JPWO2019220835A1 - パターン形成方法及び感放射線性組成物 - Google Patents
パターン形成方法及び感放射線性組成物 Download PDFInfo
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- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGDSVONAYZTTDA-UHFFFAOYSA-N tert-butylphosphonic acid Chemical compound CC(C)(C)P(O)(O)=O OGDSVONAYZTTDA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PYKSLEHEVAWOTJ-UHFFFAOYSA-N tetrabutoxystannane Chemical compound CCCCO[Sn](OCCCC)(OCCCC)OCCCC PYKSLEHEVAWOTJ-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- JDKSZLFJOLSRHU-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,1,1,2-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(CC)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 JDKSZLFJOLSRHU-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- OVZUSPADPSOQQN-UHFFFAOYSA-N tri(propan-2-yloxy)indigane Chemical compound [In+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] OVZUSPADPSOQQN-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
当該パターン形成方法は、基板に直接又は間接に[A]粒子、[B]ラジカル捕捉剤及び[C]有機溶媒を含有する感放射線性組成物(X)を塗工する工程(以下、「塗工工程」ともいう)と、上記塗工工程により形成された膜をEUV又はEBで露光する工程(以下、「露光工程」ともいう)と、上記露光工程後の膜を現像する工程(以下、「現像工程」ともいう)とを備える。当該パターン形成方法によれば、高い感度で、スカムが抑制されたパターンを形成することができる。以下、各工程について説明する。
本工程では、基板に直接又は間接に感放射線性組成物(X)を塗工する。これにより膜を形成する。以下、感放射線性組成物(X)について説明する。
感放射線性組成物(X)は、[A]粒子、[B]ラジカル捕捉剤及び[C]有機溶媒を含有する。感放射線性組成物(X)は、感放射線性酸発生剤(以下、「[D]酸発生剤」ともいう)を含有することが好ましく、本発明の効果を損なわない範囲において、その他の成分を含有していてもよい。
[A]粒子は、金属酸化物を主成分とする粒子である。感放射線性組成物(X)は、[A]粒子を複数個含有する。「金属酸化物」とは、金属原子と酸素原子とを含む化合物をいう。「主成分」とは、粒子を構成する物質のうち最も含有率が高いものをいい、好ましくは含有率が50質量%以上、より好ましくは60質量%以上であるものをいう。[A]粒子は、金属酸化物を主成分としているので、放射線を吸収して二次電子を生成することができ、この二次電子の作用によって[D]酸発生剤等の分解による酸の発生が促進される。その結果、感放射線性組成物(X)の感度を高いものとすることができる。感放射線性組成物(X)は、形成された膜の露光によって、[A]粒子の現像液への溶解性が変化することにより、パターンを形成することができる。
