JP2011074298A - Adhesive resin composition for silicon wafer - Google Patents
Adhesive resin composition for silicon wafer Download PDFInfo
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- JP2011074298A JP2011074298A JP2009229185A JP2009229185A JP2011074298A JP 2011074298 A JP2011074298 A JP 2011074298A JP 2009229185 A JP2009229185 A JP 2009229185A JP 2009229185 A JP2009229185 A JP 2009229185A JP 2011074298 A JP2011074298 A JP 2011074298A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/44—Amides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/20—Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
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- Power Engineering (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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Abstract
Description
本発明は接着性樹脂組成物に関し、特に、シリコンウエハとの接着性に著しく優れた、ウレア構造を有する化合物を一定量以上含有するエポキシ樹脂組成物に関する。 The present invention relates to an adhesive resin composition, and particularly to an epoxy resin composition containing a certain amount or more of a compound having a urea structure, which is remarkably excellent in adhesiveness to a silicon wafer.
近年、IT技術の発展に伴って多様な実装技術が開発されている。特に、半導体素子の直接固定や絶縁性、基板との接着性等は、多様な実装技術の工程や実装信頼性に必要不可欠なものであるので、半導体であるシリコンウエハと他基材とを接着する接着剤が重要視されている。接着剤の塗布方法は、半導体の実装形態により限定され、その主な塗布方法としてはアンダーフィル、スクリーン印刷、インクジェット、ドライフィルムラミネート、スピンコート等の方法が挙げられる。このような方法で塗布される接着性樹脂には、用途によって、低粘度、無溶剤、接着後の耐熱性等が要求される。また、硬化機構としては、簡便に上記の要求を満たすことのできる熱硬化機構が好ましい。 In recent years, various mounting technologies have been developed with the development of IT technology. In particular, direct fixing of semiconductor elements, insulation, adhesion to substrates, etc. are indispensable for various mounting technology processes and mounting reliability. Adhesive is important. The method of applying the adhesive is limited by the mounting form of the semiconductor, and examples of the main application method include underfill, screen printing, ink jet, dry film laminating, and spin coating. The adhesive resin applied by such a method is required to have low viscosity, no solvent, heat resistance after adhesion, and the like depending on the application. Moreover, as a hardening mechanism, the thermosetting mechanism which can satisfy said request | requirement simply is preferable.
しかしながら、シリコンウエハに対して良好な接着性を有する樹脂としては、従来、可溶化ポリイミド等、ごく一部の樹脂しか存在せず、熱硬化性樹脂でシリコンウエハに対して良好な接着性を有するものは未だ知られていない。 However, as a resin having good adhesion to a silicon wafer, only a small part of resin such as solubilized polyimide exists conventionally, and a thermosetting resin has good adhesion to a silicon wafer. Things are not yet known.
したがって本発明の目的は、シリコンウエハに対して良好な接着性を発揮する熱硬化性樹脂組成物を提供することにある。 Accordingly, an object of the present invention is to provide a thermosetting resin composition that exhibits good adhesion to a silicon wafer.
本発明者等は、上記の目的を達成するために鋭意検討を重ねた結果、ウレア構造を一定量以上含有するエポキシ樹脂組成物が極めて良好であることを見出し、本発明に到達した。
即ち本発明は、エポキシ樹脂100質量部に対して、ウレア構造を有する化合物を、該化合物中のウレア構造部分が0.1〜50質量部となるように含有してなることを特徴とする、シリコンウエハ接着性樹脂組成物である。
本発明においては更に、アミノ基と隣接する位置にフェノール性水酸基を有し、かつ、フェノール性水酸基を有する芳香族ジアミン由来の構造を有するポリアミド化合物、及び、フェノール樹脂からなる群の中から選択される少なくとも１種の樹脂を含有しても良い。
また、前記エポキシ樹脂は、ビスフェノールＡ骨格又はビスフェノールＦ骨格を有するエポキシ樹脂であることが好ましく、前記ウレア構造を有する化合物は、アミン化合物とイソシアネート化合物との反応生成物であることが好ましい。
As a result of intensive studies to achieve the above object, the present inventors have found that an epoxy resin composition containing a certain amount or more of a urea structure is extremely good, and have reached the present invention.
