JP2023017948A - Adhesive composition, film-like adhesive, adhesive sheet, and method for manufacturing semiconductor device - Google Patents

Adhesive composition, film-like adhesive, adhesive sheet, and method for manufacturing semiconductor device Download PDF

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JP2023017948A
JP2023017948A JP2022179719A JP2022179719A JP2023017948A JP 2023017948 A JP2023017948 A JP 2023017948A JP 2022179719 A JP2022179719 A JP 2022179719A JP 2022179719 A JP2022179719 A JP 2022179719A JP 2023017948 A JP2023017948 A JP 2023017948A
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adhesive
film
adhesive composition
semiconductor element
mass
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JP7472954B2 (en
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慎太郎 橋本
Shintaro Hashimoto
祐樹 中村
Yuki Nakamura
智陽 山崎
Tomoaki Yamazaki
健太 菊地
Kenta Kikuchi
大輔 舛野
Daisuke MASUNO
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Resonac Holdings Corp
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Resonac Holdings Corp
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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
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    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
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    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
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    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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    • C09J7/00—Adhesives in the form of films or foils
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    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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    • H01L21/52—Mounting semiconductor bodies in containers
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  • Engineering & Computer Science (AREA)
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  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Die Bonding (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Encapsulation Of And Coatings For Semiconductor Or Solid State Devices (AREA)
  • Dicing (AREA)

Abstract

PROBLEM TO BE SOLVED: To provide an adhesive composition which can suppress bleeding while having good embedding property at the time of thermocompression bonding.
SOLUTION: An adhesive composition contains a thermosetting resin, a curing agent and an elastomer, wherein the thermosetting resin contains an epoxy resin having an alicyclic ring, the epoxy resin having the alicyclic ring is an epoxy resin represented by the following general formula (1a), and a content of the total of the thermosetting resin and the curing agent is 30-55 mass% based on the total amount of the adhesive composition. In formula (1a), n1 represents an integer of 1 to 10.
SELECTED DRAWING: None
COPYRIGHT: (C)2023,JPO&INPIT

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。 TECHNICAL FIELD The present invention relates to an adhesive composition, a film adhesive, an adhesive sheet, and a method for manufacturing 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 supporting member for mounting the semiconductor chip. However, along with the recent miniaturization and integration of semiconductor chips, there is a demand for miniaturization and fineness of supporting members used. On the other hand, in the case of using a silver paste, there may be problems such as the occurrence of problems during wire bonding due to the protrusion of the paste or the inclination of the semiconductor chip, the difficulty of controlling the film thickness, the occurrence of voids, and the like.

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, film-like adhesives have been used for bonding semiconductor chips and supporting members (see, for example, Patent Document 1). When using an adhesive sheet comprising a dicing tape and a film-like adhesive layered on the dicing tape, the film-like adhesive is attached to the back surface of a semiconductor wafer, and the semiconductor wafer is singulated by dicing to obtain a film-like adhesive. A semiconductor chip with an adhesive can be obtained. The obtained semiconductor chip with a film-like adhesive can be attached to a supporting member via the film-like adhesive and bonded by thermocompression bonding.

特開２００７－０５３２４０号公報JP 2007-053240 A

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。 In addition, when the film-like adhesive is used as FOW (Film Over Wire), which is a wire-embedded film-like adhesive, or FOD (Film Over Die), which is a semiconductor chip-embedded film-like adhesive, it is necessary to improve the embedding property. Therefore, high fluidity is required during thermocompression bonding. Therefore, the frequency and amount of bleeding tend to increase. In some cases, bleeds can occur up to the top surface of the semiconductor chip, which can lead to electrical failures or wire bonding failures.

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 the main object thereof is to provide an adhesive composition capable of suppressing bleeding while having good embedding properties during thermocompression bonding. 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, wherein the thermosetting resin comprises an epoxy resin having an alicyclic ring. According to such an adhesive composition, it is possible to suppress bleeding while having good embedding properties during 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。 Curing agents may include phenolic resins. Also, 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 having no alicyclic ring. Aromatic epoxy resins without cycloaliphatic rings 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. Moreover, 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 onto a substrate via a first wire, and a second semiconductor element is crimped onto the first semiconductor element. , may be used to crimp the second semiconductor element and to embed at least a portion 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 provides a composition containing a thermosetting resin, a curing agent, and an elastomer, wherein the thermosetting resin includes an epoxy resin having an alicyclic ring, on a substrate through a first wire. are connected by wire bonding, and a second semiconductor element is pressure-bonded onto the first semiconductor element, wherein the second semiconductor element is pressure-bonded and at least a part of the first wire is It may also relate to applications as adhesives or applications for the production of adhesives, which are used to embed .

