JP6834941B2 - 樹脂組成物、樹脂層、永久接着剤、仮貼り接着剤、積層フィルム、ウエハ加工体および電子部品または半導体装置の製造方法 - Google Patents
樹脂組成物、樹脂層、永久接着剤、仮貼り接着剤、積層フィルム、ウエハ加工体および電子部品または半導体装置の製造方法 Download PDFInfo
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- JP6834941B2 JP6834941B2 JP2017506946A JP2017506946A JP6834941B2 JP 6834941 B2 JP6834941 B2 JP 6834941B2 JP 2017506946 A JP2017506946 A JP 2017506946A JP 2017506946 A JP2017506946 A JP 2017506946A JP 6834941 B2 JP6834941 B2 JP 6834941B2
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Classifications
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Description
また、本発明は、本発明の樹脂組成物が塗膜形成された樹脂層である。
本発明の(a)一般式(1)で表される構造を含むポリイミド樹脂について説明する。
ポリシロキサン系ジアミンの平均分子量は、ポリシロキサン系ジアミンのアミノ基の中和滴定をすることによりアミノ基当量を算出し、このアミノ基当量を2倍することで求めることができる。例えば、試料となるポリシロキサン系ジアミンを所定量採取してビーカーに入れ、これを所定量のイソプロピルアルコール(以下、IPAとする。)とトルエンの1:1混合溶液に溶解し、この溶液に撹拌しながら0.1N塩酸水溶液を滴下していき、中和点となったときの0.1N塩酸水溶液の滴下量からアミノ基当量を算出することができる。このアミノ基当量を2倍した値が平均分子量である。
本発明の(b)フルオレン基を含む架橋剤は、汎用性の観点から、架橋性官能基としてエポキシ基、アクリル基、エピスルフィド基を有するフルオレン化合物が好ましく、耐熱性とコストに優れるエポキシ基を有するフルオレン化合物がより好ましい。
R19およびR20は、それぞれ同じでも異なっていてもよく、炭素数1〜30および窒素数0〜3を有する一価の有機基を示す。例えば、アルキル基、アルキレン基、アルコキシ基、フェニル基、フェノキシ基、アミノ基、カルボキシル基、水酸基、エポキシ基、オキセタン基、エーテル基、アラルキル基、アミド基、イミド基、ニトロ基、エステル基を有する構造などを用いることができる。
R27は、炭素数2〜20および窒素数1〜3を有する一価の有機基を示す。例えば、アミノ基、イソシアネート基、ウレイド基を有する構造などを用いることができる。一般式(7)で表される化合物の具体例として下記構造を挙げられるが、これらに限定されない。
一般式(8)で示される溶媒は、具体的には、プロピレングリコールモノ−t−ブチルエーテル、エチレングリコールモノ−t−ブチルエーテル、プロピレングリコールモノ−n−ブチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノエチルエーテル、エチレングリコールモノ−n−ブチルエーテル、エチレングリコールモノプロピルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル、ジプロピレングリコールジプロピルエーテル、ジプロピレングリコールジ−n−ブチルエーテル、ジプロピレングリコールジ−t−ブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル、トリプロピレングリコールモノプロピルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジメチルエーテルが挙げられるが、これに限定されない。
