JP2005307015A - Curable composition for sealing optical material - Google Patents
Curable composition for sealing optical material Download PDFInfo
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Description
本発明は、半導体素子等の封止材料として用いられる硬化性組成物に関するものである。 The present invention relates to a curable composition used as a sealing material for semiconductor elements and the like.
光学用のプラスチック材料には、高い透明性および高屈折率が要求され、従来はエポキシ樹脂、ポリメチルメタクリレート、ポリカーボネートが多用されていたが、これらの材料は長期にわたる高温の環境下では変形、変色などが生じるので、耐熱性が求められる状況では光学材料として適さない。 Optical plastic materials are required to have high transparency and a high refractive index. Conventionally, epoxy resin, polymethyl methacrylate, and polycarbonate have been widely used. However, these materials are deformed and discolored under long-term high-temperature environments. Therefore, it is not suitable as an optical material in a situation where heat resistance is required.
これらの用途に用いうる材料としてシリコーン樹脂が注目されてきており、光学材料として必要な高屈折率を得るためには、ポリオルガノシロキサンベースポリマーの一部または全部としてフェニル変性ポリオルガノシロキサンを用いるのが一般的である（特許文献１）。 Silicone resin has attracted attention as a material that can be used in these applications, and in order to obtain a high refractive index required as an optical material, phenyl-modified polyorganosiloxane is used as part or all of the polyorganosiloxane base polymer. Is common (Patent Document 1).
ところが、このようなフェニル基変性されたシロキサンポリマーは、一般のジメチル系シロキサンポリマーに比べ非常に脆く、強度不足であるという欠点があり、特にフェニル基変性されたシロキサンポリマーを光学材料用の封止材として用いる場合、ハンダ熱等の加熱により、硬化物が容易にクラックを発生し、基材との剥離を起こしてしまうという問題がある。これは、フェニル基変性シロキサンポリマーをベースとしたシリコーンゴムは、同程度の粘度のジメチル系シリコーンゴムに比べ、ポリマー鎖が短いため、硬化物の伸びが小さく、加熱による硬化物の膨張、収縮に追従できないことが要因の一つと考えられる。 However, such phenyl group-modified siloxane polymers are disadvantageous in that they are very brittle and insufficient in strength compared to general dimethyl-based siloxane polymers. In particular, phenyl group-modified siloxane polymers are encapsulated for optical materials. When used as a material, there is a problem that the cured product easily cracks due to heating such as soldering heat and peels off from the substrate. This is because silicone rubber based on a phenyl group-modified siloxane polymer has a shorter polymer chain than dimethyl silicone rubber of the same viscosity, so that the cured product has a small elongation and can be expanded and contracted by heating. The inability to follow is one of the factors.
この問題を回避する手段として、硬化物の低硬度化（ゲル状物の使用を含む）が考えられるが、硬化物がベタツキ、作業性が悪くなるという問題がある。
本発明は、高屈折率を有するフェニル変性ポリオルガノシロキサンをベースポリマーとしつつ、加熱によってもクラック発生、基材との剥離を生じない光学材料封止用硬化性組成物の提供を目的とする。 An object of the present invention is to provide a curable composition for encapsulating an optical material that uses a phenyl-modified polyorganosiloxane having a high refractive index as a base polymer, and does not generate cracks or peel off from a substrate even when heated.
本発明者らは上記目的を達成するために鋭意検討した結果、フェニル変性ポリオルガノシロキサンとして、低沸点物を除去したものを使用することにより、加熱による重量減少、冷却による収縮を抑えることが可能であり、且つ低沸点物による屈折率低下にも有効に作用することを見出し、本発明を完成するに至った。 As a result of intensive studies to achieve the above object, the present inventors can suppress weight reduction by heating and shrinkage by cooling by using a phenyl-modified polyorganosiloxane from which low-boiling substances are removed. And the present invention has been found to be effective in reducing the refractive index due to low boiling point substances.
