JP7532883B2 - Active energy ray curable composition, cured product, lens and camera module - Google Patents

Description

The present invention relates to an active energy ray-curable composition, a cured product, a lens, and a camera module.

In recent years, the demand for small camera modules for electronic devices such as smartphones and mobile PCs has been expanding rapidly, and development efforts aimed at improving the production efficiency of camera modules have been actively underway. In addition, as electronic devices have become thinner, the demand for thinner camera modules has also become stricter. Conventionally, camera modules have been produced by molding resin lenses using injection molding or the like using thermoplastic resins such as cycloolefin polymers, and assembling them into a lens unit. However, the conventional method had limitations in productivity and thinning. In response to this market trend, a production method for camera modules that achieves both productivity and thinning has been disclosed (Patent Document 1), in which wafer-level lenses molded by a replica method are stacked together to assemble a lens unit.

In general, a lens unit is made by superposing a plurality of lenses having different optical constants, mainly refractive index (n _d ) and Abbe number (ν _d ), to correct chromatic aberration and realize high pixel count. In addition, as a material used for the wafer level lens, an active energy ray curable resin composition is preferably used from the viewpoints of productivity, transparency, heat resistance, etc. In particular, a resin composition using polycarbonate diol (meth)acrylate having an aliphatic skeleton has been disclosed as a wafer level lens material having optical constants of a medium refractive index and a high Abbe number (Patent Document 2).

Since wafer-level lenses are expected to be directly mounted on a substrate, they are required to have heat resistance that can withstand solder reflow (170°C to 260°C). Methods of adding thiol compounds or antioxidants to improve heat resistance have been disclosed (Patent Document 3, Patent Document 4). In addition, they are required to have moist heat resistance that can withstand a temperature and humidity test (85°C-85% RH-1000h), which is an index of long-term reliability of physical properties according to the mode of use. However, there have been no reports of wafer-level lenses that have excellent moist heat resistance without substrate peeling or defects inside the lens under the harsh temperature and humidity test conditions of 85°C-85% RH. In particular, there is a problem that aliphatic skeletons that show optical constants with a medium refractive index and high Abbe number are hydrophobic and prone to abnormalities after moist heat testing.

Therefore, there was a demand for a material capable of forming lenses with high Abbe number and transmittance, as well as excellent heat resistance and moist heat resistance.

JP 2009-251368 A International Publication No. 2019/124156 JP 2014-52424 A International Publication No. 2018/030351

The problem that the present invention aims to solve is to provide an active energy ray-curable composition capable of forming lenses that have a high Abbe number and transmittance, exhibit little change in transmittance even after solder reflow, and have excellent heat resistance and moist heat resistance.

As a result of intensive research into solving the above problems, the present inventors discovered that the above problems can be solved by using an active energy ray-curable composition that contains a specific polycarbonate diol di(meth)acrylate, a specific compound having a (meth)acryloyl group and a cyclic structure, and a specific compound having a (meth)acryloyl group and an alkylene glycol structure, and thus completed the present invention.

That is, the present invention relates to an active energy ray curable composition, a cured product, a lens, and a camera module, which are characterized by containing a polycarbonate diol di(meth)acrylate (A) represented by the following general formula (1), a compound (B) other than the polycarbonate diol di(meth)acrylate (A) having one or two (meth)acryloyl groups and a cyclic structure in one molecule, and a compound (C) other than the polycarbonate diol di(meth)acrylate (A) and the compound (B) having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule.

（式中、Ｒ^１は、それぞれ独立して、水素原子又はメチル基を示し、Ｒ^２は、それぞれ独立して、炭素原子数１～１０の炭化水素基を示す。ｎは１～１０の整数である。）

(In the formula, each R ¹ independently represents a hydrogen atom or a methyl group, each R ² independently represents a hydrocarbon group having 1 to 10 carbon atoms, and n is an integer from 1 to 10.)

The lens formed by the active energy ray-curable composition of the present invention has a high Abbe number and can reduce chromatic aberration. In addition, the lens has heat resistance with a small change in transmittance before and after solder reflow, and can be suitably used for camera modules. Furthermore, since the lens has humidity and heat resistance that does not cause peeling or defects from the substrate even under high temperature and high humidity conditions, it can be suitably used as a wafer-level lens with excellent long-term stability.

The active energy ray-curable composition of the present invention can be easily cured by irradiation with active energy rays, and can be suitably used for lens production by photoimprinting.

The active energy ray-curable composition of the present invention contains a polycarbonate diol di(meth)acrylate (A) represented by the general formula (1), a compound (B) having one or two (meth)acryloyl groups and a cyclic structure in one molecule, and a compound (C) having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule.

In the present invention, "(meth)acrylate" means acrylate and/or methacrylate. Furthermore, "(meth)acryloyl" means acryloyl and/or methacryloyl. Furthermore, "(meth)acrylic" means acrylic and/or methacrylic.

The polycarbonate diol di(meth)acrylate (A) (hereinafter abbreviated as "component (A)") represented by the general formula (1) has a structure represented by the following general formula (1). By using the component (A), an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance can be obtained.

（式中、Ｒ^１は、それぞれ独立して、水素原子又はメチル基を示し、Ｒ^２は、それぞれ独立して、炭素原子数１～１０の炭化水素基を示す。ｎは１～１０の整数である。）

(In the formula, each R ¹ independently represents a hydrogen atom or a methyl group, each R ² independently represents a hydrocarbon group having 1 to 10 carbon atoms, and n is an integer from 1 to 10.)

As the component (A), among the compounds represented by the general formula (1), an active energy ray-curable composition capable of obtaining a higher Abbe number and refractive index and capable of forming a lens having more excellent transparency, flexibility and heat resistance is obtained, so that in the general formula (1), R ¹ is preferably a hydrogen atom, R ² are each independently preferably a linear hydrocarbon group having 5 to 6 carbon atoms or a cyclic hydrocarbon group having 6 to 10 carbon atoms, and n is preferably an integer from 4 to 10. Furthermore, from the viewpoint of easily preventing crystallization and warping of the lens over time, it is more preferable that R ² are each independently a linear hydrocarbon group having 5 to 6 carbon atoms, a cyclohexane structure, or an isosorbide structure, and n is more preferably an integer from 4 to 6.

In addition, in the general formula (1), when R ² represents a linear hydrocarbon group having 5 to 6 carbon atoms and a cyclic hydrocarbon group having 6 to 10 carbon atoms, and n represents an integer of 4 to 6, the mass ratio of the linear hydrocarbon group having 5 to 6 carbon atoms to the cyclic hydrocarbon group having 6 to 10 carbon atoms is preferably in the range of 10/90 to 90/10, more preferably in the range of 20/80 to 80/20, and particularly preferably in the range of 60/40 to 80/20.

Examples of the (A) component include a reaction product of polycarbonate diol with (meth)acrylic acid and/or (meth)acrylic acid ester.

The polycarbonate diol may be, for example, a reaction product of a compound having two or more hydroxyl groups with a carbonate ester.

Examples of the compound having two or more hydroxyl groups include alkylene diols having a linear structure, alkylene diols having a branched structure, alkylene diols having a cyclic structure, and diols having a heterocyclic structure. These compounds can be used alone or in combination of two or more.

Examples of the alkylene diol having a linear structure include 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, and 1,10-decanediol.

Examples of alkylene diols having a branched chain structure include 1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 2-methyl-1,3-propanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,2-dimethyl-1,3-propanediol, 3-methyl-1,3-butanediol, 2-methyl-1,3-butanediol, 1,2-hexanediol, 1,5-hexanediol, 2,5-hexanediol, 3-methyl-1,5-pentanediol, 2,3-dimethyl-2,3-butanediol, 2-ethylenediol, ethyl-2-methyl-1,3-propanediol, 1,2-heptanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 3,6-octanediol, 2,2,4-trimethyl-1,3-pentanediol, 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 1,2-nonanediol, 1,8-nonanediol, 2,8-nonanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 1,2-decanediol, 2,2-diisobutyl-1,3-propanediol, etc.

Examples of the alkylene diol having a cyclic structure include 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 1,3-adamantanediol, and 1-hydroxy-3-adamantylmethanol.

Examples of diols having a heterocyclic structure include 3,4-tetrahydrofuran diol, 1,4-dioxane-2,3-diol, 1,1-bicyclohexyl-4,4-diol, and hexahydrofuro[3,2-b]furan-3,6-diol.

Examples of the carbonate ester include dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, etc. These compounds can be used alone or in combination of two or more.

Examples of the (meth)acrylic acid esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, and n-octyl (meth)acrylate. These (meth)acrylic acid esters can be used alone or in combination of two or more.

