Jubilees 5:6
4 He said that he would obliterate people and all animate beings that were on the surface of the earth which he had created. 5 He was pleased with Noah alone. 6 Against his angels whom he had sent to the earth he was angry enough to uproot them from all their (positions of) authority. He told us to tie them up in the depths of the earth; now they are tied within them and are alone. 7 Regarding their children there went out from his presence an order to strike them with the sword and to remove them from beneath the sky.
1 Peter 3:19
18 Because Christ also suffered once for sins, the just for the unjust, to bring you to God, by being put to death in the flesh but by being made alive in the spirit. 19 In it he went and preached to the spirits in prison, 20 after they were disobedient long ago when God patiently waited in the days of Noah as an ark was being constructed. In the ark a few, that is eight souls, were delivered through water.
Notes and References
"... The greatest theological puzzle in 1 Peter involves the interpretation of two enigmatic texts which refer to proclamations made to the “spirits” and the “dead.” “He was put to death in the flesh, but made alive in the spirit, in which also he went and made proclamation to the spirits in prison, who in former times did not obey, when God waited patiently in the days of Noah” (3:18–20). “For this is the reason the gospel was proclaimed even to the dead, so that, though they had been judged in the flesh as everyone is judged, they might live in the spirit as God does” (4:6). These two texts have commonly been interpreted in light of one another, with the assumption being that they refer to the same event. The most compelling explanation of each, however, allows for their separate interpretation (Reicke 1946; Dalton 1965). In 1 Peter 3:18–20 the reference to the days of Noah, the use of pneuma or “spirit” (the common way of referring to a supernatural being), the qualifier “disobedient,” and the mention of imprisonment, suggest that the disobedient “sons of God” of Genesis 6:1–4 are in view. An extensive body of Second Temple literature developed elaborate scenarios concerning these rebellious angels. Variously referred to as “spirits,” “sons of heaven,” “giants,” and “watchers,” these supernatural beings were judged in Noah's flood and were thought to be imprisoned until the time of their final judgment (1 Enoch 10:11–12; Jubilees 5:6). In this interpretation, Christ “proclaimed” judgment upon the sons of God after achieving his victory on the cross. ..."
Gregg, Brian Han "1 Peter" in Aune, David Edward, (ed.) The Blackwell Companion to the New Testament (p. 591) Wiley-Blackwell, 2010