JPH05226700A - Epoxy resin composition for sealing light emitting diode and light emitting diode sealed with same - Google Patents
Epoxy resin composition for sealing light emitting diode and light emitting diode sealed with sameInfo
- Publication number
- JPH05226700A JPH05226700A JP4025214A JP2521492A JPH05226700A JP H05226700 A JPH05226700 A JP H05226700A JP 4025214 A JP4025214 A JP 4025214A JP 2521492 A JP2521492 A JP 2521492A JP H05226700 A JPH05226700 A JP H05226700A
- Authority
- JP
- Japan
- Prior art keywords
- emitting diode
- light emitting
- epoxy resin
- acid anhydride
- resin composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、発光ダイオード封止用
エポキシ樹脂組成物及び該組成物で封止された発光ダイ
オードに関する。TECHNICAL FIELD The present invention relates to an epoxy resin composition for encapsulating a light emitting diode and a light emitting diode encapsulated with the composition.
【０００２】[0002]
【従来の技術】従来、発光ダイオードは、その発光に寄
与する面の保護と発光効率を向上するため、少なくとも
発光に寄与する面が透明な樹脂で覆われている（封止さ
れている）。この封止用の樹脂としては、エポキシ樹脂
組成物が従来広く使用されている。2. Description of the Related Art Conventionally, a light emitting diode is covered (sealed) with at least the surface contributing to light emission in order to protect the surface contributing to light emission and to improve the light emission efficiency. Epoxy resin compositions have hitherto been widely used as the sealing resin.
【０００３】しかしながら、一般にエポキシ樹脂で封止
された発光ダイオードは、可撓性に乏しく、歪みに対し
て脆いという欠点があり、最近の発光ダイオードの大型
化に伴い、大きな障害となる。すなわち、エポキシ樹脂
が硬化する際のエポキシ樹脂の収縮変形などによる内部
応力のために、発光に寄与する面との界面にクラックを
生じることがある。このようなクラックの発生は、たと
え微小であっても耐湿性を低下させ、長時間使用すると
故障の原因となる。However, a light emitting diode encapsulated with an epoxy resin generally has the drawbacks of poor flexibility and brittleness against distortion, which is a major obstacle to the recent increase in size of the light emitting diode. That is, cracks may occur at the interface with the surface that contributes to light emission due to internal stress due to shrinkage deformation of the epoxy resin when the epoxy resin cures. The generation of such cracks deteriorates the moisture resistance even if they are minute, and causes a failure when used for a long time.
【０００４】これらの欠点を解決するためには、一般
に、封止剤組成物への可撓性付与剤の添加、可撓性硬化
剤の添加などの方法が考えられるが、このような方法で
は熱変形温度が大幅に低下し、電気特性が悪化する。ま
た、不飽和カルボン酸の添加による改良が試みられてい
るが、透明性が損なわれるという欠点がある。In order to solve these drawbacks, generally, a method of adding a flexibility-imparting agent to the encapsulant composition, a method of adding a flexible curing agent, and the like can be considered. The heat distortion temperature is significantly lowered, and the electrical characteristics are deteriorated. Further, although improvement has been attempted by adding an unsaturated carboxylic acid, there is a drawback that transparency is impaired.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、上記の従来
技術の欠点を解消し、クラックを発生せず、透明性に優
れた硬化膜を形成しうる発光ダイオード封止用エポキシ
樹脂組成物及び該組成物で封止した発光ダイオードを提
供することを目的とする。DISCLOSURE OF THE INVENTION The present invention solves the above-mentioned drawbacks of the prior art, does not cause cracks, and can form a cured film having excellent transparency. It is an object to provide a light emitting diode encapsulated with the composition.
