WO2016067588A1 - 研磨層用非多孔性成形体,研磨パッド及び研磨方法 - Google Patents
研磨層用非多孔性成形体,研磨パッド及び研磨方法 Download PDFInfo
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- WO2016067588A1 WO2016067588A1 PCT/JP2015/005371 JP2015005371W WO2016067588A1 WO 2016067588 A1 WO2016067588 A1 WO 2016067588A1 JP 2015005371 W JP2015005371 W JP 2015005371W WO 2016067588 A1 WO2016067588 A1 WO 2016067588A1
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- polishing
- thermoplastic polyurethane
- polishing layer
- porous molded
- polishing pad
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Images
Classifications
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- B24B37/11—Lapping tools
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- B24B37/24—Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture 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
- H01L21/18—Manufacture 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
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture 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
- H01L21/18—Manufacture 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
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment 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
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/30625—With simultaneous mechanical treatment, e.g. mechanico-chemical polishing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Definitions
- the present invention relates to a polishing pad, and more particularly to a polishing pad for polishing a semiconductor wafer, a semiconductor device, a silicon wafer, a hard disk, a glass substrate, an optical product, or various metals.
- CMP Chemical mechanical polishing
- a polishing method used for mirror-finishing a semiconductor wafer or planarizing the surface of an insulating film or a conductor film of a semiconductor device.
- CMP is a method in which the surface of a material to be polished such as a wafer is polished with a polishing pad using a polishing slurry containing abrasive grains and a reaction liquid (hereinafter also simply referred to as slurry).
- non-woven polishing pads have been widely used as polishing pads for CMP.
- the nonwoven fabric type polishing pad is a flexible polishing pad including a nonwoven fabric impregnated with polyurethane.
- Nonwoven polishing pads have the advantage of good contact with the material to be polished because they are flexible.
- the nonwoven fabric since the nonwoven fabric has voids, it also has the advantage of good slurry retention.
- the nonwoven fabric type polishing pad is flexible, it has a disadvantage in that the performance of flattening the surface to be polished (referred to as flattening property) is low.
- the nonwoven fabric type polishing pad also has a drawback that it becomes easy to cause scratches on the surface to be polished when the voids of the nonwoven fabric are clogged with abrasive grains or polishing scraps. Furthermore, when abrasive grains or polishing debris penetrates deeply into the voids of the nonwoven fabric, it cannot be sufficiently removed by washing, thereby shortening the life.
- a polishing pad mainly composed of a polymer foam having a closed cell structure is known as a polishing pad of a type different from the nonwoven fabric type polishing pad.
- a polishing pad mainly composed of a polymer foam has a higher rigidity than a non-woven fabric type polishing pad, and therefore has excellent flatness.
- the polishing pad mainly composed of a polymer foam has a closed cell structure, it is difficult for abrasive grains and polishing debris to penetrate deeply into the void as in the case of a non-woven type polishing pad. Therefore, it is relatively easy to remove abrasive grains and polishing debris by cleaning, so that the life is relatively long.
- polishing pad mainly composed of a polymer foam
- a foamed polyurethane molded product obtained by casting and molding a two-component curable polyurethane as disclosed in Patent Documents 1 to 6 below is polished. Polishing pads provided as layers are known.
- the foamed polyurethane molded body is preferably used as a polishing layer from the viewpoint of excellent wear resistance.
- polishing pads used for planarization of semiconductor devices are required to have higher planarity.
- a polishing pad with high flatness is a polishing pad that has a high polishing rate for a portion to be polished and a low polishing rate for a portion that should not be polished.
- a polishing pad with high flatness is required to have high hardness.
- a polishing pad provided with a foamed polyurethane molded body as a polishing layer has high flatness because the hardness of the polishing layer is relatively high.
- Patent Documents 7 and 8 below disclose high-hardness polishing pads mainly composed of non-foamed resin.
- JP 2000-178374 A Japanese Patent Laid-Open No. 2000-248034 JP 2001-89548 A Japanese Patent Laid-Open No. 11-322878 JP 2002-371154 A International Publication No. 2007/034980 JP 2014-038916 A JP 2009-101487 A
- a polishing pad used in CMP is usually formed with grooves and holes (hereinafter simply referred to as recesses) for supplying the slurry uniformly and sufficiently to the surface to be polished of the material to be polished. Such recesses are useful for discharging polishing scraps that cause scratches and preventing wafer breakage due to adsorption of the polishing pad.
- the material to be polished or the conditioner When recesses are formed on the polishing surface of a hard polishing layer mainly composed of non-porous resin (non-foamed resin), the material to be polished or the conditioner repeatedly contacts the corners (edges, shoulders) of the recesses for a long time. As a result, there is a problem that burrs are generated over time in the corner portion. The generated burrs gradually close the recesses and gradually reduce the amount of slurry supplied. As a result, there has been a problem that the polishing rate and the polishing uniformity are gradually reduced.
- An object of the present invention is to provide a polishing layer of a polishing pad in which the generation of burrs at the corners of recesses formed on the polishing surface is suppressed.
