JP6090547B2 - 硬化性組成物、レジスト材料及びレジスト膜 - Google Patents
硬化性組成物、レジスト材料及びレジスト膜 Download PDFInfo
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- JP6090547B2 JP6090547B2 JP2016557510A JP2016557510A JP6090547B2 JP 6090547 B2 JP6090547 B2 JP 6090547B2 JP 2016557510 A JP2016557510 A JP 2016557510A JP 2016557510 A JP2016557510 A JP 2016557510A JP 6090547 B2 JP6090547 B2 JP 6090547B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/043—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of metal
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
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Description
光インプリント法では、レジスト膜を成型して得られるパターンを鋳型とし、エッチングを行うことで、基板にパターンを転写する。この時、パターンが形成されたレジスト膜には高いエッチング耐性が要求される。光インプリント法において、基板に直接パターンを転写する方法や、レジスト膜を第一レジスト層とし、基板が第二レジスト層と下層基板とを有する、2層レジスト法などが知られている。2層レジスト層としては、例えば、第一レジスト層に含ケイ素樹脂を用いた上で、酸素系ガスのプラズマによるエッチングを行って第二レジスト層にパターンを転写し、パターンが転写された第二レジスト層にさらにエッチングを行って、下層基板にパターンを転写する方法が知られている。
また、酸処理により可溶化する樹脂をレジストに用いることで、モールド残渣物を除去する方法が特許文献1に開示されている。しかし、用いられている樹脂はケイ素が含有されておらず、硬化性官能基濃度も低いことから、酸素系ガスによるドライエッチング耐性が低く、基板へのパターン転写精度が低くなる恐れがあった。
−O−R−Y ・・・(1)
(上記式(1)において、酸素原子はケイ素原子に結合し、Rはヘテロ原子を含んでもよい非置換または置換の炭素数0〜25のアルキル基を表し、Yは重合性不飽和基を表す)
単量体のモル比が(A):(B)=100:0〜10:90であって、(A):(C)=80:20〜100:0であることを特徴とする硬化性組成物を提供する。
本発明の硬化性樹脂は、多官能重合性単量体(A)を含有することを特徴とする。本発明の多官能重合性単量体(A)は、重合性基を有する基を二つ以上有する多官能重合性単量体であって、下記式(1)で表される重合性基を有する基Qを少なくとも1つ有することを特徴とする。
−O−R−Y ・・・(1)
(上記式(1)において、酸素原子はケイ素原子に結合し、Rはヘテロ原子を含んでもよい非置換または置換の炭素数0〜25のアルキル基を表し、Yは重合性基を表す)
重合性基を有する基Qは、多官能重合性単量体(A)内に少なくとも1つ有するが、2つ以上であると洗浄性が向上するため好ましい。
本発明の硬化性組成物は、単官能重合性単量体(B)を含有しても構わない。単官能重合性単量体(B)は、重合性基を1個有する化合物である。重合性基とは、重合反応が可能な官能基を表し、具体的にはラジカル重合性基やカチオン重合性基等が挙げられる。単官能重合性単量体(B)が有する重合性基は、上記多官能重合性単量体(A)の有する重合性基と反応する基であることが好ましく、例えば多官能重合性単量体(A)の有する重合性基が(メタ)アクリロイル基である場合、単官能重合性単量体(B)の有する重合性基も(メタ)アクリロイル基であることが好ましい。