Examples of commercially available products of component (A) include "UH-100DA", "UM-90(1/3)DA", "UM-90(1/1)DA", "UM-90(3/1)DA", "UH-100DM", "UM-90(1/3)DM", "UM-90(1/1)DM", and "UM-90(3/1)DM" manufactured by Ube Industries, Ltd.

The content of the component (A) in the active energy ray-curable composition is preferably in the range of 10 to 80% by mass, more preferably in the range of 15 to 60% by mass, and particularly preferably in the range of 20 to 50% by mass, since an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance can be obtained.

The compound (B) having one or two (meth)acryloyl groups and a cyclic structure in one molecule (hereinafter abbreviated as "component (B)") essentially has one or two (meth)acryloyl groups and a cyclic structure in one molecule. By using component (B), an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance can be obtained.

Examples of the cyclic structure include single ring structures such as a cyclopentane structure, a cyclohexane structure, a cyclooctane structure, and a cyclodecane structure, a perhydroindene structure, a perhydroanthracene structure, a perhydrofluorene structure, a perhydrophenanthrene structure, a perhydroacenaphthene structure, a perhydrophenalene structure, a norbornane structure, an isobornane structure, an isobornyl structure, an adamantane structure, a bicyclo[3.3.0]octane structure, a tricyclo[5.2.1.0 ^2,6 ]decane structure, and a tricyclo[6.2.1.0 ^2,7 ]octane structure. ]undecane structure, dicyclopentanyl structure, dicyclopentenyl structure, and other polycyclic structures; tetrahydrofuran structure, 1,3-dioxolane structure, 1,3-dioxane structure, 1,4-dioxane structure, hexahydrofuro[3,2-b]furan structure, and other heterocyclic structures; benzene structure, naphthalene structure, fluorene structure, acenaphthene structure, phenalene structure, anthracene structure, phenanthrene structure, tetracene structure, chrysene structure, pyrene structure, triphenylene structure, pentacene structure, benzopyrene structure, perylene structure, and other aromatic ring structures. These cyclic structures may be present alone or in one molecule. Among these, the cyclohexane structure, tricyclo[5.2.1.0 ^2,6 ]decane structure, and 1,3-dioxane structure are preferred because they provide an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance.

In the (B) component, the cyclic structure and the (meth)acryloyl group may be bonded directly or via a linking group.

Examples of the linking group include an oxygen atom, a linear and/or branched hydrocarbon group having 1 to 10 carbon atoms, an alkylene oxide group having 1 to 10 repeating numbers, an alkyl ester group having 1 to 10 repeating numbers which is a ring-opening polymer of caprolactone, an amide group, etc.

Specific examples of the component (B) include cyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 4-tertiarybutylcyclohexyl (meth)acrylate, 2-cyclohexylpropanyl (meth)acrylate, hydrogenated bisphenol A di(meth)acrylate, hydrogenated bisphenol A alkylene oxide modified di(meth)acrylate, hydrogenated bisphenol A caprolactone modified di(meth)acrylate, hydrogenated bisphenol A glycidyl ether modified di(meth)acrylate, hydrogenated bisphenol F di(meth)acrylate, hydrogenated bisphenol F Caprolactone modified di(meth)acrylate, hydrogenated bisphenol F alkylene oxide modified di(meth)acrylate, hydrogenated bisphenol F glycidyl ether modified di(meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenyl alkylene oxide modified (meth)acrylate, nonylphenol (meth)acrylate, nonylphenol alkylene oxide modified (meth)acrylate, phenoxybenzyl (meth)acrylate, phenylbenzyl acrylate, biphenyl (meth)acrylate, biphenyl alkylene oxide modified (meth)acrylate, bisphenol A di(meth)acrylate, bisphenol A alkylene oxide modified di(meth)acrylate, bisphenol A caprolactone modified di(meth)acrylate, bisphenol A glycidyl ether modified di(meth)acrylate meth)acrylate, bisphenol F di(meth)acrylate, bisphenol F caprolactone modified di(meth)acrylate, bisphenol F alkylene oxide modified di(meth)acrylate, bisphenol F glycidyl ether modified di(meth)acrylate, fluorene di(meth)acrylate, fluorene alkylene oxide modified di(meth)acrylate, isobornyl (meth)acrylate, isobornyl di(meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyl alkylene oxide modified (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyl alkylene oxide modified (meth)acrylate, tricyclodecane diol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, adamantyl (meth)acrylate, adamantyl Manthyl di(meth)acrylate, 2-methyladamantyl (meth)acrylate, 2-ethyladamantyl (meth)acrylate, 2-isopropyladamantyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, (2-oxo-1,3-dioxolan-4-yl)methyl (meth)acrylate, mevalonic acid lactone (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate, dioxane glycol di(meth)acrylate, (3,4-epoxycyclohexyl)methyl (meth)acrylate, isosorbide di(meth)acrylate, isosorbide alkylene oxide modified di(meth)acrylate, and the like. These compounds can be used alone or in combination of two or more. Among these, compounds having two (meth)acryloyl groups and an alicyclic structure or a heterocyclic structure are preferred, since they can provide an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance, and hydrogenated bisphenol A alkylene oxide-modified di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, and dioxane glycol di(meth)acrylate are more preferred. Cyclohexane dimethanol mono(meth)acrylate containing a hydroxyl group may also be used.

In addition, examples of commercially available products of the component (B) include Miramer M1110, Miramer M1122, Miramer M1130, Miramer M1142, Miramer M1150, Miramer M1182, Miramer M1192, Miramer M140, Miramer M142, Miramer M144, Miramer M150, Miramer M164, Miramer M166, Miramer M1602, Miramer M240, Miramer M244, Miramer M2100, Miramer M220, Miramer M230, Miramer M240, Miramer M244, Miramer M250, Miramer M260, Miramer M270, Miramer M280, Miramer M290, Miramer M300, Miramer M310, Miramer M320, Miramer M330, Miramer M340, Miramer M350, Miramer M360, Miramer M370, Miramer M380, Miramer M390, Miramer M390, Miramer M40 ... M2200, Miramer M2300, Miramer M262, Miramer M290, Miramer M1183, Miramer M141, Miramer M151, Miramer M241, Miramer M245, Miramer M2101, Miramer M2301 manufactured by Shin-Nakamura Chemical Co., Ltd., NK Ester A-IB, NK Ester AMP-10G, NK Ester AMP-20GY, NK Ester A-LEN-10, NK Ester 401P, NK Ester A-DOG, NK Ester A-DCP, NK Ester A-BPEF, NK Ester A-BPE-2, NK Ester A-BPE-2.2", "NK Ester ABE-100", "NK Ester A-BPE-10", "NK Ester A-BPE-20", "NK Ester A-BPE-30", "NK Ester A-BPP3", "NK Ester A-B1206PE", "NK Ester IB", "NK Ester PHE-1G", "NK Ester PHE-2G", "NK Ester DCP", "NK Ester BPE-80N", "NK Ester BPE-100", "NK Ester BPE-200", "NK Ester BPE-300", "NK Ester BPE-500", "NK Ester BPE-900", "NK Ester BPE-1300N, Osaka Organic Chemical Industry Co., Ltd.'s IBXA, MEDOL-10, OXE-10, OXE-30, Viscoat #150, Viscoat #150D, Viscoat #155, Viscoat #160, Viscoat #192, Viscoat #196, Viscoat #200, Viscoat #700HV, Kyoeisha Chemical Co., Ltd.'s Light Ester CH, Light Ester THF (1000), Light Ester BZ, Light Ester PO , "Light Ester IB-X", "Light Ester BP-2EMK", "Light Acrylate PO-A", "Light Acrylate POB-A", "Light Acrylate P2H-A", "Light Acrylate P-200A", "Light Acrylate THF-A", "Light Acrylate IB-XA", "Light Acrylate BA-104", "Light Acrylate DCP-A", "Light Acrylate BP-4EAL", "Light Acrylate BP-4PA", "KAYARAD R-551", "KAYARAD R-712", "KAYARAD R-604", "KAYARAD R-712 ... R-684, Daiichi Kogyo Seiyaku Co., Ltd.'s "New Frontier PHE", "New Frontier PHE-2", "New Frontier PHE-2D", "New Frontier NP-1", "New Frontier NP-4", "New Frontier N-177E", "New Frontier OPPE", "New Frontier BPE-4", "New Frontier BPE-10", "New Frontier BPE-20", "New Frontier BPEM-4", "New Frontier BPEM-10", "New Frontier HBPE-4", "New Frontier HBPEM-10", Hitachi Chemical Co., Ltd.'s "Fancryl FA-512" AS", "Fancryl FA-513AS", "Fancryl FA-BZA", "Fancryl FA-310A", "Fancryl FA-314A", "Fancryl FA-318A", "Fancryl FA-THFA", "Fancryl FA-321A", "Fancryl FA-324A", "Fancryl FA-512M", "Fancryl FA-512MT", "Fancryl FA-513M", "Fancryl FA-BZM", "Fancryl FA-310M", "Fancryl FA-THFM", "Fancryl FA-320M", "Fancryl FA-321M", "Fancryl FA-3218M", etc.

