JP2020117729A - Silicone adhesive composition, adhesive article, laminate for optical device arrangement, solar cell module, organic el element and method for manufacturing laminate for optical device configuration - Google Patents

Abstract

To provide an adhesive article with a release film, which has both of adhesive characteristics at room temperature and low temperature characteristics.SOLUTION: The adhesive article with a release film has a release film and an adhesive layer thereon formed of a composition comprising (A) a photoactive catalyst, (B) a linear organopolysiloxane having an organic functional group bonded to a silicon atom and curable by the photoactive catalyst, and (C) a branched organopolysiloxane. The (B) linear organopolysiloxane and the (C) branched organopolysiloxane are incompatible with each other. The adhesive layer can be cured by irradiation with light and shows, after irradiated with light under the following conditions, at least one peak temperature of a loss tangent each in the range from -140°C to -100°C or lower and in the range from -50°C to 100°C or lower by dynamic viscoelasticity measurement at a frequency of 1 Hz. The irradiation conditions comprises irradiating the adhesive layer with UV rays by using a high-pressure mercury lamp so as to impart a cumulative light quantity of 2 J/cmat a wavelength of 365 nm.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a silicone pressure-sensitive adhesive composition, an adhesive article using the composition, and the like. In particular, mobile terminals (PDAs) such as smartphones, tablets, personal computers, game consoles, TVs (TV), car navigation systems, touch panels, image display devices such as pen tablets, solar cell modules such as organic thin films and dye sensitization, or The present invention relates to a silicone pressure-sensitive adhesive composition and the like that can be suitably used as a constituent member of an organic EL element.

Silicone adhesives have excellent heat resistance, weather resistance, electrical insulation, and chemical resistance, so when used in harsh environments, acrylic adhesives and rubber adhesives that are inferior in these properties are used. Used as an alternative to.

In general, a silicone pressure-sensitive adhesive is used after being molded using a solvent, followed by curing to scatter the solvent and improve various properties.

As the silicone pressure-sensitive adhesive, benzoyl peroxide or the like is used to cure with peroxide at 150° C. for about 10 minutes, or a platinum catalyst is used to cure with hydrosilylation reaction at about 100° C. for about 1 minute. There are things.

However, such a conventional thermosetting type silicone adhesive is often mixed with a reaction control agent for ensuring pot life. Therefore, there is a problem in that it needs to be cured at a high temperature for a long time and cannot be used for an adherend having a thin thickness or low heat resistance.

For example, Patent Document 1 discloses an addition reaction type tacky polyorganosiloxane composition that is cured at room temperature and exhibits tackiness.

In addition, in Patent Document 2, a room-temperature-curing-type addition-type tackiness that cures even at room temperature and exhibits tackiness, has excellent flexibility of a cured product, and suppresses cracking even when cured at higher temperatures. A polyorganosiloxane composition is disclosed.

The thermosetting type silicone pressure-sensitive adhesives disclosed in Patent Documents 1 and 2 can be cured at room temperature, but the curing reaction does not occur in the step of mixing to produce a composition or in the step of molding into a sheet or the like. A photo-curing type silicone pressure-sensitive adhesive has been demanded because it progresses.

For example, Patent Document 3 proposes a solventless UV-curable pressure-sensitive adhesive composition comprising an ultraviolet-functional catalyst composed of an epoxy-functional silicone polymer, a silicone MQ resin, and a halonium salt.

Further, Patent Document 4 discloses a UV-curable silicone pressure-sensitive adhesive composition that includes an alkenyl group-containing polyorganosiloxane, a mercapto group-containing polyorganosiloxane, and a polyorganosiloxane having a resin structure and can be cured at low temperature and in a short time. The thing is disclosed.

JP, 2004-323764, A JP, 2008-156441, A Japanese Patent Publication No. 01-28792 JP, 2002-371261, A

In the invention described in Patent Document 3, the halonium salt is difficult to be compatible with the silicone polymer, and thus curing may be insufficient. Further, the presence of a basic substance or a hydroxyl group-containing substance may hinder the curing. Therefore, there is a concern that the adhesion between the adhesive layer and the substrate/member becomes insufficient, or the curability is deteriorated.

Further, in Patent Document 4, there is a problem that the raw material is likely to be thermally deteriorated, so that the heat resistance is inferior, and the yellowing causes difficulty in use especially for optical applications. Further, there are problems that the odor of the raw material is strong and the handling property is poor.

