JPH01213336A - Resin composition for sealing semiconductor - Google Patents
Resin composition for sealing semiconductorInfo
- Publication number
- JPH01213336A JPH01213336A JP3752288A JP3752288A JPH01213336A JP H01213336 A JPH01213336 A JP H01213336A JP 3752288 A JP3752288 A JP 3752288A JP 3752288 A JP3752288 A JP 3752288A JP H01213336 A JPH01213336 A JP H01213336A
- Authority
- JP
- Japan
- Prior art keywords
- group
- aminophenoxy
- bis
- bismaleimide
- resin
- 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
- 239000004065 semiconductor Substances 0.000 title claims description 13
- 239000011342 resin composition Substances 0.000 title claims description 10
- 238000007789 sealing Methods 0.000 title abstract description 12
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 28
- -1 bismaleimide compound Chemical class 0.000 claims abstract description 22
- 239000005011 phenolic resin Substances 0.000 claims abstract description 16
- 229920003986 novolac Polymers 0.000 claims abstract description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 3
- 238000005538 encapsulation Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 229920005989 resin Polymers 0.000 abstract description 21
- 239000011347 resin Substances 0.000 abstract description 21
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 9
- 229920001568 phenolic resin Polymers 0.000 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 230000035939 shock Effects 0.000 abstract description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005476 soldering Methods 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 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 5
- 239000012778 molding material Substances 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000001066 destructive effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000010680 novolac-type phenolic resin 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
- YZGJLGUCTISYPI-UHFFFAOYSA-N 1,3-bis(2-butylperoxypropan-2-yl)benzene Chemical compound CCCCOOC(C)(C)C1=CC=CC(C(C)(C)OOCCCC)=C1 YZGJLGUCTISYPI-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- AZOLINCJQHVOOI-UHFFFAOYSA-N 3-[(3-aminophenoxy)methoxy]aniline Chemical compound NC1=CC=CC(OCOC=2C=C(N)C=CC=2)=C1 AZOLINCJQHVOOI-UHFFFAOYSA-N 0.000 description 1
- NQZOFDAHZVLQJO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 NQZOFDAHZVLQJO-UHFFFAOYSA-N 0.000 description 1
- JERFEOKUSPGKGV-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(SC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 JERFEOKUSPGKGV-UHFFFAOYSA-N 0.000 description 1
- VTHWGYHNEDIPTO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfinylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 VTHWGYHNEDIPTO-UHFFFAOYSA-N 0.000 description 1
- SEVNPMKAEISHJM-UHFFFAOYSA-N C1(C=CC(N1)=O)=O.C1(C=CC(N1)=O)=O.CCC Chemical compound C1(C=CC(N1)=O)=O.C1(C=CC(N1)=O)=O.CCC SEVNPMKAEISHJM-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、低応力、低熱膨張率で、なおかつ耐熱性を損
なうことなく、耐熱衝撃性、半田耐熱性に優れた、高信
鎖性を要求される半導体等電子部品の封止用に適した半
導体封止用樹脂組成物に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention is intended for applications that require low stress, low coefficient of thermal expansion, excellent thermal shock resistance, soldering heat resistance, and high reliability without impairing heat resistance. The present invention relates to a semiconductor encapsulating resin composition suitable for encapsulating electronic components such as semiconductors.
近年、半導体を封止する方法としてエポキシ樹脂に代表
される熱硬化性樹脂を使用したいわゆるプラスチック封
止が原料の低度、大量生産に適するといった経済的利点
をいかして広く実用化されている。特に多官能エポキシ
樹脂、ノボラック型フェノール樹脂、無機質充填材を主
成分とした樹脂組成物が耐熱性、成形性、電気特性に優
れているため封止樹脂の主流となっている。In recent years, so-called plastic encapsulation using thermosetting resins such as epoxy resins has been widely put into practical use as a method for encapsulating semiconductors, taking advantage of its economic advantages such as low raw material requirements and suitability for mass production. In particular, resin compositions containing polyfunctional epoxy resins, novolac type phenolic resins, and inorganic fillers as main components have become mainstream as sealing resins because they have excellent heat resistance, moldability, and electrical properties.
