JP2019168680A - 感光性樹脂組成物、感光性樹脂積層体、及びパターン形成方法 - Google Patents
感光性樹脂組成物、感光性樹脂積層体、及びパターン形成方法 Download PDFInfo
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- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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Classifications
-
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Abstract
Description
1.(A)1級アルコール性ヒドロキシ基を1.0×10-7eq/g〜8.0×10-3eq/g含むポリイミドシリコーン、
(B)架橋剤、
(C)光酸発生剤、
(D)多官能エポキシ化合物、
(E)(A)成分のポリイミドシリコーン100質量部に対し、1〜70質量部の平均粒径が0.01〜20.0μmのフィラー、及び
(F)(A)成分のポリイミドシリコーン100質量部に対し、0.01〜30質量部の着色剤
を含む感光性樹脂組成物。
2.更に、(G)有機溶剤を含む1の感光性樹脂組成物。
3.(G)有機溶剤が、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、乳酸エチル、シクロヘキサノン、シクロペンタノン、メチルイソブチルケトン及びγ−ブチロラクトンからなる群から選ばれる少なくとも1種である1又は2の感光性樹脂組成物。
4.(A)ポリイミドシリコーンが、下記式(1−1)で表される繰り返し単位及び下記式(1−2)で表される繰り返し単位を含むものである1〜3のいずれかの感光性樹脂組成物。
Y1は、下記式(3)で表される基である。
X2は、式(2)で表される基以外の4価の有機基である。
p及びqは、正の整数であり、0.01≦p/(p+q)<1を満たす。
破線は、結合手である。]
5.X2が、下記式で表される基から選ばれる基である4の感光性樹脂組成物。
6.(F)着色剤が、カーボンブラックである1〜5のいずれかの感光性樹脂組成物。
7.(D)成分が、ビスフェノール骨格を有する多官能エポキシ化合物、フェノールノボラック多官能エポキシ化合物及び多官能エポキシシリコーンからなる群から選ばれる少なくとも1種を含む1〜6のいずれかの感光性樹脂組成物。
8.基材フィルム層と、1〜7のいずれかの感光性樹脂組成物から得られる感光性樹脂層と、カバーフィルム層とを備える感光性樹脂積層体。
9.(i)1〜7のいずれかの感光性樹脂組成物を用いて感光性樹脂膜を基板上に形成する工程、
(ii)前記感光性樹脂膜を露光する工程、及び
(iii)現像液で現像する工程
を含むパターン形成方法。
10.(i)8の感光性樹脂積層体を用いて感光性樹脂膜を基板上に形成する工程、
(ii)前記感光性樹脂膜を露光する工程、及び
(iii)現像液で現像する工程
を含むパターン形成方法。
(A)成分として、1級アルコール性ヒドロキシ基を1.0×10-7eq/g〜8.0×10-3eq/g含むポリイミドシリコーン、
(B)成分として、架橋剤、
(C)成分として、光酸発生剤、
(D)成分として、多官能エポキシ化合物、
(E)成分として、平均粒径が0.01〜20.0μmのフィラー、及び
(F)成分として、着色剤
を含むものである。
(A)成分であるポリイミドシリコーンは、1.0×10-7eq/g〜8.0×10-3eq/gの1級アルコール性ヒドロキシ基を含む。前記1級アルコール性ヒドロキシ基の含有量が前記範囲を外れると、現像時に樹脂が基板から剥離したり、未露光部の溶解性が低下したりする。なお、1級アルコール性ヒドロキシ基とは、1級炭素原子に結合しているヒドロキシ基を意味する。すなわち、(A)成分のポリイミドシリコーンは、1級アルコール構造を有するものである。
(B)成分の架橋剤は、(A)成分と架橋反応を起こし、パターンの形成を容易になし得るための成分であるとともに、膜の強度を更に上げるものである。
(C)成分の光酸発生剤は、光照射によって分解し、酸を発生するものであれば特に限定されないが、波長240〜500nmの光を照射することによって酸を発生するものが好ましい。前記光酸発生剤は、硬化触媒として機能する。前記光酸発生剤としては、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。
(D)成分の多官能エポキシ化合物は、パターニング後の加熱硬化時にベースポリマー(すなわち(A)成分)と架橋反応を行い、皮膜の信頼性や基板との密着性に寄与する。
