JPWO2010013406A1 - 半導体封止用樹脂組成物、およびこれを用いる半導体装置 - Google Patents
半導体封止用樹脂組成物、およびこれを用いる半導体装置 Download PDFInfo
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- JPWO2010013406A1 JPWO2010013406A1 JP2010522599A JP2010522599A JPWO2010013406A1 JP WO2010013406 A1 JPWO2010013406 A1 JP WO2010013406A1 JP 2010522599 A JP2010522599 A JP 2010522599A JP 2010522599 A JP2010522599 A JP 2010522599A JP WO2010013406 A1 JPWO2010013406 A1 JP WO2010013406A1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
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Abstract
Description
(一般式(2)において、R5、R6、R8およびR9は、互いに独立して、水素原子、または炭素数1〜6の炭化水素基であり、R4およびR7は、互いに独立して、炭素数1〜6の炭化水素基であり、bは、0〜3の整数であり、cは0〜4の整数である)
エポキシ樹脂(B)と、
無機充填剤(C)と、
を含む、半導体封止用樹脂組成物が提供される。
前記フェノール樹脂(A)以外の硬化剤をさらに含み、前記フェノール樹脂(A)が全硬化剤中に15質量%以上、100質量%以下含み得る。
エポキシ樹脂(B)と、
無機充填剤(C)と、
(i)極性基を有さないために、アルデヒド類との重合反応性が極めて低い。
(ii)一般式(5)で表される化合物(芳香族架橋基)との反応が可能である。
(iii)比較的かさ高いアルキル基による立体障害のため、一般式(5)で表される化合物との反応において、分子鎖の延長がほとんど起こらない。
したがって、アルキル置換芳香族化合物は、分子鎖の片末端、または両末端に結合してフェノール樹脂の分子鎖延長・成長を抑制する。これにより、得られるフェノール樹脂の流動性の向上に寄与する。
(第1の製法)
フェノール化合物1モルに対して、一般式(5)で表される化合物とアルデヒド類とを合計0.2〜0.8モル、アルキル置換芳香族化合物を0.05〜0.25モル、蟻酸、シュウ酸、p−トルエンスルホン酸、塩酸、硫酸、燐酸、酢酸、ルイス酸などの酸性触媒0.01〜0.05モルを50〜200℃の温度で、窒素フローにより発生ガスおよび水分を系外へ排出しながら、2〜20時間反応させ、反応終了後に残留するモノマーを減圧蒸留、水蒸気蒸留などの方法で留去することによって得ることができる。また、反応操作として、フェノール化合物と一般式(5)で表される化合物とアルデヒド類とを、酸性触媒を用いて縮合反応させながら、反応の中盤から終盤にかけてアルキル置換芳香族化合物を反応系に添加する方法をとってもよい。この場合、反応の進行はアルキル置換芳香族化合物とフェノールとの反応で副生成する水、ハロゲン化水素、アルコールのガスの発生状況や、あるいは反応途中の生成物をサンプリングしてゲルパーミエーションクロマトグラフ法により分子量で確認することもできる。
なお、フェノール樹脂(A)中の一般式(1)および一般式(2)の構造単位の比率は、使用した原料の比率をほぼ反映する。
一般式(35)で表されるアルキル置換芳香族化合物1モルに対して、アルデヒド類を1〜2.5モル、 触媒として水酸化ナトリウム、水酸化カリウムなどのアルカリ金属触媒、またはパラトルエンスルホン酸、キシレンスルホン酸、硫酸などの強酸を0.1〜2.5モル加えて、アルカリ金属触媒の場合には5〜80℃の温度で、酸性触媒の場合には100〜150℃の温度で、0.5〜5時間反応して反応中間体を得る。次いで、一般式(33)で表される化合物0.2〜5モル及びフェノール化合物1〜20モル、シュウ酸、p−トルエンスルホン酸、メタンスルホン酸、塩酸、硫酸、燐酸、酢酸、ルイス酸などの酸性触媒0.005〜0.05モルを加えて50〜200℃の温度にて窒素フローにより発生ガスを系外へ排出しながら、2〜20時間共縮合反応させ、反応終了後に残留するモノマー及び水分を減圧蒸留、水蒸気蒸留などの方法で留去することによって得ることができる。一般式(33)においてXがハロゲン原子である場合、微量の水分の存在に起因して発生するハロゲン化水素を酸触媒として用いることができる。
1)フェニレン骨格を有するフェノールアラルキル樹脂と同様の構造であって、フェニレン骨格の水素原子の一部が炭素数1〜6の炭化水素基で置換された樹脂
2)フェニレン骨格を有するフェノールアラルキル樹脂とフェノールノボラック型樹脂を共重合したフェノール樹脂と同様の構造であって、フェニレン骨格の水素原子の一部が炭素数1〜6の炭化水素基で置換された樹脂
