Photocurable resin composition, optical molded product, and optical device

Abstract

A photocurable resin composition applicable to an optical molded body, comprising a (meth)acrylate monomer and a polysiloxane compound, wherein the (meth)acrylate monomer contains a bifunctional or higher (meth)acrylate monomer, and the polysiloxane compound has a polyoxyalkylene skeleton.

Description

Photocurable resin composition, optical molded body, and optical device

[0001] The present invention relates to a photocurable resin composition, an optically molded article, and an optical device.

[0002] In recent years, thermoplastic resins and UV-curable resin compositions have been studied for use in optical lenses from the viewpoint of heat resistance and low birefringence. Among these, methacrylic resin compositions, which are thermoplastic resins, have been studied. For example, the technologies for methacrylic resin compositions are described in Patent Documents 1 and 2.

[0003] Patent Document 1 aims to provide a methacrylic resin composition with high heat resistance, highly controlled birefringence, high light transmittance in long-path light, and excellent color tone and transparency, comprising a methacrylic resin containing structural units derived from at least N-substituted maleimide monomers in the main chain, with a glass transition temperature greater than 120°C and 160°C or less, and a resin temperature of 270°C with a shear rate of 1000 sec. ―１ Under these conditions, the melt viscosity is 250 Pa·s or less, and the absolute value of the photoelastic coefficient is 1 × 10⁻⁶. ―１２ pa ―１ The following describes a methacrylic resin composition, wherein a solution of the resin composition dissolved in chloroform at a ratio of 20 mass to volume yields a light transmittance of 94% or more when measured under conditions of a path length of 100 mm and a wavelength of 470 nm, and a light transmittance of 96% or more when measured under conditions of a wavelength of 700 nm.

[0004] Patent Document 2 describes a photocurable composition that is fast-curing, non-anaerobic, low viscosity, low odor, and has excellent storage stability, and in particular, the cured product is excellent in various properties necessary for lenses, such as colorless transparency, low optical distortion, heat resistance, low water absorption, toughness, and high hardness. The photocurable composition contains a tricyclodecane skeleton di(meth)acrylate (A), a trifunctional or tetrafunctional secondary thiol (B), a cleavage-type photopolymerization initiator (C), and a hindered phenol antioxidant (D), characterized in that the photocurable composition does not contain a primary thiol, and the content ratio (weight ratio) of components (A), (B), (C), and (D) is within the following range. Component (A) / Component (B) = 75 / 25 to 95 / 5 Component (C): 2 to 10 parts by weight per 100 parts by weight of the total of components (A) and (B) Component (D): 0.1 to 1 part by weight per 100 parts by weight of the total of components (A) and (B)

[0005] Japanese Patent Publication No. 2019-35015 Japanese Patent Publication No. 2022-32186

[0006] The present invention provides a photocurable resin composition that can improve the performance balance between the contact angle of the surface of an optically molded body and the transparency of the optically molded body.

[0007] The inventors diligently conducted research to achieve the above objectives. As a result, they discovered that the compounds contained in the photocurable resin composition used to produce optical molded articles are related to the balance between the contact angle of the optical molded article's surface and its transparency. Based on this finding, the inventors further diligently conducted research and discovered that including a polysiloxane compound having a polyoxyalkylene skeleton in the photocurable resin composition used to produce optical molded articles can improve the balance between the contact angle of the optical molded article's surface and its transparency, thus completing the present invention.

[0008] According to the present invention, there are provided a photocurable resin composition, an optical molded body, and an optical device as shown below. [1] A photocurable resin composition capable of being used for an optical molded body, comprising a (meth)acrylate monomer and a polysiloxane compound, wherein the (meth)acrylate monomer includes a bifunctional or higher-functional (meth)acrylate monomer, and the polysiloxane compound has a polyoxyalkylene skeleton. [2] The photocurable resin composition according to [1] above, wherein the polysiloxane compound contains one or more compounds selected from the group consisting of a compound represented by the following formula (1) and a compound represented by the following formula (2). (In the above formula (1), R １ each independently represents an alkyl group having 1 to 4 carbon atoms, R ２ and R ３ each independently represents an alkylene group having 1 to 4 carbon atoms, R ４ is an alkylene group having 1 to 4 carbon atoms different from R ３ , R ５ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group, l and m each independently represent an integer in the range of 0 to 1000, (l + m) is an integer of 1 or more, a and b each independently represent an integer in the range of 0 to 100, and (a + b) is an integer of 1 or more.) (In the above formula (2), R ６ each independently represents an alkyl group having 1 to 4 carbon atoms, R ７ and R ８ each independently represents an alkylene group having 1 to 4 carbon atoms, R ９ is an alkylene group having 1 to 4 carbon atoms different from R ８ , R １０(wherein is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group, n is an integer in the range of 0 to 1000, c and d are each independently integers in the range of 0 to 100, and (c + d) is an integer of 1 or more.) [3] The photocurable resin composition according to [1] or [2], wherein the content of the polysiloxane compound is 0.00005 parts by mass or more and 0.5 parts by mass or less, when the content of the (meth)acrylate monomer is 100 parts by mass. [4] The photocurable resin composition according to any one of [1] to [3], wherein the bifunctional or more (meth)acrylate monomer comprises one or more selected from the group consisting of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers. [5] The photocurable resin composition according to [4], wherein the total content of the alicyclic bifunctional (meth)acrylate monomer and the linear bifunctional (meth)acrylate monomer is 60 parts by mass or more and 100 parts by mass or less when the total content of the bifunctional or more (meth)acrylate monomers is 100 parts by mass. [6] The photocurable resin composition according to any one of [1] to [5], wherein the content of the bifunctional or more (meth)acrylate monomer is 5 parts by mass or more and 100 parts by mass or less when the total content of the (meth)acrylate monomers is 100 parts by mass. [7] The photocurable resin composition according to any one of [1] to [6], wherein the (meth)acrylate monomer further comprises a monofunctional (meth)acrylate monomer. [8] The photocurable resin composition according to [7], wherein the monofunctional (meth)acrylate monomer has an alicyclic skeleton. [9] The photocurable resin composition according to any one of [1] to [8], further comprising an antioxidant.

[10] A photocurable resin composition according to any one of [1] to [9], further comprising a photopolymerization initiator.

[11] A photocurable resin composition according to

[10] , wherein the photopolymerization initiator comprises a photoradical polymerization initiator.

[12] A photocurable resin composition according to any one of [1] to

[11] , further comprising a light stabilizer.

[13] A photocurable resin composition according to any one of [1] to

[12] , which can be used in a casting method.

[14] A photocurable resin composition according to any one of [1] to

[13] , which can be used for one or more lenses selected from the group consisting of virtual reality device lenses (VR lenses), mixed reality device lenses (MR lenses), augmented reality device lenses (AR lenses), cross-reality device lenses (xR lenses), and head-mounted display lenses (HMD lenses).

[15] An optical molded body comprising a cured product of the photocurable resin composition according to any one of [1] to

[14] .

[16] The optical molded body according to

[15] , wherein the optical molded body comprises a lens.

[17] The optical molded body according to

[16] , wherein the lens comprises one or more lenses selected from the group consisting of virtual reality device lenses (VR lenses), mixed reality device lenses (MR lenses), augmented reality device lenses (AR lenses), cross-reality device lenses (xR lenses), and head-mounted display lenses (HMD lenses).

[18] The optical molded body according to

[15] , wherein the optical molded body includes a cover display.

[19] The optical molded body according to

[18] , wherein the cover display includes one or more selected from the group consisting of a cover display for a virtual reality device, a cover display for a mixed reality device, a cover display for an augmented reality device, a cover display for a cross-reality device, and a cover display for a head-mounted display.

[20] The optical molded body according to any one of

[15] to

[19] , wherein the maximum thickness portion is 20 mm or less.

[21] The optical molded body according to any one of

[15] to

[20] , wherein the maximum thickness portion is 0.01 mm or more.

