Active energy ray-curable composition, cured product, and optical member

Abstract

Provided are: an active energy ray-curable composition comprising a component (A) as a curable component, wherein the content of the component (A) is not less than 50.0 mass% of curable components; a cured product obtained by curing the active energy ray-curable composition; and an optical member.　The component (A) is an alicyclic compound which has at least one aliphatic hydrocarbon ring structure and at least one epoxy group or hydroxyl group, wherein a ratio obtained by dividing the mass of a carbon atom group constituting the aliphatic hydrocarbon ring structure by the mass of an entire molecule thereof is in the range of 60.0-80.0%.

Description

Active energy ray curable composition, cured product, and optical component

[0001] This disclosure relates to active energy ray curable compositions, cured products, and optical components.

[0002] Optical transparent resins, which are lighter and less prone to breakage than glass, are widely used as materials for optical components such as lenses and prisms. While various polymer materials are used for this purpose, cycloolefin polymers, which exhibit high transparency, excellent heat resistance, and a high Abbe number, have become increasingly popular in recent years. The Abbe number is an index used to evaluate the wavelength dependence of refractive index; a higher value indicates less change in refractive index with wavelength. Optical transparent resins with a high Abbe number are suitable as optical materials because, for example, they exhibit less chromatic aberration (color fringing such as red or blue appearing in the field of view) when used in lenses or prisms. Ideally, adhesives used with optical transparent resins should have the exact same refractive index and Abbe number as the adherend. This is because if the refractive index and Abbe number differ, reflection at the adhesive interface increases, chromatic aberration occurs, and optical performance deteriorates. Various materials have been proposed as adhesives for optical transparent resins, but a curable adhesive composition mainly composed of epoxy compounds has been proposed as an adhesive with a high Abbe number and excellent transparency.

[0003] For example, Patent Document 1 proposes an active energy ray curable adhesive composition comprising (A) an alicyclic epoxy resin without an aromatic ring, (B) a dicyclopentadiene-type epoxy resin without an aromatic ring, (C) a photoacid generator, (D1) an aliphatic epoxy resin without an aromatic ring, (D2) a polyfunctional oxetane resin without an aromatic ring, and (D3) a monofunctional oxetane resin without an aromatic ring, having a refractive index of 1.500 to 1.520 and an Abbe number of 54 to 57.

[0004] Furthermore, Patent Document 2 proposes an active energy ray curable adhesive composition comprising (A1) a dicyclopentadiene type epoxy resin without an aromatic ring, (A2) an alicyclic epoxy without an aromatic ring, (B1) a monofunctional oxetane resin without an aromatic ring, (B2) a bifunctional oxetane resin without an aromatic ring, and (C) a photoacid generator, with a refractive index of 1.508 to 1.520 and an Abbe number of 54 to 57.

[0005] Japanese Patent Publication No. 2017-141357 Japanese Patent Publication No. 2017-141356

[0006] However, because the aforementioned active energy ray curing compositions have a low refractive index, when used with cycloolefin polymers such as Zeon Corporation's "Zeonex K22R" (refractive index 1.535) or Mitsui Chemicals, Inc.'s "Apel APL5014CL" (refractive index 1.544), the difference in refractive index causes problems such as reduced transmittance and blurred images. Furthermore, since increasing the refractive index generally tends to decrease the Abbe number, raising the refractive index of the aforementioned adhesive composition to the same level as the aforementioned cycloolefin polymers would decrease the Abbe number, resulting in the problem of chromatic aberration. In addition, cycloolefin polymers have low polarity, making it difficult to increase their adhesive strength.

[0007] This disclosure has been made in view of the above, and aims to provide an active energy ray curable composition having a high refractive index and Abbe number in the resulting cured product, as well as a cured product and an optical component obtained by curing the active energy ray curable composition.

