JP2006321832A - Resin composition for sealing optical semiconductor and optical semiconductor device using the same - Google Patents
Resin composition for sealing optical semiconductor and optical semiconductor device using the same Download PDFInfo
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Abstract
Description
この発明は、光透過性、耐熱性及び耐光性に優れた光半導体封止用樹脂組成物及び該樹脂組成物を用いて光半導体素子を封止してなる光半導体装置に関するものである。 The present invention relates to a resin composition for sealing an optical semiconductor excellent in light transmittance, heat resistance, and light resistance, and an optical semiconductor device formed by sealing an optical semiconductor element using the resin composition.
現在、種々の表示板、画像読み取り用光源、交通信号、大型ディスプレイ用ユニット、液晶ディスプレイ用バックライト等に実用化されている発光ダイオード（以下「ＬＥＤ」と略す）等の光半導体発光装置は、大部分が封止樹脂よって製造されている。これに使用されている封止用の樹脂は、熱硬化性エポキシ樹脂組成物や熱硬化性シリコン樹脂組成物が使用されている。 Currently, optical semiconductor light-emitting devices such as light-emitting diodes (hereinafter abbreviated as “LEDs”) that have been put to practical use in various display panels, image reading light sources, traffic signals, large display units, liquid crystal display backlights, etc. Most are made of sealing resin. As the sealing resin used for this, a thermosetting epoxy resin composition or a thermosetting silicone resin composition is used.
今日のＬＥＤの飛躍的な進歩により、ＬＥＤの高出力化および短波長化が急速に現実のものとなり始めていて、特に窒化物半導体を用いた高出力な発光が可能となっている。一例を挙げると、発光ピーク波長が３５０〜４９０ｎｍの紫外〜青色光の励起エネルギーの高いＬＥＤと蛍光体を組み合わせ、次世代の照明用途をターゲットとした研究や開発がなされている。 Due to the dramatic progress of today's LEDs, higher output and shorter wavelength of LEDs are rapidly becoming a reality, and particularly high output light emission using a nitride semiconductor is possible. As an example, research and development have been conducted targeting a next-generation lighting application by combining an LED having a high emission energy of ultraviolet to blue light having an emission peak wavelength of 350 to 490 nm and a phosphor.
熱硬化性エポキシ樹脂組成物としては、一般にビスフェノールＡ型エポキシ樹脂又は脂環式エポキシ樹脂等のエポキシ樹脂と酸無水物系硬化剤を用いて得られるものが用いられている（特許文献１、特許文献２）。 As the thermosetting epoxy resin composition, one obtained by using an epoxy resin such as bisphenol A type epoxy resin or alicyclic epoxy resin and an acid anhydride curing agent is generally used (Patent Document 1, Patent). Reference 2).
しかし、かかる透明エポキシ樹脂組成物においても、ＬＥＤの高輝度・短波長化に対応した耐熱性や耐光性が十分でなく、経時的に劣化し、基本性能である光透過性が顕著に低下するという問題があった。 However, even in such a transparent epoxy resin composition, the heat resistance and light resistance corresponding to the high brightness and short wavelength of the LED are not sufficient, and it deteriorates with time, and the light transmittance as a basic performance is remarkably lowered. There was a problem.
そのため、耐熱性及び耐光性が優れる、熱硬化性シリコン樹脂組成物が提案されている（特許文献３、特許文献４）。 Therefore, thermosetting silicon resin compositions having excellent heat resistance and light resistance have been proposed (Patent Documents 3 and 4).
しかし、これらの熱硬化性シリコン樹脂組成物は、発光素子およびフレーム等との接着性が低く、また、その硬化物は硬度が低いために、耐擦傷性が十分でなく、砲弾型ＬＥＤやトップビュータイプの表面実装型ＬＥＤには適さず、サイドビュー等の一部の表面実装型ＬＥＤにしか適用できないという問題があった。 However, these thermosetting silicone resin compositions have low adhesion to light-emitting elements and frames, and the cured product has low hardness, so that the scratch resistance is not sufficient, so that bullet-type LEDs and tops can be used. There is a problem that it is not suitable for a view-type surface-mounted LED, and can only be applied to some surface-mounted LEDs such as a side view.
また更に、発光素子に使用されるＳｉＣ、ＧａＡｓ、ＧａＰ、ＧａＡｓＰ、ＧａＡｌＡｓ、ＩｎＡｌＧａＰ、ＩｎＧａＮ、ＧａＮ等の各種化合物半導体は光学結晶の屈折率が高いため、封止樹脂の屈折率がジメチル系シロキサンのように低い場合、封止樹脂と光学結晶との界面で反射して発光効率が低下する欠点があった。 Furthermore, since various compound semiconductors such as SiC, GaAs, GaP, GaAsP, GaAlAs, InAlGaP, InGaN, and GaN used in the light emitting element have a high refractive index of the optical crystal, the refractive index of the sealing resin is dimethyl siloxane. In the case of such a low value, there is a drawback in that the light emission efficiency decreases due to reflection at the interface between the sealing resin and the optical crystal.
このため、発光効率を高めるため、反射防止膜をつけるなどの手法が提案されている（特許文献５）。しかし、反射防止膜を作製するためには工程が増え、コスト高になってしまう。 For this reason, in order to improve luminous efficiency, a method such as attaching an antireflection film has been proposed (Patent Document 5). However, the number of steps is increased to produce an antireflection film, resulting in an increase in cost.
更に最近に至り、（ａ）一分子中に２個以上の脂肪族不飽和結合を有するポリオルガノシロキサン、（ｂ）ポリオルガノハイドロジェンシロキサン及び白金族金属系触媒に、特定の単位からなるレジン構造のオルガノポリシロキサンを所定量配合されてなるシリコーンゴム組成物が知られるに至った（特許文献６）。しかし、本発明の目的とする課題、すなわち耐衝撃性および耐擦傷性、発光素子及びフレーム等との接着性等において、なお充分とは言えない。 More recently, (a) a polyorganosiloxane having two or more aliphatic unsaturated bonds in one molecule, (b) a polyorganohydrogensiloxane and a platinum group metal catalyst, a resin structure comprising specific units. A silicone rubber composition containing a predetermined amount of the organopolysiloxane has been known (Patent Document 6). However, it cannot be said that the objects of the present invention, i.e., impact resistance and scratch resistance, adhesion to light emitting elements and frames, etc., are still sufficient.
