WO2021044833A1 - Bande abrasive arrière - Google Patents

Bande abrasive arrière Download PDF

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Publication number
WO2021044833A1
WO2021044833A1 PCT/JP2020/030939 JP2020030939W WO2021044833A1 WO 2021044833 A1 WO2021044833 A1 WO 2021044833A1 JP 2020030939 W JP2020030939 W JP 2020030939W WO 2021044833 A1 WO2021044833 A1 WO 2021044833A1
Authority
WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
pressure
meth
polyurethane
mass
Prior art date
Application number
PCT/JP2020/030939
Other languages
English (en)
Japanese (ja)
Inventor
達宏 池谷
中西　健一
Original Assignee
昭和電工株式会社
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 昭和電工株式会社 filed Critical 昭和電工株式会社
Priority to JP2021543681A priority Critical patent/JPWO2021044833A1/ja
Priority to KR1020217041627A priority patent/KR102589564B1/ko
Priority to CN202080045154.6A priority patent/CN113993663B/zh
Publication of WO2021044833A1 publication Critical patent/WO2021044833A1/fr

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Classifications

    • 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]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D11/00—Constructional features of flexible abrasive materials; Special features in the manufacture of such materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
    • B24D11/00—Constructional features of flexible abrasive materials; Special features in the manufacture of such materials
    • B24D11/02—Backings, e.g. foils, webs, mesh fabrics
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the present invention relates to a back grind tape preferably used for processing semiconductor wafers.
  • the present application claims priority based on Japanese Patent Application No. 2019-162092 filed in Japan on September 5, 2019, the contents of which are incorporated herein by reference.
  • a semiconductor wafer backgrinding process is being performed in the semiconductor device manufacturing process.
  • the front surface (front surface) of the semiconductor wafer is protected with a back grind tape, and then the back surface of the semiconductor wafer is ground to make the semiconductor wafer thinner.
  • Patent Document 1 describes a base material layer, an unevenness absorbing resin layer, an antistatic layer, and an adhesive resin layer. Adhesive films for processing semiconductor wafers provided in order are disclosed.
  • the adhesive film for semiconductor wafer processing described in Patent Document 1 needs to be manufactured by laminating each layer after forming a sheet, so that the manufacturing procedure is complicated. Further, the back grind tape is required to have an adhesive force capable of fixing an adherend such as a semiconductor wafer to the back grind tape with sufficient strength. However, when the back grind tape with high adhesive strength is attached to the adherend, the adherend is processed, and then the back grind tape is peeled off, the adhesive layer of the back grind tape is transferred to the adherend. The rest may occur.
  • the present invention has been made in view of the above circumstances, has sufficient unevenness absorbing property, antistatic property, and adhesive strength, is less likely to leave adhesive residue after peeling the backgrinding tape, and requires less manufacturing process. It is an object of the present invention to provide a manufacturable back grind tape.
  • the first aspect of the present invention is the following back grind tape.
  • a back grind tape having a sheet-shaped base material and an adhesive layer formed on one side of the base material.
  • the pressure-sensitive adhesive layer is made of a cured product of the pressure-sensitive adhesive composition and has a thickness of 50 to 500 ⁇ m.
  • the pressure-sensitive adhesive composition contains a polyurethane (A), a (meth) acrylate monomer (B), a chain transfer agent (C), a photopolymerization initiator (D), and an ionic liquid (E).
  • the polyurethane (A) contains a polyurethane (a1) having a skeleton containing a structure derived from a polyoxyalkylene polyol and a structure derived from a polyisocyanate, and having a (meth) acryloyl group at a plurality of ends.
  • the backgrinding tape of the first aspect of the present invention can preferably include the following features as described below.
  • the following features may preferably be a combination of two or more.
  • [2] The back grind tape according to [1], wherein the pressure-sensitive adhesive layer has a single-layer structure.
  • [3] The back grind tape according to [1] or [2], wherein the (meth) acrylate monomer (B) contains a monofunctional (meth) acrylate and a polyfunctional (meth) acrylate.
  • the ionic liquid (E) is any of [1] to [3], which is a compound containing an organic cation selected from the group consisting of a quaternary ammonium ion, an iminium ion, and a sulfonium ion.
  • the back grind tape described.
  • the ionic liquid (E) is 1-ethyl-3-methylimidazolium cation and / or 4-methyl-1-octyl pyridinium cation, bis (fluorosulfonyl) imide anion ((FSO 2) 2 N -
  • [7] The backgrinding tape according to any one of [1] to [6], wherein the chain transfer agent (C) is a polyfunctional thiol.
  • the pressure-sensitive adhesive composition 20 to 50% by mass of the polyurethane (A), 35-79% by mass of the (meth) acrylate monomer (B), 0.5 to 8.0% by mass of the chain transfer agent (C), 0.01 to 5.0% by mass of the photopolymerization initiator (D), The ionic liquid (E) is contained in an amount of 0.4 to 6.0% by mass.
  • the back grind tape according to any one of [1] to [10].
  • the present invention it is possible to provide a backgrinding tape having sufficient unevenness absorbing property, antistatic property, and adhesive strength, and in which adhesive residue is unlikely to occur after the backgrinding tape is peeled off.
  • the pressure-sensitive adhesive layer is a cured product of the pressure-sensitive adhesive composition, and has sufficient unevenness absorption, antistatic property, and adhesive strength. Therefore, it is not necessary to separately provide the layer having the unevenness absorbing property, the layer having the antistatic property, and the layer having the adhesive force, and the tape can be manufactured in a small number of manufacturing steps. Therefore, the backgrinding tape of the present invention is used to protect the surface of an adherend having an uneven portion on the surface, such as a semiconductor wafer having bumps formed on the surface. Suitable as a tape.
  • the back grind tape (hereinafter, also referred to as “BG tape”) in the present embodiment has a sheet-like base material and an adhesive layer formed on one side of the base material.
  • the pressure-sensitive adhesive layer is composed of a cured product of the pressure-sensitive adhesive composition described later, and preferably has a single-layer structure.
  • the shape of the "tape” referred to here is not limited to a strip shape, but may be any shape, and includes a rectangular or disc-shaped sheet.
  • the material of the base material can be appropriately selected, and examples thereof include a resin material.
  • Resin materials include polyolefins such as polyethylene (PE) and polypropylene (PP); polyester sheets such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyethylene naphthalate; polyvinyl chloride (PVC); polyimide (PI). ; Polyphenylene terephide (PPS); ethylene vinyl acetate (EVA); polytetrafluoroethylene (PTFE) and the like.
  • PE, PP, and PET are preferably used because a sheet having appropriate flexibility can be obtained.
  • As the resin material only one kind may be used alone, or two or more kinds may be mixed and used.
  • the substrate may be transparent or opaque.
  • the resin sheet When a resin sheet made of a resin material is used as the base material, the resin sheet may have a single layer or a multi-layer structure having two or more layers (for example, a three-layer structure).
  • the resin material constituting each layer may be a resin material containing only one type alone or a resin material containing two or more types.
  • a base material that has been subjected to antistatic treatment may be used as the base material.
  • the antistatic treatment applied to the base material is not particularly limited, but a method of providing an antistatic layer on at least one surface of the base material, a method of kneading an antistatic agent into the base material, and the like can be used. Further, the surface on which the pressure-sensitive adhesive layer of the base material is formed is subjected to easy-adhesion treatment such as acid treatment, alkali treatment, primer treatment, corona treatment, plasma treatment, ultraviolet treatment, ozone treatment, etc., if necessary. You may.
  • the thickness of the base material can be appropriately selected according to the material of the base material and the like.
  • the thickness of the base material is, for example, 10 to 1000 ⁇ m. It is preferably 50 to 300 ⁇ m.
  • the thickness of the base material is 10 ⁇ m or more, the rigidity (stiffness) of the BG tape becomes high. Therefore, when the BG tape is attached to or peeled off from the semiconductor wafer as an adherend, the BG tape tends to be less likely to have wrinkles and floats. Further, when the thickness of the base material is 1000 ⁇ m or less, the BG tape attached to the semiconductor wafer can be easily peeled off from the semiconductor wafer, and workability (handleability, handling) is improved.
