JP6569250B2 - ポジ型感光性樹脂組成物、感光性エレメント、及びレジストパターンを形成する方法 - Google Patents
ポジ型感光性樹脂組成物、感光性エレメント、及びレジストパターンを形成する方法 Download PDFInfo
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- JP6569250B2 JP6569250B2 JP2015049201A JP2015049201A JP6569250B2 JP 6569250 B2 JP6569250 B2 JP 6569250B2 JP 2015049201 A JP2015049201 A JP 2015049201A JP 2015049201 A JP2015049201 A JP 2015049201A JP 6569250 B2 JP6569250 B2 JP 6569250B2
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- Prior art keywords
- cresol
- resin composition
- photosensitive
- photosensitive layer
- compound
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- 229930003836 cresol Natural products 0.000 claims description 39
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 37
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 16
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 11
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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 6
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- GXYCPGOCXLHIAT-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxyphenyl)-(2-hydroxyphenyl)methyl]phenol Chemical class OC1=CC=CC=C1C(C=1C(=C(C2CCCCC2)C=CC=1)O)C1=CC=CC(C2CCCCC2)=C1O GXYCPGOCXLHIAT-UHFFFAOYSA-N 0.000 description 3
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Images
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- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
(A)成分として用いるクレゾール樹脂は、メタクレゾール、パラクレゾール、オルトクレゾールから選ばれる1種以上のクレゾール化合物を含むフェノール化合物と、アルデヒド化合物との重縮合生成物である。クレゾール樹脂は、ノボラック型クレゾール樹脂であることが好ましい。重縮合は、例えば酸等の触媒存在下で行われる。
(B)成分である光酸発生剤は、光により酸を発生する化合物(又は感光剤)ともいえる。このような(B)成分は、光照射により酸を発生させ、光照射した部分のアルカリ水溶液への可溶性を増大させる機能を有する。(B)成分の具体例としては、o−キノンジアジド化合物、アリールジアゾニウム塩、ジアリールヨードニウム塩、トリアリールスルホニウム塩等が挙げられる。これらの中で、感度が高いことから、1,2−キノンジアジド化合物が好ましい。
当該ポジ型感光性樹脂組成物は、(C)成分としてエポキシ基を有するシラン化合物を含有する。(C)成分を含有させることで、当該ポジ型感光性樹脂組成物と種々の基板又は基材、特にガラスへの密着性を付与することができる。
本実施形態の感光性樹脂組成物は、必要に応じて、粘度を調整するために後述する溶剤を含有させてもよく、増感剤、吸光剤(染料)、可塑剤、顔料、充填材、難燃剤、安定剤、香料、熱架橋剤等を含有させてもよい。これらのその他の成分の含有量は上述した特性を実質的に損なわない範囲であれば、特に限定されない。
本実施形態に係る感光性エレメントは、支持体と、該支持体上に設けられた上記ポジ型感光性樹脂組成物から形成された感光層とを備える。感光層の支持体と反対側の面には、必要に応じて、保護層を積層してもよい。
本実施形態に係る支持体3は、少なくとも一方の面が離型処理されていることが好ましい。支持体の離型処理面上に上記ポジ型感光性樹脂組成物から形成された感光層を備えることによって、支持体を除去する際に、感光層に欠け等の不良が発生しにくくなる。ここで、離型処理とは、シリコーン系界面活性剤、シリコーン樹脂等のシリコーン系化合物、フッ素系界面活性剤、フッ素樹脂等のフッ素含有化合物、アルキッド樹脂等の離型剤で支持体の表面を薄く塗布する化学処理や、支持体をコロナ処理する等の物理処理を指す。
