Curable composition, optical device, and method for manufacturing optical device

Abstract

The present disclosure provides a curable composition with which it is possible to realize improvement in a shear adhesive strength of a cured product and a durability of the cured product. The curable composition contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group, the second thiol compound different from the first thiol compound (B1).

Description

Curable composition, optical device, and method for producing optical device

[0001] The present disclosure relates to a curable composition, an optical device, and a method for producing an optical device, and more particularly to a curable composition containing a thiol compound, an optical device including a cured product of the curable composition, and a method for producing an optical device.

[0002] Patent Document 1 describes a one-component resin composition containing an epoxy resin, a compound having two thiol groups in the molecule but not containing an ester skeleton, and a compound having three thiol groups in the molecule but not containing an ester skeleton.

[0003] Patent No. 6983380

[0004] An object of the present disclosure is to provide a curable composition, an optical device, and a method for producing an optical device, which can improve the shear adhesive strength and durability of the cured product.

[0005] A curable composition according to one embodiment of the present disclosure contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group and different from the first thiol compound (B1).

[0006] An optical device according to an aspect of the present disclosure includes an optical component, a peripheral component different from the optical component, and a cured product interposed between the optical component and the peripheral component and adhering the optical component to the peripheral component. The cured product is obtained by curing the curable composition.

[0007] A method for manufacturing an optical device according to one aspect of the present disclosure is a method for manufacturing an optical device including an optical component and a peripheral component different from the optical component, the method including bonding the optical component and the peripheral component using an adhesive. The adhesive contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group, the second thiol compound (B2) being different from the first thiol compound (B1).

[0008] [Embodiments] Embodiments of the present disclosure will be described. Note that the following embodiments are merely a portion of various embodiments of the present disclosure. Furthermore, the following embodiments can be modified in various ways depending on the design, etc., as long as the object of the present disclosure can be achieved. Furthermore, the mechanism of action described below is speculated, and the present disclosure is not bound by the explanation of the mechanism of action below.

[0009] (Summary) The curable composition according to this embodiment (hereinafter also referred to as composition (X)) contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group, which is different from the first thiol compound (B1). This enables composition (X) to achieve improved shear adhesive strength and durability of the cured product.

[0010] In this disclosure, the term "shear adhesive strength" refers to the strength of adhesion of a cured product to an adherend and the shear fracture strength of the cured product, which can be confirmed using a bonding strength tester. The term "durability" refers to the resistance of the shear adhesive strength to deterioration even under high temperature and high humidity conditions.

[0011] Furthermore, in the present disclosure, as described above, the second thiol compound (B2) is different from the first thiol compound (B1). Therefore, the second thiol compound (B2) does not have a glycoluril structure. In other words, a thiol compound having a thioether group and a glycoluril group is included in the first thiol compound (B1). Furthermore, the thiol compound (B) may contain another thiol compound (a third thiol compound (B3)) that does not fall under the first thiol compound (B1) or the second thiol compound (B2), as long as the object of the present disclosure is not impaired.

[0012] Composition (X) is suitable for use in producing optical devices. That is, a cured product can be obtained by curing composition (X), and this cured product can be used to bond components that constitute optical devices, for example.

[0013] (Components) The components of composition (X) will be described in detail.

[0014] <Epoxy Compound> The number of epoxy groups that the epoxy compound (A) has in one molecule is not particularly limited, but is preferably 2 or more in one molecule. In other words, the epoxy compound (A) preferably contains an epoxy compound having 2 or more epoxy groups in one molecule.

