导体的设计中，基于这些官能团的新型结构半导体的开发对于进一步提高有机电子器件的性能具有重要意义。在此，我们设计并合成了两种具有不同侧链的新型5,10-二氢二噻吩[3,2-c:3',2'-h][2,6]萘啶-4,9-二酮（TVTDA）基醌型分子、TVTDA-CN-EH 和 TVTDA-CN-OD。两种分子均表现出深部最低未占分子轨道（LUMO）和深部最高占据分子轨道（HOMO）能级以及在长波长区域的强吸收。基于TVTDA-CN-EH和TVTDA-CN-OD的有机场效应晶体管（OFET）表现出单极n型电子传输行为，迁移率分别为0.04和0.0064 cm ² ·V ⁻¹ 。具有较短烷基侧链的TVTDA-CN-EH表现出更好的电子传输性能，这归因于薄膜中较大的晶粒尺寸有利于电荷传输。此外，基于TVTDA-CN-EH薄膜的有机光电晶体管（OPT）在红光到近红外区域表现出良好的光检测性能。我们的工作为有机半导体的设计和合成提供了新的思路，特别是在长波长下具有光响应的n型有机半导体。