Gas barrier optical film, laminate, display device and solar cell

Abstract

To provide a gas barrier optical film having high refractive index and gas barrier properties.SOLUTION: There is provided a gas barrier optical film containing a poly(thio)urethane (P), wherein the poly(thio)urethane (P) contains a cured product of a polymerizable composition comprising an isocyanate compound (A) and an active hydrogen compound (B) containing one or two or more selected from the group consisting of a bi- or more-functional polythiol compound (B1), a hydroxyl thiol compound (B2) having a thiol group and a hydroxyl group and a bi- or more-functional polyol compound (B3) and the water vapor transmission rate of the gas barrier optical film is 10.0 g / (m2 / day) or less, as measured under conditions of 40°C and 90% RH in accordance with JIS K 7129B.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a gas barrier optical film, a laminate, a display device, and a solar cell.

Background Art

[0002] Optical films are used in display devices and solar cells. As a document related to such an optical film, Patent Document 1 can be cited.

[0003] Patent Document 1 aims to provide a resin composition having a low birefringence, good transparency and toughness, which is composed of a polyester resin composition and a polystyrene resin composition, and a film made of the resin composition. A resin composition containing a polyester resin composition A and a polystyrene resin composition B represented by a specific chemical formula and satisfying formula (I) is described. ΔCOOH (eq / ton) < 150 Formula (I) Note that ΔCOOH is the difference COOH2 - COOH1 between the amount of terminal carboxyl groups COOH1 in the resin composition and the amount of terminal carboxyl groups COOH2 after melting the resin composition at 290°C for 30 minutes in a nitrogen atmosphere.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention provides an optical film having a high refractive index and gas barrier properties.

Means for Solving the Problems

[0006] According to the present invention, there are provided a gas barrier optical film, a laminate, a display device, and a solar cell as described below.

[0007] [1] A gas barrier optical film containing poly(thio)urethane (P), wherein the poly(thio)urethane (P) contains a cured product of a polymerizable composition containing an isocyanate compound (A) and an active hydrogen compound (B) selected from the group consisting of a polyol compound (B1) having two or more functional groups, a hydroxy thiol compound (B2) having a thiol group and a hydroxyl group, and a polyol compound (B3) having two or more functional groups, The water vapor transmission rate of the gas barrier optical film measured under the conditions of 40 °C and 90% RH in accordance with JIS K 7129B is 10.0 g / (m 2 ·day) or less, a gas barrier optical film. [2] The oxygen transmission rate of the gas barrier optical film measured under the conditions of 23 °C and 60% RH in accordance with JIS K 7126-2 is 5.0 cc / (m 2 ·day·atm) or less, the gas barrier optical film according to [1]. [3] The gas barrier optical film according to [1] or [2], wherein the polymerizable composition further contains a photopolymerization initiator (C). [4] The gas barrier optical film according to [3], wherein the photopolymerization initiator (C) contains boron. [5] The gas barrier optical film according to any one of [1] to [4], wherein the isocyanate compound (A) contains an aromatic isocyanate compound (a). [6] The gas barrier optical film according to [5], wherein the aromatic isocyanate compound (a) contains one or more selected from the group consisting of xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate. [7] The gas barrier optical film according to any one of [1] to [6], wherein the polythiol compound (B1) contains one or more selected from the group consisting of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl) sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane. [8] The gas barrier optical film according to any one of [1] to [7], wherein the polythiol compound (B1) contains one or more selected from the group consisting of a bifunctional polythiol compound (b1) and a trifunctional or higher polythiol compound (b2). [9] The gas barrier optical film according to [8], wherein the thiol equivalent of the polythiol compound (b1) is 1% or more and 95% or less with respect to 100% of the total thiol equivalent of the polythiol compound (b1) and the polythiol compound (b2).

[10] The gas barrier optical film according to any one of [1] to [9], having a thickness of 15 μm or more and 1000 μm or less.

[11] The gas barrier optical film according to any one of [1] to

[10] , having a refractive index nd at 23°C of 1.50 or more and 1.75 or less.

[12] The gas barrier optical film according to any one of [1] to

[11] , having a birefringence in the thickness direction at 25 ° C. and a wavelength of 590 nm measured by the rotation retardation method of less than 10 nm.

[13] The gas barrier optical film according to any one of [1] to

[12] , which can be used for the outermost layer or the intermediate layer of a liquid crystal panel, an organic EL display, or a solar cell.

[14] The gas barrier optical film according to any one of [1] to

[13] , and On at least one surface of the gas barrier optical film, an SiO2 layer and A laminate comprising.

[15] The laminate according to

[14] , further comprising a layer containing clay.

[16] The water vapor transmission rate of the laminate, measured under the conditions of 40 ° C. and 90% RH in accordance with JIS K 7129B, is 1.0 g / (m 2 · day) or less, the laminate according to

[14] or

[15] .

[17] A display device including the gas barrier optical film according to any one of [1] to

[13] .

[18] A solar cell including the gas barrier optical film according to any one of [1] to

[13] .

Advantages of the Invention

[0008] According to the present invention, a gas barrier optical film having a high refractive index can be provided.

Embodiments for Carrying Out the Invention

[0009] Hereinafter, embodiments of the present invention will be described. In this embodiment, "A to B" indicating a numerical range represents A or more and B or less unless otherwise specified. Also, when the numerical ranges are described stepwise, the upper and lower limits of each numerical range can be arbitrarily combined. In the present embodiment, "film" is a concept including what is generally called "sheet". In this embodiment, thiourethane refers to a compound having a thiourethane bond formed by the reaction of a polythiol component and an isocyanate component. In an embodiment of the present invention, a gas barrier refers to a function of shielding the permeation of oxygen, water vapor, etc.