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。 Another aspect WHEREIN: This invention provides the film adhesive formed 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 aforementioned film 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 substrate may be a dicing tape. In this specification, an adhesive sheet whose substrate 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 adhesive opposite to the substrate.

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。 Furthermore, in another aspect, the present invention includes a wire bonding step of electrically connecting a first semiconductor element on a substrate via a first wire, and a film-like film on one side of a second semiconductor element. At least part of the first wire is attached to the film adhesive by laminating the adhesive and pressing the second semiconductor element to which the film adhesive is attached through the film adhesive. and a die bonding step of 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, a first semiconductor chip is wire-bonded onto a semiconductor substrate via a first wire, and a second semiconductor chip is pressure-bonded onto the first semiconductor chip via an adhesive film. A wire-embedded semiconductor device in which at least a portion of the first wire is embedded in the adhesive film may be provided, and the first wire and the first semiconductor chip are embedded in the adhesive film. It may also 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。 ADVANTAGE OF THE INVENTION According to this invention, the adhesive composition which can suppress bleeding is provided, while having favorable embedding property at the time of thermocompression bonding. Therefore, a film-like adhesive obtained 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. Over Wire). Further, according to the present invention, an adhesive sheet using such a film-like adhesive and a method for manufacturing a semiconductor device are provided.

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。1 is a schematic cross-sectional view showing a film-like adhesive according to one embodiment; FIG. 一実施形態に係る接着シートを示す模式断面図である。1 is a schematic cross-sectional view showing an adhesive sheet according to one embodiment; FIG. 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。FIG. 10 is a schematic cross-sectional view showing an adhesive sheet according to another 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。1 is a schematic cross-sectional view showing a semiconductor device according to one embodiment; FIG. 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。1A to 1D are schematic cross-sectional views showing a series of steps of a method for manufacturing a semiconductor device according to 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。1A to 1D are schematic cross-sectional views showing a series of steps of a method for manufacturing a semiconductor device according to 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。1A to 1D are schematic cross-sectional views showing a series of steps of a method for manufacturing a semiconductor device according to 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。1A to 1D are schematic cross-sectional views showing a series of steps of a method for manufacturing a semiconductor device according to 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。1A to 1D are schematic cross-sectional views showing a series of steps of a method for manufacturing a semiconductor device according to 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。 BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, embodiments of the present invention will be described with appropriate reference to the drawings. 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 its corresponding methacrylic acid. The same applies to other similar expressions such as (meth)acryloyl groups.

［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 this embodiment contains (A) a thermosetting resin, (B) a curing agent, and (C) an elastomer. The adhesive composition is thermosetting and can go through a semi-cured (B stage) state and become a fully cured (C stage) state after 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。 <(A) component: thermosetting resin>
The thermosetting resin may contain an epoxy resin from the viewpoint of adhesiveness. The adhesive composition according to this 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。 Component (A-1) is a compound having an alicyclic ring and an epoxy group in the molecule. The epoxy group may be bonded to the alicyclic ring of the compound or a site other than the alicyclic ring via a single bond or a linking group (eg, an alkylene group, an oxyalkylene group, etc.). The compound may also be a compound having an epoxy group formed with two carbon atoms forming an alicyclic ring (that is, an alicyclic epoxy compound). By including component (A-1) as a thermosetting resin, it is possible to suppress bleeding while maintaining good embedding properties during 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 component (A-1) is not particularly limited, but may be 90-600 g/eq, 100-500 g/eq, or 120-450 g/eq. When the epoxy equivalent of component (A-1) is within this 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。 Component (A-1) may be, for example, any one of epoxy resins represented by the following general formulas (1) to (4).

Figure 2023017948000001
Figure 2023017948000001

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 formula (1), E represents an alicyclic ring, G represents a single bond or an alkylene group, and each R 1 independently represents a hydrogen atom or a monovalent hydrocarbon group. n1 represents an integer of 1-10 and m represents an integer of 1-3.

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。 E may have 4-12, 5-11, or 6-10 carbon atoms. E may be monocyclic or polycyclic, preferably polycyclic, more preferably a dicyclopentadiene ring. The alkylene group for G may be an alkylene group having 1 to 5 carbon atoms such as a methylene group, ethylene group, propylene group, butylene group and pentylene group. G is preferably a single bond. The monovalent hydrocarbon group for R 1 is, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group, an aryl group such as a phenyl group or a naphthyl group, or a heteroaryl group such as a pyridyl group. It's okay. 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 2023017948000002
Figure 2023017948000002

式（１ａ）中、ｎ１は上記と同義である。 In formula (1a), n1 has the same meaning as 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。 Examples of commercially available epoxy resins represented by formula (1a) include HP-7200L, HP-7200H, and HP-7200 (all manufactured by DIC Corporation) and XD-1000 (manufactured by Nippon Kayaku Co., Ltd.). etc.

