US-12617944-B2 - Curable resin composition, temporary fixing material, and electronic component manufacturing method

Abstract

The present invention aims to provide a curable resin composition that can reduce the occurrence of voids and partial detachment between the composition and a support even in high-temperature processing at 300° C. or higher with an adherend fixed to the support with the composition, and is easily separable after the high-temperature processing. The present invention also aims to provide a temporary fixing material including an adhesive layer containing the curable resin composition and a method of producing an electronic component using the temporary fixing material. Provided is a curable resin composition containing: a maleimide group-containing reactive compound (1); and a resin (2) having an imide skeleton in a backbone repeating unit.

Inventors

• Toshio Takahashi
• Tokushige Shichiri
• Satoshi Hayashi
• Izumi DAIDO
• Fumika HOSHINO

Assignees

• SEKISUI CHEMICAL CO., LTD.

Dates

Publication Date

20260505

Application Date

20210922

Priority Date

20200923

Claims (20)

1. 1 . A curable resin composition comprising: a maleimide group-containing reactive compound (1); a resin (2) having an imide skeleton in a backbone repeating unit; and wherein the resin (2) having an imide skeleton in a backbone repeating unit is a resin (2-I) containing no maleimide group and having an imide skeleton in a backbone repeating unit.
2. 2 . The curable resin composition according to claim 1 , having a 5% weight loss temperature of 350° C. or higher.
3. 3 . The curable resin composition according to claim 1 , wherein at least one selected from the group consisting of the maleimide group-containing reactive compound (1) and the resin (2) having an imide skeleton in a backbone repeating unit contains an aliphatic group derived from a dimer diamine.
4. 4 . The curable resin composition according to claim 1 , wherein the maleimide group-containing reactive compound (1) is a bismaleimide compound (1-I) or a compound (1-II) containing a maleimide group and having an imide skeleton in a backbone repeating unit.
5. 5 . The curable resin composition according to claim 4 , wherein the bismaleimide compound (1-1) is a compound containing two maleimide groups and an aliphatic group derived from a dimer diamine, and the aliphatic group derived from a dimer diamine is at least one selected from the group consisting of a group represented by the following formula (4-1), a group represented by the following formula (4-2), a group represented by the following formula (4-3), and a group represented by the following formula (4-4): wherein R 1 to R 8 and R 13 to R 20 each independently represent a linear or branched hydrocarbon group.
6. 6 . The curable resin composition according to claim 4 , wherein the compound (1-II) containing a maleimide group and having an imide skeleton in a backbone repeating unit is a compound (1-ii) containing a structural unit represented by the following formula (1a), a structural unit represented by the following formula (1b), and a structural unit represented by the following formula (1c), and having ends represented by X 1 and X 2 : wherein s>0, t≥0, and u≥0 are satisfied; P 1 , P 2 , and P 3 each independently represent an aromatic group; Q 1 represents a substituted or unsubstituted linear, branched, or cyclic aliphatic group; Q 2 represents a substituted or unsubstituted aromatic structure-containing group, R represents a substituted or unsubstituted branched aliphatic or aromatic group; and at least one selected from the group consisting of X 1 , X 2 , and X 3 represents a maleimide group-containing group.
7. 7 . The curable resin composition according to claim 1 , wherein the resin (2-I) containing no maleimide group and having an imide skeleton in a backbone repeating unit is a resin (2-i) containing a structural unit represented by the following formula (1d) and a structural unit represented by the following formula (1e), and having ends represented by X 4 and X 5 : wherein s>0 and t≥0 are satisfied; P 4 and P 5 each independently represent an aromatic group; Q 3 represents a substituted or unsubstituted linear, branched, or cyclic aliphatic group; Q 4 represents a substituted or unsubstituted aromatic structure-containing group; and X 4 and X 5 represents groups containing no maleimide group.
8. 8 . The curable resin composition according to claim 1 , wherein the resin (2) having an imide skeleton in a backbone repeating unit has a weight average molecular weight (Mw) of 20,000 or greater.
9. 9 . The curable resin composition according to claim 1 , wherein the amount of the resin (2) having an imide skeleton in a backbone repeating unit is 20 parts by weight or greater and 80 parts by weight or less in 100 parts by weight of the total amount of the maleimide group-containing reactive compound (1) and the resin (2) having an imide skeleton in a backbone repeating unit.
10. 10 . The curable resin composition according to claim 1 , wherein the amount of the maleimide group-containing reactive compound (1) is 20 parts by weight or greater and 80 parts by weight or less in 100 parts by weight of the total amount of the maleimide group-containing reactive compound (1) and the resin (2) having an imide skeleton in a backbone repeating unit.
11. 11 . The curable resin composition according to claim 1 , further comprising a polymerization initiator.
12. 12 . The curable resin composition according to claim 11 , wherein the polymerization initiator is a photopolymerization initiator, and the photopolymerization initiator contains a photopolymerization initiator having a molar absorption coefficient at 405 nm of 1 or greater.
13. 13 . The curable resin composition according to claim 1 , further comprising a silicone compound or a fluorine compound.
14. 14 . The curable resin composition according to claim 1 , further comprising an inorganic filler.
15. 15 . The curable resin composition according to claim 14 , wherein the inorganic filler has an average particle size of 5 nm or greater and 20 μm or less.
16. 16 . The curable resin composition according to claim 14 , wherein the amount of the inorganic filler is 1 part by weight or greater and 20 parts by weight or less in 100 parts by weight of the total amount of the maleimide group-containing reactive compound (1) and the resin (2) having an imide skeleton in a backbone repeating unit.
17. 17 . The curable resin composition according to claim 1 , further comprising a gas generating agent.
18. 18 . The curable resin composition according to claim 17 , wherein the gas generating agent has a weight loss rate at 300° C. of 5% or less when heated from 30° C. to 300° C. at a heating rate of 10° C./min in a nitrogen atmosphere in thermogravimetry-differential thermal analysis (TG-DTA) measurement.
19. 19 . A temporary fixing material comprising an adhesive layer containing the curable resin composition according to claim 1 .
20. 20 . A temporary fixing material comprising: a first adhesive layer containing the curable resin composition according to claim 17 ; and a second adhesive layer.

