WO2023054331A1 - 研磨層用熱可塑性ポリウレタン、研磨層、及び研磨パッド - Google Patents

研磨層用熱可塑性ポリウレタン、研磨層、及び研磨パッド Download PDF

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WO2023054331A1
WO2023054331A1 PCT/JP2022/035870 JP2022035870W WO2023054331A1 WO 2023054331 A1 WO2023054331 A1 WO 2023054331A1 JP 2022035870 W JP2022035870 W JP 2022035870W WO 2023054331 A1 WO2023054331 A1 WO 2023054331A1
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Prior art keywords
polishing
thermoplastic polyurethane
polishing layer
water
sheet
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PCT/JP2022/035870
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English (en)
French (fr)
Japanese (ja)
Inventor
梓紗 砂山
佑有子 合志
充 加藤
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Kuraray Co Ltd
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Kuraray Co Ltd
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Priority to US18/695,389 priority Critical patent/US20240399530A1/en
Priority to EP22876197.9A priority patent/EP4410478A4/en
Priority to JP2023551511A priority patent/JPWO2023054331A1/ja
Priority to KR1020247009870A priority patent/KR20240087742A/ko
Priority to IL311635A priority patent/IL311635A/en
Priority to CN202280064671.7A priority patent/CN117980110A/zh
Publication of WO2023054331A1 publication Critical patent/WO2023054331A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0895—Manufacture of polymers by continuous processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00—Lapping machines or devices; Accessories
    • B24B37/11—Lapping tools
    • B24B37/20—Lapping pads for working plane surfaces
    • B24B37/24—Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
    • B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
    • B24D3/20—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent and being essentially organic
    • B24D3/22—Rubbers synthetic or natural
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4808—Mixtures of two or more polyetherdiols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P52/00—Grinding, lapping or polishing of wafers, substrates or parts of devices
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00—Lapping machines or devices; Accessories
    • B24B37/11—Lapping tools
    • B24B37/20—Lapping pads for working plane surfaces
    • B24B37/22—Lapping pads for working plane surfaces characterised by a multi-layered structure

Definitions

  • the present invention relates to a thermoplastic polyurethane for a polishing layer, a polishing layer, and a polishing pad.
  • Polishing methods for planarizing the surface of a semiconductor wafer include CMP (Chemical Mechanical Polishing (Planarization)).
  • CMP is a method of polishing an object to be polished with high precision using a polishing pad while supplying a slurry containing abrasive grains and a reaction liquid to the surface of the object to be polished.
  • Thermoplastic polyurethane is used as a material constituting the polishing layer of the polishing pad used in this method (for example, Patent Documents 1 to 7).
  • JP 2009-274208 A Japanese Patent Application Laid-Open No. 2018-39105 WO2020/036038 WO2016/067588 Japanese Patent Publication No. 2018-531157 WO2011/077999 WO2007/034980
  • Patent Documents 1 and 2 there is a problem that defects such as foreign matter, scratches, and pits occur.
  • Patent Documents 3 to 6 there is a problem that the polishing speed is lowered.
  • Patent Document 7 there is a problem that the slurry retention force on the surface of the polishing pad is lowered and the polishing rate is lowered.
  • An object of the present invention is to provide a plastic polyurethane, a polishing layer using the same, and a polishing pad.
  • the present inventors conducted extensive studies and found that the use of a thermoplastic polyurethane for a polishing layer, in which the D hardness and the contact angle with water are adjusted within a predetermined range, reduces the polishing temperature and reduces defects.
  • the inventors have found that it is possible to produce a polishing layer capable of polishing at a high polishing rate while suppressing the occurrence of , thus completing the present invention.
  • the present invention relates to the following [1] to [10].
  • a sheet with a thickness of 2 mm has a D hardness of less than 50 after saturated swelling with water at 50° C., and a sheet with a thickness of 200 ⁇ m has a contact angle with water of 70 degrees or less.
  • Thermoplastic polyurethane for the polishing layer [2] The thermoplastic polyurethane for a polishing layer according to [1] above, wherein the sheet having a thickness of 200 ⁇ m has a change in contact angle calculated from the following formula (1) of 40 to 60%.
  • thermoplastic polyurethane for a polishing layer according to [1] or [2] above, wherein the sheet having a thickness of 500 ⁇ m has a tensile modulus of 100 MPa or less after being saturated with water at 50°C.
  • any of the above [1] to [3], wherein the temperature at which the loss tangent (tan ⁇ ) is maximum in the range of -30 to 100 ° C in the sheet with a thickness of 500 ⁇ m is in the range of -15 to 25 ° C.
