JP6313397B2 - 熱酸発生剤及びフォトレジストパターントリミング組成物ならびに方法 - Google Patents
熱酸発生剤及びフォトレジストパターントリミング組成物ならびに方法 Download PDFInfo
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- JP6313397B2 JP6313397B2 JP2016204736A JP2016204736A JP6313397B2 JP 6313397 B2 JP6313397 B2 JP 6313397B2 JP 2016204736 A JP2016204736 A JP 2016204736A JP 2016204736 A JP2016204736 A JP 2016204736A JP 6313397 B2 JP6313397 B2 JP 6313397B2
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Images
Classifications
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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- C07C309/58—Carboxylic acid groups or esters thereof
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
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- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/60—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
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- C07C321/30—Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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Description
フォトレジストパターントリミング組成物は、マトリックスポリマー、1つ以上のフッ素化アルコール基を含む芳香族スルホン酸のアニオン及びカチオンを含むイオン性熱酸発生剤、ならびに溶媒を含み、かつ1つ以上の任意の追加成分を含み得る。本発明によるフォトレジストトリミング組成物は、フォトレジストパターン上にコーティングされるとき、レジストパターン寸法が制御可能に縮小された、微細リソグラフィーパターンを提供することができる。本発明の好ましいフォトレジスト組成物は、好ましい線幅粗さ(LWR)及び/または等密度バイアス特性を提供することもできる。
(BH)+ (I)
これは、窒素含有塩基Bのモノプロトン化の形態である。好適な窒素含有塩基Bには、例えば、任意に置換されたアミン、例えば、アンモニア、ジフルオロメチルアンモニア、C1−20アルキルアミン、及びC3−30アリールアミン、例えば、ピリジンまたは置換されたピリジン(例えば、3−フルオロピリジン)、ピリミジン、及びピラジン等の窒素含有複素芳香族塩基;窒素含有複素環式基、例えば、オキサゾール、オキサゾリン、またはチアゾリンが含まれる。前述の窒素含有塩基Bは、例えば、アルキル、アリール、ハロゲン原子(好ましくはフッ素)、シアノ、ニトロ、及びアルコキシから選択される1つ以上の基で任意に置換され得る。これらの中で、塩基Bは、好ましくは複素芳香族塩基である。
ここで、本発明に従ったフォトレジストパターントリミング技術を用いてフォトリソグラフィーパターンを形成するための例示的な方法フローを示す図1A〜Hを参照して、本発明による方法について説明する。示される方法フローはポジティブ型現像方法のものであるが、ネガティブ型現像(NTD)方法にも本発明を適用することができる。また、示される方法フローは、単一のレジストマスクを使用してトリミングされたフォトレジストパターンを下部基板に転写するパターン形成方法についても説明するが、本トリミング方法は、他のリソグラフィー方法、例えば、リソ−リソ−エッチ(LLE)、リソ−エッチ−リソ−エッチ(LELE)、もしくは自己整合二重パターン形成(SADP)等の二重パターン形成方法で、イオン注入マスクとして使用することができるか、または、フォトレジストパターンのトリミングが有利となるであろう他の任意の他のリソグラフィー方法で使用することができることを、明確にされたい。
実施例1:TAG−3の合成
3−フルオロピリジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホン酸(3FP SIPA−DiHFA)(TAG−3)を、スキーム1で以下に示される反応順序に従って調製した。
ピリジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホネート(Pyr SIPA−DiHFA)(TAG−4)を、スキーム2で以下に示される反応順序に従って調製した。
ピリミジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホネート(ピリミジニウムSIPA−DiHFA)(TAG−5)を、スキーム3で以下に示される反応順序に従って調製した。
以下のモノマーM1〜M5を使用して、以下に記載されるフォトレジスト(フォトレジスト組成物A)を調製するためのポリマーを形成した。
80nmのBARC層(AR(商標)40A反射防止剤(antireflectant)、Dow Electronic Materials,Marlborough,MA USA)でコーティングされた8インチのケイ素ウエハを、フォトレジスト組成物Aを用いてスピンコーティングして、100℃で60秒間ソフトベーキングしたところ、900Åのレジスト層厚さがもたらされた。このウエハを、NA=0.75であるASML ArF 1100スキャナー、双極子35Y照明(0.89/0.64シグマ)、及びアウター/インナーシグマが0.89/0.64である双極子−35Yの下、120nmで1:1及び1:8のPSM形状を有する線ならびに空間パターンを有するマスクを用いて露光した。その露光されたウエハを、100℃で60秒間露光後ベーキングして、0.26N TMAH溶液を用いて現像したところ、120nmの1:1及び1:8の線及び空間パターン(デューティー比=1:1)画像化レジスト層がもたらされた。パターンのCDは、500ボルト(V)の加速電圧ならびに5.0ピコアンペア(pA)のプローブ電流で動作するHitachi 9380 CD−SEMを使用する、150Kxの倍率を用いたトップダウン走査電子顕微鏡(SEM)によって取り込まれた画像を処理して決定した。各ウエハに対して3つの露光寛容度を取得して平均化した。次いで、多項式回帰を用いて、その平均化された露光寛容度を適合させて、レジストパターントリミングを行わない場合の120nmの線の正確なサイジング線量を決定した。次いで、このサイジング線量を、レジストパターントリミングされたウエハの多項式回帰を用いて使用して、パターントリミングされたウエハそれぞれの最終CDを算出した。CD測定の結果を表2に示す。
実施例4(比較)(PTC−1)
n−ブチルメタクリレート/メタクリル酸ポリマー(77/23重量比)の0.202gのコポリマーと、0.014gの3−フルオロピリジン−1−イウム1,1,2,2,3,3,4,4,4−ノナフルオロブタン−1−スルホネートTAG−1(3FP PFBuS)と、7.827gのメチルイソブチルカルビノールと、1.957gのイソアミルエーテルと、を、全成分が溶解するまで混合した。その混合物を0.2ミクロンのナイロンフィルタで濾過したところ、フォトレジストトリミング組成物PTC−1がもたらされた。PTC−1の60nmのフィルムを、上で調製されたように、フォトレジストパターン形成されたウエハ上でスピンコーティングし、熱板上で60秒間、70℃または90℃でベーキングして、SHノズルを用いて、2.38重量%のTMAH現像液中で12秒間現像した。トリミングされたパターンのCDを、予めトリミングされたパターンと同じ様式で測定し、その結果を表2に示す。
n−ブチルメタクリレート/メタクリル酸ポリマー(77/23重量比)の0.203gのコポリマーと、0.013gのピリミジン−1−イウム1,1,2,2,3,3,4,4,4−ノナフルオロブタン−1−スルホネートTAG−2(ピリミジニウムPFBuS)と、7.827gのメチルイソブチルカルビノールと、1.957gのイソアミルエーテルと、を、全成分が溶解するまで混合した。PTC−2中のTAG−2の含有量は、実施例1のTAG−1含有量に対して等モルである。その混合物を0.2ミクロンのナイロンフィルタを用いて濾過したところ、フォトレジストトリミング組成物PTC−2がもたらされた。PTC−2の60nmのフィルムを、上で調製されたように、フォトレジストパターン形成されたウエハ上でスピンコーティングし、熱板上で60秒間、70℃または90℃の温度でベーキングして、SHノズルを用いて、2.38重量%のTMAH現像液中で12秒間現像した。トリミングされたパターンのCDを、予めトリミングされたパターンと同じ様式で測定し、その結果を表2に示す。
n−ブチルメタクリレート/メタクリル酸ポリマー(77/23重量比)の0.191gのコポリマーと、0.025gの3−フルオロピリジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホネートTAG−3(3FP SIPA−DiHFA)と、7.827gのメチルイソブチルカルビノールと、1.957gのイソアミルエーテルと、を、全成分が溶解するまで混合した。PTC−3中のTAG−3の含有量は、実施例1のTAG−1含有量に対して等モルである。その混合物を0.2ミクロンのナイロンフィルタで濾過したところ、フォトレジストトリミング組成物PTC−3がもたらされた。PTC−3の60nmのフィルムを、上で調製されたように、フォトレジストパターン形成されたウエハ上でスピンコーティングし、熱板上で60秒間、90℃の温度でベーキングして、SHノズルを用いて、2.38重量%のTMAH現像液中で12秒間現像した。トリミングされたパターンのCDを、予めトリミングされたパターンと同じ様式で測定し、その結果を表2に示す。
