Why does delocalization of π electrons bring stability?
In simple terms electrons repel each other, so distributing them over a geater number of bonds will reduce the repulsive force between them so resulting in a lower energy state. In the case of phenol the oxygen p orbital lone pair at right angles to the ring can overlap with the delocalised p orbital above and below the ring enabling a degree of delocalisation into the ring system so leaving a slight + charge on the oxygen. This in turn will reduce the electron density in the OH bond so weakening it and accounting for the weak acidity of phenol.