CN113286860A - Adhesive sheet for processing workpiece and method for producing same - Google Patents

Adhesive sheet for processing workpiece and method for producing same Download PDF

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Publication number
CN113286860A
CN113286860A CN202080007514.3A CN202080007514A CN113286860A CN 113286860 A CN113286860 A CN 113286860A CN 202080007514 A CN202080007514 A CN 202080007514A CN 113286860 A CN113286860 A CN 113286860A
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China
Prior art keywords
adhesive
workpiece
processing
adhesive sheet
base material
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Granted
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CN202080007514.3A
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Chinese (zh)
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CN113286860B (en
Inventor
小田直士
坂本美纱季
山口征太郎
佐伯尚哉
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Lintec Corp
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Lintec Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/255—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29—Laminated material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Materials For Medical Uses (AREA)
  • Absorbent Articles And Supports Therefor (AREA)

Abstract

The present invention provides an adhesive sheet for processing a workpiece, which comprises a substrate and an adhesive layer laminated on one surface of the substrate, wherein the adhesive layer is composed of an active energy ray-curable adhesive, the adhesive is formed by an adhesive composition containing an acrylic polymer with an active energy ray-curable group introduced into a side chain, the glass transition temperature (Tg) of the acrylic polymer is more than or equal to minus 80 ℃ and less than or equal to minus 30 ℃, and a coating layer containing a pyrrolidone compound is formed on the surface of the substrate, which is in contact with the adhesive layer. According to the adhesive sheet for processing a workpiece, adhesive residue on the workpiece can be suppressed.

Description

Adhesive sheet for processing workpiece and method for producing same
Technical Field
The present invention relates to an adhesive sheet for workpiece processing that can be suitably used for processing a workpiece such as a semiconductor wafer, and a method for producing the same.
Background
Semiconductor wafers such as silicon and gallium arsenide and various packages are manufactured in a large-diameter state, cut (diced) into device chips (semiconductor chips), and are separated (picked up) before being transferred to a mounting process which is a next process. In this case, a work such as a semiconductor wafer is subjected to processing such as back grinding, dicing, washing, drying, spreading, picking up, and mounting (mounting) in a state of being attached to a work processing adhesive sheet provided with a base material and an adhesive layer.
In the dicing step, a chip may be broken (chipped) at a cut surface due to insufficient fixation of the object to be cut, or the like. This edge breakage reduces the bending strength of the chip itself, and causes air to be trapped in the package of the IC to be sealed, thereby causing package cracks to easily occur. In recent years, the thinning of semiconductor wafers has been progressing, and the thinner the thickness is, the higher the possibility of occurrence of the edge chipping is.
In order to prevent the occurrence of the edge chipping, it is conceivable to improve the adhesion. For example, patent document 1 proposes an adhesive sheet for dicing having an adhesion temperature at which the adhesive sheet for dicing has an adhesion of 10N/25mm or more when peeled at 180 ° at 23 ℃ (stretching speed 300 mm/min) after being adhered to a silicon mirror surface wafer.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2003-142433
Disclosure of Invention
Technical problem to be solved by the invention
However, when a work processing adhesive sheet having a high adhesive force is used, there is a problem that when the work processing adhesive sheet is separated from the work (for example, when a chip is picked up), an adhesive constituting the adhesive layer is easily attached to the work, so-called adhesive residue. This problem of adhesive residue is particularly likely to occur when the surface of the workpiece has minute recesses.
Specifically, the surface of the adhesive layer side of the adhesive sheet for workpiece processing is attached to the surface of the workpiece having the concave portion, and after the workpiece is subjected to a predetermined processing on the adhesive sheet for workpiece processing, the adhesive sheet for workpiece processing and the workpiece are separated. In this separation, there is a problem that an adhesive constituting an adhesive layer of the adhesive sheet for workpiece processing is easily attached to a surface of the workpiece to which the adhesive sheet for workpiece processing is attached.
The present invention has been made in view of the above circumstances, and an object thereof is to provide an adhesive sheet for workpiece processing that can suppress adhesive residue on a workpiece, and a method for manufacturing the same.
Means for solving the problems
In order to achieve the above object, the first aspect of the present invention provides an adhesive sheet for processing a workpiece, comprising a substrate and an adhesive layer laminated on one surface of the substrate, wherein the adhesive layer is composed of an active energy ray-curable adhesive, the adhesive is composed of an adhesive composition containing an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof, the acrylic polymer has a glass transition temperature (Tg) of-80 ℃ or higher and-30 ℃ or lower, and a coating layer containing a pyrrolidone-based compound is formed on a surface of the substrate that is in contact with the adhesive layer (invention 1).
In the adhesive sheet for processing a workpiece according to the invention (invention 1), the adhesive layer is composed of an active energy ray-curable adhesive agent formed of an adhesive composition containing an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof, the acrylic polymer has a glass transition temperature (Tg) within the above range, and a coating layer containing a pyrrolidone compound is formed on a surface of the substrate which is in contact with the adhesive layer, whereby the problem of adhesive residue can be reduced.
In the above invention (invention 1), it is preferable that: the acrylic polymer has a structure derived from an alkyl (meth) acrylate in the main chain of the polymer, and the number of carbon atoms of an acrylic group in the alkyl (meth) acrylate is 1 to 4 (invention 2).
In the above inventions (inventions 1 and 2), it is preferable that: the acrylic polymer has a structure derived from a functional group-containing monomer in the main chain of the polymer, and the proportion of the structural moiety derived from the functional group-containing monomer in the entire polymer is 0.1 mass% or more and 12 mass% or less (invention 3).
In the above invention (inventions 1 to 3), it is preferable that: the pyrrolidone-based compound is a polymer having vinylpyrrolidone as a main structural unit (invention 4).
In the above inventions (inventions 1 to 4), it is preferable that: the base material has a storage modulus of 1000MPa or more at 25 ℃ (invention 5).
In the above invention (invention 5), it is preferable that: the substrate has a polyethylene terephthalate film as a substrate body (invention 6).
In the above inventions (inventions 1 to 6), the adhesive sheet for processing a workpiece is preferably a dicing sheet (invention 7).
Second, the present invention provides a method for producing an adhesive sheet for workpiece processing (inventions 1 to 7), comprising: forming a coating layer containing a pyrrolidone-based compound on one surface of a base material body to obtain the base material; a step of applying the adhesive composition to a release surface of a release sheet to form the adhesive layer; and a step of bonding the surface of the substrate on the coating layer side to the adhesive layer (invention 8).
A third aspect of the present invention provides a method for producing an adhesive sheet for workpiece processing (invention 3), comprising: a step for preparing a (meth) acrylate polymer obtained by copolymerizing a functional group-containing monomer in an amount of 5 to 35 mass%, and reacting the (meth) acrylate polymer with an active energy ray-curable group-containing compound having a functional group to prepare an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof, thereby preparing an adhesive composition containing the acrylic polymer; forming a coating layer containing a pyrrolidone-based compound on one surface of a base material body to obtain the base material; a step of applying the adhesive composition to a release surface of a release sheet to form the adhesive layer; and a step of bonding the surface of the substrate on the coating layer side to the adhesive layer (invention 9).
In the above invention (invention 9), it is preferable that: the amount of the active energy ray-curable group-containing compound having a functional group is 60 mol% or more and 99 mol% or less relative to the amount of the functional group-containing monomer (invention 10).
Effects of the invention
The adhesive sheet for processing a workpiece can inhibit adhesive residue on the workpiece. Further, according to the method for producing an adhesive sheet for workpiece processing of the present invention, an adhesive sheet for workpiece processing that can suppress adhesive residue on a workpiece can be efficiently produced.
Drawings
FIG. 1 is a sectional view of an adhesive sheet for workpiece processing according to an embodiment of the present invention.
Detailed Description
Hereinafter, embodiments of the present invention will be described.
The pressure-sensitive adhesive sheet for processing a workpiece according to one embodiment of the present invention includes a base and a pressure-sensitive adhesive layer laminated on one surface of the base. The adhesive layer is composed of an active energy ray-curable adhesive, the adhesive is formed by an adhesive composition containing an acrylic polymer with an active energy ray-curable group introduced into a side chain, and the glass transition temperature (Tg) of the acrylic polymer is more than-80 ℃ and less than-30 ℃. Further, a coating layer containing a pyrrolidone-based compound is formed on the surface of the base material that is in contact with the adhesive agent layer.