[A]粒子の金属酸化物を構成する金属原子(以下、「[m]金属原子」ともいう)としては、例えば第3族〜第16族の金属原子等が挙げられる。
第4族の金属原子としては、例えばチタン、ジルコニウム、ハフニウム等が、
第5族の金属原子としては、例えばバナジウム、ニオブ、タンタル等が、
第6族の金属原子としては、例えばクロム、モリブデン、タングステン等が、
第7族の金属原子としては、マンガン、レニウム等が、
第8族の金属原子としては、鉄、ルテニウム、オスミウム等が、
第9族の金属原子としては、コバルト、ロジウム、イリジウム等が、
第10族の金属原子としては、ニッケル、パラジウム、白金等が、
第11族の金属原子としては、銅、銀、金等が、
第12族の金属原子としては、亜鉛、カドミウム、水銀等が、
第13族の金属原子としては、アルミニウム、ガリウム、インジウム等が、
第14族の金属原子としては、ゲルマニウム、スズ、鉛等が、
第15族の金属原子としては、アンチモン、ビスマス等が、
第16族の金属原子としては、テルル等が挙げられる。
[z]金属含有化合物は、加水分解性基を有する金属化合物(以下、「金属化合物(I)」ともいう)、金属化合物(I)の加水分解物若しくは加水分解縮合物又はこれらの組み合わせである。金属化合物(I)は、1種単独で又は2種以上組み合わせて使用できる。
エチレン、プロピレン等の鎖状オレフィン;
シクロペンテン、シクロヘキセン、ノルボルネン等の環状オレフィン;
ブタジエン、イソプレン等の鎖状ジエン;
シクロペンタジエン、メチルシクロペンタジエン、ペンタメチルシクロペンタジエン、シクロヘキサジエン、ノルボルナジエン等の環状ジエン;
ベンゼン、トルエン、キシレン、ヘキサメチルベンゼン、ナフタレン、インデン等の芳香族炭化水素などが挙げられる。
ギ酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、2−エチルヘキサン酸、オレイン酸、アクリル酸、メタクリル酸、trans−2,3−ジメチルアクリル酸、ステアリン酸、リノール酸、リノレン酸、アラキドン酸、サリチル酸、安息香酸、p−アミノ安息香酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、トリフルオロ酢酸、ペンタフルオロプロピオン酸、没食子酸、シキミ酸等のモノカルボン酸;
シュウ酸、マロン酸、マレイン酸、メチルマロン酸、フマル酸、アジピン酸、セバシン酸、フタル酸、酒石酸等のジカルボン酸;
クエン酸等の3以上のカルボキシ基を有するカルボン酸などが挙げられる。
カテコール、レゾルシノール、ハイドロキノン、1,2−ナフタレンジオール等の2価のフェノール類;
ピロガロール、2,3,6−ナフタレントリオール等の3価以上のフェノール類などが挙げられる。
マレイミド、コハク酸イミド等のカルボン酸イミド;
ジ(トリフルオロメタンスルホン酸)イミド、ジ(ペンタフルオロエタンスルホン酸)イミド等のスルホン酸イミドなどが挙げられる。
ベンズアルドキシム、サリチルアルドキシム等のアルドキシム;
ジエチルケトキシム、メチルエチルケトキシム、シクロヘキサノンオキシム等のケトキシムなどが挙げられる。
メチル基、エチル基、n−プロピル基、i−プロピル基、t−ブチル基等のアルキル基;
エテニル基、プロペニル基、ブテニル基等のアルケニル基;
エチニル基、プロピニル基、ブチニル基等のアルキニル基などが挙げられる。
シクロペンチル基、シクロヘキシル基等の単環の脂環式飽和炭化水素基;
シクロペンテニル基、シクロヘキセニル基等の単環の脂環式不飽和炭化水素基;
ノルボルニル基、アダマンチル基、トリシクロデシル基等の多環の脂環式飽和炭化水素基;
ノルボルネニル基、トリシクロデセニル基等の多環の脂環式不飽和炭化水素基などが挙げられる。
フェニル基、トリル基、キシリル基、ナフチル基、アントリル基等のアリール基;
ベンジル基、フェネチル基、ナフチルメチル基、アントリルメチル基等のアラルキル基などが挙げられる。
アザシクロプロパン構造、アザシクロブタン構造、アザシクロペンタン構造、アザシクロヘキサン構造等のアザシクロアルカン構造;
アザビシクロ[2.2.2]オクタン構造、アザビシクロ[2.2.1]へプタン構造等のアザビシクロアルカン構造;
