JP6590269B1 - UV curable resin composition for sealing organic EL element, method for producing organic EL light emitting device, organic EL light emitting device, and touch panel - Google Patents

Abstract

The present invention provides an ultraviolet curable resin composition for organic EL sealing that can be molded by an ink jet method and can easily reduce the dielectric constant of a cured product. An ultraviolet curable resin composition for sealing an organic EL includes an acrylic compound (A) and a photopolymerization initiator (B), and has a relative dielectric constant of 3.0 when the frequency is 100 kHz. It is the following and is shape | molded by the inkjet method. [Selection] Figure 1

Description

  The present disclosure provides an ultraviolet curable resin composition for sealing an organic EL element, a method for producing an organic EL light emitting device, an organic EL light emitting device, and a touch panel. Specifically, the present disclosure relates to an ultraviolet curable resin composition for sealing an organic EL element suitable for producing a sealing material for an organic EL light-emitting device, a method for producing an organic EL light-emitting device using the composition, and the above The present invention relates to an organic EL light emitting device including a sealing material and a touch panel including the organic EL light emitting device.

  In a top emission type organic EL light emitting device, for example, an organic EL element is disposed on a support substrate, a transparent substrate is disposed to face the support substrate, and a transparent sealing material is provided between the support substrate and the transparent substrate. Filled. The sealing material is produced by, for example, an ink jet method.

Patent Document 1 shows an example of an ultraviolet curable resin composition that is used for producing a sealing material for an organic EL light emitting device and is molded by an ink jet method. Specifically, Patent Document 1 discloses an ink composition containing a polyethylene glycol di (meth) acrylate monomer, a mono (meth) acrylate monomer, a polyfunctional (meth) acrylate crosslinker, and a crosslinkable photopolymerization initiator. Things are disclosed.

International Publication No. 2017/39857

  In recent years, an organic EL light-emitting device has been applied to a display (touch panel) provided with a touch sensor. In the touch panel, for example, a touch sensor is disposed on a transparent substrate of an organic EL light emitting device. When the touch panel is used, the touch sensor may malfunction. The inventor has found that a high dielectric constant of the sealing material causes malfunction.

  An object of the present disclosure is to form an organic EL light-emitting device, an organic EL light-emitting device manufacturing method, and an organic EL light-emitting device that can be molded by an ink jet method and can easily lower the dielectric constant of a cured product. The object is to provide a device and a touch panel.

  The ultraviolet curable resin composition for sealing an organic EL according to one embodiment of the present disclosure includes an acrylic compound (A) and a photopolymerization initiator (B). The organic EL sealing ultraviolet curable resin composition has a relative dielectric constant of 3.0 or less when the frequency is 100 kHz. The organic EL sealing ultraviolet curable resin composition is molded by an inkjet method.

The manufacturing method of the organic EL light-emitting device which concerns on 1 aspect of this indication is a method of manufacturing an organic EL light-emitting device provided with an organic EL element and the sealing material which covers the said organic EL element. In the method for producing an organic EL light emitting device, the ultraviolet curable resin composition for sealing an organic EL element is molded by an inkjet method, and then the ultraviolet curable resin composition for sealing an organic EL element is irradiated with ultraviolet rays. It includes making the sealing material by curing.

  An organic EL light emitting device according to an aspect of the present disclosure includes an organic EL element and a sealing material that covers the organic EL element, and the sealing material includes the ultraviolet curable resin composition for sealing the organic EL element. It is a cured product.

  A touch panel according to an aspect of the present disclosure includes the organic EL light emitting device and a touch sensor.

  According to the present disclosure, an ultraviolet curable resin composition for organic EL sealing that can be molded by an ink jet method and can easily reduce the dielectric constant of a cured product, a method for manufacturing an organic EL light emitting device, and an organic EL light emitting device And a touch panel can be provided.

FIG. 1A is a schematic cross-sectional view illustrating a first example of an organic EL light emitting device according to an embodiment of the present disclosure. FIG. 1B is a schematic cross-sectional view showing a second example of the above organic EL light emitting device. FIG. 2 is a schematic cross-sectional view illustrating a touch panel according to an embodiment of the present disclosure.

1. Outline The ultraviolet curable resin composition for organic EL sealing according to an embodiment of the present disclosure (hereinafter also referred to as a resin composition (X)) includes an acrylic compound (A) and a photopolymerization initiator (B). In the resin composition (X), the relative dielectric constant of the cured product when the frequency is 100 kHz is 3.0 or less. Resin composition (X) is shape | molded by the inkjet method. When the relative dielectric constant of the cured product of the resin composition (X) is 3.0 or less, the cured product of the resin composition (X) can have a low dielectric constant. Thereby, malfunction of a touch sensor provided with the sealing material which consists of hardened | cured material of resin composition (X) can be suppressed.

  In this embodiment, the acrylic compound (A) is at least one selected from the group consisting of a compound having an isobornyl skeleton, a compound having a dicyclopentanyl skeleton, and a compound having a 3,3,5-trimethylcyclohexyl skeleton. It is preferable that the compound (z) which is a component is included. When the acrylic compound (A) contains the compound (z), the cured product of the resin composition (X) can be easily reduced in dielectric constant, that is, the sealing material produced from the resin composition (X) has a low dielectric constant. Can be Moreover, since the dielectric constant of the cured product can be reduced by the compound (z) in the acrylic compound (A), the viscosity of the resin composition (X) can hardly be increased even if the cured product has a reduced dielectric constant, and the resin composition ( X) is easily formed by an ink jet method.

2. Details Hereinafter, the organic EL light-emitting device 1, the manufacturing method of the organic EL light-emitting device 1, the touch panel 100, and the ultraviolet curable resin composition for sealing an organic EL will be described in detail.

2-1. Organic EL Light Emitting Device A first example organic EL light emitting device 1 shown in FIG. 1A and a second example organic EL light emitting device 1 shown in FIG. 1B include an organic EL element 4 and a sealing material 5 covering the organic EL element 4 Is provided. This sealing material 5 is formed from the resin composition (X). Hereinafter, the structure of the organic EL light emitting device 1 of the first example and the organic EL light emitting device 1 of the second example will be described.

(1) Organic EL Light Emitting Device of First Example The configuration of the organic EL light emitting device 1 of the first example will be described with reference to FIG. 1A.

  The organic EL light emitting device 1 of the first example is a top emission type. The organic EL light emitting device 1 of the first example includes a support substrate 2, a transparent substrate 3 that faces the support substrate 2 with a gap, an organic EL element 4 on a surface of the support substrate 2 that faces the transparent substrate 3, and A sealing material 5 filled between the support substrate 2 and the transparent substrate 3 is provided. Further, the organic EL light emitting device 1 of the first example includes a passivation layer 6 that covers the surface of the support substrate 2 facing the transparent substrate 3 and the organic EL element 4.

  The support substrate 2 is made of, for example, a resin material or glass, but the material of the support substrate 2 is not particularly limited. The support substrate 2 may be plate-shaped or film-shaped.

  The transparent substrate 3 is made from a material having translucency. The transparent substrate 3 is made of, for example, glass or transparent resin, but the material of the support substrate 2 is not particularly limited. The transparent substrate 3 may be plate-shaped or film-shaped.

  The organic EL element 4 is also called an organic light emitting diode. The organic EL element 4 includes, for example, a pair of electrodes and an organic light emitting layer located between the electrodes.

  The sealing material 5 is formed from the resin composition (X). The thickness of the sealing material 5 is, for example, 5 μm or more and 50 μm or less.

  The passivation layer 6 is preferably made from silicon nitride or silicon oxide.

