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Looking at Ben's  time  with respect to Philadelphia

2PM  Fri + 14 hrs   =   4AM    Sat  (Philadelphia time)

But Tokyo is  14 hrs  ahead of Philadelphia which  means that  he arrives in Tokyo at 6PM Sat

Looking at Matt's time  with respect to Philadelphia

12 PM  Fri +    12 hr flight + 3 hr layover = 

12PM Fri  +  15 hrs  =    3 AM Sat     (Philadelphia time )

Adding 14 hours to this =  5 PM  Sat   (Tokyo time)

So Matt arrives   first     and  Ben   arrives in  Tokyo   on Sat  at 6PM  

Thank you!