即ち本発明は、
２００℃×１時間の加熱減量が１．５重量％以下である、アルケニル基及びフェニル基含有ポリオルガノシロキサンをベースポリマーとしたことを特徴とする光学材料封止用硬化性組成物である。
That is, the present invention
An curable composition for encapsulating an optical material, characterized in that a base polymer is an alkenyl group- and phenyl group-containing polyorganosiloxane having a weight loss by heating of 200 ° C. × 1 hour of 1.5% by weight or less.
以下、本発明につき詳細に説明する。本発明の光学材料封止用硬化性組成物は、２００℃×１時間の加熱減量が１．５重量％以下である、アルケニル基及びフェニル基含有ポリオルガノシロキサンをベースポリマーとしたことを特徴とするものであり、必要量のオルガノハイドロジェンシロキサンとヒドロシリル化反応用触媒を含有するものを使用できるが、本発明の具体的に好ましい組成物としては、
（Ａ）１分子中に少なくとも２個のアルケニル基を有し、ＰｈＳｉＯ３／２及び／又はＰｈ２ＳｉＯ２／２単位（ただし、Ｐｈはフェニル基である）を５モル％以上有し、２００℃×１時間の加熱減量が１．５重量％以下であるポリオルガノシロキサン
（Ｂ）アルケニル基含有環状イソシアネート化合物；（Ａ）成分中のアルケニル基１モルに対してアルケニル基が０．０１〜２モルとなる量
（Ｃ）１分子中に少なくとも３個のＳｉＨ結合を有するオルガノハイドロジェンシロキサン；（Ａ）、（Ｂ）成分中のアルケニル基１モルに対してＳｉＨ結合が０．４〜５モルとなる量
（Ｄ）ヒドロシリル化反応用触媒
を含有することを特徴とする光学材料封止用硬化性組成物である。
Hereinafter, the present invention will be described in detail. The curable composition for encapsulating an optical material according to the present invention is characterized in that an alkenyl group- and phenyl group-containing polyorganosiloxane having a loss on heating at 200 ° C. × 1 hour of 1.5 wt% or less is used as a base polymer. Although it is possible to use what contains the required amount of organohydrogensiloxane and hydrosilylation reaction catalyst, as a specifically preferred composition of the present invention,
(A) having at least two alkenyl groups in one molecule, having 5 mol% or more of PhSiO 3/2 and / or Ph 2 SiO 2/2 units (where Ph is a phenyl group), Polyorganosiloxane (B) alkenyl group-containing cyclic isocyanate compound having a heat loss of 1.5% by weight or less at 1 ° C for 1 hour; 0.01-2 alkenyl groups relative to 1 mol of alkenyl groups in component (A) (C) organohydrogensiloxane having at least 3 SiH bonds per molecule; (A), 0.4 to 5 moles of SiH bonds per mole of alkenyl group in component (B) (D) A curable composition for encapsulating an optical material, comprising a hydrosilylation reaction catalyst.
（Ａ）成分のポリオルガノシロキサンは本発明組成物のベースポリマーとなるものであり、１分子中に少なくとも２個のアルケニル基を有し、ＰｈＳｉＯ３／２及び／又はＰｈ２ＳｉＯ２／２単位（ただし、Ｐｈはフェニル基である）を５モル％以上有するものが好ましい。 The polyorganosiloxane of component (A) serves as the base polymer of the composition of the present invention, has at least two alkenyl groups in one molecule, and has PhSiO 3/2 and / or Ph 2 SiO 2/2 units. Those having 5 mol% or more (where Ph is a phenyl group) are preferred.
ＰｈＳｉＯ３／２及び／又はＰｈ２ＳｉＯ２／２単位が５モル％未満では、光学材料用として必要な高屈折率（２５℃における屈折率が１．４３以上）を得られない場合が多い。 When the PhSiO 3/2 and / or Ph 2 SiO 2/2 units are less than 5 mol%, the high refractive index necessary for optical materials (refractive index at 25 ° C. of 1.43 or more) is often not obtained.
（Ａ）成分のポリオルガノシロキサンは、その分子構造が直鎖状であっても、あるいはＰｈＳｉＯ３／２単位により分岐した構造を有するものであってもよく、またそれらを併用してもよい。 The polyorganosiloxane of the component (A) may have a linear molecular structure or a structure branched by PhSiO 3/2 units, or may be used in combination.
