WO2022054637A1 - 粘着シート貼付品の製造方法 - Google Patents

粘着シート貼付品の製造方法 Download PDF

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Publication number
WO2022054637A1
WO2022054637A1 PCT/JP2021/031869 JP2021031869W WO2022054637A1 WO 2022054637 A1 WO2022054637 A1 WO 2022054637A1 JP 2021031869 W JP2021031869 W JP 2021031869W WO 2022054637 A1 WO2022054637 A1 WO 2022054637A1
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WO
WIPO (PCT)
Prior art keywords
pressure
sensitive adhesive
adhesive layer
meth
adhesive sheet
Prior art date
Application number
PCT/JP2021/031869
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English (en)
French (fr)
Japanese (ja)
Inventor
大輔 水野
武史 仲野
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.)
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Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Priority to KR1020237007539A priority Critical patent/KR20230062826A/ko
Priority to CN202180061839.4A priority patent/CN116075567A/zh
Publication of WO2022054637A1 publication Critical patent/WO2022054637A1/ja

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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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a method for manufacturing an adhesive sheet-attached product.
  • a display panel such as an organic EL panel has a laminated structure including a pixel panel and a cover member.
  • a transparent adhesive sheet is used for bonding the elements included in the laminated structure.
  • Patent Document 1 specifically describes an adhesive sheet having a colored portion containing a carbon black pigment.
  • the deterioration of the colored portion include deformation of the colored portion due to deformation of the pressure-sensitive adhesive layer.
  • Examples of the deterioration of the discolored portion include bleeding, fading, and non-uniformity of the color of the colored portion due to the diffusion of the coloring component contained in the colored portion.
  • the present invention provides a method for manufacturing an adhesive sheet-attached product, which is capable of discoloring at least a part of the adhesive sheet after being attached to an adherend and is suitable for suppressing deterioration of the discolored portion.
  • an adhesive sheet provided with an adhesive layer that can be discolored and cured by irradiation with a first active light beam and can be cured by irradiation with a second active light beam is attached to an adherend.
  • a method for producing an adhesive sheet-attached product which comprises a bonding step, wherein the pressure-sensitive adhesive layer on the adherend is irradiated with the second active light beam to cure the pressure-sensitive adhesive layer.
  • a discoloration step of forming a discolored portion in the pressure-sensitive adhesive layer by irradiating at least a part of the pressure-sensitive adhesive layer with the first active light beam after the curing step is further included, or the said on the adherend.
  • the present invention includes a method for producing an adhesive sheet-attached product, further comprising a second curing step of curing the second portion.
  • the pressure-sensitive adhesive layer contains a polymerizable compound, a photopolymerization initiator, a compound that develops color by reaction with an acid, and a photoacid generator, according to the above [1].
  • a method for manufacturing adhesive sheet affixed products includes a method for manufacturing adhesive sheet affixed products.
  • the pressure-sensitive adhesive layer has a wavelength region in which the ratio of the absorbance Y of the photopolymerization initiator to the absorbance X of the photoacid generator is 2 or more within a wavelength range of 300 nm or more and 500 nm or less.
  • the method for producing the adhesive sheet-attached product according to the above [2] is included.
  • At least one light source selected from the group consisting of a UV-LED lamp, a black light, a high-pressure mercury lamp, and a metal halide lamp is used as the light source of the second active light in the curing step.
  • the present invention [6] is described in any one of the above [1] to [5], wherein the first active light ray in the discoloration step and / or the discoloration curing step contains light having a wavelength of less than 300 nm.
  • the first active light ray in the discoloration step and / or the discoloration curing step contains light having a wavelength of less than 300 nm.
  • the present invention [7] is selected from the group consisting of a UV-LED lamp, a black light, a high-pressure mercury lamp, and a metal halide lamp as a light source of the first active light in the discoloration step and / or the discoloration curing step.
  • an adhesive sheet provided with an adhesive layer that can be discolored by irradiation with a first active light beam is attached to an adherend in the bonding step. Therefore, after the bonding step, at least a part of the pressure-sensitive adhesive layer can be discolored by irradiating the portion to be discolored in the pressure-sensitive adhesive layer with the first active light beam (color-changing step, first discoloration curing step, Or a second discoloration curing step).
  • the pressure-sensitive adhesive layer is cured while suppressing the discoloration of the pressure-sensitive adhesive layer, and the pressure-sensitive adhesive layer has a desired pattern. Suitable for forming discolored parts of the shape.
  • the above configuration for carrying out the first discoloration curing step is suitable for efficiently discoloring and curing the entire pressure-sensitive adhesive layer.
  • a discolored portion having a desired pattern shape is formed in the pressure-sensitive adhesive layer, and discoloration other than the discolored portion in the pressure-sensitive adhesive layer is suppressed. Suitable for curing the adhesive layer while doing so.
  • these configurations suitable for forming a discolored portion in at least a part of the pressure-sensitive adhesive layer and curing the entire pressure-sensitive adhesive layer provide a softness suitable for bonding to an adherend. It is suitable for suppressing deterioration of the discolored portion in the pressure-sensitive adhesive layer (after curing) of the manufactured pressure-sensitive adhesive sheet-attached product while ensuring the layer (before curing) at the time of bonding.
  • FIG. 1A shows a step of preparing an adhesive sheet and a first member
  • FIG. 1B shows a step of attaching an adhesive sheet to a first member (bonding step)
  • FIG. 1C shows a first member and a second member.
  • FIG. 2A represents a step of curing the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet (first curing step)
  • FIG. 2B represents a step of discoloring a part of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet (color-changing step).
  • FIG. 4A shows a step of discoloring and curing a part of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet (second discoloration curing step)
  • FIG. 4B shows a step of curing the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet (second curing step).
  • the present manufacturing method includes a preparation step, a bonding step, a first curing step, and a discoloration step.
  • the adhesive sheet S and the first member M1 are prepared.
  • the adhesive sheet S includes an adhesive layer 10.
  • the adhesive sheet S has a sheet shape having a predetermined thickness and extends in a direction (plane direction) orthogonal to the thickness direction.
  • the pressure-sensitive adhesive layer 10 is a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive layer 10 has transparency (visible light transmission). Further, the pressure-sensitive adhesive layer 10 can be discolored and cured by irradiation with a first active ray described later, and can be cured by irradiation with a second active ray described later different from the first active ray.
  • the tacky composition contains a base polymer, a polymerizable compound, and a photopolymerization initiator.
  • the photopolymerization initiator receives a second active light beam to initiate a polymerization reaction of the polymerizable compound.
  • a photoacid generator and a color-developing compound are used in the adhesive composition.
  • the photoacid generator receives the first active light beam to generate an acid.
  • the color-developing compound develops color by reacting with an acid. More specifically, the components of the adhesive composition are as described below, for example.
  • the first member M1 is, for example, a display panel such as an organic EL panel.
  • the first member M1 may be another electronic device and an optical device.
  • the adhesive sheet S is bonded to the first member M1 as shown in FIG. 1B.
  • the adhesive sheet S is attached to one side of the first member M1 in the thickness direction.
  • the adhesive sheet S is arranged on one surface of the first member M1 in the thickness direction.
  • the first member M1 and the second member M2 are joined via the adhesive sheet S (joining step).
