ADHESIVE COMPOSITION, ADHESIVE TAPE, AND METHOD FOR PROCESSING ELECTRONIC COMPONENT

Abstract

The present invention aims to provide an adhesive composition that is easily separable by irradiation with light even after high-temperature processing at 300° C. or higher with an adherend fixed thereon, an adhesive tape including an adhesive layer formed of the adhesive composition, and a method for processing an electronic component. The present invention is an adhesive composition including: a reactive resin having an imide backbone and containing a double bond-containing functional group in a side chain or at an end; and a silicone compound or a fluorine compound.

Claims

1. An adhesive composition comprising: a reactive resin having an imide backbone and containing a double bond-containing functional group in a side chain or at an end; and a silicone or fluorine compound.

2. The adhesive composition according to claim 1, wherein the silicone or fluorine compound contains a functional group capable of crosslinking with the reactive resin.

3. The adhesive composition according to claim 1, wherein the double bond-containing functional group is an optionally substituted maleimide group, an optionally substituted citraconimide group, an optionally substituted vinyl ether group, an optionally substituted allyl group, or an optionally substituted (meth)acrylic group.

4. The adhesive composition according to claim 1, wherein the double bond-containing functional group is in a side chain of the reactive resin.

5. The adhesive composition according to claim 1, wherein the reactive resin has a double bond-containing functional group equivalent (weight average molecular weight/number of double bond-containing functional groups) of 4,000 or less.

6. The adhesive composition according to claim 1, wherein the reactive resin has a weight average molecular weight of 5,000 or more.

7. The adhesive composition according to claim 1, wherein the reactive resin is a reactive resin (1) comprising 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: ##STR00015## where s≥1, 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, wherein at least one selected from the group consisting of X.sup.1, X.sup.2, and X.sup.3 represents a double bond-containing functional group.

8. The adhesive composition according to claim 7, wherein, in the formulas (1a) to (1c), P.sup.1, P.sup.2, and P.sup.3 each independently represent a C5-C50 aromatic group; Q.sup.1 represents a substituted or unsubstituted linear, branched, or cyclic C2-C100 aliphatic group; Q.sup.2 represents a substituted or unsubstituted C5-C50 aromatic structure-containing group; and R represents a substituted or unsubstituted branched C2-C100 aliphatic or aromatic group.

9. The adhesive composition according to claim 7, wherein, in the formula (1c), X.sup.3 represents a double bond-containing functional group.

10. The adhesive composition according to claim 7, wherein, in the formula (1c), R represents an aromatic ester group or aromatic ether group-containing aromatic group wherein the aromatic ester group or the aromatic ether group binds to X.sup.3.

11. The adhesive composition according to claim 7, wherein Q.sup.1 in the formula (1a) represents a dimer diamine-derived aliphatic group, and the dimer diamine-derived aliphatic group 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): ##STR00016## where R.sup.1 to R.sup.8 and R.sup.13 to R.sup.20 each independently represent a linear or branched hydrocarbon group.

12. The adhesive composition according to claim 2, wherein the silicone compound containing a functional group capable of crosslinking with the reactive resin is a silicone compound having a siloxane backbone and containing a double bond-containing functional group in a side chain or at an end, and the silicone compound having a siloxane backbone and containing a double bond-containing functional group in a side chain or at an end contains at least one selected from the group consisting of a silicone compound represented by the following formula (I), a silicone compound represented by the following formula (II), and a silicone compound represented by the following formula (III): ##STR00017## where X and Y each independently represent an integer of 0 to 1,200 and R represents a double bond-containing functional group.

13. The adhesive composition according to claim 1, further comprising a polyfunctional monomer or polyfunctional oligomer containing two or more double bond-containing functional groups in a molecule and having a molecular weight of 5,000 or less.

14. The adhesive composition according to claim 1, further comprising a photopolymerization initiator.

15. The adhesive composition according to claim 1, further comprising a gas generating agent that generates gas by irradiation with light.

16. An adhesive tape comprising an adhesive layer comprising the adhesive composition according to claim 1.

17. A method for processing an electronic component, the method comprising; temporarily fixing an electronic component on the adhesive tape according to claim 16; irradiating the adhesive tape with light; heat processing the electronic component; and separating the adhesive tape from the electronic component.

