JP2020105499A - 研磨パッド用組成物、研磨パッドおよびその製造方法 - Google Patents
研磨パッド用組成物、研磨パッドおよびその製造方法 Download PDFInfo
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- JP2020105499A JP2020105499A JP2019226191A JP2019226191A JP2020105499A JP 2020105499 A JP2020105499 A JP 2020105499A JP 2019226191 A JP2019226191 A JP 2019226191A JP 2019226191 A JP2019226191 A JP 2019226191A JP 2020105499 A JP2020105499 A JP 2020105499A
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- oligomer
- urethane
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- composition
- prepolymer
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Classifications
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- B24—GRINDING; POLISHING
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- B24B37/11—Lapping tools
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- B24B37/24—Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
- B24D18/00—Manufacture of grinding tools or other grinding devices, e.g. wheels, not otherwise provided for
- B24D18/0009—Manufacture of grinding tools or other grinding devices, e.g. wheels, not otherwise provided for using moulds or presses
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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Abstract
Description
本発明の一実施形態による組成物は、ウレタン系プレポリマー、硬化剤、および発泡剤を含む。以下、各構成成分別に具体的に説明する。
プレポリマー(prepolymer)とは、一般的に最終成形品を製造するに当たり、成形しやすいように重合度を中間段階で中止させた比較的低い分子量を有する高分子のことを指す。例えば、前記ウレタン系プレポリマーの重量平均分子量(Mw)は、500g/mol〜3000g/mol、600g/mol〜2000g/mol、または700g/mol〜1500g/molであり得る。プレポリマーは、それ自体で、または他の重合性化合物や硬化剤とさらに反応させた後、最終製品として形成され得る。
前記ウレタン系プレポリマーは、ジイソシアネートモノマーとポリオールとの間の様々な分子量の重合反応物を含む。
または、前記pは1〜100、3〜50、または10〜20の整数であり得る。
前記ウレタン系プレポリマー内において、前記ジイソシアネートモノマーは、少なくとも1つのNCO基が反応され(つまり、2つのNCO基が反応されるか、または1つのNCO基が反応され)プレポリマー内の鎖を構成し得る。
また、前記ウレタン系プレポリマーの調製のための反応に使用された化合物のうちの一部は反応に関与しないことがあり得る。
前記ウレタン系プレポリマーは、これに含まれているポリマー、オリゴマーまたはモノマーの末端に未反応のNCO基を有し得る。
前記硬化剤は、アミン化合物およびアルコール化合物中の1種以上であり得る。具体的に、前記硬化剤は、芳香族アミン、脂肪族アミン、芳香族アルコール、および脂肪族アルコールからなる群より選択される1つ以上の化合物を含み得る。
前記発泡剤は、研磨パッドの空隙形成に通常用いられるものであれば特に制限しない。
前記組成物は、硬化によってゲル化されるまで一定の時間がかかるが、これをゲル化時間(gel time)と言う。
前記ゲル化時間は、例えば70℃にて測定された値であり得る。
