In the last three decades, p-type (hole-transporting) organic and polymeric semiconductors have achieved great success in terms of materials diversity and device performance, while the development of n-type (electron-transporting) analogues greatly lags behind, which is limited by the scarcity of highly electron-deficient building blocks with compact geometry and good solubility. However, such n-type semiconductors are essential due to the existence of the p–n junction and a complementary metal oxide semiconductor (CMOS)-like circuit in organic electronic devices. Among various electron-deficient building blocks, imide-functionalized arenes, such as naphthalene diimide (NDI) and perylene diimide (PDI), have been proven to be the most promising ones for developing n-type organic and polymeric semiconductors. Nevertheless, phenyl-based NDI and PDI lead to sizable steric hindrance with neighboring (hetero)arenes and a high degree of backbone distortion in the resultant semiconductors, which greatly limits their microstructural ordering and charge transport. To attenuate the steric hindrance associated with NDI and PDI, a novel imide-functionalized heteroarene, bithiophene imide (BTI), was designed; however, the BTI-based semiconductors suffer from high-lying frontier molecular orbital (FMO) energy levels as a result of their electron-rich thiophene framework and monoimide group, which is detrimental to n-type performance.

中文翻译：

---

基于联噻吩酰亚胺衍生物的 n 型有机和聚合物半导体

在过去的 30 年中，p 型（空穴传输）有机和聚合物半导体在材料多样性和器件性能方面取得了巨大成功，而 n 型（电子传输）类似物的发展却大大滞后，这是受限于具有紧凑几何形状和良好溶解性的高度缺电子结构单元的稀缺性。然而，由于有机电子器件中存在 p-n 结和类似互补金属氧化物半导体 (CMOS) 的电路，因此这种 n 型半导体是必不可少的。在各种缺电子结构单元中，亚胺功能化芳烃，如萘二亚胺 (NDI) 和苝二亚胺 (PDI)，已被证明是开发 n 型有机和聚合物半导体最有前途的化合物。尽管如此，基于苯基的 NDI 和 PDI 导致与相邻（杂）芳烃的相当大的空间位阻和所得半导体的高度骨架畸变，这极大地限制了它们的微观结构排序和电荷传输。为了减弱与 NDI 和 PDI 相关的空间位阻，设计了一种新型的酰亚胺功能化杂芳烃，即联噻吩酰亚胺 (BTI)；然而，基于 BTI 的半导体由于其富含电子的噻吩骨架和单酰亚胺基团而受到高位前沿分子轨道 (FMO) 能级的影响，这对 n 型性能不利。为了减弱与 NDI 和 PDI 相关的空间位阻，设计了一种新型的酰亚胺功能化杂芳烃，即联噻吩酰亚胺 (BTI)；然而，基于 BTI 的半导体由于其富含电子的噻吩骨架和单酰亚胺基团而受到高位前沿分子轨道 (FMO) 能级的影响，这对 n 型性能不利。为了减弱与 NDI 和 PDI 相关的空间位阻，设计了一种新型的酰亚胺功能化杂芳烃，即联噻吩酰亚胺 (BTI)；然而，基于 BTI 的半导体由于其富含电子的噻吩骨架和单酰亚胺基团而受到高位前沿分子轨道 (FMO) 能级的影响，这对 n 型性能不利。