JP2020536137A - ランダム共重合体およびこれを含むピニング組成物 - Google Patents
ランダム共重合体およびこれを含むピニング組成物 Download PDFInfo
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- JP2020536137A JP2020536137A JP2020517386A JP2020517386A JP2020536137A JP 2020536137 A JP2020536137 A JP 2020536137A JP 2020517386 A JP2020517386 A JP 2020517386A JP 2020517386 A JP2020517386 A JP 2020517386A JP 2020536137 A JP2020536137 A JP 2020536137A
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- 150000002736 metal compounds Chemical class 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical class C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
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- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- GRKRIZFAMXKNHZ-UHFFFAOYSA-N phosphonooxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOP(O)(O)=O GRKRIZFAMXKNHZ-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
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- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 150000003462 sulfoxides Chemical class 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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Abstract
Description
NMR分析は、三重共鳴の5mmのプローブ(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程度の濃度で希釈して使用し、化学的移動は、ppmで表現した。
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および分子量分布は、ゲル浸透クロマトグラフィー(GPC)を使用して測定した。5mLのバイアル(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等の分析対象物質を入れ、約1mg/mL程度の濃度になるようにテトラヒドロフラン(THF)に希釈する。その後、キャリブレーション用標準試料と分析しようとする試料をシリンジフィルタ(細孔サイズ:0.45μm)を介して濾過させた後に測定した。分析プログラムは、Agilent technologies社のChemStationを使用し、試料の溶出時間(elution time)を検量線(calibration curve)と比較して重量平均分子量Mwおよび数平均分子量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。
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、200μL注入
標準試料:ポリスチレン(Mp:3900000、723000、316500、52200、31400、7200、3940、485)
ブロック共重合体の各ブロックの体積分率は、各ブロックの常温での密度とGPCにより測定された分子量に基づいて計算した。前記で密度は、浮力法を用いて測定した。具体的に、密度は、空気中での質量と密度を知っている溶媒(エタノール)内に分析しようとする試料を入れ、その質量を用いて計算した。
下記化学式Aの化合物(DPM−C12)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)および1−ブロモドデカン(1−Bromododecane)(23.5g、94.2mmol)を入れ、100mLのアセトニトリル(acetonitrile)に溶かした後、過量のポタシウムカーボネート(potassium carbonate)を添加し、75℃で約48時間の間窒素条件下で反応させた。反応後、残存するポタシウムカーボネートをフィルタリングして除去し、反応に使用したアセトニトリルをも除去した。これにジクロロメタン(DCM)と水の混合溶媒を添加してウォークアップし、分離した有機層を集めて、MgSO4に通過させて脱水した。次に、カラムクロマトグラフィーでジクロロメタン(DCM)を使用して白色固体状の目的物(4−ドデシルオキシフェノール)(9.8g、35.2mmol)を約37%の収率で得た。
1H−NMR(CDCl3):δ6.77(dd、4H);δ4.45(s、1H);δ3.89(t、2H);δ1.75(p、2H);δ1.43(p、2H);δ1.33−1.26(m、16H);δ0.88(t、3H)。
1H−NMR(CDCl3):δ7.02(dd、2H);δ6.89(dd、2H);δ6.32(dt、1H);δ5.73(dt、1H);δ3.94(t、2H);δ2.05(dd、3H);δ1.76(p、2H);δ1.43(p、2H);1.34−1.27(m、16H);δ0.88(t、3H)。
