TW201942175A - Polishing pad, polishing pad production method, and method for polishing surface of optical material or semiconductor material - Google Patents

Polishing pad, polishing pad production method, and method for polishing surface of optical material or semiconductor material Download PDF

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Publication number
TW201942175A
TW201942175A TW108109477A TW108109477A TW201942175A TW 201942175 A TW201942175 A TW 201942175A TW 108109477 A TW108109477 A TW 108109477A TW 108109477 A TW108109477 A TW 108109477A TW 201942175 A TW201942175 A TW 201942175A
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Taiwan
Prior art keywords
polishing pad
polishing
glycol
isocyanate
pad according
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TW108109477A
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Chinese (zh)
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松岡立馬
栗原浩
鳴島早月
高見沢大和
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日商富士紡控股股份有限公司
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Priority claimed from JP2018068370A external-priority patent/JP7405500B2/en
Priority claimed from JP2018068376A external-priority patent/JP2019177455A/en
Application filed by 日商富士紡控股股份有限公司 filed Critical 日商富士紡控股股份有限公司
Publication of TW201942175A publication Critical patent/TW201942175A/en

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B24GRINDING; POLISHING
    • B24BMACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00Lapping machines or devices; Accessories
    • B24B37/11Lapping tools
    • B24B37/20Lapping pads for working plane surfaces
    • B24B37/24Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/304Mechanical treatment, e.g. grinding, polishing, cutting

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  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The purpose of the present invention is to provide a polishing pad that minimizes defects in a polished object, is capable of achieving a flat topography, and exhibits excellent defect performance and topography performance. Provided is a polishing pad having a polishing layer that contains a polyurethane resin, wherein: the polyurethane resin is a cured product of a curable resin composition comprising an isocyanate-terminated urethane prepolymer and a curing agent; the isocyanate-terminated urethane prepolymer is a reaction product between a polyisocyanate component and a polyol component containing a glycol having a molecular weight of 50-300; and the content of the glycol is more than 0 wt% but less than 5 wt% with respect to the total amount of the isocyanate-terminated urethane prepolymer.

Description

研磨墊、研磨墊之製造方法及光學材料或半導體材料之表面研磨方法Polishing pad, manufacturing method of polishing pad, and surface polishing method of optical material or semiconductor material

本發明係關於一種研磨墊、研磨墊之製造方法及光學材料或半導體材料之表面研磨方法。本發明之研磨墊用於光學材料、半導體晶圓、半導體裝置、硬碟用基板等之研磨,尤其適宜用於對半導體晶圓上形成有氧化物層、金屬層等之裝置進行研磨。The invention relates to a polishing pad, a manufacturing method of the polishing pad, and a surface polishing method of an optical material or a semiconductor material. The polishing pad of the present invention is used for polishing optical materials, semiconductor wafers, semiconductor devices, substrates for hard disks, and the like, and is particularly suitable for polishing devices having an oxide layer and a metal layer formed on a semiconductor wafer.

光學材料、半導體晶圓、硬碟基板、液晶用玻璃基板、半導體裝置需要非常精密之平坦性。又,於半導體裝置之研磨中,伴隨著近年來積體電路之微細化、高密度化,對於被研磨物之刮痕(劃痕)等缺陷(缺損)之抑制或平坦之形貌(凹陷、磨蝕等之抑制),逐漸需要更嚴格之水準。為了將此類各種材料之表面研磨得平坦,通常使用硬質研磨墊。Optical materials, semiconductor wafers, hard disk substrates, glass substrates for liquid crystals, and semiconductor devices require very precise flatness. In the polishing of semiconductor devices, along with the miniaturization and high density of integrated circuits in recent years, suppression of defects (defects) such as scratches (scratches) on the object to be polished or flat morphology (depression, Suppression of abrasion, etc.), and increasingly stricter levels are required. In order to smooth the surface of such various materials, a hard polishing pad is usually used.

當前,多數硬質研磨墊係利用所謂預聚物法進行製造,即:將作為硬化劑之聚胺類或多元醇類及作為添加劑之發泡劑、觸媒等與作為多元醇成分與異氰酸酯成分之反應物之胺基甲酸酯預聚物混合,而製造聚胺基甲酸酯組合物,且使該聚胺基甲酸酯組合物硬化。多數胺基甲酸酯預聚物係由甲苯二異氰酸酯(TDI)或二苯基甲烷二異氰酸酯(MDI)等異氰酸酯成分、聚氧四亞甲基二醇(PTMG)或聚丙烯二醇(PPG)等高分子量多元醇、及二乙二醇(DEG)等低分子量多元醇製造。並且,於研磨墊用胺基甲酸酯預聚物中,通常使用:以相對於胺基甲酸酯預聚物整體大致5~10重量%之相對較高之含量使用二乙二醇(DEG)作為低分子量多元醇者、或僅使用二乙二醇(DEG)作為低分子量多元醇者。Currently, most hard polishing pads are manufactured by the so-called prepolymer method, that is, polyamines or polyols as hardeners, foaming agents, catalysts, etc. as additives, and polyol components and isocyanate components. The urethane prepolymers of the reactants are mixed to produce a polyurethane composition, and the polyurethane composition is hardened. Most urethane prepolymers are made from isocyanate components such as toluene diisocyanate (TDI) or diphenylmethane diisocyanate (MDI), polyoxytetramethylene glycol (PTMG), or polypropylene glycol (PPG). Manufactured from high molecular weight polyols such as low molecular weight polyols such as diethylene glycol (DEG). In addition, in the urethane prepolymer for polishing pads, it is generally used: diethylene glycol (DEG) is used at a relatively high content of approximately 5 to 10% by weight relative to the entire urethane prepolymer. ) As a low molecular weight polyol, or only using diethylene glycol (DEG) as a low molecular weight polyol.

[發明所欲解決之問題][Problems to be solved by the invention]

然而,本發明者等人經研究發現:如下述比較例所示,由以二乙二醇(DEG)相對於胺基甲酸酯預聚物整體5重量%之相對較高之含量含有二乙二醇(DEG)作為低分子量二醇之異氰酸酯封端胺基甲酸酯預聚物所形成之研磨墊、或由僅含有二乙二醇(DEG)作為低分子量二醇之異氰酸酯封端胺基甲酸酯預聚物所形成之研磨墊於被研磨物中會產生缺陷,從而無法獲得平坦之形貌。However, the inventors of the present inventors have studied and found that, as shown in the following comparative examples, diethylene glycol (DEG) is contained in a relatively high content of 5% by weight relative to the entire urethane prepolymer. Diol (DEG) is a polishing pad formed of an isocyanate-terminated urethane prepolymer of a low molecular weight diol, or an isocyanate-terminated amine group containing only diethylene glycol (DEG) as a low molecular weight diol The polishing pad formed by the formate prepolymer may cause defects in the object to be polished, so that a flat morphology cannot be obtained.

如上所述,期望一種研磨墊,其能夠抑制被研磨物中之缺陷並實現平坦之形貌,且缺陷性能及形貌性能優異。As described above, there is a demand for a polishing pad that can suppress defects in an object to be polished and achieve a flat topography, and has excellent defect performance and topography performance.

本發明之目的在於提供一種研磨墊、研磨墊之製造方法及光學材料或半導體材料之表面研磨方法,該研磨墊能夠抑制被研磨物中之缺陷並實現平坦之形貌,且缺陷性能及形貌性能優異。
[解決問題之技術手段]
An object of the present invention is to provide a polishing pad, a manufacturing method of the polishing pad, and a surface polishing method of an optical material or a semiconductor material. The polishing pad can suppress defects in the object to be polished and realize a flat topography, and the defect performance and topography Excellent performance.
[Technical means to solve the problem]

本發明者等人為了解決上述問題而進行潛心研究,結果發現:將用作異氰酸酯封端胺基甲酸酯預聚物之成分之二乙二醇(DEG)等聚氧伸烷基二醇之含量抑制得較低,或使用特定之伸烷基二醇代替二乙二醇(DEG)而作為異氰酸酯封端胺基甲酸酯預聚物之成分,藉此可解決上述問題,從而完成了本發明。本發明之具體態樣如下所述。
再者,於本說明書中,當使用「~」表示數值範圍時,其範圍包括兩端之數值。
The present inventors conducted diligent research in order to solve the above-mentioned problems, and as a result, found that polyoxyalkylene glycols such as diethylene glycol (DEG), which is used as a component of the isocyanate-terminated urethane prepolymer, have been found. The content is suppressed to a low level, or a specific alkylene glycol is used instead of diethylene glycol (DEG) as a component of the isocyanate-terminated urethane prepolymer, thereby solving the above problems, thereby completing the present invention. invention. Specific aspects of the invention are described below.
In addition, in this specification, when "~" is used to indicate a numerical range, the range includes numerical values at both ends.

[1]一種研磨墊,其具有含聚胺酯樹脂之研磨層,且
上述聚胺酯樹脂係包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物之硬化物,上述異氰酸酯封端胺基甲酸酯預聚物係包括分子量50~300之二醇之多元醇成分與聚異氰酸酯成分之反應產物,且上述二醇之含量相對於上述異氰酸酯封端胺基甲酸酯預聚物整體超過0重量%且未達5重量%。
[2]如[1]之研磨墊,其中上述二醇為聚氧伸烷基二醇。
[3]如[2]之研磨墊,其中上述聚氧伸烷基二醇為二乙二醇。
[4]如[1]之研磨墊,其中上述二醇為伸烷基二醇。
[5]如[4]之研磨墊,其中上述伸烷基二醇係分子末端具有羥基之直鏈狀化合物。
[6]如[5]之研磨墊,其中上述伸烷基二醇為1,4-丁二醇。
[7]如[1]至[6]中任一項之研磨墊,其中上述異氰酸酯封端胺基甲酸酯預聚物之NCO當量(g/eq)未達500。
[8]如[1]至[7]中任一項之研磨墊,其中上述聚異氰酸酯成分包含甲苯二異氰酸酯。
[9]如[1]至[8]中任一項之研磨墊,其中上述多元醇成分進而包含聚氧四亞甲基二醇。
[10]如[1]至[9]中任一項之研磨墊,其中上述硬化劑包含3,3'-二氯-4,4'-二胺基二苯甲烷。
[11]如[1]至[10]中任一項之研磨墊,其中上述硬化性樹脂組合物進而包含微小中空球體。
[12]一種方法,其係如[1]至[11]中任一項之研磨墊之製造方法,且
上述方法包括使上述研磨層成形之步驟。
[13]一種方法,其係光學材料或半導體材料之表面研磨方法,且上述方法使用如[1]至[11]中任一項之研磨墊。
[1] A polishing pad having a polishing layer containing a urethane resin, and the urethane resin is a hardened product of a curable resin composition containing an isocyanate-terminated urethane prepolymer and a hardener, and the isocyanate-terminated The urethane prepolymer is a reaction product of a polyol component and a polyisocyanate component of a diol having a molecular weight of 50 to 300, and the content of the diol is relative to the entire isocyanate-terminated urethane prepolymer. More than 0% by weight and less than 5% by weight.
[2] The polishing pad according to [1], wherein the diol is polyoxyalkylene glycol.
[3] The polishing pad according to [2], wherein the polyoxyalkylene glycol is diethylene glycol.
[4] The polishing pad according to [1], wherein the diol is an alkylene glycol.
[5] The polishing pad according to [4], wherein the alkylene glycol-based linear compound has a hydroxyl group at a molecular terminal.
[6] The polishing pad according to [5], wherein the alkylene glycol is 1,4-butanediol.
[7] The polishing pad according to any one of [1] to [6], wherein the NCO equivalent (g / eq) of the isocyanate-terminated urethane prepolymer is less than 500.
[8] The polishing pad according to any one of [1] to [7], wherein the polyisocyanate component includes toluene diisocyanate.
[9] The polishing pad according to any one of [1] to [8], wherein the polyol component further includes polyoxytetramethylene glycol.
[10] The polishing pad according to any one of [1] to [9], wherein the hardener comprises 3,3'-dichloro-4,4'-diaminodiphenylmethane.
[11] The polishing pad according to any one of [1] to [10], wherein the curable resin composition further contains fine hollow spheres.
[12] A method, which is a method for manufacturing a polishing pad according to any one of [1] to [11], and the method includes a step of forming the polishing layer.
[13] A method which is a surface polishing method of an optical material or a semiconductor material, and the above method uses a polishing pad according to any one of [1] to [11].