- thermoplastic polyurethane having low rebound resilience and high toughness When the molded article of thermoplastic polyurethane having low rebound resilience and high toughness is used as a polishing layer, the present inventors easily stretch the thermoplastic polyurethane by the force repeatedly applied to the corners of the recesses, and burrs. I noticed that it was likely to occur. Moreover, when thermoplastic polyurethane which has a soft segment and a hard segment with good compatibility was used, the knowledge that a burr
- one aspect of the present invention is a non-porous molded body of thermoplastic polyurethane, and thermoplastic polyurethane has a maximum loss tangent (tan ⁇ ) in the range of ⁇ 70 to ⁇ 50 ° C. of 4.00 ⁇ 10. It is a non-porous molded body for polishing layer (hereinafter also simply referred to as a non-porous molded body) that is ⁇ 2 or less. When such a non-porous molded body is used as the polishing layer, burrs are less likely to occur at the corners of the recesses formed on the polished surface even after long-time CMP polishing.
- the present inventors presume a mechanism for suppressing the generation of burrs in a polishing pad using such a non-porous molded body as a polishing layer as follows.
- a thermoplastic polyurethane having a high tan ⁇ value in a low temperature region is easily deformed and has high toughness.
- the polished surface is subjected to high frequency impacts, for example, by contacting with the diamond particles of the conditioner.
- the damping characteristics of the polishing pad against high frequency impact correlate with tan ⁇ in the low temperature region.
- a thermoplastic polyurethane having a low tan ⁇ value in the low temperature region has low impact resistance, low toughness, and is brittle.
- the generation of burrs is suppressed by the abrasion of the thermoplastic polyurethane at the corners of the recesses before the burrs are generated. Then, according to the polishing layer in which the generation of burrs is suppressed, the slurry can be supplied uniformly over the entire polishing surface for a long time. Therefore, the polishing rate at each point becomes uniform on the surface to be polished of a material to be polished such as a wafer. As a result, polishing with excellent polishing uniformity is realized.
- thermoplastic polyurethane is obtained by polymerizing a polymer diol having a number average molecular weight of 650 to 1400, an organic diisocyanate, and a chain extender, and the nitrogen content ratio derived from the isocyanate group of the organic diisocyanate is 5.7 to 6 It is preferably 5% by mass.
- the thermoplastic polyurethane preferably has a laser transmittance of 70% or more with respect to a laser wavelength of 660 nm in a sheet having a thickness of 0.5 mm.
- Such thermoplastic polyurethane has high compatibility between the soft segment and the hard segment. According to such a thermoplastic polyurethane, it is easy to obtain a non-porous molded body of thermoplastic polyurethane having a maximum loss tangent value in the range of ⁇ 70 to ⁇ 50 ° C. of 4.00 ⁇ 10 ⁇ 2 or less.
- the laser transmittance is 70% or more, an optical means for determining a polishing end point while polishing a surface to be polished such as a wafer or inspecting the material to be polished is used. It is preferable because it is suitable for inspection.
- thermoplastic polyurethane has a tensile modulus of 130 to 800 MPa after being saturated and swelled with hot water at 50 ° C., so that a polishing layer having a hardness high enough to prevent generation of scratches during polishing can be obtained. It is preferable from the point.
- the hardness of the polishing pad decreases with time, the flatness tends to decrease and the polishing efficiency tends to decrease.
- thermoplastic polyurethane sheet has a contact angle with water of 80 degrees or less from the viewpoint of hardly generating scratches.
- thermoplastic polyurethane is calculated from the following formula: A / B ⁇ 100 (A is the tensile elastic modulus when saturated and swollen with hot water at 50 ° C., B is the tensile elastic modulus when not saturated and swollen), It is preferable that the retention rate at the time of water saturation swelling of the tensile elastic modulus is 55% or more from the viewpoint that the polishing characteristics hardly change with time during polishing.
- another aspect of the present invention is a polishing pad comprising any of the above-described non-porous molded bodies for a polishing layer as a polishing layer. According to such a polishing pad, polishing excellent in polishing uniformity can be realized.
- the polishing pad includes the above-described polishing layer and a cushion layer having a hardness lower than the hardness of the polishing layer laminated on the polishing layer. It is preferable from the viewpoint that a polished surface excellent in balance between the property and (local planarization) can be formed.
- Another aspect of the present invention is a chemical mechanical polishing method using the above-described polishing pad.
- FIG. 1 is an explanatory diagram illustrating CMP using a polishing pad.
- FIG. 2 is a scanning electron microscope (SEM) photograph of a cross section of the polishing layer after performing an 8-hour accelerated dress test using the polishing pad produced in Example 1.
- FIG. 3 is an SEM photograph of a cross-section of the polishing layer after performing an 8-hour accelerated dress test using the polishing pad manufactured in Comparative Example 3.
- FIG. 4 is a chart showing measurement results of loss tangent (tan ⁇ ) including a range of 70 to ⁇ 50 ° C. of the thermoplastic polyurethane used in Example 1 and Comparative Example 3.
- the non-porous molded body for polishing layer of the present embodiment is a non-porous molded body (non-foamed molded body) of thermoplastic polyurethane, and has a maximum loss tangent (tan ⁇ ) in the range of ⁇ 70 to ⁇ 50 ° C.
- the molded product has a value of 4.00 ⁇ 10 ⁇ 2 or less.
- the maximum value of the loss tangent in the range of ⁇ 70 to ⁇ 50 ° C. is 4.00 ⁇ 10 ⁇ 2 or less, 3.50 ⁇ 10 ⁇ 2 or less, and further 3.00 ⁇ It is preferably 10 ⁇ 2 or less.
- a thermoplastic polyurethane has a high compatibility between the soft segment and the hard segment, a high impact resilience, and a low toughness thermoplastic polyurethane.