[0015] The epoxy compound (A) preferably contains an aromatic epoxy compound (A1). The aromatic epoxy compound (A1) has a rigid structure, which can increase the elastic modulus of the cured product. As a result, the shear adhesive strength of the cured product can be increased. In particular, the shear adhesive strength of the cured product can be particularly increased compared to when the epoxy compound (A) does not contain the aromatic epoxy compound (A1) and contains only an aliphatic epoxy compound. Examples of the aromatic epoxy compound (A1) include alkylphenol novolac epoxy resins such as phenol novolac epoxy resins and cresol novolac epoxy resins; naphthol novolac epoxy resins; phenol aralkyl epoxy resins having a phenylene structure, biphenylene structure, etc.; biphenyl aralkyl epoxy resins; naphthol aralkyl epoxy resins having a phenylene structure, biphenylene structure, etc.; polyfunctional epoxy resins such as triphenolmethane epoxy resins and alkyl-modified triphenolmethane epoxy resins; triphenylmethane epoxy resins; The aromatic epoxy compound (A1) preferably contains at least one selected from the group consisting of epoxy resins, tetrakisphenolethane epoxy resins, dicyclopentadiene epoxy resins, stilbene epoxy resins, bisphenol epoxy resins such as bisphenol A epoxy resins and bisphenol F epoxy resins, biphenyl epoxy resins, naphthalene epoxy resins, bromine-containing epoxy resins such as bisphenol A bromine-containing epoxy resins, and glycidylamine epoxy resins obtained by reacting polyamines such as diaminodiphenylmethane and isocyanuric acid with epichlorohydrin. In particular, the aromatic epoxy compound (A1) preferably contains at least one of bisphenol A epoxy resins and bisphenol F epoxy resins.

[0016] The epoxy group equivalent of the epoxy compound (A) is, for example, 50 g / eq. or more and 1000 g / eq. or less. The epoxy group equivalent is preferably 70 g / eq. or more, and more preferably 100 g / eq. or more. The epoxy group equivalent is the number of grams of the epoxy compound (A) containing 1 gram equivalent of epoxy groups, that is, the value obtained by dividing the mass of 1 mole of the epoxy compound (A) by the number of epoxy groups per molecule of the epoxy compound (A).

[0017] The epoxy compound (A) may be liquid at room temperature or may be solid at room temperature. The epoxy compound (A) may contain both a compound that is liquid at room temperature and a compound that is solid at room temperature.

[0018] <Thiol Compound> The composition (X) contains a thiol compound (B). The thiol compound (B) can enhance the curability of the composition (X).

[0019] As described above, the thiol compound (B) contains a first thiol compound (B1) and a second thiol compound (B2), but for example, the thiol compound (B) does not contain an aliphatic thiol compound. In the present disclosure, an aliphatic thiol compound is a thiol compound consisting solely of an aliphatic structure. The aliphatic structure includes, for example, a linear or branched hydrocarbon group or an alicyclic structure. When the thiol compound (B) does not contain an aliphatic thiol compound, the elastic modulus of the cured product is more likely to be increased. This can further improve the shear adhesive strength of the cured product. Note that, among the aliphatic thiol compounds, compounds that do not fall into either the first thiol compound (B1) or the second thiol compound (B2) are included in the third thiol compound (B3).

[0020] Furthermore, for example, the thiol compound (B) does not contain a thiol compound having an ester bond. In this case, even if the cured product is placed under high temperature and high humidity conditions, the shear adhesive strength of the cured product does not decrease due to hydrolysis of the ester bond. Therefore, the shear adhesive strength of the cured product is less likely to decrease. Among compounds having an ester bond, compounds that do not fall into either the first thiol compound (B1) or the second thiol compound (B2) are included in the third thiol compound (B3).

[0021] The equivalent ratio of the thiol group of the thiol compound (B) to the epoxy group of the epoxy compound (A) is preferably 0.30 or more and 1.50 or less. This equivalent ratio is more preferably 0.40 or more, and even more preferably 0.80 or more. This equivalent ratio is more preferably 1.30 or less, and even more preferably 1.00 or less.

[0022] (First thiol compound) The first thiol compound (B1) has a glycoluril structure. This can prevent a decrease in the shear adhesive strength of the cured product even when the cured product is exposed to high-temperature and high-humidity conditions. As described above, the first thiol compound (B1) may have a thioether group.

[0023] The thiol group equivalent of the first thiol compound (B1) is preferably 80 or more. In this case, outgassing of the cured product can be further suppressed. The thiol equivalent is the number of grams of the thiol compound (B) containing 1 gram equivalent of thiol groups, that is, the value obtained by dividing the mass of 1 mole of the thiol compound (B) by the number of thiol groups per molecule of the thiol compound (B).

[0024] The first thiol compound (B1) preferably contains a polyfunctional thiol compound having two or more thiol groups in one molecule, and more preferably contains a compound having four or more thiol groups in one molecule.

[0025] The first thiol compound (B1) preferably contains a compound represented by formula (1). In this case, the increased shear adhesive strength of the cured product can be further maintained even when the cured product is exposed to high-temperature and high-humidity conditions.