[1']一種研磨墊,其具有含聚胺酯樹脂之研磨層,且
上述聚胺酯樹脂係包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物之硬化物,上述異氰酸酯封端胺基甲酸酯預聚物係包括分子量50~300之聚氧伸烷基二醇之多元醇成分與聚異氰酸酯成分之反應產物,且上述聚氧伸烷基二醇之含量相對於上述異氰酸酯封端胺基甲酸酯預聚物整體超過0重量%且未達5重量%。
[2']如[1']之研磨墊,其中上述聚氧伸烷基二醇為二乙二醇。
[3']如[1']或[2']之研磨墊,其中上述異氰酸酯封端胺基甲酸酯預聚物之NCO當量(g/eq)未達500。
[4']如[1']至[3']中任一項之研磨墊,其中上述聚異氰酸酯成分包含甲苯二異氰酸酯。
[5']如[1']至[4']中任一項之研磨墊,其中上述多元醇成分進而包含聚氧四亞甲基二醇。
[6']如[1']至[5']中任一項之研磨墊,其中上述硬化劑包含3,3'-二氯-4,4'-二胺基二苯甲烷。
[7']如[1']至[6']中任一項之研磨墊,其中上述硬化性樹脂組合物進而包含微小中空球體。
[8']一種方法,其係如[1']至[7']中任一項之研磨墊之製造方法,且
上述方法包括使上述研磨層成形之步驟。
[9']一種方法,其係光學材料或半導體材料之表面研磨方法,且上述方法使用如[1']至[7']中任一項之研磨墊。
[1 '] A polishing pad having a polishing layer containing a polyurethane resin, and the polyurethane resin is a hardened product of a hardening resin composition containing an isocyanate-terminated urethane prepolymer and a hardener, and the isocyanate seal The urethane-terminated prepolymer is a reaction product of a polyol component and a polyisocyanate component of a polyoxyalkylene glycol having a molecular weight of 50 to 300, and the content of the polyoxyalkylene glycol relative to the isocyanate The total amount of the blocked urethane prepolymer is more than 0% by weight and less than 5% by weight.
[2 '] The polishing pad according to [1'], wherein the polyoxyalkylene glycol is diethylene glycol.
[3 '] The polishing pad according to [1'] or [2 '], wherein the NCO equivalent (g / eq) of the isocyanate-terminated urethane prepolymer is less than 500.
[4 '] The polishing pad according to any one of [1'] to [3 '], wherein the polyisocyanate component includes toluene diisocyanate.
[5 '] The polishing pad according to any one of [1'] to [4 '], wherein the polyol component further includes polyoxytetramethylene glycol.
[6 '] The polishing pad according to any one of [1'] to [5 '], wherein the hardener comprises 3,3'-dichloro-4,4'-diaminodiphenylmethane.
[7 '] The polishing pad according to any one of [1'] to [6 '], wherein the curable resin composition further contains fine hollow spheres.
[8 '] A method for manufacturing a polishing pad according to any one of [1'] to [7 '], and the method includes a step of forming the polishing layer.
[9 '] A method which is a surface polishing method of an optical material or a semiconductor material, and the above method uses a polishing pad according to any one of [1'] to [7 '].

[1'']一種研磨墊,其具有含聚胺酯樹脂之研磨層,且
上述聚胺酯樹脂係包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物之硬化物,上述異氰酸酯封端胺基甲酸酯預聚物係包括分子量50~300之伸烷基二醇之多元醇成分與聚異氰酸酯成分之反應產物,且上述伸烷基二醇之含量相對於上述異氰酸酯封端胺基甲酸酯預聚物整體超過0重量%且未達5重量%。
[2'']如[1'']之研磨墊,其中上述伸烷基二醇係分子末端具有羥基之直鏈狀化合物。
[3'']如[2'']之研磨墊,其中上述伸烷基二醇為1,4-丁二醇。
[4'']如[1'']至[3'']中任一項之研磨墊,其中上述聚異氰酸酯成分包含甲苯二異氰酸酯。
[5'']如[1'']至[4'']中任一項之研磨墊,其中上述多元醇成分進而包含聚氧四亞甲基二醇。
[6'']如[1'']至[5'']中任一項之研磨墊,其中上述硬化劑包含3,3'-二氯-4,4'-二胺基二苯甲烷。
[7'']如[1'']至[6'']中任一項之研磨墊,其中上述硬化性樹脂組合物進而包含微小中空球體。
[8'']一種方法,其係如[1'']至[7'']中任一項之研磨墊之製造方法,且
上述方法包括使上述研磨層成形之步驟。
[9'']一種方法,其係如光學材料或半導體材料之表面研磨方法,且上述方法使用如[1'']至[7'']中任一項之研磨墊。
[發明之效果]
[1 ''] A polishing pad having a polishing layer containing a polyurethane resin, and the polyurethane resin is a hardened product of a hardening resin composition containing an isocyanate-terminated urethane prepolymer and a hardener, and the isocyanate The blocked urethane prepolymer includes a reaction product of a polyol component of a polyalkylene glycol having a molecular weight of 50 to 300 and a polyisocyanate component, and the content of the polyalkylene glycol relative to the isocyanate blocked amine The urethane prepolymer as a whole exceeds 0% by weight and less than 5% by weight.
[2 "] The polishing pad according to [1"], wherein the alkylene glycol-based linear compound having a hydroxyl group at a molecular terminal.
[3 "] The polishing pad according to [2"], wherein the alkylene glycol is 1,4-butanediol.
[4 ''] The polishing pad according to any one of [1 ''] to [3 ''], wherein the polyisocyanate component includes toluene diisocyanate.
[5 "] The polishing pad according to any one of [1"] to [4 "], wherein the polyol component further includes polyoxytetramethylene glycol.
[6 ''] The polishing pad according to any one of [1 ''] to [5 ''], wherein the hardener comprises 3,3'-dichloro-4,4'-diaminodiphenylmethane.
[7 "] The polishing pad according to any one of [1"] to [6 "], wherein the curable resin composition further includes fine hollow spheres.
[8 "] A method, which is a method for manufacturing a polishing pad according to any one of [1"] to [7 "], and the method includes a step of forming the polishing layer.
[9 ''] A method which is a surface polishing method such as an optical material or a semiconductor material, and the above method uses a polishing pad such as any one of [1 "] to [7"].
[Effect of the invention]

本發明之研磨墊能夠抑制被研磨物中之缺陷並實現平坦之形貌,且缺陷性能及形貌性能優異。The polishing pad of the present invention can suppress defects in the object to be polished and achieve a flat topography, and has excellent defect performance and topography performance.

(作用1)
於本發明中,關於分子量50~300之聚氧伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量,設為超過0重量%且未達5重量%代替先前之相對較高之含量。
(Action 1)
In the present invention, the content of the polyoxyalkylene glycol having a molecular weight of 50 to 300 with respect to the entire isocyanate-terminated urethane prepolymer is set to exceed 0% by weight and less than 5% by weight to replace the previous one. Relatively high content.

本發明者等人亦出乎意料地發現:藉由將分子量50~300之聚氧伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量設為超過0重量%且未達5重量%,可獲得能夠抑制被研磨物中之缺陷並實現平坦之形貌且缺陷性能及形貌性能優異之研磨墊。獲得該等特性之具體理由尚未明確,但,推測如下。The inventors also unexpectedly discovered that by setting the content of polyoxyalkylene glycol with a molecular weight of 50 to 300 to the isocyanate-terminated urethane prepolymer as a whole to exceed 0% by weight and If it is less than 5% by weight, a polishing pad capable of suppressing defects in the object to be polished, achieving a flat topography, and having excellent defect performance and topography performance can be obtained. The specific reasons for obtaining these characteristics have not been clarified, but it is speculated as follows.

認為:二乙二醇等分子量50~300之聚氧伸烷基二醇由於2個羥基間之分子鏈內含有氧原子故而親水性較高,於大量使用此種聚氧伸烷基二醇作為異氰酸酯封端預聚物之原料之情形時,所得之異氰酸酯封端預聚物亦同樣地具有較高之親水性。並且認為:若作為研磨層之成分之異氰酸酯封端預聚物之親水性較高,則於研磨時容易將含水之漿料吸引至研磨層側,且存在於漿料中之研磨碎屑等亦一併受到吸引,故而容易產生刮痕或凹陷、磨蝕。
另一方面,認為:僅少量使用聚氧伸烷基二醇作為異氰酸酯封端預聚物之原料之情形與大量使用聚氧伸烷基二醇之情形相比,所得之異氰酸酯封端預聚物之疏水性變高(親水性變低)。並且認為:若作為研磨層之成分之異氰酸酯封端預聚物之疏水性較高,則不容易吸引存在於漿料中之研磨碎屑等,從而不容易產生刮痕或凹陷、磨蝕。
It is believed that polyoxyalkylene glycols having a molecular weight of 50 to 300, such as diethylene glycol, have high hydrophilicity because the molecular chain between the two hydroxyl groups contains oxygen atoms. Such polyoxyalkylene glycols are widely used as In the case of the raw material of the isocyanate-terminated prepolymer, the obtained isocyanate-terminated prepolymer also has high hydrophilicity. In addition, it is considered that if the isocyanate-terminated prepolymer as a component of the polishing layer has high hydrophilicity, it is easy to attract the slurry containing water to the polishing layer side during grinding, and the grinding debris existing in the slurry is also Attracted together, it is easy to produce scratches, depressions, and abrasion.
On the other hand, it is considered that in the case where only a small amount of polyoxyalkylene glycol is used as a raw material of the isocyanate-terminated prepolymer, the obtained isocyanate-terminated prepolymer is compared with the case where a large amount of polyoxyalkylene glycol is used. The hydrophobicity becomes higher (hydrophilicity becomes lower). It is also considered that if the isocyanate-terminated prepolymer, which is a component of the polishing layer, has high hydrophobicity, it is not easy to attract the grinding debris and the like existing in the slurry, so that it is not easy to generate scratches, dents, and abrasion.

