JP5827853B2 - Composition and cured product thereof - Google Patents

Description

  The present invention relates to a resin composition and a cured product thereof. More specifically, for electronic device applications such as organic electroluminescence devices, light-emitting diode devices (LED devices), and displays that require a sealing material having a high refractive index and excellent in low moisture permeability. The present invention relates to a resin composition and a cured product thereof preferably used, a sealant containing the resin composition, and an organic electroluminescence device, an LED device, and a display containing the cured product of the resin composition.

  Currently, various electronic devices such as organic electroluminescence devices, light emitting diode devices (LED devices), liquid crystal display devices, and displays such as touch panels are widely used. In these electronic devices, in order to prevent moisture from entering inside the device and causing deterioration of electronic elements, short circuit of electric circuits, corrosion of electrodes, etc. Electronic elements, electric circuits, and the like are sealed with materials (sealing material, sealing material). Among these electronic devices, in particular, in an organic electroluminescence device, since an organic electroluminescence element is fragile with respect to moisture, use of a sealing material or a sealing material with particularly low moisture permeability is required.

20-80 parts by weight of an epoxy compound having an aliphatic cyclic skeleton and 80-20 parts by weight of an epoxy compound having an aromatic ring as a sealant for forming a sealing material for an organic electroluminescence element A resin composition containing a cationic polymerization initiator has been proposed (see Patent Document 1). Specifically, compounds having an epoxy group at both ends are disclosed as an epoxy compound having an aliphatic cyclic skeleton and an epoxy compound having an aromatic ring. However, the cured product of the resin composition containing the above compound showed a moisture permeability of 55 g / m ² · 24 h or more under the conditions of 85 ° C. and 85% RH, and could not be said to have a sufficiently low moisture permeability.

In addition, as an adhesive for an element package such as an organic electroluminescence device, a resin composition containing (A) an epoxy compound, (B) a novolak resin, (C) a photocationic polymerization initiator, and (D) a filler is proposed. (See Patent Document 2). However, in order to obtain sufficient low moisture permeability, filler blending into the resin composition is essential, and the moisture permeability of the cured product of the resin composition without blending the filler is 60 ° C. and 90% RH. Under the conditions, it was 60 g / m ² · 24 h, and it did not have a sufficiently low moisture permeability.

  On the other hand, in the above-mentioned electronic device, a member having a high refractive index (high refractive index member) is often used, such as an electrode or a passivation film in an organic electroluminescence device. For this reason, in addition to the above-mentioned low moisture permeability, the encapsulant used in these electronic devices has a high refractive index member even when it is disposed so as to be in contact with the high refractive index member. In order to suppress the reflection of light generated at the interface, it is required to have a high refractive index.

  For example, as a curable resin composition for producing a resin having low water absorption and high refractive index, 100 to 5% by weight of a vinyl oligomer having a specific structure containing a sulfur atom, and copolymerizable with the vinyl oligomer are possible. A curable resin composition composed of 0 to 95% by weight of a compound is known (see Patent Document 3).

JP 2007-46035 A JP 2010-24364 A JP-A-8-183816

  However, although the hardened | cured material of the curable resin composition disclosed by patent document 3 showed comparatively low hygroscopicity, it did not have sufficient low moisture permeability. In particular, it was difficult for the cured product to satisfy the low moisture permeability required for a sealing material for an organic electroluminescence device. Thus, the present condition has not yet obtained the material which has a high refractive index and has low moisture permeability, and can be preferably used especially as a sealing material for an organic electroluminescence device.

Accordingly, an object of the present invention is to provide a resin composition (curable resin composition) that forms a cured product (resin cured product) having a high refractive index and excellent in low moisture permeability.
Another object of the present invention is to provide a cured product having a high refractive index and excellent in low moisture permeability.
Furthermore, the other object of this invention is to provide the sealing agent for forming the sealing material which has a high refractive index and was excellent in low moisture permeability.
Still another object of the present invention is to provide an organic electroluminescence device, an LED device, and a display in which an electronic element in an electronic device is sealed with the cured product, and an adverse effect due to moisture (humidity) hardly occurs. .

  As a result of intensive studies to solve the above problems, the present inventors have two or more reactive functional groups and one or more cyclic skeletons in one molecule, and at least one of the reactive functional groups is the above. A cured product of a resin composition comprising a compound bonded to a cyclic skeleton via a sulfur atom, a compound having one reactive functional group and two or more cyclic skeletons in one molecule, and a polymerization initiator, The present invention was completed by finding that it has a high refractive index and exhibits sufficiently low moisture permeability.

  That is, the present invention is a compound having two or more reactive functional groups and one or more cyclic skeletons in one molecule, wherein at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom. A resin composition comprising (A), a compound (B) having one reactive functional group and two or more cyclic skeletons in one molecule, and a polymerization initiator (C) is provided. To do.

  Furthermore, the said resin composition whose cyclic skeleton of the said compound (A) is an aromatic cyclic skeleton is provided.

（式（１）中、Ｒ^aは、それぞれ独立に、反応性官能基を示す。Ｒ¹は、それぞれ独立に、ハロゲン原子、アルキル基、ハロアルキル基、アリール基、保護基で保護されていてもよいヒドロキシル基、保護基で保護されていてもよいヒドロキシアルキル基、保護基で保護されていてもよいアミノ基、保護基で保護されていてもよいカルボキシル基、保護基で保護されていてもよいスルホ基、ニトロ基、シアノ基、又は保護基で保護されていてもよいアシル基を示す。Ｒ²は単結合又は連結基を示す。ｍは、それぞれ独立に、０〜４の整数を示す。ｎは、０〜１０の整数を示す。） Furthermore, the said resin (A) provides the said resin composition which is a compound represented by following formula (1).

(In Formula (1), each R ^a independently represents a reactive functional group. Each R ¹ may be independently protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A good hydroxyl group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, and optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group which may be protected with a protecting group, R ² represents a single bond or a linking group, and m independently represents an integer of 0 to 4. n represents an integer of 0 to 10.)

  Furthermore, the said resin composition whose cyclic skeleton of the said compound (B) is an aromatic cyclic skeleton is provided.

（式（２）中、Ｒ^bは反応性官能基を示す。Ｒ³は、それぞれ独立に、ハロゲン原子、アルキル基、ハロアルキル基、アリール基、保護基で保護されていてもよいヒドロキシル基、保護基で保護されていてもよいヒドロキシアルキル基、保護基で保護されていてもよいアミノ基、保護基で保護されていてもよいカルボキシル基、保護基で保護されていてもよいスルホ基、ニトロ基、シアノ基、又は保護基で保護されていてもよいアシル基を示す。Ｒ⁴は単結合又は連結基を示す。ｐは０〜４の整数を示す。ｑは０〜５の整数を示す。） Furthermore, the said resin composition whose said compound (B) is a compound represented by following formula (2) is provided.

(In formula (2), R ^b represents a reactive functional group. R ³ independently represents a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a hydroxyl group optionally protected with a protecting group, or a protected group. A hydroxyalkyl group optionally protected with a group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, a sulfo group optionally protected with a protecting group, a nitro group , A cyano group, or an acyl group which may be protected with a protecting group, R ⁴ represents a single bond or a linking group, p represents an integer of 0 to 4, and q represents an integer of 0 to 5. )

  Furthermore, the said resin composition is content of 1-1000 weight part with respect to 100 weight part of said compound (A).

  Furthermore, the said resin composition containing an inorganic filler (D) is provided.

  Furthermore, the said resin composition containing a silane coupling agent (E) is provided.

  Furthermore, it provides the resin composition, wherein the polymerization initiator (C) is a light or thermal cationic polymerization initiator or a light or thermal radical polymerization initiator.

  Moreover, this invention provides the hardened | cured material formed by hardening | curing the said resin composition.

  Moreover, this invention provides the sealing agent characterized by including the said resin composition.

  Moreover, this invention provides the organic electroluminescent apparatus containing the said hardened | cured material.

  Moreover, this invention provides the LED device containing the said hardened | cured material.

  Moreover, this invention provides the display containing the said hardened | cured material.

  Since the resin composition of the present invention has the above-described configuration, a cured product having a high refractive index and excellent in low moisture permeability can be obtained by curing. For this reason, the resin composition of this invention can be preferably used as sealing agent in electronic devices, such as an organic electroluminescent apparatus, an LED apparatus, and a display. An electronic device obtained by encapsulating an electronic element or the like using the resin composition (encapsulant) of the present invention has an excellent durability because adverse effects due to the ingress of moisture into the device are minimized. Have. Furthermore, the electronic device has a high refractive index of the cured product (encapsulant) of the resin composition of the present invention, for example, the light generated at the interface between the encapsulant and the high refractive index member. It has high quality such that reflection is suppressed.

<Resin composition>
The resin composition of the present invention has two or more reactive functional groups and one or more cyclic skeletons in one molecule, and at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom. A composition (resin) containing at least the compound (A), a compound (B) having one reactive functional group (b) and two or more cyclic skeletons in one molecule, and a polymerization initiator (C) Composition).