この発明は、このような事情を鑑みなされたもので、光透過性、耐熱性及び耐光性に優れ、且つ発光素子及びフレーム等との接着性に優れ、しかも硬度が高く、耐衝撃性及び耐擦傷性に優れた光半導体封止用樹脂組成物及び該樹脂組成物を用いて光半導体素子を封止してなる光半導体装置を提供することにある。 The present invention has been made in view of such circumstances, and is excellent in light transmittance, heat resistance and light resistance, excellent in adhesion to a light emitting element and a frame, and has high hardness, impact resistance and resistance to light. An object of the present invention is to provide an optical semiconductor encapsulating resin composition having excellent scratch resistance and an optical semiconductor device in which an optical semiconductor element is encapsulated using the resin composition.
すなわち、本発明は、
（Ａ）一分子中に２個以上の脂肪族不飽和結合を有するポリオルガノシロキサン、
（Ｂ）ポリオルガノハイドロジェンシロキサン及び白金族金属系触媒、
（Ｃ）ポリオルガノシルセスキオキサン、
を含有することを特徴とする光半導体封止用樹脂組成物である（請求項１）。
また、本発明は、上記において、特に
（Ｃ）成分のポリオルガノシルセスキオキサンが、下記式〔１〕及び式〔２〕
That is, the present invention
(A) a polyorganosiloxane having two or more aliphatic unsaturated bonds in one molecule;
(B) polyorganohydrogensiloxane and platinum group metal catalyst,
(C) polyorganosilsesquioxane,
It is a resin composition for optical semiconductor sealing characterized by containing (Claim 1).
In the present invention, the polyorganosilsesquioxane as the component (C) is preferably represented by the following formulas [1] and [2].
（式中、Ｒ1、Ｒ２及びＲ４は同じか又は異なる非置換基もしくは置換一価炭化水素基であり、Ｒ３、Ｒ５及びＲ６は水素原子およびアルキル基を示す。）
で表される末端基を有するポリオルガノシルセスキオキサンであることを特徴とする請求項１に記載の光半導体封止用樹脂組成物である（請求項２）。
(In the formula, R 1 , R 2 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and R 3 , R 5 and R 6 represent a hydrogen atom and an alkyl group.)
The resin composition for sealing an optical semiconductor according to claim 1, wherein the resin composition is a polyorganosilsesquioxane having a terminal group represented by the formula (Claim 2).
また本発明は、（Ｃ）成分のポリオルガノシルセスキオキサンが、平均粒子径が１００ｎｍ以下の微粒子状高分子量体のポリオルガノシルセスキオキサンであることを特徴とする請求項１乃至請求項２記載の光半導体封止用樹脂組成物である（請求項３）。 Further, in the present invention, the polyorganosilsesquioxane of component (C) is a polyorganosilsesquioxane having a fine particle high molecular weight having an average particle size of 100 nm or less. 2. A resin composition for sealing an optical semiconductor according to claim 2 (claim 3).
更に本発明は、（Ｃ）成分のポリオルガノシルセスキオキサンが、（Ａ）及び／又は（Ｂ）成分に分散してなることを特徴とする請求項１乃至請求項３記載の光半導体封止用樹脂組成物である（請求項４）。 Furthermore, the present invention provides the photosemiconductor encapsulation according to claims 1 to 3, wherein the polyorganosilsesquioxane of component (C) is dispersed in component (A) and / or (B). A resin composition for stopping.
また（Ｃ）成分は、（Ａ）、（Ｂ）及び（Ｃ）成分の合計量に対して５〜９０重量％の量で配合されていることを特徴とする請求項１乃至請求項４記載の光半導体封止用樹脂組成物である（請求項５）。 The component (C) is blended in an amount of 5 to 90% by weight based on the total amount of the components (A), (B) and (C). This is a resin composition for sealing an optical semiconductor.
更にまた本発明は、請求項１乃至請求項５記載の光半導体封止用樹脂組成物を用いて光半導体素子を封止してなることを特徴とする光半導体装置である（請求項６）。 Furthermore, the present invention is an optical semiconductor device comprising an optical semiconductor element sealed with the optical semiconductor sealing resin composition according to any one of claims 1 to 5 (claim 6). .
本発明の特徴は、（Ａ）成分及び（Ｂ）成分に対して特定のポリオルガノシルセスキオキサン（Ｃ）成分を所定量配合することにより、光透過性、耐熱性及び耐光性に優れ、且つ発光素子及びフレーム等との接着性に優れ、しかも硬度が高く、耐衝撃性及び耐擦傷性に優れた光半導体封止剤用樹脂組成物が得られることを見出した点にある。 The characteristics of the present invention are excellent in light transmittance, heat resistance and light resistance by blending a predetermined amount of a specific polyorganosilsesquioxane (C) component with respect to the component (A) and the component (B), In addition, it is found that a resin composition for an optical semiconductor encapsulant that is excellent in adhesion to a light emitting element, a frame, and the like, has high hardness, and has excellent impact resistance and scratch resistance can be obtained.
本発明によれば、光透過性、耐熱性及び耐光性に優れ、且つ発光素子及びフレーム等との接着性に優れ、しかも硬度が高く、耐衝撃性及び耐擦傷性に優れた光半導体封止用樹脂組成物を提供すること及び該樹脂組成物を用いて光半導体素子を封止してなる光半導体装置を提供することができる。
なおまた、本発明の光半導体封止用樹脂組成物は、以下のような種々の用途に好ましく用いられ、または用いられることが期待される。
（１）ＬＥＤの封止
（２）有機ＥＬ、無機ＥＬ、レーザーダイオード等の封止（又はコート剤、周辺部材等）、
（３）その他、ＤＶＤやメガネ等のコート剤、光導波路、光ファィバー、接着剤等の光通信関連部材、熱可塑性樹脂や熱硬化性樹脂等の汎用樹脂の改質、層間絶縁膜、光硬化（造型）材料 等々
According to the present invention, an optical semiconductor encapsulating having excellent light transmission, heat resistance and light resistance, excellent adhesion to a light emitting element and a frame, etc., and having high hardness, impact resistance and scratch resistance. It is possible to provide a resin composition for use and an optical semiconductor device in which an optical semiconductor element is sealed using the resin composition.
