JP2020164881A - Ultraviolet curable resin composition, method for manufacturing light-emitting device, and light-emitting device - Google Patents

Abstract

To provide an ultraviolet curable resin composition the characteristics of which is hardly changed due to storage.SOLUTION: An ultraviolet curable resin composition contains a polymerizable compound and a polymerization initiator. The polymerizable compound contains a radically-polymerizable compound. The polymerization initiator contains a photo-radical initiator. When ultraviolet with a peak wavelength of 395nm is irradiated on the coating film of the ultraviolet curable resin composition with the thickness of 10 μm within a range of an integrated light quantity of 800 mJ/cm2 - 4000 mJ/cm2, the irradiation intensity of the ultraviolet is 1 W/cm2 or less, and the reaction rate of the polymerizable compound is less than 70%. The viscosity at a temperature 25°C is 1 mPa s - 20 mPa s.SELECTED DRAWING: Figure 1

Description

The present disclosure relates to an ultraviolet curable resin composition, a method for producing a light emitting device, and a light emitting device. More specifically, the present disclosure relates to an ultraviolet curable resin composition containing a polymerizable compound and a polymerization initiator, and a light emitting device using the same. Regarding the manufacturing method and the light emitting device.

Patent Document 1 describes a sealing agent for an organic EL display element. This sealant for an organic EL display element contains a polymerizable compound and a polymerization initiator, has a viscosity at 25 ° C. of 5 to 50 mPa · s, and has a surface tension of 15 to 35 mN / m at 25 ° C. The Poisson's ratio of the cured product at 25 ° C. is 0.28 to 0.40. Further, it is described that the sealant for an organic EL display element of Patent Document 1 can be easily applied by an inkjet method.

WO2018 / 074506

The sealant for an organic EL display element applied by the inkjet method has a problem in storage stability. That is, the sealant for an organic EL display element may be stored for a long period of time in an inkjet device due to the convenience of the process of sealing the organic EL display element, for example, for about 6 months in the inkjet device. After storage, it may be used for sealing the organic EL display element. Therefore, a sealing agent for an organic EL display element whose properties do not change with storage is desired.

The present disclosure has been made in view of the above reasons, and an object of the present invention is to provide an ultraviolet curable resin composition whose properties are unlikely to change due to storage. Another object of the present disclosure is to provide a method for manufacturing a light emitting device and a light emitting device using an ultraviolet curable resin composition whose properties are unlikely to change due to storage.

The ultraviolet curable resin composition according to one aspect of the present disclosure is an ultraviolet curable resin composition containing a polymerizable compound, a polymerization initiator and a sensitizer, and the polymerizable compound is a radical polymerizable compound. The polymerization initiator contains a photoradical initiator, and ultraviolet rays having a peak wavelength of 395 nm are applied to a coating film of the ultraviolet curable resin composition having a thickness of 10 μm with an integrated light amount of 800 mJ / cm ² or more and 4000 mJ / cm ^2. When irradiated within the following range, the irradiation intensity of the ultraviolet rays is 1 W / cm ² or less, the reaction rate of the polymerizable compound in the coating film is less than 70%, and the viscosity at 25 ° C. is 1 mPa. It is s or more and 20 mPa · s or less.

The ultraviolet curable resin composition according to one aspect of the present disclosure is an ultraviolet curable resin composition containing a polymerizable compound and a polymerization initiator, and the polymerizable compound contains a cationically polymerizable compound. The polymerization initiator contains a photocation initiator, and the ratio of the photocation initiator to the cationically polymerizable compound is in the range of 1 to 4% by mass, and the ultraviolet curable resin composition having a thickness of 10 μm. When the coating film is irradiated with ultraviolet rays having a peak wavelength of 395 nm at an integrated light amount of 1.6 mJ / cm ² , the irradiation intensity of the ultraviolet rays is 1 W / cm ² , and the reaction rate of the polymerizable compound in the coating film is Is less than 70%, and the viscosity at 25 ° C. is 1 mPa · s or more and 20 mPa · s or less.

The method for manufacturing a light emitting device according to one aspect of the present disclosure is a method for manufacturing a light emitting device including a light source and an optical component that transmits light emitted by the light source, and the ultraviolet curable resin composition is molded by an inkjet method. After that, the ultraviolet curable resin composition molded by the inkjet method is irradiated with ultraviolet rays and cured to produce an optical component.

The light emitting device according to one aspect of the present disclosure includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the ultraviolet curable resin composition.

According to the present disclosure, there is an advantage that it is possible to provide an ultraviolet curable resin composition whose properties are unlikely to change due to storage.

FIG. 1 is a schematic cross-sectional view showing an embodiment of a light emitting device according to the present disclosure. FIG. 2 is a schematic cross-sectional view showing an embodiment of the light emitting device according to the present disclosure.

[UV curable resin composition]
The ultraviolet curable resin composition (hereinafter, may be referred to as composition (X)) according to the present embodiment contains a polymerizable compound and a polymerization initiator. The composition (X) is cured by being irradiated with ultraviolet rays. That is, when the composition (X) is irradiated with ultraviolet rays, the polymerizable compound starts a polymerization reaction by the action of the polymerization initiator, and the polymerizable compound undergoes a polymerization reaction to generate a compound having a large molecular weight and cure. To do. The polymerizable compound contains, for example, at least one component selected from the group consisting of monomers, oligomers and prepolymers. The polymerization initiator may include a curing catalyst.

The polymerizable compound contains, for example, at least one of a radically polymerizable compound and a cationically polymerizable compound. When the polymerizable compound contains a radically polymerizable compound, the composition (X) further contains a photoradical initiator as a polymerization initiator. When the polymerizable compound contains a cationically polymerizable compound, the composition (X) further contains a photocation initiator (cationic curing catalyst) as a polymerization initiator.

[Radical polymerizable compound]
The radically polymerizable compound (Y1) reacts by radical polymerization. That is, the photoradical initiator generates active radicals and attacks the radically polymerizable compound (Y1), whereby the reaction of the radically polymerizable compound (Y1) proceeds.

When the polymerizable compound (Y) contains the radically polymerizable compound (Y1), the radically polymerizable compound (Y1) preferably contains the acrylic compound (A). The acrylic compound (A) has one or more (meth) acryloyl groups in one molecule. In addition, "(meta) akuri" is at least one of "akuri" and "methacry".

The viscosity of the entire acrylic compound (A) at 25 ° C. is preferably 50 mPa · s or less. In this case, the acrylic compound (A) can make the composition (X) particularly low in viscosity. The viscosity of the entire acrylic compound (A) is more preferably 30 mPa · s or less, further preferably 25 mPa · s or less, and particularly preferably 20 mPa · s or less. The viscosity of the entire acrylic compound (A) is, for example, 3 mPa · s or more.

It is also preferable that the viscosity of the entire acrylic compound (A) at 40 ° C. is 50 mPa · s or less. In this case, the acrylic compound (A) can make the composition (X) particularly low in viscosity when heated. The viscosity of the entire acrylic compound (A) is more preferably 30 mPa · s or less, further preferably 25 mPa · s or less, and particularly preferably 20 mPa · s or less. The viscosity of the entire acrylic compound (A) is, for example, 3 mPa · s or more. The viscosity in the present disclosure is measured using a rheometer under the condition of a shear rate of 100s- ¹ . As the rheometer, for example, model number DHR-2 manufactured by Anton Pearl Japan Co., Ltd. can be used.

The acrylic compound (A) preferably contains a polyfunctional acrylic compound (A) having two or more (meth) acryloyl groups in one molecule. In this case, the polyfunctional acrylic compound (A1) can increase the glass transition temperature of the cured product, and therefore the heat resistance of the cured product (sealing material) can be increased. The amount of the polyfunctional acrylic compound (A1) is, for example, 50% by mass or more and 100% by mass or less with respect to the entire acrylic compound (A). The acrylic compound (A) may contain only the polyfunctional acrylic compound (A1).

The polyfunctional acrylic compound (A1) is, for example, 1,3-butylene glycol di (meth) acrylate, 1,4-butanediol oligoacrylate, diethylene glycol diacrylate, 1,6-hexanediol oligoacrylate, neopentyl glycol diacrylate, Triethylene glycol diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, cyclohexanedimethanol diacrylate, tricyclodecane dimethanol diacrylate, bisphenol A polyethoxydiacrylate, bisphenol F polyethoxydiacrylate, pentatriester tetra Acrylate, propoxylation (2) neopentyl glycol diacrylate, trimethylolpropan triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated (3) trimethylol propantriacrylate, propoxylation (2) 3) Glyceryl triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, ethoxylated (4) pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, hexadiol diacrylate, Polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tripropylene glycol triacrylate, bispentaerythritol hexaacrylate, ethylene glycol diacrylate, 1,6-hexanediol diacrylate, ethoxylated 1,6-hexanediol diacrylate, polypropylene glycol diacrylate Acrylate, 1,4-butanediol diacrylate, 1,9-nonanediol diacrylate, tetraethylene glycol diacrylate, 2-n-butyl-2-ethyl-1,3-propanediol diacrylate, neopentyl hydroxypivalate Glycoldiacrylate, Trimethylolpropan triacrylate of hydroxypivalate, Triacrylate of ethoxylated phosphate, Tripropylene glycol diacrylate ethoxylated, Neopentyl glycol-modified trimethylolpropandiacrylate, Stearate-modified pentaerythritol diacrylate, Tetramethylol propanthria Acrylate Rate, tetramethylolmethane triacrylate, caprolactone-modified trimethylolpropane triacrylate, propoxylate glyceryl triacrylate, tetramethylolmethane tetraacrylate, ethoxylated pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexaacrylate, di Pentaerythritol hydroxypentaacrylate, neopentyl glycol oligoacrylate, trimethylolpropane oligoacrylate, pentaerythritol oligoacrylate, ethoxylated neopentyl glycol di (meth) acrylate, propoxylated neopentyl glycol di (meth) acrylate, tripropylene glycol di ( It contains at least one compound selected from the group consisting of meth) acrylates, ethoxylated trimethylolpropane triacrylates, and propoxylated trimethylolpropane triacrylates. The components that the polyfunctional acrylic compound (A1) can contain are not limited to the above.

The acrylic equivalent of the polyfunctional acrylic compound (A1) is preferably 150 g / eq or less, and more preferably 90 g / eq or more and 150 g / eq or less. The weight average molecular weight of the polyfunctional acrylic compound (A1) is, for example, 100 or more and 1000 or less, and more preferably 200 or more and 800 or less.

The polyfunctional acrylic compound (A1) may contain a compound having at least one of a benzene ring, an alicyclic ring and a polar group. The polar group is, for example, at least one of an OH group and an NHCO group. In this case, shrinkage when the composition (X) is cured can be particularly reduced. Further, the adhesion between the cured product and the member made of the inorganic material can be enhanced. The polyfunctional acrylic compound (A1) is at least selected from the group consisting of tricyclodecanedimethanol diacrylate, bisphenol A polyethoxydiacrylate, bisphenol F polyethoxydiacrylate, trimethylolpropane triacrylate and pentatriester tetraacrylate. It may contain a kind of compound. These compounds can particularly reduce shrinkage as the composition (X) cures. Furthermore, these compounds can also enhance the adhesion between the cured product and the member made of the inorganic material.

The polyfunctional acrylic compound (A1) preferably contains a compound (A11) having a structure represented by the following formula (1).

CH ₂ = CR ¹ −COO− (R ³⁻ O) _n −CO−CR ² = CH ₂ … (1)
In the formula (1), each of R ¹ and R ² is a hydrogen or methyl group, n is an integer of 1 or more, R ³ is an alkylene group having 3 or more carbon atoms, and when n is 2 or more, it is in one molecule. The plurality of R ^3s may be the same as or different from each other.

The compound (A11) has a structure represented by the formula (1), and in particular, the encapsulant (cured product of the composition (X)) because R ³ of the formula (1) has 3 or more carbon atoms. It is difficult to increase the affinity with water. Therefore, the sealing material is not easily deteriorated by water. The carbon number of R ³ is, for example, 3 or more and 15 or less. Further, the compound (A11) has a structure represented by the formula (1), and in particular, by having two (meth) acryloyl groups in one molecule, the glass transition temperature of the cured product can be increased. Therefore, the heat resistance of the cured product (sealing material) can be improved. Further, n in the equation (1) is, for example, an integer of 1 or more and 12 or less.

The percentage of the compound (A11) to the acrylic compound (A) is preferably 50% by mass or more. In this case, it is difficult to increase the affinity of the sealing material for water. The percentage of the compound (A11) to the acrylic compound (A) is, for example, 100% by mass or less, or 95% by mass or less, preferably 80% by mass or less.

