1-5 tells of the Lord disfavoring the people, because they made a covenant with the inhabitants of the land, and did not break their altars as commanded. Perhaps the covenant in question was the proposed marriage of Shechem & Dinah, and the order to break the altars of the inhabitants would have come in , so this passage comes some time after that.
6-10 tells of the death of Joshua son of Nun (i.e., Jacob, who died in ).
11-15 tells of the people being given over to plunderers, who could have been the Hebrews, anytime in the range of .
16-23 says that the Lord provided judges to deliver the people from the plunderers, but the people still wouldn't obey. So the Lord did not drive out the inhabitants of the land as he had promised, and instead left them as thorns in the side of the people. The first initiative involving judges was Horemheb's attempt to decentralize authority, to undermine the Atenists, beginning in earnest in , though this initiative could have been later.
The whole chapter is worded so vaguely, and so consistent with the general Deuteronomic style, that it could be just an introduction to the recurring theme, which later on gets more accurate, but at this stage, it's just some vague references to a covenant with the locals, and not suppressing their religions, whereupon they got plundered, and not even judges appointed by the Lord could save them.
Judah got his daughter-in-law Tamar pregnant with the twins Perez & Zerah. [The significance of this hasn't been determined. He would have been ~40 years old, to have a married son, and he was born in , so this would have been , after the relocation to Goshen.]