(2) Organic EL Light Emitting Device of Second Example The configuration of the organic EL light emitting device 1 of the second example will be described with reference to FIG. 1B. In addition, about the element which is common in the 1st example shown to FIG. 1A, the same code | symbol as FIG. 1A is attached | subjected and detailed description is abbreviate | omitted suitably.

  The organic EL light emitting device 1 of the second example is also a top emission type. The organic EL light emitting device 1 of the second example includes a support substrate 2, a transparent substrate 3 facing the support substrate 2 with a gap, an organic EL element 4 on the surface of the support substrate 2 facing the transparent substrate 3, and The sealing material 5 which covers the organic EL element 4 is provided. The organic EL light emitting device 1 of the second example includes a passivation layer 6 that covers the organic EL element 4.

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

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

The passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62. The first passivation layer 61 covers the organic EL element 4 by covering the element array 9 while in direct contact with the element array 9. The second passivation layer 62 is disposed 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 organic EL element 4 and the sealing material 5 that covers the organic EL element 4. The sealing material 5 can be formed from the resin composition (X).

  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.

2-2. Manufacturing Method of Organic EL Light Emitting Device As described above, the organic EL light emitting device 1 includes the organic EL element 4 and the sealing material 5 formed from the resin composition (X). For example, after the resin composition (X) is molded by an ink jet method, the sealing material 5 can be produced by irradiating the resin composition (X) with ultraviolet rays and curing it.

  In order for the resin composition (X) to be molded by the inkjet method, the resin composition (X) preferably has a sufficiently low viscosity at room temperature. Specifically, the viscosity at 25 ° C. of the resin composition (X) is preferably 50 mP · s or less. In this case, the resin composition (X) is easily molded by the ink jet method.

(1) Manufacturing Method of Organic EL Light Emitting Device of First Example A manufacturing method of the organic EL light emitting device 1 of the first example shown in FIG. 1A will be described.

  First, the support substrate 2 is prepared.

  Next, the organic EL element 4 is disposed on one surface of the support substrate 2. The organic EL element 4 can be produced by a coating method such as an inkjet method. The organic EL element 4 has the configuration of the first example shown in FIG. 1A.

  Next, the passivation layer 6 is disposed. The passivation layer 6 is formed so as to cover one surface of the support substrate 2 and the organic EL element 4. The passivation layer 6 can be produced by, for example, a vapor deposition method.

  Next, the resin composition (X) is molded by an inkjet method so as to cover one surface of the support substrate 2 and the organic EL element 4. In the present embodiment, the resin composition (X) is molded so as to cover the passivation layer 6. The production efficiency of the organic EL light-emitting device 1 can be improved by performing both the molding of the organic EL element 4 and the application of the resin composition (X) by the inkjet method.

  Next, the transparent substrate 3 is overlaid on the molded resin composition (X).

  Next, ultraviolet rays are irradiated from the outside toward the transparent substrate 3. The ultraviolet rays that have passed through the transparent substrate 3 reach the resin composition (X). By this ultraviolet ray, radical polymerization reaction proceeds in the resin composition (X), the resin composition (X) is cured, and the sealing material 5 made of a cured product of the resin composition (X) is produced. .

  Through the above steps, the organic EL light emitting device 1 of the first example can be manufactured.

(2) Manufacturing Method of Organic EL Light Emitting Device of Second Example A manufacturing method of the organic EL light emitting device 1 of the second example shown in FIG. 1B will be described.

  First, the support substrate 2 is prepared.

  Next, the partition wall 7 is formed on one surface of the support substrate 2. The partition wall 7 can be produced by, for example, a photolithography method using a photosensitive resin material.

  Next, a plurality of organic EL elements 4 are arranged on one surface of the support substrate 2. The plurality of organic EL elements 4 can be manufactured by, for example, a vapor deposition method or a coating method, and can be manufactured by an inkjet method among the coating methods. The plurality of organic EL elements 4 constitutes an element array 9.

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

  Next, a coating film of the resin composition (X) is produced on the first passivation layer 61. This coating film can be produced by, for example, an ink jet method. The production efficiency of the organic EL light-emitting device 1 can be improved by performing both the molding of the organic EL element 4 and the application of the resin composition (X) by the inkjet method. The sealing material 5 made of a cured product of the resin composition (X) can be produced by irradiating the coating film with ultraviolet rays and curing it.

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

  Next, after disposing an ultraviolet curable resin material so as to cover the second passivation layer 62, the transparent substrate 3 is overlaid on the resin material.

  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. The resin material is cured by the ultraviolet rays, and the second sealing material 52 made of a cured resin material is produced.

  Through the above steps, the organic EL light emitting device 1 of the second example shown in FIG. 1B is manufactured.

2-3. Touch Panel The configuration of the touch panel 100 of the present embodiment will be described with reference to FIG.

  The touch panel 100 includes an organic EL light emitting device 1 and a touch sensor 10. The organic EL light emitting device 1 is a display device, for example. The touch sensor 10 is disposed on the organic EL light emitting device 1. The touch panel 100 further includes a polarizing plate 11 and a protective layer 12. In the touch panel 100, the organic EL light emitting device 1, the touch sensor 10, the polarizing plate 11, and the protective layer 12 are laminated in this order.

  The organic EL light emitting device 1 is not particularly limited as long as it includes the sealing material 5 made of the resin composition (X). For example, the organic EL light emitting device 1 may be the organic EL light emitting device 1 of the first example, or the organic EL light emitting device 1 of the second example. A touch panel 100 shown in FIG. 2 includes the organic EL light emitting device 1 of the second example.

The touch sensor 10 is disposed on the organic EL light emitting device 1. For this reason, the touch sensor 10 is arrange | positioned on the transparent substrate 3 with which the organic EL light-emitting device 1 is provided. The touch sensor 10 may be a capacitance type or a pressure sensitive type. In this embodiment, the malfunction of the touch sensor 10 can be easily suppressed by reducing the dielectric constant of the resin composition (X). In particular, when the touch sensor 10 is a capacitance type, it is easy to suppress malfunction of the touch sensor 10.

  The polarizing plate 11 is disposed on the touch sensor 10. The visibility of the touch panel 100 can be improved by the polarizing plate 11. The polarizing plate 11 may be plate-shaped or film-shaped. As the polarizing plate 11, a known polarizing plate used for a display can be used. Although the material of the polarizing plate 11 is not specifically limited, For example, it is resin.

  The protective layer 12 is disposed on the polarizing plate 11. The polarizing plate 11 can be protected by the protective layer 12. The protective layer 12 may be plate-shaped or film-shaped. Although the material of the protective layer 12 is not specifically limited, For example, it is resin or glass.

  The touch panel 100 can be manufactured by, for example, stacking the touch sensor 10, the polarizing plate 11, and the protective layer 12 on the organic EL light emitting device 1 in this order.

2-4. Details of the resin composition (X) according to this embodiment will be described.

  Resin composition (X) contains an acrylic compound (A) and a photoinitiator (B). Moreover, resin composition (X) can contain components other than an acrylic compound (A) and a photoinitiator (B).

  In the following description, “(meth) acryl” is a general term for “acryl” and “methacryl”.

(1) Acrylic compound (A)
The acrylic compound (A) is a compound having a (meth) acryloyl group.

  The acrylic compound (A) is a compound (z) that is at least one component selected from the group consisting of a compound having an isobornyl skeleton, a compound having a dicyclopentanyl skeleton, and a compound having a 3,3,5-trimethylcyclohexyl skeleton. ) Is preferably contained. Since compounds having these skeletons are low in polarity, the cured product of the resin composition (X) can be easily reduced in dielectric constant when the resin composition (X) contains the compound (z).

  The compound having an isobornyl skeleton can contain, for example, one or more compounds selected from the group consisting of isobornyl acrylate and isobornyl methacrylate.