The content of the (B) component in the active energy ray-curable composition is preferably in the range of 5 to 70% by mass, more preferably in the range of 10 to 60% by mass, and particularly preferably in the range of 20 to 50% by mass, since an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance can be obtained.

The compound (C) having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule (hereinafter abbreviated as "component (C)") essentially has one or two (meth)acryloyl groups and an alkylene glycol structure in one molecule. By using component (C), an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance can be obtained.

Examples of the alkylene glycol structure include 1,2-ethanediol (ethylene glycol), 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,2-propanediol (propylene glycol), 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 2-methyl-1,3-propanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 3-methyl-1,3-butanediol, 2-methyl-1,3-butanediol, 1,2-hexanediol, ethanol, 1,5-hexanediol, 2,5-hexanediol, 3-methyl-1,5-pentanediol, 2,3-dimethyl-2,3-butanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,2-heptanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 3,6-octanediol, 2,2,4-trimethyl 1,3-pentanediol, 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 1,2-nonanediol, 1,8-nonanediol, 2,8-nonanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 1,2-decanediol, 2,2-diisobutyl-1,3-propanediol, etc. These alkylene glycol structures may be present in one molecule, or may have two or more types. Among these, ethylene glycol, propylene glycol, and neopentyl glycol are preferred, since they provide an active energy ray-curable composition capable of forming a lens having excellent heat resistance and moist heat resistance. Furthermore, it is preferred that the number of repeating units of the alkylene glycol structure is 2 to 15, since they provide an active energy ray-curable composition capable of forming a lens having even better moist heat resistance.

In addition, examples of commercially available products of the component (C) include Miramer M170, Miramer M202, Miramer M210, Miramer M216, Miramer M220, Miramer M222, Miramer M232, Miramer M280, Miramer M282, Miramer M284, Miramer M286, Miramer M2040, Miramer M231, Miramer M233, Miramer M235, Miramer M281, and Miramer M283 manufactured by MIWON Co., Ltd., and NK Ester manufactured by Shin-Nakamura Chemical Co., Ltd. A-30G", "NK Ester A-90G", "NK Ester A-130G", "NK Ester AM-30PG", "NK Ester A-200", "NK Ester A-400", "NK Ester A-600", "NK Ester APG-100", "NK Ester APG-200", "NK Ester APG-400", "NK Ester APG-700", "NK Ester A-PTMG-65", "NK Ester M-20G", "NK Ester M-30G", "NK Ester M-40G", "NK Ester M-90G", "NK Ester M-130G", "NK Ester M-30PG", "NK Ester EH-4E", "NK Ester B-20G", "NK Ester S-12E", "NK Ester 2G", "NK Ester 3G", "NK Ester 4G", "NK Ester 9G", "NK Ester 14G", "NK Ester 3PG", "NK Ester 9PG", Kyoeisha Chemical Co., Ltd.'s "Light Ester BC", "Light Ester 130MA", "Light Ester BC", "Light Ester 2EG", "Light Ester 3EG", "Light Ester 4EG", "Light Ester 9EG", "Light Ester 14EG", "Light Acrylate EC-A", "Light Acrylate MTG-A", "Light Acrylate EHDG-AT", "Light Acrylate 130A", "Light Acrylate DPM-A", "Light Acrylate P2H-A", "Light Acrylate P-200A", "Light Acrylate 3EG-A", "Light Acrylate 4EG-A", "Light Acrylate 9EG-A", "Light Acrylate 14EG-A", "Light Acrylate PTMGA-250", Hitachi Chemical Co., Ltd.'s "Fancryl FA-240A", "Fancryl FA-P240A", "Fancryl FA-P270A", "Fancryl FA-PTG9A", "Fancryl FA-400M (100)", "Fancryl FA-240M", "Fancryl FA-PTG9M", Daiichi Kogyo Seiyaku Co., Ltd.'s "New Frontier ME-3," "New Frontier ME-4S," "New Frontier MPE-600," "New Frontier PE-200," "New Frontier PE-300," "New Frontier PE-400," "New Frontier PE-600," "New Frontier MPEM-400," "New Frontier TEGDMA," "KAYARAD PEG400DA" and "KAYARAD PEG400DA" manufactured by Nippon Kayaku Co., Ltd., and "Viscoat #190," "Viscoat #MTG," "MPE400A," "MPE550A," and "Viscoat #310HP" manufactured by Osaka Organic Chemical Industry Co., Ltd. are examples of such products.

The content of the component (C) in the active energy ray-curable composition is preferably in the range of 1 to 30% by mass, more preferably in the range of 5 to 25% by mass, and particularly preferably in the range of 10 to 20% by mass, since an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance can be obtained.

In addition to the components (A), (B) and (C), the active energy ray-curable composition of the present invention may contain, as necessary, a compound (D) having one or two (meth)acryloyl groups in one molecule and at least one hydroxyl group in one molecule (hereinafter abbreviated as "component (D)") for the purpose of further improving moist heat resistance.

Examples of the component (D) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxy-1-methylethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-hydroxy-3-phenylphenolpropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 3-hydroxy-3-methylbutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 5-hydroxypropyl (meth)acrylate, 6-hydroxypropyl (meth)acrylate, 7-hydroxypropyl (meth)acrylate, 8-hydroxypropyl (meth)acrylate, 9-hydroxypropyl (meth)acrylate, 10-hydroxypropyl (meth)acrylate, 11-hydroxypropyl (meth)acrylate, 12-hydroxypropyl (meth)acrylate, 13-hydroxypropyl (meth)acrylate, 14-hydroxypropyl (meth)acrylate, 15-hydroxypropyl (meth)acrylate, 16-hydroxypropyl (meth)acrylate, 17-hydroxypropyl (meth)acrylate, 18-hydroxypropyl (meth)acrylate, 19-hydroxypropyl (meth)acrylate, 20-hydroxypropyl (meth)acrylate, 21-hydroxypropyl (meth)acrylate, 22-hydroxypropyl (meth)acrylate, 23-hydroxypropyl (meth)acrylate, 24-hydroxypropyl (meth)acrylate, 25-hydroxypropyl (meth)acrylate, 26-hydroxypropyl (meth)acrylate, 27-hydroxypropyl (meth)acrylate, 28-hydroxypropyl (meth)acrylate, 29-hydroxypropyl (meth)acrylate, 30-hydroxypropyl (meth)acrylate, 31-hydroxypropyl (meth)acrylate, 32-hydroxypropyl (meth)acrylate, 33-hydroxypropyl (meth)acrylate, 34-hydroxypropyl (meth)acrylate, 35-hydroxypropyl (meth)acrylate, 36-hydroxypropyl (meth)acrylate , 37-hydroxy -hydroxy-1-adamantyl (meth)acrylate, 3,5-dihydroxy-1-adamantyl (meth)acrylate, glycerin mono(meth)acrylate, glycerin di(meth)acrylate, trimethylolpropane mono(meth)acrylate, trimethylolpropane di(meth)acrylate, ditrimethylolpropane mono(meth)acrylate, ditrimethylolpropane di(meth)acrylate, pentaerythritol mono(meth)acrylate, pentaerythritol di(meth)acrylate, dipentaerythritol mono(meth)acrylate, dipentaerythritol di(meth)acrylate, sorbitol mono(meth)acrylate, sorbitol di(meth)acrylate, mannitol mono(meth)acrylate, and mannitol di(meth)acrylate. In addition, compounds in which some or all of the hydroxyl groups of the above-mentioned compounds are modified with alkylene oxide or caprolactone can also be used. These compounds can be used alone or in combination of two or more. Among these, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate , and sorbitol ethylene oxide-modified di(meth)acrylate are preferred from the viewpoint of obtaining even higher Abbe number, heat resistance, and moist heat resistance.

The component (D) may also be an epoxy (meth)acrylate, such as a reaction product of a compound having one or two glycidyl groups in one molecule with (meth)acrylic acid, or a reaction product of a compound having a (meth)acryloyl group and a glycidyl group in one molecule with a carboxylic acid and/or a dicarboxylic acid anhydride.