The inventor of the present application has studied such conventional techniques. As a result, in the inventions described in Patent Documents 1 and 2, a large amount of branched polyorganosiloxane was added to the silicone resin for adhesion at room temperature (tack). ), the adhesive property (hereinafter referred to as "low temperature property") under a low temperature environment below room temperature, which is a characteristic of the linear polydimethylsiloxane skeleton, is significantly reduced. Turns out to be a concern.

As described above, the conventional silicone pressure-sensitive adhesive composition cannot satisfy the two contradictory properties of the adhesive property at room temperature and the low-temperature property, and the addition of other components and the intended use are limited. I can say.

Then, the subject which this invention tends to solve is providing the silicone adhesive composition which has the adhesive property at room temperature and the low temperature property simultaneously.

The present invention relates to (A) a photoactive catalyst, (B) a linear organopolysiloxane that has a silicon atom-bonded organic functional group and is curable by a photoactive catalyst, and (C) a branched chain. A silicone pressure-sensitive adhesive composition containing organopolysiloxane in the form of particles, wherein such composition after light irradiation under specific light irradiation conditions has a peak loss tangent (Tan δ) at a frequency of 1 Hz measured by dynamic viscoelasticity. The main feature is to have one or more temperatures in the ranges of −140° C. to −100° C. or lower and −50° C. to 100° C. or lower, respectively.

Since the silicone pressure-sensitive adhesive composition of the present invention can have adhesive properties at room temperature and low-temperature properties at the same time, and is excellent in optical properties, moisture and heat resistance reliability, low dielectric constant properties, etc., it can be used in optical applications, particularly in image display. There is an advantage that it can be used particularly preferably for device applications. The silicone pressure-sensitive adhesive composition of the present invention is also suitably used as a pressure-sensitive adhesive to an adherend that is generally difficult to adhere, particularly to an adherend such as a fluororesin-based molding or a silicone resin-based molding. be able to.

Hereinafter, an example of the embodiment of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

(Silicone adhesive composition)
The silicone pressure-sensitive adhesive composition of the present invention (hereinafter abbreviated as “the present composition”) is (A) a photoactive catalyst (hereinafter abbreviated as “component (A)”), ( B) A linear organopolysiloxane having an organic functional group bonded to a silicon atom and curable by the photoactive catalyst (hereinafter, abbreviated as “component (B)”), and (C). ) A branched organopolysiloxane (hereinafter, also abbreviated as “component (C)”) is included.

This composition shows the peak temperature of loss tangent (Tan δ) at a frequency of 1 Hz measured by dynamic viscoelasticity after light irradiation under the following light irradiation conditions from −140° C. to −100° C. or lower and −50° C. It is characterized by having one or more each in the range of 100° C. or less.

This indicates that the component (B) and the component (C) are in an incompatible state, and by having two peak temperatures, it is possible to simultaneously have an adhesive property at room temperature and a low temperature property. The term "incompatible" means a state in which the component (B) and the component (C) are not completely mixed, and means a state in which they may be partially mixed. A macroscopic observation by means of a state in which a microphase-separated structure such as a sea-island structure is observed. The method for measuring the peak temperature of the loss tangent (Tan δ) complies with the description of the examples and comparative examples described below.
[Light irradiation conditions]
Ultraviolet rays are radiated using a high pressure mercury lamp so that the integrated light amount at a wavelength of 365 nm is ² J/cm ² .

The composition has an incompatible combination of the component (B) and the component (C) in order to have the above-mentioned loss tangent (Tan δ) peak temperature within a predetermined range after light irradiation under the above light irradiation conditions. (Incompletely compatible combination), in addition, the primary structure of component (B) may be linear, its melt viscosity may be adjusted, and the primary structure of component (C) may be branched. The loss tangent (Tan δ) peak temperature can be kept within a predetermined range by selecting the branched structure and further adjusting the contents of the component (B) and the component (C) in the composition. ..

Among them, the melt viscosity of the component (B) at a temperature of 130° C. is preferably in the range of 50 Pa·s or more and 10000 Pa·s or less, more preferably in the range of 100 Pa·s or more and 5000 Pa·s or less, and 200 Pa·s. Most preferably, it is in the range of s or more and 4000 Pa·s or less.

