Isaiah 24:21
19 The earth is broken in pieces, the earth is ripped to shreds, the earth shakes violently. 20 The earth will stagger around like a drunk; it will sway back and forth like a hut in a windstorm. Its sin will weigh it down, and it will fall and never get up again. 21 At that time the Lord will punish the heavenly forces in the heavens and the earthly kings on the earth. 22 They will be imprisoned in a pit, locked up in a prison, and after staying there for a long time, they will be punished. 23 The full moon will be covered up, the bright sun will be darkened; for the Lord of Heaven’s Armies will rule on Mount Zion in Jerusalem in the presence of his assembly, in majestic splendor.
2 Enoch 7:1
Secrets of Enoch1 Those men took me and led me up to the second heaven, and showed me darkness, greater than earthly darkness. There I saw prisoners hanging, watched, awaiting the immense and boundless judgment, and these spirits appeared darker than earthly darkness, constantly weeping at all hours. 2 I said to the men who were with me: 'Why are these being constantly tortured?' They answered me: 'These are God's defectors, who did not obey God's commands but followed their own will, and turned away with their leader, who is also confined on the fifth heaven.'
Notes and References
"... Some scholars are content to say that this latter activity is an aspect of Jesus’ postresurrection activity and is not directly linked to the ascension. W. J. Dalton and P. J. Achtemeier, with the aid of Jewish apocalyptic reflection, make their cases for the “preaching to spirits in prison” as proclaiming victory or confirming condemnation to fallen angels, the sons of God (Genesis 6:1–6) now in bondage in one of the heavens Jesus passes through on his ascent to the Father’s presence (2 Enoch 7:1–3; 18:3–6; Testament of Levi 3:2; 1 Enoch 12:4–6; 13:3; 14:3–6; 16:3) ... Although Jewish angelology is far more systematic and imaginative following the exile, several precedents for angel typology suggest themselves in the Old Testament: Isaiah 14:5–23, a taunt against “the king of Babylon”; Isaiah 24:21–22, a symbolic representation of Yahweh’s judgment; and Ezekiel 28:1–19, a prophetic funeral dirge against the “king of Tyre.” With the angels these figures share a common fate: each is stripped of an exalted rank. While the idea of “imprisoned spirits” is unrefined in the Old Testament and pronounced in Jewish apocalyptic, Jude appears to combine typological treatment of the OT with conventional notions of angelology. Apocalyptic mythology frequently exhibits a conspicuous pattern: war erupts in heaven (depicted in astral terms), followed by a spilling over of this rebellion to earth, resulting in ultimate vindication and punishment by the king of heaven ..."
Martin, Ralph P. Dictionary of the Later New Testament & Its Developments (p. 205, 1211) InterVarsity Press, 1997