The compound (A11) preferably contains the compound (A12) having a boiling point of 270 ° C. or higher. That is, the acrylic compound (A) preferably contains the compound (A12) having the structure represented by the formula (1) and having a boiling point of 270 ° C. or higher. In this case, the acrylic compound (A) is less likely to volatilize from the composition (X) during storage of the composition (X) and when the composition (X) is heated. Therefore, the storage stability of the composition (X) is not easily impaired. Further, even if the compound (A12) remains unreacted in the cured product of the composition (X), outgas caused by the compound (A12) is unlikely to be generated from the cured product. Therefore, voids due to outgas are unlikely to occur in the sealing material. If there are voids in the encapsulant, moisture may enter the encapsulant through the voids, but if voids are less likely to occur, it is difficult for moisture to enter the encapsulant. The boiling point is the boiling point under normal pressure obtained by converting the boiling point under reduced pressure, and is obtained by, for example, the method shown in Science of Petroleum, Vol.II. P.1281 (1938). The boiling point of compound (A12) is more preferably 280 ° C. or higher.

The percentage of the compound (A12) to the acrylic compound (A) is preferably 50% by mass or more. In this case, the storage stability of the composition (X) is effectively enhanced, the outgas generation from the encapsulant is effectively reduced, and the affinity of the encapsulant with water is particularly difficult to be enhanced. The percentage of the compound (A12) to the acrylic compound (A) is, for example, 100% by mass or less, or 95% by mass or less, preferably 80% by mass or less.

The viscosity of compound (A12) at 25 ° C. is preferably 25 mPa · s or less. In this case, compound (A12) can reduce the viscosity of composition (X). The viscosity of compound (A12) at 25 ° C. is more preferably 25 mPa · s or less, further preferably 20 mPa · s or less, and particularly preferably 15 mPa · s or less. The viscosity of compound (A12) at 25 ° C. is, for example, 1 mPa · s or more, preferably 3 mPa · s or more, and even more preferably 5 mPa · s or more.

The compound (A12) is, for example, a group consisting of a di (meth) acrylic acid ester of an alkylene glycol, a di (meth) acrylic acid ester of a polyalkylene glycol, and a di (meth) acrylic acid ester of an alkylene oxide-modified alkylene glycol. Contains at least one compound selected from.

The di (meth) acrylic acid ester of the alkylene glycol is a compound in which n is 1 in the formula (1). In this case, the carbon number of R ³ in the formula (1) is preferably 4 to 12. R ³ may be linear or may have a branch. In particular, the di (meth) acrylic acid ester of alkylene glycol is 1,4-butanediol diacrylate, 1,3-butylene glycol diacrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, 1,9. -Nonandiol diacrylate, 1,10-decanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol dimethacrylate, 1, It preferably contains at least one compound selected from the group consisting of 9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate and 1,12-dodecanediol dimethacrylate. The di (meth) acrylic acid ester of alkylene glycol is a product number SR213 manufactured by Sartmer, a product number V195 manufactured by Osaka Organic Chemical Industry, a product number SR212 manufactured by Sartmer, a product number SR247 manufactured by Sartmer, and a product number SR247 manufactured by Kyoei Chemical Industry Co., Ltd. Product name Light acrylate NP-A, product number SR238NS manufactured by Sartmer, product number V230 manufactured by Osaka Organic Chemical Industry Co., Ltd., product number HDDA manufactured by Daicel Co., Ltd., product number 1,6HX-A manufactured by Kyoei Chemical Industry Co., Ltd., Osaka Organic Chemical Industry Co., Ltd. Product number V260, product number 1,9-ND-A manufactured by Kyoei Chemical Industry Co., Ltd., product number A-NOD-A manufactured by Shin-Nakamura Chemical Industry Co., Ltd., product number CD595 manufactured by Ester, product number SR214NS manufactured by Sartmer Co., Ltd., Shin-Nakamura Product number BD manufactured by Chemical Industry Co., Ltd., Product number SR297 manufactured by Sartmer, Product number SR248 manufactured by Sartmer, Product name Light Ester NP manufactured by Kyoei Chemical Industry Co., Ltd., Product number SR239NS manufactured by Sartmer Co., Ltd. , 6HX, product number HD-N manufactured by Shin-Nakamura Chemical Industry Co., Ltd., product name Light Ester 1,9ND manufactured by Kyoei Chemical Industry Co., Ltd., product number NOD-N manufactured by Shin-Nakamura Chemical Industry Co., Ltd., product name Light Ester 1 manufactured by Kyoei Chemical Industry Co., Ltd. , 10DC, product number DOD-N manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and product number SR262 manufactured by Sartmer Co., Ltd. preferably contain at least one compound selected from the group.

The di (meth) acrylic acid ester of the polyalkylene glycol is a compound in which n is 2 or more in the formula (1). n is, for example, 2 to 10, preferably 2 to 7, preferably 2 to 6, and preferably 2 to 3. The carbon number of R ³ is, for example, 2 to 5. The larger the number of carbon atoms, the higher the hydrophobicity of the cured product and the color resist 1, and the more difficult it is for the color resist 1 to permeate moisture. Di (meth) acrylic acid esters of polyalkylene glycol are particularly diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, hexaethylene glycol dimethacrylate, dipropylene glycol diacrylate, and tripropylene glycol dimethacrylate. It preferably contains at least one compound selected from the group consisting of acrylates, tripropylene glycol dimethacrylates and tritetramethylene glycol diacrylates. Further, the di (meth) acrylic acid ester of polyalkylene glycol is particularly the product number SR230 manufactured by Sartmer, the product number SR508NS manufactured by Sartmer, the product number DPGDA manufactured by Daicel, the product number SR306NS manufactured by Sartmer, and the product number TPGDA manufactured by Daicel. , Product number V310HP manufactured by Osaka Organic Chemical Industry Co., Ltd., Product number APG200 manufactured by Shin-Nakamura Chemical Industry Co., Ltd., Product name Light Acrylate PTMGA-250 manufactured by Kyoei Chemical Industry Co., Ltd., Product number SR231NS manufactured by Sartmer Co., Ltd., Product name Light manufactured by Kyoei Chemical Industry Co., Ltd. Ester 2EG, Sartmer product number SR205NS, Kyoei Chemical Industry Co., Ltd. product name Light Ester 3EG, Sartmer product number SR210NS, Kyoei Chemical Industry Co., Ltd. product name Light Ester 4EG, Mitsubishi Chemical Co., Ltd. product name Acrylate HX and new It is preferable to contain at least one compound selected from the group consisting of product number 3PG manufactured by Nakamura Chemical Industry Co., Ltd.

The di (meth) acrylic acid ester of the alkylene oxide-modified alkylene glycol contains, for example, propylene oxide-modified neopentyl glycol. Further, the di (meth) acrylic acid ester of the alkylene oxide-modified alkylene glycol contains, for example, product number EBECRYL145 manufactured by Daicel Corporation.

The percentage of the component having a boiling point of 270 ° C. or higher in the acrylic compound (A) is preferably 80% by mass or more. When the acrylic compound (A) contains the compound (A12), the percentage of the components in the acrylic compound (A) including the compound (A12) having a boiling point of 270 ° C. or higher is 80% by mass or more. Is preferable. In this case, the storage stability of the composition (X) is not particularly impaired, and outgas is particularly unlikely to be generated from the cured product. It is more preferable that the percentage of the component having a boiling point of 280 ° C. or higher in the acrylic compound (A) is 80% by mass or more.

The compound (A11) may contain a compound (A13) other than the compound (A12).

The polyfunctional acrylic compound (A1) may contain a compound (A14) having three or more (meth) acryloyl groups in one molecule. That is, the acrylic compound (A) may contain the compound (A14). In this case, compound (A14) can contain at least one selected from the group consisting, for example, trimethylolpropane triacrylate and trimethylolpropane trimethacrylate. When the acrylic compound (A) contains the compound (A14), the compound (A14) can particularly increase the glass transition temperature of the cured product, and therefore the heat resistance of the encapsulant can be particularly increased.

When the acrylic compound (A) contains the compound (A14), the percentage of the compound (A14) to the acrylic compound (A) is preferably more than 0% by mass and 25% by mass or less. The percentage of compound (A14) is more preferably 10% by mass or more. In this case, the glass transition temperature of the cured product can be particularly increased. Further, when the content of the compound (A14) is 25% by mass or less, the viscosity of the composition (X) due to the compound (A14) is unlikely to increase. When the percentage of the compound (A14) is 20% by mass or less, the increase in the viscosity of the composition (X) is particularly unlikely to occur.

The acrylic compound (A) may contain a monofunctional acrylic compound (A2) having only one (meth) acryloyl group in one molecule. The monofunctional acrylic compound (A2) can suppress shrinkage of the composition (X) during curing. Further, the monofunctional acrylic compound (A2) can contribute to the reduction of the viscosity of the composition (X). When the acrylic compound (A) contains the monofunctional acrylic compound (A2), the percentage of the monofunctional acrylic compound (A2) to the total amount of the acrylic compound (A) is preferably more than 0% by mass and 70% by mass or less. .. If the percentage of the monofunctional acrylic compound (A2) is more than 0% by mass, the monofunctional acrylic compound (A2) can suppress the shrinkage of the composition (X) during curing. It is more preferable that the percentage of the monofunctional acrylic compound (A2) is 5% by mass or more. When the percentage of the monofunctional acrylic compound (A2) is 70% by mass or less, outgas caused by the monofunctional acrylic compound (A2) is unlikely to be generated from the composition (X) and the cured product. Further, when the amount of the monofunctional acrylic compound (A2) is 70% by mass or less, the amount of the polyfunctional component in the acrylic compound (A) can be secured, so that the heat resistance of the cured product is particularly improved by the polyfunctional component. Can be improved. It is more preferable that the percentage of the monofunctional acrylic compound (A2) is 50% by mass or less, more preferably 40% by mass or less of the monofunctional acrylic compound (A2), and particularly preferably 30% by mass or less.

The monofunctional acrylic compound (A2) is, for example, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylicate, 3,3,5-trimethylcyclohexyl (meth) acrylate, 4-tershalbutylcyclohexyl (meth). Acrylate, dicyclopentenyloxyethyl (meth) acrylicate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl ( Meta) acrylate, isooctyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethyl (meth) ) Acrylate, Butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydixylethyl (meth) acrylate, ethyldiglycol (meth) acrylate, cyclic trimethylolpropaneformal mono (meth) acrylate, imide (meth) acrylate , Isoamyl (meth) acrylate, ethoxylated succinic acid (meth) acrylate, trifluoroethyl (meth) acrylate, ω-carboxypolycaprolactone mono (meth) acrylate, cyclohexyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (Meta) acrylate, stearyl (meth) acrylate, diethylene glycol monobutyl ether (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, octyl / decyl (meth) acrylate, tridecyl (meth) acrylate , Caprolactone (meth) acrylate, ethoxylated (4) nonylphenol (meth) acrylate, methoxypolyethylene glycol (350) mono (meth) acrylate, methoxypolyethylene glycol (550) mono (meth) acrylate, phenoxyethyl (meth) acrylate, cyclohexyl (Meta) acrylate, dicyclopentanyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, methylphenoxyethyl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) ac. Relate, tribromophenyl (meth) acrylate, tribromophenyl (meth) acrylate ethoxylated, 2-phenoxyethyl (meth) acrylate, ethylene oxide adduct of 2-phenoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) From the group consisting of propylene oxide adducts of acrylates, phenoxydiethylene glycol (meth) acrylates, 2-hydroxy-3-phenoxypropyl (meth) acrylates, 3-methacryloyloxymethylcyclohexene oxides, and 3- (meth) acryloyloxymethylcyclohexene oxides. Contains at least one compound of choice. The components that the monofunctional acrylic compound (A2) can contain are not limited to the above.

The monofunctional acrylic compound (A2) preferably contains a compound having an alicyclic structure. Compounds having an alicyclic structure include, for example, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, and di. It contains at least one compound selected from the group consisting of cyclopentenyloxyethyl (meth) acrylicate, 3,3,5-trimethylcyclohexyl (meth) acrylate and 4-talshalbutylcyclohexyl (meth) acrylate. The components that can be contained in the compound having an alicyclic structure are not limited to the above.

The monofunctional acrylic compound (A2) also preferably contains the compound (A21) represented by the following formula (10). In this case, it is easy to reduce the viscosity of the composition (X), and it is easy to impart adhesion to a member made of an inorganic material to an optical component such as a sealing material produced from the composition (X). Further, the compound (A21) has a property of being hard to volatilize in spite of having a low viscosity. Therefore, even if the composition (X) is stored, the composition (X) is unlikely to change in composition due to volatilization of the monofunctional acrylic compound (A2).