3)フェニレン骨格を有するフェノールアラルキル樹脂
4)フェノールノボラック型樹脂
5)フェニレン骨格を有するフェノールアラルキルとフェノールノボラック型を共重合したフェノール樹脂
6)上記の1)〜5)のフェノール樹脂で、分子の末端部又はヒドロキシフェニル基の置換基に、炭素数1〜6の炭化水素基が1〜4個置換したフェニル基が、メチレン基またはパラキシリレン基を介して結合した重合体
フェノール樹脂1:フェノール(関東化学製特級試薬、フェノール、融点40.9℃、分子量94、純度99.3%)100質量部、p−キシリレングリコール(東京化成工業製p−キシリレングリコール、融点118℃、分子量138、純度98%)34.5質量部、およびp−トルエンスルホン酸一水和物(和光純薬工業製p−トルエンスルホン酸、分子量190、純度99%)0.5質量部をセパラブルフラスコに秤量し、窒素置換しながら加熱し、溶融の開始に併せて攪拌を開始した。系内が150℃に達したのを確認してから、ホルムアルデヒド37%水溶液(和光純薬工業製ホルマリン37%)13.5質量部を30分かけて添加した。系内の温度を145℃から155℃の範囲を維持しながら90分間反応させた後、系内へ1,3,5−トリメチルベンゼン(東京化成工業製鹿特級試薬、沸点165℃、分子量120、純度99%)22.5質量部を30分かけて添加しながら、反応系の温度を下げ、120℃〜130℃の範囲を維持しながら、さらに240分間反応させた。上記のホルムアルデヒドの添加開始から反応終了までの間、反応によって系内に発生、または、ホルマリン添加に伴い系内に混入した水分については、窒素気流によって系外へ排出した。反応終了後、150℃2mmHgの減圧条件で未反応成分を留去し、ついでトルエン200質量部を添加し、均一溶解させた後、分液漏斗に移し、蒸留水150質量部を加えて振とうした後に、水層を棄却する操作(水洗)を洗浄水が中性になるまで繰り返し行った後、油層を125℃減圧処理することによってトルエン、残留未反応成分などの揮発成分を留去し、下記式(12)、式(13)および式(14)で表される重合体の混合物であるフェノール樹脂1(水酸基当量159、軟化点67℃、150℃におけるICI粘度0.65dPa・s)を得た。得られたフェノール樹脂1の、GPC分析とFD−MS分析を行った結果、下記式(12)、式(13)および式(14)で表される重合体の質量比は、それぞれ、63.2質量%、34.6質量%、2.2質量%であり、下記式(12)、式(13)および式(14)におけるa1〜a3、b1〜b3の平均値は、a1=1.04、a2=0.94、a3=1.45、b1=0.92、b2=0.79、b3=0.60であった。フェノール樹脂1のGPCチャートを図2に、FD−MSチャートを図3に示す。
フェノール樹脂1のGPC測定は、次の条件で行った。フェノール樹脂1の試料20mgに溶剤テトラヒドロフラン(THF)を6ml加えて十分溶解しGPC測定に供した。GPCシステムは、WATERS社製モジュールW2695、東ソー株式会社製のTSK GUARDCOLUMN HHR−L(径6.0mm、管長40mm、ガードカラム)、東ソー株式会社製のTSK−GEL GMHHR−L(径7.8mm、管長30mm、ポリスチレンジェルカラム)2本、WATERS社製示差屈折率(RI)検出器W2414を直列に接続したものを用いた。ポンプの流速は0.5ml/分、カラム及び示差屈折率計内温度を40℃とし、測定溶液を100μlインジェクターより注入して測定を行った。
フェノール樹脂1のFD−MS測定は次の条件で行なった。フェノール樹脂1の試料10mgに溶剤ジメチルスルホキシド(DMSO)1gを加えて十分溶解したのち、FDエミッターに塗布の後、測定に供した。FD−MSシステムは、イオン化部に日本電子株式会社製のMS−FD15Aを、検出器に日本電子株式会社製のMS−700機種名二重収束型質量分析装置とを接続して用い、検出質量範囲(m/z)50〜2000にて測定した。
内径29mm、高さ10cmのポリプロピレン製の円筒容器内に、予め5℃に冷却した顆粒状のフェノール樹脂を20g入れ、円筒容器内に外形29mm・質量200gのピストンを挿入し、所定温度に設定した恒温槽内で所定時間垂直に立てた状態でフェノール樹脂に荷重を与え、その後に円筒容器を逆さまにしてフェノール樹脂を取り出したとき、もとの顆粒状で容器から容易に取り出すことが出来たものを◎、ピストンの内部形状を保つが手で容易にほぐれる場合は○、ピストンの内部形状のまま手でほぐれない場合は×、樹脂が溶融して取り出すことが出来ない場合を××とした。フェノール樹脂1、2、A,Bは、三井化学製XLC−3Lと比較して、低粘度でありながらブロッキング性に優れる結果であった。
以下のエポキシ樹脂1〜9を使用した。