ペンタフルオロスチレン1.677g、(メタクリロイルオキシ)メチルホスホン酸((methacryloyloxy)methyl phosphonic acid,hMAPC1)0.084g、可逆的付加開裂連鎖移動(RAFT:Reversible Addition−Fragmentation Chain Transfer)試薬(2−cyano−2−propyl benzodithioate)10mg、V−40(1,1′−アゾビス(シクロヘキサンカルボニトリル)6mgおよびトリフルオロトルエン(trifluorotoluene)1.777gを10mLのフラスコ(シュレンクフラスコ)に入れ、窒素雰囲気下で常温で30分間撹拌した後、95℃で3時間の間可逆的付加開裂連鎖移動(RAFT)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200mLに沈殿させ、減圧濾過した後、乾燥させて、ランダム共重合体Bを製造した。ランダム共重合体Bにおいて、ペンタフルオロスチレン由来単位の含量は、約94.3重量%であった。
製造例1のモノマーA2.974g、(メタクリロイルオキシ)メチルホスホン酸(hMAPC1)0.081g、可逆的付加開裂連鎖移動(RAFT)試薬(2−cyano−2−propyl benzodithioate)10mg、V−40(1,1′-アゾビス(シクロヘキサンカルボニトリル)6mgおよびトリフルオロトルエン1.777gを10mLのフラスコ(シュレンクフラスコ)に入れ、窒素雰囲気下で常温で30分間撹拌した後、95℃で3時間の間可逆的付加開裂連鎖移動(RAFT)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200mLに沈殿させ、減圧濾過した後、乾燥させて、ランダム共重合体を製造した。ランダム共重合体Cにおいて、製造例1のモノマーA由来単位の含量は、約96.8重量%であった。
製造例1のモノマーA0.520g、ペンタフルオロスチレン1.456g、グリシジルメタクリレート(glycidyl methacrylate)0.142g、アゾビスイソブチロニトリル(AIBN)3.3mgおよびテトラヒドロフラン(tetrahydrofuran)1.62mLを10mLのフラスコ(シュレンクフラスコ)に入れ、窒素雰囲気下で常温で30分間撹拌した後、60℃で12時間の間重合反応を行った。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、減圧濾過した後、乾燥させて、ランダム共重合体を製造した。ランダム共重合体の数平均分子量Mnおよび分子量分布Mw/Mnは、それぞれ、39,400g/molおよび1.96であり、ランダム共重合体の各成分別の含量比は、製造例1のモノマーA15モル%、ペンタフルオロスチレン75モル%およびグリシジルメタクリレート10モル%であった。
製造例1のモノマーA2.0gと可逆的付加開裂連鎖移動(RAFT)試薬(2−cyano−2−propyl benzodithioate)64mg、ラジカル開始剤であるアゾビスイソブチロニトリル(AIBN)23mgおよびベンゼン5.34mLを10mLのシュレンクフラスコに入れ、窒素雰囲気下で常温で30分間撹拌した後、70℃で4時間の間可逆的付加開裂連鎖移動(RAFT)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、減圧濾過して乾燥させて、ピンク色の巨大開始剤を製造した。前記巨大開始剤の収率は、約82.6重量%であり、数平均分子量Mnおよび分子量分布Mw/Mnは、それぞれ、13,200g/molおよび1.16であった。巨大開始剤0.3g、ペンタフルオロスチレンモノマー2.7174gおよびベンゼン1.306mLを10mLのシュレンクフラスコに入れ、窒素雰囲気下で常温で30分間撹拌した後、115℃で4時間の間可逆的付加開裂連鎖移動(RAFT)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、減圧濾過し、乾燥させて、淡いピンク色のブロック共重合体を製造した。前記ブロック共重合体は、製造例1のモノマーAに由来したものであって、鎖形成原子が12個(化学式AのRの炭素数)である第1ブロックと、前記ペンタフルオロスチレン単量体に由来した第2ブロックを含む。前記で第1ブロックの体積分率は、約0.40程度であり、第2ブロックの体積分率は、約0.60程度であり、製造されたブロック共重合体Eは、数平均分子量Mnおよび分子量分布Mw/Mnは、それぞれ44,700g/molおよび1.19であった。
ペンタフルオロスチレン2.39g、可逆的付加開裂連鎖移動(RAFT)試薬(2−hydroxyethyl−2−(((dodecylthio)carbonothioyl)thio−2−methylpropanoate)30mg、アゾビスイソブチロニトリル(AIBN)5mgおよびアニソール0.80gを10mLのフラスコ(シュレンクフラスコ)に入れ、窒素雰囲気下で常温で30分間撹拌した後、70℃で6時間の間可逆的付加開裂連鎖移動(RAFT)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200mLに沈殿させ、減圧濾過した後、乾燥させて、高分子Fを製造した。高分子Fの数平均分子量Mnおよび分子量分布Mw/Mnは、それぞれ10,000g/molおよび1.10であった。
