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.

Claims

1. A curable resin composition comprising: a maleimide group-containing reactive compound (1); and a resin (2) having an imide skeleton in a backbone repeating unit.

2. The curable resin composition according to claim 1, having a 5% weight loss temperature of 350° C. or higher.

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. 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. The curable resin composition according to claim 1, 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.

6. The curable resin composition according to claim 4, wherein the bismaleimide compound (1-I) 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): ##STR00008## wherein R.sup.1 to R.sup.8 and R.sup.13 to R.sup.20 each independently represent a linear or branched hydrocarbon group.

7. 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.sup.1 and X.sup.2: ##STR00009## wherein s>0, t≥0, and u≥0 are satisfied; P.sup.1, P.sup.2, and P.sup.3 each independently represent an aromatic group; Q.sup.1 represents a substituted or unsubstituted linear, branched, or cyclic aliphatic group; Q.sup.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.sup.1, X.sup.2, and X.sup.3 represents a maleimide group-containing group.

8. The curable resin composition according to claim 5, 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.sup.4 and X.sup.5: ##STR00010## wherein s>0 and t≥0 are satisfied; P.sup.4 and P.sup.5 each independently represent an aromatic group; Q.sup.3 represents a substituted or unsubstituted linear, branched, or cyclic aliphatic group; Q.sup.4 represents a substituted or unsubstituted aromatic structure-containing group; and X.sup.4 and X.sup.5 represents groups containing no maleimide group.

9. 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.

10. 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.

11. 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.

12. The curable resin composition according to claim 1, further comprising a polymerization initiator.

13. The curable resin composition according to claim 12, 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.

14. The curable resin composition according to claim 1, further comprising a silicone compound or a fluorine compound.

15. The curable resin composition according to claim 1, further comprising an inorganic filler.

16. The curable resin composition according to claim 15, wherein the inorganic filler has an average particle size of 5 nm or greater and 20 μm or less.

17. The curable resin composition according to claim 15, 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.

18. The curable resin composition according to claim 1, further comprising a gas generating agent.

19. The curable resin composition according to claim 18, 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.

20. A temporary fixing material comprising an adhesive layer containing the curable resin composition according to claim 1.

21. A temporary fixing material comprising: a first adhesive layer containing the curable resin composition according to claim 18; and a second adhesive layer.

22. The temporary fixing material according to claim 21, wherein the first adhesive layer has a gel fraction of 50% by weight or more after being cured.

23. The temporary fixing material according to claim 21, further comprising a substrate, wherein the first adhesive layer and the second adhesive layer are stacked on one surface and an opposite surface of the substrate, respectively.

24. The temporary fixing material according to claim 20, having an adhesion to glass at 25° C. of 1.5 N/inch or less after being cured and heated at 300° C. for 10 minutes.

25. A method for producing an electronic component, comprising: a temporary fixing step of temporarily fixing an electronic component to the temporary fixing material according to claim 20; a curing step of curing the adhesive layer of the temporary fixing material; a heat treatment step of heat-treating the electronic component; and a separation step of separating the electronic component from the temporary fixing material.

26. A method for producing an electronic component using the temporary fixing material according to claim 21, comprising: a support bonding step of bonding the first adhesive layer of the temporary fixing material and a support; an adherend bonding step of bonding the second adhesive layer of the temporary fixing material and an electronic component; a curing step of curing the first adhesive layer and the second adhesive layer; a heat treatment step of heat-treating the electronic component; a gas generation step of generating gas from the first adhesive layer; and a separation step of separating the support and the temporary fixing material from each other.

Description

EXAMPLE 1

(1) Production of Temporary Fixing Material

[0155] To 150 mL of toluene were added 70 parts by weight of the compound (1-II) containing a maleimide group and having an imide skeleton in a backbone repeating unit and 30 parts by weight of the resin (2-I) containing no maleimide group and having an imide skeleton in a backbone repeating unit. Further, 5 parts by weight of bifunctional silicone acrylate (produced by Daicel-Allnex Ltd., EBECRYL 350) as a silicone compound and 2 parts by weight of Irgacure 819 (produced by BASF) as a photopolymerization initiator were added, whereby a toluene solution of a curable resin composition was prepared.

