US20130012108A1 - Polishing pad and method of making the same - Google Patents

Polishing pad and method of making the same Download PDF

Info

Publication number
US20130012108A1
US20130012108A1 US13/518,475 US201013518475A US2013012108A1 US 20130012108 A1 US20130012108 A1 US 20130012108A1 US 201013518475 A US201013518475 A US 201013518475A US 2013012108 A1 US2013012108 A1 US 2013012108A1
Authority
US
United States
Prior art keywords
polishing
layer
polishing pad
composition
polymer particles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/518,475
Other languages
English (en)
Inventor
Naichao Li
William D. Joseph
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to US13/518,475 priority Critical patent/US20130012108A1/en
Assigned to 3M INNOVATIVE PROPERTIES COMPANY reassignment 3M INNOVATIVE PROPERTIES COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JOSEPH, WILLIAM D., LI, NAICHAO
Publication of US20130012108A1 publication Critical patent/US20130012108A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • 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
    • B24D3/28—Resins or natural or synthetic macromolecular compounds
    • 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
    • B24D3/34—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties
    • B24D3/342—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties incorporated in the bonding agent
    • B24D3/344—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents characterised by additives enhancing special physical properties, e.g. wear resistance, electric conductivity, self-cleaning properties incorporated in the bonding agent the bonding agent being organic
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • 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
    • H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting

Definitions

  • CMP chemical mechanical planarization
  • a substrate such as a wafer is pressed against and relatively moved with respect to a polishing pad in the presence of a working liquid that is typically a slurry of abrasive particles in water and/or an etching chemistry.
  • a working liquid typically a slurry of abrasive particles in water and/or an etching chemistry.
  • Various CMP polishing pads for use with abrasive slurries have been disclosed, for example, U.S. Pat. Nos. 5,257,478 (Hyde et al.); 5,921,855 (Osterheld et al.); 6,126,532 (Sevilla et al.); 6,899,598 (Prasad); and 7,267,610 (Elmufdi et al.).
  • the present disclosure provides porous polishing pads with a polishing layer having a thermally cured component and a radiation cured component and methods of making such polishing pads. Pores are incorporated into the polishing layer through the use of polymer particles.
  • the pores in the porous polishing pads disclosed herein are closed cell pores that generally have lower pore size non-uniformity and smaller pore size than the pores of conventional thermally cured polishing pads. The control over pore size and distribution may be advantageous, for example, for the polishing performance of the polishing pad.
  • the present disclosure provides a polishing pad comprising:
  • a compliant layer having first and second opposing sides
  • porous polishing layer disposed on the first side of the compliant layer, the porous polishing layer comprising:
  • the present disclosure provides a method of making a polishing pad, the method comprising:
  • composition comprising a thermally curable resin composition, a radiation curable resin composition, and polymer particles;
  • the method further comprises adhesively bonding a compliant layer to a surface of the support layer opposite the porous polishing layer.
  • the present disclosure provides a method of polishing comprising:
  • polishing pads according to the present disclosure have various features and characteristics that enable their use in a variety of polishing applications.
  • polishing pads of the present disclosure may be particularly well suited for chemical mechanical planarization (CMP) of wafers used in manufacturing integrated circuits and semiconductor devices.
  • CMP chemical mechanical planarization
  • the polishing pad described in this disclosure may provide some or all of the following advantages.
  • a polishing pad according to the present disclosure may act to better retain a working liquid used in the CMP process at the interface between the polishing surface of the pad and the substrate surface being polished, thereby improving the effectiveness of the working liquid in augmenting polishing.
  • a polishing pad according to the present disclosure may reduce or eliminate dishing and/or edge erosion of the wafer surface during polishing.
  • use of a polishing pad according to the present disclosure in a CMP process may result in improved within wafer polishing uniformity, a flatter polished wafer surface, an increase in edge die yield from the wafer, and improved CMP process operating conditions and consistency.
  • use of a polishing pad according to the present disclosure may permit processing of larger diameter wafers while maintaining the required degree of surface uniformity to obtain high chip yield, processing of more wafers before conditioning of the pad surface is needed in order to maintain polishing uniformity of the wafer surfaces, or reducing process time and wear on the pad conditioner.
  • Pore size non-uniformity refers to the standard deviation of the pore size mean divided by the mean pore size multiplied by 100.
  • polyurethane refers to a polymer having more than one urethane linkage (—NH—C(O)—O—), urea linkage (—NH—C(O)—NH— or —NH—C(O)—N(R)—, wherein R can be hydrogen, an aliphatic, cycloaliphatic or aromatic group), biuret, allophanate, uretdione, or isocyanurate linkage in any combination.
  • (meth)acrylate refers to acrylates and methacrylates, which can include urethane acrylates, methacrylates and combinations of acrylates and methacrylates.
  • polymeric refers to a molecule having a structure that includes the multiple repetition of units derived from molecules of low relative molecule mass.
  • polymeric includes “oligomeric”.
  • phrases “at least one of” and “comprises at least one of” followed by a list refers to any one of the items in the list and any combination of two or more items in the list.
  • FIGS. 1A and 1B are micrographs of a cross-section and top view, respectively, of a porous polishing pad in the prior art
  • FIG. 2 is a schematic side view of one embodiment of a polishing pad according to the present disclosure
  • FIG. 3 is a side view of a polishing pad having projecting polishing elements according to another embodiment of the present disclosure
  • FIG. 4 is a side view of a polishing pad having projecting polishing elements according to yet another embodiment of the present disclosure
  • FIGS. 5A and 5B are micrographs of a cross-section and top view, respectively, of the cured composition of Example 2 useful for forming polishing layers according to the present disclosure
  • FIGS. 6A and 6B are micrographs of a cross-section and a top view, respectively, of the cured composition of Comparative Example 3;
  • FIGS. 7A and 7B are micrographs of a cross-section and top view, respectively, of the cured composition of Example 15 useful for forming polishing layers according to the present disclosure.
  • FIG. 8 is a micrograph of a cross-section view of the cured composition of Example 11 useful for forming polishing layers according to the present disclosure.
  • Typical CMP pads are constructed from thermoset (e.g., polyurethane) materials having pores.
  • the pores can be generated using a variety of methods such as microballoons, soluble fibers, gas entrapment (e.g., in-situ or ex-situ generated), and physical air entrapment. Control of the pore size, pore volume, and pore distribution through the pad can be challenging when using these methods due to temperature gradients created during polymerization, skin/core effects resulting from molding operations, distribution of the fibers, dissolving rate of the soluble fibers, and polishing chemistry.
  • FIG. 1 shows cross-section and top views of a commercially made open cell CMP pad available from PPG Industries, Pittsburgh, Pa., under the trade designation “S7”. As shown in FIG. 1 , the size, shape, and distribution for the pores in this pad is not controlled.
  • the present disclosure is directed to improved porous polishing pads, in which typically closed cell pores are formed with controlled size and uniformity.
  • Various exemplary embodiments of the disclosure will now be described. Exemplary embodiments of the present disclosure may take on various modifications and alterations without departing from the spirit and scope of the disclosure. Accordingly, it is to be understood that the embodiments of the present invention are not to be limited to the following described exemplary embodiments, but are to be controlled by the limitations set forth in the claims and any equivalents thereof.
  • the porous polishing pad 2 a comprises a compliant layer 10 a and a porous polishing layer 12 a disposed on one side of (that is, one major surface of) the compliant layer. Interposed between the porous polishing layer 12 a and the compliant layer 10 a is optional support layer 8 a , which is useful for some embodiments of the porous polishing pad and method of the present disclosure.
  • the porous polishing layer comprises a crosslinked network, polymer particles dispersed within the crosslinked network, and closed cell pores dispersed within the crosslinked network.
  • the polishing pads according to the present disclosure are porous before the polishing process begins.
  • Exemplary polymer particles in the polishing layer can include thermoplastic polymer particles, thermoset polymer particles, and mixtures thereof.
  • thermoplastic polymer refers to a polymeric material that is essentially not crosslinked and essentially does not form a three-dimensional network.
  • thermoset refers to a polymer that is at least substantially crosslinked wherein said polymer has essentially a three-dimensional network.
  • the polymer particles can be chosen such that there is minimal sintering of the particles upon heating (i.e., there is minimal plastic flow at the boundary of the polymer particles, and little to no coalescence between the particles of the polymer particles in the polishing pad of the present disclosure).
  • the polishing pad can be prepared below the melting or sintering point of the particulate thermoplastic polymer.
  • the polymer particles comprise thermoset polymers.
  • Polymer particles useful for practicing the present disclosure can be prepared by various methods (e.g., a condensation reaction, a free radical initiated reaction, or combinations thereof).
  • the polymer can include an interpenetrating polymer network formed by stepwise or simultaneous condensation and free radical polymerization reactions.
  • interpenetrating polymer network refers to a combination of two polymers both in network form, at least one of which is synthesized or crosslinked in the immediate presence of the other. Typically in IPNs, there are no induced covalent bonds between the two polymers. Thus, in addition to mechanical blending and copolymerization, IPNs represent another mechanism by which different polymers can be physically combined.
  • the polymer particles can be prepared by various methods.
  • bulk polymers can be cryogenically ground and classified into desired particle size ranges.
  • the shape of the polymer particles can be regular or irregular, and can include the following shapes: sphere, fiber, disk, flake, and combinations or mixtures thereof.
  • the polymer particles are substantially spherical.
  • the term “substantially spherical” refers to a particle having a sphericity of at least 0.75 (in some embodiments, at least 0.8, 0.85, 0.9, 0.95, 0.96, 0.97, or 0.98).
  • the polymer particles are fibers.
  • Fibers useful for practicing the present disclosure typically have an aspect ratio (that is, longest dimension over shortest dimension) of at least 1.5:1, for example, at least 2:1, 3:1, 4:1, 5:1, 10:1, 25:1, 50:1, 75:1, 100:1, or more. Fibers useful for practicing the present disclosure may have an aspect ratio in a range from 2:1 to 100:1, 5:1 to 75:1, or 10:1 to 50:1.
  • the polymer particles can have an average particle size of at least 5 (in some embodiments, at least 7, 10, 15, 20, 25, 30, 40, or 50) microns. In some embodiments, the polymer particles can have an average particle size of up to 500 (in some embodiments, up to 400, 300, 200, or 100) microns.
  • the particle size generally refers to the diameter of the particle; however, in embodiments when the particles are not spherical (e.g., fibers), the particle size can refer to the largest dimension of the particle.
  • the average particle size of the polymer particles can be determined by conventional methods.
  • the average particle size of the polymer particles can be determined using light scattering techniques, such as a Coulter LS particle size analyzer which is manufactured and commercially available from Beckman Coulter Incorporated.
  • particle size refers to the diameter or largest dimension of the particle based on volume percent as determined by light scattering using a Coulter Counter LS particle size analyzer. In this light scattering technique, the size is determined from a hydrodynamic radius of gyration regardless of the actual shape of the particle.
  • the “average” particle size is the average diameter of the particle based on volume percent.
  • the fibers have a maximum particle size of up to about 600, 500, or 450 microns (30, 35, or 40 U.S. Mesh) as determined by conventional screening techniques. For example, in some embodiments, at least 97, 98, or 99 percent of the fibers pass through a screen having openings of 600, 500, or 400 microns (30, 35, or 40 U.S. Mesh).
  • the polymer particles have a high degree of uniformity.
  • the non-uniformity of the size of polymer particles is up to 75 (in some embodiments, up to 70, 65, 60, 65, or 50) percent.
  • Particle size non-uniformity refers to the particle size standard deviation divided by the average particle size multiplied by 100.
  • the polymer particles are substantially solid.
  • substantially solid means that the particulate polymer is not hollow, for example, the polymer particles are not in the form of hollow microcapsules.
  • the substantially solid polymer particles can contain entrapped gas bubbles.
  • Suitable polymer particles include polyvinylchloride, polyvinylfluoride, polyethylene, polypropylene, nylon, polycarbonate, polyester, poly(meth)acrylate, polyether, polyamide, polyurethane, polyepoxide, polystyrene, polyimide (e.g., polyetherimide), polysulfone and mixtures thereof.
  • the polymer particles can be chosen from poly(meth)acrylate, polyurethane, polyepoxide and mixtures thereof.
  • the polymer particles comprise water-soluble particles.
  • Exemplary useful water soluble particles include particles made of saccharides (e.g., polysaccharides such as dextrin, cyclodextrin, starch, mannitol, and lactose), celluloses (e.g., hydroxypropylcelluloses and methylcelluloses), protein, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, polyethylene oxide, water-soluble photosensitive resin, sulfonated polyisoprene, sulfonated polyisoprene copolymer, and any combination of these.
  • the polymer particles comprise a cellulose.
  • the polymer particles comprise methylcellulose. Even though in these embodiments, the polymer particles comprise water-soluble particles, the polymer particles can form pores in the polishing layer when the polishing layer is formed. A working liquid that can dissolve the particles during polishing is not required to form pores.
  • the polymer particles comprise a polyurethane, which can be prepared, for example, from a resin comprising at least two isocyanate groups, and/or a capped isocyanate reactant having at least two capped isocyanate groups; and a second resin that has at least two groups that are reactive with isocyanate groups.
  • the first and second resins can be mixed together and polymerized or cured to form a bulk polyurethane, which can then be ground (e.g., cryogenically ground), and optionally classified.
  • the polymer particles can be formed by mixing the first and second resins together, slowly pouring the mixture into heated deionized water under agitation (optionally in the presence of an organic cosolvent and/or surfactant), isolating the formed particulate material (e.g., by filtration), drying the isolated particulate material, and optionally classifying the dried particulate polyurethane.
  • the isocyanate and hydrogen materials can be mixed together in the presence of an organic solvent (e.g., alcohols, water-insoluble ethers, branched and straight hydrocarbons, ketones, toluene, xylene and mixtures thereof).
  • an organic solvent e.g., alcohols, water-insoluble ethers, branched and straight hydrocarbons, ketones, toluene, xylene and mixtures thereof.
  • the first resin comprising at least two isocyanate groups can be chosen from isocyanate functional monomers, isocyanate functional prepolymers and combinations thereof.
  • exemplary suitable isocyanate monomers include aliphatic polyisocyanates; ethylenically unsaturated polyisocyanates; alicyclic polyisocyanates; aromatic polyisocyanates wherein the isocyanate groups are not bonded directly to the aromatic ring, for example, alpha,alpha′-xylene diisocyanate; aromatic polyisocyanates wherein the isocyanate groups are bonded directly to the aromatic ring, for example, benzene diisocyanate; halogenated, alkylated, alkoxylated, nitrated, carbodiimide modified, urea modified, and biuret modified derivatives of these polyisocyanates; and dimerized and trimerized products of these polyisocyanates.
  • Exemplary aliphatic polyisocyanates include ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2′-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate, 2,4,4,-trimethylhexamethylene diisocyanate, 1,6,1-undecanetriisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanato-4-(isocyanatomethyl)octane, 2,5,7-trimethyl-1,8-diisocyanato-5-(isocyanatomethyl)octane, bis(isocyanatoethyl)-carbonate, bis(isocyanatoethyl)ether, 2-isocyanatoprop
  • Exemplary suitable ethylenically unsaturated polyisocyanates can include butene diisocyanate and 1,3-butadiene-1,4-diisocyanate.
  • Exemplary suitable alicyclic polyisocyanates include isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-5-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-isocyanatomethyl-bicyclo[2.2.1
  • Exemplary aromatic polyisocyanates wherein the isocyanatc groups are not bonded directly to the aromatic ring include bis(isocyanatoethyl)benzene, alpha, alpha, alpha′, alpha′-tetramethylxylene diisocyanate, 1,3-bis(1-isocyanato-1-methylethyl)benzene, bis(isocyanatobutyl)benzene, bis(isocyanatomethyl)naphthalene, bis(isocyanatomethyl)diphenyl ether, bis(isocyanatoethyl)phthalate, mesitylene triisocyanate, 2,5-di(isocyanatomethyl)furan and mixtures thereof.
  • Exemplary suitable aromatic polyisocyanates having isocyanate groups bonded directly to the aromatic ring include phenylene diisocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, methylnaphthalene diisocyanate, biphenyl diisocyanate, ortho-tolidine diisocyanate, 4,4′-diphenylmethane diisocyanate, bis(3-methyl-4-isocyanatophenyl)methane, bis(isocyanatophenyl)ethylene, 3,3′-dimethoxy-biphenyl-4,4′-diisocyanate, triphenylmethane triiso
  • the first resin comprising at least two isocyanate groups is selected from the group consisting of alpha, alpha′-xylene diisocyanate, alpha, alpha, alpha′, alpha′-tetramethylxylene diisocyanate, isophorone diisocyanate, bis(isocyanatocyclohexyl)methane, toluene diisocyanate, 4,4′-diphenylmethane diisocyanate, and mixtures thereof.
  • the first resin having at least two isocyanate groups can comprise an isocyanate functional polyurethane prepolymer.
  • Isocyanate functional polyurethane prepolymers can be prepared by various conventional techniques.
  • at least one polyol such as a diol, and at least one isocyanate functional monomer such as a diisocyanate monomer can be reacted together to form a polyurethane prepolymer having at least two isocyanate groups.
  • Exemplary suitable isocyanate functional monomers include the aforementioned isocyanate functional monomers.
  • Suitable isocyanate functional polyurethane prepolymers useful for practicing the present disclosure can have molecular weights that vary within a wide range.
  • the isocyanate functional polyurethane prepolymer can have a number average molecular weight (Mn) of from 500 to 15,000, or from 500 to 5000, as determined, for example, by gel permeation chromatography (GPC) using polystyrene standards.
  • Mn number average molecular weight
  • Exemplary polyols useful for preparing isocyanate functional polyurethane prepolymers include straight or branched chain alkane polyols, such as 1,2-ethanediol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, glycerol, neopentyl glycol, trimethylolethane, trimethylolpropane, di-trimethylolpropane, erythritol, pentaerythritol and di-pentaerythritol; polyalkylene glycols, such as di-, tri- and tetraethylene glycol, and di-, tri- and tetrapropylene glycol; cyclic alkane polyols, such as cyclopentanediol, cyclohexanediol, cyclohexanetriol, cyclohe
  • suitable polyols useful for preparing isocyanate functional polyurethane prepolymers include higher polyalkylene glycols, such as polyethylene glycols having a number average molecular weight (Mn) of from 200 to 2000 grams per mole; hydroxyl-bearing acrylics, such as those formed from the copolymerization of (meth)acrylates and hydroxy functional (meth)acrylates, such as methyl methacrylate and hydroxyethyl methacrylate copolymers; and hydroxy functional polyesters, such as those formed from the reaction of diols, such as butane diol, and diacids or diesters, such as adipic acid or diethyl adipate.
  • the polyol useful for practicing the present disclosure can have a number average molecular weight (Mn) of from 200 to 2000 grams per mole.
  • an isocyanate functional polyurethane prepolymer can be prepared by reacting a diisocyanate such as toluene diisocyanate, with a polyalkylene glycol such as poly(tetrahydrofuran).
  • a diisocyanate such as toluene diisocyanate
  • a polyalkylene glycol such as poly(tetrahydrofuran).
  • an isocyanate functional polyurethane prepolymer can be prepared in the presence of a catalyst.
  • the amount of catalyst used can be less than 5 percent by weight, or less than 3 percent by weight, or less than 1 percent by weight, based on the total weight of the polyol and isocyanate functional monomer.
  • exemplary suitable catalysts include a stannous adduct of an organic acid, such as stannous octoate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin mercaptide, dibutyl tin dimaleate, dimethyl tin diacetate, dimethyl tin dilaurate, 1,4-diazabicyclo[2.2.2]octane, and mixtures thereof.
  • the catalyst can be zinc octoate, bismuth, or ferric acetylacetonate.