[0010] <Gas barrier optical film> The gas barrier optical film of this embodiment contains poly(thio)urethane (P), and the poly(thio)urethane (P) is an isocyanate compound (A) and a polyfunctional or higher polythiol compound (B1), a hydroxythiol compound (B2) having a thiol group and a hydroxyl group, and a polyol compound (B3) having two or more functional groups. It contains a cured product of a polymerizable composition containing one or more selected from the group consisting of active hydrogen compounds (B), and the water vapor permeability of the gas barrier optical film measured under the conditions of 40 ° C and 90% RH in accordance with JIS K 7129B is 10.0 g / (m 2 ·day) or less.

[0011] According to the studies of the present inventors, it has been found that a gas barrier optical film having a high refractive index can be obtained by containing a specific poly(thio)urethane (P).

[0012] <Poly(thio)urethane (P)> Poly(thio)urethane (P) contains a cured product of a polymerizable composition containing an isocyanate compound (A) and an active hydrogen compound (B).

[0013] <Isocyanate compound (A)> The polymerizable composition of this embodiment contains an isocyanate compound (A). The isocyanate compound (A) preferably contains one or more selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate, and more preferably contains one or more selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and xylylene diisocyanate.

[0014] Also, from the viewpoint of further improving the gas barrier property, the isocyanate compound (A) preferably contains an aromatic isocyanate compound (a), and more preferably contains one or more selected from the group consisting of xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate.

[0015] The equivalent ratio of the active hydrogen-containing group in the active hydrogen compound (B) to the isocyanato group in the isocyanate compound (A) (active hydrogen-containing group / isocyanato group) is preferably 0.8 or more, more preferably 0.85 or more, still more preferably 0.9 or more, and preferably 1.2 or less, more preferably 1.15 or less, still more preferably 1.1 or less. Thereby, a poly(thio)urethane (P) suitably used as a gas barrier optical film can be obtained.

[0016] <Active hydrogen compound (B)> The polymerizable composition of this embodiment contains an active hydrogen compound (B). The active hydrogen compound (B) contains one or more selected from the group consisting of a polyol compound (B1) having two or more functional groups (hereinafter sometimes abbreviated as "polythiol compound (B1)"), a hydroxy thiol compound (B2) having a thiol group and a hydroxyl group (hereinafter sometimes abbreviated as "hydroxy thiol compound (B2)"), and a polyol compound (B3) having two or more functional groups (hereinafter sometimes abbreviated as "polyol compound (B3)").

[0017] [Polyol compound (B1) having two or more functional groups] As the polythiol compound (B1), preferably one or more selected from the group consisting of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl) sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane are included.

[0018] The polyol compound (B1) having two or more functional groups preferably contains one or more selected from the group consisting of a polyol compound (b1) having two functional groups (hereinafter sometimes abbreviated as "polythiol compound (b1)") and a polyol compound (b2) having three or more functional groups (hereinafter sometimes abbreviated as "polythiol compound (b2)"), and contains the polyol compound (b2) from the viewpoint of further improving the gas barrier properties. Further, the polyol compound (B1) having two or more functional groups preferably contains both a difunctional polyol compound (b1) and a polyol compound (b2) having three or more functional groups. Thereby, the flexibility of the obtained film becomes more appropriate, and it can be suitably used even in applications such as foldable displays that require flexibility.

[0019] Examples of the polyol compound (b1) include methanedithiol, ethanedithiol, 1,3-propanedithiol, 1,2-cyclohexanedithiol, bis(2-mercaptoethyl) ether, diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), bis(mercaptomethyl) sulfide, bis(mercaptomethyl) disulfide, bis(mercaptoethyl) disulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio) methane, bis(2-mercaptoethylthio) methane, bis(3-mercaptopropylthio) methane, 1,2-bis(mercaptomethylthio) ethane, 1,2-bis(2-mercaptoethylthio) ethane, 1,2-bis(3-mercaptopropylthio) ethane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, and esters of these thioglycolic acid and mercaptopropionic acid; Bis(2-mercaptoethyl) sulfide, hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3-mercaptopropionate), thiodiglycolic acid bis(2-mercaptoethyl ester), thiodipropionic acid bis(2-mercaptoethyl ester), dithiodiglycolic acid bis(2-mercaptoethyl ester), dithiodipropionic acid bis(2-mercaptoethyl ester), aliphatic polythiol compounds such as 4,6-bis(mercaptomethylthio)-1,3-dithiane; Aromatic polythiol compounds such as 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol; Heterocyclic polythiol compounds such as 2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol, bismuthiol, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane; etc. are included.

[0020] Among these, the polythiol compound (b1) preferably contains one or more selected from the group consisting of 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(2-mercaptoethyl) sulfide, and 4,6-bis(mercaptomethylthio)-1,3-dithiane, and more preferably contains bis(2-mercaptoethyl) sulfide.

[0021] Examples of the polythiol compound (b2) include 1,2,3-propanetrithiol, tetrakis(mercaptomethyl)methane, trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolethane tris(2-mercaptoacetate), trimethylolethane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl) sulfide, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, thio glycolic acid esters and mercaptopropionic acid esters thereof; Aliphatic polythiol compounds such as 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, tris(mercaptomethylthio)methane, and tris(mercaptoethylthio)methane; Aromatic polythiol compounds such as 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyleneoxy)benzene, 1,3,5-tris(mercaptoethyleneoxy)benzene; Heterocyclic polythiol compounds such as 2,4,6-trimercapto-s-triazine, 2,4,6-trimercapto-1,3,5-triazine, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane; etc.

[0022] The polythiol compound (b2) preferably contains one or more selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 1,1,3,3-tetrakis(mercaptomethylthio)propane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane, more preferably contains one or two selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and pentaerythritol tetrakis(3-mercaptopropionate), and still more preferably contains 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.