Description

DESCRIPTION OF EMBODIMENTS

[0087] Embodiments of the present invention are more specifically described in the following with reference to, but not limited to, examples.

(Preparation of Reactive Resin)

(1) Preparation of Reactive Resin 1

[0088] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 56 g (0.1 mol) of dimer diamine (Priamine 1075, available from Croda) and 19.1 g (0.09 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of amine-terminated diimide. After cooling to room temperature or lower, the reaction product was blended with 12.8 g (0.13 mol) of maleic anhydride and then with 5 g (0.05 mol) of methanesulfonic anhydride. The mixture was further refluxed for 12 hours and then cooled to room temperature. To the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by removal of the solvent in vacuum. Thus, an amber wax-like reactive resin 1 having an imide backbone and containing a maleimide group at both ends, represented by the following formula (1-1) was obtained.

[0089] The weight average molecular weight of the obtained reactive resin 1 was 5,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00004##

(2) Preparation of Reactive Resin 2

[0090] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 28 g (0.05 mol) of dimer diamine (Priamine 1075, available from Croda), 4.5 g (0.05 mol) of 1,3-diamino-2-propanol, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of hydroxy group-containing polyimide. After cooling to room temperature, the reaction mixture was blended with 10.5 g (0.05 mol) of maleimidehexanoic acid (available from Tokyo Chemical Industry Co., Ltd.) and further refluxed for 12 hours. After cooling to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by removal of the solvent in vacuum. Thus, an amber wax-like reactive resin 2 having an imide backbone and containing a maleimide group in a side chain, represented by the following formula (1-2) was obtained.

[0091] The weight average molecular weight of the obtained reactive resin 2 was 30,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00005##

(3) Preparation of Reactive Resin 3

[0092] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 28 g (0.05 mol) of diner diamine (Priamine 1075, available from Croda), 4.5 g (0.05 mol) of 1,3-diamino-2-propanol, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of hydroxy group-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 200 g of a large excess of butyl vinyl ether (available from Tokyo Chemical Industry Co., Ltd.) and 0.1 g of palladium acetate phenanthroline complex, followed by reflux at 60° C. for 14 hours. The excess butyl vinyl ether was removed using evaporator. After cooling to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by removal of the solvent. Thus, an amber wax-like reactive resin 3 having an imide backbone and containing a vinyl ether group in a side chain, represented by the following formula (1-3) was obtained.

[0093] The weight average molecular weight of the obtained reactive resin 3 was 30,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00006##

(4) Preparation of Reactive Resin 4

[0094] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 28 g (0.05 mol) of dimer diamine (Priamine 1075, available from Croda), 7.6 g (0.05 mol) of 3,5-diaminobenzoic acid, and 21.8 (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for synthesis of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, and then blended with 13.3 g (0.05 mol) of diallylmonoglycidyl isocyanurate (available from Shikoku Chemicals Corporation) and 3 g (0.3 mol) of triethylamine, followed by heating for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber wax-like reactive resin 4 having an imide backbone and containing a diallylisocyanurate group in a side chain, represented by the formula (1-4) was obtained.

[0095] The weight average molecular weight of the obtained reactive resin 4 was 35,000, as determined by gel permeation chromatography (GPO) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00007##

(5) Preparation of Reactive Resin 5

[0096] A 500-ml, round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 47.8 g (0.09 mol) of dimer diamine (Priamine 1075, available from Croda), 3.7 g (0.01 mol) of Bis-AP-AF, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by addition of 4.2 g (0.02 mol) of maleimide hexanoic acid and 3 g (0.3 mol) of trimethylamine. The mixture was then heated for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber wax-like reactive resin 5 having an imide backbone and containing maleimide groups in side chains, represented by the following formula (1-5) was obtained.

