WO2019124156A1

WO2019124156A1 - Active energy ray-curable composition, cured product thereof, and lens

Info

Publication number: WO2019124156A1
Application number: PCT/JP2018/045436
Authority: WO
Inventors: 巌服部; 優子井口
Original assignee: Dic株式会社
Priority date: 2017-12-22
Filing date: 2018-12-11
Publication date: 2019-06-27
Also published as: JPWO2019124156A1; TW201930461A

Abstract

The present invention provides an active energy ray-curable composition characterized by containing: a (meth)acrylic compound (A) having a carbonate structure; and a (meth)acrylic compound (B) having a cyclic structure. The present invention also provides a cured product characterized by being formed from the active energy ray-curable composition. The present invention also provides a lens characterized by being formed from the active energy ray-curable composition. The mass ratio of the (meth)acrylic compound (A) to the (meth)acrylic compound (B) is preferably in the range of 10/90-99/1. The lens preferably has an Abbe number of at least 53 and preferably has a water absorption of 1% or less when immersed for 24 hours in 23°C water.

Description

Active energy ray curable composition, cured product thereof, and lens

The present invention relates to an active energy ray curable composition.

In the production of a lens unit of a lens module using a CCD or CMOS image sensor, a method of injection molding, in which a thermoplastic resin such as cycloolefin resin is melted and molded into a lens shape, has been widely used. However, in such a method, the thermoplastic resin is molded as a combination of the lens-shaped portion and the spool and runner portions, and among these, only the lens-shaped portion is used for actual lens manufacturing. The other part, which accounts for about 97%, is an extremely wasteful process that becomes unnecessary.

Therefore, as an alternative, liquid resin is coated on a wafer, then sandwiched between lens molds, shape-transferred, several hundreds of lenses are cured and molded at one time, and then cut into lenses one by one. Examination of the WLO (wafer level optics) manufacturing method is in progress. According to this method, unlike the injection molding method, there is an advantage that waste of material hardly occurs.

As liquid resin which can be used for the said WLO manufacturing method, two types, a thermosetting resin and a photocurable resin, are mentioned. Among them, the use of a photocurable resin having high curability and good productivity is considered desirable, and in recent years, various studies have begun to be made.

As a photocurable resin which can be used for the said WLO manufacturing method, the photocurable resin composition containing a urethane (meth) acrylate is disclosed, for example (refer the patent document 1). However, with such a composition, a lens having a high Abbe number can not be obtained, and there is a problem that chromatic aberration can not be reduced.

Further, in order to be actually used for lens applications, it is also important that the material has a low water absorbability so as not to deteriorate the lens performance such as blurring caused by successive use as well as the Abbe number. However, the fact is that no material compatible with these at high levels has been found yet.

International Publication No. 2008/149766

The problem to be solved by the present invention is to provide an active energy ray-curable composition capable of producing a lens having a high Abbe number and a low water absorption.

The present invention comprises an active energy ray-curable composition comprising a (meth) acrylic compound (A) having a carbonate structure and a (meth) acrylic compound (B) having a cyclic structure, and a cured product thereof And provide a lens.

The lens formed of the active energy ray curable composition of the present invention has a high Abbe number, and can reduce chromatic aberration. In addition, since the lens has low water absorbability, lens performance is unlikely to be deteriorated by successive use.

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 the WLO process.

The active energy ray curable composition of the present invention contains a (meth) acrylic compound (A) having a carbonate structure and a (meth) acrylic compound (B) having a cyclic structure as essential components.

The (meth) acrylic compound (A) having a carbonate structure has high Abbe's number, low water absorption and excellent transparency (especially low water absorption), and imparts flexibility to a cured product, which is suitable as a lens It is an essential ingredient to be able to use in As the (meth) acrylic compound (A), for example, a compound having at least one or more (meth) acrylic groups obtained by reacting a polycarbonate polyol and (meth) acrylic acid and / or (meth) acrylic acid ester Can be used.

In the present invention, “(meth) acrylic compound” refers to one or both of an acrylic compound and a methacrylic compound, and “(meth) acrylic acid” refers to one or both of acrylic acid and methacrylic acid, "(Meth) acryloyl" refers to one or both of acryloyl and methacryloyl, and "(meth) acrylate" refers to one or both of acrylate and methacrylate.