When the adhesive sheet for workpiece processing of the present embodiment is used, a workpiece is stuck to the surface (hereinafter, sometimes referred to as "adhesive surface") of the adhesive layer of the adhesive sheet for workpiece processing on the opposite side to the substrate, and the workpiece is subjected to predetermined processing on the adhesive sheet for workpiece processing. Next, the adhesive layer is cured by irradiating the adhesive layer with an energy ray, and then the work processing adhesive sheet and the work are separated. The adhesive sheet for processing a workpiece according to the present embodiment, having the above-described configuration, can effectively suppress adhesive residue on the workpiece when separated from the workpiece. In particular, when the adhesive layer is formed of an active energy ray-curable adhesive agent formed of an adhesive composition containing an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof, the adhesive force to the workpiece is easily reduced by irradiation with an active energy ray, and the adhesive agent is less likely to remain on the workpiece side when separated from the workpiece. Further, when the glass transition temperature (Tg) of the adhesive is-30 ℃ or lower, the adhesion to the base material becomes high, and the adhesive is less likely to remain on the workpiece side when separated from the workpiece. Further, by having the coating layer containing the pyrrolidone-based compound on the surface of the base material that is in contact with the adhesive agent layer, the adhesion between the base material and the adhesive agent layer becomes higher, and the adhesive agent is less likely to remain on the workpiece side when separated from the workpiece. Even if a minute recess is present on the surface of the workpiece that is in contact with the adhesive surface of the adhesive sheet for workpiece processing, the effect of suppressing adhesive residue can be exhibited well.
From the viewpoint of suppressing the residual gel, the glass transition temperature (Tg) of the acrylic polymer needs to be-30 ℃ or lower, preferably-32 ℃ or lower, and particularly preferably-35 ℃ or lower. Further, the glass transition temperature (Tg) of the acrylic polymer is preferably-80 ℃ or higher, more preferably-70 ℃ or higher, and particularly preferably-55 ℃ or higher, from the same viewpoint of suppressing the residual gel. The glass transition temperature (Tg) in the present specification is a calculated value obtained by the Fox equation.
On the other hand, the storage modulus at 25 ℃ of the base material in the present embodiment is preferably 1000MPa or more. By providing the base material with such a storage modulus, the occurrence of wobbling of the work processing adhesive sheet during dicing is reduced, and the movement of the work attached to the work processing adhesive sheet is restricted, with the result that the occurrence of edge chipping is suppressed. In general, when the base material has the large storage modulus, the adhesion between the base material and the adhesive agent layer is reduced, and when the base material is separated from the workpiece, the adhesive agent is likely to remain on the workpiece side.
From the above-mentioned viewpoint, the storage modulus of the base material at 25 ℃ is more preferably 1200MPa or more, and particularly preferably 1500MPa or more. On the other hand, the storage modulus of the base material at 25 ℃ is preferably 3000MPa or less. By setting the upper limit value of the storage modulus to the above value, the work processing adhesive sheet has appropriate elasticity, and separation from the work (including pickup of a chip) can be performed well. The method of measuring the storage modulus of the base material is shown in test examples described later.
Fig. 1 shows a specific configuration of the pressure-sensitive adhesive sheet for processing a workpiece according to the present embodiment. As shown in fig. 1, an adhesive sheet 1 for processing a work according to one embodiment includes a substrate 2, an adhesive layer 3 laminated on one surface side of the substrate 2, and a release sheet 4 laminated on the adhesive layer 3 on the side opposite to the substrate 2. The substrate 2 includes a substrate body 21 and a coating layer 22 containing a pyrrolidone-based compound, and the coating layer 22 is located on the side in contact with the adhesive layer 3. The release sheet 4 is provided so that the release surface of the release sheet 4 is in contact with the adhesive layer 3. The release surface of the release sheet in the present specification means a surface having releasability in the release sheet, and includes any of a surface subjected to a release treatment and a surface showing releasability even if the release treatment is not performed.
1. Structural member of adhesive sheet for working workpiece
(1) Base material
The base material 2 in this embodiment includes a base material body 21, and a coating layer 22 containing a pyrrolidone-based compound provided on the adhesive layer 3 side of the base material body 21.
(1-1) substrate body
The base material main body 21 in the present embodiment is not particularly limited as long as it can exhibit a desired function when the adhesive sheet for workpiece processing is used. However, the base material 2 is preferably a base material that can exhibit the storage modulus from the viewpoint of suppressing edge chipping at the time of cutting. In addition, in the present embodiment, since the coating layer 22 hardly affects the storage modulus of the base material 2, the storage modulus of the base material 2 and the storage modulus of the base material body 21 can be regarded as the same.
When the workpiece is a workpiece such as a semiconductor wafer that has no or low transmissivity for active energy rays (particularly ultraviolet rays), the base material body 21 preferably has good transmissivity for active energy rays. By irradiating the adhesive layer 3 with active energy rays through the substrate 2, the adhesive layer 3 can be cured satisfactorily. When the workpiece is a workpiece made of a material having good transparency to active energy rays, such as a glass member, and there is a possibility that unevenness (for example, unevenness formed by printing) exists on the surface of the glass member and further the active energy rays (particularly, ultraviolet rays) cannot sufficiently exhibit transparency due to the unevenness, the substrate main body 21 is preferably good in transparency to active energy rays.
The base body 21 is preferably a resin film mainly made of a resin material. Specific examples thereof include polyester-based films such as polyethylene terephthalate films, polybutylene terephthalate films, and polyethylene naphthalate films; an ethylene-vinyl acetate copolymer film; ethylene copolymer films such as ethylene-methyl (meth) acrylate copolymer films and other ethylene-methyl (meth) acrylate copolymer films; polyolefin films such as polyethylene films, polypropylene films, polybutylene films, polybutadiene films, polymethylpentene films, ethylene-norbornene copolymer films, and norbornene resin films; polyvinyl chloride films such as polyvinyl chloride films and vinyl chloride copolymer films; a (meth) acrylate copolymer film; a polyurethane film; a polyimide film; a polystyrene film; a polycarbonate film; fluororesin films, and the like. Examples of the polyethylene film include a Low Density Polyethylene (LDPE) film, a Linear Low Density Polyethylene (LLDPE) film, and a High Density Polyethylene (HDPE) film. Further, modified membranes such as crosslinked membranes and ionic polymer membranes can also be used. The substrate may be a laminated film obtained by laminating a plurality of the above-described films. In this laminated film, the materials constituting each layer may be the same type or different types. In the present specification, "(meth) acrylic" refers to acrylic and methacrylic.
Other similar terms are also the same.
As the base body 21 in the present embodiment, among the above films, a polyester film, a hard vinyl chloride film, a polystyrene film, a polycarbonate film, and the like are preferable, and a polyester film is particularly preferable. Among polyester-based films, polyethylene terephthalate films are particularly preferable. The above film easily satisfies the storage modulus, and therefore, the occurrence of edge chipping is easily suppressed.
The base material body 21 may contain various additives such as a flame retardant, a plasticizer, an antistatic agent, a lubricant, an antioxidant, a colorant, an infrared absorber, an ultraviolet absorber, and an ion scavenger. The content of these additives is not particularly limited, but is preferably within a range in which the base material body 21 can exert a desired function.
The thickness of the base body 21 can be appropriately set according to the method of using the adhesive sheet 1 for processing a workpiece, and is preferably 20 μm or more, particularly preferably 25 μm or more, and more preferably 40 μm or more, from the viewpoint of suppressing occurrence of chipping. The thickness is preferably 450 μm or less, more preferably 300 μm or less, and still more preferably 200 μm or less.
(1-2) coating
The coating 22 in this embodiment contains a pyrrolidone-based compound. The presence of the coating layer 22 increases the adhesion between the base material 2 and the adhesive layer 3, and effectively suppresses adhesive residue when separating from the work. The reason is not necessarily clear, but it is presumed that the pyrrolidone-based compound bonds or reacts with a functional group, particularly a hydroxyl group, contained in the adhesive constituting the adhesive layer 3, and thereby the adhesive layer 3 is easily adhered to the coating layer 22.
The pyrrolidone-based compound may be a monomer or a polymer as long as it is a compound having a pyrrolidone skeleton. Among them, from the viewpoint of adhesion of the adhesive layer 3 to the coating layer 22, a polymer having a pyrrolidone skeleton is preferable, and a polymer having vinylpyrrolidone as a main structural unit is particularly preferable. The polymer may be a homopolymer of vinylpyrrolidone (polyvinylpyrrolidone) or a copolymer of vinylpyrrolidone and another monomer. In the case of such a copolymer, the content ratio of the vinylpyrrolidone component is preferably 50% by mass or more.