In addition, the resin composition for encapsulating an optical semiconductor of the present invention is preferably used or expected to be used for various applications as described below.
(1) LED sealing (2) Organic EL, inorganic EL, laser diode sealing (or coating agent, peripheral member, etc.),
(3) Other coating agents such as DVD and glasses, optical communication-related members such as optical waveguides, optical fibers and adhesives, modification of general-purpose resins such as thermoplastic resins and thermosetting resins, interlayer insulating films, and photocuring (Molding) materials etc.
（Ａ）ポリオルガノシロキサン
（Ａ）成分のポリオルガノシロキサンとしては、例えば、特許文献７に記載されている一分子中に２個以上のビニル基、アリル基等の炭素数２〜８、特に２〜６のアルケニル基で代表される脂肪族不飽和結合を有するものが使用することができる。つまり、（Ｂ）成分のポリオルガノハイドロジェンシロキサン及び白金族金属系触媒と付加重合反応を行い硬化体を形成するものであれば、特に限定されるものではなく、直鎖状、環状、分岐状、三次元網目構造のいずれであってもよい。
(A) Polyorganosiloxane (A) The polyorganosiloxane of component (A) is, for example, 2 to 8 carbon atoms such as 2 or more vinyl groups and allyl groups in one molecule described in Patent Document 7, particularly 2 Those having an aliphatic unsaturated bond represented by -6 alkenyl groups can be used. That is, it is not particularly limited as long as it forms a cured product by performing an addition polymerization reaction with the polyorganohydrogensiloxane and the platinum group metal catalyst as the component (B), and is linear, cyclic, branched. Any of a three-dimensional network structure may be used.
ここで、ポリオルガノシロキサンの有機官能基としては、一価炭化水素基では、炭素数１〜１０、特に１〜６のものが好ましく、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ネオペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、ノニル基、デシル基等のアルキル基、フェニル基、トリル基、キシリル基、ナフチル基等のアリール基、ベンジル基、フェニルエチル基、フェニルプロピル基等のアラルキル基、ビニル基、アリル基、プロペニル基、イソプロペニル基、ブテニル基、ヘキセニル基、シクロヘキセニル基、オクテニル基等のアルケニル基や、これらの基の水素原子の一部又は全部をフッ素、臭素、塩素等のハロゲン原子、シアノ基等で置換したもの、例えばクロロメチル基、クロロプロピル基、ブロモエチル基、トリフロロプロピル基等のハロゲン置換アルキル基やシアノエチル基等が挙げられる。 Here, the organic functional group of the polyorganosiloxane is preferably a monovalent hydrocarbon group having 1 to 10 carbon atoms, particularly 1 to 6 carbon atoms, specifically, methyl group, ethyl group, propyl group, isopropyl group. Group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group, alkyl group such as decyl group, phenyl group, tolyl group, xylyl group, naphthyl group, etc. Aralkyl groups such as aryl group, benzyl group, phenylethyl group, phenylpropyl group, vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, hexenyl group, cyclohexenyl group, octenyl group and the like, Place some or all of the hydrogen atoms in these groups with halogen atoms such as fluorine, bromine and chlorine, cyano groups, etc. Which was, for example, chloromethyl group, chloropropyl group, bromoethyl group, and a halogen-substituted alkyl group or cyanoethyl group such trifluoropropyl group.
（Ｂ）ポリオルガノハイドロジェンシロキサン及び白金族金属系触媒
（Ｂ）成分のポリオルガノハイドロジェンシロキサンとしては、一分子中に２個以上のケイ素原子に結合した水素原子を有するポリオルガノハイドロジェンシロキサンであり、上記のポリオルガノシロキサンの脂肪族不飽和結合とケイ素原子に結合した水素原子とが付加重合反応することにより硬化体を形成するものであり、直鎖状、環状、分岐状、三次元網目構造のいずれであってもよい。
(B) Polyorganohydrogensiloxane and platinum group metal-based catalyst (B) The polyorganohydrogensiloxane is a polyorganohydrogensiloxane having hydrogen atoms bonded to two or more silicon atoms in one molecule. A cured product is formed by an addition polymerization reaction between the aliphatic unsaturated bond of the polyorganosiloxane and a hydrogen atom bonded to a silicon atom, and a linear, cyclic, branched, three-dimensional network. Any of the structures may be used.
具体的には、１，１，３，３−テトラメチルジシロキサン、１，３，５，７−テトラメチルシクロテトラシロキサン、両末端トリメチルシロキシ基封鎖メチルハイドロジェンポリシロキサン、両末端トリメチルシロキシ基封鎖ジメチルシロキサン・メチルハイドロジェンシロキサン共重合体、両末端ジメチルハイドロジェンシロキシ基封鎖ジメチルポリシロキサン、両末端ジメチルハイドロジェンシロキシ基封鎖ジメチルシロキサン・メチルハイドロジェンシロキサン共重合体、両末端トリメチルシロキシ基封鎖メチルハイドロジェンシロキサン・ジフェニルシロキサン共重合体、両末端トリメチルシロキシ基封鎖メチルハイドロジェンシロキサン・ジフェニルシロキサン・ジメチルシロキサン共重合体、（ＣＨ3）2ＨＳｉＯ1/2単位とＳｉＯ4/2単位とから成る共重合体、（ＣＨ3）2ＨＳｉＯ1/2単位とＳｉＯ4/2単位と（Ｃ6Ｈ5）3ＳｉＯ3/2単位とから成る共重合体などが挙げられる。 Specifically, 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, both ends trimethylsiloxy group blocked methylhydrogenpolysiloxane, both ends trimethylsiloxy group blocked Dimethylsiloxane / methylhydrogensiloxane copolymer, both ends dimethylhydrogensiloxy group-blocked dimethylpolysiloxane, both ends dimethylhydrogensiloxy group-blocked dimethylsiloxane / methylhydrogensiloxane copolymer, both ends trimethylsiloxy group-blocked methylhydro Disiloxane / diphenylsiloxane copolymer, trimethylsiloxy group-blocked methylhydrogensiloxane / diphenylsiloxane / dimethylsiloxane copolymer, (CH 3 ) 2 HSiO 1/2 unit and Si Copolymers composed of O 4/2 units, copolymers composed of (CH 3 ) 2 HSiO 1/2 units, SiO 4/2 units, and (C 6 H 5 ) 3 SiO 3/2 units. It is done.