  • Further exemplary suitable catalysts include tertiary amines such as triethylamine, triisopropylamine and N,N-dimethylbenzylamine.
  • the first resin having at least two isocyanate groups includes a capped isocyanate compound having at least two capped isocyanate groups.
  • capped isocyanate compound refers to a monomer or prepolymer having terminal and/or pendent capped isocyanate groups which can be converted to decapped (i.e., free) isocyanate groups and separate or free capping groups. Any of the aforementioned examples of suitable isocyanate compounds can be capped.
  • Exemplary nonfugitive capping groups of the capped isocyanate include 1H-azoles, such as 1H-imidazole, 1H-pyrazole, 3,5-dimethyl-1H-pyrazole, 1H-1,2,3-triazole, 1H-1,2,3-benzotriazole, 1H-1,2,4-triazole, 1H-5-methyl-1,2,4-triazole and 1H-3-amino-1,2,4-triazole; lactams, such as ⁇ -caprolactam and 2-pyrrolidinone; morpholines such as 3-aminopropyl morpholine; and N-hydroxy phthalimide.
  • 1H-azoles such as 1H-imidazole, 1H-pyrazole, 3,5-dimethyl-1H-pyrazole, 1H-1,2,3-triazole, 1H-1,2,3-benzotriazole, 1H-1,2,4-triazole, 1H-5-methyl-1,2,4-triazole and 1H
  • Exemplary fugitive capping groups of the capped isocyanate compound include alcohols, such as propanol, isopropanol, butanol, isobutanol, tert-butanol and hexanol; alkylene glycol monoalkyl ethers, such as ethylene glycol monoalkyl ethers (e.g., ethylene glycol monobutyl ether and ethylene glycol monohexyl ether), and propylene glycol monoalkyl ethers (e.g., propylene glycol monomethyl ether); and ketoximes, such as methyl ethyl ketoxime.
  • alcohols such as propanol, isopropanol, butanol, isobutanol, tert-butanol and hexanol
  • alkylene glycol monoalkyl ethers such as ethylene glycol monoalkyl ethers (e.g., ethylene glycol monobutyl
  • the inclusion of capped isocyanate material in the first resin having at least two isocyanate groups can result in the formation of covalent bonds: (a) between at least a portion of the particulate polyurethane particles; and/or (b) between at least a portion of the particulate polyurethane and at least a portion of the crosslinked network.
  • the capped isocyanate compound can be present in an amount such that the first resin capped isocyanate groups in an amount of at least 5 mole percent, or at least 10 mole percent, or less than 40 mole percent, or less than 50 mole percent, based on the total molar equivalents of free isocyanate and capped isocyanate groups.
  • the second resin that has at least two groups that are reactive with isocyanate groups can be chosen from a wide variety of materials.
  • the second resin has functional groups chosen from hydroxyl, mercapto, primary amine, secondary amine and combinations thereof.
  • Exemplary suitable second resins include the aforementioned polyols.
  • the second resin which can have at least two groups that are reactive with isocyanate groups includes a polyamine.
  • exemplary polyamines include ethyleneamines such as ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), piperazine, diethylenediamine (DEDA), and 2-amino-1-ethylpiperazine.
  • suitable polyamines include one or more isomers of dialkyl toluenediamine, such as 3,5-dimethyl-2,4-toluenediamine, 3,5-dimethyl-2,6-toluenediamine, 3,5-diethyl-2,4-toluenediamine, 3,5-diethyl-2,6-toluenediamine, 3,5-diisopropyl-2,4-toluenediamine, 3,5-diisopropyl-2,6-toluenediamine and mixtures thereof.
  • the polyamine can be chosen from methylene dianiline, trimethyleneglycol di(para-aminobenzoate), and amine-terminated oligomers and prepolymers.
  • suitable polyamines can be chosen from those based on 4,4′-methylene-bis(dialkylaniline) (e.g., 4,4′-methylene-bis(2,6-dimethylaniline), 4,4′-methylene-bis(2,6-diethylaniline), 4,4′-methylene-bis(2-ethyl-6-methylaniline), 4,4′-methylene-bis(2,6-diisopropylaniline), 4,4′-methylene-bis(2-isopropyl-6-methylaniline), 4,4′-methylene-bis(2,6-diethyl-3-chloroaniline) and mixtures thereof.
  • 4,4′-methylene-bis(dialkylaniline) e.g., 4,4′-methylene-bis(2,6-dimethylaniline), 4,4′-methylene-bis(2,6-diethylaniline), 4,4′-methylene-bis(2-ethyl-6-methylaniline), 4,4′-methylene-bis(2-iso
  • preparation of a particulate polyurethane from a first resin comprising at least two isocyanate groups and a second resin comprising at least two groups that are reactive with an isocyanate can be carried out in the presence of a catalyst.
  • Suitable catalysts include those listed above for the preparation of an isocyanate functional polyurethane prepolymer.
  • the molar equivalent ratio of isocyanate groups and optional capped isocyanate groups to isocyanate-reactive groups useful for preparing particulate polyurethanes is from 0.5:1.0 to 1.5:1.0, e.g., from 0.7:1.0 to 1.3:1.0 or from 0.8:1.0 to 1.2:1.0.
  • a crosslinked polyurethane can be prepared by using less than the stoichiometrically required amount of the second resin such that the urethane or urea linkages will react with remaining isocyanates.
  • the partial replacement of difunctional by trifunctional compounds will result in more thermally stable chemical crosslinks.
  • Some useful particulate polyurethanes are commercially available, for example, from Dainichiscika Color & Chemicals Mfg. Co., Ltd. Advanced Polymers Group, Tokyo, Japan, under the trade designation “DAIMIC-BEAZ” in grades “UCN-5350D”, “UCN-5150D”, and “UCN-5070D”; polyurethane particles available from Negami Chemical Industrial Co., Ltd., Nomi-city, Japan, under the trade designation “ART PEARL”; and aliphatic polyether-based thermoplastic polyurethanes available, for example, from Bayer Corporation under the trade designation “TEXIN”.
  • suitable polymer particles useful for practicing the present disclosure include particulate polyepoxides.
  • a particulate polyepoxide can be prepared, for example, from a reaction product of a first resin having at least two epoxide groups; and a second resin having at least two groups that are reactive with the epoxide groups of the epoxide.
  • the first resin comprising at least two epoxide groups and the second resin can be mixed together and polymerized or cured to form bulk polyepoxide, which then can be ground (e.g., cryogenically ground), and optionally classified.
  • the particulate polyepoxide can be formed by mixing the epoxide functional and hydrogen functional materials together, slowly pouring the mixture into heated deionized water under agitation, isolating the formed particulate material (e.g., by filtration), drying the isolated particulate material, and optionally classifying the dried particulate polyepoxide.
  • suitable epoxide functional materials useful for practicing the present disclosure include epoxide functional monomers, epoxide functional prepolymers and combinations thereof.
  • exemplary suitable epoxide functional monomers can include aliphatic polyepoxides, such as 1,2,3,4-diepoxybutane, 1,2,7,8-diepoxyoctane; cycloaliphatic polyepoxides, such as 1,2,4,5-diepoxycyclohexane, 1,2,5,6-diepoxycyclooctane, 7-oxa-bicyclo[4.1.0]heptane-3-carboxylic acid 7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester, 1,2-epoxy-4-oxiranyl-cyclohexane and 2,3-(epoxypropyl)cyclohexane; aromatic polyepoxides, such as bis(4-hydroxyphenyl)methane diglycidyl ether;
  • Epoxide functional monomers that may be useful in the present disclosure are typically prepared from the reaction of a polyol and an epihalohydrin, for example, epichlorohydrin.
  • Polyols that may be used to prepare epoxide functional monomers include those recited previously herein with regard to the preparation of the isocyanate functional prepolymer.
  • a useful class of epoxide functional monomers include those prepared from the reaction of a bisphenol and epichlorohydrin (e.g., the reaction of 4,4′-isopropylidenediphenol and epichlorohydrin to make 4,4′-isopropylidenediphenol diglycidyl ether).
  • an epoxide functional prepolymer useful for preparing particular epoxides can be prepared by reacting a polymeric polyol and epichlorohydrin.
  • exemplary suitable polymeric polyols can include polyalkylene glycols, such as polyethylene glycol and polytetrahydrofuran; polyester polyols; polyurethane polyols; poly((meth)acrylate) polyols; and mixtures thereof.
  • the epoxide functional prepolymer can include an epoxy functional poly((meth)acrylate) polymer which can be prepared from a (meth)acrylate monomer and an epoxide functional radically polymerizable monomer (e.g., glycidyl (meth)acrylate).
  • Suitable epoxide functional prepolymers can have a wide range of molecular weight.
  • the molecular weight of the epoxide functional prepolymer can be from 500 to 15,000 grams per mole, or from 500 to 5000 grams per mole, as determined, for example, by gel permeation chromatography (GPC) using polystyrene standards.
  • the second resin having at least two groups reactive with epoxides can comprise at least one of hydroxyl, mercapto, carboxylic acid, primary amine, or secondary amine.
  • the second resin can include polyols recited previously herein.
  • the second resin can include polyamines recited previously herein.
  • suitable polyamines can include polyamide prepolymers having at least two amine groups selected from primary amines, secondary amines and combinations thereof.
  • Suitable exemplary polyamide prepolymers can include those available, for example, from Cognis Corporation, Coating & Inks Division, Monheim, Germany, under the trade designation “VERSAMID”.
  • preparation of a particulate epoxide from a first resin comprising at least two epoxide groups and a second resin comprising at least two groups that are reactive with an epoxide can be carried out in the presence of a catalyst.
  • a catalyst include tertiary amines such as triethylamine, triisopropylamine, tri-tertiarybutyl amine, tetrafluoroboric acid and N,N-dimethylbenzylamine.
  • the catalyst can be incorporated into the second resin before it is combined with the epoxide functional material.
  • the amount of catalyst used can be less than 5 percent by weight, or less than 3 percent by weight, or less than 1 percent by weight, based on the total weight of the combined first and second resins.
  • the molar equivalents ratio of epoxide groups to epoxide-reactive groups of the reactants used to prepare the particulate crosslinked polyepoxide is typically from 0.5:1.0 to 2.0:1.0, e.g., from 0.7:1.0 to 1.3:1.0 or from 0.8:1.0 to 1.2:1.0.
  • the first resin having at least two isocyanate groups or at least two epoxide groups, and/or the second resin can optionally comprise known conventional additives.
  • additives include heat stabilizers, antioxidants, mold release agents, static dyes, pigments, flexibilizing additives, such as alkoxylated phenol benzoates and poly(alkylene glycol) dibenzoates, and surfactants, such as ethylene oxide/propylene oxide block copolymeric surfactants.
  • such additives can be present in an amount totaling up to 10 percent by weight, or up to 5 percent by weight, or up to 3 percent by weight, based on the total weight of the combined first and second resins.
  • polymer particles useful for practicing the present disclosure include thermoplastic poly(meth)acrylates commercially available, for example, from ROHM America, Incorporated, Lawrenceville, Ga., under the trade designation “ROHADON” and from Negami Chemical Industrial Co., Ltd., under the trade designation “ART PEARL”.
  • polymer particles useful for practicing the present disclosure include cellulose particles commercially available, for example, from Dow Chemical Company, Midland, Mich., under the trade designation “METHOCEL”.
  • the amount of polymer particles present in the polishing pad according to the present disclosure can vary. Interestingly, it was found that in some embodiments the amount of polymer particles mixed using certain techniques affects the porosity of the resulting polishing layer in an unexpected way. For example, when using a mixer that combines revolution and rotation, it was found that particle levels up to 20 percent by weight provided fewer pores than particle levels up to 15 percent by weight. However, other mixing techniques may provide different results.
  • the polymer particles are present in an amount of at least 1 percent by weight, or at least 2.5 percent by weight, or at least 5 percent by weight, based on the total weight of the particulate polymer and the crosslinked network. In some embodiments, the polymer particles can be present in an amount of up to 25 percent by weight, or up to 20 percent by weight, or less than 20 percent by weight, based on the total weight of the polymer particles and the crosslinked network.
  • the polymer particles can be present in an amount of up to 10 percent by weight, or up to 5 percent by weight, or less than 5 percent by weight, based on the total weight of the polymer particles and the crosslinked network.
  • polymer particles in the form of fibers may provide a useful level of porosity even at a level of up to 2 percent by weight, based on the total weight of the polymer particles and the crosslinked network.
  • the polymer particles are water-soluble fibers (e.g., methylcellulose fibers).
  • methylcellulose fibers As shown in the Tables 1 and 2 in the Examples, a higher level of porosity is obtained with methylcellulose fibers than with an equivalent amount by weight of spherical polyurethane particles.
  • FIG. 8 which is a micrograph of a cross-section view of the cured composition of Example 12, and FIGS. 7A and 7B , which are micrographs of a cross-section and top view, respectively, of the cured composition of Example 15, shows that about the same level of porosity can be obtained with two percent by weight fibers ( FIG. 8 ) as with ten percent by weight particles ( FIGS. 7A and 7B ).
  • Incorporating a lower level of particles to obtain the same porosity may be advantageous, for example, for improving uniformity in the particle distribution throughout the crosslinked network and for maintaining hardness at the pad surface during polishing
  • Polishing pads according to the present disclosure comprise a polishing layer comprising polymer particles and a crosslinked network comprising a thermally cured component and a radiation cured component.
  • a thermally cured component comprises at least one of a polyurethane, a polyepoxide, or a urethane-modified polyepoxide.
  • the crosslinked network of the present disclosure is formed in the presence of the polymer particles.
  • a thermally curable resin composition and a radiation curable resin composition can react to form the crosslinked network while the curable compositions are in the presence of the polymer particles.
  • the polishing layer disclosed herein can comprise at least 75 percent by weight, or at least 80 percent by weight, or at least 85 percent by weight of the crosslinked network, based on the total weight of the polymer particles and the crosslinked network.
  • the crosslinked network can be present in the polishing layer in an amount of up to 99 percent by weight, or up to 95 percent by weight, or up to 90 percent by weight, based on the total weight of the polymer particles and the crosslinked network.
  • the crosslinked network can be prepared by conventional polymerization techniques methods.
  • the crosslinked network can be formed by condensation reactions, free radical initiated reactions, or combinations thereof.
  • the thermally cured component can comprise a polyurethane formed by the condensation of a thermally curable resin composition comprising a polyurethane prepolymer with a polyamine.
  • the radiation cured component can comprise a urethane-polyacrylate or urethane-polymethacrylate formed by the polymerization of a urethane-diacrylate or urethane-dimethacrylate in the presence of a photoinitiator.
  • the crosslinked network is interpenetrating polymer network formed by stepwise or simultaneous thermal curing and radiation curing polymerizations.
  • the radiation cured component in some embodiments a polyacrylate or polymethacrylate
  • the thermally cured component for example, through urethane or urea linking groups.
  • Suitable thermally curable resin compositions useful for practicing the present disclosure can include monomers, prepolymers, and mixtures thereof.
  • the thermally curable resin composition can contain catalysts, crosslinking agents, curing agents, solvents, and other conventional additives that are known in the art.
  • the thermally curable resin composition comprises a first resin having at least two isocyanate groups, which may also be capped isocyanate groups, or at least two epoxide groups; and a second resin having at least two groups that are reactive with isocyanates and/or epoxides (e.g., hydroxyl, amino, carboxy, or mercaptan groups).
  • Exemplary suitable first and second resins that may be used to prepare the thermally cured component can be chosen from the isocyanates (including prepolymers), capped isocyanates, polyols and polyamines described previously herein, respectively, relative to the particulate polyurethanes.
  • Use of capped isocyanates may, for example, delay the onset of gelation when the first and second resins are combined, which may allow for more time for mixing the first and second resins and the polymer particles.
  • isocyanate prepolymers that are useful as the first resin are commercially available, for example, an isocyanate prepolymer available under the trade designation “AIRTHANE PHP-75D” from Air Products and Chemicals, Inc., Allentown, Pa.
  • diamines that are useful as the second resin are commercially available, for example, oligomeric diamine available under the trade designation “VERSALINK P250” and “VERSALINK P650” from Air Products and Chemicals, Inc.
  • the composition comprising a radiation curable resin and a thermally curable resin comprising the first resin having at least two isocyanate groups and the second resin having at least two groups reactive with isocyanate groups can further comprise a catalyst.
  • a catalyst can include those recited previously herein with regard to the preparation of the particulate polyurethane, (e.g., tertiary amines such as triethylamine and organometallic compounds such as dibutyltin dilaurate).
  • the catalyst can be incorporated into the second resin before combining the first and second resins.
  • the catalyst can be present in an amount of less than 5 percent by weight, or less than 3 percent by weight or less than 1 percent by weight, based on the total weight of the combined first and second resins.
  • the molar equivalents ratio of isocyanate groups and optional capped isocyanate groups to isocyanate-reactive groups in the first and second resins, respectively, can be from 0.5:1.0 to 2.0:1.0, or from 0.7:1.0 to 1.3:1.0, or from 0.8:1.0 to 1.2:1.0.
  • the thermally cured component can be prepared by reacting a first resin having at least two epoxide groups; and a second resin having at least two groups reactive with the epoxide groups (e.g., hydroxyl, amino, carboxy, or mercaptan groups).
  • a first resin having at least two epoxide groups e.g., hydroxyl, amino, carboxy, or mercaptan groups
  • exemplary suitable first resins having at least two epoxide groups and second resins include any of those epoxides, polyamines, and polyols used to prepare the particulate polyepoxide as discussed previously herein.
  • the composition comprising a radiation curable resin and a thermally curable resin comprising the first and second resins used to prepare a polyepoxide themally cured component can further comprise an epoxide ring opening catalyst.
  • epoxide ring opening catalyst Exemplary suitable catalysts for ring-opening of epoxides include any of those described above (e.g., tertiary amines such as tri-tert-butyl amine) and tetrafluoroboric acid).
  • the catalyst can be added to the second resin before mixing the first and second resins.
  • the epoxide ring opening catalyst can be present in an amount of less than 5 percent by weight, or less than 3 percent or 1 percent by weight, based on the total weight of the first and second resins.
  • the molar equivalents ratio of epoxide groups to epoxide-reactive groups in the first and second resins, respectively, can be from 0.5:1.0 to 2.0:1.0, or from 0.7:1.0 to 1.3:1.0, or from 0.8:1.0 to 1.2:1.0.
  • the thermally curable resins can comprise conventional additives.
  • suitable conventional additives include any of those additives as described previously herein with regard to preparation of the particulate polyurethanes and particulate polyepoxides, such as mold release agents, dyes, and flexibilizing agents.
  • additives can be present in an amount totaling less than 10 percent by weight, or less than 5 percent by weight, or less than 3 percent by weight, based on the total weight of the crosslinked network.
  • the conventional additives can be added, for example, to either the first or second resins.
  • Porous polishing pads according to the present disclosure comprise a polishing layer having a radiation cured component.
  • the radiation cured component comprises at least one of a polyacrylate, polymethacrylate, poly(vinyl ether), a polyvinyl, or a polyepoxide.
  • the radiation cured component comprises at least one of a polyacrylate or polymethacrylate.
  • the radiation cured component may be prepared from a radiation curable resin comprising at least two acrylate, methacrylate, vinyl (e.g., vinyl, allyl, or styryl groups), or epoxide groups.