一方、半導体チップの高集積化が進み、それに伴いチッ
プサイズが大型化してきた。またパッケージの形状は基
板への高密度実装化、表面実装化に伴い、チップの大型
化とは逆にフラットパッケージに見られる如く小型化・
薄型化の傾向にある、このため従来の封止樹脂では見ら
れなかった不良現象が派生するようになった。すなわち
、封止樹脂とチップの熱膨張率の差に起因する樹脂の応
力がチップの大型化、樹脂層の薄肉化のため、熱衝撃に
よりパッシベーション膜のクラック、あるいは封止樹脂
のクラックといった破壊現象を引き起こし、又表面実装
化に伴いパッケージそのものが半田浴温度にさらされる
ため、パッケージ内の水分が２．激に膨張し、パッケー
ジにクラックといった破壊現象を引き起こし、半導体の
耐湿性を低下させ、ひいては信転性を低下させる原因と
なっている。従って、封止樹脂としてはこの応力の小さ
く、半田耐熱性の優れた封止樹脂の開発が望まれている
。On the other hand, as semiconductor chips have become more highly integrated, their chip sizes have become larger. In addition, the shape of packages has become smaller and smaller, as seen in flat packages, as opposed to larger chips due to higher density mounting on substrates and surface mounting.
There is a trend toward thinner products, and this has led to defects that were not seen with conventional sealing resins. In other words, stress in the resin due to the difference in thermal expansion coefficient between the sealing resin and the chip increases the size of the chip and thins the resin layer, causing thermal shock that causes destructive phenomena such as cracks in the passivation film or cracks in the sealing resin. Also, since the package itself is exposed to the solder bath temperature due to surface mounting, the moisture inside the package is 2. It expands rapidly, causing destructive phenomena such as cracks in the package, reducing the moisture resistance of the semiconductor, and ultimately reducing reliability. Therefore, it is desired to develop a sealing resin that has less stress and excellent solder heat resistance.
応力を小さくする方法としては、樹脂の熱膨張率を小さ
くしてチップのそれとの差を小さくする事が考えられる
が、樹脂の熱膨張率とチップのそれとの差は大きく、こ
れを縮めるためには熱膨張率の小さい無機質充填材を樹
脂中に多量に使用しなければならないが、現在すでにか
なり多量の無機質充填材が使用されていて、更にこれを
増量する事は成形性の悪化の原因となる。一方、樹脂の
弾性率を下げて応力を小さくするという目的で可塑材を
添加したり、可撓性を有したエポキシ樹脂あるいはフェ
ノール樹脂を用いたりする事が試みられたが、この方法
により得られた硬化物は耐熱性の点で問題があった。One possible way to reduce stress is to reduce the coefficient of thermal expansion of the resin to reduce the difference between it and that of the chip, but the difference between the coefficient of thermal expansion of the resin and that of the chip is large, so in order to reduce this requires the use of a large amount of inorganic filler with a low coefficient of thermal expansion in the resin, but currently a considerable amount of inorganic filler is already being used, and further increasing this amount may cause deterioration of moldability. Become. On the other hand, attempts have been made to add plasticizers or to use flexible epoxy resins or phenolic resins in order to lower the elastic modulus of the resin and reduce stress, but these methods have not produced results. The cured product had a problem in heat resistance.
また特開昭５８−１０８２２０に代表される如くゴム粒
子を封止樹脂中に分散させる事により耐熱性を保持しつ
つ、耐クラツク性を付与する方法等も発明されているが
、半田浴の如き封止樹脂のガラス転移温度を超える高温
における耐衝撃性に劣る等いくつかの問題点があった。In addition, as exemplified by JP-A-58-108220, a method of dispersing rubber particles in a sealing resin to provide crack resistance while maintaining heat resistance has also been invented, but methods such as solder bath etc. There were several problems such as poor impact resistance at high temperatures exceeding the glass transition temperature of the sealing resin.
本発明は、高集積回路等の高い信転性を要求される半導
体の封止用樹脂に対して要求されている、応力が小さく
耐熱衝撃性、更に半田耐熱性等に優れた半導体封止用樹
脂組成物を提供することを目的とする。The present invention is intended for semiconductor encapsulation resins that have low stress, excellent thermal shock resistance, and excellent solder heat resistance, which are required for semiconductor encapsulation resins that require high reliability such as highly integrated circuits. The purpose is to provide a resin composition.
本発明者等は種々検討した結果、特定の構造を有するビ
スマレイミド化合物とノボラック型フェノール樹脂を硬
化反応せしめたものが、応力を小さくし、耐衝撃性に優
れた樹脂を提供することを見出し、本発明に達した。As a result of various studies, the present inventors discovered that a curing reaction between a bismaleimide compound having a specific structure and a novolac type phenol resin reduces stress and provides a resin with excellent impact resistance. The present invention has been achieved.