  • the second member M2 is, for example, a transparent base material.
  • the transparent base material include a transparent plastic base material and a transparent glass base material.
  • the pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S is cured.
  • the pressure-sensitive adhesive layer 10 in the laminated body W is irradiated with a second active light beam to cure the pressure-sensitive adhesive layer 10.
  • the second active ray is applied to the pressure-sensitive adhesive layer 10 from the side of the transparent second member M2.
  • the light source for irradiating the second active light include an ultraviolet LED lamp (UV-LED lamp), a black light, a high-pressure mercury lamp, and a metal halide lamp.
  • a wavelength cut filter for cutting a part of the wavelength region in the light ray emitted from the light source may be used as needed.
  • the type of the light source of the second active ray and the use of the wavelength cut filter at the time of irradiation with the second active ray are the same in the second curing step described later.
  • the wavelength range of the second active ray is different from that of the first active ray.
  • the second active ray has a wavelength that does not substantially generate an acid in the photoacid generator.
  • the second active ray preferably contains substantially no light with a wavelength less than 300 nm.
  • the lower limit of the wavelength range of the second active ray is preferably 300 nm, more preferably 320 nm, still more preferably 340 nm, still more preferably 360 nm, still more preferably 380 nm, still more preferably 390 nm, and particularly preferably 395 nm.
  • a photopolymerization initiator that initiates the polymerization reaction of the polymerizable compound by being irradiated with light having such a wavelength is used in the tacky composition.
  • the above configuration regarding the wavelength of the second active ray is the same for the second active ray used in the second curing step described later.
  • the polymerization reaction of the polymerizable compound is started by the photopolymerization initiator, and the polymerization reaction proceeds.
  • the elastic modulus of the pressure-sensitive adhesive layer 10 increases.
  • the pressure-sensitive adhesive layer 10 has a wavelength region (wavelength region R) in which the ratio of the absorbance Y of the photopolymerization initiator to the absorbance X of the photoacid generator used is 2 or more within the wavelength range of 300 nm or more and 500 nm or less. Is preferable.
  • the ratio (Y / X) in the wavelength region R is preferably 3 or more, more preferably 10 or more, and further preferably 100 or more.
  • at least a portion of the wavelength of the second active ray is within the wavelength region R. More preferably, all the wavelengths of the second active ray are in the wavelength region R.
  • Such a configuration in which the pressure-sensitive adhesive layer 10 is irradiated with a second active ray having a wavelength within the wavelength region is suitable for curing the pressure-sensitive adhesive layer 10 while suppressing discoloration in the pressure-sensitive adhesive layer 10 in the curing step. .. From the viewpoint of curing the pressure-sensitive adhesive layer 10 while suppressing discoloration in the pressure-sensitive adhesive layer 10 in the curing step, the ratio of the absorbance Y of the photopolymerization initiator to the absorbance X of the photoacid generator is larger. preferable.
  • the shear storage elastic modulus (first shear storage elastic modulus) at 25 ° C. which is shown by the dynamic viscoelasticity measurement of the pressure-sensitive adhesive layer 10 after curing under the conditions of a frequency of 1 Hz and a heating rate of 5 ° C./min, is preferable. Is 0.2 ⁇ 10 5 Pa or more, more preferably 2 ⁇ 10 5 Pa or more, and further preferably 5 ⁇ 10 5 Pa or more.
  • the shear storage elastic modulus is preferably 100 ⁇ 10 5 Pa or less, more preferably 50 ⁇ 10 5 Pa or less, and further preferably 25 ⁇ 10 5 Pa or less. Further, the shear storage elastic modulus (second shear storage elastic modulus) at 25 ° C.
  • the first shear storage elastic modulus is preferably 10 ⁇ 10 5 Pa or less, more preferably 5 ⁇ 10 5 Pa or less, and further preferably 3 ⁇ 10 5 Pa or less.
  • the ratio of the first shear storage elastic modulus to the second shear storage elastic modulus is preferably 2 or more, more preferably 5 or more, still more preferably 10 or more.
  • the ratio is preferably 100 or less, more preferably 50 or less, still more preferably 30 or less.
  • the above configuration regarding the shear storage elastic modulus is suitable for suppressing deterioration of the discolored portion formed on the pressure-sensitive adhesive layer 10 which will be described later.
  • the discolored portion 11 is formed in the pressure-sensitive adhesive layer 10 by irradiating at least a part of the pressure-sensitive adhesive layer 10 in the laminated body W with the first active light beam (in FIG. 2B, a part of the pressure-sensitive adhesive layer 10).
  • the case where the discolored portion 11 is formed in is shown as an example).
  • a mask pattern (not shown) for masking a predetermined region in the pressure-sensitive adhesive layer 10 is used from the side of the transparent second member M2.
  • the pressure-sensitive adhesive layer 10 is irradiated with the first active light beam.
  • the portion of the pressure-sensitive adhesive layer 10 that is not masked by the mask pattern is discolored.
  • Examples of the light source for irradiating the first active light include an ultraviolet LED lamp (UV-LED lamp), a black light, a high-pressure mercury lamp, and a metal halide lamp. Further, in the irradiation of the first active ray, a wavelength cut filter for cutting a part of the wavelength region of the first active ray emitted from the light source may be used, if necessary.
  • the type of the light source of the first active ray and the use of the wavelength cut filter at the time of irradiation with the first active ray are the same in the first discoloration curing step and the second discoloration curing step described later.
  • the wavelength range of the first active ray is different from that of the second active ray.
  • the wavelength range of the first active ray preferably includes at least a range smaller than the wavelength range of the second active ray (wavelength range on the short wavelength side) (the wavelength range of the first active ray is the wavelength range of the second active ray). May include a range that overlaps with). That is, the first active ray preferably includes a high energy ray that is not included in the second active ray. For example, the first active ray includes light having a wavelength of less than 300 nm.
  • the lower limit of the wavelength range of the first active ray is preferably 200 nm. , More preferably 220 nm, even more preferably 240 nm, even more preferably 250 nm, still more preferably 260 nm, still more preferably 270 nm, and particularly preferably 280 nm.
  • the first active light ray may include light having a wavelength of less than 200 nm. Light sources of such light include, for example, high pressure mercury lamps and metal halide lamps.
  • the upper limit of the wavelength range of the first active ray is preferably 400 nm. , More preferably 395 nm, more preferably 390 nm, even more preferably 385 nm, still more preferably 380 nm, still more preferably 375 nm, and particularly preferably 370 nm.
  • a photoacid generator that generates an acid by being irradiated with active energy rays having such a wavelength is preferably used in the adhesive composition.
  • the above configuration regarding the wavelength of the first active ray is the same for the first active ray used in the first color change curing step and the second color change curing step described later.
  • an acid is generated from the photoacid generator at the portion of the pressure-sensitive adhesive layer 10 irradiated with the first active light beam, and the color-developing compound is developed by the reaction with the acid.
  • the discolored portion 11 is formed on the pressure-sensitive adhesive layer 10.
  • the discolored portion 11 exhibits, for example, a dark color.
  • the adhesive sheet affixed product Z can be manufactured.
  • the metal is provided by providing the discolored portion 11 in a pattern shape corresponding to (that is, facing) the metal wiring formed on the pixel panel included in the panel. External light reflection in wiring can be suppressed.
