JP7059632B2 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP7059632B2 JP7059632B2 JP2017549537A JP2017549537A JP7059632B2 JP 7059632 B2 JP7059632 B2 JP 7059632B2 JP 2017549537 A JP2017549537 A JP 2017549537A JP 2017549537 A JP2017549537 A JP 2017549537A JP 7059632 B2 JP7059632 B2 JP 7059632B2
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- -1 naphthoquinone diazide compound Chemical class 0.000 claims description 50
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- 229910052802 copper Inorganic materials 0.000 claims description 36
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 12
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- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 9
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- 239000010936 titanium Substances 0.000 description 9
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
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- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 7
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
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- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 5
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- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 4
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Description
前記(a)樹脂が、ポリイミド前駆体、ポリアミド、ポリイミド、ポリベンゾオキサゾール、およびこれらの共重合体から選択される1種類以上の樹脂を含んでなり、
前記(b)酸化防止剤が、ヒンダードフェノール構造を有する酸化防止剤であり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を3つ以上有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
該分子量40以上の置換基が、アルコキシメチル基であることを特徴とする、樹脂組成物。
[2](a)樹脂、(b)酸化防止剤、(d)架橋剤を含有する樹脂組成物であって、
前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
前記ポリアミドと前記ポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量が2~50モル%の範囲内であることを特徴とする、樹脂組成物。
[3](a)樹脂、(b)酸化防止剤、(d)架橋剤を含有する樹脂組成物であって、
前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
前記ポリアミドが脂肪族基を有するジアミン由来の構造単位を有し、かつ、全ジアミン由来の構造単位100モル%に対する、前記脂肪族基を有するジアミン由来の構造単位の含有量が5~40モル%の範囲内であることを特徴とする、樹脂組成物。
[7]前記(a)樹脂が、一般式(2)で表される構造単位を有する、[1]~[6]のいずれかに記載の樹脂組成物。
[8]前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記ポリアミドが脂肪族基を有するジアミン由来の構造単位を有し、かつ、全ジアミン由来の構造単位100モル%に対する、前記脂肪族基を有するジアミン由来の構造単位の含有量が5~40モル%の範囲内である、[1]に記載の樹脂組成物。
前記ポリアミドと前記ポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量が2~50モル%の範囲内である、[1]に記載の樹脂組成物。
