WO2023149023A1 - Feuille adhésive - Google Patents

Feuille adhésive Download PDF

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Publication number
WO2023149023A1
WO2023149023A1 PCT/JP2022/038941 JP2022038941W WO2023149023A1 WO 2023149023 A1 WO2023149023 A1 WO 2023149023A1 JP 2022038941 W JP2022038941 W JP 2022038941W WO 2023149023 A1 WO2023149023 A1 WO 2023149023A1
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WO
WIPO (PCT)
Prior art keywords
pressure
adhesive sheet
sensitive adhesive
active energy
energy ray
Prior art date
Application number
PCT/JP2022/038941
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English (en)
Japanese (ja)
Inventor
みずほ 千葉
俊平 田中
元気 越智
Original Assignee
日東電工株式会社
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
Priority claimed from JP2022149386A external-priority patent/JP2023113108A/ja
Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Publication of WO2023149023A1 publication Critical patent/WO2023149023A1/fr

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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
    • 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
    • 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
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages

Definitions

  • the present invention relates to an adhesive sheet.
  • an electronic component arranged on a predetermined member is transferred to another member, the electronic component is received with an adhesive sheet, and then the electronic component is transferred to another member.
  • the LED chip formed on the member is once transferred onto an adhesive sheet and received, and then the LED chip is transferred from the adhesive sheet to a predetermined device or member. Then, the LED chips are transferred.
  • the present invention has been made to solve the above-mentioned conventional problems, and an object of the present invention is to provide a pressure-sensitive adhesive sheet that can be used when transferring electronic components, which can contribute to the improvement of production costs, To provide a pressure-sensitive adhesive sheet which is excellent in the positional accuracy of components, the fixability of electronic components to the pressure-sensitive adhesive sheet and the releasability thereof, and which can prevent contamination of electronic components and damage to electronic components.
  • the pressure-sensitive adhesive sheet of the present invention is a pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer composed of an active energy ray-curable pressure-sensitive adhesive, wherein the active energy ray-curable pressure-sensitive adhesive is an ultraviolet absorber and/or a photopolymerizable
  • the adhesive layer has an initial indentation modulus of 4 MPa or less at 23°C, and the indentation modulus of elasticity at 23°C of the adhesive layer is 150 MPa or more at 23°C after being irradiated with ultraviolet rays of 460 mJ/ cm2 .
  • the adhesive sheet has a light transmittance of 50% or less at a wavelength of 355 nm.
  • the adhesive sheet does not contain a substrate.
  • the stress relaxation rate of the adhesive layer after 600 seconds may be 10% or more.
  • the pressure-sensitive adhesive sheets of [1] to [3] the pressure-sensitive adhesive layer may have a thickness of 20 ⁇ m or less.
  • the active energy ray-curable pressure-sensitive adhesive contains a photopolymerization initiator, and the photopolymerization initiator has two or more photodegradable groups.
  • the active energy ray-curable adhesive contains a photopolymerization initiator, and the photopolymerization initiator is a compound containing a phosphorus atom and/or a nitrogen atom. There may be.
  • the active energy ray-curable pressure-sensitive adhesive contains an active energy ray-reactive compound, and the active energy ray-reactive compound has 5 or more functional groups. It may be a polyfunctional (meth)acrylate.
  • the pressure-sensitive adhesive sheets of [1] to [7] above may be used for transferring electronic components.
  • the pressure-sensitive adhesive sheets of [1] to [8] above may be used for transferring electronic components including catching electronic components by a laser lift-off process and then peeling off electronic components by laser light irradiation.
  • the electronic component may be a mini LED or a micro LED.
  • a method for transferring electronic components is provided. This method of transferring electronic components is a method of transferring electronic components using the adhesive sheet.
  • the method for transferring electronic components includes a first step of transferring a plurality of electronic components arranged on a substrate onto the adhesive layer of the adhesive sheet; A second step of transferring the electronic component on the sheet to another member is included. [13] In one embodiment, the same adhesive sheet is used in the first step and the second step.
  • a pressure-sensitive adhesive sheet that can be used when transferring electronic components can contribute to an improvement in production costs, and is excellent in the positional accuracy of the electronic components and in the fixability and peelability of the electronic components from the pressure-sensitive adhesive sheet. , it is possible to provide a pressure-sensitive adhesive sheet that can prevent contamination of electronic parts and damage to electronic parts.
  • (a) is a schematic cross-sectional view of an adhesive sheet according to one embodiment of the present invention.
  • (b) is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to another embodiment of the present invention.
  • FIG. 1(a) is a schematic cross-sectional view of an adhesive sheet according to one embodiment of the present invention.
  • the adhesive sheet 100 according to this embodiment comprises an adhesive layer 10 .
  • the adhesive layer 10 is composed of an active energy ray-curable adhesive.
  • the active energy ray-curable pressure-sensitive adhesive contains an ultraviolet absorber and/or a photopolymerization initiator.
  • FIG. 1(b) is a schematic cross-sectional view of an adhesive sheet according to one embodiment of the present invention.
  • the adhesive sheet 200 according to this embodiment further comprises a substrate 20 with an adhesive layer 10 disposed on at least one side of the substrate 20 .
  • the pressure-sensitive adhesive sheet of the present invention may be provided with a release liner on the outside of the pressure-sensitive adhesive layer for the purpose of protecting the pressure-sensitive adhesive surface until it is used.
  • the pressure-sensitive adhesive sheet may further contain any appropriate other layer as long as the effects of the present invention can be obtained.
  • the adherend can be peeled off satisfactorily due to the generation of strain due to the reduction in the adhesive strength of the adhesive layer and the increase in the elastic modulus.
  • the pressure-sensitive adhesive sheet can be constructed without providing a layer (so-called separation layer) other than the pressure-sensitive adhesive layer for separating the body.
  • the pressure-sensitive adhesive sheet is used for transferring electronic components. More specifically, the pressure-sensitive adhesive sheet can be used for transferring electronic parts, including receiving electronic parts by a laser lift-off process and then peeling off the electronic parts by laser light irradiation. Examples of electronic components include mini-LEDs and micro-LEDs.
  • the adhesive sheet does not contain a base material.
  • the pressure-sensitive adhesive sheet of the present invention is composed of only one pressure-sensitive adhesive layer, as shown in FIG. 1(a).
  • a pressure-sensitive adhesive sheet that does not contain a substrate is preferable because it is excellent in energy utilization efficiency when an adherend is peeled off by irradiation with a laser beam.
  • the pressure-sensitive adhesive sheet of the present invention comprises a base material and a pressure-sensitive adhesive layer, as shown in FIG. without).
  • the pressure-sensitive adhesive layer has an initial indentation elastic modulus of 4 MPa or less at 23°C.