[0026]

[0027] In formula (1), R １ ~R ４ are each independently a divalent hydrocarbon group. １ ~R ４ The number of carbon atoms in R is preferably within a specific range. In this case, the elastic modulus of the cured product can be appropriately increased, and the viscosity of the composition (X) can be appropriately reduced. １ ~R ４ The number of carbon atoms in each of these is preferably from 1 to 6, and more preferably from 1 to 4. The hydrocarbon group may be linear or branched.

[0028] The hydrocarbon group may have at least one group selected from the group consisting of a group represented by formula (2), a group represented by formula (3), and a group represented by formula (4) in the hydrocarbon chain.

[0029]

[0030]

[0031]

[0032] For example, the content of the first thiol compound (B1) is 1% by mass or more relative to the thiol compound (B). When this content is 15% by mass or more, the durability of the cured product can be further improved. Furthermore, although there is no particular upper limit for this content, by setting it to 50% by mass or less, the elastic modulus of the cured product can be appropriately increased, and the enhanced durability of the cured product can be maintained even when exposed to high-temperature and high-humidity conditions.

[0033] (Second Thiol Compound) The second thiol compound (B2) preferably has a thiol equivalent of at least 100. In this case, outgassing of the cured product can be further suppressed.

[0034] Furthermore, the second thiol compound (B2) preferably contains a polyfunctional thiol compound having two or more thiol groups in one molecule, and more preferably contains a compound having three or more thiol groups in one molecule.

[0035] The second thiol compound (B2) contains, for example, a thiol compound having a ring structure. Examples of the ring structure include an alicyclic structure, an aromatic ring structure, a heteroaromatic ring structure, and a heteroalicyclic structure. Among these, an aromatic ring structure, a heteroaromatic ring structure, and a heteroalicyclic structure are preferred. In this case, the shear adhesive strength of the cured product can be increased.

[0036] Furthermore, as the thiol compound having a heteroalicyclic structure, a compound having a 5- to 8-membered heteroalicyclic structure is preferred. Among the compounds having a heteroalicyclic structure, nitrogen-containing compounds are preferred, and specifically, thiol compounds having an isocyanuric structure are preferred. In this case, the shear adhesive strength of the cured product can be further improved.

[0037] The second thiol compound (B2) preferably contains a compound represented by formula (5), which can further improve the shear adhesive strength of the cured product.

[0038]

[0039] In formula (5), R ５ ~R １０ are each independently a linear, divalent, saturated hydrocarbon group. ５ From R １０ The number of carbon atoms in each of R is preferably within a specific range. In this case, the elastic modulus of the cured product can be appropriately increased, and the viscosity of the composition (X) can be appropriately reduced. For example, ５ and R ６ The total number of carbon atoms in R is 4 or more and 10 or less, ７ and R ８ The total number of carbon atoms in R is 4 or more and 10 or less, ９ and R １０ The total number of carbon atoms in R is 4 or more and 10 or less. ５ , R ７ and R ９ Each of R preferably has 3 carbon atoms.６ , R ８ and R １０ Each of these preferably has 2 carbon atoms.

[0040] The content of the second thiol compound (B2) is preferably 45% by mass or more relative to the thiol compound (B). When this content is 45% by mass or more, the shear adhesive strength of the cured product can be further increased. This content is more preferably 60% by mass or more. Furthermore, although there is no particular upper limit for this content, it is preferably 85% by mass or less. In this case, the increased shear adhesive strength of the cured product can be maintained even when exposed to high-temperature, high-humidity conditions.

[0041] <Curing Catalyst> The composition (X) may contain a curing catalyst (C). In this case, the curing reaction of the composition (X) is likely to proceed when the composition (X) is heated.

[0042] The curing catalyst (C) contains at least one component selected from the group consisting of, for example, imidazoles, cycloamidines, tertiary amines, organic phosphines, tetra-substituted phosphonium / tetra-substituted borates, quaternary phosphonium salts having a counter anion other than borate, and tetraphenylboron salts.

[0043] The curing catalyst (C) may contain a latent curing catalyst (C1). In this case, the reaction of the composition (X) in an unheated state is suppressed, thereby improving the storage stability of the composition (X). The latent curing catalyst (C1) may contain at least one of a liquid latent curing accelerator and a solid-dispersion latent curing accelerator. The liquid latent curing catalyst preferably contains a microencapsulated latent curing catalyst (C11). In this case, the storage stability of the composition (X) can be further improved. The microencapsulated latent curing catalyst (C11) contains, for example, a microencapsulated imidazole containing an imidazole as a compound having catalytic activity.