(作用2)
於本發明中,作為異氰酸酯封端胺基甲酸酯預聚物所包含之多元醇成分,使用分子量50~300之伸烷基二醇代替先前使用之二乙二醇。
(Action 2)
In the present invention, as the polyol component contained in the isocyanate-terminated urethane prepolymer, an alkylene glycol having a molecular weight of 50 to 300 is used instead of the diethylene glycol previously used.

本發明者等人亦出乎意料地發現:藉由使用分子量50~300之伸烷基二醇,可獲得能夠抑制被研磨物中之缺陷並實現平坦之形貌且缺陷性能及形貌性能優異之研磨墊。獲得該等特性之具體理由尚未明確,但,推測如下。The inventors also unexpectedly found that by using an alkylene glycol having a molecular weight of 50 to 300, it is possible to obtain defects that can suppress defects in the object to be polished and achieve a flat morphology, and the defect performance and morphology performance are excellent. Polishing pad. The specific reasons for obtaining these characteristics have not been clarified, but it is speculated as follows.

推測先前使用之二乙二醇由於2個羥基間之分子鏈內含有氧原子故而親水性較高,另一方面,分子量50~300之伸烷基二醇由於2個羥基間之分子鏈僅由碳原子及氫原子形成故而疏水性較高(親水性較低)。並且,認為以該等二醇為原料之異氰酸酯封端預聚物亦分別具有相同之特性。認為:若作為研磨層之成分之異氰酸酯封端預聚物之親水性較高,則於研磨時容易將含水之漿料吸引至研磨層側,且存在於漿料中之研磨碎屑等亦一併受到吸引,故而容易產生刮痕或凹陷、磨蝕。另一方面,認為:若作為研磨層之成分之異氰酸酯封端預聚物之疏水性較高,則不容易吸引存在於漿料中之研磨碎屑等,從而不容易產生刮痕或凹陷、磨蝕。It is speculated that the diethylene glycol previously used is highly hydrophilic because the molecular chain between the two hydroxyl groups contains oxygen atoms. On the other hand, the alkylene glycol with a molecular weight of 50 to 300 is only composed of the molecular chain between the two hydroxyl groups. Carbon atoms and hydrogen atoms are formed, which results in higher hydrophobicity (lower hydrophilicity). In addition, it is considered that isocyanate-terminated prepolymers using these diols as raw materials also have the same characteristics. It is considered that if the isocyanate-terminated prepolymer as a component of the polishing layer has high hydrophilicity, it is easy to attract the slurry containing water to the polishing layer side during grinding, and the grinding debris existing in the slurry is also one. And it is attracted, so it is easy to produce scratches, depressions, and abrasion. On the other hand, if the hydrophobicity of the isocyanate-terminated prepolymer as a component of the polishing layer is high, it is not easy to attract the grinding debris and the like existing in the slurry, so that it is not easy to generate scratches, dents, and abrasion. .

以下,對本發明之研磨墊、研磨墊之製造方法及光學材料或半導體材料之表面研磨方法進行說明。Hereinafter, the polishing pad, the manufacturing method of the polishing pad, and the surface polishing method of an optical material or a semiconductor material of this invention are demonstrated.

本發明之研磨墊具有含聚胺酯樹脂之研磨層,上述聚胺酯樹脂係包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物之硬化物,上述異氰酸酯封端胺基甲酸酯預聚物係包含包括分子量50~300之二醇之多元醇成分及聚異氰酸酯成分之化合物(反應產物),且上述二醇之含量相對於上述異氰酸酯封端胺基甲酸酯預聚物整體超過0重量%且未達5重量%。The polishing pad of the present invention has a polishing layer containing a polyurethane resin. The polyurethane resin is a cured product of a hardening resin composition containing an isocyanate-terminated urethane prepolymer and a hardener. The isocyanate-terminated urethane The ester prepolymer is a compound (reaction product) including a polyol component having a molecular weight of 50 to 300 and a polyisocyanate component, and the content of the diol is relative to the entire isocyanate-terminated urethane prepolymer. More than 0% by weight and less than 5% by weight.

作為上述二醇,可使用聚氧伸烷基二醇或伸烷基二醇。As the diol, polyoxyalkylene glycol or an alkylene glycol can be used.

本發明之研磨墊具有含聚胺酯樹脂之研磨層。研磨層配置於與被研磨材料直接接觸之位置,研磨墊之其他部分可由用以支持研磨墊之材料例如橡膠等富含彈性之材料構成。根據研磨墊之硬度,可將研磨層作為研磨墊。The polishing pad of the present invention has a polishing layer containing a polyurethane resin. The polishing layer is disposed at a position in direct contact with the material to be polished, and other parts of the polishing pad may be composed of a material to support the polishing pad, such as a rubber-rich material. Depending on the hardness of the polishing pad, the polishing layer can be used as a polishing pad.

本發明之研磨墊除了能夠抑制被研磨物中之缺陷並實現平坦之形貌且缺陷性能及形貌性能優異以外,與普通研磨墊相比形狀無較大差異,並且可與普通研磨墊同樣地使用,例如,可一邊使研磨墊旋轉一邊將研磨層壓抵於被研磨材料而進行研磨,亦可一邊使被研磨材料旋轉一邊將其壓抵於研磨層而進行研磨。The polishing pad of the present invention is capable of suppressing defects in the object to be polished and achieving a flat morphology, and has excellent defect performance and morphological performance. The shape of the polishing pad is not significantly different from that of ordinary polishing pads, and can be the same as that of ordinary polishing pads. In use, for example, the polishing pad may be laminated against the material to be polished while the polishing pad is rotated, or may be polished while being pressed against the polishing layer while the material to be polished is rotated.

本發明之研磨墊可利用通常已知之模鑄成形、平板成形等製造法製成。藉由如下方法製造:首先利用該等製造法形成聚胺基甲酸酯之塊體,藉由切片等使塊體成為片狀,使由聚胺酯樹脂形成之研磨層成形且貼合於支持體等。或者,亦可於支持體上直接使研磨層成形。The polishing pad of the present invention can be produced by a manufacturing method such as die casting molding and flat plate molding which are generally known. It is manufactured by the following methods: First, a polyurethane block is formed by these manufacturing methods, the block is made into a sheet shape by slicing, etc., and a polishing layer made of a polyurethane resin is formed and attached to a support. . Alternatively, the polishing layer may be directly formed on the support.

更具體而言,研磨層係於研磨層之與研磨面相反之面側貼附雙面膠帶,切割成規定形狀,而成為本發明之研磨墊。雙面膠帶並無特別限制,可自本技術領域中公知之雙面膠帶中任意地選擇使用。又,本發明之研磨墊可為僅包含研磨層之單層結構,亦可包含於研磨層之與研磨面相反之面側貼合有其他層(下層、支持層)而成之複數層。More specifically, the polishing layer is a polishing pad according to the present invention by attaching a double-sided tape to the polishing layer on the side opposite to the polishing surface and cutting it into a predetermined shape. The double-sided tape is not particularly limited, and can be arbitrarily selected and used from the double-sided tapes known in the art. In addition, the polishing pad of the present invention may have a single-layer structure including only a polishing layer, or may include a plurality of layers formed by laminating other layers (lower layer, support layer) on the side of the polishing layer opposite to the polishing surface.

研磨層係藉由製備包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物且使該硬化性樹脂組合物硬化而成形。The polishing layer is formed by preparing a curable resin composition containing an isocyanate-terminated urethane prepolymer and a curing agent, and curing the curable resin composition.

研磨層可包含發泡聚胺酯樹脂,且發泡可藉由使含有微小中空球體之發泡劑分散於聚胺酯樹脂中而進行。於此情形時,製備包含異氰酸酯封端胺基甲酸酯預聚物、硬化劑、及發泡劑之硬化性樹脂組合物,且使該硬化性樹脂組合物發泡硬化,藉此可成形。The abrasive layer may include a foamed polyurethane resin, and foaming may be performed by dispersing a foaming agent containing minute hollow spheres in the polyurethane resin. In this case, a curable resin composition containing an isocyanate-terminated urethane prepolymer, a curing agent, and a foaming agent is prepared, and the curable resin composition is foamed and hardened, thereby forming it.

硬化性樹脂組合物例如亦可為將含有異氰酸酯封端胺基甲酸酯預聚物之A液體與含有硬化劑成分之B液體混合而製備之雙液型組合物。除此以外之成分可加入A液體,亦可加入B液,但於產生不良情況之情形時進而分割成複數種液體,從而由混合3種液體以上之液體構成之組合物可作為硬化性樹脂組合物。The curable resin composition may be, for example, a two-liquid composition prepared by mixing an A liquid containing an isocyanate-terminated urethane prepolymer and a B liquid containing a hardener component. Liquids A and B can be added to other ingredients, but in the case of a bad situation, it can be divided into multiple liquids, so that a composition composed of a mixture of three or more liquids can be used as a curable resin combination. Thing.

於本發明中,異氰酸酯封端胺基甲酸酯預聚物較佳為:藉由使包括分子量50~300之二醇之多元醇成分與聚異氰酸酯成分進行反應而獲得之產物、藉由使包括分子量50~300之聚氧伸烷基二醇之多元醇成分與聚異氰酸酯成分進行反應而獲得之產物、或藉由使包括分子量50~300之伸烷基二醇之多元醇成分與聚異氰酸酯成分進行反應而獲得之產物。In the present invention, the isocyanate-terminated urethane prepolymer is preferably: a product obtained by reacting a polyol component including a diol having a molecular weight of 50 to 300 with a polyisocyanate component; A product obtained by reacting a polyol component of a polyoxyalkylene glycol having a molecular weight of 50 to 300 and a polyisocyanate component, or a polyol component including a polyalkylene glycol having a molecular weight of 50 to 300 and a polyisocyanate component. The product obtained by carrying out the reaction.

作為異氰酸酯封端胺基甲酸酯預聚物之NCO當量(g/eq),較佳為未達500,更佳為350~495,最佳為400~490。藉由使NCO當量(g/eq)於上述數值範圍內,可獲得研磨性能適當之研磨墊,若NCO當量(g/eq)低於350,則所得之研磨墊之硬度變大且缺陷性能降低故而欠佳。又,若NCO當量(g/eq)高於500,則所得之研磨墊有硬度變小且平坦化性能降低之傾向故而欠佳。The NCO equivalent (g / eq) of the isocyanate-terminated urethane prepolymer is preferably less than 500, more preferably 350-495, and most preferably 400-490. By setting the NCO equivalent (g / eq) within the above numerical range, a polishing pad with appropriate polishing performance can be obtained. If the NCO equivalent (g / eq) is less than 350, the hardness of the obtained polishing pad becomes large and the defect performance is reduced. So it's not good. In addition, if the NCO equivalent (g / eq) is higher than 500, the obtained polishing pad tends to have a reduced hardness and a flattening performance, which is not preferable.

