The way you built the conditions it would have to match all of the times of day to proceed which is impossible.
For multiple time groups, you would need to make condition groups similar to how regular time conditions app builds them which is a bit harder in the GUI since you would have to duplicate almost all of the settings using a different group number for each time set.
An easier way would be to duplicate the outbound route in GUI then edit each copy's time entry accordingly.
Make an outbound route with the first time frame and for ease of understanding, label that route as the times it matches.
Save, then copy that outbound route 6-7 times as needed for each time frame.
Edit the copies to match one specific time.