Jubilees 5:6
4 And He said that He would destroy man and all flesh upon the face of the earth which He had created. 5 But Noah found grace before the eyes of the Lord. 6 And against the angels whom He had sent upon the earth, He was exceedingly wroth, and He gave commandment to root them out of all their dominion, and He bade us to bind them in the depths of the earth, and behold they are bound in the midst of them, and are (kept) separate. 7 And against their sons went forth a command from before His face that they should be smitten with the sword, and be removed from under heaven.
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