  • the pressure-sensitive adhesive layer has such an indentation elastic modulus, when the electronic component is attached, a part of the electronic component can preferably be embedded in the pressure-sensitive adhesive layer, The electronic component can be temporarily fixed with good fixability. For example, as will be described later, in the case of transferring an electronic component from a hard substrate to an adhesive sheet, displacement of the adherend, tilting of the adherend, and the like are prevented when the hard substrate is removed.
  • the indentation modulus can be measured by the single indentation method at 23° C. with an indentation speed of 10 nm/s and an indentation depth of 100 nm.
  • the adhesive sheet transfers a plurality of electronic components (e.g., LED chips) arranged on a substrate (e.g., a hard substrate such as a sapphire substrate) to the adhesive sheet; Transferring the electronic component on to another member; thus can be used.
  • the transfer of the electronic component from the substrate to the adhesive sheet can be performed by a process including irradiating the substrate/electronic component interface portion with laser light, that is, a laser lift-off process.
  • a laser lift-off process it is possible to arrange the electronic component on the adhesive sheet in a preferable state such as preventing the electronic component to be adhered from tilting. It is possible to receive it favorably.
  • a laser lift-off process it is possible to prevent contaminants generated from the pressure-sensitive adhesive layer from adhering to the electronic component, which is the adherend, due to the influence of laser light irradiation.
  • the transfer from the adhesive sheet to another member can be performed by laser light irradiation.
  • the pressure-sensitive adhesive layer contains an ultraviolet absorber or a photopolymerization initiator
  • the adherend can be peeled off by laser light irradiation. More specifically, by irradiating the adhesive layer with laser light, the ultraviolet absorber or photopolymerization initiator is heated and the adhesive layer is distorted. sexuality emerges.
  • the pressure-sensitive adhesive layer can be distorted in a minute range. It can be peeled off. By using such a pressure-sensitive adhesive sheet, it is possible to omit cleaning of the electronic parts after peeling. In addition, even when a small electronic component that requires peeling and a small electronic component that does not require peeling are temporarily fixed side by side, only the small electronic component that requires peeling can be peeled off. can also prevent unnecessary desorption of
  • the pressure-sensitive adhesive sheet of the present invention exhibits excellent properties in both receiving electronic parts by the laser lift-off process and peeling the electronic parts by laser light irradiation. Therefore, according to the present invention, when transferring an electronic component by a method including receiving the electronic component by a laser lift-off process and peeling off the electronic component by laser light irradiation, the transfer is completed using only the adhesive sheet. can be made Since a plurality of adhesive sheets are not required, the number of transfer processes can be reduced, and as a result, electronic components can be transferred with high positional accuracy. Also, production costs can be reduced.
  • the adhesive layer is composed of an active energy ray-curable adhesive.
  • a pressure-sensitive adhesive sheet containing an active energy ray-curable pressure-sensitive adhesive the adhesive strength of the entire pressure-sensitive adhesive layer is reduced by irradiation with an active energy ray.
  • the entire adhesive layer of the adhesive sheet to which the adherend (electronic component) is attached is irradiated with active energy rays to reduce the adhesive strength, and then the laser beam is irradiated as described above to remove the adhesive. It is possible to prevent adhesive residue later.
  • By using such an adhesive sheet it is possible to omit cleaning of the electronic parts after peeling.
  • the laser output at the time of peeling can be reduced.
  • the pressure-sensitive adhesive sheet of the present invention exhibits releasability with a low-power laser beam, if the pressure-sensitive adhesive sheet is used, the damage to the electronic component that is the adherend during peeling is reduced, and the electronic component is damaged. can be prevented.
  • the peelability can be expressed by a laser beam with an output that does not cause decomposition (thermal decomposition) of the adhesive layer itself, contamination of the electronic component, which is the adherend, by the decomposition product of the adhesive layer is prevented. be able to.
  • active energy rays examples include gamma rays, ultraviolet rays, visible rays, infrared rays (heat rays), radio waves, alpha rays, beta rays, electron beams, plasma currents, ionizing rays, and particle beams.
  • Ultraviolet rays are preferred.
  • the pressure-sensitive adhesive layer is a layer having an indentation elastic modulus of 150 MPa or more at 23° C. after being irradiated with ultraviolet rays of 460 mJ/cm 2 . If the adhesive layer is provided with such an indentation elastic modulus after ultraviolet irradiation, the adhesive layer is distorted by irradiation with a low-energy laser beam, and as a result, the adherend (electronic component) is improved. can be peeled off. Also, it is possible to prevent the contamination of the electronic component at the time of peeling.
  • the light transmittance of the adhesive sheet of the present invention at a wavelength of 355 nm is 50% or less.
  • the laser output at the time of peeling can be lowered.
  • the pressure-sensitive adhesive sheet of the present invention exhibits releasability with a low-power laser beam, if the pressure-sensitive adhesive sheet is used, the damage to the electronic component that is the adherend during peeling is reduced, and the electronic component is damaged. can be prevented.
  • the light transmittance of the adhesive sheet of the present invention at a wavelength of 355 nm is preferably 40% or less, more preferably 30% or less. Within such a range, the above effects are more pronounced.
  • the light transmittance of the adhesive sheet is the light transmittance in the thickness direction of the adhesive sheet, and is the light transmittance measured for all the constituent layers of the adhesive sheet.
  • the light transmittance of the pressure-sensitive adhesive sheet at a wavelength of 355 nm can be controlled by adjusting the content of the ultraviolet absorber contained in the pressure-sensitive adhesive layer.
  • the light transmittance of the adhesive sheet at a wavelength of 355 nm can also be controlled by the composition of the base polymer and the photopolymerization initiator that constitute the adhesive layer.
  • the light transmittance of the adhesive sheet at a wavelength of 355 nm can be controlled by the type and amount of the photopolymerization initiator contained in the adhesive layer, particularly by the compatibility between the photopolymerization initiator and the base polymer.
  • the visible light transmittance of the adhesive sheet is preferably 50% or higher, more preferably 60% or higher, and even more preferably 70% or higher. Within such a range, it is possible to obtain a pressure-sensitive adhesive sheet from which the adherend to be peeled can be well visually recognized through the pressure-sensitive adhesive sheet when the adherend is peeled off by laser light irradiation.
  • the haze value of the adhesive sheet is preferably 70% or less, more preferably 65% or less. Within such a range, it is possible to obtain a pressure-sensitive adhesive sheet from which the adherend to be peeled can be well visually recognized through the pressure-sensitive adhesive sheet when the adherend is peeled off by laser light irradiation.
  • the haze value of the adhesive sheet is preferably as low as possible, but its lower limit is, for example, 0.1%.
