JPWO2017204165A1 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JPWO2017204165A1 JPWO2017204165A1 JP2017529846A JP2017529846A JPWO2017204165A1 JP WO2017204165 A1 JPWO2017204165 A1 JP WO2017204165A1 JP 2017529846 A JP2017529846 A JP 2017529846A JP 2017529846 A JP2017529846 A JP 2017529846A JP WO2017204165 A1 JPWO2017204165 A1 JP WO2017204165A1
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- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims description 36
- 239000004065 semiconductor Substances 0.000 claims description 31
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
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Abstract
(a)架橋性基を有するフェノール骨格と架橋性基を有さないフェノール骨格を含んでなり、かつ重量平均分子量が1,000〜50,000の範囲内のアルカリ可溶性樹脂を含有する樹脂組成物であって、前記架橋性基を有するフェノール骨格と前記架橋性基を有さないフェノール骨格の構造単位の合計100モル%に占める、前記架橋性基を有するフェノール骨格の含有比率が5〜90モル%の範囲内であることを特徴とする樹脂組成物。
Description
前記架橋性基を有するフェノール骨格と前記架橋性基を有さないフェノール骨格の構造単位の合計100モル%に占める、前記架橋性基を有するフェノール骨格の含有比率が5〜90モル%の範囲内であることを特徴とする樹脂組成物である。
R1およびXにおける脂肪族基は、アルキル基、フルオロアルキル基、アルキルエーテル基、シロキサン基から選ばれる少なくともひとつを有する有機基であることが好ましく、不飽和結合や脂環構造を有していてもよい。
また、樹脂組成物の保存安定性を向上させる観点からは、Yがアルコキシメチル基であることが好ましい。
一般式(1)におけるXの好ましい例としては、p−キシリレン基、4,4’−ジメチレンビフェニル基、およびビス(4−メチレンフェニル)エーテル基が挙げられる。
また、(I)の方法においては、(a)アルカリ可溶性樹脂および樹脂組成物の安定性の観点から、前記フェノール化合物と前記縮合成分との仕込みモル比を、前記フェノール化合物を1としたときに前記縮合成分を0.2〜0.99の範囲内とすることが好ましく、0.4〜0.9の範囲内とすることがより好ましい。
本発明の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。この中でもアルキルエーテル基は、伸縮性が高いため、高伸度化の効果が大きく、特に好ましい。
一般式(9)で表される構造単位において、エーテル基の持つ伸縮性により、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(9)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(9)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(9)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。
(a)アルカリ可溶性樹脂の分子量は、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(以下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)を計算した。
(a)アルカリ可溶性樹脂における架橋性基を有するフェノール骨格の含有比率を架橋性基導入率とした。架橋性基導入率である、「b/(a+b)」に100を乗じた値(単位:%)は、次の方法で測定した。測定には、400MHz、1H−NMR(核磁気共鳴)装置(日本電子株式会社製 AL−400)を用いた。まず、(a)アルカリ可溶性樹脂を重水素化クロロホルム溶液中、積算回数16回で測定した。アルコキシメチル−CH2ORにおける−CH2−のプロトン(化学シフト=4.80ppm)の積分値とフェノール基のプロトン(化学シフト=5.35ppm)の積分値をもとに、次式により、架橋性基導入率を算出した。