本発明の硬化性組成物は、多官能重合性単量体(A)以外の多官能重合性単量体(C)を含有しても構わない。多官能重合性単量体(C)としては、具体的には1,2−エタンジオールジ(メタ)アクリレート、1,2−プロパンジオールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、ジプロピレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、トリス(2−(メタ)アクリロイルオキシ)イソシアヌレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジ(トリメチロールプロパン)テトラ(メタ)アクリレート、ジ(ペンタエリスリトール)ペンタ(メタ)アクリレート、ジ(ペンタエリスリトール)ヘキサ(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、エチレンオキサイド付加ビスフェノールAジ(メタ)アクリレート、エチレンオキサイド付加ビスフェノールFジ(メタ)アクリレート、プロピレンオキサイド付加ビスフェノールAジ(メタ)アクリレート、プロピレンオキサイド付加ビスフェノールFジ(メタ)アクリレート、9、9ビスフェニルフルオレン骨格を有するジ(メタ)アクリレート、(メタ)アクリレート変性シリコーン(信越化学工業(株)製X−22−2445、X−22−1602、X−22−164、X−22−164AS、X−22−164A、X−22−164B、X−22−164C、X−22−164E、KR−513、X−40−2672B、X−40−9272B等)、(メタ)アクリレート変性シルセスキオキサン(東亞合成(株)製AC−SQ TA−100、MAC−SQ TM−100、AC−SQ SI−20、MAC−SQ SI−20等)が挙げられ、特に好ましくは(メタ)アクリレート変性シリコーン(信越化学工業(株)製X−22−2445、X−22−1602、X−22−164、X−22−164AS、X−22−164A、X−22−164B、X−22−164C、X−22−164E、KR−513、X−40−2672B、X−40−9272B等)、(メタ)アクリレート変性シルセスキオキサン(東亞合成(株)製AC−SQ TA−100、MAC−SQ TM−100、AC−SQ SI−20、MAC−SQ SI−20等)である。
本発明の硬化性組成物は、上記多官能重合性単量体(A)を含有し、不揮発分量中のケイ素原子の量が10wt%以上であることを特徴とする。不揮発分量中のケイ素原子の量が10wt%以上であることで、本発明の硬化性組成物はドライエッチング耐性が高いため、ドライエッチング用レジストとして好適である。不揮発分量中のケイ素原子の量は、好ましくは15wt%以上であり、より好ましくは20wt%以上である。
上記ノニオン界面活性剤としては、ポリオキシアルキレンアルキルエーテル系界面活性剤、ポリオキシアルキレン脂肪酸エステル系界面活性剤、ソルビタン脂肪酸エステル系界面活性剤、ポリオキシアルキレンアルキルアミン系界面活性剤、プルロニック系(ポリエチレンオキシドとポリプロピレンオキシドのトリブロック共重合体)界面活性剤、フッ素系界面活性剤、シリコーン系界面活性剤、アクリル重合系界面活性剤等が挙げられる。
アニオン界面活性剤としては、アルキルベンゼンスルホン酸塩系界面活性剤、アルキルアルコール硫酸エステル塩系界面活性剤、ポリオキシアルキレンアルキルエーテル硫酸塩系界面活性剤、アルキルアルコールリン酸エステル塩系界面活性剤、ポリオキシアルキレンアルキルエーテルリン酸塩系界面活性剤、ポリオキシアルキレンアルキルエーテル酢酸塩系界面活性剤、フッ素系界面活性剤等が挙げられ、酸型、中和型のいずれを使用してもよい。
カチオン界面活性剤としては、テトラアルキルアンモニウムハライド系界面活性剤、アルキルピリジニウムハライド系界面活性剤、アルキルイミダゾリンハライド系界面活性剤等が挙げられる。
両性界面活性剤としては、アルキルベタイン系界面活性剤、アルキルイミダゾリニウムベタイン系界面活性剤、レシチン系界面活性剤等が挙げられる。
本発明のレジスト材料は、上記硬化性組成物を含有する。本発明のレジスト材料を硬化することで、レジスト膜が得られる。本発明のレジスト材料にパターンを形成する工程と、前記パターン形成層に光を照射する工程を経てパターンを形成されたレジスト膜を得ることができる。
インプリント用モールドは平面状、ベルト状、ロール状、ロールベルト状等の任意の形状のものを選択できる。
本発明のレジスト材料に含有される多官能重合性単量体(A)は、上記重合性記を有する基Qを有する。該重合性記を有する基Qは、加水分解性基であることから、硬化後に加水分解処理を行うことで、モールドが良好に洗浄される。