  • the pressure-sensitive adhesive layer is composed of a cured product of the pressure-sensitive adhesive composition described later.
  • the pressure-sensitive adhesive layer attaches the BG tape to the surface of the adherend sufficiently.
  • the pressure-sensitive adhesive layer absorbs and smoothes the unevenness of the surface of the adherend, that is, the gaps between the unevenness of the adherend are preferably filled by the pressure-sensitive adhesive layer, thereby improving the accuracy of the back grind process. Has a role.
  • the pressure-sensitive adhesive layer reduces the peeling charge generated when the BG tape is peeled from the adherend. Further, the pressure-sensitive adhesive layer of the BG tape of the present embodiment does not leave adhesive residue even when the BG tape is peeled off. Further, the pressure-sensitive adhesive layer of the BG tape of the present embodiment is unlikely to cause contamination of the adherend after the BG tape is peeled off by the ionic liquid (E) described later.
  • the thickness of the pressure-sensitive adhesive layer of the present embodiment can be arbitrarily selected, but is preferably 50 to 500 ⁇ m, more preferably 60 to 400 ⁇ m, and even more preferably 70 to 300 ⁇ m.
  • the thickness of the pressure-sensitive adhesive layer is 50 ⁇ m or more, the unevenness absorption and adhesive strength of the BG tape become good.
  • the thickness of the pressure-sensitive adhesive layer is 500 ⁇ m or less, the film thickness of the pressure-sensitive adhesive layer can be easily controlled.
  • the thickness of the pressure-sensitive adhesive layer largely depends on the height of the uneven portion on the surface of the adherend.
  • the thickness of the pressure-sensitive adhesive layer is preferably equal to or greater than the height of the uneven portion on the surface so that sufficient uneven absorption can be obtained. Therefore, for example, when the unevenness of the surface is a bump formed on the semiconductor wafer, it is preferable that the thickness of the pressure-sensitive adhesive layer is twice or more the height dimension of the bump.
  • the bump height is usually 30-200 ⁇ m.
  • the thickness of the pressure-sensitive adhesive layer is preferably 200 ⁇ m or more, and when the bump height is 200 ⁇ m, the thickness of the pressure-sensitive adhesive layer is 400 ⁇ m or more.
  • the pressure-sensitive adhesive layer may have a single-layer structure, or may have a multi-layer structure in which the pressure-sensitive adhesive layer of the present embodiment and one or more other pressure-sensitive adhesive layers different from the pressure-sensitive adhesive layer of the present embodiment are laminated. You may.
  • a conventionally known pressure-sensitive adhesive layer can be used. In the present embodiment, when the pressure-sensitive adhesive layer has a multi-layer structure, the pressure-sensitive adhesive layer of the present embodiment needs to be present on the outermost surface.
  • a layer other than the pressure-sensitive adhesive layer may be present between the pressure-sensitive adhesive layer and the base material within a range that does not hinder the curing of the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer preferably has a single-layer structure.
  • the gel fraction of the pressure-sensitive adhesive layer can be arbitrarily selected, but is preferably 50 to 65% by mass. When the gel fraction is 50% by mass or more, the generation of adhesive residue due to peeling the BG tape attached to the adherend can be more effectively suppressed. Further, when the gel fraction is 65% by mass or less, the pressure-sensitive adhesive layer has sufficient fluidity, and the unevenness absorption of the BG tape becomes even better.
  • the gel fraction of the pressure-sensitive adhesive layer is more preferably 52% by mass or more. Further, the gel fraction of the pressure-sensitive adhesive layer is more preferably 63% by mass or less.
  • the surface resistivity of the pressure-sensitive adhesive layer is preferably less than 1 ⁇ 10 11 ⁇ / ⁇ , and more preferably less than 1 ⁇ 10 10 ⁇ / ⁇ .
  • the lower limit of the surface resistivity of the pressure-sensitive adhesive layer can be arbitrarily selected, but may be, for example, 1 ⁇ 10 6 ⁇ / ⁇ or more.
  • the BG tape may be provided with a transparent or opaque separator on the surface of the pressure-sensitive adhesive layer opposite to the base material for the purpose of protecting the pressure-sensitive adhesive layer.
  • the separator is preferably laminated directly on the surface of the pressure-sensitive adhesive layer.
  • the material of the separator can be arbitrarily selected, but for example, paper, a plastic film, or the like can be used, and it is preferable to use a plastic film from the viewpoint of excellent surface smoothness.
  • the plastic film used as the separator is not particularly limited as long as it can protect the above-mentioned pressure-sensitive adhesive layer, and examples thereof include polyethylene, polypropylene, polyethylene terephthalate (PET), and polybutene.
  • the thickness of the separator can be selected arbitrarily. For example, it is preferably 5 to 300 ⁇ m, more preferably 10 to 200 ⁇ m, and even more preferably 25 ⁇ m to 100 ⁇ m.
  • the pressure-sensitive adhesive composition of the present embodiment contains polyurethane (A), (meth) acrylate monomer (B), a chain transfer agent (C), a photopolymerization initiator (D), and an ionic liquid (E). Including.
  • the (meth) acrylate monomer may mean a methacrylate monomer and / or an acrylate monomer.
  • the polyurethane (A) includes the polyurethane (a1) described later. Although it may be composed of only polyurethane (a1), polyurethane (A) includes not only polyurethane (a1) but also polyurethane (a2), which will be described later, for the purpose of adjusting the cohesive force of the cured product of the pressure-sensitive adhesive composition. It may be included. It is preferable that the polyurethane (A) does not contain components other than the polyurethane (a1) and the polyurethane (a2) contained if necessary.
  • Polyurethane (a1) has a skeleton containing a structure derived from a polyoxyalkylene polyol and a structure derived from a polyisocyanate.
  • polyurethane (a1) has a plurality of (meth) acryloyl groups at the ends. It may have a (meth) acryloyl group at all ends.
  • the terminal (meth) acryloyl group of the polyurethane (a1) is preferably a part of the (meth) acryloyloxy group.
  • the (meth) acryloyl group may mean a meta-acryloyl group and / or an acryloyl group.
  • the (meth) acryloyloxy group may mean a metaacryloyloxy group and / or an acryloyloxy group.
  • the "plurality of ends" of polyurethane means two or more ends.
  • “Multiple ends” means two ends when the polyurethane is a linear polymer, and two or more ends out of the same number of ends as the number of each branched chain when the polyurethane is a branched polymer. is there.
  • Polyurethane (a2) Polyurethane (a2), like polyurethane (a1), has a skeleton containing a structure derived from a polyoxyalkylene polyol and a structure derived from a polyisocyanate. Polyurethane (a2), unlike polyurethane (a1), has a (meth) acryloyl group at only one end. The terminal (meth) acryloyl group of the polyurethane (a2) is preferably a part of the (meth) acryloyloxy group.
  • the terminal of the polyurethane (a2) having no (meth) acryloyl group preferably has any one selected from an isocyanato group, a structure derived from an alkyl alcohol, and a structure derived from an alkyl isocyanate, and has a structure derived from an alkyl alcohol. Is more preferable.
  • the polyoxyalkylene polyol having a structure derived from the polyoxyalkylene polyol contained in the skeletons of the polyurethane (a1) and the polyurethane (a2) preferably has an alkylene chain having 2 to 4 carbon atoms. Specific examples include polyoxyethylene polyol, polyoxypropylene polyol, polyoxybutylene polyol and the like.
  • the polyoxyalkylene polyol having a structure derived from the polyoxyalkylene polyol may contain one type of alkylene chain or may contain two or more types of alkylene chains.
  • the polyoxyalkylene polyol having a structure derived from the polyoxyalkylene polyol is preferably one having two or three hydroxyl groups at the terminal (diol type or triol type polyoxyalkylene polyol), and is preferably a polyoxyalkylene glycol (diol). Type) is more preferable, and polypropylene glycol having an alkylene chain having 3 carbon atoms is particularly preferable.