アザオキサシクロヘキサン構造等のアザオキサシクロアルカン構造などの窒素原子含有脂肪族複素環構造、
ピロール構造、イミダゾール構造、ピラゾール構造、ピリジン構造、ピラジン構造、ピリミジン構造、ピリダジン構造、キノリン構造、イソキノリン構造、アクリジン構造、フェナントロリン構造等の窒素原子含有芳香族複素環構造などが挙げられる。
トリエチルアミン、ジイソプロピルエチルアミン、トリ−n−ブチルアミン、トリ−n−オクチルアミン、N−メチルピロリジン、N−エチルピペリジン等の3級アミン;
ピロリジン、ピペリジン、ジ−n−ブチルアミン、ジ−n−オクチルアミン、モルホリン等の2級アミン;
n−ブチルアミン、n−オクチルアミン、アニリン、トルイジン等の1級アミンなどのモノアミン化合物、
ヘキサメチレンジアミン、N,N,N’,N’−テトラメチルエチレンジアミン、1,4−ジアザビシクロ[2.2.2]オクタン等のジアミン化合物;
ピリジン、ピロール、イミダゾール、ピラジン、トリアジン等の芳香族複素環式アミン化合物などが挙げられる。
[A]粒子は、例えば以下に示す[z]金属含有化合物を用いて加水分解縮合反応を行う方法、[z]金属含有化合物を用いて配位子交換反応を行う方法等により合成することができる。ここで「加水分解縮合反応」とは、[z]金属含有化合物が有する加水分解性基が加水分解して−OHに変換され、得られた2個の−OHが脱水縮合して−O−が形成される反応をいう。
[B]ラジカル捕捉剤は、生成したラジカルを捕捉して、ラジカル連鎖反応を抑制することができる化合物である。
[C]有機溶媒としては、少なくとも[A]粒子及び[B]ラジカル捕捉剤並びに必要に応じて含有される[D]酸発生剤等のその他の成分などを溶解又は分散可能な有機溶媒であれば特に限定されない。[C]有機溶媒は1種又は2種以上を用いることができる。
イソプロピルアルコール、4−メチル−2−ペンタノール、n−ヘキサノール等の炭素数1〜18の脂肪族モノアルコール系溶媒;
シクロヘキサノール等の炭素数3〜18の脂環式モノアルコール系溶媒;
1,2−プロピレングリコール等の炭素数2〜18の多価アルコール系溶媒;
プロピレングリコールモノメチルエーテル等の炭素数3〜19の多価アルコール部分エーテル系溶媒などが挙げられる。
ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジペンチルエーテル、ジイソアミルエーテル、ジヘキシルエーテル、ジヘプチルエーテル等のジアルキルエーテル系溶媒;
テトラヒドロフラン、テトラヒドロピラン等の環状エーテル系溶媒;
ジフェニルエーテル、アニソール等の芳香環含有エーテル系溶媒などが挙げられる。
アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、ジエチルケトン、メチル−iso−ブチルケトン、2−ヘプタノン、エチル−n−ブチルケトン、メチル−n−ヘキシルケトン、ジ−iso−ブチルケトン、トリメチルノナノン等の鎖状ケトン系溶媒:
シクロペンタノン、シクロヘキサノン、シクロヘプタノン、シクロオクタノン、メチルシクロヘキサノン等の環状ケトン系溶媒:
2,4−ペンタンジオン、アセトニルアセトン、アセトフェノンなどが挙げられる。
N,N’−ジメチルイミダゾリジノン、N−メチルピロリドン等の環状アミド系溶媒;
N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド等の鎖状アミド系溶媒などが挙げられる。
酢酸n−ブチル、乳酸エチル等のモノカルボン酸エステル系溶媒;
プロピレングリコールアセテート等の多価アルコールカルボキシレート系溶媒;
プロピレングリコールモノメチルエーテルアセテート(PGMEA)等の多価アルコール部分エーテルカルボキシレート系溶媒;
シュウ酸ジエチル等の多価カルボン酸ジエステル系溶媒;
ジメチルカーボネート、ジエチルカーボネート等のカーボネート系溶媒などが挙げられる。
n−ペンタン、n−ヘキサン等の炭素数5〜12の脂肪族炭化水素系溶媒;