- the upper limit of the maximum value of the loss tangent in the range of ⁇ 70 to ⁇ 50 ° C. of the thermoplastic polyurethane exceeds 4.00 ⁇ 10 ⁇ 2 , the resilience is low and the thermoplastic polyurethane has high toughness.
- the loss tangent of the thermoplastic polyurethane in the range of ⁇ 70 to ⁇ 50 ° C. is preferably 2.00 ⁇ 10 ⁇ 2 or more.
- a thermoplastic polyurethane having an appropriate impact resilience, toughness and hardness can be obtained. As a result, the polishing uniformity tends to improve.
- thermoplastic polyurethane having a maximum loss tangent value in the range of ⁇ 70 to ⁇ 50 ° C. of 4.00 ⁇ 10 ⁇ 2 or less is obtained by polymerizing a polymer diol having a number average molecular weight of 650 to 1400, an organic diisocyanate, and a chain extender It is obtained by using a thermoplastic polyurethane having a nitrogen content derived from urethane bonds of 5.7 to 6.5% by mass.
- the number average molecular weight of the polymer diol used for polymerization of the thermoplastic polyurethane is preferably 650 to 1400, more preferably 800 to 1200, and particularly preferably 800 to 1000.
- the number average molecular weight of the polymer diol is too low, the hardness and the tensile elastic modulus are lowered, and the flatness of the polishing layer tends to be lowered.
- the number average molecular weight of the polymer diol is too high, the soft segment and the hard segment are phase-separated, and the maximum value of the loss tangent exceeds 4.00 ⁇ 10 ⁇ 2 , resulting in low rebound resilience and high A tough thermoplastic polyurethane is easily obtained.
- the number average molecular weight of the polymer diol is a number average molecular weight calculated based on the hydroxyl value measured according to JIS K1557.
- polymer diol examples include polyether diol, polyester diol, and polycarbonate diol.
- polyether diol examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polymethyltetramethylene glycol, polyoxypropylene glycol, and glycerin-based polyalkylene ether glycol. These may be used alone or in combination of two or more. Among these, polyethylene glycol and polytetramethylene glycol are particularly preferable.
- polyester diol examples include those obtained by directly esterifying or transesterifying an ester-forming derivative such as dicarboxylic acid or its ester or anhydride and a low molecular weight diol.
- dicarboxylic acids examples include oxalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid
- Aliphatic dicarboxylic acids having 2 to 12 carbon atoms such as 1,3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid
- Aliphatic dicarboxylic acids such as dimerized aliphatic dicarboxylic acids having 14 to 48 carbon atoms (dimer acid) and hydrogenated products (hydrogenated dimer acid) obtained by dimerizing the obtained unsaturated fatty acid
- 1,4-cyclohexanedicarboxylic acid examples thereof include alicyclic dicarbox
- dimer acid and hydrogenated dimer acid trade names “Pripol 1004”, “Plipol 1006”, “Plipol 1009”, “Plipol 1013” and the like manufactured by Unikema Corporation may be mentioned. These may be used alone or in combination of two or more.
- low molecular diol examples include, for example, 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-octanediol , 1,9-nonanediol, 1,10-decanediol, and the like; and cycloaliphatic diols such as cyclohexanedimethanol and cyclohexanediol. These may be used alone or in combination of two or more. Of these, diols having 6 to 12 carbon atoms, diols having 8 to 10 carbon atoms, and particularly diols having 9 carbon atoms are preferable.
- polycarbonate diol examples include those obtained by reacting a carbonate compound and a low molecular diol.
- the carbonate compound examples include dialkyl carbonates such as dimethyl carbonate and diethyl carbonate, alkylene carbonates such as ethylene carbonate, diaryl carbonates such as diphenyl carbonate, and the like.
- the low molecular diol examples include the same low molecular diol as described above. These may be used alone or in combination of two or more.
- the polymer diols may be used alone or in combination of two or more.
- polyether diols selected from polyethylene glycol and polytetramethylene glycol; poly (nonamethylene adipate), poly (2-methyl-1,8-octamethylene adipate), poly (2-methyl-1,8 -Octamethylene-co-nonamethylene adipate), polyester diol selected from poly (methylpentane adipate); or at least one selected from derivatives thereof is particularly preferable from the viewpoint of excellent hydrophilicity.
- organic diisocyanate used for polymerization of thermoplastic polyurethane organic diisocyanate conventionally used for polymerization of thermoplastic polyurethane is used without particular limitation. Specific examples thereof include, for example, ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2,2,4- or 2,4,4-trimethylhexamethylene diisocyanate, dodecamethylene diisocyanate, isophorone diisocyanate, isopropylidenebis.
- the chain extender used for polymerization of thermoplastic polyurethane it has two or more active hydrogen atoms that can react with isocyanate groups, which is conventionally used for polymerization of thermoplastic polyurethane, and preferably has a molecular weight of 300 or less. These are low molecular compounds. Specific examples thereof include, for example, ethylene glycol, diethylene glycol, propylene glycol, 2,2′-diethyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, and 2,3-butanediol.
- At least one selected from 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6-hexanediol, and cyclohexanedimethanol is preferable.
- the blending ratio of each component of the monomeric polymer diol, the chain extender, and the organic diisocyanate used for the polymerization of the thermoplastic polyurethane is appropriately selected in consideration of physical properties such as intended wear resistance.
- the isocyanate group contained in the organic diisocyanate is 0.95 to 1.3 mole, more preferably 0.96 to 1 with respect to 1 mole of active hydrogen atoms contained in the polymer diol and the chain extender.