  • thermoplastic polyurethane for the abrasive layer according to 1.
  • thermoplastic polyurethane for a polishing layer containing at least a structural unit derived from a chain extender, a structural unit derived from a polyol, and a structural unit derived from a polyisocyanate, wherein the nitrogen derived from the isocyanate group of the polyisocyanate
  • thermoplastic polyurethane for a polishing layer that constitutes a polishing layer capable of polishing at a high polishing rate while suppressing the occurrence of defects by lowering the polishing temperature, a polishing layer using the thermoplastic polyurethane, and polishing. Pads can be provided.
  • FIG. 1 is a schematic diagram for explaining the polishing method using the polishing pad of the present invention.
  • the thermoplastic polyurethane for a polishing layer of the present invention has a D hardness of less than 50 after saturated swelling with water at 50° C. in a 2 mm thick sheet, and a 200 ⁇ m thick sheet that does not contact water.
  • the angle is 70 degrees or less.
  • the thermoplastic polyurethane for a polishing layer of the present invention has a D hardness of less than 50 after saturated swelling with water at 50° C. in a 2 mm thick sheet, and contact with water in a 200 ⁇ m thick sheet. When the angle is 70 degrees or less, it is possible to manufacture a polishing layer that can be polished at a high polishing rate while suppressing the occurrence of defects by reducing the polishing temperature.
  • thermoplastic polyurethane for polishing layer of the present invention is not particularly limited as long as the D hardness of a 2 mm thick sheet after saturated swelling with water at 50° C. is less than 50, but preferably 25 or more. , more preferably 30 or more, and preferably 48 or less, more preferably 46 or less.
  • the D hardness after saturated swelling with water at 50° C. is within the preferred range, the surface hardness is low and the contact area is large, so that a large amount of abrasive grains can be held between the polishing layer and the wafer. Therefore, efficient polishing becomes possible, and the polishing rate can be improved.
  • the D hardness after saturated swelling with water at 50° C. is measured according to JIS K 7311:1995 according to the method described in Examples.
  • a hydrophilic moiety is introduced into a structural unit derived from a polyol (for example, polyethylene glycol (PEG) is used as a polyol), or a compound having a branched structure with a small intermolecular force as a chain extender (for example, 3 -methyl-1,5-pentanediol (MPD), 1,3-butanediol, neopentyl glycol) or compounds with an odd number of carbon atoms as chain extenders (e.g. 1,9-nonanediol) can be used to obtain a thermoplastic polyurethane for a polishing layer having a D hardness of less than 50 after saturated swelling with water at 50°C.
  • PEG polyethylene glycol
  • MPD 1,3-butanediol
  • the thermoplastic polyurethane for a polishing layer of the present invention is not particularly limited as long as the contact angle with water in a sheet having a thickness of 200 ⁇ m is 70 degrees or less, preferably 69 degrees or less, more preferably 68 degrees. or less, more preferably 67 degrees or less.
  • the contact angle with water is within the preferred range, the hydrophilicity of the polishing surface is improved, so that scratches during polishing can be reduced, and the polishing temperature is lowered to further suppress the occurrence of defects. It can be polished at a higher polishing rate.
  • the contact angle with water means “contact angle with water (immediately after)"("contactangle" in claim 1 of the present application means “contact angle (immediately after)”), and is described in the examples. can be measured according to the method of In addition, “immediately after” means two seconds after dropping water.
  • the change in contact angle in a sheet having a thickness of 200 ⁇ m is not particularly limited, but is preferably 40 to 60%, more preferably 41 to 59%, It is more preferably 45 to 55%.
  • the change in contact angle is within the preferred range, it can be controlled to change from a "high contact angle” that facilitates molding to a "low contact angle” that is highly hydrophilic by contact with water. Polishing can be performed at a higher polishing rate while suppressing the occurrence of defects by lowering the polishing temperature.
  • the above-mentioned "change in contact angle” is calculated from the following formula (1).
  • A/B ⁇ 100 (1) (In the above formula (1), A represents the contact angle 15 minutes after dropping 2.5 ⁇ L of room temperature (23 ° C.) water, and B represents the contact angle immediately after dropping 2.5 ⁇ L of room temperature (23 ° C.) water. represents an angle.)
  • thermoplastic polyurethane having a D hardness of less than 50 after being saturated and swollen with water at 50°C is provided with a hydrophilic moiety that facilitates the movement of molecular chains when in contact with water.
  • a branched structure which is a molecular structure that easily swells when in contact, it is controlled to change from a "high contact angle” that facilitates molding by contact with water to a "low contact angle” that is highly hydrophilic. be able to.
