ADHESIVE COMPOSITION, OPTICAL COMPONENT, ELECTRONIC COMPONENT, AND ELECTRONIC MODULE

Abstract

The present invention aims to provide an adhesive composition capable of suppressing shrinkage on curing and excellent in storage stability and depth curability, or an adhesive composition excellent in adhesion on photocuring, curability by heating at low temperature, and low shrinkability on curing. The present invention also aims to provide an optical component, an electronic component, and an electronic module each including the adhesive composition. Provided is an adhesive composition including: a polymerizable compound; a photopolymerization initiator; and a radical scavenger, the polymerizable compound including a (meth)acrylic compound and a vinyl group-containing cyclic amide compound, the vinyl group-containing cyclic amide compound being contained in an amount of 20 parts by weight or more and 150 parts by weight or less relative to 100 parts by weight of the (meth)acrylic compound, or an adhesive composition including: a polymerizable compound; a photopolymerization initiator; and a heat curing agent, the polymerizable compound including a radical polymerizable compound containing no epoxy group, an epoxy compound containing no radical polymerizable group, and a compound containing an epoxy group and a radical polymerizable group, the heat curing agent including a heat curing agent having a lowest value of a starting range temperature of 80° C. or lower.

Claims

1. An adhesive composition comprising: a polymerizable compound; a photopolymerization initiator; and a radical scavenger, the polymerizable compound comprising a (meth)acrylic compound and a vinyl group-containing cyclic amide compound, the vinyl group-containing cyclic amide compound being contained in an amount of 20 parts by weight or more and 150 parts by weight or less relative to 100 parts by weight of the (meth)acrylic compound.

2. The adhesive composition according to claim 1, wherein the polymerizable compound further contains a heat-curable compound.

3. The adhesive composition according to claim 1, wherein the polymerizable compound comprises a compound containing a photopolymerizable functional group and a thermopolymerizable functional group.

4. An adhesive composition comprising: a polymerizable compound; a photopolymerization initiator; and a heat curing agent, the polymerizable compound comprising a radical polymerizable compound containing no epoxy group, an epoxy compound containing no radical polymerizable group, and a compound containing an epoxy group and a radical polymerizable group, the heat curing agent comprising a heat curing agent having a lowest value of a starting range temperature of 80° C. or lower.

5. The adhesive composition according to claim 4, wherein the radical polymerizable compound containing no epoxy group comprises a compound containing one vinyl group in one molecule.

6. The adhesive composition according to claim 5, wherein the compound containing one vinyl group in one molecule comprises a vinyl group-containing cyclic amide compound.

7. The adhesive composition according to claim 6, wherein the vinyl group-containing cyclic amide compound is at least one of N-vinyl-2-pyrrolidone or N-vinyl-ε-caprolactam.

8. The adhesive composition according to claim 4, wherein compounds containing a radical polymerizable group are contained in a total amount of 45 parts by weight or more and 90 parts by weight or less in 100 parts by weight of the polymerizable compound.

9. The adhesive composition according to claim 4, wherein the heat curing agent having a lowest value of a starting range temperature of 80° C. or lower comprises an imidazole-based curing agent.

10. The adhesive composition according to claim 1, comprising a filler.

11. The adhesive composition according to claim 10, wherein the filler comprises silica having a methyl-treated surface.

12. The adhesive composition according to claim 10, wherein the filler is contained in an amount of 5 parts by weight or more and 50 parts by weight or less relative to 100 parts by weight of the polymerizable compound.

13. The adhesive composition according to claim 1, comprising a light-blocking agent.

14. The adhesive composition according to claim 1, having a thixotropic index of 3.0 or higher and 7.0 or lower.

15. The adhesive composition according to claim 1, which is for use in fixing a movable component.

16. An optical component comprising a cured product of the adhesive composition according to claim 1.

17. An electronic component comprising a cured product of the adhesive composition according to claim 1.

18. An electronic module comprising the optical component according to claim 16.

Description

DESCRIPTION OF EMBODIMENTS

[0161] The present invention is more specifically described with reference to, but not limited to, examples.

Examples 1 to 15, Comparative Examples 1 to 5

[0162] Materials were mixed according to the compounding ratios in Tables 1 to 3 using a mixer to prepare adhesive compositions of Examples 1 to 15 and Comparative Examples 1 to 5. The mixer used was ARE-310 (available from Thinky Corporation).

