JP2017107185A - オーバーコートされたフォトレジストと共に用いるためのコーティング組成物 - Google Patents
オーバーコートされたフォトレジストと共に用いるためのコーティング組成物 Download PDFInfo
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- JP2017107185A JP2017107185A JP2016220509A JP2016220509A JP2017107185A JP 2017107185 A JP2017107185 A JP 2017107185A JP 2016220509 A JP2016220509 A JP 2016220509A JP 2016220509 A JP2016220509 A JP 2016220509A JP 2017107185 A JP2017107185 A JP 2017107185A
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
【解決手段】有機コーティング組成物、具体的には、オーバーコートされたフォトレジストと共に用いるための反射防止コーティング組成物であって、1)1つ以上のグリシジル基と、2)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基と、を含む、反射防止コーティング組成物であり、それをフォトレジスト下層に設け、露光、現像し、パターン形成を行う方法である。。
【選択図】なし
Description
上で論じたように、好ましい態様では、有機コーティング組成物、具体的には、1)1つ以上のグリシジル基と、2)各々が、ヒドロキシル(−OH)、チオール(S<)、及び/またはアミン(−N<)部分を含む2つ以上の置換基を含む1つ以上の芳香族基と、を含む1つ以上の材料を含む、オーバーコートされたフォトレジストと共に用いるための反射防止コーティングが、提供される。そのようなヒドロキシル、チオ、またはアミン基が、芳香族環原子(例えば、芳香族環の炭素原子)に直接結合されたO、S、もしくはN原子を有し得るか、またはO、S、もしくはN以外の1つ以上の原子が、それぞれのヒドロキシル、チオ、もしくはアミン部分のO、S、もしくはN原子と芳香族環との間に挿入され得ることを理解されよう。
下地コーティング組成物と用いるためのフォトレジストは典型的にポリマーと1つ以上の酸発生剤とを含む。一般的に好ましいのはポジ型レジストであり、レジストポリマーはレジスト組成物にアルカリ性の水溶解性を与える官能基を有する。例えば、好まれるのは、ヒドロキシルまたはカルボキシレート等の極性官能基、またはリソグラフィ加工のときにかかる極性部分を遊離させることができる酸不安定基を含む、ポリマーである。好ましくは、ポリマーは、水性アルカリ溶液で現像可能なレジストを行うのに十分な量でレジスト組成物に用いられる。
使用において、本発明のコーティング組成物は、スピンコーティング等の多種多様の方法の任意のものによって、コーティング層として基材に塗布される。一般的にコーティング組成物は基材上に、約0.02〜0.5μmの乾燥層厚さ、好ましくは約0.04〜0.20μmの乾燥層厚さで塗布される。基材は好適に、フォトレジストを伴う処理に用いられる任意の基材である。例えば、基材は、ケイ素、二酸化ケイ素、またはアルミニウム−酸化アルミニウムマイクロ電子ウェハであり得る。ガリウムヒ素、炭化ケイ素、セラミック、石英、または銅基材もまた使用してもよい。液晶ディスプレイまたは他のフラットパネルディスプレイ用途のための基材、例えばガラス基材、インジウムスズ酸化物でコーティングされた基材等も、好適に使用される。光学及び光学電子デバイス(例えば、導波管)のための基材もまた、使用可能である。
以下のポリマーP1〜P9を、続く実施例において説明する。ポリマーP3は、Nisso,Japanから購入され、重量平均分子量Mw=5.3K、PDI=1.1であった。ポリマーP4、P5、P6、及びP7は、Miwon Chemical,Koreaによって供給された。
実施例1:合成THEIC−TCEICコポリマーP1
BARC組成物は、表1中に示される量で構成成分を混合することによって調製される。この溶液を、0.45ミクロンの細孔径を有するPTFEフィルタを通して濾過して、BARC組成物を得る。表1中では、特定のポリマーP1〜P9は、概評の下で上に記述される構造を有する;PGMEA=プロピレングリコールモノメチルエーテルアセテート;HBM=メチル−2−ヒドロキシイソブチレート;T1=p−トルエンスルホン酸アンモニウム塩;C−1=テトラメトキシメチルグリコウリル、及びF−1=OMNOVA Solutions Incからのフッ素系界面活性剤Polyfox 656。
BARC組成物を、それぞれ、1500rpmで4cm×4cmのTiNクーポンウェハ上にスピンコートし、次いで、ミニコーティング機を使用して、215℃で1分間ベークした。ベーク後のBARCコーティング厚さは1000Åであった。回転成形したBARC膜を、SC−1混合物として知られているTiNのためのウェットエッチング化学薬品に浸漬するためにウェハ保持具上に置いた。この試験において使用されたSC−1混合物は、NH4OH:H2O2:H2O=1:4:20の重量比を有する。SC−1混合物中にBARC膜を浸漬した後、SC−1を50℃まで加熱した。ウェットエッチング耐性サンプルは、BARC膜から剥離することなく、これらの条件で長い持続時間を示すが、付着の不良なBARCは短期間で剥離した。SC−1混合物における膜剥離をモニタリングすることによる持続時間は、評価性能として使用された。