  • the following first discoloration curing step may be carried out instead of the steps shown in FIGS. 2A and 2B.
  • the pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S is discolored and cured. Specifically, by irradiating the pressure-sensitive adhesive layer 10 in the laminated body W with the first active light beam, the entire pressure-sensitive adhesive layer 10 is cured and discolored. The first active ray is applied to the pressure-sensitive adhesive layer 10 from the side of the transparent second member M2.
  • an acid is generated from the photoacid generator in the pressure-sensitive adhesive layer 10 irradiated with the first active light beam, and the color-developing compound is developed by the reaction with the acid.
  • the pressure-sensitive adhesive layer 10 is discolored (the discolored portion 11 is formed on the entire pressure-sensitive adhesive layer 10).
  • the polymerization reaction of the polymerizable compound is started by the photopolymerization initiator, and the polymerization reaction proceeds.
  • the elastic modulus of the pressure-sensitive adhesive layer 10 increases.
  • the adhesive sheet affixed product Z can also be manufactured by the above method.
  • a part of the pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S is discolored and cured. Specifically, by irradiating a part (first part) of the pressure-sensitive adhesive layer 10 in the laminated body W with the first active light beam, a discolored portion 11 is formed in a part of the pressure-sensitive adhesive layer 10 and the part is cured. Let me. In this step, the pressure-sensitive adhesive layer 10 is irradiated with the first active light beam from the side of the transparent second member M2 via a mask pattern (not shown) for masking a predetermined region in the pressure-sensitive adhesive layer 10. ..
  • an acid is generated from the photoacid generator at the portion of the pressure-sensitive adhesive layer 10 irradiated with the first active light beam, and the color-developing compound is developed by the reaction with the acid.
  • the discolored portion 11 is formed on the pressure-sensitive adhesive layer 10.
  • the polymerization reaction of the polymerizable compound is started by the photopolymerization initiator at the portion of the pressure-sensitive adhesive layer 10 irradiated with the first active light beam, and the polymerization reaction proceeds. As a result, the elastic modulus of the portion increases.
  • the pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S is cured. Specifically, at least a part of the pressure-sensitive adhesive layer 10 in the laminated body W is irradiated with a second active ray to cure the pressure-sensitive adhesive layer 10.
  • the region of the pressure-sensitive adhesive layer 10 irradiated with the second active light beam includes any part (second part) other than the discolored portion 11 of the pressure-sensitive adhesive layer 10, and is preferably the entire pressure-sensitive adhesive layer 10.
  • the second active ray is applied to the pressure-sensitive adhesive layer 10 from the side of the transparent second member M2.
  • the pressure-sensitive adhesive sheet S provided with the pressure-sensitive adhesive layer 10 that can be discolored afterwards by irradiation with the first active light beam is bonded to the first member M1 as an adherend (bonding step). Further, the first member M1 and the second member M2 as an adherend are joined via the pressure-sensitive adhesive sheet S (bonding step). According to such a manufacturing method, the presence or absence of foreign matter and air bubbles between the pressure-sensitive adhesive sheet S and the adherend after the bonding step and before the formation of the discolored portion 11 of the pressure-sensitive adhesive layer 10. Can be inspected.
  • the pressure-sensitive adhesive layer 10 is cured while suppressing the discoloration of the pressure-sensitive adhesive layer 10. It is suitable for forming a discolored portion 11 having a desired pattern shape on the pressure-sensitive adhesive layer 10.
  • the above configuration (shown in FIG. 3) for carrying out the first discoloration curing step is suitable for efficiently discoloring and curing the entire pressure-sensitive adhesive layer 10. In the above configuration (shown in FIGS.
  • the discolored portion 11 having a desired pattern shape is formed on the pressure-sensitive adhesive layer 10 and the discolored portion 11 has a desired pattern shape. It is suitable for curing the pressure-sensitive adhesive layer 10 while suppressing discoloration of the pressure-sensitive adhesive layer 10 other than the discolored portion 11. Then, after the bonding step, these configurations suitable for forming the discolored portion 11 on the pressure-sensitive adhesive layer 10 and curing the entire pressure-sensitive adhesive layer 10 provide the pressure-sensitive adhesive layer with a softness suitable for bonding to an adherend.
  • Examples of the deterioration of the discolored portion 11 include deformation of the discolored portion 11 due to deformation of the pressure-sensitive adhesive layer 10.
  • Examples of the deterioration of the discolored portion 11 include bleeding, fading, and non-uniformity of the color tint of the discolored portion 11 due to the diffusion of the color-developing compound contained in the discolored portion 11.
  • the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer 10 of the pressure-sensitive adhesive sheet S contains, for example, a base polymer, a polymerizable compound, a photopolymerization initiator, a photoacid generator, and a color-developing compound.
  • the base polymer is an adhesive component for developing adhesiveness in the adhesive layer 10.
  • the base polymer exhibits rubber elasticity at room temperature.
  • examples of the base polymer include acrylic polymers, rubber polymers, polyester polymers, urethane polymers, polyether polymers, silicone polymers, polyamide polymers, and fluoropolymers. From the viewpoint of ensuring good transparency and tackiness in the pressure-sensitive adhesive layer 10, an acrylic polymer is preferably used as the base polymer.
  • the content ratio of the base polymer in the pressure-sensitive adhesive layer 10 is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass, from the viewpoint of appropriately expressing the function of the base polymer in the pressure-sensitive adhesive layer 10. % Or more.
  • the acrylic polymer is, for example, a polymer obtained by polymerizing a monomer component containing (meth) acrylic acid ester in a proportion of 50% by mass or more.
  • (Meta) acrylic acid means acrylic acid and / or methacrylic acid.
  • Examples of the (meth) acrylic acid ester include (meth) acrylic acid alkyl ester and (meth) acrylic acid alkoxyalkyl ester.
  • Examples of the (meth) acrylic acid alkyl ester include linear or branched (meth) acrylic acid alkyl esters having an alkyl group having 1 to 20 carbon atoms.
  • Examples of such (meth) acrylic acid alkyl esters include methyl (meth) acrylic acid, ethyl (meth) acrylic acid, propyl (meth) acrylic acid, n-butyl (meth) acrylic acid, and (meth) acrylic acid.
  • an acrylic acid alkyl ester having an alkyl group having 1 to 12 carbon atoms is preferably used, and more preferably, it has methyl acrylate and an alkyl group having 2 to 12 carbon atoms.
  • Acrylic acid alkyl ester is used in combination, and more preferably, methyl acrylate and 2-ethylhexyl acrylate are used in combination.
  • Examples of the (meth) acrylic acid alkoxyalkyl ester include a (meth) acrylic acid alkoxyalkyl ester having an alkoxy group having 1 to 4 carbon atoms and an alkylene group having 1 to 4 carbon atoms.
  • Examples of such (meth) acrylic acid alkoxyalkyl esters include (meth) acrylic acid 2-methoxymethyl, (meth) acrylic acid 2-methoxyethyl, (meth) acrylic acid 2-ethoxymethyl, and (meth) acrylic.
  • Examples thereof include 2-ethoxyethyl acid, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • the (meth) acrylic acid alkoxyalkyl ester preferably, (meth) acrylic acid 2-ethoxymethyl is used, and more preferably acrylic acid 2-ethoxymethyl is used.