[0163] In Tables 1 to 3, “UVACURE 1561” is a mixture containing about 50% by weight of a partially acrylic-modified bisphenol A-type epoxy resin, about 25% by weight of bisphenol A-type epoxy acrylate, and about 25% by weight of a bisphenol A-type epoxy resin (about 75% by weight of acrylic compound content).

<Evaluation>

[0164] The following evaluations were performed on the adhesive compositions obtained in Examples 1 to 15 and Comparative Examples 1 to 5. Tables 1 to 3 show the results.

(Storage Stability)

[0165] The adhesive compositions obtained in Examples 1 to 15 and Comparative Examples 1 to 5 were each charged into a syringe and stored in a thermostatic chamber at 25° C. The viscosity was measured right after the production, after storage for 24 hours, after storage for 48 hours, and after storage for one week. The viscosity change rate was derived from (viscosity after storage for each prescribed time)/(viscosity right after the production).

[0166] The storage stability was evaluated based on the following criteria: the case where the viscosity change rate after storage for one week was less than 1.2 was rated as “00 (Excellent)”; the case where the viscosity change rate after storage for 48 hours was less than 1.2 and the viscosity change rate after storage for one week was 1.2 or more was rated as “o (Good)”; the case where the viscosity change rate after storage for 24 hours was less than 1.2 and the viscosity change rate after storage for 48 hours was 1.2 or more was rated as “A (Fair)”; and the case where the viscosity change rate after storage for 24 hours was 1.2 or more was rated as “x (Poor)”.

[0167] The viscosity of the adhesive composition was measured using an E-type viscometer (“DV-III” available from BROOK FIELD) at 25° C. and a rotation speed of 1.0 rpm.

(Depth Curability)

[0168] The adhesive compositions obtained in Examples 1 to 15 and Comparative Examples 1 to 5 were each charged into a black polycarbonate container with a hole having a diameter of 3 mm. To the hole, UV light (wavelength of 365 nm) was applied to a dose of 1,000 mJ/cm.sup.2. The curing depth from the surface of the adhesive composition was measured with a caliper.

[0169] The depth curability was evaluated based on the following criteria: the case where the curing depth was 2 mm or more was rated as “oo (Excellent)”; the case where the curing depth was 1 mm or more and less than 2 mm was rated as “o (Good)”; the case where the curing depth was 300 μm or more and less than 1 mm was rated as “Δ (Fair)”; and the case where the curing depth was less than 300 μm was rated as “x (Poor)”.

(Low Shrinkability on Curing)

[0170] The adhesive compositions obtained in Examples 1 to 15 and Comparative Examples 1 to 5 were each irradiated with UV light (wavelength of 365 nm) to a dose of 1,000 mJ/cm.sup.2, followed by heating at 80° C. for one hour. Thus, a cured product having a size of 15 mm in length, 15 mm in width, and 2 mm in thickness was obtained. Measurement of specific gravity was performed on the adhesive compositions before curing at 25° C. and the cured products of the adhesive compositions at 25° C. The curing shrinkage was calculated using the equation described above.

[0171] The low shrinkability on curing was evaluated based on the following criteria: the case where the curing shrinkage was not higher than 2.7% was rated as “oo (Excellent)”; the case where the curing shrinkage was higher than 2.7% and not higher than 3.0% was rated as “o (Good)”; the case where the curing shrinkage was higher than 3.0% and not higher than 5.0% was rated as “A (Fair)”; and the case where the curing shrinkage was higher than 5.0% was rated as “x (Poor)”.