Examples of the compounds having one or two glycidyl groups in one molecule include dodecyl glycidyl ether, tetradecyl glycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1.6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 1,2-epoxy-4-vinylcyclohexane, 3,4-epoxycyclohexane, 4-vinylcyclohexane, 5-vinylcyclohexane, 6-vinylcyclohexane, 7-vinylcyclohexane, 8-vinylcyclohexane, 9-vinylcyclohexane, 10-vinylcyclohexane, 11-vinylcyclohexane, 12-vinylcyclohexane, 13-vinylcyclohexane, 14-vinylcyclohexane, 15-vinylcyclohexane, 16-vinylcyclohexane, 17-vinylcyclohexane, 18-vinylcyclohexane, 19-vinylcyclohexane, 20-vinylcyclohexane, 21-vinylcyclohexane, 22-vinylcyclohexane, 23-vinylcyclohexane, 24-vinylcyclohexane, 25-vinylcyclohexane, 26-vinylcyclohexane, 27-vinylcyclohexane, 28-vinylcyclohexane, 29-vinylcyclohexane, 30-vinylcyclohexane, 31-vinylcyclohexane, 32-vinylcyclohexane, 33-vinylcyclohexane, 34-vinylcyclohexane, 35-vinylcyclohexane, 36-vinylcyclohexane, 37-vinylcyclohexane, 38-vinylcyclohexane, 39-vinylcyclohexane, 40-vinylcyclohexane, 41-vinylcyclohexane, 42-vinylcyclohexane, 43-vinylcyclo Cyclohexyl methyl methacrylate, 1,4-cyclohexanedimethanol monoglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 3,4,3,4-diepoxybicyclohexyl, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, ε-caprolactone-modified 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bisphenol A monoglycidyl ether, bisphenol A diglycidyl ether, bisphenol A alkylene oxide-modified monoglycidyl ether, bisphenol A alkylene oxide-modified diglycidyl ether glycidyl ether, bisphenol A caprolactone modified monoglycidyl ether, bisphenol A caprolactone modified diglycidyl ether, hydrogenated bisphenol A monoglycidyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol A alkylene oxide modified monoglycidyl ether, hydrogenated bisphenol A alkylene oxide modified diglycidyl ether, hydrogenated bisphenol A caprolactone modified monoglycidyl ether, hydrogenated bisphenol A caprolactone modified diglycidyl ether, bisphenol F monoglycidyl ether, bisphenol F diglycidyl ether, bisphenol F alkylene oxide modified diglycidyl ether Examples of the glycidyl ether include bisphenol F alkylene oxide modified monoglycidyl ether, bisphenol F caprolactone modified monoglycidyl ether, bisphenol F caprolactone modified diglycidyl ether, hydrogenated bisphenol F monoglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol F alkylene oxide modified monoglycidyl ether, hydrogenated bisphenol F alkylene oxide modified diglycidyl ether, hydrogenated bisphenol F caprolactone modified monoglycidyl ether, and hydrogenated bisphenol F caprolactone modified diglycidyl ether.

Examples of the compound having a (meth)acryloyl group and a glycidyl group in one molecule include glycidyl (meth)acrylate, 4-hydroxybutyl acrylate glycidyl ether, and 3,4-epoxycyclohexylmethyl (meth)acrylate.

Examples of the carboxylic acid and/or dicarboxylic anhydride include (meth)acrylic acid, 1,2-cyclohexanedicarboxylic anhydride, 4-methylcyclohexane-1,2-dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, succinic anhydride, octenyl succinic anhydride, tetrapropenyl Examples include succinic anhydride, 3-dodecenyl succinic anhydride, 3,3,4,4-tetrahydro-3,3-bifuran-2,2,5,5-tetraone, 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride, trimellitic anhydride, bis(1,3-dihydro-1,3-dioxo-5-isobenzofuran carboxylic acid) 2-acetyloxy-1,3-propanediyl, etc.

Commercially available products of the component (D) include, for example, Miramer M100 and Miramer M1051 manufactured by MIWON Co., Ltd., NK Ester 702A, NK Ester 401P, and NK Ester 701A manufactured by Shin-Nakamura Chemical Co., Ltd., HEA, HPA, 4-HBA, and Viscoat #540 manufactured by Osaka Organic Chemical Industry Co., Ltd., Light Ester HO-250(N), Light Ester HOP(N), Light Ester HOP-A(N), Light Ester HOA(N), Light Ester HOB(N), Light Ester G-101P, Light Ester G-201P, Light Acrylate HOB-A, Epoxy Ester M-600A, and HOA-MPE(N) manufactured by Kyoeisha Chemical Co., Ltd., New Frontier PGA manufactured by Daiichi Kogyo Seiyaku Co., Ltd., and KAYARAD manufactured by Nippon Kayaku Co., Ltd. Examples include "R-128H", "KAYARAD R-167" manufactured by Toagosei Co., Ltd., "Aronix M-920" and "Aronix M-926" manufactured by Toa Gosei Co., Ltd., "4HBA" and "CHDMMA" manufactured by Mitsubishi Chemical Corporation, and "Resist Monomer HMA" and "Resist Monomer DHMA" manufactured by Daicel Corporation.

The content of the (D) component in the active energy ray-curable composition is preferably in the range of 1 to 30% by mass, and more preferably in the range of 5 to 20% by mass, since an active energy ray-curable composition capable of forming a lens having a high Abbe number and excellent heat resistance and moist heat resistance can be obtained.

The active energy ray-curable composition of the present invention may further contain other compounds in addition to the components (A), (B), (C) and (D), if necessary.

Examples of the other compounds include (meth)acrylates having a hydroxyl group. Examples of the (meth)acrylates having a hydroxyl group include pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and further, alkylene oxide-modified and/or caprolactone-modified compounds of the (meth)acrylates having a hydroxyl group, urethane acrylate, acrylic (meth)acrylate, polyester polyol (meth)acrylate, and epoxy acrylate.

The active energy ray curable composition of the present invention can be irradiated with active energy rays to obtain a cured product or lens. The active energy ray refers to ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. When ultraviolet rays are irradiated as the active energy ray, it is preferable to add a photopolymerization initiator (E) to the active energy ray curable composition of the present invention to improve the curability. On the other hand, when ionizing radiation such as electron beams, α rays, β rays, and γ rays is used, the composition is rapidly cured without using the photopolymerization initiator (E), so there is no need to add the photopolymerization initiator (E).

Examples of the photopolymerization initiator (E) include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo{2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone}, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexylphenyl ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propane- acetophenone compounds such as 1-one and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone; benzoin compounds such as benzoin, benzoin methyl ether and benzoin isopropyl ether; acylphosphine oxide compounds such as 2,4,6-trimethylbenzoin diphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; benzyl (dibenzoyl), methylphenyl glyoxy ester, oxyphenylacetic acid 2-(2-hydroxyethoxy)ethyl ester, oxyphenyl benzyl compounds such as 2-(2-oxo-2-phenylacetoxyethoxy)ethyl ester of benzoyl acetate; benzophenones such as benzophenone, o-benzoylbenzoic acid methyl-4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, acrylated benzophenone, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 2,4,6-trimethylbenzophenone, and 4-methylbenzophenone; thioxanthone compounds such as 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone; aminobenzophenone compounds such as Michler's ketone and 4,4'-diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, camphorquinone, and 1-[4-(4-benzoylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl)propan-1-one. These photopolymerization initiators can be used alone or in combination of two or more.

Examples of commercially available photopolymerization initiators (E) include "Omnirad 1173", "Omnirad 184", "Omnirad 127", "Omnirad 2959", "Omnirad 369", "Omnirad 379", "Omnirad 907", "Omnirad 4265", "Omnirad 1000", "Omnirad 651", "Omnirad TPO", "Omnirad TPO-L", "Omnirad 819", "Omnirad 2022", "Omnirad 2100", "Omnirad 754", "Omnirad BP", and "Omnirad 1000", all manufactured by IGM. 4MBZ”, “Omnirad 4PBZ”, “Omnirad 410”, “Omnirad OMBB”, “Omnirad BMS”, “Omnirad 500”, “Omnirad 81”, “Omnirad ITX”, “Omnirad DETX ”, “Omnirad MBF”, “Omnirad EMK”, “Omnirad 784”, “Omnirad 1312”, “Omnirad BCIM”, “Omnirad BL 723”, “Omnirad BL 724”, “Omnirad BL 750” , “Omnirad BL751”, “Omnirad EDB”, “Omnirad EHA", "Omnirad IADB", "Esacure KIP 150", "Esacure KIP 100F", "Esacure KIP 75LT", "Esacure KIP IT", "Esacure TZT", "Esacure KT55 ”, “Esacure TZM”, “Esacure ONE”, “Esacure 1001M”, “Esacure KIP 160”, “Esacure A 198”, “Esacure KTO 46”, “Esacure DP 250”, “Omnipol 910”, “Omnipol 9210”, “Omnipol BP”, “Omnipol TX”, “Omnipol Examples of photopolymerization initiators include "Kayacure DETX", "Kayacure MBP", "Kayacure DMBI", "Kayacure EPA", and "Kayacure OA" manufactured by Nippon Kayaku Co., Ltd., "Vicure 10" and "Vicure 55" manufactured by Stouffer Chemical Co., Ltd., "Trigonal P1" manufactured by Akzo Co., Ltd., "Sandray 1000" manufactured by Sandoz Co., Ltd., "Deep" manufactured by Upjohn Co., Ltd., "Quantacure PDO", "Quantacure ITX", and "Quantacure EPD" manufactured by Ward Blenkinsop Co., Ltd., and "Runtecure-1104" manufactured by Runtec Co., Ltd. These photopolymerization initiators can be used alone or in combination of two or more types.