  • the thermoplastic polyurethane for a polishing layer of the present invention preferably has a tensile modulus of 100 MPa or less, more preferably 30 to 90 MPa in a sheet having a thickness of 500 ⁇ m after saturated swelling with water at 50° C. More preferably, it is 40 to 80 MPa.
  • the tensile modulus of elasticity after saturated swelling with water at 50°C is within the preferred range, the D hardness of the thermoplastic polyurethane for the polishing layer can be reduced, thereby lowering the polishing temperature and reducing defects. It is possible to polish at a higher polishing rate while further suppressing the occurrence.
  • the tensile modulus can be measured according to the method described in Examples.
  • the change in tensile elastic modulus of a sheet having a thickness of 500 ⁇ m when saturated with water is not particularly limited, but is preferably 75% or more, more preferably 77 to 77%. 100%, more preferably 79 to 95%.
  • hydrophilicity can be imparted to the polishing layer while maintaining polishing stability when in contact with water.
  • C/D ⁇ 100 (2) (In the above formula (2), C represents the tensile modulus at 23° C. and 50% RH after saturation swelling with water at 50° C., and D represents the tensile elasticity at 23° C. and 50% RH before saturation swelling. rate.)
  • the temperature at which the loss tangent (tan ⁇ ) is maximized in the range of -30 to 100°C is preferably in the range of -15 to 25°C in a sheet having a thickness of 500 ⁇ m. , more preferably in the range of -15 to 20 ° C., more preferably in the range of -12 to 18 ° C., still more preferably in the range of -12 to 10 ° C., still more preferably -12 ⁇ 8°C.
  • the D hardness of the thermoplastic polyurethane for the polishing layer can be adjusted to an appropriate range, and the polishing temperature can be lowered to reduce the occurrence of defects. can be further suppressed while polishing at a higher polishing rate.
  • the temperature at which the loss tangent (tan ⁇ ) becomes maximum can be measured according to the method described in Examples.
  • the thermoplastic polyurethane for a polishing layer of the present invention preferably has a breaking elongation of 500% or more, more preferably in the range of 510 to 800%, still more preferably 520 to 750% in a sheet having a thickness of 500 ⁇ m. %.
  • the contact area can be increased while suppressing burrs, and the polishing temperature can be lowered to further suppress the occurrence of defects, and at a higher polishing rate.
  • the elongation at break can be measured according to the method described in Examples.
  • thermoplastic polyurethane for polishing layer of the present invention preferably contains at least a structural unit derived from a chain extender, a structural unit derived from a polyol, and a structural unit derived from a polyisocyanate, for example, from the viewpoint of ease of production. , a structural unit derived from a chain extender, a structural unit derived from a polyol, and a structural unit derived from a polyisocyanate.
  • the total content of the structural units derived from the chain extender, the structural units derived from the polyol, and the structural units derived from the polyisocyanate with respect to all structural units in the thermoplastic polyurethane for the polishing layer is preferably at least 80% by mass. Yes, more preferably 85% by mass or more, still more preferably 90% by mass or more, still more preferably 95% by mass or more, and most preferably 100% by mass.
  • Chain extender used in the production of the polyurethane in the present invention, any chain extender conventionally used in the production of ordinary polyurethanes may be used. Specifically, it is preferable to use a low-molecular-weight compound having a molecular weight of 300 or less and having two or more active hydrogen atoms capable of reacting with an isocyanate group.
  • 1,4-butanediol (BD), 1,5-pentanediol (PD), 1,9-nonanediol (ND), and 3-methyl-1,5-pentanediol (MPD) are preferred.
  • BD 1,4-butanediol
  • PD 1,5-pentanediol
  • ND 1,9-nonanediol
  • MPD 3-methyl-1,5-pentanediol
  • the branched structure preferably has 1 to 4 branches, and the branched group (side chain) preferably has 1 to 6 carbon atoms.
  • the compound having the branched structure examples include 3-methyl-1,5-pentanediol (MPD), 1,3-butanediol, neopentyl glycol, 2,3-butanediol, 2,5- dimethyl-2,5-hexanediol, and the like.
  • polyols include polyether diols such as polyethylene glycol (PEG) and polytetramethylene glycol (PTMG); polycarbonate diols; polyester diols; These may be used individually by 1 type, or may be used in combination of 2 or more type. Among these, polyether diols and/or polyester diols are preferable from the viewpoint of easy availability and excellent reactivity.
  • the polyol preferably contains 15 mol % or more of polyethylene glycol, more preferably 20 mol % or more of polyethylene glycol, and even more preferably 25 mol % or more of polyethylene glycol.