  • the radiation curable resin comprises at least two acrylate or methacrylate groups.
  • the radiation curable resin can comprise a (meth)acrylate-modified polyfunctional isocyanate material having at least two (meth)acrylate-modified isocyanate groups, which can be, for example, the reaction product of a polyurethane prepolymer having terminal and/or pendent isocyanate groups (e.g., those polyurethane prepolymers described above in connection with the preparation of particulate polyurethanes) and an (meth)acrylate having an isocyanatc reactive functional group (e.g., a hydroxyl, amino group, or mercapto group).
  • a polyurethane prepolymer having terminal and/or pendent isocyanate groups e.g., those polyurethane prepolymers described above in connection with the preparation of particulate polyurethanes
  • an isocyanatc reactive functional group e.g., a hydroxyl, amino group, or mercapto group
  • hydroxy or amino functional (meth)acrylates include hydroxyalkyl acrylates and methacrylates (e.g., 2-hydroxyethylacrylate (HEA), 2-hydroxyethylmethylacrylate (HEMA), 2-hydroxypropylacrylate, 3-hydroxypropylacrylate (HPA), 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 1,3-dihydroxypropylacrylate, 2,3-dihydroxypropylacrylate and methacrylate, 2-hydroxyethylacrylamide and methacrylamide, 2-hydroxybutyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, 2-hydroxy-3-phenyloxypropyl(meth)acrylate, 1,4-butanediol mono(meth)acrylate, 2-hydroxy alkyl(meth)acryloyl phosphates, 4-hydroxycyclohexyl(meth)acrylate, 1,6-hexanediol mono(meth)acrylate, n
  • Useful hydroxyethylacrylates and hydroxypropylacrylates commercially available from Dow Chemical (Midland, Mich.) and Osaka Organic Chemical Industry Ltd. (Osaka, Japan).
  • Useful hydroxybutyl acrylates are commercially available from Osaka Organic Chemical Industry Ltd.
  • Useful hydroxy polyester acrylates are commercially available under the “TONE MONOMER M-100” trade designation from Dow Chemical Company and “VISCOAT 2308 ” from Osaka Organic Chemical Industry Ltd.
  • Useful hydroxy polyether acrylates are commercially available under the “ARCOL R-2731” trade designation from Bayer Chemicals (Pittsburgh, Pa.).
  • the (meth)acrylate groups can be located pendant, terminal, or a combination thereof on the prepolymer.
  • the prepolymer is end capped with (meth)acrylate groups.
  • the radiation curable resin can be prepared, for example, by reacting a (meth)acrylate having an isocyanate reactive functional group with a polyisocyanate prepolymer, typically in the presence of excess isocyanate.
  • the (meth)acrylate having an isocyanate reactive functional group is reacted with the isocyanate functional prepolymer in an amount such that from about 10% to about 80%, from about 20% to about 70%, or from about 30% to about 60% of the isocyanate groups on the isocyanate functional prepolymer are reacted with the (meth)acrylate having an isocyanate reactive functional group.
  • Some (meth)acrylate-modified polyfunctional isocyanate material having at least two (meth)acrylate-modified isocyanate groups are commercially available, for example, an isocyanate urethane acrylate available under the trade designations “DESMOLUX D100”, “DESMOLUX VPLS 2396”, and “DESMOLUX XP2510” from Bayer Materials Science, Pittsburgh, Pa.
  • the composition which includes the radiation curable composition and the thermally curable composition typically also includes a photoinitiator or a combination of photoinitiators.
  • Useful photoinitiators include, e.g., “alpha cleavage type” photoinitiators including, e.g., benzoin, benzoin acetals (e.g., benzyl dimethyl ketal), benzoin ethers (e.g., benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether), hydroxy alkyl phenyl ketones (e.g., 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one), benzoyl cyclohexanol, dialkoxy acetophenone derivatives (e.g., 2,
  • the photoinitiator is a acylphosphine oxide (e.g., bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, and 2,4,4-trimethylbenzoyl diphenylphosphine oxide).
  • acylphosphine oxide e.g., bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, and 2,4,4-trimethylbenzoyl diphenylphosphine oxide.
  • Exemplary useful commercially available photoinitiators are available under the following trade designations “IRGACURE 369”, “IRGACURE 819”, “IRGACURE CGI 403 ”, “IRGACURE 651”, “IRGACURE 1841”, “IRGACURE 29594”, “DAROCUR 1173”, “DAROCUR 4265”, and “CGI1700”, all of which are available from Ciba Specialty Chemicals (Ardsley, N.Y.).
  • the photoinitiator is preferably present in an amount sufficient to provide the desired rate of photopolymcrization. The amount will depend, in part, on the light source, the thickness of the layer to be exposed to radiant energy and the extinction coefficient of the photoinitiator at the wavelength.
  • the photoinitiator component will be present in an amount of at least about 0.01% by weight, at least about 0.1% by weight, at least about 0.2% by weight, up to about 10% by weight, or up to about 5% by weight.
  • the radiation curable composition and the thermally curable composition can be intimately mixed in the composition for making the porous polishing pad disclosed herein.
  • the composition comprises at least about 10 (in some embodiments, at least about 15, 20, 25, 30, or 40) weight percent of the radiation curable composition and up to about 85 (in some embodiments, up to about 80, 75, 70, 65, 60, 55, or 50) weight percent of the radiation curable composition, based on the total weight of the composition.
  • the composition comprises at least about 15 (in some embodiments, at least about 20, 25, 30, 35, 40, 45, 50, 55, of 60) weight percent of the thermally curable composition and up to about 90 (in some embodiments, up to about 85, 80, or 75) weight percent of the thermally curable composition, based on the total weight of the composition.
  • the composition comprising a thermally curable resin composition, a radiation curable resin composition, and polymer particles further comprises a surfactant.
  • the porous polishing layer that comprises a crosslinked network comprising a thermally cured component and a radiation cured component, polymer particles dispersed within the crosslinked network, and closed cell pores dispersed within the crosslinked network further comprises a surfactant dispersed within the crosslinked network.
  • surfactants that may be useful for practicing the present disclosure include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants (e.g., zwitterionic surfactants), and combinations thereof. Each of these types of surfactant can include fluorochemical, silicone, and hydrocarbon-based surfactants.
  • Exemplary useful cationic surfactants include aliphatic ammonium salts.
  • Exemplary useful anionic surfactants include carboxylic acid salts (e.g., fatty acid salts and alkylether carboxylic acid salts), sulfonic acid salts (e.g., alkylbenzenesulfonic acid salts, alkylnaphthalene sulfonic acid salts, and alpha-olefinsulfonic acid salts), sulfuric acid salts (e.g., higher alcohol sulfuric acid ester saltsand alkylether sulfuric acid salts), and phosphoric acid salts (e.g., alkylphosphoric acid salts).
  • carboxylic acid salts e.g., fatty acid salts and alkylether carboxylic acid salts
  • sulfonic acid salts e.g., alkylbenzenesulfonic acid salts, alkylnaphthalene sulfonic acid salts, and alpha-o
  • Exemplary useful nonionic surfactants include polyoxyethylene alkyl ethers, ether esters (e.g., polyoxyethylene ethers of glycerin esters), esters (e.g., polyethylene glycol fatty acid esters, glycerin esters, sorbitan esters), and silicone glycol copolymers such as those available, for example, for Air Products, Allentown, Pa., under the trade designation “DABCO”.
  • the surfactant may be present in the composition or in the polishing layer, for example, in an amount up to ten percent (in some embodiments, up to 4, 3, or 2 percent) by weight, based on the total weight of the composition or the porous polishing layer.
  • the surfactant is present in an amount of at least one percent, based on the total weight of the composition or the porous polishing layer.
  • the present disclosure provides a method of making a polishing pad described herein. The method comprises forming pores in the composition comprising the thermally curable resin composition, the radiation curable resin composition, and polymer particles. In some embodiments, forming pores in the composition is carried out by mixing the composition. Mixing can be done with a variety of techniques, for example, using a machine mixer or hand mixing. In some embodiments, the mixing process (and the machine mixer) can include both rotation and revolution. Particle size and loading of the polymer particles can affect the porosity of the resulting polishing layer, as described above.
  • the composition comprising the thermally curable resin composition, the radiation curable resin composition, and polymer particles can be mixed together and placed on a support layer.
  • An open mold e.g., a mold having no top or lid
  • the mixture can be distributed within the mold by mechanical means to uniformly fill the mold. Suitable mechanical means can include low pressure pressing or the use of compaction rollers.
  • the method of making the polishing pad disclosed herein also includes forming a polishing layer by exposing the composition to radiation to at least partially cure the radiation curable composition and heating the composition to at least partially cure the thermally curable resin.
  • the radiation is typically ultraviolet radiation (i.e., radiation in the range from about 200 nm to about 400 nm).
  • the amount of radiation necessary to at least partially cure the composition will depend on a variety of factors including, e.g., the angle of exposure to the radiation, the thickness of the composition, the amount of polymerizable groups in the composition, and the type and amount of photoinitiator.
  • a UV light source with a wavelength from about 200 nm to about 400 nm is directed at the composition that is being transported on a conveyor system that provides a rate of passage past the UV source appropriate for the radiation absorption profile of the composition.
  • Useful sources of UV light include, e.g., extra high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low intensity fluorescent lamps, metal halide lamps, microwave powered lamps, xenon lamps, laser beam sources including, e.g., excimer lasers and argon-ion lasers, and combinations thereof.
  • the composition can then can be placed in an oven at, for example, an elevated temperature up to about 180° C., up to about 150° C., up to about 135° C., or up to about 120° C.
  • Exposure to radiation and heating can be carried out in either order or simultaneously. In some embodiments, exposure to radiation is carried out before heating.
  • the polishing pad of the present disclosure can have one or more work surfaces, wherein “work surface” as used herein refers to a surface of the polishing pad that can come into contact with the surface of the article that is to be polished.
  • the article to be polished can be a silicon wafer.
  • the work surface of the polishing pad can have surface features such as channels, grooves, perforations and combinations thereof. These surface features can enhance one or more of the following characteristics: (1) the movement of the polishing slurry between the work surface of the pad and the surface of the article that is being polished; (2) the removal and transport of abraded material away from the surface of the article that is being polished; or (3) the polishing or planarization efficiency of the polishing pad.
  • Surface features can be incorporated into the work surface of the polishing pad by a variety of methods.
  • the work surface of the pad can be mechanically modified, for example, by abrading or cutting.
  • surface features can be incorporated into the work surface of the pad during the molding process, for example, by providing at least one interior surface of the mold with raised features that can be imprinted into the work surface of the pad during its formation.
  • Surface features can be distributed in the form of random or uniform patterns across the work surface of the polishing pad. Exemplary surface feature patterns can include spirals, circles, squares, cross-hatches and waffle-like patterns.
  • the polishing pad according to or made according to the present disclosure comprises separate polishing elements protruding from the support layer.
  • FIG. 3 an embodiment of a polishing pad 2 is shown, comprising a plurality of polishing elements 4 , each of the polishing elements 4 being affixed to an optional support layer 8 .
  • the polishing pad 2 further comprises a compliant layer 10 .
  • the polishing layer comprising the separate polishing elements is a continuous layer although this is not shown in FIG. 3 .
  • the film can have a thickness, for example, of up to 0.01, 0.02, or 0.03 mm.
  • the polishing layer comprising separate polishing elements may have discontinuities, for example, in the film between the separate polishing elements. Since the polishing elements 4 are affixed to the support layer in the illustrated embodiment with a thin film layer (not shown) between polishing elements 4 , lateral movement of the polishing elements 4 with respect to one or more of the other polishing elements 4 is restricted, but the polishing elements 4 typically remain independently moveable in an axis normal to a polishing surface 14 of each polishing element 4 . As shown, each of the polishing elements 4 generally have a plurality of pores 15 distributed substantially throughout the entire polishing element 4 .
  • the polishing elements 4 are shown affixed to a first major side of the support layer 10 , for example, by direct bonding to the support layer 8 .
  • the polishing elements 4 may be molded and cured directly on the support layer 8 .
  • the polishing elements 4 may be attached to the support layer 8 or directly to the compliant layer 10 using an adhesive.
  • the porous polishing layer is typically a discontinuous layer.
  • an optional pressure sensitive adhesive layer 12 which may be used to secure the polishing pad 2 to a polishing platen (not shown in FIG. 3 ) of a CMP polishing apparatus (not shown in FIG. 3 ), is shown adjacent to the compliant layer 10 , opposite the support layer 8 .
  • FIG. 4 another exemplary embodiment of a polishing pad 2 ′ is shown, the polishing pad 2 ′ comprising a compliant layer 30 having a first major side and a second major side opposite the first major side; a plurality of polishing elements 24 , each polishing element 24 having a land region 25 for affixing each polishing element 24 to the first major side of the compliant layer 30 ; and an optional guide plate 31 having a first major surface and a second major surface opposite the first major surface, the guide plate 31 positioned to arrange the plurality of polishing elements 24 on the first major side of compliant layer 30 with the first major surface of guide plate 31 distal from the compliant layer 30 .
  • each polishing element 24 extends from the first major surface of the guide plate 31 along a first direction substantially normal to the first major side.
  • each of the porous polishing elements 24 is also shown as having a plurality of pores 15 distributed substantially throughout the entire polishing element 24 .
  • three polishing elements 24 are shown, and all of the polishing elements 24 are shown as porous polishing elements including both a porous polishing surface 23 and pores 15 distributed substantially throughout the entire polishing element 24 .
  • any number of polishing elements 24 may be used, and the number of porous polishing elements may be selected to be as few as one polishing element, to as many as all of the polishing elements, or any number in between.
  • An optional polishing composition distribution layer 28 is additionally illustrated by FIG. 4 .
  • the optional polishing composition distribution layer 28 aids distribution of the working liquid and/or polishing slurry to the individual polishing elements 24 .
  • a plurality of apertures 26 may also be provided extending through at least the guide plate 31 and the optional polishing composition distribution layer 28 as illustrated by FIG. 4 .
  • guide plate 31 may also serve as a polishing composition distribution layer.
  • each polishing element 24 has a land region 25 , and each polishing element 24 is affixed to the first major side of the compliant layer 30 by engagement of the corresponding land region 25 to the second major surface of the guide plate 31 . At least a portion of each polishing element 24 extends into a corresponding aperture 26 , and each polishing element 24 also passes through the corresponding aperture 26 and extends outwardly from the first major surface of the guide plate 31 .
  • the plurality of apertures 26 of guide plate 31 serves to guide the lateral arrangement of polishing elements 24 on the support layer 30 , while also engaging with each land region 25 to affix each the corresponding polishing element 24 to the support layer 30 .
  • the polishing elements 24 are free to independently undergo displacement in a direction substantially normal to the first major side of support layer 30 , while still remaining affixed to the compliant layer 30 by the guide plate 31 .
  • this may permit use of non-compliant polishing elements, for example, porous polishing elements having pores distributed substantially at or near only the polishing surface.
  • the polishing elements 24 are additionally affixed to a first major side of the compliant layer 30 using an optional adhesive layer 34 positioned at an interface between the compliant layer 30 and the guide plate 31 .
  • an optional adhesive layer 34 positioned at an interface between the compliant layer 30 and the guide plate 31 .
  • other bonding methods may be used, including direct bonding of the polishing elements 24 to the compliant layer 30 using, for example, heat and pressure.
  • the plurality of apertures may be arranged as an array of apertures, wherein at least a portion of the apertures 26 comprise a main bore and an undercut region of guide plate 31 , and the undercut region forms a shoulder that engages with the corresponding polishing element land region 25 , thereby retaining the polishing element 24 without requiring an adhesive between the polishing element 24 and the compliant layer 30 .
  • a second optional adhesive layer 36 may be used affix the optional polishing composition distribution layer 28 to a first major surface of the guide plate 31 , as illustrated by FIG. 4 .
  • an optional pressure sensitive adhesive layer 32 which may be used to secure the polishing pad 2 ′ to a polishing platen (not shown in FIG. 4 ) of a CMP polishing apparatus (not shown in FIG. 4 ), is shown adjacent to the support layer 30 , opposite the guide plate 31 .
  • a guide plate and/or distribution layer may also be used in connection with the embodiment shown in FIG. 3 , in which the porous polishing elements 4 do not have land regions.
  • the support layer 8 may be eliminated in the presence of a guide plate, and the porous polishing elements may be affixed to the compliant layer 10 , for example, using adhesive.
  • the cross-sectional shape of the polishing elements 4 and 24 taken through a polishing element 4 and 24 in a direction generally parallel to the polishing surface 14 and 23 , may vary widely depending on the intended application.
  • FIGS. 3 and 4 show generally cylindrical polishing element 4 and 24 having a generally circular cross section, other cross-sectional shapes are possible and may be desirable in some embodiments. For example, circular, elliptical, triangular, square, rectangular, hexagonal, and trapezoidal cross-sectional shapes may be useful.
  • the cross-sectional diameter of the polishing element 4 and 24 in a direction generally parallel to the polishing surface 14 and 23 may be from about 50 ⁇ m to about 20 mm, in some embodiments the cross-sectional diameter is from about 1 mm to about 15 mm, and in other embodiments the cross-sectional diameter is from about 5 mm to about 15 mm (or even about 5 mm to about 10 mm).
  • a characteristic dimension may be used to characterize the polishing element size in terms of a specified height, width, and length. In some exemplary embodiments, the characteristic dimension may be selected to be from about 0.1 mm to about 30 mm.
  • the cross-sectional area of each polishing element 4 and 24 in a direction generally parallel to the polishing surface 14 and 23 may be from about 1 mm 2 to about 1,000 mm 2 , in other embodiments from about 10 mm 2 to about 500 mm 2 , and in yet other embodiments, from about 20 mm 2 to about 250 mm 2 .
  • the polishing elements may be distributed on a major side of the compliant layer ( 10 in FIG. 3 , 30 in FIG. 4 ) in a wide variety of patterns, depending on the intended application, and the patterns may be regular or irregular.
  • the polishing elements may reside on substantially the entire surface of the compliant layer, or there may be regions of the support layer that include no polishing elements.