  Compounds having a dicyclopentanyl skeleton include, for example, dicyclopentanyl acrylate, dicyclopentanyl methacrylate, dicyclopentanyl diacrylate, dicyclopentanyl dimethacrylate, dicyclopentenyl acrylate, dicyclopentenyl oxy One or more compounds selected from the group consisting of ethyl acrylate and dicyclopentenyloxyethyl methacrylate can be contained. In this specification, the dicyclopentanyl skeleton includes a dicyclopentenyl skeleton.

  The compound having a 3,3,5-trimethylcyclohexyl skeleton can contain, for example, one or more compounds selected from the group consisting of 3,3,5-tricyclohexyl acrylate and 3,3,5-trimethylcyclohexyl methacrylate. .

  Compound (z) is composed of a monofunctional acrylic compound (z1) having only one (meth) acryloyl group in one molecule and a polyfunctional acrylic compound (z2) having a plurality of (meth) acryloyl groups in one molecule. Among these, at least one can be contained.

  Among the monofunctional acrylic compounds (z1), compounds having a high glass transition temperature and a low viscosity are particularly preferable. When the acrylic compound (A) contains such a compound, the resin composition (X) can be easily molded by the inkjet method. Such compounds include isobornyl acrylate and dicyclopentanyl acrylate. That is, the acrylic compound (A) preferably contains at least one of isobornyl acrylate and dicyclopentanyl acrylate.

  Of the polyfunctional acrylic compound (z2), a compound having a particularly low viscosity is preferred. When the acrylic compound (A) contains such a compound, the resin composition (X) can be easily molded by the inkjet method. Such compounds include dicyclopentanyl diacrylate and dicyclopentanyl dimethacrylate. That is, the acrylic compound (A) preferably contains at least one of dicyclopentanyl diacrylate and dicyclopentanyl dimethacrylate.

  The acrylic compound (A) may contain an acrylic compound (y) other than the compound (z). The acrylic compound (y) includes a monofunctional acrylic compound (y1) having only one (meth) acryloyl group in one molecule, a polyfunctional acrylic compound (y2) having a plurality of (meth) acryloyl groups in one molecule, Among these, at least one can be contained.

The monofunctional acrylic compound (y1) is, for example, dicyclopentenyloxyethyl (meth) acrylate, 4-tert-butylcyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate 4-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, 2- Ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate Methoxydoxylethyl (meth) acrylate, ethyl diglycol (meth) acrylate, cyclic trimethylolpropane formal mono (meth) acrylate, imide (meth) acrylate, isoamyl (meth) acrylate, ethoxylated succinic acid (meth) acrylate, tri Fluoroethyl (meth) acrylate, ω-carboxypolycaprolactone mono (meth) acrylate, cyclohexyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, stearyl (meth) acrylate, diethylene glycol monobutyl ether (meth) Acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, octyl / decyl (meth) acrylate, tri Decyl (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 (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, methylphenoxyethyl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, tribromophenyl (meth) acrylate, Ethoxylated tribromophenyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate Relate ethylene oxide adduct, 2-phenoxyethyl (meth) acrylate propylene oxide adduct, phenoxydiethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-methacryloyloxymethylcyclohexene oxide, and It contains at least one compound selected from the group consisting of 3- (meth) acryloyloxymethylcyclohexene oxide.

  The monofunctional acrylic compound (y1) preferably contains a compound having an alicyclic structure. Compounds having an alicyclic structure include, for example, cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and 4-tertiary. It contains at least one compound selected from the group consisting of butylcyclohexyl (meth) acrylate.

  The monofunctional acrylic compound (y1) also preferably contains a compound (y11) represented by the following formula (10). In this case, it is easy to lower the viscosity of the resin composition (X), and adhesion to an inorganic material member such as the passivation layer 6 is easily imparted to the sealing material 5 produced from the resin composition (X). . In addition, the compound (y11) has a property of hardly volatilizing although it has a low viscosity. Therefore, even if the resin composition (X) is stored, the resin composition (X) is unlikely to change in composition due to volatilization of the monofunctional acrylic compound (y1).

In the formula (10), R ⁰ is H or a methyl group. X is a single bond or a 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.

  In Formula (10), when X is a divalent hydrocarbon group, the number of carbon atoms in 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 preferred if X is a single bond or a methylene group. In this case, there is an advantage that the compound (A31) has a small molecular weight and a low viscosity.

In Formula (10), when at least one of R ¹ to R ¹¹ is an alkyl group, the alkyl group preferably has 1 to 8 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, there is an advantage that the compound (y11) has a low 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 among R ¹ to R ¹¹ is an alkyl group or —R ¹² —OH, and each of the remaining is H. Among R ¹ to R ¹¹ , it is particularly preferred that only R ⁶ is an alkyl group or —R ¹² —OH, and the remaining each is H. In this case, the compound represented by the formula (10) can have good reactivity, and is particularly easy to impart adhesion to the sealing material 5 with a member made of an inorganic material. This is because the cyclohexane ring in the compound represented by the formula (10) has a boat-type conformation, and the bulky alkyl group at the 4-position or -R ¹² -OH is easily located at the pseudo-equatorial position. it is conceivable that. It is considered that the reactivity of the (meth) acryloyl group in the compound represented by the formula (10) is enhanced by the compound represented by the formula (10) having such a structure. Moreover, when the compound shown by Formula (10) has such a structure, the compound shown by Formula (10) can enlarge the free volume in the sealing material 5. FIG. Therefore, it is considered that the interface free energy between the sealing material 5 and the member made of an inorganic material tends to be small, and the adhesion between the sealing material 5 and the member made of an 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 the formula (10), it is also preferable that an alkyl group or —R ¹² —OH is connected to each of the 3-position and 5-position of the cyclohexane ring. That is, among R ¹ to R ¹¹ , at least 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, It is preferred that each 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 More preferably, each is H. Among 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 is particularly easy to impart adhesion to the sealing material 5 with a member made of an inorganic material. This is because the cyclohexane ring in the compound represented by the formula (10) has a boat-type conformation, and a bulky alkyl group or —R ¹² —OH in each of the 3-position and 5-position is located in the pseudo-equatorial position. This is probably because it is easy. For this reason, the reactivity of the (meth) acryloyl group in the compound represented by formula (10) is increased, as in the case where an alkyl group or —R ¹² —OH is connected only to the 4-position of the cyclohexane ring, and It is considered that the adhesion between the sealing material 5 and the member made of an 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. R12 is, for example, a methylene group, an ethylene group or a propylene group. It is particularly preferred if R ¹² is a methylene group. In this case, there is an advantage that the compound (y11) has a low molecular weight and a low viscosity.

In formula (10), it is particularly preferred that each of R ¹ to R ¹¹ is 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 resin composition (X) can have a particularly low viscosity. Therefore, it becomes particularly easy to mold the resin composition (X) by the ink jet method.

  The compound (y11) preferably contains at least one compound selected from the group consisting of a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13).

It is particularly preferable that the monofunctional acrylic compound (y1) 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 resin composition (X) is particularly likely to be lowered, the glass transition temperature of the sealing material 5 is particularly easily increased, and the adhesion between the sealing material 5 and the inorganic material member is particularly easily improved. Moreover, since the compound shown to Formula (11) and the compound shown to Formula (12) are hard to volatilize, it is easy to improve the storage stability of resin composition (X).

  The monofunctional acrylic compound (y1) also preferably contains a compound having a cyclic ether structure. The number of 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, for example, at least one compound selected from the group consisting of 3-methacryloyloxymethylcyclohexene oxide and 3-acryloyloxymethylcyclohexene oxide.

  The monofunctional acrylic compound (y1) preferably contains at least one compound having a viscosity at 25 ° C. of 20 mPa · s or less. In this case, the resin composition (X) can be reduced in viscosity.