(A)アミン系溶媒には、イミド基を開環させリワーク溶剤に溶解しやすくする効果があり、洗浄時間を短縮することができる。イミド基を開環させるには、1級アミン、2級アミンを含むアミン系溶剤が好ましく、具体的にはモノメタノールアミン、ジメタノールアミン、モノエタノールアミン、ジメタノールアミン、ジメチルアミン、モノプロパノールアミン、イソプロパノールアミン、イソプロピルアミン、ジイソプロピルアミン、などが挙げられるが、これに限定されない。より好ましくは1級アミンを含むアミン系溶剤であり、具体的にはモノメタノールアミン、モノエタノールアミン、モノプロパノールアミン、イソプロパノールアミン、イソプロピルアミンなどが挙げられるが、これに限定されない。
下記製造例1〜32の樹脂組成物(AH1〜32)を厚さ18μmの電解銅箔の光沢面に厚さ20μmになるようにバーコーターで塗布後、80℃で10分、150℃で10分乾燥し、さらに窒素雰囲気下250℃で10分加熱処理を行って、硬化し、樹脂組成物積層銅箔を得た。次に得られた樹脂組成物積層銅箔の銅箔を塩化第2鉄溶液で全面エッチングし、樹脂組成物の単膜を得た。
(b)フルオレン基を含む架橋剤約15mgをアルミ製標準容器に詰め、熱重量分析装置TGA−50(島津製作所(株)製)を用いて測定した。測定条件は、60℃で30分保持した後、昇温速度5℃/分で500℃まで昇温した。
厚さ750μmの8インチシリコンウエハ(信越化学工業(株)社製)上に、下記製造例1〜32で得られた樹脂組成物を乾燥後の厚みが20μmになるようにスピンコーターで回転数を調整して塗布し、120℃で10分熱処理して乾燥した後、200℃で3分間熱処理して硬化を行い、樹脂組成物層積層シリコン基板を得た。
A:ボイド無し
B:1cm以下のサイズのボイド有り
C:1cm以上のサイズのボイド有り。
上記で接着性評価をしたガラス基板積層シリコン基板、または、フィルム積層シリコン基板について、シリコン基板のエッジから樹脂組成物がはみ出しているかを目視で確認した。評価基準は下記のとおりである。
A:はみ出し無し
B:はみ出し有り。
上記ではみ出し評価をしたガラス基板積層シリコン基板、または、フィルム積層シリコン基板を250℃で10分間熱処理した後、ガラス、または、フィルム側から肉眼で観察し、ボイドの有無を評価した。評価基準は下記のとおりである。
A:ボイド無し
B:1cm以下のサイズのボイド有り
C:1cm以上のサイズのボイド有り。
上記で接着性評価後の耐熱評価をしたガラス基板積層シリコン基板、または、フィルム積層シリコン基板をグラインダーDAG810(DISCO製)にセットし、シリコン基板を厚み30μmまたは100μmまで研磨した。グライディング後のシリコン基板を肉眼で観察し、割れ、クラックなどの有無を評価した。評価基準は下記のとおりである。
A:30μmと100μmの両方で割れ、クラック無し
B:30μmのみで割れ、クラック有り
C:100μmのみで割れ、クラック有り
D:30μmと100μmの両方で割れ、クラック有り。
上記でバックグライディング評価をしたガラス基板積層シリコン基板、または、フィルム積層シリコン基板を270℃で10分間熱処理した後、薄シリコン基板側から肉眼で観察し、薄シリコン基板に膨れの有無を評価した。評価基準は下記のとおりである。
A:30μmと100μmの両方で膨れ無し
B:30μmのみで膨れ有り
C:100μmのみで膨れ有り
D:30μmと100μmの両方で膨れ有り。
1.室温での機械剥離法
上記でバックグライディングしたガラス基板積層シリコン基板、または、フィルム積層シリコン基板のシリコン基板にダイシングフレームを用いてダイシングテープを貼り、このダイシングテープ面を真空吸着によって吸着盤にセットした後、室温でガラス基板、または、フィルムの一点をピンセットで持ち上げることでガラス基板を剥離した。
上記8インチ無アルカリガラス基板に溶剤通過のための穴を設けた基板を用いてガラス基板積層シリコン基板を作製した。その後、製造例97で得たリワーク溶剤に23℃10分間の条件で浸した後、基板を素手で剥離した。フィルム積層シリコン基板は、室温での溶剤剥離法は行わない。
ガラス基板積層シリコン基板
A:1,2共に剥離できた。
B1:1.室温での機械剥離法のみ剥離できた。
B2:2.室温での溶剤剥離法のみ剥離できた。
C:1,2共に剥離できなかった。
フィルム積層シリコン基板
a:室温での機械剥離法で剥離できた。
c:剥離できなかった。
上記で剥離したシリコン基板に付着している樹脂層を製造例97で得たリワーク溶剤で23℃10分間の条件でリワークし、溶解性を肉眼で観察した。評価基準は下記のとおりである。
