JP2022074080A - フォトレジスト組成物及びパターン形成方法 - Google Patents
フォトレジスト組成物及びパターン形成方法 Download PDFInfo
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- JP2022074080A JP2022074080A JP2021176021A JP2021176021A JP2022074080A JP 2022074080 A JP2022074080 A JP 2022074080A JP 2021176021 A JP2021176021 A JP 2021176021A JP 2021176021 A JP2021176021 A JP 2021176021A JP 2022074080 A JP2022074080 A JP 2022074080A
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Classifications
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- 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
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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
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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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
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- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
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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
- G03F7/20—Exposure; Apparatus therefor
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- 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
- H01L21/0274—Photolithographic processes
Abstract
Description
(b)フォトレジスト組成層をソフトベークする工程と、(b)ソフトベークされたフォトレジスト組成層を活性化放射線に露光する工程と、
(d)フォトレジスト組成層を露光後ベークする工程と、
(c)レジストレリーフ像を提供するために、露光後ベークされたフォトレジスト組成層を現像する工程と、を含む。
CH2=CH-O-R17-O-CH=CH2(5-1)
(式中、R17は、C1~10直鎖アルキレン、C3~10分岐アルキレン、C3~10環式アルキレン、又はこれらの組み合わせを表し、そのそれぞれは、置換され得る又は非置換であり得る)。
モノマーM1、M2、M3、及びM4の繰り返し単位をそれぞれ35/30/25/10のモル比で含む5.0gのポリマーを、13gの2-ヒドロキシイソ酪酸メチル及び7gのプロピレングリコールモノメチルエーテルアセテートに撹拌しながら溶解し、透明な溶液を得た。撹拌溶液に、0.15gのジフルオロ酢酸及び0.30gの水を加えた。混合物を35℃に温め、撹拌したままにした。72時間後、反応混合物を室温に冷却し、反応混合物を300mLのメタノールに直接加えることによりポリマーを沈殿させた。固体を濾過により収集し、真空で乾燥させて、ポリマーP1として3.5gの白色固体を得た。分子量は、ポリスチレン標準に対するGPCによって決定され、数平均分子量(Mn)=3710Da、重量平均分子量(Mw)=5560ダルトン、PDI(多分散度指数)=1.5であることがわかった。
実施例3~5
フォトレジスト組成物は、表1に記載の材料及び量を使用して、固体成分を溶媒に溶解することによって調製した。得られた混合物は、16~50gの規模で作製され、機械振とう機で3~24時間振とうし、次いで0.2ミクロンの孔径を有するPTFEディスク形フィルターを通して濾過した。
実施例6~8
300mmのシリコンウェハーを、AR(商標)40A反射防止剤(DuPont Electronics&Imaging)を用い、205℃の硬化温度を使用し60秒間スピンコーティングして、厚さ800Åの第1のBARC層を形成した。次いで、ウェハーを、AR(商標)104反射防止剤(DuPont Electronics&Imaging)を用い、175℃の硬化温度を使用し60秒間スピンコーティングして、厚さ400Åの第2のBARC層を形成した。次いで、ウェハーを、実施例3~5で調製されたそれぞれのフォトレジスト組成物を用いスピンコーティングし、110℃で60秒間ソフトベークして、厚さ900Åのフォトレジスト層を得た。BARC層とフォトレジスト層は、TEL Clean Track Lithiusコーティングツールでコーティングした。ウェハーを、1:1のラインスペースパターン(55nmの線幅/110nmのピッチ)を有するマスクを使用して、ASML 1900i液浸スキャナー(1.3NA、0.86/0.61内側/外側シグマ、35Y偏光のダイポール照明)を使用して露光した。露光されたウェハーを、100℃で60秒間、露光後ベークし、0.26NのTMAH水溶液で12秒間現像した。次いで、ウェハーを脱イオン水で濯ぎ、スピンドライしてフォトレジストパターンを形成した。形成されたパターンのCD線幅測定は、Hitachi High Technologies Co.CG4000CD-SEMを使用して行った。パターンCDがマスクパターンのCD(55nm線幅)と等しくなる露光量であるEサイズも決定した。LWRは、線幅測定の合計100の任意のポイントの分布からの3シグマ値を使用して決定した。結果を表2に示す。