  • the polishing elements have an average surface coverage of the compliant layer from about 30 to about 95 percent of the total area of the major surface of the compliant layer, as determined by the number of polishing elements, the cross-sectional area of each polishing element, and the cross-sectional area of the polishing pad.
  • the cross-sectional area of the polishing pad in a direction generally parallel to a major surface of the polishing pad may, in some exemplary embodiments, range from about 100 cm 2 to about 300,000 cm 2 , in other embodiments from about 1,000 cm 2 to about 100,000 cm 2 , and in yet other embodiments, from about 2,000 cm 2 to about 50,000 cm 2 .
  • each polishing element ( 4 in FIG. 3 , 24 in FIG. 4 ) extends along the first direction substantially normal to the first major side of the compliant layer ( 10 in FIG. 3 , 30 in FIG. 4 ).
  • each polishing element extends along the first direction at least about 0.25 mm above a plane including the guide plate ( 31 in FIG. 4 ). In further exemplary embodiments, each polishing element extends along the first direction at least about 0.25 mm above a plane including the support layer ( 10 in FIG. 3 ). In additional exemplary embodiments, the height of the polishing surface ( 14 in FIG. 3 , 23 in FIG. 4 ) above the base or bottom of the polishing element ( 2 in FIG. 3 , 2 ′ in FIG. 4 ) may be 0.25 mm, 0.5 mm, 1.5 mm, 2.0 mm, 2.5 mm, 3.0 mm, 5.0 mm, 10 mm or more, depending on the polishing composition used and the material selected for the polishing elements.
  • the depth and spacing of the apertures 26 throughout the polishing composition distribution layer ( 28 and guide plate 31 may be varied as necessary for a specific CMP process.
  • the polishing elements 24 are each maintained in planar orientation with respect to one another and the polishing composition distribution layer 28 and guide plate 31 , and project above the surface of the polishing composition distribution layer 28 and guide plate 31 .
  • the volume created by the extension of the polishing elements ( 4 in FIG. 3 , 24 in FIG. 4 ) above the guide plate 31 and any polishing composition distribution layer ( 28 in FIG. 4 ) or support layer ( 8 in FIG. 3 ) may provide room for distribution of a polishing composition on the surface of the polishing composition distribution layer ( 28 in FIG. 4 ) or support layer ( 8 in FIG. 3 ).
  • the polishing elements ( 4 in FIG. 3 , 24 in FIG. 4 ) protrude above the polishing composition distribution layer ( 28 in FIG. 4 ) or support layer ( 8 in FIG.
  • polishing composition distribution layer 28 in FIG. 4
  • support layer 8 in FIG. 3
  • the guide plate useful for some embodiments can be made of a wide variety of materials, such as polymers, copolymers, polymer blends, polymer composites, or combinations thereof.
  • a non-conducting and liquid impermeable polymeric material is generally preferred, and polycarbonates have been found to be particularly useful.
  • the optional polishing composition distribution layer useful for some embodiments may also be made of a wide variety of polymeric materials.
  • the polishing composition distribution layer may, in some embodiments, comprise at least one hydrophilic polymer.
  • Preferred hydrophilic polymers include polyurethanes, polyacrylates, polyvinyl alcohols, polyoxymethylenes, and combinations thereof.
  • the polymeric materials are preferably porous, more preferably comprising a foam to provide a positive pressure directed toward to substrate during polishing operations when the polishing composition distribution layer is compressed. Porous or foamed materials with open or closed cells may be preferred in some embodiments.
  • the polishing composition distribution layer has between about 10 and about 90 percent porosity.
  • the polishing composition layer may comprise a hydrogel material, such as, for example a hydrophilic urethane, that can absorb water, preferably in a range of about 5 to about 60 percent by weight to provide a lubricious surface during polishing operations.
  • a hydrogel material such as, for example a hydrophilic urethane, that can absorb water, preferably in a range of about 5 to about 60 percent by weight to provide a lubricious surface during polishing operations.
  • the polishing composition distribution layer may substantially uniformly distribute a polishing composition across the surface of the substrate undergoing polishing, which may provide more uniform polishing.
  • the polishing composition distribution layer may optionally include flow resistant elements such as baffles, grooves (not shown in the figures), pores, and the like, to regulate the flow rate of the polishing composition during polishing.
  • the polishing composition distribution layer can include various layers of different materials to achieve desired polishing composition flow rates at varying depths from the polishing surface.
  • one or more of the polishing elements may include an open core region or cavity defined within the polishing element, although such an arrangement is not required.
  • the core of the polishing element can include sensors to detect pressure, conductivity, capacitance, eddy currents, and the like.
  • the support layer comprises a flexible and compliant material.
  • the support layer is typically a film that provides a surface onto which the composition comprising the thermally curable resin composition and the radiation curable resin composition can be cured.
  • the porous polishing layer includes polishing elements
  • the polishing elements at least a portion of which comprise porous polishing elements, may be formed with the support layer as a unitary sheet of polishing elements affixed to the support layer.
  • the support layer also serves to protect the compliant layer from water or other fluid in the polishing composition while the polishing pad is in use.
  • the support layer is generally fluid impermeable (although permeable materials may be used in combination with an optional barrier to prevent or inhibit fluid penetration through the support layer.
  • the support layer comprises a polymeric material selected from silicone, natural rubber, styrene-butadiene rubber, neoprene, polyurethane, polyolefin, and combinations thereof.
  • the support layer may further comprise a wide variety of additional materials, such as fillers, particulates, fibers, reinforcing agents, and the like.
  • the support layer is transparent.
  • Support layers can be made, for example, by extrusion of a material (e.g., silicone, natural rubber, styrene-butadiene rubber, neoprene, polyurethane, polyolefin, and combinations thereof) into a film.
  • a material e.g., silicone, natural rubber, styrene-butadiene rubber, neoprene, polyurethane, polyolefin, and combinations thereof
  • the material is a polyurethane available, for example, from Lubrizol Advanced Materials, Inc., Cleveland, Ohio, under the trade designation “ESTANE 58887-NAT02” or from Dow Chemical, Midland, Mich., under the trade designation “PELLETHANE” for example “PELLETHANE 2102-65D”.
  • films that are useful as support layers include polyurethane films available, for example, from Stevens Urethane, Easthampton, Mass., under the trade designations “ST-1882”, “ST-1035”, “SS-3331”, “SS-1495L”, and “ST-1880”.
  • the compliant layer comprises a flexible and compliant material, such as a compliant rubber or polymer.
  • the compliant layer is generally compressible to provide a positive pressure directed toward the polishing surface and can, for example, help provide uniformity of contact between the polishing pad and the surface of the substrate that is being polished.
  • the compliant layer is made of a compressible polymeric material (e.g., a foamed polymeric material made, for example, of natural rubber, synthetic rubber, or thermoplastic elastomer). Closed cell porous materials may be useful.
  • the compliant layer comprises a polyurethane and may be, for example, a foamed polyurethane or polyurethane impregnated felt.
  • the thickness of the compliant layer can be, for example, in a range from 0.2 to 3 mm.
  • the polishing layer includes polishing elements
  • the polishing elements at least a portion of which comprise porous polishing elements, may be formed with the compliant layer as a unitary sheet of polishing elements affixed to the compliant layer, which may be a porous compliant layer.
  • the compliant layer comprises a polymeric material selected from silicone, natural rubber, styrene-butadiene rubber, neoprene, polyolefin, polyurethane, and combinations thereof.
  • the support layer may further comprise a wide variety of additional materials, such as fillers, particulates, fibers, reinforcing agents, and the like.
  • the compliant layer is fluid impermeable (although permeable materials may be used in combination with the support layer described above).
  • Suitable commercially available compliant layers include, for example, microcellular polyurethanes available under the trade designation “PORON” from Rogers Corp., Rogers, Conn., for example, having product descriptions 4701-60-20062-04, 4701-50-20062-04, 4701-40-20062-04.
  • Other suitable compliant layers include polyurethane impregnated polyester felts available, for example, from Rodel, Incorporated, Newark, Del., under the trade designation “SUBA IV” as well as bonded rubber sheets available from Rubberite Cypress Sponge Rubber Products, Inc., Santa Ana, Calif., under the trade designation “BONDTEX”.
  • the polishing pad may include a window extending through the pad in the direction normal to the polishing surface, or may use transparent layers and/or transparent polishing elements, to allow for optical endpointing of a polishing process, as described in Int. Pat. Appl. Pub. No. WO 2009/140622 (Bajaj et al.).
  • transparent layer is intended to include a layer that comprises a transparent region, which may be made of a material that is the same or different from the remainder of the layer.
  • at least one of a polishing element, the support layer, the compliant layer, or a region of the polishing layer or support layer may be transparent, or may be made transparent by applying heat and/or pressure to the material.
  • a transparent material may be cast in place in an opening suitably positioned in a layer (e.g., using a mold) to create a transparent region (e.g., in the polishing layer, support layer, or compliant layer).
  • the polishing layer is cured in the presence of a pre-formed window to create a transparent region in the polishing layer.
  • the entire support layer and/or compliant layer may be made of a material that is or may be made transparent to energy in the range of wavelength(s) of interest utilized by an endpoint detection apparatus. Suitable transparent materials for a transparent element, layer or region include, for example, transparent polyurethanes.
  • the term “transparent” is intended to include an element, layer, and or region that is substantially transparent to energy in the range of wavelength(s) of interest utilized by an endpoint detection apparatus.
  • the endpoint detection apparatus uses one or more source of electromagnetic energy to emit radiation in the form of ultraviolet light, visible light, infrared light, microwaves, radio waves, combinations thereof, and the like.
  • the term “transparent” means that at least about 25% (e.g., at least about 35%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95%) of energy at a wavelength of interest that impinges upon the transparent element, layer or region is transmitted therethrough.
  • the support layer is transparent. In some embodiments, the polishing layer is transparent. In some exemplary embodiments, including embodiments illustrated in FIG. 3 above, at least one polishing element is transparent. In some embodiments, the support layer is transparent, at least a portion of the polishing layer (e.g., a polishing element) is transparent, and there is a hole in the compliant layer aligned with the transparent portion of the polishing layer.
  • At least one polishing element is transparent, and the adhesive layer and the compliant layer are also transparent.
  • the compliant layer, the guide plate, the polishing composition distribution layer, at least one polishing element, or a combination thereof is transparent.
  • the present disclosure is further directed to a method of using a polishing pad as described above in a polishing process, the method including contacting a surface of a substrate with the porous polishing layer of the polishing pad according to the present disclosure and relatively moving the polishing pad with respect to the substrate to abrade the surface of the substrate.
  • the porous polishing layer of the polishing pad comprises a plurality of polishing elements, at least some of which are porous.
  • a working liquid may be provided to an interface between the polishing pad surface and the substrate surface. Suitable working liquids include, for example, those described in U.S. Pat. Nos. 6,238,592 (Hardy et al) and 6,491,843 (Srinivasan et al.) and in Int. Pat. Appl. Pub. No. WO 2002/33736 (Her et al.).
  • the polishing layer in the polishing pad of the present disclosure and/or prepared according to the method of the present disclosure can have an average pore size of at least 5 microns, at least 10 microns, or at least 15 microns.
  • the polishing pad can have an average pore size of up to 100, 75, 50, 45, or 40 microns.
  • the average pore size can be in a range from 5 to 100, 5 to 75, 5 to 50, 5 to 40, or 5 to 30 microns.
  • the polishing pad can have an average pore size of up to 30, 25, or 20 microns.
  • the pore size generally refers to the diameter of the pore. However, in embodiments in which the pores are non-spherical, the pore size can refer to the largest dimension of the pore. In some embodiments, the pore size non-uniformity is in a range from 40 to 75 percent or in a range from 40 to 60 percent. In some embodiments, the pore size non-uniformity is up to 75, 70, 65, 60, 55, or 50 percent. In contrast, comparative compositions comprising thermally curable compositions can have a pore size non-uniformity that is greater than 80, 90 or 100%. In some embodiments, the polishing layer in the polishing pad according to the present disclosure can have a porosity in a range from 5 to 60 percent or in a range from 5 to 55, 10 to 50, or 10 to 40 percent.
  • FIGS. 5A , 5 B, 6 A, and 6 B The difference between the control of pore size in the polishing layer according to the present disclosure and in a comparative thermally curable composition is illustrated in FIGS. 5A , 5 B, 6 A, and 6 B.
  • FIGS. 5A and 5B are micrographs of a cross-section and top view, respectively, of the cured composition described in Example 2 in the Examples below.
  • FIGS. 6A and 6B are micrographs of a cross-section and a top view, respectively of the cured composition of Comparative Example 3.
  • Both Example 2 and Comparative Example 3 were prepared using ten percent by weight polymer particles and mixed the same way. However, Example 2 was cured both by radiation curing and by thermal curing, and Comparative Example 3 was cured by thermal curing only.
  • Example 2 The micrographs illustrate that the pores in Example 2 are better controlled than the pores of Comparative Example 3.
  • Table 1 in the following Examples also supports that there is a lower size range, lower pore size non-uniformity, and higher hardness in Example 2 than in Comparative Example 3
  • control over the pore size and pore size non-uniformity may be related to the hardness of the polishing layer.
  • the porous polishing layer has a hardness of at least 40, 45, or 50 Shore D.
  • the hardness can be measured, for example, according to Test Method 2, described in the Examples below.
  • comparative compositions comprising thermally curable compositions may have a hardness of less than 40 Shore D.
  • Surfactants are useful in the compositions and porous polishing layers disclosed herein, for example, for typically reducing the pore size and the pore size range and enhancing the pore distribution even more than with the dual cure method in the absence of surfactant.
  • the addition of a surfactant can help provide better control on the pore size distribution and the size, density, and shape of the pores, which in turn can have a positive impact on key metrics of uniform performance (e.g., removal rate and within wafer uniformity).
  • Example 7A and 7B which are micrographs of a cross-section and top view, respectively, of the cured composition described in Example 15 in the Examples below, illustrate that the addition of a surfactant can have a positive impact on the pore size range and pore distribution.
  • a surfactant can have a positive impact on the pore size range and pore distribution.
  • Example 15 there is a lower pore size range in Example 15 than there is in Example 2, which has the same number of polymer particles and is prepared in the same way but has no surfactant.
  • the present disclosure provides a polishing pad comprising:
  • a compliant layer having first and second opposing sides
  • porous polishing layer disposed on the first side of the compliant layer, the porous polishing layer comprising:
  • the present disclosure provides the polishing pad according to the first embodiment, further comprising a support layer interposed between the compliant layer and the porous polishing layer.
  • the present disclosure provides the polishing pad according to the first or second embodiment, wherein the thermally cured component comprises at least one of a polyurethane or a polyepoxide, and wherein the radiation cured component comprises at least one of a polyacrylate, a polymethacrylate, a poly(vinyl ether), a polyvinyl, or a polyepoxide.
  • the present disclosure provides the polishing pad according to the first or second embodiment, wherein thermally cured component and the polymer particles each independently comprise a polyurethane.
  • the present disclosure provides the polishing pad according to any one of the first to fourth embodiments, wherein the polymer particles are covalently bonded to at least one of the thermally cured component or the radiation cured component in the crosslinked network.
  • the present disclosure provides the polishing pad according to any one of the first to fifth embodiments, wherein the radiation cured component comprises at least one of a polyacrylate or a polymethacrylate.
  • the present disclosure provides the polishing pad according to the sixth embodiment, wherein the polyacrylate or polymethacrylate is covalently bonded to the thermally cured component through urethane or urea linking groups.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the porous polishing layer has a hardness of at least 40 Shore D as measured by Test Method 2.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polymer particles have a mean particle size in a range from 5 micrometers to 500 micrometers.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polymer particles are substantially spherical.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polymeric particles are fibers.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polymer particles are present up to 20 percent by weight, based on the total weight of the porous polishing layer.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the pores have a pore size non-uniformity up to 75 percent.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the pores have an average pore size in a range from 5 microns to 100 microns.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polishing layer comprises separate polishing elements protruding from the support layer or compliant layer.
  • the present disclosure provides the polishing pad according to the fifteenth embodiment, wherein polishing elements each have an end distal from the support layer, and wherein the distal end is movable in an axis normal to a polishing surface of the polishing elements.
  • the present disclosure provides the polishing pad according to the fifteenth or sixteenth embodiment, further comprising a guide plate having a plurality of openings therein, the separate polishing elements each protruding through one of the plurality of openings.
  • the present disclosure provides the polishing pad according to any one of the fifteenth to seventeenth embodiment, wherein the polishing elements are affixed to the compliant layer with adhesive.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the compliant layer comprises at least one of silicone, natural rubber, styrene-butadiene rubber, neoprene, polyolefin, or polyurethane.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein at least a portion of the polishing pad is transparent.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the polymer particles are soluble in water.
  • the present disclosure provides the polishing pad according to any preceding embodiment, wherein the porous polishing layer further comprises a surfactant in the crosslinked network.
  • the present disclosure provides a method of making a polishing pad, the method comprising:
  • composition comprising a thermally curable resin composition, a radiation curable resin composition, and polymer particles;
