WO2010147079A1 - 感放射線性樹脂組成物 - Google Patents
感放射線性樹脂組成物 Download PDFInfo
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- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
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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
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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
- 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
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- 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
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Definitions
- Resin (A) has a repeating unit having an acid dissociable group.
- a preferred example of the repeating unit having such an acid dissociable group is the repeating unit (2).
- the molar ratio of the addition amount of the radical polymerization initiator and the addition amount of the chain transfer agent is preferably 1: 1 to 0.005: 1.
- the weight average molecular weight (hereinafter referred to as “Mw”) in terms of polystyrene by gel permeation chromatography (GPC) of the resin (A) is usually 1,000 to 300,000 and 2,000 to 300,000. It is preferably 2,000 to 12,000. If the Mw of the resin (A) is less than 1,000, the heat resistance as a resist may decrease. On the other hand, if it exceeds 300,000, developability as a resist may be lowered.
- the acid generator (B) can be used alone or in combination of two or more.
- the content of the acid generator (B) is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the resin (A) from the viewpoint of ensuring sensitivity and developability as a resist. More preferably, it is 1 to 20 parts by mass.
- the content of the acid generator (B) is less than 0.1 parts by mass, sensitivity and developability may be deteriorated.
- it exceeds 30 parts by mass the transparency to radiation is lowered, and it tends to be difficult to obtain a rectangular resist pattern.
- the acid generator (B) may not be contained.
- Specific examples of the sulfonium cation represented by the general formula (1-1) include sulfonium cations represented by the formulas (1-1-1) to (1-1-21).
- Specific examples of the iodonium cation represented by the general formula (1-2) include iodonium cations represented by the formulas (1-2-1) to (1-227).