As the polycarbonate polyol, for example, a reaction product of a compound having two or more hydroxyl groups and a carbonic ester can be used.

Examples of the compound having two or more hydroxyl groups include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, and 2-methyl. 1,3-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,5-hexanediol, 3-methyl-1,5-pentanediol, 1,7-heptanediol 1,8-octanediol, 1,9-nonanediol, 1,8-nonanediol, 2-ethyl-2-butyl-1,3-propanediol, 1,10-decanediol, 1,12-dodecanediol , 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, trimethylolprop It can be used trimethylol ethane, glycerin and the like. These compounds may be used alone or in combination of two or more.

As said carbonate, dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate etc. can be used, for example. These compounds may be used alone or in combination of two or more.

Examples of the (meth) acrylic acid ester include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, n-pentyl (meth) acrylate Meta) acrylate, n-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl ( Meta) acrylate, methoxy polyethylene glycol mono (meth) acrylate, octoxy polyethylene glycol polypropylene glycol mono (meth) acrylate, lauroxy polyethylene glycol mono (meth) acrylate, sulfur Alloxy polyethylene glycol mono (meth) acrylate, phenoxy polyethylene glycol mono (meth) acrylate, phenoxy polyethylene glycol polypropylene glycol mono (meth) acrylate, nonyl phenoxy polypropylene glycol mono (meth) acrylate, nonyl phenoxy poly (ethylene glycol propylene glycol) Mono (meth) acrylate, 2-perfluorohexylethyl (meth) acrylate or the like can be used. These (meth) acrylic acid esters may be used alone or in combination of two or more.

Among the above-mentioned (meth) acrylic compounds (A), even higher Abbe numbers and refractive indices are obtained, and further excellent low water absorption, flexibility, transparency and heat resistance are obtained. From the point of view, it is preferable to use a compound represented by the following general formula (1).

(In the general formula (1), each R ¹ independently represents a hydrogen atom or a methyl group, and each R ² independently represents a linear glycol residue having 1 to 10 carbon atoms or a glycol having an alicyclic structure Indicates a residue, n represents an integer of 4 to 34.)

As a glycol which has the said alicyclic structure, the compound shown by following General formula (2) can be used, for example.

(In the general formula (2), each R ³ independently represents an alkylene group having 1 to 4 carbon atoms.)

Among the compounds represented by the general formula (1), as the (meth) acrylic compound (A), much higher Abbe number and refractive index can be obtained, and further low water absorption, transparency, From the viewpoint of obtaining flexibility and heat resistance, in the following general formula (1), R ² is a linear glycol residue having 4 to 8 carbon atoms, and / or R ³ is carbon in the general formula (2) It is preferable to use a glycol residue having an alicyclic structure showing an alkylene group having 1 to 2 atoms, and it is preferable to use one having n as an integer of 5 to 10, and among them, crystallization and warping of the lens over time from the viewpoint of easily preventing, R ² in the following general formula (1) is, in a linear glycol residue and the general formula of carbon atoms 4 ~ 8 (2), R 3 is 1-2 carbon atoms alkylene Using a compound which is a glycol residue having an alicyclic structure showing a group Is particularly preferred.

In the case of using the above particularly preferable compound, an alicyclic structure having the linear glycol residue having 4 to 8 carbon atoms and R ³ in the general formula (2) and having an alkylene group having 1 to 2 carbon atoms in the general formula (2) The mass ratio with the glycol residue is preferably in the range of 10/90 to 90/10, more preferably in the range of 20/80 to 80/20, and further preferably in the range of 55/45 to 80/20. preferable.

The (meth) acrylic compound (B) having a cyclic structure is an essential component for obtaining a high Abbe number and low water absorption.

Examples of the (meth) acrylic compound having a cyclic structure include a cyclo ring, a benzene ring, a tricyclodecane structure, a dicyclopentenyl structure, an isobornyl structure, and a heterocyclic structure having an oxygen atom as a hetero atom (meth) Acrylic compounds can be used. These compounds may be used alone or in combination of two or more.

As the (meth) acrylic compound having a cyclo ring, for example, cyclohexyl (meth) acrylate, 1,4-cyclohexanedimethanol monoacrylate and the like can be used. These compounds may be used alone or in combination of two or more.

As the (meth) acrylic compound having a benzene ring, for example, benzyl (meth) acrylate, phenoxy (meth) acrylate, phenoxyethyl (meth) acrylate, nonyl phenoxy polyethylene glycol (meth) acrylate and the like can be used. These compounds may be used alone or in combination of two or more.