【０００６】[0006]
【課題を解決するための手段】本発明は、特定の組成を
有する酸無水物系硬化剤を用いることによって上記の目
的を達成したものである。すなわち、本発明は、エポキ
シ樹脂、酸無水物系硬化剤及び硬化促進剤を含有してな
る発光ダイオード封止用エポキシ樹脂組成物において、
酸無水物系硬化剤として、脂環式飽和ポリカルボン酸無
水物を主成分とし、さらに脂環式飽和ポリカルボン酸無
水物と２個以上の水酸基を有するポリオールとを反応さ
せて得られるポリエステルポリカルボン酸を脂環式飽和
ポリカルボン酸無水物に対して５〜３０重量％含有して
なる硬化剤組成物を含有することを特徴とする発光ダイ
オード封止用エポキシ樹脂組成物及び少なくとも発光に
寄与する面が該エポキシ樹脂組成物で覆われ、封止され
ていることを特徴とする発光ダイオードに関する。The present invention has achieved the above object by using an acid anhydride type curing agent having a specific composition. That is, the present invention is an epoxy resin composition for encapsulating a light emitting diode, which comprises an epoxy resin, an acid anhydride-based curing agent and a curing accelerator,
As an acid anhydride-based curing agent, a polyester polyis which is obtained by reacting an alicyclic saturated polycarboxylic acid anhydride as a main component, and further reacting an alicyclic saturated polycarboxylic acid anhydride with a polyol having two or more hydroxyl groups. An epoxy resin composition for encapsulating a light-emitting diode, which comprises a curing agent composition containing 5 to 30% by weight of a carboxylic acid with respect to an alicyclic saturated polycarboxylic acid anhydride A surface of the light emitting diode is covered with the epoxy resin composition and sealed.
【０００７】本発明において、本発明のエポキシ樹脂組
成物で封止される発光ダイオードとしては、例えば、ｐ
−ｎ接合を有するＧａＡｓx Ｐ1-x 系混晶（但し、１≧
ｘ≧０）からなる発光に起用する面を有する発光素子、
数字表示素子などがある。このような発光ダイオードの
少なくとも発光に寄与する面がエポキシ樹脂組成物の硬
化物で覆われる。In the present invention, the light emitting diode sealed with the epoxy resin composition of the present invention is, for example, p
GaAs x P 1-x system mixed crystal with -n junction (1 ≥ 1
x ≧ 0), a light emitting device having a surface used for light emission,
There are numeric display elements and so on. At least the surface of such a light emitting diode that contributes to light emission is covered with a cured product of an epoxy resin composition.
【０００８】本発明の発光ダイオード封止用エポキシ樹
脂組成物は、エポキシ樹脂、酸無水物系硬化剤及び硬化
促進剤を含有してなるものである。ここで、エポキシ樹
脂としては、無色又は淡色で透明な液状又は固体状のエ
ポキシ樹脂が好ましい。代表的に使用されるエポキシ樹
脂としては、ビスフェノールＡ、ビスフェノールＦ等の
２価フェノールとエピクロルヒドリンから得られるビス
フェノール型エポキシ樹脂、脂環式型のエポキシ樹脂、
ヘキサヒドロフタル酸等の多塩基酸のグリシジルエステ
ル型のエポキシ樹脂、ノボラック型エポキシ樹脂、長鎖
ポリオールのジグリシジルエーテル型のエポキシ樹脂な
どであり、市販品の例としては、シェルケミカル社製の
商品名アラルダイトＣＹ−１８３、ＣＹ−１８２、ＣＹ
−１７５、ＧＹ−２５０、ＧＹ−２６０、ＧＹ−２５
２；油化シェルエポキシ社製の商品名エピコート８２
８、８０８、１７１、８７２、８７１、１００１、１０
０４；ダウケミカル社製の商品名ＤＥＮ−４３１、ＤＥ
Ｎ−４３８、ＤＥＲ−７３２、ＤＥＲ−３３０、ＤＥＲ
−３３１、ＤＥＲ−３３２；チッソ株式会社製の商品名
チッソノックス２２１、２８９などが挙げられる。The light emitting diode encapsulating epoxy resin composition of the present invention comprises an epoxy resin, an acid anhydride type curing agent and a curing accelerator. Here, the epoxy resin is preferably a colorless or light-colored transparent liquid or solid epoxy resin. Epoxy resins typically used include bisphenol-type epoxy resins obtained from dihydric phenols such as bisphenol A and bisphenol F and epichlorohydrin, alicyclic epoxy resins,
Examples include glycidyl ester type epoxy resins of polybasic acids such as hexahydrophthalic acid, novolac type epoxy resins, and diglycidyl ether type epoxy resins of long-chain polyols. Name Araldite CY-183, CY-182, CY
-175, GY-250, GY-260, GY-25
2; Trade name Epicoat 82 manufactured by Yuka Shell Epoxy Co., Ltd.