That is, the present invention relates to a silicon wafer comprising a compound having a urea structure with respect to 100 parts by mass of an epoxy resin so that the urea structure part in the compound is 0.1 to 50 parts by mass. It is an adhesive resin composition.
In the present invention, it is further selected from the group consisting of a polyamide compound having a phenolic hydroxyl group at a position adjacent to the amino group and having a structure derived from an aromatic diamine having a phenolic hydroxyl group, and a phenol resin. At least one kind of resin may be contained.
The epoxy resin is preferably an epoxy resin having a bisphenol A skeleton or a bisphenol F skeleton, and the compound having a urea structure is preferably a reaction product of an amine compound and an isocyanate compound.
本発明のシリコンウエハ接着性樹脂組成物は、熱硬化したときに適度なウレア構造を有するエポキシ樹脂硬化物となるので、シリコンウエハに対して極めて良好に接着する。 Since the silicon wafer adhesive resin composition of the present invention becomes an epoxy resin cured product having an appropriate urea structure when thermally cured, it adheres extremely well to a silicon wafer.
本発明に使用されるエポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物；ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール（ビスフェノールＦ）、メチレンビス（オルトクレゾール）、エチリデンビスフェノール、イソプロピリデンビスフェノール（ビスフェノールＡ）、イソプロピリデンビス（オルトクレゾール）、テトラブロモビスフェノールＡ、１，３−ビス（４−ヒドロキシクミルベンゼン）、１，４−ビス（４−ヒドロキシクミルベンゼン）、１，１，３−トリス（４−ヒドロキシフェニル）ブタン、１，１，２，２−テトラ（４−ヒドロキシフェニル）エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリジルエーテル化合物；エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール、ビスフェノールＡ−エチレンオキシド付加物等の多価アルコール類のポリグリシジルエーテル化合物；マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族又は脂環族多塩基酸のグリシジルエステル類及びグリシジルメタクリレートの単独重合体又は共重合体；Ｎ，Ｎ−ジグリシジルアニリン、ビス（４−（Ｎ−メチル−Ｎ−グリシジルアミノ）フェニル）メタン、ジグリシジルオルトトルイジン等のグリシジルアミノ基を有するエポキシ化合物；ビニルシクロヘキセンジエポキシド、ジシクロペンタンジエンジエポキサイド、３，４−エポキシシクロヘキシルメチル−３，４−エポキシシクロヘキサンカルボキシレート、３，４−エポキシ−６−メチルシクロヘキシルメチル−６−メチルシクロヘキサンカルボキシレート、ビス（３，４−エポキシ−６−メチルシクロヘキシルメチル）アジペート等の環状オレフィン化合物のエポキシ化物；エポキシ化ポリブタジエン、エポキシ化スチレン−ブタジエン共重合物等のエポキシ化共役ジエン重合体、トリグリシジルイソシアヌレート等の複素環化合物があげられる。 Examples of the epoxy resin used in the present invention include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F), Methylenebis (orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1,4-bis ( 4-hydroxycumylbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane, thiobisphenol, sulfobi Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as phenol, oxybisphenol, phenol novolak, orthocresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcin novolak, terpene phenol; ethylene glycol, propylene glycol, butylene glycol, Hexanediol, polyglycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, polyglycidyl ether compounds of polyhydric alcohols such as bisphenol A-ethylene oxide adduct; maleic acid, fumaric acid, itaconic acid, succinic acid , Glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, Limeric acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, endomethylenetetrahydrophthalic acid, etc. Homopolymers or copolymers of glycidyl esters of acid and glycidyl methacrylate; glycidyl such as N, N-diglycidylaniline, bis (4- (N-methyl-N-glycidylamino) phenyl) methane, diglycidyl orthotoluidine An epoxy compound having an amino group; vinylcyclohexene diepoxide, dicyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6 Me Epoxidized products of cyclic olefin compounds such as til cyclohexanecarboxylate and bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymer, And heterocyclic compounds such as triglycidyl isocyanurate.