In formula (10), R ⁰ is an H or methyl group. X is a single bond or divalent hydrocarbon group. Each of R ¹ to R ¹¹ is H, an alkyl group or -R ^12- OH, R ¹² is an alkylene group and at least one of R ¹ to R ¹¹ is an alkyl group or -R ^12- OH. R ¹ to R ¹¹ are not chemically bonded to each other.

When X is a divalent hydrocarbon group, the number of carbon atoms of X is preferably 1 or more and 5 or less, and more preferably 1 or more and 3 or less. The divalent hydrocarbon group is, for example, a methylene group, an ethylene group or a propylene group. It is particularly preferable if X is a single bond or a methylene group. In this case, there is an advantage that the molecular weight of the compound (A21) is small and the viscosity is low.

When at least one of R ¹ to R ¹¹ is an alkyl group, the alkyl group preferably has 1 or more and 8 or less carbon atoms. The alkyl group is, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group or an octyl group. The alkyl group may be linear or branched. That is, for example, when the alkyl group is a butyl group, the butyl group may be a t-butyl group, an n-butyl group, or a sec-butyl group. When the alkyl group is a hexyl group, the hexyl group may be a t-hexyl group, an n-hexyl group, or a sec-hexyl group. When the alkyl group is an octyl group, the octyl group may be, for example, a t-octyl group. It is particularly preferable that the alkyl group is a methyl group or a t-butyl group. In this case, the compound (A21) has an advantage of having a small molecular weight and a low viscosity.

In formula (10), it is preferable that an alkyl group or −R ¹² −OH is connected only to the 4-position of the cyclohexane ring. That is, it is preferable that at least one of R ⁶ and R ⁷ of R ¹ to R ¹¹ is an alkyl group or −R ¹² −OH, and each of the rest is H. Of R ¹ to R ¹¹ , it is particularly preferred that only R ⁶ is an alkyl group or —R ¹² −OH and each of the rest is H. In this case, the compound represented by the formula (10) can have good reactivity, and it is particularly easy to impart adhesion to the color resist 1 to a member made of an inorganic material. This is because the cyclohexane ring in the compound represented by the formula (10) has a boat conformation, and the bulky alkyl group at the 4-position or -R ^12- OH is likely to be located at the pseudo-equatorial position. it is conceivable that. It is considered that when the compound represented by the formula (10) has such a structure, the reactivity of the (meth) acryloyl group in the compound represented by the formula (10) is enhanced. Further, when the compound represented by the formula (10) has such a structure, the compound represented by the formula (10) can increase the free volume in the optical component. Therefore, it is considered that the interfacial free energy between the optical component and the member made of the inorganic material tends to be small, and as a result, the adhesion between the optical component and the member made of the inorganic material tends to be high. The higher the bulk alkyl group or ^-R 12 -OH, alkyl or ^-R 12 -OH is likely located in pseudo equatorial position. From this point of view, it is preferable that preferably larger the number of carbon atoms in the alkyl group or ^-R 12 -OH, also an alkyl group or ^-R 12 -OH and a branch. For example, the alkyl group or -R ^12- OH is preferably a t-butyl group.

In formula (10), it is also preferable that an alkyl group or -R ^12- OH is connected only to each of the 3rd and 5th positions of the cyclohexane ring. That is, of R ¹ to R ¹¹ , at least one of R ⁴ and R ⁵ is an alkyl group or -R ^12- OH, and at least one of R ⁸ and R ⁹ is an alkyl group or -R ^12- OH. It is preferred that each of the remaining is H. Of R ¹ to R ¹¹ , only one of R ⁴ and R ⁵ is an alkyl group or -R ^12- OH, at least one of R ⁸ and R ⁹ is an alkyl group or -R ^12- OH, and the rest. It is more preferable that each is H. Of R ¹ to R ¹¹ , at least one of R ⁴ and R ⁵ is an alkyl group or -R ^12- OH, only one of R ⁸ and R ⁹ is an alkyl group or -R ^12- OH, and the rest. It is also more preferable that each is H. Also in this case, the compound represented by the formula (10) can have good reactivity, and it is particularly easy to impart adhesion to the member made of an inorganic material to the optical component. This is because the cyclohexane ring in the compound represented by the formula (10) has a boat conformation, and the bulky alkyl group or -R ^12- OH at each of the 3 and 5 positions is located at the pseudo-equatorial position. It is thought that this is because it is easy. Therefore, the reactivity of the (meth) acryloyl group in the compound represented by the formula (10) is enhanced and the reactivity of the (meth) acryloyl group in the compound represented by the formula (10) is enhanced as in the case where the alkyl group or −R ¹² −OH is connected only to the 4-position of the cyclohexane ring. It is considered that the adhesion between the optical component and the member made of the inorganic material tends to be high. The higher the bulk alkyl group or ^-R 12 -OH, alkyl or ^-R 12 -OH is likely located in pseudo equatorial position. From this point of view, it is preferable that preferably larger the number of carbon atoms in the alkyl group or ^-R 12 -OH, also an alkyl group or ^-R 12 -OH and a branch. For example, the alkyl group or -R ^12- OH is preferably a t-butyl group.

When at least one of R ¹ to R ¹¹ is −R ¹² −OH, the number of carbon atoms in R ¹² is preferably 1 or more and 5 or less, and more preferably 1 or more and 3 or less. R ¹² is, for example, a methylene group, an ethylene group or a propylene group. It is particularly preferable if R ¹² is a methylene group. In this case, the compound (A21) has an advantage of having a small molecular weight and a low viscosity.

In formula (10), it is particularly preferable that each of R ¹ to R ¹¹ is an H or an alkyl group, and at least one of R ¹ to R ¹¹ is an alkyl group. In this case, the compound represented by the formula (10) can have a particularly low viscosity, so that the composition (X) can have a particularly low viscosity. Therefore, the composition (X) can be particularly easily molded by the inkjet method.

The compound (A21) preferably contains at least one compound selected from the group consisting of the compound represented by the following formula (11), the compound represented by the following formula (12), and the compound represented by the following formula (13).

It is particularly preferable that the monofunctional acrylic compound (A2) contains at least one of the compound represented by the formula (11) and the compound represented by the formula (12). In this case, the viscosity of the composition (X) tends to be particularly low, the glass transition temperature of the optical component tends to be particularly high, and the adhesion between the optical component and the member made of an inorganic material is particularly easy to increase. Further, since the compound represented by the formula (11) and the compound represented by the formula (12) are hard to volatilize, it is easy to improve the storage stability of the composition (X).

The monofunctional acrylic compound (A2) also preferably contains a compound having a cyclic ether structure. The number of ring members of the cyclic ether structure in the compound having a cyclic ether structure is preferably 3 or more, and more preferably 3 or more and 4 or less. The number of carbon atoms contained in the cyclic ether structure is preferably 2 or more and 9 or less, and more preferably 2 or more and 6 or less. The compound having a cyclic ether structure contains at least one compound selected from the group consisting of, for example, 3-methacryloyloxymethylcyclohexene oxide and 3-acryloyloxymethylcyclohexene oxide.

The monofunctional acrylic compound (A2) preferably contains at least one compound having a viscosity at 25 ° C. of 20 mPa · s or less. In this case, the composition (X) can have a low viscosity.

The monofunctional acrylic compound (A2) preferably contains at least one compound having a glass transition temperature of 80 ° C. or higher. In this case, the cured product of composition (X) can have a high glass transition temperature. The monofunctional acrylic compound (A2) is more preferably contained at least one compound having a glass transition temperature of 90 ° C. or higher, and further preferably containing at least one compound having a glass transition temperature of 100 ° C. or higher.

The monofunctional acrylic compound (A2) preferably contains at least one compound having a boiling point of 200 ° C. or higher. In this case, the monofunctional acrylic compound (A2) does not easily reduce the storage stability of the composition (X). The monofunctional acrylic compound (A2) is more preferably containing at least one compound having a boiling point of 250 ° C. or higher.

It is particularly preferable that the monofunctional acrylic compound (A2) contains at least one compound having a viscosity at 25 ° C. of 20 mPa · s or less and a glass transition temperature of 80 ° C. or more. It is also preferable that the monofunctional acrylic compound (A2) contains at least one compound having a viscosity at 25 ° C. of 20 mPa · s or less and a boiling point of 200 ° C. or more. It is also preferable that the monofunctional acrylic compound (A2) contains at least one compound having a glass transition temperature of 80 ° C. or higher and a boiling point of 200 ° C. or higher. If the monofunctional acrylic compound (A2) contains at least one compound having a viscosity at 25 ° C. of 20 mPa · s or less, a glass transition temperature of 80 ° C. or higher, and a boiling point of 200 ° C. or higher, Especially preferable.

In particular, the monofunctional acrylic compound (A2) includes isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylicate, 3,3,5-trimethylcyclohexyl (meth) acrylate and 4-tershalbutylcyclohexyl (meth). It preferably contains at least one compound selected from the group consisting of acrylates. Isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylicate, 3,3,5-trimethylcyclohexyl (meth) acrylate and 4-tershalbutylcyclohexyl (meth) acrylate have high glass transition temperature, low viscosity and Since it has a high boiling point, the properties of the composition (X) and the optical component can be particularly enhanced.

The acrylic compound (A) is selected from the group consisting of a compound having silicon in the molecular skeleton (A41), a compound having phosphorus in the molecular skeleton (A42), and a compound having nitrogen in the molecular skeleton (A43). It is preferable to further contain at least one compound. In this case, the adhesion between the optical component and the member made of the inorganic material is improved. Therefore, a gap is unlikely to occur between the optical component and the light emitting element, and moisture is unlikely to enter the optical component through the gap.

In addition, compound (A41), compound (A42) and compound (A43) are defined by the type of atoms in the molecular skeleton. Therefore, the compound contained in each of the polyfunctional acrylic compound (A1) and the monofunctional acrylic compound (A2) and the compound contained in each of the compound (A41), the compound (A42) and the compound (A43) overlap. sell.

Compound (A41) includes, for example, 3- (trimethoxysilyl) propyl acrylate (for example, product number KBM5103 manufactured by Shin-Etsu Chemical Co., Ltd.) and (meth) acrylic group-containing alkoxysilane oligomer (for example, product number KR-513 manufactured by Shin-Etsu Chemical Co., Ltd.). ) Contains at least one compound selected from the group consisting of. However, since the boiling point of 3- (trimethoxysilyl) propyl acrylate is 260 ° C., when the acrylic compound (A) contains 3- (trimethoxysilyl) propyl acrylate, the acrylic acid relative to the acrylic compound (A) The percentage of 3- (trimethoxysilyl) propyl should be 10% by mass or less.

Compound (A42) includes acid phosphoxy (meth) acrylates such as acid phosphooxypolyoxypropylene glycol monomethacrylate.

Compound (A43) includes, for example, at least one compound selected from the group consisting of acryloyl morpholine, diethyl acrylamide, dimethylaminopropyl acrylamide and pentamethylpiperidyl methacrylate.

When the acrylic compound (A) contains at least one compound selected from the group consisting of the compound (A41), the compound (A42) and the compound (A43), the compound (A41) and the compound (A42) with respect to the acrylic compound (A) ) And the compound (A43) are preferably 0.5% by mass or more and 20% by mass or less, and more preferably 1% by mass or more and 15% by mass or less.

The radically polymerizable compound (Y1) may contain a radically polymerizable compound (E) other than the acrylic compound (A). The radically polymerizable compound (E) is a polyfunctional radically polymerizable compound (E1) having two or more radically polymerizable functional groups in one molecule, and a monofunctional compound having only one radically polymerizable functional group in one molecule. Either one or both of the radically polymerizable compound (E2) can be contained. The amount of the radically polymerizable compound (E) with respect to the total amount of the acrylic compound (A) and the radically polymerizable compound (E) is, for example, 10% by mass or less. The polyfunctional radical polymerizable compound (E1) is, for example, a group consisting of aromatic urethane oligomers, aliphatic urethane oligomers, epoxy acrylate oligomers, polyester acrylate oligomers and other special oligomers having two or more ethylenic double bonds in one molecule. It may contain at least one compound selected from. The components that can be contained in the polyfunctional radically polymerizable compound (E1) are not limited to the above. The monofunctional radical polymerizable compound (E2) includes, for example, N-vinylformamide, vinylcaprolactam, vinylpyrrolidone, phenylglycidyl ether, p-tert-butylphenylglycidyl ether, butylglycidyl ether, 2-ethylhexylglycidyl ether, allylglycidyl ether, 1,2-butylene oxide, 1,3-butadiene monooxide, 1,2-epoxidodecan, epichlorohydrin, 1,2-epoxydecane, styrene oxide, cyclohexene oxide, 3-vinylcyclohexene oxide, 4-vinylcyclohexene It contains at least one compound selected from the group consisting of oxide, N-vinylpyrrolidone and N-vinylcaprolactam. The components that can be contained in the monofunctional radically polymerizable compound (E2) are not limited to the above.