  • the hydroxyl value is preferably 20 to 120 mgKOH / g, more preferably 30 to 100 mgKOH / g, and further preferably 40 to 80 mgKOH / g. preferable.
  • polypropylene glycol include polypropylene glycol (Actcol D-2000; manufactured by Mitsui Chemicals, number average molecular weight 2000, diol type) having a hydroxyl group (hydroxy group) having a hydroxyl value of 56 mgKOH / g at the end. Be done.
  • the hydroxyl value of the polyoxyalkylene polyol is the hydroxyl value of the polyoxyalkylene polyol measured according to JIS K0070. That is, it means the number of mg of potassium hydroxide required to neutralize free acetic acid when 1 g of polyoxyalkylene polyol is acetylated. Specifically, it can be obtained by acetylating the hydroxyl groups in the sample (polyoxyalkylene polyol) with acetic anhydride and titrating the free acetic acid generated at that time with a potassium hydroxide solution.
  • the number average molecular weight of the polyoxyalkylene polyol is preferably 500 to 5,000, more preferably 800 to 4,000, and even more preferably 1,000 to 3,000.
  • the BG tape having a pressure-sensitive adhesive layer made of a cured product of the pressure-sensitive adhesive composition containing polyurethane (A) synthesized using the polyoxyalkylene polyol has high peel strength. It becomes.
  • the polyurethane (A) synthesized using the polyoxyalkylene polyol contains a sufficient amount of urethane bonds. Therefore, the cured product obtained by curing the pressure-sensitive adhesive composition containing polyurethane (A) has a good cohesive force.
  • the structure derived from the polyoxyalkylene polyol contained in the skeletons of the polyurethane (a1) and the polyurethane (a2) may be of only one type, or may be a structure containing two or more types.
  • Polyurethane (a1) and polyurethane (a2) may have a structure in which two or more different polyoxyalkylene polyol-derived structures are bonded with a polyisocyanate-derived structure in between.
  • the structure derived from the polyoxyalkylene polyol contained in the skeleton of the polyurethane (a1) and the structure derived from the polyoxyalkylene polyol contained in the skeleton of the polyurethane (a2) may be the same or different. ..
  • Polyisocyanate having a structure derived from the polyisocyanate contained in the skeletons of the polyurethane (a1) and the polyurethane (a2) a compound having a plurality of isocyanato groups can be used, and it is preferable to use a diisocyanate.
  • the diisocyanate include tolylene diisocyanate and its hydrogen additive, xylylene diisocyanate and its hydrogen additive, diphenylmethane diisocyanate and its hydrogen additive, 1,5-naphthylene diisocyanate and its hydrogen additive, hexamethylene diisocyanate, and trimethyl.
  • Examples thereof include hexamethylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexyldiisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, norbornan diisocyanate and the like.
  • polystyrene resin it is preferable to use a hydrogenated isophorone diisocyanate or diphenylmethane diisocyanate from the viewpoint of controlling the light resistance of the polyurethane (A) synthesized using the polyisocyanate and the reactivity with the polyoxyalkylene polyol.
  • a hydrogenated diphenylmethane diisocyanate it is more preferable to use a hydrogenated diphenylmethane diisocyanate in terms of reactivity with a polyoxyalkylene polyol.
  • polyisocyanate having a structure derived from polyisocyanate examples include hydrogenated diphenylmethane diisocyanate (Desmodule W, manufactured by Sumika Covestro Urethane) and isophorone diisocyanate (Desmodule I, manufactured by Sumika Covestro Urethane). Can be mentioned.
  • the polyisocyanate-derived structure contained in the skeletons of the polyurethane (a1) and the polyurethane (a2) may be of only one type, or may be a structure containing two or more types. Further, the structure derived from polyisocyanate contained in the skeleton of polyurethane (a1) and the structure derived from polyisocyanate contained in the skeleton of polyurethane (a2) may be the same or different.
  • polyurethane (a1) and polyurethane (a2) can be synthesized at the same time.
  • Polyurethane (A) can be efficiently produced, which is preferable.
  • the proportion of polyurethane (a1) contained in polyurethane (A) is preferably 80 to 100%, more preferably 90 to 100%, and even more preferably 100% of polyurethane (A) on the basis of the number of molecules.
  • the proportion of polyurethane (a2) contained in polyurethane (A) is preferably 0 to 20%, more preferably 0 to 10%, and even more preferably 0% of polyurethane (A) on the basis of the number of molecules.
  • polyurethane (A) Of all the number of ends contained in polyurethane (A) (the total number of the number of ends of polyurethane (a1) and the number of ends of polyurethane (a2) contained as needed), 90 to 100 based on the number of molecules. It is preferable that a (meth) acryloyl group is introduced into%, more preferably 95 to 100%, still more preferably 100%. If necessary, it may be 90 to 93%, 93 to 97%, 97 to 100%, or the like. When the amount of the (meth) acryloyl group introduced is 90% or more based on the number of molecules among all the terminals contained in the polyurethane (A), it is obtained by curing the pressure-sensitive adhesive composition containing the polyurethane (A). The cohesive force of the cured product is sufficiently high.
  • the ratio of the number of terminals into which the (meth) acryloyl group is introduced based on the number of molecules among all the number of terminals contained in polyurethane (A) is determined by the infrared absorption spectrum (IR) method and the nuclear magnetic resonance spectrum (NMR) method. It can be calculated using the result of analyzing the polyurethane (A) using the above.
  • the ratio of the number of introduced terminals can be adjusted by the method for producing polyurethane (A) described later.
  • the mass average molecular weight of polyurethane (A) is preferably 30,000 to 200,000, more preferably 50,000 to 150,000, and even more preferably 60,000 to 100,000. ..
  • the mass average molecular weight of the polyurethane (A) is 30,000 or more, the cured product obtained by curing the pressure-sensitive adhesive composition containing the polyurethane (A) has good flexibility. Further, when the mass average molecular weight of the polyurethane (A) is 200,000 or less, the pressure-sensitive adhesive composition containing the polyurethane (A) is easy to handle and has good workability.
  • the mass average molecular weight of polyurethane (A) is a polystyrene-equivalent value measured by gel permeation chromatography (GPC-101; Showa Denko KK Shodex®) (hereinafter referred to as GPC). ..
  • GPC gel permeation chromatography
  • the measurement conditions of GPC are as follows. Column: LF-804 (manufactured by Showa Denko KK) Column temperature: 40 ° C Sample: 0.2% by mass tetrahydrofuran solution of polyurethane (A) Flow rate: 1 ml / min Eluent: Tetrahydrofuran Detector: RI detector (differential refractive index detector)
  • the content of polyurethane (A) in the pressure-sensitive adhesive composition of the present embodiment can be arbitrarily selected, but is preferably 20 to 50% by mass, more preferably 25 to 45% by mass, and 30 to 40% by mass. It is more preferably by mass%.
  • the content of the polyurethane (A) is 20% by mass or more, the cured product obtained by curing the pressure-sensitive adhesive composition has a sufficient cohesive force, and an excellent adhesive force can be obtained.
  • the softness of the pressure-sensitive adhesive layer is within an appropriate range, and air bubbles are less likely to be caught between the pressure-sensitive adhesive layer and the adherend.
  • the cured product obtained by curing the pressure-sensitive adhesive composition has sufficient flexibility. Therefore, the BG tape using this cured product as the pressure-sensitive adhesive layer has good wettability to the adherend.
  • the (meth) acrylate monomer (B) is not particularly limited as long as it is a compound other than polyurethane (A) and has a (meth) acryloyloxy group.
  • the (meth) acrylate monomer (B) only one compound having a (meth) acryloyloxy group may be used alone, or two or more thereof may be mixed and used.
  • a monofunctional (meth) acrylate may be used, a polyfunctional (meth) acrylate may be used, or a monofunctional (meth) acrylate and a polyfunctional (meth) acrylate. You may use both of.
  • the (meth) acrylate may mean a metal acrylate and / or an acrylate.
