First go theough extensive literature survey for reported TLC method of oleuropein. Than follow that method using same solvent and detection procedure.
For isolation of oleuropein, first extract powdered Olive leaves with 75 % aqueous ethanol. After evaporation of ethanol, extract the aqueous phase with chloroform and then with ethyl acetate for phenolic compounds. Evaporate the ethyl acetate phase totally evaporated to obtain dried extract. ,
Subject the EtOAC extract to column chromatography using silica gel and eluting with chloroform-methanol (9:1), then with chloroform-methanol (4:1). Combined TLC homogenous fractions may yield oleuropein. Identification of oleuropein can be done by TLC on silica gel with chloroform/methanol/ acetic acid (70:30:10) and spraying the plate with amino ethyl diphenyl borate solution (10%). Co-TLC with standard oleuropein will give more precise result.
Capasso R, Evidente A, Scognamiglio F. A simple thin layer chromatographic method to detect the main polyphenols occurring in olive oil vegetation waters. Phytochem Anal. 1992;3:270–275. doi:10.1002/pca.2800030607.
From the paper, you can have an idea about the solvent systems and the conditions useful for detecting major polyphenols in olive oil.