Examples of the other monomer include monomers having an addition polymerizable unsaturated group such as a vinyl group, (meth) acryloyl group, and allyl group. The other monomer may have an alkyl group, an alkyl ester group, an alkyl ether group, a hydroxyl group, a carboxyl group, an amide group, an amino group, a polyalkylene ether group, or the like in a side chain.
Specific examples of the other monomer include vinyl monomers such as (meth) acrylic acid, alkyl (meth) methacrylates such as methyl (meth) acrylate, monoesters of (meth) acrylic acid and diols such as hydroxyethyl (meth) acrylate, alkali metal salts of (meth) acrylic acid, ammonium salts of (meth) acrylic acid, vinyl acetate, N-vinylimidazole, N-vinylacetamide, N-vinylformamide, N-vinylcaprolactam, (meth) acrylamide, N-alkyl (meth) acrylamide, and N-methylol (meth) acrylamide.
The weight average molecular weight of the polymer having a pyrrolidone skeleton is preferably 50000 or more, and particularly preferably 100000 or more. The weight average molecular weight is preferably 1000000 or less, particularly preferably 800000 or less, and more preferably 700000 or less. Here, the weight average molecular weight in the present specification is a value in terms of standard polystyrene measured by a Gel Permeation Chromatography (GPC) method.
The coating layer 22 in the present embodiment is preferably formed by coating a coating agent containing a pyrrolidone-based compound. The coating agent preferably contains a binder resin in addition to the pyrrolidone-based compound, and more preferably contains a curing agent (crosslinking agent) that reacts with the binder resin.
The content (in terms of solid content) of the pyrrolidone-based compound in the coating agent is preferably 20% by mass or more, and particularly preferably 30% by mass or more. The content is preferably 80% by mass or less, and particularly preferably 70% by mass or less.
As the binder resin, a polyester-based binder resin, an acrylic-based binder resin, a polyether-urethane-based binder resin, and the like are preferably cited. Among them, polyester-based binder resins are preferred in view of affinity for the substrate. The polyester-based binder resin is preferably an aqueous polyester-based binder resin. The aqueous polyester-based binder resin is dissolved in water to be in the form of an aqueous solution or in the form of an aqueous dispersion dispersed in water as an emulsion.
The aqueous polyester-based binder resin preferably has an acid value of 10.0KOHmg/g or more and a hydroxyl value of 2.0KOHmg/g or more. This provides excellent adhesion to the base material body 21. From this viewpoint, the acid value of the aqueous polyester-based binder resin is more preferably 15.0KOHmg/g or more, particularly preferably 20.0KOHmg/g or more, still more preferably 30.0KOHmg/g or more, and most preferably 40.0KOHmg/g or more. The hydroxyl value of the aqueous polyester-based binder resin is more preferably 2.5KOHmg/g or more, particularly preferably 3.0KOHmg/g or more, still more preferably 3.5KOHmg/g or more, and most preferably 4.0KOHmg/g or more. The acid value and the hydroxyl value are values measured in accordance with JIS K0070-1992.
Examples of the aqueous polyester-based binder resin include a copolymer obtained by polycondensation of an alcohol component and a carboxylic acid component, and a modified product of the copolymer.
As the alcohol component, a polyol having 2 or more hydroxyl groups in 1 molecule can be used. Specific examples of the alcohol component include glycols such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, 1, 4-butanediol, 1, 3-butanediol, 2, 3-butanediol, 1, 2-butanediol, 3-methyl-1, 2-butanediol, 1, 2-pentanediol, 1, 5-pentanediol, 1, 4-pentanediol, 2, 4-pentanediol, 3-methyl-4, 5-pentanediol, 2, 4-trimethyl-1, 3-pentanediol, 1, 6-hexanediol, 1, 5-hexanediol, 1, 4-hexanediol, 2, 5-hexanediol, neopentyl glycol, and hydroxypivalyl hydroxypivalate; polylactone diols obtained by adding lactones such as epsilon-caprolactone to these diols; polyester glycols such as bis (hydroxyethyl) terephthalate; divalent cyclic alcohols such as 1, 3-cyclohexanedimethanol, 1, 4-cyclohexanedimethanol, tricyclodecanedimethanol, hydrogenated bisphenol A, hydrogenated bisphenol F, spiroglycol (spiroglycol), and dimethylol tricyclodecane; ethylene oxide or propylene oxide addition products of bisphenol a; and trivalent or higher polyhydric alcohols such as glycerin, trimethylolpropane, trimethylolethane, diglycerin (diglycerin), triglycerin (triglycerin), 1,2, 6-hexanetriol, neopentyltetraol, dipentaerythritol, sorbitol, and mannitol. These alcohol components may be used alone or in combination of two or more.
As the carboxylic acid component, a polybasic acid having 2 or more carboxyl groups in 1 molecule can be used. Specific examples of the carboxylic acid component include dicarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, 4-biphenyldicarboxylic acid, diphenylmethane-4, 4' -dicarboxylic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, chlorendic acid, maleic acid, fumaric acid, itaconic acid, cyclohexane-1, 3-dicarboxylic acid, cyclohexane-1, 4-dicarboxylic acid, hexahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalic acid, and methylhexahydrophthalic acid, and anhydrides thereof; tricarboxylic acids such as trimellitic acid, pyromellitic acid, trimesic acid, methylcyclohexanetricarboxylic acid, hexahydrotrimellitic acid, tetrachlorohexanetricarboxylic acid, and anhydrides thereof; tetracarboxylic acids such as 1,2,4, 5-cyclohexanetetracarboxylic acid, 1,2,3, 4-butanetetracarboxylic acid, 1,2,3, 4-cyclobutanetetracarboxylic acid, 1,2,3, 4-cyclopentanetetracarboxylic acid and pyromellitic acid, and acid anhydrides thereof. These carboxylic acid components may be used alone or in combination of two or more.
The weight average molecular weight of the aqueous polyester-based binder resin is preferably 1000 to 20000, more preferably 1500 to 15000, particularly preferably 2000 to 10000, and further preferably 500 to 7500, from the viewpoints of solubility in water, dispersibility in water, and adhesion to the base material body 21.
The content (in terms of solid content) of the binder resin in the coating agent is preferably 20% by mass or more, and particularly preferably 30% by mass or more. The content is preferably 80% by mass or less, and particularly preferably 70% by mass or less.
The curing agent is not particularly limited as long as it reacts with the binder resin, and examples thereof include epoxy compounds, carbodiimide compounds, oxazoline compounds, hydrazide compounds, isocyanate compounds, alkoxysilane compounds, and amine compounds. These curing agents may be used alone or in combination of two or more. Among them, from the viewpoint of reactivity with the aqueous polyester-based binder resin, an epoxy-based compound, a carbodiimide-based compound, or an oxazoline-based compound is preferable, and an oxazoline-based compound is particularly preferable. In addition, these compounds are preferably water-soluble from the viewpoint of compatibility with the aqueous polyester-based binder resin.
The epoxy compound may have 2 or more epoxy groups or glycidyl groups in the molecule. In addition, the carbodiimide-based compound may contain at least 2 carbodiimide groups in the molecule.
The oxazoline compound may contain at least 2 oxazoline groups in the molecule, and examples thereof include a homopolymer of addition polymerizable 2-oxazoline (for example, 2-isopropenyl-2-oxazoline) having a substituent having an unsaturated carbon-carbon bond at the carbon atom position at the 2-position, and a copolymer of the addition polymerizable 2-oxazoline and another unsaturated monomer.
When the oxazoline compound is a polymer, the weight average molecular weight is preferably 10000 to 300000, more preferably 50000 to 200000.
The content (in terms of solid content) of the curing agent in the coating agent is preferably 1% by mass or more, and particularly preferably 3% by mass or more. The content is preferably 20% by mass or less, and particularly preferably 15% by mass or less.
The lower limit of the thickness of the coating layer 22 is preferably 0.01 μm or more, and particularly preferably 0.03 μm or more, from the viewpoint of adhesiveness to the adhesive layer 3. From the viewpoint of blocking prevention, the upper limit of the thickness of the coating layer 22 is preferably 10 μm or less, particularly preferably 1 μm or less, and more preferably 0.2 μm or less.
(2) Adhesive layer
The adhesive layer 3 in the present embodiment is composed of an active energy ray-curable adhesive formed of an adhesive composition containing an acrylic polymer (a) having an active energy ray-curable group introduced into a side chain thereof (hereinafter, may be referred to as "adhesive composition P"). The adhesive composition P in the present embodiment preferably contains the acrylic polymer (a) and the crosslinking agent (B), and more preferably further contains the photopolymerization initiator (C).