(E)成分のフィラーとしては、シリカ、アルミナ、窒化ケイ素、酸化チタン等が挙げられるが、これらに限定されない。前記フィラーは、その表面を改質してもしなくても使用できるが、改質した場合、透明度が上がることが期待できるため、好ましい。フィラーの表面改質は、例えば、シランカップリング剤、チタネートカップリング剤、有機シリル塩化物によって行うことができる。
(F)成分の着色剤は、具体的には、顔料や染料等であり、レーザーマーキング性の点から、カーボンブラックが好ましい。(F)成分の含有量は、(A)成分100質量部に対し、0.01〜30質量部であるが、0.1〜10質量部が好ましく、0.8〜5質量部が更に好ましい。(F)成分の含有量が、0.01質量部未満だと着色剤の効果が低く、30質量部より多いと光透過率が大きく低下して、露光時に十分に硬化できなかったり、副反応を起こし、架橋反応を阻害したりするおそれがある。(F)成分は、1種単独で又は2種以上を組み合わせて使用することができる。
本発明の感光性樹脂組成物は、必要に応じ、(G)成分として有機溶剤を含んでもよい。前記有機溶剤としては、(A)成分、(B)成分、(C)成分及び(D)成分が溶解可能であって、かつ(E)成分と(F)成分とが分散可能なものが好ましい。
本発明の感光性樹脂組成物には、前記各成分以外に、更にその他の成分を添加してもよい。その他の成分としては、界面活性剤、密着助剤等が挙げられる。
本発明の感光性樹脂組成物は、フィルム状に加工して使用することができる。フィルムとする場合、基材フィルム層上に前述した感光性樹脂組成物を用いて感光性樹脂膜を形成し、その上にカバーフィルム層を形成するのが好ましい。
本発明の感光性樹脂組成物を用いて基板上にパターンを形成する方法は、以下の工程を含むものである。
(i)前述した感光性樹脂組成物又は感光性樹脂積層体を用いて感光性樹脂膜を基板上に形成する工程、
(ii)前記感光性樹脂膜を露光する工程、及び
(iii)現像液で現像する工程。
[合成例1]
攪拌機、温度計及び窒素置換装置を備えたフラスコに、4,4'−オキシジフタル酸二無水物62.0g(0.2モル)、酸無水物変性シリコーン(S−1)302.3g(0.3モル)及びN−メチル−2−ピロリドン800gを仕込んだ。そこへ、反応系の温度が50℃を超えないように調節しながら、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)ヘキサフルオロプロパン183.1g(0.5モル)を加えた。その後、更に室温で10時間攪拌した。次に、前記フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン120gを加え、170℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。前記褐色溶液を室温(25℃)まで冷却した後、フェノール性ヒドロキシ基を有するポリイミドシリコーン溶液を得た。
攪拌機、温度計及び窒素置換装置を備えたフラスコに、4,4'−ヘキサフルオロプロピリデンビスフタル酸二無水物111.1g(0.25モル)、酸無水物変性シリコーン(S−2)264.0g(0.25モル)及びγ−ブチロラクトン800gを仕込んだ。そこへ、反応系の温度が50℃を超えないように調節しながら、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)ヘキサフルオロプロパン183.1g(0.5モル)を加えた。その後、更に室温で10時間攪拌した。次に、前記フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン200gを加え、170℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。前記褐色溶液を室温(25℃)まで冷却した後、フェノール性ヒドロキシ基を有するポリイミドシリコーン溶液を得た。
攪拌機、温度計及び窒素置換装置を備えたフラスコに、4,4'−オキシジフタル酸二無水物62.0g(0.2モル)、酸無水物変性シリコーン(S−3)325.0g(0.2モル)及びγ−ブチロラクトン800gを仕込んだ。そこへ、反応系の温度が50℃を超えないように調節しながら、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)ヘキサフルオロプロパン73.3g(0.2モル)及び1,3−ビス(3−アミノフェノキシ)ベンゼン58.5g(0.2モル)を加えた。その後、p−アミノフェノール1.1g(0.01モル)を加え、更に室温で10時間攪拌した。次に、前記フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン250gを加え、170℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。前記褐色溶液を室温(25℃)まで冷却した後、フェノール性ヒドロキシ基を有するポリイミドシリコーン溶液を得た。