本発明では、アルケニル基及びフェニル基含有ポリオルガノシロキサンは、２００℃×１時間の加熱減量が１．５重量％以下であることが、本発明所期の効果を得る上で必須である。 In the present invention, it is essential for the alkenyl group- and phenyl group-containing polyorganosiloxane that the weight loss on heating at 200 ° C. × 1 hour is 1.5% by weight or less in order to obtain the intended effect of the present invention.
２００℃×１時間の加熱減量が１．５重量％を超えるものを使用したのでは、前述の如く、ハンダ熱等の加熱により、硬化物が容易にクラックを発生し、基材との剥離を起こしてしまうという問題がある。 When using a material whose weight loss on heating at 200 ° C. × 1 hour exceeds 1.5% by weight, as described above, the cured product easily cracks due to heating such as soldering heat and peels off from the substrate. There is a problem of waking up.
２００℃×１時間の加熱減量が１．５重量％以下のポリオルガノシロキサンを得る手段としては、環状シロキサン等の平衡化反応やクロロシラン類の加水分解反応等、周知の製造方法により製造されたポリオルガノシロキサンを薄膜化し、２ｍｍHg以下の減圧下で１５０℃以上に加熱する方法が挙げられる。 As means for obtaining a polyorganosiloxane having a weight loss of 1.5% by weight or less at 200 ° C. for 1 hour, a polyorganosiloxane produced by a well-known production method such as an equilibration reaction of cyclic siloxane or the like or a hydrolysis reaction of chlorosilanes is used. An example is a method in which an organosiloxane is thinned and heated to 150 ° C. or higher under a reduced pressure of 2 mmHg or lower.
尚、従来より、半導体素子被覆剤のベースポリマーとして、200℃で10mmHg以上の蒸気圧を有する低分子シロキサンの含有量を0.2重量％以下としたものを用いることにより、揮発する低分子シロキサンによる半導体装置部品表面の汚染を防止する技術（特許第３２０７９２９号）や、半導体ペレットと該ペレット取付部材とを接合するためのシリコーン接着剤のベースポリマーとして、200℃で10mmHg以上の蒸気圧を有する低分子シロキサンの含有量を500ppm以下としたものを用いることにより、接着性等を向上させる技術（特許第２８８２８２３号）が知られているが、何れも封止材料に関するものではなく、且つ本発明とはベースポリマー及び組成物の構成が異なり、本発明が解決しようとする課題に対する認識もなく、本発明を連想させるものではない。 Conventionally, a semiconductor with a low molecular weight siloxane that volatilizes by using a low molecular weight siloxane with a vapor pressure of 10 mmHg or higher at 200 ° C. of 0.2% by weight or lower as the base polymer of the semiconductor element coating agent. Low molecule having a vapor pressure of 10 mmHg or more at 200 ° C. as a base polymer of a silicone adhesive for joining a technology (Patent No. 3207929) for preventing contamination of the surface of equipment parts and a semiconductor pellet and the pellet mounting member A technique (Patent No. 2888223) for improving adhesiveness and the like by using a siloxane having a content of 500 ppm or less is known, but none relates to a sealing material, and the present invention The composition of the base polymer and the composition is different, and there is no recognition of the problems to be solved by the present invention, which is reminiscent of the present invention. No.
次に本発明で用いる（Ｂ）成分はアルケニル基含有環状イソシアネート化合物であり、組成物の高硬度化に作用するものである。 Next, the component (B) used in the present invention is an alkenyl group-containing cyclic isocyanate compound, which acts to increase the hardness of the composition.
（Ｂ）成分の具体例としては、トリアリルイソシアネート、ジアリル[３−(トリメトキシシリル)プロピル]イソシアネート等のＳｉＨ含有化合物とトリアリルイソシアネートとの反応物等が例示される。 Specific examples of the component (B) include a reaction product of a SiH-containing compound such as triallyl isocyanate and diallyl [3- (trimethoxysilyl) propyl] isocyanate and triallyl isocyanate.