TABLE-US-00001 TABLE 1 Example 1 2 3 4 5 6 7 8 9 10 11 Composition Polymerizable (Meth)acrylic 2-(((Butylamino)- 28.5 19.0 3.1 3.1 3.1 3.1 3.1 3.1 3.1 3.1 3.1 (parts by compound compound carbonyl)oxy) weight) ethyl (meth)acrylate (“H-ABEI” available from Osaka Organic Chemical Industry Ltd.) 2-Phenoxyethyl 4.5 3.0 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 acrylate (“Viscoat #192” available from Osaka Organic Chemical Industry Ltd) Isodecyl acrylate 7.5 5.0 1.3 1.3 1.3 1.3 1.3 1.3 1.3 1.3 1.3 (“IDAA” available from Osaka Organic Chemical Industry Ltd.) (3-Ethyloxetan-3-yl) 7.5 5.0 1.3 1.3 1.3 1.3 1.3 1.3 1.3 1.3 1.3 methyl acrylate (“OXE-10” available from Osaka Organic Chemical Industry Ltd.) N-acryloyl 1.5 1.0 4.9 4.9 4.9 4.9 4.9 4.9 4.9 4.9 4.9 morpholine (“ACMO” available from KJ Chemicals Corporation) Partially acrylic- — — 24.3 24.3 24.3 24.3 24.3 24.3 24.3 24.3 24.3 modified bisphenol A-type epoxy resin (“UVACURE 1561” available from Daicel-Allnex Ltd.) (Acrylic compound content: about 75 wt %) Vinyl group- N-vinyl-ϵ- 24.8 16.5 11.7 11.7 11.7 11.7 11.7 11.7 11.7 7.0 16.3 containing caprolactam cyclic amide (“NVC” compound available from Tokyo Chemical Industry Co., Ltd.) Heat curable Propylene — — 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 compound oxide-added bisphenol A-type epoxy resin (“EP-4003S” available from ADEKA) Bisphenol — — 19.4 19.4 19.4 19.4 19.4 19.4 19.0 19.0 19.0 F-type epoxy resin (“EXA- 830CRP” available from DIC) Photoradical Bis(2,4,6-trimethylbenzoyl)phenyl- 0.5 0.5 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 polymerization phosphine oxide (“Omnirad 819” initiator available from iGM resins) Radical heat curing 2-Methylimidazole — — 8.0 2.0 4.0 4.0 — 8.0 4.0 4.0 4.0 scavenger agent (“CUREZOL 2MZ-H” available from Shikoku Chemicals Corporation) Polyamine- — — — — — 4.0 15.0 — — — — based curing agent (ADEKA Hardener EH-5057PK” available from ADEKA) Polyvinyl butyral (“S-LEC — — 5.0 — — — — — — — — KS-1” available from Sekisui Chemical Co., Ltd.) Polycarbonate-based — 45.0 — — — — — — — — — urethane prepolymer Hydroquinone (available 0.5 — — — — — — — — — — from Tokyo Chemical Industry Co., Ltd.) Filler Molten silica (“SANSIL 24.8 — 14.9 24.2 22.9 19.9 12.9 19.9 24.3 29.0 19.7 SSP-07M” available from Tokuyama Corporation) Viscosity Fumed silica (“AEROSIL — 5.0 5.0 6.7 6.0 5.0 5.0 5.0 5.0 5.0 5.0 modifier RY200” available from Nippon Aerosil Co., Ltd.) Amount of vinyl group-containing cyclic amide compound 50 50 40 40 40 40 40 40 40 24 55 relative to 100 parts by weight of (meth)acrylic compound (parts by weight) Evaluation Storage stability ∘∘ ∘∘ ∘ ∘ ∘ Δ Δ ∘ ∘ ∘ ∘ Depth curability ∘ ∘ ∘∘ ∘∘ ∘∘ ∘ ∘∘ ∘ ∘∘ ∘∘ ∘∘ Low shrinkability on curing Δ ∘ ∘∘ ∘ ∘∘ ∘∘ ∘∘ ∘ ∘∘ ∘∘ ∘∘