[22] An optical device comprising the optical molded body according to any one of

[15] to

[21] .

[0009] According to the present invention, it is possible to provide a photocurable resin composition that can improve the performance balance between the contact angle of the surface of an optically molded body and the transparency of the optically molded body.

[0010] In this specification, the term "(meth)acrylate" refers to a concept that encompasses both acrylate and methacrylate. The same applies to similar terms such as "(meth)acryloyl." For each component in this embodiment, one type may be used, or two or more types may be used in combination. Furthermore, unless otherwise specified, the numerical range "A to B" refers to a range of A or greater and B or less.

[0011] Conventionally, optical molded articles obtained from photocurable resin compositions, such as those obtained from acrylic resin compositions, have been known to have high surface polarity. However, high surface polarity of an optical molded article increases its surface free energy, making it easier for foreign matter to adhere to its surface. When foreign matter adheres to the surface of an optical molded article, it can cause defects in the optical molded article and products using it. One way to reduce the adhesion of foreign matter to the surface of an optical molded article is to decrease its surface free energy (increase the contact angle of the optical molded article's surface). As a result of further investigation by the inventors, it became clear that if the surface free energy of the optical molded article is reduced too much (if the contact angle of the optical molded article's surface is increased too much), the transparency of the optical molded article deteriorates. In other words, the inventors found that there is a trade-off relationship between the size of the contact angle of the optical molded article's surface and the transparency of the optical molded article.

[0012] (Photocurable Resin Composition) The photocurable resin composition of this embodiment (hereinafter also referred to simply as "resin composition" as appropriate) is a photocurable resin composition that can be used in optical molded articles. The photocurable resin composition of this embodiment comprises a (meth)acrylate monomer and a polysiloxane compound. The (meth)acrylate monomer comprises a (meth)acrylate monomer with two or more functions. The polysiloxane compound has a polyoxyalkylene skeleton. By having the above configuration, the photocurable resin composition of this embodiment can improve the balance between the contact angle of the surface of the optical molded article and the transparency of the optical molded article.

[0013] The reason for this is not entirely clear, but the following reasons can be inferred. It is thought that the inclusion of a polysiloxane compound in the photocurable resin composition of this embodiment reduces the surface free energy of the optically molded body obtained from the photocurable resin composition of this embodiment. This is thought to allow for a larger contact angle on the surface of the optically molded body. Furthermore, it is thought that the polysiloxane compound in this embodiment has a polyoxyalkylene skeleton, which improves the compatibility between the (meth)acrylate monomer and the polysiloxane compound. Therefore, it is thought that the transparency of the optically molded body can be maintained while increasing the contact angle on the surface of the optically molded body obtained from the photocurable resin composition containing the polysiloxane compound. And, by improving the performance balance between the size of the contact angle on the surface of the optically molded body and the transparency of the optically molded body, it is thought that the performance balance between the resistance to foreign matter adhesion to the surface of the optically molded body and the transparency of the optically molded body can also be improved.

[0014] The properties of the photocurable resin composition are not particularly limited. However, from the viewpoint of suitability for forming optical molded articles by injection molding or casting, the photocurable resin composition is preferably in liquid form. Furthermore, from the viewpoint of improving the design freedom of the optical molded article, the photocurable resin composition is preferably used for molding by casting.

[0015] Next, specific examples of the components of the photocurable resin composition will be given. The photocurable resin composition contains a (meth)acrylate monomer (A) and a polysiloxane compound (E). The photocurable resin composition may consist of (meth)acrylate monomer (A) and polysiloxane compound (E), and may also contain components other than (meth)acrylate monomer (A) and polysiloxane compound (E). As specific examples of other components, the photocurable resin composition may also contain one or more selected from the group consisting of antioxidants (B), photopolymerization initiators (C), and light stabilizers (D), which will be described later.

[0016] <(meth)acrylate monomer (A)> (meth)acrylate monomer (A) is a compound having a (meth)acryloyl group. (meth)acrylate monomer (A) is a molecule that can bond with other molecules through radical polymerization of the (meth)acryloyl group.

[0017] The (meth)acrylate monomer (A) of this embodiment includes a bifunctional or more (meth)acrylate monomer (A2) from the viewpoint of improving the performance balance between the contact angle on the surface of the optical molded body and the transparency of the optical molded body.

[0018] The content of bifunctional or more (meth)acrylate monomer (A2) in the photocurable resin composition of this embodiment is preferably 5 parts by mass or more and 100 parts by mass or less, more preferably 8 parts by mass or more and 90 parts by mass or less, even more preferably 10 parts by mass or more and 70 parts by mass or less, even more preferably 13 parts by mass or more and 50 parts by mass or less, even more preferably 15 parts by mass or more and 40 parts by mass or less, even more preferably 15 parts by mass or more and 35 parts by mass or less, even more preferably 15 parts by mass or more and 30 parts by mass or less, and even more preferably 15 parts by mass or more and 25 parts by mass or less, when the total content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass or less.

[0019] In this embodiment, the (meth)acrylate monomer (A) preferably further comprises a monofunctional (meth)acrylate monomer (A1) from the viewpoint of further improving the performance balance between the contact angle on the surface of the optical molded body and the transparency of the optical molded body.

[0020] The content of monofunctional (meth)acrylate monomer (A1) in the photocurable resin composition of this embodiment is preferably 0 to 95 parts by mass, more preferably 10 to 92 parts by mass, even more preferably 30 to 90 parts by mass, even more preferably 50 to 87 parts by mass, even more preferably 60 to 85 parts by mass, even more preferably 65 to 85 parts by mass, even more preferably 70 to 85 parts by mass, and even more preferably 75 to 85 parts by mass, when the total content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.

[0021] In the photocurable resin composition of this embodiment, the mass ratio (A1 / A2) of the content of bifunctional or more (meth)acrylate monomers (A2) to the content of monofunctional (meth)acrylate monomers (A1) is preferably 0.50 to 10.0, more preferably 1.0 to 8.0, even more preferably 1.5 to 7.0, even more preferably 2.0 to 6.0, even more preferably 2.0 to 5.5, even more preferably 2.0 to 5.0, and even more preferably 2.0 to 4.5, from the viewpoint of further improving the performance balance between the contact angle on the surface of the optically molded body and the transparency of the optically molded body.

[0022] The content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is preferably 70% to 100% by mass, more preferably 80% to 99% by mass, even more preferably 85% to 98% by mass, and even more preferably 90% to 97% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0023] <Mono-functional (meth)acrylate monomer (A1)>The mono-functional (meth)acrylate monomer (A1) includes, for example, one or more selected from the group consisting of aromatic ring mono-functional (meth)acrylate monomers, alicyclic mono-functional (meth)acrylate monomers, and chain mono-functional (meth)acrylate monomers. The chain mono-functional (meth)acrylate monomer includes one or more selected from the group consisting of linear mono-functional (meth)acrylate monomers and branched mono-functional (meth)acrylate monomers. The linear mono-functional (meth)acrylate monomer includes a mono-functional (meth)acrylate monomer having a linear hydrocarbon skeleton. The branched mono-functional (meth)acrylate monomer includes a mono-functional (meth)acrylate monomer having a branched hydrocarbon skeleton.

