The effect of hole length to diameter ratio on flat plate film cooling effectiveness and flow structures of axial and compound angle hole is investigated by large eddy simulation (LES). Film cooling simulations are performed for three blowing ratios (M) ranging from 0.4 to 1.2, three hole length-to-diameter ratios (L/D) from 0.5 to 5 and two compound angle (β: 0°, 45°). The prediction accuracy is validated by the reported hydrodynamic data and present film effectiveness data measured by pressure sensitive paint (PSP). Results indicate that discrete hole with L = 0.5 show highest film cooling effectiveness regardless of compound angle. Round hole generally shows an increasing trend as L increases from 2 to 5, while compound angle hole shows a complex trend concerning with blowing ratios and length to diameter ratios. This is associated with the fact that length-to-diameter ratio influences the in-tube flow behavior, formation of Kelvin-Helmholtz (K-H) structures, and development of single asymmetric main vortex (SAMV). Scalar field transportation features are investigated to clarify how different vortex structures affect the temperature distribution and the film cooling effectiveness. It is also demonstrated that the counter rotating vortex pair (CRVP) which is observed in the time-averaged flow field of axial hole is originated in different vortex structures with varying blowing ratios and length to diameter ratios.