JPWO2016152794A1 - 感光性樹脂組成物 - Google Patents
感光性樹脂組成物 Download PDFInfo
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- JPWO2016152794A1 JPWO2016152794A1 JP2016518460A JP2016518460A JPWO2016152794A1 JP WO2016152794 A1 JPWO2016152794 A1 JP WO2016152794A1 JP 2016518460 A JP2016518460 A JP 2016518460A JP 2016518460 A JP2016518460 A JP 2016518460A JP WO2016152794 A1 JPWO2016152794 A1 JP WO2016152794A1
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- Prior art keywords
- photosensitive resin
- resin composition
- film
- general formula
- mol
- Prior art date
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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Abstract
Description
[1]脂肪族ジアミンに由来する有機基を有するアルカリ可溶性樹脂を含むことを特徴とする感光性樹脂組成物。
[2]前記脂肪族ジアミンに由来する有機基を有するアルカリ可溶性樹脂が、(A)一般式(1)で表されるアルカリ可溶性ポリアミドである、[1]に記載の感光性樹脂組成物。
[3]前記一般式(1)中のY2が、一般式(2)で表される構造単位を有する[1]または[2]に記載の感光性樹脂組成物。
[4]前記一般式(1)中のY2が、150以上かつ2,000以下の分子量を有する[1]〜[3]のいずれかに記載の感光性樹脂組成物。
[5]前記(A)一般式(1)で表されるアルカリ可溶性ポリアミド、(B)光により酸を発生する化合物、および(C)熱架橋剤を含有する[1]〜[4]のいずれかに記載の感光性樹脂組成物。
[6]さらに、(D)一般式(3)で表される化合物を含有する、[1]〜[5]のいずれかに記載の感光性樹脂組成物。
[7][1]〜[6]のいずれかに記載の感光性樹脂組成物から形成された感光性シート。
[8][1]〜[6]のいずれかに記載の感光性樹脂組成物を基材上に塗布し、乾燥する工程を含む、感光性シートの製造方法。
[9][1]〜[6]のいずれかに記載の感光性樹脂組成物を硬化した硬化膜。
[10][7]に記載の感光性シートを硬化した硬化膜。
[11][9]に記載の硬化膜が配置された、層間絶縁膜または半導体保護膜。
[12][1]〜[6]のいずれかに記載の感光性樹脂組成物を基板上に塗布し、乾燥して感光性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する工程と、および現像後の感光性樹脂膜を加熱処理する工程により得られることを特徴とする硬化レリーフパターンの製造方法。
[13][7]に記載の感光性シートまたは[8]に記載の方法により製造された感光性シートを基材上にラミネートした後に紫外線照射工程と現像工程を経てパターンを形成し、さらに加熱して硬化膜のレリーフパターン層を形成することを特徴とする半導体電子部品または半導体装置の製造方法。
[14][9]または[10]に記載の硬化膜のレリーフパターン層を有することを特徴とする半導体電子部品または半導体装置。
[15][9]または[10]に記載の硬化膜が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。
[16]前記再配線と層間絶縁膜が2〜10層繰り返し配置された、[15]に記載の半導体電子部品または半導体装置。
[17][9]または[10]に記載の硬化膜が2種以上の材質で構成される隣接する基板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。
X1(COZ)2及びX2(COZ)2の構造を有するジカルボン酸誘導体としては、Zが炭素数1〜12の有機基、もしくはハロゲン元素から選ばれた基であり、下記の構造式から選ばれた基であることが好ましい。
Y1(NH2)2(OH)2の構造を有するアミノフェノールとしては、例えば、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、ビス(3−アミノ−4−ヒドロキシフェニル)スルホン、ビス(3−アミノ−4−ヒドロキシフェニル)プロパン、ビス(3−アミノ−4−ヒドロキシフェニル)メチレン、ビス(3−アミノ−4−ヒドロキシフェニル)エーテル、ビス(3−アミノ−4−ヒドロキシ)ビフェニル、ビス(3−アミノ−4−ヒドロキシフェニル)フルオレンなどのヒドロキシル基含有ジアミンなどを挙げることができる。また、これら2種以上のジアミン成分を組み合わせて用いてもよい。