[0008] The means for solving the above problems include the following embodiments: <1> An active energy ray curable composition comprising the following component (A) as a curable component, wherein the content of component (A) is 50.0% by mass or more of the curable component. (A): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total mass of the molecule is in the range of 60.0% to 80.0%. <2> The active energy ray curable composition according to <1>, further comprising the following component (B) as a curable component. (B): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total mass of the molecule is in the range of 25.0% or more and less than 60.0%. <3> The active energy ray curable composition according to <2>, wherein the content of component (B) is 0.1% by mass to 50.0% by mass of the curable component. <4> An active energy ray curable composition according to any one of <1> to <3>, further comprising the following component (C) as a curable component: (C): Brominated bisphenol A type epoxy compound or brominated bisphenol F type epoxy compound <5> An active energy ray curable composition according to <4>, wherein the content of component (C) is 0.1% to 50.0% by mass of the curable component. <6> An active energy ray curable composition according to <2>, further comprising the following component (C) as a curable component: (C): Brominated bisphenol A type epoxy compound or brominated bisphenol F type epoxy compound <7> An active energy ray curable composition according to any one of <1> to <6>, further comprising a photocationic polymerization initiator as component (D). <8> An active energy ray curable composition according to <7>, wherein the content of component (D) is 0.1 to 15.0 parts by mass per 100.0 parts by mass of the curable component. <9> An active energy ray curable composition according to any one of <1> to <8>, wherein the refractive index at 589 nm after curing is 1.525 to 1.560 and the Abbe number is 45 to 65. <10> An active energy ray curable composition according to any one of <1> to <9>, which is an adhesive composition. <11> A cured product obtained by curing an active energy ray curable composition according to any one of <1> to <10>.<12> An optical member obtained by curing an active energy ray curable composition described in any one of <1> to <10>.

[0009] According to this disclosure, it is possible to provide an active energy ray curable composition having a high refractive index and Abbe number in the resulting cured product, as well as a cured product and an optical member obtained by curing the active energy ray curable composition.

[0010] The embodiments for implementing this disclosure will be described in detail below. However, this disclosure is not limited to the embodiments described below. In the embodiments described below, the components (including element steps, etc.) are not essential unless otherwise specified. The same applies to numerical values ​​and their ranges, and they do not limit this disclosure. In this specification, numerical ranges indicated using "~" include the numerical values ​​before and after "~" as the minimum and maximum values, respectively. In numerical ranges described stepwise in this specification, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another stepwise numerical range. Also, in numerical ranges described in this specification, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples. Furthermore, in this specification, a combination of two or more preferred embodiments is a more preferred embodiment.

[0011] (Active Energy Ray Curable Composition) The active energy ray curable composition according to this disclosure contains the following component (A) as a curable component, and the content of component (A) is 50.0% by mass or more of the curable component. (A): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total mass of the molecule is in the range of 60.0% to 80.0%. Carbon atoms that do not constitute the aliphatic hydrocarbon ring structure that are substituted on the aliphatic hydrocarbon ring are not included in the group of carbon atoms constituting the aliphatic hydrocarbon ring structure as referred to herein. In addition, the two carbon atoms constituting the epoxy group are not included in the group of carbon atoms constituting the aliphatic hydrocarbon ring structure as referred to herein, but if they are shared with the two carbon atoms of the aliphatic hydrocarbon ring, they are included in the group of carbon atoms constituting the aliphatic hydrocarbon ring structure.

[0012] As described above, conventional active energy ray curable compositions have resulted in cured products with low refractive indices and Abbe numbers, which were insufficient. As a result of diligent research by the present inventors, it has been found that by adopting the above configuration, it is possible to provide an active energy ray curable composition in which the cured product has a high refractive index and Abbe number. The content of alicyclic compounds, which are component (A) and have one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, and in which the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total mass of the molecule is in the range of 60.0% to 80.0%, is 50.0% by mass or more of the curable components. Therefore, it is estimated that a cured product with a high refractive index and Abbe number is obtained because the proportion of aliphatic hydrocarbon ring structures is large.

[0013] Furthermore, the active energy ray curable composition according to this disclosure also exhibits excellent adhesive properties and can be suitably used as an adhesive composition.

