JP2014189668A - Resin, resin composition, optical member using these, and former for the optical member - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a resin and a resin composition which satisfy suitable hardenability, heat resistance, and a thermal expansion coefficient required in use of an optical member by increasing the variety of resin materials, and to provide an optical member using the resin and the resin composition, and a former for the optical member.SOLUTION: A resin includes a compound represented by the following formula (1). (wherein Rrepresents a linkage group; and Ato Aeach independently represents a hydrogen atom or a substituent and at least one of them is a substituent represented by the following formula (2)) (wherein Rrepresents a hydrogen atom or a substituent; Arepresents a hydroxyl group, an alkoxy group, a thiol group, a thioalkoxy group, or an amino group; and * represents a binding hand)

Description

  The present invention relates to a resin, a resin composition, an optical member using these, and a forming agent thereof.

  Semiconductor light-emitting devices are expected as next-generation light sources to replace incandescent lamps and fluorescent lamps, and technological development for improving output and the like is being actively promoted in Japan and overseas. The range of application is wide-ranging, and its use is expanding not only for indoor lighting but also as a backlight for liquid crystal display devices. On the other hand, the semiconductor light emitting device itself is still under development, and it cannot be said that the material has been sufficiently researched. The same applies to transparent optical materials such as encapsulants and lens forming agents, and currently epoxy or silicone resins are the mainstream, but development studies and material searches for further performance improvements are required.

  On the other hand, there are fields where high-quality transparent optical materials are required, such as wafer level lens modules. The lens, coating film, and the like are also required to be a material having good processability and optically suitable properties. There is an example in which an alicyclic hydrocarbon acrylic material that can be used as a transparent optical material including the semiconductor light emitting device has been proposed (see Patent Documents 1 to 3).

International Publication No. 2006/051803 Pamphlet JP 2010-159410 A JP 2012-46726 A

  In view of the above technical background, the present invention proposes a resin that is enriched in material types by proposing different ones from the conventional ones and that satisfies the preferable curability, heat resistance, and coefficient of thermal expansion required for optical member applications. It aims at providing the resin composition, the optical member using these, and its formation agent.

  Based on the recognition of the above problems, the present inventors have searched for materials suitable for optical members in various substances and their blends. As a result, it was felt that the isocyanurate compound may satisfy the required characteristics. However, it has been found that not only using an isocyanurate compound but an acrylic compound having a specific polar group satisfies all of the above required properties at a high level. The present invention has been completed based on such findings.

（式中、Ｒ^１は連結基を表す。Ａ^１〜Ａ^３はそれぞれ独立に水素原子または置換基を表し、そのうち少なくとも一つは下記式（２）で表される置換基である。）

（式中、Ｒ^２は水素原子または置換基を表す。Ａ^４は水酸基、アルコキシ基、チオール基、チオアルコキシ基、アミノ基を表す。＊は結合手を表す。）
〔２〕式（１）において、Ａ^１〜Ａ^３のうち少なくとも２つが式（２）で表される置換基である〔１〕に記載の樹脂。
〔３〕式（１）において、Ａ^１〜Ａ^３のすべてが式（２）で表される置換基である〔１〕に記載の樹脂。
〔４〕式（１）において、Ｒ^１がエチレン基である〔１〕〜〔３〕のいずれか１項に記載の樹脂。
〔５〕式（２）において、Ｒ^２が水素原子またはメチル基である〔１〕〜〔４〕のいずれか１項に記載の樹脂。
〔６〕式（１）で表される化合物が、下記式（３−ａ）、（３−ｂ）、（３−ｃ）、（３−ｄ）、（３−ｅ）、または（３−ｆ）で表される化合物である〔１〕〜〔５〕のいずれか１項に記載の樹脂。

〔７〕硬化性を有する〔１〕〜〔６〕のいずれか１項に記載の樹脂。
〔８〕〔１〕〜〔７〕のいずれか１項に記載の樹脂とともに他の成分を含有させた樹脂組成物。
〔９〕〔１〕〜〔７〕のいずれか１項に記載の樹脂を含有してなる光学部材形成剤。
〔１０〕〔９〕に記載の光学部材形成剤を硬化してなる光学部材。
〔１１〕〔１０〕に記載の光学部材を具備する半導体発光装置。
〔１２〕下記式（１）で表される化合物。

（式中、Ｒ^１は連結基を表す。Ａ^１〜Ａ^３はそれぞれ独立に水素原子または置換基を表し、そのうち少なくとも一つは下記式（２）で表される置換基である。）

（式中、Ｒ^２は水素原子または置換基を表す。Ａ^４は水酸基、アルコキシ基、チオール基、チオアルコキシ基、アミノ基を表す。＊は結合手を表す。） That is, the present invention provides the following means for solving the above-mentioned problems.
[1] A resin containing a compound represented by the following formula (1).

(In the formula, R ¹ represents a linking group. A ^{1 to} A ³ each independently represents a hydrogen atom or a substituent, and at least one of them is a substituent represented by the following formula (2).)

(In the formula, R ² represents a hydrogen atom or a substituent. A ⁴ represents a hydroxyl group, an alkoxy group, a thiol group, a thioalkoxy group, or an amino group. * Represents a bond.)
[2] The resin according to [1], wherein in formula (1), at least two of A ^{1 to} A ³ are substituents represented by formula (2).
[3] The resin according to [1], wherein in formula (1), all of A ^{1 to} A ³ are substituents represented by formula (2).
[4] The resin according to any one of [1] to [3], wherein in formula (1), R ¹ is an ethylene group.
[5] The resin according to any one of [1] to [4], wherein in formula (2), R ² is a hydrogen atom or a methyl group.
[6] The compound represented by the formula (1) is represented by the following formula (3-a), (3-b), (3-c), (3-d), (3-e), or (3- The resin according to any one of [1] to [5], which is a compound represented by f).

[7] The resin according to any one of [1] to [6], which has curability.
[8] A resin composition containing other components together with the resin according to any one of [1] to [7].
[9] An optical member forming agent comprising the resin according to any one of [1] to [7].
[10] An optical member obtained by curing the optical member forming agent according to [9].
[11] A semiconductor light emitting device comprising the optical member according to [10].
[12] A compound represented by the following formula (1).

(In the formula, R ¹ represents a linking group. A ^{1 to} A ³ each independently represents a hydrogen atom or a substituent, and at least one of them is a substituent represented by the following formula (2).)

(In the formula, R ² represents a hydrogen atom or a substituent. A ⁴ represents a hydroxyl group, an alkoxy group, a thiol group, a thioalkoxy group, or an amino group. * Represents a bond.)