(2-1) Components
(2-1-1) acrylic Polymer (A) having an active energy ray-curable group introduced into a side chain thereof
The acrylic polymer (a) having an active energy ray-curable group introduced into the side chain is preferably a polymer obtained by reacting a (meth) Acrylate Polymer (AP) having a functional group with an active energy ray-curable group-containing compound (a3) having a functional group reactive with the functional group.
The (meth) Acrylate Polymer (AP) is preferably a polymer obtained by copolymerizing at least an alkyl (meth) acrylate (a1) and a functional group-containing monomer (a2) having a reactive functional group.
The alkyl (meth) acrylate (A1) preferably has an alkyl group having 1 to 18 carbon atoms, and particularly preferably has 1 to 4 carbon atoms. By setting the number of carbon atoms to 1 to 4, the adhesive layer 3 obtained has higher adhesiveness to the base material 2.
Specific examples of the alkyl (meth) acrylate (a1) include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-decyl (meth) acrylate, lauryl (meth) acrylate, myristyl (meth) acrylate, palmityl (meth) acrylate, and stearyl (meth) acrylate. Among them, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, or n-butyl (meth) acrylate is preferable, and methyl methacrylate or n-butyl acrylate is particularly preferable. These alkyl (meth) acrylates may be used alone or in combination of two or more.
The proportion by mass of the structural moiety derived from the alkyl (meth) acrylate (a1) in the (meth) Acrylate Polymer (AP) is preferably 50 to 98% by mass, particularly preferably 60 to 95% by mass, and further preferably 70 to 90% by mass.
As the functional group-containing monomer (a2), a monomer having a reactive functional group that can react with a functional group of the active energy ray-curable group-containing compound (A3) can be used. Examples of the functional group-containing monomer (a2) include a hydroxyl group, a carboxyl group, an amino group, a substituted amino group, and an epoxy group, and among them, a hydroxyl group or a carboxyl group is preferable, and a hydroxyl group is particularly preferable. When the crosslinking agent (B) is used, the reactive functional group of the functional group-containing monomer (a2) is preferably reacted with the crosslinking agent (B).
When a monomer having a hydroxyl group (hydroxyl group-containing monomer) is used as the functional group-containing monomer (a2), examples thereof include hydroxyalkyl (meth) acrylates, and specific examples thereof include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Among them, 2-hydroxyethyl (meth) acrylate is preferable from the viewpoint of reactivity and copolymerizability of hydroxyl groups. These hydroxyl group-containing monomers may be used alone or in combination of two or more.
When a monomer having a carboxyl group (carboxyl group-containing monomer) is used as the functional group-containing monomer (a2), examples thereof include ethylenically unsaturated carboxylic acids, and specific examples thereof include acrylic acid, methacrylic acid, crotonic acid, maleic acid, itaconic acid, citraconic acid, and the like. Among these, acrylic acid is preferable in view of reactivity and copolymerizability of the carboxyl group. These carboxyl group-containing monomers may be used alone or in combination of two or more.
In addition, different kinds of functional group-containing monomers (A2) may be used in combination. For example, the above-mentioned hydroxyl group-containing monomer and carboxyl group-containing monomer may be used in combination.
The proportion of the mass of the structural moiety derived from the functional group-containing monomer (a2) in the (meth) Acrylate Polymer (AP) is preferably 5 mass% or more, particularly preferably 7 mass% or more, and more preferably 10 mass% or more. The ratio is preferably 35% by mass or less, particularly preferably 30% by mass or less, and further preferably 17% by mass or less. By setting the ratio of the mass of the structural moiety derived from the functional group-containing monomer (a2) within the above range, the amount of the active energy ray-curable group-containing compound (A3) introduced into the acrylic polymer (a) having an energy ray-curable group introduced into the side chain can be set within an appropriate range. When the functional group-containing monomer (a2) is reacted with the crosslinking agent (B) using the crosslinking agent (B), the degree of crosslinking by the crosslinking agent (B), that is, the gel fraction, can be controlled within an appropriate range, and the physical properties such as the cohesive force of the adhesive agent layer 3 can be controlled. Further, when the ratio is 17% by mass or less, the effect of suppressing the residual gum is more excellent.
The (meth) Acrylate Polymer (AP) may be a polymer obtained by copolymerizing the alkyl (meth) acrylate (a1) and the functional group-containing monomer (a2) together with other monomers.
Examples of the other monomer include alkoxyalkyl group-containing (meth) acrylates such as methoxymethyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, and ethoxyethyl (meth) acrylate; alicyclic ring-containing (meth) acrylates such as cyclohexyl (meth) acrylate; aromatic ring-containing (meth) acrylates such as phenyl (meth) acrylate; monomers having a nitrogen-containing heterocycle such as N- (meth) acryloylmorpholine, N-vinyl-2-pyrrolidone, and N- (meth) acryloylpyrrolidone; non-crosslinkable acrylamides such as (meth) acrylamide and N, N-dimethyl (meth) acrylamide; (meth) acrylic esters having a non-crosslinkable tertiary amino group such as N, N-dimethylaminoethyl (meth) acrylate and N, N-dimethylaminopropyl (meth) acrylate; vinyl acetate; styrene, and the like. Among these, monomers having a nitrogen-containing heterocycle, non-crosslinkable acrylamide or vinyl acetate are preferable, N- (meth) acryloylmorpholine, dimethyl (meth) acrylamide or vinyl acetate is particularly preferable, and N-acryloylmorpholine or dimethylacrylamide is more preferable. By copolymerizing the monomers, the obtained adhesive layer 3 is more excellent in adhesion to the base material 2. These other monomer monomers may be used alone or in combination of two or more.
The proportion by mass of the structural moiety derived from the other monomer in the (meth) Acrylate Polymer (AP) is preferably 1% by mass or more, particularly preferably 3% by mass or more, and further preferably 5% by mass or more. The ratio is preferably 20% by mass or less, particularly preferably 18% by mass or less, and further preferably 15% by mass or less. This provides the adhesive layer 3 having more excellent adhesion to the base material 2.
The polymerization form of the (meth) Acrylate Polymer (AP) may be a random copolymer or a block copolymer. The polymerization method is not particularly limited, and polymerization can be carried out by a conventional polymerization method, for example, a solution polymerization method.
On the other hand, the active energy ray-curable group-containing compound (a3) contains: a functional group reactive with the functional group of the functional group-containing monomer (a2), and an active energy ray-curable group containing a carbon-carbon double bond cleaved by irradiation with an active energy ray.
Examples of the functional group reactive with the functional group of the functional group-containing monomer (a2) include an isocyanate group and an epoxy group, and among them, an isocyanate group having high reactivity with a hydroxyl group is preferable.
The active energy ray-curable group having a carbon-carbon double bond is preferably a (meth) acryloyl group or the like. In addition, 1 molecule of the active energy ray-curable group-containing compound (a3) preferably has 1 to 5, particularly preferably 1 to 3, carbon-carbon double bonds cleaved by irradiation with active energy rays.
Examples of the active energy ray-curable group-containing compound (a3) include 2-methacryloyloxyethyl isocyanate, m-isopropenyl- α, α -dimethylbenzyl isocyanate, methacryloyl isocyanate, allyl isocyanate, and 1,1- (bisacryloxymethyl) ethyl isocyanate; an acryloyl monoisocyanate compound obtained by the reaction of a diisocyanate compound or a polyisocyanate compound with hydroxyethyl (meth) acrylate; and acryloyl monoisocyanate compounds obtained by reacting a diisocyanate compound or a polyisocyanate compound with a polyol compound and hydroxyethyl (meth) acrylate. Among them, 2-methacryloyloxyethyl isocyanate is particularly preferable. The active energy ray-curable group-containing compound (a3) may be used alone or in combination of two or more.
In addition to the production of the acrylic polymer (a), the production of the (meth) Acrylate Polymer (AP) and the reaction of the (meth) Acrylate Polymer (AP) with the active energy ray-curable group-containing compound (a3) can be carried out by a conventional method. In this reaction step, the reactive functional group derived from the functional group-containing monomer (a2) in the (meth) Acrylate Polymer (AP) reacts with the functional group in the active energy ray-curable group-containing compound (A3). Thus, the acrylic polymer (a) having an energy ray-curable group introduced into the side chain can be obtained. The reaction of the (meth) Acrylate Polymer (AP) with the active energy ray-curable group-containing compound (a3) is preferably carried out in the presence of a catalyst such as an organometallic catalyst.
