JPWO2019150446A1 - Methods for Manufacturing Adhesive Compositions, Film Adhesives, Adhesive Sheets, and Semiconductor Devices - Google Patents

Methods for Manufacturing Adhesive Compositions, Film Adhesives, Adhesive Sheets, and Semiconductor Devices Download PDF

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JPWO2019150446A1
JPWO2019150446A1 JP2019568439A JP2019568439A JPWO2019150446A1 JP WO2019150446 A1 JPWO2019150446 A1 JP WO2019150446A1 JP 2019568439 A JP2019568439 A JP 2019568439A JP 2019568439 A JP2019568439 A JP 2019568439A JP WO2019150446 A1 JPWO2019150446 A1 JP WO2019150446A1
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adhesive
film
component
adhesive composition
resin
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JP7176536B2 (en
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慎太郎 橋本
慎太郎 橋本
祐樹 中村
祐樹 中村
智陽 山崎
智陽 山崎
健太 菊地
健太 菊地
大輔 舛野
大輔 舛野
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Resonac Corp
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Hitachi Chemical Co Ltd
Showa Denko Materials Co Ltd
Resonac Corp
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Priority to JP2022179719A priority Critical patent/JP7472954B2/en
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    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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  • Dicing (AREA)

Abstract

熱硬化性樹脂と硬化剤とエラストマーとを含有し、熱硬化性樹脂が脂環式環を有するエポキシ樹脂を含む接着剤組成物が開示される。また、このような接着剤組成物を用いたフィルム状接着剤が開示される。さらに、このようなフィルム状接着剤を用いた接着シート及び半導体装置の製造方法が提供される。An adhesive composition containing a thermosetting resin, a curing agent, and an elastomer, and the thermosetting resin containing an epoxy resin having an alicyclic ring is disclosed. Further, a film-like adhesive using such an adhesive composition is disclosed. Further, a method for manufacturing an adhesive sheet and a semiconductor device using such a film-like adhesive is provided.

Description

本発明は、接着剤組成物、フィルム状接着剤、接着シート、及び半導体装置の製造方法に関する。 The present invention relates to a method for manufacturing an adhesive composition, a film-like adhesive, an adhesive sheet, and a semiconductor device.

従来、半導体チップと半導体チップ搭載用の支持部材との接合には、主に銀ペーストが使用されている。しかし、近年の半導体チップの小型化・集積化に伴い、使用される支持部材にも小型化、細密化が要求されるようになっている。その一方で、銀ペーストを用いる場合では、ペーストのはみ出し又は半導体チップの傾きに起因するワイヤボンディング時における不具合の発生、膜厚制御の困難性、ボイド発生等の問題が生じる場合がある。 Conventionally, silver paste is mainly used for joining a semiconductor chip and a support member for mounting the semiconductor chip. However, with the recent miniaturization and integration of semiconductor chips, the support members used are also required to be miniaturized and densified. On the other hand, when a silver paste is used, problems such as protrusion of the paste or inclination of the semiconductor chip during wire bonding, difficulty in controlling the film thickness, and void generation may occur.

そのため、近年、半導体チップと支持部材とを接合するためのフィルム状接着剤が使用されている（例えば、特許文献１参照）。ダイシングテープとダイシングテープ上に積層されたフィルム状接着剤とを備える接着シートを用いる場合、半導体ウェハの裏面にフィルム状接着剤を貼り付け、ダイシングによって半導体ウェハを個片化することによって、フィルム状接着剤付き半導体チップを得ることができる。得られたフィルム状接着剤付き半導体チップは、フィルム状接着剤を介して支持部材に貼り付け、熱圧着により接合することができる。 Therefore, in recent years, a film-like adhesive for joining a semiconductor chip and a support member has been used (see, for example, Patent Document 1). When an adhesive sheet including a dicing tape and a film-like adhesive laminated on the dicing tape is used, the film-like adhesive is attached to the back surface of the semiconductor wafer, and the semiconductor wafer is separated by dicing to form a film. A semiconductor chip with an adhesive can be obtained. The obtained semiconductor chip with a film-like adhesive can be attached to a support member via a film-like adhesive and bonded by thermocompression bonding.

特開２００７−０５３２４０号公報Japanese Unexamined Patent Publication No. 2007-053240

しかしながら、半導体チップのサイズが小さくなるにつれて、熱圧着時に単位面積当たりにかかる力が大きくなり、フィルム状接着剤が半導体チップからはみ出す、ブリードという現象が発生する場合がある。 However, as the size of the semiconductor chip decreases, the force applied per unit area during thermocompression bonding increases, and a phenomenon called bleeding may occur in which the film-like adhesive protrudes from the semiconductor chip.

また、フィルム状接着剤をワイヤ埋め込み型フィルム状接着剤であるＦＯＷ（Ｆｉｌｍ Ｏｖｅｒ Ｗｉｒｅ）又は半導体チップ埋め込み型フィルム状接着剤であるＦＯＤ（Ｆｉｌｍ Ｏｖｅｒ Ｄｉｅ）として用いる場合は、埋め込み性を向上させる観点から、熱圧着時に高い流動性が求められる。そのため、ブリードの発生頻度及び量がさらに増大する傾向にある。場合によっては、ブリードが半導体チップ上面にまで生じることがあり、これによって、電気不良又はワイヤボンディング不良につながるおそれがある。 Further, when the film-like adhesive is used as FOW (Film Over Ware) which is a wire-embedded film-like adhesive or FOD (Film Over Die) which is a semiconductor chip-embedded film-like adhesive, the viewpoint of improving the embedding property Therefore, high fluidity is required during thermocompression bonding. Therefore, the frequency and amount of bleeding tend to increase further. In some cases, bleeding may occur even on the upper surface of the semiconductor chip, which may lead to electrical failure or wire bonding failure.

本発明は、このような実情に鑑みてなされたものであり、熱圧着時に良好な埋め込み性を有しつつ、ブリードを抑制することが可能な接着剤組成物を提供することを主な目的とする。 The present invention has been made in view of such circumstances, and an object of the present invention is to provide an adhesive composition capable of suppressing bleeding while having good embedding property at the time of thermocompression bonding. To do.

本発明の一側面は、熱硬化性樹脂と硬化剤とエラストマーとを含有し、熱硬化性樹脂が脂環式環を有するエポキシ樹脂を含む接着剤組成物を提供する。このような接着剤組成物によれば、熱圧着時に良好な埋め込み性を有しつつ、ブリードを抑制することが可能となる。 One aspect of the present invention provides an adhesive composition containing a thermosetting resin, a curing agent, and an elastomer, and the thermosetting resin contains an epoxy resin having an alicyclic ring. According to such an adhesive composition, it is possible to suppress bleeding while having good embedding property at the time of thermocompression bonding.

硬化剤は、フェノール樹脂を含んでいてよい。また、エラストマーは、アクリル樹脂を含んでいてよい。 The curing agent may contain a phenol resin. Further, the elastomer may contain an acrylic resin.

熱硬化性樹脂は、脂環式環を有しない芳香族エポキシ樹脂をさらに含んでいてもよい。脂環式環を有しない芳香族エポキシ樹脂は、２５℃で液体であってよい。 The thermosetting resin may further contain an aromatic epoxy resin that does not have an alicyclic ring. The aromatic epoxy resin having no alicyclic ring may be liquid at 25 ° C.

接着剤組成物は、無機フィラーをさらに含有していてもよい。また、接着剤組成物は、硬化促進剤をさらに含有していてもよい。 The adhesive composition may further contain an inorganic filler. In addition, the adhesive composition may further contain a curing accelerator.

接着剤組成物は、基板上に第１のワイヤを介して第１の半導体素子がワイヤボンディング接続されると共に、第１の半導体素子上に、第２の半導体素子が圧着されてなる半導体装置において、第２の半導体素子を圧着すると共に第１のワイヤの少なくとも一部を埋め込むために用いられるものであってよい。 The adhesive composition is used in a semiconductor device in which a first semiconductor element is wire-bonded on a substrate via a first wire, and a second semiconductor element is crimped onto the first semiconductor element. , It may be used for crimping the second semiconductor element and embedding at least a part of the first wire.

本発明はさらに、熱硬化性樹脂と硬化剤とエラストマーとを含有し、熱硬化性樹脂が脂環式環を有するエポキシ樹脂を含む組成物の、基板上に第１のワイヤを介して第１の半導体素子がワイヤボンディング接続されると共に、第１の半導体素子上に、第２の半導体素子が圧着されてなる半導体装置において、第２の半導体素子を圧着すると共に第１のワイヤの少なくとも一部を埋め込むために用いられる、接着剤としての応用又は接着剤の製造のための応用に関してもよい。 The present invention further comprises a composition comprising a thermosetting resin, a curing agent and an elastomer, and the thermosetting resin containing an epoxy resin having an alicyclic ring, on a substrate via a first wire. In a semiconductor device in which the semiconductor elements of the above are bonded and connected by wire bonding and the second semiconductor element is crimped onto the first semiconductor element, the second semiconductor element is crimped and at least a part of the first wire is crimped. It may also relate to an application as an adhesive or an application for manufacturing an adhesive, which is used for embedding.

別の側面において、本発明は、上述の接着剤組成物をフィルム状に形成してなるフィルム状接着剤を提供する。 In another aspect, the present invention provides a film-like adhesive obtained by forming the above-mentioned adhesive composition into a film.

別の側面において、本発明は、基材と基材上に設けられた上述のフィルム状接着剤とを備える接着シートを提供する。 In another aspect, the present invention provides an adhesive sheet comprising a substrate and the film-like adhesive provided on the substrate.

基材は、ダイシングテープであってよい。なお、本明細書において、基材がダイシングテープである接着シートを「ダイシングダイボンディング一体型接着シート」という場合がある。 The base material may be a dicing tape. In the present specification, an adhesive sheet whose base material is a dicing tape may be referred to as a “dicing die bonding integrated adhesive sheet”.

接着シートは、フィルム状接着剤の基材とは反対側の面に積層された保護フィルムをさらに備えてもよい。 The adhesive sheet may further include a protective film laminated on the surface of the film-like adhesive opposite to the base material.

さらに、別の側面において、本発明は、基板上に第１のワイヤを介して第１の半導体素子を電気的に接続するワイヤボンディング工程と、第２の半導体素子の片面に、上述のフィルム状接着剤を貼付するラミネート工程と、フィルム状接着剤が貼付された第２の半導体素子を、フィルム状接着剤を介して圧着することで、第１のワイヤの少なくとも一部をフィルム状接着剤に埋め込むダイボンド工程と、を備える、半導体装置の製造方法を提供する。 Further, in another aspect, the present invention has a wire bonding step of electrically connecting the first semiconductor element on the substrate via the first wire, and the above-mentioned film-like film on one side of the second semiconductor element. By crimping the laminating step of applying the adhesive and the second semiconductor element to which the film-like adhesive is attached via the film-like adhesive, at least a part of the first wire is made into the film-like adhesive. Provided is a method for manufacturing a semiconductor device, comprising a die bonding process for embedding.

なお、半導体装置は、半導体基板上に第１のワイヤを介して第１の半導体チップがワイヤボンディング接続されると共に、第１の半導体チップ上に、第２の半導体チップが接着フィルムを介して圧着されることで、第１のワイヤの少なくとも一部が接着フィルムに埋め込まれてなるワイヤ埋込型の半導体装置であってもよく、第１のワイヤ及び第１の半導体チップが接着フィルムに埋め込まれてなるチップ埋込型の半導体装置であってもよい。 In the semiconductor device, the first semiconductor chip is wire-bonded to the semiconductor substrate via the first wire, and the second semiconductor chip is crimped onto the first semiconductor chip via an adhesive film. By doing so, a wire-embedded semiconductor device in which at least a part of the first wire is embedded in the adhesive film may be used, and the first wire and the first semiconductor chip are embedded in the adhesive film. It may be a chip-embedded semiconductor device.

