本研究聚焦於可拉伸N型高分子半導體之分子設計，透過將不同類型之共軛中斷單元（CBSs）導入萘二醯亞胺（NDI）的N型高分子主鏈中，探討其對有機場效電晶體在形變條件下之電性穩定性與可拉伸性的影響。本研究主要分為兩部分：(1) 不同結構與構型 CBS 之影響，以及 (2) 鉸鏈與平面型CBS 結構之應變響應行為。第一部分比較單環tCH、對稱三環TCD，以及三環異構混合物rTCDs作為 CBS 時的影響。研究結果顯示，TCD的高剛性三環結構可促進主鏈 π–π 堆疊並提供較高初始電子遷移率，但在拉伸下機械穩定性較差；tCH 則因具有較高鏈段柔順性，有助於形成較高的結晶性與較緊密的分子排列，但也可能限制高分子鏈在反覆形變下的重組與應力釋放，因而不利於循環拉伸下的電性維持。相較之下，rTCDs 因異構混合所帶來適度結構無序，可形成雙峰分子取向並增加自由體積，因而能維持穩定的載子傳輸。於 40% 應變下經1000 次拉伸循環後，rTCDs 聚合物於平行與垂直方向仍分別保有 77% 與 104% 的電子遷移率。第二部分則探討具鉸鏈型結構之噻蒽（TA）CBS 的應變響應。結果顯示，TA可在拉伸下發生構形平面化，降低局部應力集中並延長有效共軛長度，同時還部分補償形變造成的電性衰減。此外，掠角入射廣角X光散射分析顯示，TA系統的層間距與π–π堆疊距離隨應變增加呈現先縮短後回復的部分可逆變化。此動態結構響應使TA系統於60% 應變下仍能維持近似各向同性的載子傳輸，且經循環拉伸後性能甚至較初始狀態提升。綜合兩部分研究結果，異構CBS所引入的適度結構無序，可藉由增加自由體積與取向多樣性提供被動應力緩衝，而鉸鏈型TA單元則進一步將應變誘導的動態構形調適導入高分子主鏈，使材料可透過局部平面化重新分配應力，並部分恢復有效共軛與分子堆疊。此由靜態結構無序延伸至動態應變響應的CBS設計策略，可進一步緩解電子傳輸效能與可拉伸性之間的權衡，並為下一代穿戴式與可變形電子材料提供新的分子設計方向。

This study investigates stretchable N-type semiconducting polymers by incorporating conjugation-break spacers (CBSs) with distinct molecular structures into naphthalene diimide (NDI)-based polymer backbones. The effects of CBS incorporation on the electrical stability and stretchability of organic field-effect transistors under mechanical deformation were investigated. This study consists of two main parts: (1) the effects of CBSs with different structures and configurations and (2) the strain-responsive behavior of hinge-type and planar CBS structures. The first part compares a monocyclic tCH unit, a symmetric tricyclic TCD unit, and a mixture of tricyclic structural isomers, rTCDs as CBSs. The results show that the highly rigid tricyclic structure of TCD promotes π–π stacking between polymer backbones and provides a relatively high initial electron mobility. However, its limited structural adaptability results in poor mechanical stability under tensile deformation. In contrast, the greater segmental flexibility of tCH facilitates the formation of higher crystallinity and more compact molecular packing. Nevertheless, the excessively ordered structure may restrict polymer-chain reorganization and stress relaxation during repeated deformation, thereby compromising the retention of electrical performance over long-term stretch–release cycling. By comparison, the moderate structural disorder introduced by the isomeric mixture of rTCDs promotes bimodal molecular orientation and increases free volume, thereby enabling stable charge transport. After 1000 stretch–release cycles at 40% strain, the electron mobilities of the rTCDs-based polymer measured parallel and perpendicular to the strain direction retained 77% and 104% of their respective initial values. The second part investigates the effects of thianthrene (TA), which possesses a hinge-like geometry as a CBS unit. The results indicate that TA undergoes conformational planarization under tensile strain, reducing local stress concentration and extending the effective conjugation length, thereby partially compensating for the electrical degradation caused by mechanical deformation. In addition, grazing-incidence wide-angle X-ray scattering analysis reveals that both the lamellar spacing and π–π stacking distance of the TA-based system initially decrease and subsequently recover with increasing strain, indicating a reversible structural response. This dynamic conformational adaptability enables the TA-based polymer to maintain nearly isotropic charge transport at 60% strain. Moreover, its electrical performance was maintained and even slightly improved after repeated stretch–release cycling compared with the initial state. Taken together, the moderate structural disorder introduced by isomeric CBSs provides passive stress buffering by increasing free volume and molecular-orientation diversity. The hinge-type TA unit further introduces strain-induced dynamic conformational adaptability into the polymer backbone, allowing local planarization to redistribute stress and partially restore effective conjugation length and molecular packing. This CBS design strategy, which progresses from static structural disorder to dynamic strain responsiveness, further mitigates the trade-off between charge-transport performance and stretchability and provides a new molecular design direction for next-generation wearable and deformable electronic materials.

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