A:残渣無し
B:溶解するが、基板上に残渣が残る
C:溶解しない。
試料となるポリシロキサン系ジアミン5gをビーカーに採取し、ここに、IPA:トルエンが1:1の混合溶液を50mL入れ溶解した。次に、京都電子工業(株)製の電位差自動測定装置AT−610を用い、0.1N塩酸水溶液を撹拌しながら滴下し、中和点となる滴下量を求めた。得られた0.1N塩酸水溶液の滴下量から下式(9)を用いて平均分子量を算出した。
2×〔10×36.5×(滴下量(g))〕/5=平均分子量 (9)
次に、用いたポリシロキサン系ジアミンがn=1であった場合およびn=10であった場合の分子量を化学構造式から計算し、nの数値と分子量の関係を一次関数の関係式として求めた。この関係式に上記平均分子量をあてはめ、nの平均値を求めた。
ODPA:3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物
APPS1:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:860、式(1)においてn=9)
APPS2:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:1600、式(1)においてn=19)
APPS3:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:4400、式(1)においてn=57)
APB:1,3−ビス(3−アミノフェノキシ)ベンゼン
FDA:9,9−ビス(3−アミノ−4−ヒドロキシフェニル)フルオレン
BAFL:9,9−ビス(4−アミノフェニル)フルオレン
PG−100:フルオレン基含有エポキシ樹脂(大阪ガスケミカル(株)製)
CG−500:フルオレン基含有エポキシ樹脂(大阪ガスケミカル(株)製)
EG−200:フルオレン基含有エポキシ樹脂(大阪ガスケミカル(株)製)
EG−280:フルオレン基含有エポキシ樹脂(大阪ガスケミカル(株)製)
CG−400:フルオレン基含有エポキシ樹脂(大阪ガスケミカル(株)製)
CS−500:フルオレン基含有エピスルフィド樹脂(大阪ガスケミカル(株)製)
EA−0300:フルオレン基含有アクリル樹脂(大阪ガスケミカル(株)製)
JER828:2,2−ビス(4−グリシジルオキシフェニル)プロパン(三菱化学(株)製)
MEK−ST−40:有機溶剤分散シリカ(溶剤:MEK シリカ:40wt%)(日産化学工業(株)製)
DMM:ジプロピレングリコールジメチルエーテル。
温度計、乾燥窒素導入口、温水・冷却水による加熱・冷却装置、および、撹拌装置を付した反応釜に、APPS1 602.0g(0.7mol)、APB 43.8g(0.15mol)、FDA 57.1g(0.15mol)をDMM 1013.1gと共に仕込み、溶解させた後、ODPA 310.2g(1mol)を添加し、室温で1時間、続いて60℃で5時間反応させて、50質量%のポリアミド酸溶液PA1を得た。
酸二無水物、ジアミンの種類と仕込量を表1のように変えた以外は製造例1と同様の操作を行い、50質量%のポリアミド酸溶液(PA2〜PA5)を得た。
500mlのフラスコにヘキサン500gを入れ、これにアミノフェニルトリメトキシシラン(3−アミノフェニルトリメトキシシランと4−アミノフェニルトリメトキシシランが6:4の重量比で混合されているもの)21.33g(0.1mol)を加えた。ついで、無水酢酸10.21g(0.1mol)をゆっくり滴下し、室温で3時間反応させた。沈殿物を濾別して乾燥し、得られた合成物をAcAPMSとした。AcAPMSの構造を下記に示す。
撹拌装置を付した反応釜に、合成例1で得たポリアミド酸溶液(PA1)200.0g、エポキシ樹脂であるCG500 10.0g、フィラー溶液であるMEK−ST−40 12.0gを共に仕込み、室温で2時間撹拌して、樹脂組成物(AH1)を得た。
(a)ポリイミド樹脂、(b)エポキシ樹脂、(c)シロキサン重合体、(d)シランカップリング剤、(e)フィラーの種類と仕込量を表2のように変えた以外は製造例1と同様の操作を行い、樹脂組成物(AH2〜32)を得た。