[0023] The polyol compound (B1) having two or more functional groups in the present embodiment preferably contains one or more bifunctional polyols selected from the group consisting of 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(2-mercaptoethyl) sulfide, and 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane which is a polyol having three or more functional groups. More preferably, it contains bis(2-mercaptoethyl) sulfide and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.

[0024] The thiol equivalent of the polythiol compound (b1) can be appropriately selected according to the type of the isocyanate compound (A). From the viewpoint of moderately improving the flexibility of the obtained film, it is preferably 0% or more, more preferably 1% or more, still more preferably 5% or more, still more preferably 10% or more, still more preferably 15% or more, still more preferably 18% or more, still more preferably 20% or more, still more preferably 30% or more, still more preferably 40% or more, based on 100% of the total thiol equivalent of the polythiol compound (b1) and the polythiol compound (b2). From the viewpoint of moderately hardening the obtained film, it is preferably 95% or less, more preferably 90% or less, still more preferably 85% or less, still more preferably 80% or less, still more preferably 70% or less, still more preferably 60% or less.

[0025] [Hydroxythiol compound (B2) having a thiol group and a hydroxyl group] The hydroxy thiol compound (B2) preferably contains one or more selected from the group consisting of 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris(3-mercaptopropionate), pentaerythritol mono(3-mercaptopropionate), pentaerythritol bis(3-mercaptopropionate), pentaerythritol tris(thioglycolate), pentaerythritol pentakis(3-mercaptopropionate), hydroxymethyl-tris(mercaptoethylthiomethyl)methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptophenyl sulfone, 2-(2-mercaptoethylthio)ethanol, dihydroxyethyl sulfide mono(3-mercaptopropionate), dimercaptoethane mono(salicylate), and hydroxyethylthiomethyl-tris(mercaptoethylthio)methane.

[0026] [Polyol compound (B3) having two or more functional groups] The polyol compound (B3) having two or more functional groups preferably contains one or more selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, 1,4-dihydroxy-2-butene, glycerin, 2-methyl-2-hydroxymethyl-1,3-propanediol, 2,4-dihydroxy-3-hydroxymethylpentane, 1,2,6-hexanetriol, trimethylolpropane, 2,2-bis(hydroxymethyl)-3-butanol, tetramethylolmethane (pentaerythritol), and diglycerin.

[0027] When the total content of the isocyanate compound (A) and the active hydrogen compound (B) in the polymerizable composition of the present embodiment is 100% by mass of the entire polymerizable composition, it is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, still more preferably 90% by mass or more, still more preferably 95% by mass or more, still more preferably 97% by mass or more, still more preferably 98% by mass or more, and preferably less than 100% by mass.

[0028] <Photoinitiator (C)> The polymerizable composition of the present embodiment preferably further contains a photoinitiator (C). The photoinitiator (C) is an initiator capable of photopolymerization, and preferably contains one or more selected from the group consisting of radical polymerization initiators and base generators, and more preferably contains a base generator from the viewpoint of further improving the photopolymerizability.

[0029] The photoinitiator (C) of this embodiment preferably contains a metal element. Here, the metal element contained in the photoinitiator (C) may include a metalloid. A metalloid is an element that exhibits intermediate properties between metals and non-metals, and examples thereof include boron, silicon, germanium, arsenic, antimony, and tellurium. From the viewpoint of further promoting the polymerization of the polymerizable composition and making it easier to form a gas barrier optical film, the photoinitiator (C) more preferably contains boron.

[0030] Moreover, the photoinitiator (C) of this embodiment is an initiator capable of photopolymerization, and preferably contains a base generator from the viewpoint of further improving the photopolymerizability. As the base generator, preferably one or two selected from the group consisting of a compound composed of an organic boron anion and a counter cation, or a compound composed of an organic silicon anion and a counter cation are included. From the viewpoint of further improving the photopolymerizability, the base generator more preferably contains a compound composed of an organic boron anion and a counter cation. The organic boron anion preferably contains one or more selected from the group consisting of a phenyl group, an alkyl group, and an aryl group, and more preferably contains one or more selected from the group consisting of a phenyl group and an alkyl group. The counter cation preferably contains one or more selected from the group consisting of ammonium or an ammonium salt, and more preferably contains an ammonium salt.

[0031] The base generator more preferably further contains a compound represented by the following formula (1).

[0032]

Chemical formula

[0033] In formula (1), R1 to R4 preferably each independently represent an alkyl group having 1 to 8 carbon atoms, and R5 to R8 preferably each independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group, a naphthyl group, an anthracenyl group or a phenanthryl group, and the phenyl group, naphthyl group, anthracenyl group and phenanthryl group may be substituted by a halogen atom, an alkyl group, an aryl group, an alkenyl group, a cycloalkyl group or a heterocyclic group.

[0034] In formula (1), R1 to R4 are preferably the same. R1 to R4 are more preferably an alkyl group having 2 to 5 carbon atoms, even more preferably a linear alkyl group, and even more preferably an n-butyl group. In formula (1), R8 is more preferably an alkyl group having 2 to 5 carbon atoms, even more preferably a linear alkyl group, and even more preferably an n-butyl group. In formula (1), R5 to R7 are preferably the same. R5 to R7 are more preferably a phenyl group, a butylphenyl group or a naphthyl group, and even more preferably a phenyl group, a 4-tert-butylphenyl group, a 1-naphthyl group or a 4-methyl-1-naphthyl group. When R5 to R7 contain an aromatic ring, the aromatic ring may be substituted by an alkyl group, an aryl group or the like.