本発明によれば、熱圧着時に良好な埋め込み性を有しつつ、ブリードを抑制することが可能な接着剤組成物が提供される。そのため、当該接着剤組成物をフィルム状に形成してなるフィルム状接着剤は、半導体チップ埋め込み型フィルム状接着剤であるＦＯＤ（Ｆｉｌｍ Ｏｖｅｒ Ｄｉｅ）又はワイヤ埋め込み型フィルム状接着剤であるＦＯＷ（Ｆｉｌｍ Ｏｖｅｒ Ｗｉｒｅ）として有用となり得る。また、本発明によれば、このようなフィルム状接着剤を用いた接着シート及び半導体装置の製造方法が提供される。 According to the present invention, there is provided an adhesive composition capable of suppressing bleeding while having good embedding property at the time of thermocompression bonding. Therefore, the film-like adhesive formed by forming the adhesive composition into a film is FOD (Film Over Die), which is a semiconductor chip-embedded film-like adhesive, or FOW (Film), which is a wire-embedded film-like adhesive. It can be useful as OverWire). Further, according to the present invention, there is provided a method for manufacturing an adhesive sheet and a semiconductor device using such a film-like adhesive.

一実施形態に係るフィルム状接着剤を示す模式断面図である。It is a schematic cross-sectional view which shows the film-like adhesive which concerns on one Embodiment. 一実施形態に係る接着シートを示す模式断面図である。It is a schematic cross-sectional view which shows the adhesive sheet which concerns on one Embodiment. 他の実施形態に係る接着シートを示す模式断面図である。It is a schematic cross-sectional view which shows the adhesive sheet which concerns on other embodiment. 一実施形態に係る半導体装置を示す模式断面図である。It is a schematic cross-sectional view which shows the semiconductor device which concerns on one Embodiment. 一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。It is a schematic cross-sectional view which shows a series of steps of the manufacturing method of the semiconductor device which concerns on one Embodiment. 一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。It is a schematic cross-sectional view which shows a series of steps of the manufacturing method of the semiconductor device which concerns on one Embodiment. 一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。It is a schematic cross-sectional view which shows a series of steps of the manufacturing method of the semiconductor device which concerns on one Embodiment. 一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。It is a schematic cross-sectional view which shows a series of steps of the manufacturing method of the semiconductor device which concerns on one Embodiment. 一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。It is a schematic cross-sectional view which shows a series of steps of the manufacturing method of the semiconductor device which concerns on one Embodiment.

以下、図面を適宜参照しながら、本発明の実施形態について説明する。ただし、本発明は以下の実施形態に限定されるものではない。 Hereinafter, embodiments of the present invention will be described with reference to the drawings as appropriate. However, the present invention is not limited to the following embodiments.

本明細書において、（メタ）アクリル酸はアクリル酸又はそれに対応するメタクリル酸を意味する。（メタ）アクリロイル基等の他の類似表現についても同様である。 As used herein, (meth) acrylic acid means acrylic acid or methacrylic acid corresponding thereto. The same applies to other similar expressions such as (meth) acryloyl group.

［接着剤組成物］
本実施形態に係る接着剤組成物は、（Ａ）熱硬化性樹脂と、（Ｂ）硬化剤と、（Ｃ）エラストマーと、を含有する。接着剤組成物は、熱硬化性であり、半硬化（Ｂステージ）状態を経て、硬化処理後に完全硬化物（Ｃステージ）状態となり得る。[Adhesive composition]
The adhesive composition according to the present embodiment contains (A) a thermosetting resin, (B) a curing agent, and (C) an elastomer. The adhesive composition is thermosetting and can be in a semi-cured (B stage) state and then in a fully cured (C stage) state after the curing treatment.

＜（Ａ）成分：熱硬化性樹脂＞
熱硬化性樹脂は、接着性の観点から、エポキシ樹脂を含んでいてよい。本実施形態に係る接着剤組成物は、熱硬化性樹脂として、（Ａ−１）脂環式環を有するエポキシ樹脂を含む。<Component (A): Thermosetting resin>
The thermosetting resin may contain an epoxy resin from the viewpoint of adhesiveness. The adhesive composition according to the present embodiment contains (A-1) an epoxy resin having an alicyclic ring as a thermosetting resin.

（Ａ−１）成分は、分子内に脂環式環及びエポキシ基を有する化合物である。エポキシ基は、当該化合物の脂環式環又は脂環式環以外の部位に、単結合又は連結基（例えば、アルキレン基、オキシアルキレン基等）を介して結合していてよい。また、当該化合物は、脂環式環を構成する２つの炭素原子とともに形成されるエポキシ基を有する化合物（すなわち、脂環式エポキシ化合物）であってもよい。熱硬化性樹脂として（Ａ−１）成分を含むことによって、熱圧着時に良好な埋め込み性を有しつつ、ブリードを抑制することが可能となる。 The component (A-1) is a compound having an alicyclic ring and an epoxy group in the molecule. The epoxy group may be bonded to a site other than the alicyclic ring or the alicyclic ring of the compound via a single bond or a linking group (for example, an alkylene group, an oxyalkylene group, etc.). Further, the compound may be a compound having an epoxy group formed together with two carbon atoms constituting the alicyclic ring (that is, an alicyclic epoxy compound). By containing the component (A-1) as the thermosetting resin, it is possible to suppress bleeding while having good embedding property at the time of thermocompression bonding.

（Ａ−１）成分のエポキシ当量は、特に制限されないが、９０〜６００ｇ／ｅｑ、１００〜５００ｇ／ｅｑ、又は１２０〜４５０ｇ／ｅｑであってよい。（Ａ−１）成分のエポキシ当量がこのような範囲にあると、より良好な反応性及び流動性が得られる傾向にある。 The epoxy equivalent of the component (A-1) is not particularly limited, but may be 90 to 600 g / eq, 100 to 500 g / eq, or 120 to 450 g / eq. When the epoxy equivalent of the component (A-1) is in such a range, better reactivity and fluidity tend to be obtained.

（Ａ−１）成分は、例えば、下記一般式（１）〜（４）で表されるエポキシ樹脂のいずれかであってよい。 The component (A-1) may be, for example, any of the epoxy resins represented by the following general formulas (1) to (4).

Figure 2019150446
Figure 2019150446

式（１）中、Ｅは脂環式環を示し、Ｇは単結合又はアルキレン基を示し、Ｒ１はそれぞれ独立に水素原子又は１価の炭化水素基を示す。ｎ１は１〜１０の整数を示し、ｍは１〜３の整数を示す。In the formula (1), E represents an alicyclic ring, G represents a single bond or an alkylene group, and R 1 independently represents a hydrogen atom or a monovalent hydrocarbon group. n1 represents an integer of 1 to 10, and m represents an integer of 1 to 3.

Ｅの炭素原子数は、４〜１２、５〜１１、又は６〜１０であってよい。Ｅは、単環であっても、多環であってもよいが、多環であることが好ましく、ジシクロペンタジエン環であることがより好ましい。Ｇにおけるアルキレン基は、メチレン基、エチレン基、プロピレン基、ブチレン基、ペンチレン基等の炭素数１〜５のアルキレン基であってよい。Ｇは、単結合であることが好ましい。Ｒ１における１価の炭化水素基は、例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基等のアルキル基、フェニル基、ナフチル基等のアリール基、ピリジル基等のヘテロアリール基であってよい。Ｒ１は、水素原子であることが好ましい。The number of carbon atoms of E may be 4 to 12, 5 to 11, or 6 to 10. E may be monocyclic or polycyclic, but is preferably a polycyclic ring, more preferably a dicyclopentadiene ring. The alkylene group in G may be an alkylene group having 1 to 5 carbon atoms such as a methylene group, an ethylene group, a propylene group, a butylene group and a pentylene group. G is preferably a single bond. Monovalent hydrocarbon group for R 1 is, for example, a methyl group, an ethyl group, a propyl group, a butyl group, an alkyl group such as a pentyl group, an aryl group such as phenyl group and naphthyl group, a heteroaryl group such as pyridyl group It may be there. R 1 is preferably a hydrogen atom.

一般式（１）で表されるエポキシ樹脂は、下記一般式（１ａ）で表されるエポキシ樹脂であってよい。 The epoxy resin represented by the general formula (1) may be an epoxy resin represented by the following general formula (1a).

Figure 2019150446
Figure 2019150446

式（１ａ）中、ｎ１は上記と同義である。 In formula (1a), n1 is synonymous with the above.

一般式（１ａ）で表されるエポキシ樹脂の市販品としては、例えば、ＨＰ−７２００Ｌ、ＨＰ−７２００Ｈ、ＨＰ−７２００（いずれもＤＩＣ株式会社製）、ＸＤ−１０００（日本化薬株式会社製）等が挙げられる。 Commercially available epoxy resins represented by the general formula (1a) include, for example, HP-7200L, HP-7200H, HP-7200 (all manufactured by DIC Corporation), and XD-1000 (manufactured by Nippon Kayaku Corporation). And so on.

Figure 2019150446
Figure 2019150446

式（２）中、Ｒ２は２価の炭化水素基を示す。In formula (2), R 2 represents a divalent hydrocarbon group.

Ｒ２における２価の炭化水素基は、例えば、メチレン基、エチレン基、プロピレン基、ブチレン基、ペンチレン基等のアルキレン基、フェニレン基、ナフチレン基等のアリーレン基、ピリジレン基等のヘテロアリーレン基であってよい。Ｒ２は、炭素原子数１〜５のアルキレン基であることが好ましい。Divalent hydrocarbon group for R 2 is, for example, methylene group, ethylene group, propylene group, butylene group, an alkylene group such as pentylene group, a phenylene group, an arylene group such as a naphthylene group, a hetero arylene group such as pyridylene group It may be there. R 2 is preferably an alkylene group having 1 to 5 carbon atoms.

一般式（２）で表されるエポキシ樹脂の市販品としては、例えば、セロキサイド２０２１Ｐ、セロキサイド２０８１（いずれも株式会社ダイセル製）等が挙げられる。 Examples of commercially available epoxy resins represented by the general formula (2) include celoxide 2021P and celoxide 2081 (both manufactured by Daicel Corporation).

Figure 2019150446
Figure 2019150446

式（３）中、Ｒ３、Ｒ４、及びＲ５はそれぞれ独立に２価の炭化水素基を示す。In formula (3), R 3 , R 4 , and R 5 each independently represent a divalent hydrocarbon group.

Ｒ３、Ｒ４、及びＲ５における２価の炭化水素基としては、Ｒ２における２価の炭化水素基で例示したものと同様のものが挙げられる。R 3, R 4, and examples of the divalent hydrocarbon group for R 5, include the same ones as exemplified in the divalent hydrocarbon group for R 2.

一般式（３）で表されるエポキシ樹脂の市販品としては、例えば、Ｓｙｎａ−Ｅｐｏｘｙ２８（ＳＹＡＮＡＳＩＡ社製）等が挙げられる。 Examples of commercially available epoxy resins represented by the general formula (3) include Syna-Epoxy28 (manufactured by SYNASIA).

Figure 2019150446
Figure 2019150446

式（４）中、Ｒ６は水素原子又は１価の炭化水素基を示し、ｎ２は１〜１０の整数を示す。In formula (4), R 6 represents a hydrogen atom or a monovalent hydrocarbon group, and n2 represents an integer of 1 to 10.