また白金族金属系触媒としては、本発明の組成物の付加重合反応を生じさせるために配合されるものであり、白金系、パラジウム系、ロジウム系のものがあるが、コスト等の見地から白金、白金黒、塩化白金酸などの白金系のもの、例えば、Ｈ2ＰｔＣｌ6・ｍＨ2Ｏ，Ｋ2ＰｔＣｌ6，ＫＨＰｔＣｌ6・ｍＨ2Ｏ，Ｋ2ＰｔＣｌ4，Ｋ2ＰｔＣｌ4・ｍＨ2Ｏ，ＰｔＯ2・ｍＨ2Ｏ（ｍは、正の整数）等や、これらと、オレフィン等の炭化水素、アルコール又はビニル基含有オルガノポリシロキサンとの錯体等を例示することができ、これらは単独でも、２種以上の組み合わせでも使用することができる。これらの触媒成分の配合量は、いわゆる触媒量でよく、（Ａ）成分及び（Ｂ）成分の合計量に対して白金族金属換算（重量）で０．１〜１，０００ｐｐｍ、好ましくは０．５〜２００ｐｐｍの範囲で使用される。 In addition, platinum group metal-based catalysts are blended to cause the addition polymerization reaction of the composition of the present invention, and include platinum-based, palladium-based, and rhodium-based catalysts. Platinum series such as platinum black, chloroplatinic acid, for example, H 2 PtCl 6 · mH 2 O, K 2 PtCl 6 , KHPtCl 6 · mH 2 O, K 2 PtCl 4 , K 2 PtCl 4 · mH 2 O , PtO 2 · mH 2 O (m is a positive integer) and the like, and complexes of these with hydrocarbons such as olefins, alcohols or vinyl group-containing organopolysiloxanes, etc. Two or more combinations can also be used. The compounding amount of these catalyst components may be a so-called catalyst amount, and is 0.1 to 1,000 ppm in terms of platinum group metal (weight) with respect to the total amount of component (A) and component (B), preferably 0.00. Used in the range of 5 to 200 ppm.
ここで、ポリオルガノハイドロジェンシロキサンの有機官能基としては、一価炭化水素基では、炭素数１〜１０、特に１〜６のものが好ましく、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ネオペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、ノニル基、デシル基等のアルキル基、フェニル基、トリル基、キシリル基、ナフチル基等のアリール基、ベンジル基、フェニルエチル基、フェニルプロピル基等のアラルキル基、これらの基の水素原子の一部又は全部をフッ素、臭素、塩素等のハロゲン原子、シアノ基等で置換したもの、例えばクロロメチル基、クロロプロピル基、ブロモエチル基、トリフロロプロピル基等のハロゲン置換アルキル基やシアノエチル基等が挙げられる。 Here, the organic functional group of the polyorganohydrogensiloxane is preferably a monovalent hydrocarbon group having 1 to 10 carbon atoms, particularly 1 to 6 carbon atoms, specifically, a methyl group, an ethyl group, or a propyl group. , Isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group, decyl group and other alkyl groups, phenyl group, tolyl group, xylyl group, naphthyl group Aryl groups such as aralkyl groups, aralkyl groups such as benzyl groups, phenylethyl groups, phenylpropyl groups, etc., and some or all of the hydrogen atoms of these groups substituted with halogen atoms such as fluorine, bromine, chlorine, cyano groups, etc. For example, halogen-substituted alkyl groups such as chloromethyl group, chloropropyl group, bromoethyl group, trifluoropropyl group, etc. Anoechiru group, and the like.
なお、本発明に用いられる（Ａ）成分及び（Ｂ）成分としては、具体的には、例えば熱硬化性シリコン封止剤として信越化学工業株式会社から、商品名：ＬＰＳ−７５２０、ＬＰＳ−７５３０、東レ・ダウコーニング株式会社から、商品名：ＥＧ６３０１、ＳＲ７０１０として、２液性の形態で商品化されており、本発明に用いることができる。 As the component (A) and the component (B) used in the present invention, specifically, for example, as thermosetting silicone sealants, Shin-Etsu Chemical Co., Ltd. has trade names: LPS-7520, LPS-7530. From Toray Dow Corning Co., Ltd., they are commercialized in a two-part form as product names: EG6301 and SR7010, and can be used in the present invention.
（Ｃ）ポリオルガノシルセスキオキサン
本発明に（Ｃ）成分として用いられるポリオルガノシルセスキオキサンは、中でも下記式〔１〕及び式〔２〕
(C) Polyorganosilsesquioxane The polyorganosilsesquioxane used as the component (C) in the present invention includes the following formulas [1] and [2].
（式中、Ｒ1、Ｒ２及びＲ４は同じか又は異なる非置換基もしくは置換一価炭化水素基であり、Ｒ３、Ｒ５及びＲ６は水素原子およびアルキル基を示す。）
で表される末端基を有するポリオルガノシルセスキオキサンが好ましく用いられる。
(In the formula, R 1 , R 2 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and R 3 , R 5 and R 6 represent a hydrogen atom and an alkyl group.)
A polyorganosilsesquioxane having a terminal group represented by the formula is preferably used.