[0035] The compound represented by formula (1) preferably contains one or more selected from the group consisting of tetra(n-butyl)ammonium = n-butyltriphenylborate, tetra(n-butyl)ammonium = n-butyltri(4-tert-butylphenyl)borate, tetra(n-butyl)ammonium = n-butyltri(1-naphthyl)borate and tetra(n-butyl)ammonium = n-butyltri(4-methyl-1-naphthyl)borate. "=" in the compound name means an ionic bond. Among these, from the viewpoint of further improving the performance balance of solubility, polymerizability, and pot life, the compound represented by the formula (1) more preferably contains one or two selected from the group consisting of tetra(n-butyl)ammonium = n-butyltriphenylborate and tetra(n-butyl)ammonium = n-butyltri(1-naphthyl)borate.

[0036] As the compound composed of the above-mentioned organic boron anion and counter cation, commercially available products can also be used. Examples of commercially available products include, for example, Calenz (registered trademark) N3B, Calenz (registered trademark) P3B (both manufactured by Resonac Co., Ltd.), WPBG-300, WPBG-345 (both manufactured by Fujifilm Corporation), and the like.

[0037] <Other components> The polymerizable composition of this embodiment may further contain an ultraviolet absorber, an antioxidant, a light stabilizer, a sensitizer, a release agent, a solvent, a bluing agent, an IR cut agent, a blue light cut agent, a reactive diluent, an oil-soluble dye, a pigment, a coloring agent, a fragrance, a filler, an adhesion improver such as a coupling agent, a chain extender, a crosslinking agent, an antifoaming agent, a precipitation inhibitor, a dispersant, a plasticizer, a sagging inhibitor, an antifouling agent, a preservative, a bactericide, an antibacterial agent, an antifungal agent, a matting agent, a thickener, a pigment dispersant, an anti-cissing agent, an anti-scratch improver, a slip agent, a surface modifier, a color separation inhibitor, an emulsifier, a skinning inhibitor, a desiccant, an antistatic agent, a conductive agent (electrostatic aid), a flame retardant, a thermal conductivity improver, a plasticizer, an ion exchange resin, etc.

[0038] Examples of the release agent include, for example, an acidic phosphate ester compound, a polyether-modified silicone, an alkyl-modified silicone, a polyester-modified silicone, a dimethylpolysiloxane, a polyoxyalkylene glycol monoalkyl ether compound, a polyoxyalkylene glycol monoester compound, a fluorine atom-containing compound, a surfactant, a nonionic surfactant, an acrylic surfactant, and the like.

[0039] The content of the mold release agent in the polymerizable composition of the present embodiment is preferably 100 ppm or more, more preferably 500 ppm or more, still more preferably 1000 ppm or more, still more preferably 1500 ppm or more, based on the total of the isocyanate compound (A) and the active hydrogen compound (B), and is preferably 5000 ppm or less, more preferably 4500 ppm or less, still more preferably 4000 ppm or less, still more preferably 3500 ppm or less.

[0040] <Gas barrier optical film> The gas barrier optical film of the present embodiment contains poly(thio)urethane (P). Hereinafter, the physical properties and the like of the gas barrier optical film of the present embodiment will be described.

[0041] The thickness of the gas barrier optical film of the present embodiment is preferably 15 μm or more, more preferably 30 μm or more, still more preferably 50 μm or more, still more preferably 70 μm or more, still more preferably 100 μm or more, still more preferably 130 μm or more, still more preferably 150 μm or more, and is preferably 1000 μm or less, more preferably 800 μm or less, still more preferably 600 μm or less, still more preferably 500 μm or less, still more preferably 400 μm or less. By setting the thickness of the gas barrier optical film within the above range, the winding property of the gas barrier optical film can be further improved. Further, by setting the thickness of the gas barrier optical film to be equal to or greater than the above lower limit value, the oxygen permeability and the water vapor permeability can be further reduced. The thickness of the gas barrier optical film can be measured using a digital indicator.

[0042] In the gas barrier optical film of the present embodiment, the water vapor permeability measured under the conditions of 40 °C and 90% RH in accordance with JIS K 7129B is preferably 10.0 g / (m 2 ·day) or less, more preferably 5.0 g / (m 2 ·day) or less, still more preferably 2.5 g / (m 2 ·day) or less, still more preferably 2.0 g / (m2 ·day) or less, more preferably 1.5 g / (m 2 ·day) or less, more preferably 1.0 g / (m 2 ·day) or less, more preferably 0.5 g / (m 2 ·day) or less, more preferably 0.3 g / (m 2 ·day) or less, more preferably 0.2 g / (m 2 ·day) or less. Since the lower the water vapor permeability, the better, the lower limit value of the water vapor permeability is not particularly limited. For example, it is 0.001 g / (m 2 ·day) or more, and may be 0.01 g / (m 2 ·day) or more, and may be 0.1 g / (m 2 ·day) or more.

[0043] In the gas barrier optical film of this embodiment, the oxygen permeability measured under the conditions of 23 °C and 60% RH in accordance with JIS K 7126-2 is preferably 5.0 cc / (m 2 ·day·atm) or less, more preferably 2.5 cc / (m 2 ·day·atm) or less, still more preferably 1.5 cc / (m 2 ·day·atm) or less, still more preferably 1.0 cc / (m 2 ·day·atm) or less, still more preferably 0.5 cc / (m 2 ·day·atm) or less, still more preferably 0.3 cc / (m 2 ·day·atm) or less, still more preferably 0.2 cc / (m 2 ·day·atm) or less, still more preferably 0.15 cc / (m 2 ·day·atm) or less.

[0044] In the high refractive index gas barrier optical film of the present embodiment, the refractive index nd at a temperature of 23°C is preferably 1.50 or more, more preferably 1.55 or more, still more preferably 1.60 or more, still more preferably 1.61 or more, still more preferably 1.63 or more, and preferably 1.75 or less, more preferably 1.70 or less, still more preferably 1.67 or less.