[0097] The weight average molecular weight of the obtained reactive resin 5 was 35,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00008##

(6) Preparation of Reactive Resin 6

[0098] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 31.9 g (0.06=1) of dimer diamine (Priamine 1075, available from Croda), 14.7 g (0.04 mol) of Bis-AP-AF, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by addition of 16.9 g (0.08 mol) of maleimide hexanoic acid and 3 g (0.3 mol) of trimethylamine. The mixture was then heated for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber wax-like reactive resin 6 having an imide backbone and containing maleimide groups in side chains, represented by the formula (1-5) was obtained.

[0099] The weight average molecular weight of the obtained reactive resin 6 was 35,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

(7) Preparation of Reactive Resin 7

[0100] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 42.5 g (0.08 mol) of dimer diamine (Priamine 1075, available from Croda), 7.3 g (0.02 mol) of Bis-AP-AF, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by addition of 8.6 g (0.04 mol) of glycidyloxybutyl vinyl ether (GO-BVE, available from Nippon Carbide Industries Co., Inc.), and 3 g (0.3 mol) of trimethylamine. The mixture was then heated for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber wax-like reactive resin 7 having an imide backbone and containing vinyl ether groups in side chains, represented by the following formula (1-6) was obtained.

[0101] The weight average molecular weight of the obtained reactive resin 7 was 35,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THE and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00009##

(8) Preparation of Reactive Resin 8

[0102] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 42.5 g (0.08 mol) of dimer diamine (Priamine 1075, available from Croda), 7.3 g (0.02 mol) of Bis-AP-AF, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by addition of 10.6 g (0.04 mol) of diaminomonogivcidyl isocyanurate (DA-MGIC, available from Shikoku Chemicals Corporation) and 3 g (0.3 mol) of trimethylamine. The mixture was then heated for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber wax-like reactive resin 8 having an imide backbone and containing allyl groups in side chains, represented by the following formula (1-7) was obtained.

[0103] The weight average molecular weight of the obtained reactive resin 8 was 35,000, as determined by gel permeation chromatography (GPO) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00010##

(9) Preparation of Reactive Resin 9

[0104] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of methanesulfonic anhydride were added, and the mixture was stirred to form salt. After stirring for 10 minutes, 21.2 g (0.04 mol) of dimer diamine (Priamine 1075, available from Croda), 12.3 g (0.03 mol) of 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 11.0 g (0.03 mol) of Bis-AP-AF, and 21.8 g (0.1 mol) of pyromellitic anhydride were added in this order. A Dean-Stark trap and a condenser were fitted to the flask and the mixture was refluxed for two hours for formation of carboxylic acid-containing polyimide. After cooling of the reaction mixture to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated impurities. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by addition of 15.9 g (0.06 mol) of diaminomonoglycidyl isocyanurate (DA-MGIC, available from Shikoku Chemicals Corporation) and 3 g (0.3 mol) of trimethylamine. The mixture was then heated for three hours. After cooling to room temperature and removal of the solvent in vacuum, an amber solid reactive resin 9 having an imide backbone and containing allyl groups in side chains, represented by the following formula (1-8) was obtained.

[0105] The weight average molecular weight of the obtained reactive resin 9 was 35,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THF and the column used was HR-MB-M (trade name, available from Waters Corporation).

##STR00011##

(Preparation of Acrylic Reactive Resin)

[0106] A reactor equipped with a thermometer, a stirrer, and a condenser was charged with 94 parts by weight of 2-ethylhexyl acrylate as a (meth)acrylic acid alkyl ester, 6 parts by weight of hydroxyethyl methacrylate as a functional group-containing monomer, 0.01 parts by weight of lauryl mercaptan, and 80 parts by weight of ethyl acetate. The reactor was heated to initiate reflux. To the reactor was subsequently added 0.01 parts by weight of 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane as a polymerization initiator to initiate polymerization under reflux. Then, 0.01 parts by weight of 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane was added one hour after and two hours after the start of the polymerization. Four hours after the start of the polymerization, 0.05 parts by weight of t-hexyl peroxypivalate was added to continue the polymerization reaction. Eight hours after the start of the polymerization, an ethyl acetate solution of a functional group-containing (meth)acrylic polymer having a solid content of 55% by weight and a weight average molecular weight of 500,000 was obtained.