- a ratio of .10 mol, particularly 0.97 to 1.05 mol is preferable from the viewpoint of excellent mechanical strength, abrasion resistance, productivity of thermoplastic polyurethane and storage stability. If the ratio of isocyanate groups is too low, the mechanical strength and wear resistance of the non-porous molded product tend to decrease, and if it is too high, the productivity and storage stability of thermoplastic polyurethane tend to decrease. There is.
- thermoplastic polyurethane in this embodiment uses, for example, a monomer including a high molecular diol having a number average molecular weight of 650 to 1400, an organic diisocyanate, and a chain extender, and a known prepolymer method or one-shot method. It is obtained by polymerization by the urethanization reaction used.
- a method is used in which a single-screw or multi-screw extruder is used for continuous melt polymerization while the above-mentioned monomers are melt-mixed in the substantial absence of a solvent.
- the nitrogen content derived from the isocyanate group of the organic diisocyanate in the thermoplastic polyurethane is preferably 5.7 to 6.5% by mass, more preferably 5.7 to 6.1% by mass.
- the nitrogen content derived from the isocyanate group of the organic diisocyanate is preferably 5.7 to 6.5% by mass, more preferably 5.7 to 6.1% by mass.
- the nitrogen content derived from the isocyanate group of the organic diisocyanate is too low, when a non-porous molded body of thermoplastic polyurethane is used as the polishing layer, it tends to be too soft and the flatness and polishing efficiency tend to decrease. is there.
- the nitrogen content derived from the isocyanate group of the organic diisocyanate is too high, the maximum loss tangent at ⁇ 70 to ⁇ 50 ° C. tends to exceed 4.00 ⁇ 10 ⁇ 2 .
- the thermoplastic polyurethane preferably has a laser transmittance of 70% or more, further 80% or more, particularly 90% or more for a laser wavelength of 660 nm in a sheet having a thickness of 0.5 mm.
- the laser transmittance for the laser wavelength of 660 nm is as follows: laser wavelength (660 nm), laser output (310 ⁇ W), distance between detection head and output head (100 mm), sample position (intermediate point between detection head and output head). This is the value when measured under conditions.
- the maximum value of loss tangent at ⁇ 70 to ⁇ 50 ° C. is more than 4.00 ⁇ 10 ⁇ 2 because the soft polyurethane hard segment and the hard segment are easily phase separated. It tends to be higher.
- thermoplastic polyurethane having low rebound resilience and high toughness, and there is a tendency that burrs that close the recesses formed on the polished surface tend to occur over time. Further, when the laser transmittance is too low, it tends to be difficult to use for inspection of a material to be polished and detection of a polishing end point.
- the thermoplastic polyurethane preferably has a tensile modulus of 130 to 800 MPa, further 180 to 750 MPa, particularly 230 to 700 MPa, and more preferably 280 to 650 MPa after being saturated and swelled with water at 50 ° C.
- a tensile modulus of 130 to 800 MPa, further 180 to 750 MPa, particularly 230 to 700 MPa, and more preferably 280 to 650 MPa after being saturated and swelled with water at 50 ° C.
- the polishing layer tends to be soft and flatness and polishing efficiency tend to decrease.
- scratches tend to be generated on the surface to be polished.
- thermoplastic polyurethane in the present embodiment is Following formula (1): A / B ⁇ 100 (A is the tensile elastic modulus when saturated and swollen with hot water at 50 ° C., B is tensile elastic modulus when not saturated and swollen with hot water at 50 ° C.) (1) It is preferable that the retention rate at the time of water saturation swelling of the tensile elastic modulus calculated by the above is 55% or more, more preferably 60% or more, and particularly preferably 75% or more. If the retention rate of the tensile elastic modulus during water saturation swelling is too low, the property change of the polishing layer due to moisture is large. For example, the polishing rate is high when the pad is left wet for several hours to several days after polishing. It tends to decrease.
- the non-porous molded body of the present embodiment is preferably produced as a sheet by extruding or injection-molding the above-described thermoplastic polyurethane that does not contain a component such as a foaming agent using a T die.
- a sheet obtained by extrusion molding using a T-die is preferable because a sheet having a uniform thickness can be obtained.
- the thickness of the sheet is not particularly limited, and is adjusted as appropriate according to the layer configuration and application of the polishing pad. Specifically, it is preferably 1.5 to 3.0 mm, more preferably 1.7 to 2.8 mm, and particularly preferably 2.0 to 2.5 mm.
- the sheet preferably has a contact angle with water of 80 degrees or less, more preferably 75 degrees or less, and particularly preferably 70 degrees or less. When the contact angle with water is too high, scratches tend to occur on the surface to be polished.
- the hardness of the sheet is preferably 55 or more in JIS-D hardness, more preferably 60 to 80, and particularly preferably 65 to 75. If the JIS-D hardness is too low, the local flattening property tends to decrease, and if it is too high, scratches tend to occur.
- the polishing pad of the present embodiment includes a polishing layer formed by cutting out a circular sheet or the like from the sheet of the non-porous molded body as described above.
- the polishing pad may be a single-layer polishing pad of a non-porous molded sheet or a multilayer polishing pad in which a cushion layer is laminated on a non-porous molded sheet.
- the cushion layer is preferably a layer having a hardness lower than that of the polishing layer.
- the hard polishing layer can easily follow the local unevenness of the surface to be polished, and the warpage and undulation of the entire polishing material Since the cushion layer follows, it is possible to perform polishing with a good balance between global flatness and local flatness.