From the viewpoint of obtaining sufficient curability, the amount of the photopolymerization initiator (E) used is preferably in the range of 0.05 to 20 parts by mass, more preferably in the range of 0.1 to 10 parts by mass, and particularly preferably in the range of 0.5 to 5 parts by mass, relative to 100 parts by mass of the total mass of the components (A), (B), (C), and (D).

In addition, a heat stabilizer (F) may be added to the active energy ray-curable composition of the present invention in order to further improve heat resistance.

Examples of the heat resistance stabilizer include ethanethiol, 2-methylpropane-2-thiol, n-dodecanethiol, 2,3,3,4,4,5-hexamethylhexane-2-thiol, 2-mercaptoethanol, 4-mercapto-1-butanol, methyl mercaptoacetate, methyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, 3-methoxybutyl 3-mercaptopropionate, n-octyl 3-mercaptopropionate, stearyl 3-mercaptopropionate, 3-(trimethoxysilyl)propane-1-thiol, 3-(triethoxysilyl)propane-1-thiol, benzenethiol, benzylthiol, 3-methylbenzenethiol, 4-methylbenzenethiol, naphthalene-2-thiol, pyridine-2-thiol, benzimidazole- 2-Thiol, benzothiazole-2-thiol, 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,10-decanedithiol, 2,3-dihydroxy-1,4-butanedithiol, 3,6-dioxa-1,8-octanedithiol 3,7-dithia-1,9-nonanedithiol, 1,4-bis(3-mercaptopropionyloxy)butane, 1,4-bis(3-mercaptobutyryloxy)butane, tetraethylene glycol bis(3-mercaptopropionate), 1,2-benzenedithiol, 1,3-benzenedithiol, 1,4-benzenedithiol, 2,3-diamino-1,4-benzenedithiol, 4,5-dimethyl-O-xylylenedithiol, toluene-3,4-dithiol, 4,4'-biphenyldithiol, 1,5-naphthalenedithiol, 6-(dibutylamino)-1,3,5-triazine-2,4-dithiol, 2-amino-1,3,5-triazine-4,6-dithiol, 6-anilino-1,3,5-triazine-2,4-dithiol, 6-(4'-anilinophenyl-isopropylamino) )-1,3,5-triazine-2,4-dithiol, 6-(3',5'-tert-butyl-4'-hydroxyanilino)-1,3,5-triazine-2,4-dithiol, quinoxaline-2,3-dithiol, purine-2,6-dithiol, 1,3,4-thiadiazole-2,5-dithiol, bis(2-mercaptoethyl)ether, trimethylolethane tris(3-mercaptopropione ester), trimethylolethane tris(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptopropionate), trimethylolpropane tris(3-mercaptobutyrate), 1,3,5-benzenetrithiol, 1,3,5-triazine-2,4,6-trithiol, tris[2-(3-mercaptopropionyloxy)ethyl]isocyanurate, tris[2-(3-mercaptobutyryloxy)ethyl]isocyanurate, pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptobutyrate), and other compounds having a mercapto group. These heat stabilizers can be used alone or in combination of two or more.

Examples of commercially available heat stabilizers include "Chiokalcol 20" manufactured by Kao Corporation, "Karenz MT PE1", "Karenz MT BD1", "Karenz MT NR1", "TPMB", and "TEMB" manufactured by Showa Denko K.K., and "TMMP", "TEMPIC", "PEMP", "EGMP-4", "DPMP", "TMMP II-20P", and "PEMP II-20P" manufactured by SC Organic Chemical Co., Ltd.

The amount of the heat stabilizer (F) used is preferably in the range of 0.01 to 10 parts by mass, more preferably in the range of 0.1 to 5 parts by mass, and particularly preferably in the range of 0.5 to 3 parts by mass, per 100 parts by mass of the total mass of the (A), (B), (C) and (D) components, from the viewpoint of obtaining sufficient heat resistance.

The active energy ray-curable composition of the present invention may further contain other additives in addition to the components (A) to (F) as necessary.

Examples of the other additives include additives such as polymerization inhibitors, photosensitizers, surface conditioners, antistatic agents, defoamers, viscosity modifiers, light stabilizers, weather stabilizers, ultraviolet absorbers, antioxidants, leveling agents, organic pigments, inorganic pigments, pigment dispersants, silica beads, and organic beads; and inorganic fillers such as silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, cerium oxide, and antimony oxide. These other additives can be used alone or in combination of two or more kinds. Among these, antioxidants are preferred because they can improve heat resistance.

Examples of the antioxidant include phenol-based antioxidants, phosphite-based antioxidants, and sulfur-based antioxidants. These antioxidants can be used alone or in combination of two or more.

Examples of the phenol-based antioxidants include styrenated phenol, 2,6-ditertiary butyl-p-cresol, 2,5-ditertiary butyl hydroquinone, 2,5-ditertiary amyl hydroquinone, 3-(3,5-ditertiary butyl-4-hydroxyphenyl)octadecyl propionate, 2,4-bis(octylthiomethyl)-6-methylphenol, 2,2-methylenebis(6-tertiary butyl-p-cresol), 2,2-methylenebis(6-tertiary butyl-4-ethylphenol), 4 ,4-butylidenebis(6-tert-butyl-m-cresol), 4,4-thiobis(6-tert-butyl-m-cresol), 2,2-thiodiethylbis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propionate], 1,6-hexanediol bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propionate], bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate][ethylene bis(oxyethylene)], bis[3-[3- (tert-butyl)-4-hydroxy-5-methylphenyl]propanoic acid]2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diylbis(2-methylpropane-2,1-diyl), N,N-bis[2-[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]ethyl]oxamide, N,N-(hexane-1,6-diyl)bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide], 2,4,6-tris(3,5-ditert-butyl) 1,3,5-tris(3,5-ditertiarybutyl-4-hydroxybenzyl)mesitylene, 1,3,5-tris(3,5-ditertiarybutyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,3-tris(2-methyl-4-hydroxy-5-tertiarybutylphenyl)butane, pentaerythritol tetrakis[3-(3,5-ditertiarybutyl-4-hydroxyphenyl)propionate], diethyl(3,5-ditertiarybutyl-4-hydroxybenzyl)phosphonate, etc.

Examples of commercially available phenol-based antioxidants include "IRGANOX 1010", "IRGANOX 1010FF", "IRGANOX 1035", "IRGANOX 1035FF (W&C)", "IRGANOX 1076", "IRGANOX 1076FD", "IRGANOX 1098", "IRGANOX 1135", "IRGANOX 1330", "IRGANOX 1520L", "IRGANOX 245", "IRGANOX 245FF", "IRGANOX 259", and "IRGANOX 3114" manufactured by BASF Corporation, and "ANTAGE BHT", "ANTAGE DAH", and "ANTAGE 3114" manufactured by Kawaguchi Chemical Industry Co., Ltd. DBH", "ANTAGE W-300", "ANTAGE W-400", "ANTAGE W-500", "ANTAGE Crystal", "ANTAGE SP", "ANTAGE HP-200", "ANTAGE HP-300", manufactured by ADEKA CORPORATION, "ADK STAB AO-20", "ADK STAB AO-30", "ADK STAB AO-40", "ADK STAB AO-50", "ADK STAB AO-50F", "ADK STAB AO-50T", "ADK STAB AO-60", "ADK STAB AO-60G", "ADK STAB AO-80", "ADK STAB AO-330", manufactured by Sumitomo Chemical Co., Ltd., "SUMILIZER GA-80", "SUMILIZER GP," "SUMILIZER MDP-S," "SUMILIZER WX-R," "SUMILIZER WX-RC," Mitsubishi Chemical Corporation's "Yoshinox BB," and Johoku Chemical Industry Co., Ltd.'s "JC-356."

