JP2017505356A - ブロック共重合体 - Google Patents
ブロック共重合体 Download PDFInfo
- Publication number
- JP2017505356A JP2017505356A JP2016536909A JP2016536909A JP2017505356A JP 2017505356 A JP2017505356 A JP 2017505356A JP 2016536909 A JP2016536909 A JP 2016536909A JP 2016536909 A JP2016536909 A JP 2016536909A JP 2017505356 A JP2017505356 A JP 2017505356A
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- Prior art keywords
- block
- group
- block copolymer
- atom
- chain
- Prior art date
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- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 47
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
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Abstract
Description
化学式1で、Yの1価置換基は、少なくとも8個の鎖形成原子で形成される鎖構造を含む。
したがって、化学式1の好適な例示の単量体としては、下記化学式3の単量体を挙げることができる。
このような第2ブロックは、前述した第1ブロックと優れた相互作用を示し、ブロック共重合体が優れた自己組織化特性などを示すようにすることができる。
また、化学式7に含まれるハロゲン原子としては、フッ素原子または塩素原子などを例示することができ、好適には、フッ素原子を使用することができるが、これに制限されるものではない。
例えば、第2Bブロックである化学式7は、下記化学式8で表示することができる。
第2Bブロックは、例えば、下記化学式9で表示することができる。
化学式9でX2は、他の例示で、単一結合、酸素原子、アルキレン基、−C(=O)−O−または−O−C(=O)−であることができる。
化学式11の前記芳香族構造は、炭素数6〜12の芳香族構造、例えば、アリール基またはアリレン基であることができる。
化学式11の第2Dブロックは、例えば、下記化学式12で表示することができる。
このようなアリール基において前記金属原子または準金属原子を含む置換基は、少なくとも1個または1個〜3個含まれ、前記ハロゲン原子は、1個以上、2個以上、3個以上、4個以上または5個以上含まれることができる。
化学式12の第2Dブロックは、例えば、下記化学式13で表示することができる。
化学式13でR1〜R5には、ハロゲン原子が1個以上、2個以上、3個以上、4個以上または5個以上含まれることができる。R1〜R5に含まれるハロゲン原子は、10個以下、9個以下、8個以下、7個以下または6個以下であることができる。
第2Eブロックは、前記電気陰性度が3以上の非ハロゲン原子とともに1個以上、2個以上、3個以上、4個以上または5個以上のハロゲン原子、例えば、フッ素原子を含むことができる。第2Eブロックに含まれるフッ素原子のようなハロゲン原子は、10個以下、9個以下、8個以下、7個以下または6個以下であることができる。
第2Eブロックは、下記化学式14で表示することができる。
化学式14の前記芳香族構造は、炭素数6〜12の芳香族構造、例えば、アリール基またはアリレン基であることができる。
化学式14のブロックは、他の例示で下記化学式15で表示することができる。
前記でWは、電気陰性度が3以上の非ハロゲン原子を含む置換基及び少なくとも1個のハロゲン原子を含む炭素数6〜12のアリール基であることができる。
化学式15のブロックは、他の例示で下記化学式16で表示することができる。
化学式16でR1〜R5には、ハロゲン原子が1個以上、2個以上、3個以上、4個以上または5個以上含まれることができる。R1〜R5に含まれるハロゲン原子は、10個以下、9個以下、8個以下、7個以下または6個以下であることができる。
第2Fブロックは、下記化学式17で表示することができる。
化学式17の芳香族構造は、必要な場合に、1つ以上がハロゲン原子を含むことができる。
化学式17の単位は、下記化学式18で表示することができる。