TABLE-US-00002 TABLE 2 Example 12 13 14 15 Composition Polymerizable (Meth)acrylic 2-(((Butylamino)carbonyl)oxy) — — 8.5 2 (parts by weight) compound compound ethyl (meth)acrylate (“H-ABEI” available from Osaka Organic Chemical Industry Ltd.) 2-Phenoxyethyl acrylate — — 1.0 0.3 (“Viscoat #192” available from Osaka Organic Chemical Industry Ltd.) Isodecyl acrylate — — 2.0 0.8 (“IDAA” available from Osaka Organic Chemical Industry Ltd.) (3-Ethyloxetan-3-yl) methyl acrylate — — 2.0 0.5 (“OXE-10” available from Osaka Organic Chemical Industry Ltd.) N-acryloyl morpholine — — 5.0 1 (“ACMO” available from KJ Chemicals Corporation) Partially acrylic-modified bisphenol 13.5 10.0 8.0 — A-type epoxy resin (“UVACURE 1561” available from Daicel-Allnex Ltd.) (Acrylic compound content: about 75 wt %) Vinyl group- N-vinyl-ϵ-caprolactam 9.7 7.0 5.0 — containing cyclic (“NVC” available from Tokyo amide compound Chemical Industry Co., Ltd.) Heat curable Propylene oxide-added bisphenol 24.1 24.1 — 18.5 compound A-type epoxy resin (“EP-4003S” available from ADEKA) Bisphenol F-type epoxy resin 17.6 29.1 15.8 19.4 (“EXA-830CRP” available from DIC) Photoradical Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide — — 0.3 0.3 polymerization (“Omnirad 819“ available from iGM resins) initiator Radical heat curing agent 2-Methylimidazole — — 19.4 19.4 scavenger (“CUREZOL 2MZ-H” available from Shikoku Chemicals Corporation) Polyamine-based curing agent 0.2 0.2 0.2 0.6 (ADEKA Hardener EH-5057PK” available from ADEKA) Polyvinyl butyral (“S-LEC KS-1” available from 0.5 0.5 — 0.6 Sekisui Chemical Co., Ltd.) Polycarbonate-based urethane prepolymer 0.2 0.2 — — Hydroquinone (available from Tokyo Chemical 5.0 6.0 2.0 8 Industry Co., Ltd.) Filler Molten silica (“SANSIL SSP-07M” available 24.2 17.9 24.2 23.6 from Tokuyama Corporation) Viscosity Fumed silica (“AEROSIL RY200” available from 5.0 5.0 6.7 5 modifier Nippon Aerosil Co., Ltd.) Amount of vinyl group-containing cyclic amide compound relative to 43 83 50 140 100 parts by weight of (meth)acrylic compound (parts by weight) Evaluation Storage stability ∘ ∘ ∘ ∘ Depth curability ∘∘ ∘ ∘∘ Δ Low shrinkability on curing ∘∘ ∘∘ Δ ∘

TABLE-US-00003 TABLE 3 Comparative Example 1 2 3 4 5 Composition Polymerizable (Meth)acrylic 2-(((Butylamino)carbonyl)oxy) 14.8 10.0 3.0 14.8 — (parts by weight) compound compound ethyl (meth)acrylate (“H-ABEI” available from Osaka Organic Chemical Industry Ltd.) 2-Phenoxyethyl acrylate 0.6 0.6 0.6 0.6 — (“Viscoat #192” available from Osaka Organic Chemical Industry Ltd.) Isodecyl acrylate 1.3 1.3 1.0 1.3 — (“IDAA” available from Osaka Organic Chemical Industry Ltd.) (3-Ethyloxetan-3-yl) methyl acrylate 1.3 1.3 1.0 1.3 — (“OXE-10” available from Osaka Organic Chemical Industry Ltd.) N-acryloyl morpholine 4.9 4.9 2.8 4.9 — (“ACMO ” available from KJ Chemicals Corporation) Isobornyl acrylate — — — — 13.5 (“IBOA-B” available from Daicel-Allnex Ltd.) Tricyclodecane dimethanol diacrylate — — — — 9.7 (“IRR214-K” available from Daicel-Allnex Ltd.) Partially acrylic-modified 24.3 24.3 18.5 24.3 24.1 bisphenol A-type epoxy resin (“UVACURE 1561” available from Daicel-Allnex Ltd.) (Acrylic compound content: about 75 wt %) Vinyl group- N-vinyl-ϵ-caprolactam — 3.0 35.3 — — containing cyclic (“NVC” available from Tokyo amide compound Chemical Industry Co., Ltd.) Heat curable Propylene oxide-added bisphenol 0.3 0.3 0.3 0.3 — compound A-type epoxy resin (“EP-4003S” available from ADEKA) Bisphenol F-type epoxy resin 19.4 19.4 15.0 19.4 — (“EXA-830CRP” available from DIC) Photoradical Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide 0.2 0.2 0.2 0.2 0.2 polymerization (“Omnirad 819” available from iGM resins) initiator 1-Hydroxycyclohexyl phenyl ketone — — — — 0.5 (“Ominirad 184” available from iGM resins) 2-(Dimethylamino)-2-((4-methylphenyl)methyl) — — — — 0.2 1-(4-(4-morpholinyl)phenyl)-1-butanone (“Omnirad 379” available from iGM resins) Radical Heat curing agent 2-Methylimidazole 2.0 4.0 8.0 — — scavenger (“CUREZOL 2MZ-H” available from Shikoku Chemicals Corporation) Polyamine-based curing agent — — — 15.0 19.0 (ADEKA Hardener EH-5057PK” available from ADEKA) Filler Molten silica (“SANSIL SSP-07M” 24.2 24.7 9.3 11.2 27.8 available from Tokuyama Corporation) Viscosity Fumed silica (“AEROSIL RY200” 6.7 6.0 5.0 6.7 5.0 modifier available from Nippon Aerosil Co., Ltd.) Amount of vinyl group-containing cyclic amide compound relative to 100 parts — 8 158 — — by weight of (meth)acrylic compound (parts by weight) Evaluation Storage stability ∘ ∘ ∘ x x Depth curability x x x x x Low shrinkability on curing x Δ ∘ Δ x

