JP6002857B1 - インクジェット用光及び熱硬化性接着剤、半導体装置の製造方法及び電子部品 - Google Patents
インクジェット用光及び熱硬化性接着剤、半導体装置の製造方法及び電子部品 Download PDFInfo
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- JP6002857B1 JP6002857B1 JP2015548085A JP2015548085A JP6002857B1 JP 6002857 B1 JP6002857 B1 JP 6002857B1 JP 2015548085 A JP2015548085 A JP 2015548085A JP 2015548085 A JP2015548085 A JP 2015548085A JP 6002857 B1 JP6002857 B1 JP 6002857B1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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Abstract
Description
上記光硬化性化合物は、光硬化性反応基を有する化合物である。上記光硬化性化合物としては、(メタ)アクリロイル基を有する硬化性化合物、ビニル基を有する硬化性化合物及びマレイミド基を有する硬化性化合物等が挙げられる。硬化した接着剤層をより一層高精度に形成する観点からは、上記光硬化性化合物の上記光硬化性反応基は、(メタ)アクリロイル基であることが好ましく、上記光硬化性化合物は、(メタ)アクリロイル基(1個以上)を有することが好ましい。上記光硬化性化合物は、1種のみが用いられてもよく、2種以上が併用されてもよい。
接着剤層の厚み精度をより一層高め、更に接着剤層にボイドをより一層生じ難くし、冷熱サイクル等の信頼性を向上させる観点からは、上記接着剤は、光及び熱硬化性化合物を含むことが好ましい。上記光及び熱硬化性化合物としては、各種の光硬化性官能基(光硬化性反応基)と各種の熱硬化性官能基とを有する化合物が挙げられる。硬化した接着剤層をより一層高精度に形成する観点からは、上記光及び熱硬化性化合物の上記光硬化性反応基は、(メタ)アクリロイル基であることが好ましい。硬化した接着剤層をより一層高精度に形成する観点からは、上記光及び熱硬化性化合物は、(メタ)アクリロイル基と環状エーテル基又は環状チオエーテル基とを有することが好ましく、また(メタ)アクリロイル基と環状エーテル基とを有することが好ましく、(メタ)アクリロイル基とエポキシ基とを有することが好ましい。上記光及び熱硬化性化合物は、環状チオエーテル基を有していてもよい。上記光及び熱硬化性化合物は、1種のみが用いられてもよく、2種以上が併用されてもよい。
上記熱硬化性化合物としては、環状エーテル基を有する熱硬化性化合物、及びチイラン基を有する熱硬化性化合物等が挙げられる。硬化した接着剤層をより一層高精度に形成する観点からは、上記熱硬化性化合物は、環状エーテル基又はチイラン基を有する熱硬化性化合物であることが好ましく、エポキシ基又はチイラン基を有する熱硬化性化合物であることがより好ましく、また環状エーテル基を有する熱硬化性化合物であることも好ましく、エポキシ基を有する熱硬化性化合物(エポキシ化合物)であることが特に好ましい。上記熱硬化性化合物は、チイラン基を有する熱硬化性化合物であってもよい。硬化した接着剤層をより一層高精度に形成する観点からは、上記熱硬化性化合物が、エポキシ基又はチイラン基を有する熱硬化性化合物であり、上記光及び熱硬化性化合物が、(メタ)アクリロイル基を有する光及び熱硬化性化合物であることが好ましい。上記熱硬化性化合物は、1種のみが用いられてもよく、2種以上が併用されてもよい。