Figure 2023017948000003
Figure 2023017948000003

式（２）中、Ｒ２は２価の炭化水素基を示す。 In formula ( 2 ), R2 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。 The divalent hydrocarbon group for R 2 is, for example, an alkylene group such as a methylene group, an ethylene group, a propylene group, a butylene group or a pentylene group, an arylene group such as a phenylene group or a naphthylene group, or a heteroarylene group such as a pyridylene group. It's okay. 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 formula (2) include Celoxide 2021P and Celoxide 2081 (both manufactured by Daicel Corporation).

Figure 2023017948000004
Figure 2023017948000004

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。 The divalent hydrocarbon group for R 3 , R 4 and R 5 includes the same divalent hydrocarbon groups as those exemplified 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 formula (3) include Syna-Epoxy28 (manufactured by SYANASIA).

Figure 2023017948000005
Figure 2023017948000005

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 1-10.

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 for R 6 include those exemplified for the monovalent hydrocarbon group for 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 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, component (A-1) is preferably an epoxy resin represented by general formula (1), more preferably an epoxy resin represented by 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 component (A-1) may be 15 to 100% by mass based on the total amount of component (A). The content of 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 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 component (A-1) is 5% by mass or more based on the total amount of the adhesive composition, there is a tendency that bleeding can be well suppressed while having better embedding properties during 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 component (A-1), component (A) may further contain (A-2) an aromatic epoxy resin having no 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. Component (A-2) includes, for example, 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, bisphenol F Novolak-type epoxy resin, stilbene-type epoxy resin, triazine skeleton-containing epoxy resin, fluorene skeleton-containing epoxy resin, triphenol phenol-methane-type epoxy resin, biphenyl-type epoxy resin, xylylene-type epoxy resin, phenylaralkyl-type epoxy resin, biphenylaralkyl-type epoxy Resins, naphthalene-type epoxy resins, polyfunctional phenols, diglycidyl ether compounds of polycyclic aromatics such as anthracene, and the like. You may use these individually by 1 type or in combination of 2 or more types. Among these, component (A-2) may be 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 component (A-2) is not particularly limited, but may be 90-600 g/eq, 100-500 g/eq, or 120-450 g/eq. When the epoxy equivalent of component (A-2) is within this 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 component (A-2) may be 0 to 85% by mass based on the total amount of component (A). The content of 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。 <(B) Component: Curing Agent>
Component (B) is not particularly limited, and can be one commonly used as a curing agent for thermosetting resins. When the thermosetting resin contains an epoxy resin, examples of component (B) include phenolic resins, ester compounds, aromatic amines, aliphatic amines, and acid anhydrides. You may use these individually by 1 type or in combination of 2 or more types. 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。 Phenolic resins can be used without particular limitation as long as they have a phenolic hydroxyl group in the molecule. Examples of phenolic resins include phenols such as phenol, cresol, resorcinol, catechol, bisphenol A, bisphenol F, phenylphenol and aminophenol, and/or naphthols such as α-naphthol, β-naphthol and dihydroxynaphthalene, and formaldehyde. Novolac-type phenol resin obtained by condensation or co-condensation of a compound having an aldehyde group in the presence of an acidic catalyst, allylated bisphenol A, allylated bisphenol F, allylated naphthalene diol, phenol novolac, phenols such as phenol and / Alternatively, phenol aralkyl resins synthesized from naphthols and dimethoxyparaxylene or bis(methoxymethyl)biphenyl, naphthol aralkyl resins, biphenyl aralkyl phenol resins, phenyl aralkyl phenol resins, and the like can be mentioned. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of heat resistance, the phenol resin has a water absorption of 2% by mass or less under conditions of 48 hours in a constant temperature and humidity chamber at 85 ° C. and 85% RH, and a thermogravimetric analyzer (TGA). is less than 5% by mass at 350° C. (heating rate: 5° C./min, atmosphere: nitrogen).