ワニスを6インチのシリコンウエハ上に塗布した。塗布現像装置Mark−7を用い、120℃で3分間プリベークした後の膜厚が11μmとなるようにした。塗布方法はスピンコート法を用いた。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200℃まで昇温し、200℃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、膜厚を測定後、70℃でジメチルスルホキシド(DMSO)の溶剤にそれぞれウエハを100分浸漬した。溶剤から取り出したウエハを純水で洗浄した後、再度膜厚を測定し、その変化率の絶対値が15%を超えるものや硬化膜が剥離したものを不十分(D)、15%以内であって10%を超えるものを可(C)、10%以内であって5%を超えるものを良好(B)5%以内であるものをより良好(A)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。その後、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、その硬化膜の応力を応力測定装置FLX2908(KLA Tencor社製)にて確認した。その結果が、30MPa以上のものを不十分(D)、20MPa以上30MPa未満の場合は可(B)、20MPa未満の場合は良好(A)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。その後、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、破断点伸度の値が、60%以上のものを非常に良好(A)、40%以上60%未満のものを可(B)、20%以上40%未満のものを可(C)、20%未満のものを不十分(D)とした。
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、(0−1)ノボラック樹脂EP−4080G(商品名、旭有機材社製、Mw=10,600)11g、エピクロルヒドリン45g(0.5モル)、ジメチルスルホキシド370gを仕込み溶解させた。65℃に昇温した後、共沸する圧力まで減圧して,49%水酸化ナトリウム水溶液90g(1.1モル)を5時間かけて滴下した。その後、同条件で0.5時間撹拌を続けた。この間、共沸によって留出してきた留出分をディーンスタークトラップで分離し、水層を除去し、油層を反応系内に戻しながら、反応を行った。その後、未反応のエピクロルヒドリンおよびジメチルスルホキシドを減圧蒸留によって留去させた。それで得られた粗エポキシ樹脂にガンマブチロラクトン500mLを加え溶解した。更にこの溶液に10%水酸化ナトリウム水溶液10gを添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水150gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密ろ過を経た後に、溶媒を減圧下で留去してエポキシ基を含む固形分濃度50%の(A−1)樹脂溶液を得た。Mwは12,000であり、架橋性基導入率は45%であった。
窒素置換した三口フラスコ1,000ml中にm−クレゾールを108.0g、メタノール108.0g、水酸化ナトリウム40.0gを仕込み、撹拌しながら、67℃まで昇温後、30分間還流反応を行なった。その後、反応液を40℃まで冷却し、92質量%パラホルムアルデヒド53gを仕込み、再び67℃まで昇温後、5時間還流反応を行なった。反応終了後、反応液を30℃以下にまで冷却し、30質量%硫酸140.0gを反応液が35℃以上にならない様に30分かけて滴下した。得られた反応液のpHは4.9であった。さらに反応液中にイオン交換水540.0gを添加し、20分撹拌、20分静置後、分離した水層を除去した。反応液に洗浄分離溶剤であるメチルイソブチルケトン(MIBK)216.0g、イオン交換水324.0gを加え、30℃にて、20分撹拌、20分静置し、分離した水層を除去した。さらにイオン交換水324.0gを加え、除去水の電気伝導度が100μScm以下になるまで洗浄操作を繰り返した。洗浄終了後、γ―ブチロラクトン300gを加え、70℃、圧力を0.08MPaにてイオン交換水およびMIBKの留去を行い、固形分50質量%の(A−2)樹脂溶液を得た。Mwは3000であり、架橋性基導入率は85%であった。
(0−3)フェノール/ビフェニレン樹脂であるMEH−7851M(商品名、明和化成社製、Mw=2,400)をメタノール300mLに溶解させ、硫酸2gを加えて室温で24時間撹拌した。この溶液にアニオン型イオン交換樹脂(Rohmand Haas社製、アンバーリストIRA96SB)15gを加え1時間撹拌し、ろ過によりイオン交換樹脂を除いた。その後、ガンマブチロラクトン500mLを加え、ロータリーエバポレーターでメタノールを除き、固形分50質量%の(A−3)樹脂溶液にした。Mwは11,000であり、架橋性基導入率は35%であった。
容量0.5リットルのディーン・スターク装置付きセパラブルフラスラスコ中で、ピロガロール50.4g(0.4mol)、4,4’−ビス(メトキシメチル)ビフェニル72.7g(0.3mol)、ジエチル硫酸2.1g(0.15mol)、ジエチレングリコールジメチルエーテル27gを70℃で混合撹拌し、固形物を溶解させた。混合溶液をオイルバスにより120℃に加温し、反応液よりメタノールの発生を確認した。そのまま120℃で反応液を2時間撹拌した。次に反応容器を大気中で冷却し、これに別途テトラヒドロフラン100gを加えて撹拌した。前記反応希釈液を4Lの水に高速撹拌下で滴下し樹脂を分散析出させ、これを回収し、適宜水洗、脱水の後に真空乾燥を施し、フェノール樹脂(0−4)を得た。