[Compound (A)]
As described above, the compound (A) constituting the resin composition of the present invention has two or more (two or more) reactive functional groups ("reactive functional group (a)" in one molecule (inside the molecule). At least one cyclic skeleton (sometimes referred to as “cyclic skeleton (a)”), and at least one of the reactive functional groups (a) is a sulfur atom ( It has a structure bonded to the cyclic skeleton (a) through S).

  Specific examples of the reactive functional group (a) include a cationic polymerizable group (cation polymerizable functional group) such as an epoxy group, an oxetanyl group, and a vinyl ether group, a vinyl group, and a (meth) acryloyl group. And a radically polymerizable group (radical polymerizable functional group). In addition, the said vinyl group may have cationic polymerizability. Especially, as said reactive functional group (a), a vinyl group, an epoxy group, and a (meth) acryloyl group are preferable.

  The number of reactive functional groups (a) in one molecule of compound (A) is not particularly limited as long as it is 2 or more, but is preferably 2 to 30, more preferably 2 to 10, and still more preferably. 2 to 6, particularly preferably 2 or 3. The plurality of reactive functional groups (a) in the compound (A) may be the same or different.

  Although it does not specifically limit as cyclic skeleton (a) which a compound (A) has, For example, an alicyclic cyclic skeleton and an aromatic cyclic skeleton are mentioned. More specifically, examples of the cyclic skeleton (a) include monocyclic or condensed polycyclic aromatic rings such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, and fluorene ring; cyclopentane ring, cyclohexane ring, deca Examples thereof include monocyclic or polycyclic aliphatic rings such as hydronaphthalene ring, norbornane ring and adamantane ring. Among these, as the cyclic skeleton (a) of the compound (A), an aromatic cyclic skeleton (aromatic ring) is preferable, and a benzene ring, a naphthalene ring, or a fluorene ring is particularly preferable. In the present specification, the number of polycyclic ring skeletons in which N rings (N represents an integer of 2 or more) is condensed is N. In addition, in the cyclic skeleton (a) in the compound (A), a cyclic skeleton corresponding to the reactive functional group (a) such as an epoxy group or an oxetanyl group (that is, a cyclic skeleton having radical polymerizability or cationic polymerizability) It shall not be included.

  The number of the cyclic skeleton (a) that the compound (A) has (the number of the cyclic skeleton (a) in one molecule of the compound (A)) may be one or more, and is not particularly limited. The number is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 5. In addition, when the compound (A) has two or more cyclic skeletons (a), the plurality of cyclic skeletons (a) may be the same or different.

  As described above, the compound (A) is a compound having a structure in which at least one of the reactive functional groups (a) is bonded to the cyclic structure (a) via a sulfur atom. That is, the compound (A) has two or more reactive functional groups (a), one or more cyclic skeletons (a), and one or more sulfur atoms in the molecule (in one molecule), and , A structure in which at least one of the reactive functional groups (a) is bonded to a cyclic skeleton (a) (more specifically, for example, a carbon atom constituting an alicyclic ring or an aromatic ring) via a sulfur atom. Is a compound having at least

  The number of sulfur atoms in the compound (A) may be one or more, and is not particularly limited, but is preferably 3 to 20, more preferably 3 to 15, in terms of increasing the refractive index of the cured product. More preferably, it is 3-10.

The form of the sulfur atom contained in the compound (A) is not particularly limited. Specifically, the compound (A) includes, for example, a thiol group (—SH), a thioether bond (—S—), a sulfo group (—SO ₃ H), a thioxo group (═S), a sulfino group (—SO ₂ ). H), an isothiocyanate group (—NCS), a p-toluenesulfonyl group, a benzenesulfonyl group, a thienyl group, and other functional groups. Among these, the compound (A) preferably has at least a thioether bond. That is, the compound (A) preferably has at least a structure in which the reactive functional group (a) and the cyclic structure (a) are linked by a thioether bond.

  Although the molecular weight of a compound (A) is not specifically limited, 100-1 million are preferable, More preferably, it is 200-100000, More preferably, it is 250-10000. By controlling the molecular weight of the compound (A) within the above range, a uniform resin composition tends to be easily obtained efficiently.

  Although the refractive index with respect to the light (sodium D line | wire) of wavelength 589nm in 25 degreeC of a compound (A) is not specifically limited, 1.5500-1.9000 are preferable, More preferably, it is 1.6000-1.8500, More preferably Is 1.6500 to 1.8500. In addition, the refractive index of a compound (A) can be measured by the method based on JISK0062, for example.

  More specifically, the compound (A) has two or more cationic polymerizable functional groups and one or more aromatic rings in one molecule, and at least one of the cationic polymerizable functional groups is sulfur. Compound (A-1) bonded to an aromatic ring (carbon atom constituting the aromatic ring) via an atom; two or more radically polymerizable functional groups and one or more aromatic rings in one molecule And a compound (A-2) in which at least one of the radical polymerizable functional groups is bonded to an aromatic ring (carbon atom constituting the aromatic ring) via a sulfur atom; two or more cations in one molecule A compound having a polymerizable functional group and one or more aliphatic rings, wherein at least one of the cationic polymerizable functional groups is bonded to an aliphatic ring (a carbon atom constituting the aliphatic ring) via a sulfur atom ( A-3); two or more radically polymerizable functional groups and one in one molecule And a compound (A-4) having at least one of the above-mentioned aliphatic rings and having at least one of the above radical polymerizable functional groups bonded to an aliphatic ring (carbon atom constituting the aliphatic ring) via a sulfur atom. It is done.

Especially, as a compound (A), the compound represented by following formula (1) is preferable at the point which raises the refractive index of hardened | cured material at a higher level, and reduces moisture permeability.

R ^a in the formula (1) (two R ^a) are each independently a (may be the same or may be different), showing a reactive functional group (reactive functional group (a)). In particular, Ra is preferably ^a vinyl group, an epoxy group, a glycidyl group, an oxetanyl group, a vinyl ether group, or a (meth) acryloyl group, and more preferably a vinyl group, an epoxy group, or a (meth) acryloyl group.

R ¹ in the above formula (1) (a plurality of R ¹ shown in the formula (1)) may be independently (may be the same or different), a halogen atom, an alkyl group, a haloalkyl group, An aryl group, a hydroxyl group optionally protected with a protecting group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group that may be protected with a protecting group. In addition, when m is an integer of 2-4, 2-4 R < ¹ > couple | bonded with the same aromatic ring may respectively be the same, and may differ. When m is an integer of 2 to 4, 2 to 4 R ¹ bonded to the same aromatic ring are bonded to each other to form a 4-membered ring or more together with carbon atoms constituting the aromatic ring. May be.

Examples of the halogen atom in R ¹ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group in R ¹ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, hexyl group, heptyl group, octyl group, and nonyl group. And a C _1-10 alkyl group such as a decyl group (preferably a C _1-5 alkyl group). Examples of the haloalkyl group include C _1-10 haloalkyl groups (preferably C _1-5 haloalkyl groups) such as a chloromethyl group, a trifluoromethyl group, a trifluoroethyl group, and a pentafluoroethyl group. Examples of the aryl group for R ¹ include a phenyl group and a naphthyl group. The aromatic ring of the aryl group includes, for example, a halogen atom such as a fluorine atom, a C _1-4 alkyl group such as a methyl group, a C _1-5 haloalkyl group such as a trifluoromethyl group, a hydroxyl group, and a methoxy group. A C _1-4 alkoxy group, an amino group, a dialkylamino group, a carboxyl group, an alkoxycarbonyl group such as a methoxycarbonyl group, and a substituent such as an acyl group such as a nitro group, a cyano group, and an acetyl group may be included.

Examples of the hydroxyalkyl group, e.g., C _1-10 at least one C _1-10 hydroxyalkyl group substituted with a hydroxyl group (preferably a C _1-5 hydroxyalkyl hydrogen atom of the alkyl group such as hydroxymethyl group Group). Examples of the protecting group for hydroxyl group and hydroxyalkyl group in R ¹ include protecting groups commonly used in the field of organic synthesis, such as alkyl groups (for example, C _1-4 alkyl such as methyl group and t-butyl group). Alkenyl group (eg, allyl group); cycloalkyl group (eg, cyclohexyl group); aryl group (eg, 2,4-dinitrophenyl group); aralkyl group (eg, benzyl group); A substituted methyl group (eg, methoxymethyl group, methylthiomethyl group, benzyloxymethyl group, t-butoxymethyl group, 2-methoxyethoxymethyl group, etc.), substituted ethyl group (eg, 1-ethoxyethyl group, etc.), tetrahydropyrani Group, tetrahydrofuranyl group, 1-hydroxyalkyl group (for example, 1-hydroxyethyl group ) Hydroxyl groups and acetal or hemiacetal group capable of forming groups such as; acyl group (e.g., formyl group, acetyl group, a propionyl group, a butyryl group, an isobutyryl group, C _1-6 aliphatic acyl group such as pivaloyl group; An acetoacetyl group; an aromatic acyl group such as a benzoyl group; an alkoxycarbonyl group (eg, a C _1-4 alkoxy-carbonyl group such as a methoxycarbonyl group); an aralkyloxycarbonyl group; a substituted or unsubstituted carbamoyl group; Silyl group (for example, trimethylsilyl group); when two or more hydroxyl groups or hydroxymethyl groups are present in the molecule, a divalent hydrocarbon group (for example, methylene group, ethylidene group, isopropyl group) which may have a substituent. Ridene group, cyclopentylidene group, cyclohexylidene group, benzyl And the like).

Examples of the protecting group for the amino group in R ¹ include a protecting group commonly used in the field of organic synthesis, for example, an alkyl group, an aralkyl group, an acyl group, an alkoxycarbonyl group and the like exemplified as the protecting group for the hydroxyl group.

Examples of the protecting group for carboxyl group and sulfo group for R ¹ include protecting groups commonly used in the field of organic synthesis, for example, alkoxy groups (for example, C _1-6 alkoxy such as methoxy group, ethoxy group, butoxy group). Group), cycloalkyloxy group, aryloxy group, aralkyloxy group, trialkylsilyloxy group, optionally substituted amino group, hydrazino group, alkoxycarbonylhydrazino group, aralkylcarbonylhydrazino group, etc. Is mentioned.

Examples of the acyl group in R ¹ include C _1-6 aliphatic acyl groups such as formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, and pivaloyl group, and aromatic acyl groups such as acetoacetyl group and benzoyl group. Group and the like. As the protecting group for the acyl group, a protecting group commonly used in the field of organic synthesis can be used. Examples of the form in which the acyl group is protected include acetal (including hemiacetal).

When two or more of the above R ¹ are bonded per aromatic ring (that is, when m is 2 to 4), these are bonded to each other together with the carbon atoms constituting the aromatic ring in formula (1) Examples of the 4-membered or higher ring to be formed include alicyclic such as a 5-membered alicyclic carbocycle, a 6-membered alicyclic carbocycle, a condensed ring of 2 or more alicyclic carbocycles (monocyclic) Carbon ring; lactone rings such as 5-membered lactone ring and 6-membered lactone ring are exemplified.

R ² in the above formula (1) represents a single bond or a linking group (a divalent group having one or more atoms). Examples of the linking group include a divalent hydrocarbon group, a carbonyl group, an ether group (ether bond), a thioether group (thioether bond), an ester group (ester bond), a carbonate group (carbonate bond), and an amide group (amide). Bond), or a group in which a plurality of these are linked. The linking group may have a substituent such as a hydroxyl group or a carboxyl group, and examples of such a linking group include a divalent hydrocarbon group having one or more hydroxyl groups.

  As said bivalent hydrocarbon group, a C1-C18 linear or branched alkylene group, a bivalent alicyclic hydrocarbon group, etc. are mentioned. Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group. Examples of the divalent alicyclic hydrocarbon group include 1,2-cyclopentylene group, 1,3-cyclopentylene group, cyclopentylidene group, 1,2-cyclohexylene group, 1,3-cyclohexene group. And divalent cycloalkylene groups (including cycloalkylidene groups) such as a silylene group, a 1,4-cyclohexylene group, and a cyclohexylidene group.

A plurality of m (the number of substituents R ¹ on each aromatic ring) in the above formula (1) are each independently (may be the same or different), and an integer of 0 to 4 Indicates. N (the number of repeating structural units in parentheses to which n is attached) represents an integer of 0 to 10.

Specific examples of the compound (A) (the compound represented by (1) above) in the resin composition of the present invention include, for example, compounds represented by the following formula.

上記式中のＲは、それぞれ独立に、水素原子又はメチル基を示す。

R in said formula shows a hydrogen atom or a methyl group each independently.

  In addition, in the resin composition of this invention, a compound (A) can be used individually by 1 type or in combination of 2 or more types.

  The content (blending amount) of the compound (A) in the resin composition (100% by weight) of the present invention is not particularly limited, but is preferably 5 to 95% by weight, more preferably 10 to 90% by weight, still more preferably. 20 to 85% by weight. By controlling the content of the compound (A) within the above range, the coating properties of the resin composition are improved, and the effect of improving the refractive index tends to be easily obtained.

It does not specifically limit as a manufacturing method of a compound (A), A well-known thru | or usual method is applicable. For example, a compound having two or more mercapto groups and one or more cyclic structures in one molecule (for example, 4,4′-thiobisbenzenethiol) and a halide of vinyl halide, acrylic acid or methacrylic acid , Epihalohydrin and the like can be produced by a method of reacting in the presence of a base. For the compound in which R ^a in formula (1) is a vinyl group, for example, a compound having two or more mercapto groups and one or more cyclic structures in one molecule is reacted with dihaloethane, It can also be produced by a dehydrohalogenation method; a method in which an epihalohydrin is added to a compound having two or more mercapto groups and one or more cyclic structures in one molecule, followed by a ring closure reaction.

[Compound (B)]
The compound (B) constituting the resin composition of the present invention has one reactive functional group (sometimes referred to as “reactive functional group (b)”) and two or more cyclic skeletons (“ A compound having a cyclic skeleton (sometimes referred to as “b”).

  As a reactive functional group (b) which a compound (B) has, the reactive functional group illustrated as said reactive functional group (a) is mentioned, for example. Specifically, when the reactive functional group (a) is a cationic polymerizable functional group, the reactive functional group (b) is a cationic polymerizable functional group, and the reactive functional group (a) is radically polymerizable. In the case of a functional group, the reactive functional group (b) is preferably a radical polymerizable functional group. As a combination of the reactive functional group (a) and the reactive functional group (b), both are preferably epoxy groups, and particularly preferably both are glycidyl groups.

  Although it does not specifically limit as cyclic skeleton (b) which a compound (B) has, For example, an alicyclic cyclic skeleton, an aromatic cyclic skeleton, etc. are mentioned. More specifically, examples of the cyclic skeleton (b) include monocyclic or condensed polycyclic aromatic rings such as a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring; a cyclopentane ring, a cyclohexane ring, Examples thereof include monocyclic or polycyclic aliphatic rings such as a decahydronaphthalene ring, a norbornane ring, and an adamantane ring. Especially, as a cyclic skeleton (b) which a compound (B) has, an aromatic cyclic skeleton (especially benzene ring) or a cyclohexane ring is preferable. In addition, in the cyclic skeleton (b) in the compound (B), a cyclic skeleton corresponding to the reactive functional group (b) such as an epoxy group or an oxetanyl group (that is, a cyclic skeleton having radical polymerizability or cationic polymerizability) It shall not be included.

  The number of the cyclic skeleton (b) of the compound (B) (the number of the cyclic skeleton (b) in one molecule of the compound (B)) may be two or more, and is not particularly limited. The number is preferably 2-4. In addition, two or more cyclic skeletons (b) in the compound (B) may be the same or different.

  Although the molecular weight of a compound (B) is not specifically limited, 50-1000 are preferable, More preferably, it is 50-500. By controlling the molecular weight of the compound (B) within the above range, the moisture permeability of the cured product tends to be efficiently reduced.

  Although the refractive index with respect to the light (sodium D line | wire) of wavelength 589nm in 25 degreeC of a compound (B) is not specifically limited, 1.4000-1.9000 are preferable, More preferably, it is 1.5000-1.8500, More preferably Is 1.5500-1.8500. In addition, the refractive index of a compound (B) can be measured by the method based on JISK0062, for example.

  Specifically, as the compound (B), for example, a compound (B-1) having two or more aromatic rings and one cationic polymerizable functional group; two or more aromatic rings and one radical polymerizable Compound (B-2) having functional group, compound (B-3) having two or more aliphatic rings and one cationic polymerizable functional group; two or more aliphatic rings and one radical polymerizable functional group (B-4) etc. which have these.

Examples of the compound (B-1) having two or more aromatic rings and one cationic polymerizable functional group include benzene rings and epoxy groups such as phenylphenol glycidyl ether, diphenylphenol glycidyl ether, and triphenylphenol glycidyl ether. An alkyl-substituted phenylphenol glycidyl ether such as methylphenylphenol glycidyl ether, ethylphenylphenol glycidyl ether, propylphenylphenol glycidyl ether, n-butylphenylphenol glycidyl ether, t-butylphenylphenol glycidyl ether (for example, C _{1) -9} alkyl-substituted phenylphenol glycidyl ethers); phenylbenzyl glycidyl ethers such as phenylbenzyl glycidyl ethers Compound: Vinyl ether compound having two benzene rings such as phenylphenol vinyl ether, (phenylphenoxy) methyl vinyl ether, (2-phenylphenoxy) ethyl vinyl ether; phenylphenol oxetane, (phenylphenoxy) methyl oxetane, (2-phenylphenoxy) ) Oxetane compounds having two benzene rings such as ethyl oxetane, and halides thereof. Examples of the C _1-9 alkyl substituent include a methyl group, an ethyl group, a propyl group, and a t-butyl group.

Examples of the compound (B-2) having two or more aromatic rings and one radical polymerizable functional group include phenylphenol (meth) acrylate, (phenylphenoxy) methyl (meth) acrylate, and (2-phenylphenoxy). ) A compound having two benzene rings and a (meth) acryloyl group such as ethyl (meth) acrylate; and a halide thereof, or a C _1-9 alkyl substituent thereof. _{Examples of the} C _1-9 alkyl substituent in the C _1-9 alkyl substituent include a methyl group, an ethyl group, a propyl group, and a t-butyl group. Examples of the halogen in the halide include F, Cl, Br and the like.

Examples of the compound (B-3) having two or more aliphatic rings and one cationically polymerizable functional group include C _5-20 cycloalkyl glycidyl ether compounds such as dicyclohexyl glycidyl ether and tricyclohexyl glycidyl ether; dicyclohexyl oxetanyl. C _5-20 cycloalkyl oxetanyl ether compounds such as ether and tricyclohexyl oxetanyl ether; C _5-20 cycloalkyl vinyl ether compounds such as dicyclohexyl vinyl ether and tricyclohexyl vinyl ether, and the like.

Examples of the compound (B-4) having two or more aliphatic rings and one radical polymerizable functional group include C _5-20 cycloalkyl (meta) such as dicyclohexyl (meth) acrylate and tricyclohexyl (meth) acrylate. ) Acrylate compounds and the like.

As the compound (B), in particular, from the viewpoint of increasing the refractive index of the cured product, the compound (B-1) having two or more aromatic rings and one cationic polymerizable functional group, two or more aromatics A compound (B-2) having a ring and one radical polymerizable functional group is preferred, and more specifically, a compound represented by the following formula (2) having a biphenyl structure is preferred. By using a compound represented by the following formula (2) as the compound (B), moisture permeability can be efficiently reduced while maintaining a high refractive index of the cured product.

In the above formula (2), R ^b represents a reactive functional group (reactive functional group (b)). Examples of R ^b include those exemplified as the reactive functional group (b). In particular, R ^b is preferably a vinyl group, an epoxy group, an oxetanyl group, a vinyl ether group, or a (meth) acryloyl group.

In the above formula (2), R ³ (several R ^{3 s} ) are each independently (may be the same or different) and are protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A hydroxyl group that may be protected, a hydroxyalkyl group that may be protected with a protecting group, an amino group that may be protected with a protecting group, a carboxyl group that may be protected with a protecting group, and a protective group that is protected with And an optionally substituted sulfo group, nitro group, cyano group, or acyl group which may be protected with a protecting group. When p and q are integers of 2 or more, two or more R ³ bonded to the same aromatic ring may be the same or different. When p and q are integers of 2 or more, two or more R ³ bonded to the same aromatic ring are bonded to each other to form a 4-membered or higher ring with the carbon atoms constituting the aromatic ring. May be.

Specific examples of R ³ in the above formula (2) are the same as R ¹ in the above formula (1).

In the above formula (2), R ⁴ represents a single bond or a linking group (a divalent group having one or more atoms). Examples of R ⁴ include the same as R ² in the above formula (1).

P in the formula (2) (the number of substituents R ³ on the left aromatic ring of the formula (2)) represents an integer of 0 to 4. q (the number of substituents R ³ on the right aromatic ring of the formula (2)) represents an integer of 0 to 5.

  As the compound (B) (compound represented by the above formula (2)) in the resin composition of the present invention, particularly preferable compounds include, for example, phenylphenol glycidyl ether, diphenylphenol glycidyl ether, triphenylphenol glycidyl ether, methyl Phenylphenol glycidyl ether, ethylphenylphenol glycidyl ether, propylphenylphenol glycidyl ether, n-butylphenylphenol glycidyl ether, t-butylphenylphenol glycidyl ether, phenylbenzyl glycidyl ether, phenylphenol vinyl ether, (phenylphenoxy) methyl vinyl ether, ( 2-phenylphenoxy) ethyl vinyl ether, phenylphenol oxetane, (phenyl) Enoxy) methyl oxetane, (2-phenylphenoxy) ethyl oxetane, phenylphenol (meth) acrylate, (phenylphenoxy) methyl (meth) acrylate, (2-phenylphenoxy) ethyl (meth) acrylate, 4-vinylbiphenyl, 3- Examples thereof include vinyl biphenyl and 2-vinyl biphenyl.

  In addition, in the resin composition of this invention, a compound (B) can be used individually by 1 type or in combination of 2 or more types.

  Although content (blending amount) of a compound (B) is not specifically limited, 1-1000 weight part is preferable with respect to 100 weight part of compound (A), More preferably, it is 10-250 weight part, More preferably, it is 20 -150 parts by weight. When the content of the compound (B) is controlled within the above range, the free volume of the cured product is packed more effectively, and the moisture permeability of the cured product can be further reduced.

  In general, a cured product (resin cured product) obtained by curing a crosslinkable polyfunctional group-containing resin material has inherent moisture permeability due to the material skeleton. In addition, a cured product is usually prepared by blending a polymerization initiator with a resin having two or more reactive functional groups, and crosslinking and curing by activating the polymerization initiator with heat or light. It is thought that it permeates mainly from the free volume formed when the material crosslinks.

  The resin composition of this invention is obtained by hardening the resin composition of this invention by including the above-mentioned compound (A), a compound (B), and the below-mentioned polymerization initiator (C) as an essential component. The cured product (resin cured product) has a high refractive index and exhibits excellent low moisture permeability. Thus, the resin composition of the present invention exhibits such excellent low moisture permeability, in particular, by copolymerizing the monofunctional compound (B) having a specific structure with the compound (A). While the crosslink density of the cured product is reduced, it is presumed that the structural unit derived from the compound (B) in the cured product exhibits the effect of packing the free volume of the cured product. For this reason, the hardened | cured material of the resin composition of this invention shows very low moisture permeability compared with the hardened | cured material obtained by hardening | curing resin which consists only of a compound (A), for example.

The free volume packing structure in the cured product of the resin composition of the present invention is schematically shown below. The ellipse with A represents the monomer unit derived from the compound (A) (in the case of bifunctionality), the ellipse with B represents the monomer unit derived from the compound (B), and the wavy lines on both sides represent the polymer main chain. In the cured product of the resin composition of the present invention, it is presumed that the monomer units derived from the compound (B) are filled in the gaps between the monomer units derived from the compound (A), and the free volume is packed.

  In particular, as described above, since both the compound (A) and the compound (B) have a cyclic skeleton, the above-described packing becomes more effective, and the free volume in the cured product is more easily reduced. The cured product exhibits extremely low moisture permeability.

  The total amount of the compound (A) and the compound (B) in the resin composition of the present invention is not particularly limited, but from the viewpoints of the refractive index and moisture permeability of the cured product, all polymerizable compounds (reactions) contained in the resin composition 50 to 100% by weight, more preferably 70 to 100% by weight, and still more preferably 80 to 100% by weight with respect to 100% by weight of the total amount of compounds having a functional functional group (polymerizable functional group).

[Polymerization initiator (C)]
It does not specifically limit as a polymerization initiator (C) which comprises the resin composition of this invention, A well-known and usual polymerization initiator can be used. Specifically, for example, as the polymerization initiator (C), a photocationic polymerization initiator or a thermal cationic polymerization initiator (light or thermal cationic polymerization initiator), a photoradical polymerization initiator or a thermal radical polymerization initiator ( A light or thermal radical polymerization initiator) can be preferably used. In addition, a polymerization initiator (C) can be used individually by 1 type or in combination of 2 or more types.

(Photocationic polymerization initiator)
Examples of the cationic photopolymerization initiator include Cyracure UVI-6970, Cyracure UVI-6974, Cyracure UVI-6990, Cyracure UVI-950 (trade name, manufactured by Union Carbide, USA), Irgacure 250, Irgacure 261, Irgacure. H.264 (trade name, manufactured by Ciba Specialty Chemicals), SP-150, SP-151, SP-170, Optmer SP-171 (above, product name, manufactured by ADEKA), CG-24-61 (Ciba)・ Specialty Chemicals Co., Ltd., trade name), DAICAT II (Daicel Chemical Industries, trade name), UVAC1590, UVAC1591 (Daicel Cytec Co., trade name), CI-2064, CI-2539, CI -2624, CI-24 1, CI-2734, CI-2855, CI-2823, CI-2758, CIT-1682 (above, Nippon Soda Co., Ltd., product name), PI-2074 (manufactured by Rhodia, trade name, pentafluorophenyl borate) Toluylcumyl iodonium salt), FFC509 (product of 3M, trade name), BBI-102, BBI-101, BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, NAT-103, NDS -103 (Midori Chemical Co., Ltd., trade name), CD-1010, CD-1011, CD-1012 (US, Sartomer, trade name), CPI-100P, CPI-101A (San Apro Co., Ltd.) Diazonium salts, iodonium salts, sulfonium salts, phosphoniu represented by commercial products such as (trade name) And selenium salts, oxonium salts, ammonium salts, and the like.

(Thermal cationic polymerization initiator)
Examples of the thermal cationic polymerization initiator include Sun-Aid SI-45, Same as left SI-47, Same as left SI-60, Same as left SI-60L, Same as left SI-80L, Same as left SI-80L, Same as left SI-100, Same as left SI-100L SI-110L, left SI-145, left SI-150, left SI-160, left SI-110L, left SI-180L, left SI-B3, left SI-B4 (Sanshin Chemical Industry Co., Ltd.) Product, trade name), TA-1, same as left TA-2 (above, San Apro Co., Ltd. product, trade name) CI-2921, CI-2920, CI-2946, CI-3128, CI-2624, CI-2638, CI-2064 (Nippon Soda Co., Ltd., product name), PP-33, CP-66, CP-77 (ADEKA product, product name), FC-509, F -520 (3M's products, trade name) diazonium salt typified by, iodonium salt, sulfonium salt, phosphonium salt, selenium salts, oxonium salts, ammonium salts, and the like can be used. Furthermore, a chelate compound of a metal such as aluminum or titanium and a acetoacetate or diketone compound and a silanol such as triphenylsilanol, or a chelate compound of a metal such as aluminum or titanium and acetoacetate or diketone and bisphenol S The compound with phenols, such as these, may be sufficient.

  Although it does not specifically limit as content (blending amount) of a photocationic polymerization initiator or a thermal cationic polymerization initiator, It has all the polymerizable compounds (reactive functional group (polymerizable functional group) contained in a resin composition. The total amount of the compound) is preferably from 0.01 to 15 parts by weight, more preferably from 0.01 to 12 parts by weight, still more preferably from 0.05 to 10 parts by weight, particularly preferably from 0.1 to 100 parts by weight. 5 parts by weight. By using a light or thermal cationic polymerizable initiator within the above range, a cured product excellent in low moisture permeability can be obtained.

(Curing accelerator)
The resin composition of the present invention may contain a curing accelerator. The said hardening accelerator is a compound which has a function which accelerates | stimulates a cure rate, when the polymeric compound in the resin composition of this invention hardens | cures with light or a thermal cationic polymerization initiator. As the curing accelerator, known and commonly used curing accelerators can be used. For example, 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), and salts thereof (for example, phenol salts, Octylate, p-toluenesulfonate, formate, tetraphenylborate salt); 1,5-diazabicyclo [4.3.0] nonene-5 (DBN), and salts thereof (eg, phosphonium salts, sulfonium salts) Quaternary ammonium salts, iodonium salts); tertiary amines such as benzyldimethylamine, 2,4,6-tris (dimethylaminomethyl) phenol, N, N-dimethylcyclohexylamine; 2-ethyl-4-methylimidazole, Imidazoles such as 1-cyanoethyl-2-ethyl-4-methylimidazole; phosphate ester, triphenylphos Phosphines such as fin; tetraphenylphosphonium tetra (p- tolyl) phosphonium compounds such as borate, tin octylate, organic metal salts such as zinc octylate; metal chelate and the like. In addition, a hardening accelerator can be used individually by 1 type or in combination of 2 or more types.

  Moreover, as said hardening accelerator, U-CAT SA506, U-CAT SA102, U-CAT5003, U-CAT18X, 12XD (development product) (above, the San Apro Co., Ltd. product), TPP-K, Commercial products such as TPP-MK (made by Hokuko Chemical Co., Ltd.) and PX-4ET (made by Nippon Chemical Industry Co., Ltd.) can also be used.

  The content (blending amount) of the curing accelerator is not particularly limited, but is 0.05 with respect to 100 parts by weight of the total amount of the polymerizable compound (total amount of the compound having a reactive functional group) contained in the resin composition. -5 parts by weight is preferable, more preferably 0.1-3 parts by weight, still more preferably 0.2-3 parts by weight, and particularly preferably 0.25-2.5 parts by weight. If the content of the curing accelerator is less than 0.05 parts by weight, the curing acceleration effect may be insufficient. On the other hand, when content of a hardening accelerator exceeds 5 weight part, hardened | cured material may color and a hue may deteriorate.

(Photo radical polymerization initiator)
Examples of the photo radical polymerization initiator include benzophenone, acetophenone benzyl, benzyl dimethyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxyacetophenone, dimethoxyphenylacetophenone, diethoxyacetophenone, 2-hydroxy-2. -Methylpropiophenone, diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, diphenyl disulfite, methyl orthobenzoylbenzoate, ethyl 4-dimethylaminobenzoate (Kayacure EPA, manufactured by Nippon Kayaku Co., Ltd.) 2,4-diethylthioxanthone (Nippon Kayaku Co., Ltd. Kayacure DETX), 2-methyl-1- [4- (methyl) phenyl] -2-morpholinopropa 2-amino-2-benzoyl-1-phenylalkane compounds such as 2-methylamino-2- (4-morpholino) benzoyl-1-phenylpropane, tetra-1 (Ciba-Geigy Co., Ltd. Irgacure 907 etc.), tetra Aminobenzene derivatives such as (t-butylperoxycarbonyl) benzophenone, benzyl, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 4,4-bisdiethylaminobenzophenone, 2,2′-bis ( Imidazole compounds such as 2-chlorophenyl) -4,5,4 ′, 5′-tetraphenyl-1,2′-biimidazole (B-CIM, etc. manufactured by Hodogaya Chemical Co., Ltd.), 2,6-bis ( Halomethylated triazine compounds such as trichloromethyl) -4- (4-methoxynaphthalen-1-yl) -1,3,5-triazine, 2 -Halomethyloxadiazole compounds such as trichloromethyl-5- (2-benzofuran-2-yl-ethenyl) -1,3,4-oxadiazole. These radical photopolymerization initiators can be used alone or in combination of two or more. Moreover, a photosensitizer can be added to the resin composition of this invention as needed. As the radical photopolymerization initiator, the compound represented by the formula (1) may have absorption with respect to light having a wavelength of 400 nm or less, and therefore, for example, diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide. In addition, those activated by light having a wavelength of around 400 nm are preferable.

(Thermal radical polymerization initiator)
Examples of the thermal radical polymerization initiator include organic peroxides. Examples of the organic peroxides that can be used include dialkyl peroxides, acyl peroxides, hydroperoxides, ketone peroxides, and peroxyesters. Specific examples of the organic peroxide include benzoyl peroxide, t-butylperoxy-2-ethylhexanate, 2,5-dimethyl-2,5-di (2-ethylhexanoyl) peroxyhexane, t-butyl. Peroxybenzoate, t-butyl peroxide, cumene hydroperoxide, dicumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-dibutylperoxyhexane, 2,4-dichlorobenzoyl peroxide, Di-t-butylperoxy-diisopropylbenzene, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, methyl ethyl ketone peroxide, 1,1,3,3-tetramethylbutylperoxy -2-ethylhexanoate and the like.

  Furthermore, together with the thermal radical polymerization initiator, naphthenic acid such as cobalt naphthenate, manganese naphthenate, zinc naphthenate, cobalt octenoate or the like, or metal salts such as cobalt octenoate, manganese, lead, zinc, vanadium, etc. Can do. Similarly, tertiary amines such as dimethylaniline can be used.

  One of the above-mentioned light or thermal radical polymerization initiators may be used alone, or two or more thereof may be used in combination at any ratio. The amount to be used is preferably 0.1 to 5 parts by weight, more preferably 0.8 parts per 100 parts by weight of the total amount of polymerizable compounds (total amount of compounds having reactive functional groups) contained in the resin composition. 5 to 4 parts by weight.

[Inorganic filler (D)]
The resin composition of the present invention may further contain an inorganic filler (D). The inorganic filler (D) is not particularly limited, but silica, alumina, mica, synthetic mica, talc, calcium oxide, calcium carbonate, zirconium oxide, titanium oxide, barium titanate, kaolin, bentonite, diatomaceous earth, boron nitride, nitriding. Examples include aluminum, silicon carbide, zinc oxide, cerium oxide, cesium oxide, magnesium oxide, glass beads, glass fiber, graphite, calcium hydroxide, magnesium hydroxide, aluminum hydroxide, and cellulose. In addition, an inorganic filler (D) can be used individually by 1 type or in combination of 2 or more types.

These inorganic fillers (D) can be produced, for example, by a known method such as a flame hydrolysis method, a flame pyrolysis method, or a plasma method described in International Publication No. 96/31572. As the preferred inorganic filler (D), nano colloidal inorganic dispersion sols can be used, and commercially available products include silica sol manufactured by BAYER, SnO ₂ sol manufactured by Goldschmidt, and MERCK. Commercially available products such as TiO ₂ sols from the company, SiO ₂ , ZrO ₂ , Al ₂ O ₃ and Sb ₂ O ₃ sols from Nissan Chemicals or Aerosil dispersions from DEGUSSA are available.

  The inorganic filler (D) can change these viscosity behaviors by surface modification. The surface modification of the particles can be performed using a known surface modifier. As such a surface modifier, for example, a compound capable of interacting with a functional group present on the surface of the inorganic filler (D) such as a covalent bond or complex formation, or a compound capable of interacting with a polymer matrix. Can be used. Examples of such surface modifiers include carboxyl groups, (primary, secondary, and tertiary) amino groups, quaternary ammonium groups, carbonyl groups, glycidyl groups, vinyl groups, ) A compound having a functional group such as acryloxy group or mercapto group can be used. Such a surface modifier is usually a liquid under normal temperature and pressure conditions, and has a low molecular weight of 15 or less (more preferably 10 or less, more preferably 8 or less) in the molecule. Surface modifiers composed of organic compounds are preferred. The molecular weight of the low molecular weight organic compound is not particularly limited, but is preferably 500 or less, more preferably 350 or less, and still more preferably 200 or less.

Examples of the surface modifier include formic acid, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, acrylic acid, methacrylic acid, crotonic acid, citric acid, adipic acid, succinic acid, glutaric acid, oxalic acid and maleic acid. acid and saturated or unsaturated mono- and polycarboxylic acids having 1 to 12 carbon atoms such as fumaric acid (preferably monocarboxylic acids); and C ₁ -C ₄ alkyl esters of these esters (preferably such as methyl methacrylate Amides; β-dicarbonyl compounds such as acetylacetone, 2,4-hexanedione, 3,5-heptanedione, acetoacetic acid and C ₁ -C ₄ alkylacetoacetic acids. Moreover, although it does not specifically limit, a well-known and usual silane coupling agent can also be used as a surface modifier.

  Although the particle size of an inorganic filler (D) is not specifically limited, 0.01 nm-1 micrometer are preferable, More preferably, it is 0.01 nm-100 nm, More preferably, it is 0.01 nm-50 nm.

  The content (blending amount) of the inorganic filler (D) is not particularly limited, but is 1 to 2000 with respect to 100 parts by weight of the total amount (total content) of the compound (A) and the compound (B) in the resin composition. A weight part is preferable, More preferably, it is 10-1000 weight part. Moreover, the content of the inorganic filler (D) with respect to the total amount (100% by weight) of the resin composition is not particularly limited, but is preferably 5 to 70% by weight, and more preferably 5 to 50% by weight.

[Silane coupling agent (E)]
The resin composition of the present invention may further contain a silane coupling agent (E) in order to improve adhesion to an adherend such as a substrate. It does not specifically limit as a silane coupling agent (E), A well-known and usual silane coupling agent can be used. As the silane coupling agent (E), specifically, for example, tetramethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, Vinyltris (methoxyethoxysilane), phenyltrimethoxysilane, diphenyldimethoxysilane, vinyltriacetoxysilane, γ- (meth) acryloxypropyltriethoxysilane, γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) Acryloxypropylmethyldimethoxysilane, γ- (meth) acryloxypropylmethyldiethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-g Sidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, p-styryltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, N -(Β-aminoethyl) -γ-aminopropylmethyldimethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyldiethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane N- (β-aminoethyl) -γ-aminopropyltriethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, 3-mercaptopropyl Trimethoxysilane, 3-mercapto It can be selected from those that are relatively stable in an aqueous solution such as propyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, bis (triethoxysilylpropyl) tetrasulfide, and 3-isocyanatopropyltriethoxysilane. it can.

  The content (blending amount) of the silane coupling agent (E) is not particularly limited, but is 0 with respect to 100 parts by weight of the total amount (total content) of the compound (A) and the compound (B) in the resin composition. 0.1 to 20 parts by weight is preferable, 0.3 to 8 parts by weight is more preferable, and 0.5 to 5 parts by weight is still more preferable. If the content of the silane coupling agent (E) is less than 0.1 parts by weight, the resin crosslinking effect by the silane coupling agent (E) is poor, so a dense film cannot be obtained, and the metal base material is obtained. The coupling effect is poor, the adhesion is inferior, and desirable alkali resistance and rust preventive power may be difficult to obtain. If the content of the silane coupling agent (E) exceeds 20 parts by weight, degradation of various performances such as water resistance and alkali resistance due to hydrolysis will be remarkable, causing problems in film-forming properties, and disadvantageous in terms of economy. There is a case.

[Other additives]
If necessary, the resin composition of the present invention may be, for example, a polymerization inhibitor, an antioxidant, a light stabilizer, a plasticizer, a leveling agent, an antifoaming agent, a pigment, an organic solvent, an ultraviolet absorber, an ion adsorbent, Conventional additives such as pigments, phosphors, and release agents may be contained.

<Method for producing resin composition>
The resin composition of the present invention comprises the above component (A), component (B), component (C), and, if necessary, component (D), component (E), and other components (additives, etc.). It can be obtained by mixing uniformly. In obtaining the resin composition of the present invention, each component is made as uniform as possible by using generally known mixing equipment such as a revolving type stirring deaerator, a homogenizer, a planetary mixer, a three-roll mill, a bead mill and the like. It is desirable to perform stirring, dissolution, mixing, dispersion, and the like. Each component may be mixed simultaneously or sequentially.

<Hardened product>
A cured product (resin cured product) can be obtained by curing the resin composition of the present invention with light or heat. When the resin composition of the present invention is cured by light, for example, the resin composition can be cured by irradiating light of 1000 mJ / cm ² or more with a mercury lamp or the like. When the resin composition of the present invention is cured by heat, for example, the resin composition is heated at a temperature of 50 to 200 ° C. (more preferably 50 to 190 ° C., more preferably 50 to 150 ° C.) and 10 It can be cured by heating for ~ 600 minutes (more preferably for 10 to 480 minutes, even more preferably for 15 to 240 minutes). When the heating temperature (curing temperature) and time (curing time) are lower than the lower limit of the above range, the resin composition may be insufficiently cured, which may be undesirable. On the other hand, when the curing temperature and the curing time are higher than the upper limit value in the above range, decomposition of the resin component may occur, which is not preferable. The curing conditions of the resin composition of the present invention depend on various conditions, but can be appropriately adjusted by shortening the curing time when the curing temperature is high and increasing the curing time when the curing temperature is low. . By curing the resin composition of the present invention, a cured product having a high refractive index and excellent low moisture permeability can be obtained.

Since the cured product obtained by curing the resin composition of the present invention has low moisture permeability, it is excellent in moisture resistance. The moisture permeability of the cured product can be calculated by measuring the moisture permeability of the cured product adjusted to a thickness of 100 μm in accordance with JIS L1099 and JIS Z0208 under the conditions of 60 ° C. and 90% RH. The cured product of the present invention is not particularly limited, moisture permeability was measured by the above ^{methods, 50g / m 2 · atm ·} day or less ^{(e.g., 0~50g / m 2 · atm ·} day) is preferably , more preferably 40g / m ² · atm · day or less ^{(e.g., 0~40g / m 2 · atm ·} day), more preferably 30g / m ² · atm · day or less (e.g., 0~30g / m ² · atm · day). Further, by blending the inorganic filler (D) with the resin composition of the present invention, the moisture permeability of the cured product is, for example, preferably 20 g / m ² · atm · day or less (for example, 0 to 20 g / m ² · atm · day), particularly preferably 15 g / m ² · atm · day or less (for example, 0 to 15 g / m ² · atm · day).

  Moreover, the refractive index with respect to the light (sodium D line | wire) of wavelength 589nm in 25 degreeC of the said hardened | cured material is although it does not specifically limit, 1.550-1.900 are preferable, More preferably, 1.600-1.850, Preferably it is 1.650-1.850. In addition, the refractive index of hardened | cured material can be measured by the method based on JISK7142, or the method using a prism coupler, for example.

<Sealant>
Since the cured product of the resin composition of the present invention has a high refractive index and is excellent in low moisture permeability, sealing in electronic devices such as organic electroluminescence devices, LED devices, displays (for example, touch panels, etc.) in particular. It can be preferably used as a sealant for forming a material. More specifically, the encapsulant containing the resin composition of the present invention as an essential component can be used as an encapsulant for electronic devices that require a particularly high refractive index and low moisture permeability encapsulant. In addition, as conditions at the time of hardening the said sealing agent, the conditions similar to at the time of obtaining the above-mentioned hardened | cured material are employable. Moreover, the resin composition of this invention can be used also as an adhesive agent and a sealing agent.

<Electronic devices such as organic electroluminescence devices, LED devices, displays>
By using the resin composition of the present invention as a sealing agent in an electronic device, an adverse effect due to moisture (humidity) is minimized, and an electron with high quality due to the high refractive index of the cured product is provided. A device (an electronic device including a cured product of the resin composition of the present invention) can be obtained. Examples of the electronic device include displays such as an organic electroluminescence device, a light emitting diode device (LED device), and a touch panel. In particular, when the resin composition of the present invention is used for an organic electroluminescence device that requires the use of a sealing material having a high refractive index and a low moisture permeability, the organic composition is more durable and has a higher quality. An electroluminescent device can be obtained.

  Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Production Example 1 [Production of bis [4- (2-chloroethyl) thiophenyl] sulfide]
To a 1 L 4-necked flask equipped with a condenser, a stirrer, and a thermometer, 4,4′-thiobisbenzenethiol (50.6 g, 202.1 mmol), tetrabutylammonium bromide [nBu ₄ NBr] (1.71 g) 5.30 mmol) and 1,2-dichloroethane (410.3 g, 4146 mmol) were added, and 30 wt% aqueous potassium hydroxide solution (87.3 g, 466.8 mmol) was added dropwise thereto at room temperature. After stirring the reaction solution for 2 hours, water was added, and a white solid was filtered off using a buch funnel. The filtered white solid was washed with water and dried under reduced pressure to obtain bis [4- (2-chloroethyl) thiophenyl] sulfide represented by the following formula as a white solid (74.9 g, yield: 99%). ).

Production Example 2 [Production of bis (4-vinylthiophenyl) sulfide (MPV)]
To a 1 L four-necked flask equipped with a condenser, a stirrer, and a thermometer, bis [4- (2-chloroethyl) thiophenyl] sulfide (100.1 g, 266.8 mmol) obtained in Production Example 1 and nBu ₄ NBr (4.51 g, 14.0 mmol) and n-heptane (239.5 g) were added, and a 50 wt% aqueous sodium hydroxide solution (107.0 g, 882.0 mmol) was added dropwise thereto at 85 ° C. After completion of the dropwise addition, the reaction solution was stirred for 5 hours, after which water was added and transferred to a separatory funnel for separation. Further, the organic layer was washed twice with water and dehydrated with anhydrous sodium sulfate, and then the solvent was distilled off to obtain a liquid crude product. After purification by silica gel column chromatography (hexane / ethyl acetate = 40/1), 1.0 mg / ml 2,6-di-tert-butylhydroxytoluene in hexane (11.0 g) was added, and the pressure was reduced. The resultant was dried to obtain bis (4-vinylthiophenyl) sulfide (MPV) represented by the following formula as a colorless transparent liquid (23.0 g, yield: 28%).
¹ H-NMR (500 MHz, CDCl ₃ ): δ 5.39-5.40 (m, 4H), 6.52 (dd, J = 16.4, 9.6 Hz, 2H), 7.27-7.30 (M, 8H)

¹Ｈ−ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ₃）：δ３．９６（ｔ，Ｊ＝５．０Ｈｚ，２Ｈ）、４．１７−４．２１（ｍ，３Ｈ）、６．４４（ｄｄ，Ｊ＝１４．１，６．５Ｈｚ，１Ｈ）、６．９８−７．０１（ｍ，１Ｈ）、７．０４−７．０７（ｍ，１Ｈ）、７．２８−７．４１（ｍ，６Ｈ）、７．５６−７．５７（ｍ，２Ｈ） Production Example 3 [Production of (2-phenylphenoxy) ethyl vinyl ether (OPP-EVE)]
A 2 L 4-neck flask equipped with a condenser, stirrer, and thermometer was charged with sodium hydride (55% in mineral oil) (15.4 g, 352.9 mmol) and DMSO (510.6 g). After cooling to ° C., a solution prepared by dissolving o-phenylphenol (50.6 g, 297.3 mmol) in DMSO (191.0 g) was added dropwise thereto. Thereafter, the solution was placed in a 60 ° C. oil bath, and a solution of 2-chloroethyl vinyl ether (38.2 g, 358.5 mmol) dissolved in DMSO (61.4 g) was added dropwise. The reaction solution was stirred for 6 hours, then cooled to 0 ° C., and then slowly quenched by dropwise addition of water, and transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated brine. Thereafter, the organic layer was separated and dehydrated with anhydrous sodium sulfate, and then the solvent was distilled off to obtain a liquid crude product. This was purified by silica gel column chromatography (hexane / ethyl acetate = 10/1), and 55.5 g (yield: 78%, purity) of (2-phenylphenoxy) ethyl vinyl ether represented by the following formula as a colorless transparent liquid. : 98%).

¹ H-NMR (500 MHz, CDCl ₃ ): δ 3.96 (t, J = 5.0 Hz, 2H), 4.17-4.21 (m, 3H), 6.44 (dd, J = 14.1) , 6.5 Hz, 1H), 6.98-7.01 (m, 1H), 7.04-7.07 (m, 1H), 7.28-7.41 (m, 6H), 7.56 -7.57 (m, 2H)

Example 1
60 parts by weight of MPV obtained in Production Example 2, 38 parts by weight of HRD-01 ((2-phenylphenoxy) ethyl acrylate, manufactured by Nippon Distilled Industries Co., Ltd.), and thermal radical initiator perocta O (manufactured by NOF Corporation) 2 parts by weight were charged into a self-revolving agitation deaerator (model AR-250, manufactured by Shinkey Co., Ltd.), stirred, dissolved, mixed, and dispersed to prepare a resin composition. The obtained resin composition was cast into a mold using a Teflon (registered trademark) spacer having a thickness of 100 μm, and cured by heating in a constant temperature air oven at 100 ° C. for 1 hour to prepare a cured product.

Examples 2-6
The same as Example 1 except that the compound (A), the compound (B), the polymerization initiator (C), the inorganic filler (D), and the silane coupling agent (E) were changed to the types and amounts shown in Table 1. Thus, a resin composition and a cured product were produced. In Example 5, MEK dispersion (NZD-4E61-EE0) of inorganic filler was added to and mixed with the mixed resin liquid of compound (A) and compound (B), and polymerization was started after MEK was distilled off with an evaporator. The resin composition was prepared by adding the agent (C) and cured in the same manner to produce a cured product.

Comparative Example 1
99 parts by weight of the MPV obtained in Production Example 2 and 1 part by weight of the thermal cation initiator Sun-Aid SI-B3 (manufactured by Sanshin Chemical Industry Co., Ltd.) are mixed into a self-revolving stirring deaerator (model AR-250, Co., Ltd.). The resin composition was prepared by stirring, dissolving, mixing, and dispersing. The obtained resin composition was cast into a mold using a Teflon (registered trademark) spacer having a thickness of 100 μm, and cured by heating in a constant temperature air oven at 100 ° C. for 1 hour to prepare a cured product.

Comparative Examples 2-6
A resin composition and a cured product were prepared in the same manner as in Comparative Example 1 except that the compound (A), the compound (B), and the polymerization initiator (C) were changed to the types and amounts shown in Table 1.

Example 7
60 parts by weight of MPV obtained in Production Example 2, 38 parts by weight of HRD-01 (manufactured by Nippon Distilling Industry Co., Ltd.), 1 part by weight of UV radical initiator H0991 (manufactured by Tokyo Chemical Industry Co., Ltd.), and UV radical initiator D3358 1 part by weight (manufactured by Tokyo Chemical Industry Co., Ltd.) is put into a self-revolving stirring deaerator (model AR-250, manufactured by Shinky Co., Ltd.), and the mixture is stirred, dissolved, mixed, and dispersed. Things were prepared. The obtained resin composition was cast into a mold using a Teflon (registered trademark) spacer having a thickness of 100 μm, irradiated with 5000 mJ / cm ² of light with a mercury lamp, and then heated in a constant temperature air oven at 100 ° C. It was cured by heating for a time to produce a cured product.

Examples 8-10
The compound (A), the compound (B), the polymerization initiator (C), and the photosensitizer (406317 (manufactured by Aldrich)) were changed to the types and amounts shown in Table 2 in the same manner as in Example 1. A resin composition and a cured product were prepared.

Comparative Example 7
Revolution of 98 parts by weight of MPV obtained in Production Example 2, 1 part by weight of UV radical initiator H0991 (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1 part by weight of UV radical initiator D3358 (manufactured by Tokyo Chemical Industry Co., Ltd.) The resin composition was prepared by charging the mixture into a stirring and degassing apparatus (model AR-250, manufactured by Shinkey Co., Ltd.), stirring, dissolving, mixing and dispersing. The obtained resin composition was cast into a mold using a Teflon (registered trademark) spacer having a thickness of 100 μm, irradiated with 5000 mJ / cm ² of light with a mercury lamp, and then heated in a constant temperature air oven at 100 ° C. It was cured by heating for a time to produce a cured product.

Comparative Examples 8-12
The compound (A), the compound (B), the polymerization initiator (C), and the photosensitizer (406317 (manufactured by Aldrich)) were the same as in Comparative Example 7 except that the types and amounts shown in Table 2 were changed. A resin composition and a cured product were prepared.

<Measurement of water vapor transmission rate>
The cured product having a thickness of 100 μm obtained in Examples and Comparative Examples was attached to a moisture permeable cup, and the water vapor permeability of the cured product was measured in accordance with JIS L1099 under the conditions of 60 ° C. and 90% RH. The results are shown in Tables 1 and 2.

<Measurement of refractive index>
About the 100 micrometer-thick cured material obtained by the Example and the comparative example, the refractive index (25 degreeC) with respect to the light of wavelength 589nm was measured using the Model 2010 prism coupler by a metricon company. The results are shown in Tables 1 and 2.

<Measurement of adhesion>
Using the resin compositions obtained in the examples (Examples 1 and 6), the glass-glass adhesion (tensile shear adhesion strength) was measured according to JIS K6850. The test piece was prepared by sandwiching the resin composition between two glasses and heating at 100 ° C. for 1 hour. The results are shown in Table 3.

The compounds used in Examples and Comparative Examples are as follows.
MPV: Bis (4-vinylthiophenyl) sulfide MPSMA (manufactured by Tokyo Chemical Industry Co., Ltd., B1662): Bis (4-methacryloylthiophenyl) sulfide OPP-EVE: (2-phenylphenoxy) ethyl vinyl ether HRD-01 (Japan) Distilled Industrial Co., Ltd.): (2-phenylphenoxy) ethyl acrylate S0095 (manufactured by Tokyo Chemical Industry Co., Ltd.): Styrene SI-B3 (manufactured by Sanshin Chemical Industry Co., Ltd.): 4-hydroxyphenylbenzylmethylsulfonium = Tetrakis (pentafluorophenyl) borate Perocta O (manufactured by NOF Corporation): t-butyl peroxy-2-ethylhexanoate NZD-4E61-EE0 (manufactured by Sumitomo Osaka Cement Co., Ltd.): Surface-modified nano zirconia MEK Dispersion (Surface modified nano zirconia 12.6w % Content)
A1597 (Tokyo Chemical Industry Co., Ltd.): 3- (trimethoxysilyl) propyl acrylate D3358 (Tokyo Chemical Industry Co., Ltd.): Diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide H0991 (Tokyo Chemical Industry) (Manufactured by Co., Ltd.): 2-hydroxy-2-methylpropiophenone CPI-101A (manufactured by San Apro Co., Ltd.): 4- (phenylthio) phenyldiphenylsulfonium = hexafluoroantimonate 406317 (manufactured by Aldrich): isopropyl-9H- Thioxanthen-9-one

Claims (15)

A compound (A) having two or more reactive functional groups and one or more cyclic skeletons in one molecule, wherein at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom; A compound (B) having one reactive functional group and two or more cyclic skeletons in the molecule, and a polymerization initiator (C);
The compound (A) is represented by the following formula (1)

(In Formula (1), each R ^a independently represents a reactive functional group. Each R ¹ may be independently protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A good hydroxyl group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, and optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group which may be protected with a protecting group, R ² represents a single bond or a linking group, and m independently represents an integer of 0 to 4. n represents an integer of 0 to 10.)
A compound represented by
The compound (B) is represented by the following formula (2 ′ )

(In the formula (2 ′ ), R ^b represents a reactive functional group. Each R ³ independently represents a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a hydroxyl group optionally protected by a protecting group, Hydroxyalkyl group which may be protected with a protecting group, amino group which may be protected with a protecting group, carboxyl group which may be protected with a protecting group, sulfo group which may be protected with a protecting group, nitro An acyl group which may be protected with a group, a cyano group, or a protecting group, R ⁴ represents a single bond or a linking group, p represents an integer of 0 to 4, and q represents an integer of 0 to 5. .)
A compound represented by
Moisture permeability of a cured product obtained by curing [moisture permeability calculated by measuring the moisture permeability of a cured product adjusted to a thickness of 100 μm according to JIS L1099 and JIS Z0208 under the conditions of 60 ° C. and 90% RH] Of 32 g / m ² · atm · day or less (excluding a composition for colloidal crystals containing 25 to 65% by weight of core-shell particles having a core part and a shell part).   The composition according to claim 1, wherein the content of the compound (B) is 1-1000 parts by weight with respect to 100 parts by weight of the compound (A).   Furthermore, the composition of Claim 1 or 2 containing an inorganic filler (D).   Furthermore, the composition of any one of Claims 1-3 containing a silane coupling agent (E).   The composition according to any one of claims 1 to 4, wherein the polymerization initiator (C) is a light or thermal cationic polymerization initiator or a light or thermal radical polymerization initiator.   Content of the said compound (A) in a composition (100 weight%) is 5-95 weight%, The composition of any one of Claims 1-5.   The total amount of the compound (A) and the compound (B) is 50 to 100% by weight with respect to 100% by weight of all polymerizable compounds contained in the composition. The composition as described.   Hardened | cured material formed by hardening | curing the composition of any one of Claims 1-7.   The sealing agent characterized by including the composition of any one of Claims 1-7.   The organic electroluminescent apparatus containing the hardened | cured material of Claim 8.   The LED device containing the hardened | cured material of Claim 8.   A display comprising the cured product according to claim 8. A compound (A) having two or more reactive functional groups and one or more cyclic skeletons in one molecule, wherein at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom; A compound (B) having one reactive functional group and two or more cyclic skeletons in the molecule, and a polymerization initiator (C);
The compound (A) is represented by the following formula (1)

(In Formula (1), each R ^a independently represents a reactive functional group. Each R ¹ may be independently protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A good hydroxyl group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, and optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group which may be protected with a protecting group, R ² represents a single bond or a linking group, and m independently represents an integer of 0 to 4. n represents an integer of 0 to 10.)
A compound represented by
The compound (B) is represented by the following formula (2)

(In formula (2), R ^b represents a reactive functional group. R ³ independently represents a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a hydroxyl group optionally protected with a protecting group, or a protected group. A hydroxyalkyl group optionally protected with a group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, a sulfo group optionally protected with a protecting group, a nitro group , A cyano group, or an acyl group which may be protected with a protecting group, R ⁴ represents a single bond or a linking group, p represents an integer of 0 to 4, and q represents an integer of 0 to 5. )
The organic electroluminescent apparatus containing the hardened | cured material formed by hardening | curing the composition which is a compound represented by these. A compound (A) having two or more reactive functional groups and one or more cyclic skeletons in one molecule, wherein at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom; A compound (B) having one reactive functional group and two or more cyclic skeletons in the molecule, and a polymerization initiator (C);
The compound (A) is represented by the following formula (1)

(In Formula (1), each R ^a independently represents a reactive functional group. Each R ¹ may be independently protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A good hydroxyl group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, and optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group which may be protected with a protecting group, R ² represents a single bond or a linking group, and m independently represents an integer of 0 to 4. n represents an integer of 0 to 10.)
A compound represented by
The compound (B) is represented by the following formula (2)

(In formula (2), R ^b represents a reactive functional group. R ³ independently represents a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a hydroxyl group optionally protected with a protecting group, or a protected group. A hydroxyalkyl group optionally protected with a group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, a sulfo group optionally protected with a protecting group, a nitro group , A cyano group, or an acyl group which may be protected with a protecting group, R ⁴ represents a single bond or a linking group, p represents an integer of 0 to 4, and q represents an integer of 0 to 5. )
LED device containing the hardened | cured material formed by hardening | curing the composition which is a compound represented by these. A compound (A) having two or more reactive functional groups and one or more cyclic skeletons in one molecule, wherein at least one of the reactive functional groups is bonded to the cyclic skeleton via a sulfur atom; A compound (B) having one reactive functional group and two or more cyclic skeletons in the molecule, and a polymerization initiator (C);
The compound (A) is represented by the following formula (1)

(In Formula (1), each R ^a independently represents a reactive functional group. Each R ¹ may be independently protected with a halogen atom, an alkyl group, a haloalkyl group, an aryl group, or a protecting group. A good hydroxyl group, a hydroxyalkyl group optionally protected with a protecting group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, and optionally protected with a protecting group A sulfo group, a nitro group, a cyano group, or an acyl group which may be protected with a protecting group, R ² represents a single bond or a linking group, and m independently represents an integer of 0 to 4. n represents an integer of 0 to 10.)
A compound represented by
The compound (B) is represented by the following formula (2)

(In formula (2), R ^b represents a reactive functional group. R ³ independently represents a halogen atom, an alkyl group, a haloalkyl group, an aryl group, a hydroxyl group optionally protected with a protecting group, or a protected group. A hydroxyalkyl group optionally protected with a group, an amino group optionally protected with a protecting group, a carboxyl group optionally protected with a protecting group, a sulfo group optionally protected with a protecting group, a nitro group , A cyano group, or an acyl group which may be protected with a protecting group, R ⁴ represents a single bond or a linking group, p represents an integer of 0 to 4, and q represents an integer of 0 to 5. )
The display containing the hardened | cured material formed by hardening | curing the composition which is a compound represented by as a sealing material of an electronic device.