[Cationally polymerizable compound]
The cationically polymerizable compound (Y2) reacts by cationic polymerization. That is, the photocation initiator generates an acid by irradiation with ultraviolet rays, and this acid attacks the cationically polymerizable compound (Y2), so that the process of addition polymerization or ring-opening polymerization of the cationically polymerizable compound (Y2) is sequential. Proceed to.

When the polymerizable compound (Y) contains a cationically polymerizable compound (Y2), the cationically polymerizable compound (Y2) may be, for example, a polyfunctional cationically polymerizable compound (C1) and a monofunctional cationically polymerizable compound (C2). Contains at least one of them.

The polyfunctional cationically polymerizable compound (C1) is either one or both of a polyfunctional cationically polymerizable compound (C11) having no siloxane skeleton and a polyfunctional cationically polymerizable compound (C12) having a siloxane skeleton. Can be contained.

The polyfunctional cationically polymerizable compound (C11) does not have a siloxane skeleton and has two or more cationically polymerizable functional groups per molecule. The number of cationically polymerizable functional groups per molecule of the polyfunctional cationically polymerizable compound (C11) is preferably 2 to 4, more preferably 2 to 3.

The cationically polymerizable functional group is at least one group selected from the group consisting of, for example, an epoxy group, an oxetane group and a vinyl ether group.

The polyfunctional cationic polymerizable compound (C11) is, for example, a group consisting of a polyfunctional alicyclic epoxy compound, a polyfunctional heterocyclic epoxy compound, a polyfunctional oxetane compound, an alkylene glycol diglycidyl ether, and an alkylene glycol monovinyl monoglycidyl ether. Contains at least one compound among the compounds selected from. The components that can be contained in the polyfunctional cationically polymerizable compound (C11) are not limited to the above.

The polyfunctional alicyclic epoxy compound contains, for example, one or both of the compound represented by the following formula (20) and the compound represented by the following formula (30).

In formula (20), each of R ^{1 to} R ¹⁸ is independently a hydrogen atom, a halogen atom, or a hydrocarbon group. The number of carbon atoms of the hydrocarbon group is preferably in the range of 1 to 20. The hydrocarbon group is an alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group and a propyl group; an alkenyl group having 2 to 20 carbon atoms such as a vinyl group and an allyl group; or an alkenyl group having 2 to 20 carbon atoms such as an ethylidene group and a propylidene group. There are 20 alkylidene groups. The hydrocarbon group may contain an oxygen atom or a halogen atom. Each of R ^{1 to} R ¹⁸ is preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms independently, more preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.

In formula (20), X is a single bond or divalent organic group, and the organic group is, for example, -CO-O-CH _2- .

Examples of the compound represented by the formula (20) include a compound represented by the following formula (20a) and a compound represented by the following formula (20b). The components that can be contained in the compound represented by the formula (20) are not limited to the above.

In formula (30), each of R ^{1 to} R ¹² is independently a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms. The halogen atom is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. The hydrocarbon group having 1 to 20 carbon atoms is, for example, an alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group or a propyl group; an alkenyl group having 2 to 20 carbon atoms such as a vinyl group or an allyl group; or an ethylidene group or propyridene. It is an alkylidene group having 2 to 20 carbon atoms such as a group. The hydrocarbon group having 1 to 20 carbon atoms may contain an oxygen atom or a halogen atom.

Each of R ^{1 to} R ¹² is preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms independently, more preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.

Examples of the compound represented by the formula (30) include a tetrahydroindene epoxide represented by the following formula (30a).

The polyfunctional heterocyclic epoxy compound contains, for example, a trifunctional epoxy compound as shown in the following formula (42).

The polyfunctional oxetane compound contains, for example, a bifunctional oxetane compound as represented by the following formula (43).

The alkylene glycol diglycidyl ether contains, for example, at least one compound selected from the group consisting of the compounds represented by the following formulas (44) to (47).

The alkylene glycol monovinyl monoglycidyl ether contains, for example, the compound represented by the following formula (48).

More specifically, the polyfunctional cationically polymerizable compound (C11) includes, for example, celoxide 2021P and celoxide 8010 manufactured by Daicel, TEPIC-VL manufactured by Nissan Chemical Industries, OXT-221 manufactured by Toagosei, and 1, It can contain at least one component selected from the group consisting of 3-PD-DEP, 1,4-BG-DEP, 1,6-HD-DEP, NPG-DEP and butylene glycol monovinyl monoglycidyl ether.

The polyfunctional cationically polymerizable compound (C11) preferably contains a polyfunctional alicyclic epoxy compound. In this case, the composition (X) can have a particularly high cationic polymerization reactivity.

The polyfunctional alicyclic epoxy compound preferably contains either one or both of the compound represented by the formula (20) and the compound represented by the formula (30). In this case, the composition (X) can have a higher cationic polymerization reactivity.

When the polyfunctional alicyclic epoxy compound contains the compound represented by the formula (20), the compound represented by the formula (20) preferably contains the compound represented by the formula (20a). In this case, the composition (X) can have a higher cationic polymerization reactivity and a particularly low viscosity.

Further, in particular, since the compound represented by the formula (30) has a low viscosity, the composition (X) can have good ultraviolet curability and has good ultraviolet curability when the compound represented by the formula (30) is contained. It can have a particularly low viscosity. Further, the compound represented by the formula (30) has a property of being hard to volatilize in spite of having a low viscosity. Therefore, even if the composition (X) contains the compound represented by the formula (30), the composition (X) is unlikely to change in composition due to volatilization of the compound represented by the formula (30). Therefore, the composition (X) can be reduced in viscosity by containing the compound represented by the formula (30) without impairing the storage stability.

The compound represented by the formula (30) can be synthesized, for example, by oxidizing a cyclic olefin compound having a tetrahydroindene skeleton with an oxidizing agent.

The compound represented by the formula (30) may contain four stereoisomers based on the configuration of the two epoxy rings. The compound represented by the formula (30) may contain any of the four stereoisomers. That is, the compound represented by the formula (30) can contain at least one component selected from the group consisting of four stereoisomers. The ratio of the total amount of the exo-end form and the end-end form to the four stereoisomers in the compound represented by the formula (30) is 10% by mass or less with respect to the entire epoxy compound (A1). Is preferable, and more preferably 5% by mass or less. In this case, the heat resistance of the cured product can be improved. The ratio of a specific stereoisomer in the compound represented by the formula (30) can be determined based on the peak area ratio appearing in the chromatogram obtained by gas chromatography.

In order to reduce the amount of the exo-end compound and the endo-end compound in the compound represented by the formula (30), a method for precision distillation of the compound represented by the formula (30), column chromatography using silica gel or the like as a filler. Appropriate methods can be applied, such as the method of applying chromatography.

When the composition (X) contains the polyfunctional cationically polymerizable compound (C11), the ratio of the polyfunctional cationically polymerizable compound (C11) to the cationically polymerizable compound (Y2) is in the range of 5 to 95% by mass. It is preferable to have. When the proportion of the polyfunctional cationically polymerizable compound (C11) is 5% by mass or more, the composition (X) can have particularly excellent reactivity during the photocationic polymerization reaction, and thus the cured product is high. It can have strength (hardness). Further, when the ratio of the polyfunctional cationically polymerizable compound (C11) is 95% by mass or less, when the composition (X) contains the hygroscopic agent (F), the hygroscopic agent (F) is contained in the composition (X). ) Can be easily dispersed evenly. The proportion of the polyfunctional cationically polymerizable compound (C11) is more preferably 12% by mass or more, further preferably 15% by mass or more, further preferably 20% by mass or more, and 25% by mass or more. Is particularly preferable. The proportion of the polyfunctional cationically polymerizable compound (C11) is more preferably 85% by mass or less, and further preferably 60% by mass or less. For example, the proportion of the polyfunctional cationically polymerizable compound (C11) is preferably in the range of 20 to 60% by mass.

When the polyfunctional cationically polymerizable compound (C11) contains a polyfunctional alicyclic epoxy compound, the polyfunctional alicyclic epoxy compound may be a part of the polyfunctional cationically polymerizable compound (C11), and all of them may be. It may be. The ratio of the polyfunctional alicyclic epoxy compound to the polyfunctional cationically polymerizable compound (C11) is preferably in the range of 15 to 100% by mass. When this ratio is 15% by mass or more, the polyfunctional alicyclic epoxy compound can particularly contribute to the improvement of the ultraviolet curability of the composition (X).

The polyfunctional cationically polymerizable compound (C12) has a siloxane skeleton and two or more cationically polymerizable functional groups per molecule. The number of cationically polymerizable functional groups per molecule of the polyfunctional cationically polymerizable compound (C12) is preferably 2 to 6, and more preferably 2 to 4. The polyfunctional cationically polymerizable compound (C12) can contribute to the improvement of the cationic polymerization reactivity of the composition (X) and the heat-resistant discoloration of the cured product (optical component). In addition, the polyfunctional cationically polymerizable compound (C12) can contribute to lowering the elastic modulus of the cured product, and therefore, it is possible to impart flexibility to the cured product.

The polyfunctional cationically polymerizable compound (C12) is preferably liquid at 25 ° C. In particular, the viscosity of the polyfunctional cationically polymerizable compound (C12) at 25 ° C. is preferably in the range of 10 to 300 mPa · s. In this case, the increase in viscosity of the composition (X) can be suppressed.

The cationically polymerizable functional group contained in the polyfunctional cationically polymerizable compound (C12) is at least one group selected from the group consisting of, for example, an epoxy group, an oxetane group and a vinyl ether group.

The siloxane skeleton of the polyfunctional cationically polymerizable compound (C12) may be linear, branched or cyclic. The number of Si atoms contained in the siloxane skeleton is preferably in the range of 2 to 14. In this case, the composition (X) can have a particularly low viscosity. The number of Si atoms is more preferably in the range of 2 to 10, further preferably in the range of 2 to 7, and particularly preferably in the range of 3 to 6.

The polyfunctional cationically polymerizable compound (C12) contains, for example, at least one of a compound represented by the formula (50) and a compound represented by the formula (51).

R in each of the formula (50) and the formula (51) is a single bond or a divalent organic group, and is preferably an alkylene group. Y is a siloxane skeleton, which may be linear, branched or cyclic, and the number of Si atoms thereof is preferably in the range of 2 to 14, and preferably in the range of 2 to 10. Is more preferable, more preferably in the range of 2 to 7, and particularly preferably in the range of 3 to 6. n is an integer of 2 or more, preferably in the range of 2-4.

More specifically, for example, the polyfunctional cationically polymerizable compound (C12) contains the compound represented by the following formula (50a).

R in the formula (50a) is a single bond or a divalent organic group, and is preferably an alkylene group having 1 to 4 carbon atoms. N in the equation (50a) is an integer of 0 or more. n is preferably in the range of 0 to 12, more preferably in the range of 0 to 8, further preferably in the range of 0 to 5, and particularly preferably in the range of 1 to 4. preferable.

The compound represented by the formula (50a) preferably contains the compound represented by the following formula (60). That is, the polyfunctional cationically polymerizable compound (C12) preferably contains the compound represented by the following formula (60).

In the formula (60), n is an integer of 0 or more, preferably in the range of 0 to 12, more preferably in the range of 0 to 8, and further in the range of 0 to 5. It is preferable, and it is particularly preferable if it is within the range of 1 to 4.

Examples of the compound represented by the formula (60) include the compound represented by the following formula (60a-1).

The polyfunctional cationically polymerizable compound (C12) may be used in place of the compound represented by the formula (50a) or together with the compound represented by the formula (50a) in the following formulas (50b) to (50d) and (51a) to (51b). It may contain at least one compound among the compounds shown in.

R in the formula (50d) is a single bond or a divalent organic group, and is preferably an alkylene group having 1 to 4 carbon atoms. N in the formula (50d) is an integer of 0 or more. M in the formula (50d) is an integer of 2 or more.

R in the formula (51a) is a single bond or a divalent organic group, and is preferably an alkylene group having 1 to 4 carbon atoms. N in the formula (51a) is an integer of 0 or more, and is preferably in the range of 8 to 80. M in the formula (51a) is an integer of 2 or more, and is preferably in the range of 2 to 6.

R in the formula (51b) is a single bond or a divalent organic group, and is preferably an alkylene group having 1 to 4 carbon atoms. N in the formula (51b) is an integer of 0 or more, and is preferably in the range of 8 to 80.