(A)成分の樹脂の分子量は、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、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。(A)成分の樹脂におけるY2成分の分子量は、Y2構造を含むジアミンモノマーに関して、LC−MS(Q Exactive、Thermo SCIENTIFIC, Inc.製)で測定し、主要シグナルの分子量として求めることができる。
ワニスを、120℃で3分間プリベーク後の膜厚が10μmになるように、8インチのシリコンウエハ上に塗布現像装置ACT−8(東京エレクトロン製)を用いてスピンコート法で塗布した。プリベーク後の基板を露光機i線ステッパーNSR−2005i9C(ニコン製)を用いて露光した。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溶液(以下TMAH、多摩化学工業製)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、露光部が完全に溶解している時の最低露光量を感度とした。その結果が、感度が500mJ/cm2以上であるもの、または露光部が完全に溶解せず残渣があるものを不十分(1)、300mJ/cm2以上500mJ/cm2未満のものを良好(2)、300mJ/cm2未満のものをきわめて良好(3)とした。
ワニスを、シリコンウエハ上に120℃で3分間プリベークを行った後の膜厚が10μm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し、プリベークした後、イナートオーブンCLH−21CD−Sを用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で220℃まで昇温し、220℃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シリコンウエハを取り出し、その硬化膜をストレス装置FLX2908(KLA Tencor社製)にて測定した。その結果が、30MPa以上のものを1、20MPa以上30MPa未満の場合は2、20MPa未満のものは3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220℃まで昇温し、220℃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、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより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60%以上のものを3、30%以上60%未満のものを2、30%未満のものを1とした。
次の方法にて金属材料との接着性試験を行なった。
シリコンウエハ上に銅をスパッタリングし、それぞれ200〜500nmの厚みで形成された金属材料層を表面に有する基板(銅スパッタ基板)を用意した。この基板上にワニスをスピンナー(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8μm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)、110℃で30分、次いでさらに昇温して220℃にて1時間キュアし、感光性樹脂硬化膜を得た。
基板を2分割し、それぞれの基板についてキュア後の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。このうち一方のサンプル基板を用い、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/樹脂硬化膜間の接着性の評価を行なった。また、もう一方のサンプル基板については、プレッシャークッカーテスト(PCT)装置(タバイエスペエック(株)製HAST CHAMBER EHS−211MD)を用いて121℃、2気圧の飽和条件で200時間PCT処理を行なった後、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10未満を2(良好)、10以上を1(不良)とした。
大日本スクリーン製造(株)製ラムダエースSTM−602を使用し、プリベーク後、現像後の膜は屈折率1.629として、キュア後の膜は屈折率1.773として測定した。
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)(25.64g、0.070モル)をNMP185gに溶解させた。ここに、1,1’−(4,4’−オキシベンゾイル)ジイミダゾール(以降PBOMと呼ぶ)(17.20g、0.048モル)をNMP20gとともに加えて、85℃で3時間反応させた。続いて、1,12−ジアミノドデカン(5.01g、0.025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(1.24g、0.0050モル)、PBOM(14.33g、0.044モル)をNMP30gとともに加えて、85℃で1時間反応させた。さらに、末端封止剤として、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)をNMP10gとともに加えて、85℃で30分反応させた。反応終了後、室温まで冷却し、酢酸(26.41g、0.50モル)をNMP58gとともに加えて、室温で1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、アルカリ可溶性ポリアミド樹脂(A−1)の粉末を得た。上記の方法で評価した結果、樹脂(A−1)の重量平均分子量は33,000、PDIは2.1であった。