[0045] In the gas barrier optical film of the present embodiment, the birefringence in the thickness direction at 25°C and a wavelength of 590 nm, measured by the rotating analyzer method, is preferably less than 10 nm, more preferably less than 5 nm. Birefringence can be measured, for example, by the method described in the examples.

[0046] The gas barrier optical film of the present embodiment is preferably obtained by irradiating the polymerizable composition of the present embodiment with ultraviolet rays to polymerize and cure a part of the polymerizable composition, and then heating the polymerizable composition to further polymerize and cure it. Thereby, the winding property of the gas barrier optical film can be further improved. Also, thereby, the thickness of the gas barrier optical film can be made more appropriate.

[0047] Further, by performing heating after ultraviolet irradiation, the unpolymerized portion in the ultraviolet irradiation can be polymerized to obtain a completely polymerized cured product. Also, thereby, unreacted isocyanate groups and the like in the isocyanate compound (A) react, suppressing an increase in the hygroscopicity of the cured product of the polymerizable composition, and suppressing appearance defects due to the generation of bubbles and water bubbles when the gas barrier optical film is attached to a substrate.

[0048] Ultraviolet rays include UVC with a wavelength of 250 to 260 nm and UVA with a wavelength of 320 to 390 nm, and it is UVC that affects photopolymerization. When using ultraviolet rays, light sources such as sunlight, chemical lamps, mercury lamps, metal halide lamps, and UV LEDs can be used.

[0049] The integrated light quantity of ultraviolet irradiation is preferably 500 mJ or more, more preferably 1000 mJ or more, still more preferably 1500 mJ or more, and preferably 6000 mJ or less, more preferably 5000 mJ or less, still more preferably 3000 mJ or less, from the viewpoint of making the appearance of the resulting film better. The integrated light quantity of ultraviolet irradiation represents the total integrated light quantity of UVC and UVA. The irradiation intensity of ultraviolet irradiation is preferably 100 mW or more, still more preferably 150 mW or more, and preferably 1000 mW or less, more preferably 800 mW or less, still more preferably 600 mW or less, still more preferably 400 mW or less, from the viewpoint of making the appearance of the resulting film better. The irradiation intensity of ultraviolet irradiation represents the total irradiation intensity of UVC and UVA.

[0050] The integrated light quantity of UVC in ultraviolet irradiation is preferably 100 mJ or more, more preferably 150 mJ or more, still more preferably 200 mJ or more, and preferably 2000 mJ or less, more preferably 1000 mJ or less, still more preferably 500 mJ or less, still more preferably 300 mJ or less, from the viewpoint of making the appearance of the resulting film better. The irradiation intensity of UVC in ultraviolet irradiation is preferably 10 mW or more, more preferably 20 mW or more, still more preferably 30 mW or more, and preferably 200 mW or less, more preferably 150 mW or less, still more preferably 100 mW or less, from the viewpoint of making the appearance of the resulting film better.

[0051] The integrated light quantity of UVA in ultraviolet irradiation is preferably 500 mJ or more, more preferably 1000 mJ or more, still more preferably 1300 mJ or more, and preferably 5000 mJ or less, more preferably 3000 mJ or less, still more preferably 2000 mJ or less. The irradiation intensity of UVA in ultraviolet irradiation is preferably 50 mW or more, more preferably 100 mW or more, still more preferably 150 mW or more, and preferably 800 mW or less, more preferably 500 mW or less, still more preferably 300 mW or less.

[0052] Ultraviolet irradiation of the polymerizable composition can be carried out after forming a film with a certain thickness from the polymerizable composition. The thickness of the film formed from the polymerizable composition is preferably 20 μm or more, more preferably 100 μm or more, still more preferably 150 μm or more, still more preferably 200 μm or more, and preferably 3000 μm or less, more preferably 2000 μm or less, still more preferably 1000 μm or less, still more preferably 700 μm or less, still more preferably 400 μm or less. By setting the thickness of the film of the polymerizable composition within the above range, the thickness of the obtained gas barrier optical film can be set within the range described above. The formation of the film from the polymerizable composition is not limited, but for example, two glass plates can be arranged with a gap within the above range, a PTFE sheet can be installed around the four sides of the glass plates, the polymerizable composition can be injected, and the two glass plates can be fixed by clamping them with clips.

[0053] In addition, the formation of the film using the polymerizable composition can also be carried out by applying it on a substrate by a conventionally known method such as a bar coater, a spin coater, a dip coater, roll-to-roll. A release film can be used as the substrate, and the release film includes at least one selected from the group consisting of polyethylene terephthalate and fluororesin.

[0054] Also, when the formation of the film using the polymerizable composition is carried out by applying it on a substrate, when the film is heated after ultraviolet irradiation, the film preferably further includes a protective film on the surface opposite to the substrate. By providing a protective film, it is possible to prevent oxygen and moisture from coming into contact during the polymerization of the polymerizable composition, and it is possible to prevent bubbles from forming in the resulting gas-barrier optical film. The protective film should be able to prevent the intrusion of oxygen and moisture, and there is no limitation as long as it has heat resistance. From the perspective of being easily peeled off after the heating is completed, it is preferably a release film. As the release film, for example, a film made of polyethylene terephthalate can be used. Also, from the perspective of being easily peeled off after the heating is completed, the thickness of the protective film is preferably 5 μm or more and 150 μm or less.