More specifically, the polyfunctional cationic polymerizable compound (C12) is, for example, product numbers X-40-2669, X-40-2670, X-40-2715, X-40-2732, manufactured by Shin-Etsu Chemical Co., Ltd. Contains at least one component selected from the group consisting of X-22-169AS, X-22-169B, X-22-2046, X-22-343, X-22-163, and X-22-163B. Is preferable.

The polyfunctional cationically polymerizable compound (C12) preferably has an alicyclic epoxy structure, and it is particularly preferable that the polyfunctional cationically polymerizable compound (C12) contains a compound represented by the formula (50a). The compound represented by the formula (50a) can particularly contribute to the improvement of the cationic polymerization reactivity of the composition (X) and the reduction of the viscosity, and can particularly contribute to the improvement of the heat-resistant discoloration property of the cured product and the reduction of the elastic modulus.

When the composition (X) contains the polyfunctional cationically polymerizable compound (C12), the ratio of the polyfunctional cationically polymerizable compound (C12) to the cationically polymerizable compound (Y2) is in the range of 5 to 95% by mass. It is preferable to have. When the proportion of the polyfunctional cationically polymerizable compound (C12) is 95% by mass or less, the composition (X) can have a particularly high photocationic polymerization reactivity, and therefore the cured product has a particularly high strength (hardness). Can have. The proportion of the polyfunctional cationically polymerizable compound (C12) is more preferably 6% by mass or more, more preferably 13% by mass or more, and particularly preferably 20% by mass or more. Further, the proportion of the polyfunctional cationically polymerizable compound (C12) is more preferably 70% by mass or less, and in this case, the cured product can have a high refractive index. The proportion of the polyfunctional cationically polymerizable compound (C12) is more preferably 45% by mass or less. For example, the proportion of the polyfunctional cationically polymerizable compound (C12) is preferably in the range of 20 to 70% by mass.

The monofunctional cationically polymerizable compound (C2) has only one cationically polymerizable functional group per molecule. The cationically polymerizable functional group is at least one group selected from the group consisting of, for example, an epoxy group, an oxetane group and a vinyl ether group.

The viscosity of the monofunctional cationically polymerizable compound (C2) at 25 ° C. is preferably 8 mPa · s or less. In this case, even if the composition (X) does not contain a solvent, the monofunctional cationically polymerizable compound (C2) can reduce the viscosity of the composition (X). In particular, the viscosity of the monofunctional cationically polymerizable compound (C2) at 25 ° C. is preferably in the range of 0.1 to 8 mPa · s.

The monofunctional cationically polymerizable compound (C2) can contain, for example, at least one compound selected from the group consisting of the compounds represented by the following formulas (62) to (67) and limonene oxide.

The monofunctional cationically polymerizable compound (C2) preferably contains the compound represented by the above formula (66). In this case, the viscosity of the composition (X) can be reduced. Further, since the compound represented by the formula (66) has a high boiling point and low volatility among the components that can be contained in the monofunctional cationically polymerizable compound (C2), the viscosity of the composition (X) with time is changed. Can effectively suppress the rise. Therefore, the composition (X) can have good coatability even when stored for a long period of time, and can maintain good inkjet coatability.

The ratio of the monofunctional cationically polymerizable compound (C2) to the cationically polymerizable compound (Y2) is preferably in the range of 5 to 50% by mass. When the proportion of the monofunctional cationically polymerizable compound (C2) is 5% by mass or more, the viscosity of the composition (X) can be particularly reduced. Further, when the proportion of the monofunctional cationically polymerizable compound (C2) is 50% by mass or less, the composition (X) can have particularly excellent reactivity at the time of the photocationic polymerization reaction, and thereby the cured product. Can have high strength (hardness). The proportion of the monofunctional cationically polymerizable compound (C2) is more preferably 10% by mass or more, and further preferably 15% by mass or more. The proportion of the monofunctional cationically polymerizable compound (C2) is more preferably 40% by mass or less, further preferably 35% by mass or less, and particularly preferably 30% by mass or less. When the proportion of the monofunctional cationically polymerizable compound (C2) is particularly 35% by mass or less, the amount of volatilization of the components in the composition (X) during storage of the composition (X) can be effectively reduced. Therefore, even if the composition (X) is stored for a long period of time, the characteristics of the composition (X) are not easily impaired. Further, it is possible to particularly suppress the occurrence of tack (adhesiveness) in the cured product. For example, the proportion of the monofunctional cationically polymerizable compound (C2) is preferably in the range of 10 to 35% by mass.

Further, particularly when the composition (X) contains a polyfunctional cationically polymerizable compound (C11) and a polyfunctional cationically polymerizable compound (C12), it is polyfunctionally cationically polymerizable with respect to the cationically polymerizable compound (Y2). The ratio of the compound (C11) is in the range of 30 to 60% by mass, the ratio of the polyfunctional cationically polymerizable compound (C12) is in the range of 15 to 30% by mass, and the ratio of the monofunctional cationically polymerizable compound (C2) is. It is preferably in the range of 15 to 40% by mass. In this case, good storage stability, low viscosity, and good cationic polymerization reactivity of the composition (X) can be achieved in a well-balanced manner, and excellent transparency, excellent hygroscopicity, and high refractive index of the cured product can be balanced. Can be achieved well.

[Photoradical initiator]
When the composition (X) contains a radically polymerizable compound (Y1), the composition (X) preferably further contains a photoradical initiator (B). The photoradical initiator (B) is not particularly limited as long as it is a compound that produces radical species when irradiated with ultraviolet rays. The photoradical initiator (B) includes, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.), hexaarylbiimidazole compounds. , Ketooxime ester compound, borate compound, azinium compound, metallocene compound, active ester compound, compound having carbon halogen bond, and at least one compound selected from the group consisting of an alkylamine compound. The amount of the photoradical initiator (B) with respect to 100 parts by mass of the composition (X) is, for example, 1 part by weight or more and 10 parts by mass or less.

The photoradical initiator (B) may contain a sensitizer as part of the photoradical initiator (B). The sensitizer can accelerate the radical generation reaction of the photoradical initiator (B), improve the reactivity of radical polymerization, and improve the crosslink density. The sensitizers are, for example, 9,10-dibutoxyanthracene, 9-hydroxymethylanthracene, thioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, anthraquinone, 1,2-. Dihydroxyanthraquinone, 2-ethylanthraquinone, 1,4-diethoxynaphthalene, p-dimethylaminoacetophenone, p-diethylaminoacetophenone, p-dimethylaminobenzophenone, p-diethylaminobenzophenone, 4,4'-bis (dimethylamino) benzophenone, It can contain at least one compound selected from the group consisting of 4,4'-bis (diethylamino) benzophenone, p-dimethylaminobenzaldehyde, and p-diethylaminobenzaldehyde. The components that the sensitizer can contain are not limited to the above.

The content of the sensitizer in the composition (X) is, for example, 0.1 part by mass or more and 5 parts by mass or less, preferably 0.1 part by mass, with respect to 100 parts by mass of the solid content of the composition (X). It is not less than 3 parts by mass. When the content of the sensitizer is within such a range, the composition (X) can be cured in air, and the composition (X) needs to be cured in an inert atmosphere such as a nitrogen atmosphere. It disappears.

The composition (X) may contain a polymerization accelerator in addition to the photoradical initiator (B). The polymerization accelerator includes, for example, ethyl p-dimethylaminobenzoate, -2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, -2-dimethylaminoethyl benzoate, butoxy p-dimethylaminobenzoate. Contains amine compounds such as ethyl. The components that can be contained in the polymerization accelerator are not limited to the above.

The photoradical polymerization initiator (B) preferably contains a component having photobleaching properties. The component having photobleaching property preferably contains an acylphosphine oxide-based photoinitiator, and it is also preferable to include a compound having photobleaching property among the oxime ester-based photoinitiators.

The photoradical polymerization initiator (B) also preferably contains a component having a sensitizer skeleton in the molecule. The sensitizer skeleton includes, for example, at least one of a 9H-thioxanthene-9-one skeleton and an anthracene skeleton. That is, the photoradical polymerization initiator (B) preferably contains a component having at least one of a 9H-thioxanthene-9-one skeleton and an anthracene skeleton.

From the viewpoint of improving the curability and making it difficult for outgas to be generated from the cured product, the photoradical polymerization initiator (B) preferably contains an oxime ester-based photoinitiator regardless of the presence or absence of photobleaching property.

The oxime ester-based photoinitiator is aromatic in order to prevent contamination of the composition (X) and the manufacturing apparatus due to the decomposition product from the composition (X), and to further reduce outgas from the cured product. It is preferable to include a compound having a ring, more preferably to contain a compound having a fused ring containing an aromatic ring, and further preferably to contain a compound having a fused ring containing a benzene ring and a heterocycle.

Oxime ester-based photoinitiators include, for example, 1,2-octadion-1- [4- (phenylthio)-, 2- (o-benzoyloxime)], and etanone, 1- [9-ethyl-6- (2-). Methylbenzoyl) -9H-carbazole-3-yl]-, 1- (o-acetyloxime), and JP-A-2000-80068, JP-A-2001-233842, JP-A-2010-527339, JP-A-2010- It can contain at least one compound selected from the group consisting of oxime ester-based photoinitiators described in 527338, JP2013-041153A, JP2015-93842A, and the like. The oxime ester-based photoinitiators are commercially available Irgacure OXE-02 (manufactured by BASF), ADEKA Arkuru's NCI-831, N-1919 (manufactured by ADEKA) and TR-PBG-304 (manufactured by Changshu Strong Electronics) having a carbazole skeleton. New Materials Co., Ltd.), Irgacure OXE-01 with diphenylsulfide skeleton, ADEKA Arkuru's NCI-930 (manufactured by ADEKA), TR-PBG-345 and TR-PBG-3057 (manufactured by Joshu Strong Electronics New Materials Co., Ltd.) , And at least one compound selected from the group consisting of TR-PBG-365 (manufactured by Changshu Strong Electronics New Materials Co., Ltd.) and SPI-04 (manufactured by Sanyo) having a fluorene skeleton may be contained. In particular, when the oxime ester-based photoinitiator contains a compound having a diphenyl sulfide skeleton or a fluorene skeleton, it is preferable because the cured product is less likely to be colored by photobleaching. It is also preferable that the oxime ester-based photoinitiator contains a compound having a carbazole skeleton because the exposure sensitivity tends to increase.

It is also preferable that the oxime ester-based photoinitiator contains two or more compounds. In this case, for example, the oxime ester-based photoinitiator contains two or more compounds having different exposure sensitivities, so that the amount of the photoradical polymerization initiator (B) can be reduced while maintaining good exposure sensitivity. Therefore, it is possible to further reduce the generation of outgas from the cured product.

[Photocation initiator]
When the composition (X) contains a cationically polymerizable compound (Y2), the composition (X) preferably further contains a photocation initiator (cationic curing catalyst) (D). The photocation initiator (D) is not particularly limited as long as it is a catalyst that generates protonic acid or Lewis acid by being irradiated with light. The photocation initiator (D) can contain at least one of an ionic photoacid-generating photocation initiator and a non-ionic photoacid-generating photocation initiator.

The ionic photoacid-generating photocation initiator can contain at least one of an onium salt and an organometallic complex. Examples of onium salts include aromatic diazonium salts, aromatic halonium salts, and aromatic sulfonium salts. Examples of organometallic complexes include iron-allene complexes, titanosen complexes, and arylsilanol-aluminum complexes. The ionic photoacid-generating photocation initiator can contain at least one of these components.

The nonionic photoacid-generating photocation initiator is at least selected from the group consisting of, for example, nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenolsulfonic acid ester, diazonaphthoquinone, and N-hydroxyimidephosphonate. Can contain a kind of ingredient. The components that can be contained in the nonionic photoacid-generating photocation initiator are not limited to the above.