保護層5としては、例えば、ポリエチレン、ポリプロピレン、ポリエチレンテレフタレート等の重合体フィルムを用いることができる。また、支持体と同様に、離型処理を施した重合体フィルムを用いてもよい。感光性エレメントをロール状に巻き取る際の柔軟性の観点からは、保護層5として、ポリエチレンフィルムが特に好ましい。また、保護層5、感光層表面の凹みを低減できるよう、低フィッシュアイのフィルムであることが好ましい。
次に、レジストパターンの形成方法について説明する。
本実施形態に係る基板の加工方法は、基板(例えば、ガラス基板、金属表面を有する基板、透明導電層(ITO等)を有する基板)上に、上述したレジストパターンの形成方法によって、パターンを有する感光層(R1)形成する工程と、感光層R1をマスクとして、エッチング液を用いて前記基板をエッチングする第一のエッチング工程と、を備える。本実施形態に係る方法は、感光層R1の一部を露光し、露光後の感光層R1の一部を除去(現像)して、基板の表面の一部を露出させるパターンを有する感光層(R2)を形成する工程と、その後、感光層R2をマスクとして、エッチング液を用いて前記基板をエッチングする第二のエッチング工程と、を更に備えてもよい。これによって、異なる深さで基板を加工することができる。この場合も上述する感光性樹脂組成物を用いることで、優れたスループットが得られる。
(A)成分として、乾性油で変性したクレゾールから得られる変性ノボラック型フェノール樹脂(A1)及び(A2)を合成した。
メタクレゾール及びパラクレゾールが質量比40:60で混合されたクレゾール混合体450質量部に、亜麻仁油50質量部を加え15分間撹拌した。その後、50質量%トリフルオロ酢酸水溶液を1.12質量部加え、120℃で2時間撹拌した。2時間撹拌した後、混合物を室温(25℃、以下同様)まで冷却し、92%パラホルムアルデヒド75質量部、メタノール18質量部及びシュウ酸2質量部を加え、90℃で3時間撹拌した。次いで、減圧蒸留することで未反応のクレゾールを除去し、不飽和炭化水素基を有する変性クレゾール樹脂(A1)を得た。(A1)の重量平均分子量(Mw)は12000であった。
ポンプ:L−6200型(株式会社日立製作所製、商品名)
カラム:TSKgel−G5000HXL(東ソー株式会社製、商品名)
検出器:L−3300RI型(株式会社日立製作所製、商品名)
溶離液:テトラヒドロフラン
温度:30℃
流量:1.0mL/分
メタクレゾール及びパラクレゾールからなるクレゾール混合体をオルトクレゾールに変更し、メタノールの量を50質量部に変更した以外は、合成例A1と同様に操作して、不飽和炭化水素基を有する変性クレゾール樹脂(A2)を得た。(A2)のMwは2000であった。
(合成例A3)
メタクレゾール及びパラクレゾールが質量比40:60で混合されたクレゾール混合体500質量部に、92%パラホルムアルデヒド83質量部、メタノール18質量部及びシュウ酸1質量部を加え、90℃で3時間撹拌した。その後、減圧蒸留することで未反応のクレゾールを除去し、メタ−パラクレゾール樹脂(A3)を得た。(A3)のMwは12000であった。
メタノール添加量を130質量部に変更した以外は、合成例A3と同様に操作して、メタ−パラクレゾール樹脂(A4)を得た。(A4)のMwは1000であった。
オルトクレゾール336質量部に92%パラホルムアルデヒド60質量及びシュウ酸1.2質量部を加え、120℃で4時間撹拌した。その後、減圧蒸留することで未反応のオルトクレゾールを除去し、オルトクレゾール樹脂(A5)を得た。(A5)のMwは1000であった。
(実施例1)
(A)成分としての(A1)20質量部、(A3)20質量部及び(A5)45質量部と、(B)成分としての1,2−キノンジアジド化合物であるジアゾナフトキノン系感光剤(ダイトーケミックス株式会社製、商品名「PA−28」)(以下、「PA−28」と略記する)15質量部と、(C)成分としての3−グリシドキシプロピルトリメトキシシラン(以下、「KBM−403」と略記する)(信越化学工業株式会社製、商品名「KBM−403」)1質量部と、溶媒としてのメチルエチルケトン(以下、「MEK」と略記する)113質量部及びプロピレングリコールモノメチルエーテルアセタート(以下、「PGMEA」と略記する)70質量部とを混合した。その後、混合物をミックスローターで1日攪拌することで、感光性樹脂組成物を調製した。
表1に示す組成(単位:質量部)に変更した以外は、実施例1と同様にして、感光性樹脂組成物を調製した。表1に(C)成分として記載のシランカップリング剤の詳細は以下のとおりである。
KBM−403:3−グリシドキシプロピルトリメトキシシラン(信越化学工業株式会社製、商品名)
KBE−403:3−グリシドキシプロピルトリエトキシシラン(信越化学工業株式会社製、商品名)
KBE−402:3−グリシドキシプロピルメチルジエトキシシラン(信越化学工業株式会社製、商品名)
KBM−573:N−フェニル−3−アミノプロピルトリメトキシシラン(信越化学工業株式会社製、商品名)
KBM−503:3−メタクリロキシプロピルトリメトキシシラン(信越化学工業株式会社製、商品名)
KBE−585:3−ウレイドプロピルトリアルコキシシラン(信越化学工業株式会社製、商品名)
(実施例1〜10、及び比較例1〜5)