即ち本発明は、一般式（１）
（式中、ＲはＯまたは−Ｑ−Ｘ−Ｑ−よりなる２価の基
を表わし、Ｘは直結、炭素数１〜１０の２価の炭化水素
基、６フツ素化されたイソプロピリデン基、カルボニル
基、チオ基、スルフィニル基、スルホニル基又はオキシ
ドから成る群より選ばれた基を表わす、）
にて表わされるビスマレイミド化合物とノボラック型フ
ェノール樹脂を必須成分とする半導体封止用樹脂組成物
である。That is, the present invention relates to the general formula (1) (wherein R represents a divalent group consisting of O or -Q-X-Q-, and X is a directly bonded divalent hydrocarbon group having 1 to 10 carbon atoms). , 6 representing a group selected from the group consisting of a fluorinated isopropylidene group, a carbonyl group, a thio group, a sulfinyl group, a sulfonyl group, or an oxide) and a novolak type phenolic resin. This is a resin composition for semiconductor encapsulation.
前記一般式（１）で表されるビスマレイミド化合物は通
常公知の方法により一般式（ｎ）で表されるジアミン化
合物と無水マレイン酸を縮合・脱水反応させて容易に製
造できる。The bismaleimide compound represented by the general formula (1) can be easily produced by a condensation/dehydration reaction between a diamine compound represented by the general formula (n) and maleic anhydride using a commonly known method.
（式中、Ｒは前記と同様の意味を表す）（ＩＩ）のジア
ミン化合物は、具体的には１．３−ビス（３−アミノフ
ェノキシ）ベンゼン、ビス（３−アミノフェノキシ）メ
タン、１．１−ビス（４−（３−アミノフェノキシ）フ
ェニル〕エタン、ｌ、２−ビス〔４−（３−アミノフェ
ノキシ）フェニル〕エタン、２．２＝ビス（４−（３−
アミノフェノキシ）フェニル〕プロパン、２．２−ビス
（４−（３−アミノフェノキシ）フェニルコブタン、２
．２−ビス（４−（３−アミノフェノキシ）フェニル）
−１，１，１，３，３，３−へキサフルオロプロパン、
４．４°−ビス（３−アミノフェノキシ）ビフェニル、
ビス（４−（３−アミノフェノキシ）フェニルコケトン
、ビス（４−（３−アミノフェノキシ）フェニル〕スル
フィド、ビス（４−（３−アミノフエノキシ）フェニル
〕スルホキシド、ビス（４−（３−アミノフェノキシ）
フェニル〕スルホン、ビス〔４−（３−アミノフェノキ
シ）フェニルフェーテル等があげられ、これらは単独あ
るいは二種以上混合して用いられる。(In the formula, R represents the same meaning as above.) Specifically, the diamine compound (II) is 1.3-bis(3-aminophenoxy)benzene, bis(3-aminophenoxy)methane, 1. 1-bis(4-(3-aminophenoxy)phenyl)ethane, l,2-bis[4-(3-aminophenoxy)phenyl]ethane, 2.2=bis(4-(3-
aminophenoxy)phenyl]propane, 2,2-bis(4-(3-aminophenoxy)phenylcobutane, 2
．． 2-bis(4-(3-aminophenoxy)phenyl)
-1,1,1,3,3,3-hexafluoropropane,
4.4°-bis(3-aminophenoxy)biphenyl,
Bis(4-(3-aminophenoxy)phenylkoketone, bis(4-(3-aminophenoxy)phenyl) sulfide, bis(4-(3-aminophenoxy)phenyl) sulfoxide, bis(4-(3-aminophenoxy)phenyl) )
Examples include phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl ether, etc., and these may be used alone or in combination of two or more.