Examples of the (meth) acrylic compound having a tricyclodecane (dicyclopentanyl) structure include dicyclopentanyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, and dimethyloltriol. Cyclodecanedi (meth) acrylate, tricyclodecanediol di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate or the like can be used. These compounds may be used alone or in combination of two or more. Among these, dicyclopentanyloxyethyl (meth) acrylate and / or dimethylol tricyclodecane di (meth) acrylate are used in that higher Abbe numbers and low water absorption can be obtained. Is preferred, and dimethylol tricyclodecane di (meth) acrylate is more preferred.

As the (meth) acrylic compound having a dicyclopentenyl structure, for example, dicyclopentenyl (meth) acrylate, dicyclopentenyl oxyethyl (meth) acrylate and the like can be used. These compounds may be used alone or in combination of two or more.

As the (meth) acrylic compound having an isobornyl structure, for example, isobornyl (meth) acrylate, isobornyl di (meth) acrylate and the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use isobornyl (meth) acrylate from the viewpoint of obtaining a further higher Abbe number and low water absorption.

Examples of the (meth) acrylic compound having a heterocyclic structure having an oxygen atom as a hetero atom include cyclic trimethylol propane formal acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl) Methyl (meth) acrylate, (3-ethyloxetan-3-yl) methyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, neopentyl glycol-modified trimethylolpropane di (meth) acrylate and the like can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use tetrahydrofurfuryl (meth) acrylate and / or neopentyl glycol-modified trimethylolpropane di (meth) acrylate from the viewpoint of obtaining a further higher Abbe number and low water absorption.

Among the above-mentioned (meth) acrylic compounds (B), tricyclodecane structure, dicyclopentenyl structure, isobornyl structure, and oxygen atom can be obtained from the viewpoint that higher Abbe number and lower water absorption can be obtained among the above-mentioned. It is preferable to use a (meth) acrylic compound having at least one cyclic structure selected from the group consisting of heterocyclic structures having hetero atoms.

Among the above, when a (meth) acrylic compound having a tricyclodecane structure is used as the (meth) acrylic compound (B), a higher Abbe number and refractive index can be obtained, and a further excellent low water absorption The (meth) acrylic compound (A) and the (meth) acrylic compound (B) from the viewpoints that flexibility, transparency and heat resistance can be obtained, and crystallization and warping of the lens over time can be easily prevented The following are particularly preferable as a combination with

As the (meth) acrylic compound (A), in the general formula (1), R ¹ represents a hydrogen atom, and R ² represents a linear glycol residue having 4 to 8 carbon atoms and in the general formula (2): A compound in which R ³ represents a glycol residue having an alicyclic structure showing an alkylene group having 1 to 2 carbon atoms, and n represents an integer of 5 to 10,
The methacryl compound which has a tricyclodecane structure as a (meth) acrylic compound (B).

As the (meth) acrylic compound (A), in the general formula (1), R ¹ represents a hydrogen atom, and R ² represents a linear glycol residue having 4 to 8 carbon atoms and in the general formula (2): A compound in which R ³ represents a glycol residue having an alicyclic structure showing an alkylene group having 1 to 2 carbon atoms, and n represents an integer of 5 to 10,
The acrylic compound which has a tricyclodecane structure as a (meth) acrylic compound (B).

As the mass ratio [(A) / (B)] of the (meth) acrylic compound (A) to the (meth) acrylic compound (B), a higher Abbe number and refractive index can be obtained, and further, It is preferably in the range of 10/90 to 99/1, more preferably in the range of 40/60 to 90/10, from the viewpoint of obtaining further excellent low water absorption, flexibility, transparency and heat resistance. The range of / 50 to 90/10 is more preferable, and the range of 60/40 to 80/20 is particularly preferable.

In addition, the active energy ray curable composition of the present invention can be made into a cured product or a lens by irradiation with active energy rays. The active energy ray refers to ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. When irradiating an ultraviolet-ray as an active energy ray, it is preferable to add a photoinitiator (C) in the active energy ray curable composition of this invention, and to improve curability. In addition, if necessary, a photosensitizer (D) can be further added to improve the curability. On the other hand, in the case of using ionizing radiation such as electron beam, alpha ray, beta ray, gamma ray, etc., curing is performed rapidly without using the photopolymerization initiator (C) or the photosensitizer (D). There is no need to add a photopolymerization initiator (C) or a photosensitizer (D).