The monofunctional acrylic compound (y1) preferably contains at least one compound having a glass transition temperature of 80 ° C. or higher. In this case, the cured product of the resin composition (X) can have a high glass transition temperature. The monofunctional acrylic compound (y1) preferably contains at least one compound having a glass transition temperature of 90 ° C. or higher, and more preferably contains at least one compound having a glass transition temperature of 100 ° C. or higher.

  The monofunctional acrylic compound (y1) preferably contains at least one compound having a boiling point of 200 ° C. or higher. In this case, the monofunctional acrylic compound (y1) is difficult to reduce the storage stability of the resin composition (X). It is more preferable that the monofunctional acrylic compound (y1) contains at least one compound having a boiling point of 250 ° C. or higher.

  It is particularly preferred if the monofunctional acrylic compound (y1) 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 (y1) 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 (y1) 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 (y1) 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, Particularly preferred.

  In particular, the monofunctional acrylic compound (y1) preferably contains at least one compound selected from the group consisting of dicyclopentenyloxyethyl (meth) acrylate and 4-tertiarybutylcyclohexyl (meth) acrylate. Dicyclopentenyloxyethyl (meth) acrylate and 4-tertiarybutylcyclohexyl (meth) acrylate have a high glass transition temperature, a low viscosity and a high boiling point, so that the resin composition (X), the curing agent and the sealing agent The characteristics of the material 5 can be particularly enhanced.

  The polyfunctional acrylic compound (y2) includes a compound (y20) having two (meth) acryloyl groups in one molecule and a compound (y21) having three or more (meth) acryloyl groups in one molecule. At least one of them can be contained.

  Compound (y20) is, for example, 1,3-butylene glycol di (meth) acrylate, diethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, cyclohexane di Methanol diacrylate, tricyclodecane dimethanol diacrylate, bisphenol A polyethoxy diacrylate, bisphenol F polyethoxy diacrylate propoxylated (2) neopentyl glycol diacrylate, 2- (2-ethoxyethoxy) ethyl acrylate, hexadiol Diacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, ethylene glycol Diacrylate, 1,6-hexanediol diacrylate, ethoxylated 1,6-hexanediol diacrylate, polypropylene glycol diacrylate, 1,4-butanediol diacrylate, 1,9-nonanediol diacrylate, tetraethylene glycol diacrylate Acrylate, 2-n-butyl-2-ethyl-1,3-propanediol diacrylate, hydroxypivalate neopentyl glycol diacrylate, ethoxylated tripropylene glycol diacrylate, neopentyl glycol modified trimethylolpropane diacrylate, stearic acid Modified pentaerythritol diacrylate, ethoxylated neopentyl glycol di (meth) acrylate, propoxylated neopentyl glycol di (meth) acrylate , And it may contain at least one compound selected from the group consisting of tripropylene glycol di (meth) acrylate.

  Compound (21) is, for example, 1,4-butanediol oligoacrylate, 1,6-hexanediol oligoacrylate, pentatriestol tetraacrylate, trimethylolpropane triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, Pentaerythritol triacrylate, ethoxylated (3) trimethylolpropane triacrylate, propoxylated (3) glyceryl triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, ethoxylated (4) pentaerythritol tetraacrylate, dipentaerythritol penta Acrylate, tripropylene glycol triacrylate, bispentaerythritol hexaacrylate, Roxypivalate trimethylolpropane triacrylate, ethoxylated phosphate triacrylate, tetramethylolpropane triacrylate, tetramethylolmethane triacrylate, caprolactone-modified trimethylolpropane triacrylate, propoxylate glyceryl triacrylate, tetramethylolmethane tetraacrylate, ethoxylated penta Erythritol tetraacrylate, dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexaacrylate, dipentaerythritol hydroxypentaacrylate, neopentyl glycol oligoacrylate, trimethylolpropane oligoacrylate, pentaerythritol oligoacrylate, ethoxylated trimethylo Le propane triacrylate, and it may contain at least one compound selected from the group consisting of propoxylated trimethylol propane triacrylate.

  Among the monofunctional acrylic compounds (y1), compounds having a high glass transition temperature and a low viscosity are particularly preferable. When the acrylic compound (A) contains such a compound, the resin composition (X) is easily molded by an ink jet method. An example of such a compound is 4-t-butylcyclohexyl acrylate. That is, the acrylic compound (A) preferably contains 4-t-butylcyclohexyl acrylate.

  Of the polyfunctional acrylic compound (y2), a compound having a particularly low viscosity is preferred. When the acrylic compound (A) contains such a compound, the resin composition (X) is easily molded by an ink jet method. Such compounds include polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, pentaerythritol tetraacrylate, and trimethylolpropane triacrylate. That is, the acrylic compound (A) preferably contains one or more selected from the group consisting of polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, pentaerythritol tetraacrylate, and trimethylolpropane triacrylate.

  The acrylic compound (A) may contain a crosslinking agent having a (meth) acrylate group. Also in this case, the cured product of the resin composition (X) can have a low dielectric constant. Furthermore, the adhesiveness (adhesive force) of the resin composition (X) can be improved, and the glass transition temperature (Tg) of the resin composition (X) can be improved. Crosslinking agents having a (meth) acrylate group include, for example, alkyl (meth) acrylate, tricyclodecanol (meth) acrylate, fluorene (meth) acrylate, isocyanurate (meth) acrylate, and trimethylolpropane (meth) acrylate. One or more selected from the group can be included.

  The acrylic compound (A) may contain an acrylic compound having a cationic polymerizable functional group. In this case, it is easy to ensure a high glass transition temperature of the cured product of the resin composition (X) by crosslinking the acrylic compound having a cationic polymerizable functional group. Examples of the acrylic compound having a cationic polymerizable functional group include 3,4-epoxycyclohexylmethyl methacrylate. As a commercial item of the acrylic compound which has a cation polymerizable functional group, the product name cyclomer M100 by Daicel Corporation is mentioned, for example.

  The acrylic compound (A) includes a monofunctional acrylic compound (A1) having only one (meth) acryloyl group in one molecule, and the monofunctional (meth) acrylic compound (A1) with respect to the total amount of the acrylic compound (A). The ratio is preferably 50% by mass or more. The monofunctional acrylic compound (A1) is a compound composed of at least one of the monofunctional acrylic compound (z1) and the monofunctional acrylic compound (y1). That is, the acrylic compound (A) contains at least one of the monofunctional acrylic compound (z1) and the monofunctional acrylic compound (y1), and the total of the monofunctional acrylic compound (z1) and the monofunctional acrylic compound (y1). The percentage of the amount is preferably 50% by mass or more based on the total amount of the acrylic compound (A). In this case, the amount of carbonyl groups in the resin composition (X) can be reduced, and the relative dielectric constant of the cured product of the resin composition (X) can be reduced. Moreover, 85 mass% or less is preferable and, as for the ratio of the monofunctional (meth) acryl compound (A1) with respect to acrylic compound (A) whole quantity, 80 mass or less is more preferable. In this case, the glass transition temperature of the cured product of the resin composition (X) can be improved.

  The acrylic compound (A) can include a polyfunctional acrylic compound (A2) having a plurality of (meth) acryloyl cages in one molecule. The polyfunctional acrylic compound (A2) is a compound comprising at least one of the polyfunctional acrylic compound (z2) and the polyfunctional acrylic compound (y2).