In the acrylic polymer (a), the amount of the active energy ray-curable group-containing compound (A3) is preferably 60 mol% or more, and particularly preferably 70 mol% or more, relative to the amount of the reactive functional group of the functional group-containing monomer (a 2). The amount of the active energy ray-curable group-containing compound (a3) is preferably 99 mol% or less, particularly preferably 95 mol% or less, and more preferably 90 mol% or less.
The proportion of the moiety derived from the functional group-containing monomer (a2) in the entire acrylic polymer (a) is preferably 0.1% by mass or more, particularly preferably 0.5% by mass or more, and more preferably 1% by mass or more. The ratio is preferably 12% by mass or less, particularly preferably 10% by mass or less, and further preferably 8% by mass or less. Thus, the obtained adhesive layer 3 is more excellent in adhesion to the base material 2 (coating layer 21).
The weight average molecular weight (Mw) of the acrylic polymer (a) is preferably 1 ten thousand or more. The weight average molecular weight (Mw) is preferably 150 ten thousand or less. When the weight average molecular weight (Mw) of the acrylic polymer (a) is in the above range, the coatability of the adhesive composition P can be ensured, and the cohesive property of the adhesive layer 3 is good, so that physical properties suitable for dicing and the like can be obtained.
The glass transition temperature (Tg) of the acrylic polymer (a) having an energy ray-curable group introduced into the side chain is as described above.
(2-1-2) crosslinking agent (B)
The adhesive composition P preferably contains a crosslinking agent (B) capable of crosslinking the acrylic polymer (a) having an energy ray-curable group introduced into a side chain thereof. In this case, the adhesive agent layer 3 in the present embodiment contains a crosslinked product obtained by a crosslinking reaction of the acrylic polymer (a) and the crosslinking agent (B). By using the crosslinking agent (B), the gel fraction of the adhesive forming the adhesive layer 3 can be easily adjusted to an appropriate range, and physical properties suitable for dicing and the like can be obtained.
Examples of the type of the crosslinking agent (B) include epoxy compounds, polyisocyanate compounds, polyimide compounds such as metal chelate compounds and aziridine compounds, melamine resins, urea resins, dialdehydes, methylol polymers, metal alkoxides, and metal salts. Among these, epoxy compounds and polyisocyanate compounds are preferably used, and polyisocyanate compounds are particularly preferably used, for the reason of easy control of the crosslinking reaction and the like.
Examples of the epoxy compound include 1, 3-bis (N, N '-diglycidylaminomethyl) cyclohexane, N' -tetraglycidyl-m-xylylenediamine, ethylene glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, diglycidylaniline, and diglycidylamine.
The polyisocyanate compound is a compound having 2 or more isocyanate groups per 1 molecule. Specific examples thereof include aromatic polyisocyanates such as tolylene diisocyanate, diphenylmethane diisocyanate, and xylylene diisocyanate; aliphatic polyisocyanates such as hexamethylene diisocyanate; and alicyclic polyisocyanates such as isophorone diisocyanate and hydrogenated diphenylmethane diisocyanate. Further, biuret, isocyanurate and adduct thereof are exemplified. Examples of the adduct include reaction products with low-molecular active hydrogen-containing compounds such as ethylene glycol, propylene glycol, neopentyl glycol, trimethylolpropane, and castor oil.
The crosslinking agent (B) may be used alone or in combination of two or more.
The content of the crosslinking agent (B) in the adhesive composition P is preferably 0.01 to 15 parts by mass, particularly preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 2 parts by mass, based on 100 parts by mass of the acrylic polymer (a) having an energy ray-curable group introduced into a side chain thereof.
(2-1-3) photopolymerization initiator (C)
When ultraviolet rays are used as the active energy rays used for curing the active energy ray-curable adhesive, the adhesive composition P preferably further contains a photopolymerization initiator (C). By containing the photopolymerization initiator (C), the acrylic polymer (a) having an energy ray-curable group introduced into a side chain thereof can be efficiently polymerized and cured, and the polymerization curing time and the irradiation dose of active energy rays can be reduced.
Examples of the photopolymerization initiator (C) include benzophenone, acetophenone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin benzoic acid, benzoin methyl benzoate, benzoin dimethyl ketal, 2, 4-diethylthioxanthone, 1-hydroxycyclohexylphenyl ketone, benzyldiphenyl sulfide, tetramethylthiuram monosulfide, azobisisobutyronitrile, benzil, butanedione, β -chloroanthraquinone, (2,4, 6-trimethylbenzyldiphenyl) phosphine oxide, 2-benzothiazole N, N-diethyldithiocarbamate, oligo { 2-hydroxy-2-methyl-1- [4- (1-propenyl) phenyl ] acetone }, 2-dimethoxy-1, 2-diphenylethan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one, and the like. These photopolymerization initiators may be used alone or in combination of two or more.
The content of the photopolymerization initiator (C) in the adhesive composition P is preferably 0.1 to 10 parts by mass, and particularly preferably 0.5 to 8 parts by mass, per 100 parts by mass of the acrylic polymer (a) having an energy ray-curable group introduced into a side chain thereof.
(2-1-4) other Components
The adhesive composition P of the present embodiment may contain additives such as antistatic agents, tackifiers, antioxidants, light stabilizers, softeners, and fillers as required, as long as the above effects of the adhesive sheet 1 for processing workpieces of the present embodiment are not impaired. The following dilution solvents are not included in the additives constituting the adhesive composition P.
(2-2) preparation of adhesive composition
The adhesive composition P in the present embodiment can be prepared by: an acrylic polymer (a) is prepared, and a crosslinking agent (B), a photopolymerization initiator (C) and additives are mixed with the acrylic polymer (a) obtained as needed. At this time, a diluting solvent may be added as needed to obtain a coating liquid of the adhesive composition P.
Examples of the diluting solvent include aliphatic hydrocarbons such as hexane, butane and cyclohexane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and dichloroethane, alcohols such as methanol, ethanol, propanol, butanol and 1-methoxy-2-propanol, ketones such as acetone, methyl ethyl ketone, 2-pentanone, isophorone and cyclohexanone, esters such as ethyl acetate and butyl acetate, and cellosolve solvents such as ethyl cellosolve.
The concentration and viscosity of the coating liquid prepared in the above manner are not particularly limited as long as they are within a range in which the coating liquid can be applied, and may be appropriately selected depending on the case. For example, the concentration of the adhesive composition P is diluted so as to be 10 mass% or more and 60 mass% or less. In addition, when obtaining the coating liquid, the addition of a diluting solvent or the like is not an essential condition, and if the adhesive composition P has a coatable viscosity or the like, the addition of a diluting solvent may not be necessary. In this case, the adhesive composition P is a coating solution in which the polymerization solvent of the acrylic polymer (a) is used as it is as a diluting solvent.
(2-3) thickness of adhesive layer
The thickness of the adhesive layer 3 in the present embodiment is preferably 10 μm or more, particularly preferably 15 μm or more, and more preferably 20 μm or more. Thus, the adhesive sheet 1 for work processing easily exhibits a good adhesive force, and for example, can effectively suppress chip scattering during dicing. The thickness of the adhesive layer 3 is preferably 100 μm or less, and particularly preferably 50 μm or less. Accordingly, after the irradiation with the active energy ray, the adhesive force to the workpiece after the processing is appropriately reduced, and the workpiece is easily separated from the adhesive sheet 1 for processing the workpiece.
(3) Release sheet
In the adhesive sheet 1 for processing a work of the present embodiment, a release sheet 4 is laminated on an adhesive layer 3. The release sheet 4 may be a process material for forming the adhesive layer 3, or may protect the adhesive surface of the adhesive layer 3 during a period until the work processing adhesive sheet 1 is attached to the work. In the adhesive sheet 1 for processing a workpiece according to the present embodiment, the release sheet 4 may be omitted.
The release sheet 4 may be of any configuration, and examples thereof include those obtained by subjecting a plastic film to a release treatment with a release agent or the like. Specific examples of the plastic film include polyester films such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate, and polyolefin films such as polypropylene and polyethylene. As the release agent, silicone (silicone) based, fluorine based, long chain alkyl based release agents and the like can be used, and among them, silicone based release agents which are inexpensive and can obtain stable performance are preferable. The thickness of the release sheet 4 is not particularly limited, but is usually 20 μm or more and 250 μm or less.
