The solubilities of five organic semiconductors and four nonsteroidal anti-inflammatory drugs (NSAIDs) were measured by a static analytical method in a set of seven representative organic solvents at 298.15 K and 0.10 MPa to determine the Hansen solubility parameter (HSP) of the solutes by a quantitative correlation with the extended Hansen model. Solubilities of the organic semiconductors (N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (NPB), 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP), anthracene, tetracene, and perylene) exhibited similar solvent dependence to each other, increasing in the order of ethanol < acetonitrile < hexane < acetone < carbon tetrachloride < chlorobenzene chloroform due to the large dispersion parameter delta(D) approximate to 21 and the small polarity and hydrogen bonding parameters (delta(P), delta(H)) approximate to (5, 5) of the solutes. In contrast, the solubilities of NSAIDs (naproxen, diclofenac, indomethacin, and niflumic acid) were hexane < carbon tetrachloride < acetonitrile approximate to chlorobenzene < ethanol approximate to chloroform < acetone, indicating the smaller delta(D) approximate to 19 and the larger (delta(P), delta(H)) approximate to (10, 11). The HSP analysis enabled us to estimate the solubilities in other solvents and solvent mixtures; for example, the solubility maximum of indomethacin in the mixtures of ethanol with ethyl acetate, acetone, and acetonitrile was well described by the minimum Hansen distance.