上記のエポキシ樹脂は、末端イソシアネートのプレポリマーによって内部架橋されたもの、あるいは、多価の活性水素化合物（多価フェノール、ポリアミン、カルボニル基含有化合物、ポリリン酸エステル等）で高分子量化したものでもよい。 The above epoxy resin may be one internally crosslinked by a terminal isocyanate prepolymer, or one having a high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.). Good.
本発明で使用するウレア構造を有する化合物としては、アミン化合物とイソシアネート化合物との反応生成物が好ましい。前記アミン化合物としては、例えば、エチレンジアミン、１，２−ジアミノプロパン、１，３−ジアミノプロパン、１，３−ジアミノブタン、１，４−ジアミノブタン等のアルキレンジアミン類；ジエチレントリアミン、トリエチレントリアミン、テトラエチレンペンタミン等のポリアルキルポリアミン類；１，３−ジアミノメチルシクロヘキサン、１，２−ジアミノシクロヘキサン、１，４−ジアミノ−３，６−ジエチルシクロヘキサン、イソホロンジアミン等の脂環式ポリアミン類；ｍ−キシリレンジアミン、ジアミノジフェニルメタン、ジアミノジフェニルスルホン等の芳香族ポリアミン類；ベンゾグアナミン、アセトグアナミン等のグアナミン類；２−メチルイミダゾール、２−エチル−４−メチルイミダゾール、２−イソプロピルイミダゾール、２−ウンデシルイミダゾール、２−ヘプタデシルイミダゾール、２−フェニルイミダゾール、２−フェニル−４−メチルイミダゾール、２−アミノプロピルイミダゾール等のイミダゾール類；シュウ酸ジヒドラジド、マロン酸ジヒドラジド、コハク酸ジヒドラジド、グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、スベリン酸ジヒドラジド、アゼライン酸ジヒドラジド、セバシン酸ジヒドラジド、フタル酸ジヒドラジド等のジヒドラジド類；Ｎ，Ｎ−ジメチルアミノエチルアミン、Ｎ，Ｎ−ジエチルアミノエチルアミン、Ｎ，Ｎ−ジイソプロピルアミノエチルアミン、Ｎ，Ｎ−ジアリルアミノエチルアミン、Ｎ，Ｎ−ベンジルメチルアミノエチルアミン、Ｎ，Ｎ−ジベンジルアミノエチルアミン、Ｎ，Ｎ−シクロヘキシルメチルアミノエチルアミン、Ｎ，Ｎ−ジシクロヘキシルアミノエチルアミン、Ｎ−（２−アミノエチル）ピロリジン、Ｎ−（２−アミノエチル）ピペリジン、Ｎ−（２−アミノエチル）モルホリン、Ｎ−（２−アミノエチル）ピペラジン、Ｎ−（２−アミノエチル）−Ｎ’−メチルピペラジン、Ｎ，Ｎ−ジメチルアミノプロピルアミン、Ｎ，Ｎ−ジエチルアミノプロピルアミン、Ｎ，Ｎ−ジイソプロピルアミノプロピルアミン、Ｎ，Ｎ−ジアリルアミノプロピルアミン、Ｎ，Ｎ−ベンジルメチルアミノプロピルアミン、Ｎ，Ｎ−ジベンジルアミノプロピルアミン、Ｎ，Ｎ−シクロヘキシルメチルアミノプロピルアミン、Ｎ，Ｎ−ジシクロヘキシルアミノプロピルアミン、Ｎ−（３−アミノプロピル）ピロリジン、Ｎ−（３−アミノプロピル）ピペリジン、Ｎ−（３−アミノプロピル）モルホリン、Ｎ−（３−アミノプロピル）ピペラジン、Ｎ−（３−アミノプロピル）−Ｎ’−メチルピペリジン、４−（Ｎ，Ｎ−ジメチルアミノ）ベンジルアミン、４−（Ｎ，Ｎ−ジエチルアミノ）ベンジルアミン、４−（Ｎ，Ｎ−ジイソプロピルアミノ）ベンジルアミン、Ｎ，Ｎ，−ジメチルイソホロンジアミン、Ｎ，Ｎ−ジメチルビスアミノシクロヘキサン、Ｎ，Ｎ，Ｎ’−トリメチルエチレンジアミン、Ｎ’−エチル−Ｎ，Ｎ−ジメチルエチレンジアミン、Ｎ，Ｎ，Ｎ’−トリメチルエチレンジアミン、Ｎ’−エチル−Ｎ，Ｎ−ジメチルプロパンジアミン、Ｎ’−エチル−Ｎ，Ｎ−ジベンジルアミノプロピルアミン；Ｎ，Ｎ−（ビスアミノプロピル）−Ｎ−メチルアミン、Ｎ，Ｎ−ビスアミノプロピルエチルアミン、Ｎ，Ｎ−ビスアミノプロピルプロピルアミン、Ｎ，Ｎ−ビスアミノプロピルブチルアミン、Ｎ，Ｎ−ビスアミノプロピルペンチルアミン、Ｎ，Ｎ−ビスアミノプロピルヘキシルアミン、Ｎ，Ｎ−ビスアミノプロピル−２−エチルヘキシルアミン、Ｎ，Ｎ−ビスアミノプロピルシクロヘキシルアミン、Ｎ，Ｎ−ビスアミノプロピルベンジルアミン、Ｎ，Ｎ−ビスアミノプロピルアリルアミン、ビス〔３−（Ｎ，Ｎ−ジメチルアミノプロピル）〕アミン、ビス〔３−（Ｎ，Ｎ−ジエチルアミノプロピル）〕アミン、ビス〔３−（Ｎ，Ｎ−ジイソプロピルアミノプロピル）〕アミン、ビス〔３−（Ｎ，Ｎ−ジブチルアミノプロピル）〕アミン等があげられる。 