[11]さらに、(f)下記一般式(4)で表される構造単位を有する熱架橋剤を含有する、[1]~[10]のいずれかに記載の樹脂組成物。
[12][1]~[11]のいずれかに記載の樹脂組成物から形成された樹脂シート。
その上にシリコンチップと封止樹脂を配置する工程と、
その後、仮貼り材料が配置された支持基板と再配線を剥離する工程を含む、
半導体電子部品または半導体装置の製造方法。
前記(a)樹脂が、ポリイミド前駆体、ポリアミド、ポリイミド、ポリベンゾオキサゾール、およびこれらの共重合体から選択される1種類以上の樹脂を含んでなり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であることを特徴とする。
一般式(2)で表される構造単位において、エーテル基のもつ伸縮性により、硬化膜としたときに高伸度性を付与することができる。また、前記エーテル基の存在により、金属と錯形成や水素結合することができ、金属との高い密着性を得ることができる。
本発明において、肪族基を有するジアミンは、アルキル基、およびアルキルエーテル基から選ばれる少なくともひとつを有する有機基であって、これらは、主鎖が直鎖となっている非環化構造である方が、柔軟性および伸縮性が得られ、硬化膜としたときに低応力化、高伸度化を達成できるため好ましい。
一般式(2)で表される構造単位において、エーテル基のもつ伸縮性により、硬化膜としたときに高伸度性を付与することができる。また、前記エーテル基の存在により、金属と錯形成や水素結合することができ、金属との高い密着性を得ることができる。
また、一般式(2)で表される構造単位の数平均分子量は、150以上2,000以下が好ましい。一般式(2)で表される構造単位の数平均分子量は、柔軟性および伸縮性が得られるため、150以上が好ましく、600以上がより好ましく、900以上がさらに好ましい。また、一般式(2)で表される構造単位の数平均分子量は、アルカリ溶液への溶解性を維持することができるため、2,000以下が好ましく、1,800以下がより好ましく、1,500以下がさらに好ましい。
また、前記(a)樹脂100質量部に対する前記(d)架橋剤の含有量は15~70質量部の範囲内であることが好ましい。15質量部以上の場合、硬化膜の高密度化と酸化防止効果が得られ、信頼性評価後の伸度低下を大きく抑制できる。70質量部以下であると、硬化膜の伸度向上効果が得られ、膜のクラックを低減し、また、金属配線との密着性も向上させることができる。
上記構造の中でも、耐熱性と伸度向上を両立する点から、nは1~2、mは3~7であることが好ましい。
(a)樹脂の重量平均分子量(Mw)は、GPC(ゲルパーミエーションクロマトグラフィー)装置Waters2690-996(日本ウォーターズ(株)製)を用いて確認した。展開溶媒をN-メチル-2-ピロリドン(以降NMPと呼ぶ)として測定し、ポリスチレン換算で重量平均分子量(Mw)及び分散度(PDI=Mw/Mn)を計算した。
ワニスを、8インチのシリコンウエハ上に塗布現像装置ACT-8(東京エレクトロン(株)製)を用いてスピンコート法で膜厚が10.5μm~12μmとなるように塗布し、120℃で3分間のプリベークを行なった。露光機i線ステッパーDSW-8000(GCA社製)に円形のビアパターンの切られたレチクルをセットし、1500mJ/cm2の露光量で露光した。露光後、ACT-8の現像装置を用いて、2.38質量%のテトラメチルアンモニウム水溶液(以下TMAH、多摩化学工業(株)製)を用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、膜厚10μmのパターンを得た。パターンをフラットパネルディスプレイ顕微鏡MX61(オリンパス(株)製)を用い、倍率20倍で観察し、ビアパターンが解像している最小寸法を解像度とした。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で3.5℃/分で190℃まで昇温し、190℃で1時間加熱処理を行なった。温度が50℃以下になったところでウエハを取り出し、徐冷した後、8インチウエハを中央から左右2cm間隔で9点の膜厚をフラットパネルディスプレイ顕微鏡MX61(オリンパス(株)製)を用いて測定し、膜厚の最小値と最大値の差を膜厚の面内均一性とした。膜厚の面内均一性の値が0.15μm未満のものをきわめて良好(A)、0.15~0.4μm未満のものを良好(B)、0.4~0.8μm未難のものを可(C)、0.8μm以上のものを不良(D)とした。