Examples 16 to 29, Comparative Examples 6 to 8

[0172] Materials were mixed according to the compounding ratios in Tables 4 and 5 using a mixer to prepare adhesive compositions of Examples 16 to 29 and Comparative Examples 6 to 8. The mixer used was ARE-310 (available from Thinky Corporation).

[0173] In Tables 4 and 5, “UVACURE 1561” is a mixture containing about 50% by weight of a partially acrylic-modified bisphenol A-type epoxy resin, about 25% by weight of bisphenol A-type epoxy acrylate, and about 25% by weight of a bisphenol A-type epoxy resin (about 75% by weight of radical polymerizable group-containing compound content).

[0174] The viscosity of each obtained adhesive composition was measured using an E-type viscometer (“DV-III” available from BROOK FIELD) under the conditions of 25° C. and 0.5 rpm and under the conditions of 25° C. and 5.0 rpm. The thixotropic index was calculated by dividing the viscosity measured under the conditions of 25° C. and 0.5 rpm by the viscosity measured under the conditions of 25° C. and 5.0 rpm. Tables 4 and 5 show the results.

<Evaluation>

[0175] The following evaluations were performed on the adhesive compositions obtained in Examples 16 to 29 and Comparative Examples 6 to 8. Tables 4 and 5 show the results.

(Storage Stability)

[0176] Measurement of the initial viscosity right after the production and the viscosity after storage at 25° C. for 24 hours was performed on the adhesive compositions of Examples 16 to 29 and Comparative Examples 6 to 8. The viscosity change rate was derived from (viscosity after storage at 25° C. for 24 hours)/(initial viscosity).

[0177] The storage stability was evaluated based on the following criteria: the viscosity change rate of 2 or lower was rated as “o (Good)”; and the viscosity change rate of higher than 2 was rated as “x (Poor)”.

[0178] The viscosity of the adhesive composition was measured using an E-type viscometer (“DV-III” available from BROOK FIELD) at 25° C. and a rotation speed of 1.0 rpm.

(Low Shrinkability on Curing)

[0179] The adhesive compositions obtained in Examples 16 to 29 and Comparative Examples 6 to 8 were each irradiated with UV light (wavelength of 365 nm) to a dose of 1,000 mJ/cm.sup.2, followed by heating at 80° C. for one hour. Thus, a cured product having a size of 15 mm in length, 15 mm in width, and 2 mm in thickness was obtained. Measurement of specific gravity was performed on the adhesive compositions before curing at 25° C. and the cured products of the adhesive compositions at 25° C. The curing shrinkage was calculated using the equation described above.

[0180] The low shrinkability on curing was evaluated based on the following criteria: the case where the curing shrinkage was not higher than 3% was rated as “o (Good)”; the case where the curing shrinkage was higher than 3% and not higher than 3.5% was rated as “Δ (Fair)”; and the case where the curing shrinkage was higher than 3.5% was rated as “x (Poor)”.

