JP6814772B2 - 熱酸発生剤を含む反射防止組成物 - Google Patents
熱酸発生剤を含む反射防止組成物 Download PDFInfo
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- JP6814772B2 JP6814772B2 JP2018163315A JP2018163315A JP6814772B2 JP 6814772 B2 JP6814772 B2 JP 6814772B2 JP 2018163315 A JP2018163315 A JP 2018163315A JP 2018163315 A JP2018163315 A JP 2018163315A JP 6814772 B2 JP6814772 B2 JP 6814772B2
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Classifications
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- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
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- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- 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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/38—Masks having auxiliary features, e.g. special coatings or marks for alignment or testing; Preparation thereof
- G03F1/46—Antireflective coatings
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- 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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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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Description
a)基板上に、1)樹脂と2)式(I)の構造を含む熱酸発生剤であって、
b)コーティング組成物層上にフォトレジスト組成物の層を塗布することと、を含む方法が提供される。
R2は、独立して、水素、C1−C6アルキル、C3−C6シクロアルキル、またはフェニルであり、これらは任意に置換されてもよく、nは1〜5の整数であり、Xは有機または無機アニオン成分である、熱酸発生剤と、を含む。式IIAの好ましいR1基は、−CF3、−CN及び−NO2、アセチル、ならびにエステルが含まれる。好ましいエステルR1基は、リソグラフィ処理中(例えば、オーバーコーティングされたフォトレジスト層の像形成の熱処理中)に反応性ではない(例えば、結合破壊反応を起こさないか、または著しく結合破壊反応を起こす)。好ましいX基は、トシルレートなどの有機成分である。
R2は、独立して、水素、C1−C6アルキル、C3−C6シクロアルキルまたは、フェニルであり、これらは任意に置換されていてもよく、
nは0〜5の整数であり、
Xは有機または無機アニオン成分である、熱酸発生剤と、を含む。
本発明の反射防止組成物に用いられる好ましい熱酸発生剤化合物は、下記一般式(A)、(B)、または(C)の構造を有していてもよい。
下地コーティング組成物と共に使用するためのフォトレジストは、典型的には、ポリマー及び1つ以上の酸発生剤を含む。一般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性を付与する官能基を有する。例えば、ヒドロキシルまたはカルボキシレートのような極性官能基、またはリソグラフィ処理の際にそのような極性部分を遊離させ得る酸不安定基を含むポリマーが好ましい。好ましくは、ポリマーは、レジストをアルカリ性水溶液で現像可能にするのに十分な量でレジスト組成物に使用される。
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などの様々な方法のいずれかによって基板にコーティング層として塗布される。一般に、コーティング組成物は、約0.02〜0.5μmの乾燥層厚、好ましくは約0.04〜0.20μmの、乾燥層厚で基板上に塗布される。基板は、フォトレジストを含むプロセスで使用される任意の基板であることが適切である。例えば、基板は、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エレクトロニクスウエハであってもよい。ガリウム砒素、炭化珪素、セラミック、石英、または銅基板を使用することもできる。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板、例えばガラス基板、酸化インジウムスズコーティングされた基板など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)のための基板もまた使用することができる。
実施例2:3−フルオロピリジン−1−イウム4−メチルベンゼンスルホネートの合成
4−メチルベンゼンスルホン酸水和物(75.0g、1.0当量)をテトラヒドロフラン(1500mL)に溶解し、10〜20℃において0.5時間激しく撹拌しながら、3−フルオロピリジン(40.2g、1.05当量)を滴加した。添加後、反応混合物を室温で16時間撹拌した。これをろ過し、テトラヒドロフラン(750mL)を用いて洗浄した。白色固体を真空下で乾燥させた。
4−メチルベンゼンスルホン酸水和物(25.0g、1.0当量)をテトラヒドロフラン(500mL)中に溶解し、10〜20℃において0.5時間激しく撹拌しながら、4−フルオロピリジン(13.4g、1.05当量)を滴加した。添加後、反応混合物を室温で16時間撹拌した。それをろ過し、ジエチルエーテル(250mL)を用いて洗浄した。白色固体を真空下で乾燥させた。
4−メチルベンゼンスルホン酸水和物(6.0g、1.0当量)をテトラヒドロフラン(120mL)(4.9g、1.05当量)に溶解し、10〜20℃において0.5時間激しく撹拌しながら4−(トリフルオロメチル)ピリジンを滴加した。添加後、反応混合物を室温で16時間撹拌した。それをろ過し、ジエチルエーテル(60mL)を用いて洗浄した。白色固体を真空下で乾燥させた。