[0156] A 50-μm-thick PET film one surface of which was release-treated was provided. The obtained toluene solution of a curable resin composition was applied with a doctor knife to the release-treated surface to a dry film thickness of 40 μm, and the applied solution was dried by heating at 110° C. for five minutes. The dried film was allowed to stand still at 40° C. for three days. Thus, a temporary fixing material including an adhesive layer was obtained.

(2) Measurement of 5% Weight Loss Temperature

[0157] The adhesive layer of the obtained temporary fixing material was cured and then weighed into an aluminum pan. The aluminum pan was set in the device.

[0158] The measurement sample was heated from 25° C. to 500° C. at a heating rate of 10° C./min in a nitrogen atmosphere using a thermogravimetry device (STA7200, produced by Hitachi High-Tech Science Corporation), and the temperature at which a 5% weight loss occurred was measured. The adhesive layer was cured by irradiation with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds, or by heating in an oven at 150° C. for 10 minutes instead of UV irradiation.

(3) Measurement of Gel Fraction After Curing

[0159] The adhesive layer of each obtained temporary fixing material was irradiated with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using an ultra-high pressure mercury lamp. The gel fraction was then measured by the following method.

[0160] The temporary fixing material was cut into a flat rectangular specimen having a size of 50 mm×100 mm. The specimen was immersed in toluene at 23° C. for 24 hours, then taken out of the toluene, and dried at 110° C. for one hour.

[0161] The weight of the dried specimen was measured, and the gel fraction was calculated using the following equation (1). No release film to protect the adhesive layer was stacked on the specimen.

Gel fraction (% by weight)=100×(W.sub.2−W.sub.0)/(W.sub.1−W.sub.2)   (1)

(W.sub.0: the weight of the substrate, W.sub.1: the weight of the specimen before immersion, W.sub.2: the weight of the specimen after immersion and drying)

[0162] In Example 18 described later, the first adhesive layer of the obtained temporary fixing material was irradiated with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds to cure the first and second adhesive layers. The adhesive layers were then each weighed out and used as specimens. In Example 19 described later, the first and second adhesive layers were cured by heating in an oven at 150° C. for 10 minutes instead of UV irradiation. The adhesive layers were then each weighed out and used as specimens. As these specimens included no substrate, W.sub.0 was 0.

EXAMPLES 2 TO 11 AND COMPARATIVE EXAMPLES 1 TO 4

[0163] A curable resin composition and a temporary fixing material were obtained as in Example 1 except that the composition of the curable resin composition was changed as shown in Table 1. The materials used were as follows. [0164] Fluorine compound (photoreactive fluorine compound, produced by DIC Corporation, MEGAFACE RS-56) [0165] Gas generating agent (5,5′-Bi-1H-tetrazole disodium salt (BHT-2Na))

EXAMPLES 12 TO 17

[0166] A curable resin composition and a temporary fixing material were obtained as in Example 1 except that the composition of the curable resin composition was changed as shown in Table 2. The materials used were as follows. [0167] Inorganic filler (silica particles, produced by Tokuyama Corporation, MT-10, average particle size 15 nm) [0168] Inorganic filler (silica particles, produced by Tatsumori Ltd., 5×, average particle size 1 μm)

EXAMPLE 18

(1) Formation of First Adhesive Layer (Gas Generating Agent-Containing Curable Adhesive Layer)

[0169] To 300 mL of toluene were added 100 parts by weight of the reactive resins shown in Table 3, 30 parts by weight of 5,5′-Bi-1H-tetrazole disodium salt (BHT-2Na) as a gas generating agent, 5 parts by weight of EBECRYL 350 as a silicone compound, and 3 parts by weight of Irgacure 369 (produced by BASF) as a photopolymerization initiator. Thus, a toluene solution of a curable resin composition in which 5,5′-Bi-1H-tetrazole disodium salt (BHT-2Na) was dispersed was prepared.