  • the (meth) acrylic acid ester may be used alone or in combination of two or more.
  • the ratio of the (meth) acrylic acid ester in the monomer component is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably 60% by mass or more, from the viewpoint of appropriately expressing basic properties such as adhesiveness in the pressure-sensitive adhesive layer 10. It is 70% by mass or more. The same ratio is, for example, 99% by mass or less.
  • the monomer component may contain a copolymerizable monomer copolymerizable with the (meth) acrylic acid ester.
  • the copolymerizable monomer include a monomer having a polar group.
  • the polar group-containing monomer include a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and a carboxy group-containing monomer.
  • the polar group-containing monomer is useful for modifying the acrylic polymer, such as introducing a cross-linking point into the acrylic polymer and ensuring the cohesive force of the acrylic polymer.
  • the copolymerizable monomer preferably contains at least one selected from the group consisting of a hydroxyl group-containing monomer, a monomer having a nitrogen atom-containing ring, and a carboxy group-containing monomer. More preferably, the copolymerizable monomer comprises a hydroxyl group-containing monomer and / or a monomer having a nitrogen atom-containing ring.
  • Examples of the hydroxyl group-containing monomer include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and (meth). ) 4-Hydroxybutyl acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, and ( Examples include 4-hydroxymethylcyclohexyl) methyl (meth) acrylate.
  • 2-hydroxyethyl (meth) acrylate is preferably used, and 2-hydroxyethyl acrylate is more preferably used.
  • the ratio of the hydroxyl group-containing monomer in the monomer component is preferably 1% by mass or more, more preferably 3% by mass or more, from the viewpoint of introducing a crosslinked structure into the acrylic polymer and ensuring the cohesive force in the pressure-sensitive adhesive layer 10. More preferably, it is 5% by mass or more. The same ratio is preferable from the viewpoint of adjusting the viscosity of the polymerization reaction solution during the polymerization of the acrylic polymer and adjusting the polarity of the acrylic polymer (related to the compatibility between various additive components in the pressure-sensitive adhesive layer 10 and the acrylic polymer). Is 30% by mass or less, more preferably 20% by mass or less.
  • Examples of the monomer having a nitrogen atom-containing ring include N-vinyl-2-pyrrolidone, N-methylvinylpyrrolidone, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, and N-vinylpyrazine.
  • N-vinyl-2-caprolactam N-vinyl-1,3-oxadin-2-one, N-vinyl-3,5-morpholindione
  • N-vinylpyrazole N-vinylisoxazole
  • N -Vinylthiazole N-vinylisothiazole
  • monomer having a nitrogen atom-containing ring N-vinyl-2-pyrrolidone is preferably used.
  • the ratio of the monomer having a nitrogen atom-containing ring in the monomer component is preferably 1% by mass from the viewpoint of ensuring the cohesive force in the pressure-sensitive adhesive layer 10 and the adhesion to the adherend in the pressure-sensitive adhesive layer 10. As mentioned above, it is more preferably 3% by mass or more, still more preferably 5% by mass or more. The same ratio is preferably 30 mass from the viewpoint of adjusting the glass transition temperature of the acrylic polymer and adjusting the polarity of the acrylic polymer (related to the compatibility between various additive components in the pressure-sensitive adhesive layer 10 and the acrylic polymer). % Or less, more preferably 20% by mass or less.
  • carboxy group-containing monomer examples include acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid.
  • the ratio of the carboxy group-containing monomer in the monomer component is determined from the viewpoint of introducing a crosslinked structure into the acrylic polymer, ensuring the cohesive force in the pressure-sensitive adhesive layer 10, and ensuring the adhesion to the adherend in the pressure-sensitive adhesive layer 10. It is preferably 1% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more. The same ratio is preferably 30% by mass or less, more preferably 20% by mass or less, from the viewpoint of adjusting the glass transition temperature of the acrylic polymer and avoiding the risk of corrosion of the adherend by acid.
  • the monomer component may contain other copolymerizable monomers.
  • other copolymerizable monomers include acid anhydride monomers, sulfonic acid group-containing monomers, phosphate group-containing monomers, epoxy group-containing monomers, cyano group-containing monomers, amide group-containing monomers, monomers having a succinimide skeleton, and maleimides. , Itaconimides, alkoxy group-containing monomers, vinyl esters, vinyl ethers, and aromatic vinyl compounds.
  • Examples of the acid anhydride monomer include maleic anhydride and itaconic anhydride.
  • sulfonic acid group-containing monomer examples include styrene sulfonic acid, allyl sulfonic acid, sodium vinyl sulfonic acid, 2- (meth) acrylamide-2-methylpropane sulfonic acid, (meth) acrylamide propane sulfonic acid, and sulfopropyl (meth).
  • Examples of the phosphate group-containing monomer include 2-hydroxyethylacryloyl phosphate.
  • epoxy group-containing monomer examples include epoxy group-containing acrylates such as glycidyl (meth) acrylate and -2-ethyl glycidyl ether (meth) acrylate, allyl glycidyl ether, and glycidyl ether (meth) acrylate.
  • Examples of the cyano group-containing monomer include acrylonitrile and methacrylonitrile.
  • Examples of the amide group-containing monomer include N-vinylcarboxylic acid amides such as (meth) acrylamide, N, N-dialkyl (meth) acrylamide, N-alkyl (meth) acrylamide, and N-vinylacetamide, and N-hydroxyalkyl.
  • Examples include (meth) acrylamide, N-alkoxyalkyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, and N- (meth) acryloylmorpholin.
  • N, N-dialkyl (meth) acrylamide examples include N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N-dipropyl (meth) acrylamide, and N, N-diisopropyl ( Examples include meth) acrylamide, N, N-di (n-butyl) (meth) acrylamide, and N, N-di (t-butyl) (meth) acrylamide.
  • N-alkyl (meth) acrylamide examples include N-ethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butyl (meth) acrylamide, and Nn-butyl (meth) acrylamide.
  • N-hydroxyalkyl (meth) acrylamide examples include N- (2-hydroxyethyl) (meth) acrylamide, N- (2-hydroxypropyl) (meth) acrylamide, and N- (1-hydroxypropyl) (meth).
  • N- (3-hydroxypropyl) (meth) acrylamide N- (2-hydroxybutyl) (meth) acrylamide, N- (3-hydroxybutyl) (meth) acrylamide, and N- (4-hydroxybutyl) Examples include (meth) acrylamide.
  • N-alkoxyalkyl (meth) acrylamide include N-methoxymethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, and N-butoxymethyl (meth) acrylamide.
  • Examples of the monomer having a succinimide skeleton include N- (meth) acryloyloxymethylene succinimide, N- (meth) acryloyl-6-oxyhexamethylene succinimide, and N- (meth) acryloyl-8-oxyhexamethylene succinimide. Be done.
  • maleimides examples include N-cyclohexylmaleimide, N-isopropylmaleimide, N-laurylmaleimide, and N-phenylmaleimide.
  • Examples of the itaconimides include N-methylitaconimide, N-ethylitaconimide, N-butylitaconimide, N-octylitaconimide, N-2-ethylhexylitaconimide, N-cyclohexylitaconimide, and N-laurylitaconimide can be mentioned.