The resin of the present invention, the resin composition, the optical member using these, and the forming agent thereof are enriched by proposing different ones from the above-mentioned conventional resins, and suitable for optical member applications. Satisfactory curability, heat resistance and thermal expansion coefficient.
Moreover, the specific isocyanurate compound of the present invention is a novel compound, and has industrial utility including use as a material for forming the optical member.

It is sectional drawing which showed typically an example of the semiconductor light-emitting device of this invention. It is sectional drawing which showed typically another example of the semiconductor light-emitting device of this invention. It is a NMR spectrum figure of a compound (3-a).

  The resin of the present invention comprises as a constituent component a compound having an acryloyl group having a specific polar group at the α-position and an isocyanuric acid skeleton (hereinafter sometimes referred to as a specific isocyanurate compound). The reason why this resin exhibited suitable performance as a material for optical members is presumed as follows. The specific resin increases the electron density of the acryloyl group by introducing an electron donating group into the α-position of the acryloyl group. It is understood that this makes it easier to undergo one-electron oxidation under aerobic conditions, and the curability is improved by generating more radicals. Alternatively, oxygen is easily bonded directly to an acrylic group as an initiator, and as a result, it is considered that polymerization curability could be improved while taking advantage of the present compound having an isocyanuric acid skeleton. Hereinafter, preferred embodiments of the present invention will be described in detail.

[Compound represented by Formula (1)]
In the present invention, a specific isocyanurate compound represented by the following formula (1) is used.

・ R ¹
R ¹ represents a linking group. Divalent linking groups include alkylene groups (methylene group, ethylene group, propylene group, etc.), alkenylene groups (vinylene group, propylene group, etc.), arylene groups (phenylene group, naphthalenediyl group), heteroarylene groups (pyridinediyl group). Group, thiophenediyl group, etc.), imino group (—NR—) (imino group (H), methylimino group, ethylimino group, phenylimino group etc.), oxy group (—O—), thiol group (—S—), Phosphandiyl group (-PR-) (methylphosphandiyl group, ethylphosphandiyl group, phenylphosphandiyl group, etc.), silylene group (-SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), carbonyl Group, carbonyloxy group, thiocarbonyl group, thiocarbonyloxy group, or a combination thereof Can be listed. These linking groups may further have a substituent. R and R ′ represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms. Three R ¹ may be different from each other.

  Among these, an alkylene group that may intervene with a hetero linking group (Lh) (preferably having 1 to 12 carbon atoms, more preferably 1 to 6 and particularly preferably 1 to 3), interposing a hetero linking group is preferable. And alkenylene groups having 2 to 12 carbon atoms and more preferably 2 to 6 carbon atoms are preferred. The hetero linking group is preferably an imino group, an oxy group, a thiol group, a phosphandiyl group, a silylene group, a carbonyl group, a carbonyloxy group, a thiocarbonyl group, a thiocarbonyloxy group, or a combination thereof. The number of hetero-linking groups (Lh) is preferably 1 to 4, and more preferably 1 or 2, in the chain. The alkylene group and alkenylene group may be cyclic or chain-like, and when chained, they may be linear or branched.

The linking group is preferably represented by the following formula (1a).

*-(L ¹ -X) _{n 1} -L ² -** 1a

L ¹ and L ² are each independently an alkylene group (preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, particularly preferably 1 to 3 carbon atoms) or an alkenylene group (preferably having 2 to 12 carbon atoms; 6 is more preferable). X is the hetero linking group (Lh). n1 is an integer of 0-4. ** is a bond on the ^Ax side. When there are a plurality of L ¹ or X, they may be different from each other. The alkylene group and alkenylene group may further have an optional postscript substituent T. The alkylene group and alkenylene group may be cyclic or chain-like, and when chained, they may be linear or branched.

· ^A 1 ~A ³
A ^{1 to} A ³ each independently represent a hydrogen atom or a substituent, and at least one of them is a substituent represented by the following formula (2).

・ R ²
R ² represents a hydrogen atom or a substituent. As the said substituent, a C1-C12 is preferable, 1-6 are more preferable, 1-3 are especially preferable, and an alkenyl group (C2-C12 is preferable and 2-6 are more preferable). Or an aryl group (preferably having 6 to 22 carbon atoms, more preferably 6 to 14 carbon atoms). The alkyl group, alkenyl group, and aryl group may further have an arbitrary substituent. The alkylene group and alkenyl group may be cyclic or chain-like, and when chained, they may be linear or branched. The alkylene group and alkenylene group may further have an arbitrary substituent. The alkylene group and alkenylene group may be cyclic or chain-like, and when chained, they may be linear or branched.
Among them, R ² is preferably a hydrogen atom or the alkyl group, and more preferably a hydrogen atom or a methyl group.

・ A ⁴
A ⁴ represents a hydroxyl group, an alkoxy group (preferably having 1 to 6 carbon atoms, particularly preferably 1 to 3), a thiol group, a thioalkoxy group (preferably having 1 to 6 carbon atoms, particularly preferably 1 to 3), an amino group ( A carbon number of 0 to 6 is preferable, and 0 to 3 is particularly preferable. Of these, a hydroxyl group or an alkoxy group is preferable, and a hydroxyl group is more preferable. When A ⁴ is present in a plurality of molecules, they may be the same as or different from each other.

  * Represents a bond.

In the formula ^(1), it is preferable that at least two of the A 1 to A ³ is a substituent represented by the formula (2) is ^represented by all the formulas A 1 to A ³ (2) It is more preferable that it is a substituent. When A ^{1 to} A ³ are substituents other than the formula (2), specific examples thereof include the substituent T described later, and among them, examples of the substituents R ^{11 to} R ¹³ of the formula (11) described below are preferable. .

  Examples of the compound represented by the formula (1) include the formulas (3-a) to (3-f) and (4-a) to (4-g) used in the examples. A compound represented by 3-a), (3-b), (3-c), (3-d), (3-e), or (3-f) is preferable.

  In each formula, a methyl group may be substituted at the α-position of the acryloyl group. Further, the alkylene group between O of the acryloyloxy group and N of the isocyanuric acid skeleton may be further substituted with an alkyl group having 1 to 3 carbon atoms or a hydroxyl group.

  The resin according to the present invention may be composed of one kind or two or more kinds of specific isocyanurate compounds. Or the resin composition contained with another component may be sufficient. The resin or resin composition according to the present invention is preferably curable. The curing method is not limited, but may be curing by heating or curing by light (electron beam) irradiation. The resin or resin composition according to the present invention is preferably used as an optical member forming agent, and in particular, a sealing agent for a semiconductor light emitting device or a lens forming agent.