トルエン、キシレン等の炭素数6〜16の芳香族炭化水素系溶媒などが挙げられる。
[D]酸発生剤は、放射線の照射により酸を発生する成分である。[D]酸発生剤から発生する酸の作用により、感放射線性組成物(X)における[A]粒子の現像液への溶解性等の変化をより促進することができ、その結果、感度及びスカム抑制性をより向上させることができる。
その他の成分としては、例えば感放射線性ラジカル発生剤、酸拡散制御剤、界面活性剤等が挙げられる。感放射線性組成物(X)は、その他の成分を1種又は2種以上用いてもよい。
感放射線性ラジカル発生剤は、放射線の照射によりラジカルを発生する成分である。感放射線性ラジカル発生剤としては、公知の化合物を用いることができる。
酸拡散制御剤は、露光により[D]酸発生剤等から生じる酸の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効果を奏する。また、感放射線性組成物(X)の保存安定性がより向上すると共に、解像性がより向上する。さらに、露光から現像処理までの引き置き時間の変動によるパターンの線幅変化を抑えることができ、プロセス安定性に優れた感放射線性組成物が得られる。
n−ヘキシルアミン等のモノアルキルアミン;ジ−n−ブチルアミン等のジアルキルアミン;トリエチルアミン等のトリアルキルアミン;アニリン等の芳香族アミンなどのモノアミン、
エチレンジアミン、N,N,N’,N’−テトラメチルエチレンジアミン等のジアミン、
ポリエチレンイミン、ポリアリルアミン等のポリアミン、
ジメチルアミノエチルアクリルアミド等の重合体などのアミン化合物、
ホルムアミド、N−メチルホルムアミド等のアミド基含有化合物、
尿素、メチルウレア等のウレア化合物、
ピリジン、2−メチルピリジン等のピリジン化合物;N−プロピルモルホリン、N−(ウンデシルカルボニルオキシエチル)モルホリン等のモルホリン化合物;ピラジン、ピラゾール等の含窒素複素環化合物、
N−t−ブトキシカルボニルピペリジン、N−t−ブトキシカルボニルイミダゾール等の酸解離性基を有する含窒素複素環化合物などが挙げられる。
界面活性剤は、塗布性、ストリエーション等を改良する作用を示す成分である。上記界面活性剤としては、例えばポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンn−オクチルフェニルエーテル、ポリオキシエチレンn−ノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等のノニオン系界面活性剤などが挙げられる。また、上記界面活性剤の市販品としては、例えばKP341(信越化学工業(株))、ポリフローNo.75、同No.95(以上、共栄社化学(株))、エフトップEF301、同EF303、同EF352(以上、(株)トーケムプロダクツ)、メガファックF171、同F173(以上、DIC(株))、フロラードFC430、同FC431(以上、住友スリーエム(株))、アサヒガードAG710、サーフロンS−382、同SC−101、同SC−102、同SC−103、同SC−104、同SC−105、同SC−106(以上、旭硝子(株))などが挙げられる。
感放射線性組成物(X)は、例えば[A]粒子、[B]ラジカル捕捉剤及び[C]有機溶媒並びに必要に応じて[D]酸発生剤、その他の成分等を所定の割合で混合し、好ましくは、得られた混合物を孔径0.2μm程度のフィルターで濾過することにより調製することができる。感放射線性組成物(X)の固形分濃度の下限としては、0.1質量%が好ましく、0.5質量%がより好ましく、1質量%がさらに好ましく、3質量%が特に好ましい。一方、上記固形分濃度の上限としては、50質量%が好ましく、30質量%がより好ましく、15質量%がさらに好ましく、7質量%が特に好ましい。「固形分濃度」とは、感放射線性組成物(X)の[C]有機溶媒以外の全成分の濃度(質量%)をいう。
本工程では、塗工工程により得られた膜をEUV又はEBで露光する。具体的には、例えば所定のパターンを有するマスクを介して上記膜に放射線を照射する。本工程では、必要に応じ、水等の液浸媒体を介した放射線の照射、つまり液浸露光を採用してもよい。