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), Milex XLC series, XL series (manufactured by Mitsui Chemicals, Inc.), HE series (manufactured by Air Water Inc.), and the like. 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 equivalent of the phenolic resin is not particularly limited, but may be 80-400 g/eq, 90-350 g/eq, or 100-300 g/eq. When the hydroxyl group equivalent weight of the phenolic resin is within this 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 phenolic resin, the ratio of the epoxy equivalent of the epoxy resin to the hydroxyl equivalent of the phenolic resin (epoxy equivalent of epoxy resin/hydroxyl equivalent of phenolic 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/ 0.40, or 0.45/0.55 to 0.55/0.45. When the corresponding amount ratio is 0.30/0.70 or more, more sufficient curability tends to be obtained. When the corresponding amount ratio is 0.70/0.30 or less, it is possible to prevent the viscosity from becoming too high and 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 components (A) and (B) may be 30 to 70% by mass based on the total amount of the adhesive composition. The total content of component (A) and component (B) may be 33% by mass or more, 36% by mass or more, or 40% by mass or more, and may be 65% by mass or less, 60% by mass or less, or 55% by mass. % or less. When the total content of components (A) and (B) is 30% by mass or more based on the total amount of the adhesive composition, the adhesiveness tends to improve. When the total content of components (A) and (B) is 70% by mass or less based on the total amount of the adhesive composition, the viscosity can be prevented from becoming too low, and bleeding can be further suppressed. tends to be possible.

＜（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。 <(C) Component: Elastomer>
The adhesive composition according to this embodiment contains (C) an elastomer. Component (C) preferably has a glass transition temperature (Tg) of 50° C. or lower for the polymer constituting the elastomer.

（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。 Component (C) includes, for example, acrylic resins, polyester resins, polyamide resins, polyimide resins, silicone resins, butadiene resins, acrylonitrile resins 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, acrylic resin means a polymer containing structural units derived from (meth)acrylic acid ester. The acrylic resin is preferably a polymer containing, as a structural unit, 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 carboxyl group. The acrylic resin may also be 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 flexibility of the adhesive composition from becoming too high. This makes it easier to cut the film-like adhesive during wafer dicing, making it possible to prevent the occurrence of burrs. When the Tg of the acrylic resin is 50°C or less, it tends to be possible to suppress a decrease in the flexibility of the adhesive composition. This tends to make it easier to sufficiently fill voids when the film-like adhesive is attached to the wafer. Also, it is possible to prevent chipping during dicing due to deterioration in adhesion of the wafer. Here, the glass transition temperature (Tg) means a value measured using a DSC (differential scanning calorimeter) (for example, "Thermo Plus 2" manufactured by Rigaku Corporation).

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 acrylic resin may have a weight average molecular weight (Mw) of 100,000 to 3,000,000 or 500,000 to 2,000,000. When the Mw of the acrylic resin is in such a range, it is possible to appropriately control the film formability, the strength in the form of a film, the flexibility, the tackiness, etc., and the reflow property 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 standard polystyrene calibration curve.

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, HTR-860P-3CSP-3DB (all available from Nagase ChemteX Corporation). manufactured 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 component (C) may be 20 to 200 parts by mass or 30 to 100 parts by mass with respect to 100 parts by mass as the total of components (A) and (B). When the content of component (C) is 20 parts by mass or more with respect to 100 parts by mass of the total amount of components (A) and (B), the handling properties (e.g., bending properties) of the film-like adhesive are better. tends to be When the content of component (C) is 200 parts by mass or less with respect to 100 parts by mass of the total amount of components (A) and (B), it is possible to further prevent the flexibility of the adhesive composition from becoming too high. tends to be possible. This tends to make it easier to cut the film-like adhesive during wafer dicing, making it even more possible to 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。 <(D) component: inorganic filler>
The adhesive composition according to the present embodiment may further contain (D) an inorganic filler. Examples of inorganic fillers include aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, aluminum nitride, aluminum borate whiskers, boron nitride, and crystals. crystalline silica, amorphous silica, and the like. These may be used individually by 1 type, and may be used in combination of 2 or more type. The inorganic filler may contain aluminum oxide, aluminum nitride, boron nitride, crystalline silica, or amorphous silica from the viewpoint of further improving the thermal conductivity of the resulting film-like adhesive. In addition, from the viewpoint of adjusting the melt viscosity of the adhesive composition and from the viewpoint of imparting thixotropic properties to the adhesive composition, the inorganic filler includes aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, 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 component (D) may be 0.005 to 0.5 μm or 0.05 to 0.3 μm from the viewpoint of further improving adhesiveness. Here, the average particle diameter 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。 Component (D) may be surface-treated with a surface-treating agent from the viewpoint of compatibility between its surface and solvents, other components, etc., and adhesive strength. Examples of surface treatment agents include silane coupling agents. Examples of the functional group of the silane coupling agent include vinyl group, (meth)acryloyl group, epoxy group, mercapto group, amino group, diamino group, alkoxy group and ethoxy group.