−Ｃ式（ＩＩ）のジアミン化合物と無水マレイン酸を縮
合・脱水反応して得られるビスマレイミド化合物は、具
体的には、Ｎ、Ｎ’−１，３−ビス（３−アミノフェノ
キシ）ベンゼンビスマレイミド、Ｎ、Ｎ“−ビス（４−
（３−アミノフェノキシ）フェニルコメタンビスマレイ
ミド、Ｎ、Ｎ’−１，１−ビス（４−（３−アミノフェ
ノキシ）フェニル〕エタンビスマレイミド、Ｎ、Ｎ’−
１，２−（４−（３−アミノフェノキシ）フェニル］エ
タンビスマレイミド、Ｎ、Ｎ’−１，２−（４−（３−
アミノフェノキシ）フェニル〕エタンビスマレイミド、
Ｎ、Ｎ’−２，２−ビス（４−（３−アミノフェノキシ
）フェニル〕プロパンビスマレイミド、Ｎ、Ｎ’−２，
２−ビス（４−（３−アミノフェノキシ）フェニルコブ
タンビスマレイミド、 Ｎ、Ｎ’−２，２−ビス（４−
（３−アミノフェノキシ）フェニル−１，１，１，３，
３，３−へキサフルオロプロパンビスマレイミド、Ｎ、
Ｎ’−４，４’−ビス（３−アミノフェノキシ）ビフェ
ニルビスマレイミド、Ｎ、Ｎ“−ビス（４−（３−アミ
ノフェノキシ）フェニル］ケトンビスマレイミド、Ｎ、
Ｎ’−ビス〔４−（３−アミノフェノキシ）フェニル〕
スルフィドビスマレイミド、Ｎ、 Ｎ’−ビス（４−（
３−アミノフェノキシ）フェニル〕スルホキシドビスマ
レイミド、Ｎ、 Ｎ’−ビス（４−（３−アミノフェノ
キシ）フェニル〕スルホンビスマレイミド、Ｎ、Ｎ’−
ビス（４−（３−アミノフェノキシ）フェニルフェーテ
ル等があげられる。-C The bismaleimide compound obtained by the condensation/dehydration reaction of the diamine compound of formula (II) and maleic anhydride is specifically, N,N'-1,3-bis(3-aminophenoxy)benzene bis Maleimide, N, N"-bis(4-
(3-Aminophenoxy)phenylcomethanebismaleimide, N,N'-1,1-bis(4-(3-aminophenoxy)phenyl)ethanebismaleimide, N,N'-
1,2-(4-(3-aminophenoxy)phenyl]ethane bismaleimide, N,N'-1,2-(4-(3-
aminophenoxy)phenyl]ethane bismaleimide,
N, N'-2,2-bis(4-(3-aminophenoxy)phenyl)propane bismaleimide, N, N'-2,
2-bis(4-(3-aminophenoxy)phenylcobutane bismaleimide, N,N'-2,2-bis(4-
(3-aminophenoxy)phenyl-1,1,1,3,
3,3-hexafluoropropane bismaleimide, N,
N'-4,4'-bis(3-aminophenoxy)biphenylbismaleimide, N,N"-bis(4-(3-aminophenoxy)phenyl)ketone bismaleimide, N,
N'-bis[4-(3-aminophenoxy)phenyl]
Sulfide bismaleimide, N, N'-bis(4-(
3-Aminophenoxy)phenyl]sulfoxide bismaleimide, N, N'-bis(4-(3-aminophenoxy)phenyl)sulfone bismaleimide, N, N'-
Examples include bis(4-(3-aminophenoxy)phenyl ether).
本発明に用いられるノボラック型フェノール樹脂は通常
のものであって良いが、フリーフェノールがなるべく少
ないもので、軟化点が８０〜１０５°Ｃのものが好まし
い。The novolac type phenolic resin used in the present invention may be any ordinary one, but it is preferably one that contains as little free phenol as possible and has a softening point of 80 to 105°C.
ノボラック型フェノール樹脂の使用量は通常ビスマレイ
ミド１００重量部に対し１０〜５００重量部の範囲であ
る。The amount of novolac type phenol resin used is usually in the range of 10 to 500 parts by weight per 100 parts by weight of bismaleimide.
本発明において、樹脂組成物を硬化せしめるにあたって
は硬化促進剤としてホスフィン類を用いると良い、ホス
フィン類としては、例えばトリフェニルホスフィン、ト
リー４−メチルフェニルホスフィン、トリー４−メトキ
シフェニルホスフィン、トＩｊブチルホスフィン、トリ
オクチルホスフィン、トリー２−シアノエチルホスフィ
ンなどをあげることができる。In the present invention, when curing the resin composition, it is preferable to use phosphines as a curing accelerator. Examples of the phosphines include triphenylphosphine, tri-4-methylphenylphosphine, tri-4-methoxyphenylphosphine, and tri-butyl. Examples include phosphine, trioctylphosphine, and tri-2-cyanoethylphosphine.
