JP2017145379A - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JP2017145379A JP2017145379A JP2016094709A JP2016094709A JP2017145379A JP 2017145379 A JP2017145379 A JP 2017145379A JP 2016094709 A JP2016094709 A JP 2016094709A JP 2016094709 A JP2016094709 A JP 2016094709A JP 2017145379 A JP2017145379 A JP 2017145379A
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Abstract
Description
A<B
を満たすことが好ましい。
硬化反応により体積が収縮する硬化性成分(A1)としては、硬化反応により体積が収縮する硬化性を有していれば、特に制限なく従来公知の材料を用いることができるが、好ましくは、イオン性の開環重合反応または重付加の重合反応性の硬化成分であることが好ましい。本明細書中において、イオン性の開環重合とは、開環して重合する単量体を用いて重合反応を進行させた際に、成長鎖がイオンである重合を意味するものとする。また、重付加反応とは、環状構造を有する官能基を2個以上有する単量体と、両末端に当該環状構造を有する官能基と反応し得る官能基を有する単量体とが、付加反応を繰り返しながら重合が進行する反応を意味するものとする。このようなイオン性の開環重合反応または重付加の重合反応性硬化成分としては、エポキシやオキセタン等の環状エーテル類が好ましく、その中でもエポキシ樹脂を用いることが好ましい。エポキシ樹脂には反応前の形状から固形、半固形、液状のエポキシ樹脂がある。これらは1種単独で、または2種以上を組み合わせて用いることができる。このような環状エーテル類を硬化性成分(A1)として含有することにより、後記するように硬化性成分(A1)が硬化した際に擬似ウェハとの密着性が向上し、より一層、FO−WLPの反りを抑制することができる。
硬化促進剤成分として金属触媒を使用する場合、その含有量は、硬化性成分100質量部に対して金属換算で10〜550ppmが好ましく、25〜200ppmが好ましい。
本発明による硬化性樹脂組成物は、上記した硬化性成分(A1)とは異なる硬化反応により体積が収縮する硬化性成分(B1)を含む。硬化性成分(A1)が例えば上記したようなイオン性の開環重合反応または重付加の重合反応により硬化し得る材料である場合、硬化性成分(B1)としては、イオン性の開環重合反応または重付加の重合反応により硬化し得る材料以外の公知の材料から選択できるが、例えば、ラジカル性の付加重合反応により硬化し得る硬化性成分を好ましく使用することができる。本明細書において、ラジカル性の付加重合とは、ラジカルにより重合が開始され、二重結合あるいは三重結合をもった不飽和化合物が付加して重合体になる反応を意味するものとする。このようなラジカル性付加重合反応により硬化し得る硬化性成分としては、分子中に1個以上のエチレン性不飽和基を有する化合物が好ましい。
(1)1分子中に複数のフェノール性水酸基を有する化合物とアルキレンオキシドとを反応させて得られる反応生成物に、不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られる不飽和基含有ポリマー、
(2)2官能またはそれ以上の多官能エポキシ樹脂に(メタ)アクリル酸を反応させ、側鎖に存在する水酸基に2塩基酸無水物を付加させたアクリル含有ポリマー、
(3)2官能エポキシ樹脂の水酸基をさらにエピクロロヒドリンでエポキシ化した多官能エポキシ樹脂に(メタ)アクリル酸を反応させ、生じた水酸基に2塩基酸無水物を付加させたアクリル含有ポリマー、
(4)1分子中に複数のフェノール性水酸基を有する化合物と環状カーボネート化合物とを反応させて得られる反応生成物に不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られる不飽和基含有ポリマー、