[0014] <Component (A): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 60.0% to 80.0%> The active energy ray curable composition according to this disclosure contains component (A) as a curable component. Component (A) preferably contains a compound having epoxy groups from the viewpoint of curability and the refractive index and Abbe number of the resulting cured product. Component (A) preferably has a total of two or more epoxy and hydroxyl groups, more preferably two to eight, and particularly preferably two to four.

[0015] (A) The ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure in component (A) to the total mass of the molecule is in the range of 60.0% to 80.0%, and from the viewpoint of the refractive index and Abbe number of the resulting cured product, it is preferably in the range of 62.0% to 80.0%, preferably in the range of 65.0% to 80.0%, and particularly preferably in the range of 70.0% to 80.0%.

[0016] (A) Component (A) is preferably an alicyclic epoxy compound in which an aliphatic hydrocarbon ring and an epoxy ring are fused, from the viewpoint of the refractive index and Abbe number of the resulting cured product.

[0017] (A) Specifically, preferred components include, for example, (3,3',4,4'-diepoxy)bicyclohexyl, dicyclopentadiene diepoxide, cyclohexene oxide, and dicyclopentadiene dimethanol. In particular, from the viewpoint of the refractive index and Abbe number of the resulting cured product, it is especially preferable to include at least one selected from the group consisting of 3,3',4,4'-diepoxy)bicyclohexyl and dicyclopentadiene diepoxide.

[0018] Component (A) may be present as a single element or as two or more elements. The content of component (A) is 50.0% by mass or more of the curable components, and from the viewpoint of the refractive index and Abbe number of the resulting cured product, it is preferably 60.0% by mass or more, more preferably 65.0% by mass or more, even more preferably 70.0% by mass or more, and particularly preferably 75.0% by mass or more. Furthermore, the content of component (A) is 100.0% by mass or less of the curable components, preferably 99.9% by mass or less, and more preferably 99.8% by mass or less.

[0019] <Component (B): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 25.0% or more and less than 60.0%> The active energy ray curable composition according to this disclosure preferably contains the following component (B) as a curable component from the viewpoint of ease of adjusting the refractive index and Abbe number of the cured product. (B): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 25.0% or more and less than 60.0% Component (B) preferably contains a compound having an epoxy group from the viewpoint of curability and ease of adjusting the refractive index and Abbe number of the cured product. Component (B) preferably has a total of two or more epoxy groups and hydroxyl groups, more preferably two to eight, and particularly preferably two to four, from the viewpoint of curability and ease of adjusting the refractive index and Abbe number of the resulting cured product.

[0020] The ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure in component (B) to the total mass of the molecule is in the range of 25.0% or more and less than 60.0%, and from the viewpoint of the refractive index and Abbe number of the resulting cured product, it is preferably in the range of 30.0% or more and less than 60.0%, preferably in the range of 35.0% or more and less than 60.0%, and particularly preferably in the range of 40.0% or more and less than 60.0%.

[0021] (B) Specifically, preferred components include, for example, 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxylate, an epoxidized product of a 1,2-epoxy-4-vinylcyclohexane addition polymer of trimethylolpropane, 1,4-cyclohexanedimethanol diglycidyl ether, and dicyclopentadienedimethanol diglycidyl ether. In particular, from the viewpoint of the refractive index and Abbe number of the resulting cured product, it is especially preferable to include at least one selected from the group consisting of 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxylate, an epoxidized product of a 1,2-epoxy-4-vinylcyclohexane addition polymer of trimethylolpropane, and dicyclopentadienedimethanol diglycidyl ether.

[0022] Component (B) may be present as a single element or as two or more elements. The content of component (B) is preferably 0.1% to 50.0% by mass, more preferably 5.0% to 40.0% by mass, and particularly preferably 10.0% to 30.0% by mass, from the viewpoint of the refractive index and Abbe number of the resulting cured product, among the curable components.