[0044] The content of the curing catalyst (C) relative to the total of the epoxy compound (A) and the thiol compound (B) is preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 20% by mass or less, and even more preferably 8% by mass or more and 15% by mass or less.

[0045] <Stabilizer> The composition (X) may contain a stabilizer (D). The stabilizer (D) is a compound that can suppress the reactivity of the epoxy compound (A) and the thiol compound (B), which are reactive components in the composition (X). When the composition (X) contains the stabilizer (D), the storage stability of the composition (X) can be improved.

[0046] The stabilizer (D) preferably contains an anionic polymerization inhibitor. The epoxy compound (A) and the thiol compound (B) can undergo an anionic polymerization reaction, but this reaction can be inhibited by the anionic polymerization inhibitor.

[0047] An anionic polymerization inhibitor is preferably incorporated into composition (X), particularly when composition (X) contains a curing catalyst (C). The anionic polymerization inhibitor can suppress the progress of the curing reaction in composition (X) caused by the curing catalyst (C) during storage of composition (X). The anionic polymerization inhibitor preferably contains at least one of a boron compound (D1) and a hydroxynaphthalene compound (D2). The boron compound (D1) contains at least one borate ester selected from the group consisting of, for example, triethyl borate, tributyl borate, and triisopropyl borate. The hydroxynaphthalene compound contains at least one selected from the group consisting of, for example, 2,3-dihydroxynaphthalene and 4-methoxy-1-naphthol. Note that the compounds that can be contained in the anionic polymerization inhibitor are not limited to those listed above.

[0048] The content of the stabilizer (D) relative to the total of the epoxy compound (A) and the thiol compound (B) is preferably 0.01% by mass or more and 1.0% by mass or less. If this content is 0.01% by mass or more, the storage stability of the composition (X) can be further improved. If this content is 1.0% by mass or less, the curability of the composition (X) is less likely to be impaired, and good shear adhesive strength can be maintained when the composition (X) is cured under appropriate conditions. If this content is 0.3% by mass or less, this content is more preferably 0.3% by mass or less.

[0049] <Coupling Agent> The composition (X) contains a coupling agent (E). In this case, the cured product can more easily bond components constituting the optical device. The coupling agent (E) contains, for example, a silane coupling agent. Examples of the silane coupling agent include vinyl silanes such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; styryl silanes such as p-styryltrimethoxysilane; methacryl silanes such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane; acrylic silanes such as 3-acryloxypropyltrimethoxysilane; N-2-(aminoethyl) ... and 3-isocyanatopropyltriethoxysilane.

[0050] <Colorant> The composition (X) contains a colorant (F). The colorant (F) contains at least one selected from the group consisting of, for example, carbon black, red iron oxide, and titanium oxide.

[0051] <Reactive Compound> The composition (X) may contain a reactive compound (G) different from the epoxy compound (A). For example, the reactive compound (G) contains a compound having an unsaturated bond such as (meth)acrylate.

[0052] <Additives> The composition (X) may further contain an additive (H) other than those described above, as long as the effects of the present disclosure are not excessively impaired. The additive (H) may include at least one selected from the group consisting of, for example, silicone powder, inorganic filler, carbodiimide compound, radical scavenger, diluent, solvent, pigment, flexibility imparting agent, coupling agent, antioxidant, thixotropy imparting agent (thixotropy imparting agent), dispersant, etc.

[0053] (Application Examples) <Optical Devices> A cured product can be obtained by curing composition (X), and this cured product can be used to bond components constituting optical devices. As described above, the use of thiol compound (B) can increase the elastic modulus of the cured product, thereby increasing the shear adhesive strength of the cured product. This makes it difficult for the components to slip, thereby maintaining the performance of the optical device. Furthermore, thiol compound (B) is less likely to volatilize when composition (X) is heated and cured, thereby suppressing outgassing of the cured product. This can therefore reduce the contamination of devices that are sensitive to dirt, such as lens units and sensors. Therefore, composition (X) is suitable for use in producing optical devices such as camera modules, microscopes, and endoscopes. Furthermore, among the above optical devices, composition (X) is particularly suitable for use in producing camera modules.