  • monofunctional (meth) acrylate means a (meth) acrylate having only one (meth) acryloyloxy group.
  • polyfunctional in the polyfunctional (meth) acrylate means a (meth) acrylate having two or more (meth) acryloyloxy groups.
  • the (meth) acrylate monomer (B) includes a monofunctional (meth) acrylate and a polyfunctional (meth) acrylate from the viewpoint of the cohesiveness of the cured product obtained by curing the pressure-sensitive adhesive composition and the curability of the pressure-sensitive adhesive composition. It is preferable to use it in combination with an acrylate, and it is more preferable to contain a monofunctional (meth) acrylate and a trifunctional or higher (meth) acrylate, in particular, a monofunctional (meth) acrylate and three (meth) acrylates. Most preferably, it contains a trifunctional (meth) acrylate having an acryloyloxy group.
  • Examples of the monofunctional (meth) acrylate include cyclic alkyl (meth) acrylate such as alkyl (meth) acrylate and isobornyl (meth) acrylate, alkoxyalkyl (meth) acrylate, alkoxy (poly) alkylene glycol (meth) acrylate, and hydroxy.
  • the adhesive strength (peeling force) and gel fraction of the cured product obtained by curing the pressure-sensitive adhesive composition are such that when the cured product is used as the pressure-sensitive adhesive layer of the BG tape.
  • the alkyl (meth) acrylate it is more preferable to use an alkyl (meth) acrylate having an alkyl group having 4 to 10 carbon atoms.
  • alkyl (meth) acrylate examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
  • 2-ethylhexyl (meth) acrylate and / or n-butyl (meth) acrylate examples include 2-ethylhexyl (meth) acrylate and / or n-butyl (meth) acrylate.
  • the polyfunctional (meth) acrylate is a compound other than polyurethane (A) and having a plurality of (meth) acryloyloxy groups.
  • the polyfunctional (meth) acrylate it is preferable to use a poly (meth) acrylate of a polyol compound.
  • Specific examples of the polyfunctional (meth) acrylate include polyethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and tripropylene glycol.
  • trimethylolpropane tri (meth) acrylate is preferably used as the polyfunctional (meth) acrylate from the viewpoint of curability of the pressure-sensitive adhesive
  • both monofunctional (meth) acrylate and polyfunctional (meth) acrylate are contained as the (meth) acrylate monomer (B), when the total of the (meth) acrylate monomer (B) is 100 mol%, it is simple. It is preferable to contain 85 to 99 mol% of functional (meth) acrylate and 1 to 15 mol% of polyfunctional (meth) acrylate. In this case, the content of the monofunctional (meth) acrylate is more preferably 90 to 99 mol%, further preferably 95 to 98 mol%. The content of the polyfunctional (meth) acrylate is more preferably 1 to 10 mol%, further preferably 2 to 5 mol%.
  • the BG tape using this cured product as the pressure-sensitive adhesive layer can obtain sufficient unevenness absorption, and when it is attached to an adherend having an uneven portion on the surface, it is placed between the BG tape and the uneven portion of the adherend. It is preferable because voids are less likely to occur.
  • the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer is less likely to remain adhesive when peeled from the adherend. ,preferable.
  • the content of the polyfunctional (meth) acrylate is 1 mol% or more, the cured product obtained by curing the pressure-sensitive adhesive composition It is preferable that the fluidity does not become too large. Further, when the content of the polyfunctional (meth) acrylate is 15 mol% or less, the fluidity of the cured product obtained by curing the pressure-sensitive adhesive composition is high when the cured product is used as the pressure-sensitive adhesive layer of the BG tape. This is a preferable range.
  • the BG tape using the cured product as the pressure-sensitive adhesive layer has sufficient unevenness absorbing property, and when it is attached to an adherend having an uneven portion on the surface, it is placed between the BG tape and the uneven portion of the adherend. It is preferable because voids are less likely to occur.
  • the content of the (meth) acrylate monomer (B) in the pressure-sensitive adhesive composition of the present embodiment can be arbitrarily selected, but is preferably 35 to 79% by mass, more preferably 40 to 73% by mass. , 40 to 66% by mass, more preferably 45 to 65% by mass. If necessary, it may be 45 to 60% by mass, 50 to 58% by mass, or the like.
  • the content of the (meth) acrylate monomer (B) is 35% by mass or more, the viscosity of the pressure-sensitive adhesive composition does not become too high and the coatability is excellent, which is preferable.
  • the content of the (meth) acrylate monomer (B) is 79% by mass or less, the viscosity of the pressure-sensitive adhesive composition does not become too low, and the thickness of the coating film made of the pressure-sensitive adhesive composition can be easily controlled. ,preferable.
  • the chain transfer agent (C) is contained in the pressure-sensitive adhesive composition for the purpose of controlling the unevenness absorption and gel fraction of the cured product obtained by curing the pressure-sensitive adhesive composition.
  • the chain transfer agent (C) it is preferable to use a thiol compound.
  • polyfunctional thiols can be preferably used.
  • a polyfunctional thiol is a compound having two or more mercapto groups in the molecule.
  • the polyfunctional thiol is not particularly limited, and is, for example, 1,2-ethanedithiol, 1,4-bis (3-mercaptobutylyloxy) butane, tetraethylene glycol bis (3-mercaptopropionate), and trimethylol.
  • the chain transfer agent (C) it is preferable to use pentaerythritol tetrakis (3-mercaptobutyrate)
  • the content of the chain transfer agent (C) in the pressure-sensitive adhesive composition of the present embodiment can be arbitrarily selected, but is preferably 0.5 to 8.0% by mass, preferably 0.7 to 6.0% by mass. It is more preferably 1.0 to 5.0% by mass, and particularly preferably 3.0 to 4.5% by mass.
  • the content of the chain transfer agent (C) is 0.5% by mass or more, the fluidity of the cured product obtained by curing the pressure-sensitive adhesive composition is high when the cured product is used as the pressure-sensitive adhesive layer of the BG tape. It is in a preferable range.
  • the BG tape using the cured product as the pressure-sensitive adhesive layer has sufficient unevenness absorbing property and is less likely to generate voids between the cured product and the uneven portion of the adherend.
  • the content is 8.0% by mass or less, it is preferable that the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer is less likely to leave adhesive residue when peeled from the adherend.
  • the photopolymerization initiator (D) is not particularly limited, but a photoradical polymerization initiator is preferable.
  • the photopolymerization initiator (D) include a carbonyl-based photopolymerization initiator, a sulfide-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, a quinone-based photopolymerization initiator, and a sulfochloride-based photopolymerization initiator.
  • a thioxanthone-based photopolymerization initiator or the like can be used.
  • a carbonyl-based photopolymerization initiator and / or an acylphosphine oxide-based photopolymerization initiator is used from the viewpoint of transparency of the cured product obtained by photocuring the pressure-sensitive adhesive composition.
  • a 2,4,6-trimethylbenzoyldiphenylphosphine oxide agent and / or a 1-hydroxycyclohexyl-phenylketone is preferable to use.
  • the content of the photopolymerization initiator (D) in the pressure-sensitive adhesive composition of the present embodiment is preferably 0.01 to 5.0% by mass, and preferably 0.05 to 3.0% by mass. More preferably, it is 0.1 to 2.0% by mass. If necessary, it may be 0.2 to 1.5% by mass, 0.3 to 1.2% by mass, or the like.
  • the content of the photopolymerization initiator (D) is 0.01% by mass or more, the photocuring of the pressure-sensitive adhesive composition proceeds sufficiently. Further, when the content of the photopolymerization initiator (D) is 5% by mass or less, the low molecular weight component does not become too large during photocuring of the pressure-sensitive adhesive composition. Therefore, it is preferable that the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer is less likely to leave adhesive residue when peeled from the adherend.
  • the ionic liquid (E) in the present embodiment refers to a molten salt compound (ionic compound) having a melting point of 100 ° C. or lower. More preferably, it is a molten salt compound having a melting point of room temperature (25 ° C.) or lower.
