Previous studies have mainly focused on the source rocks of the 7th Member of Yanchang Formation (Chang 7 Member) in the Ordos Basin, with very few studies focusing on the extracts from the source rocks. These extracts have important guiding significance for studying the in situ conversion process of shale oil. Taking the shale source rock of the Chang 7 Member as an example, this paper selected the extract of shale source rock (i.e., retained oil), which has been less studied previously, as the sample to carry out the hydrocarbon-generating pyrolysis simulation experiment of a semi-open–semi-closed system. Seven groups of parallel simulation experiments were designed with a pressure of 20 MPa. The generated oil and gas were collected and quantified, and their geochemical characteristics were researched. In addition, the generated oil and gas were investigated from aspects of cumulative yield and net increased yield, and the chromatographic and mass spectral characteristics of the generated oil were also researched. Based on this, an inductive hydrocarbon generation model of retained oil in shale source rocks was established: slow hydrocarbon generation stage (300–320 °C), rapid hydrocarbon generation stage (320–360 °C), and residual oil pyrolysis stage (0.79%Ro–1.47%Ro). This study is of important significance to guide the research on the in situ conversion process of shale source rock.