攪拌機、温度計及び窒素置換装置を備えたフラスコに、4,4'−オキシジフタル酸二無水物91.6g(0.25モル)、酸無水物変性シリコーン(S−3)406.2g(0.25モル)及びγ−ブチロラクトン1000gを仕込んだ。そこへ、反応系の温度が50℃を超えないように調節しながら、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)ヘキサフルオロプロパン146.5g(0.40モル)及び1,3−ビス(3−アミノフェノキシ)ベンゼン29.2g(0.10モル)を加えた。その後、p−アミノフェノール2.7g(0.025モル)を加え、更に室温で10時間攪拌した。次に、前記フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン300gを加え、170℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。前記褐色溶液を室温(25℃)まで冷却した後、フェノール性ヒドロキシ基を有するポリイミドシリコーン溶液を得た。
攪拌機、温度計及び窒素置換装置を備えたフラスコに、4,4'−オキシジフタル酸二無水物62.0g(0.2モル)、無水物変性シリコーン(S−1)302.3g(0.3モル)及びN−メチル−2−ピロリドン800gを仕込んだ。そこへ、反応系の温度が50℃を超えないように調節しながら、2,2−ビス(4−アミノ−3−ヒドロキシフェニル)ヘキサフルオロプロパン183.1g(0.5モル)を加えた。その後、更に室温で10時間攪拌した。次に、前記フラスコに水分受容器付き還流冷却器を取り付けた後、キシレン120gを加え、170℃に昇温してその温度を6時間保持したところ、褐色の溶液が得られた。前記褐色溶液を室温(25℃)まで冷却した後、メタノール中に投入し、析出した沈殿を濾過し、乾燥後、目的とするフェノール性ヒドロキシ基を有するポリイミドシリコーンA'−1を得た。GPC分析の結果、ポリイミドシリコーンA'−1のMwは、17,800であった。
[実施例1〜16、比較例1〜8]
表1及び2に記載した組成になるように、(A)成分、(B)成分、(C)成分、(D)、(E)成分、(F)成分及び(G)成分を配合して、攪拌、混合し、感光性樹脂組成物を調製した。表1及び2中、各成分は以下のとおりである。
ポリイミドシリコーンA−1〜A−4、A'−1
D−1:エピコート828(三菱ケミカル(株)製)2官能エポキシ樹脂
D−2:セロキサイド(登録商標)2021P((株)ダイセル製)2官能エポキシ樹脂
E−1:(株)アドマテックス製シリカ(平均粒径0.5μm)
E−2:(株)アドマテックス製シリカ(平均粒径8.0μm)
E−3:(株)アドマテックス製シリカ(平均粒径20.0μm)
顔料として、F−1:カーボンブラック(三菱ケミカル(株)製)
染料として、F−2:VALIFAST(登録商標)1821(オリヱント化学工業(株)製)
G−1:シクロペンタノン
G−2:プロピレングリコールモノメチルエーテル
表1及び2に記載された各感光性樹脂組成物を、厚さ100μmのPETフィルム上にブレードナイフを使用してコーティングし、その後、100℃の乾燥機で10分間加熱して、PETフィルム上に膜厚50μmの感光性樹脂層を形成した。前記感光性樹脂層上にポリエチレンのカバーフィルムをラミネートすることで、感光性樹脂積層体を作製した。評価は以下の方法にて行った。なお、樹脂厚みは、接触式厚み計によって測定した。
前記感光性樹脂積層体のカバーフィルムを剥がし、フィルムラミネータで8インチシリコンウエハにラミネートした後、基材のPETフィルムを剥離して、シリコンウエハ上に感光性樹脂層を転写した。ホットプレートで90℃、2分間加熱して乾燥させた後、ズース社製マスクアライナーMA8(光源波長:ブロードバンド)を用いて、直径200μmのホールを等間隔に有する石英製マスクを介して、ブロードバンドの紫外線を2,000mJ/cm2で照射した。照射後、ホットプレートで90℃、2分間加熱し、冷却後、2.38質量%TMAH水溶液に5分間浸し、未露光部を溶解除去し、パターンを形成した。パターンが形成され、ホール部分が底まで開口していた場合を「○」、底まで達していなかった場合を「×」とした。結果を表3及び4に示す。