化学式18の単位は、下記化学式19で表示することができる。
本出願のブロック共重合体は、XRD分析(X線回折分析、X−ray Diffraction analysis)時に所定範囲の散乱ベクトル(q)内で少なくとも1つのピークを示すことができる。
3nm−1〜5nm−1=nq/(2×π)
このような範囲でブロック共重合体は、好適な自己組織化特性を示すことができる。ブロック共重合体の数平均分子量などは、目的する自己組織化構造などを勘案して調節することができる。
例えば、ブロック共重合体において前記第1または第2ブロックまたはそれと共有結合された他のブロックのセグメント内で他のセグメントがラメラ形態またはシリンダー形態などのような規則的な構造を形成していてもよい。
また、選択的にブロックが除去された高分子膜をマスクとして基板をエッチングする段階は、特に制限されず、例えば、CF4/Arイオンなどを使用した反応性イオンエッチング段階を通じて行うことができ、この過程に引き続いて酸素プラズマ処理などによって高分子膜を基板から除去する段階をさらに行うことができる。
NMR分析は、三重共鳴5mmプローブ(probe)を有するVarian Unity Inova(500MHz)分光計を含むNMR分光計を使用して常温で行った。NMR測定用溶媒(CDCl3)に分析対象物質を約10mg/ml程度の濃度で希釈させて使用し、化学的移動はppmで表現した。
〈適用略語〉
br=広い信号、s=単一線、d=二重線、dd=二重二重線、t=三重線、dt=二重三重線、q=四重線、p=五重線、m=多重線。
数平均分子量(Mn)及び分子量分布は、GPC(Gel permeation chromatography)を使用して測定した。5mLバイアル(vial)に実施例または比較例のブロック共重合体または巨大開始剤などの分析対象物質を入れ、約1mg/mL程度の濃度となるようにTHF(tetrahydro furan)に希釈する。その後、Calibration用標準試料と分析しようとする試料をsyringe filter(pore size:0.45μm)を通じて濾過させた後、測定した。分析プログラムは、Agilent technologies社のChemStationを使用し、試料のelution timeをcalibration curveと比較し、重量平均分子量(Mw)及び数平均分子量(Mn)をそれぞれ求め、その比率(Mw/Mn)で分子量分布(PDI)を計算した。GPCの測定条件は、下記の通りである。
〈GPC測定条件〉
機器:Agilent technologies社の1200 series
カラム:Polymer laboratories社のPLgel mixed B 2個使用
溶媒:THF
カラム温度:35℃
サンプル濃度:1mg/mL、200L注入
標準試料:ポリスチレン(Mp:3900000、723000、316500、52200、31400、7200、3940、485)
化学式Fの化合物(DPM−N2)を次の方式で合成した。500mLのフラスコにPd/C(palladium on carbon)(1.13g、1.06mmol)及び2−プロパノール200mLを添加し、水20mLに溶解させたギ酸アンモニウム(ammonium formate)(6.68g、106.0mmol)を追加し、1分間常温で反応させてPd/Cを活性化させた。引き続いて、4−アミノフェノール(4−amino phenol)(1.15g、10.6mmol)とラウリックアルデヒド(lauric aldehyde)(1.95g、10.6mmol)を追加し、常温で約1時間窒素条件の下で撹拌して反応させた。反応後、Pd/Cを除去し、反応に使用した2−プロパノールを除去した後、水とメチレンクロライドで抽出し、未反応物を除去した。有機層を採取し、MgSO4で脱水後、溶媒を除去した。粗生性物(crude product)をカラムクロマトグラフィーで精製(移動相:hexane/ethyl acetate)し、無色の固体状の中間体(1.98、7.1mmolg)を得た(収得率:67重量%)。
〈中間体NMR分析結果〉
1H−NMR(DMSO−d):d6.69(dd、2H);d6.53(dd、2H);d3.05(t、2H);d1.59(p、2H);d1.40−1.26(m、16H);d0.88(t、3H).
〈DPM−N2 NMR分析結果〉
1H−NMR(CDCl3):d6.92(dd、2H);d6.58(dd、2H);d6.31(dt、1H);d5.70(dt、1H);d3.60(s、1H);d3.08(t、2H);d2.05(dd、3H);d1.61(p、2H);d1.30−1.27(m、16H);d0.88(t、3H).