  • the initial adhesive force A at 23° C. immediately after the adhesive sheet is attached to a stainless steel plate is preferably 0.1 N/20 mm to 15 N/20 mm, more preferably 0.5 N/20 mm to 10 N/20 mm. Within such a range, it is possible to obtain a pressure-sensitive adhesive sheet that can hold an adherend well. Adhesion is measured according to JIS Z 0237:2000. Specifically, the pressure-sensitive adhesive sheet was attached to a stainless steel plate (arithmetic mean surface roughness Ra: 50 ⁇ 25 nm) by reciprocating a 2 kg roller once, left at 23 ° C. for 30 minutes, and then peeled at a peel angle of 180 °.
  • the pressure-sensitive adhesive layer changes its adhesive strength due to irradiation with active energy rays and laser light.
  • the term "initial adhesive strength” means the adhesive strength before irradiation with active energy rays and laser light. .
  • the adhesive force B at 23° C. after the adhesive sheet is attached to a stainless steel plate and irradiated with ultraviolet rays of 300 mJ/cm 2 is preferably 0.2 N. /20 mm or less, more preferably 0.01 N/20 mm to 0.2 N/20 mm, and more preferably 0.02 N/20 mm to 0.15 N/20 mm. Within such a range, a pressure-sensitive adhesive sheet with little adhesive residue can be obtained.
  • the ultraviolet irradiation is performed by, for example, using an ultraviolet irradiation device (manufactured by Nitto Seiki Co., Ltd., trade name “UM-810”) and applying ultraviolet light from a high-pressure mercury lamp (characteristic wavelength: 365 nm, integrated light amount: 300 mJ/cm 2 ) to the adhesive layer. is performed by irradiating to an ultraviolet irradiation device (manufactured by Nitto Seiki Co., Ltd., trade name “UM-810”) and applying ultraviolet light from a high-pressure mercury lamp (characteristic wavelength: 365 nm, integrated light amount: 300 mJ/cm 2 ) to the adhesive layer. is performed by irradiating to a high-pressure mercury lamp (characteristic wavelength: 365 nm, integrated light amount: 300 mJ/cm 2 ) to the adhesive layer. is performed by irradiating to an ultraviolet irradiation device (manufactured by Nitto Seiki Co., Ltd.
  • the reduction rate of the post-curing adhesive strength B with respect to the initial adhesive strength A is preferably 90% or more, more preferably 95% or more. Within such a range, a pressure-sensitive adhesive sheet with excellent peelability can be obtained.
  • the rate of decrease (%) can be obtained from the formula (initial adhesive strength A ⁇ adhesive strength after curing B)/initial adhesive strength A ⁇ 100.
  • the thickness of the adhesive sheet is preferably 1 ⁇ m to 300 ⁇ m, more preferably 5 ⁇ m to 200 ⁇ m.
  • the thickness of the adhesive layer is preferably 20 ⁇ m or less. Within such a range, it is possible to lower the laser output at the time of peeling, and to obtain a pressure-sensitive adhesive sheet with excellent peelability.
  • the thickness of the adhesive layer is more preferably 15 ⁇ m or less, still more preferably 10 ⁇ m or less, and more preferably 1 ⁇ m to 10 ⁇ m. With such a range, the above effect becomes remarkable.
  • the pressure-sensitive adhesive layer has an initial indentation elastic modulus of 4 MPa or less at 23°C.
  • the initial indentation modulus of the pressure-sensitive adhesive layer at 23° C. is preferably 3 MPa or less, more preferably 2 MPa or less. Within such a range, the above effects of the present invention become remarkable.
  • the initial indentation modulus of the pressure-sensitive adhesive layer at 23° C. is preferably 0.1 MPa or more, more preferably 0.2 MPa or more, still more preferably 0.3 MPa or more, and particularly preferably 0.7 MPa. That's it. Within such a range, it is possible to obtain a pressure-sensitive adhesive sheet that is less likely to stain an adherend and has excellent releasability.
  • the pressure-sensitive adhesive layer is a layer having an indentation modulus of elasticity at 23° C. of 150 MPa or more after being irradiated with ultraviolet rays of 460 mJ/cm 2 .
  • the pressure-sensitive adhesive layer preferably has an indentation modulus of 200 MPa or more at 23° C., more preferably 300 MPa or more, more preferably 400 MPa or more, after irradiation with ultraviolet rays of 460 mJ/cm 2 . It is more preferable to be a layer having a tensile strength of 500 MPa or higher, particularly preferably a layer having a tensile strength of 800 MPa or higher. With such a range, the above effect becomes remarkable.
  • the upper limit of the indentation modulus of the pressure-sensitive adhesive layer after irradiation with ultraviolet rays of 460 mJ/cm 2 is, for example, 8000 MPa (preferably 5000 MPa, more preferably 4000 MPa).
  • the stress relaxation rate of the pressure-sensitive adhesive layer after 600 seconds is preferably 10% or more, more preferably 15% or more, and even more preferably 20% or more. Within such a range, it is possible to obtain a pressure-sensitive adhesive sheet with excellent chip retention. Specifically, it is possible to obtain a pressure-sensitive adhesive sheet in which the adherend (electronic component) is less likely to tilt on the pressure-sensitive adhesive layer even with the lapse of time after placement of the adherend (electronic component). By using such an adhesive sheet, electronic components can be transferred with good positional accuracy.
  • the upper limit of the stress relaxation rate of the adhesive layer after 600 seconds is, for example, 100% (preferably 80%).
  • the adhesive layer is composed of an active energy ray-curable adhesive.
  • the active energy ray-curable pressure-sensitive adhesive may contain the ultraviolet absorber and/or the photopolymerization initiator.
  • the active energy ray-curable pressure-sensitive adhesive is an active energy ray-curable adhesive containing a base polymer as a base material and an active energy ray-reactive compound (monomer or oligomer) capable of bonding with the base polymer.
  • An adhesive (A1) is used.
  • an active energy ray-curable pressure-sensitive adhesive (A2) containing an active energy ray-reactive polymer as a base polymer is used.
  • the base polymer has functional groups capable of reacting with the photoinitiator. Examples of the functional group include hydroxyl group and carboxyl group.
  • Examples of the base polymer used in the adhesive (A1) include natural rubber, polyisobutylene rubber, styrene/butadiene rubber, styrene/isoprene/styrene block copolymer rubber, recycled rubber, butyl rubber, polyisobutylene rubber, and nitrile rubber.
  • rubber-based polymers such as (NBR); silicone-based polymers; and acrylic polymers. These polymers may be used alone or in combination of two or more. Among them, acrylic polymers are preferred.
  • acrylic polymers include homopolymers and copolymers of hydrocarbon group-containing (meth)acrylic esters such as (meth)acrylic acid alkyl esters, (meth)acrylic acid cycloalkyl esters, and (meth)acrylic acid aryl esters.