上記光重合開始剤としては、光ラジカル重合開始剤及び光カチオン重合開始剤等が挙げられる。上記光重合開始剤は、光ラジカル重合開始剤であることが好ましい。上記光重合開始剤は、1種のみが用いられてもよく、2種以上が併用されてもよい。
上記熱硬化剤としては、有機酸、アミン化合物、アミド化合物、ヒドラジド化合物、イミダゾール化合物、イミダゾリン化合物、フェノール化合物、ユリア化合物、ポリスルフィッド化合物及び酸無水物等が挙げられる。上記熱硬化剤として、アミン−エポキシアダクトなどの変性ポリアミン化合物を用いてもよい。これら以外の熱硬化剤を用いてもよい。上記熱硬化剤は、1種のみが用いられてもよく、2種以上が併用されてもよい。
上記硬化促進剤としては、第三級アミン、イミダゾール、第四級アンモニウム塩、第四級ホスホニウム塩、有機金属塩、リン化合物及び尿素系化合物等が挙げられる。
上記接着剤は溶剤を含まないか又は含む。上記接着剤は、溶剤を含んでいてもよく、含んでいなくてもよい。接着剤層の厚み精度をより一層高め、更に接着剤層にボイドをより一層生じ難くする観点からは、上記接着剤における溶剤の含有量は少ないほどよい。
上記接着剤はフィラーを含まないか又は含む。上記接着剤は、フィラーを含んでいてもよく、含んでいなくてもよい。接着剤層の厚み精度をより一層高め、更に接着剤層にボイドをより一層生じ難くする観点からは、上記接着剤におけるフィラーの含有量は少ないほどよい。さらに、上記接着剤におけるフィラーの含有量が少ないほど、インクジェット装置による吐出不良の発生が抑えられる。
上記接着剤は、他の成分を含んでいてもよい。他の成分としては特に限定されないが、カップリング剤等の接着助剤、顔料、染料、レベリング剤、消泡剤、及び重合禁止剤等が挙げられる。
以下、本発明の一実施形態に係るインクジェット用光及び熱硬化性接着剤を用いて得られる電子部品の他の具体例について説明する。
攪拌機、冷却機及び温度計を備えた2Lの反応機内に、エタノール250mLと、純水250mLと、チオシアン酸カリウム20gとを加え、チオシアン酸カリウムを溶解させ、第1の溶液を調製した。その後、容器内の温度を20〜25℃の範囲内に保持した。次に、20〜25℃に保持された容器内の第1の溶液を攪拌しながら、ビスフェノールA型エポキシ樹脂160gを5mL/分の速度で滴下した。滴下後、30分間さらに攪拌し、エポキシ化合物含有混合液を得た。次に、純水100mLと、エタノール100mLとを含む溶液に、チオシアン酸カリウム20gを溶解させた第2の溶液を用意した。得られたエポキシ化合物含有混合液に、得られた第2の溶液を5mL/分の速度で添加した後、30分攪拌した。攪拌後、純水100mLとエタノール100mLとを含む溶液に、チオシアン酸カリウム20gを溶解させた第2の溶液をさらに用意し、該第2の溶液を5mL/分の速度で容器内にさらに添加し、30分間攪拌した。その後、容器内の温度を10℃に冷却し、2時間攪拌し、反応させた。次に、容器内に飽和食塩水100mLを加え、10分間攪拌した。攪拌後、容器内にトルエン300mLをさらに加え、10分間攪拌した。その後、容器内の溶液を分液ロートに移し、2時間静置し、溶液を分離させた。分液ロート内の下方の溶液を排出し、上澄み液を取り出した。取り出された上澄み液にトルエン100mLを加え、攪拌し、2時間静置した。更に、トルエン100mLをさらに加え、攪拌し、2時間静置した。次に、トルエンが加えられた上澄み液に、硫酸マグネシウム50gを加え、5分間攪拌した。攪拌後、ろ紙により硫酸マグネシウムを取り除いて、溶液を分離した。真空乾燥機を用いて、分離された溶液を80℃で減圧乾燥することにより、残存している溶剤を除去した。このようにして、エポキシ基がチイラン基に置換されたチイラン基を有する25℃で液状の化合物(A)を得た。
チイラン基を有する化合物(A)の合成において、ビスフェノールA型エポキシ樹脂を4−ヒドロキシブチルアクリレートグリシジルエーテルに変更したこと以外は同様の操作を行い、エポキシ基がチイラン基に置換されたチイラン基を有する25℃で液状の化合物(B)を得た。