（Ｂ）成分は、（Ａ）成分中のアルケニル基１モルに対してアルケニル基が０．０１〜２モルとなる量が用いられる。０．０1モルに満たない量では組成物の硬度にほとんど作用することなく、２モルを超える量では硬化反応の遅延効果が大きくなるばかりか、硬化物の伸びが著しく損なわれる。 The component (B) is used in such an amount that the alkenyl group is 0.01 to 2 mol with respect to 1 mol of the alkenyl group in the component (A). If the amount is less than 0.01 mol, the hardness of the composition is hardly affected. If the amount exceeds 2 mol, the effect of retarding the curing reaction is increased, and the elongation of the cured product is remarkably impaired.
次に本発明で用いる（Ｃ）成分は１分子中に少なくとも３個のＳｉＨ結合を有するオルガノハイドロジェンシロキサンである。かかる（Ｃ）成分は架橋成分として作用するものであり、一般的に周知のオルガノハイドロジェンシロキサンを使用することができる。 Next, the component (C) used in the present invention is an organohydrogensiloxane having at least three SiH bonds in one molecule. The component (C) acts as a crosslinking component, and generally known organohydrogensiloxanes can be used.
（Ｃ）成分の配合量は、（Ａ）、（Ｂ）成分中のアルケニル基１モルに対してＳｉＨ結合が０．４〜５モルとなる量である。０．４モルに満たない量では十分な架橋が得られず、５モルを超える量では未反応のＳｉＨ結合が残存し、物性が不安定となる。 The amount of component (C) is such that SiH bonds are 0.4 to 5 moles per mole of alkenyl groups in components (A) and (B). If the amount is less than 0.4 mol, sufficient crosslinking cannot be obtained, and if it exceeds 5 mol, unreacted SiH bonds remain and the physical properties become unstable.
本発明の（Ｄ）成分は、ヒドロシリル化反応用触媒であり、白金黒、塩化第二白金、塩化白金酸、塩化白金酸と一価アルコールとの反応物、塩化白金酸とオレフィン類やビニルシロキサンとの錯体、白金ビスアセトアセテート、パラジウム系触媒、ロジウム系触媒等が例示される。 Component (D) of the present invention is a catalyst for hydrosilylation reaction, such as platinum black, platinous chloride, chloroplatinic acid, a reaction product of chloroplatinic acid and monohydric alcohol, chloroplatinic acid and olefins, and vinyl siloxane. And complexes thereof, platinum bisacetoacetate, palladium-based catalysts, rhodium-based catalysts and the like.
好ましくは白金系触媒が用いられ、その使用量は硬化必要量であれば特に制限されず、（Ａ）〜（Ｃ）成分の種類、所望の硬化速度などに応じて適宜増減すべきであるが、一般的には、本発明の組成物の合計重量に対して０．０１〜１０００ｐｐｍの範囲とすればよい。特に１〜５００ｐｐｍであることが、硬化性、コストの面からも好ましい。 A platinum-based catalyst is preferably used, and the amount used thereof is not particularly limited as long as it is a necessary amount for curing, and should be appropriately increased or decreased depending on the types of components (A) to (C), a desired curing rate, and the like. In general, the content may be in the range of 0.01 to 1000 ppm based on the total weight of the composition of the present invention. In particular, 1 to 500 ppm is preferable from the viewpoint of curability and cost.
上記組成からなる本発明の硬化性組成物は、光学材料用としての用途から２５℃における屈折率が１．４３以上であることが望ましい。 The curable composition of the present invention having the above composition desirably has a refractive index of 1.43 or more at 25 ° C. for use as an optical material.
本発明は、（Ａ）特定のフェニル基変性ポリオルガノシロキサン、（Ｃ）オルガノハイドロジェンシロキサン、（Ｄ）ヒドロシリル化反応用触媒を基本的構成成分とする液状付加硬化型シリコーンゴム組成物に対し、（Ｂ）アルケニル基含有環状イソシアネート化合物を配合したものであり、低沸点物の少ない（Ａ）特定のフェニル基変性ポリオルガノシロキサンの使用により、加熱による重量減少、冷却による収縮を抑えることが可能であり、該（Ａ）成分と（Ｂ）成分との組合せにより硬化物に適度な硬度と強度を与えることが可能である。 The present invention relates to a liquid addition-curable silicone rubber composition comprising (A) a specific phenyl group-modified polyorganosiloxane, (C) an organohydrogensiloxane, and (D) a hydrosilylation reaction catalyst as basic components. (B) Blended with an alkenyl group-containing cyclic isocyanate compound. (A) Use of a specific phenyl group-modified polyorganosiloxane with few low-boiling substances can reduce weight loss due to heating and shrinkage due to cooling. There is a combination of the component (A) and the component (B), and it is possible to give the cured product appropriate hardness and strength.