The compound having a urea structure used in the present invention is preferably a reaction product of an amine compound and an isocyanate compound. Examples of the amine compound include alkylenediamines such as ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, and 1,4-diaminobutane; diethylenetriamine, triethylenetriamine, tetra Polyalkylpolyamines such as ethylenepentamine; alicyclic polyamines such as 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane, isophoronediamine; Aromatic polyamines such as xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone; guanamines such as benzoguanamine, acetoguanamine; 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropyl Imidazoles such as midazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-aminopropylimidazole; oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, Dihydrazides such as glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, phthalic acid dihydrazide; N, N-dimethylaminoethylamine, N, N-diethylaminoethylamine, N, N-diisopropylaminoethylamine N, N-diallylaminoethylamine, N, N-benzylmethylaminoethylamine, N, N-dibenzylaminoethylamine, N, N-cyclohexyl Tylaminoethylamine, N, N-dicyclohexylaminoethylamine, N- (2-aminoethyl) pyrrolidine, N- (2-aminoethyl) piperidine, N- (2-aminoethyl) morpholine, N- (2-aminoethyl) Piperazine, N- (2-aminoethyl) -N′-methylpiperazine, N, N-dimethylaminopropylamine, N, N-diethylaminopropylamine, N, N-diisopropylaminopropylamine, N, N-diallylaminopropyl Amine, N, N-benzylmethylaminopropylamine, N, N-dibenzylaminopropylamine, N, N-cyclohexylmethylaminopropylamine, N, N-dicyclohexylaminopropylamine, N- (3-aminopropyl) pyrrolidine N- (3-aminopropyl) pi Peridine, N- (3-aminopropyl) morpholine, N- (3-aminopropyl) piperazine, N- (3-aminopropyl) -N′-methylpiperidine, 4- (N, N-dimethylamino) benzylamine, 4- (N, N-diethylamino) benzylamine, 4- (N, N-diisopropylamino) benzylamine, N, N, -dimethylisophoronediamine, N, N-dimethylbisaminocyclohexane, N, N, N′- Trimethylethylenediamine, N′-ethyl-N, N-dimethylethylenediamine, N, N, N′-trimethylethylenediamine, N′-ethyl-N, N-dimethylpropanediamine, N′-ethyl-N, N-dibenzylamino Propylamine; N, N- (bisaminopropyl) -N-methylamine, N, N-bisaminop Pyrethylamine, N, N-bisaminopropylpropylamine, N, N-bisaminopropylbutylamine, N, N-bisaminopropylpentylamine, N, N-bisaminopropylhexylamine, N, N-bisaminopropyl- 2-ethylhexylamine, N, N-bisaminopropylcyclohexylamine, N, N-bisaminopropylbenzylamine, N, N-bisaminopropylallylamine, bis [3- (N, N-dimethylaminopropyl)] amine, Examples include bis [3- (N, N-diethylaminopropyl)] amine, bis [3- (N, N-diisopropylaminopropyl)] amine, and bis [3- (N, N-dibutylaminopropyl)] amine. .