[0054] The optical device according to this embodiment includes an optical component, a peripheral component different from the optical component, and a cured product interposed between the optical component and the peripheral component to bond the optical component and the peripheral component. The cured product is obtained by curing composition (X). The optical component and the peripheral component can be bonded using the cured product.

[0055] Examples of optical components include lens units, diffractive optical elements (DOEs), optical fibers, optical disks, and substrates. Examples of peripheral components include camera housings and printed circuit boards. When the optical device is a camera module, examples of bonding between optical components and peripheral components include bonding between a substrate and a camera housing, and bonding between a lens unit and a camera housing. However, the optical components and peripheral components are not limited to these examples.

[0056] The materials of the optical components and peripheral components include, but are not limited to, resin materials such as liquid crystal polymer, polycarbonate, polyester, polyimide, etc., metals such as nickel and copper, ceramic, glass, or various other substrate materials.

[0057] <Method for Producing Optical Device> A method for bonding an optical component and a peripheral component using composition (X), and a method for producing an optical device comprising an optical component, a peripheral component, and a cured product will be described.

[0058] First, composition (X) is applied to either the optical component or the peripheral component. This causes composition (X) to be interposed between the optical component and the peripheral component. In this state, composition (X) is further heated to sufficiently cure composition (X) to produce a cured product, which can bond the optical component and the peripheral component. The conditions for heating composition (X) are appropriately set so that composition (X) is sufficiently cured. The heating conditions are, for example, a heating temperature of 80°C or higher and 120°C or lower, and a heating time of 30 minutes or higher and 120 minutes or lower.

[0059] The composition (X) may be used not only for producing optical devices but also for producing electronic devices including optical devices, such as semiconductor devices, integrated circuits, large-scale integrated circuits, transistors, thyristors, diodes, and capacitors.

[0060] [Aspects] The present disclosure includes the following aspects.

[0061] The curable composition according to the first aspect of the present disclosure contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group, which is different from the first thiol compound (B1).

[0062] According to this embodiment, it is possible to provide a curable composition that can improve the shear adhesive strength and durability of the cured product.

[0063] The curable composition of the second aspect of the present disclosure is the first aspect, in which both the first thiol compound (B1) and the second thiol compound (B2) contain a compound having two or more thiol groups in one molecule.

[0064] In the curable composition of the third aspect of the present disclosure, in the first or second aspect, the equivalent ratio of the thiol groups of the thiol compound (B) to the epoxy groups of the epoxy compound (A) is 0.30 or more and 1.50 or less.

[0065] According to this embodiment, the shear adhesive strength of the cured product can be further improved.

[0066] In the curable composition of the fourth aspect of the present disclosure, in any one of the first to third aspects, the first thiol compound (B1) contains a compound represented by formula (1).

[0067]

[0068] In formula (1), R １ ~R ４ are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms.

[0069] According to this embodiment, in this case, the increased shear adhesive strength of the cured product can be maintained even when the cured product is exposed to high temperature and high humidity conditions.

[0070] In the curable composition of the fifth aspect of the present disclosure, in any one of the first to fourth aspects, the second thiol compound (B2) contains a compound represented by formula (5).

[0071]

[0072] In formula (5), R ５ ~R １０ Each of R is a linear, divalent, saturated hydrocarbon group. ５ and R ６ The total number of carbon atoms in R is 4 or more and 10 or less. ７ and R ８ The total number of carbon atoms in R is 4 or more and 10 or less. ９ and R １０ The total number of carbon atoms is 4 or more and 10 or less.

[0073] According to this embodiment, the shear adhesive strength of the cured product can be further improved.

[0074] In the curable composition of the sixth aspect of the present disclosure, in any one of the first to fifth aspects, the content of the second thiol compound (B2) relative to the thiol compound (B) is 45 mass% or more.

[0075] According to this embodiment, the shear adhesive strength of the cured product can be further increased.

[0076] The curable composition according to the seventh aspect of the present disclosure is any one of the first to sixth aspects, in which the epoxy compound (A) contains an aromatic epoxy compound (A1).

[0077] According to this embodiment, the shear adhesive strength of the cured product can be increased.