n−ブチルメタクリレート/メタクリル酸ポリマー(77/23重量比)の0.191gのコポリマーと、0.025gのピリジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホネートTAG−4(Pyr SIPA−DiHFA)と、7.827gのメチルイソブチルカルビノールと、1.957gのイソアミルエーテルと、を、全成分が溶解するまで混合した。PTC−4中のTAG−4の含有量は、実施例1のTAG−1含有量に対して等モルである。その混合物を0.2ミクロンのナイロンフィルタで濾過したところ、フォトレジストトリミング組成物PTC−4がもたらされた。PTC−4の60nmのフィルムを、上で調製されたように、フォトレジストパターン形成されたウエハ上でスピンコーティングし、熱板上で60秒間、90℃または105℃の温度でベーキングして、SHノズルを用いて、2.38重量%のTMAH現像液中で12秒間現像した。トリミングされたパターンのCDを、予めトリミングされたパターンと同じ様式で測定し、その結果を表2に示す。
n−ブチルメタクリレート/メタクリル酸ポリマー(77/23重量比)の0.191gのコポリマーと、0.025gのピリミジン−1−イウム3,5−ビス((4,4,4−トリフルオロ−3−ヒドロキシ−3−(トリフルオロメチル)ブトキシ)カルボニル)ベンゼンスルホネートTAG−5(ピリミジニウムSIPA−DiHFA)と、7.827gのメチルイソブチルカルビノールと、1.957gのイソアミルエーテルと、を、全成分が溶解するまで混合した。PTC−5中のTAG−5の含有量は、実施例1のTAG−1含有量に対して等モルである。その混合物を0.2ミクロンのナイロンフィルタで濾過したところ、フォトレジストトリミング組成物PTC−5がもたらされた。PTC−5の60nmのフィルムを、上で調製されたように、フォトレジストパターン形成されたウエハ上でスピンコーティングし、熱板上で60秒間、90℃または105℃の温度でベーキングして、SHノズルを用いて、2.38重量%のTMAH現像液中で12秒間現像した。トリミングされたパターンのCDを、予めトリミングされたパターンと同じ様式で測定し、その結果を表2に示す。
等密度バイアスを、以下の等式を使用して様々な試料について算出した:
IDB=ΔCD1:8−ΔCD1:1
式中、IDB=等密度バイアスであり、ΔCD1:8=[(トリミング前の120nmの1:8パターンのCD)−(トリミング後の120nmの1:8パターンのCD)]であり、及びΔCD1:1=[(トリミング前の120nmの1:1パターンのCD)−(トリミング後の120nmの1:1パターンのCD)]である。10nm以上の等密度バイアスは不十分、10nm未満は十分とみなされ、より低い値は、高い値に対して改善された等密度バイアスを示す。結果は、表2に提供される。
Claims (9)
- 1つ以上のフッ素化アルコール基を含む芳香族スルホン酸のアニオンと、カチオンと、を含み、前記フッ素化アルコール基は、ヒドロキシル基のアルファ位で炭素に結合したフッ素原子、及び/またはヒドロキシル基のアルファ位で炭素にペンダント状に結合したフッ素化基を含む、イオン性熱酸発生剤。
- 前記アニオンは、式−C(CF3)2OHのフルオロアルコール基を含む、請求項1に記載のイオン性熱酸発生剤。
- 前記アニオンは、式−C(CF3)2OHの複数のフッ素化アルコール基を含む、請求項2に記載のイオン性熱酸発生剤。
- 前記フッ素化アルコール基は、エステル基を介して前記アニオンの芳香族環に結合している、請求項1〜3のいずれかに記載のイオン性熱酸発生剤。
- 前記熱酸発生剤は、以下の一般式(I)のものであり、
- 請求項1〜6のいずれかに記載のイオン性熱酸発生剤と、マトリックスポリマーと、溶媒と、を含むフォトレジストパターントリミング組成物。
- 前記溶媒は、有機溶媒である、請求項7に記載のフォトレジストパターントリミング組成物。
- フォトレジストパターンをトリミングする方法であって、
(a) 基板を提供することと、
(b) 酸不安定基を含むマトリックスポリマーと、光酸発生剤と、溶媒とを含むフォトレジスト組成物から形成されるフォトレジストパターンを、前記基板上に形成することと、
(c) 請求項7または8のいずれかに記載のフォトレジストトリミング組成物を前記基板上で前記フォトレジストパターン上にコーティングすることと、
(d) 前記コーティングされた基板を加熱し、それによって、前記フォトレジストパターンの表面領域内の前記フォトレジストマトリックスポリマーの極性を変化させることと、
(e) 前記フォトレジストパターンをリンス剤と接触させて前記フォトレジストパターンの前記表面領域を除去し、それによって、トリミングされたフォトレジストパターンを形成することと、を含む、方法。
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