Examples of the photopolymerization initiator (C) include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo {2-hydroxy-2-methyl-1- [4- (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-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) Acetophenone compounds such as butanone; benzoin, benzoin methyl ether, benzo Benzoin compounds such as isopropyl ether; acyl phosphine oxide compounds such as 2,4,6-trimethylbenzoin diphenyl phosphine oxide, bis (2,4,6-trimethyl benzoyl) -phenyl phosphine oxide; benzyl (dibenzoyl), methyl Benzyl compounds such as phenylglyoxy ester, oxyphenylacetic acid 2- (2-hydroxyethoxy) ethyl ester, oxyphenylacetic acid 2- (2-oxo-2-phenylacetoxyethoxy) ethyl ester; benzophenone, o-benzoylbenzoic acid Methyl-4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, acrylated benzophenone, 3,3 ' Benzophenone compounds such as 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone; 2-isopropylthioxanthone , Thioxanthone compounds such as 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone; aminobenzophenone compounds such as Michael-ketone, 4,4'-diethylaminobenzophenone; 10-butyl-2 -Chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, camphorquinone, 1- [4- (4-benzoylphenylsulfanyl) phenyl] -2-methyl-2- (4-methylphenyl) Sulfonyl ) Propane-1-one or the like can be used. These photopolymerization initiators may be used alone or in combination of two or more.

Further, as the photosensitizer (D), for example, tertiary amine compounds such as diethanolamine, N-methyldiethanolamine, tributylamine, urea compounds such as o-tolylthiourea, sodium diethyl dithiophosphate, s-benzylisothiolo Sulfur compounds such as sodium-p-toluenesulfonate can be used. These photosensitizers may be used alone or in combination of two or more.

As a total usage-amount in the case of using said photoinitiator (C) and photosensitizer (D), the total mass 100 mass of said (meth) acrylic compound (A) and (meth) acrylic compound (B) The amount is preferably 0.05 to 20 parts by mass, and more preferably 0.1 to 10 parts by mass.

Other additives may be added to the active energy ray-curable composition of the present invention in addition to the components (A) to (D) described above.

Examples of the other additives include a polymerization inhibitor, a surface control agent, an antistatic agent, an antifoaming agent, a viscosity control agent, a light resistance stabilizer, a weathering stabilizer, a heat resistance stabilizer, an ultraviolet light absorber, and an antioxidant. Additives such as leveling agents, organic pigments, inorganic pigments, pigment dispersants, silica beads, organic beads and the like; inorganic fillers such as silicon oxide, aluminum oxide, titanium oxide, zirconia, antimony pentoxide and the like can be blended. These other compounds may be used alone or in combination of two or more.

As a method of obtaining the hardened | cured material of the said active energy ray curable composition, the method of coating the said active energy ray curable composition on a base material, and irradiating the active energy ray after that is mentioned, for example.

Examples of the substrate include polyester resins such as polyethylene terephthalate, polybutylene terephthalate and polyethylene naphthalate; polyolefin resins such as polypropylene, polyethylene and polymethylpentene-1; cellulose acetate (diacetyl cellulose, triacetyl cellulose etc.) Cellulose-based resins such as cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate and cellulose nitrate; acrylic resins such as polymethyl methacrylate; polyvinyl chloride, polyvinylidene chloride and the like Vinyl chloride resin; polyvinyl alcohol; ethylene-vinyl acetate copolymer; polystyrene; polyamide; polycarbonate; Polyphone sulfone; Polyether ether ketone; Polyimide resin such as polyimide and polyether imide; norbornene resin (for example, "Zeonor" manufactured by Nippon Zeon Co., Ltd.), modified norbornene resin (for example, "JSR Co., Ltd." Resin films such as ARTON "), cyclic olefin copolymers (for example," APEL "manufactured by Mitsui Chemicals, Inc.); wafers; glass etc. can be used.

As a method of applying the active energy ray-curable composition of the present invention to the film substrate, for example, die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, kiss coating, spray coating, dip coating Spinner coat, brush coating, silk screen beta coat, wire bar coat, flow coat, dispenser, inkjet printing, screen printing, offset printing and the like.

