JP6261091B2 - フォトレジストパターントリミング組成物及び方法 - Google Patents
フォトレジストパターントリミング組成物及び方法 Download PDFInfo
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- JP6261091B2 JP6261091B2 JP2015245014A JP2015245014A JP6261091B2 JP 6261091 B2 JP6261091 B2 JP 6261091B2 JP 2015245014 A JP2015245014 A JP 2015245014A JP 2015245014 A JP2015245014 A JP 2015245014A JP 6261091 B2 JP6261091 B2 JP 6261091B2
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- BGYICJVBGZQOCY-UHFFFAOYSA-N heptyl propanoate Chemical compound CCCCCCCOC(=O)CC BGYICJVBGZQOCY-UHFFFAOYSA-N 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229920000847 nonoxynol Polymers 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N octan-4-ol Chemical compound CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 150000003377 silicon compounds Chemical class 0.000 description 1
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- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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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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- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
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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、及び溶媒を含み、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、化学増幅フォトレジスト組成物から形成された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。また、本発明のフォトレジスト組成物は、好ましいLWRならびに等密度バイアス特性を提供することもできる。
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
以下のスキーム1に示される反応順序に従って、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(SIPA−DiHFA)(酸A)を調製した。
実施例2
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 ArF1100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1に示す。
実施例3(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0.628gのコポリマーと、0.02gのp−トルエンスルホン酸(PTSA)と、23.48gのメチルイソブチルカルビノールと、5.87gのイソアミルエーテルとを、全ての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、実施例3のフォトレジストコーティングされたウエハ上でスピンコーティングし、熱板上で120秒間、70℃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1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0.579gのコポリマーと、0.069gの酸A(SIPA−DiHFA)と、12.007gのメチルイソブチルカルビノールと、5.87gのイソアミルエーテルとを、全ての成分が溶解するまで混合した。PCT−2中の酸の含有量は、実施例3のPTSA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−3の60nmのフィルムを、実施例3のフォトレジストコーティングされたウエハ上でスピンコーティングし、熱板上で70℃、80℃、90℃、及び100℃の各温度で60秒間ベーキングし、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1に示す。
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。等密度バイアスによって、従来のフォトマスクを使用して、光近接効果補正(OPC)を行う必要なく、孤立したパターンならびに密なパターンをマスク上に印刷することができるか否かの示唆がもたらされる。OPCが必要である場合は、典型的には、新規のフォトマスクが必要とされる。10nm以上の等密度バイアスは不十分とみなされ、10nm未満は十分とみなされる。CD、LWR、及び等密度バイアスの結果を表2に示す。
Claims (12)
- フォトレジストパターントリミング組成物であって、マトリックスポリマー、非重合体芳香族スルホン酸、及び溶媒を含み、前記芳香族スルホン酸が1つ以上のフッ素化アルコール基を含む、前記フォトレジストパターントリミング組成物。
- 前記芳香族スルホン酸が以下の一般式(I)によって表される酸である、請求項1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トリミング組成物であって、マトリックスポリマー、芳香族スルホン酸、及び溶媒を含み、前記芳香族スルホン酸が1つ以上のフッ素化アルコール基を含み、前記フッ素化アルコール基が、前記アルコールのヒドロキシルのアルファ位で炭素に結合されるフッ素原子を含む、前記フォトレジストパターントリミング組成物。
- 前記フッ素化アルコール基が、前記アルコールのヒドロキシルのアルファ位で炭素にペンダント状に結合されるフッ素化基を含む、請求項1〜3のいずれか一項に記載の前記フォトレジストパターントリミング組成物。
- 前記芳香族スルホン酸がヘキサフルオロアルコール基を含む、請求項1〜4のいずれかに記載の前記フォトレジストパターントリミング組成物。
- 前記芳香族スルホン酸が複数のフッ素化アルコール基を含む、請求項1または2に記載の前記フォトレジストパターントリミング組成物。
- 前記フッ素化アルコール基が、エステル基を介して前記芳香族スルホン酸の芳香族環に結合される、請求項1〜6のいずれかに記載の前記フォトレジストパターントリミング組成物。
- 前記マトリックスポリマーが、ポリ(メタ)アクリレートポリマーである、請求項1〜8のいずれかに記載の前記フォトレジストパターントリミング組成物。
- 前記芳香族スルホン酸が、前記トリミング組成物の全固形分に基づいて、0.01〜20重量%、の量で存在する、請求項1〜9のいずれかに記載の前記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)半導体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、光酸発生剤、及び溶媒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1〜9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の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とリンス剤とを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、前記方法。 - 前記フォトレジストパターンが液浸リソグラフィー方法で形成される、請求項11に記載の前記方法。
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