モールドの洗浄に用いる加水分解可能な洗浄液としては、酸、アルカリ、熱水等が挙げられる。酸洗浄液としては、硫酸、塩酸、硝酸、炭酸、酢酸、リン酸、王水、希フッ酸、硫酸過水、塩酸過水等が挙げられ、アルカリ洗浄液としては苛性ソーダ、苛性カリなどの苛性アルカリや、各種のケイ酸塩、リン酸塩、炭酸塩等の無機アルカリだけでなく、テトラメチルアンモニウムヒドロキサイドなどの有機アルカリ、アンモニア水、アンモニア水素水、アンモニア過水等が挙げられる。アルカリ洗浄液はSiO2を溶解する恐れがあるため、モールドがガラスや石英の場合には酸洗浄液が好ましく、特に好ましくは硫酸過水である。特に100nm以下の微細パターンをもつ石英モールドの洗浄においては、アルカリ洗浄液にSiO2の溶解作用によりモールドの矩形性を損なう恐れがあるため、酸洗浄液を用いることで微細パターンの損傷無くモールドが洗浄され、繰り返し用いることが出来る。
洗浄方法としては、特に限定は無いが、スプレー、シャワー、浸漬、加温浸漬、超音波浸漬、スピン法、バブリング、揺動法、ブラッシング、スチーム、研磨等が挙げられ、洗浄された汚染物の再付着防止のためには、スピン法が特に好ましい。
また、第二レジスト層と下層基板とを有する二層レジスト用の基材であってもかまわない。二層レジスト用の基材の組み合わせとしては特に限定は無いが、第二レジスト層の材質としてはCr、Al、Ni等のメタルマスクや、ノボラック樹脂等のフェノール樹脂、ヒドロキシビニルナフタレン共重合体、ポリビニルフェノール協重合体等のビニル樹脂、ノルトリシクレン共重合体、インデン共重合体、アセナフチレン共重合、フラーレン誘導体等の多環芳香族系樹脂、これら樹脂の硬化物等からなるSOC層や、CVDで形成されるアモルファスカーボン膜等が挙げられる。また、3層、4層と異なる材料が積層された多層基材であってもよく、本発明のレジスト膜を下層膜として用いることもできる。
本発明のレジスト材料からなるレジスト膜は、ドライエッチング耐性に優れるため、ドライエッチングの際にもパターン等の崩れがなく、ナノサイズの微細なエッチングパターンであっても、基材に転写が可能である。
これらのエッチングガスを用いてエッチングすることにより、基材上に所望のパターンを形成することができる。
<1,3−ビス(アクリロイロキシエチルオキシ)−1,1,3,3−テトラメチルジシロキサン(多官能重合性単量体(A−1))の合成>
窒素雰囲気下、1,3−ジクロロ−1,1,3,3−テトラメチルジシロキサン(4.064g,0.02mol)、トリエチルアミン(4.048g,0.04mol)、テトラヒドロフラン(60mL)に溶解させ、氷浴により0℃に冷却した。そこに2−ヒドロキシエチルアクリレート(4.644g,0.04mol)のテトラヒドロフラン(40mL)溶液を滴下し、0℃で2時間撹拌させて反応させた後、濾過により塩酸塩を除去し、エバポレーションにより濃縮した。酢酸エチルとヘキサン溶剤を用いたシリカゲルカラムクロマトグラフィーにより精製し、減圧分留により多官能重合性単量体(A−1)を5.42g(収率75%)得た。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.42(dd,2H,CH=C),6.16(m,2H,C=CH−C=O),5.87(dd,2H,H=C),4.25(m,4H,CH2−O−C=O),3.90(m,4H,CH2−O−Si),0.12(m,12H,Si−CH3).
<1,5−ビス(アクリロイロキシエチルオキシ)−1,1,3,3,5,5−ヘキサメチルトリシロキサン(多官能重合性単量体(A−2))の合成>
1,3−ビス(アクリロイロキシエチルオキシ)−1,1,3,3−テトラメチルジシロキサンの合成と同様の手法で合成した。原料としては1,3−ジクロロ−1,1,3,3−テトラメチルジシロキサンの代わりに1,5−ジクロロ−1,1,3,3,5,5−ヘキサメチルトリシロキサンを用いた。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.42(dd,2H,CH=C),6.14(m,2H,C=CH−C=O),5.83(dd,2H,H=C),4.25(m,4H,CH2−O−C=O),3.89(m,4H,CH2−O−Si),0.12(m,18H,Si−CH3).