本工程では、現像液を用い、露光工程後の膜を現像する。これにより、所定パターンが形成される。現像液としては例えばアルカリ水溶液、有機溶媒含有液等が挙げられる。すなわち、現像方法としては、アルカリ現像でも有機溶媒現像でもよい。
[合成例1]
ジルコニウム(IV)テトライソプロポキシド2.7gをメタクリル酸9gに溶解させ、この溶液を65℃で2時間加熱した。反応溶液を複数回ヘキサンで洗浄した後、乾燥させることで、金属原子と有機酸に由来する配位子とを主に含む粒子(A−1)を得た。
ジルコニウム(IV)テトライソプロポキシド2.5g及びメタクリル酸1.4gを酢酸エチル40.0gに溶解させた。この溶液にトリエチルアミン2.2gを滴下して65℃で10時間加熱した。減圧濃縮により酢酸エチルを留去させることで、金属原子と有機酸に由来する配位子と塩基に由来する配位子を含む粒子(A−2)を得た。
感放射線性組成物の調製に用いた[B]ラジカル捕捉剤、[C]有機溶媒及び[D]酸発生剤を以下に示す。
B−1:ヒドロキノン(下記式(B−1)で表される化合物)
B−2:4−メトキシフェノール(下記式(B−2)で表される化合物)
B−3:2,6−ジ−tert−ブチル−4−メチルフェノール(下記式(B−3)で表される化合物)
B−4:2−ヒドロキシ−1,4−ナフトキノン(下記式(B−4)で表される化合物)
B−5:4−オキソ−2,2,6,6−テトラメチルピペリジン1−オキシルフリーラジカル(下記式(B−5)で表される化合物)
B−6:フェノチアジン(下記式(B−6)で表される化合物)
B−7:N,N’−ジ−sec−ブチル−1,4−フェニレンジアミン(下記式(B−7)で表される化合物)
C−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(下記式(C−1)で表される化合物)
D−1:N−(トリフルオロメチルスルホニルオキシ)−1,8−ナフタルイミド(下記式(D−1)で表される化合物)
[A]粒子としての(A−1)100質量部、[C]有機溶媒としての(C−1)及び[D]酸発生剤としての(D−1)10質量部を混合し、固形分濃度5質量%の混合液とした。得られた混合液を孔径0.20μmのメンブランフィルターでろ過することで感放射線性組成物(R−1)を調製した。なお、下記表1における「−」は、「[B]ラジカル捕捉剤」を添加していないことを示す。
[A]粒子としての(A−1)100質量部、[B]ラジカル捕捉剤としての(B−1)20質量部、[C]有機溶媒としての(C−1)及び[D]酸発生剤としての(D−1)10質量部を混合し、固形分濃度5質量%の混合液とした。得られた混合液を孔径0.20μmのメンブランフィルターでろ過することで感放射線性組成物(R−2)を調製した。
下記表1に示す種類及び含有量の各成分を用いた以外は、実施例1と同様に操作して感放射線性組成物(R−3)〜(R−10)を調製した。
[比較例1及び実施例1〜9]
簡易スピンコーターで、シリコンウエハ上に下記表2に示す感放射線性組成物をスピンコートした後、40℃、60秒間の条件でPBし、平均厚さ50nmの膜を形成した。次に、この膜に、真空紫外光露光装置(NA:0.3、ダイポール照明、30nmSpace60nmPitchのパターンのマスクを介して露光した。)を用いて露光し、パターニングを行った。EUV光照射は、線幅50nmのライン部と、隣り合うライン部の間に形成される間隔50nmのスペース部とが1:1となるライン・アンド・スペースパターン(1L1S)形成用のマスクパターンを用いて行った。トルエンにより現像した後、乾燥させることでネガ型パターンを形成した。
上記調製した感放射線性組成物について、感度及びスカム抑制性を、以下の方法に従い評価した。評価結果を下記表2に合わせて示す。
上記パターンの形成において、ライン・アンド・スペースパターン(1L1S)が露光量30mJ/cm2以下でパターンを形成できた場合は「A」(非常に良好)と、露光量30mJ/cm2以下ではパターンを形成できないが露光量30mJ/cm2超40mJ/cm2以下でパターンを形成できた場合は「B」(良好)と、露光量40mJ/cm2以下でパターンを形成できなかった場合は「C」(良好でない)と評価した。
