Zhaoyang Chen, Rui Li, Qianhui Jia, Junhao Deng, Dongxu Liang, Lan Cao, Jun Zhang, Cheng Wang, Jianhua Hu, Yongqiang Shi, Haichang Zhang
Abstract Developing simple and effective molecular design strategies to optimize charge transport mobility remains a key challenge in high‐performance organic semiconductors. In this study, we integrate hydrogen bonding (H‐B) and ring‐fusion (R‐F) into a diketopyrrolopyrrole (DPP)‐based polymer, yielding a novel material, P‐HF. For comparison, a reference polymer (P‐B) and a hydrogen‐bonded analogue (P‐H) were synthesized. The synergistic effects of H‐B and R‐F dramatically not only enhance both inter‐ and intramolecular charge transport but also optimize the frontier orbital levels; H‐B strengthens intermolecular interactions, enabling localized ordered molecular packing and tighter π–π stacking, while R‐F further amplifies these effects meanwhile improving backbone planarity, extending π‐conjugation, and optimizing frontier orbital levels. As a result, P‐HF achieves an outstanding hole mobility of 5.02 cm 2 V −1 s −1 , surpassing P‐B (0.71 cm 2 V −1 s −1 ) and P‐H (2.13 cm 2 V −1 s −1 ), placing it among the highest‐performing DPP‐based polymers reported. This work demonstrates that combining R‐F and H‐B offers a viable strategy for designing high‐mobility conjugated materials, potentially advancing organic semiconductor development. This dual‐engineering strategy is particularly suitable for π‐conjugated polymers containing both hydrogen‐bonding sites and ring‐fused backbones.