Examples of the phosphite antioxidants include tris(2-ethylhexyl)phosphite, tridecyl phosphite, triisodecyl phosphite, trilauryl phosphite, tris(tridecyl)phosphite, tri(stearyl)phosphite, diphenyl mono(2-ethylhexyl)phosphite, diphenyl monodecyl phosphite, diphenyl isodecyl phosphite, diphenyl mono(tridecyl)phosphite, triphenyl phosphite, tricresyl phosphite, tris(2,4-ditertiary butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetraphenyl dipropylene glycol diphosphite, 4,4-butylidene bis(3-methyl-6-tertiary butylphenyl ditridecyl phosphite), tetra(C12 to C15 alkyl)-4,4-isopropylidenediphenyl diphosphite, 3,9-bis(octadecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,6-ditertiarybutyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 2,4,8,10-tetrakis(1,1-dimethylethyl)-6-[(2-ethylhexyl)oxy]-12H-dibenzo[d,g][1,3,2]dioxaphosphocin, bis(decyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, hydrogenated bisphenol A pentaerythritol phosphite polymer, etc.

Examples of commercially available phosphite antioxidants include "IRGAFOS 168" and "IRGAFOS 168FF" manufactured by BASF, and "ADK STAB PEP-8", "ADK STAB PEP-36", "ADK STAB HP-10", "ADK STAB 2112", "ADK STAB 2112RG", "ADK STAB 1178", "ADK STAB 1500", "ADK STAB C", "ADK STAB 135A", "ADK STAB 3010", and "ADK STAB 135A" manufactured by ADEKA CORPORATION. TPP" and Johoku Chemical Industry Co., Ltd.'s "JP-360", "JP-351", "JP-3CP", "JP-308E", "JPE-308E", "JP-310", "JP-312L", "JP-333E", "JPM-308", "JPM-311", "JPM-313", "JPP-100", "JA-805", "JPH-1200", "JPP-88", "JPE-10", "JPE-13R", "JP-318E", "JPP-2000PT", "JP-650", "JPH-3800", etc.

Examples of the sulfur-based antioxidant include didodecyl 3,3-thiodipropionate, ditridecyl 3,3-thiobispropionate, dioctadecyl 3,3-thiodipropionate, and pentaerythritol tetrakis[3-(dodecylthio)propionate].

Examples of commercially available sulfur-based antioxidants include "IRGANOX PS800FL" and "IRGANOX PS802FL" manufactured by BASF, "ADEKA STAB AO-412S" and "ADEKA STAB AO-503" manufactured by ADEKA CORPORATION, "KEMINOX PLS" manufactured by Chemipro Chemical Co., Ltd., and "SUMILIZER TP-D" manufactured by Sumitomo Chemical Co., Ltd.

As the other additives, inorganic fillers are preferably used to adjust the refractive index and thermal expansion coefficient. Examples of the inorganic fillers include silica fine particles, zirconia fine particles, other fine particles, etc., and each of these can be used independently, or in combination of two or more. The particle size of the inorganic filler is preferably 1000 nm or less, more preferably 500 nm or less, and particularly preferably 100 nm or less.

Commercially available products of the silica fine particles include, for example, "Methanol Silica Sol", "MA-ST-M", "MA-ST-L", "IPA-ST", "IPA-ST-L", "IPA-ST-ZL", "IPA-ST-UP", "EG-ST", "NPC-ST-30", "PGM-ST", "DMAC-ST", "MEK-ST-40", "MEK-ST-L", "MEK-ST-ZL", "MEK-ST-UP", and MIBK-ST", "MIBK-ST-L", "CHO-ST-M", "EAT-ST", "PMA-ST", "TOL-ST", "MEK-AC-2140Z", "MEK-AC-4130Y", "MEK-AC-5140Z", "MIBK-AC-2140 Z”, “MIBK-SD-L”, “PGM-AC-2140Y”, “PGM-AC-4140Y”, “MEK-EC-2130Y”, “Seahoster” manufactured by Nippon Shokubai Co., Ltd. KE-E10", "SeaHoster KE-E30", "SeaHoster KE-E150", "SeaHoster KE-W10", "SeaHoster KE-W30", "SeaHoster KE-W50", "SeaHoster KE-P10", "SeaHoster KE-P30", "SeaHoster KE-P50", "SeaHoster KE-P100", "SeaHoster KE-P150", "SeaHoster KE-P250", "SeaHoster KE-S10", "SeaHoster KE-S30", "SeaHoster KE-S50", "SeaHoster KE-S100", "SeaHoster KE-S150", "SeaHoster Examples include "KE-S250" manufactured by Shin-Etsu Chemical Co., Ltd., "QSG-10", "QSG-30", "QSG-100", and "QSG-170" manufactured by Shin-Etsu Chemical Co., Ltd., "Admanano YA010C", "YA050C", and "YA100C" manufactured by Admatechs Co., Ltd., and "DLSB-001" and "DLSB-002" manufactured by Daiken Chemical Co., Ltd.

Examples of commercially available zirconia fine particles include "ZHR-101", "ZHR-103", and "ZHR-200" manufactured by Daiichi Kogyo Seiyaku Co., Ltd., "Zircostar ZP-153" and "Zircostar HR-101" manufactured by Nippon Shokubai Co., Ltd., "SZR-W", "SZR-M", "SZR-CW", "SZR-CM", "SZR-KM", and "SZR-K" manufactured by Sakai Chemical Industry Co., Ltd., "DLZ-001", "DLZ-007", "DLZ-003U", "DLM-001", and "DLM-002" manufactured by Daiken Chemical Industry Co., Ltd., "ZSL-10A", "ZSL-10T", "ZSL-20N", and "ZSL-00014" manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd., "Zirconeo-Cw" and "Zirconeo-Ck" manufactured by ITEC Co., Ltd., and "TZP-103" manufactured by Taisei Kako Co., Ltd.

Examples of commercially available products of the other fine particles include titania fine particles such as "TTP-113" and "TTP-1132" manufactured by Taisei Chemical Industry Co., Ltd., barium titanate fine particles such as "DLB-001", "DLB-002", and "DLB-003" manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd., antimony tin oxide fine particles such as "DLAT-001" manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd., and indium tin oxide fine particles such as "DLIT-001" manufactured by Daiichi Kigenso Kagaku Kogyo Co., Ltd.

As a method for obtaining a cured product of the active energy ray-curable composition, for example, a method of coating the active energy ray-curable composition on a substrate and then irradiating the substrate with active energy rays can be mentioned.

Examples of the substrate include polyester-based resins such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate; polyolefin-based resins such as polypropylene, polyethylene, and polymethylpentene; cellulose-based resins such as cellulose acetate (diacetyl cellulose, triacetyl cellulose, etc.), cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate, and cellulose nitrate; acrylic resins such as polymethyl methacrylate; vinyl chloride-based resins such as polyvinyl chloride and polyvinylidene chloride; polyvinyl alcohol; ethylene-vinyl acetate copolymer; polystyrene; polyamide; polycarbonate polyimide, polyetherimide, and other polyimide-based resins; norbornene-based resins (e.g., Zeonor manufactured by Zeon Corporation), modified norbornene-based resins (e.g., Arton manufactured by JSR Corporation), and cyclic olefin copolymers (e.g., Apel manufactured by Mitsui Chemicals, Inc.) and other resin films; semiconductor wafers such as silicon, silicon carbide, silicon nitride, sapphire, aluminum nitride, gallium nitride, gallium phosphide, gallium arsenide, and indium phosphide; and glasses such as quartz glass, borosilicate glass, soda-lime glass, silicate glass, and optical glass (crown glass, flint glass), etc., can be used.

Methods for applying the active energy ray-curable composition of the present invention to the substrate include, for example, die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, kiss coating, spray coating, dip coating, spinner coating, brush coating, solid coating by silk screen, wire bar coating, flow coating, dispenser, inkjet printing, screen printing, offset printing, etc.

The active energy rays that cure the active energy ray-curable composition are, as described above, ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. Here, when ultraviolet rays are used as the active energy rays, examples of devices that irradiate the ultraviolet rays include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, electrodeless lamps (fusion lamps), chemical lamps, black light lamps, mercury-xenon lamps, short arc lamps, helium-cadmium lasers, argon lasers, sunlight, and LED lamps.

The irradiation amount (accumulated light amount) of the active energy rays is preferably 100 to 10,000 mJ/cm ² , and more preferably 300 to 8,000 mJ/cm ^2. The irradiation amount of the active energy rays is based on a value measured using an actinometer suitable for the desired excitation wavelength, and examples of the irradiation amount include Iwasaki Electric Co., Ltd. Ai ultraviolet integrated illuminometer UVPF-A2 series, Hamamatsu Photonics Co., Ltd. ultraviolet actinometer C9536/H9535 series, C9536/H9958 series, C10427/H10428 series, Ushio Electric Co., Ltd. ultraviolet integrated actinometer UIT-201, UIT-250, UIT-θ series, etc. can be used. In particular, in the present invention, the integrated light amount measured using Iwasaki Electric Co., Ltd. Ai ultraviolet integrated illuminometer UVPF-A2 (PD-365) is used as the standard.