[0023] <Component (C): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 25.0% or more and less than 60.0%> The active energy ray curable composition according to this disclosure preferably contains the following component (C) as a curable component, from the viewpoint of the refractive index and Abbe number of the cured product obtained, and the ease of adjusting the refractive index and Abbe number of the cured product obtained. (C): Brominated bisphenol A type epoxy compound or brominated bisphenol F type epoxy compound Component (C) is not particularly limited as long as it is a compound having a brominated bisphenol A structure or a brominated bisphenol F structure and an epoxy group. Component (C) preferably contains a brominated bisphenol A type epoxy compound. Component (C) preferably has two or more epoxy groups, more preferably two to eight, and particularly preferably two to four, from the viewpoint of curability and the ease of adjusting the refractive index and Abbe number of the cured product obtained.

[0024] The epoxy equivalent of component (C) is not particularly limited, but is preferably 200 g / eq to 1,000 g / eq, and more preferably 300 g / eq to 600 g / eq.

[0025] Component (C) may be present as a single type or as two or more types. The content of component (C) is preferably 0.1% to 50.0% by mass, more preferably 5.0% to 40.0% by mass, and particularly preferably 10.0% to 30.0% by mass, from the viewpoint of the refractive index and Abbe number of the resulting cured product, among the curable components.

[0026] Furthermore, the active energy ray curable composition according to this disclosure preferably contains components (B) and (C) as curable components, from the viewpoint of the refractive index and Abbe number of the resulting cured product, and the ease of adjusting the refractive index and Abbe number of the resulting cured product.

[0027] <(D) component: Photo cationic polymerization initiator> The active energy ray-curable composition according to the present disclosure preferably contains a photo cationic polymerization initiator as a component (D) in addition to the curable components. Known compounds may be used as the photo cationic polymerization initiator.

[0028] Examples of the photo cationic polymerization initiator include onium salts such as iodonium salts, sulfonium salts, diazonium salts, selenium salts, pyridinium salts, ferrocenium salts, and phosphonium salts. Among these, iodonium salts or sulfonium salts are preferred. When the photo cationic polymerization initiator is an iodonium salt or a sulfonium salt, examples of the counter anion include BF

[0029] － , AsF ６ － , SbF ６ － , PF ６ － , B(C ６ F ５ ) ４ － etc.

[0029] The iodonium salts mentioned above include (tricumyl)iodonium tetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis(dodecylphenyl)iodonium hexafluoroantimonate, and bis(dodecylphenyl)iodonium tetraf Examples include ruoborates, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrafluoroborate, and 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate. Furthermore, commercially available iodonium salts can also be used, specifically, for example, "UV9380C" (product name) from Mentive Performance Materials Japan, "PHOTOINITIATOR2074" (product name) from Solvay Japan, "WPI-116" (product name) and "WPI-113" (product name) from Fujifilm Wako Pure Chemical Corporation, "TR-PAG-30201" from Changzhou Strong Electronic New Materials Co., Ltd., "Omnicat250" from IGM RESINS, and "IK-1" and "IK-1FG" from Sunapro.

[0030] The sulfonium salts include bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluoroantimonate, bis[4-(diphenylsulfonio)phenyl]sulfide bistetrafluoroborate, bis[4-(diphenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate, diphenyl-4-(phenylthio)phenylsulfonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, diphenyl-4-(phenylthio)phenylsulfonium tetrakis(pentafluorophenyl)borate, and Examples include riphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrafluoroborate, triphenylsulfonium tetrakis(pentafluorophenyl)borate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bishexafluoroantimonate, bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide bistetrafluoroborate, and bis[4-(di(4-(2-hydroxyethoxy))phenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate.In addition, commercially available sulfonium salts can also be used. Specifically, for example, "Silicyure UVI-6990" (trade name), "Silicyure UVI-6992" (trade name) and "Silicyure UVI-6974" manufactured by Dow Chemical Japan, "ADEKA Optomer SP-150" (trade name), "ADEKA Optomer SP-152" (trade name), "ADEKA Optomer SP-170" (trade name) and "ADEKA Optomer SP-172" (trade name) manufactured by ADEKA Corporation, "WPAG-370" (trade name) and "WPAG-638" (trade name) manufactured by Fuji Film Wako Pure Chemical Corporation, "CPI-100P", "CPI-110P", "CPI-101A", "CPI-200K", "CPI-210S", "CPI-100B(40)", "CPI-110B", "CPI-310B", "CPI-310FG", "VC-1S", "VC-1FG", "CPI-410S", "CPI-410B" and "ES-1B" etc. manufactured by San-Apro Ltd. can be mentioned.