Furthermore, for the same reason as above, the softening point of the component (C) at a temperature of 130° C. is 40° C.
It is preferably above, more preferably above 100°C, most preferably above 180°C.

For the same reason as above, the melt viscosity of the present composition at 130° C. is preferably in the range of 10 Pa·s or more and 5000 Pa·s or less, and in the range of 50 Pa·s or more and 3000 Pa·s or less. The range is more preferably 100 Pa·s or more and 1000 Pa·s or less.

The melt viscosity at the temperature of 130° C. is a value measured according to JIS K7244, and the softening point is a value measured according to JIS K7210.

The content of the component (B) and the component (C) is preferably 5 to 70 parts by mass when the total amount of the component (B) and the component (C) is 100 parts by mass. It is more preferably 10 to 60 parts by mass, and most preferably 20 to 50 parts by mass.

The storage shear elastic modulus (G′) at a temperature of 30° C. and a frequency of 1 Hz is 10 kPa or more and 5000 kPa or less, and the storage shear elastic modulus (G′) at a temperature of 100° C. and a frequency of 1 Hz is 1 kPa or more and 100 kPa or less. Is preferred. Within such a range, it is possible to obtain the advantages that the adhesive force is easily obtained and the reliability is excellent in a humidity and heat resistant environment. Further, the difference in elastic modulus between the storage shear modulus (G') of the composition at a temperature of 30°C and a frequency of 1 Hz (G') and the storage shear modulus (G') of the composition at a temperature of 100°C and a frequency of 1 Hz [G'(30 [°C·1 Hz)/G′(100° C.·1 Hz)] is preferably large, and specifically, it is preferably 1.5 or more and 1000 or less, more preferably 2 or more and 500 or less, and 3 or more. Most preferably, it is 300 or less. By setting it as such a range, it can have more excellent adhesive force. The method for measuring the storage shear elastic modulus (G') is based on the description of the examples and comparative examples described below.

In order to bring the storage shear modulus (G′) of the composition at a temperature of 30° C. and a frequency of 1 Hz into a predetermined range, the mixing parts of the component (B) and the component (C) may be adjusted or the component (B) may be mixed. It suffices to adjust the melt viscosity (molecular weight), the content of the organic functional group that contributes to curing, and the content of the branched skeleton of the component (C) and the content of the organic functional group.

The component (B) contained in the present composition imparts low temperature characteristics, impact resistance, flexibility, etc. to the cured product of the present composition, and the component (C) contained in the present composition is the component of the present composition. It imparts adhesive properties (tackiness) at room temperature, suitability for heat processing, fixing strength, handling properties, etc. to the cured product.

In addition, since the component (B) in the present composition has an organic functional group that can be a crosslinking point during curing or can form a three-dimensional network structure by an addition reaction, the component (B) can be formed by the action of the photoactive catalyst. The composition can be cured. In addition, by introducing an organic functional group into the component (C) or adding a cross-linking agent having an organic functional group as the component (D) described in detail below, the present composition has the same effect. It can be cured by irradiation with light, and the degree of curing of the composition (storage shear modulus G′) can also be adjusted.

(Component (A): Photoactive catalyst)
The photoactive catalyst contained in the present composition is a photoactive catalyst, and specifically, platinum group metal catalysts such as platinum-based, paradium-based and rhodium-based catalysts, nickel-based catalysts and photoradical polymerization. A catalyst etc. can be mentioned. Among these, platinum-based metal catalysts and radical polymerization catalysts are particularly preferable. Platinum-based metal catalysts include trimethyl(methylcyclopentadienyl)platinum complex, bis(acetylacetonate)platinum complex, 2,4,6,8. -Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane platinum complex, [1,3-bis(2,6-diisopropylphenyl)imidazole-2-yridine][1,3-bis(cyclohexyl)imidazole -2-yridin][1,3-divinyl-1,1,3,3-tetramethyldisiloxane] platinum complex, trimethyl(acetylacetonato)platinum complex, trimethyl(3,5-heptanedionate)platinum complex, Trimethyl(methylacetoacetate) platinum complex, bis(2,4-pentanedionato)platinum complex, bis(2,4-hexandionato)platinum complex, bis(2,4-heptanedionato)platinum complex, bis(3,3 5-heptanedionato)platinum complex, bis(1-phenyl-1,3-butanedionate)platinum complex, bis(1,3-diphenyl-1,3-propanedionato)platinum complex and (methylcyclopentadienyl)trimethylplatinum Can be mentioned.