  When the resin composition is obtained by combining the specific isocyanurate compound with another compound, the content of the specific isocyanurate compound is preferably 1% by mass or more, preferably 5% by mass or more in the organic curing component. Is more preferable, and it is especially preferable that it is 10 mass% or more. Although there is no upper limit in particular, when considering a combination with a compound represented by the following formula (A), the specific isocyanurate compound is preferably 90% by mass or less, and preferably 60% by mass or less. More preferably, it is particularly preferably 50% by mass or less. By setting it to the lower limit value or more, the action of the specific isocyanurate compound can be sufficiently extracted. By setting it to the upper limit value or less, interaction with a component to be combined (such as a compound represented by the formula (11)) can be expected. In a preferred embodiment of the present invention, the organic curing component of the resin composition refers to a curing component composed of a compound containing a carbon atom (a component that contributes directly to curing by polymerization or the like). This means that it does not contain a polymer, a polymerization initiator, or an organic solvent. In addition, when it is necessary to make a strict comparison, it is meant to exclude trace components such as water and inorganic salts.

[Any acrylate monomer]
When the resin or resin composition of the present invention is used as an optical member forming agent, any of the following arbitrary acrylate monomers may be blended together.

(Any isocyanurate compound)
In the present invention, it is preferable to use a compound having an isocyanurate skeleton represented by the following formula (11) as an arbitrary isocyanurate compound.

・Ｒ^１１、Ｒ^１２、Ｒ^１３
式中のＲ^１１、Ｒ^１２、Ｒ^１３は、それぞれ独立に、水酸基、炭素数１〜１０のアルキル基、炭素数１〜１０のアルコキシ基、炭素数６〜２４のアリールオキシ基、炭素数６〜２４のアリール基、下記式（Ｉ）で表されるアクリロイルオキシ基、又は下記式（ＩＩ）で表されるアシルオキシ基を表す。ただし、式（１１）において、Ｒ^１１、Ｒ^１２、及びＲ^１３の少なくとも１つは前記アクリロイルオキシ基である。なお、本明細書において「アクリロイル」というときには、α位に置換基（メチル、エチル、ハロゲン、シアノなど）を有するものを含む意味である。

・ R ¹¹ , R ¹² , R ¹³
R ¹¹ , R ¹² and R ¹³ in the formula are each independently a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, or 6 carbon atoms. Represents an aryl group of ˜24, an acryloyloxy group represented by the following formula (I), or an acyloxy group represented by the following formula (II). However, in Formula (11), at least one of R ¹¹ , R ¹² , and R ¹³ is the acryloyloxy group. In the present specification, “acryloyl” is meant to include those having a substituent (methyl, ethyl, halogen, cyano, etc.) at the α-position.

式中、Ｒ^ａは水素原子又は炭素数１〜３のアルキル基を表す。＊は結合手を表す。

In the formula, R ^a represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. * Represents a bond.

式中、Ｒ^ｂは炭素数１〜１０のアルキル基又は炭素数６〜２４のアリール基を表す。＊は結合手を表す。

In the formula, R ^b represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 24 carbon atoms. * Represents a bond.

In R ¹¹ , R ¹² , R ¹³ , and R ^b , examples of the alkyl group having 1 to 10 carbon atoms include a linear alkyl group, a branched alkyl group, and a cyclic alkyl group. A linear alkyl group, a branched alkyl group having 3 to 6 carbon atoms, and a cyclic alkyl group having 6 to 10 carbon atoms are preferable.
When R ¹¹ , R ¹² , R ¹³ , and R ^b are an aryl group, the aryl group may be monocyclic or multicyclic. Among them, a phenyl group is preferable as the aryl group.
In the present specification, the alkyl group and the aryl group may further have a substituent, and examples thereof include the substituent T described below.

L ^a has the same meaning as the linking group of a single bond or R ¹ to R ^3, is preferably a single bond or an alkylene group having 1 to 4 carbon atoms. Among them, an ethylene group or an isopropylene group (N—CH ₂ —CH (CH ₃ ) —R direction: R is R ¹¹ , R ¹² , or R ¹³ ) is preferable, and an ethylene group is more preferable. The three Las may be the same or different from each other.

In the compound represented by the formula (11), it is preferable that at least one of R ¹¹ , R ¹² and R ¹³ is a hydroxyl group or a group having this. Especially, it is preferable that the compound represented by said Formula (11) is what is represented by following formula (11-1), (11-2), or (11-3).

・ R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴
In the formula, R ⁷¹ , R ⁷² , and R ⁷³ are each independently hydrogen or a methyl group. R ⁷⁴ is any one of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an acyloxy group represented by the formula (II).

In the present invention, R ⁷⁴ is preferably a substituent containing a hydroxyl group, and more preferably a hydroxyl group.

· ^{L a}
L ^a is as defined for formula (11), it is also similar to the preferred ranges.

  The arbitrary isocyanurate compound may be a compound represented by the following formula (11-4).

* R ^<71> , R ^{<72 >} , R ^{< b} > is synonymous with Formula (11-1) and Formula (II). L ^a have the same meanings as in formula (11).

  The amount of the optional isocyanurate compound added is not particularly limited, but it is preferably 1 to 50% by mass, more preferably 3 to 40% by mass in the organic curing component of the composition. It is particularly preferably 5% by mass or more and 30% by mass or less. By applying an optional isocyanurate compound within the above range, the water absorption rate can be reduced without deteriorating the thermal shock resistance (crack resistance) of the cured product and the heat resistance colorability, and failure due to water absorption (for example, , Moisture absorption reflow cracks generated when the reflow treatment is performed in a water-absorbed state can be reduced, and as a result, a highly reliable semiconductor light emitting device can be provided.

(Acrylate monomer having bisphenylene group)
The acrylate monomer is preferably represented by the following formula (21).

· ^{R 21, R 22}
R ²¹ and R ²² each represent a substituent, and preferred examples thereof include the substituent T described later. When there are a plurality of R ²¹ and R ²² , they may be the same as or different from each other.

・ Ac
Ac represents an acryloyloxy group, and preferred examples thereof include the group represented by the formula (I).

・ L ^e
Le represents a single bond or a linking group. The preferred range is cyclic or chain (branched or straight chain) alkylene group, arylene group, heteroarylene group, oxy group (—O—), carbonyl group, amino group (—NR—: where R is a hydrogen atom or Organic group), or a combination thereof. Among them, an alkylene group having 1 to 10 carbon atoms or an alkylene group that may have an oxy group having 1 to 10 carbon atoms is preferable, and more preferably, the number of carbon atoms bonded to the benzene ring in the formula by an oxygen atom It is an alkylene group which may have 1 to 4 oxy groups.
As defined above, and acrylate monomer preferably has a hydroxyl group, it is preferable that the linking group L ^e may have a hydroxyl group.