[0170] A 50-μm-thick polyethylene terephthalate film having a release-treated surface was provided as a separator. The obtained toluene solution of a curable resin composition was applied with a doctor knife to the film to a dry film thickness of 50 μm. The applied solution was dried by heating for 10 minutes in an oven preheated to 110° C. Thus, a first adhesive layer (gas generating agent-containing curable adhesive layer) was obtained.

(2) Formation of Second Adhesive Layer

[0171] To 300 mL of toluene were added 100 parts by weight of the reactive resins shown in Table 3, 5 parts by weight of EBECRYL 350 as a silicone compound, and 3 parts by weight of Irgacure 369 (produced by BASF) as a photopolymerization initiator. Thus, a toluene solution of a curable resin composition was prepared.

[0172] A 50-μm-thick polyethylene terephthalate film having a release-treated surface was provided as a separator. The obtained toluene solution of a curable resin composition was applied with a doctor knife to the film to a dry film thickness of 50 μm. The applied solution was dried by heating for 10 minutes in an oven preheated to 110° C. Thus, a second adhesive layer was obtained.

(3) Production of Temporary Fixing Material

[0173] The adhesive layer surfaces of the first adhesive layer (gas generating agent-containing curable adhesive layer) and the second adhesive layer were laminated, whereby a temporary fixing material in which both surfaces were covered with separators were obtained.

EXAMPLE 19

[0174] A curable resin composition and a temporary fixing material were obtained as in Example 1 except that the composition of the curable resin composition was changed as shown in Table 3 and a substrate was used as described below.

[0175] Specifically, in the formation of the second adhesive layer, a 25-μm-thick polyimide film (produced by Ube Industries, Ltd., Kapton film) one surface of which was corona-treated was provided, and the obtained toluene solution of a curable resin composition was applied with a doctor knife to the corona-treated surface to a dry film thickness of 50 μm. The applied solution was dried by heating for 10 minutes in an oven preheated to 110° C. After drying, a 50-μm-thick polyethylene terephthalate film having a release-treated surface, provided as a separator, was laminated on the adhesive layer surface opposite from the Kapton film. Thus, a second adhesive layer was obtained. The polymerization initiator used was PERBUTYL 0 produced by NOF Corporation.

<Evaluation>

[0176] The temporary fixing materials obtained in the examples and the comparative examples were evaluated by the following methods. Tables 1 to 3 show the results.

(1) Evaluation of Voids and Partial Detachment

[0177] Each obtained temporary fixing material was cut into a width of 1 inch and then heat-laminated onto a glass plate (produced by Matsunami Glass Ind., Ltd., Large white glass slide with polished edges No. 2) using a heat laminator (Leon13DX) at 100° C. with the speed set at 3 on the scale. In Examples 18 and 19, the second adhesive layer side was heat-laminated onto the glass plate.

[0178] After lamination, the temporary fixing material was irradiated from the glass side with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using an ultra-high pressure mercury lamp. In Example 19, the first and second adhesive layers were cured by heating in an oven at 150° C. for 10 minutes instead of UV irradiation. After curing, the release PET film of the temporary fixing material was removed, followed by heating from the glass side on a hot plate at 300° C. for 10 minutes.

[0179] The appearance of the temporary fixing material after being cured and heated at 300° C. was visually observed and evaluated in accordance with the following criteria. [0180] ○ (Good): No void or partial detachment was observed between the temporary fixing material and the glass plate. [0181] x (Poor): A fine void was observed between the temporary fixing material and the glass plate, or partial detachment was observed in some portion(s) between the temporary fixing material and the glass plate.

(2) Evaluation of Separability After Curing and Heating at 300° C. for 10 Minutes

[0182] Each obtained temporary fixing material was cut into a width of 1 inch and then heat-laminated onto a wafer having a photosensitive polyimide film using a laminator at 100° C. In Examples 18 and 19, the second adhesive layer side was heat-laminated onto the wafer.

