Photosensitive composition, cured product, laminated film, and article

Abstract

The purpose of the present invention is to provide a photosensitive composition that can yield a cured product exhibiting excellent appearance, hardness, wear resistance, and flex resistance. The present invention relates to a photosensitive composition characterized by containing a polyfunctional compound (A) represented by the following general formula (1), inorganic particles (B) having an average primary particle size of 1 to 100 nm, and a photopolymerization initiator (C). In formula (1), X represents a trivalent or higher organic group or a divalent organic group having a cyclic structure. n is an integer greater than or equal to 2).

Description

Photosensitive compositions, cured products, laminated films and articles

[0001] The present invention relates to photosensitive compositions, cured products, laminated films, and articles. More specifically, it relates to photosensitive compositions, cured products, laminated films, and articles that can provide cured products with excellent appearance, hardness, abrasion resistance, and flexibility.

[0002] Photosensitive compositions that react to and harden in response to light are being considered for various applications in optical components such as color filters, photoresists, inks, hard coats, and optical films used in liquid crystal displays, as well as in electrical and electronic equipment. Development is underway to create photosensitive compositions with excellent properties required for each application.

[0003] Image display devices such as liquid crystal displays and organic EL displays have a hard coat applied to the outermost layer to prevent scratches on the screen. In recent years, flexible foldable displays and other image display devices have become known. The hard coat applied to such image display devices requires not only excellent hardness and scratch resistance (abrasion resistance), but also flexibility that prevents cracking even when repeatedly bent. A highly transparent appearance is also required. Various studies have been conducted on photosensitive compositions for forming such hard coats (Patent Documents 1 to 3).

[0004] International Publication No. 2018 / 037488, Japanese Patent Publication No. 2021-59040, Japanese Patent Publication No. 2022-77715

[0005] However, conventional photosensitive compositions have not been able to form cured products that are superior in appearance, hardness, abrasion resistance, and flexibility.

[0006] This invention has been made in view of the above-mentioned circumstances, and aims to provide a photosensitive composition that can give a cured product that is excellent in appearance, hardness, wear resistance, and flexibility.

[0007] The inventors of the present invention conducted various studies on photosensitive compositions and discovered that by including a specific polyfunctional compound, inorganic particles having a specific particle size range, and a photopolymerization initiator, a cured product with excellent appearance, hardness, abrasion resistance, and flexibility can be obtained, thus completing the present invention.

[0008] The present invention includes the following embodiments: <1> A photosensitive composition characterized by comprising a polyfunctional compound (A) represented by the following general formula (1), inorganic particles (B) having an average primary particle diameter of 1 to 100 nm, and a photopolymerization initiator (C).

[0009]

[0010] (In formula (1), X represents a divalent organic group having a cyclic structure, or a trivalent or greater organic group. n is an integer of 2 or more.) <2> The photosensitive composition according to <1>, further characterized by comprising a polyfunctional urethane (meth)acrylate (D). <3> The photosensitive composition according to <1> or <2>, characterized in that the inorganic particles (B) comprise at least one particle selected from the group consisting of silica, zirconia, titania, and alumina. <4> The photosensitive composition according to any one of <1> to <3>, characterized in that the content of the inorganic particles (B) is 10 to 1000 parts by mass per 100 parts by mass of the polyfunctional compound (A). <5> The photosensitive composition according to any one of <2> to <4>, characterized in that the content of the polyfunctional urethane (meth)acrylate (D) is 10 to 1000 parts by mass per 100 parts by mass of the polyfunctional compound (A). <6> A cured product of the photosensitive composition described in any of <1> to <5> above. <7> A laminated film characterized by having a hard coat layer containing the cured product described in <6> above. <8> An article characterized by comprising the cured product described in <6> above.

[0011] The photosensitive composition of the present invention can provide a cured product with excellent appearance, hardness, abrasion resistance, and flexibility. The photosensitive composition of the present invention can be suitably used in hard coat films for flexible devices and the like.

[0012] The present invention is described in detail below. Furthermore, combinations of two or more of the individual preferred embodiments of the present invention described below are also preferred embodiments of the present invention. In this specification, "(meth)acrylate" means "methacrylate and / or acrylate," and "(meth)acrylic acid" means "acrylic acid and / or methacrylic acid."

[0013] 1. Photosensitive Composition The photosensitive composition of the present invention is characterized by comprising a polyfunctional compound (A) represented by the above general formula (1), inorganic particles (B) having an average primary particle diameter of 1 to 100 nm, and a photopolymerization initiator (C). The photosensitive composition of the present invention can provide a cured product with excellent appearance, hardness, abrasion resistance, and flexural resistance because the inclusion of the polyfunctional compound improves the hardness and flexural resistance of the resulting cured product, and the inclusion of the inorganic particles improves the appearance, hardness, and abrasion resistance. Each component contained in the photosensitive composition of the present invention will be described in detail below.

[0014] (A) Polyfunctional compound The photosensitive composition of the present invention contains a polyfunctional compound represented by the above general formula (1) (hereinafter also referred to as polyfunctional compound (A)). The above polyfunctional compound (A) is a compound having two or more allyloxymethylacryloyloxy groups (allyloxymethylacrylic acid derivative). By including such a polyfunctional compound, a cured product with excellent hardness, wear resistance and flexure resistance can be obtained.

[0015] In the above general formula (1), X represents a divalent organic group having a cyclic structure, or an organic group with three or more valencies. That is, in the above general formula (1), when n is 2, X is a divalent organic group having a cyclic structure, and when n is 3 or more, X is an organic group with three or more valencies.

[0016] The above-mentioned cyclic structure is not particularly limited as long as it contains at least one aliphatic or aromatic ring, and may consist of a single ring or multiple rings. The above-mentioned cyclic structure may consist of multiple rings joined together, fused together, or linked together via a single atom.

[0017] The above aliphatic ring may be monocyclic or polycyclic, but polycyclic is preferred in that it improves hardness. Examples of the above aliphatic ring include aliphatic hydrocarbon rings and aliphatic heterocyclic rings.

