The invention relates to a chiral thermal activation delayed fluorescence material and a preparation method thereof. The delayed fluorescence material is R / S-18,21-di(10H-phenoxazine-10-yl)-3,4,5,6,7,8,9,10-octahydrodibenzo[a,c]dinaphtho[2',1':5,6;1',2'':7,8][1,4]dioxin[2,3i]phenazine, or R / S-16,17-bis(4-(10H-phenoxazine-10-yl)phenyl)3,4,5,6,7,8,9,10-octahydronaphthalo[2',1':5,6; 1',2'':7,8][1,4]dioxane[2,3g] quinoxaline. The compound provided by the invention has the characteristics of a rigid large-plane twisted structure and a remarkable internal charge transfer (ICT) effect, and has the advantages of typical thermal activation delayed fluorescence (TADF) property, circular polarization (CPL) property, high fluorescence quantum yield (PLQY), good thermal stability and the like. The method has the advantages of few synthesis and preparation steps, readily available raw materials, simple synthesis and purification processes and high yield, and can be used for large-scale synthesis andpreparation.