JPH04363054A - Epoxy resin composition for optical-semiconductor sealing use - Google Patents
Epoxy resin composition for optical-semiconductor sealing useInfo
- Publication number
- JPH04363054A JPH04363054A JP41831490A JP41831490A JPH04363054A JP H04363054 A JPH04363054 A JP H04363054A JP 41831490 A JP41831490 A JP 41831490A JP 41831490 A JP41831490 A JP 41831490A JP H04363054 A JPH04363054 A JP H04363054A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- formula
- temperature
- optical
- hardener
- 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.)
- Granted
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 32
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 239000004065 semiconductor Substances 0.000 title claims abstract description 7
- 238000007789 sealing Methods 0.000 title abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002834 transmittance Methods 0.000 abstract description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract description 3
- 230000006866 deterioration Effects 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000004848 polyfunctional curative Substances 0.000 abstract 3
- 239000004593 Epoxy Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- -1 glycerin fatty acid ester Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は光透過性に優れた光半導
体封止用エポキシ樹脂に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin for encapsulating optical semiconductors having excellent light transmittance.
【０００２】0002
【従来の技術】オプトエレクトロニクス関連分野に於い
て酸無水物硬化タイプのエポキシ樹脂組成物は透明性に
優れ、かつ波長９００〜１０００ｎｍの近赤外光領域で
の透過率が優れているのでフォトセンサー等に使用され
ている。しかし、従来の酸無水物硬化タイプのエポキシ
樹脂組成物は温度１００〜１２５℃、湿度８５〜１００
％の高温高湿雰囲気下では耐湿性に難点があり、このた
め光透過率が著しく低下する欠点があった。これらの欠
点を改良するためシリコーンオイルを添加して耐湿性を
良くする方法（特開昭６１−１２７７２３）、カップリ
ング剤を添加し耐湿性を良くする方法（特開昭６１−１
２７７２４）等が試みられているが、いまだ満足できる
ものでなかった。従って耐湿性が必要とされるエリアセ
ンサー等の用途にはガラスを用いて気密封止した光半導
体が用いられているが組立てコストが高いという欠点が
あり、生産性に優れたエポキシ成形材料の開発が望まれ
ていた。[Prior Art] In the field of optoelectronics, acid anhydride curing type epoxy resin compositions have excellent transparency and excellent transmittance in the near-infrared light region with a wavelength of 900 to 1000 nm, so they can be used for photosensors. etc. is used. However, conventional acid anhydride curing type epoxy resin compositions have a temperature of 100 to 125°C and a humidity of 85 to 100°C.
% in a high-temperature, high-humidity atmosphere, there was a drawback in that the moisture resistance was poor, and the light transmittance was therefore significantly reduced. In order to improve these drawbacks, there is a method to improve moisture resistance by adding silicone oil (Japanese Patent Laid-Open No. 61-127723), a method to improve moisture resistance by adding a coupling agent (Japanese Patent Laid-Open No. 61-1
27724) have been attempted, but they have not yet been satisfactory. Therefore, optical semiconductors hermetically sealed with glass are used for applications such as area sensors that require moisture resistance, but they have the disadvantage of high assembly costs, and the development of epoxy molding materials with excellent productivity. was desired.
【０００３】0003
【発明が解決しようとする課題】本発明は高温高湿下で
光透過率が劣化しない光半導体封止用エポキシ樹脂組成
物を提供するものである。SUMMARY OF THE INVENTION The present invention provides an epoxy resin composition for encapsulating optical semiconductors whose light transmittance does not deteriorate under high temperature and high humidity conditions.
【０００４】0004
【課題を解決するための手段】本発明は下記式〔Ｉ〕で
示されるエポキシ樹脂を総エポキシ樹脂量の２０〜１０
０重量％と[Means for Solving the Problems] The present invention uses an epoxy resin represented by the following formula [I] in an amount of 20 to 10% of the total amount of epoxy resin.
0% by weight
【０００５】[0005]
【化２】[Chemical 2]
【０００６】（式中のＲはＣｎＨ２ｎ＋１でｎ＝１〜６
）硬化剤および硬化促進剤からなる半導体封止用エポキ
シ樹脂組成物である。(R in the formula is CnH2n+1 and n=1 to 6
) An epoxy resin composition for semiconductor encapsulation comprising a curing agent and a curing accelerator.