ホスフィン類の使用量はビスマレイミド化合物とノボラ
ック型フェノール樹脂の総量１００重量部に対し０．１
〜１０重量部が好ましい。The amount of phosphines used is 0.1 parts by weight per 100 parts by weight of the bismaleimide compound and novolak phenol resin.
~10 parts by weight is preferred.
又必要に応じて有機過酸化物を併用することもできる。Moreover, an organic peroxide can also be used in combination if necessary.
有機過酸化物としては、ジ−ｔ−ブチルパーオキサイド
、ｔ−ブチルクミルパーオキサイド、ジクミルパーオキ
サイド、１．３−ビス−（を−ブチルパーオキシ−イソ
プロビル）ベンゼン、１．１−ジ−ｔ−ブチルパーオキ
シ−３，３，５−）リメチルシクロヘキサン、１．１−
ジ−ｔ−ブチルパーオキシシクロヘキサンなどのジアル
キルパーオキサイド、ｔ−ブチルパーベンゾエートなど
のアルキルパーエステルをあげることができる。有機過
酸化物の添加量は、ビスマレイミド樹脂１００重量部に
対し０．１〜５重量部が好ましい。Examples of organic peroxides include di-t-butyl peroxide, t-butylcumyl peroxide, dicumyl peroxide, 1,3-bis-(butylperoxy-isopropyl)benzene, and 1,1-di-butyl peroxide. -t-butylperoxy-3,3,5-)limethylcyclohexane, 1.1-
Examples include dialkyl peroxides such as di-t-butyl peroxycyclohexane and alkyl peresters such as t-butyl perbenzoate. The amount of organic peroxide added is preferably 0.1 to 5 parts by weight per 100 parts by weight of the bismaleimide resin.
本発明の組成物は前述のものの外、必要に応じてエポキ
シ樹脂、シリコーンオイル、充填剤、シランカップリン
グ剤、離型剤、着色剤、難燃剤などを配合し、混合、混
練し成形材料とする。In addition to the above-mentioned compositions, the composition of the present invention may contain epoxy resin, silicone oil, filler, silane coupling agent, mold release agent, coloring agent, flame retardant, etc. as necessary, and is mixed and kneaded to form a molding material. do.
実施例１
第１表に示す配合で、一般式（１）で表されるビスマレ
イミド化合物、ノボラック型フェノール樹脂、硬化促進
剤、有機過酸化物、シリカ粉末、シランカップリング剤
、ワックス、着色剤、難燃剤を配合し、ロール混練して
成形材料を得た。Example 1 A bismaleimide compound represented by the general formula (1), a novolac type phenol resin, a curing accelerator, an organic peroxide, a silica powder, a silane coupling agent, a wax, and a coloring agent in the formulation shown in Table 1. , a flame retardant was blended and roll kneaded to obtain a molding material.
比較例１
第１表に示す配合で、−ｉ式（＋）で表されるビスマレ
イミド化合物以外のビスマレイミド化合物とノボラック
型フェノール樹脂を実施例と同様に配合混練し成形材料
を得た。Comparative Example 1 A molding material was obtained by blending and kneading a bismaleimide compound other than the bismaleimide compound represented by the -i formula (+) and a novolak type phenol resin in the same manner as in the example, using the formulation shown in Table 1.
比較例２
第１表に示す配合で、エポキシ樹脂、ノボラック型フェ
ノール樹脂を実施例と同様に配合、混練し成形材料を得
た。Comparative Example 2 A molding material was obtained by blending and kneading an epoxy resin and a novolac type phenol resin in the same manner as in the example, according to the formulation shown in Table 1.
各成形材料を用い、トランスファー成形（１８０’Ｃ，
３０Ｋｇ／ｃＪ ３分間）により、試験用の１００ピ
ンフラツトパツケージ（２０＋１１１１１Ｘ３０１１１
１１１Ｘ ２．５ｍｍ 、１０ｍｍ Ｘ ＩＱｍｍの試
験用素子搭載）及び物性測定用の試験片を成形し、１８
０’Ｃで６時間後硬化した。Using each molding material, transfer molding (180'C,
30Kg/cJ for 3 minutes), the 100-pin flat package for testing (20+11111X30111
111 x 2.5 mm, 10 mm x IQ mm test elements) and test pieces for measuring physical properties were molded.
Postcured for 6 hours at 0'C.
試験結果を表−２に示す。The test results are shown in Table-2.