  • hydrocarbon group-containing (meth)acrylic esters such as (meth)acrylic acid alkyl esters, (meth)acrylic acid cycloalkyl esters, and (meth)acrylic acid aryl esters.
  • (Meth)acrylic acid alkyl esters include, for example, (meth)acrylic acid methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, isobutyl ester, s-butyl ester, t-butyl ester, pentyl ester, iso Pentyl ester, hexyl ester, heptyl ester, octyl ester, 2-ethylhexyl ester, isooctyl ester, nonyl ester, decyl ester, isodecyl ester, undecyl ester, dodecyl ester or lauryl ester, tridecyl ester, tetradecyl ester, hexa Decyl esters, octa
  • (Meth)acrylic acid cycloalkyl esters include, for example, cyclopentyl and cyclohexyl esters of (meth)acrylic acid.
  • (Meth)acrylic acid aryl esters include, for example, phenyl (meth)acrylate and benzyl (meth)acrylate.
  • the content of structural units derived from the hydrocarbon group-containing (meth)acrylic acid ester is preferably 40 parts by weight or more, more preferably 60 parts by weight or more, relative to 100 parts by weight of the base polymer.
  • Examples of other copolymerizable monomers include carboxy group-containing monomers, acid anhydride monomers, hydroxy group-containing monomers, glycidyl group-containing monomers, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, acrylamide, and acrylonitrile.
  • Examples include functional group-containing monomers.
  • Carboxy group-containing monomers include, for example, acrylic acid, methacrylic acid, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate, itaconic acid, maleic acid, fumaric acid, and crotonic acid.
  • Anhydride monomers include, for example, maleic anhydride and itaconic anhydride.
  • hydroxy group-containing monomers examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, ( 8-hydroxyoctyl meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, and (4-hydroxymethylcyclohexyl)methyl (meth)acrylate.
  • Glycidyl group-containing monomers include, for example, glycidyl (meth)acrylate and methylglycidyl (meth)acrylate.
  • Sulfonic acid group-containing monomers include, for example, styrenesulfonic acid, allylsulfonic acid, 2-(meth)acrylamido-2-methylpropanesulfonic acid, (meth)acrylamidopropanesulfonic acid, sulfopropyl (meth)acrylate, and (meth) ) acryloyloxynaphthalene sulfonic acid.
  • Phosphate group-containing monomers include, for example, 2-hydroxyethyl acryloyl phosphate.
  • Acrylamides include, for example, N-acryloylmorpholine. These may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the content of structural units derived from the copolymerizable monomer is preferably 60 parts by weight or less, more preferably 40 parts by weight or less, relative to 100 parts by weight of the base polymer.
  • the acrylic polymer may contain structural units derived from polyfunctional monomers in order to form a crosslinked structure in the polymer backbone.
  • polyfunctional monomers include hexanediol di(meth)acrylate, (poly)ethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol di(meth)acrylate, (meth)acrylates, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, epoxy (meth)acrylate (i.e.
  • polyglycidyl (meth)acrylate polyglycidyl (meth)acrylate), polyester (meth)acrylate ) acrylates, and urethane (meth)acrylates. These may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the content of the structural unit derived from the polyfunctional monomer is preferably 40 parts by weight or less, more preferably 30 parts by weight or less, relative to 100 parts by weight of the base polymer.
  • the weight average molecular weight of the acrylic polymer is preferably 100,000 to 3,000,000, more preferably 200,000 to 2,000,000.
  • a weight average molecular weight can be measured by GPC (solvent: THF).
  • Examples of the active energy ray-reactive compound that can be used in the adhesive (A1) include a functional group having a polymerizable carbon-carbon multiple bond such as an acryloyl group, a methacryloyl group, a vinyl group, an allyl group, and an acetylene group.
  • photoreactive monomers or oligomers having Specific examples of the photoreactive monomer include trimethylolpropane tri(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol mono Hydroxy penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, polyethylene glycol di (meth) acrylate ( Esterified product of meth)acrylic acid and polyhydric alcohol; polyfunctional urethane (meth)acrylate; epoxy (meth)acrylate; oligoester (meth)acrylate and the like.
  • Monomers such as methacryloylisocyanate, 2-methacryloyloxyethyl isocyanate (2-isocyanatoethyl methacrylate), m-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate may also be used.
  • Specific examples of photoreactive oligomers include dimers to pentamers of the above monomers. The molecular weight of the photoreactive oligomer is preferably 100-3000.
  • a polyfunctional (meth)acrylate having 5 or more functional groups or a polyfunctional (meth)acrylate oligomer having 5 or more functional groups is used as the active energy ray-reactive compound.
  • an active energy ray-reactive compound By using such an active energy ray-reactive compound, it is possible to form a pressure-sensitive adhesive layer that can become highly elastic when irradiated with an active energy ray (for example, ultraviolet rays). If the elastic modulus of the pressure-sensitive adhesive layer can be increased, the peeling operation can be performed with a low-power laser beam.
  • active energy ray-reactive compound monomers such as epoxidized butadiene, glycidyl methacrylate, acrylamide, and vinylsiloxane; or oligomers composed of such monomers may be used.
  • the active energy ray-reactive compound a mixture of an organic salt such as an onium salt and a compound having a plurality of heterocycles in the molecule may be used.
  • an active energy ray e.g., ultraviolet rays, electron beams
  • the organic salt is cleaved to generate ions, which act as starting species to cause a heterocyclic ring-opening reaction to form a three-dimensional network structure.
  • the organic salts include iodonium salts, phosphonium salts, antimonium salts, sulfonium salts, borate salts and the like.
  • the heterocyclic ring in the compound having a plurality of heterocyclic rings in the molecule include oxirane, oxetane, oxolane, thiirane, aziridine and the like.
  • the content of the active energy ray-reactive compound is preferably 0.1 parts by weight to 500 parts by weight, more preferably 5 parts by weight to 300 parts by weight, with respect to 100 parts by weight of the base polymer. parts by weight, more preferably 40 to 150 parts by weight.
  • Examples of the active energy ray-reactive polymer (base polymer) contained in the adhesive (A2) include functional groups having carbon-carbon multiple bonds such as acryloyl groups, methacryloyl groups, vinyl groups, allyl groups, and acetylene groups.
  • polymer having Specific examples of active energy ray-reactive polymers include polymers composed of polyfunctional (meth)acrylates; photo-cationically polymerizable polymers; cinnamoyl group-containing polymers such as polyvinyl cinnamate; diazotized amino novolak resins; ; and the like.
  • the active energy configured by introducing an active energy ray-polymerizable carbon-carbon multiple bond into the side chain, main chain and/or main chain end of the acrylic polymer (precursor resin)
  • a linear reactive polymer is used.