8, 808, 171, 872, 871, 1001, 10
04; trade name DEN-431, DE manufactured by Dow Chemical Company
N-438, DER-732, DER-330, DER
-331, DER-332; trade name Chisso Knox 221, 289 manufactured by Chisso Corporation, and the like.
【０００９】本発明においては、酸無水物系硬化剤とし
て、脂環式飽和ポリカルボン酸無水物を主成分とし、さ
らに、脂環式飽和ポリカルボン酸無水物と２個以上の水
酸基を有するポリオールとを反応させて得られるポリエ
ステルポリカルボン酸を５〜３０重量％含有してなる硬
化剤組成物を使用する。In the present invention, as the acid anhydride-based curing agent, an alicyclic saturated polycarboxylic acid anhydride as a main component, an alicyclic saturated polycarboxylic acid anhydride, and a polyol having two or more hydroxyl groups are used. A curing agent composition containing 5 to 30% by weight of a polyester polycarboxylic acid obtained by reacting
【００１０】ここで、脂環式飽和ポリカルボン酸無水物
としては、ヘキサヒドロ無水フタル酸、４−メチルヘキ
サヒドロ無水フタル酸、３−メチルヘキサヒドロ無水フ
タル酸などが挙げられ、これらの混合物でもよい。これ
らの脂環式飽和ポリカルボン酸無水物は、テトラヒドロ
無水フタル酸、４−テトラヘキサヒドロ無水フタル酸、
３−テトラヘキサヒドロ無水フタル酸などを水素化する
ことによって得られるが、脂環式飽和ポリカルボン酸無
水物中に含まれる未水素化物又はそれらの構造異性体、
例えば、３−メチル−Δ3 −テトラヒドロ無水フタル酸
などは、硬化時の着色性の上で、１重量％以下であるこ
とが好ましく、0.１重量％以下であることがより好まし
い。Here, examples of the alicyclic saturated polycarboxylic acid anhydride include hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, 3-methylhexahydrophthalic anhydride and the like, and a mixture thereof may be used. .. These alicyclic saturated polycarboxylic acid anhydrides are tetrahydrophthalic anhydride, 4-tetrahexahydrophthalic anhydride,
Although obtained by hydrogenating 3-tetrahexahydrophthalic anhydride or the like, unhydrogenated compounds or their structural isomers contained in alicyclic saturated polycarboxylic acid anhydride,
For example, 3-methyl-Δ 3 -tetrahydrophthalic anhydride or the like is preferably 1% by weight or less, more preferably 0.1% by weight or less in terms of colorability during curing.
【００１１】ポリエステルポリカルボン酸の原料となる
脂環式飽和ポリカルボン酸無水物は、上記の主成分とな
る脂環式飽和ポリカルボン酸無水物と同じものであって
もよく、また、異なるものであってもよい。The alicyclic saturated polycarboxylic acid anhydride as a raw material for the polyester polycarboxylic acid may be the same as or different from the alicyclic saturated polycarboxylic acid anhydride as the main component. May be
【００１２】他方、ポリエステルポリカルボン酸の原料
となるポリオールは、２個以上の水酸基を有するもので
あればよく、例えば、エチレングリコール、プロピレン
グリコール、ジエチレングリコール等のポリグリコー
ル、ネオペンチルグリコール等のジオール類、グリセリ
ン、トリメチロールプロパン等のトリオール類、ペンタ
エリトリット等のテトラオール類などが挙げられる。On the other hand, the polyol used as the raw material for the polyester polycarboxylic acid may be one having two or more hydroxyl groups, and examples thereof include polyglycols such as ethylene glycol, propylene glycol and diethylene glycol, and diols such as neopentyl glycol. , Triglycerides such as glycerin and trimethylolpropane, and tetraols such as pentaerythritol.