(5)ジイソシアネートと、2官能エポキシ樹脂の(メタ)アクリレートもしくはその部分酸無水物変性物、カルボキシル基含有ジアルコール化合物およびジオール化合物との重付加反応によるアクリル含有ウレタン樹脂、
(6)不飽和カルボン酸と、不飽和基含有化合物との共重合により得られる不飽和基含有ポリマー、
(7)ジイソシアネートと、カルボキシル基含有ジアルコール化合物およびジオール化合物との重付加反応による樹脂の合成中に、分子内に1つの水酸基と1つ以上の(メタ)アクリロイル基を有する化合物を加え、末端(メタ)アクリル化したアクリル含有ウレタン樹脂、
(8)ジイソシアネートと、カルボキシル基含有ジアルコール化合物およびジオール化合物との重付加反応による樹脂の合成中に、分子内に1つのイソシアネート基と1つ以上の(メタ)アクリロイル基を有する化合物を加え、末端(メタ)アクリル化したアクリル含有ウレタン樹脂、
(9)前記(5)の樹脂の合成中に、分子内に1つの水酸基と1つ以上の(メタ)アクリロイル基を有する化合物を加え、末端(メタ)アクリル化したアクリル含有ウレタン樹脂、
(10)前記(5)の樹脂の合成中に、分子内に1つのイソシアネート基と1つ以上の(メタ)アクリロイル基を有する化合物を加え末端(メタ)アクリル化したアクリル含有ウレタン樹脂、および
(11)上記(1)〜(10)の樹脂にさらに1分子内に1つのエポキシ基と1個以上の(メタ)アクリロイル基を有する化合物を付加してなるアクリル含有ポリマー、
等を単独でまたは2種以上を組み合わせて、あるいは上記した分子中に1個以上のエチレン性不飽和基を有するモノマーと併用して、用いることができる。
1)硬化性成分(A1)および硬化性成分(A1)を硬化させ得る硬化剤成分(A2)として熱硬化剤成分(A2−1)と、硬化性成分(B1)および硬化性成分(B1)を硬化させ得る硬化剤成分(B2)として光硬化剤成分(B2−2)との組合せ、
2)硬化性成分(A1)および硬化性成分(A1)を硬化させ得る硬化剤成分(A2)として光硬化剤成分(A2−2)と、硬化性成分(B1)および硬化性成分(B1)を硬化させ得る硬化剤成分(B2)として熱硬化剤成分(B2−1)との組合せ、
等が挙げられる。
体積収縮率(%)=(1−(硬化前の硬化性成分の密度/硬化後の硬化性成分の密度))×100
例えば、硬化前のモノマー溶液の密度が1.0g/cm3であり、モノマーが硬化した硬化物(ポリマー)の密度が1.2g/cm3であったとすると、体積収縮率(%)は約17%となる。硬化性成分が液状の場合の密度は、例えば25℃の雰囲気下での一定の体積をはかりとり、その質量から密度を測定できる。硬化性成分が固形物の場合や硬化後の硬化性成分の場合は、水中置換法(アルキメデス法)により密度を測定できる。より具体的には、例えばメトラー社製XS205分析天秤と密度測定キット「固体及び液体の密度測定キット」を用い、置換液として蒸留水を用いて、下記式にて密度(ρ)を求めることができる。
ρ=(α×ρ0)/(α―β)
(上記式中、ρは固形物の密度、αは大気中での固形物の質量、βは置換液中での固形物の質量、ρ0は測定温度での蒸留水の密度、を表す。)
体積収縮率(%)=(1−(硬化前の硬化性樹脂組成物全体の密度/硬化後の硬化性樹脂組成物全体の密度))×100
測定装置:Waters製「Waters 2695」
検出器:Waters製「Waters2414」、RI(示差屈折率計)
カラム:Waters製「HSPgel Column,HR MB−L,3μm,6mm×150mm」×2+Waters製「HSPgel Column,HR1,3μm,6mm×150mm」×2
測定条件:
カラム温度:40℃
RI検出器設定温度:35℃
展開溶媒:テトラヒドロフラン
流速:0.5ml/分
サンプル量:10μl
サンプル濃度:0.7wt%
無機フィラー成分(D)が含有されることによりたとえばFO−WLPの個片化(ダイシング)での切断が容易になる。また、保護膜にレーザーマーキングを施すことにより、レーザー光により削り取られた部分に無機フィラー成分(D)が露出して、反射光が拡散するために白色に近い色を呈する。これにより、FO−WLP用反り矯正材が後述する着色剤成分(E)を含有する場合、レーザーマーキング部分と他の部分とでコントラスト差が得られ、マーキング(印字)が明瞭になるという効果がある。