作為多元醇成分包含於異氰酸酯封端胺基甲酸酯預聚物中之二醇(較佳為聚氧伸烷基二醇或伸烷基二醇)之分子量為50~300,較佳為60~250,最佳為70~200。藉由使二醇(較佳為聚氧伸烷基二醇或伸烷基二醇)之分子量於上述數值範圍內,可調整NCO當量(g/eq),但,若分子量未達50,則於製造預聚物時反應性較高而不容易控制反應速度,若分子量大於300,則NCO當量(g/eq)之調整需要大量之二醇(較佳為聚氧伸烷基二醇或伸烷基二醇),故而親水性變高,因此欠佳。The molecular weight of the diol (preferably polyoxyalkylene glycol or alkylene glycol) contained in the isocyanate-terminated urethane prepolymer as a polyol component is 50 to 300, preferably 60 ~ 250, most preferably 70 ~ 200. The NCO equivalent (g / eq) can be adjusted by setting the molecular weight of the diol (preferably polyoxyalkylene glycol or alkylene glycol) within the above numerical range, but if the molecular weight is less than 50, then In the manufacture of prepolymers, the reactivity is high and it is not easy to control the reaction speed. If the molecular weight is greater than 300, the adjustment of the NCO equivalent (g / eq) requires a large amount of diol (preferably polyoxyalkylene glycol or elongation). Alkyl glycol), so that the hydrophilicity is high, so it is not good.

(分子量50~300之聚氧伸烷基二醇)
分子量50~300之聚氧伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量超過0重量%且未達5重量%,較佳為0.5~4重量%,最佳為1~3重量%。藉由使聚氧伸烷基二醇之含量於上述數值範圍內,可抑制被研磨物中之缺陷並實現平坦之形貌。
(Polyoxyalkylene glycol with a molecular weight of 50 to 300)
The content of the polyoxyalkylene glycol having a molecular weight of 50 to 300 relative to the entire isocyanate-terminated urethane prepolymer exceeds 0% by weight and less than 5% by weight, preferably 0.5 to 4% by weight, and most preferably It is 1 to 3% by weight. By making the content of the polyoxyalkylene glycol within the above-mentioned numerical range, defects in the object to be polished can be suppressed and a flat morphology can be realized.

作為分子量50~300之聚氧伸烷基二醇,例如,可使用二乙二醇、三乙二醇、四乙二醇、五乙二醇、六乙二醇等,就NCO當量(g/eq)之調整之觀點而言,較佳為使用分子量較低之二乙二醇。As the polyoxyalkylene glycol having a molecular weight of 50 to 300, for example, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, etc. can be used, and the NCO equivalent (g / From the viewpoint of adjustment of eq), diethylene glycol having a relatively low molecular weight is preferably used.

於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之聚氧伸烷基二醇之情形時,作為異氰酸酯封端胺基甲酸酯預聚物所包含之除分子量50~300之聚氧伸烷基二醇以外之多元醇成分,例如可列舉:乙二醇,1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、新戊二醇、1,5-戊二醇、3-甲基-1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇等低分子量(分子量50~300之)伸烷基二醇;聚氧四亞甲基二醇(PTMG)、聚乙二醇、聚丙烯二醇等聚醚多元醇;乙二醇與己二酸之反應物或丁二醇與己二酸之反應物等聚酯多元醇;聚碳酸酯多元醇;聚己內酯多元醇等。
該等中,就預聚物之處理性或所得之研磨墊之機械強度等觀點而言,較佳為使用聚氧四亞甲基二醇。又,作為聚氧四亞甲基二醇之數量平均分子量,較佳為500~2000,更佳為600~1000,最佳為650~850。
In the case where the isocyanate-terminated urethane prepolymer contains a polyoxyalkylene glycol having a molecular weight of 50 to 300, the isocyanate-terminated urethane prepolymer contains a molecular weight other than 50 to 300. Examples of the polyol component other than polyoxyalkylene glycol include ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, and 1 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1 Low molecular weight (molecular weight 50-300, such as 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol) Of) polyalkylene glycols; polyoxytetramethylene glycol (PTMG), polyethylene glycol, polypropylene glycol and other polyether polyols; reactants of ethylene glycol and adipic acid or butanediol and Polyester polyols such as adipic acid reactants; polycarbonate polyols; polycaprolactone polyols.
Among these, polyoxytetramethylene glycol is preferably used from the viewpoints of the rationality of the prepolymer or the mechanical strength of the obtained polishing pad. The number average molecular weight of the polyoxytetramethylene glycol is preferably 500 to 2000, more preferably 600 to 1,000, and most preferably 650 to 850.

於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之聚氧伸烷基二醇之情形時,異氰酸酯封端胺基甲酸酯預聚物可包含作為多元醇成分列舉之上述低分子量(分子量50~300之)伸烷基二醇,亦可不包含。作為低分子量(分子量50~300之)伸烷基二醇,可使用作為多元醇成分列舉之上述者。
於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之聚氧伸烷基二醇且進而包含分子量50~300之伸烷基二醇之情形時,分子量50~300之伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量較佳為0~5重量%,更佳為0.5~4重量%,最佳為1~3重量%。又,此處「不含低分子量(分子量50~300之)伸烷基二醇」係指不作為刻意之添加物含有,即便於作為雜質含有之情形時,相對於異氰酸酯封端胺基甲酸酯預聚物整體亦較佳為0.1質量%以下,更佳為0.05質量%以下,最佳為0.01質量%以下。藉由使低分子量(分子量50~300之)伸烷基二醇之含量於上述數值範圍內,可抑制被研磨物中之缺陷並實現平坦之形貌。
In the case where the isocyanate-terminated urethane prepolymer includes a polyoxyalkylene glycol having a molecular weight of 50 to 300, the isocyanate-terminated urethane prepolymer may include the above-mentioned lows listed as a polyol component The molecular weight (50 to 300 molecular weight) of alkylene glycol may or may not be included. As the low molecular weight (50 to 300 molecular weight) alkylene glycol, the above-mentioned ones listed as the polyol component can be used.
When the isocyanate-terminated urethane prepolymer contains a polyoxyalkylene glycol having a molecular weight of 50 to 300 and further contains an alkylene glycol having a molecular weight of 50 to 300, an alkylene having a molecular weight of 50 to 300 The content of the diol with respect to the entire isocyanate-terminated urethane prepolymer is preferably 0 to 5% by weight, more preferably 0.5 to 4% by weight, and most preferably 1 to 3% by weight. Here, the term "excluding low-molecular-weight (50-300 molecular weight) alkylene glycol" means that it is not contained as an intentional additive, and even when contained as an impurity, the isocyanate-blocked urethane The entire prepolymer is also preferably 0.1% by mass or less, more preferably 0.05% by mass or less, and most preferably 0.01% by mass or less. By setting the content of the low molecular weight (50 to 300 molecular weight) alkylene glycol within the above-mentioned numerical range, defects in the object to be polished can be suppressed and a flat morphology can be achieved.

(分子量50~300之伸烷基二醇)
分子量50~300之伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量超過0重量%且未達5重量%,較佳為0.5~4重量%,最佳為1~3重量%。藉由使伸烷基二醇之含量於上述數值範圍內,可抑制被研磨物中之缺陷並實現平坦之形貌。
(Dialkylene glycol with a molecular weight of 50 to 300)
The content of the alkylene glycol with a molecular weight of 50 to 300 relative to the entire isocyanate-terminated urethane prepolymer exceeds 0% by weight and less than 5% by weight, preferably 0.5 to 4% by weight, and most preferably 1 ~ 3% by weight. By setting the content of the alkylene glycol within the above numerical range, defects in the object to be polished can be suppressed and a flat morphology can be realized.

作為分子量50~300之伸烷基二醇,並無特別限定,可使用直鏈狀、支鏈狀者,又,可使用分子末端具有羥基者。作為分子量50~300之伸烷基二醇,例如可使用:乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、新戊二醇、1,5-戊二醇、3-甲基-1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇等,就NCO當量(g/eq)之調整之觀點而言,較佳為使用1,4-丁二醇,原因在於其分子量與先前使用之二乙二醇相近。The alkylene glycol having a molecular weight of 50 to 300 is not particularly limited, and a linear or branched one may be used, and a molecular end having a hydroxyl group may be used. As the alkylene glycol having a molecular weight of 50 to 300, for example, ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1, 4-butanediol, neopentyl glycol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1, 8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, etc., in terms of NCO equivalent (g / eq From the standpoint of adjustment, 1,4-butanediol is preferably used because its molecular weight is similar to that of diethylene glycol previously used.

於本發明中,可使用分子量50~300之伸烷基二醇代替先前使用之二乙二醇之全部或一部分而製造異氰酸酯封端胺基甲酸酯預聚物。In the present invention, an alkylene glycol having a molecular weight of 50 to 300 can be used to replace all or part of the diethylene glycol previously used to produce an isocyanate-terminated urethane prepolymer.

於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之伸烷基二醇之情形時,作為異氰酸酯封端胺基甲酸酯預聚物所包含之除分子量50~300之伸烷基二醇以外之多元醇成分,例如可列舉:二乙二醇、三乙二醇、四乙二醇、五乙二醇、六乙二醇等低分子量(分子量50~300之)聚氧伸烷基二醇;聚氧四亞甲基二醇(PTMG)、聚乙二醇、聚丙烯二醇等聚醚多元醇;乙二醇與己二酸之反應物或丁二醇與己二酸之反應物等聚酯多元醇;聚碳酸酯多元醇;聚己內酯多元醇等。
該等中,就預聚物之處理性或所得之研磨墊之機械強度等觀點而言,較佳為使用聚氧四亞甲基二醇。又,作為聚氧四亞甲基二醇之數量平均分子量,較佳為500~2000,更佳為600~1000,最佳為650~850。
In the case where the isocyanate-terminated urethane prepolymer contains an alkylene glycol having a molecular weight of 50 to 300, the isocyanate-terminated urethane prepolymer contains an alkylene glycol having a molecular weight other than 50 to 300. Examples of polyhydric alcohol components other than glycols include low molecular weight (50 to 300 molecular weight) polyoxyethylene such as diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, and hexaethylene glycol. Alkyl glycols; polyetherpolyols such as polyoxytetramethylene glycol (PTMG), polyethylene glycol, and polypropylene glycol; reactants of ethylene glycol and adipic acid or butanediol and adipic acid Reactants such as polyester polyols; polycarbonate polyols; polycaprolactone polyols.
Among these, polyoxytetramethylene glycol is preferably used from the viewpoints of the rationality of the prepolymer or the mechanical strength of the obtained polishing pad. The number average molecular weight of the polyoxytetramethylene glycol is preferably 500 to 2000, more preferably 600 to 1,000, and most preferably 650 to 850.