・ L ^f
L ^f represents a linking group. Examples thereof include —O—, —CH ₂ —, —C (CH ₃ ) H—, —C (CH ₃ ) ₂ —, —C (CH ₃ ) (Ph) —, and —C (CF ₃ ) ₂ —. _{, -C (CH 3) (C} 2 H 5) -, - C (Ph) 2 -, C (= CCl 2) -, - C (CH 3) H -, - SO 2 - , and the like. In addition, examples of L ^f include those represented by the following formula.

式中、＊は結合手を表す。Ｒ^３１、Ｒ^３２は、炭素原子数１〜５のアルキレン基を表し、メチレン基、エチレン基、プロピレン基が好ましく、なかでも２，２−プロパンジイル基がより好ましい。Ｒ^３３は、置換基を表し、炭素原子数１〜３のアルキル基、炭素数６〜１２のアリール基、ヒドロキシル基、ハロゲン原子等が挙げられる。ｎ３は０〜４の整数を表し、０であることが好ましい。

In the formula, * represents a bond. R ³¹ and R ³² represent an alkylene group having 1 to 5 carbon atoms, preferably a methylene group, an ethylene group or a propylene group, and more preferably a 2,2-propanediyl group. R ³³ represents a substituent, and examples thereof include an alkyl group having 1 to 3 carbon atoms, an aryl group having 6 to 12 carbon atoms, a hydroxyl group, and a halogen atom. n3 represents an integer of 0 to 4, and is preferably 0.

-N21 and n22 represent the integer of 0-4.

(Acrylate monomer having an alicyclic hydrocarbon skeleton)
Examples of the acrylate monomer having an alicyclic hydrocarbon skeleton suitably used in the present invention include the acrylate monomer having the norbornane skeleton or the acrylate monomer having an adamantane skeleton. Specific examples include monomers represented by the following formula (11) or (12).

・Ｒ^１１、Ｒ^１２
Ｒ^１１、Ｒ^１２は置換基を表す。複数あるＲ^１１、Ｒ^１２は互いに結合して環を形成していてもよい。置換基の好ましい範囲としては、後記置換基Ｔの例が挙げられる。Ｒ^１１、Ｒ^１２は複数あるとき、互いに同じであっても異なっていてもよい。

・ R ¹¹ , R ¹²
R ¹¹ and R ¹² represent a substituent. A plurality of R ¹¹ and R ¹² may be bonded to each other to form a ring. As a preferable range of the substituent, examples of the substituent T described later can be given. When there are a plurality of R ¹¹ and R ¹² , they may be the same as or different from each other.

・ L ^d
L ^d represents a single bond or a linking group. Its preferred range is the same as the L ^a. When there are a plurality of R ¹¹ and L ^d , they may be the same as or different from each other.

・ Ac
Ac represents an acryloyloxy group which may have a substituent. The preferable thing of Ac is synonymous with postscript formula (I). When there are a plurality of Ac, they may be the same or different.

  n11 represents an integer of 0 to 6. n12 represents the integer of 0-9. na represents an integer of 1 to 4.

  In the present specification, when the term “compound” is added at the end or indicated by a specific name or chemical formula, it is used in the meaning including its salt and its ion in addition to the compound itself. Moreover, it is the meaning including the derivative modified with the predetermined form in the range with the desired effect. In addition, in the present specification, a substituent or a linking group for which substitution or non-substitution is not specified means that the group may have an arbitrary substituent. This is also synonymous for compounds that do not specify substitution / non-substitution. Preferred substituents include the following substituent T.

Examples of the substituent T include the following.
An alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, pentyl, heptyl, 1-ethylpentyl, benzyl, 2-ethoxyethyl, 1-carboxymethyl, etc.), alkenyl A group (preferably an alkenyl group having 2 to 20 carbon atoms, such as vinyl, allyl, oleyl, etc.), an alkynyl group (preferably an alkynyl group having 2 to 20 carbon atoms, such as ethynyl, butadiynyl, phenylethynyl, etc.), A cycloalkyl group (preferably a cycloalkyl group having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, etc.), an aryl group (preferably an aryl group having 6 to 26 carbon atoms, for example, Phenyl, 1-naphthyl, 4-methoxyphenyl, -Chlorophenyl, 3-methylphenyl, etc.), heterocyclic groups (preferably heterocyclic groups having 2 to 20 carbon atoms, such as 2-pyridyl, 4-pyridyl, 2-imidazolyl, 2-benzimidazolyl, 2-thiazolyl, 2 -Oxazolyl etc.), an alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms, such as methoxy, ethoxy, isopropyloxy, benzyloxy etc.), an aryloxy group (preferably an aryloxy group having 6 to 26 carbon atoms) , For example, phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, etc.), alkoxycarbonyl groups (preferably C2-C20 alkoxycarbonyl groups such as ethoxycarbonyl, 2-ethylhexyloxycarbonyl, etc.) ), Amino group (preferably carbon Amino group having 0 to 20 children, such as amino, N, N-dimethylamino, N, N-diethylamino, N-ethylamino, anilino, etc.), sulfonamide group (preferably sulfonamide having 0 to 20 carbon atoms) A group such as N, N-dimethylsulfonamide, N-phenylsulfonamide, etc., an acyloxy group (preferably an acyloxy group having 1 to 20 carbon atoms such as acetyloxy, benzoyloxy, etc.), a carbamoyl group (preferably A carbamoyl group having 1 to 20 carbon atoms, such as N, N-dimethylcarbamoyl, N-phenylcarbamoyl, etc.), an acylamino group (preferably an acylamino group having 1 to 20 carbon atoms, such as acetylamino, benzoylamino, etc.) , A cyano group, a hydroxyl group, or a halogen atom (for example, a fluorine atom, A chlorine atom, a bromine atom, an iodine atom, etc., more preferably an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an amino group, an acylamino group, a cyano group, or a halogen An atom, particularly preferably an alkyl group, an alkenyl group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, an amino group, an acylamino group, or a cyano group.

  The specific isocyanurate compound may be synthesized by a conventional method, and the synthesis method is not particularly limited. For information on such commercial products, reference can be made to, for example, Japanese Patent Application Laid-Open No. 2003-213159.