[0183] After lamination, the temporary fixing material was irradiated from the temporary fixing material side with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using an ultra-high pressure mercury lamp. In Example 19, the first and second adhesive layers were cured by heating in an oven at 150° C. for 10 minutes instead of UV irradiation. After curing, the release PET film of the temporary fixing material was removed, and the side having the wafer having a photosensitive polyimide film was heated on a hot plate at 300° C. for 10 minutes.

[0184] The temporary fixing material after being cured and heated at 300° C. was subjected to a 180° peel test under the conditions of 25° C. and a tensile speed of 300 mm/min. A surface of the wafer having a photosensitive polyimide film after separation of the temporary fixing material was observed and evaluated in accordance with the following criteria. [0185] ○ (Good): No adhesive deposits were observed. [0186] x (Poor): No adhesive deposits were observed but the separated surface was clouded. [0187] xx (Very poor): Adhesive deposits were observed.

(3) Measurement of Adhesion to Glass at 25° C. After Curing and Heating at 300° C. for 10 Minutes

[0188] Each obtained temporary fixing material was cut into a width of 1 inch and then heat-laminated onto a 1-mm-thick glass (produced by Matsunami Glass Ind., Ltd., Large white glass slide with polished edges No. 2) using a laminator (produced by Lami Corporation Inc., Leon13DX, speed 5 on the scale) at 100° C. After lamination, the temporary fixing material was irradiated from the glass side with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using an ultra-high pressure mercury lamp. In Example 19, the first and second adhesive layers were cured by heating in an oven at 150° C. for 10 minutes instead of UV irradiation. After curing, the release PET film of the temporary fixing material was removed, followed by heating from the glass side on a hot plate at 300° C. for 10 minutes.

[0189] The temporary fixing material after being cured, heated at 300° C. for 10 minutes, and left to cool was subjected to a 180° peel test under the conditions of 25° C. and a tensile speed of 300 mm/min.

[0190] In Examples 18 and 19, the measurement was performed on the surface of the first adhesive layer and the surface of the second adhesive layer separately. For the adhesion of the first adhesive layer to glass, the temporary fixing material after being heated at 300° C. for 10 minutes and left to cool was irradiated from the glass side with UV light at 254 nm at an intensity of 20 mW/cm.sup.2 for 180 seconds using a high pressure mercury lamp so that gas was generated. The 180° peel test was then performed under the conditions of 25° C. and a tensile speed of 300 mm/min.

[0191] The adhesion was unmeasurable in Comparative Examples 1, 2, and 4 because voids or partial detachment occurred between the temporary fixing material and the glass plate after heating at 300° C. for 10 minutes. The adhesion could not be measured in Comparative Example 3 because the temporary fixing material was firmly adhered to the glass plate after heating at 300° C. for 10 minutes.

(4) Evaluation of Detachment and Separability After Curing and Heating at 300° C. for 20 Minutes

[0192] The temporary fixing materials obtained in Examples 2 to 4 and 12 to 17 were further evaluated as follows.

[0193] Each obtained temporary fixing material was cut into 5 a width of 1 inch and then heat-laminated onto a 1-mm-thick glass using a heat laminator (Leon13DX) at 100° C. with the speed set at 3 on the scale. After lamination, the temporary fixing material was irradiated from the glass side with UV light at 405 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using an ultra-high pressure mercury lamp.

[0194] After curing, the release PET film was removed, followed by heating from the glass side on a hot plate at 300° C. for 20 minutes. This test was performed five times.

[0195] The appearance of the temporary fixing material after being cured and heated at 300° C. for 20 minutes was visually observed and evaluated in accordance with the following criteria. [0196] Detachment observed: No detachment was observed between the temporary fixing material and the glass in any of the five tests. [0197] No detachment observed: Partial detachment was observed in some portion(s) between the temporary fixing material and the glass plate in one or more of the five tests.

