JP2014071424A - 微細レジストパターン形成用組成物およびそれを用いたパターン形成方法 - Google Patents
微細レジストパターン形成用組成物およびそれを用いたパターン形成方法 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/22—Oxygen
- C08F12/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】化学増幅型レジスト組成物を用いてネガ型レジストパターンを形成させる方法において、レジストパターンを太らせることによってパターンを微細化するために用いられる、ヒドロキシアリール基を有する繰り返し単位を含むポリマーと、前記ネガ型レジストパターンを溶解させない有機溶剤とを含んでなる微細パターン形成用組成物とそれを用いたパターン形成方法。パターン形成方法において、レジスト組成物の塗布とその微細パターン形成用組成物とを同一の塗布装置で塗布することにより、配管詰まりを防止することができる。
【選択図】なし
Description
(1)形成されたレジストパターンを酸によって架橋しえる微細パターン形成用組成物で覆い、加熱によりレジストパターン中に存在する酸を拡散させ、レジストとの界面に架橋層をレジストパターンの被覆層として形成させ、現像液で非架橋部分を取り除くことでレジストパターンを太らせ、レジストパターンのホール径または分離幅が微細化される方法(特許文献1および2参照)。
(2)形成されたレジストパターンに、(メタ)アクリル酸モノマーと水溶性ビニルモノマーとからなるコポリマーを含む微細パターン形成用組成物レジストパターンに塗布し、熱処理により、レジストパターンを熱収縮させてパターンを微細化させる方法(特許文献3参照)。
(3)アミノ基、特に1級アミンを含むポリマーを含有する、フォトレジストパターンを被覆するための水溶性微細パターン形成用組成物(特許文献4参照)。
ところが、本発明者らの検討によると、レジスト組成物の塗布と微細パターン形成用組成物の塗布とを同一の塗布装置により行うと問題が起こり得ることが判明した。すなわち、塗布装置においては組成物の塗布を行うと、一般的に過剰の組成物が廃液として排出される。また、エッジリンス液などの洗浄液により過剰の組成物が除去される際、組成物と洗浄液との混合物も廃液として排出される。この廃液は配管を通過して装置外に排出されるが、その都度配管洗浄を行わない限りは廃液が配管内に付着して残留するのが一般的である。このため、レジスト組成物の塗布と、微細パターン形成用組成物とを同一の塗布装置で塗布した場合、配管内でレジスト組成物と微細パターン形成用組成物とが接触する。このとき、従来の微細パターン形成用組成物では固形物が析出することがあった。そのような固形物が発生すると、配管の詰りが起こるので生産性が低下してしまうのでその改良が求められていた。
(1)半導体基板上に化学増幅型フォトレジスト組成物を塗布してフォトレジスト層を形成する工程、
(2)前記フォトレジスト層で被覆された前記半導体基板を露光する工程、
(3)前記露光後に有機溶剤現像液で現像する工程、
(4)前記フォトレジストパターンの表面に、前記微細パターン形成用組成物を塗布する工程、
(5)塗布済みのフォトレジストパターンを加熱する工程、および
(6)過剰の微細パターン形成用組成物洗浄して除去する工程
を含んでなることを特徴とするものである。
本発明による微細パターン形成用組成物は、特定の構造を含むポリマーと溶剤とを含んでなる。本発明において用いられるポリマーは、繰り返し単位中にヒドロキシアリール基を含むものである。ここでヒドロキシアリール基とは、ベンゼン骨格、ナフタレン骨格、アントラセン骨格など、芳香環を含む骨格に、一つ以上のヒドロキシ基(−OH)が結合したものである。中心となる骨格は、芳香族を含むものであれば特に限定されないが、溶剤に対する溶解性などの観点から、ベンゼン骨格またはナフタレン骨格であることが好ましい。また、ヒドロキシ基は2以上結合していてもよい。また本発明の効果を損なわない範囲で、ヒドロキシ基以外の置換基が結合してもよい。具体的にはアルキル基、アルコキシ基、アリール基、ハロゲン、カルボニル基、カルボキシ基、スルホ基、およびアミノ基などが挙げられる。また、アリール基を構成する二つの炭素原子に結合した炭化水素鎖が環状構造を形成してもよい。
次に、本発明による微細なレジストパターンの形成方法について説明する。本発明の微細パターン形成用組成物が適用される代表的なパターン形成方法をあげると、次のような方法が挙げられる。
スピンコーター(東京エレクトロン株式会社製)にて、下層反射防止膜AZ ArF−1C5D(商品名、AZエレクトロニックマテリアルズ株式会社製)を8インチシリコンウェハーに塗布し、200℃にて、60秒間ベークを行い、膜厚37nmの反射防止膜を得た。その上に感光性樹脂組成物AZ AX2110P(商品名、AZエレクトロニックマテリアルズ株式会社製)を、110℃にて60秒間ベークを行い120nmの膜厚を得た。得られたウエハーをArF線(193nm)の露光波長を有する露光装置(株式会社ニコン製)を用いて、パターン露光を行い、110℃にて、60秒間ベークした。さらに、2−ヘプタノンを現像液として30秒間現像処理(ネガ型現像)を行い、ピッチ110nm、ホールサイズ60nmのレジストパターンを得た。
撹拌器、凝縮器および温度制御装置を取り付けた反応器にメチルアミルケトン(2100部)、4−ヒドロキシフェニルメタクリレート(PQMA、670部)、2−メチルアダマンタン−2−イルメタクリレート(MAdMA、220部)、ジメチル2,2’−アゾビス(2−メチルイソブチレート)(ラジカル重合開始剤、9部)を投入し、溶解させてモノマー溶液を調製し、窒素ガスで30分間パージした。さらに、80℃に保持された加熱装置に反応器を入れて、モノマー溶液を80℃で6時間保持した。
白色粉体状のPQMA/MAdMA(80/20)コポリマーを得た。
各種ポリマーを各種溶媒に溶解させて、微細パターン形成用組成物を調製した。それぞれの組成物に含まれる成分およびその含有量は表1に示された通りであった。