上記表1の感光性樹脂組成物を用い、以下の手順に従って感光性エレメントを作製した。まず、スピンコーター(ダイトロンテクノロジー株式会社製)を用いて、片面がシリコーン系化合物で離型処理された支持体としてのポリエチレンテレフタレート(PET)フィルム(帝人デュポンフィルム株式会社製、商品名「ピューレックス A53」)の離型処理面に、感光性樹脂組成物を塗布した。支持体の離型処理面の、膜厚25μmの粘着テープ(日東電工株式会社製、商品名「NITTO31B」)を用いた23℃での180°剥離試験により測定される剥離強度は3.861N/mであり、離型処理面の表面張力は44mN/mであった。スピンコートの条件は、回転速度300min−1で5秒間、次いで回転速度600min−1で30秒間の条件とした。その後、クリーンオーブン(タバイエスペック株式会社製、PVHC−231MS)にて、95℃で10分間乾燥を行い、厚み10μmの感光層を支持体上に有する感光性エレメントを得た。
ロールラミネータ(日立化成テクノプラント株式会社製、商品名)を用いて、上記感光性エレメントの感光層をガラス基板にラミネートし、評価サンプルを得た。ラミネートの条件は、圧力0.5MPa、上下ロール温度120℃、ラミネート速度0.5m/分とした。
後述する評価を行った。結果を表2に示す。
(露光工程及び現像工程)
得られた評価サンプルから支持体を剥がし、UV露光機(大日本スクリーン株式会社製、商品名「大型マニュアル露光機 MAP−1200」)を用いて400mJ/cm2の露光量(エネルギー量)で、フォトマスクを介して、感光層を露光した。フォトマスクとして、露光部及び未露光部の幅が1:1となるパターンを1μm:1μm〜50μm:50μmの範囲で有するガラスマスク(凸版印刷株式会社製、商品名「TOPPAN−TEST−CHART−NO1−N L78I1」)を用いた。次いで、現像液として25℃の2.38質量%水酸化テトラメチルアンモニウム水溶液を用い、最短現像時間(露光部が除去される最短時間)の1.5倍に相当する時間で浸漬することで現像した。次いで、蒸留水で洗浄した後、窒素ブローにて乾燥し、レジストパターンをガラス基板上に形成した。
露光及び現像によって形成したレジストパターンとガラス基板との密着性(基板密着性)を以下の3段階で評価した。密着性の評価には、ガラス基板に代えて、2種類の基板(シリコンウェハ、Cu/Ni合金基板)上にガラス基板の場合と同様の手順でレジストパターンを形成し、各基板とレジストパターンとの密着性も同様の方法で評価した。
A:円形のレジスト欠けの発生が確認できない。
B:円形のレジスト欠けが発生する割合が、レジストパターン全体を基準として10%未満。
C:レジストパターンの全面に、円形のレジスト欠けが発生。
露光及び現像によって形成したレジストパターンを観察し、耐現像液性を以下の3段階で評価した。
A:クラックの発生が確認できない。
B:発生したクラックの割合が、レジストパターン全体を基準として10%未満。
C:レジストパターンの全面に、クラックが発生。
露光及び現像後に、現像残渣の有無を以下の3段階で評価した。
A:現像残渣の発生が確認できない。
B:発生した現像残渣の割合が、露光部の領域全体を基準として10%未満。
C:露光部の全面に、現像残渣が発生。
評価サンプルを、ポリプロピレン製の容器に入った15%弗化水素酸溶液(富士技研工業社製、商品名:FCS−AD)に浸漬し、100分間静置した。その後、純水に1分間浸漬させて洗浄した。洗浄を3回行った後で、感光層を観察し、感光層のエッチング耐性を以下の3段階で評価した。
A:感光層の剥離が発生しない。
B:剥離した感光層の割合が、感光層の領域全体の10%未満。
C:剥離した感光層の割合が、感光層の領域全体の10%以上。
Claims (6)
- (A)クレゾール樹脂、
(B)光酸発生剤、及び
(C)エポキシ基を有するシラン化合物
を含有し、ガラス基板上に、弗化水素酸含有水溶液を用いて前記ガラス基板をエッチングするためのマスクとしてのレジストパターンを形成するために用いられる、ポジ型感光性樹脂組成物。 - 前記シラン化合物の含有量が、前記クレゾール樹脂及び前記光酸発生剤の総量100質量部に対し、0.1〜8質量部である、請求項1に記載のポジ型感光性樹脂組成物。
- 前記クレゾール樹脂が、不飽和炭化水素基を有するクレゾール樹脂を含む、請求項1又は2に記載のポジ型感光性樹脂組成物。
- 前記クレゾール樹脂が、
前記不飽和炭化水素基を有するクレゾール樹脂と、
パラクレゾール及びメタクレゾールを含むフェノール化合物から得られる、不飽和炭化水素基を有しないノボラック型クレゾール樹脂と、
オルトクレゾールを含むフェノール化合物から得られる、不飽和炭化水素基を有しないノボラック型クレゾール樹脂と、
を含む、
請求項3に記載のポジ型感光性樹脂組成物。 - 支持体と、
該支持体上に設けられた感光層と、を備え、
前記感光層が、請求項1〜4のいずれか一項に記載のポジ型感光性樹脂組成物を含む層である、
感光性エレメント。 - ガラス基板上に形成された、請求項1〜4のいずれか一項に記載のポジ型感光性樹脂組成物を含む感光層の一部を露光する工程と、
露光後の前記感光層を現像して、前記基板の表面の一部を露出させるレジストパターンを形成させる工程と、
を備える、レジストパターンを形成する方法。
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