(4) Other structural elements
The pressure-sensitive adhesive sheet 1 for processing a workpiece of the present embodiment may have a pressure-sensitive adhesive layer laminated on the pressure-sensitive adhesive surface of the pressure-sensitive adhesive layer 3. In this case, the adhesive sheet 1 for processing a workpiece of the present embodiment can be used as a dicing/bonding wafer by providing the adhesive layer as described above. In the dicing/bonding wafer, a work is attached to the surface of the adhesive layer opposite to the adhesive layer 3, and the adhesive layer is diced together with the work, whereby a chip having a singulated (singulated) adhesive layer stacked thereon can be obtained. The chip can be easily fixed to the object on which the chip is mounted by the singulated adhesive layer. As a material constituting the pressure-sensitive adhesive layer, a material containing a thermoplastic resin and a low-molecular-weight thermosetting pressure-sensitive adhesive component, or a material containing a B-stage (semi-cured) thermosetting pressure-sensitive adhesive component is preferably used.
In the adhesive sheet 1 for processing a workpiece according to the present embodiment, a protective film-forming layer may be laminated on the adhesive surface of the adhesive layer 3. In this case, the adhesive sheet 1 for processing a work of the present embodiment can be used as a sheet for forming a protective film and also for processing a work. In this sheet, for example, a work is stuck to the surface of the protective film forming layer opposite to the adhesive agent layer 3, and the protective film forming layer is cut together with the work, whereby a chip in which the singulated protective film forming layers are stacked can be obtained. In this case, generally, a protective film forming layer is laminated on the surface opposite to the surface on which the circuit is formed. The protective film having sufficient durability can be formed on the chip by forming the protective film layer by singulation and curing the protective film layer at a specific timing. The protective film-forming layer is preferably composed of an uncured curable adhesive.
2. Physical Properties of adhesive sheet for working
In the adhesive sheet 1 for processing a workpiece of the present embodiment, the surface of the adhesive sheet 1 for processing a workpiece on the adhesive layer 3 side is fixed to a support, and after the adhesive layer 3 is cured by irradiating the adhesive layer 3 with an active energy ray, the interlayer strength between the substrate 2 and the adhesive layer 3, measured as a peeling force when the substrate 2 is peeled from the adhesive layer 3 at a peeling angle of 180 ° and a peeling speed of 300 mm/min, is preferably 1000mN/25mm or more, particularly preferably 3000mN/25mm or more, and further preferably 5000mN/25mm or more. By setting the interlayer strength to the above value, the residual glue at the time of separation from the workpiece can be effectively suppressed. The adhesive sheet 1 for processing a work of the present embodiment can achieve the above interlayer strength by having the above-described configuration and physical properties. The upper limit of the interlayer strength is not particularly limited, but is preferably 50000mN/25mm or less. The details of the method for measuring the interlayer strength are described in the following test examples.
3. Method for producing adhesive sheet for processing work
The method for producing the adhesive sheet 1 for processing a workpiece of the present embodiment is not particularly limited. A preferred production method includes: forming a coating layer 22 containing a pyrrolidone-based compound on one surface of a base material body 21 to obtain a base material 2; a step of applying (a coating liquid of) the adhesive composition P onto the release surface of the release sheet 4 to form the adhesive layer 3; and a step of bonding the surface of the substrate 2 on the coating layer 22 side to the adhesive layer 3.
The coating layer 22 can be formed on one side of the base material body 21 by a known method. For example, the coating layer 22 can be formed by applying a coating agent for forming the coating layer 22 on one surface of the base material body 21 by a bar coating method, a blade coating method, a roll coating method, a blade coating method, a die coating method, a gravure coating method, or the like to form a coating film, and drying the coating film.
The adhesive layer 3 can be formed on the release surface of the release sheet 4 by a known method. For example, the adhesive layer 3 can be formed by applying a coating liquid of the adhesive composition P to the release surface of the release sheet 4 by a bar coating method, a blade coating method, a roll coating method, a blade coating method, a die coating method, a gravure coating method, or the like to form a coating film, and drying the coating film.
When the adhesive composition P contains the crosslinking agent (B), it is preferable that: by changing the drying conditions (temperature, time, etc.) or by separately providing a heating treatment, the crosslinking reaction between the acrylic polymer (a) and the crosslinking agent (B) in the coating film proceeds, and a crosslinked structure is formed in the adhesive agent layer 3 at a desired density.
After the surface of the substrate 2 on the coating layer 22 side is bonded to the adhesive layer 3, so-called aging (aging) may be performed in order to sufficiently progress the above-mentioned crosslinking reaction, for example, by leaving the substrate in an environment of 23 ℃ and a relative humidity of 50% for several days.
The method of transferring the adhesive layer 3 formed on the release sheet 4 to the substrate 2 in the above manner is preferable because the production efficiency is high. In general, the method using this transfer tends to reduce adhesion between the base material and the adhesive layer. However, the adhesive sheet 1 for processing a workpiece of the present embodiment has the above-described configuration and physical properties, and thus, even when produced by this method, the adhesive layer 3 has high adhesion to the base material 2, and therefore, the adhesive residue on the workpiece when separated from the workpiece can be effectively suppressed.
In addition, although the production efficiency is lowered, the adhesive layer 3 formed on the release sheet 4 may be formed directly on the coating layer 22 of the substrate 2 instead of transferring the adhesive layer 3 onto the substrate 2 in the above-described manner. In this case, the release sheet 4 may be laminated on the adhesive layer 3, or the release sheet 4 may not be laminated.
4. Method for using adhesive sheet for processing workpiece
The adhesive sheet 1 for workpiece processing of the present embodiment can be used for processing a workpiece. That is, the adhesive surface of the adhesive sheet 1 for workpiece processing according to the present embodiment may be attached to a workpiece, and then the workpiece may be processed on the adhesive sheet 1 for workpiece processing.
The workpiece to be processed using the adhesive sheet 1 for processing a workpiece of the present embodiment is not particularly limited. Examples of the work include semiconductor wafers, semiconductor members such as semiconductor packages, and glass members such as glass plates. According to the adhesive sheet 1 for processing a workpiece of the present embodiment, the adhesive residue on the processed workpiece can be suppressed, and therefore, it is preferably used for a workpiece requiring no occurrence of such adhesive residue.
Examples of the processing using the adhesive sheet 1 for processing a workpiece according to the present embodiment include back grinding, dicing, spreading, and picking up. The various processes described above can be performed using one adhesive sheet 1 for workpiece processing, or the adhesive sheet 1 for workpiece processing can be replaced during a series of processes.
After the completion of the processing, when the processed work is separated from the work processing adhesive sheet 1, the adhesive layer 3 is preferably irradiated with an active energy ray before the separation. This can reduce the adhesive force to the processed work, and the separation can be easily performed. As the active energy ray, ultraviolet rays, electron rays, and the like can be generally used, and ultraviolet rays which are easy to handle are particularly preferable.
The irradiation of the ultraviolet ray may be performed by a high-pressure mercury lamp, a fusion lamp (fusion lamp), a xenon lamp, or the like, and the illuminance is preferably 50mW/cm with respect to the irradiation amount of the ultraviolet ray2Above 1000mW/cm2The following. The amount of ultraviolet light is preferably 50mJ/cm2Above, 80mJ/cm is particularly preferable2The above is more preferably 100mJ/cm2The above. Further, the light amount of the ultraviolet ray is preferably 2000mJ/cm2The concentration is preferably 1000mJ/cm2Hereinafter, more preferably 500mJ/cm2The following.
For example, a semiconductor wafer or a glass plate as a workpiece is diced into a plurality of semiconductor chips on the adhesive sheet 1 for processing a workpiece, and then the adhesive sheet 1 for processing a workpiece is spread as necessary. Then, the adhesive layer 3 is irradiated with active energy rays to cure the adhesive layer 3, and then semiconductor chips or glass chips are picked up one by one from the work processing adhesive sheet 1.
The adhesive sheet 1 for processing a workpiece of the present embodiment has the above-described composition and physical properties, and thus can prevent the adhesive constituting the adhesive layer 3 from adhering to the surface of the picked-up semiconductor chip or glass chip. That is, the adhesive residue on the semiconductor chip or the glass chip can be suppressed.
In particular, the adhesive sheet 1 for processing a workpiece according to the present embodiment is particularly suitable for use in a workpiece having a recessed portion on the surface. In this case, the adhesive surface of the adhesive sheet 1 for workpiece processing may be adhered to the surface of the workpiece where the recess exists. Examples of such a workpiece having a concave portion include a semiconductor wafer having a protective film or a sealing resin layer in which a minute concave portion is formed by laser irradiation (laser marking), a glass plate in which minute concave portions such as a groove are formed, and the like. The adhesive sheet 1 for processing a workpiece according to the present embodiment can satisfactorily achieve the effect of suppressing adhesive residue even when used for a workpiece having a concave portion on the surface.
The embodiments described above are described for easy understanding of the present invention, and are not described for limiting the present invention. Therefore, each element disclosed in the above embodiments also includes all design changes and equivalents within the technical scope of the present invention.