  • alkoxy group-containing monomer examples include (meth) acrylate alkoxyalkyls and (meth) acrylate alkoxyalkylene glycols.
  • examples of the (meth) acrylate alkoxyalkyls include (meth) acrylate 2-methoxyethyl, (meth) acrylate 3-methoxypropyl, (meth) acrylate 2-ethoxyethyl, and (meth) acrylate propoxyethyl. , Butoxyethyl (meth) acrylate, and ethoxypropyl (meth) acrylate.
  • examples of the (meth) acrylate alkoxyalkylene glycols include (meth) methoxyethylene glycol (meth) acrylate and methoxypolypropylene glycol (meth) acrylate.
  • vinyl esters examples include vinyl acetate and vinyl propionate.
  • vinyl ethers examples include methyl vinyl ether and ethyl vinyl ether.
  • aromatic vinyl compound examples include styrene, ⁇ -methylstyrene, and vinyltoluene.
  • olefins examples include ethylene, butadiene, isoprene, and isobutylene.
  • the copolymerizable monomer may be used alone or in combination of two or more.
  • Acrylic polymer can be formed by polymerizing the above-mentioned monomer components.
  • the polymerization method include solution polymerization, bulk polymerization, and emulsion polymerization, and solution polymerization is preferable.
  • solution polymerization for example, a monomer component and a polymerization initiator are mixed with a solvent to prepare a reaction solution, and then the reaction solution is heated. Then, an acrylic polymer solution containing an acrylic polymer can be obtained by undergoing a polymerization reaction of the monomer components in the reaction solution.
  • the polymerization initiator for example, a thermal polymerization initiator is used.
  • the amount of the polymerization initiator used is, for example, 0.05 parts by mass or more and, for example, 1 part by mass or less with respect to 100 parts by mass of the monomer component.
  • thermal polymerization initiator examples include an azo polymerization initiator and a peroxide polymerization initiator.
  • examples of the azo polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-methylbutyronitrile, and 2,2'-azobis (2-methylpropionic acid) dimethyl.
  • 4,4'-Azobis-4-cyanovaleric acid 4,4'-Azobis-4-cyanovaleric acid, azobisisobutyvaleronitrile, 2,2'-azobis (2-amidinopropane) dihydrochloride, 2,2'-azobis [2- (5-methyl-2-) Imidazoline-2-yl) propane] dihydrochloride, 2,2'-azobis (2-methylpropionamidine) disulfate, and 2,2'-azobis (N, N'-dimethyleneisobutyramidin) dihydrochloride Can be mentioned.
  • the peroxide polymerization initiator include dibenzoyl peroxide, t-butyl permaleate, and lauroyl peroxide.
  • the weight average molecular weight of the acrylic polymer is preferably 100,000 or more, more preferably 300,000 or more, still more preferably 500,000 or more, from the viewpoint of ensuring the cohesive force in the pressure-sensitive adhesive layer 10.
  • the weight average molecular weight is preferably 5,000,000 or less, more preferably 3,000,000 or less, still more preferably 2000000 or less.
  • the weight average molecular weight of the acrylic polymer is measured by gel permeation chromatography (GPC) and calculated in terms of polystyrene.
  • the glass transition temperature (Tg) of the base polymer is preferably 0 ° C. or lower, more preferably ⁇ 10 ° C. or lower, still more preferably ⁇ 20 ° C. or lower.
  • the glass transition temperature is, for example, ⁇ 80 ° C. or higher.
  • the glass transition temperature (Tg) of the polymer the glass transition temperature (theoretical value) obtained based on the Fox formula below can be used.
  • the Fox formula is a relational expression between the glass transition temperature Tg of the polymer and the glass transition temperature Tgi of the homopolymer of the monomer constituting the polymer.
  • Tg represents the glass transition temperature (° C.) of the polymer
  • Wi represents the weight fraction of the monomer i constituting the polymer
  • Tgi represents the glass transition of the homopolymer formed from the monomer i. Indicates the temperature (° C).
  • Literature values can be used for the glass transition temperature of homopolymers, for example, "Polymer Handbook” (4th edition, John Wiley & Sons, Inc., 1999) and “New Polymer Bunko 7 Introduction to Synthetic Resins for Paints”. (Kyozo Kitaoka, Polymer Publications, 1995) lists the glass transition temperatures of various homopolymers. On the other hand, the glass transition temperature of the homopolymer of the monomer can also be obtained by the method specifically described in JP-A-2007-51271.
  • the adhesive composition may contain a cross-linking agent from the viewpoint of introducing a cross-linked structure into the base polymer.
  • a cross-linking agent examples include an isocyanate cross-linking agent, an epoxy cross-linking agent, an oxazoline cross-linking agent, an aziridine cross-linking agent, a carbodiimide cross-linking agent, and a metal chelate cross-linking agent.
  • the cross-linking agent may be used alone or in combination of two or more.
  • Examples of the isocyanate cross-linking agent include tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylylene diisocyanate, naphthalin diisocyanate, and triphenylmethane tri. Examples thereof include isocyanates and polymethylene polyphenyl isocyanates. Further, examples of the isocyanate cross-linking agent include derivatives of these isocyanates.
  • isocyanate derivative examples include isocyanurate-modified products and polyol-modified products.
  • isocyanate cross-linking agents include coronate L (trimethylolpropane adduct of tolylene diisocyanate, manufactured by Tosoh), coronate HL (trimethylolpropane adduct of hexamethylene diisocyanate, manufactured by Tosoh), and coronate HX (hexa).
  • Examples thereof include isocyanurate form of methylene diisocyanate (manufactured by Toso) and Takenate D110N (trimethylolpropane adduct form of xylylene diisocyanate, manufactured by Mitsui Kagaku).
  • epoxy cross-linking agent examples include bisphenol A, epichlorohydrin type epoxy resin, ethylene glycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol glycidyl ether, and trimethylolpropane triglycidyl ether.
  • the blending amount of the cross-linking agent is, for example, 0.01 part by mass or more, preferably 0.05 part by mass or more, based on 100 parts by mass of the base polymer. It is preferably 0.07 parts by mass or more.
  • the blending amount of the cross-linking agent with respect to 100 parts by mass of the base polymer is, for example, 10 parts by mass or less, preferably 5 parts by mass or less, and more preferably 3 parts by mass. It is as follows.
  • a cross-linking catalyst may be used to effectively promote the cross-linking reaction.
  • the cross-linking catalyst include dibutyltin dilaurate, tetra-n-butyl titanate, tetraisopropyl titanate, ferric nasem, and butyltin oxide, and dibutyltin dilaurate is preferably used.
  • the amount of the cross-linking catalyst used is, for example, 0.0001 parts by mass or more and 1 part by mass or less with respect to 100 parts by mass of the base polymer.
  • a cross-linking inhibitor that can be removed ex post facto from the sticky composition may be added to the sticky composition.
  • dibutyltin dilaurate is used as the cross-linking catalyst
  • acetylacetone is preferably used as the cross-linking inhibitor. In this case, in the adhesive composition, acetylacetone coordinates with dibutyltin dilaurate, and the cross-linking reaction of the cross-linking agent with the veil polymer is suppressed.