光学特性及び溶媒耐性について試験した各サンプル溶液を、Siウェハ上にスピンコートし、215℃で60秒間ベークした。Siウェハ上のn/k値及び膜厚さは、偏光解析を使用して測定された。次に、フォトレジスト分野で一般に使用されるPGME/PGMEA=70:30重量%の混合溶液を、BARC膜の表面上に注ぎ、90秒間静置した。次に、ウェハを4000rpmで60秒間スピン乾燥させた。添加後、溶媒除去のために、110℃で60秒間ベークする。最終厚さと初期厚さとの差を溶媒ストリップ値として報告する。
実施例8及び10のBARC組成物を、それぞれ、1500rpmで150mmのシリコンウェハ上にスピンコートし、次いで、TEL ACT 8ウェハコーティング追跡機を使用して、215℃で1分間ベークした。ベーク後のBARCコーティング厚さは1000Åであった。Dow EPIC2150フォトレジストを、BARCコーティング上にスピンコートし、125℃で60秒間ベークして、厚さ170nmのフォトレジスト層を得た。次に、フォトレジストを、0.78NAでNikon 306C 193nmのArFスキャナーを使用して標的マスクを通して露光した。フォトレジスト層を105℃で60秒間、露光後ベークして、続いて、標準の60秒間のシングルパドルプロセスにおいてDow MF(商標)CD−26 TMAH現像機を使用して現像した。走査電子顕微鏡法を、150,000倍率で、フォトレジストのパターンプロファイルの品質を試験するために行った。
Claims (10)
- フォトレジストレリーフ像を形成するための方法であって、
a)基材上に、
1)1つ以上のグリシジル基と、
2)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基と、を含む1つ以上の材料を含むコーティング組成物の層を塗布することと、
b)前記コーティング組成物層の上にフォトレジスト組成物の層を塗布することと、を含む、方法。 - 前記コーティング組成物が、1)1つ以上のグリシジル基を含む第1の樹脂と、2)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基を含む第2の樹脂と、を含む、請求項1に記載の方法。
- 前記コーティング組成物が、1)1つ以上のグリシジル基、ならびに2)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基の両方を含む樹脂を含む、請求項1に記載の方法。
- 前記1つ以上の芳香族基が、カテコール部分を含む、請求項1〜3のいずれか1項に記載の方法。
- 前記フォトレジスト組成物が、活性化放射線で像形成され、前記像形成されたフォトレジスト組成物層が、現像されてフォトレジストレリーフ像を提供する、請求項1〜4のいずれか1項に記載の方法。
- フォトレジストレリーフ像が、ウェットエッチングプロセスによって基材に転写される、請求項1〜5のいずれか1項に記載の方法。
- カテコール部分を含む樹脂を生成するための方法であって、
1)樹脂と、2)反応部分を含むカテコール化合物とを反応させることを含む、方法。 - 請求項7に記載の方法によって得られる、ポリマー。
- コーティングされた基材であって、
基材を備え、その上に、
a)
1)1つ以上のグリシジル基と、
2)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基と、を含む1つ以上の材料を含むコーティング組成物と、
b)前記コーティング組成物層の上にフォトレジスト組成物の層と、を有する、基材。 - オーバーコートされたフォトレジスト組成物と共に用いるためのコーティング組成物であって、
(a)1つ以上のグリシジル基と、
(b)各々が、ヒドロキシ、チオール、及び/またはアミン部分を含む2つ以上の置換基を含む1つ以上の芳香族基と、を含む1つ以上の樹脂を含む、コーティング組成物。
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US10527942B2 (en) | 2020-01-07 |
KR20170071412A (ko) | 2017-06-23 |
KR101909884B1 (ko) | 2018-10-22 |
TWI662370B (zh) | 2019-06-11 |
CN106814543B (zh) | 2021-03-23 |
US20170153547A1 (en) | 2017-06-01 |
TW201721288A (zh) | 2017-06-16 |
JP6509797B2 (ja) | 2019-05-08 |
CN106814543A (zh) | 2017-06-09 |
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