1 Enoch 22:11
7 And he answered me saying: 'This is the spirit of Abel, whom his brother Cain killed, and he pleads against him until his seed is wiped from the face of the earth, and his descendants are destroyed among the seed of men.' 8 Then I asked about it, and about all the hollow places: 'Why is one separated from the other?' 9 And he answered me and said: 'These three have been made so that the spirits of the dead might be separated. And such a division has been made for the spirits of the righteous, which includes the bright spring of 10 water. And one has been made for sinners when they die and are buried in the earth and judgement has not been executed on them in their 11 lifetime. Here their spirits shall be kept in great pain until the great day of judgement and punishment and torment of those who are cursed forever, and retribution for their spirits. There
Jude 1:6
4 For certain men have secretly slipped in among you—men who long ago were marked out for the condemnation I am about to describe—ungodly men who have turned the grace of our God into a license for evil and who deny our only Master and Lord, Jesus Christ. 5 Now I desire to remind you (even though you have been fully informed of these facts once for all) that Jesus, having saved the people out of the land of Egypt, later destroyed those who did not believe. 6 You also know that the angels who did not keep within their proper domain but abandoned their own place of residence, he has kept in eternal chains in utter darkness, locked up for the judgment of the great Day. 7 So also Sodom and Gomorrah and the neighboring towns, since they indulged in sexual immorality and pursued unnatural desire in a way similar to these angels, are now displayed as an example by suffering the punishment of eternal fire. 8 Yet these men, as a result of their dreams, defile the flesh, reject authority, and insult the glorious ones.
Notes and References
"... Older exegetes understood Jude 6 to refer to the fall of Satan and his angels before the fall of Adam; but Jude’s dependence on 1 Enoch is clear from the close parallels in this verse and also from the allusion in verse 7 to the fact that the angels’ sin was sexual intercourse with mortal women. Dubarle (“Péché”) accepts the allusions to 1 Enoch in verse 6, but suggests that Jude is making primary reference, in terms of the myth of the fallen angels, to the spies (ἀγγέλους = messengers) in Numbers 13, who forsook their eminent position among the people and abandoned the land which God had promised them. But it is hard to see how Jude’s readers could have detected this supposedly primary layer of meaning, and again the allusion in verse 7 to the angels’ intercourse with women rules it out ... The precise phrase “great day of judgment” is unusual, compare with 1 Enoch 22:11; 84:4; Targum Neofiti Deuteronomy 32:34; more usual is “great day of the Lord” (Joel 2:11, 31 [= Acts 2:20]; Zephaniah 1:14; Malachi 4:5; 2 Enoch 18:6), compare Revelation 6:17 (“great day of their wrath”); 16:18 (“great day of God Almighty”); 1 Enoch 54:6 (“that great day”) ..."
Bauckham, Richard Word Biblical Commentary: Jude-2 Peter (pp. 38-39) Zondervan, 1983