[0018] Examples of the above-mentioned aliphatic hydrocarbon rings include cyclopropane rings, cyclopropene rings, cyclobutane rings, cyclopentane rings, cyclopentene rings, cyclohexane rings, cycloheptane rings, cyclooctane rings, bicyclo[2.1.0]pentane rings, bicyclo[2.2.1]heptane rings (norbornane rings), norbornene rings, dicyclopentanyl rings, dicyclopentenyl rings, bicyclo[3.2.1]octane rings, tricyclo[3.3.1.13,7]decane rings (adamantane rings), and tricyclo[5.2.1.02,6]decane rings (tricyclodecane rings). Among these, aliphatic hydrocarbon rings having 1 to 12 carbon atoms are preferred, and tricyclo[5.2.1.02,6]decane rings (tricyclodecane rings) are more preferred.

[0019] Examples of the above aliphatic heterocycles include aziridine rings, oxirane rings, thiirane rings, azetidine rings, oxetane rings, pyrrolidine rings, imidazolidine rings, imidazoline rings, dioxolane rings, tetrahydrofuran rings, tetrahydrothiophene rings, tetrahydrofuran rings, dioxane rings, piperazine rings, morpholine rings, quinuclidine rings, hydantoin rings, nurate rings, and 2,4,8,10-tetraoxaspiro[5.5]undecane rings.

[0020] The number of carbon atoms in the above aliphatic heterocycle is preferably 1 to 13, with a nulate ring and a 2,4,8,10-tetraoxaspiro[5.5]undecane ring being more preferred.

[0021] Examples of the aromatic rings mentioned above include aromatic hydrocarbon rings and aromatic heterocycles. Examples of the aromatic hydrocarbon rings include monocycles such as benzene rings, condensed rings such as naphthalene rings, anthracene rings, phenanthrene rings, triphenylene rings, pyrene rings, perylene rings, fluorene rings, and fluorantene rings, and bonded rings such as biphenyl rings, terphenyl rings, and binaphthalene rings.

[0022] Examples of the above aromatic heterocyclic ring include monocyclic rings such as a furan ring, a pyran ring, a thiophene ring, a thiopyran ring, a pyrrole ring, a pyridine ring, an imidazole ring, a pyrazole ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an oxazole ring, an isoxazole ring, a furazan ring, a thiazole ring, an isothiazole ring, etc., polycyclic condensed rings such as a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, an indole ring, an isoindole ring, a carbazole ring, a quinoline ring, a phenanthridine ring, a benzimidazole ring, a purine ring, a phenothiazine ring, etc., and polycyclic bonded rings such as a bipyridine ring, a bithiophene ring, a phenylpyridine ring, a phenylthiophene ring, a diphenylthiophene ring, etc.

[0023] The above aliphatic ring and aromatic ring may have a substituent such as an alkyl group.

[0024] Examples of the divalent organic group having the above cyclic structure include, for example, a group represented by the following general formula (2). -R １ -X １ -R ２ - (2) (In formula (2), R １ and R ２ are the same or different and represent a direct bond, or a divalent aliphatic hydrocarbon group, -O-, -CO-, -COO-, -NH-, -S-, -SO-, -SO ２ - or a group combining these. X １ represents an aliphatic ring group or an aromatic ring group which may have a substituent.)

[0025] As the above divalent aliphatic hydrocarbon group, a chain-like saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms is preferable, and a chain-like saturated aliphatic hydrocarbon group having 1 to 4 carbon atoms is more preferable.

[0026] Among them, R １ and R ２ are preferably the same or different and are a divalent aliphatic hydrocarbon group, or a group combining a divalent aliphatic hydrocarbon group and -O-, and more preferably a divalent aliphatic hydrocarbon group.

[0027] X １Examples of the aliphatic cyclic group represented by include divalent groups formed by removing two hydrogen atoms from the above-described aliphatic ring. X １ Examples of the aromatic cyclic group represented by include divalent groups formed by removing two hydrogen atoms from the above-described aromatic ring. The above aliphatic cyclic group and aromatic cyclic group may have a substituent such as an alkyl group.

[0028] Examples of the trivalent or higher-valent organic group represented by X include a hydrocarbon group or heterocyclic group which may have a substituent, or a combination of a hydrocarbon group and / or heterocyclic group which may have a substituent and a linking group such as -O-, -CO-, -COO-, -NH-, -S-, -SO- or -SO ２ -. Examples of the group composed of the combination of the above hydrocarbon group and / or heterocyclic group and the above linking group include a group containing one or more of the above hydrocarbon groups and / or heterocyclic groups and one or more of the above linking groups.

[0029] Examples of the above hydrocarbon group include a divalent or trivalent or higher-valent aliphatic hydrocarbon group, alicyclic hydrocarbon group, or aromatic hydrocarbon group. Examples of the divalent aliphatic hydrocarbon group include chain-like saturated or unsaturated aliphatic hydrocarbon groups such as a methylene group, ethylene group, propylene group, isopropylene group, butylene group, isobutylene group, t-butylene group, pentylene group and the like.

[0030] Examples of the divalent alicyclic hydrocarbon group include divalent groups formed by removing two hydrogen atoms from the above-described aliphatic hydrocarbon ring.

[0031] Examples of the divalent aromatic hydrocarbon group include divalent groups formed by removing two hydrogen atoms from the above-described aromatic hydrocarbon ring.

[0032] Examples of the trivalent or higher-valent aliphatic hydrocarbon group, alicyclic hydrocarbon group, or aromatic hydrocarbon group include n-valent groups formed by removing (n - 2) hydrogen atoms (n is an integer of 3 or more) from the above-described divalent aliphatic hydrocarbon group, alicyclic hydrocarbon group, or aromatic hydrocarbon group, respectively.

[0033] The number of carbon atoms of the above hydrocarbon group is preferably 1 to 30, more preferably 2 to 25, and still more preferably 3 to 15.

[0034] Examples of the above heterocyclic group include divalent or higher aliphatic heterocyclic groups and aromatic heterocyclic groups formed by removing two or more hydrogen atoms from the above-mentioned aliphatic heterocycles and aromatic heterocycles.