ここで、ポリオルガノシルセスキオキサンの有機官能基としては以下のようなものが例示される。すなわち、Ｒ1、Ｒ２およびＲ４の一価炭化水素基としては、炭素数１〜２０、特に１〜６のものが好ましく、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ネオペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、ノニル基、デシル基、アダマンチル機等のアルキル基、フェニル基、トリル基、キシリル基、ナフチル基等のアリール基、ベンジル基、フェニルエチル基、フェニルプロピル基等のアラルキル基、ビニル基、アリル基、プロペニル基、イソプロペニル基、ブテニル基、ヘキセニル基、シクロヘキセニル基、オクテニル基等のアルケニル基や、これらの基の水素原子の一部又は全部をフッ素、臭素、塩素等のハロゲン原子、シアノ基、エポキシ基、アクリロキシ基、アミノ基等の反応性官能基等で置換したもの、例えばクロロメチル基、クロロプロピル基、ブロモエチル基、トリフロロプロピル基等のハロゲン置換アルキル基、シアノエチル基、３−グリシドキシプロピル基、３−メタクリロキシプロピル基や３−アミノプロピル基等が挙げられる。 Here, examples of the organic functional group of polyorganosilsesquioxane include the following. That is, as the monovalent hydrocarbon group for R 1 , R 2 and R 4 , those having 1 to 20 carbon atoms, particularly 1 to 6 carbon atoms are preferred, and specifically, methyl group, ethyl group, propyl group, isopropyl group Butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group, decyl group, alkyl group such as adamantyl machine, phenyl group, tolyl group, xylyl group, naphthyl Aryl groups such as benzyl groups, aralkyl groups such as benzyl groups, phenylethyl groups, phenylpropyl groups, alkenyl groups such as vinyl groups, allyl groups, propenyl groups, isopropenyl groups, butenyl groups, hexenyl groups, cyclohexenyl groups, octenyl groups, etc. Or some or all of the hydrogen atoms in these groups may be halogen atoms such as fluorine, bromine, chlorine, cyano groups, Substituted by reactive functional groups such as xy group, acryloxy group, amino group, for example, halogen-substituted alkyl groups such as chloromethyl group, chloropropyl group, bromoethyl group, trifluoropropyl group, cyanoethyl group, 3-glycid Examples include a xylpropyl group, a 3-methacryloxypropyl group, and a 3-aminopropyl group.
また、Ｒ３、Ｒ５およびＲ６のアルキル基としては、炭素数１〜１０、特に１〜６のものが好ましく、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ネオペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、ノニル基、デシル基等のアルキル基が挙げられる。 The alkyl group of R 3, R 5 and R 6, 1 to 10 carbon atoms, particularly preferably having 1 to 6, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group And alkyl groups such as isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group and decyl group.
なお、本発明に用いられる（Ｃ）成分であるポリオルガノシルセスキオキサンとしては、具体的には、例えばラダー型のポリオルガノシルセスキオキサンのオリゴマーとして昭和電工株式会社から、ポリフェニルシルセスキオキサン（商品名:ＧＲ９５０）、ポリメチルシルセスキオキサン（商品名:ＧＲ６５０）、ポリメチルフェニルシルセスキオキサン（商品名:ＧＲ１００）等が商品化されており、（Ａ）及び／又は（Ｂ）成分に相溶させて本発明に用いることができる。 The polyorganosilsesquioxane, component (C) used in the present invention, specifically, for example, as a ladder-type polyorganosilsesquioxane oligomer from Showa Denko K.K. Oxan (trade name: GR950), polymethylsilsesquioxane (trade name: GR650), polymethylphenylsilsesquioxane (trade name: GR100), etc. are commercialized, and (A) and / or ( It can be used in the present invention by being dissolved in component B).
また、上記の様なオリゴマーのポリオルガノシルセスキオキサンではなく、平均粒子径が１００ｎｍ以下の微粒子状高分子量体のポリオルガノシルセスキオキサンを（Ａ）及び／又は（Ｂ）成分に分散させて本発明に用いることができる。なお、平均粒子径としては、光透過性の面で５０ｎｍ以下が好ましく、更に好ましくは２０ｎｍ以下が用いられる。 Also, instead of the oligomeric polyorganosilsesquioxane as described above, a finely divided high molecular weight polyorganosilsesquioxane having an average particle size of 100 nm or less is dispersed in the component (A) and / or (B). Can be used in the present invention. In addition, as an average particle diameter, 50 nm or less is preferable at the surface of a light transmittance, More preferably, 20 nm or less is used.
上記（Ｃ）成分のポリオルガノシルセスキオキサンは、特に光半導体装置の耐衝撃性および耐擦傷性を改善するために配合されるものであり、（Ａ）成分、（Ｂ）及び（Ｃ）成分の合計量当り、５〜９０重量％の量で配合される。好ましくは１０〜７０重量％、更に好ましくは２０〜６０重量％配合される。（Ｃ）成分の配合量が少なすぎると、上記効果が十分達成されず、多すぎると、組成物の粘度が著しく高くなったり、硬化物にクラックが発生し易くなるなどの不利が生ずる。 The polyorganosilsesquioxane of the component (C) is blended particularly for improving the impact resistance and scratch resistance of the optical semiconductor device, and includes the components (A), (B) and (C). It is blended in an amount of 5 to 90% by weight based on the total amount of the components. Preferably it is 10 to 70 weight%, More preferably, 20 to 60 weight% is mix | blended. If the blending amount of the component (C) is too small, the above effect cannot be achieved sufficiently, and if it is too large, there are disadvantages such as the viscosity of the composition being remarkably increased or cracks being easily generated in the cured product.