3,4,5,6,8,9,12,14,15,16,17,21,22,23,31,32,112,114,146,147,151,170,184,187,188,193,210,245,253,258,266,267,268,269等のモノアゾ系赤色着色剤、PigmentRed37,38,41等のジスアゾ系赤色着色剤、PigmentRed48:1,48:2,48:3,48:4,49:1,49:2,50:1,52:1,52:2,53:1,53:2,57:1,58:4,63:1,63:2,64:1,68等のモノアゾレーキ系赤色着色剤、PigmentRed171、PigmentRed175、PigmentRed176、PigmentRed185、PigmentRed208等のベンズイミダゾロン系赤色着色剤、SolventRed135、SolventRed179、PigmentRed123、PigmentRed149、PigmentRed166、PigmentRed178、PigmentRed179、PigmentRed190、PigmentRed194、PigmentRed224等のぺリレン系赤色着色剤、PigmentRed254、PigmentRed255、PigmentRed264、PigmentRed270、PigmentRed272等のジケトピロロピロール系赤色着色剤、PigmentRed220、PigmentRed144、PigmentRed166、PigmentRed214、PigmentRed220、PigmentRed221、PigmentRed242等の縮合アゾ系赤色着色剤、PigmentRed168、PigmentRed177、PigmentRed216、SolventRed149、SolventRed150、SolventRed52、SolventRed207等のアンスラキノン系赤色着色剤、PigmentRed122、PigmentRed202、PigmentRed206、PigmentRed207、PigmentRed209等のキナクリドン系赤色着色剤が挙げられる。
SolventYellow163、PigmentYellow24、PigmentYellow108、PigmentYellow193、PigmentYellow147、PigmentYellow199、PigmentYellow202等のアントラキノン系黄色着色剤、PigmentYellow110、PigmentYellow109、PigmentYellow139、PigmentYellow179、PigmentYellow185等のイソインドリノン系黄色着色剤、PigmentYellow93、PigmentYellow94、PigmentYellow95、PigmentYellow128、PigmentYellow155、PigmentYellow166、PigmentYellow180等の縮合アゾ系黄色着色剤、PigmentYellow120、PigmentYellow151、PigmentYellow154、PigmentYellow156、PigmentYellow175、PigmentYellow181等のベンズイミダゾロン系黄色着色剤、PigmentYellow1,2,3,4,5,6,9,10,12,61,62,62:1,65,73,74,75,97,100,104,105,111,116,167,168,169,182,183等のモノアゾ系黄色着色剤、PigmentYellow12,13,14,16,17,55,63,81,83,87,126,127,152,170,172,174,176,188,198等のジスアゾ系黄色着色剤等を使用することができる。
上記した硬化性樹脂組成物をFO−WLPの反り矯正層の形成用組成物として用いる場合について、反り矯正層を設けるFO−WLPの擬似ウェハについて説明する。
また、粘着層材料として、エチレン性不飽和基を有するカルボキシル基含有樹脂と、上記したようなラジカル重合開始剤を含有させることもでき、このような樹脂を含有させることにより、加熱または活性エネルギー線の照射により、粘着層の粘着性を変化させることもできる。