More specific examples of compounds that can be contained in the photocation initiator (D) are the DPI series (105, 106, 109, 201, etc.), BI-105, MPI series (103, 105, 106, 109) manufactured by Midori Kagaku. , BBI series (101, 102, 103, 105, 106, 109, 110, 200, 210, 300, 301, etc.), TSP series (102, 103, 105, 106, 109, 200, 300, 1000, etc.) , HDS-109, MDS series (103, 105, 109, 203, 205, 209, etc.), BDS-109, MNPS-109, DTS series (102, 103, 105, 200, etc.), NDS series (103, 105, 155, 165, etc.), DAM series (101, 102, 103, 105, 201, etc.), SI series (105, 106, etc.), PI-106, NDI series (105, 106, 109, 1001, 1004, etc.), PAI Series (01, 101, 106, 1001, 1002, 1003, 1004, etc.), MBZ-101, PYR-100, NB series (101, 201, etc.), NAI series (100, 1002, 1003, 1004, 101, 105, etc.) 106, 109, etc.), TAZ series (100, 101, 102, 103, 104, 107, 108, 109, 110, 113, 114, 118, 122, 123, 203, 204, etc.), NBC-101, ANC-101 , TPS-Actate, DTS-Actate, Di-Boc Bisphinol A, tert-Butyl lithocholate, tert-Butyl deoxycholate, tert-Butyl cholate, BX, BC-2, MPI-103, BDS-105, TPS-103 103, BMS-105, and TMS-105;
Union Carbide, USA Cyracure UVI-6970, Cyracure UVI-6974, Cyracure UVI-6990, and Cyracure UVI-950;
BASF's Irgacure 250, Irgacure 261 and Irgacure 264;
CG-24-61 manufactured by Ciba Geigy Co., Ltd .;
ADEKA Corporation ADEKA OPTMER SP-150, ADEKA OPTMER SP-151, ADEKA OPTMER SP-170 and ADEKA OPTMER SP-171;
DAICAT II manufactured by Daicel Corporation;
UVAC1590 and UVAC1591 manufactured by Daicel Cytec Co., Ltd .;
CI-2064, CI-2369, CI-2624, CI-2481, CI-2734, CI-2855, CI-2823, CI-2758, and CIT-1682; manufactured by Nippon Soda Co., Ltd .;
PI-2074, a tetrakis (pentafluorophenyl) borate toluyl cumyl iodonium salt manufactured by Rhodia;
3M FFC509;
CD-1010, CD-1011 and CD-1012 manufactured by Sartomer, USA;
Includes CPI-100P, CPI-101A, CPI-110P, CPI-110A and CPI-210S from Sun Appro Co., Ltd .; and UVI-6992 and UVI-6976 from Dow Chemical. The photocation initiator (D) can contain at least one compound selected from the group consisting of these compounds.

The ratio of the photocation initiator (D) to the cationically polymerizable compound (Y2) is preferably in the range of 1 to 4% by mass. When this ratio is 1% by mass or more, the composition (X) can have a particularly good cationic polymerization reactivity. Further, when this ratio is 4% by mass or less, the composition (X) can have good storage stability, and the production cost can be reduced by not containing an excess photocation initiator (D). It is possible.

[Other ingredients]
The composition (X) may further contain a hygroscopic agent. When the composition (X) contains a moisture absorbing agent, even if the cured product of the composition (X) is exposed to moisture, the moisture absorbing agent absorbs the moisture, so that the cured product is less likely to deteriorate. The average particle size of the hygroscopic agent is preferably 200 nm or less. In this case, the cured product can have high transparency. The hygroscopic agent is preferably inorganic particles having hygroscopicity, and preferably contains at least one component selected from the group consisting of, for example, zeolite particles, silica gel particles, calcium chloride particles, and titanium oxide nanotube particles. The components that can be contained in the hygroscopic agent are not limited to the above. It is particularly preferable that the hygroscopic agent contains zeolite particles.

When the composition (X) contains the cationically polymerizable compound (Y2), the composition (X) preferably further contains a sensitizer. In this case, the composition (X) can have a particularly high cationic polymerization reactivity. The sensitizer contains, for example, one or both of 9,10-dibutoxyanthracene and 9,10-diethoxyanthracene. The ratio of the sensitizer to the cationically polymerizable compound (Y2) is preferably more than 0% by mass and preferably in the range of 1% by mass or less. In this case, the sensitizer does not easily inhibit the transparency of the cured product, so that the cured product can have good transparency.

The ultraviolet curable resin composition according to the present embodiment can be prepared by mixing the above-mentioned components. The composition (X) is preferably liquid at 25 ° C.

[Physical properties]
When the coating film having a thickness of 10 μm of the ultraviolet curable resin composition according to the present embodiment is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the ultraviolet rays The irradiation intensity of the above is 1 W / cm ² or less, and the reaction rate of the polymerizable compound in the coating film is less than 70%. In other words, ultraviolet rays having a peak wavelength of 395 nm are applied to a coating film having a thickness of 10 μm of the composition (X) within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, and an irradiation intensity of 1 W / cm ² or less. When irradiated, the reaction rate of the polymerizable compound in the coating film is less than 70%. The above conditions are set under normal temperature (25 ° C.) and normal pressure (1 MPa). In addition, ultraviolet irradiation is performed in the atmosphere.

Here, in the present disclosure, "ultraviolet rays" means light rays having a wavelength in the range of 200 nm or more and 410 nm or less, but in the composition (X) according to the present embodiment, the wavelength is in the range of 385 nm or more and 405 nm or less. It cures efficiently with ultraviolet rays. In the present disclosure, it is preferable that the peak wavelength of ultraviolet rays is 395 nm in the range of 385 nm or more and 405 nm or less. The peak wavelength refers to the wavelength of light having the highest emission intensity among the wavelengths of light having a predetermined range.

Further, in the present disclosure, the "integrated light amount" is an exposure amount due to ultraviolet rays, and is a value calculated by multiplying the irradiation intensity and the irradiation time (total amount of ultraviolet rays irradiated during the irradiation time). The irradiation intensity is illuminance, and the unit is W / cm ² . The irradiation time is the time during which ultraviolet rays are irradiated, and the unit is seconds (sec).

Further, in the present disclosure, the "reaction rate" indicates the rate at which the polymerizable compound in the coating film has reacted by irradiation with ultraviolet rays. That is, the polymerizable compound in the coating film before irradiation with ultraviolet rays is reduced by polymerizing and reacting with irradiation with ultraviolet rays, and the ratio of the reduced polymerizable compound is the reaction rate. Specifically, the reaction rate is calculated by the infrared absorption spectrum method (IR method). That is, first, the coating film before irradiation with ultraviolet rays is measured by the IR method to obtain an IR spectrum derived from the polymerizable compound in the coating film. Next, the coating film is irradiated with ultraviolet rays. As a result, at least a part of the polymerizable compounds in the coating film reacts, and the amount of unreacted polymerizable compounds in the coating film is reduced. Next, the coating film after irradiation with ultraviolet rays is measured by the IR method to obtain an IR spectrum derived from the polymerizable compound in the coating film. Then, the IR spectrum obtained before the irradiation with the ultraviolet rays is compared with the IR spectrum obtained after the irradiation with the ultraviolet rays, and the reaction rate is obtained from the reduction rate of the peak. That is, in order to convert the change in absorbance into the reaction rate, the initial state before the reaction is set to 0, the state in which the reactive functional groups are almost completely consumed, and the peak intensity becomes zero is set to 100. Obtained by equation (1) (CMC Publishing, "LED-Current Status and Prospects of UV Curing Technology and Curing Materials-UV Curing Technology Using Light Emitting Diodes-", Chapter 6 Current Status and Prospects of Analytical Methods in UV Curing, 290 See page).
Reaction rate (%) = 100 × {1- (A _v ) _t / (A _v ) ₀ }… (1)
Here, A _v represents a peak intensity of any wave number, t is the elapsed time (0 before the start of the reaction).

In the ultraviolet curable resin composition according to the present embodiment, when the coating film having a thickness of 10 μm is irradiated with ultraviolet rays having a peak wavelength of 395 nm within the range of an integrated light amount of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the above. Since the irradiation intensity of ultraviolet rays is 1 W / cm ² or less and the reaction rate of the polymerizable compound in the coating film is less than 70%, curing does not proceed easily. That is, under the above conditions, the polymerization reaction of the polymerizable compound is difficult to proceed, and the reaction rate of the polymerizable compound remains low at less than 70%. Therefore, although the composition (X) is somewhat sticky (tack) and viscous, it is a fluid liquid and is not completely cured, and is unlikely to change with time, that is, Its properties do not change easily due to storage, and it has excellent storage stability. In particular, if the composition (X) is applied by an inkjet method, clogging of nozzles and curing that impairs circulation in the inkjet device are less likely to occur, and coating defects and damage to the device are reduced. ..

Further, when the coating film having a thickness of 10 μm of the ultraviolet curable resin composition according to the present embodiment is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light amount of 800 mJ / cm ² or more and 4000 mJ / cm ² or less. When the irradiation intensity of the ultraviolet rays exceeds 1 W / cm ² , the reaction rate of the polymerizable compound in the coating film is 70% or more, but particularly when the irradiation intensity of the ultraviolet rays exceeds 5 W / cm ^2. The reaction rate of the polymerizable compound in the coating film is preferably 70% or more. In other words, ultraviolet rays having a peak wavelength of 395 nm are applied to a coating film having a thickness of 10 μm of the composition (X) within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, and an irradiation intensity of more than 5 W / cm ² . When irradiated in some cases, the reaction rate of the polymerizable compound in the coating film is preferably 70% or more. In this case, the polymerization reaction of the composition (X) proceeds not so slowly, and the composition (X) can be cured efficiently.

Further, when the coating film having a thickness of 10 μm of the ultraviolet curable resin composition according to the present embodiment is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less. In particular, when the irradiation intensity of the ultraviolet rays exceeds 8 W / cm ² , the reaction rate of the polymerizable compound in the coating film is preferably 80% or more. In other words, ultraviolet rays having a peak wavelength of 395 nm are applied to a coating film having a thickness of 10 μm of the composition (X) within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, and an irradiation intensity of more than 8 W / cm ² . When irradiated in some cases, the reaction rate of the polymerizable compound in the coating film is preferably 80% or more. In this case, the polymerization reaction of the composition (X) is almost completed and it becomes difficult to proceed, and the curing of the composition (X) can be completed.

As described above, in the ultraviolet curable resin composition according to the present embodiment, when the coating film having a thickness of 10 μm is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less. In addition, the reaction rate of the polymerizable compound changes according to the irradiation intensity of the ultraviolet rays. That is, in the composition (X), even if the thickness of the coating film is constant and the range of the wavelength of the ultraviolet rays to be irradiated and the range of the integrated light amount are constant, the reaction rate of the polymerizable compound depends on the irradiation intensity of the irradiated ultraviolet rays. Is changed, and the degree of curing is different. Specifically, an ultraviolet ray having a peak wavelength of 395 nm is applied to a coating film having a thickness of 10 μm of the composition (X) within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, and an irradiation intensity of 1 W / cm ^2. When irradiated below, the reaction rate of the polymerizable compound in the coating film is less than 70%, and when the irradiation intensity exceeds 1 W / cm ² and is irradiated at 8 W or less, the reaction rate of the polymerizable compound in the coating film is 70. When the irradiation intensity is more than 8 W / cm ² and the irradiation intensity is more than 8 W / cm ² , the reaction rate of the polymerizable compound in the coating film is preferably 80% or more.

In the present disclosure, when the integrated light intensity is at least one value within the range of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the irradiation intensity of ultraviolet rays is 1 W / cm ² or less, and the polymerization in the coating film. The reaction rate of the sex compound may be less than 70%.

In addition, in this disclosure, "curing" means a state in which composition (X) becomes hard and hardly shows fluidity and stickiness (tack). For example, when the tack of the composition (X) is eliminated (reaction rate of 80% or more), it can be considered that the composition (X) is cured (cured).

In the ultraviolet curable resin composition according to the present embodiment, when the coating film having a thickness of 10 μm is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light amount of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the above. When the irradiation intensity of ultraviolet rays is 1 W / cm ² or less, heat is generated by DSC (Differential Scanning Calorimeter) derived from unreacted components in the cured product of the coating film, and the irradiation intensity exceeds 8 W / cm ² . It is preferable that no heat is generated by DSC derived from the unreacted component in the cured product of the coating film.

It is preferable that the composition (X) does not contain a solvent, or the content of the solvent is 1% by mass or less. Therefore, outgas is less likely to be generated from the composition (X) and the cured product. In addition, the storage stability of the composition (X) is further increased.

The composition (X) preferably has a viscosity at 25 ° C. of 1 mPa · s or more and 30 mPa · s or less. In this case, the composition (X) can be applied and molded at room temperature by a casting method, an inkjet method, or the like. In particular, when the viscosity is 30 mPa · s or less, when the composition (X) is applied by the inkjet method, the ejection speed of the composition (X) from the nozzle is less likely to decrease, and satellites are less likely to be generated. It is more preferable that the viscosity is 20 mPa · s or less, and further preferably 15 mPa · s or less. It is also preferable that this viscosity is 5 mPa · s or more.

The light transmittance (total light transmittance) of the composition (X) is preferably 90% or more when the thickness dimension of the cured product is 10 μm. In this case, if the cured product is applied to an optical component in a light emitting device, the efficiency of extracting light that is transmitted through the optical component and emitted to the outside can be particularly improved.