調製された組成物をレジストパターン1にスピンコーターを用いて塗布し、130℃で60秒間加熱したのち、2−ヘプタノンによって洗浄し、乾燥した。得られたホールパターンの寸法を測定し、微細パターン形成用組成物によるホールパターンの縮小量を測定した。また、形成された微細パターン形状を目視により評価した。評価基準は以下の通りである。
A: パターン形状が矩形である
B: 形状が歪んでいるが、パターン形状を確認できる
C:パターンが崩れている状態で、形状を確認することができない
レジスト組成物として、感光性樹脂組成物AZ AX2110P(以下、レジスト1という)およびAZ AX1120P(以下、レジスト2という)(いずれも商品名、AZエレクトロニックマテリアルズ株式会社製)を準備した。これらの組成物50gと微細パターン形成用組成物50gとを混合し、1時間振盪した後、混合物の状態を目視評価した。評価基準は以下に示す通りとした。
A: 混合物が透明で、沈殿、浮遊物が確認されない
B: 混合物に濁りが認められるが、沈殿物または浮遊物は認められない
C: 混合物中に沈殿物または浮遊物が確認される
得られた結果は表1に示す通りであった。
スピンコーター(東京エレクトロン株式会社製)にて、感光性樹脂組成物(商品名、AZエレクトロニックマテリアルズ株式会社製)をシリコンウェハーに塗布し、130℃にて、60秒間ベークを行い、膜厚F1(レジスト)を測定した。つぎにドライエッチング装置(株式会社アルバック製)を用い、エッチングを行った後に、ドライエッチング後の膜厚F2(レジスト)を測定した。
(エッチング耐性)=(F1−F2)/(F1(レジスト1)−F2(レジスト1))
Claims (9)
- 化学増幅型レジスト組成物を用いてネガ型レジストパターンを形成させる方法において、レジストパターンを太らせることによってパターンを微細化するために用いられる微細パターン形成用組成物であって、ヒドロキシアリール基を有する繰り返し単位を含むポリマーと、前記ネガ型レジストパターンを溶解させない有機溶剤とを含んでなることを特徴とする微細パターン形成用組成物。
- 前記ヒドロキシアリール基が、モノヒドロキシフェニル基、ジヒドロキシフェニル基、モノヒドロキシナフチル基、ジヒドロキシナフチル基からなる群から選択される、請求項1に記載の微細パターン形成用組成物。
- 前記ポリマーを構成する全繰り返し単位のモル数を基準として、ヒドロキシアリール基を有する繰り返し単位の割合が60モル%以上である、請求項1〜3のいずれか1項に記載の微細パターン形成用組成物。
- 前記有機溶剤が、2−ヘプタノン、または酢酸ブチルを含んでなる、請求項1〜4のいずれか1項に記載の微細パターン形成用組成物。
- 前記組成物が、2−ヘプタノン、または酢酸ブチルを80重量%以上含んでなる、請求項5に記載の組成物。
- (1)半導体基板上に化学増幅型フォトレジスト組成物を塗布してフォトレジスト層を形成する工程、
(2)前記フォトレジスト層で被覆された前記半導体基板を露光する工程、
(3)前記露光後に有機溶剤現像液で現像する工程、
(4)前記フォトレジストパターンの表面に、請求項1〜6のいずれか1項に記載の微細パターン形成用組成物を塗布する工程、
(5)塗布済みのフォトレジストパターンを加熱する工程、および
(6)過剰の微細パターン形成用組成物洗浄して除去する工程
を含んでなることを特徴とする微細化されたネガ型レジストパターンの形成方法。 - 前記工程(1)と、前記工程(4)とで、同一の塗布装置を用いる、請求項7に記載の方法。
- 前記工程(6)において、2−ヘプタノンあるいは酢酸ブチルを使用する、請求項7または8に記載の方法。
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SG11201501629VA SG11201501629VA (en) | 2012-10-01 | 2013-10-01 | Composition for forming fine resist pattern and pattern formation method using same |
EP13844490.6A EP2905657A4 (en) | 2012-10-01 | 2013-10-01 | COMPOSITION FOR PREPARING A FINE RESIST PATTERN AND STRUCTURE FORMING METHOD USING THE COMPOSITION |
US14/431,512 US9360756B2 (en) | 2012-10-01 | 2013-10-01 | Composition for forming fine resist pattern and pattern formation method using same |
TW102135507A TWI564663B (zh) | 2012-10-01 | 2013-10-01 | 微細光阻圖案形成用組成物及使用其之圖案形成方法 |
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WO2016158507A1 (ja) * | 2015-03-31 | 2016-10-06 | 日産化学工業株式会社 | レジストパターン被覆用塗布液及びパターンの形成方法 |
JP2016177071A (ja) * | 2015-03-19 | 2016-10-06 | 東京応化工業株式会社 | レジストパターン修復方法 |
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TWI564663B (zh) | 2017-01-01 |
US9360756B2 (en) | 2016-06-07 |
CN104737077B (zh) | 2019-06-04 |
US20150253669A1 (en) | 2015-09-10 |
EP2905657A1 (en) | 2015-08-12 |
KR101738376B1 (ko) | 2017-05-22 |
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