Underfill material, underfill film, and method for manufacturing semiconductor device using same
US-2020109292-A1 · Apr 9, 2020 · US
US12534559B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12534559-B2 |
| Application number | US-202017620999-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 26, 2020 |
| Priority date | Jun 28, 2019 |
| Publication date | Jan 27, 2026 |
| Grant date | Jan 27, 2026 |
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A resin composition containing a bismaleimide compound (A) containing a constituent unit represented by the following formula (1) and maleimide groups at both ends of the molecular chain, a radical polymerizable resin or compound (B) other than the bismaleimide compound (A), and a curing accelerator (C), wherein the radical polymerizable resin or compound (B) contains at least one selected from the group consisting of a citraconimide group, a vinyl group, a maleimide group, a (meth)acryloyl group and an allyl group.
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The invention claimed is: 1 . A resin composition comprising: a bismaleimide compound (A) containing a constituent unit represented by the following formula (1), and maleimide groups at both ends of the molecular chain; a radical polymerizable resin or compound (B) other than the bismaleimide compound (A); and a curing accelerator (C), wherein the radical polymerizable resin or compound (B) contains at least one selected from the group consisting of a citraconimide group, a vinyl group, a maleimide group, a (meth)acryloyl group and an allyl group: wherein Q 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms; Q 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms; each Q 3 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms; and each n 1 independently represents an integer of 1 to 10. 2 . The resin composition according to claim 1 , wherein the radical polymerizable resin or compound (B) contains a maleimide group. 3 . The resin composition according to claim 1 , wherein the radical polymerizable resin or compound (B) contains at least one selected from 2,2-bis[4-(4-maleimidophenoxy)phenyl}propane, a maleimide compound represented by the following formula (2), a maleimide compound represented by the following formula (3), a maleimide compound represented by the following formula (4), a maleimide compound represented by the following formula (5), a compound represented by the following formula (6), a compound represented by the following formula (7), a compound represented by the following formula (10), a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13): wherein each R 1 independently represents a hydrogen atom or a methyl group, and n 2 represents an integer of 1 to 10; wherein n 3 represents an integer of 1 to 30; wherein each R 2 independently represents a hydrogen atom, a methyl group, or an ethyl group; and each R 3 independently represents a hydrogen atom or a methyl group; wherein each R 4 independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group; each 1 independently represents an integer of 1 to 3; and n 4 represents an integer of 1 to 10; wherein R 5 and R 7 each independently represent a hydrocarbon group in which 8 or more atoms are linearly linked; each R 6 independently represents a substituted or unsubstituted cyclic hydrocarbon group optionally having a heteroatom in which 4 to 10 atoms constitute the ring; and n 5 represents an integer of 1 to 10; wherein each R 8 independently represents an alkylene group; each R 9 independently represents an alkylene group, a group represented by the following formula (8), a group represented by the formula “—SO 2 —”, a group represented by the formula “—CO—”, a group represented by the following formula (9), an oxygen atom, or a single bond; and n 6 represents an integer of 1 to 10; wherein Z is an alkylene group or a hydrocarbon group having 6 to 30 carbon atoms and having an aromatic ring; and n 7 represents an integer of 0 to 5; wherein R 21 represents at least one selected from a linear or branched alkylene group having 1 to 40 carbon atoms, a cyclic hydrocarbon group optionally having a heteroatom in which 3 to 20 atoms constitute the ring, an oxygen atom, a group represented by “—NH—”, a sulfur atom, and a group represented by the formula “—SO 2 —”; wherein n 8 represents an integer of 1 to 10; and m1 represents an integer of 8 to 40; wherein n° represents an integer of 1 to 10; and m2 represents an integer of 8 to 40; and wherein n 10 represents an integer of 1 to 10; and m3 represents an integer of 8 to 40. 4 . The resin composition according to claim 1 , wherein the curing accelerator (C) contains at least one selected from the group consisting of a thermal radical polymerization initiator (D) and an imidazole compound (E). 5 . The resin composition according to claim 4 , wherein the thermal radical polymerization initiator (D) has a 10 hour half-life period temperature of 100° C. or higher. 6 . The resin composition according to claim 4 , wherein the thermal radical polymerization initiator (D) contains an organic peroxide. 7 . The resin composition according to claim 4 , wherein the thermal radical polymerization initiator (D) has a peroxy ester, a peroxy ketal, a dialkyl peroxide, or a hydroperoxide skeleton. 8 . The resin composition according to claim 4 , wherein the thermal radical polymerization initiator (D) contains at least one selected from dicumyl peroxide, di(2-tert-butylperoxyisopropyl)benzene, 1,1,3,3-tetramethylbutyl hydroperoxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy) hexyne-3, and tert-butyl hydroperoxide. 9 . The resin composition according to claim 1 , wherein a content of the bismaleimide compound (A) is 1 part by mass to 99 parts by mass based on 100 parts by mass in total of the bismaleimide compound (A) and the radical polymerizable resin or compound (B). 10 . The resin composition according to claim 1 , wherein a content of the curing accelerator (C) is 0.05 parts by mass to 10 parts by mass based on 100 parts by mass in total of the bismaleimide compound (A) and the radical polymerizable resin or compound (B). 11 . The resin composition according to claim 1 , further comprising a thermosetting compound (F) other than the bismaleimide compound (A) and the radical polymerizable resin or compound (B). 12 . The resin composition according to claim 11 , wherein the thermosetting compound (F) has a molecular weight of 400 or more. 13 . The resin composition according to claim 11 , wherein the thermosetting compound (F) contains a benzoxazine compound. 14 . The resin composition according to claim 13 , wherein the benzoxazine compound contains at least one selected from a compound represented by the following formula (14), a compound represented by the following formula (15), a compound represented by the following formula (16) an
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Imides, e.g. cyclic imides · CPC title
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