[0055] When heating the polymerizable composition, the heating temperature is preferably 80 °C or higher, more preferably 85 °C or higher, still more preferably 90 °C or higher, still more preferably 100 °C or higher, still more preferably 110 °C or higher, from the perspective of polymerizing the polymerizable composition more sufficiently. Also, from the perspective of further improving the winding property of the resulting gas-barrier optical film, it is preferably 140 °C or lower, more preferably 130 °C or lower. When heating the polymerizable composition, the heating time is preferably 30 minutes or more, more preferably 60 minutes or more, still more preferably 120 minutes or more, still more preferably 150 minutes or more, and preferably 300 minutes or less, more preferably 240 minutes or less, still more preferably 200 minutes or less.

[0056] For the gas-barrier optical film of this embodiment, a known easy-adhesion treatment or easy-sliding treatment may be performed on the surface of the film. Further, an antireflection treatment, an anti-Newton ring treatment, an antistatic treatment, or a hard coat treatment may be performed by a known treatment method.

[0057] Since the gas-barrier optical film of this embodiment has a high refractive index, it can be suitably used for the outermost layer or the intermediate layer of a liquid crystal panel, an organic EL display, or a solar cell.

[0058] <Laminate> The laminate of this embodiment includes, for example, a base material and a hard coat layer. The base material includes the gas barrier optical film of this embodiment, and preferably consists of the gas barrier optical film of this embodiment. The hard coat layer is a coating layer for imparting scratch resistance, abrasion resistance, and light resistance to the surface of the gas barrier optical film of this embodiment, and its film thickness is 0.09 μm or more and 300 μm or less. Generally, the hard coat layer uses one or more kinds of oxide fine particles of an element selected from the element group of curable organosilicon compounds and Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti.

[0059] From the viewpoint of further improving the water vapor barrier property, the laminate of this embodiment preferably includes the gas barrier optical film of this embodiment and an SiO2 layer on at least one surface of the gas barrier optical film of this embodiment, and more preferably further includes a layer containing clay. The laminate of this embodiment includes, for example, one or more layer structures selected from the group consisting of a clay layer / SiO2 layer / gas barrier optical film, a clay layer / SiO2 layer / X layer / gas barrier optical film, an X layer / clay layer / SiO2 layer / gas barrier optical film, a clay layer / X layer / SiO2 layer / gas barrier optical film, an SiO2 layer / clay layer / gas barrier optical film, and an X layer / SiO2 layer / clay layer / gas barrier optical film. The clay layer is a layer formed by applying and drying a polyurethane dispersion mixed with a filler. Examples of the filler include organic nanofibers and layered inorganic compounds. From the viewpoint of gas barrier, layered inorganic compounds are preferred. Examples of the X layer include a hard coat layer containing a metal oxide and a layer containing a scratch-resistant layer containing urethane or the like.

[0060] From the perspective of improving the scratch resistance and impact resistance of the laminate, the laminate of this embodiment preferably includes one or more layer structures selected from the group consisting of a clay layer / SiO2 layer / X layer / gas barrier optical film, a SiO2 layer / clay layer / gas barrier optical film, and an X layer / SiO2 layer / clay layer / gas barrier optical film.

[0061] The hard coat layer is formed, for example, by applying a hard coat composition by a known coating method such as spin coating, dip coating, roll-to-roll, etc., and then curing it. Examples of the curing method include heat curing and curing by irradiation with energy rays such as ultraviolet rays and visible light. In order to further suppress the generation of interference fringes, the refractive index of the hard coat layer is preferably in the range where the difference in refractive index from the gas barrier optical film is ±0.1.

[0062] The gas barrier optical film may further include an antireflection layer. When the gas barrier optical film includes an optical substrate and an adhesive layer, the antireflection layer is preferably provided on the surface opposite to the optical substrate and the adhesive layer. When the gas barrier optical film includes both a hard coat layer and an antireflection layer, for example, after forming the hard coat layer on the gas barrier optical film, the antireflection layer can be formed on the hard coat layer.

[0063] The antireflection layer may be a single layer or a multilayer. The antireflection layer includes inorganic and organic types. In the case of the inorganic type, inorganic oxides such as SiO2 and TiO2 are used and formed by a dry method such as vacuum evaporation, sputtering, ion plating, ion beam assist method, CVD method, etc. In the case of the organic type, a composition containing an organosilicon compound and silica-based fine particles having internal cavities is used and formed by a wet method.

[0064] An antifogging coat layer, an antifouling layer, a water repellent layer, etc. may be formed on the antireflection layer as needed. The method for forming the antifogging coat layer, the antifouling layer, the water repellent layer, etc. is not particularly limited, and a conventionally known method can be applied.

[0065] When the gas barrier optical film of the present embodiment includes one or more selected from the group consisting of an optical substrate, an adhesive layer, a hard coat layer, and an antireflection layer, the laminated structure can be, for example, a gas barrier optical film / adhesive layer, a hard coat layer / gas barrier optical film, an antireflection layer / hard coat layer / gas barrier optical film, a hard coat layer / gas barrier optical film / adhesive layer, an antireflection layer / hard coat layer / gas barrier optical film / adhesive layer, a gas barrier optical film / adhesive layer / optical substrate, a hard coat layer / gas barrier optical film / adhesive layer / optical substrate, an antireflection layer / hard coat layer / gas barrier optical film / adhesive layer / optical substrate, etc.

[0066] The laminate of the present embodiment preferably has a water vapor transmission rate measured under the conditions of 40 °C and 90% RH in accordance with JIS K 7129B of 1.0 g / (m 2 ·day) or less.

[0067] <Display device> The display device of the present embodiment is a device including the gas barrier optical film of the present embodiment, preferably a display device including a layer formed of the gas barrier optical film of the present embodiment. For example, the gas barrier optical film of the present embodiment is included in an optical film or a surface protection film. Examples of the display device include a liquid crystal display, an organic EL display, a plasma display, a micro LED display, etc. When the display device includes a hard coat layer, an antireflection layer, etc., the laminated structure can be the same as the above-described lamination order.