本発明の光半導体封止用樹脂組成物には、その他任意の成分として、２−メチル−３−ブチン−２−オール、３，５−ジメチル−１−ヘキシン−３−オール、２−フェニル−３−ブチン−２−オール等のアルキンアルコール；３−メチル−３−ペンテン−１−イン等のエンイン化合物；１，３，５，７−テトタメチル−１，３，５，７−テトラビニルシクロテトラシロキサン、ベンゾトリアゾール等の反応抑制剤を含有してもよい。この反応抑制剤の含有量は限定されないが、（Ａ）成分及び（Ｂ）成分の合計量に対して０．０００１〜５重量部の範囲であることが好ましい。 In the resin composition for encapsulating an optical semiconductor of the present invention, as other optional components, 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, 2-phenyl- Alkyne alcohols such as 3-butyn-2-ol; Enyne compounds such as 3-methyl-3-penten-1-yne; 1,3,5,7-tetamethyl-1,3,5,7-tetravinylcyclotetra You may contain reaction inhibitors, such as siloxane and a benzotriazole. Although content of this reaction inhibitor is not limited, It is preferable that it is the range of 0.0001-5 weight part with respect to the total amount of (A) component and (B) component.
また、本発明の光半導体封止用樹脂組成物には、その接着性を向上させるための接着付与剤を含有していてもよい。この接着付与剤としては、３−グリシドキシプロピル基、４−グリシドキシブチル基等のグリシドキシアルキル基；２−（３，４−エポキシシクロヘキシル）エチル基、３−（３，４−エポキシシクロヘキシル）プロピル基等のエポキシシクロヘキシルアルキル基；４−オキシラニルブチル基、８−オキシラニルオクチル基等のオキシラニルアルキル基等のエポキシ基含有一価有機基であるシランカップリング剤が好ましく、（Ａ）、（Ｂ）及び（Ｃ）成分と反応し得る基を有するものであってもよいし、これらの官能基を有するオルガノシロキサンオリゴマーであってもよい。また、上記組成物において、この接着付与剤の含有量は限定されないが、（Ａ）、（Ｂ）及び（Ｃ）成分の合計１００重量部に対して０．０１〜１０重量部の範囲内であることが好ましい。 Moreover, the resin composition for optical semiconductor sealing of this invention may contain the adhesion imparting agent for improving the adhesiveness. Examples of the adhesion promoter include glycidoxyalkyl groups such as 3-glycidoxypropyl group and 4-glycidoxybutyl group; 2- (3,4-epoxycyclohexyl) ethyl group, 3- (3,4- A silane coupling agent which is an epoxy group-containing monovalent organic group such as an epoxycyclohexylalkyl group such as epoxycyclohexyl) propyl group; an oxiranylalkyl group such as 4-oxiranylbutyl group and 8-oxiranyloctyl group; Preferably, it may have a group capable of reacting with the components (A), (B) and (C), or may be an organosiloxane oligomer having these functional groups. Moreover, in the said composition, although content of this adhesion | attachment imparting agent is not limited, within the range of 0.01-10 weight part with respect to a total of 100 weight part of (A), (B) and (C) component. Preferably there is.
また、本発明の光半導体封止用樹脂組成物には、イットリウム・アルミニウム・ガーネット系（ＹＡＧ）等の蛍光体を含有してもよい。この蛍光体の含有量は限定されないが、本発明の光半導体封止用樹脂組成物の１〜２０重量％の範囲内であることが好ましく、特に、５〜１５重量％の範囲内であることが好ましい。また、本発明の光半導体封止用樹脂組成物には、本発明の目的を損なわない限り、その他任意の成分として、シリカ、ガラス、アルミナ、酸化亜鉛等の無機質充填剤、ポリメタクリレート樹脂等の有機樹脂微粉末、耐熱剤、染料、顔料、難燃性付与剤、溶剤等を含有してもよい。 The resin composition for encapsulating an optical semiconductor of the present invention may contain a phosphor such as yttrium / aluminum / garnet (YAG). Although content of this fluorescent substance is not limited, it is preferably in the range of 1 to 20% by weight of the resin composition for sealing an optical semiconductor of the present invention, and particularly in the range of 5 to 15% by weight. Is preferred. Further, in the resin composition for encapsulating an optical semiconductor of the present invention, as long as the purpose of the present invention is not impaired, as other optional components, inorganic fillers such as silica, glass, alumina, zinc oxide, polymethacrylate resin, etc. You may contain organic resin fine powder, a heat-resistant agent, dye, a pigment, a flame-retarding agent, a solvent, etc.
なお、本発明の光半導体用封止樹脂組成物の硬化条件は、室温（２５℃）〜２００℃の範囲で、その作業条件に合わせて任意に時間を設定でき、生産性と発光素子や筐体耐熱性とのバランスから適宜選定することができる。 The curing condition of the encapsulating resin composition for optical semiconductors of the present invention is in the range of room temperature (25 ° C.) to 200 ° C., and the time can be arbitrarily set according to the working conditions. It can select suitably from balance with body heat resistance.
以下、実施例と比較例を示し、本発明を更に具体的詳細に説明するが、本発明は下記の実施例に制限されるものではない。 EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated further in detail, this invention is not restrict | limited to the following Example.
［実施例１〜４、比較例１］
（Ａ）、（Ｂ）及び（Ｃ）成分を下表１に示す割合で配合し（配合数値の単位は重量部である。）、光半導体用封止樹脂組成物を得た。ついで、光半導体用封止樹脂組成物をディスペンサーにセットし、アルミ板（２０ｍｍ×５０ｍｍ×１ｍｍ）に１０ｍｇ±１０％×１０点をポッティング、及びφ５０ｍｍ×１ｍｍの金型に注型し、同表に示す硬化条件で硬化させ、評価用テストピースを得た。
[Examples 1 to 4, Comparative Example 1]
(A), (B), and (C) component were mix | blended in the ratio shown in the following table 1 (the unit of a mixing | blending numerical value is a weight part), and the sealing resin composition for optical semiconductors was obtained. Next, the sealing resin composition for optical semiconductors was set in a dispenser, 10 mg ± 10% × 10 points were potted on an aluminum plate (20 mm × 50 mm × 1 mm), and poured into a 50 mm × 1 mm mold. The test piece for evaluation was obtained by curing under the curing conditions shown in FIG.