前記イソシアネート化合物としては、例えば、２，４−トリレンジイソシアネート、２，６−トリレンジイソシアネート、４，４−ジフェニルメタンジイソシアネート、フェニレンジイソシアネート、キシリレンジイソシアネート、テトラメチルキシリレンジイソシアネート、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート、リジンジイソシアネートエステル、１，４−シクロへキシレンジイソシアネート、４，４’−ジシクロへキシレンメタンジイソシアネート、３，３’−ジメトキシ−４，４’−ビフェニレンジイソシアネート、１，５−ナフタレンジイソシアネート、１，５−テトラヒドロナフタレンジイソシアネート、イソホロンジイソシアネート等があげられる。 Examples of the isocyanate compound include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, phenylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, tetramethylene diisocyanate, hexamethylene. Diisocyanate, lysine diisocyanate ester, 1,4-cyclohexylene diisocyanate, 4,4′-dicyclohexylene methane diisocyanate, 3,3′-dimethoxy-4,4′-biphenylene diisocyanate, 1,5-naphthalene diisocyanate, 1, Examples include 5-tetrahydronaphthalene diisocyanate and isophorone diisocyanate.
本発明で使用することのできるウレア構造を有する化合物の市販品としては、例えば、アデカハードナーEH-4380S（（株）ADEKA製ウレア構造を有するアミン系硬化剤の商品名）「ウレア構造含有率（化合物中に占める−ＮＨＣＯＮＨ−の質量％）：２２．８質量%」、U-CAT 3502T（サンアプロ（株）製芳香族ジメチルウレア化合物）、U-CAT 3503N（サンアプロ（株）製脂肪族ジメチルウレア化合物の商品名）、Dyhard UR
500（デグサジャパン（株）製芳香族ジメチルウレア化合物の商品名）、Dyhard UR 300（デグサジャパン（株）製芳香族ジメチルウレア化合物の商品名）、Dyhard
UR 200（デグサジャパン（株）製芳香族ジメチルウレア化合物の商品名）等があげられる。
As a commercial product of a compound having a urea structure that can be used in the present invention, for example, Adeka Hardener EH-4380S (trade name of an amine-based curing agent having a urea structure manufactured by ADEKA Co., Ltd.) “Urea structure content ( -NHCONH- in the compound (% by mass): 22.8% by mass ", U-CAT 3502T (aromatic dimethylurea compound manufactured by San Apro Co., Ltd.), U-CAT 3503N (aliphatic dimethyl urea manufactured by San Apro Co., Ltd.) Compound trade name), Dyhard UR
500 (trade name of aromatic dimethylurea compound manufactured by Degussa Japan), Dyhard UR 300 (trade name of aromatic dimethylurea compound manufactured by Degussa Japan), Dyhard
UR 200 (trade name of aromatic dimethylurea compound manufactured by Degussa Japan Co., Ltd.) and the like.
本発明のシリコンウエハ接着性樹脂組成物においては、エポキシ樹脂100質量部に対して、ウレア構造を有する化合物を、該化合物中のウレア構造部分が0.1〜50質量部となるように、好ましくは0.2〜30質量部となるように使用する。ウレア構造を有する部分（−ＮＨＣＯＮＨ−）が0.1質量部未満又は50質量部を超えた場合には、十分な接着性が得られないため好ましくない。 In the silicon wafer adhesive resin composition of the present invention, with respect to 100 parts by mass of the epoxy resin, the compound having a urea structure is preferably 0.2 to 30 parts by mass of the urea structure in the compound. It is used so that it may be -30 mass parts. When the portion having a urea structure (-NHCONH-) is less than 0.1 parts by mass or exceeds 50 parts by mass, sufficient adhesiveness cannot be obtained, which is not preferable.