The irradiation of the active energy rays may be carried out in one step or in two or more steps.

The thickness of the cured product of the active energy ray-curable composition of the present invention is preferably in the range of 1 to 1000 μm, and more preferably in the range of 50 to 500 μm, in order to ensure sufficient hardness of the cured product.

The refractive index (n _d ) of the cured product is preferably in the range of 1.40 to 1.60, and more preferably in the range of 1.45 to 1.55. The refractive index of the cured product is a value measured in accordance with JIS test method K7142:2014, Method A.

The Abbe number (ν _d ) of the cured product is preferably 53 or more, more preferably in the range of 53 to 60, even more preferably in the range of 55 to 59, and particularly preferably in the range of 56 to 58. The Abbe number of the cured product is a value calculated based on the refractive index measured in accordance with JIS test method K7142:2014, Method A.

The light transmittance of the cured product at a wavelength of 410 nm is preferably 85% or more, more preferably 88% or more, and particularly preferably 90% or more, from the viewpoint of suitable use in optical lenses. The method for measuring the light transmittance will be described in detail in the Examples.

The light transmittance of the cured product after the heat resistance test is preferably within ±5% of the initial light transmittance at a wavelength of 410 nm, more preferably within ±3%, and particularly preferably within ±1%, from the viewpoint of suitable use in optical lenses having solder reflow resistance. The method for measuring the light transmittance after the heat resistance test will be described in detail in the Examples.

The water absorption rate of the cured product is preferably in the range of 0.1% to 4.0%, more preferably in the range of 0.3 to 3.5%, and particularly preferably in the range of 0.5 to 2.5%, in order to prevent defects from occurring inside the cured product in a high-temperature and high-humidity environment. The water absorption rate of the cured product is a calculated value that takes into account the amount dissolved in water, using a measured value in accordance with JIS test method K7209:2000, Method C.

The moist heat resistance of the cured product is such that, in order to prevent defects from occurring inside the cured product in a high temperature and high humidity environment, a moist heat test is performed under conditions of a temperature of 85°C, humidity of 85% RH, and time of 1000 hours. As a result, it is preferable that there is no peeling from the substrate, it is more preferable that there are no defects at the interface between the cured product and the substrate, and it is particularly preferable that there are no defects inside the cured product. The method for evaluating the moist heat resistance of the cured product will be described in detail in the Examples.

The lens of the present invention has the cured product. Furthermore, the lens may have an inorganic layer made of an inorganic compound on at least one side of the cured product, if necessary, and may further have a substrate.

The lens of the present invention can also be used as a wafer-level lens by imprint molding.

The method for producing the lens of the present invention is not particularly limited and may be any method. For example, the active energy ray curable composition is applied to a substrate such as a wafer or glass, and the substrate is shaped into a desired shape using a mold. The composition is then temporarily cured by irradiating the active energy ray. After the mold is released, the uncured active energy ray curable composition is washed with a solvent in a development step, and then the composition is again irradiated with active energy ray for full curing. If necessary, an inorganic layer made of an inorganic compound is formed on the surface of the cured product by physical vapor deposition or the like. Finally, the substrate is divided into individual pieces.

Examples of the solvent include ketone-based solvents such as methyl ethyl ketone, acetone, isobutyl ketone, cyclopentanone, and cyclohexanone; cyclic ether-based solvents such as tetrahydrofuran, dioxolane, and dioxane; ester-based solvents such as methyl acetate, ethyl acetate, and butyl acetate; aromatic solvents such as toluene, xylene, and solvent naphtha; alicyclic hydrocarbon-based solvents such as cyclohexane and methylcyclohexane; alcohol-based solvents such as carbitol, cellosolve, methanol, isopropanol, butanol, and propylene glycol monomethyl ether; and glycol ether-based solvents such as alkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether, and dialkylene glycol monoalkyl ether acetate. These solvents can be used alone or in combination of two or more.

The inorganic layer refers to a layer made of an inorganic compound, and generally has functions such as anti-reflection and scratch resistance.

Examples of the inorganic compounds include metal oxides, complex oxides, metal nitrides, metal fluorides, complex fluorides, silicon oxides, silicon nitrides, and mixtures thereof.

Examples of the metals include lithium, sodium, magnesium, aluminum, titanium, yttrium, indium, tin, zirconium, niobium, cerium, hafnium, and tantalum.

When the inorganic layer is used as an anti-reflection layer (also called an anti-reflection film layer), the anti-reflection film layer may be a single layer, or may have a low refractive index layer and a high refractive index layer. In addition, each of the low refractive index layer and the high refractive index layer may be one layer or multiple layers. The stacking order of the low refractive index layer and the high refractive index layer is not particularly limited.

Examples of inorganic compounds used in the high refractive index layer include lanthanum titanate, zirconium oxide, titanium oxide, tantalum oxide, niobium oxide, hafnium oxide, cerium oxide, yttrium oxide, and mixtures thereof.

Examples of inorganic compounds used in the low refractive index layer include silicon oxide, silicon nitride, magnesium fluoride, aluminum fluoride, and mixtures thereof.

The inorganic layer is obtained by forming a film on the surface of the resin layer. The method for forming the inorganic layer is not particularly limited, and any known film forming method can be used as appropriate, but it is preferable to form the film by physical vapor deposition (PVD) or chemical vapor deposition (CVD).

From the viewpoint of consistency and simplification of the film formation process, it is more preferable to use physical vapor deposition (PVD), and examples of the film formation method include vacuum deposition, ion plating, sputtering, etc.

For example, the vacuum deposition can be performed using a resistance heating method, a high-frequency induction heating method, an electron beam heating method, etc.

The sputtering may be DC sputtering or RF sputtering, or may be magnetron sputtering or ion beam sputtering. It may also be a parallel plate target system or a facing target system. Examples of gases to be introduced into the vacuum chamber include argon, krypton, oxygen, and nitrogen, and each may be used alone or in a mixture of two or more types.

The thickness of the inorganic layer can be adjusted as appropriate depending on the intended function, but if the intended function is anti-reflection, a thickness in the range of 10 nm to 5,000 nm is preferred, and from the standpoint of the film strength of the inorganic layer and productivity, a thickness in the range of 100 nm to 2,000 nm is more preferred, and a thickness in the range of 250 nm to 1,000 nm is particularly preferred.

As described above, the cured product formed by the active energy ray-curable composition of the present invention has a high Abbe number and high light transmittance, has excellent heat resistance and moist heat resistance, and can be easily cured by irradiation with active energy rays, and therefore can be suitably used for lens production by photoimprinting. In addition, a camera module having the above lens can be provided.

The present invention will be explained in more detail below with reference to the following examples.

[Example 1]
An active energy ray-curable composition was prepared by mixing 60 parts by mass of polycarbonate diol diacrylate ("UM-90(1/3)DA" manufactured by Ube Industries, Ltd.: R ¹ in general formula (1) is a hydrogen atom, R ² are each independently a linear hydrocarbon group having 6 carbon atoms and a cyclohexane structure arranged randomly, and n is 4 to 5) as a component (A), 20 parts by mass of tricyclodecane dimethanol dimethacrylate ("DCP-M" manufactured by Kyoeisha Chemical Co., Ltd.) as a component (B), 20 parts by mass of polyethylene glycol diacrylate (number of repeating units: 4) ("A-200" manufactured by Shin-Nakamura Chemical Co., Ltd.) as a component (C), and 1 part by mass of 1-hydroxycyclohexyl phenyl ketone ("I-184" manufactured by BASF) as a component (E). The mixture was heated to 50° C. and then stirred and mixed for 10 minutes at a rotation speed of 1,000 rpm using a homodisper.

[Examples 2 to 13, Comparative Examples 1 to 7]
Active energy ray-curable compositions were prepared in the same manner as in Example 1, except that the types and/or amounts of (A), (B), (C), (D), and (F) were changed as shown in Tables 1 to 3.

[Method of measuring refractive index]
The active energy ray curable compositions obtained in the Examples and Comparative Examples were poured into a triangular prism mold (thickness 5 mm, length of one side 10 mm) and irradiated with 3,000 mJ/ ^cm2 of ultraviolet light using a belt conveyor type ultraviolet irradiation device (120 W metal halide lamp) manufactured by Eye Graphics Co., Ltd. to produce a triangular prism. The refractive indexes of the obtained triangular prism at 25°C for the d-line, F-line, and C-line were measured using a Kalnew precision refractometer "KPR-3000" manufactured by Shimadzu Corporation. A matching liquid having a refractive index (n _d ) closest to the refractive index (n _d ) of the cured product was appropriately selected and used.

