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The synthesis and application of a series of crosslinkable bis(diphenylamine)‐substituted mixed dihydroindeno[1,2‐b]fluorenes as model systems for the fabrication of solution‐processed, multilayer organic light‐emitting diodes (OLEDs) is described. Introducing a novel functionalization approach by C(sp³)−C(sp²) Suzuki‐Miyaura reactions, the synthesis is based on a modular strategy, leading to eight nearly isoelectronic derivatives that allow for the observation of structure‐property relationships in the context of crosslinkable hole‐transport materials, e. g., for use in OLEDs. By systematically altering structural parameters, such as the number of crosslinkable oxetane moieties per molecule (2–6 moieties) and their position of attachment (geminal and/or lateral), process‐relevant thermal properties such as thermal stability (Td95, 170‐350°C) and glass‐transition temperature (15‐100°C) can be influenced and allow for the investigation of their impact on the crosslinking behavior and the resulting device performance.