実施例5:
0.863gのポリマー(実施例1)、架橋剤として0.027gのテトラメトキシメチルグリコールウリル及びTAGとして0.010gの3−フルオロピリジン−1−イウム4−メチルベンゼンスルホネート塩(実施例2)を99.0gのHBM溶媒に溶解した。
0.863gのポリマー(実施例1)、架橋剤として0.027gのテトラメトキシメチルグリコールウリル及びTAGとして0.010gの4−フルオロピリジン−1−イウム4−メチルベンゼンスルホネート塩(実施例3)を99.0gのHBM溶媒に溶解した。
0.860gのポリマー(実施例1)、架橋剤として0.027gのテトラメトキシメチルグリコールウリル及びTAGとして0.013gの4−(トリフルオロメチル)ピリジン−1−イウム4−メチルベンゼンスルホネート塩(実施例4)を99.0gのHBM溶媒に溶解した。
0.866gのポリマー(実施例1)、架橋剤として0.027gのテトラメトキシメチルグリコールウリル及びTAGとして0.007gの4−メチルベンゼンスルホン酸アンモニウム塩をHBM溶媒99.0gに溶解した。
反射防止組成物を、リソグラフィ用途に関連する以下の特性について評価した 1)コーティングされた膜層の厚さ、2)組成物膜層の硬化が最初に起こり得る開始温度、3)組成物膜層の被覆、4)光学パラメータ、5)組成物膜層の接触角、及び6)組成物膜層の昇華試験。これらの特性を評価するために、以下の表1に示すプロトコルを使用した。
パート1:光学的及び機能的な試験性能。
実施例5、6、7、及び8のそれぞれの反射防止組成物の膜層をシリコンウエハ上にスピンコートし、上記表1に記載した193nmの照射による光学パラメータ、接触角、及び相対的な昇華を評価した。結果を以下の表2に示す。
実施例5、6、7、及び8の反射防止組成物の膜層をシリコンウエハ上にスピンコートし、上記の表1に記載されているように、開始温度及び膜被覆について評価した。結果を以下の表3に示す。表3で説明したように、実施例5、6、及び7の反射防止組成物は、低い開始温度を示した(90℃→60℃)。実施例5、6、及び7の反射防止組成物はまた、実施例8(比較)よりもはるかに改善された膜被覆性を提供した。
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)基板上に、1)イソシアヌレート単位を含む樹脂及びシアヌレート置換基を含む樹脂からなる群から選択される樹脂と、2)式(I)の構造を含む熱酸発生剤であって、
b)前記コーティング組成物層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。 - 少なくとも1つのR1がFである、及び/または少なくとも1つのR1がCF3である、及び/またはXがトシレートである、請求項1に記載の方法。
- 前記熱酸発生剤化合物が、下記式(A)、(B)、または(C)の構造を有する、請求項1に記載の方法。
- 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)基板上に、1)イソシアヌレート単位を含む樹脂及びシアヌレート置換基を含む樹脂からなる群から選択される樹脂と、2)式(I)の構造を含む熱酸発生剤であって、
b)前記コーティング組成物層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。 - 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)基板上に、1)イソシアヌレート単位を含む樹脂及びシアヌレート置換基を含む樹脂からなる群から選択される樹脂と、2)式(I)の構造を含む熱酸発生剤であって、
R2は、独立して、水素、C1−C6アルキル、C3−C6シクロアルキル、またはフェニルであり、これらは任意に置換されていてもよく、
nは1〜5の整数であり、
Xはアニオン成分である、熱酸発生剤と、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。 - 前記工程a)の後かつ前記工程b)の前に、a’)55℃〜75℃の温度で前記コーティング組成物の前記塗布された層を硬化する工程をさらに含む、請求項1〜5のいずれか一項に記載の方法。
- 基板を含むコーティングされた基板であって、前記基板が、
a)1)イソシアヌレート単位を含む樹脂及びシアヌレート置換基を含む樹脂からなる群から選択される樹脂と、2)式(I)の構造を含む熱酸発生剤であって、
R2は、独立して、水素、C1−C6アルキル、C3−C6シクロアルキル、またはフェニルであり、これらは任意に置換されていてもよく、
nは1〜5の整数であり、
Xはアニオン成分である、熱酸発生剤と、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の層上のフォトレジスト組成物の層と、を含む、コーティングされた基板。 - 式(I)のYHが、以下の構造のうちの1つである、請求項7に記載の基板。
- オーバーコーティングされたフォトレジスト組成物と共に使用するための反射防止組成物であって、
1)イソシアヌレート単位を含む樹脂及びシアヌレート置換基を含む樹脂からなる群から選択される樹脂と、
2)式(IA)の構造を含む熱酸発生剤であって、
R2は、独立して、水素、任意に置換されたC1−C6アルキル、任意に置換されたC3−C6シクロアルキル、または任意に置換されたフェニルであり、nは1〜5の整数であり、Xはアニオン成分である、熱酸発生剤と、を含む、反射防止組成物。 - 式(IA)のYHが、以下の構造のうちの1つである、請求項9に記載の反射防止組成物。
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US11269252B2 (en) | 2019-07-22 | 2022-03-08 | Rohm And Haas Electronic Materials Llc | Method for forming pattern using antireflective coating composition including photoacid generator |
US11782345B2 (en) | 2019-08-05 | 2023-10-10 | Taiwan Semiconductor Manufacturing Co., Ltd. | Bottom antireflective coating materials |
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