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Polychlorinated (hetero)arenes have shown great promise for organic optoelectronics applications. However, the harsh synthetic routes for polychlorinated compounds and the possible luminescence quenching from the compact intermolecular π–π stacking induced by chlorine atoms limit their investigations and applications in luminescent materials. Herein, two isomeric polychlorinated polycyclic aromatic hydrocarbon (PAH) compounds JY‐1‐Cl and JY‐2‐Cl consisting of rigidified aryl ketones and amine are designed and synthesized under mild conditions through nucleophilic chlorination intermediated by an electron donor‐acceptor complex. Among them, as a result of the strong π–π interactions induced by chlorine atoms, JY‐2‐Cl exhibits bright monomer and dimer emissions with dual thermally activated delayed fluorescence (TADF) characters. Notably, compared with the non‐chlorinated compounds, a high photoluminescence quantum yield is maintained after introducing multiple chlorine atoms into JY‐2‐Cl. The first dual‐TADF organic light‐emitting diodes are also successfully fabricated with maximum external quantum efficiency as high as 29.1 % by employing JY‐2‐Cl as emitter. This work presents a new paradigm and synthesis of polychlorinated amine‐carbonyl PAHs and demonstrates the great potential of the chlorinated materials for luminescent applications. [ABSTRACT FROM AUTHOR]