JP6616743B2 - シリコーン骨格含有高分子化合物、光硬化性樹脂組成物、光硬化性ドライフィルム、積層体、及びパターン形成方法 - Google Patents
シリコーン骨格含有高分子化合物、光硬化性樹脂組成物、光硬化性ドライフィルム、積層体、及びパターン形成方法 Download PDFInfo
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Classifications
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Description
(i)前記光硬化性樹脂組成物を基板上に塗布することにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程、
を含むことを特徴とするパターン形成方法を提供する。
(i)前記光硬化性ドライフィルムを基板に密着させることにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程、
を含むことを特徴とするパターン形成方法を提供する。
本発明のシリコーン骨格含有高分子化合物(本発明の光硬化性樹脂組成物における(A)成分)は、下記式(1)で示される、シリコーン骨格を含み、重量平均分子量が3,000〜500,000であるシリコーン骨格含有高分子化合物である。
本発明のシリコーン骨格含有高分子化合物は、下記一般式(7)、下記一般式(8)、下記一般式(9)、下記一般式(10)、下記一般式(11)、下記一般式(12)及び下記一般式(13)で表される化合物から選択される化合物を用いて金属触媒存在下、付加重合することにより製造することができる。
本発明の光硬化性樹脂組成物は、上記シリコーン骨格含有高分子化合物(A)及び190〜500nmの光によって分解し、酸を発生する光酸発生剤(B)を含有する組成物である。このような光硬化性樹脂組成物は、幅広い膜厚範囲で皮膜形成でき、後述するパターン形成方法により微細かつ垂直性に優れたパターンを形成することが可能である。また、このような光硬化性樹脂組成物及びこのドライフィルムを用いたパターン形成方法により得られる硬化皮膜は、パターン性、耐熱性、電気絶縁性、絶縁保護膜としての信頼性、特に基板等との密着性に優れた皮膜となる。
光酸発生剤(B)としては、190〜500nmの波長の光照射により酸を発生し、これが硬化触媒となるものが挙げられる。本発明の樹脂組成物は酸発生剤の相溶性が優れるため、幅広い酸発生剤を使用することができる。そのような酸発生剤としては、例えば、オニウム塩、ジアゾメタン誘導体、グリオキシム誘導体、β−ケトスルホン誘導体、ジスルホン誘導体、ニトロベンジルスルホネート誘導体、スルホン酸エステル誘導体、イミド−イル−スルホネート誘導体、オキシムスルホネート誘導体、イミノスルホネート誘導体、トリアジン誘導体等が挙げられる。
(R19)vM+ K− (14)
(式中、R19は置換基を有してもよい炭素数1〜12の直鎖状、分岐状又は環状のアルキル基、炭素数6〜12のアリール基又は炭素数7〜12のアラルキル基を表し、M+はヨードニウム又はスルホニウムを表し、K−は非求核性対向イオンを表し、vは2又は3を表す。)
更に、本発明の光硬化性樹脂組成物は、架橋剤(C)を含有することが好ましい。本発明で使用される(C)成分は、上述した(A)成分の式(3)におけるフェノール基、あるいはR9及び/又はR10のアルコキシ基と縮合反応を起こし、パターンの形成を容易になし得るための成分であると共に、硬化物の強度を更に上げるものである。そのような(C)成分としては重量平均分子量が150〜10,000、特に200〜3,000の樹脂が好ましい。重量平均分子量が150以上であれば、十分な光硬化性を得ることができ、10,000以下であれば組成物の硬化後の耐熱性を悪化させる恐れがないために好ましい。
本発明の光硬化性樹脂組成物は、溶剤(D)を含有するものとすることができる。上述したシリコーン骨格含有高分子化合物(A)、光酸発生剤(B)、及び架橋剤(C)、後述する塩基性化合物(E)、その他各種添加剤が溶解可能な溶剤であればいずれも選択し、配合することができるが、特に有機溶剤がこれら成分の溶解性に優れている。
更に、本発明の光硬化性樹脂組成物は、塩基性化合物(E)を含有するものとすることができる。塩基性化合物(E)としては、光酸発生剤より発生した酸が光硬化性樹脂層内を拡散する際の拡散速度を抑制することができる化合物が適している。そして、上記塩基性化合物の配合により、解像度が向上し、露光後の感度変化を抑制し、基板依存性又は環境依存性を少なくし、露光余裕度やパターン形状を向上させることができる。
N( α )w( β )3−w (17)
(上記一般式(17)中、wは1、2又は3である。側鎖αは同一でも異なっていてもよく、下記一般式(18)〜(20)で表されるいずれかの置換基である。側鎖βは同一又は異種の、水素原子又は直鎖状、分岐状若しくは環状の炭素数1〜20のアルキル基を示し、エーテル結合又はヒドロキシル基を含んでもよい。また、α同士が結合して環を形成してもよい。)
本発明の光硬化性樹脂組成物には、上述した各成分以外に、更に添加剤を配合してもよい。添加剤としては、例えば、塗布性を向上させるために慣用されている界面活性剤を添加することができる。
次に、上記本発明の光硬化性樹脂組成物を用いた本発明のパターン形成方法について説明する。本発明のパターン形成方法は、下記の工程を含むパターン形成方法である。
(i)本発明の光硬化性樹脂組成物を基板上に塗布することにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程。
本発明の光硬化性ドライフィルムは、本発明の光硬化性樹脂組成物が、支持フィルム上に塗布・乾燥されたものであることを特徴とする光硬化性ドライフィルムである。
光硬化性ドライフィルムによるパターン形成は、下記の工程を含むパターン形成方法である。
(i)本発明の光硬化性ドライフィルムを基板に密着させることにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程。