Claims (10)
- 酸分解性基を含む第1のフリーラジカル重合性モノマーから形成される第1の繰り返し単位と、カルボン酸基を含む第2のフリーラジカル重合性モノマーから形成される第2の繰り返し単位とを含む酸感受性ポリマーと、
2つ以上のエノールエーテル基を含む化合物であって、前記化合物は前記酸感受性ポリマーとは異なる化合物と、
塩基不安定基を含む材料と、
光酸発生剤と、
溶媒と、
を含むフォトレジスト組成物。 - 前記化合物は、式(5-1):
CH2=CH-O-R17-O-CH=CH2(5-1)
(式中、R17は、C1~10直鎖アルキレン、C3~10分岐アルキレン、C3~10環式アルキレン、又はこれらの組み合わせを表し、そのそれぞれは、置換され得る又は非置換であり得る)のものである、請求項2に記載のフォトレジスト組成物。 - 前記化合物は、ポリマー主鎖にぶら下がっているエノールエーテル基を含む第1の繰り返し単位を含むポリマーである、請求項1に記載のフォトレジスト組成物。
- 前記化合物の前記第1の繰り返し単位は、ビニル芳香族モノマー又は(メタ)アクリレートモノマーから形成される、請求項4に記載のフォトレジスト組成物。
- 前記酸分解性基は、式-C(=O)OC(R5)3(式中、R5は、それぞれ独立して、直鎖C1~20アルキル、分岐C3~20アルキル、単環式又は多環式C3~20シクロアルキル、直鎖C2~20アルケニル、分岐C3~20アルケニル、単環式又は多環式C3~20シクロアルケニル、単環式又は多環式C6~20アリール、或いは単環式又は多環式C2~20ヘテロアリール、好ましくは直鎖C1~6アルキル、分岐C3~6アルキル、或いは単環式又は多環式C3~10シクロアルキルであり、そのそれぞれは、置換されている又は非置換であり、各R5は、任意選択で、その構造の一部として、-O-、-S-、-N(R6)-、-C(O)-、-C(O)O-、又は-C(O)N(R6)-から選択された1つ以上の基を含み、R6は、水素或いは置換又は非置換C1~10アルキルを表し、任意の2つのR5基は、一緒に任意選択で環を形成する)の3級エステル基である、請求項1~5のいずれか一項に記載のフォトレジスト組成物。
- 前記第1のフリーラジカル重合性モノマー及び前記第2のフリーラジカル重合性モノマーは、独立して、ビニル芳香族モノマー又は(メタ)アクリレートモノマーである、請求項1~6のいずれか一項に記載のフォトレジスト組成物。
- 前記感光性ポリマーは、ラクトン基を含む第3の繰り返し単位を更に含む、請求項1~7のいずれか一項に記載のフォトレジスト組成物。
- 塩基不安定基を含む前記材料は、フッ素化ポリマーである、請求項1~8のいずれか一項に記載のフォトレジスト組成物。
- (a)基板に請求項1~9のいずれか一項に記載のフォトレジスト組成物の層を塗布する工程と、
(b)前記フォトレジスト組成層をソフトベークする工程と、
(b)前記ソフトベークされたフォトレジスト組成層を活性化放射線に露光する工程と、
(d)前記フォトレジスト組成層を露光後ベークする工程と、
(c)レジストレリーフ像を提供するために、前記露光後ベークされたフォトレジスト組成層を現像する工程と、
を含むパターン形成方法。
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JP4826840B2 (ja) * | 2009-01-15 | 2011-11-30 | 信越化学工業株式会社 | パターン形成方法 |
WO2011034176A1 (ja) * | 2009-09-18 | 2011-03-24 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法、重合体及び重合性化合物 |
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JP5729392B2 (ja) * | 2010-12-02 | 2015-06-03 | Jsr株式会社 | 感放射線性樹脂組成物及び感放射線性酸発生剤 |
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JP2000029216A (ja) * | 1998-07-09 | 2000-01-28 | Fuji Photo Film Co Ltd | ポジ型レジスト組成物 |
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JP2002156764A (ja) * | 2000-11-20 | 2002-05-31 | Tokyo Ohka Kogyo Co Ltd | 微細レジストホールパターン形成方法 |
JP2015031796A (ja) * | 2013-08-01 | 2015-02-16 | 富士フイルム株式会社 | パターン形成方法、感活性光線性又は感放射線性樹脂組成物、及び、レジスト膜、並びに、これらを用いた電子デバイスの製造方法、及び、電子デバイス |
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