- the material used for the cushion layer include a composite in which a known nonwoven fabric is impregnated with polyurethane; rubber such as natural rubber, nitrile rubber, polybutadiene rubber, and silicone rubber; polyester-based thermoplastic elastomer, polyamide-based thermoplastic elastomer And thermoplastic elastomers such as fluorine-based thermoplastic elastomers; foamed plastics; polyurethane and the like.
- polyurethane having a foamed structure is particularly preferable from the viewpoint of appropriate flexibility.
- the thickness of the cushion layer is not particularly limited, but is preferably about 0.3 to 1.2 mm, and more preferably about 0.5 to 1.0 mm.
- the cushion layer is too thin, the followability to the warp and undulation of the entire workpiece is lowered, and the global flatness of the polishing pad tends to be lowered.
- the cushion layer is too thick, the entire polishing pad tends to be soft and stable polishing becomes difficult.
- concavities such as grooves and holes are formed concentrically.
- Such a concave portion is useful for discharging polishing debris that causes scratches and preventing wafer breakage due to adsorption of the polishing pad.
- the method for forming the recess on the polished surface is not particularly limited. Specifically, for example, the surface of the sheet of the non-porous molded body is cut so as to form a predetermined concave pattern on the polishing surface of the polishing layer, or is transferred with a mold during injection molding. And a method of forming a recess by a method such as forming a recess by stamping with a heated mold.
- the distance between the grooves is preferably 2.0 to 50 mm, more preferably 5.5 to 30 mm, and particularly preferably 6.0 to 15 mm.
- the groove width is preferably about 0.1 to 3.0 mm, more preferably about 0.4 to 2.0 mm.
- the depth of the groove is preferably about 0.2 to 1.8 mm, more preferably about 0.4 to 1.5 mm.
- the cross-sectional shape of the groove for example, a shape such as a rectangle, a trapezoid, a triangle, a semicircle, or the like is appropriately selected according to the purpose.
- burrs may occur at the corner portion when the material to be polished or the conditioner repeatedly contacts the corner portion (shoulder portion, end portion) of the concave portion for a long time. Such burrs gradually close the recesses and gradually reduce the amount of slurry supplied. As a result, the polishing rate and polishing uniformity are gradually reduced.
- the polishing layer using the non-porous molded body of thermoplastic polyurethane according to the present embodiment suppresses the generation of burrs that block such recesses.
- CMP using the polishing pad of this embodiment.
- a CMP apparatus 20 including a circular rotary platen 11, a slurry supply nozzle 12, a carrier 13, and a pad conditioner 14 as shown in FIG. 1 is used.
- a polishing pad 10 is affixed to the surface of the rotating surface plate 11 with a double-sided tape or the like.
- the carrier 13 supports the material 15 to be polished.
- the rotating surface plate 11 is rotated in a direction indicated by an arrow by a motor (not shown). Further, the carrier 13 is rotated in a direction indicated by an arrow by a motor (not shown) within the surface of the rotating surface plate 11.
- the pad conditioner 14 is also rotated in the direction of the arrow, for example, by a motor (not shown) within the surface of the rotating surface plate 11.
- the rotating pad conditioner 14 is pressed against the polishing surface of the polishing pad 10 that is fixed to the rotating platen 11 and rotating, and the polishing surface of the polishing pad 10 is conditioned.
- the pad conditioner for example, a conditioner in which diamond particles are fixed to the carrier surface by nickel electrodeposition or the like is used. In this way, the polishing surface of the polishing layer of the polishing pad 10 is adjusted to a surface roughness suitable for polishing the surface to be polished.
- the polishing slurry 16 is supplied from the slurry supply nozzle 12 to the polishing surface of the polishing layer of the rotating polishing pad 10.
- the polishing slurry 16 includes, for example, a liquid medium such as water or oil; a polishing agent such as silica, alumina, cerium oxide, zirconium oxide, silicon carbide; a base, an acid, a surfactant, an oxidizing agent, a reducing agent, a chelating agent, and the like. Contains. Further, when performing CMP, a lubricating oil, a coolant, or the like may be used in combination with the polishing slurry, if necessary. Then, the polishing material 15 fixed to the carrier 13 and rotating is pressed against the polishing pad 10 evenly wetted by the polishing slurry 16. Then, the polishing process is continued until a predetermined flatness is obtained. The quality of the finished product is affected by adjusting the pressing force applied during polishing and the speed of relative movement between the rotating surface plate 11 and the carrier 13.
- a polishing agent such as silica, alumina, cerium oxide, zirconium oxide, silicon carbide
- a base
- Polishing conditions are not particularly limited, but in order to perform polishing efficiently, the rotation speed of each of the surface plate and the substrate is preferably low rotation of 300 rpm or less.
- the pressure applied to the substrate is preferably 150 kPa or less in order to suppress the generation of scratches. Further, it is preferable to continuously supply the polishing slurry on the polishing surface while polishing.
- the supply amount of the polishing slurry is preferably such an amount that the entire polishing surface is always wetted with the polishing slurry.
- the material to be polished is thoroughly washed with running water, and then water droplets adhering to the material to be polished are removed by using a spin dryer or the like.
- a spin dryer or the like By polishing the surface to be polished with the polishing slurry, a flat surface can be obtained over the entire surface to be polished.
- Such CMP according to the present embodiment is preferably used for polishing in manufacturing processes of various semiconductor devices and MEMS (Micro Electro Mechanical Systems).