Ｒ６における１価の炭化水素基としては、Ｒ１における１価の炭化水素基で例示したものと同様のものが挙げられる。Examples of the monovalent hydrocarbon group in R 6 include those similar to those exemplified in the monovalent hydrocarbon group in R 1 .

一般式（４）で表されるエポキシ樹脂の市販品としては、例えば、ＥＨＰＥ３１５０（株式会社ダイセル製）等が挙げられる。 Examples of commercially available epoxy resins represented by the general formula (4) include EHPE3150 (manufactured by Daicel Corporation).

（Ａ−１）成分は、耐熱性の観点から、一般式（１）で表されるエポキシ樹脂であることが好ましく、一般式（１ａ）で表されるエポキシ樹脂であることがより好ましい。 From the viewpoint of heat resistance, the component (A-1) is preferably an epoxy resin represented by the general formula (1), and more preferably an epoxy resin represented by the general formula (1a).

（Ａ−１）成分の含有量は、（Ａ）成分全量を基準として、１５〜１００質量％であってよい。（Ａ−１）成分の含有量は、４０質量％以上、５０質量％以上、又は６０質量％以上であってもよい。 The content of the component (A-1) may be 15 to 100% by mass based on the total amount of the component (A). The content of the component (A-1) may be 40% by mass or more, 50% by mass or more, or 60% by mass or more.

（Ａ−１）成分の含有量は、接着剤組成物全量を基準として、５質量％以上、１０質量％以上、又は２０質量％以上であってもよい。（Ａ−１）成分の含有量は、接着剤組成物全量を基準として、５質量％以上であると、熱圧着時により良好な埋め込み性を有しつつ、ブリードをよく抑制できる傾向にある。 The content of the component (A-1) may be 5% by mass or more, 10% by mass or more, or 20% by mass or more based on the total amount of the adhesive composition. When the content of the component (A-1) is 5% by mass or more based on the total amount of the adhesive composition, bleeding tends to be well suppressed while having better embedding property at the time of thermocompression bonding.

（Ａ）成分は、（Ａ−１）成分に加えて、（Ａ−２）脂環式環を有しない芳香族エポキシ樹脂をさらに含んでいてもよい。ここで、脂環式環を有しない芳香族エポキシ樹脂は、分子内に芳香環及びエポキシ基を有し、かつ脂環式環を有しない化合物である。（Ａ−２）成分としては、例えば、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、ビスフェノールＳ型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールＡノボラック型エポキシ樹脂、ビスフェノールＦノボラック型エポキシ樹脂、スチルベン型エポキシ樹脂、トリアジン骨格含有エポキシ樹脂、フルオレン骨格含有エポキシ樹脂、トリフェノールフェノールメタン型エポキシ樹脂、ビフェニル型エポキシ樹脂、キシリレン型エポキシ樹脂、フェニルアラルキル型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、ナフタレン型エポキシ樹脂、多官能フェノール類、アントラセン等の多環芳香族類のジグリシジルエーテル化合物などが挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。これらの中でも、（Ａ−２）成分は、２５℃で液体であってよい。 In addition to the component (A-1), the component (A) may further contain an aromatic epoxy resin (A-2) that does not have an alicyclic ring. Here, the aromatic epoxy resin having no alicyclic ring is a compound having an aromatic ring and an epoxy group in the molecule and not having an alicyclic ring. Examples of the component (A-2) include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolac type epoxy resin, and bisphenol F. Novolac type epoxy resin, stillben type epoxy resin, triazine skeleton containing epoxy resin, fluorene skeleton containing epoxy resin, triphenolphenol methane type epoxy resin, biphenyl type epoxy resin, xylylene type epoxy resin, phenylaralkyl type epoxy resin, biphenylaralkyl type epoxy Examples thereof include resins, naphthalene-type epoxy resins, polyfunctional phenols, and polycyclic aromatic diglycidyl ether compounds such as anthracene. These may be used individually by 1 type or in combination of 2 or more type. Among these, the component (A-2) may be a liquid at 25 ° C.

（Ａ−２）成分のエポキシ当量は、特に制限されないが、９０〜６００ｇ／ｅｑ、１００〜５００ｇ／ｅｑ、又は１２０〜４５０ｇ／ｅｑであってよい。（Ａ−２）成分のエポキシ当量がこのような範囲にあると、より良好な反応性及び流動性が得られる傾向にある。 The epoxy equivalent of the component (A-2) is not particularly limited, but may be 90 to 600 g / eq, 100 to 500 g / eq, or 120 to 450 g / eq. When the epoxy equivalent of the component (A-2) is in such a range, better reactivity and fluidity tend to be obtained.

（Ａ−２）成分の含有量は、（Ａ）成分全量を基準として、０〜８５質量％であってよい。（Ａ−２）成分の含有量は、６０質量％以下、５０質量％以下、又は４０質量％以下であってもよい。 The content of the component (A-2) may be 0 to 85% by mass based on the total amount of the component (A). The content of the component (A-2) may be 60% by mass or less, 50% by mass or less, or 40% by mass or less.

＜（Ｂ）成分：硬化剤＞
（Ｂ）成分は、特に制限なく、熱硬化性樹脂の硬化剤として一般的に使用されているものを用いることができる。熱硬化性樹脂がエポキシ樹脂を含む場合、（Ｂ）成分としては、例えば、フェノール樹脂、エステル化合物、芳香族アミン、脂肪族アミン、酸無水物等が挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。これらの中でも、反応性及び経時安定性の観点から、（Ｂ）成分はフェノール樹脂を含んでいてよい。<Component (B): Hardener>
The component (B) is not particularly limited, and those generally used as a curing agent for a thermosetting resin can be used. When the thermosetting resin contains an epoxy resin, the component (B) includes, for example, a phenol resin, an ester compound, an aromatic amine, an aliphatic amine, an acid anhydride and the like. These may be used individually by 1 type or in combination of 2 or more type. Among these, the component (B) may contain a phenol resin from the viewpoint of reactivity and stability over time.

フェノール樹脂は、分子内にフェノール性水酸基を有するものであれば特に制限なく用いることができる。フェノール樹脂としては、例えば、フェノール、クレゾール、レゾルシン、カテコール、ビスフェノールＡ、ビスフェノールＦ、フェニルフェノール、アミノフェノール等のフェノール類及び／又はα−ナフトール、β−ナフトール、ジヒドロキシナフタレン等のナフトール類とホルムアルデヒド等のアルデヒド基を有する化合物とを酸性触媒下で縮合又は共縮合させて得られるノボラック型フェノール樹脂、アリル化ビスフェノールＡ、アリル化ビスフェノールＦ、アリル化ナフタレンジオール、フェノールノボラック、フェノール等のフェノール類及び／又はナフトール類とジメトキシパラキシレン又はビス（メトキシメチル）ビフェニルから合成されるフェノールアラルキル樹脂、ナフトールアラルキル樹脂、ビフェニルアラルキル型フェノール樹脂、フェニルアラルキル型フェノール樹脂などが挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。これらの中でも、耐熱性の観点から、フェノール樹脂は、８５℃、８５％ＲＨの恒温恒湿槽に４８時間の条件において、吸水率が２質量％以下であり、かつ熱重量分析計（ＴＧＡ）で測定した３５０℃での加熱質量減少率（昇温速度：５℃／ｍｉｎ、雰囲気：窒素）が５質量％未満であるものが好ましい。 The phenol resin can be used without particular limitation as long as it has a phenolic hydroxyl group in the molecule. Examples of the phenol resin include phenols such as phenol, cresol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol and aminophenol, and / or naphthols such as α-naphthol, β-naphthol and dihydroxynaphthalene, and formaldehyde and the like. Phenols such as novolak-type phenol resin, allylated bisphenol A, allylated bisphenol F, allylated naphthalenediol, phenol novolac, and phenol obtained by condensing or co-condensing with a compound having an aldehyde group of Alternatively, a phenol aralkyl resin synthesized from naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl, a naphthol aralkyl resin, a biphenyl aralkyl type phenol resin, a phenyl aralkyl type phenol resin and the like can be mentioned. These may be used individually by 1 type or in combination of 2 or more type. Among these, from the viewpoint of heat resistance, the phenol resin has a water absorption rate of 2% by mass or less and a thermogravimetric analyzer (TGA) under the condition of a constant temperature and humidity chamber at 85 ° C. and 85% RH for 48 hours. It is preferable that the heating mass reduction rate at 350 ° C. (heating rate: 5 ° C./min, atmosphere: nitrogen) measured in 1) is less than 5% by mass.

フェノール樹脂の市販品としては、例えば、フェノライトＫＡシリーズ、ＴＤシリーズ（ＤＩＣ株式会社製）、ミレックスＸＬＣシリーズ、ＸＬシリーズ（三井化学株式会社製）、ＨＥシリーズ（エア・ウォーター株式会社製）等が挙げられる。 Examples of commercially available phenolic resins include Phenolite KA series, TD series (manufactured by DIC Corporation), Millex XLC series, XL series (manufactured by Mitsui Chemicals Co., Ltd.), HE series (manufactured by Air Water Inc.), and the like. Can be mentioned.

フェノール樹脂の水酸基当量は、特に制限されないが、８０〜４００ｇ／ｅｑ、９０〜３５０ｇ／ｅｑ、又は１００〜３００ｇ／ｅｑであってよい。フェノール樹脂の水酸基当量がこのような範囲にあると、より良好な反応性及び流動性が得られる傾向にある。 The hydroxyl group equivalent of the phenol resin is not particularly limited, but may be 80 to 400 g / eq, 90 to 350 g / eq, or 100 to 300 g / eq. When the hydroxyl group equivalent of the phenol resin is in such a range, better reactivity and fluidity tend to be obtained.

（Ａ）成分がエポキシ樹脂であり、（Ｂ）成分がフェノール樹脂である場合のエポキシ樹脂のエポキシ当量とフェノール樹脂の水酸基当量との比（エポキシ樹脂のエポキシ当量／フェノール樹脂の水酸基当量）は、硬化性の観点から、０．３０／０．７０〜０．７０／０．３０、０．３５／０．６５〜０．６５／０．３５、０．４０／０．６０〜０．６０／０．４０、又は０．４５／０．５５〜０．５５／０．４５であってよい。当該当量比が０．３０／０．７０以上であると、より充分な硬化性が得られる傾向にある。当該当量比が０．７０／０．３０以下であると、粘度が高くなり過ぎることを防ぐことができ、より充分な流動性を得ることができる。 When the component (A) is an epoxy resin and the component (B) is a phenol resin, the ratio of the epoxy equivalent of the epoxy resin to the hydroxyl equivalent of the phenol resin (epoxy equivalent of the epoxy resin / hydroxyl equivalent of the phenol resin) is From the viewpoint of curability, 0.30 / 0.70 to 0.70 / 0.30, 0.35 / 0.65 to 0.65 / 0.35, 0.40 / 0.60 to 0.60 / It may be 0.40, or 0.45 / 0.55 to 0.55 / 0.45. When the equivalent amount ratio is 0.30 / 0.70 or more, more sufficient curability tends to be obtained. When the equivalent equivalent ratio is 0.70 / 0.30 or less, it is possible to prevent the viscosity from becoming too high, and it is possible to obtain more sufficient fluidity.

