We report the first example of a thermally activated delayed fluorescence (TADF) poly(dendrimer), composed of a norbornenyl-derived polymer backbone and dendritic side-chain chromophores comprising 2,3-dicyanopyrazino as the electron acceptor and a first-generation fluorenylcarbazole derivative as the electron donor. The TADF poly(dendrimer) homopolymer, with one dendritic side chain attached to each monomer unit, emitted deep-red light. The emission of the poly(dendrimer) was found to be red-shifted relative to the nonpolymeric doubly dendronized emitter composed of the same components. The simple dendrimer was found to have a solution photoluminescence quantum yield (PLQY) of around 70%. In contrast, the poly(dendrimer) had a PLQY of 9%, which was attributed to intramolecular interchromophore interactions. An interesting feature of the poly(dendrimer) was that oxygen did not quench the TADF emission. We found that the PLQY of the simple dendrimer decreased markedly in neat films, whereas that of the poly(dendrimer) did not, with both having a solid-state PLQY of around 10%. The results suggest that intrapolymer chromophore-chromophore interactions observed in solution for the poly(dendrimer) were similar to the intermolecular chromophore-chromophore interactions of the dendrimer in the solid state. Simple two-layer organic light-emitting diodes comprising nondoped films of the materials and an electron transport layer showed red emission with CIE coordinates of (x > 0.66, y < 0.34). The dendrimer-based device had a maximum external quantum efficiency of 2.4%, which is among the best for solution-processed deep-red emissive TADF-based OLEDs but in a simpler device architecture.