- materials to be polished include, for example, semiconductor wafers such as silicon wafers, silicon oxides, and silicon oxyfluorides; inorganic insulation such as silicon oxide films, glass films, and silicon nitride films formed on wiring boards having predetermined wirings Film; film mainly containing polysilicon, aluminum, copper, titanium, titanium nitride, tungsten, tantalum, tantalum nitride, etc .; optical glass such as photomask, lens, prism; inorganic conductive film such as tin-doped indium oxide (ITO); Optical integrated circuits composed of glass and crystalline materials, optical switching elements, optical waveguides, optical fiber end faces, scintillator and other optical single crystals; solid laser single crystals; blue laser LED sapphire substrates; silicon carbide, gallium phosphide Semiconductor single crystals such as gallium
- thermoplastic polyurethane A was obtained by knead
- thermoplastic polyurethane A was evaluated by the following evaluation methods.
- Thermoplastic polyurethane A was sandwiched between two metal plates and subjected to hot press molding with a hot press molding machine (desktop test press manufactured by Shinto Kogyo Co., Ltd.).
- a hot press molding machine desktop test press manufactured by Shinto Kogyo Co., Ltd.
- pressing was performed for 1 minute at a pressing pressure such that the thickness became 300 ⁇ m.
- the press molding sheet was released. The obtained press-molded sheet was dried in a vacuum dryer at 60 ° C. for 16 hours.
- test piece of 5.0x25 (mm) was cut out from the press-molded sheet.
- DVE Rheospectrer Rheology a dynamic viscoelasticity measuring device
- the maximum value of the loss tangent (tan ⁇ ) in the range of ⁇ 70 to ⁇ 50 ° C. was determined from the obtained temperature dependence chart of the dynamic viscoelastic modulus.
- a chart of the temperature dependence of the dynamic viscoelastic modulus is shown in FIG.
- thermoplastic polyurethane sheet A press-molded sheet was obtained in the same manner as the method prepared in the loss tangent measurement except that the thickness was changed to 0.5 mm (500 ⁇ m). And the press molding sheet
- -Spectral transmittance measuring device "U-4000Spectrometer” manufactured by Hitachi, Ltd. ⁇ Laser wavelength: 660 nm ⁇ Laser output: 310 ⁇ W ⁇ Detection head output head distance: 10cm ⁇ Measurement position of test piece: Intermediate position between detection head and output head
- a No. 2 type test piece (JISK7113) was punched from the same press-molded sheet used in the measurement of loss tangent. Then, it was left for 3 days under conditions of 20 ° C. and 65% RH to adjust the state. On the other hand, another No. 2 type test piece was saturated and swollen with water by immersing it in warm water at 50 ° C. for 48 hours. And after wiping off the water
- tensile elasticity modulus was measured using each No. 2 type
- the tensile elastic modulus after saturation swelling with water is A
- the tensile elastic modulus at drying that is not saturated and swollen with water is B.
- the retention of tensile elastic modulus at the time of water swelling is expressed by the following formula (1).
- thermoplastic polyurethane B was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- the thermoplastic polyurethane C was obtained by kneading the obtained prepolymer with a small kneader for 5 minutes under the conditions of
- thermoplastic polyurethane C was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- a prepolymer was prepared by mixing.
- the thermoplastic polyurethane D was obtained by knead
- thermoplastic polyurethane D was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- thermoplastic polyurethane E was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- thermoplastic polyurethane F was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- FIG. 3 shows a scanning electron microscope (SEM) photograph of the cross section of the polishing pad after the accelerated dress test was performed using the polishing pad manufactured in Comparative Example 3.
- FIG. 4 shows a temperature dependence chart of the dynamic viscoelastic modulus.
- PNOA2000 poly (2-methyl-1,8-octamethylene-co-nonamethyleneadipate) diol
- CHDM 1,4-cyclohexanedimethanol
- BD 1,4-cycl
- thermoplastic polyurethane G was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
- a polymer was prepared.
- the thermoplastic polyurethane H was obtained by kneading the obtained prepolymer with a small kneader for 5 minutes under the conditions of 240 ° C. and screw rotation speed of 100 rpm.
- thermoplastic polyurethane H was used instead of thermoplastic polyurethane A.
- the results are shown in Table 1.
