Logic behind the answer:
The biggest change in brightness is: 7->8 (+4), 0->1 (-4), 1->2 (+3), 6->7 (-3).
Changing time by "tens," the greatest increase is from :19->:20 (+4), which is better than any single digit change.
An hour change (:59->:00) results in +1 brightness, so it is "inefficient" to go down in brightness (change in a single digit, 6->7, is less than :19->:20, and going from 6:59->7:00, is only a change of (-1)). So we are looking for an increase in brightness.
So, without really looking at anything else, my initial guess is:
7:59->8:00
resulting in:
+5 brightness
Note:
There is no lateral thinking
tag, but when the clock is at 8:08, unplugging it results in a change of (-20) which is a greater change than (+6).
Edit:
Nine is 6 digits, not 5 like I originally thought.