Description

TECHNICAL FIELD The present invention relates to a curable resin composition that can reduce the occurrence of voids and partial detachment between the composition and a support even in high-temperature processing at 300° C. or higher with an adherend fixed to the support with the composition, and is easily separable after the high-temperature processing. The present invention also relates to a temporary fixing material including an adhesive layer containing the curable resin composition and a method for producing an electronic component using the temporary fixing material. BACKGROUND ART During the processing of electronic components such as semiconductors, electronic components are fixed to supports using adhesive compositions or protected by adhesive tapes attached thereto for easier handling or less breakage of the electronic components. In the case where a thick wafer cut out from a highly pure silicon single crystal is ground to a thin wafer having a predetermined thickness, for example, the thick wafer is attached to a support using an adhesive composition. Adhesive compositions and adhesive tapes thus used with electronic components are required to have high adhesiveness to firmly fix electronic components during the processing, as well as separability from the electronic components without causing damage to the electronic components after the processing (hereafter, also referred to as “high adhesion and easy separation”). As a means for achieving high adhesion and easy separation, Patent Literature 1, for example, discloses an adhesive sheet produced using an adhesive in which to a side chain or main chain of a polymer is bonded a polyfunctional monomer or oligomer containing a radiation polymerizable functional group. The polymer is cured by irradiation with UV as it has the radiation polymerizable functional group, which allows lowering of the adhesion by irradiation with UV upon separation of the adhesive sheet, enabling separation without adhesive deposits. CITATION LIST Patent Literature Patent Literature 1: JP H05-32946 A SUMMARY OF INVENTION Technical Problem Recent higher-performance electronic components are subjected to various types of processing. For example, in the process of forming a thin metal film on a surface of an electronic component by sputtering, the processing is performed at high temperature of around 300° C. to 350° C. to form a thin metal film having higher electroconductivity. However, high-temperature processing at 300° C. or higher performed on an electronic component protected using a conventional adhesive composition or adhesive tape may cause voids or partial detachment between the adhesive composition or tape and the support fixing the electronic component during the high-temperature processing, and may also cause a rise in adhesion, leading to insufficient lowering of the adhesion or the generation of adhesive deposits upon separation. Especially in recent years, polyimide resins, which are highly heat-resistant materials, have been used in many electronic components, and polyimide resin adherends have been fixed to inorganic material supports (e.g., glass supports) and subjected to various types of processing. When subjected to high-temperature processing at 300° C. or higher, polyimide resin adherends tend to suffer a greater rise in adhesion than inorganic material adherends. The adhesive composition or adhesive tape used in such a case to protect the polyimide adherend needs to reduce a rise in adhesion to the polyimide resin adherend, while also reducing the occurrence of voids and partial detachment between the composition or tape and the support. The present invention aims to provide a curable resin composition that can reduce the occurrence of voids and partial detachment between the composition and a support even in high-temperature processing at 300° C. or higher with an adherend fixed to the support with the composition, and is easily separable after the high-temperature processing. The present invention also aims to provide a temporary fixing material including an adhesive layer containing the curable resin composition and a method for producing an electronic component using the temporary fixing material. Solution to Problem The present invention relates to a curable resin composition containing a maleimide group-containing reactive compound (1) and a resin (2) having an imide skeleton in a backbone repeating unit. The present invention is described in detail below. The present inventors studied curable resin compositions containing a maleimide group-containing reactive compound (1) and a resin (2) having an imide skeleton in a backbone repeating unit. The present inventors have found out that such a curable resin composition can reduce the occurrence of voids and partial detachment between the composition and a support even in high-temperature processing at 300° C. or higher with an adherend, particularly a polyimide adherend, fixed to the support with