- Such nitrogen-containing organic compounds are not particularly limited, and mono (cyclo) alkylamines, di (cyclo) alkylamines, tri (cyclo) alkylamines, substituted alkylamines, and aromatic amines. Any compound such as a diamine compound, polyethyleneimine, polyallylamine, a polymer of 2-dimethylaminoethylacrylamide, an amide group-containing compound, a urea compound, and a nitrogen-containing heterocyclic compound may be used.
- Nitrogen-containing organic compound (D) (D-1): Nt-butoxycarbonyl-4-hydroxypiperidine
- the radiation-sensitive resin composition of the present invention can be suitably used for a photoresist that is required to have a finer line width of a resist pattern in the future.
Abstract
Description
樹脂(A)は、アルカリ不溶性又はアルカリ難溶性を示す重合体であるが、酸の作用により脱離可能な保護基(酸解離性基)を有し、酸の作用により保護基が脱離してアルカリ可溶性を示す重合体である。なお、ここでいう「アルカリ不溶性又はアルカリ難溶性」とは、樹脂(A)を含有する感放射線性樹脂組成物を用いて形成したレジスト被膜からレジストパターンを形成する際に採用されるアルカリ現像条件下で、レジスト被膜の代わりに樹脂(A)のみを用いた膜厚100nmの被膜を現像した場合に、被膜の初期膜厚の50%以上が現像後に残存する性質をいう。
樹脂(A)の調製方法は、特に限定されるものではないが、例えば、所望の分子組成を構成する各繰り返し単位に対応する重合性不飽和単量体を、ラジカル重合開始剤、連鎖移動剤等の存在下、適当な溶媒中で重合することにより調製することができる。ラジカル重合開始剤は、十分な重合速度を実現するために、十分高い濃度になる量を添加することが好ましい。但し、連鎖移動剤の添加量に対するラジカル重合開始剤の添加量の比率が高すぎると、ラジカル-ラジカルカップリング反応が発生し、望ましくない非リビングラジカル重合体が生成するので、分子量及び分子量分布等の高分子特性においてコントロールされていない特性を有する重合体が得られる。そのため、ラジカル重合開始剤の添加量と連鎖移動剤の添加量とのmol比率(ラジカル重合開始剤:連鎖移動剤)は、1:1~0.005:1であることが好ましい。
酸発生剤(B)としては、放射線が照射されることで酸を発生し得る化合物である。なお、本明細書中では、KrFエキシマレーザー(波長248nm)或いはArFエキシマレーザー(波長193nm)に代表される遠紫外線等の活性光線についても、便宜上「放射線」の概念に含めるものとする。
化合物(C)は、一般式(i)で表される化合物であり、露光によりpKaが3~8程度の弱酸を発生するものであることが好ましい。樹脂(A)における酸解離性基、例えば、繰り返し単位(2)における酸解離性基は、このような弱酸では解離しない構造を有している。一方、酸発生剤(B)から露光により発生する酸はpKaが2以下であることが望ましく、非照射部の化合物(C)は、酸発生剤(B)より発生する酸とイオン交換反応を行い、酸の拡散現象を抑制する作用を有する。一方、放射線の照射部においては、化合物(C)は分解することで酸発生剤(B)より発生する酸に対しての塩基性を失う。そのため、化合物(C)を含有する本発明の感放射線性樹脂組成物を用いれば、放射線の照射部と非照射部において良好なコントラストが得られることに加えて、微細ラインパターンを形成する場合でも、レジストパターンが倒壊することなく、正確なパターニングが可能となる。
本発明の感放射線性樹脂組成物は、必要に応じて、その他の酸拡散制御剤、脂環族添加剤、界面活性剤、増感剤等の各種の添加物をその他の成分として含有することができる。
本発明の感放射線性樹脂組成物は、その使用に際して、通常、全固形分濃度が1~50質量%、好ましくは3~25質量%となるように、溶剤に溶解した後、例えば孔径0.2μm程度のフィルターでろ過して、感放射線性樹脂組成物の溶液として調製される。感放射線性樹脂組成物の溶液の調製に使用される溶剤としては、例えば、2-ペンタノン、2-ヘキサノン、2-ヘプタノン、2-オクタノン等の直鎖状又は分岐状のケトン類;シクロペンタノン、シクロヘキサノン等の環状のケトン類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類;2-ヒドロキシプロピオン酸メチル、2-ヒドロキシプロピオン酸エチル等の2-ヒドロキシプロピオン酸アルキル類;3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル等の3-アルコキシプロピオン酸アルキル類の他、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、酢酸n-ブチル、ピルビン酸メチル、ピルビン酸エチル、N-メチルピロリドン、γ-ブチロラクトン等がある。