【００１３】ポリエステルポリカルボン酸を合成するた
めには、上記に挙げた脂環式飽和ポリカルボン酸無水物
とポリオールとを、ポリオールの水酸基１個に対し、酸
無水物基が１個になるように混合し、加熱しながら反応
させる。In order to synthesize polyester polycarboxylic acid, the above-mentioned alicyclic saturated polycarboxylic acid anhydride and polyol are prepared so that there is one acid anhydride group per one hydroxyl group of the polyol. And react with heating.
【００１４】本発明に用いる酸無水物系硬化剤におい
て、主成分である脂環式飽和カルボン酸無水物に対する
ポリエステルポリカルボン酸の混合割合は、５〜３０重
量％が好ましい。ポリエステルポリカルボン酸の量が５
重量％未満では可撓性の付与が不完全で、クラックを発
生しやすく、３０重量％を超えると、エポキシ樹脂組成
物の粘度が増大し、脱泡性が悪化し、同時に耐熱性も低
下する。In the acid anhydride curing agent used in the present invention, the mixing ratio of the polyester polycarboxylic acid to the alicyclic saturated carboxylic acid anhydride as the main component is preferably 5 to 30% by weight. The amount of polyester polycarboxylic acid is 5
If it is less than wt%, flexibility is not sufficiently imparted and cracks are likely to occur, and if it exceeds 30 wt%, the viscosity of the epoxy resin composition increases, the defoaming property deteriorates, and at the same time the heat resistance decreases. ..
【００１５】硬化促進剤としては、三級アミン、三級ア
ミン塩、四級アンモニウム塩、有機酸金属塩、有機金属
錯体などがあり、硬化時の着色をなくすためには、１，
８−ジアザ−ビシクロ（５，４，０）ウンデセン−７等
のジアザ−ビシクロ−アルケン化合物及びその有機酸塩
が好ましい。Examples of the curing accelerator include tertiary amines, tertiary amine salts, quaternary ammonium salts, organic acid metal salts, organic metal complexes, etc. In order to eliminate coloring during curing, 1,
Preferred are diaza-bicyclo-alkene compounds such as 8-diaza-bicyclo (5,4,0) undecene-7 and organic acid salts thereof.
【００１６】本発明のエポキシ樹脂組成物には、必要に
応じ、公知の充填剤、染料、可塑剤、消泡剤、チキソト
ロピー性付与剤などを添加してもよい。If desired, known fillers, dyes, plasticizers, defoamers, thixotropic agents, etc. may be added to the epoxy resin composition of the present invention.
【００１７】発光ダイオードの封止は、封止型内で少な
くとも未封止発光ダイオードの発光に寄与する面をエポ
キシ樹脂組成物に浸漬された状態として、該組成物を硬
化させることによって行なわれる。エポキシ樹脂組成物
の硬化は、通常用いられる硬化条件で行なって良好な結
果が得られるが、８０℃〜１７０℃の温度で数分間〜１
日間の硬化時間が好ましい。１３０℃〜１７０℃で数分
間〜数十分間という高温短時間硬化でもクラックは発生
しない。The encapsulation of the light emitting diode is carried out by curing the composition in a state where at least the surface of the unsealed light emitting diode that contributes to light emission is immersed in the epoxy resin composition. Curing of the epoxy resin composition can be carried out under normally used curing conditions to obtain good results, but at a temperature of 80 ° C. to 170 ° C. for several minutes to 1
Day cure times are preferred. No cracks occur even at high temperature for a short time at 130 ° C to 170 ° C for several minutes to several tens of minutes.
【００１８】[0018]
【実施例】次に、実施例により本発明を詳述するが、本
発明はこれによって制限されるものではない。EXAMPLES Next, the present invention will be described in detail with reference to examples, but the present invention is not limited thereto.