  The monofunctional acrylic compound (A1) preferably includes a compound (a1) having a methacryloyl group. The compound (a1) is a compound comprising at least one of a compound having a methacryloyl group among the compounds classified as the compound (z1) and a compound having a methacryloyl group among the compounds classified as the compound (y1). is there. That is, it is preferable that the compound (z) includes the compound (z1) and the compound (z1) includes a compound having a methacryloyl group. It is also preferred that the acrylic compound (A) includes the compound (y), the compound (y) includes the compound (y1), and the compound (y1) includes a compound having a methacryloyl group. Compound (a1) is, for example, isobornyl methacrylate, cyclohexyl methacrylate, dicyclopentanyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methacryloyloxymethylcyclohexene oxide, 3,3,5-trimethylcyclohexyl methacrylate, and 4-t-butyl. One or more selected from the group consisting of cyclohexyl methacrylate can be contained. The percentage of the compound (a1) relative to the total amount of the acrylic compound (A) is preferably 25% by mass or more and 60% by mass or less. In this case, it is easy to reduce the dielectric constant of the cured product of the resin composition (X). Thereby, it is easy to make the sealing material 5 produced from resin composition (X) low in dielectric constant, and in a touch panel provided with the organic electroluminescent light emitting device 1 containing the sealing material 5, it is easy to suppress malfunction of a touch sensor.

(2) Photopolymerization initiator (B)
The photopolymerization initiator (B) preferably contains a radical polymerization initiator that is a compound that generates radical species when irradiated with ultraviolet rays. The photopolymerization initiator (B) includes, for example, aromatic ketones, acylphosphine oxide compounds, α-hydroxyalkylphenone compounds, aromatic onium salt compounds, organic peroxides, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.) , A hexaarylbiimidazole compound, a ketoxime ester compound, a borate compound, an azinium compound, a metallocene compound, an active ester compound, a compound having a carbon halogen bond, and at least one compound selected from the group consisting of alkylamine compounds .

  The photopolymerization initiator (B) preferably contains an acylphosphine oxide compound. The photopolymerization initiator (B) can contain, for example, one or both of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and 2,4,6-trimethylbenzoyl-diphenylphosphinate. The photopolymerization initiator (B) may contain a commercially available acylphosphine oxide compound. Examples of commercially available acylphosphine oxide compounds include Irgacure TPO, Irgacure TPO-L and Irgacure 819 manufactured by BASF.

  The photopolymerization initiator (B) preferably contains an α-hydroxyalkylphenone compound. The photopolymerization initiator (B) contains 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and 2-benzyl-2- ( One or more selected from the group consisting of (dimethylamino) -4′-morpholinobutyrophenone can be included. The photopolymerization initiator (B) may contain a commercially available α-hydroxyalkylphenone compound. Examples of commercially available α-hydroxyalkylphenone compounds include Irgacure 184, Irgacure 907, Irgacure 369, and Irgacure 369E manufactured by BASF.

  The photopolymerization initiator (B) particularly preferably contains both an acylphosphine oxide compound and an α-hydroxyalkylphenone. In this case, the resin composition (X) can be easily cured when the resin composition (X) is irradiated with ultraviolet rays.

  The photopolymerization initiator (B) also preferably contains a component having photobleaching properties. The component having photobleaching property preferably includes a compound having photobleaching property among acylphosphine oxide compounds, and preferably includes a compound having photobleaching property among oxime ester compounds.

  The photopolymerization 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-thioxanthen-9-one skeleton and an anthracene skeleton. That is, the photopolymerization initiator (B) preferably includes a component having at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.

  The photopolymerization initiator (B) improves the curability of the resin composition (X) and makes it difficult to generate outgas from the cured product of the resin composition (X), regardless of the presence or absence of photobleaching properties. It is also preferable to include an oxime ester compound.

  The oxime ester-based compound is an aromatic compound for preventing the resin composition (X) and the production apparatus from being contaminated due to the generation of a decomposition product from the resin composition (X), and for further reducing the outgas from the cured product. It is preferable to include a compound having a ring, more preferable to include a compound having a condensed ring including an aromatic ring, and further preferable to include a compound having a condensed ring including a benzene ring and a hetero ring.

  Examples of oxime ester compounds include 1,2-octadion-1- [4- (phenylthio)-, 2- (o-benzoyloxime)], and ethanone, 1- [9-ethyl-6- (2-methylbenzoyl). ) -9H-carbazol-3-yl]-, 1- (o-acetyloxime), and JP-A 2000-80068, JP-A 2001-233842, Special Table 2010-527339, Special Table 2010-527338, It can contain at least one compound selected from the group consisting of oxime ester compounds described in JP2013-041153A and JP2015-93842A. Oxime ester compounds are commercially available Irgacure OXE-02 (manufactured by BASF) having a carbazole skeleton, Adeka Arcles NCI-831, N-1919 (manufactured by ADEKA) and TR-PBG-304 (Changzhou Power Electronics New Material) Irgacure OXE-01 having a diphenyl sulfide skeleton, Adeka Arcles NCI-930 (manufactured by ADEKA), TR-PBG-345 and TR-PBG-3057 (manufactured by Changzhou Power Electronics New Materials), and It may contain at least one compound selected from the group consisting of TR-PBG-365 (manufactured by Changzhou Power Electronics New Materials) and SPI-04 (manufactured by Sanyo) having a fluorene skeleton. In particular, it is preferable that the oxime ester-based compound contains a compound having a diphenyl sulfide skeleton or a fluorene skeleton in that the cured product is difficult to be colored by photobleaching. It is also preferable that the oxime ester-based compound includes a compound having a carbazole skeleton because exposure sensitivity is likely to increase.

  It is also preferred that the oxime ester compound contains two or more compounds. In this case, for example, since the oxime ester compound contains two or more compounds having different exposure sensitivities, the amount of the photopolymerization initiator (B) can be reduced while maintaining good exposure sensitivity. Outgas can be further hardly generated from the cured product of the resin composition (X).

  The ratio of the photopolymerization initiator (B) to 100 parts by mass of the resin composition (X) is, for example, 1 part by mass or more and 10 parts by mass or less. In this case, the resin composition (X) can be sufficiently cured.

  The photopolymerization initiator (B) may contain a sensitizer. The sensitizer can promote the radical generation reaction of the photopolymerization initiator (B), improve the reactivity of radical polymerization, and can improve the crosslinking density. Examples of the sensitizer include 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, At least selected from the group consisting of 4,4′-bis (diethylamino) benzophenone, p-dimethylaminobenzaldehyde, and p-diethylaminobenzaldehyde It may contain one compound.

  In the case where the photoinitiator (B) contains a sensitizer, the content of the sensitizer in the resin composition (X) is, for example, 0.1% with respect to 100 parts by mass of the solid content of the resin composition (X). 1 part by mass or more and 5 parts by mass or less, preferably 0.1 part by mass or more and 3 parts by mass or less. In this case, the resin composition (X) can be cured in air, and it is not necessary to cure the resin composition (X) under an inert atmosphere such as a nitrogen atmosphere.

(3) Components other than acrylic compound (A) and photopolymerization initiator (B) As described above, resin composition (X) contains components other than acrylic compound (A) and photopolymerization initiator (B). be able to.

  The resin composition (X) may contain, for example, a radical polymerizable compound (C) other than the acrylic compound (A). The radical polymerizable compound (C) is composed of a polyfunctional radical polymerizable compound (C1) having two or more radical polymerizable functional groups in one molecule and a monofunctional having only one radical polymerizable functional group in one molecule. Either one or both of the radical polymerizable compound (C2) may be contained. The amount of the radical polymerizable compound (C) with respect to the total amount of the acrylic compound (A) and the radical polymerizable compound (C) is, for example, 10% by mass or less.