  • a thermoplastic polyurethane can be prepared in which a hydrophilic site is introduced into the structural unit derived from the polyol.
  • the hydrophilic moiety means a compound having a hydrophilic group and/or skeleton such as a carboxy group, an ester group, a carbonyl group, or a polyoxyethylene skeleton (e.g., polyethylene glycol, poly(nonamethylene adipate)).
  • thermoplastic polyurethane in which a hydrophilic site is introduced into the structural unit derived from polyol can have a D hardness of less than 50 after saturated swelling with water at 50° C., and the abrasive grain holding power is improved. , efficient polishing becomes possible, and a polishing layer having an improved polishing rate can be obtained.
  • the number average molecular weight of the polyol is preferably 450 to 3,000, more preferably 500 to 2,700, still more preferably 550 to 2,400. When the number average molecular weight of the polyol is within the above range, it is easy to obtain a polishing layer that maintains the required properties such as rigidity, hardness and hydrophilicity.
  • the number average molecular weight of the polyol means the number average molecular weight calculated based on the hydroxyl value measured according to JIS K 1557-1:2007.
  • polyether diol Specific examples of polyether diols include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, poly(methyltetramethylene glycol), glycerin-based polyalkylene ether glycol, and the like. These may be used singly or in combination of two or more. Among these, polyethylene glycol (PEG) and polytetramethylene glycol (PTMG) are preferred.
  • Polycarbonate diols include those obtained by reacting a low-molecular-weight diol with a carbonate compound.
  • Low-molecular-weight diols for producing polycarbonate diols include the low-molecular-weight diols exemplified above.
  • Carbonate compounds for producing polycarbonate diols include dialkyl carbonates, alkylene carbonates, diaryl carbonates, and the like. Examples of dialkyl carbonate include dimethyl carbonate and diethyl carbonate, examples of alkylene carbonate include ethylene carbonate, and examples of diaryl carbonate include diphenyl carbonate.
  • Polyester diols include, for example, polyester diols obtained by direct esterification reaction or transesterification reaction of a dicarboxylic acid or an ester-forming derivative thereof such as an ester or anhydride thereof with a low-molecular-weight diol.
  • dicarboxylic acids include oxalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecane dicarboxylic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3 -aliphatic dicarboxylic acids having 2 to 12 carbon atoms such as methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid and 3,7-dimethyldecanedioic acid; triglycerides Aliphatic dicarboxylic acids such as dimerized aliphatic dicarboxylic acids having 14 to 48 carbon atoms (dimer acids) and hydrogenated products thereof (hydrogenated dimer acids) obtained by dimerizing unsaturated fatty acids obtained by fractional distillation of 1, Alicyclic dicarboxylic acids such as 4-cyclo
  • dimer acid and the hydrogenated dimer acid examples include trade names "PRIPOL 1004", “PRIPOL 1006", “PRIPOL 1009” and “PRIPOL 1013” manufactured by Uniqema. These may be used singly or in combination of two or more.
  • Specific examples of low-molecular-weight diols include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, and neopentyl.
  • Glycol 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 2-methyl-1,8-octane aliphatic diols such as diols, 1,9-nonanediol and 1,10-decanediol; alicyclic diols such as cyclohexanedimethanol and cyclohexanediol; These may be used singly or in combination of two or more. Among these, diols having 6 to 12 carbon atoms are preferred, diols having 8 to 10 carbon atoms are more preferred, and diols having 9 carbon atoms are even more preferred.
  • the polyisocyanate is not particularly limited as long as it is a polyisocyanate that is commonly used in the production of thermoplastic polyurethanes.
  • MDI 4,4′-diphenylmethane diisocyanate
  • the nitrogen content ratio derived from the isocyanate group of the polyisocyanate is not particularly limited, but is preferably 4.0 to 5.0% by mass, more preferably 4.1 to 4.9% by mass. Yes, more preferably in the range of 4.2 to 4.8% by mass. When the nitrogen content is within the preferred range, polishing layer hardness can be adjusted while maintaining polishing stability and polishing flatness.
  • the nitrogen content ratio is "(mass ratio of structural units derived from polyisocyanate contained in thermoplastic polyurethane) x ((total mass of nitrogen atoms present in isocyanate groups contained in one molecule of polyisocyanate)/ (mass of one molecule of polyisocyanate)) ⁇ 100”, and can be measured according to the method described in the Examples.
  • the thermoplastic polyurethane for a polishing layer of the present invention may optionally contain a cross-linking agent, a filler, a cross-linking accelerator, a cross-linking aid, a softening agent, a tackifier, an anti-aging agent, a foaming agent, a processing aid, and adhesion.