  • acetylacetone can be volatilized and removed from the coating film by heating at a desired timing. This makes it possible to proceed with the cross-linking reaction of the cross-linking agent.
  • the blending amount of the cross-linking inhibitor is, for example, 100 parts by mass or more, preferably 1000 parts by mass or more with respect to 100 parts by mass of the cross-linking catalyst. Further, the blending amount is, for example, 5000 parts by mass or less.
  • the polymerizable compound is a compound having a polymerizable functional group.
  • the polymerizable functional group has an ethylenically unsaturated double bond.
  • Polymerizable functional groups include, for example, (meth) acryloyl groups, vinyl groups, and propenyl groups.
  • Examples of the polymerizable compound include a monomer having one polymerizable functional group (monofunctional monomer) and a monomer having a plurality of polymerizable functional groups (polyfunctional monomer).
  • a compound having a (meth) acryloyl group as a polymerizable functional group is used from the viewpoint of reactivity.
  • the (meth) acryloyl group means an acryloyl group and / or a methacryloyl group.
  • the polymerizable compound may be used alone or in combination of two or more.
  • Examples of the monofunctional monomer include ethyl (meth) acrylate, n-butyl (meth) acrylate, ter-butyl (meth) acrylate, isobutyl methacrylate, 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, and butoxydiethylene glycol (.
  • Meta acrylate, methoxypolyethylene glycol (meth) acrylate, glycidyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) Meta) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxy (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) Meta) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol
  • polyfunctional monomer examples include a bifunctional monomer, a trifunctional monomer, and a tetrafunctional or higher polyfunctional monomer.
  • bifunctional monomer examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and tetraethierlenglucol dimethacrylate, 1,6-hexanediol di (meth).
  • trifunctional monomer examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, and tris (acryloyloxyethyl) isocyanurate.
  • tetrafunctional or higher polyfunctional monomer examples include ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, alkyl-modified dipentaerythritol pentaacrylate, and dipenta.
  • examples thereof include erythritol hexa (meth) acrylate, and isocyanuric acid EO-modified di and triacrylate.
  • the polymerizable compound is preferably a polyfunctional monomer, more preferably a tetrafunctional or higher-functional monomer, still more preferably a dipentaerythritol hexa (meth) acrylate, and particularly preferably. Dipentaerythritol hexaacrylate is used.
  • the amount of the polymerizable compound is preferably 5 parts by mass or more, more preferably 7 parts by mass or more with respect to 100 parts by mass of the base polymer. It is more preferably 9 parts by mass or more, and particularly preferably 10 parts by mass or more. From the viewpoint of ensuring sufficient adhesive strength in the cured pressure-sensitive adhesive layer 10, the blending amount of the polymerizable compound with respect to 100 parts by mass of the base polymer is preferably 50 parts by mass or less, more preferably 45 parts by mass or less, still more preferably. Is 43 parts by mass or less.
  • the photopolymerization initiator initiates the polymerization reaction of the polymerizable compound.
  • the photopolymerization initiator include a benzoin ether photopolymerization initiator, an acetophenone photopolymerization initiator, an ⁇ -ketol photopolymerization initiator, an aromatic sulfonyl chloride photopolymerization initiator, a photoactive oxime photopolymerization initiator, and a benzoin photopolymerization initiator.
  • Examples thereof include an initiator, a benzyl photopolymerization initiator, a benzophenone photopolymerization initiator, a ketal photopolymerization initiator, a thioxanthone photopolymerization initiator, and an acylphosphine oxide photopolymerization initiator.
  • Examples of the photoacid generator include onium compounds that generate acid by irradiation with ultraviolet rays (first active light beam).
  • Onium compounds are provided, for example, in the form of onium salts of onium cations and anions.
  • Examples of onium cations include iodonium and sulfonium.
  • Examples of anions include Cl- , Br- , I- , ZnCl 3- , HSO 3- , BF 4- , PF 6- , AsF 6- , SbF 6- , CH 3 SO 3- , CF 3 SO 3- . , C 4 F 9 HSO 3- , (C 6 F 5 ) 4 B- , and (C 4 H 9 ) 4 B-.
  • the photoacid generator may be used alone or in combination of two or more.
  • the tacky composition preferably contains an onium salt (onium compound) composed of sulfonium and C 4 F 9 HSO 3- as a photoacid generator.
  • the blending amount of the photoacid generator with respect to 100 parts by mass of the base polymer is preferably 1 part by mass or more, more preferably 2 parts by mass or more, further preferably 5 parts by mass or more, and particularly preferably 7 parts by mass or more.
  • the blending amount is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and further preferably 12 parts by mass or less.
  • the blending amount of the photoacid generator with respect to 100 parts by mass of the color-developing compound is, for example, 100 parts by mass or more, preferably 200 parts by mass or more, more preferably 300 parts by mass or more, and further preferably 330 parts by mass or more.
  • the blending amount is preferably 1000 parts by mass or less, more preferably 700 parts by mass or less, and further preferably 500 parts by mass or less.
  • color-developing compound examples include leuco dye, triarylmethane dye, diphenylmethane dye, fluorane dye, spiropyran dye, and rhodamine dye.
  • the color-developing compound may be used alone or in combination of two or more.
  • leuco dyes examples include 2'-anilino-6'-(N-ethyl-N-isopentylamino) -3'-methylspiro [phthalide-3,9'-[9H] xanthene], 3-dibutylamino-.
  • Examples of the triarylmethane dye include p, p', p "-tris-dimethylaminotriphenylmethane.
  • Examples of the diphenylmethane dye include 4,4-bis-dimethylaminophenylbenzhydrylbenzyl ether.
  • Examples of the fluorane dye include 3-diethylamino-6-methyl-7-chlorofluorane.
  • Examples of the spiropyran dye include 3-methylspirodinaphthopyrane.
  • Examples of the rhodamine dye include 3-methylspirodinaphthopyrane.
  • Rhodamine-B-anilinolactum can be mentioned.
  • the color-developing compound is preferably a leuco dye, more preferably 2'-anilino-6'-(N-ethyl-N-isopentylamino)-.
  • 3'-Methylspiro [phthalide-3,9'-[9H] xanthene] is used.
  • the blending amount of the color-developing compound with respect to 100 parts by mass of the base polymer is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more.
  • the blending amount is preferably 10 parts by mass or less, more preferably 7 parts by mass or less.
  • a photoacid generator having a polymerizable functional group and / or a color-developing compound having a polymerizable functional group may be used.
  • a photoacid generator having a polymerizable functional group and / or a color-developing compound having a polymerizable functional group may be used.
  • the monomer component forming the base polymer may contain a color-developing compound (second color-developing compound) having a polymerizable functional group. That is, the color-developing compound may be incorporated in the base polymer. The movement of such a color-developing compound in the pressure-sensitive adhesive layer 10 is suppressed.
  • a color-developing compound second color-developing compound having a polymerizable functional group. That is, the color-developing compound may be incorporated in the base polymer. The movement of such a color-developing compound in the pressure-sensitive adhesive layer 10 is suppressed.
  • the polymerizable compound blended with the base polymer in the adhesive composition may contain a color-developing compound having a polymerizable functional group (second color-developing compound). That is, the color-developing compound may be contained in the adhesive composition in a state in which it can be copolymerized as a polymerizable compound.