本発明のシリコンウエハ接着性樹脂組成物には、エポキシ樹脂と共に他の樹脂を併用することができる。上記他の樹脂としては、例えば、フェノール樹脂、ポリアミド樹脂、ポリイミド樹脂、シアン酸エステル化合物、フェノキシ樹脂、ポリブタジエンゴム、等があげられる。 Another resin can be used together with the epoxy resin in the silicon wafer adhesive resin composition of the present invention. Examples of the other resin include phenol resin, polyamide resin, polyimide resin, cyanate ester compound, phenoxy resin, and polybutadiene rubber.
本発明のシリコンウエハ接着性樹脂組成物は、更に、フェノール樹脂を含有することが好ましい。これによって、高ガラス転移温度、強靭性、耐水性、耐薬品性、及び高密着性等が得られる。 The silicon wafer adhesive resin composition of the present invention preferably further contains a phenol resin. Thereby, a high glass transition temperature, toughness, water resistance, chemical resistance, high adhesion, and the like are obtained.
上記フェノール樹脂としては、フェノール類とアルデヒド類より合成されるフェノール樹脂がある。上記フェノール類としては、例えば、フェノール、クレゾール、エチルフェノール、ｎ−プロピルフェノール、イソプロピルフェノール、ブチルフェノール、第三ブチルフェノール、オクチルフェノール、ノニルフェノール、ドデシルフェノール、シクロヘキシルフェノール、クロロフェノール、ブロモフェノール、レゾルシン、カテコール、ハイドロキノン、２，２−ビス（４−ヒドロキシフェニル）プロパン、４，４’−チオジフェノール、ジヒドロキシジフェニルメタン、ナフトール、テルペンフェノール、フェノール化ジシクロペンタジエン等があげられ、前記アルデヒド類としては、ホルムアルデヒドがあげられる。 Examples of the phenol resin include phenol resins synthesized from phenols and aldehydes. Examples of the phenols include phenol, cresol, ethylphenol, n-propylphenol, isopropylphenol, butylphenol, tert-butylphenol, octylphenol, nonylphenol, dodecylphenol, cyclohexylphenol, chlorophenol, bromophenol, resorcin, catechol, and hydroquinone. 2,2-bis (4-hydroxyphenyl) propane, 4,4′-thiodiphenol, dihydroxydiphenylmethane, naphthol, terpenephenol, phenolized dicyclopentadiene, etc., and the aldehydes include formaldehyde It is done.
また本発明においては、フェノール類の一部をビフェニル等の芳香族化合物に置き換えたものも使用することができる。更に、上記フェノール類をジシクロペンタジエンで連結して得られるフェノール樹脂も使用することができる。 Moreover, in this invention, what substituted some aromatic phenols, such as biphenyl, can also be used. Furthermore, a phenol resin obtained by connecting the above phenols with dicyclopentadiene can also be used.
本発明のシリコンウエハ接着性樹脂組成物は、更に、フェノール性水酸基をアミノ基と隣接する位置に有し、かつ、フェノール性水酸基含有芳香族ジアミン由来の構造を有するポリアミド化合物を含有することが好ましい。これによって、高ガラス転移温度、強靭性、高密着性、及び低熱膨張性が更に改善される。 The silicon wafer adhesive resin composition of the present invention preferably further contains a polyamide compound having a phenolic hydroxyl group adjacent to the amino group and having a structure derived from a phenolic hydroxyl group-containing aromatic diamine. . This further improves the high glass transition temperature, toughness, high adhesion, and low thermal expansion.