下記化学式Gの化合物(DPM−C4)は、次の方式で合成した。250mLのフラスコにヒドロキノン(hydroquinone)(10.0g、94.2mmol)及び1−ブロモブタン(1−Bromobutane)(23.5g、94.2mmol)を入れ、100mLのアセトニトリル(acetonitrile)にとかした後、過量のカリウムカルボネート(potassium carbonate)を添加し、75℃で約48時間窒素条件の下で反応させた。反応後、残存するカリウムカルボネート及び反応に使用したアセトニトリルをも除去した。これにDCM(dichloromethane)と水の混合溶媒を添加してウォークアップ(work up)し、分離した有機層をMgSO4で脱水した。引き続いて、CC(Column Chromatography)でDCM(dichloromethane)で精製し、白色固体状の中間体を約37%の収得率で得た。
フラスコに合成された中間体(9.8g、35.2mmol)、メタクリル酸(6.0g、69.7mmol)、DCC(dicyclohexylcarbodiimide)(10.8g、52.3mmol)及びDMAP(p−dimethylaminopyridine)(1.7g、13.9mmol)を入れ、120mLのメチレンクロライドを添加した後、常温の窒素雰囲気で24時間反応させた。反応後に、反応中に生成された塩(urea salt)をフィルターで除去し、残存するメチレンクロライドをも除去した。CC(Column Chromatography)でヘキサンとDCM(dichloromethane)を移動相にして不純物を除去し、得られた生成物をメタノールと水の混合溶媒(1:1重量比率で混合)で再結晶させて、白色固体状の目的物(DPM−C4)を得た。
〈DPM−C4 NMR分析結果〉
1H−NMR(CDCl3):d7.02(dd、2H);d6.89(dd、2H);d6.33(dt、1H);d5.73(dt、1H);d3.95(t、2H);d2.06(dd、3H);d1.76(p、2H);d1.49(p、2H);d0.98(t、3H).
AIBN(Azobisisobutyronitrile)、RAFT試薬(2−cyano−2−propyl dodecyl trithiocarbonate)及び製造例1で製造された化合物(DPM−N1)を26:1:0.5の重量比率(DPM−N1:RAFT試薬:AIBN)でベンゼンに溶解させ(濃度:70重量%)、窒素雰囲気の下で70℃で4時間反応させて巨大開始剤(数平均分子量:9700、分子量分布:1.2)を合成した。巨大開始剤、ペンタフルオロスチレン(PFS)及びAIBNを1:600:0.5の重量比率(巨大開始剤:PFS:AIBN)でベンゼンにとかし(濃度:30重量%)、窒素雰囲気で115℃で6時間反応をさせて、ブロック共重合体(数平均分子量:17300、分子量分布:1.2)を合成した。
前記ブロック共重合体は、製造例1の化合物由来の第1ブロックとペンタフルオロスチレン由来の第2ブロックを含む。
製造例2の化合物(DPM−C4)2.0g及びRAFT(Reversible Addition−Fragmentation chain Transfer)試薬(cyanoisopropyl dithiobenzoate)64mg、AIBN(Azobisisobutyronitrile)23mg及びベンゼン5.34mLを10mLのフラスコ(Schlenk flask)に入れ、窒素雰囲気の下で常温で30分間撹拌した後、70℃で4時間RAFT(Reversible Addition−Fragmentation chain Transfer)重合反応を行った。重合後、反応溶液を抽出溶媒であるメタノール250mLに沈殿させた後、減圧濾過後、乾燥させて、桃色の巨大開始剤を製造した。
製造例2の化合物(DPM−C4)の代わりに、4−メトキシフェニルメタクリレートを使用することを除いて、比較例1に準ずる方式で巨大開始剤及びペンタフルオロスチレンをモノマーとしてブロック共重合体を製造した。前記ブロック共重合体は、前記4−メトキシフェニルメタクリレートから由来する第1ブロックと前記ペンタフルオロスチレンから由来する第2ブロックを含む。