  • a technique for introducing a radiation-polymerizable carbon-carbon double bond into an acrylic polymer (precursor resin) for example, a raw material monomer containing a monomer having a predetermined functional group (first functional group) is copolymerized.
  • a predetermined functional group (second functional group) and a radiation-polymerizable carbon-carbon double a compound having a bond (hereinafter also simply referred to as a compound having a carbon double bond) with an acrylic polymer while maintaining the radiation polymerizability of the carbon-carbon double bond. , are mentioned.
  • the amount of the compound having a carbon double bond introduced is preferably 10 parts by weight or more, more preferably 12 parts by weight or more, relative to 100 parts by weight of the solid content of the acrylic polymer (precursor resin). It is preferably 15 parts by weight or more. Within such a range, it is possible to obtain a low-polarity active energy ray-reactive polymer (base polymer). Also, it is possible to detach the adherend preferably by irradiating laser light with low energy.
  • the upper limit of the introduction amount of the compound having a carbon double bond is, for example, 80 parts by weight (preferably 60 parts by weight, more preferably 50 parts by weight) with respect to 100 parts by weight of the solid content of the acrylic polymer (precursor resin). is.
  • Combinations of the first functional group and the second functional group include, for example, a carboxy group and an epoxy group, an epoxy group and a carboxy group, a carboxy group and an aziridyl group, an aziridyl group and a carboxy group, a hydroxy group and an isocyanate group, and an isocyanate group. and hydroxy groups.
  • a combination of a hydroxy group and an isocyanate group and a combination of an isocyanate group and a hydroxy group are preferable from the viewpoint of ease of reaction tracking.
  • examples of isocyanate compounds having both a radiation-polymerizable carbon-carbon double bond and an isocyanate group as the second functional group include methacryloyl isocyanate, 2-methacryloyloxyethyl isocyanate, m-isopropenyl- ⁇ , and ⁇ -dimethylbenzyl isocyanate.
  • the acrylic polymer having the first functional group preferably contains a structural unit derived from the hydroxy group-containing monomer, such as 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, and diethylene glycol monovinyl ether. It is also preferable to contain a constitutional unit derived from an ether-based compound.
  • the glass transition temperature Tg of the active energy ray-reactive polymer (base polymer) is preferably ⁇ 60° C. or higher, more preferably ⁇ 50° C. or higher, and still more preferably ⁇ 40° C. or higher. Within such a range, it is possible to obtain a low-polarity active energy ray-reactive polymer (base polymer). Also, it is possible to detach the adherend preferably by irradiating laser light with low energy.
  • the upper limit of the glass transition temperature Tg of the active energy ray-reactive polymer (base polymer) is preferably 0°C, more preferably -20°C.
  • the Tg of the base polymer is based on the Tg of the homopolymer (homopolymer) of each monomer constituting the base polymer and the weight fraction (copolymerization ratio based on weight) of the monomer, from the Fox formula It means the desired value.
  • the Fox equation is a relational expression between the Tg of a copolymer and the glass transition temperature Tgi of a homopolymer obtained by homopolymerizing each of the monomers constituting the copolymer, as shown below.
  • Tg is the glass transition temperature of the copolymer (unit: K)
  • Wi is the weight fraction of the monomer i in the copolymer (weight-based copolymerization ratio)
  • Tgi is the homopolymer of the monomer i. represents the glass transition temperature (unit: K).
  • Tg of the homopolymer the values described in known documents shall be adopted.
  • the adhesive (A2) may further contain the active energy ray-reactive compound (monomer or oligomer).
  • the active energy ray-curable adhesive may contain an ultraviolet absorber and/or a photopolymerization initiator. Details of the ultraviolet absorber and photopolymerization initiator used are as described above.
  • the active energy ray-curable pressure-sensitive adhesive may contain a photosensitizer.
  • the photosensitizer can be used in combination with the photopolymerization initiator.
  • the photosensitizer can generate radicals from the photopolymerization initiator by passing the energy obtained by itself absorbing light to the photopolymerization initiator, so the absorption peak of the photopolymerization initiator itself is Polymerization can proceed with light on the long wavelength side. Therefore, by including a photosensitizer, it is possible to increase the difference between the absorption wavelength of the ultraviolet absorber and the wavelength at which radicals can be generated from the photopolymerization initiator. As a result, the photopolymerization of the pressure-sensitive adhesive layer and the peeling by the ultraviolet absorber can be performed without affecting each other.
  • 2,2-dimethoxy-1,2-diphenylethan-1-one (for example, manufactured by BASF, trade name “Irgacure 651”) as a photopolymerization initiator, and a photosensitizer are used together.
  • photosensitizers include trade name "UVS-581” manufactured by Kawasaki Kasei Co., Ltd., 9,10-diethoxyanthracene (for example, trade name "UVS1101" manufactured by Kawasaki Kasei Co., Ltd.), and the like. be done.
  • photosensitizer examples include 9,10-dibutoxyanthracene (eg, trade name “UVS-1331” manufactured by Kawasaki Chemical Industries, Ltd.), 2-isopropylthioxanthone, benzophenone, thioxanthone derivatives, 4,4 '-bis(dimethylamino)benzophenone and the like.
  • Thioxanthone derivatives include, for example, ethoxycarbonylthioxanthone and isopropylthioxanthone.
  • the content of the photosensitizer is preferably 0.01 to 2 parts by weight, more preferably 0.5 to 2 parts by weight, relative to 100 parts by weight of the base polymer.
  • the active energy ray-curable pressure-sensitive adhesive contains a cross-linking agent.
  • cross-linking agents include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, oxazoline-based cross-linking agents, aziridine-based cross-linking agents, melamine-based cross-linking agents, peroxide-based cross-linking agents, urea-based cross-linking agents, metal alkoxide-based cross-linking agents, Examples include metal chelate cross-linking agents, metal salt cross-linking agents, carbodiimide cross-linking agents, amine cross-linking agents and the like.
  • the content of the cross-linking agent is preferably 0.5 to 10 parts by weight, more preferably 1 to 8 parts by weight, with respect to 100 parts by weight of the base polymer of the adhesive.
  • an isocyanate-based cross-linking agent is preferably used.
  • An isocyanate-based cross-linking agent is preferable because it can react with various functional groups.
  • Specific examples of the isocyanate-based cross-linking agents include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; aromatic isocyanates such as tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, xylylene diisocyanate; trimethylolpropane/tolylene diisocyanate trimer adduct (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name “Coronate L”), tri Methylolpropane/hexamethylene diisocyanate trimer adduct (manufactured by Nippon Polyurethane Industry Co., Ltd., trade name "Coronate HL”), hexamethylene diiso
  • the active energy ray-curable adhesive may further contain any suitable additive as necessary.
