Is he wanting food or attention? You could try feeding him just before bedtime. You could also try leaving some toys outside the bedroom door, I found that works quite well.
I have a 7 month old neutered male, very playful, but a gentle personality. I got kitten nr. 2. a 12 week old female, to keep him company.
I set up a separate room for her, first 24 hrs ok & nr. 1 already sniffing curiously at the door. Then the problems started, when I left nr. 2 alone she...
Matty is not mad at you, she just feels uncertain. It sounds like the kitten is quite demanding, but try to give Matty lots of attention. I would also support the recommendation of the cat tree.