JP2010066503A - 感放射線性樹脂組成物 - Google Patents
感放射線性樹脂組成物 Download PDFInfo
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- JP2010066503A JP2010066503A JP2008232552A JP2008232552A JP2010066503A JP 2010066503 A JP2010066503 A JP 2010066503A JP 2008232552 A JP2008232552 A JP 2008232552A JP 2008232552 A JP2008232552 A JP 2008232552A JP 2010066503 A JP2010066503 A JP 2010066503A
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- 125000000217 alkyl group Chemical group 0.000 claims description 32
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Abstract
【解決手段】樹脂(A)と、感放射線性の酸発生剤(B)と、酸拡散抑制剤(C)と、溶剤(D)とを含有し、前記樹脂(A)が、側鎖に環状炭酸エステル構造を有する繰り返し単位(a−1)を有する重合体であり、前記酸拡散抑制剤(C)が、特定構造の窒素含有化合物である感放射線性樹脂組成物。
【選択図】なし
Description
本発明における樹脂(A)は、下記一般式(a−1)で示される繰り返し単位(a−1)を有する重合体である。
繰り返し単位(a−1)は、前記一般式(a−1)で示される、環状炭酸エステル構造を含む繰り返し単位であり、樹脂(A)の必須繰り返し単位である。
樹脂(A)は、繰り返し単位(a−1)に加えて、ラクトン構造を含む繰り返し単位(a−2)を有する重合体であることが好ましい。
樹脂(A)は、繰り返し単位(a−1)に加えて、下記一般式(a−3a)及び(a―3b)のうちの少なくとも1種の繰り返し単位(a−3)を有する重合体であることが好ましい。
樹脂(A)は、繰り返し単位(a−1)に加えて、下記一般式(a−4a)〜(a−4b)のうちの少なくとも1種の繰り返し単位(a−4)を有する重合体であることが好ましい。繰り返し単位(a−4)は、エステル部分にアダマンタン骨格を有する繰り返し単位である。
樹脂(A)は、繰り返し単位(a−1)に加えて、一般式(a−5)で示される、構造中に多環型シクロアルキル基を有する繰り返し単位(a−5)を有する重合体であることが好ましい。
樹脂(A)は、繰り返し単位(a−1)に加えて、一般式(a−6)で示される、構造中に2つのトリフルオロメチル基と1つのヒドロキシル基が結合した炭素原子を有する繰り返し単位(a−6)を有する重合体であることが好ましい。
樹脂(A)は、繰り返し単位(a−1)に加えて、一般式(a−7)で示される、構造中にアダマンタン環の構造を有する繰り返し単位(a−7)を有する重合体であることが好ましい。
樹脂(A)を構成する重合体は、所望の機能を付与するべく、繰り返し単位(a−1)〜(a−7)以外の繰り返し単位(a−8)を更に有していてもよい。
次に、樹脂(A)の製造方法について説明する。
酸発生剤(B)は、露光により酸を発生する、感放射線性の酸発生剤である。この酸発生剤は、露光により発生した酸によって、感放射線性樹脂組成物に含有される樹脂(A)中に存在する酸解離性基を解離させて(保護基を脱離させて)、樹脂(A)をアルカリ可溶性とする。そして、その結果、レジスト被膜の露光部がアルカリ現像液に易溶性となり、これによりポジ型のレジストパターンが形成される。
R15CyF2ySO3 − :(b−1)
R15SO3 − :(b−2)
(一般式(b−1),(b−2)中、R15は、水素原子、フッ素原子、炭素数1〜12の炭化水素基を示し、yは1〜10の整数を示す。)
テトラヒドロチオフェニウムカチオン、1−(4−n−ブトキシナフチル)テトラヒドロチオフェニウムカチオン、2−(7−メトキシナフチル)テトラヒドロチオフェニウムカチオン、2−(7−エトキシナフチル)テトラヒドロチオフェニウムカチオン、2−(7−n−プロポキシナフチル)テトラヒドロチオフェニウムカチオン、2−(7−n−ブトキシナフチル)テトラヒドロチオフェニウムカチオン等が好ましい。
ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムパーフルオロ−n−オクタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム2−ビシクロ[2.2.1]ヘプタ−2−イル−1,1,2,2−テトラフルオロエタンスルホネート、シクロヘキシル・2−オキソシクロヘキシル・メチルスルホニウムトリフルオロメタンスルホネート、ジシクロヘキシル・2−オキソシクロヘキシルスルホニウムトリフルオロメタンスルホネート、2−オキソシクロヘキシルジメチルスルホニウムトリフルオロメタンスルホネート等を挙げることができる。
本発明の感放射線性樹脂組成物は、これまでに説明した樹脂(A)及び酸発生剤(B)に加えて、酸拡散抑制剤(C)を更に含有する。この酸拡散抑制剤(C)は、露光により酸発生剤から生じる酸のレジスト被膜中における拡散現象を制御し、非露光領域における好ましくない化学反応を抑制するものである。このような酸拡散抑制剤(C)を配合することにより、得られる感放射線性樹脂組成物の貯蔵安定性が向上し、またレジストとしての解像度が更に向上するとともに、露光から露光後の加熱処理までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、プロセス安定性に極めて優れた組成物が得られる。
溶剤(D)としては、少なくとも樹脂(A)、酸発生剤(B)及び酸拡散抑制剤(C)、所望により添加剤(E)を溶解可能な溶剤であれば、特に限定されるものではない。
本発明の感放射線性樹脂組成物には、必要に応じて、フッ素含有樹脂、脂環式骨格含有樹脂、界面活性剤、増感剤等の各種の添加剤(E)を配合することができる。各添加剤の配合量は、その目的に応じて適宜決定することができる。
本発明の感放射線性樹脂組成物は、化学増幅型レジストとして有用である。化学増幅型レジストにおいては、露光により酸発生剤から発生した酸の作用によって、樹脂成分、主に、樹脂(A)中の酸解離性基が解離して、カルボキシル基を生じる。その結果、レジストの露光部のアルカリ現像液に対する溶解性が高くなり、この露光部がアルカリ現像液によって溶解、除去され、ポジ型のフォトレジストパターンが得られる。
Mw及びMnは、GPCカラム(商品名「G2000HXL」2本、商品名「G3000HXL」1本、商品名「G4000HXL」1本、いずれも東ソー社製)を使用し、流量:1.0mL/分、溶出溶媒:テトラヒドロフラン、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィ(GPC)により測定した。また、分散度「Mw/Mn」は、Mw及びMnの測定結果より算出した。
それぞれの重合体の13C−NMR分析は、核磁気共鳴装置(商品名:JNM−ECX400、日本電子社製)を使用し、測定した。
ODSカラム(商品名:Inertsil ODS−25μmカラム(4.6mmφ×250mm)、ジーエルサイエンス社製)を使用し、流量:1.0mL/分、溶出溶媒:アクリロニトリル/0.1%リン酸水溶液の分析条件で、高速液体クロマトグラフィー(HPLC)により測定した。なお、低分子量成分は、モノマーを主成分とする、分子量1,000未満(即ち、トリマーの分子量以下)の成分である。
樹脂(A−1)〜(A−25)は、各合成例において、下記の単量体(M−1)〜(M−15)を用いて合成した。単量体(M−12)〜(M−15)は繰り返し単位(a−1)に相当する単量体、単量体(M−1),(M−8)は繰り返し単位(a−2)に相当する単量体、単量体(M−7),(M−10)は繰り返し単位(a−3b)に相当する単量体、単量体(M−2),(M−3),(M−11)は繰り返し単位(a−3a)に相当する単量体である。
単量体(M−6)26.50g(50モル%)、単量体(M−12)8.42g(20モル%)、単量体(M−8)15.08g(30モル%)を2−ブタノン100gに溶解し、更に開始剤としてジメチル2,2’−アゾビス(2−メチルプロピオネート)1.91g(5モル%)を投入した単量体溶液を準備した。
表1及び表2に示す配合処方とした以外は、合成例1と同様にして樹脂(A−2)〜(A−25)を合成した。
表3に、各実施例及び比較例にて調製された感放射線性樹脂組成物の組成を示す。また、上記合成例にて合成した樹脂(A−1)〜(A−25)以外の感放射線性樹脂組成物を構成する各成分(酸発生剤(B)、酸拡散抑制剤(C)及び溶剤(D))について以下に示す。