（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 component (D) may be 10 to 90 parts by mass or 10 to 50 parts by mass with respect to 100 parts by mass as the total of components (A), (B) and (C). When the content of component (D) is 10 parts by mass or more with respect to the total amount of 100 parts by mass of components (A), (B), and (C), the dicing property of the adhesive layer before curing is poor. and the adhesive strength of the adhesive layer after curing tends to improve. When the content of component (D) is 90 parts by mass or less with respect to the total amount of 100 parts by mass of components (A), (B), and (C), it is possible to suppress a decrease in fluidity and cure. It is possible to prevent the elastic modulus of the subsequent film 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。 <(E) component: curing accelerator>
The adhesive composition according to this embodiment may contain (E) a curing accelerator. The curing accelerator is not particularly limited, and commonly used ones can be used. Component (E) includes, for example, imidazoles and their derivatives, organophosphorus compounds, secondary amines, tertiary amines, quaternary ammonium salts and the like. You may use these individually by 1 type or in combination of 2 or more types. Among these, from the viewpoint of reactivity, the component (E) may be imidazoles and derivatives thereof.

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 imidazoles include 2-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole and the like. You may use these individually by 1 type or in combination of 2 or more types.

（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 component (E) is 0.04 to 3 parts by mass or 0.04 to 0.2 parts by mass with respect to the total amount of 100 parts by mass of components (A), (B), and (C). can be When the content of component (E) is within this range, there is a tendency to achieve both curability and reliability.

＜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 this embodiment may further contain, as other components, an antioxidant, a silane coupling agent, a rheology control agent, and the like. The content of these components may be 0.02 to 3 parts by mass with respect to 100 parts by mass as the total amount of 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 components other than component (D). Examples of solvents include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene and p-cymene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; cyclic ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and 4-hydroxy-4-methyl-2-pentanone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate and γ-butyrolactone; carbonic acid esters such as ethylene carbonate and propylene carbonate; amides such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl-2-pyrrolidone; You may use these individually by 1 type or in combination of 2 or more types. Among 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 solids concentration in the adhesive varnish may be 10-80% by weight, based on the total weight 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 components (A), (B), (C), a solvent, and, if necessary, components (D), (E), and other components. can be prepared by Mixing and kneading can be carried out by appropriately combining ordinary dispersing machines such as a stirrer, a milling machine, a three-roll mill, 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 adding the high-molecular-weight component. Also, after the adhesive varnish is prepared, 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 adhesive]
FIG. 1 is a schematic cross-sectional view showing a film adhesive according to one embodiment. The film adhesive 10 is obtained by forming the adhesive composition described above into a film. The film adhesive 10 may be in a semi-cured (B stage) state. Such a film 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 of polytetrafluoroethylene, polyethylene, polypropylene, polymethylpentene, polyethylene terephthalate, polyimide, and the like. The thickness of the support film may be, for example, 60-200 μm or 70-170 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 for 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, a curtain coating method, and the like. be done. The conditions for drying by heating are not particularly limited as long as the solvent used is sufficiently volatilized.

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 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 unevenness 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 one embodiment. The adhesive sheet 100 comprises a base material 20 and the above-described film 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 substrate 20 is not particularly limited, but may be a substrate film. The base film may be similar to 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 substrate 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 lamination process to the semiconductor wafer is performed once, 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. In addition, the dicing tape may be subjected to surface treatment such as primer coating, UV treatment, corona discharge treatment, polishing treatment, etching treatment, etc., if necessary. The dicing tape is preferably sticky. Such a dicing tape may be the above-described plastic film with adhesiveness, or may be the above-described plastic film having an adhesive layer provided on one side thereof.

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 in the method of forming the film adhesive described above. The method of applying the adhesive composition to the substrate 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 using a prefabricated film adhesive. In this case, the adhesive sheet 100 can be formed by laminating under predetermined conditions (for example, room temperature (20° C.) or heating) using a roll laminator, vacuum laminator, or the like. Since the adhesive sheet 100 can be continuously produced and is efficient, 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 properties such as unevenness of semiconductor chips, wires, wiring circuits of substrates, and the like. When the thickness of the film-like adhesive 10 is 20 μm or more, there is a tendency to obtain more sufficient adhesive force, and when the thickness of the film-like adhesive 10 is 200 μm or less, it is economical and a semiconductor device. It is possible to meet the demand for miniaturization of