(2)-2と同様のパターンを8インチウエハの中央から左右2cm間隔で9ショット作成し、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で3.5℃/分で190℃まで昇温し、190℃で1時間加熱処理を行なった。温度が50℃以下になったところでウエハを取り出し、徐冷した後、9ショットにおいて、それぞれ解像度のパターン寸法を走査型レーザー顕微鏡1LM21(レーザーテック(株)製)を用いて測定し、寸法の最小値と最大値の差をパターンの面内均一性とした。パターンの面内均一性の値が0.8μm未満のものをきわめて良好(A)、0.8~1.2μm未満のものを良好(B)、1.2~1.5μm未満のものを可(C)、1.5μm以上のものを不良(D)とした。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で3.5℃/分で190℃まで昇温し、190℃で1時間加熱処理を行なった。温度が50℃以下になったところでウエハを取り出し、徐冷した後、45質量%のフッ化水素酸に5分間浸漬することで、ウエハから樹脂組成物の膜を剥がした。この膜を幅1cm、長さ9cmの短冊状に切断し、テンシロンRTM-100((株)オリエンテック製)を用いて、室温23.0℃、湿度45.0%RH下で引張速度50mm/分で引っ張り、破断点伸度の測定を行なった。測定は1検体につき10枚の短冊について行ない、結果から上位5点の平均値を求めた。破断点伸度の値が80%以上のものをきわめて良好(A)、50%以上80%未満のものを良好(B)、25%以上50%未満のものを可(C)、25%未満のものを不良(D)とした。
ワニスを8インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT-8を用いてスピンコート法で塗布およびプリベークした後、イナートオーブンCLH-21CD-S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で3.5℃/分で190℃まで昇温し、190℃で1時間加熱処理を行なった。温度が50℃以下になったところでウエハを取り出し、徐冷した後、次に、熱サイクル試験機(以下TC装置)(タバイ・エスペック(株)製)を用いて、-45℃で15分間、125℃で15分間を1サイクルとして500サイクルの処理を行った。ウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハから樹脂組成物の膜を剥がした。この膜を幅1cm、長さ9cmの短冊状に切断し、テンシロンRTM-100((株)オリエンテック製)を用いて、室温23.0℃、湿度45.0%RH下で引張速度50mm/分で引っ張り、破断点伸度の測定を行なった。測定は1検体につき10枚の短冊について行ない、結果から上位5点の平均値を求めた。破断点伸度の値が50%以上のものをきわめて良好(A)、30%以上50%未満のものを良好(B)、15%以上30%未満のものを可(C)、15%未満のものを不良(D)とした。
シリコンウエハ上にチタン、銅をそれぞれ100nmの厚みでスパッタリングし、その後電解めっきにて銅めっき膜を施し、2μmの厚みで形成された金属材料層を表面に有する基板(銅めっき基板)とした。この基板上にワニスをスピンナ(ミカサ(株)製)を用いてスピンコート法で塗布し、次いでホットプレート(大日本スクリーン製造(株)製D-SPIN)を用いて120℃で3分ベークし、最終的に厚さ10μmのプリベーク膜を作製した。これらの膜をクリーンオーブン(光洋サーモシステム(株)製CLH-21CD-S)を用いて、窒素気流下(酸素濃度20ppm以下)、140℃で30分、次いでさらに昇温して190℃にて1時間キュアし、樹脂硬化膜を得た。硬化膜に片刃を使用して2mm間隔で10行10列の碁盤目状の切り込みをいれた。セロテープ(登録商標)による引き剥がしによって100マスのうち何マス剥がれたかを計数し、金属材料/樹脂硬化膜間の密着特性の評価を行なった。さらに、次に、TC装置を用いて、-45℃で15分間、125℃で15分間を1サイクルとして500サイクルの処理を行った後に、上記の引き剥がしテストを行なった。いずれの基板についても引き剥がしテストで剥がれ個数が0をきわめて良好(A)、1~20未満を良好(B)、20以上を不良(D)とした。
シリコンウエハ上に、直径60μmの銅ビアパターンが150μm間隔で、5μmの厚みで形成された銅パターンウエハを用意し、プラズマ処理装置((株)日立ハイテクインスツルメンツ製 、SPC-100B+H)を用いて、酸素流量50sccm、圧力20Pa、出力1200W、時間60 秒でプラズマエッチングを行った。
窒素気流下、250mlの三頸フラスコ中にイミダゾール27.2g(0.4モル)を入れ、塩化メチレン100gを入れて室温で攪拌した。これを-5℃以下に冷却し、4,4’-ジフェニルエーテルジカルボン酸ジクロリド29.5g(0.1モル)を100gの塩化メチレンに分散させた液体を、反応溶液の温度が0℃を越えないようにして1時間かけて滴下した。滴下後、室温にて反応溶液をさらに3時間攪拌し、反応中に生じた沈殿物を濾過した。濾過した沈殿物を純水で数回洗浄し、50℃の真空オーブンで100時間乾燥して、下記式で示される酸Aを得た。
乾燥窒素気流下、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン(以降BAHFと呼ぶ)(18.3g、0.05モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)、をNMP125gに溶解させた。ここに4,4’-オキシジフタル酸無水物(13.95g、0.045モル)をNMP25gとともに加えて、60℃で1時間攪拌し、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリイミド樹脂(A-1)の粉末を得た。このようにして得られた樹脂のイミド化率は97%であった。重量平均分子量は38,800、PDIは1.9であった。