  • Additives such as additives, thickeners, antioxidants, and conductive agents may also be contained.
  • the content of the additive in the thermoplastic polyurethane for the polishing layer is not particularly limited, but is preferably 50% by mass or less, more preferably 20% by mass or less, and still more preferably 10% by mass or less.
  • a hydrophilic site is introduced into a structural unit derived from a polyol (for example, polyethylene glycol (PEG) is used as a polyol), or a compound having a branched structure with a small intermolecular force as a chain extender (for example, 3-methyl -
  • a polyol for example, polyethylene glycol (PEG) is used as a polyol
  • a compound having a branched structure with a small intermolecular force as a chain extender for example, 3-methyl -
  • MPD 1,5-pentanediol
  • thermoplastic polyurethane for the polishing layer is obtained by polymerizing the raw materials described above through a urethanization reaction using a known prepolymer method or one-shot method. More specifically, in the absence of a solvent substantially, the above-described components are blended in a predetermined ratio and melt-mixed using a single-screw or multi-screw extruder by melt polymerization. and a method of producing by polymerization by a prepolymer method in the presence of a solvent. In addition, you may perform melt polymerization continuously. In the present invention, it is preferable to use melt polymerization from the viewpoint of stably producing the thermoplastic polyurethane for a polishing layer of the present invention.
  • thermoplastic polyurethane for abrasive layer is, for example, pelletized and then molded into a sheet-like molding by various molding methods such as extrusion molding, injection molding, blow molding, and calender molding.
  • extrusion molding using a T-die yields a sheet-like molding with a uniform thickness.
  • the abrasive layer of the present invention is formed by molding the thermoplastic polyurethane for abrasive layer of the present invention into a sheet.
  • the content of the thermoplastic polyurethane for polishing layer in the polishing layer is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 90% by mass or more, and most preferably 100% by mass. is.
  • the abrasive layer may be either foamed or non-foamed thermoplastic polyurethane for abrasive layer, preferably non-foamed.
  • the polishing layer is a non-foamed thermoplastic polyurethane for the polishing layer
  • the uniformity of polishing is high, and the occurrence of defects due to variations due to distribution of foams and aggregates in the foams can be suppressed, resulting in polishing properties. is less likely to fluctuate and stable polishing can be achieved.
  • the density of the thermoplastic polyurethane molding for the polishing layer is preferably 0.75 g/cm 3 or more, more preferably 0.85 g/cm 3 or more, and still more preferably 1.0 g/cm 3 or more. .
  • the density of the molded thermoplastic polyurethane for the polishing layer is equal to or higher than the lower limit, the polishing layer will have appropriate flexibility.
  • a non-foamed thermoplastic polyurethane for the polishing layer is particularly preferable from the viewpoint of excellent polishing stability due to high rigidity and homogeneity of the material.
  • the shape of the abrasive layer of the present invention can be appropriately adjusted, for example, by cutting, slicing, punching, or the like, a sheet-like molding of thermoplastic polyurethane for the abrasive layer.
  • the thickness of the polishing layer is not particularly limited, it is preferably 0.5 to 5.0 mm, more preferably 1.0 to 3.0 mm, still more preferably 1.2 to 2.5 mm. When the thickness of the polishing layer is within the above range, the productivity and handleability are improved, and the stability of the polishing performance is also improved.
  • the polished surface of the polishing layer has a predetermined shape such as concentric, lattice, spiral, or radial shape by a method such as grinding, laser processing, transferring with a mold during injection molding, or stamping with a heated mold.
  • recesses such as grooves and holes are formed in a pattern of .
  • Such recesses supply slurry uniformly and sufficiently to the polishing surface, and are useful for discharging polishing debris that causes scratches and preventing damage to the wafer due to adsorption of the polishing layer.
  • the distance between the grooves is preferably 1.0 to 50 mm, more preferably 1.5 to 30 mm, still more preferably 2.0 to 15 mm.
  • the width of the groove is preferably 0.1 to 3.0 mm, more preferably 0.2 to 2.0 mm.
  • the depth of the grooves is less than the thickness of the polishing layer, preferably 0.2-1.8 mm, more preferably 0.4-1.5 mm.
  • the cross-sectional shape of the groove may be appropriately selected from, for example, rectangular, trapezoidal, triangular, and semicircular shapes depending on the purpose.
  • the polishing pad of the present invention uses the polishing layer of the present invention.
  • the polishing pad of the present invention may consist of only the polishing layer of the present invention, or may be a laminate in which a cushion layer is laminated on the non-polishing surface of the polishing layer.
  • the cushion layer is preferably a layer having hardness lower than that of the polishing layer.