【０００７】本発明の式〔Ｉ〕のエポキシ樹脂は多官能
の分子構造のため耐熱性が上がり、温度１００〜１２５
℃、湿度８５〜１００％のような高温高湿雰囲気下での
吸湿劣下が少なくなり光透過性の低下が抑えられる。式
〔Ｉ〕中のｍは２以下では耐熱性が充分に上がらず、高
温高湿雰囲気下での光透過性の低下が抑えられなくなる
。またｍが２０を超えると軟化点が高すぎて、樹脂組成
物の製造が困難となる。[0007] The epoxy resin of formula [I] of the present invention has increased heat resistance due to its polyfunctional molecular structure,
℃ and a humidity of 85 to 100%, moisture absorption deterioration is reduced and light transmittance deterioration is suppressed. If m in formula [I] is 2 or less, the heat resistance will not be sufficiently improved, and the decrease in light transmittance will not be suppressed in a high-temperature, high-humidity atmosphere. Moreover, if m exceeds 20, the softening point will be too high, making it difficult to produce a resin composition.
【０００８】式〔Ｉ〕に配合するエポキシ樹脂はビスフ
ェノールＡ型エポキシ樹脂、ノボラック型エポキシ樹脂
、脂環式エポキシ樹脂等が挙げられ特に限定するもので
はないが１種または２種以上併用することができる。[0008] Epoxy resins to be blended in formula [I] include bisphenol A type epoxy resins, novolac type epoxy resins, alicyclic epoxy resins, etc., and are not particularly limited, but one type or two or more types can be used in combination. can.
【０００９】式〔Ｉ〕のエポキシ樹脂の配合量は総エポ
キシ樹脂量の２０〜１００重量％で好ましくは５０重量
％以上である。２０重量％未満であると耐熱性が充分に
上がらず、高温高湿雰囲気下で光透過性の低下が抑えら
れない。硬化剤としては多塩基カルボン酸無水物、フェ
ノール型ノボラック樹脂などがある。多塩基カルボン酸
無水物としては無水フタル酸、無水へキサヒドロフタル
酸、無水テトラヒドロフタル酸、無水マレイン酸、無水
ナジック酸等が挙げられる。フェノール型ノボラック樹
脂にはフェノール型、クレゾール型、ビスフェノールＡ
型などがある。これらは１種または２種以上併用しても
よい。硬化剤とエポキシ樹脂の配合割合はエポキシ当量
１に対して０．５〜１．２当量の硬化剤が望ましく、こ
の範囲外では成形性に欠陥を起こす場合がある。The amount of the epoxy resin of formula [I] to be blended is 20 to 100% by weight, preferably 50% by weight or more, based on the total amount of epoxy resin. If it is less than 20% by weight, the heat resistance will not be sufficiently improved, and the decrease in light transmittance will not be suppressed in a high temperature and high humidity atmosphere. Examples of hardening agents include polybasic carboxylic acid anhydrides and phenolic novolac resins. Examples of the polybasic carboxylic anhydride include phthalic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, maleic anhydride, nadic anhydride, and the like. Phenol type novolac resins include phenol type, cresol type, and bisphenol A.
There are types, etc. These may be used alone or in combination. The mixing ratio of the curing agent and the epoxy resin is preferably 0.5 to 1.2 equivalents of the curing agent per 1 epoxy equivalent; outside this range, defects in moldability may occur.
【００１０】硬化促進剤にはトリメチルアミン、トリエ
タノールアミンなどの第３級アミン、トリフェニルホス
フィン、トリシクロヘキシルホスフィン等などの有機ホ
スフィン化合物、２−メチルイミダゾールなどのイミダ
ゾール類が挙げられる。また、本発明には公知のアゾ系
、キノン系の染料を１種または２種以上を混合して添加
してもよい。本発明の組成物の製造は各成分を混合し、
加熱ロールを用いて５０〜９０℃で混練し冷却固化後、
粉砕して粉末状とする。Examples of the curing accelerator include tertiary amines such as trimethylamine and triethanolamine, organic phosphine compounds such as triphenylphosphine and tricyclohexylphosphine, and imidazoles such as 2-methylimidazole. Furthermore, one or a mixture of two or more of known azo and quinone dyes may be added to the present invention. The production of the composition of the present invention involves mixing each component,
After kneading at 50 to 90°C using heating rolls and solidifying by cooling,
Grind into powder.