(接着剤Aの調製)
光硬化性化合物としてトリシクロデカンジメタノールジアクリレート(ダイセル・オルネクス社製「IRR−214K」)2重量部、ラウリルアクリレート(共栄社化学社製「L−A」)11重量部、光及び熱硬化性化合物として4−ヒドロキシブチルアクリレートグリシジルエーテル(日本化成社製「4HBAGE」)41重量部、熱硬化性化合物としてビスフェノールA型エポキシ樹脂(新日鐵住金化学社製「YD−127」)20重量部、熱硬化剤としてテルペン骨格を有する酸無水物(三菱化学社製「YH306」)20重量部、硬化促進剤としてDBU−オクチル酸塩(サンアプロ社製「UCAT SA−102」)1重量部、及び光重合開始剤として2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1(BASF社製「IRGACURE369」)5重量部を均一に混合し、接着剤Aを得た。
(接着剤B〜Pの調製)
下記の表1に示す成分を下記の表2,3に示す配合量で配合したこと以外は上記接着剤Aの調製と同様にして、接着剤B〜Sを調製した。
(接着剤の25℃及び10rpmでの粘度)
JIS K2283に準拠して、E型粘度計(東機産業社製「TVE22L」)を用いて、25℃及び10rpmでの接着剤の粘度を測定した。粘度を下記の基準で評価した。
A:粘度が1600mPa・sを超える
B:粘度が1000mPa・sを超え、1600mPa・s以下
C:粘度が500mPa・sを超え、1000mPa・s以下
D:粘度が160mPa・s以上、500mPa・s以下
E:粘度が5mPa・s以上、160mPa・s未満
F:粘度が5mPa・s未満
厚みが20μmになるように基材の上にスピンコーターで接着剤を塗布した。この塗布物に対して、25℃で、照度計(ウシオ電機社製「UIT−201」)で測定した365nmでの照度が100mW/cm2になるように調節した露光装置(超高圧水銀ランプ、オーク製作所社製、「JL−4300−3」)を用いて10秒間光を照射した(積算光量1000mJ/cm2)。得られたBステージ化サンプルについて、ティー・エイ・インスツルメント社製の粘弾性測定装置ARESを用いて、25℃、測定プレート:直径8mmの平行プレート及び周波数1Hzの条件で弾性率の測定を行った。
配線の段差が5μmあるBGA基板(厚み0.3mm、市販のソルダーレジストが塗布されている、縦10mm×横10mmの半導体チップが置かれる場所が5行×16列で90か所設けられている)を用意した。上述した本発明の一実施形態に係る電子部品の製造方法に従って、図2(a)〜(e)に示す各工程を経て、接着剤層を形成した。上記接着剤を70℃で循環させながら、塗布する上記塗布工程と、上記第1の光照射工程(365nmを主波長とするUV−LEDランプ、100mW/cm2、0.1秒)とを繰り返して、厚み30μmの接着剤層を形成し、第2の光照射工程(超高圧水銀ランプ、100mW/cm2、10秒)で光硬化させた。その後、接着剤層上に、ダイボンド装置を用いて、半導体チップ(縦10mm×横10mm×厚み80μm)に見立てたシリコンベアチップを110℃で0.2MPaの条件で積層して、積層体を得た。シリコンベアチップを積層した後、光学顕微鏡(キーエンス社製「デジタルマイクロスコープVH−Z100」)を用いて接着剤層のはみ出しが100μm未満であることを確認した。得られた積層体を160℃のオーブン内に入れ、3時間加熱することで、熱硬化させることにより、90個の半導体装置(積層構造体)を得た。
○○:ボイドがほとんど観察されなかった
○:ボイドがわずかに観察された(使用上問題がない)
×:ボイドが観察された(使用上問題あり)
光学顕微鏡(キーエンス社製「デジタルマイクロスコープVH−Z100」)を用いて、ボイドの確認の評価で得られた半導体装置における半導体チップの移動を観察し、下記の基準で評価した。なお、半導体チップが移動している場合に、接着剤層の厚み精度が悪いことを確認した。