次に、水酸化ナトリウム80g(2.0モル)を純水800gに溶解させた溶液に、フェノール樹脂(0−4)を溶解させた。完全に溶解させた後、25℃で37質量%のホルマリン水溶液36gを2時間かけて滴下した。その後25℃で17時間撹拌した。これに硫酸98gを加えて中和を行い、そのまま2日間放置した。放置後に溶液に生じた白色固体を水100mLで洗浄した。この白色固体を50℃で48時間真空乾燥した。
次に、このようにして得た樹脂をメタノール300mLに溶解させ、硫酸2gを加えて室温で24時間撹拌した。この溶液にアニオン型イオン交換樹脂(Rohmand Haas社製、アンバーリストIRA96SB)15gを加え1時間撹拌し、ろ過によりイオン交換樹脂を除いた。その後、ガンマブチロラクトン500mLを加え、ロータリーエバポレーターでメタノールを除き、固形分50質量%の(A−4)樹脂溶液にした。Mwは11,000であり、架橋性基導入率は25%であった。
窒素置換した三口フラスコ1,000ml中にm−クレゾールを108.0g、メタノール108.0g、水酸化ナトリウム40.0gを仕込み、撹拌しながら、67℃まで昇温後、30分間還流反応を行なった。その後、反応液を40℃まで冷却し、92質量%パラホルムアルデヒド300gを仕込み、再び67℃まで昇温後、5時間還流反応を行なった。反応終了後、反応液を30℃以下にまで冷却し、30質量%硫酸140.0gを反応液が35℃以上にならない様に30分かけて滴下した。得られた反応液のpHは4.9であった。さらに反応液中にイオン交換水540.0gを添加し、20分撹拌、20分静置後、分離した水層を除去した。反応液に洗浄分離溶剤であるメチルイソブチルケトン(MIBK)216.0g、イオン交換水324.0gを加え、30℃にて、20分撹拌、20分静置し、分離した水層を除去した。更にイオン交換水324.0gを加え、除去水の電気伝導度が100μScm以下になるまで洗浄操作を繰り返した。洗浄終了後、γ―ブチロラクトン300gを加え、70℃、圧力を0.08MPaにてイオン交換水およびMIBKの留去を行い、固形分50質量%の樹脂溶液を得た。得られた(A−5)樹脂溶液のMwは3000であり、架橋性基導入率は120%であった。
合成例4と同様の方法で得られたフェノール樹脂(0−4)と、水酸化ナトリウム80g(2.0モル)をテトラヒドロフラン800gに溶解させた溶液に、アクリロイルクロリド 30mL(0.4mol)を加え,還流管を取り付けた後,70℃のオイルバス中で4時間反応させた。反応後の溶液を,自然濾過し,溶液をエバポレーションした。
残存溶液をクロロホルム30mL に溶解させ,分液漏斗に溶液を移した。そこに水 50ml を加えて洗浄を行った。3回クロロホルムで抽出を行い,得られたクロロホルム溶液に硫酸ナトリウムを加え 1 晩放置後,綿濾過を行った。得られた溶液をエバポレーションした後に生成物を回収した。その後、ガンマブチロラクトン500mLを加え、固形分50質量%の(A−6)樹脂溶液にした。Mwは11,000であり、架橋性基導入率は30%であった。
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、白色重合体をアセトン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(B−1)が得られた。(B−1)はGPCによる分析により重量平均分子量(Mw)が3,500であった。
乾燥窒素気流下、BAHF29.30g(0.08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(0.005モル)、末端封止剤として、4−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにビス(3,4−ジカルボキシフェニル)エーテル二無水物(以下ODPAと呼ぶ、マナック(株)製)31.2g(0.1モル)をNMP20gとともに加えて、200℃で5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。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(B−2)の粉末を得た。前記の方法で評価した結果、樹脂(B−2)の重量平均分子量は25,000、イミド化率は100%と見積もられた。
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(52.82g、0.50モル)、NMP352gを用いて同様に行い、アルカリ可溶性ポリアミド樹脂(B−3)の粉末を得た。前記の方法で評価した結果、樹脂(B−3)の重量平均分子量は35,800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(以下BAHFと呼ぶ)(27.47g、0.075モル)をNMP257g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(以下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、プロピレンオキシドおよびテトラメチレンエーテルグリコール構造を含む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)、PBOM(14.33g、0.044モル)をNMP50g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(52.82g、0.50モル)をNMP87g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。