  • second color-developing compound Such a color-developing compound is incorporated into the polymer network after being cured by irradiation with a second active ray (that is, after the polymerization reaction of the polymerizable compound has proceeded), and the movement within the pressure-sensitive adhesive layer 10 is suppressed.
  • the monomer component forming the base polymer may contain a color-developing compound having a polymerizable functional group, and the polymerizable compound may contain a color-developing compound having a polymerizable functional group.
  • These configurations in which the movement of the color-developing compound (second color-developing compound) is suppressed are suitable for suppressing the diffusion of the color-developing compound in the discolored portion 11 formed on the pressure-sensitive adhesive layer 10, and therefore. It is suitable for suppressing deterioration (bleeding, fading, non-uniformity of color, etc.) of the discolored portion 11.
  • Examples of the second color-developing compound (having a polymerizable functional group) include a leuco dye having a polymerizable functional group, a triarylmethane dye having a polymerizable functional group, a diphenylmethane dye having a polymerizable functional group, and polymerizable. Examples thereof include a fluorane dye having a functional group, a spiropyran dye having a polymerizable functional group, and a rhodamine dye having a polymerizable functional group.
  • the polymerizable functional group has an ethylenically unsaturated double bond.
  • Examples of the polymerizable functional group include a vinyl group, a propenyl group, and a (meth) acryloyl group.
  • the (meth) acryloyl group means an acryloyl group and / or a methacryloyl group.
  • Examples of the vinyl group include a styrene group.
  • the second color-developing compound may be used alone or in combination of two or more.
  • a leuco dye having a polymerizable functional group is preferably used, a leuco dye having a (meth) acryloyl group is more preferably used, and a leuco dye having an acryloyl group is more preferable. Used.
  • Examples of the leuco dye having a polymerizable functional group include the acryloyl group-containing leuco dye described in International Publication No. 2013/048993.
  • the second color-developing compound may be used together with the first color-developing compound, or may be used in place of the first color-developing compound.
  • the total amount of the first color-developing compound and the second color-developing compound used is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and more preferably 1 part by mass with respect to 100 parts by mass of the base polymer. Is 10 parts by mass or less, more preferably 7 parts by mass or less.
  • the monomer component forming the base polymer may contain a photoacid generator having a polymerizable functional group (second photoacid generator). That is, the photoacid generator may be incorporated in the base polymer.
  • the movement of such a photoacid generator in the pressure-sensitive adhesive layer 10 is suppressed.
  • the movement of the color-developing compound in the pressure-sensitive adhesive layer 10 that develops color by the interaction with the acid generated by such a photoacid generator is also suppressed.
  • the polymerizable compound to be blended with the base polymer in the adhesive composition may contain a photoacid generator having a polymerizable functional group (second photoacid generator). That is, the photoacid generator may be contained in the tacky composition in a state in which it can be copolymerized as a polymerizable compound.
  • a photoacid generator is incorporated into the polymer network after being cured by irradiation with a second active ray (that is, after the polymerization reaction of the polymerizable compound has proceeded), and movement within the pressure-sensitive adhesive layer 10 is suppressed. Will be done. The movement of the color-developing compound in the pressure-sensitive adhesive layer 10 that develops color by the interaction with the acid generated by such a photoacid generator is also suppressed.
  • the monomer component forming the base polymer may contain a photoacid generator having a polymerizable functional group, and the polymerizable compound may contain a photoacid generator having a polymerizable functional group.
  • Examples of the second photoacid generator include an onium compound that generates an acid by irradiation with ultraviolet rays and has a polymerizable functional group.
  • Examples of the polymerizable functional group include the above-mentioned polymerizable functional groups with respect to the second color-developing compound.
  • Onium compounds are provided, for example, in the form of onium salts of onium cations and anions.
  • Examples of onium cations include iodonium and sulfonium.
  • Examples of the anion include a sulfonic acid derivative anion, a sulfonimide derivative anion, and a sulfonmethide derivative anion.
  • the anion has a polymerizable functional group.
  • an onium salt of a sulfonic acid derivative anion having a polymerizable functional group and sulfonium is preferably used, and more preferably, a sulfonic acid derivative anion having a (meth) acryloyl group and sulfonium.
  • the onium salt of and is used, and more preferably, triphenylsulfonium / 4-vinylbenzenesulfonate is used.
  • the method for synthesizing this photoacid generator is described in, for example, "Novel Polymeric anionic photoacid generators (PAGs) and corresponding polymers for 193 nm lithography" (Journal of Materials Chemistry, 2006, Vol. 16, p3701-3707). ..
  • the second photoacid generator may be used alone or in combination of two or more.
  • the second photoacid generator may be used together with the first photoacid generator or may be used in place of the first photoacid generator.
  • the amount of the first photoacid generator and the second photoacid generator to be used with respect to 100 parts by mass of the color-developing compound is preferably 100 parts by mass or more, more preferably 200 parts by mass or more, still more preferably 300 parts by mass or more. Is.
  • the amount used is preferably 1000 parts by mass or less, more preferably 700 parts by mass or less, and further preferably 500 parts by mass or less.
  • the adhesive composition may contain other components as needed.
  • Other components include, for example, silane coupling agents, tackifiers, plasticizers, softeners, antioxidants, surfactants, and antistatic agents.
  • the pressure-sensitive adhesive sheet S can be produced, for example, by applying the above-mentioned adhesive composition on a release film (first release film) to form a coating film, and then drying the coating film (in FIG. 5).
  • the adhesive sheet S is arranged on the release film L indicated by the virtual line).
  • Examples of the release film include a flexible plastic film.
  • Examples of the plastic film include polyethylene terephthalate film, polyethylene film, polypropylene film, and polyester film.
  • the thickness of the release film is, for example, 3 ⁇ m or more, and is, for example, 200 ⁇ m or less.
  • the surface of the release film is preferably mold-released.
  • Examples of the method of applying the adhesive composition include roll coat, kiss roll coat, gravure coat, reverse coat, roll brush, spray coat, dip roll coat, bar coat, knife coat, air knife coat, curtain coat, and lip coat. , And die coat.
  • the drying temperature of the coating film is, for example, 50 ° C to 200 ° C.
  • the drying time is, for example, 5 seconds to 20 minutes.
  • the cross-linking reaction proceeds at the same time as the above-mentioned drying or by aging thereafter.
  • the aging conditions are appropriately set depending on the type of the cross-linking agent.
  • the aging temperature is, for example, 20 ° C to 160 ° C.
  • the aging time is, for example, 1 minute to 7 days.
  • a release film (second release film) may be further laminated on the pressure-sensitive adhesive layer 10 on the first release film.
  • the second release film is a flexible plastic film that has been subjected to a surface release treatment, and the same film as described above can be used for the first release film.
  • the pressure-sensitive adhesive sheet S whose adhesive surface is covered and protected by the release film can be manufactured.
  • Each release film is peeled off from the pressure-sensitive adhesive sheet S as needed when using the pressure-sensitive adhesive sheet S.