  • the ionic liquid (E) may be composed of one kind of compound or two or more kinds of compounds.
  • the ionic liquid may mean a salt compound that exists in a liquid state in the above temperature range, and may not contain a solvent.
  • the ionic liquid (E) it is preferable to use an organic salt compound in which an organic cation and an inorganic anion or an organic anion are combined.
  • Q 1 represents an alkyl group, an aryl group, substituent such as a heterocyclic group.
  • organic cations quaternary nitrogen atoms such as ammonium, iminium, and sulfonium are preferable.
  • these organic cations include pyridinium cation, piperidinium cation, pyrrolidinium cation, imidazolium cation, tetrahydropyrimidinium cation, dihydropyrimidinium cation, pyrazolium cation, tetraalkylammonium cation and trialkyl.
  • examples include sulfonium cations.
  • imidazolium cations and pyridinium cations are preferably used.
  • a pressure-sensitive adhesive layer containing an ionic liquid (E) using an imidazolium cation or a pyridinium cation as an organic cation is preferable because it has excellent antistatic properties.
  • imidazolium cation used as an organic cation examples include 1-methylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, and 1-butyl. Examples thereof include -3-methylimidazolium cation and 1,2,3-trimethylimidazolium cation. Among these imidazolium cations, 1-ethyl-3-methylimidazolium cation is preferably used.
  • pyridinium cation used as the organic cation include, for example, 1-ethylpyridinium cation, 1-butylpyridinium cation, 1-hexylpyridinium cation, 1-butyl-3-methylpyridinium cation, 1-butyl-4- Methylpyridinium cation, 1-hexyl-3-methylpyridinium cation, 1-hexyl-4-methylpyridinium cation, 1-butyl-3,4-dimethylpyridinium cation, 4-methyl-1-octylpyridinium cation, etc. Be done.
  • 1-hexyl-4-methylpyridinium cation, 4-methyl-1-octylpyridinium cation and the like are preferably used.
  • the inorganic anion is not particularly limited as long as it can form a molten salt compound having a melting point of 100 ° C. or lower.
  • the inorganic anions such as, Cl -, Br -, I -, AlCl 4 -, Al 2 Cl 7 -, BF 4 -, PF 6 -, ClO 4 -, NO 3 -, AsF 6 -, SbF 6 -, NbF 6 -, TaF 6 -, F (HF) m - (. m is an integer of 0 or more) - and the like, 2 N (CN).
  • the organic anion is not particularly limited as long as it can form a molten salt compound having a melting point of 100 ° C. or lower.
  • the organic anions for example, CH 3 COO -, CF 3 COO -, CH 3 SO 3 -, CF 3 SO 3 -, (CF 3 SO 2) 2 N -, (FSO 2) 2 N -, (CF 3 SO 2) 3 C -, C 4 F 9 SO 3 -, (C 2 F 5 SO 2) 2 N -, C 3 F 7 COO - and the like -, (CF 3 SO 2) (CF 3 CO) N Be done.
  • an anion containing a fluorine atom as the inorganic anion or the organic anion.
  • an anion containing a fluorine atom By using an anion containing a fluorine atom, an ionic liquid (E) having excellent ionic conductivity can be obtained. Therefore, the BG tape using the ionic liquid (E) containing a fluorine-containing anion is particularly excellent in antistatic property.
  • the fluorine-containing organic anion are preferable among anions containing fluorine atoms, in particular, (FSO 2) 2 N - , (CF 3 SO 2) 2 N - is preferably used, (FSO 2 ) It is more preferable to use 2 N ⁇ .
  • the ionic liquid (E) As the ionic liquid (E), a commercially available one may be used. Of these, 1-ethyl-3-methylimidazolium cation and bis (fluorosulfonyl) imide anion ((FSO 2) 2 N -) ionic liquid consisting of (Dai-ichi Kogyo Seiyaku Co., Ltd., trade name: Erekuseru AS-110 ), 4-methyl-1-octyl - pyridinium cations and bis (fluorosulfonyl) imide anion ((FSO 2) 2 N -) ionic liquid consisting of (Dai-ichi Kogyo Seiyaku Co., Ltd., trade name: Erekuseru aS-804 ) Is preferable.
  • the pressure-sensitive adhesive layer containing AS-110 and / or AS-804 as the ionic liquid (E) is preferable because it has excellent antistatic properties.
  • the content of the ionic liquid (E) in the pressure-sensitive adhesive composition of the present embodiment can be arbitrarily selected, but is preferably 0.4 to 6.0% by mass, preferably 0.5 to 5.0% by mass. More preferably, it is more preferably 1.0 to 3.0% by mass. If necessary, it may be 0.4 to 2.0% by mass, 2.0 to 4.0% by mass, or the like.
  • the content of the ionic liquid (E) is 0.4% by mass or more, the surface resistance value of the pressure-sensitive adhesive layer becomes sufficiently low. As a result, the antistatic performance of the BG tape having the adhesive layer is improved.
  • the pressure-sensitive adhesive composition of the present embodiment contains polyurethane (A), (meth) acrylate monomer (B), a chain transfer agent (C), a photopolymerization initiator (D), and an ionic liquid (E). It may be contained, and if necessary, a fatty acid ester (F) may be contained.
  • the fatty acid ester (F) controls the adhesive force of the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer, and also has the adhesiveness (wetting property) and the foam removal property (on the adherend) of the pressure-sensitive adhesive layer.
  • the BG sheet is contained in the pressure-sensitive adhesive composition for the purpose of improving (easiness of removal of air bubbles sandwiched during bonding).
  • an ester of a fatty acid and an alkyl alcohol can be used, and from the viewpoint of compatibility with other components, a fatty acid having 8 to 18 carbon atoms and a branched hydrocarbon group having 3 to 18 carbon atoms It is preferable to use an ester with a monofunctional alcohol having, and / or a fatty acid ester selected from an ester of an unsaturated fatty acid having 14 to 18 carbon atoms and an alcohol having 2 to 4 functionalities.
  • ester of a fatty acid having 8 to 18 carbon atoms and a monofunctional alcohol having a branched hydrocarbon group having 3 to 18 carbon atoms examples include isostearyl laurate, isopropyl myristate, isosetyl myristate, octyldodecyl myristate, and isopropyl palmitate.
  • isostearyl palmitate isosetyl stearate, 2-ethylhexyl stearate, octyldodecyl oleate, diisostearyl adipate, diisocetyl sebacate, trioleyl trimeritate, triisocetyl trimeritate and the like.
  • isopropyl myristate, isopropyl palmitate, and 2-ethylhexyl stearate are preferably used, and isopropyl myristate and / or 2-ethylhexyl stearate is particularly preferable.
  • esters of unsaturated fatty acids having 14 to 18 carbon atoms and alcohols having 2 to 4 functionalities include unsaturated fatty acids such as myristoleic acid, oleic acid, linoleic acid, linolenic acid, isostriatic acid, and isostearic acid, and ethylene.
  • esters with alcohols such as glycols, propylene glycols, glycerins, trimethylolpropanes, pentaerythritols, and sorbitans.
  • the content of the fatty acid ester (F) in the pressure-sensitive adhesive composition of the present embodiment can be arbitrarily selected, but is preferably 3 to 18% by mass, more preferably 5 to 15% by mass.
  • the adhesive strength of the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer is in a preferable range, and the adhesiveness of the pressure-sensitive adhesive layer and the laminating property and Good defoaming property.
  • the BG tape using the cured product of the pressure-sensitive adhesive composition as the pressure-sensitive adhesive layer contains the fatty acid ester (F) when peeled from the adherend. It is preferable because adhesive residue is unlikely to occur.
  • the pressure-sensitive adhesive composition of the present embodiment may contain a solvent, but is more preferably a solvent-free one containing substantially no solvent.
  • a solvent for example, a solvent can be used as a leveling agent and / or a softening agent.
  • the pressure-sensitive adhesive composition of the present embodiment is solvent-free, excellent productivity can be obtained because the step of heating and drying the solvent can be omitted when forming the pressure-sensitive adhesive layer of the BG tape using the pressure-sensitive adhesive composition.