また、本発明のシリコンウエハ接着性樹脂組成物には、必要に応じて、ガラス繊維、炭素繊維、セルロース、ケイ砂、セメント、カオリン、クレー、水酸化アルミニウム、ベントナイト、タルク、シリカ、微粉末シリカ、二酸化チタン、カーボンブラック、グラファイト、酸化鉄、瀝青物質、金属粒子、金属で被覆された樹脂粒子等の充填剤若しくは顔料；増粘剤；チキソトロピック剤；難燃剤；消泡剤；防錆剤；コロイダルシリカ、コロイダルアルミナ等の常用の添加物を含有させても良く、更に、キシレン樹脂、石油樹脂等の粘着性の樹脂類を併用することもできる。 In addition, the silicon wafer adhesive resin composition of the present invention includes glass fiber, carbon fiber, cellulose, silica sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, fine powder silica as necessary. , Titanium dioxide, carbon black, graphite, iron oxide, bitumen, metal particles, resin particles coated with metal, etc .; thickeners; thixotropic agents; flame retardants; antifoaming agents; Conventional additives such as colloidal silica and colloidal alumina may be contained, and adhesive resins such as xylene resin and petroleum resin may be used in combination.
特にシリカフィラーを併用した場合には、組成物の熱膨張係数の制御が容易となるだけでなく、本発明のシリコンウエハ接着性樹脂組成物が熱硬化した後の、硬化樹脂の弾性率を向上させ、これによって熱硬化後の樹脂が高強度となるので好ましい。 In particular, when silica filler is used in combination, not only the thermal expansion coefficient of the composition can be easily controlled, but also the elastic modulus of the cured resin after the silicon wafer adhesive resin composition of the present invention is thermally cured is improved. This is preferable because the resin after thermosetting has high strength.
以下実施例を示して本発明のシリコンウエハ接着性樹脂組成物を更に詳細に説明するが、本発明はこれらによって限定されるものではない。
［実施例１〜１１及び比較例１〜５］
Hereinafter, the silicon wafer adhesive resin composition of the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
[Examples 1 to 11 and Comparative Examples 1 to 5]
下記表１又は２に示した配合の樹脂組成物とプロピレングリコールモノメチルエーテルを混合し、シリコンウエハ上に、硬化後の膜厚みが３０〜４０μｍとなるように塗布した後、１００℃で１０分間かけて溶媒を除去して乾燥し、その後１８０℃で1時間かけて樹脂を硬化させた。得られた試験片を用いて、ＪＩＳ Ｄ０２０２の碁盤面試験方法に準拠したセロハン粘着テープによるピールテスト（クロスカット試験）を行い、残部の個数を表に示した。更に、121℃/2.1気圧/100％RH条件下でプレッシャークッカー試験を９６時間行った後にクロスカット試験を行い、残部の個数を表に示した。 A resin composition having the composition shown in Table 1 or 2 below and propylene glycol monomethyl ether are mixed and applied on a silicon wafer so that the film thickness after curing is 30 to 40 μm, and then at 100 ° C. for 10 minutes. The solvent was removed and dried, and then the resin was cured at 180 ° C. for 1 hour. Using the obtained test piece, a peel test (cross-cut test) was performed using a cellophane adhesive tape in accordance with the grid surface test method of JIS D0202, and the number of remaining parts was shown in the table. Further, a pressure cooker test was performed for 96 hours under the conditions of 121 ° C./2.1 atm / 100% RH, and then a cross cut test was performed.
参考例（ウレア含有化合物１の合成）
イソブタノール１６２．５ｇ、キシレン１６２．５ｇ、Ｎ，Ｎ−ジメチルアミノプロピルアミン４０８ｇ、及び１，２−プロパンジアミン１４８ｇを仕込み、６０〜７０℃で３０分間混合攪拌した。次いで、アデカレジンＥＰ−４１００Ｅ（株式会社ＡＤＥＫＡ製ビスフェノールＡ型エポキシ樹脂；エポキシ当量１９０の商品名）１９０ｇを、反応系内の温度が上昇しないようにゆっくりと滴下し、２時間還流して熟成した。
Reference example (synthesis of urea-containing compound 1)
162.5 g of isobutanol, 162.5 g of xylene, 408 g of N, N-dimethylaminopropylamine, and 148 g of 1,2-propanediamine were charged and mixed and stirred at 60 to 70 ° C. for 30 minutes. Next, 190 g of Adeka Resin EP-4100E (bisphenol A type epoxy resin manufactured by ADEKA Corporation; trade name of epoxy equivalent 190) was slowly added dropwise so that the temperature in the reaction system did not rise, and the mixture was refluxed for 2 hours for aging.