<1,7−ビス(アクリロイロキシエチルオキシ)−1,1,3,3,5,5,7,7−オクタメチルテトラシロキサン(多官能重合性単量体(A−3))の合成>
1,3−ビス(アクリロイロキシエチルオキシ)−1,1,3,3−テトラメチルジシロキサンの合成と同様の手法で合成した。原料としては1,3−ジクロロ−1,1,3,3−テトラメチルジシロキサンの代わりに1,7−ジクロロ−1,1,3,3,5,5,7,7−オクタメチルテトラシロキサンを用いた。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.42(dd,2H,CH=C),6.14(m,2H,C=CH−C=O),5.83(dd,2H,H=C),4.25(m,4H,CH2−O−C=O),3.89(m,4H,CH2−O−Si),0.12(m,24H,Si−CH3).
<多官能重合性単量体(A−4)の合成>
メチル系シリコーンレジンKC−89S(商品名、信越化学工業社製)(137.9g)、2−ヒドロキシエチルアクリレート(81.3g,0.7mol)、パラトルエンスルホン酸一水和物(44mg)を混合し、120℃で反応させながら生成したメタノールを留去し、3時間撹拌して反応させ、多官能重合性単量体(A−4)を197.8g得た。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.43(m,CH=C),6.12(m,C=CH−C=O),5.83(m,CH=C),4.25(br,CH2−O−C=O),3.97(br,CH2−O−Si),3.52(s,Si−OCH3),0.16(s,Si−CH3).重量平均分子量を測定したところ、770であった。
式(1)で表される重合性基を有する基Qの形成を、以下の方法で確認した。
1H−NMRスペクトルで、原料である2−ヒドロキシエチルアクリレート由来のピーク(δ=3.87ppm,C−O−C−CH2−)が消失し、メチル系シリコーンレジンのメトキシ基のピーク(δ=3.52,Si−OCH3)が減少したことから、アルコール交換反応が定量的に進行したことを確認した。また、新たなピーク(δ=3.97,CH2−O−Si)が表れていることから、2−ヒドロキシエチルアクリレートとメチル系シリコーンレジンがSi−O−C結合により結合し、式(1)で表される重合性基を有する基Qが形成したことを確認した。
多官能重合性単量体(A−4)に含まれるケイ素原子の量は次の式により計算した。
ここで、T0成分、T1成分、T2成分、T3成分とは、下記の意味である。
原料であるメチル系シリコーンレジンはT単位からなる。T単位とは、1個のケイ素原子を有し、そのケイ素原子に結合した1個のメチル基と、他のケイ素原子に結合した酸素原子または他のケイ素原子に結合していない官能基3個とを有する単位である。T0は他のケイ素原子に結合した酸素原子の数が0個、T1はその酸素原子の数が1個、T2はその酸素原子の数が2個、T3はその酸素原子の数が3個である。T0/T1/T2/T3のモル%比率は29Si−NMRスペクトル(シングルパルス法)の積分比から算出することができる。
アルコール交換反応の前後でオリゴマー一分子中に含まれるケイ素原子の個数は変わらないので、次の式により原料のシリコーンレジン一分子中に含まれるケイ素原子の個数を算出し、その個数と同じである多官能重合性単量体(A−4)一分子中に含まれるケイ素原子の個数を算出した。
多官能重合性単量体(A−4)一分子中に含まれる、式(1)で表される重合性基を有する基Qの個数は次の式により計算した。
<多官能重合性単量体(A−5)の合成>
メチル系シリコーンレジンKR−500(商品名、信越化学工業社製)(110.8g)、2−ヒドロキシエチルアクリレート(58.1g,0.5mol)、パラトルエンスルホン酸一水和物(34mg)を混合し、120℃で反応させながら生成したメタノールを留去し、3時間撹拌して反応させ、多官能重合性単量体(A−5)を153.9g得た。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.43(m,CH=C),6.13(m,C=CH−C=O),5.83(m,CH=C),4.25(br,CH2−O−C=O),3.96(br,CH2−O−Si),3.50(s,Si−OCH3),0.15(s,Si−CH3).重量平均分子量を測定したところ、1650であった。
