The development of crosslinkable materials for the fabrication of solution processable OLEDs presents challenges, especially regarding the adjustment of the glass transition (T_g), which has a significant influence on crosslinking kinetics and device life-time. Crosslinkable hole transport materials based on poly(N,N-bis(4-(9H-carbazol-9-yl)phenyl)-4-vinylaniline) (poly-TCTA) with covalently attached plasticizers for T_g control and azide functionalities for azide-alkyne crosslinking are presented. These polymers have an optimal T_g of around 150 °C and show superior crosslinking performances and solution resistibilities. Incorporation of electron-pushing alkoxides to the pendant groups combines the T_g adjustment approach with a systematic tuning of the HOMO level from −5.7 to −5.3 eV. All presented polymers have good charge transport and injection properties and are ideal for applications in phosphorescent OLEDs due to their high triplet energies (>2.8 eV). The new crosslinkable poly-TCTA-based materials are applied as hole-transport layers (HTLs) in fully solution-processed OLEDs. An improvement of the device performance is demonstrated for OLEDs with additional crosslinked HTL.