（Ａ）成分及び（Ｂ）成分の合計の含有量は、接着剤組成物全量を基準として、３０〜７０質量％であってよい。（Ａ）成分及び（Ｂ）成分の合計の含有量は、３３質量％以上、３６質量％以上、又は４０質量％以上であってもよく、６５質量％以下、６０質量％以下、又は５５質量％以下であってもよい。（Ａ）成分及び（Ｂ）成分の合計の含有量が、接着剤組成物全量を基準として、３０質量％以上であると、接着性が向上する傾向にある。（Ａ）成分及び（Ｂ）成分の合計の含有量が、接着剤組成物全量を基準として、７０質量％以下であると、粘度が低くなりすぎることを防ぐことができ、ブリードをより抑えることができる傾向にある。 The total content of the component (A) and the component (B) may be 30 to 70% by mass based on the total amount of the adhesive composition. The total content of the component (A) and the component (B) may be 33% by mass or more, 36% by mass or more, or 40% by mass or more, and 65% by mass or less, 60% by mass or less, or 55% by mass. It may be less than or equal to%. When the total content of the component (A) and the component (B) is 30% by mass or more based on the total amount of the adhesive composition, the adhesiveness tends to be improved. When the total content of the component (A) and the component (B) is 70% by mass or less based on the total amount of the adhesive composition, it is possible to prevent the viscosity from becoming too low and further suppress bleeding. Tend to be able to.

＜（Ｃ）成分：エラストマー＞
本実施形態に係る接着剤組成物は、（Ｃ）エラストマーを含有する。（Ｃ）成分は、エラストマーを構成する重合体のガラス転移温度（Ｔｇ）が５０℃以下であるものが好ましい。<Component (C): Elastomer>
The adhesive composition according to this embodiment contains (C) an elastomer. The component (C) preferably has a glass transition temperature (Tg) of a polymer constituting the elastomer of 50 ° C. or lower.

（Ｃ）成分としては、例えば、アクリル樹脂、ポリエステル樹脂、ポリアミド樹脂、ポリイミド樹脂、シリコーン樹脂、ブタジエン樹脂、アクリロニトリル樹脂及びこれらの変性体等が挙げられる。 Examples of the component (C) include acrylic resin, polyester resin, polyamide resin, polyimide resin, silicone resin, butadiene resin, acrylonitrile resin, and modified products thereof.

（Ｃ）成分は、溶剤への溶解性、流動性の観点から、アクリル樹脂を含んでいてよい。ここで、アクリル樹脂とは、（メタ）アクリル酸エステルに由来する構成単位を含むポリマーを意味する。アクリル樹脂は、構成単位として、エポキシ基、アルコール性又はフェノール性水酸基、カルボキシ基等の架橋性官能基を有する（メタ）アクリル酸エステルに由来する構成単位を含むポリマーであることが好ましい。また、アクリル樹脂は、（メタ）アクリル酸エステルとアクリルニトリルとの共重合体等のアクリルゴムであってもよい。 The component (C) may contain an acrylic resin from the viewpoint of solubility in a solvent and fluidity. Here, the acrylic resin means a polymer containing a structural unit derived from a (meth) acrylic acid ester. The acrylic resin is preferably a polymer containing a structural unit derived from a (meth) acrylic acid ester having a crosslinkable functional group such as an epoxy group, an alcoholic or phenolic hydroxyl group, or a carboxy group as a structural unit. Further, the acrylic resin may be an acrylic rubber such as a copolymer of (meth) acrylic acid ester and acrylonitrile.

アクリル樹脂のガラス転移温度（Ｔｇ）は、−５０〜５０℃又は−３０〜３０℃であってよい。アクリル樹脂のＴｇが−５０℃以上であると、接着剤組成物の柔軟性が高くなり過ぎることを防ぐことができる傾向にある。これにより、ウェハダイシング時にフィルム状接着剤を切断し易くなり、バリの発生を防ぐことが可能となる。アクリル樹脂のＴｇが５０℃以下であると、接着剤組成物の柔軟性の低下を抑えることができる傾向にある。これにより、フィルム状接着剤をウェハに貼り付ける際に、ボイドを充分に埋め込み易くなる傾向にある。また、ウェハの密着性の低下によるダイシング時のチッピングを防ぐことが可能となる。ここで、ガラス転移温度（Ｔｇ）は、ＤＳＣ（熱示差走査熱量計）（例えば、株式会社リガク製「Ｔｈｅｒｍｏ Ｐｌｕｓ ２」）を用いて測定した値を意味する。 The glass transition temperature (Tg) of the acrylic resin may be −50 to 50 ° C. or -30 to 30 ° C. When the Tg of the acrylic resin is −50 ° C. or higher, it tends to be possible to prevent the adhesive composition from becoming too flexible. This makes it easier to cut the film-like adhesive during wafer dicing, and it is possible to prevent the occurrence of burrs. When the Tg of the acrylic resin is 50 ° C. or lower, the decrease in flexibility of the adhesive composition tends to be suppressed. As a result, when the film-like adhesive is attached to the wafer, the voids tend to be sufficiently embedded. In addition, it is possible to prevent chipping during dicing due to a decrease in wafer adhesion. Here, the glass transition temperature (Tg) means a value measured using a DSC (thermal differential scanning calorimeter) (for example, "Thermo Plus 2" manufactured by Rigaku Co., Ltd.).

アクリル樹脂の重量平均分子量（Ｍｗ）は、１０万〜３００万又は５０万〜２００万であってよい。アクリル樹脂のＭｗがこのような範囲にあると、フィルム形成性、フィルム状における強度、可撓性、タック性等を適切に制御することができると共に、リフロー性に優れ、埋め込み性を向上することができる。ここで、Ｍｗは、ゲルパーミエーションクロマトグラフィー（ＧＰＣ）で測定し、標準ポリスチレンによる検量線を用いて換算した値を意味する。 The weight average molecular weight (Mw) of the acrylic resin may be 100,000 to 3 million or 500,000 to 2 million. When the Mw of the acrylic resin is in such a range, the film formability, the strength in the film form, the flexibility, the tackiness, etc. can be appropriately controlled, and the reflowability is excellent and the embedding property is improved. Can be done. Here, Mw means a value measured by gel permeation chromatography (GPC) and converted using a calibration curve using standard polystyrene.

アクリル樹脂の市販品としては、例えば、ＳＧ−７０Ｌ、ＳＧ−７０８−６、ＷＳ−０２３ ＥＫ３０、ＳＧ−２８０ ＥＫ２３、ＨＴＲ−８６０Ｐ−３ＣＳＰ、ＨＴＲ−８６０Ｐ−３ＣＳＰ−３ＤＢ（いずれもナガセケムテックス株式会社製）が挙げられる。 Examples of commercially available acrylic resins include SG-70L, SG-708-6, WS-023 EK30, SG-280 EK23, HTR-860P-3CSP, and HTR-860P-3CSP-3DB (all of which are Nagase ChemteX stocks). Made by the company).

（Ｃ）成分の含有量は、（Ａ）成分及び（Ｂ）成分の総量１００質量部に対して、２０〜２００質量部又は３０〜１００質量部であってよい。（Ｃ）成分の含有量が（Ａ）成分及び（Ｂ）成分の総量１００質量部に対して、２０質量部以上であると、フィルム状接着剤の取り扱い性（例えば折り曲げ性など）がより良好となる傾向にある。（Ｃ）成分の含有量が（Ａ）成分及び（Ｂ）成分の総量１００質量部に対して、２００質量部以下であると、接着剤組成物の柔軟性が高くなり過ぎることをより防ぐことができる傾向にある。これにより、ウェハダイシング時にフィルム状接着剤を切断し易くなり、バリの発生を防ぐことがより一層可能となる傾向にある。 The content of the component (C) may be 20 to 200 parts by mass or 30 to 100 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). When the content of the component (C) is 20 parts by mass or more with respect to 100 parts by mass of the total amount of the components (A) and (B), the handleability of the film-like adhesive (for example, bendability) is better. It tends to be. When the content of the component (C) is 200 parts by mass or less with respect to 100 parts by mass of the total amount of the components (A) and (B), it is possible to further prevent the adhesive composition from becoming too flexible. Tend to be able to. This makes it easier to cut the film-like adhesive during wafer dicing, and tends to further prevent the occurrence of burrs.

＜（Ｄ）成分：無機フィラー＞
本実施形態に係る接着剤組成物は、（Ｄ）無機フィラーをさらに含有していてもよい。無機フィラーとしては、例えば、水酸化アルミニウム、水酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム、ケイ酸カルシウム、ケイ酸マグネシウム、酸化カルシウム、酸化マグネシウム、酸化アルミニウム、窒化アルミニウム、ホウ酸アルミウィスカ、窒化ホウ素、結晶性シリカ、非晶性シリカ等が挙げられる。これらは１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。得られるフィルム状接着剤の熱伝導性がより向上する観点から、無機フィラーは、酸化アルミニウム、窒化アルミニウム、窒化ホウ素、結晶性シリカ又は非晶性シリカを含んでいてよい。また、接着剤組成物の溶融粘度を調整する観点及び接着剤組成物にチキソトロピック性を付与する観点から、無機フィラーは、水酸化アルミニウム、水酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム、ケイ酸カルシウム、ケイ酸マグネシウム、酸化カルシウム、酸化マグネシウム、酸化アルミニウム、結晶性シリカ又は非晶性シリカを含んでいてよい。<Component (D): Inorganic filler>
The adhesive composition according to the present embodiment may further contain (D) an inorganic filler. Examples of the inorganic filler include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, aluminum borate whisker, boron nitride, and crystals. Examples thereof include sex silica and amorphous silica. One of these may be used alone, or two or more thereof may be used in combination. From the viewpoint of further improving the thermal conductivity of the obtained film-like adhesive, the inorganic filler may contain aluminum oxide, aluminum nitride, boron nitride, crystalline silica or amorphous silica. Further, from the viewpoint of adjusting the melt viscosity of the adhesive composition and imparting thixotropic properties to the adhesive composition, the inorganic fillers include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, and the like. It may contain magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, crystalline silica or amorphous silica.

（Ｄ）成分の平均粒径は、接着性がより向上する観点から、０．００５〜０．５μｍ又は０．０５〜０．３μｍであってよい。ここで、平均粒径は、ＢＥＴ比表面積から換算することによって求められる値を意味する。 The average particle size of the component (D) may be 0.005 to 0.5 μm or 0.05 to 0.3 μm from the viewpoint of further improving the adhesiveness. Here, the average particle size means a value obtained by converting from the BET specific surface area.

（Ｄ）成分は、その表面と溶剤、他の成分等との相溶性、接着強度の観点から表面処理剤によって表面処理されていてよい。表面処理剤としては、例えば、シランカップリング剤等が挙げられる。シランカップリング剤の官能基としては、例えば、ビニル基、（メタ）アクリロイル基、エポキシ基、メルカプト基、アミノ基、ジアミノ基、アルコキシ基、エトキシ基等が挙げられる。 The component (D) may be surface-treated with a surface treatment agent from the viewpoint of compatibility between the surface and the solvent, other components and the like, and adhesive strength. Examples of the surface treatment agent include a silane coupling agent and the like. Examples of the functional group of the silane coupling agent include a vinyl group, a (meth) acryloyl group, an epoxy group, a mercapto group, an amino group, a diamino group, an alkoxy group, an ethoxy group and the like.