式(1)で表される重合性基を有する基Qの形成、多官能重合性単量体(A−5)に含まれるケイ素原子の量、多官能重合性単量体(A−5)一分子中に含まれるケイ素原子の個数、多官能重合性単量体(A−5)一分子中に含まれる式(1)で表される重合性基を有する基Qの個数は、合成例4と同様の方法で算出した。
<多官能重合性単量体(A−6)の合成>
メチル系シリコーンレジンX−40−9225(商品名、信越化学工業社製)(129.3g)、2−ヒドロキシエチルアクリレート(58.1g,0.5mol)、パラトルエンスルホン酸一水和物(38mg)を混合し、120℃で反応させながら生成したメタノールを留去し、3時間撹拌して反応させ、多官能重合性単量体(A−6)を172.4g得た。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.43(m,CH=C),6.13(m,C=CH−C=O),5.83(m,CH=C),4.24(br,CH2−O−C=O),3.95(br,CH2−O−Si),3.48(s,Si−OCH3),0.15(s,Si−CH3).重量平均分子量を測定したところ、3580であった。
式(1)で表される重合性基を有する基Qの形成、多官能重合性単量体(A−6)に含まれるケイ素原子の量、多官能重合性単量体(A−6)一分子中に含まれるケイ素原子の個数、多官能重合性単量体(A−6)一分子中に含まれる式(1)で表される重合性基を有する基Qの個数は、合成例4と同様の方法で算出した。
多官能重合性単量体(A)の具体的な構造は下記に示す構造式の通りである。
2−ヒドロキシエチルアクリレート変性シリコーンレジン・・・(A−5)
2−ヒドロキシエチルアクリレート変性シリコーンレジン・・・(A−6)
B−1:アクリロイロキシプロピルトリメトキシシラン(KBM−5103:信越化学工業社製)
B−2:ベンジルアクリレート(ビスコート#160:大阪有機化学工業社製)
C−2:合成例7に記載の化合物
<多官能重合性単量体(C−2)の合成>
1,3−アダマンタンジカルボン酸(1.9g,8.5mmol)をフラスコに入れ、窒素下で塩化チオニル(25mL)を加えた。フラスコの内容物を3時間還流したのち、過剰の塩化チオニルを留去して蒸発乾固し、白色固体であるトリシクロ[3.3.1.13,7]デカン−1,3−ジカルボニルジクロリドを得た。2−ビニロキシエタノール(2.0g,22.7mmol)、トリエチルアミン(4.0mL)、クロロホルム(10mL)を3つ口フラスコに入れ、窒素下、0度でトリシクロ[3.3.1.13,7]デカン−1,3−ジカルボニルジクロリド(2.1g,8.1mmol)のクロロホルム(15mL)溶液を滴下したのち、室温で18時間攪拌した。反応混合物を分液漏斗に移して1M塩酸で中性になるまで洗浄したのち、飽和炭酸水素ナトリウム水溶液及びイオン交換水で洗浄した。有機層を分取して、無水硫酸マグネシウムで乾燥し、溶媒を留去した。残留した無色透明液体をシリカゲル中圧カラム(展開溶媒:クロロホルム)で精製し、無色粘性液体であるトリシクロ[3.3.1.13,7]デカン−1,3−ジカルボン酸ビス(2−ビニルオキシエチレン)エステルを得た。窒素下で、p−トルエンスルホン酸(36mg,0.21mmol)のTHF(6mL)溶液、メタクリル酸(1.08g,12.6mmol)を3つ口フラスコに入れ、トリシクロ[3.3.1.13,7]デカン−1,3−ジカルボン酸ビス(2−ビニルオキシエチレン)エステル(1.53g,4.2mmol)のTHF溶液10mLを3つ口フラスコに入れ、水浴中で6時間攪拌した。反応混合物からTHFをエバポレータで留去したのち、ジエチルエーテルを加えた。このジエチルエーテル溶液を分液漏斗に移し、飽和炭酸水素ナトリウム水溶液、飽和食塩水でそれぞれ3回ずつ洗浄した。有機層を分取して、無水硫酸マグネシウムで乾燥し、溶媒をエバポレータで留去した。残留した無色透明液体をシリカゲル中圧カラム(展開溶媒:クロロホルム)で精製し、無色粘性液体である多官能重合性単量体(C−2)を得た。