本発明における積層体は、開口幅が10〜100μmであり、かつ深さが10〜120μmである溝及び孔のいずれか一方又は両方を有する基板に、本発明の光硬化性樹脂組成物の硬化物層、又は本発明の光硬化性ドライフィルムにおける光硬化性樹脂層の硬化物層が形成されたものであることを特徴とする積層体である。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−1)で示される化合物135.5g(0.25モル)、上記式(S−3a)で示される化合物28.5g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.2モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率69.1質量%、S−3aのモル数fを1とした場合、d=4、c+e=5、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は42,000であった。得られた樹脂を樹脂(1)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−2)で示される化合物66.3g(0.25モル)、上記式(S−3a)で示される化合物28.5g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率71.7質量%、S−3aのモル数fを1とした場合、d=4、c+e=5、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は45,000であった。得られた樹脂を樹脂(2)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−2)で示される化合物53.0g(0.20モル)、上記式(S−3a)で示される化合物57.0g(0.10モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率70.4質量%、S−3aのモル数fを1とした場合、d=2、c+e=2、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は44,000であった。得られた樹脂を樹脂(3)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−2)で示される化合物26.5g(0.10モル)、上記式(S−3a)で示される化合物57.0g(0.10モル)、上記式(S−4)で示される化合物18.6g(0.10モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=20)317g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率56.3質量%、S−3aのモル数fを1とした場合、d=2、c+e=1、g=1)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は40,000であった。得られた樹脂を樹脂(4)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−1)で示される化合物135.5g(0.25モル)、上記式(S−3b)で示される化合物28.5g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.2モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率69.0質量%、S−3bのモル数fを1とした場合、d=4、c+e=5、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は43,000であった。得られた樹脂を樹脂(5)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−2)で示される化合物66.3g(0.25モル)、上記式(S−3b)で示される化合物28.5g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率71.7質量%、S−3bのモル数fを1とした場合、d=4、c+e=5、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は44,000であった。得られた樹脂を樹脂(6)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−1)で示される化合物108.4g(0.20モル)、上記式(S−2)で示される化合物53.0g(0.20モル)、上記式(S−3a)で示される化合物57.0g(0.10モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率68.6質量%、S−3aのモル数fを1とした場合、d=0、c+e=4、g=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は43,000であった。得られた樹脂を樹脂(7)とし、実施例に供した。なお、得られた樹脂は、1H NMR(Bluker製)により、一般式(1)である樹脂であると断定した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−1)で示される化合物135.5g(0.25モル)、上記式(S−4)で示される化合物9.3g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率70.6質量%、S−3を含まないためS−3モル数f=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は41,000であった。得られた樹脂を樹脂(8)とし、比較例に供した。