The polyfunctional radically polymerizable compound (C1) is, for example, a group consisting of an aromatic urethane oligomer, an aliphatic urethane oligomer, an epoxy acrylate oligomer, a polyester acrylate oligomer, and other special oligomers having two or more ethylenic double bonds in one molecule. You may contain the at least 1 sort (s) of compound selected from these. More specifically, the polyfunctional radical polymerizable compound (C1) is, for example, UV-2000B, UV-2750B, UV-3000B, UV-3010B, UV-3200B, UV-3300B manufactured by Nippon Synthetic Chemical Industry Co., Ltd. UV-3700B, UV-6640B, UV-8630B, UV-7000B, UV-7610B, UV-1700B, UV-7630B, UV-6300B, UV-6640B, UV-7550B, UV-7600B, UV-7605B, UV- 7610B, UV-7630B, UV-7640B, UV-7650B, UT-5449, UT-5454; CN902, CN902J75, CN929, CN940, CN944, CN944B85, CN959, CN961E75, CN961H81, C manufactured by Sartomer 962, CN963, CN963A80, CN963B80, CN963E75, C
N963E80, CN963J85, CN964, CN965, CN965A80, CN966, CN966A80, CN966B85, CN966H90, CN966J75, CN968, CN969, CN970, CN970A60, CN970E60, CN971, CN971A80, CN971J75, CN972, CN973, CN973A80, CN973H85, CN973J75, CN975, CN977, CN977C70, CN978, CN980, CN981, CN981A75, CN981B88, CN982, CN982A75, CN982B88, CN982E75, CN983, CN984, CN985, CN985B88, CN986, C9998, C999, C991, C999 997, CN999, CN9001, CN9002, CN9004, CN9005, CN9006, CN9007, CN9008, CN9009, CN9010, CN9011, CN9013, CN9018, CN9019, CN9024, CN9025, CN9026, CN9028, C9029, CN9028, C90 CN9290, CN9782, CN9783, CN9788, CN9893; EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, KRM8200, EBECRYL5129, EBECRYL8210, EBECRY8R , EBECRYL9260, KRM7735, KRM8296, KRM8452, EBECRYL4858, EBECRYL8402, EBECRYL9270, EBECRYL8311, EBECRYL8701; Nippon Soda Co., Ltd. B-1000, B-2000. It contains at least one compound selected from the group consisting of B-3000. When the resin composition (X) contains the polyfunctional radical polymerizable compound (C1), the polyfunctional radical polymerizable compound (C1) preferably contains B-1000 manufactured by Nippon Soda Co., Ltd. In this case, the dielectric constant of the resin composition (X) can be easily reduced.

  Monofunctional radically polymerizable compound (C2) is, for example, N-vinylformamide, vinylcaprolactam, vinylpyrrolidone, phenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, 1,2-butylene oxide, 1,3-butadiene monooxide, 1,2-epoxydodecane, epichlorohydrin, 1,2-epoxydecane, styrene oxide, cyclohexene oxide, 3-vinylcyclohexene oxide, 4-vinylcyclohexene It can contain at least one compound selected from the group consisting of oxide, N-vinylpyrrolidone and N-vinylcaprolactam.

  The radically polymerizable compound (C) includes divinylbenzene, polybutadiene, and one or more compounds (C3) selected from the group consisting of divinylbenzene or polybutadiene as a basic skeleton and having a (meth) acrylate group. You may go out. By containing the compound (C3) in the resin composition (X), the cured product of the resin composition (X) can have a low dielectric constant. However, when the molecular weight of the compound (C3) is large, the viscosity of the resin composition (X) tends to be high, and when the molecular weight of the compound (C) is small, the volatility tends to be high. Therefore, in order to lower the dielectric constant of the cured product of the resin composition (X) and lower the viscosity of the resin composition (X), the resin composition (X) may contain the compound (z). preferable.

  The resin composition (X) may contain a polymerization accelerator (D). The polymerization accelerator (D) can promote the radical polymerization reaction of the resin composition (X). Polymerization accelerators (D) are, for example, ethyl p-dimethylaminobenzoate, p-dimethylaminobenzoic acid-2-ethylhexyl, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and p-dimethyl. One or more components selected from the group consisting of butoxyethyl aminobenzoate and the like can be contained.

  The resin composition (X) may contain a hygroscopic agent (E). The hygroscopic agent (E) can impart hygroscopicity to the cured product of the resin composition (X). The hygroscopic agent (E) is preferably inorganic particles having hygroscopicity. The hygroscopic agent (E) can contain one or more components selected from the group consisting of zeolite particles, silica gel particles, calcium chloride particles and titanium oxide nanotube particles, for example. The hygroscopic agent (E) preferably contains zeolite particles, and particularly preferably contains zeolite particles having an average particle size of 200 nm or less. Such zeolite particles preferably contain sodium ions. For this purpose, the zeolite particles are preferably produced from zeolite containing sodium ions, and are produced from at least one material selected from the group consisting of A-type zeolite, X-type zeolite and Y-type zeolite among sodium ions. More preferably. It is particularly preferred that the zeolite particles are produced from 4A type zeolites among the A type zeolites. In these cases, the zeolite particles have a crystal structure suitable for moisture adsorption. The ratio of the hygroscopic agent (E) to the total amount of the resin composition (X) is preferably 1% by mass or more and 20% by mass or less. When the ratio of the hygroscopic agent (E) is 1% by mass or more, the cured product of the resin composition (X) can have high hygroscopicity. When the ratio of the hygroscopic agent (E) is 20% by mass or less, the viscosity of the resin composition (X) can be reduced, and the resin composition (X) can be easily molded by an inkjet method.

  The resin composition (X) may contain an inorganic filler (F). For example, the resin composition (X) can contain nano-sized high refractive index particles as the inorganic filler (F). In this case, the cured product can have a high refractive index while maintaining good transparency of the cured product of the resin composition (X). Therefore, when the sealing material 5 is produced from resin composition (X), the extraction efficiency of the light which permeate | transmits the sealing material 5 and radiate | emits outside can be improved. Nano-sized high refractive index particles are, for example, zirconia particles.

  When the resin composition (X) contains a hygroscopic agent (E), the resin composition (X) may contain a dispersant (G). The dispersant (G) is a surfactant that can be adsorbed on the moisture absorbent (E). The dispersing agent (G) is, for example, an adsorbing group that can be adsorbed on the particles of the hygroscopic agent (E), and a chain-like or comb-shaped molecule that adheres to the particles of the adsorbing group adsorbed on the hygroscopic agent (E) particles. And a tail that is a skeleton. The dispersant (G) is, for example, an acrylic dispersant in which the tail is an acrylic molecular chain, a urethane dispersant in which the tail is a urethane molecular chain, and a polyester dispersion in which the tail is a polyester molecular chain. One or more components selected from the group consisting of agents can be contained. The dispersant (G) can favorably disperse the hygroscopic agent (E) in the resin composition (X) and in the cured product. Thereby, even if the hardened | cured material of resin composition (X) contains the hygroscopic agent (E), it can suppress that the transparency of hardened | cured material falls with a hygroscopic agent (E). Further, the dispersant (G) can suppress aggregation of the hygroscopic agent (E) during storage of the resin composition (X). Therefore, the storage stability of the resin composition (X) can be hardly reduced by the hygroscopic agent (E). Moreover, it can suppress that the adhesiveness between the hardened | cured material of resin composition (X), silicon nitride, and a silicon oxide is reduced with a dispersing agent (G). This is presumably because the dispersant (G) is easily adsorbed to the hygroscopic agent (E) and hardly affects the interface between the cured product and silicon nitride and silicon oxide. For this reason, when resin composition (X) contains a dispersing agent (G), the sealing material 5 can have high adhesiveness with a glass-made base material. Further, the adhesion between the passivation layer 6 made of silicon nitride or silicon oxide and the sealing material 5 can be improved. The ratio of the dispersant (G) to 100 parts by mass of the hygroscopic agent (E) is preferably 5% by mass or more and 60% by mass or less. If the amount of the dispersant (G) is 5% by mass or more, the advantage of the dispersant (G) can be exhibited particularly. If the quantity of a dispersing agent (G) is 60 mass% or less, the adhesiveness between the hardened | cured material of resin composition (X), silicon nitride, and a silicon oxide can be improved.