得られた化合物の物性値は、以下の通りである。
1H−NMR(300MHz,CDCl3)δ(ppm):6.1,5.6(4H,s,CH2=C),6.0−5.9(2H,m,O−CH(CH3)−O),4.2(4H,t,−C(=O)−CH2−),3.8−3.6(4H,m,−CH2−O)1.6−2.1(14H,m,adamantane),1.9(6H,s,−CH3),1.3(6H,m,O−CH(CH3)−O).
(硬化性組成物の調製)
実施例1〜8、比較例1〜4について、後述する表2に示す配合量(重量部)に基づいて配合したうえで、光重合開始剤として2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−1−ブタノン(Irgacure−369:BASF社製)を2重量部加え、さらに重合禁止剤として4−メトキシフェノールが重合性単量体に対して200ppmとなるように加えたうえで、0.1μmのテトラフルオロエチレン製フィルターでろ過し、硬化性組成物を調製した。
(レジスト膜の作製)
実施例1〜8及び比較例1〜4で得られた組成物を、メチルイソブチルケトン溶剤を用いて希釈し、膜厚1.0μmとなるように石英基板上にスピンコート塗布した。得られた積層体を、ピーク波長365±5nmのLED光源(ウシオ電機株式会社製)により窒素雰囲気下で樹脂組成物側から1000mJ/cm2の光量で光照射して硬化させ、硬化膜を得た。
(硫酸過水浸漬評価)
得られた硬化膜を、硫酸過水(硫酸:過酸化水素水=4:1(容量比))に5分間浸漬後、イオン交換水で30秒間リンスし、硬化膜の残存を目視観察し、硬化膜の洗浄性を下記のように評価した。
◎:硬化膜が硫酸過水に溶解し、石英基板上に残存が無い。
○:硬化膜が石英基板から剥離し、石英基板上に残存が無い。
×:硬化膜に変化が見られない。
(石英モールド閉塞物の作製)
実施例1〜8及び比較例1〜4に示す組成物を、45〜100nmのライン/スペースパターンを有し、溝深さが100nmの石英を材質とするモールド(NTTアドバンストテクノロジ社製、NIM−PHL45)に塗布し、モールドのパターンを閉塞させた。得られたモールドを、ピーク波長365±5nmのLED光源(ウシオ電機株式会社製)により窒素雰囲気下でモールドのパターン面側から1000mJ/cm2の光量で光照射して硬化させ、石英モールド閉塞物を得た。
(石英モールド洗浄性評価)
得られた石英モールド閉塞物を、硫酸過水(硫酸:過酸化水素水=4:1(容量比))に5分間浸漬後、イオン交換水で30秒間リンスし、窒素ガスで乾燥した。モールドのラインパターン形状断面を走査型電子顕微鏡により観察し、石英モールド洗浄性を下記のように評価した。
走査型電子顕微鏡観察による石英モールドのパターン断面観察において、
○:全面にわたってパターンに閉塞が無い。
×:硬化物で閉塞されている部分がある。
実施例1〜8及び比較例1〜4で作成した硬化性組成物を、シリコンウエハ基材上に1μL滴下し、SCIVAX社製ナノインプリント装置X300の下面ステージにセットした。45〜100nmのライン/スペースパターンを有し、溝深さが100nmの石英を材質とするモールド(NTTアドバンストテクノロジ社製、NIM−PHL45)を、上記装置の上面ステージにセットした。装置内を真空とした後、室温で1.5気圧の圧力でモールドを基板に圧着させ、これにモールドの裏面からピーク波長365±5nmのLED光源を用いて1000mJ/cm2の条件で露光し、モールドを剥離して基材上にパターンを形成させた。ラインパターン形状断面の走査型電子顕微鏡観察を実施し、パターン形成性を下記のように評価した。