  • forming a porous polishing layer on the support layer by exposing the composition to radiation to at least partially cure the radiation curable resin composition and heating the composition to at least partially cure the thermally curable resin composition.
  • the present disclosure provides a method according to the twenty-third embodiment, further comprising adhesively bonding a compliant layer to a surface of the support layer opposite the porous polishing layer.
  • the present disclosure provides the method according to the twenty-third or twenty-fourth embodiment, wherein the thermally curable resin composition comprises a first resin having at least two isocyanate groups or at least two epoxide groups and at least a second resin having at least two hydroxyl, amino, carboxy, or mercaptan groups, and wherein the radiation curable composition comprises at least two acrylate, methacrylate, vinyl, or epoxide groups.
  • the present disclosure provides the method according to the twenty-fifth embodiment, wherein the first resin has at least two isocyanate groups, wherein the second resin has at least two hydroxyl groups or at least two amino groups, wherein the radiation curable composition comprises at least two acrylate or methacrylate groups, and wherein the radiation curable composition further comprises at least one of an isocyanate group or a hydroxyl group.
  • the present disclosure provides the method according to the twenty-sixth embodiment, wherein the radiation curable composition is an aliphatic, isocyanate-functional urethane acrylate or methacrylate.
  • the present disclosure provides the method according to any one of the twenty-third to twenty-seventh embodiments, further comprising positioning an open mold in the composition on the support layer before the porous polishing layer is formed.
  • the present disclosure provides the method according to any one of the twenty-third to twenty-eighth embodiments, wherein the pores are closed cell pores.
  • the present disclosure provides the method according to any one of the twenty-third to twenty-ninth embodiments, wherein the composition further comprises a surfactant.
  • the present disclosure provides the method according to any one of the twenty-third to thirtieth embodiments, wherein the porous polishing layer has a hardness of at least 40 Shore D as measured by Test Method 2.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-first embodiments, wherein the polymer particles have an average particle size in a range from 5 micrometers to 500 micrometers.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-second embodiments, wherein the polymer particles are substantially spherical.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-third embodiments, wherein the polymer particles are fibers.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-fourth embodiment, wherein the polymer particles are soluble in water.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-fifth embodiments, wherein the polymer particles are present up to 20 percent by weight, based on the total weight of the porous polishing layer.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-sixth embodiments, wherein the pores have a pore size non-uniformity up to 75 percent.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-seventh embodiments, wherein the pores have an average pore size in a range from 5 microns to 100 microns.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-eighth embodiments, wherein the polishing layer comprises separate polishing elements affixed to and protruding from the support layer.
  • the present disclosure provides the method according to the thirty-ninth embodiment, wherein the separate polishing elements each have an affixed end and an end distal from the support layer, and wherein the distal end is movable in an axis normal to a polishing surface of the polishing elements.
  • the present disclosure provides the method according to any one of the twenty-third to thirty-eighth embodiments, wherein the polishing layer comprises separate polishing elements protruding from the compliant layer, wherein polishing elements each have an end distal from the support layer, and wherein the distal end is movable in an axis normal to a polishing surface of the polishing elements.
  • the present disclosure provides the method according to any one of the thirty-ninth to forty-first embodiments, further comprising a guide plate having a plurality of openings therein, the discrete polishing elements each protruding through one of the plurality of openings.
  • the present disclosure provides the method according to any one of the twenty-third to forty-second embodiments, wherein the support layer comprises at least one of silicone, natural rubber, styrene-butadiene rubber, neoprene, polyolefin, or polyurethane.
  • the present disclosure provides the method according to any one of the twenty-third to forty-third embodiments, wherein at least a portion of the polishing pad is transparent.
  • the present disclosure provides a method of polishing comprising:
  • the present disclosure provides the method of the forty-fifth embodiment, further comprising providing a working liquid to an interface between the porous polishing layer and the substrate surface.
  • TPO-L 2,4,6-trimethylbenzoylphenylphosphinic acid ethyl ester available under the trade designation “Lucirin TPO-L” available from BASF, Florham Park, New Jersey.
  • ST-1880 An aromatic polyurethane film available under the trade designation “ST-1880” from Stevens Urethane, Easthampton, Massachusetts.
  • a silicone glycol copolymer surfactant available under the trade designation “DABCO DC5604” from Air Products Chemicals, Inc., Allentown, Pennsylvania
  • Durometer measurements were taken using a Model 1500 Shore D durometer available from Rex Gauge Company, Inc., Buffalo Grove, Ill. Values reported in Table 1 are the average of five measurements, each measurement made on a different polishing feature of the example.
  • Test Method 3 Pore Size Determination via Optical Microscopy.
  • the pore size mean, pore size standard deviation (Std. Dev.), pore size range (the maximum size pore observed minus the minimum size pore observed), pore size non-uniformity (the pore size Std. Dev. divided by the mean pore size multiplied by 100) and the porosity (measured area of the image consisting of pores divided by the entire area of the image multiplied by 100) were determined using image analysis of optical images obtained using a MM-40 Nikon measuring microscope available from Nikon Instruments, Inc. Elgin, Ill., in combination with Image-pro plus analysis software available from Media Cybernetics, Bethesda, Md.
  • Step 1 8 inch diameter, 240 grit disc obtained from 3M Company under the trade designation “3M WETORDRY PSA Disc 21366”, the grinding time was 3 min with water as a grinding fluid.
  • Step 2 8 inch diameter, 600 Grit disc obtained from Buehler Ltd., under the trade designation “CARBIMET 8” PSA Disc 30-5118-600-100, the grinding time was 6 min with water as the grinding fluid.
  • Step 3 8′′ diameter pad obtained from Buehler Ltd. under the trade designation “TEXMET 1500 Polishing Pad”, 40-8618, the polishing time was 6 min with 15 ⁇ m grade polycrystalline diamond suspension 90-30035, available from Allied High Tech Products, Inc., Collinso Dominguez, Calif., as the polishing fluid.
  • Step 4 8 inch diameter pad obtained from Buehler Ltd. under the trade designation “TEXMET 1500 Polishing Pad”, 40-8618, the polishing time was 6 min with 6 ⁇ M grade polycrystalline diamond suspension 90-30025, available from Allied High Tech Products, Inc., as the polishing fluid.
  • Step 5 8 inch diameter pad obtained from Buehler Ltd. under the trade designation “TEXMET 1500 Polishing Pad”, 40-8618, the polishing time was 6 min with 3 ⁇ M grade polycrystalline diamond suspension 90-30020, available from Allied High Tech Products, Inc., as the polishing fluid.
  • Step 6 8 inch diameter pad obtained from Buehler Ltd. under the trade designation “TEXMET 1500 Polishing Pad”, 40-8618, the polishing time was 6 min with 1 ⁇ M grade polycrystalline diamond suspension 90-30015, available from Allied High Tech Products, Inc., as the polishing fluid.
  • the polished surface of the features was then coated with carbon using a sputtering coater available from Denton Vacuum, LLC, Moorestown, N.J., using conventional techniques. Optical imaging was subsequently conducted.
  • Example 1 was prepared by placing 0.28 g 5350D, 2.15 g M1, 1.83 g PHP-75D, 1.27 g D100 and 0.06 g TPO-L in a 50 mL plastic beaker. The components were mixed together by placing the beaker in an Awatori-Rentaro AR-500 Thinky Mixer (from Thinky Corporation, Tokyo, Japan) and running the AR-500 in a two step process. The first step was conducted at a rotation of 1000 rpm and a revolution of 1000 rpm for 5 minutes. The second step immediately followed the first and was conducted at a rotation of 30 rpm and a revolution of 2000 rpm for 15 seconds, forming a resin mixture.
  • Awatori-Rentaro AR-500 Thinky Mixer from Thinky Corporation, Tokyo, Japan
  • the resin mixture was poured into a teflon coated, Ni plated, aluminum mold formed from an aluminum plate having a length of 19.5 cm and width of 9.2 cm.
  • the mold consisted of a square array of tapered, cylindrical cavities.
  • the cavities had a diameter of 7.8 mm at the top of the cavity, a 6.5 mm diameter at the bottom of the cavity and a depth of 1.8 mm.
  • the center to center distance between cavities was about 11.7 mm.
  • a piece of polyurethane film, ST-1880, was used as a backing.
  • the backing was cut to size, about 12 cm ⁇ 10 cm, and placed over the region of the mold containing the resin mixture.
  • a quartz plate, 28 cm length ⁇ 17 cm width ⁇ 3.5 mm thickness was placed on top of the polyurethane backing, forcing the resin into the cavities and creating a thin land region, about 0.5 mm thick, of resin mixture between the cavities.
  • the resin mixture was UV cured by passing the mold, resin mixture, backing and quartz plate under two ultraviolet light lamps (‘V’ bulb, available from Fusion Systems Inc., Gaithersburg, Md.) that operated at about 157.5 Watts/cm (400 Watts/inch).
  • the mold passed under the lights at a speed of about 2.4 meters/minute (8 feet/minute) with the radiation passing through the quartz plate and polyurethane backing to reach the resin mixture.
  • the mold, partially cured resin mixture and polyurethane backing was then transferred to an air flow through oven having a set temperature of 100° C. for two hours to thermally cure the resin mixture.
  • the cured article was removed from the mold by gently pulling on the polyurethane backing, forming an article having structured polishing features, Example 1.
  • Example 2 was prepared identically to Example 1 except the composition of the resin mixture was 0.58 g 5350D, 2.15 g M1, 1.83 g PHP-75D, 1.27 g D100 and 0.06 g TPO-L.
  • Example 3 was prepared identically to Example 1 except the curing was conducted in the reverse order, the thermal cure first followed by the UV cure.
  • Example 4 was prepared identically to Example 2 except the curing was conducted in the reverse order, the thermal cure first followed by the UV cure.
  • Comparative Example C1 was prepared identically to Example 1 except the 5350D was omitted from the composition of the resin mixture.
  • Comparative Example C2 was prepared identically to Comparative Example C1 except the composition of the resin mixture was 0.31 g 5350D, 2.15 g M1, and 3.65 g PHP-75D and only the thermal cure at 100° C. for two hours was used, the UV curing step being omitted.
  • Comparative Example C3 was prepared identically to Comparative Example C2 except the composition of the resin mixture was 0.65 g 5350D, 2.15 g M1, and 3.65 g PHP-75D.
  • Example 5 was prepared by placing 9.49 g 5350D, 35.00 g M1, 29.69 g PHP-75D, 20.63 g D100 and 1.03 g TPO-L in a 500 ml plastic beaker. The components were mixed together by placing the beaker in the Awatori-Rentaro AR-500 Thinky Mixer and running the AR-500 in a two step process. The first step was conducted at a rotation of 1000 rpm and a revolution of 1000 rpm for 5 minutes. The second step immediately followed the first and was conducted at a rotation of 30 rpm and a revolution of 2000 rpm for 15 s forming a resin mixture.
  • an approximate 28 cm ⁇ 28 cm coating of the resin mixture was prepared on a 26 ⁇ m thick backing formed by extrusion of a thermoplastic polyurethane (TPU), ESTANE 58887-NAT02 (available from Lubrizol Advanced Materials, Inc., Cleveland, Ohio) into film form at 182° C. onto a paper release liner.
  • TPU thermoplastic polyurethane
  • ESTANE 58887-NAT02 available from Lubrizol Advanced Materials, Inc., Cleveland, Ohio
  • the coated resin mixture and backing were placed on a 12 inch ⁇ 12 inch (30.5 cm ⁇ 30.5 cm) by 0.25 inch (6.35 mm) thick aluminum plate. Thirty-six magnets, 0.375 inch (9.6 mm) in diameter by 0.125 inch (3.2 mm) thick were fitted into recesses in the back of the aluminum plate. The 36 recesses were in a square array with center to center distances between recesses of about 5 cm. The diameter and depth of the recesses were 9.8 mm and 4.3 mm, respectively.
  • a teflon coated metal screen about 41 cm ⁇ 30 cm and about 1.6 mm in thickness, having a hexagonal array of circular holes each about 6.2 mm in diameter and a center to center distance of about 8 mm was placed on top of the resin mixture coating.
  • the magnetic attraction between the screen and the magnets in the aluminum plate caused the screen to be forced through the resin mixture coating, leaving a thin land region of the coating between the metal screen and backing.
  • the UV curing of the coating was conducted identically to that of Example 1, except the quartz plate was not used. Thermal cure followed, using the identical procedure as that described in Example 1.
  • the metal screen was removed from the cured resin, forming a textured pad surface adhered to the original paper backed polyurethane backing.
  • the paper was removed exposing the opposite side of the polyurethane backing Using a 127 ⁇ m thick transfer adhesive, 3M Adhesive Transfer Tape 9672 (from 3M Company), the polyurethane backing of the textured pad surface was hand laminated to an approximate 30 cm ⁇ 30 cm by 0.0625 inch (1.59 mm) thick piece of polyurethane foam, Rogers “PORON” urethane foam, part #4701-50-20062-04 (from American Flexible Products, Inc., Chaska, Minn.). A 23 cm diameter pad with an 18 mm diameter center hole was die cut from the laminate forming a pad having structured polishing features of the present invention, Example 5.
  • Comparative Example C4 was prepared identically to Example 5, except the composition of the resin mixture was 10.48 g 5350D, 35.00 g M1, and 59.38 g PHP-75D and only the thermal cure at 100° C. for two hours was used, the UV curing step being omitted.
  • Example 6 was prepared identically to Example 1 except the composition of the resin mixture was 0.28 g 5150D, 2.15 g M1, 1.83 g PHP-75D, 1.27 g D100 and 0.06 g TPO-L.
  • Example I-1 was prepared identically to Example 1 except the composition of the resin mixture was 0.28 g 5070D, 2.15 g M1, 1.83 g PHP-75D, 1.27 g D100 and 0.06 g TPO-L.
  • Example 7 was prepared identically to Example 1 except the amount of 5350D was 0.05 g.
  • Example 8 was prepared identically to Example 1 except the amount of 5350D was 0.14 g.
  • Example 9 was prepared identically to Example 1 except the amount of 5350D was 0.93 g.
  • Example I-2 was prepared identically to Example 1 except the amount of 5350D was 1.31 g.
  • FESEM (Test Method 1) results of Examples 6-9 indicated that they had an acceptable level of porosity.
  • FESEM (Test Method 1) results of Illustrative Examples I-1 and I-2 indicated that they had a low level of porosity.
  • Example 10 was prepared identically to Example 5 except for the following changes.
  • the composition of the resin mixture was 0.62 g A15LV, 23 g P-250, 15.83 g PHP-75D, 22 g D100, 1.1 g TPO-L and 0.68 g DC5604.
  • the components were place and mixed in a 500 ml plastic container.
  • the resin mixture was UV cured by passing the screen with resin mixture and TPU backing under two ultraviolet light lamps (‘V’ bulb, available from Fusion Systems Inc.) that operated at about 157.5 Watts/cm (400 Watts/inch).
  • the resin mixture passed under the lights at a speed of about 2.4 meters/minute (8 feet/minute) with the radiation passing through the resin mixture.
  • a fluoropolymer coated polyester film release liner obtained from 3M Company under the trade designation “3M SCOTCHPAK 1022 Release Liner” was put on top of the screen and partially cured resin mixture.
  • the assembly was then flipped over such that the polyurethane backing was on top and the fluoropolymer coated polyester film/screen/partially cured resin mixture at the bottom.
  • Example 11 was prepared identically to Example 10 except that the weight of A15LV was 1.25 g.
  • Example 12 was prepared identically to Example 10 except that the weight of A15LV was 3.20 g.
  • Example 13 was prepared identically to Example 10 except that the weight of A15LV was 6.76 g.
  • Example 14 was prepared by placing 6.88 g A15LV, 127.78 g P-250, 6.11 g TPO-L and 3.51 g DC5604 in a 650 ml plastic container. The components were mixed together by placing the container in the Awatori-Rentaro AR-500 Thinky Mixer and running the AR-500 at a rotation of 1000 rpm and a revolution of 1000 rpm for 4 minutes. The container was removed from the mixer and 87.29 g PHP-75D and 122.22 g D100 were added to the container. The mixture went through a two step mixing process. The first step was conducted at a rotation of 1000 rpm and a revolution of 1000 rpm for 4 minutes. The second step immediately followed the first and was conducted at a rotation of 30 rpm and a revolution of 2000 rpm for 15 second forming a resin mixture.
  • an approximate 21 in ⁇ 23 in (53.3 cm ⁇ 58.4) coating of the resin mixture was prepared on a 4 mil (102 vim) thick backing formed by extrusion of the TPU, “ESTANE 58309-022”, into film form at 210° C. onto a conventional 4 mil polyester release liner.
  • the coated resin mixture and backing were placed on a 24 inch ⁇ 24 inch (61.0 cm ⁇ 61.0 cm) by 0.25 inch (6.35 mm) thick aluminum plate.
  • 113 magnets, 0.375 inch (9.6 mm) in diameter by 0.125 inch (3.2 mm) thick were fitted into recesses in the back of the aluminum plate.
  • the recesses were in a linear array consisting of 15 rows. Eight of the rows had 8 recesses per row while 7 of the rows had seven recesses per row. The spacing between rows was 4 mm while the spacing between recesses within a row was 7.5 mm. The first row of recesses (near an edge of the plate) had eight recesses; the second row had seven recesses. This alternating pattern continued until the fifteenth row having eight recesses. The recesses for the even numbered rows were positioned such that they were centered between the recesses of the corresponding adjacent rows. The diameter and depth of the recesses were 9.8 mm and 4.3 mm, respectively. A tape capable of handling high temperature was used to secure the magnets in the recesses.
  • a teflon coated metal screen about 24 in ⁇ 24 in (61.0 cm ⁇ 61.0 cm) and about 1.6 mm in thickness, having a hexagonal array of circular holes each about 6.2 mm in diameter and a center to center distance of about 8 mm was placed on top of the resin mixture coating.
  • the magnetic attraction between the screen and the magnets in the aluminum plate caused the screen to be forced through the resin mixture coating, leaving a thin land region of the coating between the metal screen and backing.
  • the resin mixture was cured following the identical curing procedure of Example 10. After removing from the oven, the metal screen was removed from the cured resin, forming a textured pad surface adhered to the original polyester backed polyurethane TPU backing. Using a 127 ⁇ m thick transfer adhesive, “3M ADHESIVE TRANSFER TAPE 9672” (from 3M Company), the polyester release liner of the textured pad surface was hand laminated to an approximate 21 in ⁇ 23 in (53.3 cm ⁇ 58.4) by 0.0787 inch (2 mm) thick piece of polyurethane foam. A 20.0 in (50.8 cm) diameter pad was die cut from the laminate forming a pad having structured polishing features of the present invention, Example 14.
  • Comparative Example C5 was prepared identically to Example 10 except the A15LV was omitted from the composition of the resin mixture.
  • Comparative Example C6 was prepared identically to Example 10, except the composition of the resin mixture was 1.44 g A15LV, 23 g P-250, 47.50 g PHP-75D and 0.68 g DC5604, and only the thermal cure at 100° C. for two hours was used, the UV curing step being omitted.
  • Comparative Example C7 was prepared identically to Comparative Example C6 except the A15LV was omitted from the composition of the resin mixture.
  • Example 15 was prepared identically to Example 5 except that the composition of the resin mixture was 7.58 g 5350D, 28.00 g M1, 23.75 g PHP-75D, 16.50 g D100, 0.83 g TPO-L and 0.77 g DC5604.
  • Comparative Example C8 was prepared identically to Example 15, except the composition of the resin mixture was 8.39 g 5350D, 28.00 g M1, 47.50 g PHP-75D and 3.5 g DC5604, and only the thermal cure at 100° C. for two hours was used, the UV curing step being omitted.