[Polymerization initiator]
The resin composition of the present invention preferably contains a polymerization initiator.
Among these, a radical polymerization initiator is added.
Examples of thermal radical polymerization initiators that generate initiation radicals by cleavage by heat include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; 1,1 Hydroperoxides such as 1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide and t-butyl hydroperoxide; diisobutyryl peroxide, bis-3,5,5-trimethylhexanol peroxide, lauroyl peroxide Diacyl peroxides such as oxide, benzoyl peroxide and m-toluyl benzoyl peroxide; dicumyl peroxide, 2, 5 Dimethyl-2,5-di (t-butylperoxy) hexane, 1,3-bis (t-butylperoxyisopropyl) hexane, t-butylcumyl peroxide, di-t-butyl peroxide and 2,5-dimethyl- Dialkyl peroxides such as 2,5-di (t-butylperoxy) hexene; 1,1-di (t-butylperoxy-3,5,5-trimethyl) cyclohexane, 1,1-di-t-butylperoxy Peroxyketals such as cyclohexane and 2,2-di (t-butylperoxy) butane; 1,1,3,3-tetramethylbutylperoxyneodicarbonate, α-cumylperoxyneodicarbonate, t-butylperoxyneodicarbonate , T-hexylperoxypivalate, t-butylperoxypivalate 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, t-amylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butyl Peroxyisobutyrate, di-t-butylperoxyhexahydroterephthalate, 1,1,3,3-tetramethylbutylperoxy-3,5,5-trimethylhexanate, t-amylperoxy-3,5,5-trimethyl Alkyl peresters such as hexanoate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxyacetate, t-butylperoxybenzoate and dibutylperoxytrimethyladipate; di-3-methoxybutylperoxy Dicarbonate, di-2-ethylhexyl Ruperoxydicarbonate, bis (1,1-butylcyclohexaoxydicarbonate), diisopropyloxydicarbonate, t-amylperoxyisopropylcarbonate, t-butylperoxyisopropylcarbonate, t-butylperoxy-2-ethylhexylcarbonate and 1, Peroxycarbonates such as 6-bis (t-butylperoxycarboxy) hexane; 1,1-bis (t-hexylperoxy) cyclohexane and (4-t-butylcyclohexyl) peroxydicarbonate.
Specific examples of the azo compound used as an azo-based (AIBN or the like) polymerization initiator include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 2, 2'-azobis (2,4-dimethylvaleronitrile), 1,1'-azobis-1-cyclohexanecarbonitrile, dimethyl-2,2'-azobisisobutyrate, 4,4'-azobis-4-cyano Valeric acid, 2,2′-azobis- (2-amidinopropane) dihydrochloride and the like can be mentioned (see JP 2010-189471 A).

As the radical polymerization initiator, in addition to the thermal radical polymerization initiator, a radical polymerization initiator that generates an initiation radical by light, electron beam, or radiation can be used.
Examples of such radical polymerization initiators include benzoin ether, 2,2-dimethoxy-1,2-diphenylethane-1-one [IRGACURE651, manufactured by Ciba Specialty Chemicals Co., Ltd.], 1-hydroxy-cyclohexyl. -Phenyl-ketone [IRGACURE 184, manufactured by Ciba Specialty Chemicals, Inc.], 2-hydroxy-2-methyl-1-phenyl-propan-1-one [DAROCUR1173, manufactured by Ciba Specialty Chemicals, Inc.] , Trademark], 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one [IRGACURE2959, manufactured by Ciba Specialty Chemicals, Inc.], 2-Hydroxy-1- [4- [4- (2-H Droxy-2-methyl-propionyl) -benzyl] phenyl] -2-methyl-propan-1-one [IRGACURE 127, trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.], 2-methyl-1- (4-methylthio Phenyl) -2-morpholinopropan-1-one [IRGACURE907, manufactured by Ciba Specialty Chemicals, Inc.], 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 [IRGACURE369, trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.], 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-monophorinyl) phenyl] -1- Butanone [IRGACURE 379, manufactured by Ciba Specialty Chemicals, Inc., trademark] 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide [DAROCUR TPO, manufactured by Ciba Specialty Chemicals, Inc., trademark], bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide [IRGACURE819, Ciba・ Specialty Chemicals Co., Ltd., Trademark], bis (η ⁵ -2,4-cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl ) Titanium [IRGACURE784, Ciba Specialty Chemicals Co., Ltd., Trademark], 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] [IRGACURE OXE 01, Ciba・ Specialty Chemicals Co., Ltd. Tanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime) [IRGACURE OXE 02, manufactured by Ciba Specialty Chemicals Co., Ltd. , Trademark] and the like.
These radical polymerization initiators can be used singly or in combination of two or more.
Among them, a peroxide compound is preferable, and perbutyl O (t-butylperoxy-2-ethylhexanoate, manufactured by NOF Corporation) and the like can be used.

Although the quantity of a polymerization initiator is not specifically limited, It is preferable that it is 5 mass parts or less with respect to 100 mass parts of organic hardening components, and it is more preferable that it is 2 mass parts or less. On the other hand, it is preferable to make it not more than the above upper limit value because the excellent effect of the resin composition by applying the specific isocyanurate compound can be sufficiently obtained.
In the present invention, the resin composition may be polymerized only by heating, or the polymerization initiator may not be used.

[Polymerization inhibitor]
A polymerization inhibitor may be added to the resin composition of the present invention. Examples of the polymerization inhibitor include phenols such as hydroquinone, tert-butylhydroquinone, catechol, and hydroquinone monomethyl ether; quinones such as benzoquinone and diphenylbenzoquinone; phenothiazines; copper and the like.
Although content of a polymerization inhibitor is not specifically limited, It is 0-20000 ppm (mass part reference | standard) with respect to 1 part of organic hardening components, Preferably it is 100-10000 ppm, More preferably, it is preferable to add at 200-3000 ppm.

[Antioxidant]
You may add antioxidant to the resin composition of this invention as needed. Examples of antioxidants include phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, thioether antioxidants, vitamin antioxidants, lactone antioxidants, and amine antioxidants. .

  Examples of phenolic antioxidants include Irganox 1010 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), Irganox 1076 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), Irganox 1330 (manufactured by Ciba Specialty Chemicals Co., Ltd.), Trademark), Irganox 3114 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), Irganox 3125 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), ADK STAB AO-20 (ADEKA, Inc., trade name), ADK STAB AO-50 (ADEKA Corporation, Trademark), Adeka Stub AO-60 (ADEKA Corporation, Trademark), Adeka Stub AO-80 (ADEKA Corporation, Trademark), Adeka Stub AO-30 (ADEKA Corporation, Trademark) , ADK STAB AO-40 (ADEKA, Inc., trademark), BHT (trade name, manufactured by Takeda Pharmaceutical Co., Ltd.), Cyanox 1790 (trademark, manufactured by Cyanamid Co., Ltd.), Sumizer GP (trademark, manufactured by Sumitomo Chemical Co., Ltd.) Examples include commercial products such as Sumitomo Chemical Co., Ltd., Trademark), Sumilizer GS (Sumitomo Chemical Co., Ltd., Trademark), and Sumizer GA-80 (Sumitomo Chemical Co., Ltd., Trademark).

  Examples of phosphorus compounds include IRAGAFOS 168 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), IRAGAFOS 12 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), IRAGAFOS 38 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), IRAGAFOS P-EPQ (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), IRAGAFOS 126 (trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.), ADKSTAB 329K (ADEKA, Inc.), ADKSTAP PEP-36 (stock) Company ADE KA, trademark), ADKSTAP PEP-8 (ADE KA, trademark), ADKSTAP HP-10 (ADE KA, trademark), ADKSTAB 2112 (ADE KA, quotient) Standard), ADKSTAB 260 (ADEKA, trademark), ADKSTAB 522A (ADEKA, trademark), Weston 618 (GE, trademark), Weston 619G (GE, trademark), and Weston 624 (GE) And commercial products such as trade names).

  Examples of sulfur-based antioxidants include DSTP (Yoshitomi) (trademark), DLTP (Yoshitomi) (trademark, produced by Yoshitomi Corporation), DLTOIB (trademark, produced by Yoshitomi Corporation), DMTP (Yoshitomi). ) [Trademark] made by Yoshitomi Co., Ltd., Seenox 412S [trademark made by Sipro Kasei Co., Ltd.], Cyanox 1212 (trademark made by Cyanamid Co., Ltd.) and TP-D, TPS, TPM, TPL-R [Sumitomo Chemical Co., Ltd. ), Trade name, etc.). Examples of vitamin-based antioxidants include tocopherol (trade name, manufactured by Eisai Co., Ltd.) and Irganox E201 (trade name, compound name: 2,5,7,8-tetramethyl-2 (4, manufactured by Ciba Specialty Chemicals Co., Ltd.). Commercial products such as ', 8', 12'-trimethyltridecyl) coumarone-6-ol].

  Examples of the thioether-based antioxidant include commercially available products such as ADK STAB AO-412S (trade mark, manufactured by ADE KA) and ADK STAB AO-503 (trade mark, manufactured by ADE KA). As the lactone antioxidant, those described in JP-A-7-233160 and JP-A-7-247278 can be used. Moreover, HP-136 [Ciba Specialty Chemicals Co., Ltd., trademark, compound name; 5,7-di-t-butyl-3- (3,4-dimethylphenyl) -3H-benzofuran-2-one] And other commercial products.

  Examples of amine-based antioxidants include commercially available products such as Irgastab FS042 [trade name, manufactured by Ciba Specialty Chemicals Co., Ltd.] and GENOX EP [trade name, compound name; dialkyl-N-methylamine oxide] manufactured by Crompton Co., Ltd. Can do. These antioxidants can be used singly or in combination of two or more.

  The content of the antioxidant is usually 0.01 to 10 parts by mass with respect to 100 parts by mass of the total amount of the organic curing component, preferably from the viewpoint of suppressing the transparency of the resin composition and the reduction of yellowing. It is 0.01-5 mass parts, More preferably, it is 0.02-2 mass parts.

[Light stabilizers, etc.]
The resin of the present invention or a composition thereof (hereinafter collectively referred to as a resin composition) includes, in addition to the above-described antioxidant, a lubricant, a light stabilizer, an ultraviolet absorber, a plasticizer, and an antistatic agent as necessary. Agents, inorganic fillers, colorants, antistatic agents, mold release agents, flame retardants, components for the purpose of improving adhesion with inorganic compounds such as titanium oxide and silicon oxide, and the like can be blended. As the lubricant, higher dicarboxylic acid metal salts, higher carboxylic acid esters, and the like can be used.

  Any known light stabilizer can be used, but a hindered amine light stabilizer is preferred. Specific examples of the hindered amine light stabilizer include ADKSTAB LA-77, LA-57, LA-52, LA-62, LA-67, LA-68, LA-63, and LA-94. LA-94, LA-82 and LA-87 (above, manufactured by ADEKA Corporation), Tinuvin 123, 144, 440 and 662, Chimassorb 2020, 119, 944 (above, manufactured by CSC) , Hostavin N30 (manufactured by Hoechst), Cyasorb UV-3346, UV-3526 (manufactured by Cytec), Uval 299 (GLC), and SanduvorPR-31 (Clariant). These light stabilizers can be used singly or in combination of two or more.

The usage-amount of a light stabilizer is 0.005-5 mass parts normally with respect to 100 mass parts of total amounts of the said organic hardening component, Preferably it is 0.02-2 mass parts.
Examples of the component for improving the adhesion with inorganic compounds such as titanium oxide and silicon oxide include silane coupling agents containing a methacryloxy group or an acryloxy group of the silane compound. This may be contained in the resin composition, polymerized and molded.

[Semiconductor light emitting device]
(Sealing method)
The resin composition of the present invention can be used as a sealing agent for semiconductor light emitting devices and the like. As a sealing method of the sealing agent, a method usually used for sealing a semiconductor light emitting element or a method similar to a general thermosetting resin molding can be used. Examples thereof include potting (dispensing), printing, coating, injection molding, compression molding, transfer molding, and insert molding. Potting represents an operation of discharging the sealing agent into a cavity (concave space) of the package to fill the interior. In addition, printing represents an operation of disposing a sealant at a target site using a mask, and a so-called vacuum printing method in which the surrounding pressure is reduced according to the purpose can be employed. Various types of coating methods can be used for coating. For example, a method of preparing a weir called a dam material for holding a sealing agent in advance and coating the sealing agent on the inside thereof can also be used. Moreover, in various mold shaping | molding, the method of filling the sealing agent inside a mold and thermosetting as it is is mentioned. Further, curing after sealing can be performed by heat curing, UV curing, or a combination thereof.
The semiconductor light-emitting device in preferable embodiment of this invention comprises the sealing material produced by hardening said sealing agent. As a curing method, a method similar to the molding of a normal thermosetting resin can be used. For example, the above-mentioned resin composition or a prepolymer thereof may be used for polymerization / molding by injection molding, compression molding, transfer molding, insert molding, etc. of these liquid resins. Moreover, a molded object can also be obtained by a potting process or a coating process. Furthermore, a molded body can be obtained by a method similar to the molding of a photo-curing resin such as UV curing molding.