[0024] The monofunctional (meth)acrylate monomer (A1) is preferably isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate (e.g., GM81HDA, manufactured by Kokusei Chemical Co., Ltd.), 3,3,5-trimethylcyclohexyl (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate (e.g., FA-511AS, manufactured by Hitachi Chemical Co., Ltd.), dicyclopentenyloxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-hydroxyethyl (meth) Acrylate, 4-hydroxybutyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, isooctyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxydioxyethyl (meth)acrylate, ethoxy Diglycol (meth)acrylate, cyclic trimethylolpropane formal mono(meth)acrylate, imide (meth)acrylate, isoamyl (meth)acrylate, ethoxylated succinic acid (meth)acrylate, trifluoroethyl (meth)acrylate, ω-carboxypolycaprolactone mono(meth)acrylate, cyclohexyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate (e.g., S-1800A, Shin Nakamura Chemical Industry Co., Ltd.) (Manufactured by), diethylene glycol monobutyl ether (meth)acrylate, lauryl (meth)acrylate (e.g., LA, manufactured by Osaka Organic Chemical Industry Co., Ltd.), isodecyl (meth)acrylate, octyl / decyl (meth)acrylate, tridecyl (meth)acrylate, caprolactone (meth)acrylate, ethoxylated (4) nonylphenol (meth)acrylate, methoxypolyethylene glycol (350) mono(meth)acrylate, methoxypolyethylene glycol (550) mono(meth)acrylate, phenoxyethyl (meth)acrylate,Benzyl (meth)acrylate, methylphenoxyethyl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl (meth)acrylate, tribromophenyl (meth)acrylate, ethoxylated tribromophenyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, ethylene oxide adduct of 2-phenoxyethyl (meth)acrylate, propylene oxide adduct of 2-phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth) It contains one or more selected from the group consisting of acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-methacryloyloxymethylcyclohexene oxide, 3-(meth)acryloyloxymethylcyclohexene oxide, ethoxylated-o-phenylphenol (meth)acrylate (e.g., A-LEN-10, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 2-methacryloyloxy-2-methyladamantane, and 2-methacryloyloxy-2-ethyladamantane.

[0025] The monofunctional (meth)acrylate monomer (A1) preferably has an alicyclic skeleton, from the viewpoint of further improving the performance balance between the contact angle on the surface of the optically molded article and the transparency of the optically molded article. The monofunctional (meth)acrylate monomer (A1) more preferably comprises an alicyclic monofunctional (meth)acrylate monomer, and more preferably comprises one or more selected from the group consisting of dicyclopentanyl (meth)acrylate and isobornyl (meth)acrylate, and even more preferably comprises one or more selected from the group consisting of dicyclopentanyl methacrylate and isobornyl methacrylate.

[0026] From the viewpoint of further improving the performance balance between the magnitude of the contact angle of the surface of the optical molded body and the transparency of the optical molded body, when the total content of the alicyclic monofunctional (meth)acrylate monomer in the photocurable resin composition of the present embodiment is set to 100 parts by mass of the total content of the (meth)acrylate monomer (A) in the photocurable resin composition of the present embodiment, it is preferably 50 parts by mass or more and 95 parts by mass or less, more preferably 55 parts by mass or more and 90 parts by mass or less, still more preferably 60 parts by mass or more and 85 parts by mass or less, still more preferably 63 parts by mass or more and 82 parts by mass or less, and still more preferably 65 parts by mass or more and 80 parts by mass or less.

[0027] <Bifunctional or More (Meth)acrylate Monomers (A2)> Bifunctional or more (meth)acrylate monomers (A2) include, for example, one or more selected from the group consisting of bifunctional or more aromatic ring (meth)acrylate monomers, bifunctional or more alicyclic (meth)acrylate monomers, and bifunctional or more chain (meth)acrylate monomers. Bifunctional or more chain (meth)acrylate monomers include, for example, one or more selected from the group consisting of bifunctional or more linear (meth)acrylate monomers and bifunctional or more branched (meth)acrylate monomers. Bifunctional or more linear (meth)acrylate monomers include, for example, bifunctional or more (meth)acrylate monomers having a linear hydrocarbon skeleton. Bifunctional or more branched (meth)acrylate monomers include, for example, bifunctional or more (meth)acrylate monomers having a branched hydrocarbon skeleton. The (meth)acrylate monomer (A2) comprises, for example, one or more selected from the group consisting of aromatic ring difunctional (meth)acrylate monomers, alicyclic difunctional (meth)acrylate monomers, and chain-type difunctional (meth)acrylate monomers. The chain-type difunctional (meth)acrylate monomer comprises, for example, one or more selected from the group consisting of linear difunctional (meth)acrylate monomers and branched chain difunctional (meth)acrylate monomers. The linear difunctional (meth)acrylate monomer comprises, for example, a difunctional (meth)acrylate monomer having a linear hydrocarbon skeleton. The branched chain difunctional (meth)acrylate monomer comprises, for example, a difunctional (meth)acrylate monomer having a branched hydrocarbon skeleton.

[0028] Alicyclic bifunctional (meth)acrylate monomers are bifunctional (meth)acrylate monomers having an alicyclic hydrocarbon structure in their molecular structure. From the viewpoint of improving heat resistance, the number of carbon atoms in the alicyclic hydrocarbon structure is preferably 4 to 14, more preferably 5 to 12, and even more preferably 6 to 10. The alicyclic hydrocarbon structure may be a saturated hydrocarbon structure or an unsaturated hydrocarbon structure. From the viewpoint of improving heat resistance, the alicyclic hydrocarbon structure is preferably a saturated hydrocarbon structure.

[0029] Furthermore, the alicyclic hydrocarbon structure may be a monocyclic hydrocarbon structure, or a polycyclic hydrocarbon structure such as a fused cyclic hydrocarbon structure or a bridged cyclic hydrocarbon structure. Alicyclic difunctional (meth)acrylate monomers may contain groups containing these alicyclic hydrocarbon structures in their molecular structure, preferably containing divalent groups containing alicyclic hydrocarbon structures. Specific examples of monocyclic hydrocarbon groups include groups having a cycloalkane structure such as cyclohexylene and cyclohexyl groups; and groups having a cycloalkene skeleton such as cyclodecatrienediyl and cyclodecatriene groups. Specific examples of polycyclic hydrocarbon groups include groups having a dicyclopentadiene skeleton such as tricyclodecanediyl, dicyclopentanyl, and dicyclopentenyl groups; groups having a norbornane skeleton such as norbornanediyl, isobornanediyl, norbornyl, and isobornyl groups; and groups having an adamantane skeleton such as adamantanediyl and adamantyl groups.

[0030] A linear, bifunctional (meth)acrylate monomer is a (meth)acrylate having a linear structure in its molecular structure and two (meth)acryloyl groups. The linear structure preferably includes a divalent linear hydrocarbon group, from the viewpoint of improving crack resistance during molding of optical molded articles. The number of carbon atoms in the divalent linear hydrocarbon group is, for example, 1 or more, preferably 2 or more, and more preferably 4 or more, from the viewpoint of reducing the deviation in liquid volume due to monomer volatilization during molding of optical molded articles. Furthermore, from the viewpoint of improving heat resistance, the number of carbon atoms in the divalent linear hydrocarbon group is preferably 20 or less, and more preferably 14 or less.

[0031] Specific examples of linear difunctional (meth)acrylate monomers include alkanediol di(meth)acrylates. Linear difunctional (meth)acrylate monomers are preferably 1,6-hexanediol di(meth)acrylate (e.g., A-HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; HD-N: manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,9-nonanediol di(meth)acrylate (e.g., A-NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; Light acrylate 1,9ND-A, manufactured by Kyoeisha Chemical Co., Ltd.; NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; Light acrylate 1,9ND-M, manufactured by Kyoeisha Chemical Co., Ltd.), 1,10-decanediol di(meth)acrylate (e.g., A-DOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; DOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,12-dodecanediol di It comprises one or more substances selected from the group consisting of (meth)acrylate (e.g., DDD, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; SR262, manufactured by Arkema), ethylene glycol di(meth)acrylate (e.g., SR206NS, manufactured by Arkema), triethylene glycol di(meth)acrylate (e.g., SR272, manufactured by Arkema), polyethylene glycol di(meth)acrylate (e.g., A-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), 1,3-butanediol di(meth)acrylate (e.g., BG, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), and 1,4-butanediol di(meth)acrylate (e.g., BD, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.).