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Abstract
Description
下記式(1):
A/B×100
(Aは50℃の温水で飽和膨潤させたときの引張弾性率、Bは50℃の温水で飽和膨潤させていないときの引張弾性率)・・・(1)
により算出される、引張弾性率の水飽和膨潤時保持率が55%以上、さらには60%以上、とくには75%以上であることが好ましい。引張弾性率の水飽和膨潤時保持率が低すぎる場合には、水分による研磨層の特性変化が大きく、例えば研磨終了後、数時間~数日間、湿潤状態でパッドを放置した場合に研磨速度が低下しやすくなる傾向がある。
CMPにおいては、例えば、図1に示すような円形の回転定盤11と、スラリー供給ノズル12と、キャリア13と、パッドコンディショナー14とを備えたCMP装置20が用いられる。回転定盤11の表面に、研磨パッド10が両面テープ等により貼付けられている。また、キャリア13は被研磨材15を支持している。
数平均分子量850のポリテトラメチレングリコール(PTMG850)、1,4-ブタンジオール(BD)、及び4,4'-ジフェニルメタンジイソシアネート(MDI)を、PTMG850:BD:MDI=32.5:15.6:51.9(質量比)の割合で混合し、そのプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンAを得た。そして、熱可塑性ポリウレタンAを以下のような評価方法により評価した。
熱可塑性ポリウレタンAを2枚の金属板の間に挟み、熱プレス成形機((株)神藤工業所製の卓上用テストプレス)で熱プレス成形した。熱プレス成形は、加熱温度230℃で2分間予熱した後、厚さ300μmになるようなプレス圧で1分間プレスした。そして、熱プレス成形機から熱可塑性ポリウレタンAを介在させた2枚の金属板を取り出して冷却した後、プレス成形シートを離型させた。得られたプレス成形シートを減圧乾燥機内で60℃×16時間乾燥した。そして、プレス成形シートから5.0×25(mm)の試験片を切り出した。切り出した試験片を動的粘弾性測定装置(DVEレオスペクトラー(株)レオロジー製)を用いて、-120~250℃の範囲において周波数1.59Hzで動的粘弾性率の温度依存性を測定した。そして、得られた動的粘弾性率の温度依存性のチャートから-70~-50℃の範囲における損失正接(tanδ)の最大値を求めた。動的粘弾性率の温度依存性のチャートを図4に示す。
厚さ0.5mm(500μm)に変更した以外は、損失正接の測定において作成した方法と同様にしてプレス成形シートを得た。そして、プレス成形シートを所定の大きさに切り出し、波長660nmの光透過率を下記の条件で測定した。
・分光透過率測定装置 :(株)日立製作所製の「U-4000Spectrometer」
・レーザー波長 :660nm
・レーザー出力 :310μW
・検出ヘッド出力ヘッド間距離:10cm
・試験片の測定位置 :検出ヘッドと出力ヘッドとの中間位置
損失正接の測定において用いたものと同様のプレス成形シートから2号型試験片(JISK7113)を打ち抜いた。そして、20℃、65%RHの条件下に3日間放置して状態調整した。
一方、別の2号型試験片を50℃の温水に48時間浸漬することにより水で飽和膨潤させた。そして、温水から取り出した2号型試験片の表面の水分を拭き取った後、20℃、65%RHの条件下に3日間放置して状態調整した。
そして、状態調整されたそれぞれの2号型試験片を用いて引張弾性率を測定した。引張弾性率の測定は、いずれもインストロン社製3367を用い、環境条件20℃,65%RH、チャック間距離40mm、引張速度500mm/分、N=6本の条件で行った。
そして、水で飽和膨潤させた後の引張弾性率をA、水で飽和膨潤させていない乾燥時の引張弾性率をBとして、水膨潤時の引張弾性率の保持率を、下記式(1):
A/B×100・・・(1)
(Aは50℃の温水で飽和膨潤させた後の20℃,65%RHにおける引張弾性率、Bは飽和膨潤させる前の20℃、65%RHにおける引張弾性率)
により算出した。
損失正接の測定において用いたものと同様のプレス成形シートの水との接触角を、協和界面科学(株)製のDropMaster500を用いて測定した。
はじめに、元素分析法により下記の条件で全窒素含有量を算出した。
・装置 :パーキンエルマー社製 全自動元素分析装置2400シリーズII型(オートサンプラー標準装備)C・H・N・S/O分析装置
・電気炉温度:975℃
・試料量 :2mg
・助燃剤 :なし
・試料容器:錫箔(助燃効果あり、1枚使用)
・検量線作成用標準物質:スルファニルアミド
次に、下記の条件でNMRの測定により有機ジイソシアネートに由来する窒素原子及び鎖伸長剤に由来する窒素原子を検出した。
・装置 :日本電子製核磁気共鳴装置 Lambda500
・測定条件:共鳴周波数;1H 500MHz /プローブ;TH5FG2
・溶媒 :DMSO-d6 濃度;5wt%/vol
・測定温度:80℃
・積算回数:64s
そして、元素分析法及びNMRの結果から、有機ジイソシアネートのイソシアネート基に由来する窒素含有割合を算出した。
厚さ2.0mmに変更した以外は、損失正接の測定において作成した方法と同様にしてプレス成形シートを得た。そして、プレス成形シートから20mm×50mmの試験片を切り出した。得られた試験片に幅1.0mm、深さ1.0mmの溝を形成して研磨層用のシートを作成した。そして、試験片と同形状の穴を基板のポリウレタンパッドに開け、試験片をはめ込み、研磨パッドを得た。研磨パッドを日本電産シンポ(株)製の電動ろくろ研磨機(RK-3D形)に装着した。そして、(株)アライドマテリアル製のダイヤモンドドレッサー(番手#100)を用い、スラリーを150mL/分の速度で流しながらドレッサー回転数61rpm、研磨パッド回転数60rpm、ドレッサー荷重2.75psiの条件で研磨パッド表面を8時間研削した。研削後の研磨層を目視で観察し、バリが全く発生しなかった場合には良、少しでもバリが発生した場合は否と判定した。
数平均分子量1000のポリテトラメチレングリコール(PTMG1000)、BD、及びMDIを、PTMG1000:BD:MDI=32.0:16.2:51.8(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンBを得た。
数平均分子量850のポリテトラメチレングリコール(PTMG850)、BD、及びMDIを、PTMG850:BD:MDI=28.9:16.6:54.5(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンCを得た。