於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之伸烷基二醇之情形時,異氰酸酯封端胺基甲酸酯預聚物可包含作為多元醇成分列舉之上述低分子量(分子量50~300之)聚氧伸烷基二醇,亦可不包含。作為低分子量(分子量50~300之)聚氧伸烷基二醇,可使用作為多元醇成分列舉之上述者。
於異氰酸酯封端胺基甲酸酯預聚物包含分子量50~300之伸烷基二醇且進而包含分子量50~300之聚氧伸烷基二醇之情形時,分子量50~300之聚氧伸烷基二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量較佳為超過0重量%且未達3重量%,更佳為0.1~2.8重量%,最佳為0.2~2.5重量%。又,此處「不含低分子量(分子量50~300之)聚氧伸烷基二醇」係指不作為刻意之添加物含有,即便於作為雜質含有之情形時,相對於異氰酸酯封端胺基甲酸酯預聚物整體亦較佳為0.1質量%以下,更佳為0.05質量%以下,最佳為0.01質量%以下。藉由使低分子量(分子量50~300之)聚氧伸烷基二醇之含量於上述數值範圍內,可抑制被研磨物中之缺陷並實現平坦之形貌。
When the isocyanate-terminated urethane prepolymer contains an alkylene glycol having a molecular weight of 50 to 300, the isocyanate-terminated urethane prepolymer may include the above-mentioned low molecular weight ( Polyoxyalkylene glycols (with a molecular weight of 50 to 300) may not be included. As the low molecular weight (50 to 300 molecular weight) polyoxyalkylene glycol, the above-mentioned ones listed as the polyol component can be used.
When the isocyanate-terminated urethane prepolymer contains an alkylene glycol having a molecular weight of 50 to 300 and further contains a polyoxyalkylene glycol having a molecular weight of 50 to 300, a polyoxyethylene having a molecular weight of 50 to 300 The content of the alkyl diol with respect to the entire isocyanate-terminated urethane prepolymer is preferably more than 0% by weight and less than 3% by weight, more preferably 0.1 to 2.8% by weight, and most preferably 0.2 to 2.5% by weight. %. Here, "low molecular weight (50 to 300) polyoxyalkylene glycol is not included" means that it is not contained as an intentional additive, and even when contained as an impurity, it is blocked with isocyanate-terminated aminomethyl The entire acid ester prepolymer is also preferably 0.1% by mass or less, more preferably 0.05% by mass or less, and most preferably 0.01% by mass or less. By setting the content of the low molecular weight (50 to 300) polyoxyalkylene glycol within the above numerical range, defects in the object to be polished can be suppressed and a flat morphology can be achieved.

作為異氰酸酯封端胺基甲酸酯預聚物所包含之聚異氰酸酯成分,例如可列舉:間苯二異氰酸酯、對苯二異氰酸酯、2,6-甲苯二異氰酸酯(2,6-TDI)、2,4-甲苯二異氰酸酯(2,4-TDI)、萘-1,4-二異氰酸酯、二苯基甲烷 -4,4'-二異氰酸酯(MDI)、4,4'-亞甲基-雙(環己基異氰酸酯)(氫化MDI)、3,3'-二甲氧基-4,4'-聯苯二異氰酸酯、3,3'-二甲基二苯基甲烷-4,4'-二異氰酸酯、苯二甲基-1,4-二異氰酸酯、4,4'-二苯基丙烷二異氰酸酯、三亞甲基二異氰酸酯、六亞甲基二異氰酸酯、伸丙基-1,2-二異氰酸酯、伸丁基 -1,2-二異氰酸酯、伸環己基-1,2-二異氰酸酯、伸環己基-1,4-二異氰酸酯、對苯二異硫氰酸酯、苯二甲基-1,4-二異硫氰酸酯、次乙基二異硫氰酸酯等。
該等中,就所得之研磨墊之研磨特性或機械強度等觀點而言,較佳為使用2,6-甲苯二異氰酸酯(2,6-TDI)、2,4-甲苯二異氰酸酯(2,4-TDI)等甲苯二異氰酸酯。
Examples of the polyisocyanate component included in the isocyanate-terminated urethane prepolymer include, for example, m-phenylene diisocyanate, terephthalic acid diisocyanate, 2,6-toluene diisocyanate (2,6-TDI), and 2, 4-toluene diisocyanate (2,4-TDI), naphthalene-1,4-diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), 4,4'-methylene-bis (cyclic Hexyl isocyanate) (hydrogenated MDI), 3,3'-dimethoxy-4,4'-biphenyl diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, benzene Dimethyl-1,4-diisocyanate, 4,4'-diphenylpropane diisocyanate, trimethylene diisocyanate, hexamethylene diisocyanate, propylene-1,2-diisocyanate, butylene -1,2-diisocyanate, cyclohexyl-1,2-diisocyanate, cyclohexyl-1,4-diisocyanate, p-phenylenediisothiocyanate, xylylene-1,4-diiso Thiocyanate, ethylidene diisothiocyanate, etc.
Among these, 2,6-toluene diisocyanate (2,6-TDI), 2,4-toluene diisocyanate (2,4) are preferably used from the viewpoint of the polishing characteristics or mechanical strength of the obtained polishing pad. -TDI) and other toluene diisocyanates.

作為硬化性樹脂組合物所包含之硬化劑,例如,可列舉以下說明之胺系硬化劑。
作為構成胺系硬化劑之聚胺,例如可列舉二胺,於該二胺中,可列舉:伸乙基二胺、伸丙基二胺、六亞甲基二胺等伸烷基二胺;異佛爾酮二胺、二環己基甲烷-4,4'-二胺等具有脂肪族環之二胺;3,3'-二氯-4,4'-二胺基二苯甲烷(別名:亞甲基雙-鄰氯苯胺)(以下簡稱為MOCA)等具有芳香族環之二胺;2-羥乙基伸乙基二胺、2-羥乙基伸丙基二胺、二-2-羥乙基伸乙基二胺、二-2-羥乙基伸丙基二胺、2-羥丙基伸乙基二胺、二-2-羥丙基伸乙基二胺等具有羥基之二胺,尤其是羥烷基伸烷基二胺;等。又,亦可使用3官能三胺化合物及4官能以上之聚胺化合物。
As a hardening | curing agent contained in a curable resin composition, the amine hardening | curing agent demonstrated below is mentioned, for example.
Examples of the polyamine constituting the amine-based hardener include diamines. Among the diamines, alkylene diamines such as ethylene diamine, propylene diamine, and hexamethylene diamine; Isophorone diamine, dicyclohexylmethane-4,4'-diamine and other diamines with aliphatic rings; 3,3'-dichloro-4,4'-diaminodiphenylmethane (alias: Methylene bis-o-chloroaniline) (hereinafter referred to as MOCA) diamines with aromatic rings; 2-hydroxyethyl ethylenediamine, 2-hydroxyethyl ethylenediamine, di-2-hydroxyethyl Diamines with hydroxyl groups, such as diethylene glycol diamine, di-2-hydroxyethyl ethylene diamine, 2-hydroxypropyl ethylene diamine, di-2-hydroxypropyl ethylene diamine, especially hydroxyalkane Alkylene diamine; etc. Moreover, a trifunctional triamine compound and a tetrafunctional or more polyamine compound can also be used.

尤佳之硬化劑為上述MOCA,且該MOCA之化學結構如下所述。A particularly preferred hardener is the aforementioned MOCA, and the chemical structure of the MOCA is as follows.

[化1]
[Chemical 1]

硬化劑整體之量係使用如下量,即:硬化劑之NH2 之莫耳數相對於異氰酸酯封端胺基甲酸酯預聚物之NCO之莫耳數之比率(NH2 之莫耳數/NCO之莫耳數)較佳為0.7~1.1,更佳為0.75~1.0,最佳為0.8~0.95。The amount of the entire hardener is the ratio of the mole number of NH 2 of the hardener to the mole number of NCO of the isocyanate-terminated urethane prepolymer (mole number of NH 2 / The molar number of NCO) is preferably 0.7 to 1.1, more preferably 0.75 to 1.0, and most preferably 0.8 to 0.95.

於本發明中,硬化性樹脂組合物可進而包含微小中空球體。
藉由將微小中空球體與聚胺酯樹脂混合能形成發泡體。所謂微小中空球體,係指使包含由熱塑性樹脂構成之外殼(聚合物殼)及內包於外殼之低沸點烴的未發泡之熱膨脹性微小球狀體熱膨脹而成者。作為上述聚合物殼,例如可使用丙烯腈-偏二氯乙烯共聚物、丙烯腈-甲基丙烯酸甲酯共聚物、氯乙烯-乙烯共聚物等熱塑性樹脂。同樣地,作為內包於聚合物殼之低沸點烴,例如可使用異丁烷、戊烷、異戊烷、石油醚等。
In the present invention, the curable resin composition may further include fine hollow spheres.
Foams can be formed by mixing tiny hollow spheres with a polyurethane resin. The term "small hollow sphere" refers to a product obtained by thermally expanding an outer shell (polymer shell) made of a thermoplastic resin and an unfoamed, thermally expandable microsphere containing a low boiling point hydrocarbon contained in the outer shell. Examples of the polymer shell include thermoplastic resins such as acrylonitrile-vinylidene chloride copolymer, acrylonitrile-methyl methacrylate copolymer, and vinyl chloride-ethylene copolymer. Similarly, as the low-boiling hydrocarbon contained in the polymer shell, for example, isobutane, pentane, isopentane, and petroleum ether can be used.

此外,亦可於硬化性樹脂組合物中添加本領域中通常使用之觸媒等。
又,亦可於硬化性樹脂組合物中後續追加添加上述聚異氰酸酯成分,追加之聚異氰酸酯成分之重量相對於異氰酸酯封端胺基甲酸酯預聚物與追加之聚異氰酸酯成分之合計重量之比率較佳為0.1~10重量%,更佳為0.5~8重量%,尤佳為1~5重量%。
作為於聚胺酯樹脂硬化性組合物中追加添加之聚異氰酸酯成分,並無特別限定,可使用上述聚異氰酸酯成分,但較佳為4,4'-亞甲基-雙(環己基異氰酸酯)(氫化MDI)。
In addition, a catalyst or the like commonly used in the art may be added to the curable resin composition.
In addition, the above-mentioned polyisocyanate component may be added to the curable resin composition, and the ratio of the weight of the additional polyisocyanate component to the total weight of the isocyanate-terminated urethane prepolymer and the additional polyisocyanate component may be added. It is preferably 0.1 to 10% by weight, more preferably 0.5 to 8% by weight, and even more preferably 1 to 5% by weight.
The polyisocyanate component added to the polyurethane resin curable composition is not particularly limited, and the polyisocyanate component described above can be used, but 4,4'-methylene-bis (cyclohexyl isocyanate) (hydrogenated MDI) is preferred. ).