  • the productivity improvement effect by omitting the step of heating and drying the solvent is remarkable. Therefore, it is preferable that there is no solvent.
  • the meaning of "substantially free of solvent” in the pressure-sensitive adhesive composition means that the content of the solvent in the pressure-sensitive adhesive composition is 0 to 1.0% by mass, preferably 0. It is about 0.5% by mass, more preferably 0 to 0.1% by mass.
  • the pressure-sensitive adhesive composition of the present embodiment may contain other additives, if necessary, as long as the effects of the present invention are not impaired.
  • Additives include, for example, plasticizers, surface lubricants, antioxidants, antioxidants, light stabilizers, UV absorbers, polymerization inhibitors, light stabilizers such as benzotriazoles, phosphate esters and others. Examples include flame retardants and dyes.
  • the reaction between the hydroxy group and the isocyanato group is carried out in any step in the presence of an organic solvent inert to the isocyanato group, such as dibutyltin dilaurate, dibutyltin diethylhexoate.
  • an organic solvent inert such as dibutyltin dilaurate, dibutyltin diethylhexoate.
  • a urethanization catalyst such as dioctyltin dilaurate.
  • the reaction between the hydroxy group and the isocyanato group is preferably carried out continuously at 30 to 100 ° C. for 1 to 5 hours in any of the steps.
  • the amount of the urethanization catalyst used is preferably 50 to 500 mass ppm with respect to the total mass of the reactant (raw material).
  • polyoxyalkylene polyol and polyisocyanate are mixed at a ratio in which the isocyanato group weight (molecular number standard, the same applies hereinafter) is larger than the hydroxy group weight (molecular number standard, the same applies hereinafter).
  • the polyoxyalkylene polyol is reacted with the polyisocyanate to synthesize a polyurethane having an isocyanato group at the terminal as a precursor of the polyurethane (A).
  • Specific examples of the polyoxyalkylene polyol and the polyisocyanate used as raw materials are as illustrated in the section of polyurethane (A).
  • the molecular weight (degree of polymerization) of the polyurethane having an isocyanato group at the terminal can be adjusted by adjusting the ratio of the isocyanato group amount to the hydroxy group amount contained in the raw material. Specifically, the smaller the excess amount of the isocyanato group with respect to the hydroxy group amount, the larger the molecular weight of the polyurethane having an isocyanato group at the terminal. Further, the larger the excess amount of the isocyanato group with respect to the hydroxy group amount, the smaller the molecular weight of the polyurethane having an isocyanato group at the terminal.
  • the mass average molecular weight of the target polyurethane (A) is adjusted by adjusting the molecular weight of the polyurethane having an isocyanato group at the terminal.
  • a polyurethane having an isocyanato group at the terminal is reacted with a compound having a hydroxy group and a (meth) acryloyl group to have a structure containing a polyoxyalkylene polyol-derived structure and a polyisocyanate-derived structure.
  • Polyurethane (A) containing polyurethane (a1) having a (meth) acryloyl group at the end of is produced.
  • the terminal (meth) acryloyl group of the produced polyurethane (A) is preferably a part of the (meth) acryloyloxy group.
  • the compound having a hydroxy group and a (meth) acryloyl group is not particularly limited, but is hydroxyalkyl such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • Examples thereof include monool having a (meth) acryloyl group derived from various polyols such as.
  • These compounds having a hydroxy group and a (meth) acryloyl group may be used alone or in combination of two or more.
  • 2-hydroxyethyl (meth) is obtained from the viewpoint of reactivity with the isocyanato group of polyurethane having an isocyanato group at the terminal and photocurability of the pressure-sensitive adhesive composition.
  • the polyurethane (A) has an isocyanato group at the terminal in combination with a compound having a hydroxy group and a (meth) acryloyl group and an alkyl alcohol having no (meth) acryloyl group and having one hydroxy group. It may be produced by reacting with polyurethane.
  • the alkyl alcohol may be any as long as it does not have a (meth) acryloyl group and has one hydroxy group, and linear, branched, alicyclic alkyl alcohols and the like can be used and is not particularly limited. ..
  • the above alkyl alcohol may be used alone or in combination of two or more.
  • Polyurethane (A) is obtained by reacting a compound having a hydroxy group and a (meth) acryloyl group, an alkyl alcohol having no (meth) acryloyl group and having one hydroxy group, and a polyurethane having an isocyanato group at the terminal.
  • the amount of (meth) acryloyl group introduced into polyurethane having an isocyanato group at the terminal can be adjusted by producing.
  • a polyurethane (A) containing a plurality of types of polyurethane having different amounts of introduced (meth) acryloyl groups at the ends is produced.
  • the plurality of types of polyurethanes include polyurethanes (a1) having a plurality of (meth) acryloyl groups at the ends.
  • the plurality of types of polyurethane include not only polyurethane (a1) but also polyurethane in which at least a part of the plurality of ends has a structure derived from the above alkyl alcohol.
  • the produced plurality of types of polyurethanes include polyurethanes in which at least some of the plurality of ends do not have a (meth) acryloyl group. Furthermore, among the plurality of types of polyurethane produced, polyurethane (a2) having a (meth) acryloyl group at only one terminal may be included.
  • reaction between the hydroxy group and the isocyanato group is preferably carried out continuously at 30 to 100 ° C. for 1 to 5 hours in any of the steps.
  • the amount of the urethanization catalyst used is preferably 50 to 500 mass ppm with respect to the total mass of the reactant (raw material).
  • polyurethane having a hydroxy group at the terminal is synthesized as a precursor of polyurethane (A). Specifically, first, the polyoxyalkylene polyol and the polyisocyanate are charged at a ratio in which the hydroxy group amount (based on the number of molecules, the same applies hereinafter) is larger than the amount of the isocyanato group (based on the number of molecules, the same applies hereinafter). Then, the polyoxyalkylene polyol is reacted with the polyisocyanate to synthesize a polyurethane having a hydroxy group at the terminal as a precursor of the polyurethane (A).
  • the molecular weight (degree of polymerization) of the polyurethane having a hydroxy group at the terminal can be adjusted by adjusting the ratio of the hydroxy group amount to the isocyanato group amount contained in the raw material. Specifically, the smaller the excess amount of the hydroxy group amount with respect to the isocyanato group amount, the larger the molecular weight of the polyurethane having a hydroxy group at the terminal. Further, the larger the excess amount of the hydroxy group with respect to the isocyanato group amount, the smaller the molecular weight of the polyurethane having a hydroxy group at the terminal.
  • the mass average molecular weight of the target polyurethane (A) is adjusted by adjusting the molecular weight of the polyurethane having a hydroxy group at the terminal.
  • a polyurethane having a hydroxy group at the terminal is reacted with a compound having an isocyanato group and a (meth) acryloyl group to have a structure containing a polyoxyalkylene polyol-derived structure and a polyisocyanate-derived structure.
  • Polyurethane (A) containing polyurethane (a1) having a (meth) acryloyl group at the end of is produced.
  • the terminal (meth) acryloyl group of the produced polyurethane (A) is preferably a part of the (meth) acryloyloxy group.
  • the compound having an isocyanato group and a (meth) acryloyl group is not particularly limited, but is limited to 2- (meth) acryloyloxyethyl isocyanate, 2- (meth) acryloyloxypropyl isocyanate, and 1,1-bis (acryloyloxymethyl) ethyl. Examples thereof include isocyanate. Examples of commercially available compounds having an isocyanato group and a (meth) acryloyl group include Karenz MOI (registered trademark) and Karenz AOI (registered trademark) manufactured by Showa Denko KK. These compounds having an isocyanato group and a (meth) acryloyl group may be used alone or in combination of two or more.
  • 2- (meth) acryloyl from the viewpoint of reactivity with the hydroxy group of polyurethane having a hydroxy group at the terminal and photocurability of the pressure-sensitive adhesive composition. It is preferable to use oxyethyl isocyanate.