乾燥窒素気流下、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン(以降BAHFと呼ぶ)(15.6g、0.043モル)、RT-1000(7.5g、0.0075モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)をNMP100gに溶解させた。ここに、酸A(13.51g、0.045モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)をNMP25gとともに加えて、85℃で3時間反応させた。反応終了後、室温まで冷却し、酢酸(13.20g、0.25モル)をNMP25gとともに加えて、室温で1時間攪拌した。攪拌終了後、溶液を水1.5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリアミド樹脂(A-2)の粉末を得た。重量平均分子量は32,600、PDIは1.9であった。
乾燥窒素気流下、BAHF(14.6g、0.040モル)、RT-1000(7.5g、0.0075モル)をNMP100gに溶解させた。ここに、酸A(11.26g、0.038モル)をNMP10gとともに加えて、85℃で3時間反応させた。その後、BAHF(1.0g、0.0025モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)をNMP5gとともに加え85℃で1時間反応させた後、4,4’-オキシジフタル酸無水物(2.33g、0.0075モル)をNMP5gとともに加え85℃で1時間反応させた。反応終了後、室温まで冷却し、酢酸(13.20g、0.25モル)をNMP25gとともに加えて、室温で1時間攪拌した。攪拌終了後、溶液を水1.5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリアミド-ポリイミド共重合樹脂(A-3)の粉末を得た。このようにして得られた樹脂のイミド化率は70%であった。重量平均分子量は32,600、PDIは1.9であった。ポリアミド由来の酸Aと、ポリイミド・ポリイミド前駆体由来由来の4,4’-オキシジフタル酸無水物の仕込み比、イミド化率の値から、ポリアミドとポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量は12%だった。
テトラヒドロフラン500ml、開始剤としてsec-ブチルリチウム0.01モルを加えた混合溶液に、p-t-ブトキシスチレンとスチレンをモル比3:1の割合で合計20gを添加し、3時間撹拌しながら重合させた。重合停止反応は反応溶液にメタノール0.1モルを添加して行った。次にポリマーを精製するために反応混合物をメタノール中に注ぎ、沈降した重合体を乾燥させたところ白色重合体が得られた。更に、アセトン400mlに溶解し、60℃で少量の濃塩酸を加えて7時間撹拌後、水に注ぎ、ポリマーを沈澱させ、p-t-ブトキシスチレンを脱保護してヒドロキシスチレンに変換し、洗浄乾燥したところ、精製されたp-ヒドロキシスチレンとスチレンの共重合体であるポリヒドロキシスチレン樹脂としてフェノール樹脂(A-4)が得られた。
4,4’-オキシジフタル酸二無水物(155.1g、0.5モル)を2l容量のセパラブルフラスコに入れ、2-ヒドロキシエチルメタクリレート125gとγ―ブチロラクトン400mlを入れて室温下で攪拌し、攪拌しながらピリジン81.5gを加えて反応混合物を得た。反応による発熱の終了後に室温まで放冷し、16時間放置した。
乾燥窒素気流下、BAHF(14.6g、0.040モル)、RT-1000(7.5g、0.0075モル)をNMP100gに溶解させた。ここに、酸A(13.06g、0.044モル)をNMP10gとともに加えて、85℃で3時間反応させた。その後、BAHF(1.0g、0.0025モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)をNMP5gとともに加え85℃で1時間反応させた後、4,4’-オキシジフタル酸無水物(0.47g、0.0015モル)をNMP5gとともに加え85℃で1時間反応させた。反応終了後、室温まで冷却し、酢酸(13.20g、0.25モル)をNMP25gとともに加えて、室温で1時間攪拌した。攪拌終了後、溶液を水1.5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリアミド-ポリイミド共重合樹脂(A-6)の粉末を得た。このようにして得られた樹脂のイミド化率は71%であった。重量平均分子量は32,300、PDIは1.9であった。ポリアミド由来の酸Aと、ポリイミド・ポリイミド前駆体由来由来の4,4’-オキシジフタル酸無水物の仕込み比、イミド化率の値から、ポリアミドとポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量は2%だった。