PTMG850、BD、3-メチル1,5-ペンタンジオール(MPD)及びMDIを、PTMG850:BD:MPD:MDI=18.5:15.0:6.6:59.9(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンDを得た。
数平均分子量1400のポリテトラメチレングリコール(PTMG1400)、BD、MPD及びMDIを、PTMG1400:BD:MPD:MDI=32.4:12.2:5.4:50.0(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンEを得た。
数平均分子量2000のポリテトラメチレングリコール(PTMG2000)、BD、MPD及びMDIを、PTMG2000:BD:MPD:MDI=31.7:12.7:5.6:50.0(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンFを得た。
PTMG2000、数平均分子量2000のポリ(2-メチル-1,8-オクタメチレン-co-ノナメチレンアジペート)ジオール(PNOA2000;ノナメチレン単位と2-メチル-1,8-オクタメチレン単位とのモル比=7対3)、1,4-シクロヘキサンジメタノール(CHDM)、BD及びMDIを、PTMG2000:PNOA2000:BD:CHDM:MDI=21.7:9.3:13.6:5.4:50.0(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンGを得た。
PTMG2000、PNOA2000、CHDM、BD及びMDIを、PTMG2000:PNOA2000:BD:CHDM:MDI=17.0:7.3:15.2:6.1:54.4(質量比)の割合で混合しプレポリマーを調製した。そして、得られたプレポリマーを小型ニーダーで、240℃、スクリュー回転数100rpmの条件で5分間混練することにより熱可塑性ポリウレタンHを得た。
11 回転定盤
12 スラリー供給ノズル
13 キャリア
14 パッドコンディショナー
15 被研磨材
16 研磨スラリー
20 CMP装置
Claims (9)
- 熱可塑性ポリウレタンの非多孔性成形体であって、
前記熱可塑性ポリウレタンは、-70~-50℃の範囲における損失正接(tanδ)の最大値が4.00×10-2以下であることを特徴とする研磨層用非多孔性成形体。 - 前記熱可塑性ポリウレタンは、
数平均分子量650~1400の高分子ジオールと有機ジイソシアネートと鎖伸長剤とを重合させることにより得られ、前記有機ジイソシアネートのイソシアネート基に由来する窒素含有割合が5.7~6.5質量%である請求項1に記載の研磨層用非多孔性成形体。 - 前記熱可塑性ポリウレタンは、厚さ0.5mmのシートの660nmのレーザー波長に対するレーザー透過率が70%以上である請求項1または2に記載の研磨層用非多孔性成形体。
- 前記熱可塑性ポリウレタンは、50℃の温水で飽和膨潤させた後の引張弾性率が130~800MPaである請求項1~3の何れか1項に記載の研磨層用非多孔性成形体。
- 前記熱可塑性ポリウレタンは、下記式:
A/B×100
(Aは50℃の温水で飽和膨潤させたとき引張弾性率、Bは飽和膨潤させていないときの引張弾性率)
から算出される、引張弾性率の水飽和膨潤時保持率が55%以上である請求項1~4の何れか1項に記載の研磨層用非多孔性成形体。 - 前記熱可塑性ポリウレタンのシートは、水との接触角が80度以下である請求項1~5の何れか1項に記載の研磨層用非多孔性成形体。
- 請求項1~6の何れか1項に記載の研磨層用非多孔性成形体を研磨層として含むことを特徴とする研磨パッド。
- 前記研磨層と、前記研磨層に積層された前記研磨層の硬度よりも低い硬度を有するクッション層とを含む請求項7に記載の研磨パッド。
- 請求項7または8に記載の研磨パッドを用いたことを特徴とする化学的機械的研磨方法。
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2020036038A1 (ja) | 2018-08-11 | 2020-02-20 | 株式会社クラレ | 研磨層用ポリウレタン、研磨層及び研磨パッド |
KR20210021056A (ko) | 2018-08-11 | 2021-02-24 | 주식회사 쿠라레 | 연마층용 폴리우레탄, 연마층 및 연마 패드 |
JPWO2020036038A1 (ja) * | 2018-08-11 | 2021-08-10 | 株式会社クラレ | 研磨層用ポリウレタン、研磨層及び研磨パッド |
JP6993513B2 (ja) | 2018-08-11 | 2022-01-13 | 株式会社クラレ | 研磨層用ポリウレタン、研磨層及び研磨パッド |
JP2022056411A (ja) * | 2020-09-29 | 2022-04-08 | エスケーシー ソルミックス カンパニー,リミテッド | 研磨パッドおよびこれを用いた半導体素子の製造方法 |
JP7286227B2 (ja) | 2020-09-29 | 2023-06-05 | エスケー エンパルス カンパニー リミテッド | 研磨パッドおよびこれを用いた半導体素子の製造方法 |
WO2023054331A1 (ja) * | 2021-09-30 | 2023-04-06 | 株式会社クラレ | 研磨層用熱可塑性ポリウレタン、研磨層、及び研磨パッド |
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KR20170077122A (ko) | 2017-07-05 |
JPWO2016067588A1 (ja) | 2017-08-10 |
KR102398130B1 (ko) | 2022-05-13 |
US20170291275A1 (en) | 2017-10-12 |
IL251183A0 (en) | 2017-05-29 |
EP3213868B1 (en) | 2019-06-05 |
EP3213868A4 (en) | 2018-08-08 |
TW201620987A (zh) | 2016-06-16 |
TWI572671B (zh) | 2017-03-01 |
JP6518680B2 (ja) | 2019-05-22 |
US10625391B2 (en) | 2020-04-21 |
EP3213868A1 (en) | 2017-09-06 |
CN107073678A (zh) | 2017-08-18 |
CN107073678B (zh) | 2019-11-19 |
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