[0032] The bifunctional or more (meth)acrylate monomer (A2) of this embodiment preferably comprises one or more selected from the group consisting of bifunctional or more alicyclic (meth)acrylate monomers and bifunctional or more linear (meth)acrylate monomers, from the viewpoint of further improving the performance balance between the size of the contact angle on the surface of the optically molded body and the transparency of the optically molded body, more preferably comprises one or more selected from the group consisting of bifunctional or more alicyclic (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers, even more preferably comprises linear bifunctional (meth)acrylate monomers, even more preferably comprises one or more selected from the group consisting of 1,12-dodecanediol di(meth)acrylate and tricyclodecanedimethanol di(meth)acrylate, and even more preferably comprises one or more selected from the group consisting of 1,12-dodecanediol dimethacrylate and tricyclodecanedimethanol dimethacrylate.

[0033] From the viewpoint of further improving the balance between the contact angle of the optical molded surface and the transparency of the optical molded body, the total content of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers in the photocurable resin composition of this embodiment is preferably 60 parts by mass or more and 100 parts by mass or less, more preferably 70 parts by mass or more and 100 parts by mass or less, even more preferably 80 parts by mass or more and 100 parts by mass or less, even more preferably 90 parts by mass or more and 100 parts by mass or less, and even more preferably 95 parts by mass or more and 100 parts by mass or less, when the total content of bifunctional or more (meth)acrylate monomers (A2) in the photocurable resin composition of this embodiment is 100 parts by mass.

[0034] <Polysiloxane Compound (E)> Polysiloxane compound (E) is a compound having a polysiloxane skeleton with a repeating siloxane bond structure. In this embodiment, the polysiloxane skeleton refers to a structure in which various organic groups are located on the Si atoms of a polysiloxane having a repeating (-Si-O-) bond structure. The polysiloxane compound (E) of this embodiment is a compound in which a polyoxyalkylene skeleton is included in some of the organic groups on the Si atoms. Examples of such polysiloxane compound (E) include compounds represented by the following formula (1) or formula (2).

[0035] The polysiloxane compound (E) of this embodiment has a polyoxyalkylene skeleton, from the viewpoint of improving the balance between the contact angle on the surface of the optically molded body and the transparency of the optically molded body.

[0036] The polyoxyalkylene skeleton is, for example, (-(R-O) ｎ The polyoxyalkylene skeleton has a structure represented by the formula -). R is an alkylene group, and the number of carbon atoms in the alkylene group is, for example, 1 to 14. n is a natural number of 1 or more. Multiple Rs in a single polyalkylene skeleton may be the same or different from each other. The polyoxyalkylene skeleton has one or more constituent units selected from the group consisting of, for example, ethylene oxide units, propylene oxide units, butylene oxide units, and tetramethylene oxide units.

[0037] The polysiloxane compound (E) of this embodiment preferably comprises one or more compounds selected from the group consisting of the compound represented by the following formula (1) and the compound represented by the following formula (2), and more preferably includes the compound represented by the following formula (1), from the viewpoint of improving the performance balance between the contact angle size of the surface of the optically molded body and the transparency of the optically molded body.

[0038]

[0039] In equation (1), R １ Each of these independently represents an alkyl group having 1 to 4 carbon atoms. ２ and R ３Each of these independently represents an alkylene group having 1 to 4 carbon atoms. ４ is R ３ It exhibits an alkylene group with 1 to 4 carbon atoms, which is different from the above. ５ l represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group. l and m each independently represent an integer in the range of 0 to 1000. (l + m) is an integer of 1 or more. a and b each independently represent an integer in the range of 0 to 100. (a + b) is an integer of 1 or more. Note that in formula (1), the repeating unit having a polyoxyalkylene skeleton (with side chains is R １ (and a repeating unit which is a polyoxyalkylene group) (hereinafter also referred to as repeating unit 1) and a repeating unit which does not have a polyoxyalkylene skeleton (side chain is R １ and R １ The positional relationship between repeating unit 1 (hereinafter also referred to as repeating unit 2) and repeating unit 1 includes both cases where one or more repeating units 1 are located between repeating units 2, and cases where one or more repeating units 2 are located between repeating units 1. In other words, the compound represented by formula (1) is a copolymer containing repeating units 1 and repeating units 2. Furthermore, the compound represented by formula (1) may be a random copolymer, an alternating copolymer, or a block copolymer.

[0040] R in equation (1) １ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of methyl groups and ethyl groups, and more preferably a methyl group. ２ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably a propylene group. ３ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably an ethylene group. ４From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably a propylene group. ５ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), it is preferably one or more selected from the group consisting of a hydrogen atom, a methyl group, and a (meth)acryloyl group, and more preferably a hydrogen atom.

[0041] In formula (1), l is preferably 1 to 1000, more preferably 5 to 300, and even more preferably 5 to 100, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (1), m is preferably 10 to 1000, more preferably 50 to 1000, and even more preferably 100 to 300, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (1), (l + m) is preferably 10 to 2000, more preferably 50 to 1500, and even more preferably 100 to 400, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (1), a is preferably 2 to 100, more preferably 5 to 50, and even more preferably 5 to 20, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (1), b is preferably 0 to 50, more preferably 0 to 10, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (1), (a + b) is preferably 2 to 150, more preferably 5 to 60, and even more preferably 5 to 30, from the viewpoint of improving compatibility with (meth)acrylate monomer (A).

[0042]

[0043] In the above formula (2), R ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms. ７ and R ８ Each of these independently represents an alkylene group having 1 to 4 carbon atoms. ９ is R８ It exhibits an alkylene group with 1 to 4 carbon atoms, which is different from the above. １０ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group. n represents an integer in the range of 0 to 1000. c and d each independently represent an integer in the range of 0 to 100. (c + d) is an integer greater than or equal to 1.

[0044] R in equation (2) ６ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of methyl groups and ethyl groups, and more preferably a methyl group. ７ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably a propylene group. ８ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably an ethylene group. ９ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), R is preferably one or more selected from the group consisting of ethylene groups and propylene groups, and more preferably a propylene group. １０ From the viewpoint of improving compatibility with (meth)acrylate monomer (A), it is preferably one or more selected from the group consisting of a hydrogen atom, a methyl group, and a (meth)acryloyl group, and more preferably a hydrogen atom.

[0045] In formula (2), n is preferably 10 to 1000, more preferably 50 to 1000, and even more preferably 100 to 300, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (2), c is preferably 2 to 100, more preferably 5 to 50, and even more preferably 5 to 20, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (2), d is preferably 0 to 50, more preferably 0 to 10, from the viewpoint of improving compatibility with (meth)acrylate monomer (A). In formula (2), (c + d) is preferably 2 to 150, more preferably 5 to 60, and even more preferably 5 to 30, from the viewpoint of improving compatibility with (meth)acrylate monomer (A).

[0046] The content of polysiloxane compound (E) in the photocurable resin composition of this embodiment is preferably 0.00005 parts by mass or more and 0.5 parts by mass or less, more preferably 0.0001 parts by mass or more and 0.1 parts by mass or less, and even more preferably 0.0005 parts by mass or more, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass, from the viewpoint of further improving the balance between the contact angle of the surface of the optically molded body and the transparency of the optically molded body. . 0.5 parts by mass or less, more preferably 0.001 parts by mass or more and 0.04 parts by mass or less, more preferably 0.001 parts by mass or more and 0.03 parts by mass or less, more preferably 0.001 parts by mass or more and 0.025 parts by mass or less, more preferably 0.001 parts by mass or more and 0.02 parts by mass or less, more preferably 0.001 parts by mass or more and 0.01 parts by mass or less, more preferably 0.002 parts by mass or more and 0.01 parts by mass or less, and more preferably 0.003 parts by mass or more and 0.01 parts by mass or less.