前記合成例1に従って、BAHF(25.64g、0.070モル)、PBOM(31.53g、0.088モル)、プロピレンオキシド構造を含むD−400(10.00g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−2)の粉末を得た。上記の方法で評価した結果、樹脂(A−2)の重量平均分子量は34,000、PDIは2.2であった。
前記合成例1に従って、BAHF(25.64g、0.070モル)、PBOM(31.53g、0.088モル)、エチレンオキシド及びプロピレンオキシド構造を含むED−600(15.00g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−3)の粉末を得た。上記の方法で評価した結果、樹脂(A−3)の重量平均分子量は34,000、PDIは2.3であった。
前記合成例1に従って、BAHF(25.64g、0.070モル)、PBOM(31.53g、0.088モル)、エチレンオキシド及びプロピレンオキシド構造を含むED−900(22.50g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−4)の粉末を得た。上記の方法で評価した結果、樹脂(A−4)の重量平均分子量は41,000、PDIは2.4であった。
前記合成例1に従って、BAHF(12.82g、0.035モル)、3,3’−ジアミノ−4,4’−ジヒドロキシジフェニルスルホン
(以降DABSと呼ぶ)(9.81g、0.035モル)、PBOM(31.53g、0.088モル)、ED−900(22.50g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−5)の粉末を得た。上記の方法で評価した結果、樹脂(A−5)の重量平均分子量は51,000、PDIは2.4であった。
前記合成例1に従って、BAHF(25.64g、0.070モル)、PBOM(31.53g、0.088モル)、プロピレンオキシド及びテトラメチレンオキシド構造を含むRT−1000(25.00g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−6)の粉末を得た。上記の方法で評価した結果、樹脂(A−6)の重量平均分子量は37,000、PDIは1.8であった。
前記合成例1に従って、BAHF(27.47g、0.075モル)、PBOM(31.53g、0.088モル)、RT−1000(20.00g、0.020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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−7)の粉末を得た。上記の方法で評価した結果、樹脂(A−7)の重量平均分子量は44,000、PDIは2.2であった。
前記合成例1に従って、BAHF(25.64g、0.070モル)、PBOM(31.53g、0.088モル)、エチレンオキシド及びプロピレンオキシド構造を含むED−2003(50.00g、0.025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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−8)の粉末を得た。上記の方法で評価した結果、樹脂(A−8)の重量平均分子量は52,000、PDIは2.1であった。
前記合成例1に従って、BAHF(34.79g、0.095モル)、PBOM(31.53g、0.088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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−9)の粉末を得た。上記の方法で評価した結果、樹脂(A−9)の重量平均分子量は38,000、PDIは1.6であった。
前記合成例1に従って、BAHF(12.82g、0.035モル)、PBOM(31.53g、0.088モル)、RT−1000(120.00g、0.060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(1.24g、0.0050モル)、5−ノルボルネン−2,3−ジカルボン酸無水物(3.94g、0.024モル)、酢酸(26.41g、0.50モル)、NMP300gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(A−10)の粉末を得た。上記の方法で評価した結果、樹脂(A−10)の重量平均分子量は43,000、PDIは2.5であった。
乾燥窒素気流下、m−クレゾール(70.2g、0.65モル)、p−クレゾール(37.8g、0.35モル)、37質量%ホルムアルデヒド水溶液(75.5g、(ホルムアルデヒド0.93モル)、シュウ酸二水和物(0.63g、0.005モル)、メチルイソブチルケトン264gを仕込んだ後、油浴中に浸し、反応液を還流させながら、4時間重縮合反応を行った。その後、油浴の温度を3時間かけて昇温し、その後に、フラスコ内の圧力を30〜50mmHgまで減圧し、揮発分を除去し、溶解している樹脂を室温まで冷却して、ノボラック樹脂(A−11)の粉末を得た。上記の方法で評価した結果、樹脂(A−11)の重量平均分子量は3,500、PDIは2.8であった。