Landscapes

  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Physics & Mathematics (AREA)
  • Power Engineering (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Mechanical Treatment Of Semiconductor (AREA)
  • Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
US13/518,475 2009-12-22 2010-12-20 Polishing pad and method of making the same Abandoned US20130012108A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/518,475 US20130012108A1 (en) 2009-12-22 2010-12-20 Polishing pad and method of making the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US28898209P 2009-12-22 2009-12-22
US42244210P 2010-12-13 2010-12-13
US13/518,475 US20130012108A1 (en) 2009-12-22 2010-12-20 Polishing pad and method of making the same
PCT/US2010/061199 WO2011087737A2 (en) 2009-12-22 2010-12-20 Polishing pad and method of making the same

Publications (1)

Publication Number Publication Date
US20130012108A1 true US20130012108A1 (en) 2013-01-10

Family

ID=44247814

Family Applications (1)

Application Number Title Priority Date Filing Date
US13/518,475 Abandoned US20130012108A1 (en) 2009-12-22 2010-12-20 Polishing pad and method of making the same

Country Status (6)

Country Link
US (1) US20130012108A1 (ja)
JP (1) JP5728026B2 (ja)
KR (1) KR101855073B1 (ja)
SG (1) SG181890A1 (ja)
TW (1) TWI517975B (ja)
WO (1) WO2011087737A2 (ja)

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110183583A1 (en) * 2008-07-18 2011-07-28 Joseph William D Polishing Pad with Floating Elements and Method of Making and Using the Same
US20130323993A1 (en) * 2011-01-04 2013-12-05 Evonik Degussa Gmbh Composite semifinished products, molded parts produced therefrom, and molded parts produced directly based on hydroxy-functionalized (meth)acrylates, which are cross-linked by means of uretdiones in a thermosetting manner
US20150050866A1 (en) * 2013-08-16 2015-02-19 San Fang Chemical Industry Co., Ltd. Polishing pad, polishing apparatus and method for manufacturing polishing pad
US20160136778A1 (en) * 2014-11-17 2016-05-19 San Fang Chemical Industry Co., Ltd. Polishing pad and method for making the same
WO2016176108A1 (en) * 2015-04-30 2016-11-03 Frito-Lay North America, Inc. Method and apparatus for removing a portion of a food product with an abrasive stream
US20160339559A1 (en) * 2015-05-20 2016-11-24 FNS Tech. Co., Ltd. Polishing pad and preparing method thereof
US20160375550A1 (en) * 2015-06-26 2016-12-29 Rohm And Haas Electronic Materials Cmp Holdings, Inc. Controlled-porosity method for forming polishing pad
WO2017066077A1 (en) 2015-10-16 2017-04-20 Applied Materials, Inc. Method and apparatus for forming advanced polishing pads using an additive manufacturing process
WO2017127221A1 (en) * 2016-01-19 2017-07-27 Applied Materials, Inc. Porous chemical mechanical polishing pads
US9931728B2 (en) 2011-11-29 2018-04-03 Cabot Microelectronics Corporation Polishing pad with foundation layer and polishing surface layer
WO2018187220A1 (en) * 2017-04-03 2018-10-11 Jl Darling Llc Coating for recyclable paper
US10195714B2 (en) 2014-03-31 2019-02-05 Fujibo Holdings, Inc. Polishing pad and process for producing same
WO2019032286A1 (en) * 2017-08-07 2019-02-14 Applied Materials, Inc. ABRASIVE DISTRIBUTION POLISHING PADS AND METHODS OF MAKING SAME
US20190106607A1 (en) * 2016-05-23 2019-04-11 Tatsuta Electric Wire & Cable Co., Ltd. Conductive Adhesive Composition
CN110142687A (zh) * 2014-10-17 2019-08-20 应用材料公司 由积层制造工艺所生产的研磨垫
US10384330B2 (en) 2014-10-17 2019-08-20 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US10391605B2 (en) 2016-01-19 2019-08-27 Applied Materials, Inc. Method and apparatus for forming porous advanced polishing pads using an additive manufacturing process
US10399201B2 (en) 2014-10-17 2019-09-03 Applied Materials, Inc. Advanced polishing pads having compositional gradients by use of an additive manufacturing process
US20200171623A1 (en) * 2018-11-30 2020-06-04 Taiwan Semiconductor Manufacturing Co., Ltd. Wafer backside cleaning apparatus and method of cleaning wafer backside
US10821573B2 (en) 2014-10-17 2020-11-03 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US10875153B2 (en) 2014-10-17 2020-12-29 Applied Materials, Inc. Advanced polishing pad materials and formulations
US10875145B2 (en) 2014-10-17 2020-12-29 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US20220209324A1 (en) * 2019-04-05 2022-06-30 Ddp Specialty Electronic Materials Us, Llc Polyurethane based thermal interface material
US11471999B2 (en) 2017-07-26 2022-10-18 Applied Materials, Inc. Integrated abrasive polishing pads and manufacturing methods
US11612978B2 (en) 2020-06-09 2023-03-28 Applied Materials, Inc. Additive manufacturing of polishing pads
US11638979B2 (en) 2020-06-09 2023-05-02 Applied Materials, Inc. Additive manufacturing of polishing pads
US11685014B2 (en) 2018-09-04 2023-06-27 Applied Materials, Inc. Formulations for advanced polishing pads
US11745302B2 (en) 2014-10-17 2023-09-05 Applied Materials, Inc. Methods and precursor formulations for forming advanced polishing pads by use of an additive manufacturing process
US11794308B2 (en) * 2013-11-04 2023-10-24 Applied Materials, Inc. Printed chemical mechanical polishing pad having particles therein
US11807710B2 (en) 2020-10-19 2023-11-07 Cmc Materials, Inc. UV-curable resins used for chemical mechanical polishing pads
US11806829B2 (en) 2020-06-19 2023-11-07 Applied Materials, Inc. Advanced polishing pads and related polishing pad manufacturing methods
US11813712B2 (en) 2019-12-20 2023-11-14 Applied Materials, Inc. Polishing pads having selectively arranged porosity
US11826876B2 (en) 2018-05-07 2023-11-28 Applied Materials, Inc. Hydrophilic and zeta potential tunable chemical mechanical polishing pads
US11851570B2 (en) 2019-04-12 2023-12-26 Applied Materials, Inc. Anionic polishing pads formed by printing processes
US11878389B2 (en) 2021-02-10 2024-01-23 Applied Materials, Inc. Structures formed using an additive manufacturing process for regenerating surface texture in situ
US11964359B2 (en) 2015-10-30 2024-04-23 Applied Materials, Inc. Apparatus and method of forming a polishing article that has a desired zeta potential
US11986922B2 (en) 2015-11-06 2024-05-21 Applied Materials, Inc. Techniques for combining CMP process tracking data with 3D printed CMP consumables
WO2024137275A1 (en) * 2022-12-22 2024-06-27 Applied Materials, Inc. Uv curable printable formulations for high performance 3d printed cmp pads
US12023853B2 (en) 2014-10-17 2024-07-02 Applied Materials, Inc. Polishing articles and integrated system and methods for manufacturing chemical mechanical polishing articles

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120302148A1 (en) * 2011-05-23 2012-11-29 Rajeev Bajaj Polishing pad with homogeneous body having discrete protrusions thereon
SG11201402224WA (en) * 2011-11-29 2014-09-26 Nexplanar Corp Polishing pad with foundation layer and polishing surface layer
KR101847619B1 (ko) * 2012-01-12 2018-04-11 엠.씨.케이(주) 고함량의 연마제 성분을 포함한 연마패드 및 그 연마패드 제조방법
KR101532896B1 (ko) * 2012-03-20 2015-06-30 제이에이치 로드스 컴퍼니, 인크 자가-컨디셔닝 연마 패드 및 이를 제조하는 방법
TWI580524B (zh) * 2014-02-18 2017-05-01 中國砂輪企業股份有限公司 高性能化學機械研磨修整器及其製作方法
JP6365869B2 (ja) * 2014-03-19 2018-08-01 Dic株式会社 ウレタン組成物及び研磨材
JP2017514704A (ja) * 2014-05-01 2017-06-08 スリーエム イノベイティブ プロパティズ カンパニー 可撓性研磨物品及びその使用方法
US10086500B2 (en) * 2014-12-18 2018-10-02 Applied Materials, Inc. Method of manufacturing a UV curable CMP polishing pad
CN105150120B (zh) * 2015-09-01 2018-03-30 河南科技学院 一种Roll‑to‑Roll化学机械抛光机用固结磨料抛光辊的刚性层及其制备方法
TWI769988B (zh) * 2015-10-07 2022-07-11 美商3M新設資產公司 拋光墊與系統及其製造與使用方法
KR101894071B1 (ko) * 2016-11-03 2018-08-31 에스케이씨 주식회사 연마패드 제조용 자외선 경화형 수지 조성물, 연마패드 및 이의 제조방법
US11524390B2 (en) * 2017-05-01 2022-12-13 Rohm And Haas Electronic Materials Cmp Holdings, Inc. Methods of making chemical mechanical polishing layers having improved uniformity
JP7089905B2 (ja) * 2018-03-02 2022-06-23 富士紡ホールディングス株式会社 研磨パッド
KR102270392B1 (ko) * 2019-10-01 2021-06-30 에스케이실트론 주식회사 웨이퍼 연마 헤드, 웨이퍼 연마 헤드의 제조방법 및 그를 구비한 웨이퍼 연마 장치
TWI741753B (zh) * 2019-10-29 2021-10-01 南韓商Ｓｋｃ索密思股份有限公司 研磨墊、製造該研磨墊之方法及使用該研磨墊以製造半導體裝置之方法
KR102293765B1 (ko) * 2019-11-21 2021-08-26 에스케이씨솔믹스 주식회사 연마패드, 이의 제조방법, 및 이를 이용한 반도체 소자의 제조방법
KR102293801B1 (ko) * 2019-11-28 2021-08-25 에스케이씨솔믹스 주식회사 연마패드, 이의 제조방법 및 이를 이용한 반도체 소자의 제조방법
KR102538440B1 (ko) * 2021-05-26 2023-05-30 에스케이엔펄스 주식회사 연마 시스템, 연마 패드 및 반도체 소자의 제조방법
US20230406984A1 (en) * 2022-06-15 2023-12-21 Cmc Materials Llc Uv-curable resins for chemical mechanical polishing pads