製造例2の化合物(DPM−C4)の代わりに、ドデシルメタクリレートを使用することを除いて、比較例1に準ずる方式で巨大開始剤及びペンタフルオロスチレンをモノマーとしてブロック共重合体を製造した。前記ブロック共重合体は、前記ドデシルメタクリレートから由来する第1ブロックと前記ペンタフルオロスチレンから由来する第2ブロックを含む。
実施例1及び比較例1〜3で合成されたブロック共重合体を使用して自己組織化された高分子膜を形成し、その結果を確認した。具体的に、各共重合体を溶媒に約1.0重量%の濃度で溶解させ、シリコンウェーハ上に3000rpmの速度で60秒間スピンコーティングした。その後、溶媒熟成(solvent annealing)または熱的熟成(thermal annealing)させて自己組織化させた。各ブロック共重合体に対して適用された溶媒及び熟成方式などは、下記表1に整理した。その後、各高分子膜に対してSEM(scanning electron microscope:SEM)またはAFM(Atomic force microscopy)写真を撮影し、自己組織化効率を評価した。図1は、実施例1に関する結果であり、図2〜図4は、それぞれ比較例1〜3に関する結果である。
Claims (19)
- Xは、単一結合、酸素原子、カルボニル基、−C(=O)−O−または−O−C(=O)−である、請求項1に記載のブロック共重合体。
- 鎖は、8個〜20個の鎖形成原子を有する、請求項1に記載のブロック共重合体。
- 鎖形成原子は、炭素、酸素、窒素または硫黄である、請求項1に記載のブロック共重合体。
- 鎖は、直鎖状の炭化水素鎖である、請求項1に記載のブロック共重合体。
- 1つ以上のハロゲン原子を有する芳香族構造を含む第2ブロックをさらに有する、請求項1に記載のブロック共重合体。
- R1〜R5が含むハロゲン原子の数は、3個以上である、請求項8に記載のブロック共重合体。
- R1〜R5が含むハロゲン原子の数は、5個以上である、請求項8に記載のブロック共重合体。
- ハロゲン原子は、フッ素原子である、請求項6に記載のブロック共重合体。
- X線回折分析で0.5nm−1〜10nm−1のq値内で半値全幅が0.2nm−1〜1.5nm−1の範囲内にあるピークを示す、請求項1に記載のブロック共重合体。
- 化学式6で表示されるブロックの体積分率が0.4〜0.8の範囲内にあり、第2ブロックの体積分率が0.2〜0.6の範囲内にある、請求項6に記載のブロック共重合体。
- 化学式6で表示されるブロックと第2ブロックの表面エネルギーの差の絶対値が2.5mN/m〜7mN/mの範囲内にある、請求項6に記載のブロック共重合体。
- 化学式6で表示されるブロックの表面エネルギーが20〜35mN/mの範囲内にある、請求項1に記載のブロック共重合体。
- 化学式6で表示されるブロックと第2ブロックの密度差の絶対値が0.3g/cm3以上である、請求項6に記載のブロック共重合体。
- 自己組織化された請求項1に記載のブロック共重合体を含む高分子膜。
- 自己組織化された請求項1に記載のブロック共重合体を含む高分子膜を基板上に形成することを含む高分子膜の形成方法。
- 基板及び前記基板上に形成されており、自己組織化された請求項1に記載のブロック共重合体を含む高分子膜を有する積層体において前記ブロック共重合体の第1ブロックまたは第2ブロックを選択的に除去する過程を含むパターン形成方法。
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Also Published As
Publication number | Publication date |
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EP3078685A1 (en) | 2016-10-12 |
CN105899558A (zh) | 2016-08-24 |
JP6347356B2 (ja) | 2018-06-27 |
WO2015084123A1 (ko) | 2015-06-11 |
US20170058071A1 (en) | 2017-03-02 |
EP3078685B1 (en) | 2020-09-09 |
CN105899558B (zh) | 2018-09-18 |
EP3078685A4 (en) | 2017-09-13 |
US10227436B2 (en) | 2019-03-12 |
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