（Ｄ）成分の含有量は、（Ａ）成分、（Ｂ）成分、及び（Ｃ）成分の総量１００質量部に対して、１０〜９０質量部又は１０〜５０質量部であってよい。（Ｄ）成分の含有量が、（Ａ）成分、（Ｂ）成分、及び（Ｃ）成分の総量１００質量部に対して、１０質量部以上であると、硬化前の接着層のダイシング性が向上し、硬化後の接着層の接着力が向上する傾向にある。（Ｄ）成分の含有量が、（Ａ）成分、（Ｂ）成分、及び（Ｃ）成分の総量１００質量部に対して、９０質量部以下であると、流動性の低下を抑制でき、硬化後のフィルム状接着剤の弾性率が高くなり過ぎることを防ぐことが可能となる。 The content of the component (D) may be 10 to 90 parts by mass or 10 to 50 parts by mass with respect to 100 parts by mass of the total amount of the component (A), the component (B), and the component (C). When the content of the component (D) is 10 parts by mass or more with respect to 100 parts by mass of the total amount of the components (A), (B), and (C), the dicing property of the adhesive layer before curing becomes high. It tends to improve and the adhesive strength of the adhesive layer after curing tends to improve. When the content of the component (D) is 90 parts by mass or less with respect to 100 parts by mass of the total amount of the components (A), (B), and (C), the decrease in fluidity can be suppressed and curing is performed. It is possible to prevent the elastic modulus of the later film-like adhesive from becoming too high.

＜（Ｅ）成分：硬化促進剤＞
本実施形態に係る接着剤組成物は、（Ｅ）硬化促進剤を含有していてよい。硬化促進剤は、特に限定されず、一般に使用されるものを用いることができる。（Ｅ）成分としては、例えば、イミダゾール類及びその誘導体、有機リン系化合物、第二級アミン類、第三級アミン類、第四級アンモニウム塩等が挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。これらの中でも、反応性の観点から（Ｅ）成分はイミダゾール類及びその誘導体であってよい。<Component (E): Curing accelerator>
The adhesive composition according to this embodiment may contain (E) a curing accelerator. The curing accelerator is not particularly limited, and generally used ones can be used. Examples of the component (E) include imidazoles and derivatives thereof, organic phosphorus compounds, secondary amines, tertiary amines, quaternary ammonium salts and the like. These may be used individually by 1 type or in combination of 2 or more type. Among these, the component (E) may be imidazoles and derivatives thereof from the viewpoint of reactivity.

イミダゾール類としては、例えば、２−メチルイミダゾール、１−ベンジル−２−メチルイミダゾール、１−シアノエチル−２−フェニルイミダゾール、１−シアノエチル−２−メチルイミダゾール等が挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。 Examples of the imidazoles include 2-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole and the like. These may be used individually by 1 type or in combination of 2 or more type.

（Ｅ）成分の含有量は、（Ａ）成分、（Ｂ）成分、及び（Ｃ）成分の総量１００質量部に対して、０．０４〜３質量部又は０．０４〜０．２質量部であってよい。（Ｅ）成分の含有量がこのような範囲にあると、硬化性と信頼性とを両立することができる傾向にある。 The content of the component (E) is 0.04 to 3 parts by mass or 0.04 to 0.2 parts by mass with respect to 100 parts by mass of the total amount of the component (A), the component (B), and the component (C). It may be. When the content of the component (E) is in such a range, both curability and reliability tend to be compatible.

＜その他の成分＞
本実施形態に係る接着剤組成物は、その他の成分として、抗酸化剤、シランカップリング剤、レオロジーコントロール剤等をさらに含有していてもよい。これらの成分の含有量は、（Ａ）成分、（Ｂ）成分、及び（Ｃ）成分の総量１００質量部に対して、０．０２〜３質量部であってよい。<Other ingredients>
The adhesive composition according to the present embodiment may further contain an antioxidant, a silane coupling agent, a rheology control agent and the like as other components. The content of these components may be 0.02 to 3 parts by mass with respect to 100 parts by mass of the total amount of the components (A), (B), and (C).

本実施形態に係る接着剤組成物は、溶剤で希釈された接着剤ワニスとして用いてもよい。溶剤は、（Ｄ）成分以外の成分を溶解できるものであれば特に制限されない。溶剤としては、例えば、トルエン、キシレン、メシチレン、クメン、ｐ−シメン等の芳香族炭化水素；ヘキサン、ヘプタン等の脂肪族炭化水素；メチルシクロヘキサンなどの環状アルカン；テトラヒドロフラン、１，４−ジオキサン等の環状エーテル；アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、４−ヒドロキシ−４−メチル−２−ペンタノン等のケトン；酢酸メチル、酢酸エチル、酢酸ブチル、乳酸メチル、乳酸エチル、γ−ブチロラクトン等のエステル；エチレンカーボネート、プロピレンカーボネート等の炭酸エステル；Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチル−２−ピロリドン等のアミドなどが挙げられる。これらは、１種を単独で又は２種以上を組み合わせて用いてもよい。これらのうち、溶剤は、溶解性及び沸点の観点から、トルエン、キシレン、メチルエチルケトン、メチルイソブチルケトン、又はシクロヘキサンであってもよい。 The adhesive composition according to this embodiment may be used as an adhesive varnish diluted with a solvent. The solvent is not particularly limited as long as it can dissolve a component other than the component (D). Examples of the solvent include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene and p-simene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; tetrahydrofuran, 1,4-dioxane and the like. Cyclic ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, γ-butyrolactone; Carbonated esters such as ethylene carbonate and propylene carbonate; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone can be mentioned. These may be used individually by 1 type or in combination of 2 or more type. Of these, the solvent may be toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexane from the viewpoint of solubility and boiling point.

接着剤ワニス中の固形成分濃度は、接着剤ワニスの全質量を基準として、１０〜８０質量％であってよい。 The concentration of the solid component in the adhesive varnish may be 10 to 80% by mass based on the total mass of the adhesive varnish.

接着剤ワニスは、（Ａ）成分、（Ｂ）成分、（Ｃ）成分、及び溶剤、並びに、必要に応じて、（Ｄ）成分、（Ｅ）成分、及びその他の成分を混合、混練することによって調製することができる。混合及び混練は、通常の撹拌機、らいかい機、三本ロール、ボールミル、ビーズミル等の分散機を適宜、組み合わせて行うことができる。（Ｄ）成分を含有する場合、（Ｄ）成分と低分子量成分を予め混合した後、高分子量成分を配合することによって、混合する時間を短縮することができる。また、接着剤ワニスを調製した後、真空脱気等によってワニス中の気泡を除去してよい。 The adhesive varnish is prepared by mixing and kneading the components (A), (B), (C), and solvent, and, if necessary, the components (D), (E), and other components. Can be prepared by. Mixing and kneading can be carried out by appropriately combining a disperser such as a normal stirrer, a raft machine, a triple roll, a ball mill, and a bead mill. When the component (D) is contained, the mixing time can be shortened by mixing the component (D) and the low molecular weight component in advance and then blending the high molecular weight component. Further, after preparing the adhesive varnish, air bubbles in the varnish may be removed by vacuum degassing or the like.

［フィルム状接着剤］
図１は、一実施形態に係るフィルム状接着剤を示す模式断面図である。フィルム状接着剤１０は、上述の接着剤組成物をフィルム状に形成してなるものである。フィルム状接着剤１０は、半硬化（Ｂステージ）状態であってよい。このようなフィルム状接着剤１０は、接着剤組成物を支持フィルムに塗布することによって形成することができる。接着剤ワニスを用いる場合は、接着剤ワニスを支持フィルムに塗布し、溶剤を加熱乾燥して除去することによってフィルム状接着剤１０を形成することができる。[Film-like adhesive]
FIG. 1 is a schematic cross-sectional view showing a film-like adhesive according to an embodiment. The film-like adhesive 10 is formed by forming the above-mentioned adhesive composition into a film. The film-like adhesive 10 may be in a semi-cured (B stage) state. Such a film-like adhesive 10 can be formed by applying an adhesive composition to a support film. When an adhesive varnish is used, the film-like adhesive 10 can be formed by applying the adhesive varnish to the support film and removing the solvent by heating and drying.

支持フィルムとしては、特に制限はなく、例えば、ポリテトラフルオロエチレン、ポリエチレン、ポリプロピレン、ポリメチルペンテン、ポリエチレンテレフタレート、ポリイミド等のフィルムが挙げられる。支持フィルムの厚さは、例えば、６０〜２００μｍ又は７０〜１７０μｍであってよい。 The support film is not particularly limited, and examples thereof include films such as polytetrafluoroethylene, polyethylene, polypropylene, polymethylpentene, polyethylene terephthalate, and polyimide. The thickness of the support film may be, for example, 60 to 200 μm or 70 to 170 μm.

接着剤ワニスを支持フィルムに塗布する方法としては、公知の方法を用いることができ、例えば、ナイフコート法、ロールコート法、スプレーコート法、グラビアコート法、バーコート法、カーテンコート法等が挙げられる。加熱乾燥の条件は、使用した溶剤が充分に揮発する条件であれば特に制限はないが、例えば、５０〜２００℃で０．１〜９０分間であってもよい。 As a method of applying the adhesive varnish to the support film, a known method can be used, and examples thereof include a knife coating method, a roll coating method, a spray coating method, a gravure coating method, a bar coating method, and a curtain coating method. Be done. The conditions for heat drying are not particularly limited as long as the solvent used is sufficiently volatilized, but may be, for example, 0.1 to 90 minutes at 50 to 200 ° C.

フィルム状接着剤の厚さは、用途に合わせて、適宜調整することができる。フィルム状接着剤の厚さは、半導体チップ、ワイヤ、基板の配線回路等の凹凸などを充分に埋め込む観点から、２０〜２００μｍ、３０〜２００μｍ、又は４０〜１５０μｍであってよい。 The thickness of the film-like adhesive can be appropriately adjusted according to the application. The thickness of the film-like adhesive may be 20 to 200 μm, 30 to 200 μm, or 40 to 150 μm from the viewpoint of sufficiently embedding irregularities of semiconductor chips, wires, wiring circuits of substrates, and the like.

［接着シート］
図２は、一実施形態に係る接着シートを示す模式断面図である。接着シート１００は、基材２０と基材上に設けられた上述のフィルム状接着剤１０とを備える。[Adhesive sheet]
FIG. 2 is a schematic cross-sectional view showing an adhesive sheet according to an embodiment. The adhesive sheet 100 includes a base material 20 and the above-mentioned film-like adhesive 10 provided on the base material.

基材２０は、特に制限されないが、基材フィルムであってよい。基材フィルムは、上述の支持フィルムと同様のものであってよい。 The base material 20 is not particularly limited, but may be a base material film. The base film may be the same as the support film described above.

基材２０は、ダイシングテープであってもよい。このような接着シートは、ダイシングダイボンディング一体型接着シートとして使用することができる。この場合、半導体ウェハへのラミネート工程が１回となることから、作業の効率化が可能である。 The base material 20 may be a dicing tape. Such an adhesive sheet can be used as a dicing die bonding integrated adhesive sheet. In this case, since the laminating process on the semiconductor wafer is performed once, the work efficiency can be improved.

ダイシングテープとしては、例えば、ポリテトラフルオロエチレンフィルム、ポリエチレンテレフタレートフィルム、ポリエチレンフィルム、ポリプロピレンフィルム、ポリメチルペンテンフィルム、ポリイミドフィルム等のプラスチックフィルム等が挙げられる。また、ダイシングテープは、必要に応じて、プライマー塗布、ＵＶ処理、コロナ放電処理、研磨処理、エッチング処理等の表面処理が行われていてもよい。ダイシングテープは、粘着性を有するものであることが好ましい。このようなダイシングテープは、上述のプラスチックフィルムに粘着性を付与したものであってもよく、上述のプラスチックフィルムの片面に粘着剤層を設けたものであってもよい。 Examples of the dicing tape include plastic films such as polytetrafluoroethylene film, polyethylene terephthalate film, polyethylene film, polypropylene film, polymethylpentene film, and polyimide film. Further, the dicing tape may be subjected to surface treatment such as primer coating, UV treatment, corona discharge treatment, polishing treatment, and etching treatment, if necessary. The dicing tape is preferably one having adhesiveness. Such a dicing tape may be one in which adhesiveness is imparted to the above-mentioned plastic film, or may be one in which an adhesive layer is provided on one side of the above-mentioned plastic film.

接着シート１００は、上述のフィルム状接着剤を形成する方法と同様に、接着剤組成物を基材フィルムに塗布することによって形成することができる。接着剤組成物を基材２０に塗布する方法は、上述の接着剤組成物を支持フィルムに塗布する方法と同様であってよい。 The adhesive sheet 100 can be formed by applying the adhesive composition to the base film in the same manner as the above-mentioned method for forming the film-like adhesive. The method of applying the adhesive composition to the base material 20 may be the same as the method of applying the adhesive composition to the support film described above.

接着シート１００は、予め作製したフィルム状接着剤を用いて形成してもよい。この場合、接着シート１００は、ロールラミネーター、真空ラミネーター等を用いて所定条件（例えば、室温（２０℃）又は加熱状態）でラミネートすることによって形成することができる。接着シート１００は、連続的に製造ができ、効率が良いことから、加熱状態でロールラミネーターを用いて形成することが好ましい。 The adhesive sheet 100 may be formed by using a film-like adhesive prepared in advance. In this case, the adhesive sheet 100 can be formed by laminating under predetermined conditions (for example, room temperature (20 ° C.) or a heated state) using a roll laminator, a vacuum laminator, or the like. Since the adhesive sheet 100 can be continuously manufactured and has high efficiency, it is preferable to form the adhesive sheet 100 in a heated state using a roll laminator.

フィルム状接着剤１０の厚さは、半導体チップ、ワイヤ、基板の配線回路等の凹凸などの埋め込み性の観点から、２０〜２００μｍ、３０〜２００μｍ、又は４０〜１５０μｍであってよい。フィルム状接着剤１０の厚さが２０μｍ以上であると、より充分な接着力が得られる傾向にあり、フィルム状接着剤１０の厚さが２００μｍ以下であると、経済的であり、かつ半導体装置の小型化の要求に応えることが可能となる。 The thickness of the film-like adhesive 10 may be 20 to 200 μm, 30 to 200 μm, or 40 to 150 μm from the viewpoint of embedding the unevenness of the semiconductor chip, the wire, the wiring circuit of the substrate, and the like. When the thickness of the film-like adhesive 10 is 20 μm or more, more sufficient adhesive force tends to be obtained, and when the thickness of the film-like adhesive 10 is 200 μm or less, it is economical and a semiconductor device. It will be possible to meet the demand for miniaturization.

図３は、他の実施形態に係る接着シートを示す模式断面図である。接着シート１１０は、フィルム状接着剤１０の基材２０とは反対側の面に積層された保護フィルム３０をさらに備える。保護フィルム３０は、上述の支持フィルムと同様のものであってよい。保護フィルムの厚さは、例えば、１５〜２００μｍ又は７０〜１７０μｍであってよい。 FIG. 3 is a schematic cross-sectional view showing an adhesive sheet according to another embodiment. The adhesive sheet 110 further includes a protective film 30 laminated on the surface of the film-like adhesive 10 opposite to the base material 20. The protective film 30 may be the same as the support film described above. The thickness of the protective film may be, for example, 15 to 200 μm or 70 to 170 μm.

［半導体装置］
図４は、一実施形態に係る半導体装置を示す模式断面図である。半導体装置２００は、基板１４に、第１のワイヤ８８を介して１段目の第１の半導体素子Ｗａがワイヤボンディング接続されると共に、第１の半導体素子Ｗａ上に、第２の半導体素子Ｗａａがフィルム状接着剤１０を介して圧着されることで、第１のワイヤ８８の少なくとも一部がフィルム状接着剤１０に埋め込まれてなる半導体装置である。半導体装置は、第１のワイヤ８８の少なくとも一部が埋め込まれてなるワイヤ埋め込み型の半導体装置であっても、第１のワイヤ８８及び第１の半導体素子Ｗａが埋め込まれてなる半導体装置であってもよい。また、半導体装置２００では、基板１４と第２の半導体素子Ｗａａとがさらに第２のワイヤ９８を介して電気的に接続されると共に、第２の半導体素子Ｗａａが封止材４２により封止されている。[Semiconductor device]
FIG. 4 is a schematic cross-sectional view showing the semiconductor device according to the embodiment. In the semiconductor device 200, the first semiconductor element Wa of the first stage is wire-bonded to the substrate 14 via the first wire 88, and the second semiconductor element Wa is mounted on the first semiconductor element Wa. Is a semiconductor device in which at least a part of the first wire 88 is embedded in the film-like adhesive 10 by being crimped via the film-like adhesive 10. The semiconductor device is a wire-embedded semiconductor device in which at least a part of the first wire 88 is embedded, but is a semiconductor device in which the first wire 88 and the first semiconductor element Wa are embedded. You may. Further, in the semiconductor device 200, the substrate 14 and the second semiconductor element Waa are further electrically connected via the second wire 98, and the second semiconductor element Waa is sealed by the sealing material 42. ing.

第１の半導体素子Ｗａの厚さは、１０〜１７０μｍであってもよく、第２の半導体素子Ｗａａの厚さは、２０〜４００μｍであってもよい。フィルム状接着剤１０内部に埋め込まれている第１の半導体素子Ｗａは、半導体装置２００を駆動するためのコントローラチップである。 The thickness of the first semiconductor element Wa may be 10 to 170 μm, and the thickness of the second semiconductor element Wa may be 20 to 400 μm. The first semiconductor element Wa embedded inside the film-like adhesive 10 is a controller chip for driving the semiconductor device 200.

基板１４は、表面に回路パターン８４、９４がそれぞれ二箇所ずつ形成された有機基板９０からなる。第１の半導体素子Ｗａは、回路パターン９４上に接着剤４１を介して圧着されている。第２の半導体素子Ｗａａは、第１の半導体素子Ｗａが圧着されていない回路パターン９４、第１の半導体素子Ｗａ、及び回路パターン８４の一部が覆われるようにフィルム状接着剤１０を介して基板１４に圧着されている。基板１４上の回路パターン８４、９４に起因する凹凸の段差には、フィルム状接着剤１０が埋め込まれている。そして、樹脂製の封止材４２により、第２の半導体素子Ｗａａ、回路パターン８４及び第２のワイヤ９８が封止されている。 The substrate 14 is composed of an organic substrate 90 having two circuit patterns 84 and 94 formed on the surface thereof. The first semiconductor element Wa is crimped onto the circuit pattern 94 via an adhesive 41. The second semiconductor element Waa is via a film-like adhesive 10 so that a part of the circuit pattern 94, the first semiconductor element Wa, and the circuit pattern 84 in which the first semiconductor element Wa is not crimped is covered. It is crimped to the substrate 14. The film-like adhesive 10 is embedded in the uneven steps caused by the circuit patterns 84 and 94 on the substrate 14. Then, the second semiconductor element Waa, the circuit pattern 84, and the second wire 98 are sealed by the resin-made sealing material 42.

［半導体装置の製造方法］
本実施形態に係る半導体装置の製造方法は、基板上に第１のワイヤを介して第１の半導体素子を電気的に接続する第１のワイヤボンディング工程と、第２の半導体素子の片面に、上述のフィルム状接着剤を貼付するラミネート工程と、フィルム状接着剤が貼付された第２の半導体素子を、フィルム状接着剤を介して圧着することで、第１のワイヤの少なくとも一部をフィルム状接着剤に埋め込むダイボンド工程と、を備える。[Manufacturing method of semiconductor devices]
The method for manufacturing a semiconductor device according to the present embodiment includes a first wire bonding step of electrically connecting a first semiconductor element on a substrate via a first wire, and a method of manufacturing the semiconductor device on one side of the second semiconductor element. By crimping the above-mentioned laminating step of applying the film-like adhesive and the second semiconductor element to which the film-like adhesive is attached via the film-like adhesive, at least a part of the first wire is filmed. It includes a die bonding process of embedding in a state adhesive.

図５〜９は、一実施形態に係る半導体装置の製造方法の一連の工程を示す模式断面図である。本実施形態に係る半導体装置２００は、第１のワイヤ８８及び第１の半導体素子Ｗａが埋め込まれてなる半導体装置であり、以下の手順により製造される。まず、図５に示すとおり、基板１４上の回路パターン９４上に、接着剤４１を有する第１の半導体素子Ｗａを圧着し、第１のワイヤ８８を介して基板１４上の回路パターン８４と第１の半導体素子Ｗａとを電気的にボンディング接続する（第１のワイヤボンディング工程）。 5 to 9 are schematic cross-sectional views showing a series of steps of the method for manufacturing a semiconductor device according to an embodiment. The semiconductor device 200 according to the present embodiment is a semiconductor device in which the first wire 88 and the first semiconductor element Wa are embedded, and is manufactured by the following procedure. First, as shown in FIG. 5, the first semiconductor element Wa having the adhesive 41 is crimped onto the circuit pattern 94 on the substrate 14, and the circuit pattern 84 and the first are on the substrate 14 via the first wire 88. The semiconductor element Wa of 1 is electrically bonded and connected (first wire bonding step).

次に、半導体ウェハ（例えば、厚さ１００μｍ、サイズ：８インチ）の片面に、接着シート１００をラミネートし、基材２０を剥がすことによって、半導体ウェハの片面にフィルム状接着剤１０（例えば、厚さ１１０μｍ）を貼り付ける。そして、フィルム状接着剤１０にダイシングテープを貼り合わせた後、所定の大きさ（例えば、７．５ｍｍ角）にダイシングすることにより、図６に示すとおり、フィルム状接着剤１０が貼付した第２の半導体素子Ｗａａを得る（ラミネート工程）。 Next, the adhesive sheet 100 is laminated on one side of the semiconductor wafer (for example, thickness 100 μm, size: 8 inches), and the base material 20 is peeled off, so that the film-like adhesive 10 (for example, thickness) is attached to one side of the semiconductor wafer. Wafer 110 μm) is pasted. Then, after the dicing tape is attached to the film-like adhesive 10, the dicing tape is diced to a predetermined size (for example, 7.5 mm square), so that the second film-like adhesive 10 is attached as shown in FIG. (Laminating step).

ラミネート工程の温度条件は、５０〜１００℃又は６０〜８０℃であってよい。ラミネート工程の温度が５０℃以上であると、半導体ウェハと良好な密着性を得ることができる。ラミネート工程の温度が１００℃以下であると、ラミネート工程中にフィルム状接着剤１０が過度に流動することが抑えられるため、厚さの変化等を引き起こすことを防止できる。 The temperature condition of the laminating step may be 50 to 100 ° C. or 60 to 80 ° C. When the temperature of the laminating step is 50 ° C. or higher, good adhesion to the semiconductor wafer can be obtained. When the temperature of the laminating step is 100 ° C. or lower, the film-like adhesive 10 is suppressed from being excessively flowed during the laminating step, so that it is possible to prevent a change in thickness or the like.

ダイシング方法としては、例えば、回転刃を用いるブレードダイシング、レーザーによってフィルム状接着剤又はウェハとフィルム状接着剤の両方を切断する方法等が挙げられる。 Examples of the dicing method include blade dicing using a rotary blade, a method of cutting a film-like adhesive or both a wafer and a film-like adhesive with a laser, and the like.