[Calculation method of Abbe number]
The Abbe number (ν _d ) was calculated according to the following formula using the refractive indices of the d line, F line, and C line measured by the above-mentioned [Method of measuring refractive index].

[Method of measuring transmittance]
The active energy ray curable compositions obtained in the Examples and Comparative Examples were dropped onto a glass plate that had been subjected to a release treatment with octadecyltrichlorosilane, and 1 mm thick shim plates were placed on the left and right of the oil droplet as spacers, and the oil droplet was then sandwiched between two glass plates that had also been subjected to a release treatment with octadecyltrichlorosilane. The oil droplet of the active energy ray curable composition sandwiched between the two glass plates was irradiated with an irradiation intensity of 50 mW/cm ² and an accumulated light amount of 8000 mJ/cm ² using a UV-LED irradiation device "LHPUV365/2501" manufactured by Iwasaki Electric Co., Ltd., to obtain a coin-shaped cured product with a thickness of about 1 mm. The obtained coin-shaped cured product was heated in a blower oven at 100°C for 20 minutes, and then the initial transmittance at a wavelength of 410 nm was measured using a UV-visible near-infrared spectrophotometer "V-770" manufactured by JASCO Corporation.

[Method for measuring transmittance after heat resistance test]
The coin-shaped cured product measured by the transmittance measurement method was heated in a fan oven (1) at 175°C for 10 minutes and (2) at 260°C for 6 minutes, and then the transmittance at a wavelength of 410 nm was measured using a UV-Visible-Near-Infrared Spectrophotometer "V-770" manufactured by JASCO Corporation as transmittance after heat resistance test 1 and transmittance after heat resistance test 2. The heating temperatures used were 175°C and 260°C, which are temperature settings in accordance with the reflow process of low-temperature molten solder and normal molten solder.

[Method for measuring water absorption rate]
Using a 0.2 mm thick shim plate and a glass rod, the active energy ray curable composition obtained in the Examples and Comparative Examples was applied to an acrylic plate, and then a sheet-shaped cured product having a thickness of 0.2 mm was obtained by irradiating ultraviolet rays with an integrated light amount of 3,000 mJ/ ^cm2 using a belt conveyor type ultraviolet irradiator (120 W metal halide lamp) manufactured by Eye Graphics Co., Ltd. The obtained sheet-shaped cured product was cut into a length of 5 cm x width of 5 cm using a dumbbell cutter to prepare a test piece for measuring water absorption. The prepared test piece was dried at 50°C for 24 hours in a blower oven, and then the weight of the test piece was measured and the initial weight _m1 was obtained. After the initial weight was measured, the test piece was immersed in 300 ml of pure water at 23°C for 24 hours. The moisture remaining on the test piece pulled out of the pure water was wiped off with a nonwoven fabric "Bencotto" manufactured by Asahi Kasei Corporation, and then the weight of the test piece was measured and the weight after immersion _m2 was obtained. After the weight was measured after immersion, the test piece was dried at 50° C. for 24 hours in a fan oven, and the weight of the test piece was measured and recorded as the dry weight m _3. The water absorption rate was calculated by the following formula using the above m ₁ to m ₃ .

[Method for evaluating moist heat resistance]
The active energy ray curable compositions obtained in the examples and comparative examples were dropped onto a cover glass that had been subjected to an adhesion treatment using a silane coupling agent "KBM-5103" manufactured by Shin-Etsu Chemical Co., Ltd., and shaped using a lens replica, and then provisionally cured by irradiation with an irradiation intensity of 50 mW/cm ² and an accumulated light amount of 450 mJ/cm ² using a UV-LED irradiation device "LHPUV365/2501" manufactured by Iwasaki Electric Co., Ltd. After releasing the lens replica, a development process was performed using propylene glycol monomethyl ether to remove the uncured resin composition. Furthermore, after main curing with an accumulated light amount of 7,550 mJ/cm ² , a wafer-level lens was obtained by post-baking at 100°C for 90 minutes using a blower oven. The obtained wafer-level lens was subjected to a 1000-hour moist heat resistance test at a temperature of 85°C and a relative humidity of 85% using an environmental tester (SH-222 manufactured by Espec). After the test, the lens was observed using a microscope "VHX900" manufactured by Keyence Corporation and a laser microscope "OLS5000" manufactured by Olympus Corporation, and evaluated according to the following criteria.

⊚: No peeling, interface defects, or internal defects were observed.
◯: No peeling or interface defects observed, but 1 to 10 internal defects.
△: Medium degree of peeling, interface abnormality, and internal defects.
×: Serious peeling, interface abnormalities, and internal defects.

The abbreviations in Tables 1 to 3 represent the following:
"R-604";
Dioxane glycol diacrylate (manufactured by Nippon Kayaku Co., Ltd.)
"HBPE-4";
EO modified hydrogenated bisphenol A diacrylate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
"A-400";
Polyethylene glycol diacrylate (repeating unit 9) (manufactured by Shin-Nakamura Chemical Co., Ltd.)
"A-600";
Polyethylene glycol diacrylate (repeating unit 14) (manufactured by Shin-Nakamura Chemical Co., Ltd.)
"PE-1";
Pentaerythritol tetrakis(3-mercaptobutyrate) (Showa Denko K.K.)

The evaluation results in Tables 1 to 3 reveal that the cured products formed from the active energy ray-curable compositions of the present invention in Examples 1 to 13 have high Abbe numbers and high heat resistance, their water absorption is controlled within the range of 0.5 to 2.5, and they have high moist heat resistance. In addition, the lens samples of Examples 1 to 13 were free of warping, cracks, or chips after curing, and had good appearances.

On the other hand, Comparative Examples 1 to 3 are examples of active energy ray-curable compositions that do not contain the component (C) defined in the present invention, and it was confirmed that the moist heat resistance test showed peeling, interface abnormalities, and internal defects, and the moist heat resistance was significantly insufficient.

Comparative Example 4 is an example of an active energy ray-curable composition that does not contain the component (B) defined in the present invention, but in the moist heat resistance test, it was confirmed that the composition had insufficient moist heat resistance, with interface abnormalities and internal defects occurring.

Comparative examples 5 to 7 are examples of active energy ray-curable compositions that do not contain component (A) as defined in the present invention, but problems were confirmed, such as severe warping after molding, resulting in shape distortion, low initial transmittance, and high water absorption.

Claims (11)

A polycarbonate diol di(meth)acrylate (A) represented by the following general formula (1),
a compound (B) having one or two (meth)acryloyl groups and a cyclic structure in one molecule other than the polycarbonate diol di(meth)acrylate (A);
and a compound (C) other than the polycarbonate diol di(meth)acrylate (A) and the compound (B) having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule,
the cyclic structure is at least one selected from the group consisting of a cyclohexane structure, a tricyclodecane structure, and a 1,3-dioxane structure,
the alkylene glycol structure is one or more selected from the group consisting of ethylene glycol, propylene glycol, and neopentyl glycol;
The active energy ray-curable composition, wherein the number of repeating units of the alkylene glycol structure is an integer of 2 to 15.

(In the formula, each R ¹ independently represents a hydrogen atom or a methyl group, each R ² independently represents a hydrocarbon group having 1 to 10 carbon atoms, and n is an integer from 1 to 10.) The active energy ray-curable composition according to claim 1, wherein R ² in the general formula (1) is each independently a linear hydrocarbon group having 5 to 6 carbon atoms or a cyclohexane structure. The active energy ray curable composition according to claim 1 or 2, further comprising a compound (D) having one or two (meth)acryloyl groups in one molecule and one or more hydroxyl groups in one molecule other than the polycarbonate diol di(meth)acrylate (A), the compound (B) and the compound (C). The active energy ray-curable composition according to claim 3, wherein the compound (D) is at least one selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4 -hydroxybutyl (meth)acrylate, and sorbitol ethylene oxide-modified di(meth)acrylate. A cured product of the active energy ray-curable composition according to any one of claims 1 to 4. The cured product according to claim 5, whose water absorption rate measured using JIS test method (K7209:2000) C method is in the range of 0.1 to 4.0%. A lens comprising the cured product according to claim 5. A wafer-level lens comprising the cured product according to claim 5. A lens comprising the cured product according to claim 5, at least one of which has an inorganic compound layer formed on it. The lens according to claim 9, wherein the inorganic compound layer is an anti-reflection layer. A camera module comprising a lens according to any one of claims 7 to 10.