The active energy ray for curing the active energy ray curable composition is, as described above, ionizing radiation such as ultraviolet light, electron beam, alpha ray, beta ray, gamma ray and the like. Here, when using an ultraviolet ray as an active energy ray, as an apparatus which irradiates the ultraviolet ray, for example, a low pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, an electrodeless lamp (fusion lamp), a chemical lamp, Black light lamps, mercury-xenon lamps, short arc lamps, helium-cadmium lasers, argon lasers, sunlight, LED lamps and the like can be mentioned.

The irradiation amount (integrated light amount) of the active energy ray is, for example, in the range of 100 to 5,000 mJ / cm ² . The irradiation dose of the active energy ray is based on the value measured using Iwasaki Electric Co., Ltd. eye ultraviolet integrated illuminance meter UVPF-A1 (PD-365).

The film thickness of the cured product of the active energy ray-curable composition of the present invention is preferably in the range of 1 to 100 μm from the viewpoint that the hardness of the cured product can be made sufficient.

As a method of producing a lens by the active energy ray curable composition of the present invention, the active energy ray curable composition is coated or injected onto a wafer or a mold, and the active energy ray is irradiated to the composition. Cure. The method of cutting etc. to a desired shape is mentioned. The coating method of the said active energy ray curable composition, the irradiation method of an active energy ray, etc. are the same methods as the method at the time of obtaining the hardened | cured material of the said active energy ray curable composition.

The Abbe number of the lens is preferably 53 or more, more preferably in the range of 53 to 60, still more preferably in the range of 55 to 59, and particularly preferably in the range of 56 to 59. In addition, the measuring method of the Abbe number of the said lens is described in the Example.

The refractive index of the lens is preferably in the range of 1.5 to 1.6, and more preferably in the range of 1.5 to 1.56. In addition, the refractive index of the said lens shows the value measured based on A method of JIS test method K7142: 2014.

The glass transition temperature (Tg, midpoint glass transition temperature) of the lens is preferably in the range of 50 ° C. to 270 ° C., and is preferably in the range of 100 ° C. to 165 ° C., from the viewpoint of achieving further excellent heat resistance. More preferable. In addition, the glass transition temperature of the said lens shows the value measured based on JIS test method K7121: 2012.

The water absorption rate of the lens when immersed in water at 23 ° C. for 24 hours is preferably 1% or less, from the viewpoint of suppressing deterioration of lens performance due to continuous use, and preferably 0.05 to 0. More preferably, it is at most 0.5%. In addition, the water absorption of the said lens shows the value calculated by the mass change of the lens before and behind immersion at the time of making a lens immersed in water of 23 degreeC for 24 hours, and a measuring method is concretely described in an Example. .

As mentioned above, the lens formed with the active energy ray curable composition of this invention has a high Abbe number, and can make a chromatic aberration small. In addition, since the lens has low water absorbability, lens performance is unlikely to be deteriorated by successive use.

Hereinafter, the present invention will be more specifically described by way of examples.

Example 1
The following three components were mixed and heated to 50 ° C., and then stirred and mixed at a rotational speed of 1,000 ppm for 10 minutes using a homodispa to prepare an active energy ray-curable composition.
<(Meth) acrylic compound (A)>
Among the compounds represented by the general formula (1), a glycol having an alicyclic structure in which R ¹ is a hydrogen atom, R ² is a 1,6-hexanediol residue, and R ³ is a methylene group in the general formula (2) Indicating a residue (mass ratio: 3/1), n representing an integer of 7 (hereinafter abbreviated as (A-1)); 50 parts by mass,
<(Meth) acrylic compound (B)>
Dimethylol tricyclodecane dimethacrylate (hereinafter, abbreviated as (B-1)); 50 parts by mass <photopolymerization initiator (C)>
1-hydroxycyclohexyl phenyl ketone (hereinafter abbreviated as "Irg 184"): 1 part by mass

[Examples 2 to 20, Comparative Examples 1 to 2]
An active energy ray-curable composition in the same manner as in Example 1 except that the type and / or amount of the (meth) acrylic compound (A) and the (meth) acrylic compound (B) were changed as shown in Tables 1 to 3 Prepared.