そして、フィルム状接着剤１０が貼付した第２の半導体素子Ｗａａを、第１の半導体素子Ｗａが第１のワイヤ８８を介してボンディング接続された基板１４に圧着する。具体的には、図７に示すとおり、フィルム状接着剤１０が貼付された第２の半導体素子Ｗａａを、フィルム状接着剤１０によって第１のワイヤ８８及び第１の半導体素子Ｗａが覆われるように載置し、次いで、図８に示すとおり、第２の半導体素子Ｗａａを基板１４に圧着させることで基板１４に第２の半導体素子Ｗａａを固定する（ダイボンド工程）。ダイボンド工程は、フィルム状接着剤１０を８０〜１８０℃、０．０１〜０．５０ＭＰａの条件で０．５〜３．０秒間圧着することが好ましい。ダイボンド工程の後、フィルム状接着剤１０を６０〜１７５℃、０．３〜０．７ＭＰａの条件で、５分間以上加圧及び加熱する。 Then, the second semiconductor element Waa to which the film-like adhesive 10 is attached is crimped to the substrate 14 to which the first semiconductor element Wa is bonded and connected via the first wire 88. Specifically, as shown in FIG. 7, the second semiconductor element Waa to which the film-like adhesive 10 is attached is covered with the film-like adhesive 10 so that the first wire 88 and the first semiconductor element Wa are covered. Then, as shown in FIG. 8, the second semiconductor element Waa is fixed to the substrate 14 by crimping the second semiconductor element Waa to the substrate 14 (die bonding step). In the die bonding step, it is preferable that the film-like adhesive 10 is pressure-bonded at 80 to 180 ° C. and 0.01 to 0.50 MPa for 0.5 to 3.0 seconds. After the die bonding step, the film-like adhesive 10 is pressurized and heated at 60 to 175 ° C. and 0.3 to 0.7 MPa for 5 minutes or more.

次いで、図９に示すとおり、基板１４と第２の半導体素子Ｗａａとを第２のワイヤ９８を介して電気的に接続した後（第２のワイヤボンディング工程）、回路パターン８４、第２のワイヤ９８及び第２の半導体素子Ｗａａを封止材４２で封止する。このような工程を経ることで半導体装置２００を製造することができる。 Then, as shown in FIG. 9, after the substrate 14 and the second semiconductor element Waa are electrically connected via the second wire 98 (second wire bonding step), the circuit pattern 84 and the second wire The 98 and the second semiconductor element Wire are sealed with the sealing material 42. The semiconductor device 200 can be manufactured through such a process.

他の実施形態として、半導体装置は、第１のワイヤ８８の少なくとも一部が埋め込まれてなるワイヤ埋め込み型の半導体装置であってもよい。 As another embodiment, the semiconductor device may be a wire-embedded semiconductor device in which at least a part of the first wire 88 is embedded.

以下、本発明について実施例を挙げてより具体的に説明する。ただし、本発明はこれら実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples.

（実施例１〜８及び比較例１〜４）
＜接着シートの作製＞
以下に示す各成分を表１及び表２に示した配合割合（質量部）で混合し、溶媒としてシクロヘキサノンを用いて固形分４０質量％の接着剤組成物のワニスを調製した。次に、得られたワニスを１００メッシュのフィルターでろ過し、真空脱泡した。真空脱泡後のワニスを、基材フィルムとして、厚さ３８μｍの離型処理を施したポリエチレンテレフタレート（ＰＥＴ）フィルム上に塗布した。塗布したワニスを、９０℃で５分間、続いて１４０℃で５分間の２段階で加熱乾燥した。このようにして、基材フィルム上に、半硬化（Ｂステージ）状態にある厚さ１１０μｍのフィルム状接着剤を備える接着シートを得た。(Examples 1 to 8 and Comparative Examples 1 to 4)
<Making an adhesive sheet>
Each of the components shown below was mixed at the blending ratios (parts by mass) shown in Tables 1 and 2, and cyclohexanone was used as a solvent to prepare a varnish of an adhesive composition having a solid content of 40% by mass. Next, the obtained varnish was filtered through a 100 mesh filter and vacuum defoamed. The varnish after vacuum defoaming was applied as a base film on a polyethylene terephthalate (PET) film having a thickness of 38 μm and subjected to a mold release treatment. The applied varnish was heated and dried in two steps at 90 ° C. for 5 minutes and then at 140 ° C. for 5 minutes. In this way, an adhesive sheet having a film-like adhesive having a thickness of 110 μm in a semi-cured (B stage) state was obtained on the base film.

なお、表１及び表２中の各成分は以下のとおりである。 The components in Tables 1 and 2 are as follows.

（Ａ）熱硬化性樹脂
（Ａ−１）脂環式環を有するエポキシ樹脂
Ａ−１−１：一般式（１ａ）で表されるエポキシ樹脂（ジシクロペンタジエン構造を有するエポキシ樹脂）、ＤＩＣ株式会社製、商品名：ＨＰ−７２００Ｌ、エポキシ当量：２５０〜２８０ｇ／ｅｑ
Ａ−１−２：一般式（１ａ）で表されるエポキシ樹脂（ジシクロペンタジエン構造を有するエポキシ樹脂）、日本化薬株式会社製、商品名：ＸＤ−１０００、エポキシ当量：２５４ｇ／ｅｑ
Ａ−１―３：一般式（２）で表されるエポキシ樹脂（２５℃で液体）、株式会社ダイセル製、商品名：セロキサイド２０２１Ｐ、エポキシ当量：１２８〜１４５ｇ／ｅｑ
Ａ−１−４：一般式（４）で表されるエポキシ樹脂、株式会社ダイセル製、商品名：ＥＨＰＥ３１５０、エポキシ当量：１７０〜１９０ｇ／ｅｑ
（Ａ−２）脂環式環を有しない芳香族エポキシ樹脂
Ａ−２−１：多官能芳香族エポキシ樹脂、株式会社プリンテック製、商品名：ＶＧ３１０１Ｌ、エポキシ当量：２１０ｇ／ｅｑ
Ａ−２−２：クレゾールノボラック型エポキシ樹脂、新日鉄住金化学株式会社製、商品名：ＹＤＣＮ−７００−１０、エポキシ当量：２０９ｇ／ｅｑ
Ａ−２−３：ビスフェノールＦ型エポキシ樹脂（２５℃で液体）、ＤＩＣ株式会社製、商品名：ＥＸＡ−８３０ＣＲＰ、エポキシ当量：１５９ｇ／ｅｑ
（Ｂ）硬化剤
Ｂ−１：ビスフェノールＡノボラック型フェノール樹脂、ＤＩＣ株式会社製、商品名：ＬＦ−４８７１、水酸基当量：１１８ｇ／ｅｑ
Ｂ−２：フェニルアラルキル型フェノール樹脂、三井化学株式会社製、商品名：ＸＬＣ−ＬＬ、水酸基当量：１７５ｇ／ｅｑ
Ｂ−３：フェニルアラルキル型フェノール樹脂、エア・ウォーター株式会社製、商品名：ＨＥ１００Ｃ−３０、水酸基当量：１７０ｇ／ｅｑ
（Ｃ）エラストマー
Ｃ−１：エポキシ基含有アクリル樹脂（アクリルゴム）、ナガセケムテックス株式会社製、商品名：ＨＴＲ−８６０Ｐ、重量平均分子量：８０万、グリシジル官能基モノマー比率：３％、Ｔｇ：−７℃
Ｃ−２：アクリル樹脂（アクリルゴム）、ナガセケムテックス株式会社製、商品名：ＳＧ−７０Ｌ、重量平均分子量：９０万、酸価：５ｍｇＫＯＨ／ｇ、Ｔｇ：−１３℃
（Ｄ）無機フィラー
Ｄ−１：シリカフィラー分散液、溶融シリカ、株式会社アドマテックス製、商品名：ＳＣ２０５０−ＨＬＧ、平均粒径：０．５０μｍ
（Ｅ）硬化促進剤
Ｅ−１：１−シアノエチル−２−フェニルイミダゾール、四国化成工業株式会社製、商品名：キュアゾール２ＰＺ−ＣＮ(A) Thermosetting resin (A-1) Epoxy resin having an alicyclic ring A-1-1: Epoxy resin represented by the general formula (1a) (epoxy resin having a dicyclopentadiene structure), DIC Corporation Made by company, product name: HP-7200L, epoxy equivalent: 250-280g / eq
A-1-2: Epoxy resin represented by the general formula (1a) (epoxy resin having a dicyclopentadiene structure), manufactured by Nippon Kayaku Co., Ltd., trade name: XD-1000, epoxy equivalent: 254 g / eq
A-1-3: Epoxy resin represented by the general formula (2) (liquid at 25 ° C.), manufactured by Daicel Corporation, trade name: seroxide 2021P, epoxy equivalent: 128 to 145 g / eq
A-1-4: Epoxy resin represented by the general formula (4), manufactured by Daicel Corporation, trade name: EHPE3150, epoxy equivalent: 170 to 190 g / eq
(A-2) Aromatic Epoxy Resin Not Having an Alicyclic Ring A2-11: Polyfunctional Aromatic Epoxy Resin, manufactured by Printec Co., Ltd., trade name: VG3101L, epoxy equivalent: 210 g / eq
A-2-2: Cresol novolac type epoxy resin, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., trade name: YDCN-700-10, epoxy equivalent: 209 g / eq
A-2-3: Bisphenol F type epoxy resin (liquid at 25 ° C), manufactured by DIC Corporation, trade name: EXA-830CRP, epoxy equivalent: 159 g / eq
(B) Hardener B-1: Bisphenol A novolak type phenol resin, manufactured by DIC Corporation, trade name: LF-4871, hydroxyl group equivalent: 118 g / eq
B-2: Phenyl aralkyl type phenolic resin, manufactured by Mitsui Chemicals, Inc., trade name: XLC-LL, hydroxyl group equivalent: 175 g / eq
B-3: Phenyl aralkyl type phenolic resin, manufactured by Air Water Inc., trade name: HE100C-30, hydroxyl group equivalent: 170 g / eq
(C) Elastomer C-1: Epoxy group-containing acrylic resin (acrylic rubber), manufactured by Nagase ChemteX Corporation, trade name: HTR-860P, weight average molecular weight: 800,000, glycidyl functional group monomer ratio: 3%, Tg: -7 ℃
C-2: Acrylic resin (acrylic rubber), manufactured by Nagase ChemteX Corporation, trade name: SG-70L, weight average molecular weight: 900,000, acid value: 5 mgKOH / g, Tg: -13 ° C.
(D) Inorganic filler D-1: Silica filler dispersion, fused silica, manufactured by Admatex Co., Ltd., trade name: SC2050-HLG, average particle size: 0.50 μm
(E) Curing Accelerator E-1: 1-Cyanoethyl-2-phenylimidazole, manufactured by Shikoku Chemicals Corporation, trade name: Curesol 2PZ-CN

＜各種物性の評価＞
得られた接着シートについて、埋め込み性及びブリード量の評価を行った。<Evaluation of various physical properties>
The obtained adhesive sheet was evaluated for embedding property and bleeding amount.