[0078] The curable composition according to an eighth aspect of the present disclosure is any one of the first to seventh aspects, further comprising a curing catalyst (C). The curing catalyst (C) comprises a microcapsule-type latent curing catalyst (C11).

[0079] According to this embodiment, the storage stability of the composition (X) can be further improved.

[0080] The curable composition according to a ninth aspect of the present disclosure is any one of the first to eighth aspects, further comprising a stabilizer (D). The stabilizer (D) comprises at least one of a boron compound (D1) and a hydroxynaphthalene compound (D2).

[0081] According to this embodiment, in this case, the progress of the curing reaction in the composition (X) due to the curing catalyst (C) is further suppressed during storage of the composition (X).

[0082] The curable composition of the tenth aspect of the present disclosure, in any one of the first to ninth aspects, further contains a coupling agent (E).

[0083] According to this embodiment, the cured product can better bond components that constitute the optical device.

[0084] The curable composition of the eleventh aspect of the present disclosure, in any one of the first to tenth aspects, further contains a colorant (F).

[0085] The curable composition of the twelfth aspect of the present disclosure, in any one of the first to eleventh aspects, is used to bond an optical component included in an optical device to a peripheral component different from the optical component.

[0086] An optical device according to a thirteenth aspect of the present disclosure includes an optical component, a peripheral component different from the optical component, and a cured product interposed between the optical component and the peripheral component to bond the optical component and the peripheral component. The cured product is obtained by curing the curable composition according to any one of the first to twelfth aspects.

[0087] A fourteenth aspect of the present disclosure provides a method for manufacturing an optical device including an optical component and a peripheral component different from the optical component, the method including bonding the optical component and the peripheral component together using an adhesive. The adhesive contains an epoxy compound (A) and a thiol compound (B). The thiol compound (B) contains a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group and different from the first thiol compound (B1).

[0088] 1. Preparation of Compositions Compositions were prepared by mixing the raw materials shown in Tables 1 and 2. Details of the raw materials shown in Tables 1 and 2 are as follows.

[0089] (1) Epoxy Compounds - Epoxy Compound #1: Bisphenol A type epoxy compound. Manufactured by Nippon Steel Chemical & Material Co., Ltd. Product name: YD-8125. Functional group equivalent (epoxy group equivalent): 170.

[0090] - Epoxy compound #2: Bisphenol F type epoxy compound. Manufactured by Nippon Steel Chemical & Material Co., Ltd. Product name: YDF-8170. Functional group equivalent (epoxy group equivalent): 160.

[0091] (2) Thiol Compounds - Thiol Compound #1: A thiol compound shown in the following formula. Manufactured by Kawaguchi Chemical Industry Co., Ltd. Product name: ACTOCURE SS32. Functional group equivalent (thiol group equivalent): 177.

[0092]

[0093] Thiol compound #2: Glycoluril derivative shown in the following formula. Manufactured by Shikoku Chemicals Corporation. Product name: TS-G. Functional group equivalent (thiol group equivalent): 96.

[0094]

[0095] Thiol compound #3: Glycoluril derivative shown in the following formula. Manufactured by Shikoku Chemical Industry Co., Ltd. Product name: C3TS-G. Functional group equivalent (thiol group equivalent): 110.

[0096]

[0097] (3) Curing catalyst - Curing catalyst #1: Microencapsulated imidazole, manufactured by Asahi Kasei E-Materials Corporation, Product name: Novacure HX3722.

[0098] - Curing catalyst #2: Amine adduct type latent curing agent. Manufactured by Ajinomoto Fine-Techno Co., Ltd. Product name: Amicure PN23J.

[0099] (4) Stabilizers - Stabilizer #1: Anionic polymerization inhibitor. Product name: tributyl borate.

[0100] - Stabilizer #2: Anionic polymerization inhibitor. Manufactured by Air Water Performance Chemicals Inc. Product name: 2,3-dihydroxynaphthalene.

[0101] (5) Silane Coupling Agent - Silane Coupling Agent #1: Silane coupling agent. Silquest A-187J manufactured by MOMENTIVE.

[0102] (6) Colorant - Colorant #1: Carbon black, manufactured by Mitsubishi Chemical Corporation, product name MA100.

[0103] 2. Evaluation Test (1) Shear Adhesion Strength (Initial) A test piece (product name E463i, manufactured by Polyplastics Co., Ltd.) made of a liquid crystal polymer and having a smooth surface was prepared. The arithmetic mean roughness Ra (JIS B0601) of the surface of this test piece was 0.47 μm.