  • Additives include, for example, active energy ray polymerization accelerators, radical scavengers, tackifiers, plasticizers (e.g., trimellitic acid ester plasticizers, pyromellitic acid ester plasticizers, etc.), pigments, dyes, and fillers. agents, anti-aging agents, conductive materials, antistatic agents, ultraviolet absorbers, light stabilizers, release modifiers, softeners, surfactants, flame retardants, antioxidants, and the like.
  • UV absorber any suitable UV absorber can be used as long as it is a compound that absorbs UV light (for example, wavelength of 355 nm).
  • the ultraviolet absorber include benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, salicylate-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers.
  • triazine-based UV absorbers and benzotriazole-based UV absorbers are preferred, and triazine-based UV absorbers are particularly preferred.
  • triazine-based ultraviolet absorbers are preferably used because of their high compatibility with the base polymer of the acrylic pressure-sensitive adhesive.
  • the triazine-based ultraviolet absorber is more preferably composed of a compound having a hydroxyl group, and particularly preferably an ultraviolet absorber composed of a hydroxyphenyltriazine-based compound (hydroxyphenyltriazine-based ultraviolet absorber).
  • hydroxyphenyltriazine-based UV absorbers examples include 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-hydroxyphenyl and [(C10 -Reaction product with C16 (mainly C12-C13) alkyloxy)methyl]oxirane (trade name "TINUVIN 400", manufactured by BASF), 2-[4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol), 2-(2,4-dihydroxyphenyl)-4,6-bis-(2, 4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidate reaction product (trade name "TINUVIN 405", manufactured by BASF), 2,4-bis(2-hydroxy- 4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5
  • Benzotriazole-based UV absorbers include, for example, 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole (trade name "TINUVIN PS", manufactured by BASF), benzene Ester compound of propanoic acid and 3-(2H-benzotriazol-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy (C7-9 side chain and linear alkyl) (trade name "TINUVIN 384 -2", manufactured by BASF), octyl 3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate and 2-ethylhexyl-3-[ A mixture of 3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2yl)phenyl]propionate (trade name "TINUVIN 109", manufactured by BASF), 2-(2-hydroxy-5-tert-buty
  • the ultraviolet absorber may be a dye or pigment.
  • pigments include azo-based, phthalocyanine-based, anthraquinone-based, lake-based, perylene-based, perinone-based, quinacridone-based, thioindigo-based, dioxandine-based, isoindolinone-based, and quinophthalone-based pigments.
  • Dyes include azo, phthalocyanine, anthraquinone, carbonyl, indigo, quinoneimine, methine, quinoline, and nitro dyes.
  • the molecular weight of the compound constituting the ultraviolet absorber is preferably 1000 or less, more preferably 800 or less, and even more preferably 600 or less.
  • the UV absorber having a molecular weight within the above range has excellent compatibility with the base polymer. It becomes possible to peel with low laser energy. As a result, thermal decomposition of the adhesive layer can be prevented. By forming such a pressure-sensitive adhesive layer, it is possible to obtain a pressure-sensitive adhesive sheet that does not easily stain an adherend.
  • the lower limit of the molecular weight of the compound constituting the ultraviolet absorber is 100, for example.
  • the maximum absorption wavelength of the ultraviolet absorber is preferably 300 nm to 450 nm, more preferably 320 nm to 400 nm, still more preferably 330 nm to 380 nm.
  • the difference between the maximum absorption wavelength of the ultraviolet absorber and the maximum absorption wavelength of the photopolymerization initiator is preferably 10 nm or more, more preferably 25 nm or more.
  • the content of the ultraviolet absorber is preferably 1 part by weight to 50 parts by weight, more preferably 2 parts by weight to 30 parts by weight, and still more preferably 100 parts by weight of the base polymer in the pressure-sensitive adhesive layer. is 3 to 25 parts by weight. Within such a range, when the adhesive strength of the entire adhesive layer is satisfactorily lowered by irradiation with active energy rays, the curing of the adhesive layer proceeds well, and good peelability is achieved by laser light irradiation. can be obtained.
  • photopolymerization initiators Any appropriate initiator can be used as the photopolymerization initiator.
  • photopolymerization initiators include 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)ketone, ⁇ -hydroxy- ⁇ , ⁇ '-dimethylacetophenone, 2-methyl-2-hydroxypropio ⁇ -ketol compounds such as phenone and 1-hydroxycyclohexylphenyl ketone; methoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 2-methyl-1-[4-(methylthio) Acetophenone compounds such as -phenyl]-2-morpholinopropane-1; benzoin ether compounds such as benzoin ethyl ether, benzoin isopropyl ether, and anisoin methyl ether; ketal compounds such as benzyl dimethyl ketal; 2-naphthalenesulfonyl chloride, etc.
  • aromatic sulfonyl chloride compounds 1-phenone-1,1-propanedione-2-(o-ethoxycarbonyl) oxime and other photoactive oxime compounds; benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4 -benzophenone compounds such as methoxybenzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4 thioxanthone-based compounds such as diethylthioxanthone and 2,4-diisopropylthioxanthone; camphorquinone; halogenated ketones;
  • the amount of photopolymerization initiator used can be set to any appropriate amount.
  • a photopolymerization initiator having two or more (preferably two to five) photodegradable groups is used as the photopolymerization initiator.
  • a photopolymerization initiator By using such a photopolymerization initiator, it is possible to form a pressure-sensitive adhesive layer that can become highly elastic when irradiated with active energy rays (eg, ultraviolet rays). If the elastic modulus of the pressure-sensitive adhesive layer can be increased, the peeling operation can be performed with a low-power laser beam.
  • a photodegradable group means a functional group that absorbs irradiated active energy rays and generates radicals. mentioned.
  • Photopolymerization initiators having two or more photodegradable groups include, for example, 2-hydroxy-1-[4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl]-2-methyl -Propan-1-one (trade name Omnirad 127, manufactured by BASF Japan), 1-[4-(4-benzoxylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenylsulfonyl)propane-1 -one (trade name ESURE 1001M), methylbenzoylformate (trade name SPEEDCURE MBF manufactured by LAMBSON), O-ethoxyimino-1-phenylpropan-1-one (trade name SPEEDCURE PDO manufactured by LAMBSON), oligo [2-hydroxy-2 -methyl-4-(1-methylvinyl)phenyl]propanone (trade name ESCURE KIPI50 manufactured by Lamberti) and the like.
  • a compound containing a phosphorus atom and/or a nitrogen atom is used as the photopolymerization initiator.