The surface tension of the composition (X) is preferably 20 mN / cm or more and 40 mN / cm or less. In this case, satellites are less likely to occur when the composition (X) is applied by the inkjet method. This is because when the surface tension is 20 mN / cm or more, when the droplet of the composition (X) separates from the nozzle, a tail-shaped portion is less likely to occur in the droplet, and the surface tension is 40 mN / cm or less. It is considered that this is because the droplets of the composition (X) are particularly easily separated from the nozzle.

The composition (X) having such physical properties can be achieved by adjusting the composition of the composition (X). In particular, the reaction rate of the polymerizable compound can be controlled by the blending ratio of the polymerizable compound and the polymerization initiator. That is, when the total amount of the polymerizable compound and the polymerization initiator is constant, the reaction rate of the polymerizable compound tends to decrease as the compounding ratio of the polymerizable compound increases. That is, when the total amount of the polymerizable compound and the polymerization initiator is constant, the reaction rate of the polymerizable compound tends to increase as the blending ratio of the polymerization initiator increases. As described above, the composition (X) having desired curing properties can be obtained depending on the blending ratio of the polymerizable compound and the polymerization initiator.

[Light emitting device]
The light emitting device 1 according to the present embodiment will be described. The light emitting device 1 includes a light source and an optical component that transmits light emitted by the light source. For example, the light emitting device 1 includes a light emitting element 4 and a sealing material 5 that covers the light emitting element 4. In this case, the light emitting element 4 is a light source, and the sealing material 5 is an optical component. The sealing material 5 may cover the light emitting element 4 in direct contact with the light emitting element 4, or may cover the light emitting element 4 with some layer interposed between the sealing material 5 and the light emitting element 4. Good. The light emitting device 1 may be, for example, a lighting device or a display device (display).

The light emitting element 4 includes, for example, a light emitting diode. The light emitting diode includes, for example, at least one of an organic EL element (organic light emitting diode) and a micro light emitting diode. When the light emitting element 4 includes an organic light emitting diode, the light emitting device 1 provided with the light emitting element 4 is, for example, an organic EL display. When the light emitting element 4 includes a micro light emitting diode, the light emitting device 1 including the light emitting element 4 is, for example, a micro LED display. In addition, EL means electroluminescence, and LED means a light emitting diode.

A first example of the structure of the light emitting device 1 will be described with reference to FIG. This light emitting device 1 is a top emission type. The light emitting device 1 includes a support substrate 2, a transparent substrate 3 facing the support substrate 2 at intervals, a light emitting element 4 on the surface of the support substrate 2 facing the transparent substrate 3, and the support substrate 2 and the transparent substrate 3. A sealing material 5 is provided between the two. Further, in the first example, the light emitting device 1 includes a surface of the support substrate 2 facing the transparent substrate 3 and a passivation layer 6 covering the light emitting element 4. That is, the passivation layer 6 is interposed between the light emitting element 4 and the sealing material 5 that covers the light emitting element 4.

The support substrate 2 is made of, for example, a resin material, but is not limited thereto. The transparent substrate 3 is made of a translucent material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate. When the light emitting element 4 includes an organic EL element, the organic EL element includes, for example, a pair of electrodes and an organic light emitting layer between the electrodes. The organic light emitting layer includes, for example, a hole injection layer, a hole transport layer, an organic light emitting layer, and an electron transport layer, and these layers are laminated in the above order. Although only one light emitting element 4 is shown in FIG. 1, even if the light emitting device 1 includes a plurality of light emitting elements 4 and the plurality of light emitting elements 4 form an array on the support substrate 2. Good. The passivation layer 6 is preferably made of silicon nitride or silicon oxide.

A second example of the structure of the light emitting device 1 will be described with reference to FIG. The elements common to the first example shown in FIG. 1 are designated by the same reference numerals as those in FIG. 2, and detailed description thereof will be omitted as appropriate. The light emitting device 1 shown in FIG. 2 is also a top emission type. The light emitting device 1 covers the support substrate 2, the transparent substrate 3 facing the support substrate 2 at intervals, the light emitting element 4 on the surface of the support substrate 2 facing the transparent substrate 3, and the light emitting element 4. The material 5 is provided.

When the light emitting element 4 includes an organic EL element, the organic EL element includes, for example, a pair of electrodes 41 and 43 and an organic light emitting layer 42 between the electrodes 41 and 43, as in the case of the first example. The organic light emitting layer 42 includes, for example, a hole injection layer 421, a hole transport layer 422, an organic light emitting layer 423, and an electron transport layer 424, and these layers are laminated in the above order.

The light emitting device 1 includes a plurality of light emitting elements 4, and the plurality of light emitting elements 4 form an array 9 (hereinafter referred to as an element array 9) on the support substrate 2. The element array 9 also includes a partition wall 7. The partition wall 7 is located on the support substrate 2 and partitions between two adjacent light emitting elements 4. The partition wall 7 is manufactured, for example, by molding a photosensitive resin material by a photolithography method. The element array 9 also includes a connection wiring 8 that electrically connects the electrodes 43 of the adjacent light emitting elements 4 and the electron transport layers 424. The connection wiring 8 is provided on the partition wall 7.

The light emitting device 1 also includes a passivation layer 6 that covers the light emitting element 4. The passivation layer 6 is preferably made of silicon nitride or silicon oxide. The passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62. The first passivation layer 61 covers the light emitting element 4 by covering the element array 9 in a state of being in direct contact with the element array 9. The second passivation layer 62 is arranged at a position opposite to the element array 9 with respect to the first passivation layer 61, and a space is provided between the second passivation layer 62 and the first passivation layer 61. ing. A sealing material 5 is filled between the first passivation layer 61 and the second passivation layer 62. That is, the first passivation layer 61 is interposed between the light emitting element 4 and the sealing material 5 that covers the light emitting element 4.

Further, a second sealing material 52 is filled between the second passivation layer 62 and the transparent substrate 3. The second sealing material 52 is made of, for example, a transparent resin material. The material of the second sealing material 52 is not particularly limited. The material of the second sealing material 52 may be the same as or different from that of the sealing material 5.

The sealing material 5 in the light emitting device 1 having the structure exemplified above can be produced from the ultraviolet curable resin composition according to the present embodiment. That is, the ultraviolet curable resin composition is used for producing the sealing material 5 for the light emitting element 4. In other words, the ultraviolet curable resin composition is preferably a composition for producing a sealing material, a composition for encapsulating a light emitting element, or a composition for producing a light emitting device.

[Manufacturing method of light emitting device]
A method for manufacturing an optical component using the composition (X) and a method for manufacturing a light emitting device 1 which is an organic EL light emitting device will be described.

In the present embodiment, it is preferable that the composition (X) is molded by an inkjet method and then the composition (X) is irradiated with ultraviolet rays to be cured to produce a sealing material 5 which is an optical component. In the present embodiment, the composition (X) can be applied and molded by an inkjet method.

When the composition (X) is applied by the inkjet method, when the composition (X) has a sufficiently low viscosity at room temperature, for example, the viscosity at 25 ° C. is 30 mPa · s or less, particularly 15 mPa · s or less. In some cases, the composition (X) can be molded by applying it by an inkjet method without heating.

When the composition (X) has a property of lowering the viscosity by heating, the composition (X) may be heated and then the composition (X) may be applied and molded by an inkjet method. When the viscosity of the composition (X) at 40 ° C. is 30 mPa · s or less, particularly 15 mPa · s or less, the viscosity of the composition (X) can be reduced by slightly heating, and the viscosity can be reduced. The resulting composition (X) can be ejected by an inkjet method. The heating temperature of the composition (X) is, for example, 20 ° C. or higher and 50 ° C. or lower.

More specifically, for example, first, the support substrate 2 is prepared. A partition wall is formed on one surface of the support substrate 2 by a photolithography method using, for example, a photosensitive resin material. Subsequently, a plurality of organic EL elements, which are a plurality of light emitting elements 4, are provided on one surface of the support substrate 2. The organic EL element can be manufactured by an appropriate method such as a vapor deposition method or a coating method. In particular, it is preferable to manufacture the organic EL element by a coating method such as an inkjet method. As a result, the element array 9 is manufactured on the support substrate 2.

Next, the first passivation layer 61 is provided on the element array 9. The first passivation layer 61 can be produced by a vapor deposition method such as a plasma CVD method.

Next, the composition (X) is molded on the first passivation layer 61 by, for example, an inkjet method to prepare a coating film. If the inkjet method is applied to both the formation of the organic EL element and the coating of the composition (X), the production efficiency of the light emitting device 1 can be particularly improved. Subsequently, the coating film is cured by irradiating it with ultraviolet rays to prepare a sealing material 5. The thickness of the sealing material 5 is, for example, 5 μm or more and 50 μm or less.

The thickness of the sealing material 5 is preferably 4 μm or more and 50 μm or less, and more preferably 4 μm or more and 15 μm or less. As described above, in the present embodiment, since it is easy to mold small droplets of the composition (X) at high density by the inkjet method, it is easy to realize a thin sealing material 5 having a thickness of 4 μm or more and 15 μm or less. When the sealing material 5 is made thinner in this way, tensile stress and compressive stress are less likely to occur in the sealing material 5 in the light emitting device 1. Therefore, it becomes easy to realize the flexible light emitting device 1.

Next, the second passivation layer 62 is provided on the sealing material 5. The second passivation layer 62 can be produced by a vapor deposition method such as a plasma CVD method.

Next, an ultraviolet curable resin material is provided on one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is superposed on this resin material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.

Next, ultraviolet rays are irradiated from the outside toward the transparent substrate 3. Ultraviolet rays pass through the transparent substrate 3 and reach the ultraviolet curable resin material. As a result, the ultraviolet curable resin material is cured, and the second sealing material 52 is produced.

In the present embodiment, as described above, satellites are unlikely to be generated even if the composition (X) is applied by the inkjet method, so that the sealing material 5 can be accurately produced from the composition (X).

The amount of droplets of the composition (X) discharged by the inkjet method is, for example, 7 pl or more and 10 pl or less, but may be less than this. In the present embodiment, even if the droplets are miniaturized, satellites can be less likely to be generated, and therefore the amount of droplets can be reduced to less than 7 pl. In particular, satellites are unlikely to occur even when the droplets of the composition (X) ejected by the inkjet method are small, for example, when the droplets are 2 pl or more and less than 7 pl, or 2 pl or more and 5 pl or less. When the acrylic compound (A) contains a compound having an isobornyl skeleton, the droplets are particularly easy to miniaturize. Therefore, even if the droplets of the composition (X) ejected by the inkjet method for producing a thin encapsulant 5 having a thickness of 2 μm or more and 8 μm or less are made smaller, the encapsulant 5 is separated from the composition (X). Can be manufactured with high accuracy. That is, by forming small droplets at a high density, it is easy to reduce the thickness of the sealing material 5. In this embodiment, the amount of droplets and the thickness of the sealing material 5 are not limited to the above range. That is, the amount of droplets may be larger than 5 pl, and the thickness of the sealing material 5 may be larger than 8 μm.

Further, as described above, the sealing material 5 made of the cured product of the composition (X) can have good heat resistance. Therefore, when the passivation layer 6 (second passivation layer 62) is formed on the sealing material 5 by a vapor deposition method such as a plasma CVD method, the sealing material 5 deteriorates even if the temperature of the sealing material 5 rises. It's hard to do. Further, even if the temperature of the light emitting device rises when the light emitting device is used, the sealing material 5 is unlikely to deteriorate.

The application of the composition (X) according to the present embodiment is not limited to the production of the sealing material 5 for the light emitting element 4. The composition (X) can be used to make various optical components that transmit the light emitted by the light source. For example, the composition (X) may contain a phosphor to prepare a color resist in a color filter from the composition (X). In this case, particularly when the inkjet method is used, it is easy to produce a color resist in a color filter with high density and accuracy. This color filter can be provided in a display device such as an organic EL display or a micro LED display which is a light emitting device.

The compositions of Examples and Comparative Examples were prepared by mixing the components shown in the table below.

The details of the components shown in the table are as follows. The following viscosities are values measured using a rheometer (manufactured by Anton Pearl Japan, model number DHR-2) under the conditions of a temperature of 25 ° C. and a shear rate of 1000 s ^-1 .

(1) Composition (radical polymerizable compound)
PEG200 dimethacrylate: Polyethylene glycol 200 dimethacrylate manufactured by Shin Nakamura Chemical Industry Co., Ltd., viscosity 14 mPa · s (25 ° C.), glass transition temperature 41 ° C.

Pentatriestol tetraacrylate: manufactured by Shin Nakamura Chemical Industry Co., Ltd., viscosity 200 mPa · s (40 ° C.), glass transition temperature 103 ° C.