  • the polyurethane (A) has a hydroxy group at the terminal in combination with a compound having an isocyanato group and a (meth) acryloyl group and an alkyl isocyanate having no (meth) acryloyl group and having one isocyanato group. It may be produced by reacting with polyurethane.
  • the alkyl isocyanate may be any as long as it does not have a (meth) acryloyl group and has one isocyanato group, and linear type, branched type, alicyclic type alkyl isocyanate and the like can be used and is not particularly limited. ..
  • the above alkyl isocyanate may be used alone or in combination of two or more.
  • Polyurethane (A) is obtained by reacting a compound having an isocyanato group and a (meth) acryloyl group, an alkyl isocyanate having no (meth) acryloyl group and having one isocyanato group, and a polyurethane having a hydroxy group at the terminal.
  • the amount of (meth) acryloyl group introduced into polyurethane having a hydroxy group at the terminal can be adjusted by producing.
  • a polyurethane (A) containing a plurality of types of polyurethane having different amounts of introduced (meth) acryloyl groups at the ends is produced.
  • the plurality of types of polyurethanes include polyurethanes (a1) having a plurality of (meth) acryloyl groups at the ends.
  • the plurality of types of polyurethane include not only polyurethane (a1) but also polyurethane in which at least a part of the plurality of ends has a structure derived from the above-mentioned alkyl isocyanate.
  • the produced plurality of types of polyurethanes include polyurethanes in which at least some of the plurality of ends do not have a (meth) acryloyl group. Furthermore, among the plurality of types of polyurethane produced, polyurethane (a2) having a (meth) acryloyl group at only one terminal may be included.
  • the pressure-sensitive adhesive composition of the present embodiment contains the polyurethane (A) obtained by the above synthesis method, the (meth) acrylate monomer (B), the chain transfer agent (C), and the photopolymerization initiator (D).
  • the ionic liquid (E) can be produced by a method of mixing the fatty acid ester (F) added as needed and other additives.
  • the method of mixing each component contained in the pressure-sensitive adhesive composition of the present embodiment is not particularly limited, and can be carried out by using, for example, a stirring device equipped with a stirring blade such as a homodisper or a paddle blade. ..
  • the method for producing the BG tape of the present embodiment is not particularly limited, and the BG tape can be produced by using a known method.
  • an adhesive composition is applied onto a sheet-shaped base material, and a separator is laminated to form a laminate.
  • the pressure-sensitive adhesive composition is irradiated with ultraviolet rays via a separator to photo-cure the pressure-sensitive adhesive composition.
  • a BG tape having a pressure-sensitive adhesive layer made of a cured product of the pressure-sensitive adhesive composition formed on the base material can be obtained.
  • the method of applying the pressure-sensitive adhesive composition to the base material is not particularly limited and can be appropriately selected.
  • various coaters such as a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip roll coater, a bar coater, a knife coater, a spray coater, a comma coater, and a direct coater are used. Examples thereof include a method to be used and a screen printing method.
  • Examples of the light source for photocuring the pressure-sensitive adhesive composition include a black light, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, and a xenon lamp.
  • the light irradiation intensity is preferably a condition in which the pressure-sensitive adhesive composition can be sufficiently cured and the gel fraction of the cured product is in the range of 50 to 65% by mass. For example, 50 to It is preferably 3000 mW / cm 2. If the light irradiation intensity is weak, it takes time to cure and the productivity decreases.
  • the pressure-sensitive adhesive composition is irradiated with ultraviolet rays via a transparent separator, but when the base material is transparent, ultraviolet rays may be irradiated from the base material side, and an opaque separator is used. May be good.
  • the BG tape of the present embodiment can be used, for example, for applications where it is attached to an adherend having an uneven portion on the surface and then peeled off. Specifically, it can be suitably used as a back grind tape for semiconductor wafer processing, which is attached to a surface on which bumps of a semiconductor wafer are formed to protect the surface of the semiconductor wafer and is peeled off after a predetermined wafer processing step. ..
  • the peel strength (adhesive strength) of the BG tape is determined, for example, in the back grind step in the processing step of the semiconductor device. , It is necessary to have peeling strength (adhesive strength) for firmly fixing the BG tape to the semiconductor wafer. On the other hand, the peel strength of the BG tape needs to be such that the parts of the semiconductor device are not damaged when the BG tape is peeled from the semiconductor wafer after a predetermined processing step.
  • the peeling strength of the BG tape used for the above applications is such that the peeling speed is 0.3 m / min.
  • the thickness of the pressure-sensitive adhesive layer is 50 to 200 ⁇ m, it is preferably 10 to 300 gf / 25 mm, more preferably 15 to 200 gf / 25 mm, and further preferably 20 to 150 gf / 25 mm. preferable.
  • the thickness of the pressure-sensitive adhesive layer is 200 to 500 ⁇ m, it is preferably 50 to 500 gf / 25 mm, more preferably 60 to 400 gf / 25 mm, and even more preferably 70 to 300 gf / 25 mm.
  • a specific method for measuring the peel strength of the BG tape will be described later in Examples.
  • the BG tape of the present embodiment has a pressure-sensitive adhesive layer made of a cured product of the pressure-sensitive adhesive composition of the present embodiment on one side of a sheet-like base material. Therefore, the BG tape of the present embodiment has sufficient adhesive strength, and it is difficult for adhesive residue to be transferred to the adherend after the BG tape is peeled off, and moreover, unevenness absorption and antistatic are performed. Excellent in prevention. Therefore, the BG tape of the present embodiment is suitable for applications where it is attached to an adherend having an uneven portion on the surface and then peeled off.
  • the BG tape of the present embodiment can be suitably used as, for example, a BG tape that is attached when performing a back grind step of a semiconductor wafer having an uneven portion composed of bumps on the surface and is peeled off after the back grind step.
  • the semiconductor wafer is fixed with sufficient adhesive force by the BG tape of the present embodiment.
  • the BG tape has sufficient unevenness absorption, gaps are unlikely to occur between the BG tape attached to the semiconductor wafer and the periphery of the bump. Therefore, it is possible to prevent the water used in the back grind process from entering the gap between the BG tape and the periphery of the bump and contaminating the semiconductor wafer.
  • the BG tape of the present embodiment has sufficient antistatic properties, it is possible to suppress peeling charge when the BG tape attached to the semiconductor wafer is peeled off after the backgrinding step. Further, after the back grind step, adhesive residue is less likely to occur around the bumps of the semiconductor wafer from which the BG tape has been peeled off, which is preferable.
  • the BG tape of the present embodiment can have a single-layer structure in which the pressure-sensitive adhesive layer is a cured product of the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive layer can be formed only by performing the step of forming one layer. Therefore, the BG tape of the present embodiment has fewer manufacturing steps than, for example, a case where a BG tape having a layer having unevenness absorbing property, a layer having antistatic property, and a layer having adhesive strength is formed. Can be easily manufactured with.
  • Neostan U-810 manufactured by Nitto Kasei Co., Ltd. was charged with 0.8 g.
  • the obtained polyurethane (A-1) was analyzed using the infrared absorption spectrum (IR) method. As a result, no peak derived from the isocyanato group was observed. Therefore, it was confirmed that the polyurethane (A-1) is a polyurethane (a1) in which an acryloyloxy group is introduced at all terminals.
  • IR infrared absorption spectrum
  • the obtained polyurethane (A-2) was analyzed using the infrared absorption spectrum (IR) method. As a result, no peak derived from the isocyanato group was observed. Therefore, it was confirmed that the polyurethane (A-2) is a polyurethane (a1) in which an acryloyloxy group is introduced at all terminals.