前記感光性樹脂積層体のカバーフィルムを剥がし、フィルムラミネータで8インチシリコンウエハにラミネートした後、PETフィルムを剥離することによって、シリコンウエハ上に感光性樹脂層を転写した。ホットプレートで90℃、2分間加熱して乾燥させた後、マスクを使用せず、ウエハ全面に、波長365nmの光を露光量800mJ/cm2で照射した。照射後、90℃で2分間加熱し、冷却後、200℃で2時間加熱して硬化させた。その後、レーザーマーキング装置MD-V9900((株)キーエンス製)を用いて、1,064nmで5W、0.6秒での照射条件でレーザーマークを施し、レーザーマークを視認できるか確認した。確認できた場合を「○」、視認できなかったり、刻印されても薄い等の理由により読みづらかったりした場合を「×」とした。結果を表3及び4に示す。
前記感光性樹脂積層体を外径8.5cmのプラスチック製の円筒に巻きつけ、10秒間静置後、前記積層体を元に戻し、前記積層体に異常がないか確認した。変化がない場合を「○」、割れ等が発生していた場合を「×」とした。結果を表3及び4に示す。
(株)日立ハイテクサイエンス製U-3900H形分光光度計を用いて、前記感光性樹脂積層体の感光性樹脂層の波長365nmの光の透過率を測定した。結果を表3及び4に示す。
フィルムをそのまま露光し、オーブンで90℃で2分間加熱し、その後、オーブンで200℃で2時間加熱し、硬化させた。その後、硬化したフィルムを粘弾性測定装置((株)日立ハイテクサイエンス製DMA7100)を用いて、−10〜320℃の範囲で昇温測定し、25℃の弾性率を読み取った。結果を表3及び4に示す。
Claims (10)
- (A)1級アルコール性ヒドロキシ基を1.0×10-7eq/g〜8.0×10-3eq/g含むポリイミドシリコーン、
(B)架橋剤、
(C)光酸発生剤、
(D)多官能エポキシ化合物、
(E)(A)成分のポリイミドシリコーン100質量部に対し、1〜70質量部の平均粒径が0.01〜20.0μmのフィラー、及び
(F)(A)成分のポリイミドシリコーン100質量部に対し、0.01〜30質量部の着色剤
を含む感光性樹脂組成物。 - 更に、(G)有機溶剤を含む請求項1記載の感光性樹脂組成物。
- (G)有機溶剤が、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、乳酸エチル、シクロヘキサノン、シクロペンタノン、メチルイソブチルケトン及びγ−ブチロラクトンからなる群から選ばれる少なくとも1種である請求項1又は2記載の感光性樹脂組成物。
- (A)ポリイミドシリコーンが、下記式(1−1)で表される繰り返し単位及び下記式(1−2)で表される繰り返し単位を含むものである請求項1〜3のいずれか1項記載の感光性樹脂組成物。
Y1は、下記式(3)で表される基である。
X2は、式(2)で表される基以外の4価の有機基である。
p及びqは、正の整数であり、0.01≦p/(p+q)<1を満たす。
破線は、結合手である。] - (F)着色剤が、カーボンブラックである請求項1〜5のいずれか1項記載の感光性樹脂組成物。
- (D)成分が、ビスフェノール骨格を有する多官能エポキシ化合物、フェノールノボラック多官能エポキシ化合物及び多官能エポキシシリコーンからなる群から選ばれる少なくとも1種を含む請求項1〜6のいずれか1項記載の感光性樹脂組成物。
- 基材フィルム層と、請求項1〜7のいずれか1項記載の感光性樹脂組成物から得られる感光性樹脂層と、カバーフィルム層とを備える感光性樹脂積層体。
- (i)請求項1〜7のいずれか1項記載の感光性樹脂組成物を用いて感光性樹脂膜を基板上に形成する工程、
(ii)前記感光性樹脂膜を露光する工程、及び
(iii)現像液で現像する工程
を含むパターン形成方法。 - (i)請求項8記載の感光性樹脂積層体を用いて感光性樹脂膜を基板上に形成する工程、
(ii)前記感光性樹脂膜を露光する工程、及び
(iii)現像液で現像する工程
を含むパターン形成方法。
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WO2022210797A1 (ja) * | 2021-03-29 | 2022-10-06 | 株式会社カネカ | ネガ型感光性組成物、光半導体装置、固体撮像装置、及び電子機器 |
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JP7111031B2 (ja) | 2022-08-02 |
EP3553601A1 (en) | 2019-10-16 |
CN110297398A (zh) | 2019-10-01 |
US11294283B2 (en) | 2022-04-05 |
US20190294045A1 (en) | 2019-09-26 |
EP3553601B1 (en) | 2020-09-23 |
KR20190111797A (ko) | 2019-10-02 |
TWI802667B (zh) | 2023-05-21 |
TW201945849A (zh) | 2019-12-01 |
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