このような本発明によれば、従来のシリコーンゴムには必須であった補強性向上（ゴム物性向上）のためのフィラー（補強性シリカ）の配合が実質的に不要であり、高屈折率、高透明性に優れた光学材料封止用硬化性組成物を提供することを可能とするが、本発明では、高屈折率を阻害しない範囲であれば補強性シリカを配合することはできる。 According to the present invention, it is substantially unnecessary to add filler (reinforcing silica) for improving reinforcing properties (improving rubber properties), which is essential for conventional silicone rubber, and has a high refractive index. Although it is possible to provide a curable composition for sealing an optical material excellent in high transparency, in the present invention, reinforcing silica can be blended as long as the high refractive index is not inhibited.
その他、本発明の組成物には、必要に応じて反応を制御するための反応制御剤、例えば、リン、窒素、硫黄などの化合物またはアセチレン系化合物を添加してもよい。また、接着性を付与するためにエポキシ基含有アルコキシシラン等のシランカップリング剤を添加してもよい。 In addition, a reaction control agent for controlling the reaction, for example, a compound such as phosphorus, nitrogen, sulfur, or an acetylene compound may be added to the composition of the present invention as necessary. Moreover, in order to provide adhesiveness, you may add silane coupling agents, such as an epoxy-group containing alkoxysilane.
以下、実施例と比較例を示すが、本発明は下記の実施例に制限されるものではない。なお、各例中の部はいずれも重量部であり、物理的特性は２５℃における値である。
（ビニル基含有ポリオルガノシロキサンベースの調製）
ＰｈＳｉＯ３／２単位５５モル％、Ｐｈ２ＳｉＯ２／２単位３３モル％、ＶｉＭｅＳｉＯ２／２単位１０モル％、Ｍｅ２ＳｉＯ２／２単位２モル％からなる分岐状ポリオルガノシロキサンとヘキサメチルジシラザンの反応生成物のキシレン溶液(５０ｗｔ％溶液)１００部と、Ｐｈ２ＳｉＯ２／２単位を４０モル％含有し、両末端がＶｉＭｅ２ＳｉＯ１／２単位で封止された２５℃における粘度が５Ｐａ．ｓの直鎖状ポリオルガノシロキサン５０部を混合した。
Hereinafter, although an Example and a comparative example are shown, this invention is not restrict | limited to the following Example. In addition, all the parts in each example are parts by weight, and the physical characteristics are values at 25 ° C.
(Preparation of vinyl group-containing polyorganosiloxane base)
Branched polyorganosiloxane and hexamethyldi consisting of 55 mol% of PhSiO 3/2 units, 33 mol% of Ph 2 SiO 2/2 units, 10 mol% of ViMeSiO 2/2 units, 2 mol% of Me 2 SiO 2/2 units Viscosity at 25 ° C. containing 100 parts of xylene solution of silazane reaction product (50 wt% solution) and 40 mol% of Ph 2 SiO 2/2 units sealed at both ends with ViMe 2 SiO 1/2 units 5 Pa. 50 parts of a linear polyorganosiloxane of s were mixed.
このキシレン溶液を真空下、１５０℃に加熱し、キシレンを除去し、ビニル基含有ポリオルガノシロキサンベースを得た（低沸分２．５ｗｔ％）。 This xylene solution was heated to 150 ° C. under vacuum to remove xylene and obtain a vinyl group-containing polyorganosiloxane base (low boiling point 2.5 wt%).