[0198] The temporary fixing material after being cured and heated at 300° C. for 20 minutes was subjected to a 180° peel test under the conditions of 25° C. and a tensile speed of 300 mm/min. This test was performed five times. The peelability of the temporary fixing material was evaluated in accordance with the following criteria. The temporary fixing materials in which partial detachment occurred (“Detachment observed”) in the above detachment test were not evaluated. [0199] ○○ (Excellent): Separable in all the five tests. [0200] ○ (Good): Separable in one to four tests. [0201] x (Poor): Not separable in all the five tests.

TABLE-US-00001 TABLE 1 Example 1 2 3 4 5 6 7 8 Curable resin Maleimide group- Bismaleimide — 30 — 25 20 — — — composition containing reactive compound (1-I) (parts by weight) compound (1) Compound (1-II) 70 — 30 25 — 80 70 70 containing maleimide group and having imide skeleton in backbone repeating unit Resin (2) having Resin (2-I) 30 70 70 50 80 20 30 30 imide skeleton in containing no backbone repeating maleimide group unit and having imide skeleton in backbone repeating unit Other reactive resin (acrylic reactive resin) — — — — — — — — Silicone compound EBECRYL 350  5  5  5  5  5  5  1 — Fluorine compound MEGAFACE — — — — — — —  5 Gas generating agent BHT-2Na — — — — — — — — Photopolymerization Irgacure 819  2  2  2  2  2  2  2  2 initiator Physical 5% Weight loss temperature (° C.) 422  422  426  420  423  430  425  423  properties Gel fraction after curing (% by weight) 87 82 80 85 81 88 86 86 Evaluation Voids/partial detachment ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Separability after curing and ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ heating at 300° C. for 10 minutes Adhesion to glass at 25° C. after   0.1   0.2   0.2   0.2   0.2   0.1   0.3   0.1 curing and heating at 300° C. for 10 minutes (N/inch) Example Comparative Example 9 10 11 1 2 3 4 Curable resin Maleimide group- Bismaleimide — — 30 — 100 — — composition containing reactive compound (1-I) (parts by weight) compound (1) Compound (1-II) 70 70 — 100 — — 70 containing maleimide group and having imide skeleton in backbone repeating unit Resin (2) having Resin (2-I) 30 30 70 — — 100  — imide skeleton in containing no backbone repeating maleimide group unit and having imide skeleton in backbone repeating unit Other reactive resin (acrylic reactive resin) — — — — — — 30 Silicone compound EBECRYL 350  5  5  5  5  5 5  5 Fluorine compound MEGAFACE — — — — — — — Gas generating agent BHT-2Na  5 50 30 — — — — Photopolymerization Irgacure 819  2  2  2  2  2 2  2 initiator Physical 5% Weight loss temperature (° C.) 423  424  421  425 411 426  393  properties Gel fraction after curing (% by weight) 85 84 82  85  84 0 90 Evaluation Voids/partial detachment ∘ ∘ ∘ x x ∘ x Separability after curing and ∘ ∘ ∘ ∘ ∘ x xx heating at 300° C. for 10 minutes Adhesion to glass at 25° C. after   0.2   0.2   0.1 Not Not Firmly Not curing and heating at 300° C. for measurable measurable adhered measurable 10 minutes (N/inch)