The photoradical polymerization catalyst is a catalyst that is activated by irradiation with light, and specifically, acetophenone, 4-methylacetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone. , Benzyl dimethyl ketal (2,2-dimethoxy-1,2-diphenyl-ethane-1-one), 2,2-diethoxy-1-phenyl-ethane-1-one, acetophenone derivatives, benzophenone, 4,4 ,-Dimethoxybenzophenone, 4,4,-dimethylaminobenzophenone and other benzophenone derivatives, thioxanthone, 2,4-diethylthioxanthone, 2,-chlorothioxanthone and other thioxanthone derivatives, benzoin, benzoin methyl ether, benzoin isobutyl ether, etc. Examples thereof include a benzoin derivative, ethylanthraquinone, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

The above photoactive catalysts can be used alone or in combination of two or more. The content thereof is preferably 0.001 part by mass to 5 parts by mass, and 0.01 part by mass to 100 parts by mass when the total amount of the component (B) and the component (C) is 100 parts by mass. More preferably, it is 2 parts by mass. Further, it may be used in combination with other catalysts such as a heat activation type catalyst.

(Component (B): linear organopolysiloxane)
The linear organopolysiloxane (A) having a silicon-bonded organic functional group contained in the present composition and curable by a photoactive catalyst is a straight chain whose main chain is composed of R ₂ SiO units. A photopolymerizable silicone that is a polymer and has an organic functional group that reacts with a photoactive catalyst introduced into at least one of the R ₂ , and specifically, R ₂ is a vinyl group or an aryl group. , Butenyl group, hexenyl group, octenyl group, (meth)acryloyloxyethyl group, (meth)acryloyloxymethyl group, cyclohexenylethyl group, vinyloxypropyl group and other alkenyl groups as well as hydrogen groups (ie, for addition reaction) A straight-chain organopolysiloxane having a hydrogen atom bonded to a contributing silicon atom can be mentioned. Of these, R ₂ is particularly preferably a vinyl group, a (meth)acryloylalkenyl group or a hydrogen group.

It is preferable that two or more of these organic functional groups (R ₂ ) are contained in one molecule of the linear organopolysiloxane. The content of the organic functional group is preferably 0.001 wt% or more and 5 wt% or less, more preferably 0.005 wt% or more and 1 wt%, or 0.1 wt% or more and 0.5 wt% or less with respect to the weight of the component (B). Is more preferable. When the content is within the above range, it becomes easy to obtain a well-balanced adhesive strength and wet heat resistance of the adhesive composition after curing.

In the molecule of the linear organopolysiloxane, the organic functional group bonded to the silicon atom may be present at either the molecular chain terminal or the molecular chain side chain, or both of them. Good.

As the organic functional group bonded to the silicon atom other than the organic functional group bonded to the silicon atom, those having no aliphatic unsaturated bond are preferable, and examples thereof include an unsubstituted or substituted one having 1 to 12 carbon atoms. A valent hydrocarbon group can be mentioned.

Examples of the unsubstituted or substituted monovalent hydrocarbon group include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group, a cycloalkyl group such as a cyclohexyl group, and the like. Aryl groups such as phenyl group, tolyl group, xylyl group and naphthyl group, aralkyl groups such as benzyl group and phenethyl group, and some or all of hydrogen atoms of these groups are chlorine atom, fluorine atom, bromine atom, etc. And halogenated alkyl groups such as a chloromethyl group and a 3-chloropropyl group, which are substituted with the halogen atom.

The term "straight chain" means not only a completely straight chain, but also a straight chain partially having a branched chain. If the branched chain has a molecular weight smaller than that of the main chain, the straight chain is linear. And

The linear organopolysiloxane having an organic functional group bonded to a silicon atom contained in the present composition and curable by the photoactive catalyst, that is, the component (B) is composed of the component (B) and the component (B). When the total amount of C) is 100 parts by mass, it is preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and most preferably 20 to 50 parts by mass.