温度計、窒素導入装置兼アルキレンオキシド導入装置、および撹拌装置を備えたオートクレーブに、ノボラック型クレゾール樹脂(昭和電工社製、ショーノールCRG951、OH当量:119.4)119.4部、水酸化カリウム1.19部およびトルエン119.4部を仕込み、撹拌しつつ系内を窒素置換し、加熱昇温した。次に、プロピレンオキシド63.8部を徐々に滴下し、125〜132℃、0〜4.8kg/cm2で16時間反応させた。その後、室温まで冷却し、この反応溶液に89%リン酸1.56部を添加混合して水酸化カリウムを中和し、不揮発分62.1%、水酸基価が182.2g/eq.であるノボラック型クレゾール樹脂のプロピレンオキシド反応溶液を得た。これは、フェノール性水酸基1当量当りアルキレンオキシドが平均1.08モル付加しているものであった。
クレゾールノボラック型エポキシ樹脂(日本化薬社製、EOCN−104S、エポキシ当量220g/eq)220部(1当量)、カルビトールアセテート140.1部、およびソルベントナフサ60.3部をフラスコに仕込み、90℃に加熱・攪拌し、溶解した。
得られた溶液を一旦60℃まで冷却し、アクリル酸72部(1モル)、メチルハイドロキノン0.5部、トリフェニルホスフィン2部を加え、100℃に加熱し、約12時間反応させ、酸価が0.2mgKOH/gの反応物を得た。これにテトラヒドロ無水フタル酸80.6部(0.53モル)を加え、90℃に加熱し、約6時間反応させ、固形分の酸価85mgKOH/g、固形分64.9%の硬化性成分(B1)2であるアクリル含有ポリエーテル化合物溶液を得た。
攪拌機と冷却管を備えた2,000mlのフラスコに、トリプロピレングリコールモノメチルエーテル377gを入れ、窒素気流下で90℃に加熱した。スチレン104.2g、メタクリル酸246.5、ジメチル2,2’−アゾビス(2−メチルプロピオネート)(和光純薬工業社製:V−601)20.7gを混合溶解したものを、4時間かけてフラスコに滴下した。このようにして、硬化剤成分(A2−1)1であるのカルボキシル基含有樹脂溶液を得た。このカルボキシル基含有樹脂溶液は、固形分酸価が120mgKOH/g、固形分が50%、重量平均分子量2×104であった。
ジエチレングリコールモノエチルエーテルアセテート(CA)75gに、Y−X−Y型ブロック共重合体(アルケマ社製M52N)を25gを加え、攪拌し、80℃にて加熱することにより溶解させた。これをフィルム性付与ポリマーC1とした。
下記の表1中に示す配合に従い、各成分を配合し、攪拌機にて予備混合した後、3本ロールミルで分散させ、混練して、それぞれ硬化性樹脂組成物を調製した。なお、表中の配合量は、質量部を示す。なお、表中の硬化性成分(B1)、硬化剤成分(A2−1)およびフィルム性付与ポリマ(C1)は固形分としての値である。
N−770:DIC社製 フェノールノボラック型エポキシ エピクロンN−770
EP−828:三菱化学製基本液状タイプエポキシ“828”
EP1007:三菱化学製基本固形タイプエポキシ“1007”
1B2PZ:四国化成製1B2PZ 1 − ベンジル − 2 − フェニルイミダゾール
DICY7:三菱化学製DICY7 ジシアンジアミド
SP−152:(株)ADEKA製 アデカオプトマーSP−152 トリアリールスルホニウム塩:
TMPTA:ダイセル・オルネクス株式会社製TMPT トリメチロールプロパントリアクリレート
DPHA:ダイセル・オルネクス株式会社製DPHA ジペンタエリスリトールヘキサアクリレート
DCPA:共栄社化学製 ライトアクリレートDCPA
IRGACURE TPO:BASFジャパン社製 IRGACURE TPO
IRGACURE 907:BASFジャパン社製 IRGACURE 907
IRGACURE OXE02:BASFジャパン社製 IRGACURE OXE02
パークミルD:日本油脂株式会社製 パークミルD ジクミルパーオキサイド
M52N:アルケマ社製 ナノストレングスM52N Y−X−Y型ブロック共重合体
シリカ:アドマテックス社製 アドマファインSO−E2
硫酸バリウム:B−30:堺化学工業社製 表面処理硫酸バリウム
青色着色剤:C.I.Pigment Blue 15:3
黄色着色剤:C.I.Pigment Yellow 147
赤色発色剤:BASFジャパン社製 Paliogen Red K3580