(合成例8)ポリアミド-ポリイミド共重合樹脂(A-7)
乾燥窒素気流下、BAHF(14.6g、0.040モル)、RT-1000(7.5g、0.0075モル)をNMP100gに溶解させた。ここに、酸A(6.76g、0.023モル)をNMP10gとともに加えて、85℃で3時間反応させた。その後、BAHF(1.0g、0.0025モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)をNMP5gとともに加え85℃で1時間反応させた後、4,4’-オキシジフタル酸無水物(6.93g、0.023モル)をNMP5gとともに加え85℃で1時間反応させた。反応終了後、室温まで冷却し、酢酸(13.20g、0.25モル)をNMP25gとともに加えて、室温で1時間攪拌した。攪拌終了後、溶液を水1.5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリアミド-ポリイミド共重合樹脂(A-7)の粉末を得た。このようにして得られた樹脂のイミド化率は82%であった。重量平均分子量は35,300、PDIは1.9であった。ポリアミド由来の酸Aと、ポリイミド・ポリイミド前駆体由来由来の4,4’-オキシジフタル酸無水物の仕込み比、イミド化率の値から、ポリアミドとポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量は45%だった。
乾燥窒素気流下、BAHF(14.6g、0.040モル)、RT-1000(7.5g、0.0075モル)をNMP100gに溶解させた。ここに、酸A(9.30g、0.03モル)をNMP10gとともに加えて、85℃で3時間反応させた。その後、BAHF(1.0g、0.0025モル)、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン(0.62g、0.0025モル)、5-ノルボルネン-2,3-ジカルボン酸(0.82g、0.005モル)をNMP5gとともに加え85℃で1時間反応させた後、4,4’-オキシジフタル酸無水物(9.30g、0.03モル)をNMP5gとともに加え85℃で1時間反応させた。反応終了後、室温まで冷却し、酢酸(13.20g、0.25モル)をNMP25gとともに加えて、室温で1時間攪拌した。攪拌終了後、溶液を水1.5Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリアミド-ポリイミド共重合樹脂(A-6)の粉末を得た。このようにして得られた樹脂のイミド化率は80%であった。重量平均分子量は35,500、PDIは1.9であった。ポリアミド由来の酸Aと、ポリイミド・ポリイミド前駆体由来由来の4,4’-オキシジフタル酸無水物の仕込み比、イミド化率の値から、ポリアミドとポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量は55%だった。
(a)樹脂として、上記樹脂(A-1)~(A-3)を用い、各樹脂(A-1)~(A-3)成分10gに対し、(b)成分、(c)成分、(d)成分、(e)成分、(f)成分を表1に示した所定量にて配合し、γ-ブチロラクトンを20g加えてワニスを作製した。
(a)樹脂成分の代わりに上記フェノール樹脂(A-4)を用いて、(A-4)成分10gに対し、(b)成分、(c)成分、(d)成分を表1に示した所定量にて配合し、γ-ブチロラクトンを20gを加えてワニスを作製した。
(a)樹脂として上記樹脂(A-5)を用い、樹脂(A-5)成分10gに対し、(b)成分、(c)成分、(d)成分、を表1に示した所定量にて配合し、(c)ナフトキノンジアジド化合物の変わりに重合開始剤(C-2)2.0gと光重合性化合物(C-3)2.0gを加え、γ-ブチロラクトンを20g加えてワニスを作製した。
(a)樹脂として上記樹脂(A-5)を用い、樹脂(A-5)成分10gに対し、(b)成分、(d)成分、を表1に示した所定量にて配合し、γ-ブチロラクトンを20g加えてワニスを作製した。
(a)樹脂として上記樹脂(A-5)を用い、樹脂(A-5)成分10gに対し、(b)成分を表1に示した所定量にて配合し、γ-ブチロラクトンを20g加えてワニスを作製した。
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属(Cr、Ti等)膜
6 金属配線(Al、Cu等)
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
11 封止樹脂
12 基板
13 絶縁膜
14 絶縁膜
15 金属(Cr、Ti等)膜
16 金属配線(Ag、Cu等)
17 金属配線(Ag、Cu等)
18 電極
19 封止樹脂
20 支持基板(ガラス基板、シリコンウェハ)
21 電極バッド(Cu)
22 絶縁膜
23 金属配線(Cu)
24 Cuポスト
25 ハンダバンプ
26 半導体チップ
27 TFT(薄膜トランジスタ)
28 配線
29 TFT絶縁層
30 平坦化層
31 ITO(透明電極)
32 基板
33 コンタクトホール
34 絶縁層
Claims (26)
- (a)樹脂、(b)酸化防止剤、(d)架橋剤を含有する樹脂組成物であって、