無機充填剤としては、電気化学工業製溶融球状シリカFB560(平均粒径30μm)100質量部、アドマテックス製合成球状シリカSO−C2(平均粒径0.5μm)6.5質量部、アドマテックス製合成球状シリカSO−C5(平均粒径30μm)7.5質量部のブレンドを使用した。
以下の硬化促進剤1〜5を使用した。
化合物Eとして、下記式(24)で表される化合物(東京化成工業株式会社製、2,3−ナフタレンジオール、純度98%)を使用した。
以下のシランカップリング剤1〜3を使用した。
シランカップリング剤1:γ−メルカプトプロピルトリメトキシシラン(信越化学工業株式会社製、KBM−803)。
シランカップリング剤2:γ−グリシドキシプロピルトリメトキシシラン(信越化学工業株式会社製、KBM−403)。
シランカップリング剤3:N−フェニル−3−アミノプロピルトリメトキシシラン(信越化学工業株式会社製、KBM−573)。
着色剤として、三菱化学工業株式会社製のカーボンブラック(MA600)を使用した。
離型剤として、日興ファイン株式会社製のカルナバワックス(ニッコウカルナバ、融点83℃)を使用した。
以下の難燃剤1〜2を使用した。
難燃剤1:水酸化アルミニウム(住友化学株式会社製、CL310)
難燃剤2:水酸化マグネシウム・水酸化亜鉛固溶体複合金属水酸化物(タテホ化学工業株式会社製、エコーマグZ−10)
スパイラルフロー:低圧トランスファー成形機(コータキ精機株式会社製、KTS−15)を用いて、EMMI−1−66に準じたスパイラルフロー測定用金型に、175℃、注入圧力6.9MPa、保圧時間120秒の条件でエポキシ樹脂組成物を注入し、流動長を測定した。スパイラルフローは、流動性のパラメータであり、数値が大きい方が、流動性が良好である。単位はcm。
以下の成分をミキサーを用いて、常温で混合し、80℃〜100℃の加熱ロールで溶融混練し、その後冷却し、次いで粉砕して、半導体封止用樹脂組成物を得た。
フェノール樹脂1 5.45質量部
エポキシ樹脂1 7.55質量部
無機充填剤 86質量部
硬化促進剤1 0.4質量部
シランカップリング剤1 0.1質量部
シランカップリング剤2 0.1質量部
着色剤 0.3質量部
離型剤 0.1質量部
得られた半導体封止用樹脂組成物を、評価した。評価結果を表3、表4に示す。
表3、表4の配合に従い、実施例1と同様にしてエポキシ樹脂組成物を製造し、評価した。評価結果を表3、表4に示す。
表5〜8の配合に従い、実施例1と同様にしてエポキシ樹脂組成物を製造し、評価した。評価結果を表5〜8に示す。
Claims (21)
- 下記一般式(1)および一般式(2)で表される構造単位を含み、少なくとも一方の末端に、少なくとも1つの炭素数1〜3のアルキル基を有する芳香族基を有する、1又は2以上の成分からなる重合体(A0)を含むフェノール樹脂(A)と;
エポキシ樹脂(B)と、
無機充填剤(C)と、
を含む、半導体封止用樹脂組成物。 - 前記フェノール樹脂(A)は、下記一般式(31)および一般式(32)で表される構造単位を有する、1又は2以上の成分からなる重合体(A1)を含み、重合体(A0)及び重合体(A1)の前記成分の一部または全部が同じであってもよい、請求項1に記載の半導体封止用樹脂組成物。
- 電界脱離質量分析による測定で、重合体(A1)に該当する重合体の相対強度の合計が、前記フェノール樹脂(A)の合計相対強度に対して10%以上、80%以下含まれることを特徴とする請求項2に記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)が、一般式(31)で表される構造単位を含み、かつ一般式(32)で表される構造単位を含まない重合体からなる成分(A2)をさらに含むことを特徴とする請求項2または3に記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)が、一般式(32)で表される構造単位を含み、一般式(31)で表される構造単位を含まない重合体からなる成分(A3)をさらに含むことを特徴とする請求項2乃至4いずれかに記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)全体における一般式(31)で表される構造単位の合計の数と、一般式(32)で表される構造単位の合計の数との比が30/70〜95/5であることを特徴とする請求項2乃至5いずれかに記載の半導体封止用樹脂組成物。
- 一般式(32)で表される構造単位におけるR56がメチル基であり、bが1〜3であることを特徴とする請求項2乃至6いずれかに記載の半導体封止用樹脂組成物。
- 少なくとも1つの炭素数1〜3のアルキル基を有する前記芳香族基は、トリメチルフェニル基である、請求項1に記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)は、下記一般式(3)で表される重合体を含む、請求項1または8に記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)は、下記一般式(4)で表される重合体を含む、請求項1、9または10いずれかに記載の半導体封止用樹脂組成物。