(Adhesion on Photocuring)

[0181] To a liquid crystal polymer (“SUMIKA SUPER LCP E4008” available from Nippon Testpanel Co., Ltd.) having a size of 100 mm in length, 25 mm in width, and 2.0 mm in thickness as a substrate was applied each of the adhesive compositions obtained in Examples 16 to 29 and Comparative Examples 6 to 8, and a silicon wafer substrate (2 mm in length, 2 mm in width, 0.7 mm in thickness) was laminated thereon. Subsequently, the resulting laminate was irradiated with UV light (wavelength of 365 nm) to a dose of 1,000 mJ/cm.sup.2, thereby photocuring the adhesive composition. Thus, a test piece was obtained. The obtained test piece was subjected to measurement of the die shear strength using a die shear tester at a speed of 300 μm/s at 25° C. The die shear tester used was a bond tester DAGE 4000 (available from Nordson DAGE).

[0182] The adhesion was evaluated based on the following criteria: the case where the die shear strength was 1 N or higher was rated as “o (Good)”; and the case where the die shear strength was lower than 1N was rated as “x (Poor)”.

(Heat Curing Property at Low Temperature)

[0183] To a liquid crystal polymer (“SUMIKA SUPER LCP E4008” available from Nippon Testpanel Co., Ltd.) having a size of 100 mm in length, 25 mm in width, and 2.0 mm in thickness as a substrate was applied each of the adhesive compositions obtained in Examples 16 to 29 and Comparative Examples 6 to 8, and a silicon wafer substrate (2 mm in length, 2 mm in width, 0.7 mm in thickness) was laminated thereon. Subsequently, the resulting laminate was irradiated with UV light (wavelength of 365 nm) to a dose of 1,000 mJ/cm.sup.2 and then heated at 80° C. for one hour, thereby curing the adhesive composition. Thus, a test piece was obtained. The obtained test piece was subjected to measurement of the die shear strength using a die shear tester at a speed of 300 μm/s at 25° C. The die shear tester used was a bond tester DAGE 4000 (available from Nordson DAGE).

[0184] The curability by heating at low temperature was evaluated based on the following criteria: the case where the die shear strength was 100 N or higher was rated as “o (Good)”; and the case where the die shear strength was lower than 100 N was rated as “x (Poor)”.

TABLE-US-00004 TABLE 4 Example 16 17 18 19 20 21 22 23 Composition Polymerizable Radical polymerizable N-vinyl-2-pyrrolidone 30 30 20 30 30 — 30 30 (parts by compound compound containing (available from Fujifilm Wako weight) no epoxy group Pure Chemical Corporation) N-vinyl-ϵ-caprolactam — — — — — 30 — — (“NVC” available from Tokyo Chemical Industry Ltd.) Isobornyl acrylate 10 25 10 25 — 10 10 10 (“IBOA-B” available from Daicel-Allnex Ltd.) N-acryloyl morpholine — — — — 10 — — — (“ACMO” available from KJ Chemicals Corporation) Epoxy compound Bisphenol F-type epoxy resin 20 35 40 10 20 20 20 20 containing no radical (“EXA-830CRP” polymerizable group available from DIC) Compound containing Partially acrylic-modified 40 10 30 35 40 40 40 40 epoxy group and radical bisphenol A-type epoxy polymerizable group resin (“UVACURE 1561 ” available from Daicel-Allnex Ltd.) (Acrylic compound content: about 75 wt %) Photoradical Oxime ester compound 2 2 2 2 2 2 2 2 polymerization (“ADEKA Arkls NCI-930” available from ADEKA) initiator Heat radical Azo initiator — — — — — — — — polymerization (“V-501” available from Fujifilm Wako initiator Pure Chemical Corporation) Heat curing 2-Methylimidazole (“CUREZOL 2MZ-H” 3 3 3 3 3 3 3 3 agent available from Shikoku Chemicals Corporation, starting range temperature: 76° C.- 92° C.) Modified polyamine-based curing agent — — — — — — — — (“ADEKA Hardener EH-5057PK” available from ADEKA, starting range temperature: 80° C. or lower) 2-Phenylimidazole — — — — — — — — (“CUREZOL 2PZ” available from Shikoku Chemicals Corporation, starting range temperature: 96° C.-107° C.) Filler Methyl-treated silica (“SANSIL SSP-07M” 20 20 20 20 20 20 5 50 available from Tokuyama Corporation) Viscosity Hydrophobic fumed silica (“AEROSIL R202” 5 5 5 5 5 5 5 5 modifier available from Nippon Aerosil Co., Ltd.) Light- Titanium black (“13M-C” available — — — — — — — — blocking agent from Mitsubishi Materials Corporation) Total amount of compounds containing radical polymerizable group in 100 parts by 70 62.5 52.5 81.3 70 70 70 70 weight of polymerizable compound (parts by weight) Thixotropic index 5.5 5.4 5.2 5.3 5.5 5.6 4.1 6.5 Evaluation Storage stability ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Low shrinkability on curing ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Adhesion on photocuring ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Heat curing property at low temperature ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘

TABLE-US-00005 TABLE 5 Comparative Example Example 24 25 26 27 28 29 6 7 8 Composition Polymerizable Radical polymerizable N-vinyl-2-pyrrolidone 30 30 — 30 30 30 30 30 30 (parts by compound compound containing (available from Fujifilm Wako weight) no epoxy group Pure Chemical Corporation) N-vinyl-ϵ-caprolactam — — — — — — — — — (“NVC” available from Tokyo Chemical Industry Ltd.) Isobornyl acrylate 10 10 40 10 10 10 10 70 10 (“IBOA-B” available from Daicel-Allnex Ltd.) N-acryloyl morpholine — — — — — — — — — (“ACMO” available from KJ Chemicals Corporation) Epoxy compound Bisphenol F-type epoxy resin 20 20 20 20 20 20 60 — 20 containing no radical (“EXA-830CRP” available polymerizable group from DIC) Compound containing Partially acrylic-modified 40 40 40 40 40 40 — — 40 epoxy group and radical bisphenol A-type epoxy resin polymerizable group (“UVACURE 1561” available from Daicel-Allnex Ltd.) (Acrylic compound content: about 75 wt %) Photoradical Oxime ester compound 2 2 2 2 2 2 2 2 2 polymerization (“ADEKA ArkIs NCI-930” available from ADEKA) initiator Heat radical Azo initiator 0.5 0.5 — — — — — — — polymerization (“V-501” available from Fujifilm Wako initiator Pure Chemical Corporation) Heat curing 2-Methylimidazole (“CUREZOL 2MZ-H ” 3 3 3 3 3 — 3 3 — agent available from Shikoku Chemicals Corporation, starting range temperature: 76° C.-92° C.) Modified polyamine-based curing agent (“ADEKA — — — — — 30 — — — Hardener EH-5057PK” available from ADEKA, starting range temperature: 80° C. or lower) 2-Phenylimidazole (“CUREZOL 2PZ” — — — — — — — — 3 available from Shikoku Chemicals Corporation, starting range temperature: 96° C.-107° C.) Filler Methyl-treated silica (“SANSIL SSP-07M ” 20 20 20 — 60 20 20 20 20 available from Tokuyama Corporation) Viscosity Hydrophobic fumed silica (“AEROSIL R202 ” 5 5 5 5 5 5 5 5 5 modifier available from Nippon Aerosil Co.. Ltd.) Light-blocking Titanium black (“13M-C” available — 1 — — — — — — — agent from Mitsubishi Materials Corporation) Total amount of compounds containing radical polymerizable group in 100 parts 70 70 70 70 70 70 40 100 70 by weight of polymerizable compound (parts by weight) Thixotropic index 5.5 5.6 5.5 3.5 7.1 6.2 4.2 4.4 5.5 Evaluation Storage stability ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ ∘ Low shrinkability on curing ∘ ∘ Δ ∘ ∘ ∘ ∘ x ∘ Adhesion on photocuring ∘ ∘ ∘ ∘ ∘ ∘ x ∘ ∘ Heat curing property at low temperature ∘ ∘ ∘ ∘ ∘ ∘ ∘ x x

INDUSTRIAL APPLICABILITY

[0185] The present invention can provide an adhesive composition capable of suppressing shrinkage on curing and excellent in storage stability and depth curability, or an adhesive composition excellent in adhesion on photocuring, curability by heating at low temperature, and low shrinkability on curing. The present invention can also provide an optical component, an electronic component, and an electronic module each including the adhesive composition.