[0107] To 100 parts by weight of the resin solid content of the obtained ethyl acetate solution containing a functional group-containing (meth)acrylic polymer was added 3.5 parts by weight of 2-isocyanatoethyl methacrylate as a functional group-containing unsaturated compound and reacted. Thus, an acrylic reactive resin was obtained.

[0108] The weight average molecular weight of the obtained acrylic reactive resin was 550,000, as determined by gel permeation chromatography (GPC) in which the eluent used was THE and the column used was HR-MB-M (trade name, available from Waters Corporation).

(Preparation of Polyfunctional Monomer)

(1) Preparation of Polyfunctional Monomer 1

[0109] A 500-mL round flask with a Teflon (®) stirrer placed therein was charged with 250 mL of toluene. To the flask was added 56 g (0.1 mol) of dimer diamine (Priamine 1075, available from Croda) and 19.6 g (0.2 mol) of maleic anhydride, followed by addition of 5 g of methanesulfonic anhydride. After reflux of the solution for 12 hours and subsequent cooling to room temperature, to the flask was added 300 mL of toluene, and the flask was allowed to stand still for removal of precipitated salt. The obtained solution was filtered through a glass frit funnel filled with silica gel, followed by removal of the solvent in vacuum. Thus, a brown liquid polyfunctional monomer 1 represented by the following formula (2-1) was obtained.

##STR00012##

(2) Purchase of Polyfunctional Monomer 2

[0110] SR-387 (available from ARKEMA, tris(2-acryloxyethyl)isocyanurate), trifunctional acrylate represented by the following formula (2-2), was purchased and used as a polyfunctional monomer 2.

##STR00013##

(Preparation of Silicone Bismaleimide)

[0111] A 300-mL round flask with a Teflon (®) stirrer placed therein was charged with 100 mL of toluene, followed by addition of 10.5 g (0.05 mol) of maleimide hexanoic acid (available from Tokyo Chemical Industry Co., Ltd., reagent), 25 g (0.025 mol) of X-21-5841 (available from Shin-Etsu Chemical Co., Ltd.) which is a silicone resin containing a hydroxy group at both ends, and 1 g (mol) of p-toluenesulfonic acid monohydrate. Then, the mixture was stirred under heating at 100° C. for three hours. After cooling to room temperature, 5 g of triethylamine was added thereto. After stirring for one hour, the reaction product was washed with 100 g of water, followed by vaporization of the solvent. Thus, silicone bismaleimide represented by the following formula (3) (m=11, n=5) was obtained.

##STR00014##

Example 1

[0112] To 150 mL of toluene were added 100 parts by weight of the reactive resin 1, 0.3 parts by weight of bifunctional silicone acrylate (EBECRYL 350, available from Daicel-Allnex Ltd.) as a silicone compound, and 1 part by weight of IRGACURE 369 (available from BASF SE) as a photopolymerization initiator. Thus, a toluene solution of an adhesive composition was prepared.

[0113] A 25-μm-thick polyimide film (Kapton, available from Ube Industries, Ltd.) one surface of which was corona-treated was prepared. The obtained toluene solution of an adhesive composition was applied to the corona-treated surface of the polyimide film to a dry thickness of 40 μm with a doctor knife, and the applied solution was dried by heating at 110° C. for one minute. The dried film was allowed to stand still at 40° C. for three days. Thus, an adhesive tape was obtained.

Examples 2 to 20, Comparative Examples 1 to 3

[0114] Adhesive compositions and adhesive tapes were obtained as in Example 1, except that the types and amounts of the reactive resin, polyfunctional monomer, silicone or fluorine compound, and photopolymerization initiator were changed as shown in Tables 1 and 2.

[0115] In Example 8, the silicone compound used was hexafunctional silicone acrylate (EBECRYL1360, available from Daicel-Allnex Ltd.).

[0116] In Example 9 and Comparative Example 1, the fluorine compound used was a photoreactive fluorine compound (MEGAFACE RS-56 available from DIC Corporation).

[0117] In Example 15, the gas generating agent used was 5-phenyl-1H tetrazole (available from Masuda Chemical Industries Co., Ltd.) and the photosensitizer used was 9,10-diglycidyl oxyanthracene (available from Kawasaki Kasei Chemicals ltd.).