［埋め込み性評価］
接着シートの埋め込み性を以下の評価サンプルを作製して評価した。上記で得られたフィルム状接着剤（厚さ１１０μｍ）を、基材フィルムを剥がし、ダイシングテープに貼り付け、ダイシングダイボンディング一体型接着シートを得た。次に、厚さ１００μｍの半導体ウェハ（８インチ）を、接着剤側に７０℃に加熱して貼り付けた。その後、この半導体ウェハを７．５ｍｍ角にダイシングすることによって、半導体チップＡを得た。次に、ダイシングダイボンディング一体型接着シート（日立化成株式会社製、商品名：ＨＲ９００４−１０）（厚さ１０μｍ）を用意し、厚さ５０μｍの半導体ウェハ（８インチ）に７０℃に加熱して貼り付けた。その後、この半導体ウェハを４．５ｍｍ角にダイシングすることによって、ダイボンディングフィルム付きの半導体チップＢを得た。次いで、ソルダーレジスト（太陽日酸株式会社製、商品名：ＡＵＳ３０８）を塗布した総厚さ２６０μｍの評価用基板を用意し、ダイボンディングフィルム付きの半導体チップＢのダイボンディングフィルムと評価用基板のソルダーレジストとが接するように、１２０℃、０．２０ＭＰａ、２秒間の条件で圧着した。その後、半導体チップＡのフィルム状接着剤と半導体チップＢの半導体ウェハとが接するように、１２０℃、０．２０ＭＰａ、１．５秒間の条件で圧着し、評価サンプルを得た。この際、先に圧着している半導体チップＢが半導体チップＡの中央となるように位置合わせを行った。このようにして得られた評価サンプルを超音波デジタル画像診断装置（インサイト株式会社製、プローブ：７５ＭＨｚ）にてボイドの観測の有無を観測し、ボイドが観測された場合は、単位面積あたりのボイドの面積の割合を算出し、これらの分析結果を埋め込み性として評価した。評価基準は、以下のとおりである。結果を表１及び表２に示す。
Ａ：ボイドが観測されなかった。
Ｂ：ボイドが観測されたが、その割合が５面積％未満であった。
Ｃ：ボイドが観測され、その割合が５面積％以上であった。[Embedability evaluation]
The embedding property of the adhesive sheet was evaluated by preparing the following evaluation samples. The film-like adhesive (thickness 110 μm) obtained above was peeled off from the base film and attached to a dicing tape to obtain a dicing die bonding integrated adhesive sheet. Next, a semiconductor wafer (8 inches) having a thickness of 100 μm was attached to the adhesive side by heating to 70 ° C. Then, the semiconductor chip A was obtained by dicing this semiconductor wafer into a 7.5 mm square. Next, a dicing die bonding integrated adhesive sheet (manufactured by Hitachi Kasei Co., Ltd., trade name: HR9004-10) (thickness 10 μm) is prepared, and a semiconductor wafer (8 inches) having a thickness of 50 μm is heated to 70 ° C. I pasted it. Then, by dicing this semiconductor wafer into a 4.5 mm square, a semiconductor chip B with a die bonding film was obtained. Next, an evaluation substrate having a total thickness of 260 μm coated with a solder resist (manufactured by Taiyo Nissin Co., Ltd., trade name: AUS308) was prepared, and the die bonding film of the semiconductor chip B with the die bonding film and the solder of the evaluation substrate were prepared. The pressure was applied under the conditions of 120 ° C., 0.20 MPa, and 2 seconds so as to be in contact with the resist. Then, the film-like adhesive of the semiconductor chip A and the semiconductor wafer of the semiconductor chip B were pressure-bonded under the conditions of 120 ° C., 0.20 MPa, and 1.5 seconds to obtain an evaluation sample. At this time, the alignment was performed so that the semiconductor chip B crimped first was centered on the semiconductor chip A. The evaluation sample obtained in this way is observed with an ultrasonic digital diagnostic imaging device (manufactured by Insight Co., Ltd., probe: 75 MHz) for the presence or absence of voids, and if voids are observed, per unit area. The ratio of the area of voids was calculated, and these analysis results were evaluated as implantability. The evaluation criteria are as follows. The results are shown in Tables 1 and 2.
A: No voids were observed.
B: Voids were observed, but the proportion was less than 5 area%.
C: Voids were observed, and the ratio was 5 area% or more.

［ブリード量評価］
上記埋め込み性評価で作製した評価サンプルと同様にして、ブリード量評価の評価サンプルを作製した。顕微鏡を用いて、評価サンプルの４辺の中心から、フィルム状接着剤のはみ出し量を測長し、その最大値をブリード量とした。結果を表１及び表２に示す。[Bleed amount evaluation]
An evaluation sample for bleed amount evaluation was prepared in the same manner as the evaluation sample prepared for the embedding property evaluation. Using a microscope, the amount of protrusion of the film-like adhesive was measured from the center of the four sides of the evaluation sample, and the maximum value was taken as the bleed amount. The results are shown in Tables 1 and 2.

［ブリード量評価］
上記埋め込み性評価で「Ａ」又は「Ｂ」であったものについて、ブリード量評価を行った。上記埋め込み性評価で作製した評価サンプルと同様にして、ブリード量評価の評価サンプルを作製した。顕微鏡を用いて、評価サンプルの４辺の中心から、フィルム状接着剤のはみ出し量を測長し、その最大値をブリード量とした。結果を表１及び表２に示す。[Bleed amount evaluation]
The bleed amount was evaluated for those having "A" or "B" in the above-mentioned embedding property evaluation. An evaluation sample for bleed amount evaluation was prepared in the same manner as the evaluation sample prepared for the embedding property evaluation. Using a microscope, the amount of protrusion of the film-like adhesive was measured from the center of the four sides of the evaluation sample, and the maximum value was taken as the bleed amount. The results are shown in Tables 1 and 2.

Figure 2019150446
Figure 2019150446

Figure 2019150446
Figure 2019150446

表１に示すとおり、脂環式環を有するエポキシ樹脂を含む実施例１〜３は、それを含まない比較例１〜３に比べて、良好な埋め込み性を維持しつつ、ブリードを抑制することができた。また、表２の実施例４〜８から、他の脂環式環を有するエポキシ樹脂を用いた場合においても、同様の傾向があることが判明した。これらの結果から、本発明に係る接着剤組成物が、熱圧着時に良好な埋め込み性を有しつつ、ブリードを抑制することが可能であることが確認された。 As shown in Table 1, Examples 1 to 3 containing an epoxy resin having an alicyclic ring suppress bleeding while maintaining good embedding property as compared with Comparative Examples 1 to 3 not containing the epoxy resin. Was made. Further, from Examples 4 to 8 in Table 2, it was found that there is a similar tendency even when another epoxy resin having an alicyclic ring is used. From these results, it was confirmed that the adhesive composition according to the present invention can suppress bleeding while having good embedding property at the time of thermocompression bonding.

以上の結果のとおり、本発明に係る接着剤組成物は、熱圧着時の埋め込み性が良好で、ブリードが抑制できることから、接着剤組成物をフィルム状に形成してなるフィルム状接着剤は、チップ埋め込み型フィルム状接着剤であるＦＯＤ（Ｆｉｌｍ Ｏｖｅｒ Ｄｉｅ）又はワイヤ埋め込み型フィルム状接着剤であるＦＯＷ（Ｆｉｌｍ Ｏｖｅｒ Ｗｉｒｅ）として有用となり得る。 As described above, the adhesive composition according to the present invention has good embedding property at the time of thermal pressure bonding and bleeding can be suppressed. Therefore, the film-like adhesive obtained by forming the adhesive composition into a film form is It can be useful as FOD (Film Over Die), which is a chip-embedded film-like adhesive, or FOW (Film Over Wire), which is a wire-embedded film-like adhesive.

１０…フィルム状接着剤、１４…基板、２０…基材、３０…保護フィルム、４１…接着剤、４２…封止材、８４、９４…回路パターン、８８…第１のワイヤ、９０…有機基板、９８…第２のワイヤ、１００、１１０…接着シート、２００…半導体装置、Ｗａ…第１の半導体素子、Ｗａａ…第２の半導体素子。 10 ... film-like adhesive, 14 ... substrate, 20 ... base material, 30 ... protective film, 41 ... adhesive, 42 ... encapsulant, 84, 94 ... circuit pattern, 88 ... first wire, 90 ... organic substrate , 98 ... second wire, 100, 110 ... adhesive sheet, 200 ... semiconductor device, Wa ... first semiconductor element, Wa ... second semiconductor element.

Claims (12)

熱硬化性樹脂と、硬化剤と、エラストマーと、を含有し、
前記熱硬化性樹脂が脂環式環を有するエポキシ樹脂を含む、接着剤組成物。Contains a thermosetting resin, a curing agent, and an elastomer,
An adhesive composition comprising an epoxy resin in which the thermosetting resin has an alicyclic ring. 前記硬化剤がフェノール樹脂を含む、請求項１に記載の接着剤組成物。 The adhesive composition according to claim 1, wherein the curing agent contains a phenol resin. 前記エラストマーがアクリル樹脂を含む、請求項１又は２に記載の接着剤組成物。 The adhesive composition according to claim 1 or 2, wherein the elastomer contains an acrylic resin. 前記熱硬化性樹脂が脂環式環を有しない芳香族エポキシ樹脂をさらに含む、請求項１〜３のいずれか一項に記載の接着剤組成物。 The adhesive composition according to any one of claims 1 to 3, further comprising an aromatic epoxy resin in which the thermosetting resin does not have an alicyclic ring. 前記脂環式環を有しない芳香族エポキシ樹脂が２５℃で液体である、請求項４に記載の接着剤組成物。 The adhesive composition according to claim 4, wherein the aromatic epoxy resin having no alicyclic ring is a liquid at 25 ° C. 無機フィラーをさらに含有する、請求項１〜５のいずれか一項に記載の接着剤組成物。 The adhesive composition according to any one of claims 1 to 5, further comprising an inorganic filler. 硬化促進剤をさらに含有する、請求項１〜６のいずれか一項に記載の接着剤組成物。 The adhesive composition according to any one of claims 1 to 6, further comprising a curing accelerator. 請求項１〜７のいずれか一項に記載の接着剤組成物をフィルム状に形成してなる、フィルム状接着剤。 A film-like adhesive obtained by forming the adhesive composition according to any one of claims 1 to 7 in the form of a film. 基材と、
前記基材上に設けられた、請求項８に記載のフィルム状接着剤と、
を備える、接着シート。With the base material
The film-like adhesive according to claim 8 provided on the base material and
Adhesive sheet. 前記基材がダイシングテープである、請求項９に記載の接着シート。 The adhesive sheet according to claim 9, wherein the base material is a dicing tape. 前記フィルム状接着剤の前記基材とは反対側の面に積層された保護フィルムをさらに備える、請求項９又は１０に記載の接着シート。 The adhesive sheet according to claim 9 or 10, further comprising a protective film laminated on the surface of the film-like adhesive opposite to the base material. 基板上に第１のワイヤを介して第１の半導体素子を電気的に接続するワイヤボンディング工程と、
第２の半導体素子の片面に、請求項８に記載のフィルム状接着剤を貼付するラミネート工程と、
前記フィルム状接着剤が貼付された第２の半導体素子を、前記フィルム状接着剤を介して圧着することで、前記第１のワイヤの少なくとも一部を前記フィルム状接着剤に埋め込むダイボンド工程と、
を備える、半導体装置の製造方法。A wire bonding step of electrically connecting a first semiconductor element on a substrate via a first wire,
A laminating step of attaching the film-like adhesive according to claim 8 to one side of the second semiconductor element, and
A die bonding step of embedding at least a part of the first wire in the film-like adhesive by crimping the second semiconductor element to which the film-like adhesive is attached via the film-like adhesive.
A method for manufacturing a semiconductor device.
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