[0104] The composition was applied to the surface of this adherend to produce a film 6 mm in diameter and 0.5 mm in thickness. This film was thermally cured by heating at 80°C for 1 hour to produce a cured product. The shear adhesive strength of the cured product to a test piece was then measured using a shear tester (Nordson Corporation, Model DAGE4000 Optima) at a test temperature of 25°C, a test speed of 0.1 mm / sec, and a test height of 50 μm. The results are shown in Tables 1 and 2.

[0105] (2) Shear adhesive strength (after high-temperature, high-humidity test) A cured product obtained in the same manner as in "(1) Shear adhesive strength (initial)" above was placed on an adherend and placed in a high-temperature, high-humidity chamber at 85°C / 85% RH for 250 hours, 500 hours, and 1000 hours, and then removed. 30 to 60 minutes after the cured product was removed from the high-temperature, high-humidity chamber, the shear adhesive strength of the cured product to the adherend was measured in the same manner as in "(1) Shear adhesive strength (initial)" above. The results are shown in Tables 1 and 2.

[0106] (3) Storage stability (pot life) The curable composition was placed in a light-shielding container and stored in a water bath at 25°C, and the viscosity was measured periodically until the viscosity reached at least 1.2 times the initial viscosity. The results are shown in Tables 1 and 2. The viscosity was measured using a B-type viscometer (manufactured by Toki Sangyo Co., Ltd., model number TVB-10) at a temperature of 25°C and a rotation speed of 50 rpm.

[0107]

[0108]

Claims

1. A curable composition comprising an epoxy compound (A) and a thiol compound (B), wherein the thiol compound (B) comprises a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group, different from the first thiol compound (B1).

2. The curable composition according to claim 1, wherein both the first thiol compound (B1) and the second thiol compound (B2) contain a compound having two or more thiol groups in one molecule.

3. The curable composition according to claim 1, wherein the equivalent ratio of the thiol groups of the thiol compound (B) to the epoxy groups of the epoxy compound (A) is 0.30 or more and 1.50 or less.

4. The first thiol compound (B1) contains a compound represented by formula (1), In formula (1), R １ ~R ４ The curable composition according to claim 1 , wherein each of the groups independently represents a divalent hydrocarbon group having from 1 to 6 carbon atoms.

5. The second thiol compound (B2) contains a compound represented by formula (5), In formula (5), R ５ ~R １０ are each independently a linear divalent saturated hydrocarbon group, ５ and R ６ The total number of carbon atoms in R is 4 or more and 10 or less, ７ and R ８ The total number of carbon atoms in R is 4 or more and 10 or less, ９ and R １０ The curable composition according to claim 1 , wherein the total number of carbon atoms in the groups is 4 or more and 10 or less.

6. The curable composition according to claim 1, wherein the content of the second thiol compound (B2) is 45 mass% or more relative to the thiol compound (B).

7. The curable composition according to claim 1, wherein the epoxy compound (A) contains an aromatic epoxy compound (A1).

8. The curable composition according to claim 1, further comprising a curing catalyst (C), wherein the curing catalyst (C) comprises a microcapsule-type latent curing catalyst (C11).

9. The curable composition according to claim 1, further comprising a stabilizer (D), wherein the stabilizer (D) contains at least one of a boron compound (D1) and a hydroxynaphthalene compound (D2).

10. The curable composition according to claim 1, further comprising a coupling agent (E).

11. The curable composition according to claim 1, further comprising a colorant (F).

12. The curable composition according to claim 1, which is used to bond an optical component of an optical device to a peripheral component different from the optical component.

13. An optical device comprising an optical component, a peripheral component different from the optical component, and a cured product interposed between the optical component and the peripheral component to bond the optical component to the peripheral component, wherein the cured product is obtained by curing the curable composition according to any one of claims 1 to 12.

14. A method for manufacturing an optical device comprising an optical component and a peripheral component different from the optical component, the method comprising bonding the optical component and the peripheral component together using an adhesive, the adhesive containing an epoxy compound (A) and a thiol compound (B), the thiol compound (B) containing a first thiol compound (B1) having a glycoluril structure and a second thiol compound (B2) having a thioether group and different from the first thiol compound (B1).

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