前記(a)樹脂が、ポリイミド前駆体、ポリアミド、ポリイミド、ポリベンゾオキサゾール、およびこれらの共重合体から選択される1種類以上の樹脂を含んでなり、
前記(b)酸化防止剤が、ヒンダードフェノール構造を有する酸化防止剤であり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を3つ以上有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
該分子量40以上の置換基が、アルコキシメチル基であることを特徴とする、樹脂組成物。 - (a)樹脂、(b)酸化防止剤、(d)架橋剤を含有する樹脂組成物であって、
前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
前記ポリアミドと前記ポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量が2~50モル%の範囲内であることを特徴とする、樹脂組成物。 - (a)樹脂、(b)酸化防止剤、(d)架橋剤を含有する樹脂組成物であって、
前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記(d)架橋剤が、一分子中にフェノール性水酸基を有し、かつ前記フェノール性水酸基の両オルト位に分子量40以上の置換基を有する架橋剤であり、
前記ポリアミドが脂肪族基を有するジアミン由来の構造単位を有し、かつ、全ジアミン由来の構造単位100モル%に対する、前記脂肪族基を有するジアミン由来の構造単位の含有量が5~40モル%の範囲内であることを特徴とする、樹脂組成物。 - 前記(a)樹脂が、フェノール性水酸基を有するアルカリ可溶性樹脂であり、さらに、(c)ナフトキノンジアジド化合物を含有する請求項1~3のいずれかに記載の樹脂組成物。
- 前記(d)架橋剤が、一分子中にフェノール性水酸基を3以上有する架橋剤である、請求項2または3に記載の樹脂組成物。
- 前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記ポリアミドが脂肪族基を有するジアミン由来の構造単位を有し、かつ、全ジアミン由来の構造単位100モル%に対する、前記脂肪族基を有するジアミン由来の構造単位の含有量が5~40モル%の範囲内である、請求項1に記載の樹脂組成物。 - 前記(a)樹脂が、少なくともポリアミドとポリイミドの共重合体を含んでなり、
前記ポリアミドと前記ポリイミドの構造単位合計100モル%に対する、前記ポリイミドの構造単位の含有量が2~50モル%の範囲内である、請求項1に記載の樹脂組成物。 - 請求項1~11のいずれかに記載の樹脂組成物から形成された樹脂シート。
- 請求項1~11のいずれかに記載の樹脂組成物を硬化した硬化膜。
- 請求項12に記載の樹脂シートを硬化した硬化膜。
- 破断点伸度が50%以上である、請求項13または14に記載の硬化膜。
- 請求項4~11のいずれかに記載の樹脂組成物を基板上に塗布し、または請求項12に記載の樹脂シートを基板上にラミネートし、乾燥して樹脂膜を形成する工程と、マスクを介して露光する工程と、照射部をアルカリ溶液で溶出または除去して現像する工程と、および現像後の樹脂膜を加熱処理する工程を含む、硬化膜のレリーフパターンの製造方法。
- 前記樹脂組成物を基板上に塗布し、乾燥して樹脂膜を形成する工程が、スリットノズルを用いて基板上に塗布する工程を含む、請求項16に記載の硬化膜のレリーフパターンの製造方法。
- 請求項13~15のいずれかに記載の硬化膜が銅金属の再配線間の層間絶縁膜として配置された、半導体電子部品または半導体装置。
- 前記再配線が酸化処理された銅金属配線で構成された、請求項18に記載の半導体電子部品または半導体装置。
- 前記再配線が銅金属配線であり、銅金属配線の幅と隣り合う配線同士の間隔が5μm以下である、請求項18または19に記載の半導体電子部品または半導体装置。
- 請求項13~15のいずれかに記載の硬化膜が、シリコンチップが配置された封止樹脂基板上に、再配線間の層間絶縁膜として配置された、半導体電子部品または半導体装置。
- 前記再配線が銅金属配線であって、更にバンプを介して半導体チップと銅金属配線とを接続している請求項18~21に記載の半導体電子部品または半導体装置。
- 前記再配線層が、半導体チップに近づくにつれ、金属配線の幅と隣り合う配線同士の間隔が狭くなる請求項18~22に記載の半導体電子部品または半導体装置。
- 前記層間絶縁膜の厚みが、半導体チップに対して近づくにつれ、薄くなる請求項18~23に記載の半導体電子部品または半導体装置。
- 請求項13~15のいずれかに記載の硬化膜を具備する有機EL表示装置。
- 請求項13~15のいずれかに記載の硬化膜を、仮貼り材料が配置された支持基板上に再配線間の層間絶縁膜として配置する工程と、
その上にシリコンチップと封止樹脂を配置する工程と、
その後、仮貼り材料が配置された支持基板と再配線を剥離する工程を含む、
半導体電子部品または半導体装置の製造方法。
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