- 前記フェノール樹脂(A)以外の硬化剤をさらに含み、前記フェノール樹脂(A)が全硬化剤中に15質量%以上、100質量%以下含まれることを特徴とする請求項1乃至10いずれかに記載の半導体封止用樹脂組成物。
- 前記エポキシ樹脂(B)が、ビフェニル型エポキシ樹脂、ビスフェノール型エポキシ樹脂、スチルベン型エポキシ樹脂、アントラセンジオール型エポキシ樹脂、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、トリフェノールメタン型エポキシ樹脂、アルキル変性トリフェノールメタン型エポキシ樹脂、フェニレン骨格を有するフェノールアラルキル型エポキシ樹脂、ビフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂、フェニレン骨格を有するナフトールアラルキル型エポキシ樹脂、ジヒドロキシナフタレン型エポキシ樹脂、ジヒドロキシナフタレンの2量体をグリシジルエーテル化して得られるエポキシ樹脂、メトキシナフタレン骨格を有するノボラック型エポキシ樹脂、トリグリシジルイソシアヌレート、モノアリルジグリシジルイソシアヌレート、ジシクロペンタジエン変性フェノール型エポキシ樹脂からなる群から選択される少なくとも1種のエポキシ樹脂であることを特徴とする請求項1乃至11いずれかに記載の半導体封止用樹脂組成物。
- 前記無機充填剤(C)の含有量が80質量%以上、93質量%以下であることを特徴とする請求項1乃至12いずれかに記載の半導体封止用樹脂組成物。
- 硬化促進剤(D)をさらに含む、請求項1乃至13いずれかに記載の半導体封止用樹脂組成物。
- 前記硬化促進剤(D)は、テトラ置換ホスホニウム化合物、ホスホベタイン化合物、ホスフィン化合物とキノン化合物との付加物およびホスホニウム化合物とシラン化合物との付加物から選択される少なくとも1種を含む、請求項14に記載の半導体封止用樹脂組成物。
- 芳香環を構成する2個以上の隣接する炭素原子にそれぞれ水酸基が結合した化合物(E)をさらに含むことを特徴とする請求項1乃至15いずれかに記載の半導体封止用樹脂組成物。
- カップリング剤(F)をさらに含むことを特徴とする請求項1乃至16いずれかに記載の半導体封止用樹脂組成物。
- 前記カップリング剤(F)が2級アミノ基を有するシランカップリング剤を含むことを特徴とする請求項17に記載の半導体封止用樹脂組成物。
- 無機系難燃剤をさらに含むことを特徴とする請求項1乃至18いずれかに記載の半導体封止用樹脂組成物。
- 前記無機系難燃剤が、金属水酸化物、または複合金属水酸化物を含むことを特徴とする請求項19に記載の半導体封止用樹脂組成物。
- 半導体素子を、請求項1乃至20いずれかに記載の半導体封止用樹脂組成物で封止して得られる、半導体装置。
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JP5651968B2 (ja) * | 2010-03-02 | 2015-01-14 | 住友ベークライト株式会社 | 半導体封止用樹脂組成物及び半導体装置 |
JP5868573B2 (ja) * | 2010-03-02 | 2016-02-24 | 住友ベークライト株式会社 | 半導体封止用樹脂組成物及び半導体装置 |
JP5573344B2 (ja) * | 2010-05-12 | 2014-08-20 | 住友ベークライト株式会社 | 封止用樹脂組成物及び電子部品装置 |
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CN102558769B (zh) * | 2010-12-31 | 2015-11-25 | 第一毛织株式会社 | 用于封装半导体器件的环氧树脂组合物以及由该环氧树脂组合物封装的半导体器件 |
JP2013023661A (ja) * | 2011-07-25 | 2013-02-04 | Nitto Denko Corp | 半導体封止用エポキシ樹脂組成物およびそれを用いた半導体装置 |
WO2014050789A1 (ja) * | 2012-09-28 | 2014-04-03 | Dic株式会社 | エポキシ化合物、その製造方法、エポキシ樹脂組成物およびその硬化物 |
KR101518502B1 (ko) | 2012-12-26 | 2015-05-11 | 제일모직주식회사 | 반도체 소자 밀봉용 에폭시 수지 조성물 및 이를 사용하여 밀봉된 반도체 소자 |
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TWI667746B (zh) * | 2018-04-03 | 2019-08-01 | 南茂科技股份有限公司 | 半導體封裝結構及其製造方法 |
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