この沈殿をろ過で集めて、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(B−4)の粉末を得た。前記の方法で評価した結果、樹脂(B−4)の重量平均分子量は40,000であった。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と5−ナフトキノンジアジドスルホニル酸クロリド26.86g(0.10モル)、4−ナフトキノンジアジドスルホニル酸クロリド13.43g(0.05モル)を1,4−ジオキサン50gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように注意しながら滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩をろ過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物を得た。
(a)アルカリ可溶性樹脂として、合成例1〜6の樹脂溶液10gに、(b)アルカリ可溶性樹脂として合成例7〜10のアルカリ可溶性樹脂5.0g、(c)感光剤として合成例10で得られたキノンジアジド化合物1.2g、架橋剤としてHMOM−TPHAP(本州化学工業(株)製)、溶剤としてGBLを10g加えてワニスを作製し、前記の方法で評価を行なった。
(a)アルカリ可溶性樹脂として、合成例1〜6の樹脂溶液10gに、(c)感光剤として合成例10で得られたキノンジアジド化合物1.2g、架橋剤としてHMOM−TPHAP(本州化学工業(株)製)、溶剤としてGBLを10g加えてワニスを作製し、前記の方法で評価を行なった。
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
Claims (20)
- (a)架橋性基を有するフェノール骨格と架橋性基を有さないフェノール骨格を含んでなり、かつ重量平均分子量が1,000〜50,000の範囲内のアルカリ可溶性樹脂を含有する樹脂組成物であって、
前記架橋性基を有するフェノール骨格と前記架橋性基を有さないフェノール骨格の構造単位の合計100モル%に占める、前記架橋性基を有するフェノール骨格の含有比率が5〜90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)アルカリ可溶性樹脂が、一般式(1)で表される構造を有する、請求項1に記載の樹脂組成物。
- 前記一般式(1)におけるaおよびbが、a>bの関係を満たす、請求項2〜4のいずれかに記載の樹脂組成物。
- 前記一般式(1)におけるn1が2または3である、請求項2〜5のいずれかに記載の樹脂組成物。
- 一般式(1)におけるaおよびbが、5≦{b/(a+b)}×100≦30の関係を満たす、請求項2〜6のいずれかに記載の樹脂組成物。
- さらに、(b)ポリイミド前駆体、ポリアミドイミド、ポリイミド、ポリベンゾオキサゾール前駆体、ポリベンゾオキサゾール、から選択される1種類以上のアルカリ可溶性樹脂を含有し、かつ
前記(b)アルカリ可溶性樹脂の含有量が、前記(a)アルカリ可溶性樹脂100質量部に対して1〜1000質量部の範囲内である、請求項1〜7のいずれかに記載の樹脂組成物。 - 前記(b)アルカリ可溶性樹脂が、アルキル基、フルオロアルキル基、アルキルエーテル基、およびシロキサン基から選択される1種類以上の有機基を有する、請求項8に記載の樹脂組成物。
- 前記(b)アルカリ可溶性樹脂が、アルキルエーテル基をもつジアミン残基を有する、請求項8または9に記載の樹脂組成物。
- さらに(c)感光剤と、(d)架橋剤を含有する、請求項1〜10のいずれかに記載の樹脂組成物。
- 前記一般式(1)におけるYが、アクリル構造を有する有機基である、請求項2〜11のいずれかに記載の樹脂組成物。
- 請求項1〜12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1〜12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13に記載の樹脂シートを硬化した硬化膜。
- 請求項1〜12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13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14または15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。
- 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18に記載の半導体電子部品または半導体装置。
- 請求項14または15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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