【００１１】以下、本発明を実施例で具体的に示す。[0011] The present invention will be specifically illustrated below with examples.
【実施例】実施例１〜３、比較例１〜３表１のエポキシ
樹脂１００重量部にテトラヘキサ無水フタル酸をエポキ
シ当量１に対し０．９当量添加し、更に２−メチルイミ
ダゾール１重量部、グリセリン脂肪酸エステル３重量部
を配合し、７０〜９０℃の加熱ロールを用い加熱混練し
た後冷却固化、粉砕して樹脂組成物の粉末を得た。該樹
脂組成物を低圧トランスファー成形機を用いて温度１５
０℃で厚さ１ｍｍの試験片を成形し、さらに１２０℃で
６時間ポストキュアーした。この試験片を用いて、未処
理および吸湿後の光透過率を評価した。
結果を表１に示す。[Examples] Examples 1 to 3, Comparative Examples 1 to 3 To 100 parts by weight of the epoxy resin shown in Table 1, 0.9 equivalents of tetrahexaphthalic anhydride per 1 epoxy equivalent were added, and further 1 part by weight of 2-methylimidazole, 3 parts by weight of glycerin fatty acid ester was blended, heated and kneaded using heated rolls at 70 to 90°C, cooled to solidify, and pulverized to obtain a resin composition powder. The resin composition was molded at a temperature of 15% using a low pressure transfer molding machine.
A test piece with a thickness of 1 mm was molded at 0°C and further post-cured at 120°C for 6 hours. Using this test piece, the light transmittance of untreated and after moisture absorption was evaluated. The results are shown in Table 1.
【００１２】評価方法
※光透過率
試験片を１００℃の純水で２００時間煮沸し、分光光度
計を用いて波長９５０ｎｍの光透過率を測定。
※ガラス転移温度
１５ｍｍ×３ｍｍ×４ｍｍの試験片をＴＭＡ試験装置を
用いて室温より２６０℃まで加熱して測定。Evaluation method *Light transmittance test piece was boiled in pure water at 100°C for 200 hours, and the light transmittance at a wavelength of 950 nm was measured using a spectrophotometer. *Glass transition temperature was measured by heating a 15 mm x 3 mm x 4 mm test piece from room temperature to 260°C using a TMA test device.
【００１３】[0013]
【表１】[Table 1]
【００１４】※１ Ａ：ビスフェノールＡ型エポキシ
樹脂（エポキシ当量４９０、軟化点６８℃）Ｂ：クレゾ
ールノボラック型エポキシ樹脂（エポキシ当量２００、
軟化点７０℃）
Ｃ：式〔ＩＩ〕のエポキシ樹脂（エポキシ当量１９０、
軟化点７３℃）*1 A: Bisphenol A type epoxy resin (epoxy equivalent: 490, softening point: 68°C) B: Cresol novolac type epoxy resin (epoxy equivalent: 200,
Softening point: 70°C) C: Epoxy resin of formula [II] (epoxy equivalent: 190,
Softening point 73℃)
【００１５】[0015]
【化３】[C3]
【００１６】※２ 光透過率 ◎：９０％以上
：８５〜９０％
×：８５％未満*2 Light transmittance ◎: 90% or more: 85-90% ×: less than 85%
【００１７】[0017]
【発明の効果】本発明のエポキシ樹脂組成物は透明性に
優れ、かつ耐熱性があり高温高湿下での耐湿性が優れて
おり、近赤外光領域での光透過率の低下が抑えら、エリ
アセンサー等のような耐湿性を要求される用途への展開
ができる。またガラスを用いた気密封止に較べ組立コス
トを低減できる。[Effects of the Invention] The epoxy resin composition of the present invention has excellent transparency and heat resistance, and has excellent moisture resistance under high temperature and high humidity conditions, and suppresses a decrease in light transmittance in the near-infrared light region. Furthermore, it can be used in applications that require moisture resistance, such as area sensors. Furthermore, assembly costs can be reduced compared to hermetic sealing using glass.