【００１９】合成例１ ＨＮ−５５００Ｅ（日立化成工業株式会社製メチルヘキ
サヒドロ無水フタル酸の商品名）１３７.6ｇとネオペン
チルグリコール４２.6ｇを、攪拌機、温度計、還流管及
びＮ2 導入管の付いた１０００mlの四つ口フラスコに入
れ、窒素気流下で１７０℃まで攪拌しながら昇温した。
１６０〜１７０℃で２時間反応させた時の酸価は２５
４.2（理論値２５５.0）であった。そこにＨＮ−５５０
０Ｅを８２０ｇ加え、均一に溶解し、酸無水物系硬化剤
を得た。Synthesis Example 1 137.6 g of HN-5500E (trade name of methylhexahydrophthalic anhydride manufactured by Hitachi Chemical Co., Ltd.) and 42.6 g of neopentyl glycol were added to a stirrer, a thermometer, a reflux pipe and an N 2 introduction pipe. The mixture was placed in a 1000 ml four-necked flask equipped with a flask, and the temperature was raised to 170 ° C. with stirring under a nitrogen stream.
The acid value when reacted at 160-170 ° C for 2 hours is 25.
It was 4.2 (theoretical value 255.0). HN-550 there
820 g of OE was added and uniformly dissolved to obtain an acid anhydride-based curing agent.
【００２０】合成例２ 合成例１でＨＮ−５５００Ｅの代わりにＨＮ−２２００
（日立化成工業株式会社製メチルテトラヒドロ無水フタ
ル酸の商品名）を用いた以外は、合成例１と同様にして
酸無水物系硬化剤を得た。Synthesis Example 2 Instead of HN-5500E in Synthesis Example 1, HN-2200
An acid anhydride-based curing agent was obtained in the same manner as in Synthesis Example 1 except that (trade name of methyltetrahydrophthalic anhydride manufactured by Hitachi Chemical Co., Ltd.) was used.
【００２１】実施例１ エピコート８２８（油化シェルエポキシ社製エポキシ樹
脂の商品名）１００重量部、合成例１の酸無水物系硬化
剤１００重量部及び１，８−ジアザ−ビシクロ−（５，
４，０）−ウンデセン（以下、ＤＢＵと略記する）2.５
重量部をよく混合し、均一な樹脂液とした。未封止発光
ダイオードを金型に装着し、上記樹脂液を注入して１３
０℃で６時間加熱した。次に、金型から樹脂で封止され
た発光ダイオードを取り出し、発光に寄与する面と樹脂
との界面におけるクラックの有無を目視により判定し
た。一方、透明性の指標として発光ダイオードの硬化物
部分の色を目視により判定し、さらに、樹脂で封止した
発光ダイオードに直流電圧を印加して輝度を測定した。
結果を表１に示す。Example 1 100 parts by weight of Epicoat 828 (trade name of epoxy resin manufactured by Yuka Shell Epoxy Co., Ltd.), 100 parts by weight of the acid anhydride-based curing agent of Synthesis Example 1, and 1,8-diaza-bicyclo- (5.
4,0) -Undecene (hereinafter abbreviated as DBU) 2.5
The parts by weight were mixed well to form a uniform resin liquid. Attach the unsealed light emitting diode to the mold, inject the above resin solution, and
Heated at 0 ° C. for 6 hours. Next, the light emitting diode sealed with the resin was taken out from the mold, and the presence or absence of cracks at the interface between the surface contributing to light emission and the resin was visually determined. On the other hand, the color of the cured part of the light emitting diode was visually determined as an index of transparency, and a direct current voltage was applied to the light emitting diode sealed with resin to measure the brightness.
The results are shown in Table 1.
【００２２】実施例２及び比較例１〜２ 表１に示す配合からなるエポキシ樹脂組成物を使用した
以外は、実施例１と同様にして封止発光ダイオードを製
造し、その評価を行なった。Example 2 and Comparative Examples 1 and 2 A sealed light emitting diode was manufactured and evaluated in the same manner as in Example 1 except that the epoxy resin composition having the composition shown in Table 1 was used.