  It is preferable that the semiconductor light-emitting device or its member of this embodiment is manufactured by a liquid resin molding method. Liquid resin molding includes liquid resin injection molding in which a liquid resin composition or a prepolymer thereof at room temperature is pressed into a high-temperature mold and cured by heating, and the liquid resin composition is placed in a mold and pressed by a press. Examples thereof include compression molding for pressing and curing, transfer molding for curing a sealant by applying pressure to a heated liquid resin composition and press-fitting it into a mold.

(Lens formation)
The resin composition of the present invention can also be used as a lens forming material. The lens may be incorporated into any product, and may be a lens of a semiconductor light emitting device or a lens such as a wafer level lens, a CCD camera, or a CMOS camera. An example of use as a lens of a semiconductor light emitting device is schematically shown in FIG. Although the manufacturing method of this lens 9 is not specifically limited, After forming the sealing material 3 as mentioned above, the desired lens 9 can be formed by dripping the resin composition on the surface. If a resin composition having an appropriate surface tension and viscosity is used, a lens having a predetermined convex surface can be obtained only by the dropping treatment. Or it is good also as a lens of a predetermined convex surface or a concave surface using a mold. Furthermore, the aspect which manufactures the said sealing material and a lens once with the same resin composition is also mentioned.

  According to the resin or the composition thereof of the present invention, it is possible to make use of the advantages because it has high aerobic curability regardless of the formation of the sealing material or the lens. The aerobic curability specifically means the property that the resin cures rapidly and uniformly even in the presence of oxygen in the air. Usually, when a compound having an ethylenically unsaturated bond group undergoes radical polymerization with the group, if oxygen in the air is present, this may become an inhibiting factor and the polymerization reaction may not proceed. If it does so, reaction will not advance only on the resin surface part which contacts oxygen (air), the hardened | cured material of a desired form may not be obtained, and a liquid part or a rubber-like part may remain on the surface. When it is inferior, the polymerization reaction does not proceed at all and a cured product may not be obtained. The resin or composition thereof of the present invention allows the polymerization reaction to proceed suitably even in such an environment where it comes into contact with air (oxygen), and a good cured product with no unevenness can be obtained. Therefore, it is not necessary to carry out the production under supply of a nitrogen atmosphere or the like, which greatly contributes to the improvement of the production process and the improvement of the production quality.

(Semiconductor light emitting device)
As the semiconductor light emitting element, a blue light emitting LED chip made of a gallium nitride (GaN) based semiconductor, an ultraviolet light emitting LED chip, a laser diode, or the like is used. In addition, for example, a substrate in which a nitride semiconductor such as InN, AlN, InGaN, AlGaN, InGaAlN or the like is formed as a light emitting layer on a substrate by MOCVD or the like can be used. Either a semiconductor light-emitting element that is mounted face-up or a semiconductor light-emitting element that is flip-chip mounted can be used. The semiconductor light emitting device is an example of a semiconductor light emitting device having an n-side electrode and a p-side electrode on the same plane, but a semiconductor light-emitting device having an n-side electrode on one surface and a p-side electrode on the opposite surface is also used. be able to.

(package)
As the package, a package in which electrodes are integrally formed, and a package in which electrodes are provided as circuit wiring by plating after the package is molded can be used. As the shape of the package, any shape such as a cylinder, an elliptical column, a cube, a rectangular parallelepiped, a shape between a rectangular parallelepiped and an elliptical column, or a combination thereof can be adopted. As the shape of the inner wall portion, an arbitrary angle can be selected with respect to the bottom portion, and a box shape that is perpendicular to the bottom surface or a mortar shape that is obtuse can be selected. As the shape of the bottom of the concave portion, any shape such as a flat shape or a concave shape can be selected. Moreover, a package corresponding to an arbitrary mounting method such as a top view or a side view can be used as a mounting method.
As a material constituting the package, an electrically insulating material excellent in light resistance and heat resistance is suitably used. For example, a thermoplastic resin such as polyphthalamide (PPA), a thermosetting resin such as an epoxy resin, Glass epoxy, ceramics, etc. can be used. Moreover, in order to reflect the light from a semiconductor light emitting element efficiently, white pigments, such as a titanium oxide, can be mixed with these resins. As a method for molding the package, insert molding, injection molding, extrusion molding, transfer molding, or the like performed by previously setting the electrode in a mold can be used.

(electrode)
The electrode is electrically connected to the semiconductor light emitting element, and may be, for example, a plate-like electrode inserted into a package or a conductive pattern formed on a substrate such as glass epoxy or ceramic. As the material of the electrode, there can be used silver or an alloy containing silver, or a material in which silver or an alloy containing silver is plated on a part of an electrode containing copper or iron as a main component.

(Evaluation method)
The semiconductor light emitting device can be evaluated by a conventional test method. For example, electrical characteristics, optical characteristics, temperature characteristics, thermal characteristics, lifetime, reliability, safety, and the like can be given. As a technique, for example, the technique and standard described in pages 71 to 84 of Chapter 2 of the book “LED Lighting Handbook, LED Lighting Promotion Council Edition” published by Ohm Co., Ltd. can be adopted.

(Use)
The resin or resin composition of the present invention can be suitably applied to an optical member forming agent. Examples of the optical member include a semiconductor light emitting device and a wafer level lens module. Semiconductor light-emitting devices are used in various applications that require maintenance of luminous intensity, such as backlights for liquid crystal displays, mobile phones or information terminals, LED displays, flashlights, indoor / outdoor lighting, OLED lighting, OLED displays, solar cell members, etc. Can be widely used. The lens module is widely incorporated in various image pickup apparatuses and mobile phones.

  Further, the novel specific isocyanurate compound according to the present invention is useful as a functional additive coordinated to a resin, a raw material (monomer) of various polymers, etc., including the above-described resin applications.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated in detail, this invention is limited and interpreted by the following examples.
The following compounds were synthesized or obtained and procured.

(1) Synthesis of compounds (3-a) (3-d) (3-e) In a 100 mL flask, 30 g of Aronics M-315 (manufactured by Toagosei Co., Ltd.), 20.8 g of a 37 wt% formaldehyde aqueous solution, 1,4- Diazabicyclo [2.2.2] octane 0.24 g and dimethyl sulfoxide 30 mL were mixed, stirred at room temperature for 16 hours, and subjected to column chromatography to obtain compounds (3-a), (3-d), (3-e ) For the compound (3-a), the NMR spectrum is shown in FIG. For other compounds, those synthesized were similarly identified by NMR.