乾燥窒素気流下、N−メチルピロリドン100gを仕込み、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(32.96g、0.090モル)、m−アミノフェノール(2.18g、0.020モル)を添加し、室温で撹拌溶解した後、反応溶液の温度を−10〜0℃に保ちながら、ドデカン二酸ジクロリド(20.04g、0.075モル)を10分間で滴下した後、4,4’−ジフェニルエーテルジカルボン酸クロリド(7.38g、0.025モル)を加え、室温で3時間撹拌を続けた。反応溶液を3リットルの水に投入し、析出物を回収、純水で3回洗浄した後、50℃の通風乾燥機で3日間乾燥し、ポリベンゾオキサゾール前駆体樹脂(A−12)の粉末を得た。上記の方法で評価した結果、樹脂(A−12)の重量平均分子量は31,000、PDIは2.3であった。
乾燥窒素気流下、BAHF(31.13g、0.085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(1.24g、0.0050モル)、m−アミノフェノール(2.18g、0.020モル)をNMP250gに溶解させた。ここに4,4’−オキシジフタル酸無水物(31.02g、0.10モル)をNMP50gとともに加えて、60℃で1時間反応させ、次いで200℃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日間乾燥し既閉環ポリイミド樹脂(A−13)の粉末を得た。上記の方法で評価した結果、樹脂(A−13)の重量平均分子量は27,000、PDIは2.0であった。
得られた樹脂(A−1〜13)10gに(B)成分として下記式で表される光酸発生剤を2.0g、(C)熱架橋剤としてHMOM−TPHAPを0.5g、MW−100LMを0.5g、溶剤としてγ−ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。
得られた樹脂(A−6)10gに(B)成分として下記式で表される光酸発生剤を2.0g、溶剤としてγ−ブチロラクトンを20g加えてワニスを作製し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。
実施例4または7で得られたワニスに対して、(D)化合物として下記式で表される化合物を0.02g、0.06g、0.2g、0.5g、1.5g添加し、これらの特性を上記評価方法により測定した。得られた結果を表1に示す。
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
Claims (17)
- 脂肪族ジアミンに由来する有機基を有するアルカリ可溶性樹脂を含むことを特徴とする感光性樹脂組成物。
- 前記脂肪族ジアミンに由来する有機基を有するアルカリ可溶性樹脂が、(A)一般式(1)で表されるアルカリ可溶性ポリアミドである、請求項1に記載の感光性樹脂組成物。
- 前記一般式(1)中のY2が、150以上かつ2,000以下の分子量を有する、請求項1〜3のいずれかに記載の感光性樹脂組成物。
- 前記(A)一般式(1)で表されるアルカリ可溶性ポリアミド、(B)光により酸を発生する化合物、および(C)熱架橋剤を含有する、請求項1〜4のいずれかに記載の感光性樹脂組成物。
- 請求項1〜6のいずれかに記載の感光性樹脂組成物から形成された感光性シート。
- 請求項1〜6のいずれかに記載の感光性樹脂組成物を基材上に塗布し、乾燥する工程を含む、感光性シートの製造方法。
- 請求項1〜6のいずれかに記載の感光性樹脂組成物を硬化した硬化膜。
- 請求項7に記載の感光性シートを硬化した硬化膜。
- 請求項9または10に記載の硬化膜が配置された、層間絶縁膜または半導体保護膜。
- 請求項1〜6のいずれかに記載の感光性樹脂組成物を基板上に塗布し、乾燥して感光性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、および現像後の感光性樹脂膜を加熱処理する工程により得られることを特徴とする硬化レリーフパターンの製造方法。
- 請求項7に記載の感光性シートまたは請求項8に記載の方法により製造された感光性シートを基材上にラミネートした後に紫外線照射工程と現像工程を経てパターンを形成し、さらに加熱して硬化膜のレリーフパターン層を形成することを特徴とする半導体電子部品または半導体装置の製造方法。
- 請求項9または10に記載の硬化膜のレリーフパターン層を有することを特徴とする半導体電子部品または半導体装置。
- 請求項9または10に記載の硬化膜が再配線間の層間絶縁膜として配置された、請求項14に記載の半導体電子部品または半導体装置。
- 前記再配線と層間絶縁膜が2〜10層繰り返し配置された、請求項15に記載の半導体電子部品または半導体装置。
- 請求項9または10に記載の硬化膜が2種以上の材質で構成される隣接する基板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。
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