製造例2のランダム共重合体B(hMAPC1を約2.65重量%含む)または製造例3のランダム共重合体C(hMAPC1を約 4.77重量%含む)を、濃度が約1.0重量%になるように、フルオロベンゼンに溶解させて、ピニング組成物を製造した。次に、前記ピニング組成物を、シリコンウェハー(未処理基材層)上に約30nmの厚さでコーティングし、下記表1のように調節された温度で(実施例1〜3)5分間熱的アニーリングした後、フルオロベンゼンに10分間浸漬させて、未反応のランダム共重合体Bまたは未反応のランダム共重合体Cを除去して、ピニング層を形成した。次に、製造例4のブロック共重合体Eを、濃度が約0.8重量%になるように、フルオロベンゼンに溶解させて高分子組成物を製造し、これを前記ピニング層上に約30nmの厚さでスピンコーティングし、230℃で約5分間熱的アニーリングして、高分子膜を形成した。高分子膜内のブロック共重合体Eのパターンを走査型電子顕微鏡(SEM;Scanning Electron Microscope)を用いて確認した。
ランダム共重合体Bまたはランダム共重合体Cの代わりに、製造例6の高分子Fを使用し、下記表1のように調節された温度で熱的アニーリングしたことを除いて、実施例と同じ条件で高分子膜を形成した。
製造例4のランダム共重合体Dの濃度が約0.5重量%になるようにフルオロベンゼンに溶解させた中性層組成物をシリコンウェハー(基材層)上にスピンコーティングし、200℃の温度で約5分間熱処理した。次に、フルオロベンゼンに約1分間浸漬させて、残余のランダム共重合体Dを除去して、厚さが約10nmである中性層のパターンが形成された基板(中性層基板)を準備した。
Claims (21)
- 下記化学式1で表される単位および下記化学式3または化学式4で表される単位を含むランダム共重合体:
[化学式1]
[化学式2]
[化学式3]
- 化学式3でWのハロゲン原子は、フッ素原子である、請求項1に記載のランダム共重合体。
- 化学式4でYの環構造は、芳香環構造または脂環族環構造である、請求項1に記載のランダム共重合体。
- 化学式3または化学式4で表される単位は、全体ランダム共重合体に80重量%〜99.9重量%の比率で含まれる、請求項1から3のいずれか一項に記載のランダム共重合体。
- 化学式3または化学式4で表される単位100重量部に対して化学式1で表される単位を1重量部〜30重量部で含む、請求項1から4のいずれか一項に記載のランダム共重合体。
- 請求項1から5のいずれか一項に記載のランダム共重合体を含むピニング組成物。
- ランダム共重合体を0.1重量%〜20重量%の比率で含む、請求項6に記載のピニング組成物。
- 基材層と、該基材層の表面に存在するピニング層とを含み、前記ピニング層は、請求項1から5のいずれか一項に記載のランダム共重合体を含む基板。
- ピニング層は、基材層の表面でストライプパターンを形成している、請求項8に記載の基板。
- 基材層の表面に存在する中性層をさらに含み、前記中性層とピニング層は、交互に繰り返されるストライプパターンを形成している、請求項8または9に記載の基板。
- 中性層は、下記化学式3で表される単位および下記化学式4で表される単位を含むランダム共重合体を含む、請求項10に記載の基板:
[化学式3]
- 中性層に含まれるランダム共重合体は、化学式4で表される単位を9モル%〜32モル%の比率で含む、請求項11に記載の基板。
- 中性層に含まれるランダム共重合体において、化学式4で表される単位のモル数Aと化学式3で表される単位のモル数Bとの比率B/Aは、2〜10の範囲内である、請求項11または12に記載の基板。
- ピニング層またはピニング層と中性層上に形成された高分子膜をさらに含み、高分子膜は、第1ブロックおよび前記第1ブロックとは異なる第2ブロックを含むブロック共重合体を含む、請求項8から13のいずれか一項に記載の基板。
- ブロック共重合体は、スフィア、シリンダー、ジャイロイドまたはラメラ構造を形成している、請求項14に記載の基板。
- ブロック共重合体の第1ブロックまたは第2ブロックは、前記化学式3または前記化学式4の単位を含む、請求項14または15に記載の基板。
- 基材層上に請求項6または7に記載のピニング組成物をコーティングし、130℃未満の温度でアニーリングしてピニング層を形成する段階を含むパターン化基板の製造方法。
- アニーリングは、熱的アニーリングである、請求項17に記載のパターン化基板の製造方法。
- アニーリングされる基材層は、中性層が形成されている、請求項17または18に記載のパターン化基板の製造方法。
- ピニング層上に第1ブロックおよび前記第1ブロックとは異なる第2ブロックを含むブロック共重合体を含む高分子膜を自己組織化した状態で形成する段階をさらに含む、請求項17から19のいずれか一項に記載のパターン化基板の製造方法。
- 高分子膜から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段階をさらに含む、請求項20に記載のパターン化基板の製造方法。
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WO2019013602A1 (ko) * | 2017-07-14 | 2019-01-17 | 주식회사 엘지화학 | 중성층 조성물 |
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KR102522189B1 (ko) | 2023-04-14 |
EP3677644A4 (en) | 2021-05-05 |
KR20220153557A (ko) | 2022-11-18 |
KR20190047638A (ko) | 2019-05-08 |
US12006384B2 (en) | 2024-06-11 |
CN111164146B (zh) | 2022-08-16 |
WO2019083337A1 (ko) | 2019-05-02 |
EP3677644A1 (en) | 2020-07-08 |
US20200239701A1 (en) | 2020-07-30 |
CN111164146A (zh) | 2020-05-15 |
JP7120517B2 (ja) | 2022-08-17 |
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