For example, the release sheet 4 may be omitted, or another layer may be provided on the surface of the substrate 2 opposite to the adhesive layer 3.
Examples
The present invention will be described in more detail with reference to examples and the like, but the scope of the present invention is not limited to these examples and the like.
[ production example 1] (production of base Material X)
(1) Preparation of coating Agents
938g of water and 0.046mg of copper (II) sulfate are poured into the reaction vessel and the temperature is raised to 60 ℃. Subsequently, 1kg of N-vinylpyrrolidone, 6g of 25% aqueous ammonia and 34g of 35% by mass aqueous hydrogen peroxide were added dropwise thereto over 180 minutes while maintaining 60 ℃. After the completion of the dropwise addition, 2g of 25 mass% aqueous ammonia was added. After 4 hours from the start of the reaction, the temperature was raised to 80 ℃ and 5g of 35 mass% hydrogen peroxide water was added. Subsequently, 5.5 hours after the start of the reaction, 5g of 35 mass% hydrogen peroxide water was added, and the mixture was maintained at 80 ℃ for 1 hour, thereby obtaining a 50 mass% aqueous polyvinylpyrrolidone solution. The weight average molecular weight (Mw) of the polyvinylpyrrolidone thus obtained was 30 ten thousand.
A coating agent (10 mass% aqueous solution) was obtained by mixing 40 parts by mass (in terms of solid content; the same applies hereinafter) of the aqueous polyvinylpyrrolidone solution obtained above, 50 parts by mass of a polyester-based binder resin (GOO CHEMICAL CO., manufactured by LTD., product name "PLAS COAT: Z-730", weight average molecular weight: 3000, acid value: 50.0KOHmg/g, hydroxyl value: 5.0KOHmg/g), and 5 parts by mass of a water-soluble curing agent for oxazoline group-containing polymer (NIPPON SHOKUBA CO., manufactured by LTD., product name "EPOCROS: WS-300", weight average molecular weight: 120000).
(2) Formation of the coating
The coating agent obtained above was coated on one side of a polyethylene terephthalate film (manufactured by Mitsubishi Chemical corporation, product name "PET 100T-100 ミツビシ", thickness 100 μm) as a substrate body using a meyer bar. Then, the coating film was dried at 110 ℃ for 1 minute to form a coating layer (pyrrolidone-based coating layer) having a thickness of 0.05 μm on the substrate body, which was used as the substrate X.
[ production example 2] (production of base Material Y)
(1) Preparation of coating Agents
40 parts by mass of a water-soluble polyvinyl alcohol resin (KURARAAY CO., manufactured by LTD, product name "POVAL"), 50 parts by mass of an alcohol binder resin (GOO CHEMICAL CO., manufactured by LTD, product name "PLAS COAT: Z-565"), and 5 parts by mass of a water-soluble curing agent for an oxazoline group-containing polymer (NIPPON SHOKUBAI CO., manufactured by LTD, product name "EPOCROS: WS-300", weight-average molecular weight: 120000) were mixed to obtain a coating agent (10 mass% aqueous solution).
(2) Formation of the coating
The coating agent obtained above was coated on one side of a polyethylene terephthalate film (product name "PET 100T-100 ミツビシ", thickness 100 μm, manufactured by Mitsubishi Chemical corporation) as a substrate body using a meyer rod. Then, the coating film was dried at 110 ℃ for 1 minute to form a coating layer (non-pyrrolidone-based coating layer) having a thickness of 0.05 μm on the substrate body, which was used as the substrate Y.
[ example 1]
(1) Preparation of adhesive composition
By a solution polymerization method, 75 parts by mass of n-Butyl Acrylate (BA), 10 parts by mass of Methyl Methacrylate (MMA), and 15 parts by mass of 2-hydroxyethyl acrylate (HEA) were polymerized to obtain a (meth) acrylate polymer. This (meth) acrylate polymer was reacted with 30g (80 mol% relative to 2-hydroxyethyl acrylate) of methacryloyloxyethyl isocyanate (MOI) per 100g of the (meth) acrylate polymer to obtain an acrylic polymer having an active energy ray-curable group introduced into the side chain. The weight average molecular weight (Mw) of the acrylic polymer was 60 ten thousand.
100 parts by mass of the acrylic polymer having an active energy ray-curable group introduced into a side chain obtained as described above, 7 parts by mass of 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one (product name "Omnirad 127", manufactured by BASF CORPORATION) as a photopolymerization initiator, and 0.2 parts by mass of trimethylolpropane-modified toluene diisocyanate (product name "CORONATE L", manufactured by TOSOH CORPORATION) as a crosslinking agent were mixed in a solvent to obtain a coating liquid of an adhesive composition.
(2) Formation of adhesive layer
A coating liquid of the above adhesive composition was applied to a release surface of a release sheet (product name "SP-PET 381031", manufactured by linec CORPORATION) formed by forming a silicone-based release agent layer on one surface of a polyethylene terephthalate (PET) film having a thickness of 38 μm, and dried by heating, thereby forming an adhesive agent layer having a thickness of 25 μm on the release sheet.
(3) Production of adhesive sheet for workpiece processing
The exposed surface of the adhesive layer formed in the step (2) was bonded to the surface of the substrate X on the coating layer side prepared in production example 1, thereby obtaining an adhesive sheet for workpiece processing.
Examples 2 to 6 and comparative examples 1 to 2
An adhesive sheet for workpiece processing was produced in the same manner as in example 1, except that the kinds and proportions of the monomers constituting the acrylic polymer having an active energy ray-curable group introduced into the side chain ((meth) acrylate polymer) and the weight average molecular weight (Mw) of the acrylic polymer were changed as shown in table 1.
Comparative examples 3 to 4
An adhesive sheet for workpiece processing was produced in the same manner as in example 1, except that the kinds and proportions of the monomers constituting the acrylic polymer having an active energy ray-curable group introduced into the side chain ((meth) acrylate polymer), and the weight average molecular weight (Mw) of the acrylic polymer were changed as shown in table 1, and the substrate X was changed to the substrate Y.
Comparative example 5
An adhesive sheet for workpiece processing was produced in the same manner as in example 1, except that the substrate X was changed to the substrate Y.
Comparative example 6
An EMAA film having a thickness of 80 μm obtained by extrusion molding of an ethylene-methacrylic acid copolymer (EMAA) (DuPont-Mitsui Polychemicals Co., Ltd., product name "NUCREL N0903 HC") by a small T die extruder (Toyo Seiki Seisaku-sho, Ltd., product name "LABO PLASTOMILL") was irradiated with 110kGy of electron rays for 2.2 seconds. An adhesive sheet for workpiece processing was produced in the same manner as in example 1, except that the thus-obtained EMAA film was used in place of the substrate X.
The abbreviations and the like shown in table 1 are as follows.
BA: acrylic acid n-butyl ester
MMA: methacrylic acid methyl ester
HEA: 2-hydroxyethyl acrylate
ACMO: n-acryloyl morpholine
DMAA: n, N-dimethylacrylamide
2 EHA: 2-ethylhexyl acrylate
VAc: vinyl acetate ester
The weight average molecular weight (Mw) is a weight average molecular weight in terms of standard polystyrene measured by Gel Permeation Chromatography (GPC) under the following conditions (GPC measurement).
< measurement conditions >
The measurement device: HLC-8320 manufactured by TOSOH CORPORATION
GPC column (passage in the following order): TOSOH CORPORATION (TOSOH CORPORATION)
TSK gel SuperH-H
TSK gel superHM-H
TSK gel superH2000
Determination of the solvent: tetrahydrofuran (THF)
Measurement temperature: 40 deg.C
[ test example 1] (measurement of storage modulus of substrate)
The storage modulus at 25 ℃ of the substrates prepared and used in examples and comparative examples was measured by the following apparatus under the following conditions. The results are shown in Table 1.
A measuring device: dynamic modulus measuring apparatus, product name "RHEOVIBRON DDV-01 FP", manufactured by A & D Company, Limited "
Test start temperature: 0 deg.C
Test end temperature: 200 deg.C
Temperature rise rate: 3 ℃/min
Frequency: 11Hz
Amplitude: 20 μm
[ test example 2] (calculation of glass transition temperature)
The glass transition temperature (Tg) of the acrylic polymers having active energy ray-curable groups introduced into the side chains, prepared in examples and comparative examples, was calculated by the Fox equation. The results are shown in Table 1.