GEヘルスケアバイオサイエンス社製のイオン交換樹脂(QAE Sephadex A-25)20gを超純水にて一昼夜膨潤させた後、カラム管に充填した。イオン交換樹脂を充填したカラム管に、式(X-1)で表されるナトリウム塩28gをメタノールに溶解した溶液を流し込み、スルホンアミドアニオンをイオン交換樹脂に担持した。十分量のメタノールにてフラッシュバックした後、トリフェニルスルホニウムクロライド5.2gをメタノールに溶解した溶液をカラム管に流し込み、アニオン交換反応を行った。得られた溶液をエバポレーターにて溶剤留去した後、室温で一昼夜乾燥して、式(C-1)で表される化合物(以下、「化合物(C-1)」という)を得た(収量8.0g)。
前記イオン交換樹脂20gを超純水にて一昼夜膨潤させた後、カラム管に充填した。イオン交換樹脂を充填したカラム管に、式(X-1)で表されるナトリウム塩28gをメタノールに溶解した溶液を流し込み、スルホンアミドアニオンをイオン交換樹脂に担持した。十分量のメタノールにてフラッシュバックした後、ジフェニルヨードニウムクロライド5.6gをメタノールに溶解した溶液をカラム管に流し込み、アニオン交換反応を行った。得られた溶液をエバポレーターにて溶剤留去した後、室温で一昼夜乾燥して、式(C-2)で表される化合物(以下、「化合物(C-2)」という)を得た(収量8.2g)。
前記イオン交換樹脂20gを超純水にて一昼夜膨潤させた後、カラム管に充填した。イオン交換樹脂を充填したカラム管に、式(X-2)で表されるナトリウム塩28gをメタノールに溶解させた溶液を流し、スルホンアミドアニオンを樹脂に担持した。十分量のメタノールにてフラッシュバックした後、トリフェニルスルホニウムニウムクロライド5.8gをメタノールに溶解した溶液をカラム管に流し込み、アニオン交換を行った。得られた溶液をエバポレーターにて溶剤除去した後、室温で一昼夜乾燥して、式(C-3)で表される化合物(以下、「化合物(C-3)」という)を得た(収量8.1g)。
前記イオン交換樹脂20gを超純水にて一昼夜膨潤させた後、カラム管に充填した。そこにセントラルガラス社製の(X-3)誘導体を炭酸水素ナトリウム等の金属塩基にて脱プロトン化した下記式(X-3)で表されるナトリウム塩28gをメタノールに溶解した溶液を流し込み、スルホンアミドアニオンを樹脂に担持した。十分量のメタノールにてフラッシュバックした後、トリフェニルスルホニウムクロライド5.2gをメタノールに溶解した溶液をカラム管に流し込み、アニオン交換を行った。得られた溶液をエバポレーターにて溶剤除去した後、室温で一昼夜乾燥して、式(C-4)で表される化合物(以下、「化合物(C-4)」という)を得た(収量8.1g)。
式(M-1)で表される単量体(以下、「単量体(M-1)」ともいう)8.5g(35mol%)、式(M-4)で表される単量体(以下、「単量体(M-4)」ともいう)5.4g(15mol%)、及び式(M-6)で表される単量体(以下、「単量体(M-6)」ともいう)16.1g(50mol%)を、2-ブタノン60gに溶解し、更にジメチルアゾビスイソブチロニトリル1.2gを投入した単量体溶液を準備した。一方で、30gの2-ブタノンを投入した200mlの三口フラスコを30分窒素パージした後、反応釜を攪拌しながら80℃に加熱し、事前に準備した単量体溶液を滴下漏斗を用いて3時間かけて滴下した。滴下開始を重合開始時間とし、重合反応を6時間実施した。
表1に示す種類の単量体を、表1に示す配合処方で使用したこと以外は、合成例5と同様の方法によって、共重合体を調製した。なお、得られた共重合体のMw、Mw/Mn、収率、及び共重合体中の各単量体に由来する繰り返し単位の割合の測定結果を表2に示す。各共重合体を樹脂(A-2)~(A-14)とする。
合成例5で調製した樹脂(A-1)100部、酸発生剤(B-3)8.5部、合成例1で合成した化合物(C-1)4.5部、溶剤(E-1)1700部、溶剤(E-2)700部、及び溶剤(E-3)30部を混合して感放射線性樹脂組成物を調製した。
表3に示す配合処方としたこと以外は実施例1と同様にして感放射線性樹脂組成物を調製した。
(B-1):トリフェニルスルホニウムノナフルオロ-n-ブタンスルホネート
(B-2):トリフェニルスルホニウム2-(ビシクロ[2.2.1]ヘプタ-2’-イル)-1,1-ジフルオロエタンスルホネート
(B-3):トリフェニルスルホニウム2-(ビシクロ[2.2.1]ヘプタ-2’-イル)-1,1,2,2-テトラフルオロエタンスルホネート
(B-4):トリフェニルホスホニウム1,1,2,2-テトラフルオロ-6-(1-アダマンタンカルボニロキシ)-ヘキサン-1-スルホネート
(B-5):トリフェニルホスホニウム2-アダマンチル-1,1-ジフルオロエタンスルホネート
(B-6):下記式(4)に示す化合物
(D-1):N-t-ブトキシカルボニル-4-ヒドロキシピペリジン
(E-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
(E-2):シクロヘキサノン
(E-3):γ-ブチロラクトン
実施例1~25及び比較例1~3の感放射線性樹脂組成物について、以下のようにして各種評価を行った。これらの評価結果を表4に示す。
[最小倒壊前寸法の評価]:感度の評価の最適露光量にて解像した90nmのラインアンドスペースパターンの観測において、この最適露光量よりも大きな露光量にて露光を行った場合、得られるパターンの線幅が細くなるため、最終的にレジストパターンの倒壊が見られる。このレジストパターンの倒壊が確認されない最大の露光量における線幅を最小倒壊前寸法(nm)と定義し、パターン倒れ耐性の指標とした。具体的には、最小倒壊前寸法が40.0nm以下の場合「良好」と評価し、40.0nmを超える場合「不良」と評価した。なお、最小倒壊前寸法の測定は、前記走査型電子顕微鏡を用いた。