  The resin composition (X) may contain a cationically polymerizable compound (H). The cationic polymerizable compound (H) can contain one or both of a monofunctional cationic polymerizable compound and a polyfunctional cationic polymerizable compound. The cationic polymerizable compound (H) is an alkyl type epoxy compound, dicyclopentadiene type epoxy compound, bisphenol F type epoxy compound, bisphenol A type epoxy compound, phenol novolak type epoxy compound, naphthalene type epoxy compound, oxetane compound, and biphenyl type. It is preferable to contain one or more compounds selected from the group consisting of epoxy compounds. These compounds can lower the dielectric constant of the cured product of the resin composition (X). In order to further reduce the dielectric constant of the cured product of the resin composition (X), it is more preferable that the resin composition (X) contains the compound (z). As a particularly preferred cationically polymerizable compound (H), for example, 2,3-epoxypropyl 2- (4,4-dimethylpentan-2-yl) -5,7,7-trimethyloctanoate, (3, 3 ′, 4,4′-diepoxy) bicyclohexyl, 3-ethyl-3-{[(3-ethyloxetane-3-yl) methoxy] methyl} oxetane, and the like.

  When the resin composition (X) contains the cationic polymerizable compound (H), the photopolymerization initiator (B) preferably contains the cationic polymerization initiator (h). The cationic polymerization initiator (h) is not particularly limited as long as it is a catalyst that generates protonic acid or Lewis acid when irradiated with light. The cationic polymerization initiator (h) can contain at least one of an ionic photoacid-generating cationic curing catalyst and a nonionic photoacid generator cationic curing catalyst. Examples of the commercially available cationic polymerization initiator (h) include Midori Chemical part number DTS-200.

  In the present embodiment, as described above, when the resin composition (X) contains the compound (z), the cured product of the resin composition (X) can have a low dielectric constant. For this reason, in order to reduce the dielectric constant of the hardened | cured material of resin composition (X), it is not necessary to mix | blend an inorganic filler (F) with resin composition (X). That is, the resin composition (X) may not contain the inorganic filler (F). Moreover, when resin composition (X) contains a hygroscopic agent (E), an inorganic filler (F), and a dispersing agent (G), there exists a tendency for the viscosity of resin composition (X) to become large, and resin composition ( X) may become difficult to be formed by the inkjet method. For this reason, resin composition (X) does not need to contain a hygroscopic agent (E), an inorganic filler (F), and a dispersing agent (G).

  Compound (z), which is at least one component selected from the group consisting of a compound having an isobornyl skeleton, a compound having a dicyclopentanyl skeleton, and a compound having a 3,3,5-trimethylcyclohexyl skeleton, is a resin composition ( It is difficult to increase the viscosity of X). For this reason, when the acrylic compound (A) contains the compound (z), the resin composition (X) can be reduced in viscosity even if the resin composition (X) does not contain a solvent. The inkjet method can be applied to the molding of X). Therefore, it is also preferable that the resin composition (X) does not contain a solvent. In this case, it is not necessary to dry the resin composition (X) and volatilize the solvent when producing a cured product from the resin composition (X). In addition, the storage stability of the resin composition (X) can be improved and the generation of solvent-derived outgas can be suppressed. Moreover, when resin composition (X) contains a solvent, it is preferable that the ratio of the solvent with respect to resin composition (X) is 1.0 mass% or less. The proportion of the solvent is more preferably 0.5% by mass or less, further preferably 0.3% by mass or less, and particularly preferably 0.1% by mass or less. It is particularly preferable that the resin composition (X) does not contain a solvent or contains only a solvent that is inevitably mixed.

(4) Manufacturing method of ultraviolet curable resin composition for organic EL sealing The above-mentioned acrylic compound (A), a photoinitiator (B), and an acrylic compound (A) and a photoinitiator (if needed) The resin composition (X) can be prepared by mixing the components other than B).

(5) Properties of UV curable resin composition for sealing organic EL The viscosity of the resin composition (X) at 25 ° C. is preferably 50 mPa · s or less. In this case, the resin composition (X) can be better molded by the ink jet method. The viscosity at 25 ° C. of the resin composition (X) is more preferably 30 mPa · s or less, further preferably 25 mPa · s or less, particularly preferably 20 mPa · s or less, and 15 mPa · s or less. Is most preferable. The viscosity at 25 ° C. of the resin composition (X) is preferably 1 mPa · s or more, and more preferably 5 mPa · s or more.

  It is also preferable that the viscosity at 40 ° C. of the resin composition (X) is 50 mPa · s or less. In this case, even if the viscosity of the resin composition (X) at normal temperature is any value, the viscosity can be lowered by slightly heating the resin composition (X). For this reason, if it heats, resin composition (X) can be shape | molded more favorably by the inkjet method. In addition, since the viscosity of the resin composition (X) can be reduced without greatly heating, the composition of the resin composition (X) hardly changes due to volatilization of the components in the resin composition (X). it can. The viscosity at 40 ° C. of the resin composition (X) is more preferably 30 mPa · s or less, further preferably 25 mPa · s or less, particularly preferably 20 mPa · s or less, and preferably 15 mPa · s or less. Is most preferable. The viscosity of the resin composition (X) at 25 ° C. is preferably 1 mPa · s or more, and more preferably 5 mPa · s or more.

  The viscosity of the resin composition (X) is measured using a rheometer at a shear rate of 100 s-1. As a rheometer, for example, Model No. DHR-2 manufactured by Anton Paar Japan, Inc. can be used.

  In the resin composition (X), the relative dielectric constant of the cured product when the frequency is 100 kHz is 3.0 or less. Thereby, when the organic electroluminescent light-emitting device 1 provided with the sealing material 5 formed from resin composition (X) is applied to the touch panel 100, it is easy to suppress malfunction of the touch sensor 10. FIG. In the resin composition (X), the relative dielectric constant of the cured product when the frequency is 100 kHz is more preferably 2.8 or less, and particularly preferably 2.7 or less.

  In this embodiment, the acrylic compound (A) is at least one component selected from the group consisting of a compound having an isobornyl skeleton, a compound having a dicyclopentanyl skeleton, and a compound having a 3,3,5-trimethylcyclohexyl skeleton. By containing the compound (z), the cured product of the resin composition (X) can have a low dielectric constant. Moreover, since the compound (z) hardly increases the viscosity of the acrylic compound (A), the resin composition (X) can be reduced in viscosity even if the resin composition (X) does not contain a solvent. However, if the relative dielectric constant of the cured product of the resin composition (X) can be 3.0 or less, the resin composition (X) is not limited to the acrylic compound (A) containing the compound (z). .

  The cured product of the resin composition (X) preferably has a glass transition temperature of 90 ° C. or higher. That is, it is preferable that the glass transition temperature of the hardened | cured material of resin composition (X) and the glass transition temperature of the sealing material 5 formed from resin composition (X) are 90 degreeC or more. In this case, the heat resistance of the sealing material 5 formed from the resin composition (X) can be improved. Therefore, when the organic EL light emitting device 1 is processed at a high temperature, it is easy to suppress deterioration of the sealing material 5. As for the glass transition temperature of the hardened | cured material of resin composition (X), 100 degreeC or more is more preferable. When the resin composition (X) contains the polyfunctional acrylic compound (A3), the molecular structure of the cured product of the resin composition (X) is easily three-dimensional, and the glass transition temperature of the cured product is easily increased.

  Specific examples are presented below. However, it is not limited only to these examples.