  • photopolymerization initiators include, for example, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (trade name Omnirad 907, manufactured by BASF Japan), 2-benzyl- 2-(dimethylamino)-4'-morpholinobtyrophenone (trade name Omnirad 369, manufactured by BASF Japan), 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl) Butan-1-one (trade name Omnirad 379, manufactured by BASF Japan), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (trade name Omnirad 819, manufactured by BASF Japan), 2,4,6-trimethylbenzoyl-diphenyl Phosphine oxide (trade name: OmniradTPO, manufactured by BASF Japan), 1,2-oc
  • a photopolymerization initiator By using such a photopolymerization initiator, it is possible to form a pressure-sensitive adhesive layer that can become highly elastic when irradiated with active energy rays (eg, ultraviolet rays). If the elastic modulus of the pressure-sensitive adhesive layer can be increased, the peeling operation can be performed with a low-power laser beam.
  • active energy rays eg, ultraviolet rays
  • the content of the photopolymerization initiator is preferably 1 part by weight to 30 parts by weight, more preferably 2 parts by weight to 20 parts by weight, with respect to 100 parts by weight of the base polymer in the adhesive layer. It is preferably 3 to 15 parts by weight.
  • the adhesive strength of the entire adhesive layer is favorably reduced by irradiation with an active energy ray
  • the curing of the adhesive layer proceeds favorably, and distortion of the adhesive layer due to laser light irradiation is achieved. It is possible to obtain a pressure-sensitive adhesive sheet with a large amount and good releasability.
  • the substrate may be composed of any suitable resin.
  • the resin include polyolefin-based resins such as polyethylene-based resins, polypropylene-based resins, polybutene-based resins, and polymethylpentene-based resins, polyurethane-based resins, polyester-based resins, polyimide-based resins, polyetherketone-based resins, and polystyrene-based resins.
  • Resins, polyvinyl chloride resins, polyvinylidene chloride resins, fluorine resins, silicon resins, cellulose resins, ionomer resins, and the like can be mentioned. Among them, polyolefin resins are preferred.
  • the thickness of the base material is preferably 2 ⁇ m to 300 ⁇ m, more preferably 2 ⁇ m to 100 ⁇ m, still more preferably 2 ⁇ m to 50 ⁇ m.
  • the light transmittance of the substrate at a wavelength of 355 nm is preferably 70% or higher, more preferably 80% or higher, even more preferably 90% or higher, and particularly preferably 95% or higher.
  • the upper limit of the total light transmittance of the substrate is, for example, 98% (preferably 99%).
  • a pressure-sensitive adhesive sheet can be produced by any appropriate method.
  • a pressure-sensitive adhesive sheet can be obtained, for example, by applying the above pressure-sensitive adhesive onto a substrate or a release liner.
  • Coating methods include bar coater coating, air knife coating, gravure coating, gravure reverse coating, reverse roll coating, lip coating, die coating, dip coating, offset printing, flexographic printing, screen printing, etc.
  • Various methods can be employed.
  • a method of forming a pressure-sensitive adhesive layer on a release liner and then attaching it to a base material may be adopted.
  • the transfer method includes, for example, a first step of transferring a plurality of electronic components arranged on a substrate onto an adhesive layer of the adhesive sheet; and transferring the electronic components on the adhesive sheet to another member.
  • a second step is included.
  • the same adhesive sheet is used in the first step and the second step. That is, in the transfer method, the electronic component can be transferred without including an additional transfer step.
  • the transfer of the electronic component from the substrate to the adhesive sheet can be performed by a process including irradiating the substrate/electronic component interface portion with laser light, that is, a laser lift-off process.
  • the conditions for the laser lift-off process can be any suitable conditions.
  • a hard substrate such as a sapphire substrate may be used as the substrate.
  • the second step includes the following operations: (i) irradiating the adhesive sheet with active energy rays (e.g., ultraviolet rays) to form the adhesive layer of the adhesive sheet; (ii) irradiating a laser beam to a portion where peelability is desired to cause strain in the adhesive layer to further reduce the adhesive force.
  • active energy rays e.g., ultraviolet rays
  • the electronic component can be detached only at the location irradiated with the laser beam.
  • the adhesive force can be reduced to the extent that it naturally falls, so even very small (for example, 50 ⁇ m square) electronic components can be individually peeled off. be.
  • the active energy ray in (i) above may be irradiated to the entire surface of the pressure-sensitive adhesive layer.
  • ultraviolet rays are irradiated with an integrated light amount of 200 mJ/cm 2 to 600 mJ/cm 2 .
  • laser light in (ii) above for example, a laser light with a wavelength of 200 nm to 360 nm (preferably 355 nm) is used.
  • Laser light output is, for example, 100 mJ/cm 2 to 1200 mJ/cm 2 .
  • the electronic components are mini-LEDs or micro-LEDs.
  • PET release liner of the adhesive sheet was peeled off, and PET (Lumirror S10 manufactured by Toray) having a thickness of 25 ⁇ m was attached. After that, the PET release liner on the other side was peeled off, and a 2-kg roller was reciprocated once to bond it to SUS304. Measurement temperature: 23°C), and the adhesive force was measured as the initial adhesive force.
  • the other PET release liner was peeled off to expose the pressure-sensitive adhesive layer, and the indentation modulus was measured using a tripoindenter TI-950 manufactured by Hysitron.
  • the measurements were made by the single indentation method at 23° C. with an indentation speed of 10 nm/s and an indentation depth of 100 nm.
  • LLO Laser lift-off evaluation
  • a protective tape applying device with a vacuum + press mechanism (trade name “DV 3000”, manufactured by Nitto Seiki Co., Ltd.), vacuum time: 90 seconds, crimping conditions: 0.25 MPa, crimping time: 0 seconds.
  • the sapphire surface was irradiated with a laser (excimer laser manufactured by MRAYS) to carry out LLO.
  • the LLO conditions were wavelength: 248 nm and energy density: 900 mJ/cm 3 .
  • the sapphire glass was removed and the yield was checked. Yield: 90% or more was rated good ( ⁇ ), 80% or more and less than 90% was rated acceptable ( ⁇ ), and less than 80% was rated unsatisfactory (x).
  • the LED chips on the adhesive tape were observed using a confocal microscope (product name "OLS 5100", manufactured by Shimadzu Corporation), the tilt angles of 100 chips were measured, and the average value was calculated. If the average tilt value is 0.15° or less, it is excellent ( ⁇ ); ).
  • the adhesive was photo-cured from the quartz glass side of the obtained sample in a nitrogen atmosphere using an ultraviolet irradiation device (trade name “UM 810”, manufactured by Nitto Seiki Co., Ltd.). .
  • the curing conditions were set to 460 mJ/cm 2 in terms of wavelength of 365 nm using ultraviolet light from a high-pressure mercury lamp.