  • the hard polishing layer follows local irregularities on the surface to be polished, and the cushion layer is effective against warpage and undulation of the entire substrate to be polished.
  • polishing can be performed with an excellent balance between global flatness (a state in which large-cycle unevenness of the wafer substrate is reduced) and local flatness (a state in which local unevenness is reduced).
  • the material used as the cushion layer include a composite of nonwoven fabric impregnated with polyurethane (for example, "Suba400" (manufactured by Nitta Haas Co., Ltd.); natural rubber, nitrile rubber, polybutadiene rubber, silicone rubber, and the like. rubber; thermoplastic elastomers such as polyester thermoplastic elastomers, polyamide thermoplastic elastomers, and fluorothermoplastic elastomers; foamed plastics; polyurethanes, and the like.
  • polyurethane having a foamed structure is particularly preferable, since it is easy to obtain flexibility preferable for the cushion layer.
  • the thickness of the cushion layer is not particularly limited, it is preferably about 0.5 to 5 mm, for example. If the cushion layer is too thin, the effect of following the warp and undulation of the entire surface to be polished is reduced, and the global flatness tends to be reduced. On the other hand, if the cushion layer is too thick, the polishing pad as a whole tends to become soft, making stable polishing difficult. When laminating the cushion layer on the polishing layer, the thickness of the polishing pad is preferably about 0.3 to 5 mm.
  • CMP polishing method using the polishing pad of the present invention is performed by CMP
  • a CMP apparatus 10 having a circular rotating platen 2, a slurry supply nozzle 3, a holder 4, and a pad conditioner 6 shown in FIG. 1 is used.
  • the polishing pad 1 having the above-described polishing layer is attached to the surface of the rotating platen 2 with double-sided tape or the like.
  • the holder 4 supports the object 5 to be polished.
  • the rotating platen 2 is rotated in the direction indicated by the arrow (clockwise) by a motor (not shown). Further, the holder 4 is rotated in the direction indicated by the arrow (clockwise) by a motor (not shown) in the plane of the rotating surface plate 2 .
  • the pad conditioner 6 is also rotated in the direction indicated by the arrow (clockwise) by a motor (not shown) within the plane of the rotating platen 2 .
  • a CMP pad conditioner 6 having diamond particles fixed to the carrier surface by nickel electrodeposition or the like is pressed. Then, the polishing surface of the polishing pad 1 is conditioned. Conditioning adjusts the surface to be polished to a surface roughness suitable for polishing the surface to be polished.
  • the slurry 7 is supplied from the slurry supply nozzle 3 to the polishing surface of the rotating polishing pad 1 .
  • lubricating oil, coolant, etc. may be used together with the slurry, if necessary.
  • the slurry includes acidic slurry, alkaline slurry, and near-neutral slurry.
  • liquid media such as water and oil
  • a slurry used for CMP containing a base, an acid, a surfactant, an oxidizing agent such as a hydrogen peroxide solution, a reducing agent, a chelating agent, and the like is preferably used.
  • the object to be polished 5 fixed to the holder 4 and rotating is pressed against the polishing pad 1 in which the slurry 7 is spread evenly over the polishing surface of the polishing layer.
  • the polishing process is then continued until the desired flatness is obtained.
  • the finishing quality is affected by adjusting the pressing force applied during polishing and the speed of relative movement between the rotating platen 2 and the holder 4 .
  • the polishing conditions are not particularly limited, but in order to perform polishing efficiently, the rotational speed of each of the rotating surface plate and the holder is preferably 300 rpm or less, and the pressure applied to the object to be polished is such that scratches are generated after polishing. It is preferable to set it to 150 kPa or less so as not to During polishing, slurry is preferably continuously supplied to the polishing surface by a pump or the like. The amount of slurry to be supplied is not particularly limited, but it is preferable to supply so that the polishing surface is always covered with slurry.
  • the CMP described above can be suitably used for polishing various semiconductor materials such as silicon wafers.
  • Example 1 Polytetramethylene glycol (PTMG850) with a number average molecular weight of 850 as a polyol, polyethylene glycol (PEG600) with a number average molecular weight of 600 as a polyol, 1,9-nonanediol (ND) as a chain extender, and as a polyisocyanate 4,4′-diphenylmethane diisocyanate (MDI) of PTMG850:PEG600:ND:MDI in a mass ratio of 27.4:12.9:18.1:41.7 to prepare a prepolymer.
  • the obtained prepolymer was kneaded with a small kneader at 240° C.
  • thermoplastic polyurethane pellets were fed to a single screw extruder and extruded through a T-die to form a sheet. Then, the surface of the obtained sheet was ground to form a uniform sheet having a thickness of 2.0 mm, and then cut into a circular shape having a diameter of 740 mm to obtain a polishing layer sheet.