[0035] The above hydrocarbon group and heterocyclic group may have a substituent such as an alkyl group.

[0036] Among them, in terms of excellent weather resistance, the above trivalent or higher organic group is preferably a hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, or a group composed of a combination of a hydrocarbon group and / or a heterocyclic group which may have a substituent and -O-.

[0037] The number of carbon atoms of the above trivalent or higher organic group is preferably 1 to 30, more preferably 2 to 25, and still more preferably 5 to 20.

[0038] In the above general formula (1), n is an integer of 2 or more, but in terms of suppressing curing shrinkage, n is preferably 2 to 6, more preferably 2 to 5, and still more preferably 2 to 4.

[0039] Specific examples of the above polyfunctional compound (A) preferably include, for example, the following compounds. (Compound having two allyloxymethylacryloyloxy groups) Tricyclodecanedimethanol di(2-(allyloxymethyl)acrylate), 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5. The compounds 5]undecane di(2-(allyloxymethyl)acrylate), cyclohexanedimethanol di(2-(allyloxymethyl)acrylate), 2,2-bis(4-polyoxyethylene-oxyphenyl)propane di(2-(allyloxymethyl)acrylate), etc.

[0040] (Compounds having three or more allyloxymethylacryloyloxy groups) Tris(2-hydroxyethyl) isocyanurate tri(2-(allyloxymethyl)acrylate), trimethylolpropane tri(2-(allyloxymethyl)acrylate), ditrimethylolpropanetetra(2-(allyloxymethyl)acrylate), pentaerythritol tetra(2-(allyloxymethyl)acrylate), dipentaerythritol hexa(2-(allyloxymethyl)acrylate), etc.

[0041] The above photosensitive composition may contain only one of the above polyfunctional compound (A), or it may contain two or more. The content of the above polyfunctional compound (A) in the above photosensitive composition is not particularly limited, but in terms of further improving hardness and flexural resistance, it is preferably 10 to 90% by mass, more preferably 15 to 80% by mass, and even more preferably 20 to 70% by mass, based on 100% by mass of the total solid content of the photosensitive composition. In this specification, the total solid content means the total amount of components that form the cured product (non-volatile components excluding solvents and the like that volatilize during the formation of the cured product).

[0042] (D) Polyfunctional urethane (meth)acrylate The above photosensitive composition preferably further contains polyfunctional urethane (meth)acrylate (D) as a monomer component, in that the abrasion resistance of the cured product is further improved. The above polyfunctional urethane (meth)acrylate (D) is a polyfunctional compound having a urethane bond in the molecule and having two or more (meth)acryloyl groups (i.e., two or more functional compounds). The above polyfunctional urethane (meth)acrylate (D) is preferably 2 to 30 functional, more preferably 2 to 20 functional, and even more preferably 2 to 15 functional.

[0043] Examples of the polyfunctional urethane (meth)acrylate (D) mentioned above include urethane reaction products of polyisocyanates with polyols and hydroxyl group-containing (meth)acrylic acid esters. These urethane reaction products also include polymers such as adducts, biuretes, and nurates.

[0044] Examples of the above-mentioned polyisocyanates include aromatic isocyanates such as tolylene diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, diphenylmethane diisocyanate, and p-phenylene diisocyanate; alicyclic isocyanates such as dicyclohexylmethane diisocyanate and isophorone diisocyanate; and aliphatic isocyanates such as hexamethylene diisocyanate.

[0045] Examples of the polyols mentioned above include polyether polyols, polyester polyols, and polycarbonate polyols. There are no particular limitations on the polyether polyols, and examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, random copolymers or block copolymers of ethylene oxide and propylene oxide, and ethylene oxide and butylene oxide. Furthermore, polyether polyester polyols having ether bonds and ester bonds can also be used.

[0046] There are no particular restrictions on the polyester polyols, and examples include polyethylene adipate diol, polybutylene adipate diol, polyethylene butylene adipate diol, polyhexamethylene isophthalate adipate diol, polyethylene succinate diol, polybutylene succinate diol, polyethylene sebacate diol, polybutylene sebacate diol, poly-ε-caprolactone diol, poly(3-methyl-1,5-pentylene adipate) diol, and polycondensates of 1,6-hexanediol and dimer acid.

[0047] There are no particular restrictions on the polycarbonate polyols used. Examples include polytetramethylene carbonate diol, polyhexamethylene carbonate diol, poly(1,4-cyclohexanemethylene carbonate) diol, and poly(hexamethylene-1,4-cyclohexanemethylene carbonate) diol. Polymer polyols and plant-derived polyols (castor oil, linseed oil, etc.) can also be used.

[0048] The polyol component may be any polyol used alone, or a mixture of two or more of the polyols. In other words, the polyol component may consist of one or more of the polyols. The polyol component may be a difunctional polyol or a trifunctional polyol. A mixture of these can also be used.

[0049] Examples of the hydroxyl group-containing (meth)acrylic esters mentioned above include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 2-hydroxybutyl (meth)acrylate.

[0050] The molecular weight of the above-mentioned polyfunctional urethane (meth)acrylate (D) is preferably 1,000 to 200,000, more preferably 1,000 to 150,000, and even more preferably 1,000 to 100,000, in terms of excellent reactivity.

[0051] A commercially available product may be used as the above-mentioned polyfunctional urethane (meth)acrylate (D). Examples of commercially available polyfunctional urethane (meth)acrylate (D) products that can be used include, for example, Sartomer CN996, Sartomer CN962, Sartomer CN9009, Sartomer CN968C, Sartomer CN9006NS, Sartomer CN964, Sartomer CN9011, Sartomer CN9013, Sartomer CN8885, Sartomer CN2302, Sartomer CN2303, Sartomer CN2304 (all manufactured by Arkema Corporation), ART RESIN UN-905, ART RESIN H-575B, and ART RESIN. Examples include UN-904, ART RESIN UN-901T, ART RESIN UN-3320HA, ART RESIN UN-3320HS (all manufactured by Negami Kogyo Co., Ltd.), KRM 8452, KRM 8904, KRM 8684F, KRM 8531BA, EBECRYL 1290 (all manufactured by Daicel Ornex Co., Ltd.), Shiko UV-1700B, Shiko UV-7630B, Shiko UV-7650B (all manufactured by Mitsubishi Chemical Corporation), and others.