前記組成物は、硬化後の引張強度、伸び率、硬度などのような機械的物性が特定の範囲に調節され得る。
前記微細気孔の平均サイズは10μm〜50μm、20μm〜50μm、20μm〜40μm、20μm〜30μm、または30μm〜50μmであり得る。
本発明の一実施形態による組成物の調製方法は、前記化学式1においてnが0または1である第1オリゴマーを調製する段階と、前記化学式1においてnが2または3である第2オリゴマーを調製する段階と、前記第1オリゴマーおよび前記第2オリゴマーを含むウレタン系プレポリマーを調製する段階と、前記ウレタン系プレポリマー、硬化剤、および発泡剤を混合する段階とを含む。
本発明の一実施形態による研磨パッドの製造方法は、前記一実施形態による組成物を硬化させながら成形する段階を含む。
本発明の一実施形態による研磨パッドは、前記一実施形態による組成物の硬化物および前記硬化物内に分散されている多数の微細気孔を含む。
前記微細気孔の平均サイズは、10μm〜50μm、20μm〜50μm、20μm〜40μm、20μm〜30μm、または30μm〜50μmであり得る。具体的な一例として、前記微細気孔は21μm〜25μmの平均サイズを有し得る。
また、前記上部パッドおよび下部パッドの間には接着層が挿入され得る。
本発明の一実施形態による半導体素子の製造方法は、前記一実施形態による研磨パッドを用いて半導体基板の表面を研磨する段階を含む。
以下、実施例によりさらに具体的に説明するが、これらの実施例の範囲に限定されるものではない。
トルエン2,4−ジイソシアネート(2,4−TDI)、トルエン2,6−ジイソシアネート(2,6−TDI)、ポリテトラメチレンエーテルグリコール(PTMEG)、およびジシクロヘキシルメタンジイソシアネート(H12MDI)を4口フラスコに投入して80℃にて反応させ、ジエチレングリコール(DEG)をさらに投入して80℃で追加反応させた後精製して、様々な分子量の反応物およびこれを含むウレタン系プレポリマーを調製した。
上部パッドの具体的な工程条件を下記表にまとめた。
前記実施例および比較例から得たウレタン系プレポリマーまたは研磨パッドを下記の項目について試験し、その結果を表2に示した。
プレポリマーのサンプルをテトラヒドロフラン(THF)に溶解させ、マトリックス(matrix)および塩(salt)と混合した後、MALDI(matrix-assisted laser desorption / ionization)測定機器(UltrafleXtreme(登録商標)、Bruker社)を使用して分析した。図1および図2に実施例1および2の結果を示し、図3に比較例1の結果を示した。
5mgのプレポリマーサンプルをCDCl3に溶解し、室温にて核磁気共鳴(NMR)装置(JEOL 500MHz、90°pulse)を使用して1H−NMRおよび13C−NMR分析を行った。収得したNMRデータからTDIの反応されたメチル基と反応していないメチル基のピークとを積分することにより、プレポリマー内の反応または未反応の芳香族ジイソシアネートモノマーの含有量を算出した。
その結果を下記の表にまとめた。
サンプルを5cm×5cm(厚さ:2mm)に裁断し、温度25℃にて12時間保管した後、硬度計を用いてショアD硬度およびアスカーC硬度を測定した。
サンプルを2cm×5cm(厚さ:2mm)に裁断し、温度25℃にて12時間保管した後、比重計を用いて多層比重を測定した。
サンプルを4cm×1cm(厚さ:2mm)に裁断し、万能試験機(UTM)を用いて、50mm/分の速度において研磨パッドの破断直前の最高強度値を測定した。
サンプルを4cm×1cm(厚さ:2mm)に裁断し、万能試験機(UTM)を用いて、50mm/分の速度において研磨パッドの破断直前の最大変形量を測定した後、最初の長さに対する最大変形量の比率を百分率(%)で示した。
プレポリマーと硬化剤とを1:1当量で配合し、5000rpmで撹拌され出てくる混合液が70℃にてゲル化されるまでにかかる時間を測定した。
その結果を下記の表にまとめた。
研磨パッドの気孔を走査電子顕微鏡(SEM)で観察して図4のa〜cに示す。図4のa〜cから分かるように、実施例1および2の研磨パッドの気孔は広い面積にわたって微細かつ均一に分布している。
− 数平均直径:SEM画像上の気孔直径の合を気孔数で除した平均
− 気孔数:SEM画像上の0.3cm2当りに存在する気孔の数
− 気孔面積率:SEM画像の全面積に対する気孔のみの面積の百分率
研磨パッドの製造直後の初期研磨率を以下のように測定した。