[0047] From the viewpoint of further improving the balance between the contact angle of the optical molded surface and the transparency of the optical molded body, the content of polysiloxane compound (E) in the photocurable resin composition of this embodiment is preferably 0.0001% by mass or more and 0.1% by mass or less, more preferably 0.001% by mass or more and 0.05% by mass or less, even more preferably 0.001% by mass or more and 0.03% by mass or less, even more preferably 0.001% by mass or more and 0.02% by mass or less, even more preferably 0.001% by mass or more and 0.015% by mass or less, even more preferably 0.001% by mass or more and 0.01% by mass or less, even more preferably 0.002% by mass or more and 0.008% by mass or less, and even more preferably 0.003% by mass or more and 0.007% by mass or less, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0048] In this embodiment, the total content of (meth)acrylate monomer (A) and polysiloxane compound (E) in the photocurable resin composition is preferably 70% to 100% by mass, more preferably 80% to 99% by mass, even more preferably 90% to 98% by mass, and even more preferably 93% to 97% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0049] <Antioxidant (B)> The photocurable resin composition of this embodiment may further contain antioxidant (B). Antioxidant (B) is not particularly limited, and known antioxidants can be used. Antioxidant (B) includes, for example, one or more selected from the group consisting of phenolic antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, hindered amine-based antioxidants, and thioether-based antioxidants.

[0050] Examples of phenolic antioxidants include 2,6-di-t-butylhydroxytoluene and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Examples of commercially available phenolic antioxidants include AO-20, AO-30, AO-40, AO-50, AO-60, and AO-80 from the ADEKA Stab series manufactured by ADEKA Corporation.

[0051] Examples of phosphorus-based antioxidants include phosphines such as trialkylphosphines and triarylphosphines, trialkyl phosphites, and triaryl phosphites. Examples of commercially available phosphorus-based antioxidants include the ADEKA Stab series from ADEKA Corporation, such as PEP-4C, PEP-8, PEP-24G, PEP-36, HP-10, 260, 522A, 329K, 1178, 1500, 135A, and 3010.

[0052] Examples of sulfur-based antioxidants include dilauryl 3,3-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl 3,3-thiodipropionate, laurylstearyl 3,3-thiodipropionate, pentaerythritol-tetrakis-(β-lauryl-thio-propionate), and 3,9-bis(2-dodecylthioethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane.

[0053] Examples of hindered amine antioxidants include bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, methyl(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)amino]-6-(2-hydroxyethylamine)-1,3,5-triazine, bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) decandioate, and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate. Examples of commercially available hindered amine antioxidants include AL-72 from the ADEKA Stab series manufactured by ADEKA Corporation, and 111FDL, 123, 144, 152, 292, and 5100 from the TINUVIN series manufactured by BASF.

[0054] Examples of thioether-based antioxidants include ditridecyl 3,3'-thiobispropionate and bis[3-(dodecylthio)propionate]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl. Examples of commercially available thioether-based antioxidants include AO-26, AO-412S, and AO-503A from the ADEKA Stab series manufactured by ADEKA Corporation.

[0055] From the viewpoint of reducing discoloration of the optically molded article, antioxidant (B) preferably comprises one or more selected from the group consisting of phenolic antioxidants and thioether antioxidants. From the viewpoint of further reducing discoloration of the optically molded article, antioxidant (B) more preferably comprises one or more selected from the group consisting of bis[3-(dodecylthio)propionic acid]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl (e.g., Adekastab AO-412S, manufactured by ADEKA Corporation) and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (e.g., Adekastab AO-60, manufactured by ADEKA Corporation).

[0056] From the viewpoint of further improving the performance balance between the contact angle size of the surface of the optically molded body and the transparency of the optically molded body, the content of antioxidant (B) in the photocurable resin composition of this embodiment is preferably 0.010 parts by mass or more and 10 parts by mass or less, more preferably 0.050 parts by mass or more and 5.0 parts by mass or less, even more preferably 0.10 parts by mass or more and 3.0 parts by mass or less, even more preferably 0.20 parts by mass or more and 2.0 parts by mass or less, and even more preferably 0.50 parts by mass or more and 1.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.

[0057] From the viewpoint of further improving the balance between the contact angle of the optical molded surface and the transparency of the optical molded body, the content of antioxidant (B) in the photocurable resin composition of this embodiment is preferably 0.010% to 5.0% by mass, more preferably 0.050% to 4.0% by mass, even more preferably 0.10% to 3.0% by mass, even more preferably 0.30% to 2.0% by mass, and even more preferably 0.50% to 1.5% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0058] <Photopolymerization initiator (C)> The photocurable resin composition of this embodiment may further contain a photopolymerization initiator (C). The photopolymerization initiator (C) is not particularly limited, and known polymerization initiators can be used.

[0059] From the viewpoint of stably forming optically molded articles at low temperatures, the photopolymerization initiator (C) preferably includes a photoradical polymerization initiator. A photoradical polymerization initiator is a compound that generates radicals upon irradiation with ultraviolet or visible light. Examples of photoradical polymerization initiators include acylphosphine oxide-based initiators, oxyphenyl acetate-based initiators, benzoyl glyceride-based initiators, and hydroxyphenyl ketone-based initiators.

[0060] Examples of photopolymerization initiators (C) include benzophenone, Michlar's ketone, 4,4'-bis(diethylamino)benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, isopropylbenzoin ether, isobutylbenzoin ether, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, camphorquinone, benzantrone, 4- Ethyl dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4,4'-tri(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-hexylperoxycarbonyl)benzophenone, 3,3'-di(methoxycarbonyl)-4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4'-di(methoxycarbonyl)-4,3' -di(t-butylperoxycarbonyl)benzophenone, 4,4'-di(methoxycarbonyl)-3,3'-di(t-butylperoxycarbonyl)benzophenone, 2-(4'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine , 2-(4'-pentyloxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 4-[p-N,N-di(ethoxycarbonylmethyl)]-2,6-di(trichloromethyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(2'-chlorophenyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(4'-methoxyphenyl)-s-triazine, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzthiazole, 2-mercaptobenzothiazole, 3,3'-Carbonylbis(7-diethylaminocoumarin),2-(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole,2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-biimidazole,2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole,2,2'-bis(2,4-dibromophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 3-(2-methyl-2-dimethylaminopropionyl)carbazole, 3,6-bis(2-methyl-2-morpholinopropionyl)-9-n-dodecylcarbazole, bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1- Phenyl-1-propanone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propanone, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-1-propanone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-(dimethylamino)-1-(4-morpholinophenyl)-2-benzyl-1-butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4 -(4-morpholinyl)phenyl]-1-butanone, oxyphenyl-acetate 2-[2-oxo-2-phenylacetoxy-ethoxy]-ethyl ester, oxyphenyl-acetate 2-[2-hydroxyethoxy]-ethyl ester, methyl benzoylformate, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphinic acid ester, 1-[4-(phenylthio)phenyl]-1,Examples include 2-octanedione 2-(O-benzoyl oxime) and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-ethanone-1-(O-acetyl oxime).

[0061] The photopolymerization initiator (C) preferably contains a hydroxyphenyl ketone-based initiator, and more preferably contains 1-hydroxycyclohexylphenyl ketone (e.g., Omnirad 184, manufactured by IGM Resins), from the viewpoint of reducing discoloration of the optically molded article.

[0062] From the viewpoint of improving the curability of the photocurable resin composition, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 0.10 parts by mass or more, more preferably 0.50 parts by mass or more, even more preferably 1.0 part by mass or more, even more preferably 2.0 parts by mass or more, and even more preferably 3.0 parts by mass or more, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 10 parts by mass or less, more preferably 8.0 parts by mass or less, even more preferably 6.0 parts by mass or less, even more preferably 5.0 parts by mass or less, and even more preferably 4.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass or less, even more preferably 8.0 parts by mass or less, even more preferably 6.0 parts by mass or less, even more preferably 5.0 parts by mass or less, and even more preferably 4.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass or less. From the viewpoint of improving the curability of the photocurable resin composition and improving the uniformity of the thickness of the photocurable resin composition during curing, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 0.10 parts by mass or more and 10 parts by mass or less, more preferably 0.50 parts by mass or more and 8.0 parts by mass or less, even more preferably 1.0 parts by mass or more and 6.0 parts by mass or less, even more preferably 2.0 parts by mass or more and 5.0 parts by mass or less, and even more preferably 3.0 parts by mass or more and 4.5 parts by mass or less, when the content of (meth)acrylate monomer (A) in the photocurable resin composition of this embodiment is 100 parts by mass.