走査型電子顕微鏡を用いて、形成されたパターン間を観察し、現像液で剥離されずスペース部に残存している膜の有無を確認した。スカム抑制性は、膜の残存が認められない場合は「A」(良好)と、膜の残存が認められる場合は「B」(不良)と評価した。
Claims (24)
- 基板に直接又は間接に、金属酸化物を主成分とする粒子、ラジカル捕捉剤及び有機溶媒を含有する感放射線性組成物を塗工する工程と、
上記塗工工程により形成された膜を極端紫外線又は電子線で露光する工程と、
上記露光工程後の膜を現像する工程と
を備えるパターン形成方法。 - 上記ラジカル捕捉剤が、安定ニトロキシルラジカル化合物、スルフィド化合物、キノン化合物、フェノール化合物、アミン化合物又はこれらの組み合わせである請求項1に記載のパターン形成方法。
- 上記粒子の含有量が、上記感放射線性組成物中の上記有機溶媒以外の全成分に対して50質量%以上である請求項1又は請求項2に記載のパターン形成方法。
- 上記粒子の含有量が、上記感放射線性組成物中の上記有機溶媒以外の全成分に対して85質量%以上である請求項3に記載のパターン形成方法。
- 上記粒子100質量部に対する上記ラジカル捕捉剤の含有量が0.01質量部以上20質量部以下である請求項1から請求項4のいずれか1項に記載のパターン形成方法。
- 上記金属酸化物を構成する金属原子が、ジルコニウム、ハフニウム、亜鉛、スズ、ニッケル及びコバルトの少なくともいずれかの原子である請求項1から請求項5のいずれか1項に記載のパターン形成方法。
- 上記粒子が、上記金属酸化物を構成する金属原子及び有機酸に由来する配位子を含む請求項1から請求項7のいずれか1項に記載のパターン形成方法。
- 上記粒子が、塩基に由来する配位子をさらに含む請求項8に記載のパターン形成方法。
- 上記有機酸がメタクリル酸である請求項8又は請求項9に記載のパターン形成方法。
- 上記粒子の平均粒子径が20nm以下である請求項1から請求項10のいずれか1項に記載のパターン形成方法。
- 上記感放射線性組成物が感放射線性酸発生剤をさらに含有する請求項1から請求項11のいずれか1項に記載のパターン形成方法。
- 金属酸化物を主成分とする粒子と、
ラジカル捕捉剤と、
有機溶媒と
を含有する感放射線性組成物。 - 上記ラジカル捕捉剤が、安定ニトロキシルラジカル化合物、スルフィド化合物、キノン化合物、フェノール化合物、アミン化合物又はこれらの組み合わせである請求項13に記載の感放射線性組成物。
- 上記粒子の含有量が、上記有機溶媒以外の全成分に対して50質量%以上である請求項13又は請求項14に記載の感放射線性組成物。
- 上記粒子の含有量が、上記有機溶媒以外の全成分に対して85質量%以上である請求項15に記載の感放射線性組成物。
- 上記粒子100質量部に対する上記ラジカル捕捉剤の含有量が0.01質量部以上20質量部以下である請求項13から請求項16のいずれか1項に記載の感放射線性組成物。
- 上記金属酸化物を構成する金属原子が、ジルコニウム、ハフニウム、亜鉛、スズ、ニッケル及びコバルトの少なくともいずれかの原子である請求項13から請求項17のいずれか1項に記載の感放射線性組成物。
- 上記粒子が、上記金属酸化物を構成する金属原子及び有機酸に由来する配位子を含む請求項13から請求項19のいずれか1項に記載の感放射線性組成物。
- 上記粒子が、塩基に由来する配位子をさらに含む請求項20に記載の感放射線性組成物。
- 上記有機酸がメタクリル酸である請求項20又は請求項21に記載の感放射線性組成物。
- 上記粒子の平均粒子径が20nm以下である請求項13から請求項22のいずれか1項に記載の感放射線性組成物。
- 感放射線性酸発生剤をさらに含有する請求項13から請求項23のいずれか1項に記載の感放射線性組成物。
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