＊１：EG6301A＝ポリオルガノシロキサン(東レ・ダウコーニング株式会社製)
＊２：EG6301B＝ポリオルガノハイドロジェンシロキサン＋白金族金属系触媒(東レ・ダウコーニング株式会社製)
＊３：GR950＝ポリフェニルシルセスキオキサン（昭和電工株式会社製)
* 1 : EG6301A = polyorganosiloxane (manufactured by Dow Corning Toray)
* 2 : EG6301B = polyorganohydrogensiloxane + platinum group metal catalyst (manufactured by Dow Corning Toray)
* 3 : GR950 = polyphenylsilsesquioxane (manufactured by Showa Denko KK)
このようにして得られた実施例および比較例の硬化物について、下記の方法で接着性、耐擦傷性、硬化直後の光透過性、耐熱性、耐光性および屈折率を評価した。また、その結果を表２に示す。 The cured products of Examples and Comparative Examples thus obtained were evaluated for adhesiveness, scratch resistance, light transmittance immediately after curing, heat resistance, light resistance and refractive index by the following methods. The results are shown in Table 2.
［接着性および耐擦傷性］
アルミ板状で作製した硬化物の表面を爪で１０回こすりつけて、接着性および表面の傷つき度合いを評価した。爪を１０回こすりつけた後に、アルミ板から硬化物が外れない場合：接着性○、アルミ板から１〜３個外れた場合：接着性△、アルミ板から４個以上外れた場合：接着性×と評価した。また、爪を１０回こすりつけた後に、傷がない場合：耐擦傷性○、爪を２〜１０回こすりつけた後に、傷がある場合：耐擦傷性△、爪を１回こすりつけた後に傷がある場合：耐擦傷性×と評価した。
[Adhesion and scratch resistance]
The surface of the cured product produced in the form of an aluminum plate was rubbed 10 times with a nail to evaluate the adhesion and the degree of scratching on the surface. If the cured product does not come off the aluminum plate after rubbing the nails 10 times: Adhesiveness ○, 1 to 3 pieces removed from the aluminum plate: Adhesive Δ, 4 pieces or more removed from the aluminum plate: Adhesiveness × It was evaluated. In addition, when there is no scratch after rubbing the nail 10 times: scratch resistance ○, when there is a scratch after rubbing the nail 2 to 10 times: scratch resistance Δ, there is a scratch after rubbing the nail once Case: Evaluated as scratch resistance x.
［硬化直後の光透過性］
上記の方法で得られた硬化物を分光光度計（日立製：Ｕ−２００１）にセットし、３５０ｎｍ、４００ｎｍ、８００ｎｍの波長における透過率（％）を測定・評価した。
［耐熱性］
上記の方法で得られた硬化物を１５０℃のギヤオーブンに７２時間放置した後、上記と同様の方法で透過率を測定・評価した。
[Light transmittance immediately after curing]
The cured product obtained by the above method was set in a spectrophotometer (manufactured by Hitachi: U-2001), and the transmittance (%) at wavelengths of 350 nm, 400 nm, and 800 nm was measured and evaluated.
[Heat-resistant]
The cured product obtained by the above method was left in a gear oven at 150 ° C. for 72 hours, and the transmittance was measured and evaluated by the same method as described above.
［耐光性］
上記の方法で得られた硬化物を２６Ｗ／ｍ２（３００〜４００ｎｍ）の照度、温度５０℃の促進耐光試験機（スガ試験機製：サンテスターＸＴ７５０）に１００時間放置した後、上記と同様の方法で透過率を測定・評価した。
[Light resistance]
The cured product obtained by the above method was allowed to stand for 100 hours in an accelerated light resistance tester (Suga Test Instruments: SUNTESTER XT750) having an illuminance of 26 W / m 2 (300 to 400 nm) and a temperature of 50 ° C. The transmittance was measured and evaluated by the method.
なお、下表の表２中の硬化物の耐熱性および耐光性における評価基準は、硬化直後の透過率の９５％以上を維持しているものを「◎」、９５未満〜９０％以上のものを「○」、９０％未満〜８０％以上のものを「△」、８０％未満のものを「×」と示した。 The evaluation criteria for the heat resistance and light resistance of the cured products in Table 2 in the following table are “◎” when the transmittance immediately after curing is maintained at 95% or more, and those with less than 95 to 90% or more. Is indicated by “◯”, less than 90% to 80% or more is indicated by “Δ”, and less than 80% is indicated by “X”.
［屈折率］
上記の割合で混合した混合液を屈折計（京都電子工業社製：ＲＡ−５００Ｎ）にセットし、２５℃における屈折率を測定・評価した。
[Refractive index]
The mixed liquid mixed at the above ratio was set in a refractometer (manufactured by Kyoto Electronics Co., Ltd .: RA-500N), and the refractive index at 25 ° C. was measured and evaluated.
［実施例５］
［合成例］
ポリメチルシルセスキオキサン微粒子分散液の合成法（蒸留による有機溶媒置換）
蒸留水８８８．９ｇに１Ｎアンモニア水１１．１ｇ、硫酸ドデシルナトリウム１３．５ｇを加えた混合液に、メチルトリメトキシシラン１００ｇを２５℃で１３５分かけて滴下した後、同温度で攪拌を１６時間行い、１Ｎ硫酸水溶液でｐＨ７に調整することで、透明なポリメチルシルセスキオキサン微粒子水分散液１０１３．５ｇを得た。この水分散液を１Ｎ硫酸水溶液でｐＨ７に調整した後、蒸留対象液中の水分が５％以下となるまでメチルエチルケトン２０００ｇを滴下しつつ減圧蒸留を行うことによって、メチルエチルケトンのポリメチルシルセスキオキサン微粒子分散液２５７ｇを得た。得られたポリメチルシルセスキオキサンの平均粒子径を動的光散乱法により測定した結果、１８．４ｎｍであった。また、分散液中のポリメチルシルセスキオキサンの固形分濃度を１１０℃における重量減少より計算した結果、２０．０％であった。
[Example 5]
[Synthesis example]
Synthesis method of polymethylsilsesquioxane fine particle dispersion (substitution of organic solvent by distillation)
To a mixture of 888.9 g of distilled water and 11.1 g of 1N ammonia water and 13.5 g of sodium dodecyl sulfate, 100 g of methyltrimethoxysilane was added dropwise at 25 ° C. over 135 minutes, and the mixture was stirred at the same temperature for 16 hours. This was adjusted to pH 7 with a 1N aqueous sulfuric acid solution to obtain 1013.5 g of a transparent polymethylsilsesquioxane fine particle aqueous dispersion. This aqueous dispersion is adjusted to pH 7 with 1N sulfuric acid aqueous solution, and then distilled under reduced pressure while adding 2000 g of methyl ethyl ketone dropwise until the water in the liquid to be distilled becomes 5% or less, thereby producing polymethylsilsesquioxane fine particles of methyl ethyl ketone. 257 g of a dispersion was obtained. It was 18.4 nm as a result of measuring the average particle diameter of the obtained polymethylsilsesquioxane by the dynamic light scattering method. The solid content concentration of polymethylsilsesquioxane in the dispersion was calculated from the weight loss at 110 ° C. and found to be 20.0%.