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 adhesive 10 opposite to the substrate 20 . Protective film 30 may be similar to the support film described above. The thickness of the protective film may be, for example, 15-200 μm or 70-170 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 a semiconductor device according to one embodiment. In the semiconductor device 200, a first semiconductor element Wa in a first stage is wire-bonded to the substrate 14 via a first wire 88, and a second semiconductor element Waa is formed on the first semiconductor element Wa. are pressure-bonded via the film-like adhesive 10 to embed at least a part of the first wire 88 in the film-like adhesive 10 . The semiconductor device may be a wire-embedded semiconductor device in which at least part of the first wire 88 is embedded, or a semiconductor device in which the first wire 88 and the first semiconductor element Wa are embedded. may Further, in the semiconductor device 200, the substrate 14 and the second semiconductor element Waa are electrically connected through the second wire 98, and the second semiconductor element Waa is sealed with 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 10-170 μm, and the thickness of the second semiconductor element Waa may be 20-400 μm. The first semiconductor element Wa embedded inside the film 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 on which two circuit patterns 84 and 94 are formed respectively. The first semiconductor element Wa is pressure-bonded onto the circuit pattern 94 via an adhesive 41 . The second semiconductor element Waa is applied via the film adhesive 10 so that the circuit pattern 94 to which the first semiconductor element Wa is not pressure-bonded, the first semiconductor element Wa, and part of the circuit pattern 84 are covered. It is crimped to the substrate 14 . The film-like adhesive 10 is embedded in uneven steps caused by the circuit patterns 84 and 94 on the substrate 14 . The second semiconductor element Waa, the circuit pattern 84 and the second wires 98 are sealed with a resin 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。 [Method for manufacturing a semiconductor device]
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 to a substrate via a first wire, and At least a part of the first wire is formed into a film by laminating the above-described film-like adhesive and pressing the second semiconductor element to which the film-like adhesive is attached via the film-like adhesive. and a die-bonding step of embedding in a similar 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 a method for manufacturing a semiconductor device according to one embodiment. The semiconductor device 200 according to this 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 on the substrate 14 and the first wire 88 are connected to each other via the first wire 88. As shown in FIG. 1 is electrically bonded to the semiconductor element Wa (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, an adhesive sheet 100 is laminated on one side of a semiconductor wafer (for example, thickness 100 μm, size: 8 inches), and the substrate 20 is peeled off, so that a film adhesive 10 (for example, thickness 10) is applied to one side of the semiconductor wafer. 110 μm) is attached. Then, after affixing a dicing tape to the film-like adhesive 10, the film-like adhesive 10 is diced into a predetermined size (for example, 7.5 mm square). is obtained (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 conditions for the lamination process may be 50-100°C or 60-80°C. A semiconductor wafer and favorable adhesiveness can be obtained as the temperature of a lamination process is 50 degreeC or more. When the temperature in the lamination process is 100° C. or less, excessive flow of the film adhesive 10 is suppressed during the lamination process, so that variations in thickness can be prevented.

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。 The dicing method includes, for example, blade dicing using a rotary blade, a method of cutting the film-like adhesive or both the wafer and the 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 applied is pressure-bonded to the substrate 14 to which the first semiconductor element Wa is bonded through the first wire 88 . Specifically, as shown in FIG. 7, the second semiconductor element Waa to which the film-like adhesive 10 is adhered is placed such that the film-like adhesive 10 covers the first wire 88 and the first semiconductor element Wa. Then, as shown in FIG. 8, the second semiconductor element Waa is fixed to the substrate 14 by pressure bonding the second semiconductor element Waa to the substrate 14 (die bonding step). In the die bonding step, the film adhesive 10 is preferably pressure-bonded under conditions of 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 adhesive 10 is pressurized and heated under conditions of 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。 Next, as shown in FIG. 9, after electrically connecting the substrate 14 and the second semiconductor element Waa via the second wire 98 (second wire bonding step), the circuit pattern 84, the second wire 98 and the second semiconductor element Waa are sealed with a sealing material 42 . Through such steps, the semiconductor device 200 can be manufactured.

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 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 more specifically 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)
<Preparation of adhesive sheet>
Each component shown below was mixed at the compounding ratio (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. The resulting varnish was then filtered through a 100 mesh filter and vacuum defoamed. The varnish after vacuum defoaming was applied as a substrate film onto a release-treated polyethylene terephthalate (PET) film having a thickness of 38 μm. The applied varnish was dried by heating in two steps, 90° C. for 5 minutes and then 140° C. for 5 minutes. In this way, an adhesive sheet comprising a semi-cured (B-stage) film adhesive having a thickness of 110 μm on the base film was obtained.