製造例1で得られた樹脂組成物(AH1)をバーコーターを用いて、支持フィルム層SR7(厚さ75μm、ポリエステルフィルム、大槻工業株式会社製)上に塗布し、100℃で10分間乾燥を行った後、保護フィルム層としてSR7(大槻工業株式会社製)をラミネートして、樹脂層の厚みが20μmの積層フィルム(S1)を得た。
樹脂組成物の種類を表3のように変えた以外は製造例33と同様の操作を行い、積層フィルム(S2〜32)を得た。
製造例1で得られた樹脂組成物(AH1)をバーコーターを用いて、支持フィルム層140EN−Y(厚さ35μm、1%重量減少温度>450℃、融点>300℃、線膨張係数5ppm/℃、ポリイミドフィルム、東レ・デュポン株式会社製)上に塗布し、100℃で10分間乾燥を行った後に、200℃で3分熱処理し樹脂組成物の硬化を行った。保護フィルム層としてSR7(大槻工業株式会社製)をラミネートして、樹脂層の厚みが20μmの積層フィルム(S33)を得た
製造例66〜96
樹脂組成物の種類を表4のように変えた以外は製造例65と同様の操作を行い、積層フィルム(S34〜64)を得た。
撹拌装置を付した反応釜に、モノエタノールアミン30g、DMM30g、N−メチル−2−ピロリドン30gを仕込み、室温で1時間撹拌して、リワーク溶剤を得た。
厚さ750μmの8インチシリコン基板(信越化学工業(株)社製)上に、製造例1で得られた樹脂組成物(AH1)を乾燥後の厚みが20μmになるようにスピンコーターで回転数を調整して塗布し、120℃で10分熱処理して乾燥した後、200℃で3分間熱処理して硬化を行い、樹脂組成物積層シリコン基板を得た。
樹脂組成物を表5のように変えた以外は、実施例1と同様の操作を行い、ガラス基板積層シリコン基板を得た。
樹脂組成物を表5のように変えた以外は、実施例1と同様の操作を行い、ガラス基板積層シリコン基板を得た。
製造例33で得られた積層フィルム(S1)の保護フィルム層を剥離した後に、樹脂層と8インチシリコン基板(信越化学工業(株)社製)が接するように、真空ラミネート装置VTM−200M(株式会社タカトリ製)を用いて積層した。積層条件は、ヒーター温度100℃、ロール温度100℃、ラミネート速度5mm/秒、ラミネートロール圧力0.2MPa、チャンバー圧力150Paにて行った。得られた積層体の支持フィルム層を剥離し、樹脂組成物積層シリコン基板を得た。樹脂組成物積層シリコン基板を200℃で3分間熱処理して硬化した後に、樹脂層と別の8インチ無アルカリガラス基板(コーニング社製)が接するように重ね合わせ、上板、下板をそれぞれ180℃に設定した熱プレス機を用いて、0.5MPaの圧力で5分間圧着し、ガラス基板積層シリコン基板を得た。得られたガラス基板積層シリコン基板を用いて接着性評価、はみ出し評価、接着性評価後の耐熱評価、シリコン基板のバックグライディング評価、バックグライディング評価後の耐熱評価、剥離評価、リワーク評価を行い、結果を表6にまとめた。
積層フィルムを表6のように変えた以外は、実施例31と同様の操作を行い、ガラス基板積層シリコン基板を得た。
積層フィルムを表6のように変えた以外は、実施例31と同様の操作を行い、ガラス基板積層シリコン基板を得た。
製造例65で得られた積層フィルム(S33)の保護フィルム層を剥離した後に、樹脂層と8インチシリコン基板(信越化学工業(株)社製)が接するように、真空ラミネート装置VTM−200M(株式会社タカトリ製)を用いて積層した。積層条件は、ヒーター温度100℃、ロール温度100℃、ラミネート速度5mm/秒、ラミネートロール圧力0.2MPa、チャンバー圧力150Paにて行った。得られた積層基板を上板、下板をそれぞれ180℃に設定した熱プレス機を用いて、0.5MPaの圧力で5分間圧着し、フィルム積層シリコン基板を得た。得られたフィルム積層シリコン基板を用いて接着性評価、はみ出し評価、接着性評価後の耐熱評価、シリコン基板のバックグライディング評価、バックグライディング評価後の耐熱評価、剥離評価、リワーク評価を行い、結果を表7にまとめた。
積層フィルムを表7のように変えた以外は、実施例61と同様の操作を行い、フィルム積層シリコン基板を得た。
比較例5、6
積層フィルムを表7のように変えた以外は、実施例61と同様の操作を行い、フィルム積層シリコン基板を得た。
Claims (26)