1. Preparation of Composition Resin compositions of Examples and Comparative Examples were prepared by mixing the components shown in the following table. The details of the components shown in the table are as follows.
SR295NS: Sartomer pentaerythritol tetraacrylate, viscosity at 25 ° C. 350 mPa · s. Glass transition temperature 103 ° C.
SR351S: Trimethylolpropane triacrylate manufactured by Sartomer, viscosity of 106 mPa · s at 25 ° C.
SR506NS: Sartomer isobornyl acrylate, viscosity at 25 ° C. 8 mPa · s, glass transition temperature 97 ° C.
SR423NS: Sartomer isobornyl methacrylate, viscosity 11 mPa · s at 25 ° C., glass transition temperature 110 ° C.
FA513AS: Hitachi Chemical dicyclopentanyl acrylate, viscosity at 25 ° C. 13 mPa · s, glass transition temperature 120 ° C.
CD535: Sartomer dicyclopentanyl methacrylate, viscosity at 25 ° C. 17 mPa · s, glass transition temperature 91 ° C.
CD420: Sartomer 3,3,5-trimethylcyclohexyl acrylate, viscosity at 25 ° C. 6 mPa · s, glass transition temperature 29 °.
CD421: Sartomer 3,3,5-trimethylcyclohexyl methacrylate, viscosity at 25 ° C. 6 mPa · s, glass transition temperature 145 ° C.
TBCHA: 4-t-butylcyclohexyl acrylate manufactured by KJ Chemical, viscosity 7 mPa · s at 25 ° C., glass transition temperature 77 ° C.
SR833S: Sartomer dicyclopentanyl dimethacrylate, viscosity at 25 ° C. 110 mPa · s, glass transition temperature 214 ° C.
PEGDMA: polyethylene glycol 200 dimethacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd., viscosity at 25 ° C .: 14 mPa · s, glass transition temperature: 41 ° C.
PEGDA: Polyethylene glycol 200 diacrylate, manufactured by Osaka Organic Chemical Co., Ltd., viscosity 17 mPa · s at 25 ° C., glass transition temperature 41 ° C.
Cyclomer M100: 3,4-epoxycyclohexylmethyl methacrylate, manufactured by Daicel, viscosity of 9 mPa · s at 25 ° C.
B1000: 1,2-polybutadiene homopolymer, manufactured by Nippon Soda Co., Ltd., viscosity 2000 mPa · s at 25 ° C.
FOLDI E101: 2- (4,4-dimethylpentan-2-yl) -5,7,7-trimethyloctanoic acid 2,3-epoxypropyl, manufactured by Nissan Chemical Co., Ltd., viscosity at 25 ° C. 40 mPa · s.
Celoxide 8010: (3,3 ′, 4,4′-diepoxy) bicyclohexyl, manufactured by Daicel, viscosity of 80 mPa · s at 25 ° C.
OXT221: 3-ethyl-3-{[(3-ethyloxetane-3-yl) methoxy] methyl} oxetane, manufactured by Toagosei Co., Ltd., viscosity at 25 ° C. 10 mPa ·. s.
184: 1-hydroxy-cyclohexyl-phenyl-ketone, manufactured by BASF, product name Irgacure 184
TPO: 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, manufactured by BASF, product name Irgacure TPO.
· DTS-200: Midori Kagaku, No. _{DTS-200, C 6 H 5} -S-C 6 H 4 -S + (C 6 H 5) 2 · B (C 6 F 5) 4.

2. Evaluation Test The following evaluation tests were conducted on the examples and comparative examples. The results are shown in the table.

(1) Viscosity The viscosity of the resin composition was measured using a rheometer (manufactured by Anton Paar Japan, model number DHR-2) under conditions of a temperature of 25 ° C. and a shear rate of 1000 s ⁻¹ .

(2) Glass transition temperature of cured product A resin composition was applied to produce a coating film, and this coating film was about 100 mW / cm using an LED-UV irradiator (peak wavelength 365 nm) manufactured by Panasonic Electric Works Co., Ltd. Photocuring was performed by irradiating with ultraviolet rays for 15 seconds under the condition of cm ² to prepare a film having a thickness of 100 μm.

  The glass transition temperature of the film obtained above was measured using a viscoelastic spectrometer “DMS6100” manufactured by Seiko Instruments Inc. At this time, dynamic viscoelasticity measurement (DMA) is performed with a tensile module at a frequency of 10 Hz, and the temperature at which tan δ is maximized when the temperature is raised from room temperature to 200 ° C. under a temperature rising rate of 5 ° C./min is the glass transition It was temperature.

(3) Inkjet resin The resin composition is put into a cartridge of an inkjet printer (“MH2420” manufactured by Ricoh Co., Ltd.), and after confirming that the resin composition in the cartridge can be discharged from the nozzle in the inkjet printer, the resin from the nozzle The test pattern was continuously printed by discharging the composition. As a result, “A” indicates that the resin composition can be discharged for 1 hour and the discharge operation is stable, and “B” indicates that the resin composition can be discharged for 1 hour but the discharge operation becomes intermittently unstable. The case where the nozzle was clogged 1 hour after the start of discharge and the resin composition could not be discharged was evaluated as “C”.

(4) Relative permittivity A coating film of a resin composition having a thickness of 10 μm was produced on an aluminum substrate having dimensions of 80 mm × 40 mm × 1 mmt. This coating film was irradiated with ultraviolet rays for 15 seconds under the condition of 100 mW / cm ² to cure the coating film. Using an LCR meter (manufactured by Agilent, “E4980A”) and a jig (16034 test fixture), the relative dielectric constant of the cured coating film was measured by an electrode contact method at a frequency of 100 kHz.

DESCRIPTION OF SYMBOLS 1 Organic EL light-emitting device 4 Organic EL element 5 Sealing material 10 Touch sensor 100 Touch panel

Claims (8)

An acrylic compound (A) and a photopolymerization initiator (B),
The relative dielectric constant of the cured product when the frequency is 100 kHz is 3.0 or less,
An ultraviolet curable resin composition for sealing an organic EL element, which is molded by an inkjet method. The acrylic compound (A) is a compound that is at least one component selected from the group consisting of a compound having an isobornyl skeleton, a compound having a dicyclopentanyl skeleton, and a compound having a 3,3,5-trimethylcyclohexyl skeleton ( z),
The ultraviolet curable resin composition for sealing an organic EL device according to claim 1. The acrylic compound (A) includes a monofunctional (meth) acrylic compound (A1) having only one (meth) acryloyl group in one molecule,
The ratio of the monofunctional (meth) acrylic compound (A1) to the total amount of the acrylic compound (A) is 50% by mass or more.
The ultraviolet curable resin composition for organic EL element sealing of Claim 1 or 2. The acrylic compound (A) includes a monofunctional methacrylate (a1) having only one methacryloyl group in one molecule,
The ratio of the monofunctional methacrylate (a1) to the total amount of the acrylic compound (A) is 25% by mass or more and 60% by mass or less.
The ultraviolet curable resin composition for organic EL element sealing as described in any one of Claims 1-3. The viscosity at 25 ° C. is 50 mP · s or less,
The ultraviolet curable resin composition for organic EL element sealing as described in any one of Claims 1-4. An organic EL light emitting device comprising an organic EL element and a sealing material covering the organic EL element,
The ultraviolet curable resin composition for sealing an organic EL element according to any one of claims 1 to 5 is molded by an ink jet method, and ultraviolet rays are then applied to the ultraviolet curable resin composition for sealing an organic EL element. Including producing the sealing material by irradiation and curing;
Manufacturing method of organic EL light-emitting device. An organic EL element, and a sealing material covering the organic EL element,
The sealing material is a cured product of the ultraviolet curable resin composition for sealing an organic EL element according to any one of claims 1 to 5.
Organic EL light emitting device. The organic EL light-emitting device according to claim 7 and a touch sensor.
Touch panel.