(Component (C): branched organopolysiloxane)
The branched organopolysiloxane contained in the present composition is a polymer having a three-dimensional network structure (resin structure) having at least one unit represented by R1 _a SiO _(4-a)/2 in its molecule. Specifically, an organopolysiloxane (MQ resin) composed of a monofunctional unit (M unit) represented by R1 ₃ SiO _1/2 and a Q unit represented by SiO _4/2 , an M unit and R1SiO _{3 /} Organopolysiloxane consisting of T and Q units represented by ₂ (MTQ resin), organopolysiloxane consisting of M units and bifunctional units (D units) represented by the formula: R1 ₂ SiO _2/2 and Q units ( MDQ resin), an organopolysiloxane composed of M units, D units, T units and Q units (MDTQ resin), and an organopolysiloxane composed of only T units (T resin). Among these, MQ resin is most preferable from the viewpoint of compatibility and appearance (transparency) when kneaded with the component (B), and the MQ ratio is preferably 0.1 to 2.0 and 0. It is more preferably 0.3 to 1.5, and most preferably 0.5 to 1.0.

Examples of R1 include a substituted or unsubstituted monovalent hydrocarbon group or an alkoxy group. Specific examples of the monovalent hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, Alkyl groups such as isopropyl group, isobutyl group, cyclopentyl group and cyclohexyl group, alkenyl groups such as vinyl group, aryl group and hexenyl group, aryl groups such as phenyl group and naphthyl group and 3-chloropropyl group, 3, Halogenated alkyl groups such as 3,3-trifluoropropyl group and nonafluorobutylethyl group, halogenated aryl groups such as 4-chlorophenyl group, 3,5-dichlorophenyl group and 3,5-difluorophenyl group, and 4 A halogenated alkyl group-substituted aryl group such as a -chloromethylphenyl group and a 4-trifluoromethylphenyl group can be exemplified. Further, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and an isopropoxy group.

Among the above, R1 is preferably a vinyl group as the alkenyl group, a methyl group as the monovalent hydrocarbon group other than the alkenyl group, and a methoxy group or an ethoxy group as the alkoxy group. Further, it is particularly preferable that R1 is an organic functional group (for example, an alkenyl group such as vinyl group) that can be crosslinked by a photoactive catalyst.

The branched organopolysiloxane contained in the composition, that is, the component (C), should be contained in an amount of 30 to 95 parts by mass when the total amount of the component (B) and the component (C) is 100 parts by mass. Is preferred, 40 to 90 parts by mass is more preferred, and 50 to 80 parts by mass is most preferred.

(Crosslinking agent)
It is more preferable to add a crosslinking agent as the component (D) to the composition. By adding a cross-linking agent, it is easy to form a three-dimensional network structure by binding to the curable organic functional group contained in the component (B) or the component (C), or by binding the cross-linking agents together. Become.

The crosslinking agent used in the present composition is not particularly limited as long as it has a property of forming a three-dimensional network structure by light irradiation and curing, and examples thereof include a vinyl group, an aryl group, a butenyl group, a hexenyl group, and an octenyl group. Groups, alkenyl groups such as (meth)acryloyloxyethyl group, (meth)acryloyloxymethyl group, cyclohexenylethyl group, and vinyloxypropyl group, as well as hydrogen groups (that is, hydrogen bonded to a silicon atom that contributes to the addition reaction). A cross-linking agent having an organic functional group such as a linear organopolysiloxane having an atom can be used. Among these, crosslinking agents having an organic functional group such as vinyl group, (meth)acryloylalkenyl group or hydrogen group are particularly preferable.

In addition, the crosslinking agent preferably has two or more organic functional groups in the skeleton of the silicone monomer or oligomer from the viewpoints of handling properties, physical properties after curing of the composition, transparency, and the like.

The addition amount of the organic functional group contained in the cross-linking agent is preferably 0.01 wt% or more and 10 wt% or less, more preferably 0.05 wt% or more and 8 wt%, or 0.1 wt% or more with respect to the weight of the component (D). It is more preferably 5 wt% or less. When the content is within the above range, it becomes easy to obtain a well-balanced adhesive strength and wet heat resistance of the adhesive composition after curing.

The content of the cross-linking agent as the component (D) may be 0.1 to 20 parts by mass of the component (D) when the total amount of the components (B) and (C) is 100 parts by mass. It is more preferably 0.3 to 15 parts by mass, and most preferably 0.5 to 10 parts by mass.