- 少なくとも(a)一般式(1)で表される構造を有するポリイミド樹脂、および(b)フルオレン基を含む架橋剤を含有し、さらに、(c)一般式(6)で表されるシロキサン重合体を含有する、樹脂組成物。
- 前記(b)フルオレン基を含む架橋剤がフルオレン基を含むエポキシ樹脂である請求項1に記載の樹脂組成物。
- 前記(b)フルオレン基を含む架橋剤の5%重量減少温度が250℃以上400℃以下である、請求項1または2に記載の樹脂組成物。
- 前記(b)フルオレン基を含む架橋剤の含有量が前記(a)ポリイミド樹脂100質量%に対して0.1質量%以上40質量%以下である請求項1〜3のいずれかに記載の樹脂組成物。
- 前記(c)一般式(6)で表されるシロキサン重合体のR19およびR20がアミノ基である請求項1〜4のいずれかに記載の樹脂組成物。
- 前記(c)一般式(6)で表されるシロキサン重合体の含有量が前記(a)一般式(1)で表される構造を有するポリイミド樹脂100質量%に対して0.01質量%以上30質量%以下である請求項1〜5のいずれかに記載の樹脂組成物。
- さらに、(d)シランカップリング剤を含有する請求項1〜6のいずれかに記載の樹脂組成物。
- 前記(d)シランカップリング剤の含有量が前記(a)一般式(1)で表される構造を有するポリイミド樹脂100質量%に対して0.01質量%以上30質量%以下である請求項7に記載の樹脂組成物。
- さらに、(e)無機微粒子を含有する請求項1〜8のいずれかに記載の樹脂組成物。
- 前記(e)無機微粒子の含有量が前記(a)ポリイミド樹脂100質量%に対して0.1質量%以上40質量%以下である請求項9に記載の樹脂組成物。
- 硬化後のガラス転移温度が30℃以上150℃以下である、請求項1〜10のいずれか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が塗膜形成された樹脂層。
- 請求項1〜11のいずれかに記載の樹脂組成物を含む永久接着剤。
- 請求項1〜11のいずれかに記載の樹脂組成物を含む仮貼り接着剤。
- 電子回路形成基板または半導体回路形成基板と支持基板の貼り合わせ用である請求項14記載の仮貼り接着剤。
- 前記支持基板がシリコン基板、ガラス基板、フィルムのいずれかである請求項15に記載の仮貼り接着剤。
- 請求項1〜11のいずれかに記載の樹脂組成物を用いた電子部品または半導体装置の製造方法。
- 請求項1〜11のいずれかに記載の樹脂組成物を耐熱性絶縁フィルムの少なくとも片面に積層した積層フィルム。
- 前記耐熱性絶縁フィルムが、離型処理された表面を有する請求項18に記載の積層フィルム。
- 前記耐熱性絶縁フィルム上に積層された前記樹脂組成物の表面に、さらに離型処理された表面を有するフィルムが積層された、請求項18または19に記載の積層フィルム。
- 請求項18〜20のいずれかに記載の積層フィルムを用いた電子部品または半導体装置の製造方法。
- 電子回路形成基板または半導体回路形成基板と支持基板とが少なくとも請求項13に記載の樹脂層または請求項18〜20のいずれかに記載の積層フィルムを介して接着されたウエハ加工体。
- 電子回路形成基板または半導体回路形成基板と支持基板とが、請求項13に記載の樹脂層のみ、または請求項18〜20のいずれかに記載の積層フィルムのみを介して接着された請求項22記載のウエハ加工体。
- 前記電子回路形成基板または半導体回路形成基板の厚みが1μm以上100μm以下である請求項22または請求項23に記載のウエハ加工体。
- 請求項22〜24のいずれかに記載のウエハ加工体を用いた電子部品または半導体装置を製造する方法であって、前記ウエハ加工体における電子回路形成基板または半導体回路形成基板を熱処理する工程、前記ウエハ加工体における電子回路形成基板または半導体回路形成基板を支持基板から剥離する工程、および前記ウエハ加工体から剥離した電子回路形成基板または半導体回路形成基板に付着した樹脂層または前記ウエハ加工体における支持基板に付着した樹脂層を溶剤で洗浄する工程の少なくともどちらかを含む電子部品または半導体装置の製造方法。
- 前記ウエハ加工体における電子回路形成基板または半導体回路形成基板を230℃以上450℃以下の温度で熱処理する工程を含む請求項25記載の電子部品または半導体装置の製造方法。
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