[0031] Examples of the diazonium salt include benzenediazonium hexafluoroantimonate, benzenediazonium hexafluorophosphate, benzenediazonium hexafluoroborate and the like.

[0032] The photo cationic polymerization initiator may be used alone or in combination of two or more. From the viewpoint of curability, the content of the photo cationic polymerization initiator is preferably 0.1 to 15.0 parts by mass, more preferably 0.5 to 10.0 parts by mass, still more preferably 1.0 to 8.0 parts by mass, and particularly preferably 2.0 to 6.0 parts by mass with respect to 100.0 parts by mass of the curable component.

[0033] <Other Components> The other components are not particularly limited. For example, solvents, epoxy compounds other than those described above, oxetane compounds, resins, fillers, surfactants, antistatic agents (for example, conductive polymers), leveling agents, photosensitizers, ultraviolet absorbers, antioxidants, heat resistance improvers, stabilizers, lubricants, pigments, dyes, plasticizers, suspending agents, adhesion imparting agents, nanoparticles, nanofibers, nanosheets and the like can be mentioned.

[0034] The active energy ray curable composition according to this disclosure may or may not contain a solvent. Examples of solvents include various organic solvents such as aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents, chlorinated hydrocarbon solvents, alcohol solvents, ether solvents, amide solvents, ketone solvents, ester solvents, and cellosolve solvents.

[0035] <Applications> The applications of the active energy ray curable composition according to this disclosure are not particularly limited, but for example, because of its excellent adhesive properties, it can be suitably used as an adhesive composition. Furthermore, because the active energy ray curable composition according to this disclosure has excellent refractive index and Abbe number of the resulting cured product, it can be applied to optical components, hard coats, and the like.

[0036] (Cured Products and Optical Components) The cured products according to this disclosure are obtained by curing the active energy ray curable composition according to this disclosure. For example, the cured products according to this disclosure can be obtained by irradiating the active energy ray curable composition according to this disclosure with active energy rays. The adhesives according to this disclosure are obtained by applying the active energy ray curable composition according to this disclosure between the objects to be bonded and curing it. The objects to be bonded are not particularly limited and may be inorganic compounds, organic compounds, inorganic-organic composites, and may be made of the same material or different materials. Examples of materials for the objects to be bonded include optical components, plastics, rubber, wood, metals, inorganic materials, paper, etc. Among these, optical components are preferred as the objects to be bonded. The active energy ray curable composition according to this disclosure can be suitably used for optical components from the viewpoint of the refractive index and Abbe number of the resulting cured product. Furthermore, the optical components according to this disclosure may be the cured products according to this disclosure or the adhesives according to this disclosure. In addition, hard coats are also suitably given as cured products according to this disclosure. In the case of optical components, when applying methods such as the so-called 2P (PhotoPolymer) method or nanoimprint method, which form fine shapes such as lenses, prisms, and moth-eyes on a substrate, it is possible to make the adhesion force to one substrate extremely low so that it can be easily peeled off, and then form the fine shape on the other substrate.