直径300mmのシリコン素材の半導体基板に酸化ケイ素を化学気相蒸着(CVD)工程により蒸着した。CMP装置に研磨パッドを付着し、半導体基板の酸化ケイ素層が研磨パッドの研磨面を向くように設置した。研磨パッド上にか焼セリアスラリーを250mL/分の速度で供給しながら、4.0psiの荷重および150rpmの速度で60秒間酸化ケイ素膜を研磨した。研磨後、半導体基板をキャリアから外して、回転式脱水機(spin dryer)に装着して蒸留水で洗浄した後、窒素で15秒間乾燥した。乾燥された半導体基板に対して、分光干渉式ウェーハ厚み計(SI−F80R、Keyence社)を用いて研磨前後の膜厚変化を測定した。その後、下記式を用いて研磨率を計算した。その結果を図5に示した。
研磨率(Å/50秒)=研磨前後の膜厚変化(Å)/研磨時間(50秒)
研磨パッドを10分間脱イオン水でフリーコンディショニングを行った後、脱イオン水を1時間噴射しながらコンディショニングを行った。コンディショニングの過程で変化した厚さを測定して研磨パッドの切削率を算出した。コンディショニングに使用した装置は、CTS社のAP−300HMであり、コンディショニング圧力は6lbfで、回転速度は100rpm〜110rpmであり、コンディショニングに使用されたディスクはセソルLPX−DS2だった。その結果を図6に示した。
Claims (13)
- ウレタン系プレポリマー、硬化剤、および発泡剤を含み、
前記ウレタン系プレポリマーは、
[化1]
前記化学式1においてnが0または1である第1オリゴマーと、
前記化学式1においてnが2または3である第2オリゴマーとを含む、組成物。 - 前記ウレタン系プレポリマーが、前記第1オリゴマーおよび前記第2オリゴマーを1:0.2〜1:5の重量比で含む、請求項1に記載の組成物。
- 前記ウレタン系プレポリマーが、前記化学式1においてnが4〜6の整数である第3オリゴマーをさらに含む、請求項1に記載の組成物。
- 前記ウレタン系プレポリマーが前記第1オリゴマー、前記第2オリゴマー、および前記第3オリゴマーを1:0.2:0.1〜1:5:10の重量比で含む、請求項3に記載の組成物。
- 前記ウレタン系プレポリマーは、
[化2]
前記式においてpは5〜30の整数である、
前記化学式2で表される化合物をさらに含む、請求項1に記載の組成物。 - 前記ウレタン系プレポリマーが、前記ウレタン系プレポリマーの重量を基準に、未反応のNCO基を7重量%〜10重量%で含む、請求項1に記載の組成物。
- 前記ウレタン系プレポリマーが、前記ウレタン系プレポリマーの重量を基準に、未反応の芳香族ジイソシアネートモノマーを0.1重量%〜3重量%で含む、請求項1に記載の組成物。
- 前記組成物が、80秒〜130秒のゲル化時間を有し、
硬化後に10N/mm2〜23N/mm2の引張強度、80%〜250%の伸び率、および40ショアD〜65ショアDの硬度を有する、請求項1に記載の組成物。 - [化1]
前記化学式1においてnが0または1である第1オリゴマーを調製する段階と、
前記化学式1においてnが2または3である第2オリゴマーを調製する段階と、
前記第1オリゴマーおよび前記第2オリゴマーを含むウレタン系プレポリマーを調製する段階と、
前記ウレタン系プレポリマー、硬化剤、および発泡剤を混合する段階とを含む、組成物の調製方法。 - ウレタン系プレポリマーを含む第1原料組成物を準備する段階と、
硬化剤を含む第2原料組成物を準備する段階と、
発泡剤を含む第3原料組成物を準備する段階と、
前記第1原料組成物を前記第2原料組成物および前記第3原料組成物と順次または同時混合して原料混合物を調製する段階と、
前記原料混合物を金型内に注入して硬化する段階と、を含み、
前記ウレタン系プレポリマーは、
[化1]
前記化学式1においてnが0または1である第1オリゴマーと、
前記化学式1においてnが2または3である第2オリゴマーとを含む、研磨パッドの製造方法。 - ポリウレタン樹脂および前記ポリウレタン樹脂内に分散されている多数の微細気孔を含み、前記ポリウレタン樹脂はウレタン系プレポリマー由来のものであり、
前記ウレタン系プレポリマーは、
[化1]
前記化学式1においてnが0または1である第1オリゴマーと、
前記化学式1においてnが2または3である第2オリゴマーとを含む、研磨パッド。 - 前記微細気孔が21μm〜25μmの平均サイズを有し、
前記研磨パッドが3500Å/50秒〜3900Å/50秒の研磨率(removal rate)を有する、請求項11に記載の研磨パッド。 - 研磨パッドを用いて半導体基板の表面を研磨する段階を含み、
前記研磨パッドは、ポリウレタン樹脂および前記ポリウレタン樹脂内に分散されている多数の微細気孔を含み、前記ポリウレタン樹脂はウレタン系プレポリマー由来のものであり、
前記ウレタン系プレポリマーは、
[化1]
前記化学式1においてnが0または1である第1オリゴマーと、
前記化学式1においてnが2または3である第2オリゴマーとを含む、半導体素子の製造方法。
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