TABLE-US-00002 TABLE 2 Example 2 3 4 12 13 Curable resin Maleimide group- Bismaleimide 30 — 25 30 30 composition containing reactive compound (1-I) (parts by weight) compound (1) Compound (1-II) — 30 25 — — containing maleimide group and having imide skeleton in backbone repeating unit Resin (2) having Resin (2-I) 70 70 50 70 70 imide skeleton in containing no backbone repeating maleimide group unit and having imide skeleton in backbone repeating unit Other reactive resin (acrylic reactive resin) — — — — — Silicone compound EBECRYL 350  5  5  5  5  5 Fluorine compound MEGAFACE — — — — — Inorganic filler MT-10 (15 nm) — — —  1  5 5X (1 μm) — — — — — Photopolymerization Irgacure 819  2  2  2  2  2 initiator Physical 5% Weight loss temperature (° C.) 422  426  420  422  428  properties Gel fraction after curing (% by weight) 82 80 85 82 82 Evaluation Voids/partial detachment ∘ ∘ ∘ ∘ ∘ Separability after curing and ∘ ∘ ∘ ∘ ∘ heating at 300° C. for 10 minutes Adhesion to glass at 25° C. after   0.2   0.2   0.2   0.2   0.3 curing and heating at 300° C. for 10 minutes (N/inch) After curing and Detachment Detachment Detachment Detachment No No heating at 300° C. after heating observed observed observed detachment detachment for 20 minutes observed observed Separability — — — ∘ ∘ Example 14 15 16 17 Curable resin Maleimide group- Bismaleimide 30 30 25 composition containing reactive compound (1-I) (parts by weight) compound (1) Compound (1-II) — 30 — 25 containing maleimide group and having imide skeleton in backbone repeating unit Resin (2) having Resin (2-I) 70 70 70 50 imide skeleton in containing no backbone repeating maleimide group unit and having imide skeleton in backbone repeating unit Other reactive resin (acrylic reactive resin) — — — — Silicone compound EBECRYL 350  5 —  5  5 Fluorine compound MEGAFACE —  5 — Inorganic filler MT-10 (15 nm) 15  1 —  5 5X (1 μm) — —  5 — Photopolymerization Irgacure 819  2  2  2  2 initiator Physical 5% Weight loss temperature (° C.) 432  435  428  422  properties Gel fraction after curing (% by weight) 81 80 82 85 Evaluation Voids/partial detachment ∘ ∘ ∘ ∘ Separability after curing and ∘ ∘ ∘ ∘ heating at 300° C. for 10 minutes Adhesion to glass at 25° C. after   0.6   0.2   0.5   0.2 curing and heating at 300° C. for 10 minutes (N/inch) After curing and Detachment No No No No heating at 300° C. after heating detachment detachment detachment detachment for 20 minutes observed observed observed observed Separability ∘ ∘ ∘ ∘

TABLE-US-00003 TABLE 3 Example 18 19 First Curable resin Maleimide Bis maleimide compound (1-1) 25 25 adhesive composition group-containing Compound (1-II) containing maleimide 25 25 layer (parts by reactive compound (1) group and having imide skeleton in weight) backbone repeating unit Resin (2) having imide Resin (2-I) containing no maleimide 50 50 skeleton in backbone group and having imide skeleton repeating unit in backbone repeating unit Gas generating agent BHT-2Na 30 30 Polymerization initiator Irgacure 369 3 — PERBUTYL O — 5 Thickness (μm) 50 50 Substrate None Kapton film Second Curable resin Maleimide Bismaleimide compound (1-I) 25 25 adhesive composition group-containing Compound (1-II) containing maleimide 25 25 layer (parts by reactive compound (1) group and having imide skeleton in weight) backbone repeating unit Resin (2) having imide Resin (2-I) containing no maleimide 50 50 skeleton in backbone group and having imide skeleton repeating unit in backbone repeating unit Polymerization initiator Irgacure 369 3 — PERBUTYL O — 5 Thickness (μm) 50 50 Physical First adhesive layer 5% Weight loss temperature (° C.) 424 423 properties Gel fraction after curing (% by weight) 85 88 Second adhesive layer 5% Weight loss temperature (° C.) 422 420 Gel fraction after curing (% by weight) 85 85 Eval- Voids/partial detachment ◯ ◯ uation Separability after curing and heating at 300° C. for 10 minutes ◯ ◯ Adhesion to glass at 25° C. after curing and First adhesive layer 0.05 0.1 heating at 300° C. for 10 minutes (N/inch) Second adhesive layer 0.7 0.7

INDUSTRIAL APPLICABILITY

[0202] The present invention can 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 can also 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.