Claims (4)
- (A)酸解離性基含有樹脂と、
(C)下記一般式(i)で表される化合物と、を含有する感放射線性樹脂組成物。
- (B)感放射線性酸発生剤を更に含有する請求項1に記載の感放射線性樹脂組成物。
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JP2012018304A (ja) * | 2010-07-08 | 2012-01-26 | Tokyo Ohka Kogyo Co Ltd | ポジ型レジスト組成物及びレジストパターン形成方法 |
JP2012108447A (ja) * | 2010-10-22 | 2012-06-07 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、レジストパターン形成方法 |
TWI554528B (zh) * | 2010-12-28 | 2016-10-21 | 東京應化工業股份有限公司 | 光阻組成物,光阻圖型之形成方法 |
US20120164578A1 (en) * | 2010-12-28 | 2012-06-28 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern |
JP2012141371A (ja) * | 2010-12-28 | 2012-07-26 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、レジストパターン形成方法 |
US9494860B2 (en) * | 2010-12-28 | 2016-11-15 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern |
TWI572984B (zh) * | 2011-02-18 | 2017-03-01 | 東京應化工業股份有限公司 | 光阻組成物、光阻圖型之形成方法 |
KR20130069425A (ko) | 2011-12-14 | 2013-06-26 | 도오꾜오까고오교 가부시끼가이샤 | 레지스트 조성물, 레지스트 패턴 형성 방법 |
US9063416B2 (en) | 2011-12-14 | 2015-06-23 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern and compound |
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JP2013145255A (ja) * | 2012-01-13 | 2013-07-25 | Shin Etsu Chem Co Ltd | パターン形成方法及びレジスト組成物 |
JP2013145256A (ja) * | 2012-01-13 | 2013-07-25 | Shin Etsu Chem Co Ltd | パターン形成方法及びレジスト材料 |
US9188863B2 (en) | 2012-06-20 | 2015-11-17 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
KR20130142914A (ko) | 2012-06-20 | 2013-12-30 | 도오꾜오까고오교 가부시끼가이샤 | 레지스트 조성물 및 레지스트 패턴 형성 방법 |
KR20140074240A (ko) | 2012-12-07 | 2014-06-17 | 도쿄 오카 고교 가부시키가이샤 | 레지스트 조성물 및 레지스트 패턴 형성 방법 |
JP2020037544A (ja) * | 2018-09-05 | 2020-03-12 | 信越化学工業株式会社 | スルホニウム化合物、ポジ型レジスト組成物、及びレジストパターン形成方法 |
JP7031537B2 (ja) | 2018-09-05 | 2022-03-08 | 信越化学工業株式会社 | スルホニウム化合物、ポジ型レジスト組成物、及びレジストパターン形成方法 |
Also Published As
Publication number | Publication date |
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KR20120039628A (ko) | 2012-04-25 |
CN102804065B (zh) | 2014-07-16 |
JP5655781B2 (ja) | 2015-01-21 |
CN102804065A (zh) | 2012-11-28 |
EP2444845A1 (en) | 2012-04-25 |
US8921027B2 (en) | 2014-12-30 |
EP2444845A4 (en) | 2013-05-29 |
KR101729350B1 (ko) | 2017-04-21 |
TW201115270A (en) | 2011-05-01 |
US20120082936A1 (en) | 2012-04-05 |
TWI416256B (zh) | 2013-11-21 |
JPWO2010147079A1 (ja) | 2012-12-06 |
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