[0068] <Solar cell> The solar cell of the present embodiment is a solar cell including the gas barrier optical film of the present embodiment, preferably including a layer formed of the gas barrier optical film of the present embodiment. For example, the gas barrier optical film of the present embodiment is included in a solar cell encapsulant or a protective film in a solar cell module.

[0069] As described above, the embodiments of the present invention have been described, but these are examples of the present invention, and various configurations other than the above can also be adopted. Further, the present invention is not limited to the above-described embodiments, and modifications, improvements, etc. within a range that does not impair the effects of the present invention are included in the present invention.

Example

[0070] Hereinafter, the present invention will be described by way of examples, but the present invention is not limited to the examples.

[0071] (Raw materials) ·Polythiol 1: Bis(2-mercaptoethyl) sulfide ·Polythiol 2: 4-Mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane ·Isocyanate compound 1: A mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane ·Isocyanate compound 2: Xylylene diisocyanate ·Base generator 1: Tetra(n-butyl)ammonium = n-butyltri(1-naphthyl)borate, manufactured by Resonac Co., Ltd., Karenz (registered trademark) N3B, a compound represented by the following formula (X)

[0072]

Chemical formula

[0073] ·Release agent 1: Polyether-modified silicone (KF-351A, manufactured by Shin-Etsu Silicone Co., Ltd.)

[0074] (Example 1) A gas barrier optical film was produced by the following method. To 51.7 parts by mass of xylylene diisocyanate, 0.3 part by mass of base generator 1 and 0.3 part by mass of mold release agent 1 were added, and a mixed solution was prepared. This mixed solution was stirred until completely dissolved at room temperature. To the obtained mixture, 47.7 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added, and this was stirred at 25 °C for 30 minutes to obtain a mixed solution. This mixed solution was degassed at 600 Pa for 1 hour and filtered through a 1-μm PTFE filter to obtain a formulation (polymerizable composition). Between two glass plates with a length of 36 cm, a width of 27 cm, and a plate thickness of 5 mm, a PTFE sheet with a thickness of 350 μm processed so as to surround the four sides of the glass plate with a width of 1.5 cm was sandwiched, and the periphery of this pair of glass plates was fixed so as to be covered with tape to assemble a film forming mold. The formulation was injected into the gap between the film forming molds, and after closing the pouring port with tape, ultraviolet irradiation was performed at an irradiation intensity of UVA of 186 mW, an integrated light quantity of 1488 mJ, an irradiation intensity of UVC of 32.5 mW, and an integrated light quantity of 260 mJ to obtain a semi-cured product sandwiched between the glass plates. After heating the obtained semi-cured product at 120 °C for 3 hours, it was demolded from the glass mold to obtain a gas barrier optical film with a thickness of 350 μm.

[0075] (Example 2) A gas barrier optical film was produced by the following method. To 52.2 parts by mass of xylylene diisocyanate, 0.3 part by mass of base generator 1 and 0.3 part by mass of mold release agent 1 were added, and it was stirred until completely dissolved at room temperature. To the obtained mixture, 38.6 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 8.6 parts by mass of bis(2-mercaptoethyl) sulfide were added, and this was stirred at 25 °C for 30 minutes to obtain a uniform solution (polymerizable composition). This polymerizable composition was degassed at 600 Pa for 1 hour and filtered through a 1-μm PTFE filter to obtain a formulation. It was cast into a film forming mold prepared in the same procedure as in Example 1, irradiated with ultraviolet rays and heated under the same conditions, and demolded from the glass mold to obtain a gas barrier optical film with a thickness of 350 μm.

[0076] (Example 3) A gas barrier optical film was produced by the following method. To 55.4 parts by mass of a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, 0.3 part by mass of base generator 1 and 0.3 part by mass of release agent 1 were added, and the mixture was stirred at room temperature until completely dissolved. To the obtained mixture, 23.3 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 20.7 parts by mass of bis(2-mercaptoethyl)sulfide were added, and the mixture was stirred at 25 °C for 30 minutes to obtain a homogeneous solution (polymerizable composition). This polymerizable composition was degassed at 600 Pa for 1 hour and filtered through a 1 μm PTFE filter to obtain a prepared solution. The prepared solution was poured into a film-forming mold prepared in the same procedure as in Example 1, irradiated with ultraviolet light and heated under the same conditions, and released from the glass mold to obtain a gas barrier optical film with a thickness of 350 μm.

[0077] (Comparative Examples 1 to 5) The following commercially available products were used in the comparative examples. · Comparative Example 1: Polyethylene terephthalate film (Embret, manufactured by Unitika Ltd.) · Comparative Example 2: Nylon film (Emblem ON, manufactured by Unitika Ltd.) · Comparative Example 3: Cycloolefin polymer film (ZeonorFilm (registered trademark) ZF14, manufactured by Zeon Corporation) · Comparative Example 4: Acrylic resin film (Acrypren Soft Weatherproof G, manufactured by Mitsubishi Chemical Corporation) · Comparative Example 5: Polyethylene terephthalate film vapor-deposited with SiO2 (Tech Barrier (registered trademark) VX, manufactured by Mitsubishi Chemical Corporation)

[0078] The films obtained by the above method were measured for film thickness, glass transition temperature, refractive index nd, tensile modulus, tensile strength, tensile elongation at break, birefringence, oxygen permeability, and water vapor permeability as follows. The results obtained are shown in Table 2.

[0079] [Film thickness] The thickness of the film was measured at 10 arbitrary points on the film using a digital indicator (ID-H0560, manufactured by Mitutoyo Corporation), and the average value of each was adopted.