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した3Lフラスコ内に、上記式(S−2)で示される化合物66.3g(0.25モル)、上記式(S−4)で示される化合物9.3g(0.05モル)、上記式(S−7)で示される化合物86.0g(0.20モル)を加えた後、トルエン2,000gを加え、70℃に加温した。その後、塩化白金酸トルエン溶液(白金濃度0.5質量%)1.0gを投入し、上記式(S−5)で示される化合物58.2g(0.30モル)及び上記式(S−6)で示される化合物(y=40)604.0g(0.20モル)を1時間かけて滴下した(ヒドロシリル基の合計モル数/アルケニル基の合計モル数=1/1、シリコーン含有率73.3質量%、S−3を含まないためS−3モル数f=0)。滴下終了後、100℃まで加温し6時間熟成した後、反応溶液からトルエンを減圧留去して得られた生成物のGPCにより測定したポリスチレン換算の重量平均分子量は46,000であった。得られた樹脂を樹脂(9)とし、比較例に供した。
<光硬化性樹脂組成物の調製>
表1に記載の配合量に従って、シリコーン樹脂、光酸発生剤、架橋剤、溶剤及び塩基性化合物を配合し、その後常温にて撹拌、混合、溶解した後、テフロン(登録商標)製1.0μmフィルターで精密濾過を行い、実施例1〜12及び比較例1〜2の光硬化性樹脂組成物を得た。なお、表1中の配合量を示す数値の単位は「質量部」である。
フィルムコーターとしてダイコーター、支持フィルムとしてポリエチレンテレフタレートフィルム(厚さ38μm)を用いて、実施例1〜12及び比較例1〜2の光硬化性樹脂組成物をそれぞれ上記支持フィルム上に塗布した。次いで、100℃に設定された熱風循環オーブン(長さ4m)を5分間で通過させることにより乾燥し、支持フィルム上に光硬化性樹脂層を形成し、光硬化性ドライフィルムを得た。上記光硬化性樹脂層の上から、保護フィルムとしてのポリエチレンフィルム(厚さ50μm)をラミネートロールで圧力1MPaにて貼り合わせ、保護フィルム付き光硬化性ドライフィルムを作製した。各光硬化性樹脂層の膜厚は表2に記載した。なお、膜厚は光干渉式厚膜測定機により測定した。
Claims (16)
- 下記式(1)で示される、シリコーン骨格を含み、重量平均分子量が3,000〜500,000であるシリコーン骨格含有高分子化合物であって、
前記一般式(5)が、下記(5−1)式であることを特徴とするシリコーン骨格含有高分子化合物。
- 0≦c/X≦0.6、0≦d/X≦0.8、0≦e/X≦0.6、0<f/X≦0.8、0≦g/X≦0.6である(ただし、X=c+d+e+f+gである)ことを特徴とする請求項1に記載のシリコーン骨格含有高分子化合物。
- 0<c/X≦0.4、0<d/X≦0.7、0<e/X≦0.4、0.1≦f/X≦0.6、0≦g/X≦0.4であることを特徴とする請求項2に記載のシリコーン骨格含有高分子化合物。
- 請求項1から請求項3のいずれか1項に記載のシリコーン骨格含有高分子化合物(A)、及び190〜500nmの光によって分解し、酸を発生する光酸発生剤(B)を含有するものであることを特徴とする光硬化性樹脂組成物。
- 更に、架橋剤(C)を含有するものであることを特徴とする請求項4に記載の光硬化性樹脂組成物。
- 前記架橋剤(C)が、ホルムアルデヒド又はホルムアルデヒド−アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、及び、1分子中に平均して2個以上のエポキシ基を有するエポキシ化合物から選ばれるいずれか1種以上であることを特徴とする請求項5に記載の光硬化性樹脂組成物。
- 更に、溶剤(D)を含有するものであることを特徴とする請求項4から請求項6のいずれか1項に記載の光硬化性樹脂組成物。
- 更に、塩基性化合物(E)を含有するものであることを特徴とする請求項4から請求項7のいずれか1項に記載の光硬化性樹脂組成物。
- 請求項4から請求項8のいずれか1項に記載の光硬化性樹脂組成物が、支持フィルム上に塗布・乾燥されたものであることを特徴とする光硬化性ドライフィルム。
- 開口幅が10〜100μmであり、かつ深さが10〜120μmである溝及び孔のいずれか一方又は両方を有する基板に、請求項4から請求項8のいずれか1項記載の光硬化性樹脂組成物の硬化物層、又は請求項9に記載の光硬化性ドライフィルムにおける光硬化性樹脂層の硬化物層が形成されたものであることを特徴とする積層体。
- (i)請求項4から請求項8のいずれか1項に記載の光硬化性樹脂組成物を基板上に塗布することにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程、
を含むことを特徴とするパターン形成方法。 - (i)請求項9に記載の光硬化性ドライフィルムを基板に密着させることにより、前記基板上に光硬化性樹脂層を形成する工程、
(ii)前記光硬化性樹脂層を、フォトマスクを介して露光する工程、
(iii)露光後の加熱処理を行った後、現像液にて現像して非露光部を溶解除去してパターンを形成する工程、
を含むことを特徴とするパターン形成方法。 - 更に、(iv)現像によりパターン形成された皮膜を、100〜250℃の温度で後硬化する工程を含むことを特徴とする請求項11又は請求項12に記載のパターン形成方法。
- 前記基板が、開口幅が10〜100μmであり、かつ深さが10〜120μmである溝及び孔のいずれか一方又は両方を有するものであることを特徴とする請求項11から請求項13のいずれか一項に記載のパターン形成方法。
- 前記光硬化性樹脂組成物が、電気・電子部品保護用皮膜の材料であることを特徴とする請求項4から請求項8のいずれか1項に記載の光硬化性樹脂組成物。
- 前記光硬化性樹脂組成物が、2つの基板を接合するための基板接合用皮膜の材料であることを特徴とする請求項4から請求項8のいずれか1項に記載の光硬化性樹脂組成物。
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US10451970B2 (en) | 2019-10-22 |
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