  • the obtained thermoplastic polyurethane and polishing layer sheet were evaluated as described later. Table 2 shows the results.
  • thermoplastic polyurethanes (non-foamed bodies) of Examples 2 to 17 and Comparative Examples 1 to 9 were produced in the same manner as in Example 1 except that the formulations shown in Table 1 were used to obtain sheets for polishing layers. Table 2 shows the evaluation results.
  • N% derived from polyisocyanate The nitrogen content (N%) derived from polyisocyanate was measured for the thermoplastic polyurethanes (non-foamed bodies) of Examples 1 to 17 and Comparative Examples 1 to 9 as follows. Table 1 shows the measurement results. First, the total nitrogen content was calculated by the elemental analysis method under the following conditions. ⁇ Apparatus: Fully automatic elemental analyzer 2400 series II type (equipped with an autosampler as standard equipment) manufactured by PerkinElmer Co., Ltd.
  • thermoplastic polyurethane and each polishing layer sheet obtained in Examples 1 to 17 and Comparative Examples 1 to 9 were evaluated according to the method described later.
  • thermoplastic polyurethanes obtained in Examples 1 to 17 and Comparative Examples 1 to 9 were placed so that at least one side was in contact with the polyimide film in order to obtain a smooth surface to be measured, and then sandwiched between two metal plates.
  • hot press molding machine desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.
  • Hot press molding was performed by preheating at a heating temperature of 230° C. for 2 minutes and then pressing for 1 minute with a press pressure such that the thickness would be 200 ⁇ m. Then, the two metal plates interposed with the thermoplastic polyurethane were removed from the hot press molding machine, cooled, and then the press-molded sheet was released.
  • the resulting press-molded sheet with a thickness of 200 ⁇ m was left under conditions of room temperature (23° C.) and 50% RH for 3 days.
  • the contact angle with water was measured using a DropMaster 500 manufactured by Kyowa Interface Science Co., Ltd. 2 seconds after 5 ⁇ L was dropped and 15 minutes after 2.5 ⁇ L of water at room temperature (23° C.) was dropped on the surface. .
  • the contact angle 2 seconds after dropping 2.5 ⁇ L of water on the surface is shown in Table 2 as “contact angle (immediately after)”.
  • A is the contact angle 15 minutes after dropping 2.5 ⁇ L of room temperature (23 ° C.) water
  • B is the contact angle immediately after dropping 2.5 ⁇ L of room temperature (23 ° C.) water.
  • the change was calculated by the following formula (1).
  • the calculated results are shown in Table 2 as "change in contact angle (after 15 minutes/immediately after)".
  • thermoplastic polyurethanes obtained in Examples 1 to 17 and Comparative Examples 1 to 9 were sandwiched between two metal plates and hot press molded with a hot press molding machine (desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.). . Hot press molding was performed by preheating at a heating temperature of 230° C. for 2 minutes and then pressing for 1 minute with a press pressure such that the thickness would be 500 ⁇ m. Then, the two metal plates interposed with the thermoplastic polyurethane were removed from the hot press molding machine, cooled, and then the press-molded sheet was released.
  • a hot press molding machine desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.
  • the resulting press-molded sheet having a thickness of 500 ⁇ m was measured for elongation at break (dry) using Autograph SHIMADZU AGS-H manufactured by Shimadzu Corporation under a tensile condition of 50 mm/min. Table 2 shows the measurement results.
  • thermoplastic polyurethanes obtained in Examples 1 to 17 and Comparative Examples 1 to 9 were sandwiched between two metal plates and hot press molded with a hot press molding machine (desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.). . Hot press molding was performed by preheating at a heating temperature of 230° C. for 2 minutes and then pressing for 1 minute with a press pressure such that the thickness would be 500 ⁇ m. Then, the two metal plates interposed with the thermoplastic polyurethane were removed from the hot press molding machine, cooled, and then the press-molded sheet was released.
  • a hot press molding machine desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.
  • the resulting press-molded sheet with a thickness of 500 ⁇ m was immersed in water at 50° C. for 48 hours to make it wet, and the elongation at break (wet) was measured using an Autograph SHIMADZU AGS-H manufactured by Shimadzu Corporation to 50 mm. / min. Table 2 shows the measurement results.