走査型電子顕微鏡観察によるパターン断面観察において、
◎:パターンの欠損または倒れが1%未満である。
○:パターンの欠損または倒れが1%以上、5%未満である。
×:パターンの欠損または倒れが5%以上である。
実施例1〜8及び比較例1〜4に示す組成物を、メチルイソブチルケトン溶剤を用いて希釈し、膜厚0.2μmとなるようにシリコンウエハ基材上にスピンコート塗布した。得られた積層体を、ピーク波長365±5nmのLED光源(ウシオ電機株式会社製)により窒素雰囲気下で樹脂組成物側から1000mJ/cm2の光量で光照射して硬化させ、硬化膜を得た。
得られた硬化膜をSAMCO(株)製ドライエッチャーRIE−101iPHを用いてO2/N2=10/10(sccm)の混合ガス供給し、0.1Paの真空下で180秒間酸素プラズマエッチングを行った後、硬化膜の残存膜厚を測定し、1秒間当たりのエッチング速度を算出した。得られたエッチング速度を、実施例1のエッチング速度の値が1となるように規格化した。規格値が小さい程、ドライエッチング耐性に優れていることを示す。
Claims (11)
- 重合性基を有する基を二つ以上有する多官能重合性単量体であって、下記式(1)で表される重合性基を有する基Qを少なくとも1つ有する多官能重合性単量体(A)を含有し、不揮発分量中のケイ素原子の量が10wt%以上であり、
前記多官能性単量体(A)が、ケイ素原子を5個以上含有するものであることを特徴とするドライエッチングレジスト用硬化性組成物。
−O−R−Y ・・・(1)
(上記式(1)において、酸素原子はケイ素原子に結合し、Rはヘテロ原子を含んでもよい非置換または置換の炭素数0〜25のアルキル基を表し、Yは重合性基を表す) - 前記多官能重合性単量体(A)において、前記式(1)で表される重合性基を有する基を二つ以上有するものである、請求項1に記載のドライエッチングレジスト用硬化性組成物。
- 更に単官能重合性単量体(B)または、(A)以外の多官能重合性単量体(C)とを含有する硬化性組成物であって、
単量体の重量比が(A):(B)=100:0〜10:90であって、(A):(C)=80:20〜100:0であることを特徴とする、請求項1又は2に記載のドライエッチングレジスト用硬化性組成物。 - 重合性単量体合計量に対し、多官能重合性単量体が50重量%以上である、請求項1〜3のいずれか一項に記載のドライエッチングレジスト用硬化性組成物。
- 前記請求項1〜4のいずれかに記載のドライエッチングレジスト用硬化性組成物を含有することを特徴とする、レジスト材料。
- 請求項5に記載のレジスト材料を硬化してなることを特徴とするレジスト膜。
- パターンが形成されたものである、請求項6に記載のレジスト膜。
- パターンがナノインプリントパターンである、請求項7に記載のレジスト膜。
- 請求項6〜8のいずれかに記載のレジスト膜が基板に積層されていることを特徴とする、積層体。
- 請求項9に記載の積層体に積層されたレジスト膜に形成されたパターンをマスクとして、基板をドライエッチングすることにより基板にパターンを形成することを特徴とする、パターン形成方法。
- 前記請求項1〜4のいずれかに記載のドライエッチングレジスト用硬化性組成物を硬化してなることを特徴とする成形体。
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CN107075017B (zh) | 2019-11-05 |
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US10197916B2 (en) | 2019-02-05 |
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TW201624138A (zh) | 2016-07-01 |
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