(2) Synthesis of compounds (3-b), (3-c) and (3-f) Aronix M-215 (trade name, manufactured by Toagosei Co., Ltd.) was purified by column chromatography to produce a bifunctional acrylic (M- After obtaining 1) and a monofunctional acrylic body, (3-b), (3-c), and (3-f) were obtained in the same manner as described above using each as a raw material.

(3) Synthesis of compounds (4-a) (4-b) (4-c) Tetrahedron Vol. 51, No, 9, pp. After obtaining tris (3-acryloyloxypropyl) isosinurate by the method described in 2561-2572, 1995, α-hydroxymethylated product (4-a) was obtained by the same method as (3-a). (4-b) and (4-c) were also synthesized in the same manner.

(4) Synthesis of Compound (4-d) Acetaldehyde was used instead of formaldehyde, and synthesis was performed in the same manner as (3-a).
(5) Synthesis of compounds (4-e), (4-f) and (4-g) After bromination of (3-a) with phosphorus tribromide, methanol, methanethiol and methylamine were reacted respectively. (4-e), (4-f), and (4-g) were obtained by column chromatography.

(6) Synthesis of Compound (M-1) Compound (M-1) was obtained by purifying Aronix M-215 (trade name, manufactured by Toagosei Co., Ltd.) by column chromatography.
Compound (M-2): Dicyclopentanyl methacrylate (FA-513M manufactured by Hitachi Chemical Co., Ltd.) was used.
Compound (M-3): Adamantyl methacrylate (manufactured by Osaka Organic Industry Co., Ltd.) was used.
Compound (M-4): Tricyclodecane dimethanol acrylate (A-DCP manufactured by Shin-Nakamura Kogyo Co., Ltd.) was used.

-Other compounding components Irganox 1076: Irganox 1076 (manufactured by Ciba Specialty Chemicals) was used.
Perbutyl O: Perbutyl O (manufactured by NOF Corporation) was used.
AIBN: 2,2′-azobisisobutyronitrile (trade name: V-60, manufactured by Wako Pure Chemical Industries, Ltd.) was used.
Perhexa HC: Perhexa HC (manufactured by NOF Corporation) was used.

-Comparative sample KER 2500: KER 2500 (made by Shin-Etsu Silicone) was used.
SCR 1011: SCR 1011 (manufactured by Shin-Etsu Silicone) was used.

[Aerobic curability]
The curable resin composition shown in Table 1 was converted into a PPA resin package (trade name: FLASH LED 6PIN BASE (circular package for top view), manufactured by Enomoto Co., Ltd.) ([cavity size: depth 0.65 mm, Potting to a width of 4.4 mm and a diameter of 4.4 mm]), followed by heat curing in the air by sequentially applying heat at 70 ° C. for 30 minutes, 130 ° C. for 30 minutes, and 150 ° C. for 30 minutes. The heated resin was touched with tweezers and ranked according to the following criteria.
AA: Glassy (solidified to the surface)
A: Rubber (only the surface is soft)
B: Partially liquid surface C: Entirely liquid

[Heat resistant coloring]
An uncured liquid is sandwiched between glass plates, heat is sequentially applied at 70 ° C. for 30 minutes, 130 ° C. for 30 minutes, and 150 ° C. for 5 hours to produce a resin molded into a 1 mm thick substrate. The cured product thus prepared was further heated at 150 ° C. for 24 hours in the atmosphere, and then the transmittance was measured for light having a wavelength of 400 nm using an ultraviolet-visible measuring device UV-3100 (manufactured by Shimadzu Corporation).
AA: 88% or more A: 85% or more and less than 88% B: 80% or more and less than 85% C: Less than 80%

[Linear thermal expansion coefficient]
Using a thermal expansion measuring device (Seiko Instrumental: TMA / SS6100), linear expansion in a temperature range of 40 ° C. to 100 ° C. was measured by a compression method with a load of 49 mN, and a linear thermal expansion coefficient was calculated. : Less than 85 ppm / K A: 85 ppm / K or more, less than 120 ppm / K B: 120 ppm / K or more, less than 200 ppm / K C: 200 ppm / K or more

  It can be seen that the resin of the present invention (Example) is excellent as a forming agent for optical members, and the material type is enriched as different from the conventional resin (Comparative Example). In particular, the resin (Example) of the present invention satisfies suitable curability, heat resistance, and coefficient of thermal expansion required for optical member applications. In this test, it is shown as an example used as a sealant for semiconductor light-emitting devices, but all of the above performances are required for lenses, and excellent performance in other applications such as lenses. You can see that it works.

1 Semiconductor Light Emitting Element (Semiconductor Light Emitting Element)
2 Reflector Package Base Material 3 Sealing Material 4 Electrode 6 Bonding Wire 8 Conductive Adhesive 9 Lens 10 Semiconductor Light Emitting Device (Semiconductor Light Emitting Device)

Claims (12)

Resin containing the compound represented by following formula (1).

(In the formula, R ¹ represents a linking group. A ^{1 to} A ³ each independently represents a hydrogen atom or a substituent, and at least one of them is a substituent represented by the following formula (2).)

(In the formula, R ² represents a hydrogen atom or a substituent. A ⁴ represents a hydroxyl group, an alkoxy group, a thiol group, a thioalkoxy group, or an amino group. * Represents a bond.) The resin according to claim 1, wherein in the formula (1), at least two of A ^{1 to} A ³ are substituents represented by the formula (2). 2. The resin according to claim 1, wherein in Formula (1), all of A ^{1 to} A ³ are substituents represented by Formula (2). The resin according to any one of claims 1 to 3, wherein in the formula (1), R ¹ is an ethylene group. In the formula (2), the resin according to any one of claims 1 to 4 R ² is a hydrogen atom or a methyl group. The compound represented by the formula (1) is represented by the following formula (3-a), (3-b), (3-c), (3-d), (3-e), or (3-f). The resin according to any one of claims 1 to 5, which is a compound represented by the formula:

  Resin of any one of Claims 1-6 which has curability.   The resin composition which made the other component contain with the resin of any one of Claims 1-7.   The optical member formation agent formed by containing the resin of any one of Claims 1-7.   An optical member obtained by curing the optical member forming agent according to claim 9.   A semiconductor light emitting device comprising the optical member according to claim 10. A compound represented by the following formula (1).

(In the formula, R ¹ represents a linking group. A ^{1 to} A ³ each independently represents a hydrogen atom or a substituent, and at least one of them is a substituent represented by the following formula (2).)

(In the formula, R ² represents a hydrogen atom or a substituent. A ⁴ represents a hydroxyl group, an alkoxy group, a thiol group, a thioalkoxy group, or an amino group. * Represents a bond.)

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