(Evaluation) The adhesive tapes obtained in the examples and comparative examples were evaluated by the following methods.

[0118] Tables 1 and 2 show the results.

(1) Evaluation on Separability

[0119] The obtained adhesive tape was cut into a 1-inch-width piece, and heat laminated on a 1-mm-thick glass using a laminator at 100° C. After the lamination, the test piece was irradiated from the glass side with UV light at 365 nm at an intensity of 20 mW/cm.sup.2 for 150 seconds using a ultra-high pressure mercury lamp. After the UV irradiation, the test piece was heated from the glass side on a hot plate at 300° C. for 10 minutes.

[0120] The test piece was subjected to a 180° peeling test under the conditions of 25° C. and a tensile speed of 30 mm/sec for measurement of the adhesion strength (N/inch) after the lamination, the UV irradiation, and the heating at 300° C.

(2) Evaluation on Appearance of Adhesive Tape after Heating at 300° C.

[0121] In the evaluation on separability, the appearance of the adhesive tape after the heating at 300° C. was visually observed and evaluated based on the following criteria.

∘ (Good): No separation from the glass or foaming was observed.
Δ (Fair): Fine bubbles between the tape and the glass was observed.
x (Poor): The tape was partly separated from the glass.
(3) Evaluation on Separated Surface after Heating at 300° and Separation

[0122] In the evaluation on separability, the glass surface after heating at 300° C. and separation of the adhesive tape was visually observed and evaluated based on the following criteria.

∘ (Good): No adhesive deposits were observed.
Δ (Fair): No adhesive deposits were observed but the separated surface was clouded.
x (Poor): Adhesive deposits were observed.

TABLE-US-00001 TABLE 1 Example 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Adhesive composition Reactive resin Reactive resin 1 Functional 100 — — 80 80 80 80 80 80 80 — — — — 80 (parts by weight) (maleimide groups on both ends, weight group average molecular weight of 5,000) equivalent of 2,500 Reactive resin 2 Functional — — — — — — — — — — 80 80 — — — (maleimide group in side chain, weight group average molecular weight of 30,000) equivalent of 1,200 Reactive resin 3 Functional — 100 — — — — — — — — — — 80 — — (vinyl ether group in side chain, weight group average molecular weight of 30,000) equivalent of 1,100 Reactive resin 4 Functional — — 100 — — — — — — — — — — 80 — (allyl group in side chain, weight group average molecular weight of 35,000) equivalent of 1,300 Reactive resin 5 Functional — — — — — — — — — — — — — — — (maleimide group in side chain, weight group average molecular weight of 35,000) equivalent of 3,800 Reactive resin 6 Functional — — — — — — — — — — — — — — — (maleimide group in side chain, weight group average molecular weight of 35,000) equivalent of 1,700 Reactive resin 7 Functional — — — — — — — — — — — — — — — (vinyl ether group in side chain, weight group average molecular weight of 35,000) equivalent of 2,400 Reactive resin 8 Functional — — — — — — — — — — — — — — — (allyl group in side chain, weight group average molecular weight of 35,000) equivalent of 2,500 Reactive resin 9 Functional — — — — — — — — — — — — — — — (allyl group in side chain, weight group average molecular weight of 40,000) equivalent of 1,850 Acrylic reactive resin — — — — — — — — — — — — — — — — Polyfunctional Polyfunctional monomer 1 — — — 20 20 20 — 20 20 20 20 20 20 20 20 monomer (Bismaleimide monomer) Polyfunctional monomer 2 — — — — — — 20 — — — — — — — — (Trifunctional acrylate monomer) Silicone or fluorine EBECRYL350 0.3 0.3 0.3 0.3 5.0 10 0.3 — — — 0.3 — 0.3 — 0.3 compound (Silicone acrylate, bifunctional) EBECRYL1360 — — — — — — — 0.3 — — — — — — — (Silicone acrylate hexafunctional) MEGAFACE RS-56 — — — — — — — — 1 — — — — — — (Reactive flulorine compound) Silicone bismaleimide — — — — — — — — — 0.3 — 0.3 — 0.3 — Gas generating agent 5-Phenyl-1H tetrazole — — — — — — — — — — — — — — 10 Photopolymerization IRGACURE 369 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 initiator Photosensitizer 9,10-Dibutoxyanthracene — — — — — — — — — — — — — — 1 Evaluation Separability Adhesion strength after lamination (N/inch) 0.5 0.4 0.4 0.6 0.4 0.2 0.5 0.3 0.9 0.3 0.3 0 3 0.4 0.3 0.3 Adhesion strength after UV irradiation (N/inch) 0.3 0.3 0.2 0.2 0.2 0.2 0.4 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Adhesion strength after heating at 300° C. (N/inch) 0.4 0.3 0.3 0.2 0.2 0.2 0.4 0.2 0.3 0.2 0.2 0.1 0.3 0.1 0.2 Appearance of adhesive tape after heating at 300° C. ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Separated surface after heating at 300° C. and separation ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘

TABLE-US-00002 TABLE 2 Comparative Example Example 16 17 18 19 20 1 2 3 Adhesive composition Reactive resin Reactive resin 1 Functional — — — — — — 100 80 (parts by weight) (maleimide groups on both ends, group weight average molecular weight equivalent of 5,000) of 2,500 Reactive resin 2 Functional — — — — — — — — (maleimide group in side chain, group weight average molecular weight equivelant of 30,000) of 1,200 Reactive resin 3 Functional — — — — — — — — (vinyl ether group in side chain, group weight average molecular weight equivalent of 30,000) of 1,100 Reactive resin 4 Functional — — — — — — — — (allyl group in side chain, weight group average molecular weight equivalent of 35,000) of 1,300 Reactive resin 5 Functional 80 — — — — — — — (maleimide group in side chain, group weight average molecular weight equivalent of 35,000) of 3,800 Reactive resin 6 Functional — 80 — — — — — — (maleimide group in side chain, group weight average molecular weight equivalent of 35,000) of 1,700 Reactive resin 7 Functional — — 80 — — — — — (vinyl ether group in side chain, group weight average molecular weight equivalent of 35,000) of 2,400 Reactive resin 8 Functional — — — 80 — — — — (allyl group in side chain, group weight average molecular weight equivalent of 35,000) of 2,500 Reactive resin 9 Functional — — — — 80 — — — (allyl group in side chain, group weight average molecular weight equivalent of 40,000) of 1,850 Arcylic reactive resin — — — — — — 100 — — Polyfunctional Polyfunctional monomer 1 20 20 20 20 20 — — 20 monomer (Bismaleimide monomer) Polyfunctional monomer 2 — — — — — — — — (Trifunctional acrylate monomer) Silicone or fluorine EBECRYL350 0.3 0.3 0.3 0.3 0.3 — — — compound (Silicone acrylate, bifunctional) EBECRYL1360 — — — — — — — — (Silicone acrylate, hexafunctional) MEGAFACE RS-56 — — — — — 0.5 — — (Reactive flulorine compound) Silicone bismaleimide — — — — — — — — Gas generating agent 5-Phenyl-1H tetrazole — — — — — — — — Photopolymerization IRGACURE369 1 1 1 1 1 1 1 1 initiator Photosensitizer 9,10-Dibutoxyanthracene — — — — — — — — Evaluation Separability Adhesion strength after lamination (N/inch) 0.4 0.3 0.5 0.4 0.2 4.0 1.0 3.0 Adhesion strength after UV irradiation (N/inch) 0.3 0.2 0.4 0.2 0.4 0.2 3 0.6 Adhesion strength after heating at 300° C. 0.2 0.2 0.3 0.2 0.1 1.4 5 0.8 (N/inch) Appearcance of adhesive tape after heating at 300° C. ∘ ∘ ∘ ∘ ∘ x ∘ ∘ Separated surface after heating at 300° C. and separation ∘ ∘ ∘ ∘ ∘ x ∘ ∘

INDUSTRIAL APPLICABILITY

[0123] The present invention can provide an adhesive composition that is easily separable by irradiation with light even after high-temperature processing at 300° C. or higher with an adherend fixed thereon, an adhesive tape including an adhesive layer formed of the adhesive composition, and a method for processing an electronic component.