（Ａ）成分である東レ・ダウコーニング株式会社製のポリオルガノシロキサン（ＥＧ６３０１Ａ）４０ｇに上記で得られたポリメチルシルセスキオキサン微粒子分散液１００ｇを加え、減圧下にメチルエチルケトンを回収し、ポリメチルシルセスキオキサン微粒子を分散した（Ａ）成分を得た。 100 g of the polymethylsilsesquioxane fine particle dispersion obtained above is added to 40 g of polyorganosiloxane (EG6301A) manufactured by Toray Dow Corning Co., Ltd. as component (A), and methyl ethyl ketone is recovered under reduced pressure. A component (A) in which silsesquioxane fine particles were dispersed was obtained.
このようにして得られた（Ａ）成分及び（Ｂ）成分を下表３に示す割合で配合し（配合数値の単位は重量部である。）、光半導体用封止樹脂組成物を得た。ついで、光半導体用封止樹脂組成物をディスペンサーにセットし、アルミ板（２０ｍｍ×５０ｍｍ×１ｍｍ）に１０ｍｇ±１０％×１０点をポッティング、及びφ５０ｍｍ×１ｍｍの金型に注型し、同表に示す硬化条件で硬化させ、評価用テストピースを得た。 The component (A) and the component (B) thus obtained were blended in the proportions shown in Table 3 below (units of blending numerical values are parts by weight) to obtain an encapsulating resin composition for optical semiconductors. . Next, the sealing resin composition for optical semiconductors was set in a dispenser, 10 mg ± 10% × 10 points were potted on an aluminum plate (20 mm × 50 mm × 1 mm), and poured into a 50 mm × 1 mm mold. The test piece for evaluation was obtained by curing under the curing conditions shown in FIG.
［実施例６〜８］
（Ａ）成分に分散する（Ｃ）成分のポリメチルシルセスキオキサン微粒子分散液の添加量を下表３のとおりに変更した以外は、実施例５と同様の方法で実施例６乃至８を行った。
[Examples 6 to 8]
Examples 6 to 8 were prepared in the same manner as in Example 5 except that the addition amount of the polymethylsilsesquioxane fine particle dispersion of component (C) dispersed in component (A) was changed as shown in Table 3 below. went.
＊２：EG6301B＝ポリオルガノハイドロジェンシロキサン＋白金族金属系触媒(東レ・ダウコーニング株式会社製)
* 2 : EG6301B = polyorganohydrogensiloxane + platinum group metal catalyst (manufactured by Dow Corning Toray)
このようにして得られた実施例の硬化物について、接着性、耐擦傷性、硬化直後の光透過性、耐熱性、耐光性および屈折率を評価した。また、その結果を表４に示す。 The cured products of the examples thus obtained were evaluated for adhesiveness, scratch resistance, light transmittance immediately after curing, heat resistance, light resistance and refractive index. The results are shown in Table 4.
本発明の光半導体封止用樹脂組成物は、光透過性、耐熱性及び耐光性に優れ、且つ発光素子及びフレーム等との接着性に優れ、しかも硬度が高く、耐衝撃性及び耐擦傷性に優れた光半導体封止用樹脂組成物であり、該樹脂組成物を用いて光半導体素子を公知の方法で封止した結果、光透過性、耐熱性及び耐光性に優れ、且つ接着性、耐擦傷性が優れ、発光効率の高い光半導体装置が得られる。
The resin composition for encapsulating an optical semiconductor of the present invention is excellent in light transmittance, heat resistance and light resistance, excellent in adhesion to a light emitting element and a frame, and has high hardness, impact resistance and scratch resistance. Is a resin composition for optical semiconductor sealing excellent in, and as a result of sealing an optical semiconductor element by a known method using the resin composition, it has excellent light transmittance, heat resistance and light resistance, and adhesion, An optical semiconductor device having excellent scratch resistance and high luminous efficiency can be obtained.
Claims (6)
（Ｂ）ポリオルガノハイドロジェンシロキサン及び白金族金属系触媒、
（Ｃ）ポリオルガノシルセスキオキサン、
を含有することを特徴とする光半導体封止用樹脂組成物。 (A) a polyorganosiloxane having two or more aliphatic unsaturated bonds in one molecule;
(B) polyorganohydrogensiloxane and platinum group metal catalyst,
(C) polyorganosilsesquioxane,
A resin composition for encapsulating an optical semiconductor.
（式中、Ｒ1、Ｒ２及びＲ４は同じか又は異なる非置換基もしくは置換一価炭化水素基であり、Ｒ３、Ｒ５及びＲ６は水素原子およびアルキル基を示す。）
で表される末端基を有するポリオルガノシルセスキオキサンである請求項１記載の光半導体封止用樹脂組成物。 The polyorganosilsesquioxane of component (C) is represented by the following formula [1] and formula [2]
(In the formula, R 1 , R 2 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and R 3 , R 5 and R 6 represent a hydrogen atom and an alkyl group.)
The resin composition for optical semiconductor encapsulation according to claim 1, which is a polyorganosilsesquioxane having a terminal group represented by the formula:
6. An optical semiconductor device comprising an optical semiconductor element sealed with the optical semiconductor sealing resin composition according to claim 1.
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