＊４ ＥＯＣＮ 日本（１（ＩＩＥＯｃＮ
をシリコーン変性表−２
〔発明の効果〕
実施例及び比較例にて説明した如く、本発明による半導
体封止用樹脂組成物は、従来上として用いられて来た多
官能エポキシ樹脂、ノボラックフェノール樹脂を主成分
とした封止樹脂に比較してガラス転位温度が高く、低熱
膨張であるまた、一般式（１）で表されるビスマレイミ
ド化合物以外のビスマレイミド化合物とノボラック型フ
ェノール樹脂を主成分とした封止樹脂に比較して、吸水
率が小さく、可撓性に冨み、低応力化されており、又流
動性が高く、半田耐熱性に優れている。*4 EOCN Japan (1 (IIEOcN
Silicone Modification Table-2 [Effects of the Invention] As explained in the Examples and Comparative Examples, the resin composition for semiconductor encapsulation according to the present invention can be applied to polyfunctional epoxy resins and novolak phenol resins that have been conventionally used. It has a higher glass transition temperature and lower thermal expansion than a sealing resin whose main components are a bismaleimide compound other than the bismaleimide compound represented by the general formula (1) and a novolac type phenol resin. Compared to other sealing resins, it has lower water absorption, greater flexibility, lower stress, higher fluidity, and better soldering heat resistance.
本発明の樹脂組成物を集積度の高い大型の半導体装置、
あるいは表面実装用半導体装置の封止に用いた場合、優
れた信頬性を得ることが出来、工業的に有益な発明であ
る。A large semiconductor device with a high degree of integration, using the resin composition of the present invention,
Alternatively, when used for sealing a surface-mounted semiconductor device, excellent reliability can be obtained, making it an industrially useful invention.
特許出願人 三井東圧化学株式会社
手続ネ市正古： （自発）
昭和６３年６月２１日
特許庁長官 吉 １）文 毅 殴
ｌ。事件の表示
事件との関係 特許出願人
住所 東京都千代田区霞が関三丁目２番５号名称（３１
２） 三井東圧化学株式会社４、補正により増加する
請求項の数 零５、補正の対象
明細書の発明の詳細な説明の欄
６、補正の内容
（１）明細書の第３頁第５〜６行にｒ −、、、−クラ
ンク、あるいは −」とあるを「−クラック、アルミ配
線のスライドあるいは− 」と訂正する。Patent applicant: Mitsui Toatsu Kagaku Co., Ltd. Procedure Ne Ichi Masako: (Voluntary) June 21, 1985 Commissioner of the Patent Office Yoshi 1) Moon Takeshi. Relationship between the case and the case Patent applicant address 3-2-5 Kasumigaseki, Chiyoda-ku, Tokyo Name (31
2) Mitsui Toatsu Chemical Co., Ltd. 4. Number of claims increased by amendment: 0 5. Detailed explanation of the invention in the specification subject to amendment 6, Contents of the amendment (1) Page 3, No. 5 of the specification ~ In line 6, the text "r-,...-crank, or -" is corrected to "-crack, slide of aluminum wiring, or-."
（２）同第８頁の第１１行と１２行の間に次の文を挿入
する。(2) Insert the following sentence between lines 11 and 12 on page 8.
「作業性、成形性を含めると特にＮ、Ｎ’−２，２−ビ
ス（４−（３−アミノフェノキシ）フェニル］プロパン
ビスマレイミド、Ｎ、Ｎ’−ビス［４−（３−アミノフ
ェノキシ）フェニル］スルフィドビスマレイミドがイ３
れている。"Including workability and moldability, N,N'-2,2-bis(4-(3-aminophenoxy)phenyl]propane bismaleimide, N,N'-bis[4-(3-aminophenoxy) phenyl] sulfide bismaleimide is
It is.
また上記マレイミド化合物は単独で使用しても併用して
もよく、必要に応じて上記マレイミド化合物以外のマレ
イミド化合物を併用してもよい。」（３）同第８頁１８
行と１９行の間に次の文を挿入する。Further, the above maleimide compounds may be used alone or in combination, and if necessary, maleimide compounds other than the above maleimide compounds may be used in combination. (3) 8th page 18
Insert the following statement between lines 19 and 19.