更に、このビニル基含有ポリオルガノシロキサンベースを０．１ｍｍHgの減圧下で薄膜化し、２００℃に加熱し低沸分を除去した（低沸分０．５ｗｔ％）。
実施例１
（Ａ）ビニル基含有ポリオルガノシロキサンベース（低沸分０．５ｗｔ％）１００部に、（Ｃ）ケイ素原子に結合した水素原子が１ｗｔ％であるオルガノハイドロジェンシロキサン８．７部、（Ｄ）塩化白金酸とビニルシロキサンの錯体（組成物の２０ｐｐｍとなる量）、シランカップリング剤（γ−グリシドキシプロピルトリメトキシシラン）３．５部を加え、光学材料封止用硬化性組成物を調製した。
実施例２
更に、（Ｂ）トリアリルイソシアネート０．６部を加え、（Ｃ）成分の配合量を１０部として以外は実施例１と同様にして、光学材料封止用硬化性組成物を調製した。
比較例１、２
（Ａ）ビニル基含有ポリオルガノシロキサンベースとして低沸分２．５ｗｔ％のものを用いた以外は実施例１、２と同様にして、光学材料封止用硬化性組成物を調製した。
Further, this vinyl group-containing polyorganosiloxane base was thinned under a reduced pressure of 0.1 mmHg and heated to 200 ° C. to remove low boiling point (low boiling point 0.5 wt%).
Example 1
(A) 100 parts of a vinyl group-containing polyorganosiloxane base (low boiling point 0.5 wt%), (C) 8.7 parts of an organohydrogensiloxane having 1 wt% of hydrogen atoms bonded to silicon atoms, (D) Add a complex of chloroplatinic acid and vinyl siloxane (20 ppm of the composition), 3.5 parts of silane coupling agent (γ-glycidoxypropyltrimethoxysilane) and add a curable composition for sealing optical materials. Prepared.
Example 2
Furthermore, a curable composition for sealing an optical material was prepared in the same manner as in Example 1 except that 0.6 part of (B) triallyl isocyanate was added and the amount of component (C) was changed to 10 parts.
Comparative Examples 1 and 2
(A) A curable composition for sealing an optical material was prepared in the same manner as in Examples 1 and 2, except that a vinyl group-containing polyorganosiloxane base having a low boiling point of 2.5 wt% was used.
これら硬化性組成物の粘度、屈折率、硬さの測定結果を表１に示す。 Table 1 shows the measurement results of the viscosity, refractive index and hardness of these curable compositions.
また、クラックの発生の有無は１０ｍｍ厚ガラスセル中に組成物０．８〜０．９ｇを流し込み、１５０℃×1時間で硬化させ、その後２６０℃×１０分間のエージングを行い確認した。 The presence or absence of cracks was confirmed by pouring 0.8 to 0.9 g of the composition into a 10 mm thick glass cell and curing it at 150 ° C. for 1 hour, followed by aging at 260 ° C. for 10 minutes.
Claims (2)
（Ｂ）アルケニル基含有環状イソシアネート化合物；（Ａ）成分中のアルケニル基１モルに対してアルケニル基が０．０１〜２モルとなる量
（Ｃ）１分子中に少なくとも３個のＳｉＨ結合を有するオルガノハイドロジェンシロキサン；（Ａ）、（Ｂ）成分中のアルケニル基１モルに対してＳｉＨ結合が０．４〜５モルとなる量
（Ｄ）ヒドロシリル化反応用触媒
を含有することを特徴とする光学材料封止用硬化性組成物。 (A) having at least two alkenyl groups in one molecule, having 5 mol% or more of PhSiO 3/2 and / or Ph 2 SiO 2/2 units (where Ph is a phenyl group), Polyorganosiloxane (B) alkenyl group-containing cyclic isocyanate compound having a heat loss of 1.5% by weight or less at 1 ° C for 1 hour; 0.01-2 alkenyl groups relative to 1 mol of alkenyl groups in component (A) (C) organohydrogensiloxane having at least 3 SiH bonds per molecule; (A), 0.4 to 5 moles of SiH bonds per mole of alkenyl group in component (B) A curable composition for encapsulating an optical material, comprising an amount of (D) a catalyst for hydrosilylation reaction.
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