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030217517A1 (en) * 2001-12-20 2003-11-27 Allison William C. Polishing pad
US20040224611A1 (en) * 2003-04-22 2004-11-11 Jsr Corporation Polishing pad and method of polishing a semiconductor wafer
US20050276967A1 (en) * 2002-05-23 2005-12-15 Cabot Microelectronics Corporation Surface textured microporous polishing pads

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6077601A (en) * 1998-05-01 2000-06-20 3M Innovative Properties Company Coated abrasive article
US6477926B1 (en) * 2000-09-15 2002-11-12 Ppg Industries Ohio, Inc. Polishing pad
US7192340B2 (en) * 2000-12-01 2007-03-20 Toyo Tire & Rubber Co., Ltd. Polishing pad, method of producing the same, and cushion layer for polishing pad
US20070010169A1 (en) * 2002-09-25 2007-01-11 Ppg Industries Ohio, Inc. Polishing pad with window for planarization
JP2005538571A (ja) * 2002-09-25 2005-12-15 ピーピージー インダストリーズ オハイオ， インコーポレイテッド 平坦化するための窓を有する研磨パッド
US20040209066A1 (en) * 2003-04-17 2004-10-21 Swisher Robert G. Polishing pad with window for planarization
JP2006114666A (ja) * 2004-10-14 2006-04-27 Asahi Kasei Electronics Co Ltd 研磨パッド、その製造方法、およびそれを用いた研磨方法
DE102006035726A1 (de) * 2006-07-28 2008-01-31 Evonik Röhm Gmbh Verfahren zur Herstellung von ABA-Triblockcopolymeren auf (Meth)acrylatbasis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030217517A1 (en) * 2001-12-20 2003-11-27 Allison William C. Polishing pad
US20050276967A1 (en) * 2002-05-23 2005-12-15 Cabot Microelectronics Corporation Surface textured microporous polishing pads
US20040224611A1 (en) * 2003-04-22 2004-11-11 Jsr Corporation Polishing pad and method of polishing a semiconductor wafer

Cited By (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110183583A1 (en) * 2008-07-18 2011-07-28 Joseph William D Polishing Pad with Floating Elements and Method of Making and Using the Same
US9878500B2 (en) * 2011-01-04 2018-01-30 Evonik Degussa Gmbh Composite semifinished products, molded parts produced therefrom, and molded parts produced directly based on hydroxy-functionalized (meth)acrylates, which are cross-linked by means of uretdiones in a thermosetting manner
US20130323993A1 (en) * 2011-01-04 2013-12-05 Evonik Degussa Gmbh Composite semifinished products, molded parts produced therefrom, and molded parts produced directly based on hydroxy-functionalized (meth)acrylates, which are cross-linked by means of uretdiones in a thermosetting manner
US9931728B2 (en) 2011-11-29 2018-04-03 Cabot Microelectronics Corporation Polishing pad with foundation layer and polishing surface layer
US20150050866A1 (en) * 2013-08-16 2015-02-19 San Fang Chemical Industry Co., Ltd. Polishing pad, polishing apparatus and method for manufacturing polishing pad
US11794308B2 (en) * 2013-11-04 2023-10-24 Applied Materials, Inc. Printed chemical mechanical polishing pad having particles therein
US10195714B2 (en) 2014-03-31 2019-02-05 Fujibo Holdings, Inc. Polishing pad and process for producing same
US11446788B2 (en) 2014-10-17 2022-09-20 Applied Materials, Inc. Precursor formulations for polishing pads produced by an additive manufacturing process
US10875145B2 (en) 2014-10-17 2020-12-29 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US12023853B2 (en) 2014-10-17 2024-07-02 Applied Materials, Inc. Polishing articles and integrated system and methods for manufacturing chemical mechanical polishing articles
US11958162B2 (en) 2014-10-17 2024-04-16 Applied Materials, Inc. CMP pad construction with composite material properties using additive manufacturing processes
US10537974B2 (en) 2014-10-17 2020-01-21 Applied Materials, Inc. CMP pad construction with composite material properties using additive manufacturing processes
US10821573B2 (en) 2014-10-17 2020-11-03 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US10399201B2 (en) 2014-10-17 2019-09-03 Applied Materials, Inc. Advanced polishing pads having compositional gradients by use of an additive manufacturing process
US10875153B2 (en) 2014-10-17 2020-12-29 Applied Materials, Inc. Advanced polishing pad materials and formulations
US10384330B2 (en) 2014-10-17 2019-08-20 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
CN110142687A (zh) * 2014-10-17 2019-08-20 应用材料公司 由积层制造工艺所生产的研磨垫
US11745302B2 (en) 2014-10-17 2023-09-05 Applied Materials, Inc. Methods and precursor formulations for forming advanced polishing pads by use of an additive manufacturing process
US11724362B2 (en) 2014-10-17 2023-08-15 Applied Materials, Inc. Polishing pads produced by an additive manufacturing process
US10953515B2 (en) 2014-10-17 2021-03-23 Applied Materials, Inc. Apparatus and method of forming a polishing pads by use of an additive manufacturing process
US20160136778A1 (en) * 2014-11-17 2016-05-19 San Fang Chemical Industry Co., Ltd. Polishing pad and method for making the same
WO2016176108A1 (en) * 2015-04-30 2016-11-03 Frito-Lay North America, Inc. Method and apparatus for removing a portion of a food product with an abrasive stream
US10010106B2 (en) 2015-04-30 2018-07-03 Frito-Lay North America, Inc. Method and apparatus for removing a portion of a food product with an abrasive stream
US20160339559A1 (en) * 2015-05-20 2016-11-24 FNS Tech. Co., Ltd. Polishing pad and preparing method thereof
US9827646B2 (en) * 2015-05-20 2017-11-28 Fns Tech Co., Ltd. Polishing pad and preparing method thereof
KR102514354B1 (ko) * 2015-06-26 2023-03-28 다우 글로벌 테크놀로지스 엘엘씨 연마 패드를 형성하는 조절된 기공도 방법
JP2017052077A (ja) * 2015-06-26 2017-03-16 ローム アンド ハース エレクトロニック マテリアルズ シーエムピー ホウルディングス インコーポレイテッド 研磨パッドを形成するための気孔率制御方法
US10005172B2 (en) * 2015-06-26 2018-06-26 Rohm And Haas Electronic Materials Cmp Holdings, Inc. Controlled-porosity method for forming polishing pad
US20160375550A1 (en) * 2015-06-26 2016-12-29 Rohm And Haas Electronic Materials Cmp Holdings, Inc. Controlled-porosity method for forming polishing pad
KR20170001624A (ko) * 2015-06-26 2017-01-04 다우 글로벌 테크놀로지스 엘엘씨 연마 패드를 형성하는 조절된 기공도 방법
JP2020124801A (ja) * 2015-10-16 2020-08-20 アプライド マテリアルズ インコーポレイテッドＡｐｐｌｉｅｄ Ｍａｔｅｒｉａｌｓ，Ｉｎｃｏｒｐｏｒａｔｅｄ 付加製造プロセスを用いて高機能研磨パッドを形成する方法及び装置
EP3362224A4 (en) * 2015-10-16 2019-04-17 Applied Materials, Inc. METHOD AND APPARATUS FOR FORMING IMPROVED POLISHING PADS USING ADDITIVE MANUFACTURING PROCESS
TWI695752B (zh) * 2015-10-16 2020-06-11 美商應用材料股份有限公司 用於以積層製程形成先進拋光墊的配方
CN108136568A (zh) * 2015-10-16 2018-06-08 应用材料公司 使用增材制造工艺形成先进抛光垫的方法和设备
WO2017066077A1 (en) 2015-10-16 2017-04-20 Applied Materials, Inc. Method and apparatus for forming advanced polishing pads using an additive manufacturing process
CN112045555A (zh) * 2015-10-16 2020-12-08 应用材料公司 使用增材制造工艺形成先进抛光垫的方法和设备
CN112045557A (zh) * 2015-10-16 2020-12-08 应用材料公司 使用增材制造工艺形成先进抛光垫的方法和设备
CN112059937A (zh) * 2015-10-16 2020-12-11 应用材料公司 使用增材制造工艺形成先进抛光垫的方法和设备
JP7009542B2 (ja) 2015-10-16 2022-01-25 アプライド マテリアルズ インコーポレイテッド 付加製造プロセスを用いて高機能研磨パッドを形成する方法及び装置
US11964359B2 (en) 2015-10-30 2024-04-23 Applied Materials, Inc. Apparatus and method of forming a polishing article that has a desired zeta potential
US11986922B2 (en) 2015-11-06 2024-05-21 Applied Materials, Inc. Techniques for combining CMP process tracking data with 3D printed CMP consumables
US11772229B2 (en) 2016-01-19 2023-10-03 Applied Materials, Inc. Method and apparatus for forming porous advanced polishing pads using an additive manufacturing process
US10391605B2 (en) 2016-01-19 2019-08-27 Applied Materials, Inc. Method and apparatus for forming porous advanced polishing pads using an additive manufacturing process
US10456886B2 (en) 2016-01-19 2019-10-29 Applied Materials, Inc. Porous chemical mechanical polishing pads
KR102629800B1 (ko) * 2016-01-19 2024-01-29 어플라이드 머티어리얼스, 인코포레이티드 다공성 화학적 기계적 연마 패드들
WO2017127221A1 (en) * 2016-01-19 2017-07-27 Applied Materials, Inc. Porous chemical mechanical polishing pads
CN108698206A (zh) * 2016-01-19 2018-10-23 应用材料公司 多孔化学机械抛光垫
KR20180097759A (ko) * 2016-01-19 2018-08-31 어플라이드 머티어리얼스, 인코포레이티드 다공성 화학적 기계적 연마 패드들
US20190106607A1 (en) * 2016-05-23 2019-04-11 Tatsuta Electric Wire & Cable Co., Ltd. Conductive Adhesive Composition
US10577524B2 (en) * 2016-05-23 2020-03-03 Tatsuta Electric Wire & Cable Co., Ltd. Conductive adhesive composition
US11814795B2 (en) * 2017-04-03 2023-11-14 Jl Darling Llc Coating for recyclable paper
WO2018187220A1 (en) * 2017-04-03 2018-10-11 Jl Darling Llc Coating for recyclable paper
US11471999B2 (en) 2017-07-26 2022-10-18 Applied Materials, Inc. Integrated abrasive polishing pads and manufacturing methods
US11980992B2 (en) 2017-07-26 2024-05-14 Applied Materials, Inc. Integrated abrasive polishing pads and manufacturing methods
US11524384B2 (en) 2017-08-07 2022-12-13 Applied Materials, Inc. Abrasive delivery polishing pads and manufacturing methods thereof
WO2019032286A1 (en) * 2017-08-07 2019-02-14 Applied Materials, Inc. ABRASIVE DISTRIBUTION POLISHING PADS AND METHODS OF MAKING SAME
US11826876B2 (en) 2018-05-07 2023-11-28 Applied Materials, Inc. Hydrophilic and zeta potential tunable chemical mechanical polishing pads
US11685014B2 (en) 2018-09-04 2023-06-27 Applied Materials, Inc. Formulations for advanced polishing pads
US20200171623A1 (en) * 2018-11-30 2020-06-04 Taiwan Semiconductor Manufacturing Co., Ltd. Wafer backside cleaning apparatus and method of cleaning wafer backside
US20220209324A1 (en) * 2019-04-05 2022-06-30 Ddp Specialty Electronic Materials Us, Llc Polyurethane based thermal interface material
US11851570B2 (en) 2019-04-12 2023-12-26 Applied Materials, Inc. Anionic polishing pads formed by printing processes
US11813712B2 (en) 2019-12-20 2023-11-14 Applied Materials, Inc. Polishing pads having selectively arranged porosity
US11638979B2 (en) 2020-06-09 2023-05-02 Applied Materials, Inc. Additive manufacturing of polishing pads
US11612978B2 (en) 2020-06-09 2023-03-28 Applied Materials, Inc. Additive manufacturing of polishing pads
US11806829B2 (en) 2020-06-19 2023-11-07 Applied Materials, Inc. Advanced polishing pads and related polishing pad manufacturing methods
US11807710B2 (en) 2020-10-19 2023-11-07 Cmc Materials, Inc. UV-curable resins used for chemical mechanical polishing pads
US11878389B2 (en) 2021-02-10 2024-01-23 Applied Materials, Inc. Structures formed using an additive manufacturing process for regenerating surface texture in situ
WO2024137275A1 (en) * 2022-12-22 2024-06-27 Applied Materials, Inc. Uv curable printable formulations for high performance 3d printed cmp pads

Also Published As

Publication number Publication date
TW201130656A (en) 2011-09-16
SG181890A1 (en) 2012-07-30
WO2011087737A2 (en) 2011-07-21
TWI517975B (zh) 2016-01-21
KR101855073B1 (ko) 2018-05-09
JP5728026B2 (ja) 2015-06-03
JP2013515379A (ja) 2013-05-02
KR20120120247A (ko) 2012-11-01
WO2011087737A3 (en) 2011-09-15
CN102762340A (zh) 2012-10-31

Similar Documents

Publication Publication Date Title
US20130012108A1 (en) Polishing pad and method of making the same
US7097549B2 (en) Polishing pad
US6477926B1 (en) Polishing pad
US7291063B2 (en) Polyurethane urea polishing pad
KR100892924B1 (ko) 연마 패드
JP4884726B2 (ja) 積層研磨パッドの製造方法
KR100877388B1 (ko) 연마 패드 및 그 제조 방법
WO2011129254A1 (ja) 研磨パッド
US20070021045A1 (en) Polyurethane Urea Polishing Pad with Window
JP4884808B2 (ja) 研磨パッドの製造方法
JP2009224384A (ja) 研磨パッド及び半導体デバイスの製造方法
US11548114B1 (en) Compressible non-reticulated polyurea polishing pad
CN102762340B (zh) 抛光垫及其制造方法
US11897082B2 (en) Heterogeneous fluoropolymer mixture polishing pad
JP4831476B2 (ja) 研磨パッドの製造方法
JP2008248121A (ja) 研磨パッドの製造方法

Legal Events

Date Code Title Description
AS Assignment

Owner name: 3M INNOVATIVE PROPERTIES COMPANY, MINNESOTA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LI, NAICHAO;JOSEPH, WILLIAM D.;SIGNING DATES FROM 20120416 TO 20120418;REEL/FRAME:028425/0253

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION