1 Enoch 22:11
9 And he answered me and said unto me: 'These three have been made that the spirits of the dead might be separated. And such a division has been make (for) the spirits of the righteous, in which there is the bright spring of 10 water. And such 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 set apart in this great pain till the great day of judgement and punishment and torment of those who curse for ever and retribution for their spirits. There 12 He shall bind them for ever. And such a division has been made for the spirits of those who make their suit, who make disclosures concerning their destruction, when they were slain in the days
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 v. 7 to the fact that the angels’ sin was sexual intercourse with mortal women. Dubarle (“Péché”) accepts the allusions to 1 Enoch in v. 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 v. 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