[0037] <Hardening method> As the hardening method, active energy ray irradiation may be performed using a known active energy ray irradiation device or the like. Examples of the active energy ray include an electron beam, light such as ultraviolet rays, visible light, and X-rays, and light is preferable. From the viewpoint of being able to use an inexpensive device, ultraviolet rays are more preferable. Examples of the ultraviolet irradiation device include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an ultraviolet (UV) electrodeless lamp, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, and a light-emitting diode (LED). The light irradiation intensity on the film coated with the present composition may be selected according to the purpose, application, etc. The light irradiation intensity in the light wavelength region effective for activating the active energy ray polymerization initiator (in the case of photo-curing, referred to as a photo-polymerization initiator) (although it varies depending on the type of photo-polymerization initiator, preferably light with a wavelength of 220 nm to 460 nm is used) is 0.1 mW / cm ２ ~1000 mW / cm ２ is preferable. Also, the irradiation energy should be appropriately set according to the type of active energy ray, the composition, etc. The light irradiation time on the film may also be selected according to the purpose, application, etc. The integrated light amount represented as the product of the light irradiation intensity and the light irradiation time in the light wavelength region is 10 mJ / cm ２ ~7,000 mJ / cm ２ It is preferable that the light irradiation time is set so that. The integrated light amount is 200 mJ / cm ２ ~5,000 mJ / cm ２ is more preferable, and 500 mJ / cm ２ ~4,000 mJ / cm ２ is even more preferable. If the integrated light amount is within the above range, the hardening of the composition proceeds smoothly, and a uniform hardened product can be easily obtained.

[0038] Next, the present disclosure will be specifically described based on examples and comparative examples. The present disclosure is not limited to the following examples.

[0039] The components used in the examples and comparative examples are shown below.

[0040] (A) Components: C8010: (3,3',4,4'-diepoxy)bicyclohexyl, manufactured by Daicel Corporation, "Celoxide 8010", the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 74.1%. DCPD-DE: Dicyclopentadiene diepoxide, manufactured by Nippon Materials Technology Co., Ltd., "DCPD-DE", the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 73.1%. CHO: Cyclohexene oxide, reagent, the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 73.4%. DCPD-DM: Dicyclopentadiene dimethanol, the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 61.1%.

[0041]

[0042] (B) Components: C2021P: 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxylate, manufactured by Daicel Corporation as "Celoxide 2021P", the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total molecular mass is 57.1%. EHPE3150: Epoxydide of the 1,2-epoxy-4-vinylcyclohexane addition polymer of trimethylolpropane, manufactured by Daicel Corporation as "EHPE3150", the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total molecular mass is 48.3%. CDMDG: 1,4-cyclohexanedimethanol diglycidyl ether, manufactured by Resonaq Corporation as "Showfree CDMDG", the ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure divided by the total molecular mass is 28.1%. - DCPD-DE: Dicyclopentadiene dimethanol diglycidyl ether, ADEKA Corporation "ADEKARESIN EP-4088L". The ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 38.9%. - HBE100: Hydrogenated bisphenol A type epoxy compound, Shin Nippon Rika Co., Ltd. "RICARESIN HBE-100". The ratio of the mass of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total molecular mass is 40.8%.

[0043]

[0044] (C) Component E152: Brominated bisphenol A epoxy compound, the compound described below, "Epiclon 152" manufactured by DIC Corporation, an epoxy compound that does not have an aliphatic hydrocarbon ring structure.

[0045]

[0046] (D) Component CPI100P: Triarylsulfonium salt (50% propylene carbonate solution), manufactured by Sunapro Co., Ltd. "CPI-100P"

[0047] Table 1 shows the physical properties of each epoxy compound and oxetane compound.

[0048]

[0049] (Examples 1-17 and Comparative Examples 1-3) <Production of Active Energy Ray Curable Compositions> Active energy ray curable compositions were produced by stirring, mixing, and dissolving the compounds shown in Table 2 in the proportions shown in Table 2 in a stainless steel container.

[0050] <Method for measuring viscosity at 25°C> The viscosity of the obtained active energy ray curable composition at 25°C was measured using an E-type viscometer.