Claims (1)
シ樹脂を総エポキシ樹脂量の２０〜１００重量％【化１
】 （式中のＲはＣｎＨ２ｎ＋１でｎ＝１〜６）（Ｂ）硬化
剤および （Ｃ）硬化促進剤からなる光半導体封止用エポキシ樹脂
組成物。Claim 1: (A) An epoxy resin represented by the following formula [I] in an amount of 20 to 100% by weight of the total amount of epoxy resin.
(In the formula, R is CnH2n+1 and n=1 to 6) An epoxy resin composition for encapsulating optical semiconductors comprising (B) a curing agent and (C) a curing accelerator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP41831490A JP2807094B2 (en) | 1990-12-27 | 1990-12-27 | Epoxy resin composition for optical semiconductor encapsulation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP41831490A JP2807094B2 (en) | 1990-12-27 | 1990-12-27 | Epoxy resin composition for optical semiconductor encapsulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04363054A true JPH04363054A (en) | 1992-12-15 |
| JP2807094B2 JP2807094B2 (en) | 1998-09-30 |
Family
ID=18526182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP41831490A Expired - Fee Related JP2807094B2 (en) | 1990-12-27 | 1990-12-27 | Epoxy resin composition for optical semiconductor encapsulation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2807094B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276793A (en) * | 2011-07-14 | 2011-12-14 | 舒城金泽信环保材料有限公司 | High-temperature-resistant liquid anhydride curing agent and preparation method thereof |
| CN102276792A (en) * | 2011-07-14 | 2011-12-14 | 舒城金泽信环保材料有限公司 | Liquid anhydride curing agent capable of rapidly curing while heating and preparation method thereof |
| CN103183809A (en) * | 2011-12-27 | 2013-07-03 | 日本化药株式会社 | Epoxy resin composition for transparent circuit board, and laminated glass sheet |
| CN103221451A (en) * | 2010-11-17 | 2013-07-24 | 日本化药株式会社 | Epoxy resin composition for transparent sheets and cured product thereof |
| JP2013166878A (en) * | 2012-02-16 | 2013-08-29 | Nippon Steel & Sumikin Chemical Co Ltd | Epoxy resin composition and cured product |
-
1990
- 1990-12-27 JP JP41831490A patent/JP2807094B2/en not_active Expired - Fee Related
Cited By (10)
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|---|---|---|---|---|
| CN103221451A (en) * | 2010-11-17 | 2013-07-24 | 日本化药株式会社 | Epoxy resin composition for transparent sheets and cured product thereof |
| CN103221451B (en) * | 2010-11-17 | 2015-11-25 | 日本化药株式会社 | Clear sheet composition epoxy resin and cured article thereof |
| US9328217B2 (en) | 2010-11-17 | 2016-05-03 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin composition for transparent sheets and cured product thereof |
| US9493631B2 (en) | 2010-11-17 | 2016-11-15 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin composition for transparent sheets and cured product thereof |
| US9493630B2 (en) | 2010-11-17 | 2016-11-15 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin composition for transparent sheets and cured product thereof |
| CN102276793A (en) * | 2011-07-14 | 2011-12-14 | 舒城金泽信环保材料有限公司 | High-temperature-resistant liquid anhydride curing agent and preparation method thereof |
| CN102276792A (en) * | 2011-07-14 | 2011-12-14 | 舒城金泽信环保材料有限公司 | Liquid anhydride curing agent capable of rapidly curing while heating and preparation method thereof |
| CN103183809A (en) * | 2011-12-27 | 2013-07-03 | 日本化药株式会社 | Epoxy resin composition for transparent circuit board, and laminated glass sheet |
| CN107722563A (en) * | 2011-12-27 | 2018-02-23 | 日本化药株式会社 | Transparent circuit substrate composition epoxy resin and laminated glass piece |
| JP2013166878A (en) * | 2012-02-16 | 2013-08-29 | Nippon Steel & Sumikin Chemical Co Ltd | Epoxy resin composition and cured product |
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|---|---|
| JP2807094B2 (en) | 1998-09-30 |
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