  • PE1 Pentaerythritol tetrakis (3-mercaptobutyrate) (manufactured by Showa Denko KK)
  • NR1 1,3,5-Tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -Trione (manufactured by Showa Denko KK)
  • TPO Omnirad TPO H
  • IGM Resins BV 2,4,6-trimethylbenzoyldiphenylphosphine oxide
  • IGM Resins BV 184
  • Omnirad 184 1-Hydroxycyclohexyl-phenylketone (manufactured by IGM Resins BV)
  • Elexel AS-110 1-Ethyl-3-methylimidazolium bis (fluorosulfonyl) imide (manufactured by Dai-ichi Kogyo Seiyaku Co
  • ⁇ Making BG tape> As a sheet-like base material, a PET film having a thickness of 50 ⁇ m (manufactured by Toyobo Co., Ltd., trade name: ester (trademark) film E5100) was prepared. Then, the pressure-sensitive adhesive composition of Example 1 was applied onto the corona-treated surface of the base material using an applicator so that the thickness after curing was 150 ⁇ m.
  • a silicone-based ultra-light peeling PET film manufactured by Toyobo Co., Ltd., product name: E7006
  • a silicone-based ultra-light peeling PET film having a thickness of 75 ⁇ m was attached to the coated surface of the pressure-sensitive adhesive composition using a rubber roller.
  • an ultraviolet irradiation device manufactured by Eye Graphics Co., Ltd., UV irradiation device 3 kW, high-pressure mercury lamp
  • the pressure-sensitive adhesive composition was photocured by irradiating with ultraviolet rays under the condition of an irradiation amount of 1000 mJ / cm 2.
  • BG tape was prepared.
  • Comparative Example 4 the thickness of the pressure-sensitive adhesive composition after curing was adjusted to 30 ⁇ m. As a result, BG tapes of Examples 2 to 9 and Comparative Examples 1 to 4 were obtained.
  • the BG tape was cut into a size of 120 mm in length and 120 mm in width, and left for 3 hours in an environment of a temperature of 23 ° C. and a relative humidity of 50% RH for humidity control.
  • the peeling PET film is peeled off to expose the pressure-sensitive adhesive layer, and the pressure-sensitive adhesive layer is used under the condition of an applied voltage of 100 V ⁇ 60 seconds using a high resistivity meter (High Restor-UX manufactured by Mitsubishi Chemical Analytech Co., Ltd.).
  • the surface resistivity on the side was measured. Then, it was evaluated according to the following criteria. It can be said that the smaller the surface resistivity, the less likely it is that peeling charge is generated when the BG tape attached to the semiconductor wafer is peeled off, and the BG tape has excellent antistatic properties.
  • the BG tape was cut into a size of 25 mm in length and 50 mm in width, and the separator was peeled off to expose the adhesive layer. Then, the surface of the exposed pressure-sensitive adhesive layer and the bumps of a wafer with bumps (WALTS-TEG FC150SCJY LF (PI) manufactured by Waltz, bump height: 75 ⁇ m, bump size: diameter 90 ⁇ m) were placed facing each other. Then, a rubber roller (diameter: 85 mm, width: 50 mm) having a mass of 2 kg (load 19.6 N) is reciprocated three times at a speed of 10 mm / sec on the base material of the BG tape to transfer the BG tape and the bumped wafer. I pasted them together.
  • WALTS-TEG FC150SCJY LF (PI) manufactured by Waltz, bump height: 75 ⁇ m, bump size: diameter 90 ⁇ m
  • BG tape was cut into a size of 25 mm in length and 50 mm in width, and the separator was peeled off to expose the adhesive layer. Then, the surface of the exposed pressure-sensitive adhesive layer was placed facing the bumps of a wafer with bumps (WALTS-TEG FC150SCJY LF (PI) manufactured by Waltz, bump height: 75 ⁇ m, bump size: diameter 90 ⁇ m).
  • a rubber roller (diameter: 85 mm, width: 50 mm) having a mass of 2 kg (load 19.6 N) is reciprocated three times at a speed of 10 mm / sec on the base material of the BG tape to transfer the BG tape and the bumped wafer. I pasted them together.
  • the bumped wafer bonded to the BG tape was left at 23 ° C. for 24 hours, and then the BG tape was applied at approximately 2 m / min. It was peeled off by hand at a moderate speed. Then, the surface of the bumped wafer was observed with a digital optical microscope (RH-2000 manufactured by Hirox Co., Ltd.), and the presence or absence of adhesive residue and contamination by ionic liquid was evaluated according to the following criteria. The results are shown in Table 1.
  • the “adhesive residue” means that the adhesive layer itself remains attached to the wafer surface and the wafer surface is sticky.
  • the “contamination by the ionic liquid” means that the ionic liquid bleeding out from the pressure-sensitive adhesive layer adheres to the wafer surface and the wafer surface is wet.
  • Adhesive composition on a 75 ⁇ m-thick peeling PET film (manufactured by Higashiyama Film Co., Ltd., trade name: Clean Sepa (trademark) HY-S10-2) so that the thickness after curing is 150 ⁇ m using an applicator. I applied the thing.
  • the thickness after curing was adjusted to 30 ⁇ m.
  • the coated surface of the pressure-sensitive adhesive composition was covered with a silicone-based ultra-light peeling PET film (manufactured by Toyobo Co., Ltd., product name: E7006) having a thickness of 75 ⁇ m.
  • the irradiation distance is 25 cm
  • the lamp moving speed is 1.0 m / min
  • the irradiation amount is 1000 mJ / cm 2 .
  • Ultraviolet rays were irradiated through the ultra-light peeling PET film, and the pressure-sensitive adhesive composition was cured to obtain a cured product (adhesive layer).
  • the cured product (adhesive layer) was cut out to a size of about 1 g, and the PET films on both sides were peeled off to prepare a sample for measurement, and the mass thereof was measured.
  • B Mass of measurement sample before immersion in toluene
  • the BG tapes of Examples 1 to 9 using the pressure-sensitive adhesive composition containing 0.4 to 6% by mass of the ionic liquid all have a surface resistivity of the pressure-sensitive adhesive layer of 1 ⁇ . It was less than 10 11 ⁇ / ⁇ and had excellent antistatic properties.
  • the BG tapes of Examples 1 to 9 all had sufficient peel strength of 10 gf / 25 mm or more, and the evaluation of unevenness absorption and adhesive residue / contamination was " ⁇ (good)". ..
  • the evaluation of the surface resistivity of the pressure-sensitive adhesive layer was “x (impossible)".
  • the evaluation of adhesive residue / contamination was “x (impossible)”.
  • the BG tape of Comparative Example 3 using the pressure-sensitive adhesive composition containing no chain transfer agent and the BG tape of Comparative Example 4 having a thickness of the pressure-sensitive adhesive layer of 30 ⁇ m have a peeling force of less than 10 gf / 25 mm and absorb unevenness. The evaluation of sex was "x (impossible)”.
  • a backgrind tape that has sufficient unevenness absorption, antistatic property, adhesive strength, is less likely to cause adhesive residue, and can be manufactured with a small number of manufacturing steps.
  • the back grind tape can be preferably used as an application for protecting the surface of a semiconductor wafer in the semiconductor wafer processing process and peeling it off after the processing process.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Mechanical Treatment Of Semiconductor (AREA)

Abstract

La présente invention concerne une bande abrasive arrière qui comprend un substrat en forme de feuille et une couche d'agent adhésif formée sur une surface du substrat, la couche d'agent adhésif comprenant un produit durci d'une composition d'agent adhésif et étant épaisse de 50 à 500 µm, la composition d'agent adhésif comprenant un polyuréthane (A), un monomère de (méth)acrylate (B), un agent de transfert de chaîne (C), un initiateur de photopolymérisation (D), et 0,4 à 6 % en masse d'un liquide ionique (E), et le polyuréthane (A) comprend un polyuréthane (a1) ayant un squelette qui inclut une structure dérivée d'un polyoxyalkylène polyol et une structure dérivée d'un polyisocyanate, et ayant des groupes (méth)acryloyle au niveau d'une pluralité d'extrémités.
PCT/JP2020/030939 2019-09-05 2020-08-17 Bande abrasive arrière WO2021044833A1 (fr)

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WO2019069746A1 (fr) * 2017-10-05 2019-04-11 昭和電工株式会社 Composition adhésive et feuille adhésive

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CN113993663A (zh) 2022-01-28
TW202112998A (zh) 2021-04-01

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