なお、表１及び表２中の各成分は以下のとおりである。 In addition, each component in Table 1 and Table 2 is 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 general formula (1a) (epoxy resin having a dicyclopentadiene structure), DIC stock Company product, product name: HP-7200L, epoxy equivalent: 250 to 280 g/eq
A-1-2: Epoxy resin represented by 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 general formula (2) (liquid at 25° C.), manufactured by Daicel Corporation, trade name: Celoxide 2021P, epoxy equivalent: 128 to 145 g/eq
A-1-4: Epoxy resin represented by general formula (4), manufactured by Daicel Corporation, trade name: EHPE3150, epoxy equivalent: 170 to 190 g/eq
(A-2) Aromatic epoxy resin having no alicyclic ring A-2-1: Polyfunctional aromatic epoxy resin, manufactured by Printec Co., Ltd., trade name: VG3101L, epoxy equivalent: 210 g / eq
A-2-2: Cresol novolak 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) Curing agent B-1: Bisphenol A novolac type phenolic resin, manufactured by DIC Corporation, trade name: LF-4871, hydroxyl equivalent: 118 g/eq
B-2: Phenylaralkyl-type phenolic resin, manufactured by Mitsui Chemicals, Inc., trade name: XLC-LL, hydroxyl equivalent: 175 g/eq
B-3: Phenylaralkyl-type phenolic resin, manufactured by Air Water Inc., trade name: HE100C-30, hydroxyl 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
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 Admatechs Co., Ltd., trade name: SC2050-HLG, average particle size: 0.50 μm
(E) Curing accelerator E-1: 1-cyanoethyl-2-phenylimidazole, manufactured by Shikoku Kasei Co., Ltd., trade name: Cursol 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 resulting adhesive sheet was evaluated for embeddability 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。 [Evaluation of Embedability]
The embeddability of the adhesive sheet was evaluated by preparing the following evaluation samples. The film 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) with a thickness of 100 μm was heated to 70° C. and attached to the adhesive side. Then, the semiconductor chip A was obtained by dicing this semiconductor wafer into 7.5 mm square. Next, a dicing die bonding integrated adhesive sheet (manufactured by Hitachi Chemical Co., Ltd., trade name: HR9004-10) (thickness: 10 μm) was prepared and heated to 70° C. on a semiconductor wafer (8 inches) with a thickness of 50 μm. pasted. Then, this semiconductor wafer was diced into 4.5 mm squares to obtain semiconductor chips B with a die bonding film. Next, an evaluation substrate with a total thickness of 260 μm coated with a solder resist (manufactured by Taiyo Nippon Sanso 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 It was pressure-bonded under the conditions of 120° C., 0.20 MPa, and 2 seconds so as to be in contact with the resist. After that, the film adhesive of the semiconductor chip A and the semiconductor wafer of the semiconductor chip B were press-bonded under the conditions of 120° C., 0.20 MPa, and 1.5 seconds to obtain an evaluation sample. At this time, alignment was performed so that the semiconductor chip B, which had been pressure-bonded first, was positioned at the center of the semiconductor chip A. As shown in FIG. The evaluation sample obtained in this way is observed for the presence or absence of voids with an ultrasonic digital diagnostic imaging device (manufactured by Insight Corporation, probe: 75 MHz). The area ratio of voids was calculated, and these analysis results were evaluated as embeddability. Evaluation criteria are as follows. The results are shown in Tables 1 and 2.
A: No voids were observed.
B: Voids were observed, but their proportion was less than 5 area %.
C: Voids were observed and their proportion 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 bleeding 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 amount of bleeding. 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]
Bleeding amount evaluation was performed on those evaluated as "A" or "B" in the embeddability evaluation. An evaluation sample for bleeding 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 amount of bleeding. The results are shown in Tables 1 and 2.

Figure 2023017948000006
Figure 2023017948000006

Figure 2023017948000007
Figure 2023017948000007

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 suppressed bleeding while maintaining good embeddability compared to Comparative Examples 1 to 3 not containing it. was made. Further, from Examples 4 to 8 in Table 2, it was found that the same tendency was observed even when epoxy resins having other alicyclic rings were used. From these results, it was confirmed that the adhesive composition according to the present invention can suppress bleeding while having good embedding properties during 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 the above results show, the adhesive composition according to the present invention has good embedding properties during thermocompression bonding and can suppress bleeding. 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。 DESCRIPTION OF SYMBOLS 10... Film adhesive, 14... Substrate, 20... Base material, 30... Protective film, 41... Adhesive, 42... Sealing material, 84, 94... Circuit pattern, 88... First wire, 90... Organic substrate , 98... second wire, 100, 110... adhesive sheet, 200... semiconductor device, Wa... first semiconductor element, Waa... second semiconductor element.