[ test example 3] (measurement of interlayer Strength)
The surface on the substrate side of a high adhesion UV adhesive sheet (manufactured by linec CORPORATION, product name "adhere D-510T") comprising 3 layers of a substrate, an adhesive layer made of a high adhesion UV curable adhesive laminated on one surface of the substrate, and a release sheet laminated on the surface of the adhesive layer opposite to the substrate was fixed to one surface of a stainless steel plate (SUS304#600) as a support via a double-sided adhesive tape (manufactured by linec CORPORATION, product name "tack liner").
Next, the release sheet was peeled from the high-adhesion UV adhesive sheet to expose the surface of the adhesive layer opposite to the substrate. Next, the release sheet was peeled from the adhesive sheet for workpiece processing produced in examples and comparative examples to expose the adhesive surface, and the adhesive surface was attached to the exposed surface of the adhesive layer of the high adhesion UV adhesive sheet.
Then, the adhesive layer in the adhesive sheet for workpiece processing was irradiated with ultraviolet rays (illuminance: 230 mW/cm) from the surface on the substrate side of the adhesive sheet for workpiece processing2Light ofQuantity: 190mJ/cm2) The adhesive layer of the adhesive sheet for processing a work and the adhesive layer of the high adhesion UV adhesive sheet are cured.
Thereafter, the base material of the adhesive sheet for work processing was peeled from the adhesive layer of the adhesive sheet for work processing under conditions of a peeling angle of 180 ° and a peeling speed of 300 mm/min using a universal tensile tester (product name "AUTOGRAPH AG-IS" manufactured by Shimadzu CORPORATION), and the peeling force (mN/25mm) at that time was measured. The peel force was used as the interlayer strength (mN/25 mm). The results are shown in Table 1.
In addition, the adhesive sheets for workpiece processing of examples 1 to 3 were not able to be measured because the interlayer strength between the adhesive layer and the substrate of the adhesive sheets for workpiece processing was too high and the substrate or the adhesive layer was torn.
[ test example 4] (evaluation of residual adhesive)
The mirror surface of the silicon wafer was engraved with a laser engraving device (product name "MD-S9910A", manufactured by KEYENCE CORPORATION). Thus, the mirror surface was formed with a trench having a width of about 50 μm and a depth of about 25 μm in cross-sectional view.
Next, the adhesive surface exposed by peeling the release sheet from the adhesive sheet for workpiece processing produced in examples and comparative examples was attached to the mirror surface after laser marking using a 2kg rubber roller, and left for 20 minutes.
Then, the adhesive layer of the adhesive sheet for workpiece processing was irradiated with ultraviolet rays (illuminance: 230 mW/cm) from the surface on the substrate side of the adhesive sheet for workpiece processing2Light amount: 190mJ/cm2) The adhesive layer of the adhesive sheet for workpiece processing is cured.
Thereafter, the mirror surface was separated from the adhesive sheet for workpiece processing, and the residue (adhesion of the adhesive) on the engraved portion of the mirror surface was visually confirmed. As a result, the evaluation was "excellent" with no residual gum, the evaluation was "good" with little residual gum confirmed, and the evaluation was "poor" with residual gum.
The results are shown in Table 1.
[ test example 5] (evaluation of edge chipping)
The release sheet was peeled from the adhesive sheet for work processing produced in examples and comparative examples, and a 6-inch silicon wafer and a ring frame for dicing were attached to the exposed adhesive layer using a tape bonder (product name "advill RAD2500 m/12", manufactured by linec CORPORATION). Subsequently, the adhesive sheet for workpiece processing was cut in accordance with the outer diameter of the annular frame, and then cut from the silicon wafer side using a dicing apparatus (DFD-651, manufactured by DISCO CORPORATION) under the following dicing conditions to obtain a chip having a square width of 8 mm.
< cutting conditions >
Thickness of wafer: 350 μm
A cutting device: product name DFD-651 manufactured by DISCO CORPORATION "
A tool: manufactured by DISCO CORPORATION, product name "NBC-2H 205027 HECC"
Width of the tool: 0.025 to 0.030mm
Feed amount of tool: 0.640-0.760 mm
Tool rotation speed: 30000rpm
Cutting speed: 80 mm/sec
Depth of cut into the substrate: 20 μm
Amount of cutting water: 1.0L/min
Temperature of cutting water: 20 deg.C
Among the obtained 8mm square chips, chips located at the center and in the vicinity of the work processing adhesive sheet were observed for the presence or absence of chipping (chipping of the chip end). Specifically, 50 chip side portions were observed in the flow direction (MD direction) during the production of the base material body and 50 chip side portions were observed in the direction perpendicular to the MD direction (CD direction) using an electron microscope (product name "VHZ-100" manufactured by KEYENCE CORPORATION, magnification: 300 times). Then, a defect having a width or depth of 100 μm or more is determined as a broken edge, and the number of chips having a broken edge is counted. Based on the results, edge chipping was evaluated based on the following criteria. The evaluation results are shown in table 1.
Good: the number of chips with edge breakage is less than 5.
X: the number of chips with edge breakage is 5 or more.
[ Table 1]
Figure BDA0003136193410000281
As is clear from table 1, the adhesive sheet for workpiece processing obtained in the examples can satisfactorily suppress adhesive residue on the workpiece when the adhesive sheet is separated from the workpiece. And also can suppress occurrence of chipping at the time of cutting.
Industrial applicability
The adhesive sheet for workpiece processing of the present invention is suitably used for processing a workpiece, particularly a workpiece having a minute recessed portion on the surface, which is required to be free from adhesive residue.
Description of the reference numerals
1: an adhesive sheet for processing a workpiece; 2: a substrate; 21: a substrate body; 22: coating; 3: an adhesive layer; 4: and (4) peeling off the sheet.

Claims (10)

1. An adhesive sheet for processing a workpiece, comprising a base material and an adhesive layer laminated on one surface of the base material,
the adhesive layer is composed of an active energy ray-curable adhesive formed from an adhesive composition containing an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof,
the acrylic polymer has a glass transition temperature (Tg) of-80 ℃ or higher and-30 ℃ or lower,
a coating layer containing a pyrrolidone-based compound is formed on the surface of the base material that is in contact with the adhesive agent layer.
2. The pressure-sensitive adhesive sheet for processing a workpiece according to claim 1, wherein the acrylic polymer has a structure derived from an alkyl (meth) acrylate in a main chain of the polymer,
the number of carbon atoms of the acrylic group in the alkyl (meth) acrylate is 1 to 4.
3. The adhesive sheet for processing a workpiece according to claim 1 or 2, wherein the acrylic polymer has a structure derived from a functional group-containing monomer in a main chain of the polymer,
the proportion of the structural moiety derived from the functional group-containing monomer in the entire acrylic polymer is 0.1 to 12 mass%.
4. The adhesive sheet for processing a workpiece according to any one of claims 1 to 3, wherein the pyrrolidone-based compound is a polymer having vinylpyrrolidone as a main structural unit.
5. The adhesive sheet for processing a workpiece according to any one of claims 1 to 4, wherein the storage modulus of the base material at 25 ℃ is 1000MPa or more.
6. The pressure-sensitive adhesive sheet for processing a workpiece according to claim 5, wherein the substrate comprises a polyethylene terephthalate film as a substrate body.
7. The adhesive sheet for processing a workpiece according to any one of claims 1 to 6, which is a dicing sheet.
8. A method for producing the adhesive sheet for workpiece processing according to any one of claims 1 to 7, the method comprising:
forming a coating layer containing a pyrrolidone-based compound on one surface of a base material body to obtain the base material;
a step of applying the adhesive composition to a release surface of a release sheet to form the adhesive layer; and
and a step of bonding the coating-side surface of the base material to the adhesive layer.
9. A method for producing the adhesive sheet for workpiece processing according to claim 3, the method comprising:
a step for preparing a (meth) acrylate polymer obtained by copolymerizing a functional group-containing monomer in an amount of 5 to 35 mass%, and reacting the (meth) acrylate polymer with an active energy ray-curable group-containing compound having a functional group to prepare an acrylic polymer having an active energy ray-curable group introduced into a side chain thereof, thereby preparing an adhesive composition containing the acrylic polymer;
forming a coating layer containing a pyrrolidone-based compound on one surface of a base material body to obtain the base material;
a step of applying the adhesive composition to a release surface of a release sheet to form the adhesive layer; and
and a step of bonding the coating-side surface of the base material to the adhesive layer.
10. The method of manufacturing an adhesive sheet for processing a workpiece according to claim 9, wherein an amount of the active energy ray-curable group-containing compound having a functional group is 60 mol% or more and 99 mol% or less with respect to an amount of the functional group-containing monomer.
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