[0052] The above photosensitive composition may contain only one type of the above-mentioned polyfunctional urethane (meth)acrylate (D), or it may contain two or more types. The content of the above-mentioned polyfunctional urethane (meth)acrylate (D) is preferably 5 to 90% by mass, more preferably 7 to 70% by mass, and even more preferably 10 to 50% by mass, based on 100% by mass of the total solid content of the photosensitive composition.

[0053] The content of the above-mentioned polyfunctional urethane (meth)acrylate (D) is preferably 10 to 1000 parts by mass, more preferably 13 to 800 parts by mass, even more preferably 20 to 600 parts by mass, and still more preferably 50 to 200 parts by mass, per 100 parts by mass of the above-mentioned polyfunctional compound (A).

[0054] (E) Polyfunctional (meth)acrylate The above photosensitive composition may further contain, as a monomer component, a polyfunctional (meth)acrylate (hereinafter also referred to as polyfunctional (meth)acrylate (E)) copolymerizable with the above polyfunctional compound (A) and polyfunctional urethane (meth)acrylate (D).

[0055] The above-mentioned polyfunctional (meth)acrylate (E) is a compound other than the above-mentioned polyfunctional compound (A) and polyfunctional urethane (meth)acrylate (D), and is, for example, a bifunctional (meth)acrylate compound such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, bisphenol A alkylene oxide di(meth)acrylate; Examples include trimethylolpropane tri(meth)acrylate, ditrimethylolpropanetetra(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, ethylene oxide-added trimethylolpropane tri(meth)acrylate, ethylene oxide-added ditrimethylolpropanetetra(meth)acrylate, ethylene oxide-added pentaerythritol tetra(meth)acrylate, ethylene oxide-added dipentaerythritol hexa(meth)acrylate, and other polyfunctional (meth)acrylate compounds with three or more functions; and so on.

[0056] The above photosensitive composition may contain only one of the above polyfunctional (meth)acrylate (E), or it may contain two or more. The content of the above polyfunctional (meth)acrylate (E) is preferably 0 to 50% by mass, more preferably 0 to 30% by mass, and even more preferably 0 to 20% by mass, based on 100% by mass of the total solid content of the photosensitive composition.

[0057] (F) Other monomers The above photosensitive composition may further contain other monomers (F) other than the polyfunctional compound (A), polyfunctional urethane (meth)acrylate (D), and polyfunctional (meth)acrylate (E) described above. The above other monomer (F) is not particularly limited as long as it is a monomer that can copolymerize with the polyfunctional compound (A), polyfunctional urethane (meth)acrylate (D), and polyfunctional (meth)acrylate (E) described above, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth) ) Acrylate, Isoamyl (meth)acrylate, Hexyl (meth)acrylate, Heptyl (meth)acrylate, Octyl (meth)acrylate, Isooctyl (meth)acrylate, 2-Ethylhexyl (meth)acrylate, Nonyl (meth)acrylate, Decyl (meth)acrylate, Isodecyl (meth)acrylate, Undecyl (meth)acrylate, Dodecyl (meth)acrylate, Lauryl (meth)acrylate, Stearyl (meth)acrylate, Isostearyl (meth) Acrylate, isobornyl (meth)acrylate, 1-adamantyl (meth)acrylate, 2-methyl-2-adamantyl (meth)acrylate, 2-ethyl-2-adamantyl (meth)acrylate, bornyl (meth)acrylate, tricyclodecanyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, 1-naphthylmethyl (meth)acrylate, 2- Naphthylmethyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxy-2-methylethyl (meth)acrylate, phenoxyethoxyethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, 2-phenylphenoxyethyl (meth)acrylate, 4-phenylphenoxyethyl (meth)acrylate, 3-(2-phenylphenyl)-2-hydroxypropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate,Monofunctional (meth)acrylates such as 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, butoxyethyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, polyethylene glycol mono (meth)acrylate, polypropylene glycol mono (meth)acrylate, methoxyethylene glycol (meth)acrylate, ethoxyethyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, etc.; polyfunctional vinyl ethers such as ethylene glycol divinyl ether, diethylene glycol divinyl ether, polyethylene glycol divinyl ether; vinyl ether group-containing (meth)acrylic acid esters such as 2-vinyloxyethyl (meth)acrylate, 3-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxyethyl (meth)acrylate, 2-vinyloxypropyl (meth)acrylate, and 2-(vinyloxyethoxy)ethyl (meth)acrylate; Examples include polyfunctional allyl ethers such as ethylene glycol diallyl ether, diethylene glycol diallyl ether, polyethylene glycol diallyl ether, propylene glycol diallyl ether, butylene glycol diallyl ether, and hexanediol diallyl ether.

[0058] The above photosensitive composition may contain, as monomer components, the polyfunctional compound (A), polyfunctional urethane (meth)acrylate (D), polyfunctional (meth)acrylate (E), and other monomers (F). The total amount of monomer components in the above photosensitive composition is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and even more preferably 30 to 70% by mass, based on 100% by mass of the total solid content of the photosensitive composition. The total amount of monomer components is the sum of the polyfunctional compound (A), polyfunctional urethane (meth)acrylate (D), polyfunctional (meth)acrylate (E), and other monomers (F).

[0059] The content of the above polyfunctional compound (A) is preferably 20 to 100% by mass, more preferably 30 to 90% by mass, and even more preferably 40 to 80% by mass, based on 100% by mass of the total amount of monomer components.

[0060] The content of the above-mentioned polyfunctional urethane (meth)acrylate (D) is preferably 0 to 80% by mass, more preferably 20 to 70% by mass, and even more preferably 40 to 60% by mass, based on 100% by mass of the total amount of monomer components.

[0061] The content of the above-mentioned polyfunctional (meth)acrylate (E) is preferably 0 to 40% by mass, more preferably 0 to 30% by mass, and even more preferably 0 to 20% by mass, based on 100% by mass of the total amount of monomer components.

[0062] The content of the above-mentioned other monomer (F) is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less, based on 100% by mass of the total amount of monomer components.

[0063] (B) Inorganic particles The above photosensitive composition contains inorganic particles (B) having an average primary particle diameter of 1 to 100 nm. The inclusion of inorganic particles in the above photosensitive composition makes it possible to obtain a cured product with high transparency, good appearance, and high hardness. Furthermore, it is possible to improve the wear resistance of the cured product.

[0064] The inorganic particles (B) described above are not particularly limited as long as they contain inorganic matter as the main component, but particles containing metal or metal compounds as the main component are preferred. The metal or metal compound described above is not particularly limited, but may include one or more metallic elements from the elements of groups 2 to 15 of the periodic table or the lanthanide elements. Among these, metal compounds containing at least one element selected from the group consisting of Si, Ti, Al, and Zr are more preferred in terms of further improving hardness and wear resistance, and compounds containing Si are even more preferred. The metal compound described above may be a compound of a single metal, a solid solution of two or more metal compounds, or a composite.

[0065] Examples of the above-mentioned metal compounds include metal oxides, metal nitrides, metal carbides, metal sulfides, and metal hydroxides. Among these, metal oxides are preferred.

[0066] Specific examples of the above metal compounds include, for example, silica (silicon oxide, SiO₂). ２ ), titania (titanium dioxide, TiO ２ ), alumina (aluminum oxide, Al ２ O ３ ), Zirconia (Zirconium oxide, ZrO ２ ), tantalum oxide (In ２ O ３ ), zinc oxide (ZnO), tin oxide (SnO ２ ), cerium oxide (CeO ２ Examples include metal oxides such as niobium oxide (NbO) and nitrate.

[0067] In particular, the inorganic particles (B) preferably contain at least one metal compound particle selected from the group consisting of silica, zirconia, titania, and alumina, as this further improves the hardness and wear resistance of the cured product, and it is even more preferable that the inorganic particles contain silica particles, as this improves the dispersibility of the inorganic particles.

[0068] The inorganic particles (B) described above may be crystalline or amorphous.

[0069] The average primary particle diameter of the inorganic particles (B) is 1 to 100 nm. When the average primary particle diameter of the inorganic particles (B) is within the above range, a highly transparent cured product can be obtained. The average primary particle diameter of the inorganic particles (B) is preferably 1 to 80 nm, more preferably 1 to 50 nm, and even more preferably 1 to 30 nm, in terms of higher transparency. The average primary particle diameter is obtained by observing the inorganic particles under magnification with a transmission electron microscope (TEM) (magnification 1,000,000 times), randomly selecting 100 particles, measuring their lengths along their long axes, and calculating the arithmetic mean.

[0070] The shape of the inorganic particles (B) is not particularly limited and may be irregular, granular, plate-like, columnar, needle-like, etc., but granular is preferred, and among granular shapes, spherical is preferred. The above-mentioned granular shape means an unbiased shape with an aspect ratio of 1.5 or less. When the aspect ratio of the inorganic particles is taken as the value obtained by dividing the longest diameter within the particle by the shortest diameter, the aspect ratio is preferably 1.4 or less, more preferably 1.35 or less, and even more preferably 1.3 or less.

[0071] The inorganic particles (B) are preferably particles that have been surface-treated with a surface treatment agent. Surface treatment improves the dispersibility of the inorganic particles in the photosensitive composition, thereby improving the transparency of the resulting cured product.

[0072] The above-mentioned surface treatment agent is not particularly limited and includes known surface treatment agents commonly used to improve the dispersibility of inorganic particles, such as polyols, alkanolamines, stearic acid, silane coupling agents, and phosphate esters. Among these, silane coupling agents are preferred because they provide good dispersibility of inorganic particles.

[0073] The method for surface-treating the inorganic particles with a surface treatment agent is not particularly limited, and it is preferable to use known methods such as mixing the inorganic particles and the surface treatment agent in a solvent, heating as needed, and then removing the solvent to obtain coated particles.

[0074] The above photosensitive composition may contain only one type of inorganic particle (B), or it may contain two or more types. The amount of inorganic particles in the above photosensitive composition is preferably 10 to 90% by mass, more preferably 15 to 80% by mass, and even more preferably 20 to 70% by mass, based on 100% by mass of the total solid content of the photosensitive composition.

[0075] Furthermore, the content of the inorganic particles (B) in the above photosensitive composition is preferably 10 to 1000 parts by mass, more preferably 13 to 800 parts by mass, even more preferably 15 to 600 parts by mass, and still more preferably 50 to 300 parts by mass, per 100 parts by mass of the polyfunctional compound (A).

[0076] (C) Photopolymerization initiator The photopolymerization initiator (C) contained in the above photosensitive composition is preferably a radical polymerizable photopolymerization initiator. Specific examples of the above photopolymerization initiator include, for example, alkylphenone compounds such as 2,2-diethoxyacetophenone and 2,2-dimethoxy-2-phenylacetophenone; aminoalkylphenone compounds such as 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropanone, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methylpropanone α-hydroxyketone compounds such as 1-hydroxycyclohexylphenylketone benzophenone, 4,4'-bis(dimethylamino)benzophenone, and other benzophenone compounds; benzoin compounds such as benzoin and benzoin methyl ether; 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, ethoxyphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, ethyl(3-be Acylphosphine oxide compounds such as 2,4,6-trimethylbenzoyl)-phenylphosphofinate; thioxanthone compounds such as thioxanthone, 2-ethylthioxanthone, and 2-isopropylthioxanthone; aminobenzoate compounds such as poly(ethyl glycol)bis(p-dimethylaminobenzoate); halomethylated triazine compounds such as 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine; 2-trichloromethyl-5-(2' Halomethylated oxadiazole compounds such as -benzofuryl)-1,3,4-oxadiazole; biimidazole compounds such as 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole; oxime ester compounds such as 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyloxime)], etanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-,1-(O-acetyloxime);Examples of azo polymerization initiators include titanocene compounds such as bis(η5-2,4-cyclopentadiene-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium; benzoic acid ester compounds such as p-dimethylaminobenzoic acid and p-diethylaminobenzoic acid; and acridine compounds such as 9-phenylacridine. Among these, α-hydroxyketone compounds are preferred because they yield cured products with even higher transparency.

[0077] The above photosensitive composition may contain only one type of photopolymerization initiator (C), or it may contain two or more types. The content of the photopolymerization initiator in the above photosensitive composition is preferably 1 to 7% by mass, more preferably 1 to 5% by mass, and even more preferably 1 to 4% by mass, based on 100% by mass of the total solid content of the photosensitive composition.

[0078] (G) Other Components The above photosensitive composition may contain other components (G) as needed, in addition to the components described above. Examples of these other components include solvents, binder resins, fillers, colorants, dispersants, adhesion improvers, mold release agents, plasticizers, ultraviolet absorbers, antioxidants, matting agents, defoamers, leveling agents, surfactants, antistatic agents, slip agents, surface modifiers, coupling agents such as silane-based, aluminum-based, and titanium-based agents, acid generators, and photosensitizers. These can be appropriately selected from known sources. The amounts of these added can also be appropriately selected by referring to known technologies. For example, by adding a leveling agent, the surface smoothness of the cured product formed using the above photosensitive composition can be improved, or antifouling properties can be imparted. Furthermore, by adding an ultraviolet absorber, the weather resistance of the cured product can be improved.

[0079] The content of the other component (G) in the above photosensitive composition is preferably 10% by mass or less, more preferably 7% by mass or less, and even more preferably 5% by mass or less, based on 100% by mass of the total solid content of the photosensitive composition.

[0080] The method for preparing the above-mentioned photosensitive composition is not particularly limited and any known method may be used. For example, the composition can be prepared by mixing each of the above-mentioned components using a known mixer, disperser, kneader, or the like.

[0081] 2. Cured product The method for curing the above photosensitive composition to obtain a cured product is not particularly limited and includes heating, irradiation with active energy rays, or a combination thereof. The heating temperature is usually preferably 30 to 400°C, more preferably 50 to 350°C, and even more preferably 60 to 350°C, from the viewpoint of promoting curing and reducing thermal decomposition. When a curing accelerator is used in combination, curing can be performed at a lower temperature than when not used, preferably 0 to 400°C, more preferably 10 to 350°C, and even more preferably 20 to 350°C.

[0082] The active energy beams can be those commonly used, including electromagnetic waves such as gamma rays, X-rays, ultraviolet rays, visible light, and infrared rays, as well as particle beams such as electron beams, neutron beams, and proton beams. Of these, ultraviolet rays are preferred. The irradiation dose of the active energy beams is not particularly limited, but for example, in the case of ultraviolet irradiation, the integrated light dose is 100 to 10,000 mJ / cm². ２ Preferably, the concentration is 200 to 5000 mJ / cm². ２ It is preferable that it be so.

[0083] If the cured product is a cured film, its thickness can be appropriately selected depending on the application of the cured film, but is preferably 1 to 20 μm, more preferably 2 to 15 μm, and even more preferably 3 to 10 μm.

[0084] The cured product of the above photosensitive composition has high hardness and excellent appearance, abrasion resistance, and flexibility. Such a cured product of the above photosensitive composition is also one of the present inventions.

[0085] 3. Applications As described above, the photosensitive composition of the present invention can provide a cured product with excellent appearance, hardness, abrasion resistance, and flexibility. Therefore, the above photosensitive composition can be suitably used in applications where appearance, hardness, abrasion resistance, and flexibility are required.

[0086] The above photosensitive composition can be suitably used, for example, as a composition for forming a hard coat layer in various image display devices. More preferably, it can be used as a hard coat film for flexible devices such as foldable displays.

[0087] An article characterized by comprising a cured product of the above-mentioned photosensitive composition is also one of the present inventions. A laminated film is an example of a preferred embodiment of the above-mentioned article.

[0088] 4. Laminated Film The present invention also relates to a laminated film having a hard coat layer containing a cured product of the above-mentioned photosensitive composition. Because the laminated film of the present invention has a hard coat layer containing a cured product of the above-mentioned photosensitive composition, it has excellent appearance, hardness, abrasion resistance, and flexibility.

[0089] The hard coat layer described above can be formed by applying the above-described photosensitive composition onto a substrate and curing it. When applying the above-described photosensitive composition onto a substrate, it is preferable that the photosensitive composition contains a solvent. The application method is not particularly limited and includes known application methods such as bar coaters, spin coaters, and spray coaters. The curing method described above is an example of how to cure the above-described photosensitive composition. Alternatively, the hard coat layer may be laminated by first forming the photosensitive composition into a sheet and then laminating the molded product onto a substrate. The molding method is not particularly limited and may be carried out by known methods.

[0090] The thickness of the hard coat layer is not particularly limited, but is preferably 1 to 20 μm, more preferably 2 to 15 μm, and even more preferably 3 to 10 μm.

[0091] Examples of the above-mentioned substrates include resin substrates such as polyethylene terephthalate (PET), polyethylene naphthalate, cellulose triacetate, cellulose acetate butyrate, polyamide, transparent polyimide (CPI), polyethersulfone, polysulfone, polypropylene, polyvinyl chloride, polyvinyl acetal, polyetherketone, polymethyl methacrylate, polycarbonate, or polyurethane, as well as glass substrates.

[0092] The laminated film described above may further have one or more other functional layers, such as an adhesive layer or an impact-absorbing layer, as needed. When the laminated film has the functional layers described above, it is preferable that the hard coat layer is on the outermost surface.

[0093] The method for manufacturing the above-mentioned laminated film is not particularly limited, and one method is to sequentially laminate each layer on a substrate using a known method to achieve a desired layer structure. The lamination of each layer may be carried out by known methods such as applying various layer-forming compositions to the substrate and curing them by heating or irradiation with active energy rays to form a cured film, or by laminating a pre-formed film or sheet.

[0094] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0095] (Production Example 1) Preparation of AOMA-TC-D 3.55 g (12.5 mmol) of titanium tetraisopropoxide (TTIP), 81.7 g (416 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), 196.9 g (1248 mmol) of α-allyloxymethylmethyl acrylate (AOMA), 200 mg of polymerization inhibitor (6-t-butyl-2,4-xylenol, manufactured by Tokyo Chemical Industry Co., Ltd.) (to 1000 ppm relative to AOMA), 200 mg of polymerization inhibitor (Polystop 7300P, manufactured by Hakuto Co., Ltd.) (to 1000 ppm relative to AOMA), and 13 g of azeotropic agent heptane were weighed into a separable flask equipped with a stirrer, condenser, and distillation column. The mixture was heated to 110°C while the pressure in the system was reduced to 300 Torr and reacted under total reflux. The fractions were removed as needed, and the reaction was carried out by adding fresh heptane to the system to maintain a reaction temperature of 110°C, continuing to heat until the ratio of diester to monoester exceeded 96%. After the reaction was complete, the reaction solution was washed twice with 50 g of 7% by mass oxalic acid aqueous solution and once with 50 g of deionized water. The light boiling components in the system were then removed by distillation to obtain 120 g of a pale yellow transparent liquid (AOMA-TC-D). The residual amount of AOMA, the starting material, was 2.5% by mass.

[0096] (Production Example 2) Production of AOMA-TO-SU AOMA-TO-SU was obtained by the same method as in Production Example 1, except that 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane was used instead of tricyclodecanedimethanol. The residual amount of AOMA, the raw material, was 1.4% by mass.

[0097] (Production Example 3) Production of AOMA-TH-IC AOMA-TH-IC was obtained by the same method as in Production Example 1, except that tris(2-hydroxyethyl) isocyanurate was used instead of tricyclodecanedimethanol. The residual amount of AOMA, the raw material, was 1.3% by mass.

[0098] (Production Example 4) Production of AOMA-TM-P AOMA-TM-P was obtained by the same method as in Production Example 1, except that trimethylolpropane was used instead of tricyclodecanedimethanol. The residual amount of AOMA, the raw material, was 4.9% by mass.

[0099] (Production Example 5) Production of AOMA-DT-MP AOMA-DT-MP was obtained by the same method as in Production Example 1, except that ditrimethylolpropane was used instead of tricyclodecanedimethanol. The residual amount of AOMA, the raw material, was 2.8% by mass.

[0100] (Production Example 6) Production of AOMA-BP-E2 AOMA-BP-E2 was obtained by the same method as in Production Example 1, except that BA-2 glycol (manufactured by Nippon Emulsifier Co., Ltd., 2,2-bis(4-polyoxyethylene-oxyphenyl)propane) was used instead of tricyclodecanedimethanol. The residual amount of AOMA, the raw material, was 1.1% by mass.

[0101] (Manufacturing Example 7) Manufacturing Process 7A of Silica Nanoparticle MIBK Dispersion Particle Synthesis Process 16,500 g of methanol, 3,200 g of water, and 1,300 g of 25% aqueous ammonia were placed in a 50 L stainless steel container equipped with a stirrer, a dropping port, and a thermometer, and stirred for 30 minutes to obtain a homogeneous mixed solution. The temperature of the above mixed solution was adjusted to 49-51°C, and while stirring, 5,700 g of tetramethyl orthosilicate (manufactured by Tama Chemical Industry Co., Ltd., TMOS) was added dropwise through the dropping port over 90 minutes. After the addition was completed, stirring was continued for 30 minutes while maintaining the above temperature to obtain an alcoholic solution suspension 1A of silica particles. The average primary particle size of the silica particles was 24 nm.

[0102] Step 7B Surface Treatment Step The suspension 1A obtained in Step 7A was heated to 50°C again while stirring, and 1600 g of 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-503) was added dropwise through the dropper port over 260 minutes while maintaining the liquid temperature and stirring. After the addition was completed, stirring was continued for 15 hours while maintaining the above liquid temperature to obtain an alcoholic solution suspension 1B of silica particles having methacrylic groups on the particle surface.

[0103] Step 7C Ultrafiltration Step The suspension 1B obtained in Step 7B is subjected to solvent replacement at room temperature while adding methanol as appropriate, using a commercially available ultrafiltration membrane equipped with a ceramic tubular ultrafiltration membrane with a fractional molecular weight of approximately 10,000. ２ By concentrating the solution to a concentration of approximately 11%, a methanol suspension 1C of silica particles having methacrylic groups on their surface was obtained at pH 9.3.

[0104] Step 7D Ion exchange step The above suspension 1C was passed through a column packed with hydrogen-type strong acid cation exchange resin Amberlite IR-120B (manufactured by Organo Corporation) at room temperature conditions at a flow rate of 3 space velocity per hour to obtain a methanol suspension of silica particles having methacrylic groups with a pH of 5.5.

[0105] Step 7E Solvent Replacement Step 1800 g of the methanol suspension of silica particles having methacrylic groups obtained in Step 7D is weighed and the solvent is replaced by sequentially adding 800 g of methyl isobutyl ketone (MIBK) while concentrating it by vacuum distillation in a rotary evaporator. ２ A MIBK dispersion of silica nanoparticles containing methacrylic groups was obtained by concentrating the solution to a concentration of approximately 30%. The average primary particle size of the silica particles in the above dispersion was 20 nm.

[0106] (Examples 1-12, Comparative Examples 1-5) Photosensitive compositions were prepared by dissolving AOMAs, polyfunctional acrylates, polyfunctional urethane acrylates, leveling agents, and photopolymerization initiators in the order shown in Table 1 (the numerical values ​​(parts) representing the composition in Table 1 indicate the mass equivalent to the solid content), and finally adding inorganic particles. The components shown in Table 1 are as follows.AOMA compounds AOMA: α-Allyloxymethyl acrylate (manufactured by Nippon Shokubai Co., Ltd.) AOMA-TC-D: Tricyclodecane dimethanol di(2-(allyloxymethyl)acrylate) (Production Example 1) AOMA-TO-SU: 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecanedi(2-(allyloxymethyl)acrylate) (Production Example 2) AOMA-TH-IC: Tris(2-hydroxyethyl) isocyanurate tri(2-(allyloxymethyl)acrylate) (Production Example 3) AOMA-TM-P: Trimethylolpropane tri(2-(allyloxymethyl)acrylate) (Production Example 4) AOMA-DT-MP: Ditrimethylolpropane tetra(2-(allyloxymethyl)acrylate) (Production Example 5) AOMA-BP-E2: 2,2-bis(4-polyoxyethylene-oxyphenyl)propanedi(2-(allyloxymethyl)acrylate) (Production Example 6) • Polyfunctional acrylates A-DPH: Dipentaerythritol polyacrylate (A-DPH manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) A-DCP: Tricyclodecanedimethanol diacrylate (A-DCP manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) • Polyfunctional urethane acrylates Sartomer CN968C (manufactured by Sartomer) Sartomer CN9006NS (manufactured by Sartomer) KRM 8684F (manufactured by Daicel Ornex Co., Ltd.) ART RESIN H-575B (manufactured by Negami Kogyo Co., Ltd.) ART RESIN UN-905 (manufactured by Negami Kogyo Co., Ltd.) - Inorganic silica nanoparticles: Silica nanoparticles with an average primary particle diameter of 20 nm (Manufacturing Example 6) Seahostar S30-HG (manufactured by Nippon Shokubai Co., Ltd., silica particles with an average primary particle diameter of 0.3 μm) - Photopolymerization initiator Omnirad 184 (manufactured by IGM Resins) - Leveling agent MEGAFACE EFS-131 (manufactured by DIC Corporation).

[0107] <Formation of the coating layer> The photosensitive compositions obtained in the above examples and comparative examples were applied to a base film (Toray Industries Lumirror 50ATM1, polyethylene terephthalate film, 50 μm thick) using a #5 bar coater. After drying at 80°C for 3 minutes to remove the solvent, the coating was applied using a metal halide lamp under a nitrogen atmosphere with an integrated light intensity of 1000 mJ / cm². ２ A laminated film was obtained by irradiating the base film with ultraviolet light, forming a coating layer (5 μm thick) on the base film. The appearance, hardness, abrasion resistance, and bending resistance of the obtained laminated film were evaluated using the following method. The results are shown in Table 1.

[0108] <Appearance (Haze Evaluation)> To evaluate the appearance of the coating layer, the laminated film obtained above was used to perform haze measurement using an optical spectrometer (NDH-5000, manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with the JIS standard (JIS K7136-1). The appearance was evaluated according to the following criteria: ○: Haze value was less than 5%. ×: Haze value was 5% or more.

[0109] <Hardness (Pencil Hardness Test)> To evaluate the hardness of the coating layer, a pencil hardness test was conducted using the laminated film obtained above, in accordance with the JIS standard (JIS K5600-5-4:1999). Specifically, the surface of the coating layer was scratched with pencil leads of different hardness levels (load 750g), and the hardest pencil hardness that did not cause any scratches was defined as the pencil hardness. The pencil hardness levels, from softest to hardest, are 6B, 5B, 4B, 3B, 2B, B, HB, F, H, 2H, 3H, 4H, 5H, and 6H.

[0110] <Abrasion Resistance (Steel Wool Scratch Test)> To evaluate the scratch resistance of the coating layer, a steel wool scratch test was conducted under the following conditions. #0000 steel wool was fixed to an abrasion resistance tester (Imoto Seisakusho Co., Ltd., IMC-154A), and a load of 500g was applied to abrade the surface of the coating layer of the laminated film obtained above 100 times back and forth. After that, the surface was visually observed and the abrasion resistance was evaluated according to the following criteria. (Evaluation Criteria) ○: No scratches were observed (0 scratches). △: Almost no scratches were observed (1 to 5 scratches). ×: Scratches were observed (6 or more scratches).

[0111] <Flexural Resistance (Mandrel Test)> To evaluate the flexibility of the coating layer, a mandrel bending test was conducted in accordance with the JIS standard (JIS K5600-5-1). Specifically, with the coated layer surface of the laminated film obtained above facing outwards, the laminated film was bent 180° along a mandrel with a diameter of 2 mm, and the presence or absence of cracks in the coating layer was checked. Flexural resistance was evaluated according to the following criteria: (Evaluation Criteria) ○: No cracks occurred in the coating layer. ×: Cracks occurred in the coating layer.

[0112]

[0113] Table 1 shows that films having a coating layer formed using the photosensitive composition according to the present invention all exhibit excellent appearance, hardness, abrasion resistance, and flexibility, and are suitable for hard coat layers in displays and the like.

Claims

A photosensitive composition characterized by comprising a polyfunctional compound (A) represented by the following general formula (1), inorganic particles (B) having an average primary particle diameter of 1 to 100 nm, and a photopolymerization initiator (C). (In formula (1), X represents a divalent organic group having a cyclic structure, or an organic group with three or more valencies. n is an integer of 2 or more.) Furthermore, the photosensitive composition according to claim 1, characterized in that it further contains a polyfunctional urethane (meth)acrylate (D). The photosensitive composition according to claim 1 or 2, characterized in that the inorganic particles (B) include at least one particle selected from the group consisting of silica, zirconia, titania, and alumina. The photosensitive composition according to any one of claims 1 to 3, characterized in that the content of the inorganic particles (B) is 10 to 1000 parts by mass per 100 parts by mass of the polyfunctional compound (A). The photosensitive composition according to claim 2, characterized in that the content of the polyfunctional urethane (meth)acrylate (D) is 10 to 1000 parts by mass per 100 parts by mass of the polyfunctional compound (A). A cured product of the photosensitive composition according to any one of claims 1 to 5. A laminated film characterized by having a hard coat layer containing the cured product described in claim 6. An article characterized by comprising the cured product described in claim 6.

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