本發明之研磨墊中之研磨層相對於水之接觸角較佳為大於70°,更佳為75°以上,最佳為80°以上。若接觸角為70°以下,則親水性變高,且保持含研磨碎屑之漿料之時間變長,故而有缺陷變大之傾向。於本發明中,水之接觸角係指藉由下述利用自動接觸角計(協和界面科學股份有限公司製造 DropMaster500)之液滴法而測定者。
[實施例]
The contact angle of the polishing layer in the polishing pad of the present invention with respect to water is preferably greater than 70 °, more preferably 75 ° or more, and most preferably 80 ° or more. If the contact angle is 70 ° or less, the hydrophilicity becomes high, and the time for holding the slurry containing the grinding debris becomes longer, so that the defect tends to become larger. In the present invention, the contact angle of water is measured by a droplet method using an automatic contact angle meter (DropMaster 500 manufactured by Kyowa Interface Science Co., Ltd.) as described below.
[Example]

藉由以下例對本發明進行實驗性說明,但以下說明並非欲將本發明之範圍限定於以下例而進行解釋。The present invention is experimentally described by the following examples, but the following description is not intended to limit the scope of the present invention to the following examples.

(材料)
列舉以下例中使用之材料。
(material)
List the materials used in the following examples.

・異氰酸酯封端胺基甲酸酯預聚物:
預聚物(1)・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇作為多元醇成分之NCO當量513之胺基甲酸酯預聚物
預聚物(2)・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及二乙二醇(相對於預聚物整體1重量%)作為多元醇成分之NCO當量486之胺基甲酸酯預聚物
預聚物(3)・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及二乙二醇(相對於預聚物整體2重量%)作為多元醇成分之NCO當量463之胺基甲酸酯預聚物
預聚物(4)・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及二乙二醇(相對於預聚物整體3重量%)作為多元醇成分之NCO當量450之胺基甲酸酯預聚物
預聚物(5)・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇、數量平均分子量1000之聚四亞甲醚二醇、及二乙二醇(相對於預聚物整體5重量%)作為多元醇成分之NCO當量437之胺基甲酸酯預聚物
預聚物(1')・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及1,4-丁二醇(相對於預聚物整體1重量%)作為多元醇成分之NCO當量484之胺基甲酸酯預聚物
預聚物(2')・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及1,4-丁二醇(相對於預聚物整體2重量%)作為多元醇成分之NCO當量459之胺基甲酸酯預聚物
預聚物(3')・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇及1,4-丁二醇(相對於預聚物整體3重量%)作為多元醇成分之NCO當量439之胺基甲酸酯預聚物
預聚物(4')・・・包含甲苯二異氰酸酯作為聚異氰酸酯成分、以及數量平均分子量650之聚四亞甲醚二醇、1,4-丁二醇(相對於預聚物整體1重量%)、及二乙二醇(相對於預聚物整體1重量%)作為多元醇成分之NCO當量441之胺基甲酸酯預聚物
・ Isocyanate-terminated urethane prepolymer:
Prepolymer (1) ... Prepolymerization of urethane prepolymers containing toluene diisocyanate as a polyisocyanate component and polytetramethylene ether glycol having a number average molecular weight of 650 as an NCO equivalent of 513 as a polyol component (2) ..... Contains toluene diisocyanate as a polyisocyanate component, and polytetramethylene glycol and diethylene glycol with a number average molecular weight of 650 (1% by weight based on the entire prepolymer) as polyol components. NCO equivalent 486 urethane prepolymer prepolymer (3) .... Contains toluene diisocyanate as a polyisocyanate component, and polytetramethylene ether glycol and diethylene glycol (relative to the number average molecular weight 650 (relatively 2% by weight of the entire prepolymer) NCO equivalent of 463 as a polyol component, a urethane prepolymer prepolymer (4) ... containing toluene diisocyanate as a polyisocyanate component, and a number average molecular weight of 650 Polytetramethylene ether glycol and diethylene glycol (3% by weight based on the entire prepolymer) as urethane prepolymer prepolymers with an NCO equivalent of 450 as the polyol component (5) ... Toluene diisocyanate as a polyisocyanate NCO with polytetramethylene ether glycol having a number average molecular weight of 650, polytetramethylene ether glycol with a number average molecular weight of 1,000, and diethylene glycol (5% by weight relative to the entire prepolymer) as the polyol NCO Equivalent 437 urethane prepolymer prepolymer (1 ') ... contains toluene diisocyanate as a polyisocyanate component, and polytetramethylene ether glycol with a number average molecular weight of 650 and 1,4-butane Alcohol (1% by weight based on the entire prepolymer) NCO equivalent of 484 as a polyol component Urethane prepolymer prepolymer (2 ') ... includes toluene diisocyanate as a polyisocyanate component and quantity Polytetramethylene ether glycol having an average molecular weight of 650 and 1,4-butanediol (2% by weight based on the entire prepolymer) as urethane prepolymer prepolymers having an NCO equivalent of 459 as a polyol component (3 ') ... Polyurethane diisocyanate is included as a polyisocyanate component, and polytetramethylene glycol and 1,4-butanediol (3% by weight based on the entire prepolymer) are included as a multicomponent Urethane prepolymer prepolymer (4 ') with NCO equivalent of 439 of alcohol component Isocyanate as a polyisocyanate component, and polytetramethylene ether glycol with a number average molecular weight of 650, 1,4-butanediol (1% by weight based on the entire prepolymer), and diethylene glycol (with respect to the prepolymer) 1% by weight) Urethane prepolymer of NCO equivalent 441 as a polyol component

・硬化劑:
MOCA・・・3,3'-二氯-4,4'-二胺基二苯甲烷(別名:亞甲基雙-鄰氯苯胺)(NH2 當量=133.5)
・微小中空球體之商品名:
日本Fillite公司製造 EXPANCEL 551DE40d42
·hardener:
MOCA ... 3,3'-dichloro-4,4'-diaminodiphenylmethane (alias: methylenebis-o-chloroaniline) (NH 2 equivalent = 133.5)
・ Product name of tiny hollow sphere:
EXPLCEL 551DE40d42 made by Japan Fillite

<實施例1~3、比較例1>
(實施例1)
分別準備預聚物(2)100 g作為A成分、作為硬化劑之MOCA 24 g作為B成分、及微小中空球體(EXPANCEL 551DE40d42)4.5 g作為C成分。再者,B成分之胺系硬化劑之NH2 之莫耳數相對於A成分之預聚物之NCO之莫耳數之比率(NH2 之莫耳數/NCO之莫耳數)為0.87。再者,因表示比率而以g顯示進行記載,且根據塊體之尺寸準備所需之重量(份)。以下同樣地以g(份)記法進行記載。
將A成分與C成分混合,對A成分與C成分之混合物進行減壓消泡,其後,將A成分與C成分之混合物及B成分供給至混合機。
將所得之混合液澆鑄至加熱至80℃之模框中,於加熱1小時使其硬化之後將形成之樹脂發泡體自模框中抽出,其後於120℃下進行5小時固化。將該發泡體切片至1.3 mm厚而製成胺基甲酸酯片,獲得研磨墊。
<Examples 1 to 3 and Comparative Example 1>
(Example 1)
100 g of the prepolymer (2) was prepared as the A component, 24 g of MOCA as the hardener was used as the B component, and 4.5 g of fine hollow spheres (EXPANCEL 551DE40d42) were used as the C component. In addition, the ratio of the mole number of NH 2 of the amine hardener of the B component to the mole number of the NCO of the prepolymer of the A component (mole number of NH 2 / mole number of NCO) was 0.87. In addition, the ratio is described in g, and the required weight (parts) is prepared according to the size of the block. Hereinafter, it will be described in the same g (parts) notation.
The A component and the C component are mixed, the mixture of the A component and the C component is decompressed under reduced pressure, and thereafter, the mixture of the A component and the C component and the B component are supplied to the mixer.
The obtained mixed solution was cast into a mold frame heated to 80 ° C., and the formed resin foam was extracted from the mold frame after being heated for 1 hour to harden, and then cured at 120 ° C. for 5 hours. This foam was sliced to a thickness of 1.3 mm to prepare a urethane sheet, and a polishing pad was obtained.

(實施例2)
準備預聚物(3)100 g代替實施例1之A成分之預聚物(2)100 g。
以下,與實施例1同樣地製成胺基甲酸酯片,獲得研磨墊。
(Example 2)
100 g of the prepolymer (3) was prepared instead of 100 g of the prepolymer (2) of the component A of Example 1.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 1 to obtain a polishing pad.

(實施例3)
準備預聚物(4)100 g代替實施例1之A成分之預聚物(2)100 g。
以下,與實施例1同樣地製成胺基甲酸酯片,獲得研磨墊。
(Example 3)
100 g of the prepolymer (4) was prepared in place of 100 g of the prepolymer (2) of the component A of Example 1.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 1 to obtain a polishing pad.

(比較例1)
準備預聚物(5)100 g代替實施例1之A成分之預聚物(2)100 g。
以下,與實施例1同樣地製成胺基甲酸酯片,獲得研磨墊。
(比較例2)
準備預聚物(1)100 g代替實施例1之A成分之預聚物(2)100 g。以下,嘗試與實施例1同樣地製成胺基甲酸酯片,但由於包含A成分、B成分、及C成分之硬化性樹脂組合物至固化為止之時間較長,且未充分地進行硬化,而不容易將所得之發泡體切片,無法獲得研磨墊。
(Comparative example 1)
100 g of the prepolymer (5) was prepared in place of 100 g of the prepolymer (2) of the component A of Example 1.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 1 to obtain a polishing pad.
(Comparative example 2)
100 g of the prepolymer (1) was prepared in place of 100 g of the prepolymer (2) of the component A of Example 1. Hereinafter, an attempt was made to form a urethane sheet in the same manner as in Example 1. However, since the curable resin composition containing the A component, the B component, and the C component took a long time to cure, the curing was not sufficiently performed. It is not easy to slice the obtained foam, and it is impossible to obtain a polishing pad.

(試驗方法)
對實施例1~3及比較例1各自之胺基甲酸酯片(研磨墊)進行以下之密度、A硬度、及D硬度測定。
(密度)
密度(g/cm3 )係依據日本工業規格(JIS K 6505)進行測定。
(A硬度)
研磨墊之A硬度係依據日本工業規格(JIS-K-7311)而使用蕭氏A硬度計進行。此處,試樣係藉由以成為總厚度至少4.5 mm以上之方式視需要重疊複數片胺基甲酸酯片而獲得。
(D硬度)
研磨墊之D硬度係依據日本工業規格(JIS-K-6253)而使用D型硬度計進行測定。此處,試樣係藉由以成為總厚度至少4.5 mm以上之方式視需要重疊複數片胺基甲酸酯片而獲得。
(experiment method)
Each of the urethane sheets (polishing pads) of Examples 1 to 3 and Comparative Example 1 was subjected to the following density, A hardness, and D hardness measurements.
(density)
The density (g / cm 3 ) is measured in accordance with Japanese Industrial Standards (JIS K 6505).
(A hardness)
The A hardness of the polishing pad was measured using a Shore A hardness tester in accordance with Japanese Industrial Standards (JIS-K-7311). Here, the sample is obtained by overlapping a plurality of urethane sheets as necessary so that the total thickness is at least 4.5 mm or more.
(D hardness)
The D hardness of the polishing pad is measured using a D-type hardness tester in accordance with Japanese Industrial Standards (JIS-K-6253). Here, the sample is obtained by overlapping a plurality of urethane sheets as necessary so that the total thickness is at least 4.5 mm or more.