(Cationopolymerizable compound)
Celoxide 8010: manufactured by Daicel, trade name Celoxide 8010, compound represented by formula (20a), specific gravity 1.11, viscosity 60 mPa · s, refractive index 1.5071.

OXT-221: manufactured by Toagosei, product number OXT-221, compound represented by formula (43), specific gravity 0.998, viscosity 10 mPa · s, refractive index 1.4538.

Celoxide 2021P: A compound represented by formula (20b), manufactured by Daicel, trade name Celoxide 2021P.

X-40-2669: A compound represented by formula (60a-1), manufactured by Shin-Etsu Chemical Co., Ltd., product number X-40-2669.

AL-EOX: manufactured by Yokkaichi Chemical Co., Ltd., product name AL-EOX, 3-allyloxymethyl-3-ethyloxetane: manufactured by Yokkaichi Chemical Co., Ltd., compound represented by formula (66), viscosity 2 mPa · s.

(Photoradical initiator)
TPO: 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, manufactured by BASF, product number Irgacure TPO.

(Photocation initiator)
CPI-210S: Photocation initiator (sulfonium salt) manufactured by Sun Appro Co., Ltd., product number CPI-210S.

(Sensitizer)
DETX-s: 2,4-diethylthioxanthene-9-one, manufactured by Nippon Kayaku Co., Ltd., product number DETX-s.

UVS1331: 9,10-Dibutoxyanthracene, manufactured by Kawasaki Kasei Chemicals, part number UVS1331.

(2) Curing characteristics (reaction rate of polymerizable compound)
The reaction rate of the polymerizable compound was measured in the same manner as above. That is, after the composition is applied on a smooth table (application by the inkjet method), an LED-UV irradiator (model number E075IIHD, peak wavelength 395 nm) manufactured by Ushio Co., Ltd. is used for this in the atmosphere. It was photocured by irradiating with ultraviolet rays under predetermined output conditions. As a result, a film having a thickness of 10 μm was produced. The absorbance of this film by the IR method was measured before and after curing, and the reaction rate was determined from the reduction rate of the peak derived from the polymerizable compound. As a result, "A" is when the reaction rate of the polymerizable compound is 80% or more, "B" is when the reaction rate of the polymerizable compound is 70% or more and less than 80%, and the reaction rate of the polymerizable compound is less than 70%. In the case of, it was evaluated as "C". As the measuring device used in the IR method, the product number "Agilent Cary 610 FTIR microscope system" manufactured by Agilent Technologies was used. Table 1 shows the irradiation intensity, irradiation time, and integrated light intensity of ultraviolet rays.

(3) Evaluation (light transmittance)
The compositions of the above Examples and Comparative Examples are applied to prepare a coating film, and this coating film is applied to the coating film in the atmosphere using an LED-UV irradiator (model number E075IIHD, peak wavelength 395 nm) manufactured by Usio Co., Ltd. A film having a thickness of 10 μm was produced by irradiating with ultraviolet rays under the condition of an integrated light amount of 1.6 J / cm ² and photocuring. The total light transmittance of this film was measured according to JIS K7361-1.

(viscosity)
The viscosities of the compositions of the above Examples and Comparative Examples were measured using a rheometer (manufactured by Anton Pearl Japan, model number DHR-2) under the conditions of a temperature of 25 ° C. and a shear rate of 1000 s- ¹ .

(Storability)
Using an inkjet head "MH5421F / 5421MF" manufactured by Ricoh Co., Ltd., a circulation test of the compositions of the above Examples and Comparative Examples was carried out at a flow rate of 10 ml / min. The evaluation is as follows.
A: It is possible to eject continuously for 10 minutes without any problem, and there is little adhesion of ink (composition) to the inkjet head.
B: It is possible to eject continuously for 10 minutes without any problem, and there is a lot of ink (composition) adhering to the inkjet head.
C: Holes that cannot be ejected continuously for 10 minutes are generated in the inkjet head.

Examples and Comparative Examples have the same integrated light intensity (1.6 J / cm ² ), but in Examples, when the irradiation intensity is 1 W / cm ² , the reaction rate of the polymerizable compound is less than 70%, so that the storage stability Is high. On the other hand, in the comparative example, even if the irradiation intensity is 1 W / cm ² , the reaction rate of the polymerizable compound is 80% or more, so that the storage stability is low.

Further, among the examples, Examples 3 to 6 containing the radically polymerizable compound have a higher reaction rate of the polymerizable compound than Examples 1 and 2 containing the cationically polymerizable compound even if the irradiation intensity is stronger. It is low and tends to be easy to store. In particular, in Examples 5 and 6 in which the blending amount of the photoradical initiator is small (the blending amount is 1% by mass or less with respect to the total amount of the composition), the reaction rate of the polymerizable compound is low even if the irradiation intensity is high. The tendency for higher storability increases.

(Summary)
As described above, the ultraviolet curable resin composition according to the first aspect is an ultraviolet curable resin composition containing a polymerizable compound, a polymerization initiator, and a sensitizer. The polymerizable compound contains a radically polymerizable compound. The polymerization initiator contains a photoradical initiator. When the coating film of the ultraviolet curable resin composition having a thickness of 10 μm is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the irradiation intensity of the ultraviolet rays becomes high. At 1 W / cm ² or less, the reaction rate of the polymerizable compound in the coating film is less than 70%. The viscosity at 25 ° C. is 1 mPa · s or more and 20 mPa · s or less.

According to this aspect, there are advantages that the polymerization reaction of the polymerizable compound is difficult to proceed, the properties are not easily changed by storage, and the storage stability is excellent. In addition, there is an advantage that it is easy to apply and mold by the inkjet method.

The ultraviolet curable resin composition according to the second aspect is an ultraviolet curable resin composition containing a polymerizable compound and a polymerization initiator. The polymerizable compound contains a cationically polymerizable compound. The polymerization initiator contains a photocation initiator. The ratio of the photocation initiator to the cationically polymerizable compound is in the range of 1 to 4% by mass. When the coating film of the ultraviolet curable resin composition having a thickness of 10 μm was irradiated with ultraviolet rays having a peak wavelength of 395 nm at an integrated light intensity of 1.6 mJ / cm ² , the irradiation intensity of the ultraviolet rays was 1 W / cm ² , and the above. The reaction rate of the polymerizable compound in the coating film is less than 70%. The viscosity at 25 ° C. is 1 mPa · s or more and 20 mPa · s or less.

According to this aspect, there are advantages that the polymerization reaction of the polymerizable compound is difficult to proceed, the properties are not easily changed by storage, and the storage stability is excellent. In addition, there is an advantage that it is easy to apply and mold by the inkjet method.

In the first aspect of the ultraviolet curable resin composition according to the third aspect, the amount of the photoradical initiator with respect to 100 parts by mass of the ultraviolet curable resin composition is 1 part by mass or more and 10 parts by mass or less. ..

According to this aspect, there are advantages that the polymerization reaction of the polymerizable compound is difficult to proceed, the properties are not easily changed by storage, and the storage stability is excellent.

In the ultraviolet curable resin composition according to the fourth aspect, in any one of the first to third aspects, ultraviolet rays having a peak wavelength of 395 nm are applied to the coating film of the ultraviolet curable resin composition having a thickness of 10 μm, and the integrated light amount is applied. When the irradiation intensity of the ultraviolet rays exceeds 8 W / cm ² when irradiated in the range of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the reaction rate of the polymerizable compound in the coating film is 80%. That is all.

According to this aspect, there is an advantage that the polymerization reaction of the polymerizable compound can easily proceed and a cured product can be easily obtained.

The ultraviolet curable resin composition according to the fifth aspect contains an acrylic compound as the polymerizable compound in any one of the first to fourth aspects. A photoradical initiator is included as the polymerizable initiator.

According to this aspect, there is an advantage that a cured product having excellent light transmittance can be easily obtained and can be suitably used for an optical system member.

The ultraviolet curable resin composition according to the sixth aspect is used in any one of the first to fifth aspects to produce an optical component that transmits light emitted by a light source.

According to this aspect, there is an advantage that the transmission of light is less likely to be impaired by the optical component and the luminous efficiency is less likely to decrease.

The ultraviolet curable resin composition according to the seventh aspect is molded by an inkjet method in any one of the first to sixth aspects.

According to this aspect, there is an advantage that the polymerization reaction of the polymerizable compound is difficult to proceed and the properties are not easily changed by storage, so that clogging is unlikely to occur.

The ultraviolet curable resin composition according to the eighth aspect has a light transmittance of 90% or more of the cured product in any one of the first to seventh aspects.

According to this aspect, there is an advantage that the transmission of light is less likely to be impaired by the cured product, and it is easy to apply it to a member of an optical system.

The light emitting device (1) according to the ninth aspect includes a light source and an optical component that transmits light emitted by the light source. The optical component includes a cured product of the ultraviolet curable resin composition.

According to this aspect, there is an advantage that the transmission of light is less likely to be impaired by the optical component and the luminous efficiency is less likely to decrease.

The method for manufacturing a light emitting device according to a tenth aspect is a method for manufacturing a light emitting device (1) including a light source and an optical component that transmits light emitted by the light source. The present invention includes producing an optical component by molding the ultraviolet curable resin composition by an inkjet method and then irradiating the ultraviolet curable resin composition molded by the inkjet method with ultraviolet rays to cure the composition.

According to this aspect, the polymerization reaction of the polymerizable compound of the ultraviolet curable resin composition does not proceed easily, the properties do not easily change due to storage, and the storage stability is excellent. Therefore, there is an advantage that clogging is less likely to occur and it is easy to apply and mold by an inkjet method.

1 Light emitting device 4 Light emitting element 5 Encapsulant

Claims (10)

An ultraviolet curable resin composition containing a polymerizable compound, a polymerization initiator, and a sensitizer.
The polymerizable compound contains a radically polymerizable compound and contains
The polymerization initiator contains a photoradical initiator and
When the coating film of the ultraviolet curable resin composition having a thickness of 10 μm was irradiated with ultraviolet rays having a peak wavelength of 395 nm at an integrated light intensity of 1.6 mJ / cm ² , the irradiation intensity of the ultraviolet rays was 1 W / cm ² , and the above. The reaction rate of the polymerizable compound in the coating film is less than 70%,
The viscosity at 25 ° C. is 1 mPa · s or more and 20 mPa · s or less.
UV curable resin composition. An ultraviolet curable resin composition containing a polymerizable compound and a polymerization initiator.
The polymerizable compound contains a cationically polymerizable compound and contains
The polymerization initiator contains a photocation initiator and
The ratio of the photocation initiator to the cationically polymerizable compound is in the range of 1 to 4% by mass.
When the coating film of the ultraviolet curable resin composition having a thickness of 10 μm was irradiated with ultraviolet rays having a peak wavelength of 395 nm at an integrated light intensity of 1.6 mJ / cm ² , the irradiation intensity of the ultraviolet rays was 1 W / cm ² , and the above. The reaction rate of the polymerizable compound in the coating film is less than 70%,
The viscosity at 25 ° C. is 1 mPa · s or more and 20 mPa · s or less.
UV curable resin composition. The amount of the photoradical initiator with respect to 100 parts by mass of the ultraviolet curable resin composition is 1 part by weight or more and 10 parts by mass or less.
The ultraviolet curable resin composition according to claim 1. When the coating film of the ultraviolet curable resin composition having a thickness of 10 μm is irradiated with ultraviolet rays having a peak wavelength of 395 nm within a range of an integrated light intensity of 800 mJ / cm ² or more and 4000 mJ / cm ² or less, the irradiation intensity of the ultraviolet rays becomes high. When it exceeds 8 W / cm ² , the reaction rate of the polymerizable compound in the coating film is 80% or more.
The ultraviolet curable resin composition according to any one of claims 1 to 3. The polymerizable compound contains an acrylic compound and contains
A photoradical initiator is included as the polymerizable initiator.
The ultraviolet curable resin composition according to any one of claims 1 to 4. For producing optical components that transmit the light emitted by a light source,
The ultraviolet curable resin composition according to any one of claims 1 to 5. Molded by the inkjet method,
The ultraviolet curable resin composition according to any one of claims 1 to 6. The light transmittance of the cured product is 90% or more.
The ultraviolet curable resin composition according to any one of claims 1 to 7. A light source and an optical component that transmits light emitted by the light source are provided.
The optical component includes a cured product of the ultraviolet curable resin composition according to any one of claims 1 to 8.
Light emitting device. A method of manufacturing a light emitting device including a light source and an optical component that transmits light emitted by the light source.
The ultraviolet curable resin composition according to any one of claims 1 to 8 is molded by an inkjet method, and then the ultraviolet curable resin composition molded by the inkjet method is irradiated with ultraviolet rays to be cured. Including making the optical component in
Manufacturing method of light emitting device.