Claims (14)

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み、
前記脂環式環を有するエポキシ樹脂が下記一般式（１ａ）で表されるエポキシ樹脂であり、
前記熱硬化性樹脂及び前記硬化剤の合計の含有量が、接着剤組成物全量を基準として、３０～５５質量％である、接着剤組成物。
Figure 2023017948000008
［式（１ａ）中、ｎ１は１～１０の整数を示す。］ containing a thermosetting resin, a curing agent, and an elastomer,
The thermosetting resin contains an epoxy resin having an alicyclic ring,
The epoxy resin having the alicyclic ring is an epoxy resin represented by the following general formula (1a),
The adhesive composition, wherein the total content of the thermosetting resin and the curing agent is 30 to 55% by mass based on the total amount of the adhesive composition.
Figure 2023017948000008
[In the formula (1a), n1 represents an integer of 1 to 10. ] 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。 2. The adhesive composition of claim 1, wherein said curing agent comprises a phenolic 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。 3. The adhesive composition according to claim 1 or 2, wherein said elastomer comprises an acrylic resin. 前記脂環式環を有するエポキシ樹脂の含有量が、前記熱硬化性樹脂の全量を基準として、５０～１００質量％である、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, wherein the content of the epoxy resin having an alicyclic ring is 50 to 100% by mass based on the total amount of the thermosetting resin. . 前記熱硬化性樹脂が、前記熱硬化性樹脂の全量を基準として、５０～１００質量％の前記脂環式環を有するエポキシ樹脂と、０～５０質量％の脂環式環を有しない芳香族エポキシ樹脂とから構成される、請求項１～４のいずれか一項に記載の接着剤組成物。 The thermosetting resin contains 50 to 100% by mass of the epoxy resin having the alicyclic ring and 0 to 50% by mass of the aromatic having no alicyclic ring, based on the total amount of the thermosetting resin. The adhesive composition according to any one of claims 1 to 4, comprising an epoxy resin. 前記脂環式環を有するエポキシ樹脂の含有量が、接着剤組成物全量を基準として、５質量％以上である、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, wherein the content of the epoxy resin having an alicyclic ring is 5% by mass or more based on the total amount of the adhesive composition. 無機フィラーをさらに含有し、
前記無機フィラーの含有量が、前記熱硬化性樹脂、前記硬化剤、及び前記エラストマーの総量１００質量部に対して、１０～９０質量部である、請求項１～６のいずれか一項に記載の接着剤組成物。 Further containing an inorganic filler,
The content of the inorganic filler is 10 to 90 parts by mass with respect to the total amount of 100 parts by mass of the thermosetting resin, the curing agent, and the elastomer, according to any one of claims 1 to 6. adhesive composition. 硬化促進剤をさらに含有する、請求項１～７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 7, further comprising a curing accelerator. 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、前記第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、前記第２の半導体素子を圧着すると共に前記第１のワイヤ及び前記第１の半導体素子を埋め込むために用いられる、請求項１～８のいずれか一項に記載の接着剤組成物。 A semiconductor device in which a first semiconductor element is wire-bonded onto a substrate via a first wire, and a second semiconductor element is crimped onto the first semiconductor element, wherein The adhesive composition according to any one of claims 1 to 8, which is used for crimping a semiconductor element and embedding the first wire and the first semiconductor element. 請求項１～９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 adhesive obtained by forming the adhesive composition according to any one of claims 1 to 9 into a film. 基材と、
前記基材上に設けられた、請求項１０に記載のフィルム状接着剤と、
を備える、接着シート。 a substrate;
The film adhesive according to claim 10 provided on the substrate;
an adhesive sheet. 前記基材がダイシングテープである、請求項１１に記載の接着シート。 12. The adhesive sheet according to claim 11, wherein said substrate 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１１又は１２に記載の接着シート。 The adhesive sheet according to claim 11 or 12, further comprising a protective film laminated on the surface of the film 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１０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のワイヤ及び前記第１の半導体素子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 the first semiconductor element to the substrate via a first wire;
A laminating step of applying the film adhesive according to claim 10 to one side of the second semiconductor element;
Die bonding for embedding the first wire and the first semiconductor element in the film-like adhesive by crimping the second semiconductor element to which the film-like adhesive is attached through the film-like adhesive. process and
A method of manufacturing a semiconductor device, comprising:
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