なお、表中の硬化剤成分(A2−1)1、硬化性成分(B1)1、および硬化性成分(B1)2の値は固形分換算の値を表す。
上記表1で用いた硬化性成分(A1)を熱硬化剤成分により熱硬化させた場合の体積収縮率を測定した。表1の硬化性樹脂組成物1において用いた硬化性成分(A1)の成分を表1に記載した割合で合計10.0gとなるように混合し、必要に応じて加熱しながら撹拌し、更に熱硬化性成分である2−エチル−4−メチルイミダゾールを0.2g添加した混合物を調製した。
ρ=(α×ρ0)/(α―β)
(上記式中、ρは固形物の密度、αは大気中での固形物の質量、βは置換液中での固形物の質量、ρ0は測定温度での蒸留水の密度、を表す。)
体積収縮率=(1−(硬化性成分(A1)の硬化前の密度/硬化後の密度))×100
また、硬化性樹脂組成物2〜11において用いた硬化性成分(A1)についても、上記と同様にして体積収縮率を求めた。
硬化性樹脂組成物1〜11において用いた硬化性成分(A1)の体積収縮率(%)は、下記の表3に示される通りであった。
上記表1で用いた硬化性成分(B1)を光硬化剤成分により光硬化させた場合の体積収縮率を測定した。表1の硬化性樹脂組成物1において用いた硬化性成分(B1)の成分を表1に記載した割合で合計10.0gとなるように混合し、必要に応じて加熱しながら撹拌し、更に光硬化性成分であるBASF社製IRGACURE TPOを0.2g添加した混合物を調製した。
体積収縮率=(1−(硬化性成分(B1)の硬化前の密度/硬化後の密度))×100
また、硬化性樹脂組成物2〜11において用いた硬化性成分(B1)についても、上記と同様にして体積収縮率を求めた。
硬化性樹脂組成物1〜11において用いた硬化性成分(B1)の体積収縮率(%)は、下記の表3に示される通りであった。
各硬化性樹脂組成物1〜11をメチルエチルケトンで適宜希釈した後、アプリケーターを用いて、乾燥後の膜厚が40μmになるようにPETフィルム(東レ社製、FB−50:16μm)に塗布し、80℃で30分乾燥させドライフィルム1〜11を得た。
キャノシス株式会社製の片面に100nmのSiO2膜が形成された4inch、厚み150umのP型シリコンウエハを、ダイシング装置を用いてダイシングを行い、10mm×10mm角の半導体チップを得た。SUS製平面基板上に仮固定フィルムを配置し、上記半導体チップをSiO2面が仮固定フィルムと接触し、半導体チップの間が上下左右で10mm間隔となるように縦横5×5個配置した。この上に100mm×100mm角シート状の半導体用封止材を中心位置がおよそ一致するように積層し、加熱式プレス圧着機を用いて150℃で1時間圧縮成形させた。半導体用封止材としては、下記の組成を有する混練物を2枚の50umのカバーフィルム(帝人ピューレックスフィルム)に挟むように配置し、平板プレス法により混練物をシート状に形成し、厚さ200umのシート状に形成したものを用いた。
以下の成分を配合し、ロール混練機で70℃4分間、続いて120℃6分間加熱し、合計10分間、減圧(0.01kg/cm2)しながら溶融混練し、混練物を作製した。
・ナフタレン型エポキシ樹脂(日本化薬社製NC−7000) 30部
・ビキシレノール型エポキシ樹脂(三菱化学社製 YX−4000) 10部
・フェノール樹脂(ザ・ダウ・ケミカル・カンパニ−製 DEN−431) 10部
・アントラキノン 2部
・カーボンブラック(三菱化学社製 カーボンMA−100) 10部
・球状シリカ(アドマテックス社製 アドマファインSO−E2) 500部
・シランカップリング剤(信越化学社製 KBM−403) 2部
・2−フェニルイミダゾール(四国化成工業(株)製 2PZ) 2部
まず、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)−プロパンを、N−メチルピロリドンに溶解させ、4,4’−ジフェニルエーテルジカルボン酸クロリドのN−メチルピロリドンを滴下しながら0〜5℃で反応させて、重量平均分子量1.3×104のポリヒドロキシアミド(ポリベンゾオキサゾール前駆体)樹脂を合成した。
次いで、ポリヒドロキシアミド樹脂を含む下記の成分を配合し、この混合溶液を3μm孔のテフロン(登録商標)フィルタを用いて加圧ろ過して、再配線用樹脂組成物を調製した。