「本発明の樹脂組成物を製造するには例えば後述の実施
例のように各成分を配合、混練してもよいし、マレイミ
ドをノボラックフェノール樹脂に？８解させた後、配合
、混練してもよい。」（４）同第１０頁第２〜３行に「
本発明の−−−−−−−−−−・、シリコーンオイル
−”’−”Ｊとあるを次のように訂正する。``In order to produce the resin composition of the present invention, for example, each component may be blended and kneaded as in the examples below, or maleimide may be dissolved in novolak phenol resin, and then blended and kneaded. (4) On page 10, lines 2-3, “
The silicone oil of the present invention
-"'-"J is corrected as follows.
「更にアゾビスイソブチロニトリルのごときアブ化合物
、イミダゾール類、３級アミン類、４級アンモニウム塩
、有機金属化合物等の硬化促進剤を併用することもでき
る。``Furthermore, curing accelerators such as ab compounds such as azobisisobutyronitrile, imidazoles, tertiary amines, quaternary ammonium salts, and organometallic compounds can also be used in combination.
本発明の組成物は前述のものの外、必要に応してエポキ
シ樹脂、ノボラック型フェノール樹脂以外のフェノール
樹脂たとえばノボラック型フェノール樹脂、アミン類、
各種反応希釈剤、シリコーンオイル−”’−’−Ｊ
（５）同第１Ｏ頁第７行に「実施例１」とあるを「実施
例１〜３Ｊと訂正する。In addition to the above-mentioned compositions, the composition of the present invention may optionally contain epoxy resins, phenolic resins other than novolak-type phenolic resins, such as novolak-type phenolic resins, amines, etc.
Various reaction diluents, silicone oil -"'-'-J (5) In the same page 10, line 7, "Example 1" is corrected to "Examples 1 to 3J.
（６）同第１２真の表−１を別紙ｌのように訂正する。(6) Correct the 12th True Table-1 as shown in Attachment l.
（７）同第１３頁の表−２を別紙２のように訂正する。(7) Table 2 on page 13 of the same page is corrected as shown in Attachment 2.
以上
［′Ａ＋駈ｌ〕
（重量部）
プロパンビスマレイミド
＊３ Ｎ、Ｎ’−ビス（４−（３−アミノフェノキシ
）フェニル］スルフィドビスマレイミドAbove ['A + 1] (parts by weight) Propane bismaleimide *3 N,N'-bis(4-(3-aminophenoxy)phenyl) sulfide bismaleimide
Claims (1)
▲数式、化学式、表等があります▼よりな る２価の基を表わし、Ｘは直結、炭素数１〜１０の２価
の炭化水素基、６フッ素化されたイソプロピリデン基、
カルボニル基、チオ基、スルフィニル基、スルホニル基
又はオキシドから成る群より選ばれた基を表わす。） にて表わされるビスマレイミド化合物とノボラック型フ
ェノール樹脂を必須成分とする半導体封止用樹脂組成物
。(1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R consists of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Represents a divalent group, where X is a direct bond, a divalent hydrocarbon group having 1 to 10 carbon atoms, a hexafluorinated isopropylidene group,
Represents a group selected from the group consisting of a carbonyl group, a thio group, a sulfinyl group, a sulfonyl group, or an oxide. ) A resin composition for semiconductor encapsulation comprising a bismaleimide compound represented by the following and a novolac type phenol resin as essential components.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3752288A JPH01213336A (en) | 1988-02-22 | 1988-02-22 | Resin composition for sealing semiconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3752288A JPH01213336A (en) | 1988-02-22 | 1988-02-22 | Resin composition for sealing semiconductor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01213336A true JPH01213336A (en) | 1989-08-28 |
Family
ID=12499878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3752288A Pending JPH01213336A (en) | 1988-02-22 | 1988-02-22 | Resin composition for sealing semiconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01213336A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484157A2 (en) * | 1990-10-31 | 1992-05-06 | Kabushiki Kaisha Toshiba | Maleimide resin composition and resin encapsulated semiconductor device manufactured using the composition |
| JP2009263624A (en) * | 2008-03-31 | 2009-11-12 | Mitsubishi Plastics Inc | Bismaleimide composition |
-
1988
- 1988-02-22 JP JP3752288A patent/JPH01213336A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484157A2 (en) * | 1990-10-31 | 1992-05-06 | Kabushiki Kaisha Toshiba | Maleimide resin composition and resin encapsulated semiconductor device manufactured using the composition |
| JP2009263624A (en) * | 2008-03-31 | 2009-11-12 | Mitsubishi Plastics Inc | Bismaleimide composition |
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