[0063] From the viewpoint of further improving the balance between the contact angle of the optical molded surface and the transparency of the optical molded body, the content of the photopolymerization initiator (C) in the photocurable resin composition of this embodiment is preferably 0.10% to 10% by mass, more preferably 1.0% to 8.0% by mass, even more preferably 2.0% to 6.0% by mass, even more preferably 2.5% to 5.0% by mass, and even more preferably 3.0% to 4.5% by mass, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0064] <Light stabilizer (D)> The photocurable resin composition of this embodiment may further contain a light stabilizer (D). The light stabilizer (D) is not particularly limited, and known light stabilizers can be used. The photocurable resin composition can have improved color resistance by containing a light stabilizer (D).

[0065] The light stabilizer (D) preferably includes a hindered amine-based light stabilizer, from the viewpoint of improving color resistance.

[0066] Examples of hindered amine-based light stabilizers include: a mixture consisting of 70% by mass of the reaction product of (1,2,2,6,6-pentamethyl-piperidine-4-yl) methacrylic acid, bis(2,2,6,6-tetramethyl-1(octyloxy)-4-piperidinyl) decandioate, 1,1-dimethylethyl hydroperoxide, and octane, and 30% by mass of polypropylene; bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate; bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate; and a mixture of methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate. Examples include substances such as bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, a mixture of 2,2,6,6-tetramethyl-4-piperidyl-1,2,3,4-butanetetracarboxylate and tridecyl-1,2,3,4-butanetetracarboxylate, and a mixture of 1,2,2,6,6-pentamethyl-4-piperidyl-1,2,3,4-butanetetracarboxylate and tridecyl-1,2,3,4-butanetetracarboxylate.

[0067] The light stabilizer (D) preferably contains 1,2,2,6,6-pentamethyl-4-piperidyl methacrylic acid (for example, Adekastab LA-82, manufactured by ADEKA Corporation) from the viewpoint of improving color resistance.

[0068] From the viewpoint of reducing discoloration of the optically molded article, the content of the light stabilizer (D) in the photocurable resin composition of this embodiment is preferably 0.0010% by mass or more, more preferably 0.0050% by mass or more, even more preferably 0.010% by mass or more, even more preferably 0.050% by mass or more, and even more preferably 0.070% by mass or more, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass. From the viewpoint of reducing bleed-out, the content of the light stabilizer (D) in the photocurable resin composition of this embodiment is preferably 1.00% by mass or less, more preferably 0.60% by mass or less, even more preferably 0.50% by mass or less, even more preferably 0.40% by mass or less, and even more preferably 0.30% by mass or less, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass. In this embodiment, the content of the light stabilizer (D) in the photocurable resin composition is preferably 0.0010% by mass or more and 1.00% by mass or less, more preferably 0.0050% by mass or more and 0.60% by mass or less, even more preferably 0.010% by mass or more and 0.50% by mass or less, even more preferably 0.050% by mass or more and 0.40% by mass or less, and even more preferably 0.070% by mass or more and 0.30% by mass or less, when the total amount of solids in the photocurable resin composition (total amount of components remaining as solids when cured) is taken as 100% by mass.

[0069] <Other Components> The photocurable resin composition may contain, as specific examples of other components besides (meth)acrylate monomer (A), polysiloxane compound (E), antioxidant (B), photopolymerization initiator (C), and light stabilizer (D), one or more selected from the group consisting of fillers, curing accelerators, plasticizers, heat stabilizers, flame retardants, antistatic agents, defoamers, silane coupling agents, ultraviolet absorbers, surfactants, and leveling agents.

[0070] <Method for Producing a Photocurable Resin Composition> The photocurable resin composition according to the present invention can be obtained by mixing a (meth)acrylate monomer (A), a polysiloxane compound (E), and other components such as an antioxidant (B), a photopolymerization initiator (C), or a light stabilizer (D) as needed, using a conventionally known method.

[0071] <Physical Properties of Photocurable Resin Compositions> Next, the physical properties of photocurable resin compositions will be described.

[0072] The contact angle between the cured film and water, prepared according to the following <Cured Film Preparation Conditions> measured in accordance with JIS R 3257:1999, will be described for the photocurable resin composition of this embodiment. In the following, the contact angle between the prepared cured film and water will also be referred to as the film contact angle.

[0073] From the viewpoint of further improving the performance balance between the magnitude of the contact angle on the surface of the optically molded body and the transparency of the optically molded body, the film contact angle is preferably 75° or more, more preferably 80° or more, even more preferably 85° or more, and even more preferably 90° or more. There is no particular upper limit to the film contact angle, but it may be, for example, 120° or less, 110° or less, 105° or less, or 100° or less.

[0074] <Conditions for preparing cured film> A 3.0 mm thick, 50 mm x 50 mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35 mm diameter circular hole is placed on a 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet. Next, the circular hole is filled with a photocurable resin composition, and then another 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet is placed on top. Next, this is placed on a SUS lab jack to adjust the height. Next, the photocurable resin composition is irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes from above the alkali-free glass, then it is turned over and irradiated with 405 nm wavelength LED light at 810 mW for 3 minutes. After irradiation with LED light, it is allowed to cool at 23°C for 30 minutes, and the cured photocurable resin composition is released from the alkali-free glass and silicone sheet to obtain a cured film. Here, the conditions for producing a cured film of the photocurable resin composition of this embodiment can be more specifically those described in the examples.

[0075] The film contact angle can be adjusted, for example, by adjusting the content of (meth)acrylate monomer (A), the content of polysiloxane compound (E), the blending ratio of the photocurable resin composition, the type of (meth)acrylate monomer (A), the type of polysiloxane compound (E), the types of other components, and the manufacturing conditions of the photocurable resin composition.

[0076] The following describes the haze value for a photocurable resin composition of this embodiment, measured in accordance with JIS K 7136:2000, when a cured film prepared according to the above-described <Cured Film Preparation Conditions> is immersed in benzyl alcohol at 25°C, under conditions of a thickness of 3.0 mm.

[0077] The above haze value is preferably 1.0% or less, more preferably 0.8% or less, even more preferably 0.6% or less, and even more preferably 0.3% or less, from the viewpoint of further improving the performance balance between the contact angle on the surface of the optically molded body and the transparency of the optically molded body. The lower limit of the above haze value is not particularly limited, but may be, for example, 0.01% or more, 0.05% or more, or 0.1% or more.

[0078] The above haze value can be adjusted, for example, by adjusting the content of (meth)acrylate monomer (A), the content of polysiloxane compound (E), the blending ratio of the photocurable resin composition, the type of (meth)acrylate monomer (A), the type of polysiloxane compound (E), the types of other components, and the manufacturing conditions of the photocurable resin composition. More specifically, the method for measuring the above haze value can be the method described in the examples.

[0079] <Applications of Photocurable Resin Compositions> Next, we will explain the applications of photocurable resin compositions.

[0080] The photocurable resin composition of this embodiment can improve the balance between the contact angle of the surface of an optically molded body molded from the photocurable resin composition and the transparency of the optically molded body, and can therefore be used in methods for forming optically molded bodies such as injection molding, compression molding, injection compression molding, extrusion molding, solution casting, and casting. In particular, the photocurable resin composition of this embodiment can be used in the casting method.

[0081] The photocurable resin composition of this embodiment can improve the balance between the contact angle on the surface of an optically molded body molded from the photocurable resin composition and the transparency of the optically molded body. Therefore, the applications of optically molded bodies molded from the photocurable resin composition are not particularly limited and can be used in a variety of applications.