○:半導体チップの移動がほとんど観察されなかった(移動距離が20μm未満)
×:半導体チップの移動が観察された(移動距離が20μm以上)
ボイドの確認の評価で得られた半導体装置(90個)を85℃及び湿度85RH%に168時間放置して吸湿させた。その後、半田リフロー炉(プレヒート150℃×100秒、リフロー[最高温度260℃])に5サイクル通過させた。その吸湿リフロー試験を行った半導体装置を液槽式熱衝撃試験機(ESPEC社製「TSB−51」)を用いて、−55℃で5分間保持した後、150℃まで昇温し、150℃で5分間保持した後−50℃まで降温する過程を1サイクルとする冷熱サイクル試験を実施した。250サイクル、500サイクル及び1000サイクル後に半導体装置を取り出し、超音波探査映像装置(日立建機ファインテック社製「mi−scope hyper II」)を用いて、半導体装置の接着剤層の剥離を観察し、下記の基準で評価した。
○○:剥離していない
○:わずかに剥離している(使用上問題がない)
×:大きく剥離している(使用上問題あり)
1A…一次積層体
2…第1の電子部品本体
3…接着剤層(加熱後)
4…第2の電子部品本体
11,11X…インクジェット装置
12…接着剤層
12A…第1の光照射部により光が照射された接着剤層
12B…第2の光照射部により光が照射された接着剤層
13…第1の光照射部
14…第2の光照射部
21…インクタンク
22…吐出部
23,23X…循環流路部
23A…バッファタンク
23B…ポンプ
31…電子部品
32…多層の接着剤層(加熱後)
32A,32B,32C…接着剤層(加熱後)
51,71…半導体装置
52…積層構造体
53,53A…基板
53a…第1の接続端子
53b…第2の接続端子
54,61,72…接着剤層
55…第2の半導体ウェハ
55a,73a…接続端子
56,63,74…配線
62,73…第1の半導体ウェハ
62a…接続端子
Claims (15)
- 光及び熱硬化性化合物と、光硬化性化合物(前記光及び熱硬化性化合物を除く)と、熱硬化性化合物(前記光及び熱硬化性化合物を除く)と、光重合開始剤と、熱硬化剤とを含み、
前記光及び熱硬化性化合物が、4−ヒドロキシブチル(メタ)アクリレートグリシジルエーテルを含み、
接着剤100重量%中、前記光及び熱硬化性化合物の含有量が、0.5重量%以上、80重量%未満であり、
接着剤100重量%中、前記光硬化性化合物と前記光及び熱硬化性化合物との合計の含有量が、10重量%以上、80重量%以下であり、
365nmでの照度が100mW/cm2になるように積算光量1000mJ/cm2の光を接着剤に照射してBステージ化接着剤を得たときに、前記Bステージ化接着剤の25℃での弾性率が5.0×102Pa以上、8.0×104Pa以下である、インクジェット用光及び熱硬化性接着剤。 - 前記光硬化性化合物が、光硬化性反応基を1個有する光硬化性化合物と、光硬化性反応基を2個以上有する光硬化性化合物とを含む、請求項1に記載のインクジェット用光及び熱硬化性接着剤。
- 前記光硬化性反応基を1個有する光硬化性化合物の前記光硬化性反応基が(メタ)アクリロイル基であり、
前記光硬化性反応基を2個有する光硬化性化合物の前記光硬化性反応基が(メタ)アクリロイル基である、請求項2に記載のインクジェット用光及び熱硬化性接着剤。 - 前記光硬化性化合物の全体と、前記光及び熱硬化性化合物との合計100重量%中、前記光硬化性反応基を2個以上有する光硬化性化合物の含有量が0.1重量%以上、30重量%以下である、請求項2又は3に記載のインクジェット用光及び熱硬化性接着剤。
- 前記光硬化性反応基を1個有する光硬化性化合物が、2−エチルヘキシル(メタ)アクリレートを含む、請求項2〜4のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤。