[0051] <Method for measuring refractive index and Abbe number> The obtained active energy ray-curable composition was coated onto a polyethylene terephthalate film to a thickness of 100 μm, laminated with another polyethylene terephthalate film, and then irradiated with UV light using a 365 nm UV-LED to obtain a cured film (illuminance 200 mW / cm²). ２ (Irradiation time 60 seconds). The cured film was peeled off the substrate, and the refractive indices at 589 nm (D line), 656 nm (C line), and 486 nm (F line) at 25°C were measured using an Abbe refractometer. Furthermore, the Abbe number was calculated using the following formula: Abbe number νD = (589 nm refractive index - 1) ÷ (486 nm refractive index - 656 nm refractive index)

[0052] <Method for measuring adhesive strength> One drop of the obtained active energy ray-curable composition was placed on Zeonex K22R (2 mm thick, manufactured by Nippon Zeon Co., Ltd.), and Cosmoshine A-4360 (188 μm thick, manufactured by Toyobo Co., Ltd.) was placed over it. After adjusting the adhesive film thickness to 10 μm, UV irradiation was performed using a 365 nm UV-LED (illuminance 200 mW / cm²). ２ (Irradiation time 60 seconds). Subsequently, a shear test (tensile speed 5 mm / min) was performed one day later to measure the adhesive strength to the aforementioned Zeonex K22R.

[0053]

[0054] Note that the units of the numerical values ​​in each component column in Table 2 represent parts by mass. Also, the refractive index values ​​in Table 2 represent the refractive index at a wavelength of 589 nm.

[0055] As is clear from the results of Examples 1 to 17, the compositions according to this disclosure exhibited refractive indices close to those of cycloolefin polymers and high Abbe numbers. Furthermore, these compositions had low viscosity and excellent coating properties. On the other hand, Comparative Examples 1 to 3 were compositions in which the content of component (A) in the curable component was less than 50% by mass, and when the Abbe number was increased, the refractive index became lower than that of cycloolefin polymers.

[0056] The disclosure of Japanese Patent Application No. 2024-172780, filed on 1 October 2024, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard were specifically and individually noted to be incorporated by reference.

Claims

1. An active energy ray curable composition comprising the following component (A) as a curable component, wherein the content of component (A) is 50.0% by mass or more of the total curable component. (A): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 60.0% to 80.0%.

2. The active energy ray curable composition according to claim 1, further comprising the following component (B) as a curable component. (B): An alicyclic compound having one or more aliphatic hydrocarbon ring structures and one or more epoxy groups or hydroxyl groups, wherein the ratio of the mass of the group of carbon atoms constituting the aliphatic hydrocarbon ring structure to the total mass of the molecule is in the range of 25.0% or more and less than 60.0%.

3. The active energy ray curable composition according to claim 2, wherein the content of component (B) is 0.1% by mass to 50.0% by mass of the curable components.

4. The active energy ray curable composition according to claim 1, further comprising the following component (C) as a curable component: (C): Brominated bisphenol A type epoxy compound or brominated bisphenol F type epoxy compound 5. The active energy ray curable composition according to claim 4, wherein the content of component (C) is 0.1% by mass to 50.0% by mass of the curable components.

6. The active energy ray curable composition according to claim 2, further comprising the following component (C) as a curable component: (C): Brominated bisphenol A type epoxy compound or brominated bisphenol F type epoxy compound 7. The active energy ray curable composition according to claim 1, further comprising a photocationic polymerization initiator as component (D).

8. The active energy ray curable composition according to claim 7, wherein the content of component (D) is 0.1 to 15.0 parts by mass per 100.0 parts by mass of the curable component.

9. The active energy ray curable composition according to claim 1, wherein the refractive index at 589 nm after curing is 1.525 to 1.560 and the Abbe number is 45 to 65.

10. The active energy ray curable composition according to claim 1, which is an adhesive composition.

11. A cured product obtained by curing an active energy ray curable composition according to any one of claims 1 to 10.

12. An optical member obtained by curing an active energy ray curable composition according to any one of claims 1 to 10.

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