JP5287264B2 - 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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- JP5287264B2 JP5287264B2 JP2009002730A JP2009002730A JP5287264B2 JP 5287264 B2 JP5287264 B2 JP 5287264B2 JP 2009002730 A JP2009002730 A JP 2009002730A JP 2009002730 A JP2009002730 A JP 2009002730A JP 5287264 B2 JP5287264 B2 JP 5287264B2
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
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- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 1
- UWQPDVZUOZVCBH-UHFFFAOYSA-N 2-diazonio-4-oxo-3h-naphthalen-1-olate Chemical class C1=CC=C2C(=O)C(=[N+]=[N-])CC(=O)C2=C1 UWQPDVZUOZVCBH-UHFFFAOYSA-N 0.000 description 1
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Description
(前記一般式(2)中、R3は、水素原子又はメチル基を示し、R4は、炭素数1〜20のアルキル基あるいは脂環式炭化水素基を示す。ただし、一般式(1)で表される繰り返し単位は除く。)
(前記一般式(2)中、R3は、水素原子又はメチル基を示し、R4は、炭素数1〜20のアルキル基あるいは脂環式炭化水素基を示す。ただし、一般式(1)で表される繰り返し単位は除く。)
本発明における重合体(A)は、下記一般式(1)および(2)で表される繰り返し単位と、カーボネート構造を有する繰り返し単位(3)をそれぞれ1種類以上含む。
(前記一般式(2)中、R3は、水素原子又はメチル基を示し、R4は、炭素数1〜20のアルキル基あるいは脂環式炭化水素基を示す。ただし、一般式(1)で表される繰り返し単位は除く。)
重合体(A)は、下記一般式(1)の繰り返し単位を有する重合体である。
重合体(A)は、下記一般式(2)の繰り返し単位を有する重合体である。
繰り返し単位(3)は、環状炭酸エステル構造を含む繰り返し単位であり、重合体(A)の必須繰り返し単位である。
次に、重合体(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重合体(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)、重合体(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。
R17CyF2ySO3 − :(b−1)
R17SO3 − :(b−2)
(一般式(b−1),(b−2)中、R17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。)
本発明の感放射線性樹脂組成物は、これまでに説明した重合体(A)及び酸発生剤(B)に加えて、酸拡散抑制剤(C)を更に含有しても良い。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、少なくとも重合体(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。例えば、アルコール類、エーテル類、ケトン類、アミド類、エステル・ラクトン類、ニトリル類及びその混合溶媒等を使用することができる。
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、重合体(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。
フォトレジストパターン形成方法は、例えば、以下に示すようにしてフォトレジストパターンを形成することが一般的である。(1)感放射線性樹脂組成物を用いて、基板上にフォトレジスト膜を形成した後(工程(1))、(2)形成されたフォトレジスト膜に(必要に応じて液浸媒体を介し)、所定のパターンを有するマスクを通して放射線を照射して露光し(工程(2))、基板(露光されたフォトレジスト膜)を加熱し(工程(3))、次いで(4)現像すれば(工程(4))、フォトレジストパターンを形成することができる。
東ソー社製GPCカラム(G2000HXL 2本、G3000HXL 1本、G4000HXL 1本)を用い、流量1.0ミリリットル/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ー(GPC)により測定する。
東ソー社製GPCカラム(G2000HXL 2本、G3000HXL 1本、G4000HXL 1本)を用い、流量1.0ミリリットル/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ー(GPC)により測定する。
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。
樹脂(A−1)〜(A−4)は、各合成例において、下記の単量体(M−1)〜(M−4)を用いて合成した。単量体(M−1)〜(M−2)は繰り返し単位(1)に相当する単量体、単量体(M−4)は繰り返し単位(2)に相当する単量体、単量体(M−3)は繰り返し単位(3)に相当する単量体である。
単量体(M−1)27.42g(50モル%)、単量体(M−4)5.16g(10モル%)、単量体(M−3)17.43g(40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)2.27g(5モル%)を投入した単量体溶液を準備した。
表1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−4)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−4)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):トリフェニルスルホニウム2−ビシクロ[2.2.1]ヘプト−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
(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−1):トリフェニルスルホニウム2−ビシクロ[2.2.1]ヘプト−2−イル−1,1−ジフルオロエタンスルホネート7.5質量部、酸拡散抑制剤(C)として、(C−1):N−t−ブトキシカルボニル−4−ヒドロキシピペリジン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30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。
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)、(比較例1、2)を得た。
得られた実施例1、2、比較例1、2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。
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%以内となる場合の露光量の範囲の、最適露光量に対する割合を露光余裕とした。具体的には、露光余裕が10%以上の場合「良好」、10%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。この値は小さいほど良い。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。
上記感度で解像した線幅90nmのライン・アンド・スペースパターンの断面形状を、商品名「S−4200」(株式会社日立ハイテクノロジーズ社製)にて観察し、レジストパターンの中間での線幅Lbと、膜の上部での線幅Laを測り、0.9≦(La/Lb)≦1.1の範囲内である場合を「良好」と評価し、範囲外である場合を「不良」と評価した。
にも対応可能である。
Claims (2)
- 下記一般式(1)で表される繰り返し単位および下記一般式(2)で表される繰り返し単位と、環状カーボネート構造を有する繰り返し単位(3)をそれぞれ1種類以上含む重合体(A)、ならびに感放射線性酸発生剤(B)を含有する感放射線性樹脂組成物。
(前記一般式(2)中、R3は、水素原子又はメチル基を示し、R4は、炭素数1〜20のアルキル基あるいは脂環式炭化水素基を示す。ただし、一般式(1)で表される繰り返し単位は除く。) - 下記一般式(1)で表される繰り返し単位および下記一般式(2)で表される繰り返し単位と、環状カーボネート構造を有する繰り返し単位(3)をそれぞれ1種類以上含む重合体。
(前記一般式(2)中、R3は、水素原子又はメチル基を示し、R4は、炭素数1〜20のアルキル基あるいは脂環式炭化水素基を示す。ただし、一般式(1)で表される繰り返し単位は除く。)
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