於表1示出實施例1~3及比較例1所得之研磨墊之基本物性。Table 1 shows the basic physical properties of the polishing pads obtained in Examples 1 to 3 and Comparative Example 1.

[表1]
表1
[Table 1]
Table 1

(研磨率)
對實施例1~3及比較例1各自之研磨墊之研磨率(Å)進行測定。研磨試驗之條件如下所述。
(Grinding rate)
The polishing rate (Å) of each of the polishing pads of Examples 1 to 3 and Comparative Example 1 was measured. The conditions of the polishing test are as follows.

(研磨試驗之條件)
・使用研磨機:荏原製作所公司製造 F-REX300
・Disk:3MA188(#100)
・轉速:(壓盤)70 rpm,(頂環)71 rpm
・研磨壓力:3.5 psi、2.9 psi、或1.5 psi此3種
・研磨劑:Cabot公司製造,產品編號:SS25(使用SS25原液:純水=1:1之混合液)
・研磨劑溫度:20℃
・研磨劑噴出量:200 ml/min
・使用工件(被研磨物):使用於12英吋矽晶圓上以利用PE-CVD使四乙氧基矽烷(TEOS)成為1 μm厚度之絕緣膜之方式形成之基板。研磨之初始溫度為20℃,於研磨期間墊表面溫度上升至40~50℃。
・研磨率係於施加10分鐘修整處理之後於3.5 psi之條件下對第1~51片晶圓進行研磨、於2.9 psi之條件下對第52片晶圓進行研磨、於1.5 psi之條件下對第53片晶圓進行研磨、並關於第1、5、10、15、20、25、50、52、53片晶圓所測定出之值。
(Conditions of grinding test)
・ Using grinder: F-REX300 manufactured by Ebara Manufacturing Co., Ltd.
・ Disk: 3MA188 (# 100)
・ Rotating speed: (platen) 70 rpm, (top ring) 71 rpm
・ Grinding pressure: 3.5 psi, 2.9 psi, or 1.5 psi. ・ Abrasive: made by Cabot, product number: SS25 (using SS25 stock solution: pure water = 1: 1 mixed solution)
・ Abrasive temperature: 20 ℃
・ Abrasive discharge: 200 ml / min
・ Workpiece (object to be polished): A substrate formed on a 12-inch silicon wafer to make tetraethoxysilane (TEOS) an insulating film with a thickness of 1 μm by PE-CVD. The initial temperature of the polishing is 20 ° C, and the surface temperature of the pad rises to 40-50 ° C during the polishing.
・ The polishing rate is after grinding for 10 minutes to polish the first to 51 wafers at 3.5 psi, to polish the 52nd wafer at 2.9 psi, and to polish at 1.5 psi The 53rd wafer was polished and the values measured for the 1st, 5th, 10th, 15th, 20th, 25th, 50th, 52th, and 53th wafers.

將研磨率(Å)之評估結果示於表2及圖1。圖1表示3.5 psi(第50片晶圓)、2.9 psi(第52片晶圓)、及1.5 psi(第53片晶圓)中之研磨率(Å)。The evaluation results of the polishing rate (Å) are shown in Table 2 and FIG. 1. Figure 1 shows the polishing rate (Å) in 3.5 psi (50th wafer), 2.9 psi (52th wafer), and 1.5 psi (53rd wafer).

[表2]
表2
[Table 2]
Table 2

(缺陷)
如下所述對實施例1~3及比較例1各自之研磨墊之刮痕等缺陷進行評估。
刮痕等缺陷之評估係基於上述(研磨率)之(研磨試驗之條件)對51片基板進行研磨,於晶圓表面檢查裝置(KLA-Tencor公司製造,Surfscan SP2xpDLS)之高感度測定模式下對研磨加工後之第11片、第26片及第51片基板3片進行測定,且對基板表面中之微刮痕(0.2 μm以上10 μm以下之微細凹痕狀劃痕)之缺陷之個數進行評估。
(defect)
Defects such as scratches on the polishing pads of Examples 1 to 3 and Comparative Example 1 were evaluated as described below.
The evaluation of defects such as scratches is based on the above (polishing rate) (conditions of the polishing test) of 51 substrates, and the wafer surface inspection apparatus (manufactured by KLA-Tencor, Surfscan SP2xpDLS) is used for high-sensitivity measurement mode. The 11th, 26th, and 51th substrates were measured after grinding, and the number of defects in the surface of the substrate (fine dent-like scratches of 0.2 μm to 10 μm) was measured. to evaluate.

將缺陷之評估結果示於表3及圖2。The evaluation results of the defects are shown in Table 3 and FIG. 2.

[表3]
表3
[table 3]
table 3

由表2及圖1之結果可知,實施例1~3及比較例1之研磨墊顯示出用作研磨墊之充分之研磨率(Å),且研磨性優異。又,可知實施例1~3及比較例1之研磨墊於3.5 psi、2.9 psi、及1.5 psi中任一種之研磨壓力下均顯示出同等程度之研磨率(Å),未觀察到較大之差異。As can be seen from the results in Table 2 and FIG. 1, the polishing pads of Examples 1 to 3 and Comparative Example 1 exhibited sufficient polishing rate (Å) as a polishing pad, and had excellent polishing properties. In addition, it can be seen that the polishing pads of Examples 1 to 3 and Comparative Example 1 showed the same degree of polishing rate (Å) under the polishing pressures of any of 3.5 psi, 2.9 psi, and 1.5 psi, and no larger polishing rate was observed. difference.

由表3及圖2之結果可知,二乙二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量為1重量%、2重量%、或3重量%之實施例1~3之研磨墊產生之缺陷較少,視為良好之研磨結果。
另一方面,可知二乙二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量為5重量%之比較例1之研磨墊產生之缺陷較多。
由實施例1~3及比較例1之結果可知,隨著二乙二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量減少,刮痕等缺陷減少,視為良好之結果。
又,如比較例2所示,若將二乙二醇之含量設為0重量%,則有如下問題:反應時間變長,至硬化為止需要較多時間,故而生產性欠佳,進而於硬化後之切片步驟中無法順利地進行切片。
As can be seen from the results in Table 3 and FIG. 2, the content of diethylene glycol relative to the entire isocyanate-terminated urethane prepolymer was 1% by weight, 2% by weight, or 3% by weight of Examples 1 to 3. Abrasive pads have fewer defects and are considered good results.
On the other hand, it can be seen that the polishing pad of Comparative Example 1 in which the content of diethylene glycol relative to the entire isocyanate-terminated urethane prepolymer was 5 wt% had many defects.
From the results of Examples 1 to 3 and Comparative Example 1, it can be seen that as the content of diethylene glycol relative to the entire isocyanate-terminated urethane prepolymer decreases, defects such as scratches decrease, which is considered to be a good result.
In addition, as shown in Comparative Example 2, if the content of diethylene glycol is set to 0% by weight, there is a problem that the reaction time becomes long and it takes a long time until it is hardened. Therefore, the productivity is poor and the hardening is further accelerated. Slicing cannot be performed smoothly in the subsequent slicing step.

如上所述,實施例1~3之研磨墊之研磨率(Å)較高,研磨性優異,且能夠抑制被研磨物之缺陷。另一方面,比較例1之研磨墊雖研磨率(Å)較高且研磨性優異,但被研磨物產生之缺陷較多。As described above, the polishing pads of Examples 1 to 3 have a high polishing rate (Å), excellent polishing properties, and can suppress defects in the object to be polished. On the other hand, although the polishing pad of Comparative Example 1 had a high polishing rate (Å) and excellent polishing properties, there were many defects in the object to be polished.

根據以上結果,可確認二乙二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量超過0重量%且未達5重量%之研磨墊能夠抑制被研磨物中之缺陷並實現平坦之形貌,且缺陷性能及形貌性能優異。Based on the above results, it was confirmed that the polishing pad whose content of diethylene glycol relative to the entire isocyanate-terminated urethane prepolymer exceeds 0% by weight and less than 5% by weight can suppress defects in the object to be polished and achieve flatness. Morphology, and excellent defect performance and morphology performance.

<實施例4~7、比較例3>
(實施例4)
分別準備預聚物(1')100 g作為A成分、作為硬化劑之MOCA 24 g作為B成分、及微小中空球體(EXPANCEL 551DE40d42)4.5 g作為C成分。再者,B成分之胺系硬化劑之NH2 之莫耳數相對於A成分之預聚物之NCO之莫耳數之比率(NH2 之莫耳數/NCO之莫耳數)為0.87。再者,因表示比率而以g顯示進行記載,且根據塊體之尺寸準備所需之重量(份)。以下同樣地以g(份)記法進行記載。
將A成分與C成分混合,對A成分與C成分之混合物進行減壓消泡,其後,將A成分與C成分之混合物及B成分供給至混合機。
將所得之混合液澆鑄至加熱至80℃之模框中,於加熱1小時使其硬化之後將形成之樹脂發泡體自模框中抽出,其後於120℃下進行5小時固化。將該發泡體切片至1.3 mm厚而製成胺基甲酸酯片,獲得研磨墊。
<Examples 4 to 7, Comparative Example 3>
(Example 4)
100 g of the prepolymer (1 ′) was used as the A component, 24 g of MOCA as the hardener was used as the B component, and 4.5 g of micro hollow spheres (EXPANCEL 551DE40d42) were used as the C component. In addition, the ratio of the mole number of NH 2 of the amine hardener of the B component to the mole number of the NCO of the prepolymer of the A component (mole number of NH 2 / mole number of NCO) was 0.87. In addition, the ratio is described in g, and the required weight (parts) is prepared according to the size of the block. Hereinafter, it will be described in the same g (parts) notation.
The A component and the C component are mixed, the mixture of the A component and the C component is decompressed under reduced pressure, and thereafter, the mixture of the A component and the C component and the B component are supplied to the mixer.
The obtained mixed solution was cast into a mold frame heated to 80 ° C., and the formed resin foam was extracted from the mold frame after being heated for 1 hour to harden, and then cured at 120 ° C. for 5 hours. This foam was sliced to a thickness of 1.3 mm to prepare a urethane sheet, and a polishing pad was obtained.

(實施例5)
準備預聚物(2')100 g代替實施例4之A成分之預聚物(1')100 g。
以下,與實施例4同樣地製成胺基甲酸酯片,獲得研磨墊。
(Example 5)
100 g of the prepolymer (2 ') was prepared in place of 100 g of the prepolymer (1') of the component A of Example 4.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 4 to obtain a polishing pad.