(B−1):4−シクロヘキシルフェニル・ジフェニルスルホニウム・ノナフルオロ−n−ブタンスルホネート、
(B−2):トリフェニルスルホニウム・ノナフルオロ−n−ブタンスルホネート
(B−3):1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム・ノナフルオロ−n−ブタンスルホネート、
(B−4):1−(4−n−ブトキシナフタレン−1−イル)テトラヒドロチオフェニウム・2−(ビシクロ[2.2.1]ヘプタ−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、
(B−5):トリフェニルスルホニウム・2−(ビシクロ[2.2.1]ヘプタ−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、
(B−6):トリフェニルスルホニウム・2−(ビシクロ[2.2.1]ヘプタ−2−イル)−1,1−ジフルオロエタンスルホネート。
(C−1):N−t−ブトキシカルボニル−4−ヒドロキシピペリジン、
(C−2):R−(+)−(t−ブトキシカルボニル)−2−ピペリジンメタノール、
(C−3):N−t−ブトキシカルボニルピロリジン、
(C−4):N−t−ブトキシカルボニル−2−フェニルベンズイミダゾール、
(C−5):トリ−n−オクチルアミン、
(C−6):フェニルジエタノールアミン。
(D−1):プロピレングリコールモノメチルエーテルアセテート、
(D−2):シクロヘキサノン、
(D−3):γ−ブチロラクトン。
合成例1で得られた樹脂(A−1)100質量部、酸発生剤(B)として、(B−2)トリフェニルスルホニウム・ノナフルオロ−n−ブタンスルホネート8.4質量部、酸拡散抑制剤(C)として、(C−2)R−(+)−(t−ブトキシカルボニル)−2−ピペリジンメタノール0.9質量部を混合し、この混合物に、溶剤(D)として、(D−1)プロピレングリコールモノメチルエーテルアセテート1500質量部、(D−2)シクロヘキサノン650質量部及び(D−3)γ−ブチロラクトン40質量部を添加し、上記混合物を溶解させて混合溶液を得、得られた混合溶液を孔径0.20μmのフィルターでろ過して感放射線性樹脂組成物を調製した。表3に感放射線性樹脂組成物の配合処方を示す。
感放射線性樹脂組成物を調製する各成分の組成を表3に示すように変更したことを除いては、実施例1と同様にして、感放射線性樹脂組成物(実施例2〜13、比較例1〜11)を得た。
得られた実施例1〜13、比較例1〜11の感放射線性樹脂組成物について、ArFエキシマレーザーを光源として、感度、密集ライン焦点深度、孤立スペース焦点深度、LWR、MEEF、最小倒壊前寸法、及び現像欠陥数について評価を行った。評価結果を表4に示す。
8インチのウエハー表面に、下層反射防止膜形成剤(商品名:ARC29A、日産化学社製)を用いて、膜厚77nmの下層反射防止膜を形成した。この基板の表面に、実施例及び比較例の感放射線性樹脂組成物をスピンコートにより塗布し、ホットプレート上にて、表4に示す温度で90秒間SB(SoftBake)を行い、膜厚120nmのレジスト被膜を形成した。
最適露光量にて90nm1L/1Sマスクパターンで解像されるパターン寸法が、マスクの設計寸法の±10%以内となる場合のフォーカスの振れ幅を密集ライン焦点深度とした。具体的には、密集ライン焦点深度が0.40μm以上の場合「良好」、0.40μm未満の場合「不良」と評価した。なお、パターン寸法の観測には前記走査型電子顕微鏡を用いた。
最適露光量にて115nmS/1150nmPのマスクパターンで解像される90nmS/1150nmPパターン寸法が、81〜99nmS/1150nmPの範囲内となる場合のフォーカスの振れ幅を孤立ライン焦点深度とした。具体的には、孤立スペース焦点深度が0.20μm以上の場合「良好」、0.20μm未満の場合「不良」と評価した。なお、パターン寸法の観測には前記走査型電子顕微鏡を用いた。
前記走査型電子顕微鏡を用いて、最適露光量にて解像した90nm1L/1Sのパターンをパターン上部から観察する際に、線幅を任意のポイントで10点測定し、その測定値の3シグマ値(ばらつき)をLWRとした。具体的には、LWRが8.0nm以下の場合「良好」、8.0nmを超える場合「不良」と評価した。