[0082] The photocurable resin composition of this embodiment can, for example, preferably be used in lenses. The lens may include one or more types selected from the group consisting of spherical lenses, aspherical lenses, biconvex lenses, plano-convex lenses, convex meniscus lenses, biconcave lenses, plano-concave lenses, concave meniscus lenses, etc.

[0083] The photocurable resin composition of this embodiment can be used, for example, more preferably, in one or more lenses selected from the group consisting of lenses for virtual reality devices (VR lenses), lenses for mixed reality devices (MR lenses), lenses for augmented reality devices (AR lenses), lenses for cross-reality devices (xR lenses), and lenses for head-mounted displays (HMD lenses).

[0084] The photocurable resin composition of this embodiment can, for example, preferably be used in a display cover (hereinafter also referred to as a cover display). The cover display may include, for example, one or more selected from the group consisting of a front cover display and a full cover display.

[0085] The photocurable resin composition of this embodiment can be used, for example, more preferably, in one or more cover displays selected from the group consisting of cover displays for virtual reality devices (VR), cover displays for mixed reality devices (MR), cover displays for augmented reality devices (AR), cover displays for cross-reality devices (xR), and cover displays for head-mounted displays (HMD).

[0086] (Optical Molded Body) The optical molded body of this embodiment includes a cured product of the photocurable resin composition of this embodiment. The optical molded body of this embodiment can be manufactured using the photocurable resin composition of this embodiment. The optical molded body can be manufactured from the photocurable resin composition of this embodiment by any method such as injection molding, compression molding, injection compression molding, extrusion molding, solution casting, and casting.

[0087] The optically molded body of this embodiment includes a lens. The lens includes, for example, one or more types selected from the group consisting of spherical lenses, aspherical lenses, biconvex lenses, plano-convex lenses, convex meniscus lenses, biconcave lenses, plano-concave lenses, concave meniscus lenses, etc.

[0088] The lens of this embodiment includes one or more types selected from the group consisting of virtual reality device lenses (VR lenses), mixed reality device lenses (MR lenses), augmented reality device lenses (AR lenses), cross-reality device lenses (xR lenses), and head-mounted display lenses (HMD lenses).

[0089] The optically molded body of this embodiment includes a display cover (cover display). The cover display includes, for example, one or more types selected from the group consisting of a front cover display and a full cover display.

[0090] The cover display of this embodiment includes one or more types selected from the group consisting of cover displays for virtual reality devices (VR), cover displays for mixed reality devices (MR), cover displays for augmented reality devices (AR), cover displays for cross-reality devices (xR), and cover displays for head-mounted displays (HMD).

[0091] The maximum thickness of an optically molded body is the portion of the optically molded body where the thickness of the optical component is greatest. The location of the maximum thickness of the optically molded body is not particularly limited and can be set as appropriate depending on the application, etc.

[0092] For example, the maximum thickness of the optically molded body in this embodiment is preferably 0.01 mm or more, more preferably 0.1 mm or more, even more preferably 0.5 mm or more, even more preferably 1.0 mm or more, even more preferably 2.0 mm or more, even more preferably 3.0 mm or more, even more preferably 4.0 mm or more, and even more preferably 5.0 mm or more.

[0093] For example, the maximum thickness of the optically molded body in this embodiment is preferably 20.0 mm or less, more preferably 19.9 mm or less, even more preferably 19.8 mm or less, even more preferably 19.5 mm or less, even more preferably 18.0 mm or less, even more preferably 17.0 mm or less, even more preferably 16.0 mm or less, and even more preferably 15.0 mm or less.

[0094] For example, the maximum thickness of the optically molded body in this embodiment is preferably 0.01 mm or more and 20.0 mm or less, more preferably 0.1 mm or more and 19.9 mm or less, even more preferably 0.5 mm or more and 19.8 mm or less, even more preferably 1.0 mm or more and 19.5 mm or less, even more preferably 2.0 mm or more and 19.0 mm or less, even more preferably 3.0 mm or more and 18.0 mm or less, even more preferably 4.0 mm or more and 17.0 mm or less, even more preferably 5.0 mm or more and 16.0 mm or less, and even more preferably 5.0 mm or more and 15.0 mm or less.

[0095] Furthermore, the photocurable resin composition of this embodiment can improve the balance between the contact angle on the surface of the optically molded body and the transparency of the optically molded body, and therefore can be applied to optically molded bodies with a thickness of 0.01 mm or more.

[0096] (Optical Device) The optical device of this embodiment comprises the optical molded body of this embodiment. The type of optical device of this embodiment is not particularly limited. Examples of optical devices of this embodiment include virtual reality devices (VR devices), mixed reality devices (MR devices), augmented reality devices (AR devices), cross-reality devices (xR devices), and head-mounted displays (HMD devices).

[0097] Although embodiments of the present invention have been described above, these are merely examples, and various other configurations can be adopted. Furthermore, the present invention is not limited to the embodiments described above, and modifications, improvements, etc., that do not impair the effects of the present invention are included in the present invention.

[0098] This embodiment will be described in detail below with reference to examples and other relevant information. However, this embodiment is not limited in any way to the descriptions of these examples.

[0099] First, the materials used in each example are shown below. • (Meth)acrylate monomer (A) (Meth)acrylate monomer 1: Alicyclic monofunctional (meth)acrylate monomer (dicyclopentanyl methacrylate, GM81HDA, manufactured by Kokusei Chemical Co., Ltd.) (hereinafter also referred to as GM81HDA.) (Meth)acrylate monomer 2: Alicyclic monofunctional (meth)acrylate monomer (isobornyl methacrylate, light ester IB-X, manufactured by Kyoeisha Chemical Co., Ltd.) (hereinafter also referred to as IB-X.) (Meth)acrylate monomer 3: Alicyclic bifunctional (meth)acrylate monomer (tricyclodecanedimethanol dimethacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) (hereinafter also referred to as DCP.) (Meth)acrylate monomer 4: Linear bifunctional (meth)acrylate monomer (1,12-dodecanediol dimethacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) (hereinafter also referred to as DDD.)

[0100] • Polysiloxane compounds having a polyoxyalkylene skeleton (E) Polysiloxane compound 1: DOWSIL SH 3773 M Fluid (polydimethylsiloxane polymer having a polyoxyalkylene skeleton, manufactured by The Dow Chemical Company) (hereinafter also referred to as DOWSIL.) (DOWSIL is a registered trademark of The Dow Chemical Company.) • Polysiloxane compounds not having a polyoxyalkylene skeleton Polysiloxane compound 2: X-22-164AS (polydimethylsiloxane having methacrylic groups at both ends, manufactured by Shin-Etsu Chemical Co., Ltd.)

[0101] • Antioxidants (B) Antioxidant 1: Thioether-based antioxidant (bis[3-(dodecylthio)propionic acid]2,2-bis[[3-(dodecylthio)-1-oxopropyloxy]methyl]-1,3-propanediyl, manufactured by ADEKA Corporation, product name: Adekastab AO-412S) (hereinafter also referred to as AO-412S) Antioxidant 2: Phenolic antioxidant (pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by ADEKA Corporation, product name: Adekastab AO-60) (hereinafter also referred to as AO-60) • Photopolymerization initiator (C) Photopolymerization initiator 1: Photoradical polymerization initiator (1-hydroxycyclohexylphenyl ketone, manufactured by IGM Resins, product name: Omnirad 184) • Light stabilizer (D) Light stabilizer 1: Hindered amine-based light stabilizer (1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, manufactured by ADEKA Corporation, product name: ADEKA Stab LA-82) (hereinafter also referred to as LA-82)

[0102] (Examples 1-4, Comparative Examples 1-3) Liquid photocurable resin compositions were obtained by blending each component to achieve the formulations shown in Table 1. The units of the formulations in Table 1 are parts by mass. The physical properties of the optically molded articles obtained from the photocurable resin compositions of each example were measured by the following method. The measurement results are shown in Table 1.