【００２３】[0023]
【表１】 [Table 1]
【００２４】なお、輝度の評価は、ピーク波長約５５５
ｎｍでフートランバート単位で測定したものである。The brightness is evaluated by the peak wavelength of about 555.
It is measured in units of foot lambert in nm.
【００２５】[0025]
【発明の効果】本発明のエポキシ樹脂組成物は、可撓性
及び透明性に優れた硬化膜を生じ、高温短時間硬化を行
なってもクラックを発生しない。したがった、この樹脂
組成物を用いて封止した発光ダイオードは、透明性に優
れ、クラックを有しない。The epoxy resin composition of the present invention forms a cured film having excellent flexibility and transparency, and does not generate cracks even when it is cured at a high temperature for a short time. Therefore, the light emitting diode sealed with this resin composition has excellent transparency and does not have cracks.
Claims (2)
化促進剤を含有してなる発光ダイオード封止用エポキシ
樹脂組成物において、酸無水物系硬化剤として、脂環式
飽和ポリカルボン酸無水物を主成分とし、さらに脂環式
飽和ポリカルボン酸無水物と２個以上の水酸基を有する
ポリオールとを反応させて得られるポリエステルポリカ
ルボン酸を脂環式飽和ポリカルボン酸無水物に対して５
〜３０重量％含有してなる硬化剤組成物を含有すること
を特徴とする発光ダイオード封止用エポキシ樹脂組成
物。1. An epoxy resin composition for encapsulating a light emitting diode, comprising an epoxy resin, an acid anhydride-based curing agent, and a curing accelerator, wherein the acid anhydride-based curing agent is an alicyclic saturated polycarboxylic acid anhydride. A polyester polycarboxylic acid obtained by reacting an alicyclic saturated polycarboxylic acid anhydride with a polyol having two or more hydroxyl groups is added to the alicyclic saturated polycarboxylic acid anhydride.
An epoxy resin composition for encapsulating a light emitting diode, comprising a curing agent composition containing 30 to 30% by weight.
記載のエポキシ樹脂組成物で覆われ、封止されているこ
とを特徴とする発光ダイオード。2. A surface that contributes at least to light emission is defined in claim 1.
A light-emitting diode, which is covered with the epoxy resin composition described above and sealed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4025214A JPH05226700A (en) | 1992-02-12 | 1992-02-12 | Epoxy resin composition for sealing light emitting diode and light emitting diode sealed with same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4025214A JPH05226700A (en) | 1992-02-12 | 1992-02-12 | Epoxy resin composition for sealing light emitting diode and light emitting diode sealed with same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05226700A true JPH05226700A (en) | 1993-09-03 |
Family
ID=12159712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4025214A Pending JPH05226700A (en) | 1992-02-12 | 1992-02-12 | Epoxy resin composition for sealing light emitting diode and light emitting diode sealed with same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05226700A (en) |
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-
1992
- 1992-02-12 JP JP4025214A patent/JPH05226700A/en active Pending
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|---|---|---|---|---|
| US6960878B2 (en) | 2001-01-24 | 2005-11-01 | Nichia Corporation | Light emitting diode, optical semiconductor element and epoxy resin composition suitable for optical semiconductor element and production methods therefor |
| CN1305960C (en) * | 2001-01-24 | 2007-03-21 | 日亚化学工业株式会社 | Optical semiconductor device, epoxy resin composition suited for optical semiconductor device, and method for manufacturing the same |
| US7342357B2 (en) | 2001-01-24 | 2008-03-11 | Nichia Corporation | Light emitting diode, optical semiconductor device, epoxy resin composition suited for optical semiconductor device, and method for manufacturing the same |
| US7550096B2 (en) | 2001-01-24 | 2009-06-23 | Nichia Corporation | Light emitting diode, optical semiconductor device, epoxy resin composition and phosphor suited for optical semiconductor device, and method for manufacturing the same |
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