更に、イソホロンジイソシアネート６７質量％のキシレン溶液６６６ｇを、反応系内の温度が上昇しないようにゆっくりと滴下した。滴下終了後昇温し、１４０〜１５０℃で２時間還流熟成を行い、ＩＲによってイソシアネートの吸収である２２５０ｃｍ−１の吸収が消えたことを確認した後、２００℃まで昇温して２時間、常圧で脱溶剤処理を行った。更に１９０〜２００℃、５０〜６０ｍｍＨｇで１時間減圧脱溶剤して、淡白色の固形物を得た。
Furthermore, 666 g of a xylene solution of 67% by mass of isophorone diisocyanate was slowly added dropwise so that the temperature in the reaction system did not rise. After completion of the dropwise addition, the temperature was raised and reflux ripening was performed at 140 to 150 ° C. for 2 hours. After confirming that the absorption at 2250 cm −1 , which is the absorption of isocyanate, disappeared by IR, the temperature was raised to 200 ° C. for 2 hours. Solvent removal treatment was performed at normal pressure. Further, the solvent was removed under reduced pressure at 190 to 200 ° C. and 50 to 60 mmHg for 1 hour to obtain a pale white solid.
表１及び表２の結果は、エポキシ樹脂100質量部に対して、ウレア構造を有する化合物を、該化合物中のウレア構造部分が0.1〜50質量部となるように含有する本願発明の効果を実証するものである。 The results in Tables 1 and 2 demonstrate the effect of the present invention that contains a compound having a urea structure with respect to 100 parts by mass of the epoxy resin so that the urea structure part in the compound is 0.1 to 50 parts by mass. To do.
本発明のシリコンウエハ接着性樹脂組成物は、シリコンウエハに対して、硬化後に良好な接着性を有し、金属シリコンに対して他の材料を接着する場合、或いは半導体素子を他の基材に直接実装する場合に有用であるだけでなく、組成物それ自体を層間絶縁膜や保護膜とすることもできるので、産業上極めて有用である。 The silicon wafer adhesive resin composition of the present invention has good adhesion to a silicon wafer after curing, and when bonding other materials to metal silicon, or a semiconductor element on another substrate In addition to being useful for direct mounting, the composition itself can be used as an interlayer insulating film or a protective film, which is extremely useful in the industry.
Claims (5)
The adhesive resin composition for silicon wafers according to any one of claims 1 to 5, wherein the compound having a urea structure is a reaction product of an amine compound and an isocyanate compound.
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| JP2009229185A JP5565931B2 (en) | 2009-10-01 | 2009-10-01 | Silicon wafer adhesive resin composition |
| KR1020127007294A KR101638660B1 (en) | 2009-10-01 | 2010-09-07 | Adhesive resin composition for silicon wafers |
| PCT/JP2010/005479 WO2011039948A1 (en) | 2009-10-01 | 2010-09-07 | Adhesive resin composition for silicon wafers |
| CN201080042465.3A CN102575137B (en) | 2009-10-01 | 2010-09-07 | Adhesive resin composition for silicon wafers |
| TW099130893A TWI504710B (en) | 2009-10-01 | 2010-09-13 | Adhesive resin composition for silicon wafer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20140103902A (en) * | 2011-11-15 | 2014-08-27 | 알즈켐 아게 | Use of n,n'-dimethyl-urones and method for curing epoxy resin compositions |
| WO2021193233A1 (en) * | 2020-03-25 | 2021-09-30 | 株式会社Adeka | Curable resin composition and method for suppressing curing shrinkage of curable resin composition |
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| CN103059786A (en) * | 2011-10-21 | 2013-04-24 | 山东轻工业学院 | Adhesive for insulating materials |
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| WO2021193233A1 (en) * | 2020-03-25 | 2021-09-30 | 株式会社Adeka | Curable resin composition and method for suppressing curing shrinkage of curable resin composition |
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| KR20120090984A (en) | 2012-08-17 |
| TWI504710B (en) | 2015-10-21 |
| KR101638660B1 (en) | 2016-07-11 |
| CN102575137A (en) | 2012-07-11 |
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| WO2011039948A1 (en) | 2011-04-07 |
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