  • thermoplastic polyurethanes obtained in Examples 1 to 17 and Comparative Examples 1 to 9 were sandwiched between two metal plates and hot press molded with a hot press molding machine (desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.). . Hot press molding was performed by preheating at a heating temperature of 230° C. for 2 minutes and then pressing for 1 minute with a press pressure such that the thickness would be 500 ⁇ m. Then, the two metal plates interposed with the thermoplastic polyurethane were removed from the hot press molding machine, cooled, and then the press-molded sheet was released.
  • a hot press molding machine desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.
  • a test piece of 5.0 ⁇ 25 (mm) was cut out from the obtained press-molded sheet having a thickness of 500 ⁇ m.
  • a dynamic viscoelasticity measuring device (“Rheogel-E4000", manufactured by UBM Co., Ltd.)
  • the temperature dependence of the dynamic viscoelastic modulus of the cut test piece was measured at a frequency of 11 Hz in the range of -120 to 250 ° C. .
  • the temperature (tan ⁇ maximum value temperature) at which the loss tangent (tan ⁇ ) becomes maximum in the range of ⁇ 30 to 100° C. was obtained from the obtained chart of the temperature dependence of the dynamic viscoelastic modulus. Table 2 shows the results.
  • thermoplastic polyurethanes obtained in Examples 1 to 17 and Comparative Examples 1 to 9 was sandwiched between two metal plates and hot press molded with a hot press molding machine (desktop test press manufactured by Shindo Kinzoku Kogyo Co., Ltd.). . Hot press molding was performed by preheating at a heating temperature of 230° C. for 2 minutes and then pressing for 1 minute with a press pressure such that the thickness would be 500 ⁇ m. Then, the two metal plates interposed with the thermoplastic polyurethane were removed from the hot press molding machine, cooled, and then the press-molded sheet was released. A No.
  • a double-sided pressure-sensitive adhesive sheet was used to bond a cushion layer to the back surface of each of the polishing layer sheets obtained in Examples 1 to 17 and Comparative Examples 1 to 9.
  • As the cushion layer "PORON H48” manufactured by INOAC CORPORATION, which is a foamed polyurethane sheet with a thickness of 0.8 mm, was used.
  • polishing pad was mounted on a polishing apparatus "F-REX300" manufactured by Ebara Corporation. Then, a slurry prepared by diluting Cabot Microelectronics' slurry "SEMI-SPERSE25" by 2 times was prepared, and a platen rotation speed of 100 rpm, a head rotation speed of 99 rpm, and a polishing pressure of 20.0 kPa were applied at a speed of 200 mL/min. A silicon wafer having a diameter of 12 inches and having a silicon oxide film having a thickness of 2000 nm on its surface was polished for 60 seconds while supplying the slurry to the polishing surface of the polishing pad.
  • polishing speed Then, the film thickness of the silicon oxide film before and after polishing of the tenth silicon wafer was measured at 49 points in the wafer surface, and the polishing rate (nm/min) at each point was determined. Specifically, the average value of the polishing speeds at 49 points was taken as the polishing speed (nm/min). Table 2 shows the obtained polishing rates (nm/min).
  • polishing temperature (° C.) in the polishing of silicon wafers (60 seconds/wafer) was measured using a polishing temperature measuring device built into the polishing device “F-REX300” manufactured by Ebara Corporation, and the maximum polishing temperature (° C.) ).
  • Table 2 shows the maximum polishing temperatures (°C) obtained.
  • thermoplastic polyurethane for a polishing layer that constitutes a polishing layer that can be polished at a high polishing rate while suppressing the occurrence of defects by lowering the polishing temperature, It can be seen that a polishing layer and a polishing pad can be provided using it.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
  • Mechanical Treatment Of Semiconductor (AREA)
PCT/JP2022/035870 2021-09-30 2022-09-27 研磨層用熱可塑性ポリウレタン、研磨層、及び研磨パッド Ceased WO2023054331A1 (ja)

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US18/695,389 US20240399530A1 (en) 2021-09-30 2022-09-27 Thermoplastic polyurethane for polishing layer, polishing layer, and polishing pad
EP22876197.9A EP4410478A4 (en) 2021-09-30 2022-09-27 Thermoplastic Polyurethan for Polishing Coat, Polishing Coat and Polishing Pad
JP2023551511A JPWO2023054331A1 (https=) 2021-09-30 2022-09-27
KR1020247009870A KR20240087742A (ko) 2021-09-30 2022-09-27 연마층용 열가소성 폴리우레탄, 연마층, 및 연마 패드
IL311635A IL311635A (en) 2021-09-30 2022-09-27 Thermoplastic polyurethane for the polishing layer, the polishing layer, and the polishing pad
CN202280064671.7A CN117980110A (zh) 2021-09-30 2022-09-27 抛光层用热塑性聚氨酯、抛光层及抛光垫

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