[0080] [Glass transition temperature (Tg)] For the films of each example and each comparative example, test pieces with a width of 5 mm and a length of 30 mm were cut out, and solid viscoelastic temperature dispersion measurement was performed under the following conditions in accordance with JIS K 7244, and the glass transition temperature Tg (°C) was measured for each. Tg was taken as the peak temperature of tanδ. Apparatus: Dynamic viscoelastic measurement apparatus DMA8000 (manufactured by PerkinElmer) Deformation mode: Tension Heating rate: 2 °C / min Frequency: 1 Hz Environment: Under air atmosphere

[0081] [Refractive index (nd)] For the films of each example and each comparative example, the refractive index nd at a wavelength of 588 nm at a measurement temperature of 23 °C was measured using a refractometer (KPR-3000, manufactured by Shimadzu Corporation).

[0082] [Tensile properties] For the films of each example and each comparative example, a tensile test was performed in accordance with JIS K 6251:2017 under the conditions of a measurement temperature of 23 °C and a tensile speed of 10 mm / min, and the tensile elastic modulus, tensile strength, and tensile elongation at break of the film were measured for each. Also, the tensile strength and tensile elongation at break were measured in both the machine direction (MD) and the transverse direction (TD), and the average value of each was taken as the measured value. Also, the tensile elastic modulus was measured in the MD direction and taken as the measured value.

[0083] [Birefringence] For each example and each comparative example, annealing treatment was carried out under the conditions of 120 °C for 1 h. Then, using a strain inspection device (LSM-9001 manufactured by Lucio), the birefringence in the thickness direction at 25 °C and a wavelength of 590 nm was measured by the rotating analyzer method respectively.

[0084] [Oxygen permeability] For the films of each example and each comparative example, the oxygen permeability was measured in accordance with JIS K 7126-2 using an oxygen permeability measuring device (OX-TRAN 2 / 22L manufactured by MOCON) under the conditions of 23 °C and 60% RH. The oxygen transmission amount was measured as the transmission amount per 1 m 2 , per day and per atmospheric pressure.

[0085] [Water vapor permeability] For the films of each example and each comparative example, the water vapor permeability was measured in accordance with JIS K 7129B using a water vapor transmission rate measuring device (PERMATRAN-W 3 / 34G manufactured by MOCON). The test conditions were 40 °C and 90% RH, and the water vapor transmission amount was measured as the transmission amount per 1 m 2 , per day.

[0086]

Table 1

[0087]

Table 2

Claims

1. A gas barrier optical film containing poly(thio)urethane (P), wherein the poly(thio)urethane (P) comprises a cured product of a polymerizable composition containing an isocyanate compound (A) and an active hydrogen compound (B) selected from one or more compounds selected from the group consisting of a polyvalent thiol compound (B1) having two or more functional groups, a hydroxy thiol compound (B2) having a thiol group and a hydroxyl group, and a polyol compound (B3) having two or more functional groups, The water vapor permeability of the gas barrier optical film, measured under the conditions of 40 °C and 90% RH in accordance with JIS K 7129B, is 10.0 g / (m ２ ·day) or less, the gas barrier optical film.

2. The oxygen permeability of the gas barrier optical film, measured under the conditions of 23°C and 60% RH in accordance with JIS K 7126-2, is 5.0 cc / (m ２ ·day·atm) or less, and the gas barrier optical film according to claim 1.

3. The gas barrier optical film according to claim 1 or 2, wherein the polymerizable composition further comprises a photoinitiator (C).

4. The gas barrier optical film according to claim 3, wherein the photoinitiator (C) contains boron.

5. The gas barrier optical film according to any one of claims 1 to 4, wherein the isocyanate compound (A) contains an aromatic isocyanate compound (a).

6. The gas barrier optical film according to claim 5, wherein the aromatic isocyanate compound (a) contains one or more compounds selected from the group consisting of xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate.

7. The gas barrier optical film according to any one of claims 1 to 6, wherein the polythiol compound (B1) contains one or more selected from the group consisting of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptoethyl) sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, and tris(mercaptomethylthio)methane.

8. The gas barrier optical film according to any one of claims 1 to 7, wherein the polythiol compound (B1) contains one or more selected from the group consisting of a bifunctional polythiol compound (b1) and a trifunctional or higher polythiol compound (b2).

9. The gas barrier optical film according to claim 8, wherein the thiol equivalent of the polythiol compound (b1) is 1% or more and 95% or less based on 100% of the total thiol equivalent of the polythiol compound (b1) and the polythiol compound (b2).

10. The gas barrier optical film according to any one of claims 1 to 9, having a thickness of 15 μm or more and 1000 μm or less.

11. The gas barrier optical film according to any one of claims 1 to 10, having a refractive index nd at a temperature of 23°C of 1.50 or more and 1.75 or less.

12. The gas barrier optical film according to any one of claims 1 to 11, having a birefringence in the thickness direction at 25°C and a wavelength of 590 nm, measured by the rotating analyzer method, of less than 10 nm.

13. The gas barrier optical film according to any one of claims 1 to 12, which can be used for the outermost layer or the intermediate layer of a liquid crystal panel, an organic EL display, or a solar cell.

14. A laminate comprising the gas barrier optical film according to any one of claims 1 to 13, On at least one surface of the gas barrier optical film, SiO ２ layer and and.

15. The laminate according to claim 14, further comprising a layer containing clay.

16. The water vapor permeability of the laminate, measured under the conditions of 40°C and 90% RH in accordance with JIS K 7129B, is 1.0 g / (m ２ ·day) or less, the laminate according to claim 14 or 15.

17. A display device comprising the gas barrier optical film according to any one of claims 1 to 13.

18. A solar cell comprising the gas barrier optical film according to any one of claims 1 to 13.

Images