[Method of measuring Abbe number]
The active energy ray-curable composition obtained in Examples and Comparative Examples is poured into a triangular prism type (thickness 5 mm, length 10 mm on one side), and a conveyor belt type ultraviolet irradiation device (120 W metal halide manufactured by Eye Graphics Co., Ltd.) Using a lamp, 3,000 mJ / cm ² of ultraviolet light was irradiated to produce a triangular prism-shaped lens. The Abbe number of the obtained lens was measured using a Karnyu precision refractometer "KPR-3000" manufactured by Shimadzu Corporation.

[Method of measuring water absorption rate]
The active energy ray-curable composition obtained in Examples and Comparative Examples is coated on a glass plate so as to have a thickness of 200 μm after UV curing, and a conveyor belt type ultraviolet radiation device (Igraphics Co., Ltd.) A lens sheet sample was prepared by irradiating 3,000 mJ / cm ² of ultraviolet light using a 120 W metal halide lamp). This sample was cut into 5 cm × 5 cm, immersed purely at 23 ° C. for 24 hours, and the water absorption was calculated by the mass change (mass increase) of the sample before and after immersion.

The abbreviations in Tables 1 to 3 indicate the following.
"(A-2)";
Among the compounds represented by the general formula (1), a glycol having an alicyclic structure in which R ¹ is a methyl group, R ² is a 1,6-hexanediol residue, and R ³ is a methylene group in the general formula (2) Indicating a residue (mass ratio: 3/1), n is an integer of 7
"(A-3)";
Among the compounds represented by the general formula (1), a glycol having an alicyclic structure in which R ¹ is a methyl group, R ² is a 1,6-hexanediol residue, and R ³ is a methylene group in the general formula (2) Indicating a residue (mass ratio: 1/3), n is an integer of 7
"(A-4)";
Among the compounds represented by the general formula (1), those in which R ¹ is a hydrogen atom, R ² is a 1,6-hexanediol residue, and n is an integer of 8.
"(A-5)";
Among the compounds represented by the general formula (1), those in which R ¹ is a methyl group, R ² is a 1,6-hexanediol residue, and n is an integer of 8.

"(B-2)";
Dimethylol tricyclodecane dimethacrylate "(B-3)";
Dicyclopentenyloxyethyl methacrylate "(B-4)";
Isobornyl acrylate "(B-5)";
Tetrahydrofurfuryl acrylate "(B-6)";
Neopentyl glycol modified trimethylolpropane diacrylate

“(UA1)”; polypropylene glycol (number average molecular weight; 1,000), toluene diisocyanate, and 2-hydroxyethyl acrylate, 1 equivalent of polypropylene glycol OH, 1 mol of toluene diisocyanate, and 1 mol of 2-hydroxyethyl acrylate Urethane acrylate obtained by reacting at a ratio of

From the evaluation results of Tables 1 to 3, it was found that the lenses formed of the active energy ray curable compositions of the present invention of Examples 1 to 20 have high Abbe numbers and low water absorbency. The lens sheet samples of Examples 1 to 8 had a refractive index of 1.5 or more, no warping after curing, no cracks and cracks, and the appearance was good.

On the other hand, Comparative Examples 1 and 2 are embodiments in which urethane acrylate is used instead of the (meth) acrylic compound (A), but the Abbe number is as low as 48 and the water absorption rate is more than 1%. it was high.

Claims

An active energy ray curable composition comprising a (meth) acrylic compound (A) having a carbonate structure and a (meth) acrylic compound (B) having a cyclic structure.
The mass ratio [(A) / (B)] of the (meth) acrylic compound (A) to the (meth) acrylic compound (B) is in the range of 10/90 to 99/1. Active energy ray curable composition.
The active energy according to claim 1 or 2, wherein the (meth) acrylic compound (A) has a structure derived from a linear glycol having 1 to 10 carbon atoms and / or a glycol having an alicyclic structure. Radiation curable composition.
The (meth) acrylic compound (B) has at least one cyclic structure selected from the group consisting of a tricyclodecane structure, a dicyclopentenyl structure, an isobornyl structure, and a heterocyclic structure having an oxygen atom as a hetero atom. The active energy ray-curable composition according to any one of claims 1 to 3, which is
A cured product formed by the active energy ray-curable composition according to any one of claims 1 to 4.
A lens formed by the active energy ray curable composition according to any one of claims 1 to 4.
The lens according to claim 6, wherein an Abbe number is 53 or more, and a water absorption when immersed in water at 23 ° C for 24 hours is 1% or less.