前記走査型電子顕微鏡を用い、最適露光量において、5種類のマスクサイズ(85.0nmL/180nmP、87.5nmL/180nmP、90.0nmL/180nmP、92.5nmL/180nmP、95.0nmL/180nmP)で解像されるパターン寸法を測定した。その測定結果を、横軸をマスクサイズ、縦軸を線幅としてプロットし、最小二乗法によりグラフの傾きを求めた。この傾きをMEEFとした。具体的には、MEEFが4.0以上の場合「良好」、4.0未満の場合「不良」と評価した。
上記感度の評価の最適露光量にて解像した90nmのライン・アンド・スペースパターンの観測において、この最適露光量よりも大きな露光量にて露光を行った場合、得られるパターンの線幅が細くなるため、最終的にレジストパターンの倒壊が見られる。このレジストパターンの倒壊が確認されない最大の露光量における線幅を最小倒壊前寸法(nm)と定義し、パターン倒れ耐性の指標とした。具体的には、最小倒壊前寸法が40.0nm以下の場合「良好」、40.0nmを超える場合「不良」と評価した。なお、最小倒壊前寸法の測定は、前記走査型電子顕微鏡を用いた。
現像欠陥数は、欠陥検査装置(商品名:KLA2351、ケー・エル・エー・テンコール社製)を用いる下記方法により評価した。
欠陥検査用ウエハーは、次のように作成した。下層反射防止膜形成剤(商品名:ARC25、ブルワー・サイエンス社製)を膜厚820Åとなるようにコートし、ウエハー基板を作製した。この基板上に、実施例及び比較例の感放射線性樹脂組成物を膜厚0.30μmで塗布し、表4に示す温度で90秒間SB(SoftBake)を行った。
フルフィールド露光装置(商品名:S306C、ニコン社製)を用い、5mm×5mmのブランク露光を行い、ウエハー全面を露光させた。露光後、130℃/90秒の条件でPEBを行った後、2.38重量%のTMAH水溶液により、25℃で30秒間現像し、水洗し、乾燥して、欠陥検査用ウエハーを作成した。上記の塗布、焼成及び現像はコータ/デベロッパ(商品名:CLEAN TRACK ACT8、東京エレクトロン社製)を用い、全てインラインで実施した。
更に、感放射線性樹脂組成物を調製する各成分の組成を表5に示すように変更したことを除いては、実施例1と同様にして、感放射線性樹脂組成物(実施例15,16、比較例12,13)を得た。
得られた実施例15,16、比較例12,13の感放射線性樹脂組成物について、KrFエキシマレーザーを光源として、感度、密集ライン焦点深度、及び最小倒壊前寸法について評価を行った。評価結果を表6に示す。
8インチウエハー表面に、下層反射防止膜形成剤(商品名:DUV42P、ブルワー・サイエンス社製)を膜厚60nmとなるようにコートし、膜形成した。この基板の表面に、実施例及び比較例の感放射線性樹脂組成物をスピンコートにより塗布し、ホットプレート上にて、表1に示す温度で90秒間SBを行い、膜厚335nmのレジスト被膜を形成した。このレジスト被膜に、フルフィールド縮小投影露光装置(商品名:PASS5500/750、ASML社製、開口数0.70、露光波長248nm)を用い、マスクパターンを介して露光した。
最適露光量にて130nm1L/1Sマスクパターンで解像されるパターン寸法が、マスクの設計寸法の±10%以内となる場合のフォーカスの振れ幅を密集ライン焦点深度とした。なお、パターン寸法の観測には前記走査型電子顕微鏡を用いた。具体的には、密集ライン焦点深度が0.70μm以上の場合「良好」、0.70μm未満の場合「不良」と評価した。
130nm1L/1Sパターンの最適露光量にて解像可能な最小寸法を、前記走査型電子顕微鏡を用いてパターン上部から観察する。このレジストが解像可能な最小の線幅を最小解像寸法と定義し、解像性の指標とした。具体的には、最小倒壊前寸法が110nm以下の場合「良好」、110nmを超える場合「不良」と評価した。
Claims (3)
- 樹脂(A)と、感放射線性の酸発生剤(B)と、酸拡散抑制剤(C)と、溶剤(D)とを含有し、
前記樹脂(A)が、下記一般式(a−1)で示される繰り返し単位(a−1)を有する重合体であり、
前記酸拡散抑制剤(C)が、下記一般式(C−1)で示される窒素含有化合物である感放射線性樹脂組成物。
- 樹脂(A)が、前記繰り返し単位(a−1)に加えて、ラクトン構造を含む繰り返し単位(a−2)を有する重合体である、請求項1に記載の感放射線性樹脂組成物。
- 下記一般式(a−1)で示される繰り返し単位(a−1)と、下記一般式(a−3a)及び(a―3b)のうちの少なくとも1種の繰り返し単位(a−3)と、を有する共重合体。
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