(實施例6)
準備預聚物(3')100 g代替實施例4之A成分之預聚物(1')100 g。
以下,與實施例4同樣地製成胺基甲酸酯片,獲得研磨墊。
(Example 6)
100 g of the prepolymer (3 ') was prepared in place of 100 g of the prepolymer (1') of the component A of Example 4.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 4 to obtain a polishing pad.

(實施例7)
準備預聚物(4')100 g代替實施例4之A成分之預聚物(1')100 g。
以下,與實施例4同樣地製成胺基甲酸酯片,獲得研磨墊。
(Example 7)
100 g of the prepolymer (4 ') was prepared in place of 100 g of the prepolymer (1') of the component A of Example 4.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 4 to obtain a polishing pad.

(比較例3)
準備預聚物(5)100 g代替實施例4之A成分之預聚物(1')100 g。
以下,與實施例4同樣地製成胺基甲酸酯片,獲得研磨墊。
(Comparative example 3)
100 g of the prepolymer (5) was prepared in place of 100 g of the prepolymer (1 ′) of the component A of Example 4.
Hereinafter, a urethane sheet was prepared in the same manner as in Example 4 to obtain a polishing pad.

(試驗方法)
關於實施例4~7及比較例3各自之研磨墊,進行以下之接觸角測定並對缺陷進行評估。
(experiment method)
Regarding each of the polishing pads of Examples 4 to 7 and Comparative Example 3, the following contact angles were measured and defects were evaluated.

(接觸角)
關於實施例4~7及比較例3各自之胺基甲酸酯片之表面,測定水之接觸角。水之接觸角係藉由利用自動接觸角計(協和界面科學股份有限公司製造 DropMaster500)之液滴法進行測定。即,於自動接觸角計之注射器中加入蒸餾水,於溫度20℃、濕度50%之條件下,自注射針向研磨片表面滴下1滴(1 μL)水滴,且讀取滴下後經過300秒之接觸角。
(Contact angle)
Regarding the surfaces of the urethane sheets of Examples 4 to 7 and Comparative Example 3, the contact angle of water was measured. The contact angle of water was measured by a droplet method using an automatic contact angle meter (DropMaster 500, manufactured by Kyowa Interface Science Co., Ltd.). That is, add distilled water to the syringe of the automatic contact angle meter, and drop 1 drop (1 μL) of water droplets from the injection needle on the surface of the abrasive sheet at a temperature of 20 ° C and a humidity of 50%, and read 300 seconds after the drop. Contact angle.

(缺陷)
缺陷之評估係基於以下研磨試驗之條件對25片基板進行研磨,於晶圓表面檢查裝置(KLA-Tencor公司製造,SurfscanSP2xpDLS)之高感度測定模式下對研磨加工後之第21~25片之5片基板進行測定,且對由研磨碎屑所致之刮痕之個數進行評估。於缺陷之評估中,於12英吋(300 mm<b)晶圓上之0.16 μm以上之缺陷未達200個時視為○,200個以上時視為×。
(defect)
The evaluation of the defects is based on the polishing of 25 substrates based on the following grinding test conditions. The 5th of the 21st to 25th wafers after polishing are processed in the high-sensitivity measurement mode of a wafer surface inspection device (manufactured by KLA-Tencor, SurfscanSP2xpDLS) The substrate was measured, and the number of scratches caused by grinding debris was evaluated. In the evaluation of defects, a defect of 0.16 μm or more on a 12-inch (300 mm <b) wafer is regarded as ○ when it is less than 200, and it is regarded as × when it is more than 200.

(研磨試驗之條件)
・使用研磨機:荏原製作所公司製造,F-REX300
・Disk:3MA188(#100)
・轉速:(壓盤)70 rpm,(頂環)71 rpm
・研磨壓力:3.5 psi
・研磨劑:Cabot公司製造,產品編號:SS25(使用SS25原液:純粹=重量比1:1之混合液)
・研磨劑溫度:20℃
・研磨劑噴出量:200 ml/min
・使用工件(被研磨物):於12英吋矽晶圓上以利用PE-CVD使四乙氧基矽烷成為1 μm厚度之絕緣膜之方式形成之基板
自研磨之初始溫度20℃,於研磨期間墊表面溫度上升至40~50℃。
(Conditions of grinding test)
・ Grinding machine used: F-REX300, manufactured by Ebara Manufacturing Co., Ltd.
・ Disk: 3MA188 (# 100)
・ Rotating speed: (platen) 70 rpm, (top ring) 71 rpm
・ Grinding pressure: 3.5 psi
・ Abrasive: made by Cabot, product number: SS25 (using SS25 stock solution: pure = mixed solution with a weight ratio of 1: 1)
・ Abrasive temperature: 20 ℃
・ Abrasive discharge: 200 ml / min
・ Workpiece (object to be polished): A substrate formed on a 12-inch silicon wafer by using PE-CVD to make tetraethoxysilane into an insulating film with a thickness of 1 μm. The initial temperature of self-polishing is 20 ° C. During this period, the surface temperature of the pad rose to 40-50 ° C.

將以上結果示於表4。The above results are shown in Table 4.

[表4]
表4
*1,4-BD:1,4-丁二醇,DEG:二乙二醇
*-:係指不作為成分添加。
[Table 4]
Table 4
* 1,4-BD: 1,4-butanediol, DEG: diethylene glycol *-: It is not added as a component.

如表4所示,關於實施例4~7之研磨墊,接觸角為75°以上,與比較例3之研磨墊相比疏水性較高,能夠抑制刮痕之產生。又,由實施例4~7及比較例3之結果可知,若增加疏水性較高之作為伸烷基二醇之1,4-丁二醇之添加量或減少親水性較高之作為聚氧伸烷基二醇之二乙二醇之添加量,則研磨墊之接觸角有增大之傾向。As shown in Table 4, the polishing pads of Examples 4 to 7 had a contact angle of 75 ° or more, which was more hydrophobic than the polishing pad of Comparative Example 3, and could suppress the generation of scratches. In addition, from the results of Examples 4 to 7 and Comparative Example 3, it can be seen that if the amount of 1,4-butanediol, which is an alkylene glycol, which is relatively high in hydrophobicity, is increased, or the polyoxygen, which is relatively hydrophilic, is decreased. The amount of diethylene glycol added to the alkylene glycol tends to increase the contact angle of the polishing pad.

根據以上結果,可確認1,4-丁二醇相對於異氰酸酯封端胺基甲酸酯預聚物整體之含量超過0重量%且未達5重量%之研磨墊能夠抑制被研磨物中之缺陷並實現平坦之形貌,且缺陷性能及形貌性能優異。Based on the above results, it was confirmed that the polishing pad whose content of 1,4-butanediol relative to the entire isocyanate-terminated urethane prepolymer exceeds 0% by weight and less than 5% by weight can suppress defects in the object to be polished. And achieve a flat topography, and excellent defect performance and topography performance.

圖1係表示實施例1~3及比較例1之研磨率(Å)之評估結果之圖表。FIG. 1 is a graph showing evaluation results of polishing rates (Å) in Examples 1 to 3 and Comparative Example 1. FIG.

圖2係表示實施例1~3及比較例1之缺陷之評估結果之圖表。 FIG. 2 is a graph showing evaluation results of defects in Examples 1 to 3 and Comparative Example 1. FIG.

Claims (13)

一種研磨墊,其具有含聚胺酯樹脂之研磨層,且 上述聚胺酯樹脂係包含異氰酸酯封端胺基甲酸酯預聚物及硬化劑之硬化性樹脂組合物之硬化物,上述異氰酸酯封端胺基甲酸酯預聚物係包括分子量50~300之二醇之多元醇成分與聚異氰酸酯成分之反應產物,且上述二醇之含量相對於上述異氰酸酯封端胺基甲酸酯預聚物整體超過0重量%且未達5重量%。A polishing pad having a polishing layer containing a polyurethane resin, and The polyurethane resin is a cured product of a curable resin composition containing an isocyanate-terminated urethane prepolymer and a hardener. The isocyanate-terminated urethane prepolymer includes a diol having a molecular weight of 50 to 300. The reaction product of the polyol component and the polyisocyanate component, and the content of the diol is more than 0% by weight and less than 5% by weight relative to the entire isocyanate-terminated urethane prepolymer. 如請求項1之研磨墊,其中上述二醇為聚氧伸烷基二醇。The polishing pad according to claim 1, wherein the diol is polyoxyalkylene glycol. 如請求項2之研磨墊,其中上述聚氧伸烷基二醇為二乙二醇。The polishing pad according to claim 2, wherein the polyoxyalkylene glycol is diethylene glycol. 如請求項1之研磨墊,其中上述二醇為伸烷基二醇。The polishing pad according to claim 1, wherein the diol is an alkylene glycol. 如請求項4之研磨墊,其中上述伸烷基二醇係分子末端具有羥基之直鏈狀化合物。The polishing pad according to claim 4, wherein the alkylene glycol-based linear compound has a hydroxyl group at a molecular terminal. 如請求項5之研磨墊,其中上述伸烷基二醇為1,4-丁二醇。The polishing pad according to claim 5, wherein the alkylene glycol is 1,4-butanediol. 如請求項1至6中任一項之研磨墊,其中上述異氰酸酯封端胺基甲酸酯預聚物之NCO當量(g/eq)未達500。The polishing pad according to any one of claims 1 to 6, wherein the NCO equivalent (g / eq) of the isocyanate-terminated urethane prepolymer is less than 500. 如請求項1至7中任一項之研磨墊,其中上述聚異氰酸酯成分包含甲苯二異氰酸酯。The polishing pad according to any one of claims 1 to 7, wherein the polyisocyanate component includes toluene diisocyanate. 如請求項1至8中任一項之研磨墊,其中上述多元醇成分進而包含聚氧四亞甲基二醇。The polishing pad according to any one of claims 1 to 8, wherein the polyol component further comprises polyoxytetramethylene glycol. 如請求項1至9中任一項之研磨墊,其中上述硬化劑包含3,3'-二氯-4,4'-二胺基二苯甲烷。The polishing pad according to any one of claims 1 to 9, wherein the hardener comprises 3,3'-dichloro-4,4'-diaminodiphenylmethane. 如請求項1至10中任一項之研磨墊,其中上述硬化性樹脂組合物進而包含微小中空球體。The polishing pad according to any one of claims 1 to 10, wherein the curable resin composition further contains fine hollow spheres. 一種方法,其係如請求項1至11中任一項之研磨墊之製造方法,且 上述方法包括使上述研磨層成形之步驟。A method for manufacturing a polishing pad according to any one of claims 1 to 11, and The method includes the step of forming the polishing layer. 一種方法,其係光學材料或半導體材料之表面研磨方法,且上述方法使用如請求項1至11中任一項之研磨墊。A method which is a surface polishing method of an optical material or a semiconductor material, and the above method uses a polishing pad according to any one of claims 1 to 11.
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