- JIS K2283に準拠して測定された25℃及び10rpmでの粘度が5mPa・s以上、1600mPa・s以下である、請求項1〜5のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤。
- 溶剤を含まないか又は含み、
接着剤が前記溶剤を含む場合には、前記溶剤の含有量が1重量%以下である、請求項1〜6のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤。 - フィラーを含まないか又は含み、
接着剤が前記フィラーを含む場合には、前記フィラーの含有量が1重量%以下である、請求項1〜7のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤。 - 半導体素子搭載用の支持部材又は半導体素子の表面上に、インクジェット装置を用いて、請求項1〜8のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤を塗布して、接着剤層を形成する塗布工程と、
光の照射により前記接着剤層の硬化を進行させて、Bステージ化接着剤層を形成する工程と、
前記Bステージ化接着剤層の前記支持部材又は前記半導体素子側とは反対の表面上に、半導体素子を積層する工程と、
前記半導体素子の積層後に、前記Bステージ化接着剤層を熱硬化させる工程とを備える、半導体装置の製造方法。 - 半導体ウェハの表面上に、インクジェット装置を用いて、請求項1〜8のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤を吐出して、接着剤層を形成する塗布工程と、
光の照射により前記接着剤層の硬化を進行させて、Bステージ化接着剤層を形成する工程と、
前記Bステージ化接着剤層の前記半導体ウェハ側とは反対の表面上に、カバーガラスを積層して、積層体を得る工程と、
前記積層体における前記Bステージ化接着剤層を熱硬化させる工程と、
熱硬化後に前記積層体を切断する工程とを備える、半導体装置の製造方法。 - 前記Bステージ化接着剤層の25℃での弾性率を5.0×102Pa以上、8.0×104Pa以下にする、請求項9又は10に記載の半導体装置の製造方法。
- 前記インクジェット装置が、前記インクジェット用光及び熱硬化性接着剤が貯留されるインクタンクと、前記インクタンクと接続されておりかつ前記インクジェット用光及び熱硬化性接着剤が吐出される吐出部と、一端が前記吐出部に接続されており、他端が前記インクタンクに接続されており、かつ内部を前記インクジェット用光及び熱硬化性接着剤が流れる循環流路部とを有し、
前記塗布工程において、前記インクジェット装置内で、前記インクジェット用光及び熱硬化性接着剤を前記インクタンクから前記吐出部に移動させた後に、前記吐出部から吐出されなかった前記インクジェット用光及び熱硬化性接着剤を、前記循環流路部内を流して前記インクタンクに移動させることにより、前記インクジェット用光及び熱硬化性接着剤を循環させながら、塗布する、請求項9〜11のいずれか1項に記載の半導体装置の製造方法。 - 循環されている前記インクジェット用光及び熱硬化性接着剤の温度が40℃以上、100℃以下である、請求項12に記載の半導体装置の製造方法。
- 第1の電子部品本体と、第2の電子部品本体と、前記第1の電子部品本体と前記第2の電子部品本体とを接続している接着剤層とを備え、
前記接着剤層が、請求項1〜8のいずれか1項に記載のインクジェット用光及び熱硬化性接着剤の硬化物である、電子部品。 - 前記第1の電子部品本体が半導体素子搭載用の支持部材又は半導体素子であり、
前記第2の電子部品本体が半導体素子である、請求項14に記載の電子部品。
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