[0103] <Method for Measuring the Contact Angle Between Cured Film and Water> For each example of the photocurable resin composition, a cured film was prepared according to the <Conditions for Preparing Cured Film> described below. Next, the contact angle between the prepared cured film and water (film contact angle) was measured in accordance with JIS R 3257:1999, with a sample size of n=5. The average value calculated from the measured values ​​was defined as the contact angle between the prepared cured film and water. A contact angle meter (product name: DMo-0902, manufactured by Kyowa Interface Science Co., Ltd.) was used to measure the contact angle. In the case of the photocurable resin composition in Comparative Example 3, the cured film cracked, so the contact angle was not measured.

[0104] <Conditions for preparing cured film> A 3.0 mm thick, 50 mm x 50 mm silicone sheet (material: silicone rubber, hardness: 50 degrees) with a 35 mm diameter circular hole was placed on top of a 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet (product name: JIS R 3202, glass plate with a fine surface, manufactured by Test Piece Co., Ltd.). After filling the circular hole in the silicone sheet with a photocurable resin composition, another 0.7 mm thick, 50 mm x 50 mm alkali-free glass sheet (product name: JIS R 3202, glass plate with a fine surface, manufactured by Test Piece Co., Ltd.) was placed on top. At this time, it was confirmed that there were no air bubbles. Hereinafter, the above-mentioned alkali-free glass sheet with a silicone sheet placed on top, with the photocurable resin composition filled in the circular hole in the silicone sheet, and then another alkali-free glass sheet placed on top, may be referred to as a laminate. The above-mentioned laminate was placed on a SUS lab jack, and the height of the SUS lab jack was adjusted. The photocurable resin composition was irradiated with 405 nm LED light at 810 mW for 3 minutes using an LED light irradiation device (CCS Corporation, product name: 405 nm - 120 mm air-cooled batch irradiation device, model number: HLDL-120505-NWPSC) on top of alkali-free glass. Then, the laminate was flipped over and irradiated again with 405 nm LED light at 810 mW for another 3 minutes. After irradiation with LED light, the laminate was allowed to cool at 23°C for 30 minutes. After cooling, the cured photocurable resin composition was released from the alkali-free glass and silicone sheet to obtain a cured film of the photocurable resin composition. The LED light irradiation intensity was measured using an ultraviolet integrated light meter (product name: UIT-250, Ushio Inc.).

[0105] <Method for Evaluating Transparency> For each example of the photocurable resin composition, a cured film was prepared according to the <Conditions for Preparing Cured Films> described above. Next, the prepared cured film was immersed in benzyl alcohol at 25°C. Then, the haze value (haze value during benzyl alcohol immersion) of the cured film immersed in benzyl alcohol, at a thickness of 3.0 mm, was measured in accordance with JIS K 7136:2000. A haze value of 0.3% or less during benzyl alcohol immersion was evaluated as A, a value between 0.3% and 0.6% was evaluated as B, and a value greater than 0.6% was evaluated as C.

[0106]

[0107] This application claims priority based on Japanese Patent Application No. 2024-168818, filed on 27 September 2024, and incorporates all of its disclosures herein.

Claims

1. A photocurable resin composition that can be used in optically molded articles, comprising a (meth)acrylate monomer and a polysiloxane compound, wherein the (meth)acrylate monomer comprises a (meth)acrylate monomer with two or more functionalities, and the polysiloxane compound has a polyoxyalkylene skeleton.

2. The photocurable resin composition according to claim 1, wherein the polysiloxane compound contains one or more compounds selected from the group consisting of a compound represented by the following formula (1) and a compound represented by the following formula (2). (In the formula (1), R １ each independently represents an alkyl group having 1 to 4 carbon atoms, R ２ and R ３ each independently represents an alkylene group having 1 to 4 carbon atoms, R ４ represents an alkylene group having 1 to 4 carbon atoms different from R ３ , R ５ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group, l and m each independently represent an integer in the range of 0 to 1000, (l + m) is an integer of 1 or more, a and b each independently represent an integer in the range of 0 to 100, and (a + b) is an integer of 1 or more.) (In the formula (2), R ６ each independently represents an alkyl group having 1 to 4 carbon atoms, R ７ and R ８ each independently represents an alkylene group having 1 to 4 carbon atoms, R ９ represents an alkylene group having 1 to 4 carbon atoms different from R ８ , R １０ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a (meth)acryloyl group, n represents an integer in the range of 0 to 1000, c and d each independently represent an integer in the range of 0 to 100, and (c + d) is an integer of 1 or more.) 3. The photocurable resin composition according to claim 1 or 2, wherein the content of the polysiloxane compound is 0.00005 parts by mass or more and 0.5 parts by mass or less, when the content of the (meth)acrylate monomer is 100 parts by mass.

4. The photocurable resin composition according to any one of claims 1 to 3, wherein the bifunctional or more (meth)acrylate monomer comprises one or more selected from the group consisting of alicyclic bifunctional (meth)acrylate monomers and linear bifunctional (meth)acrylate monomers.

5. The photocurable resin composition according to claim 4, wherein the total content of the alicyclic bifunctional (meth)acrylate monomer and the linear bifunctional (meth)acrylate monomer is 60 parts by mass or more and 100 parts by mass or less, when the total content of the bifunctional or more (meth)acrylate monomers is 100 parts by mass.

6. The photocurable resin composition according to any one of claims 1 to 5, wherein the content of the bifunctional or more (meth)acrylate monomer is 5 parts by mass or more and 100 parts by mass or less when the total content of the (meth)acrylate monomer is 100 parts by mass.

7. The photocurable resin composition according to any one of claims 1 to 6, wherein the (meth)acrylate monomer further comprises a monofunctional (meth)acrylate monomer.

8. The photocurable resin composition according to claim 7, wherein the monofunctional (meth)acrylate monomer has an alicyclic skeleton.

9. A photocurable resin composition according to any one of claims 1 to 8, further comprising an antioxidant.

10. A photocurable resin composition according to any one of claims 1 to 9, further comprising a photopolymerization initiator.

11. The photocurable resin composition according to claim 10, wherein the photopolymerization initiator comprises a photoradical polymerization initiator.

12. A photocurable resin composition according to any one of claims 1 to 11, further comprising a light stabilizer.

13. A photocurable resin composition according to any one of claims 1 to 12, which can be used in a casting method.

14. A photocurable resin composition according to any one of claims 1 to 13, which can be used for one or more lenses selected from the group consisting of lenses for virtual reality devices (VR lenses), lenses for mixed reality devices (MR lenses), lenses for augmented reality devices (AR lenses), lenses for cross-reality devices (xR lenses), and lenses for head-mounted displays (HMD lenses).

15. An optically molded article comprising a cured product of a photocurable resin composition according to any one of claims 1 to 14.

16. The optical molded body according to claim 15, wherein the optical molded body includes a lens.

17. The optical molded body according to claim 16, wherein the lens includes one or more selected from the group consisting of virtual reality device lenses (VR lenses), mixed reality device lenses (MR lenses), augmented reality device lenses (AR lenses), cross-reality device lenses (xR lenses), and head-mounted display lenses (HMD lenses).

18. The optical molded body according to claim 15, wherein the optical molded body includes a cover display.

19. The optical molded body according to claim 18, wherein the cover display includes one or more selected from the group consisting of a cover display for a virtual reality device, a cover display for a mixed reality device, a cover display for an augmented reality device, a cover display for a cross-reality device, and a cover display for a head-mounted display.

20. An optical molded body according to any one of claims 15 to 19, wherein the maximum thickness of the part is 20 mm or less.

21. An optically molded body according to any one of claims 15 to 20, wherein the maximum thickness of the part is 0.01 mm or more.

22. An optical device comprising an optically molded body according to any one of claims 15 to 21.

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