  • the thickness of the pressure-sensitive adhesive layer 10 is preferably 10 ⁇ m or more, more preferably 15 ⁇ m or more, from the viewpoint of ensuring sufficient adhesiveness to the adherend. From the viewpoint of handleability of the pressure-sensitive adhesive sheet S, the thickness of the pressure-sensitive adhesive layer 10 is preferably 300 ⁇ m or less, more preferably 200 ⁇ m or less, still more preferably 100 ⁇ m or less, and particularly preferably 50 ⁇ m or less.
  • the haze of the pressure-sensitive adhesive layer 10 is preferably 3% or less, more preferably 2% or less, and more preferably 1% or less. Such a configuration is suitable for inspecting the presence or absence of foreign matter and air bubbles between the pressure-sensitive adhesive sheet S and the adherend after the pressure-sensitive adhesive sheet S is attached to the adherend.
  • the haze of the pressure-sensitive adhesive layer 10 can be measured using a haze meter in accordance with JIS K7136 (2000). Examples of the haze meter include "NDH2000" manufactured by Nippon Denshoku Kogyo Co., Ltd. and "HM-150 type” manufactured by Murakami Color Technology Research Institute.
  • the average transmittance of the pressure-sensitive adhesive layer 10 at a wavelength of 400 to 700 nm is preferably 80% or more, more preferably 85% or more, still more preferable. Is 90% or more.
  • Such a configuration is suitable for inspecting the presence or absence of foreign matter and air bubbles between the pressure-sensitive adhesive sheet S and the adherend after the pressure-sensitive adhesive sheet S is attached to the adherend.
  • the adhesive force exhibited by the adhesive sheet S on the stainless steel plate in a peeling test under the peeling conditions of 23 ° C., a peeling angle of 180 ° and a peeling speed of 300 mm / min after being bonded to the glass plate is, for example, 1 N / 25 mm or more. It is, for example, 50 N / 25 mm or less.
  • the pressure-sensitive adhesive sheet S may be a single-sided pressure-sensitive adhesive sheet with a base material, which comprises a base material 20 in addition to the pressure-sensitive adhesive layer 10.
  • the pressure-sensitive adhesive sheet S specifically includes a pressure-sensitive adhesive layer 10 and a base material 20 arranged on one side in the thickness direction thereof.
  • the substrate 20 contacts one side of the pressure-sensitive adhesive layer 10 in the thickness direction.
  • the base material 20 is an element that functions as a transparent support.
  • the base material 20 is, for example, a flexible plastic film.
  • the constituent material of the plastic film include polyolefin, polyester, polyamide, polyimide, polyvinyl chloride, polyvinylidene chloride, cellulose, polystyrene, and polycarbonate.
  • the polyolefin include polyethylene, polypropylene, poly-1-butene, poly-4-methyl-1-pentene, ethylene / propylene copolymer, ethylene / 1-butene copolymer, ethylene / vinyl acetate copolymer, and the like.
  • the plastic material of the base material 20 is preferably polyester, more preferably polyethylene terephthalate.
  • the base material 20 has transparency.
  • the haze of the base material 20 is preferably 3% or less, more preferably 2% or less, still more preferably 1% or less.
  • the haze of the base material 20 can be measured using a haze meter in accordance with JIS K7136 (2000).
  • the surface of the base material 20 on the pressure-sensitive adhesive layer 10 side may be subjected to a physical treatment, a chemical treatment, or an undercoat treatment for enhancing the adhesion to the pressure-sensitive adhesive layer 10.
  • Physical treatments include, for example, corona treatment and plasma treatment.
  • Examples of the chemical treatment include acid treatment and alkali treatment.
  • the thickness of the base material 20 is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, and more preferably 20 ⁇ m or more from the viewpoint of ensuring the strength for the base material 20 to function as a support. Further, from the viewpoint of realizing appropriate flexibility in the pressure-sensitive adhesive sheet S, the thickness of the base material 20 is preferably 200 ⁇ m or less, more preferably 150 ⁇ m or less, still more preferably 100 ⁇ m or less.
  • the pressure-sensitive adhesive sheet S shown in FIG. 6 can be manufactured by the same method as the above-mentioned pressure-sensitive adhesive sheet manufacturing method except that the base material 20 is used instead of the first release film, for example.
  • the pressure-sensitive adhesive sheet S shown in FIG. 6 a manufacturing method similar to that of the above-mentioned adhesive sheet-attached product can be carried out except that the above-mentioned joining step is not carried out with reference to FIG. 1C (the pressure-sensitive adhesive sheet shown in FIG. 6).
  • the base material 20 is arranged in place of the above-mentioned second member M2).
  • the pressure-sensitive adhesive sheet-attached product Z' can be manufactured as shown in FIG. 7.
  • the method for manufacturing an adhesive sheet-attached product of the present invention can be applied to, for example, the manufacturing process of a display panel.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
PCT/JP2021/031869 2020-09-10 2021-08-31 粘着シート貼付品の製造方法 WO2022054637A1 (ja)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7343728B1 (ja) 2023-06-07 2023-09-12 デクセリアルズ株式会社 光硬化型接着組成物、硬化物、接続構造体及び接続構造体の製造方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1160962A (ja) * 1997-08-11 1999-03-05 Asahi Chem Ind Co Ltd 注型用感光性樹脂組成物
JP2010225909A (ja) * 2009-03-24 2010-10-07 Taiyo Ink Mfg Ltd 画像形成方法と光硬化画像、およびその方法に用いる光硬化性組成物
JP2013001847A (ja) * 2011-06-17 2013-01-07 Hitachi Chemical Co Ltd 半導体用積層シート、接着剤層付き半導体チップの製造方法及び半導体装置の製造方法
WO2016051914A1 (ja) * 2014-09-29 2016-04-07 株式会社スリーボンド 光硬化性樹脂組成物
WO2016129568A1 (ja) * 2015-02-09 2016-08-18 株式会社スリーボンド 光硬化性樹脂組成物の硬化方法および硬化物
WO2019035411A1 (ja) * 2017-08-18 2019-02-21 積水化学工業株式会社 湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017203810A (ja) 2016-05-09 2017-11-16 日本化薬株式会社 有機エレクトロルミネッセンスディスプレイ用カラーフィルタに含有される光吸収層、及びそれを用いたシート

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1160962A (ja) * 1997-08-11 1999-03-05 Asahi Chem Ind Co Ltd 注型用感光性樹脂組成物
JP2010225909A (ja) * 2009-03-24 2010-10-07 Taiyo Ink Mfg Ltd 画像形成方法と光硬化画像、およびその方法に用いる光硬化性組成物
JP2013001847A (ja) * 2011-06-17 2013-01-07 Hitachi Chemical Co Ltd 半導体用積層シート、接着剤層付き半導体チップの製造方法及び半導体装置の製造方法
WO2016051914A1 (ja) * 2014-09-29 2016-04-07 株式会社スリーボンド 光硬化性樹脂組成物
WO2016129568A1 (ja) * 2015-02-09 2016-08-18 株式会社スリーボンド 光硬化性樹脂組成物の硬化方法および硬化物
WO2019035411A1 (ja) * 2017-08-18 2019-02-21 積水化学工業株式会社 湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7343728B1 (ja) 2023-06-07 2023-09-12 デクセリアルズ株式会社 光硬化型接着組成物、硬化物、接続構造体及び接続構造体の製造方法

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