  • a laser (wavelength: 355 nm, pulse width: 5 ns) was irradiated only to the target chip position from the quartz glass side to perform Laser Transfer.
  • a laser beam was irradiated from 100 mJ/cm 2 to 1200 mJ/cm 2 in steps of 100 mJ/cm 2 , and the energy with the best positional accuracy was defined as the Energy value .
  • a value of more than /cm 2 and 1000 mJ/cm 2 or less was rated as good ( ⁇ ), and a value of greater than 1000 mJ/cm 2 and transfer failure at 1200 mJ/cm 2 was rated as fail (x).
  • the chip after transfer was observed using a digital microscope (trade name “VHX2000”, manufactured by Keyence Corporation) to evaluate the positional accuracy.
  • a monomer composition was prepared by mixing 100 parts by weight of 2-methoxyethyl acrylate, 27 parts by weight of acryloylmorpholine and 22 parts by weight of 2-hydroxyethyl acrylate. Next, nitrogen was introduced into a reaction vessel equipped with a nitrogen inlet tube, a thermometer, and a stirrer, and under a nitrogen atmosphere, 500 parts by weight of toluene, 149 parts by weight of the above monomer composition, and 0.3 parts of benzoyl peroxide (BPO) were added. Parts by weight were charged and stirred at 60° C. for 5 hours.
  • BPO benzoyl peroxide
  • Example 1 (Preparation of adhesive) Acrylic polymer solution A containing 100 parts by weight of acrylic polymer A, 3 parts by weight of a cross-linking agent (manufactured by Mitsui Chemicals, trade name "Takenate D-101A"), and an ultraviolet absorber (manufactured by BASF, trade name "Tinuvin PS”. ) and 3 parts by weight of a photopolymerization initiator (manufactured by BASF, trade name “Omnirad TPO”) were added to obtain an adhesive (1). (adhesive sheet) The pressure-sensitive adhesive (1) was applied to the silicone-treated surface of a PET release liner (thickness: 38 ⁇ m) and then heated at 130° C.
  • a cross-linking agent manufactured by Mitsui Chemicals, trade name "Takenate D-101A
  • an ultraviolet absorber manufactured by BASF, trade name "Tinuvin PS”.
  • a photopolymerization initiator manufactured by BASF, trade name “Omnirad T
  • Examples 2 to 14, Comparative Examples 1 to 5 Same as Example 1 except that the acrylic polymer solution, cross-linking agent, ultraviolet absorber, active energy ray-reactive compound (oligomer), and photopolymerization initiator shown in Table 1 were used in the amounts shown in Table 1. to obtain an adhesive sheet.
  • the obtained pressure-sensitive adhesive sheet was subjected to the above evaluation.
  • Table 1 shows the results.
  • the oligomers were added during preparation of the adhesives to obtain the adhesives.
  • Compounds and the like used in Examples and Comparative Examples are as follows.
  • crosslinking agent ⁇ D-101A: isocyanate-based cross-linking agent, manufactured by Mitsui Chemicals, trade name “Takenate D-101A” ⁇ Coronate HX: isocyanate-based cross-linking agent ⁇ Manufactured by Tosoh Corporation, trade name “Coronate/HX” (Ultraviolet absorber) - Tinuvin PS: manufactured by BASF, trade name "Tinuvin PS", 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole Tinuvin 405: manufactured by BASF, trade name "Tinuvin 405", 2 Reaction product of -(2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidate Tinuvin 460: BASF Corporation, trade name "Tinuvin 460", 2,4-bis (2-hydroxy-4-but

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Abstract

L'invention concerne une feuille adhésive qui peut être utilisée dans le transfert de composants électroniques, ladite feuille adhésive pouvant contribuer à une réduction des coûts de production, ce qui permet d'obtenir une excellente précision de position de composants électroniques et une excellente fixabilité et une excellente pelabilité de composants électroniques par rapport à la feuille adhésive, et étant capable d'empêcher la contamination de composants électroniques et d'endommager des composants électroniques.　La présente invention concerne une feuille adhésive comprenant une couche adhésive composée d'un adhésif durcissable par rayonnement d'énergie active, l'adhésif durcissable par rayonnement d'énergie active contenant un absorbeur d'ultraviolets et/ou un initiateur de photopolymérisation ; la couche adhésive a un module d'indentation initial de 4 MPa ou moins à 23 °C ; la couche adhésive a un module d'indentation de 150 MPa ou plus à 23 °C après avoir été irradié avec des rayons ultraviolets de 460 mJ/cm2 ; et la feuille adhésive a une transmittance de lumière de 50 % ou moins à une longueur d'onde de 355 nm.
PCT/JP2022/038941 2022-02-02 2022-10-19 Feuille adhésive WO2023149023A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012054432A (ja) * 2010-09-01 2012-03-15 Nitto Denko Corp 半導体ウエハ保護用粘着シート
JP2018012751A (ja) * 2016-07-19 2018-01-25 日東電工株式会社 粘着シート
JP2020053558A (ja) * 2018-09-27 2020-04-02 東レエンジニアリング株式会社 転写方法およびこれを用いた画像表示装置の製造方法ならびに転写装置
WO2021131518A1 (fr) * 2019-12-27 2021-07-01 日東電工株式会社 Feuille adhésive
WO2021220662A1 (fr) * 2020-05-01 2021-11-04 日東電工株式会社 Feuille adhésive
WO2022118499A1 (fr) * 2020-12-04 2022-06-09 日東電工株式会社 Feuille adhésive
WO2022163005A1 (fr) * 2021-01-29 2022-08-04 日東電工株式会社 Feuille adhésive de transfert de composant électronique, et procédé de traitement de composant électronique mettant en œuvre une feuille adhésive de transfert de composant électronique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012054432A (ja) * 2010-09-01 2012-03-15 Nitto Denko Corp 半導体ウエハ保護用粘着シート
JP2018012751A (ja) * 2016-07-19 2018-01-25 日東電工株式会社 粘着シート
JP2020053558A (ja) * 2018-09-27 2020-04-02 東レエンジニアリング株式会社 転写方法およびこれを用いた画像表示装置の製造方法ならびに転写装置
WO2021131518A1 (fr) * 2019-12-27 2021-07-01 日東電工株式会社 Feuille adhésive
WO2021220662A1 (fr) * 2020-05-01 2021-11-04 日東電工株式会社 Feuille adhésive
WO2022118499A1 (fr) * 2020-12-04 2022-06-09 日東電工株式会社 Feuille adhésive
WO2022163005A1 (fr) * 2021-01-29 2022-08-04 日東電工株式会社 Feuille adhésive de transfert de composant électronique, et procédé de traitement de composant électronique mettant en œuvre une feuille adhésive de transfert de composant électronique

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