・ポリヒドロキシアミド樹脂(Z2) 100部
・フェノール樹脂(ザ・ダウ・ケミカル・カンパニ−製 DEN−431) 10部
・1−ナフトキノン−2−ジアジド−5−スルホン酸エステル
(AZエレクトロニックマテリアルズ社製商品名TPPA528) 10部
・Y−X−Y型ブロック共重合体
(アルケマ社製 ナノストレングスM52N) 5部
・シランカップリング剤(信越化学社製 KBM−403) 2部
・γ−ブチロラクトン 30部
・プロピレングリコールモノメチルエーテルアセテート 120部
UV1:25℃下で、メタルハライドランプを用いて3000mJ/cm2で全面照射
UV2:25℃下で、メタルハライドランプを用いて2000mJ/cm2で全面照射
UV3:25℃下で、メタルハライドランプを用いて1500mJ/cm2で全面照射
UV4:25℃下で、メタルハライドランプを用いて2000mJ/cm2で、パターンマスクを介して半導体チップが埋め込まれている位置にのみ照射
K1:170℃で1時間の加熱
上記のようにしてドライフィルムを硬化させて反り矯正層を形成した擬似ウェハの反り量を測定した。反り量は、25℃においてロングジョウノギスを用いて測定した。擬似ウェハの周辺部の2点を基準として中心部の反りが±2mm以下であれば良好(〇)とした。±2〜3mmは△、±3mmを超えるときは不良(×)と判定した。×判定のものはそのあとの評価を行わなかった。評価結果は下記の表3に示される通りであった。
上記の反り評価において良好な結果が得られたウェハはダイシングしてチップ形状に切り出し、1つの条件に付き10個のサンプルについて半田耐熱性(260℃で10秒間を3回)、冷熱サイクル500回(−40℃で15分間放置した後に125℃で15分間放置するのを1サイクルとする)の信頼性試験を行った。その後、擬似ウェハの断面の顕微鏡観察を行い、硬化性樹脂組成物が密着している境界部分を観察して、はく離が生じている不良品の有無を確認した。10個中はく離が0個のとき合格(〇)、1つ以上で剥離が生じていた場合は不合格(×)とした。評価結果は下記の表3に示される通りであった。
Claims (6)
- 少なくとも2種以上の硬化反応により硬化し得る硬化性樹脂組成物であって、前記一方の硬化反応により体積が収縮する硬化性成分(A1)と、他方の硬化反応により体積が収縮する硬化性成分(B1)とを含んでなることを特徴とする、硬化性樹脂組成物。
- 前記一方の硬化反応がイオン性の開環重合反応または重付加の重合反応であり、前記他方の硬化反応がラジカル性の付加重合反応である、請求項1に記載の硬化性樹脂組成物。
- 前記イオン性の開環重合反応または重付加の重合反応が、加熱によるイオン性の開環重合反応または重付加の重合反応であり、前記ラジカル性付加重合反応が光ラジカル性付加重合反応である、請求項2に記載の硬化性樹脂組成物。
- 前記イオン性の開環重合反応または重付加の重合反応により体積が収縮する硬化性成分(A1)が硬化した際の体積収縮率A(%)が0<A≦7の範囲にあり、且つ
前記ラジカル性付加重合反応により体積が収縮する硬化性成分(B1)が硬化した際の体積収縮率B(%)が5≦B≦30の範囲にある、請求項3に記載の硬化性樹脂組成物。 - 前記体積収縮率Aおよび体積収縮率Bが、下記式:
A<B
を満たす、請求項4に記載の硬化性樹脂組成物。 - ファンアウト型のウェハレベルパッケージの再配線層が設けられている面とは反対の面に設けられる反り矯正層の形成に用いられる、請求項1〜5のいずれか一項に記載の硬化性樹脂組成物。
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JP6998250B2 (ja) | 2018-03-27 | 2022-01-18 | 日本カーバイド工業株式会社 | 赤外線レーザ照射用樹脂組成物及び赤外線レーザ照射用樹脂フィルム |
JP2019174603A (ja) * | 2018-03-28 | 2019-10-10 | 東レ株式会社 | 感光性樹脂組成物およびそれを用いた硬化膜 |
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