(Other ingredients)
Other components that can be contained in the present composition include metal oxides as heat resistance improvers, antioxidants, flame retardant aids, conductivity imparting agents, antistatic agents, processing aids, rust preventives. In addition, an alkoxysilane group-containing compound having an alkoxysilyl group, a silane coupling agent, a titanium-based or zirconium-based condensation catalyst, and the like can be contained in the composition as a crosslinking auxiliary agent.

(Characteristics of this composition after light irradiation)
The composition preferably has an adhesion to glass after light irradiation under the above-mentioned light irradiation conditions of 3 N/cm or more at -30°C and 3 N/cm or more at 30°C, and -30°C. Is more preferably 5 N/cm or more and 5 N/cm or more at 30° C., and most preferably 8 N/cm or more at −30° C. and 8 N/cm or more at 30° C. By having such characteristics, there are advantages such as excellent reliability under a wide range of temperature conditions, and it can be suitably used for optical applications, image display apparatus applications, particularly applications used in harsh environments. In order to have such an adhesive force, it is necessary to adjust the number of blending parts of the component (B) and the component (C), the melt viscosity (molecular weight) of the component (B), the content of the organic functional group contributing to curing, and the like. It may be adjusted, or the branched skeleton of the component (C), the content of the organic functional group, and the like may be adjusted. In addition, the measuring method of the adhesive force is based on the description of Examples and Comparative Examples described below.

The haze of the composition after irradiation with light under the above conditions at a thickness of 150 μm is preferably 2% or less, more preferably 1% or less, and most preferably 0.5% or less. By having such characteristics, there are advantages such as high transparency and excellent visibility, and it can be suitably used for optical applications and the like. In order to provide such haze, the kinds and blending amounts of the component (A), the component (B) and the component (C) may be adjusted. The method for measuring haze is based on the description in Examples and Comparative Examples described below.

The composition has a refractive index of 1.30 to 1.60 after irradiation with light under the above conditions, preferably 1.35 to 1.55, and more preferably 1.40 to 1. Most preferred is 50. By having such characteristics, it is possible to reduce reflection loss when it is attached to a general glass or resin adherend, and there are advantages such as improved visibility, and it is suitable to be used for optical applications and the like. You can In order to adjust the refractive index, a phenyl group may be introduced into the component (B) or the component (C) or both components.

(Method for producing the composition)
When the present composition is produced, it can be obtained by mixing each of the components (A), (B) and (C) in a predetermined amount (the component (D) is added if necessary). The mixing method of these is not particularly limited, and for example, the component (A), the component (B) and the component (C) can be simply mixed, and the addition order of each component is not particularly limited. In addition, it is preferable to include a heat treatment step at the time of producing the mixture, and in this case, the heat treatment is performed by previously mixing the component (A), the component (B), the component (C) and other components as necessary. desirable. A mixture of several components may be supplied in advance, or an additive component may be concentrated and supplied as a masterbatch.

The heat treatment temperature can be usually 40 to 150° C. By introducing such a heat treatment step, each component can be uniformly mixed, and thus a composition having more stable characteristics such as optical characteristics can be obtained. ..

The mixing method is also not particularly limited, and for example, a universal kneader, a planetary mixer, a Banbury mixer, a kneader, a gate mixer, a pressure kneader, a triple roll, or a double roll can be used. You may mix using a solvent as needed. When a component (C) having a high softening point is used, it is possible to uniformly mix the components at a low temperature for a shorter time by dissolving the component in an organic solvent and then adding the component.

(Adhesive article)
The composition can be used as it is as a pressure-sensitive adhesive composition, but can also be used as a pressure-sensitive adhesive article as a molded product of a cured product of the composition. Examples of the method for producing the pressure-sensitive adhesive article as such a molded article include a method of molding by compression molding, injection molding, injection molding, etc., a method of molding on a metal substrate or a resin substrate by insert molding, or dipping, coating, screen. There is a method of obtaining a molded body integrated with a substrate by printing or the like. Examples of the curing conditions include a method of curing by irradiating light such as ultraviolet rays or visible rays, and among them, ultraviolet rays are preferable from the viewpoint of suppressing damage to the optical device constituting member and controlling the reaction. Further, the irradiation energy of light, irradiation time, irradiation method, etc. are not particularly limited, and the present composition can be cured by activating the component (A) which is a photoactive catalyst and promoting crosslinking. Good. Examples of the light irradiation method include a high pressure mercury lamp, a metal halide lamp, and an LED lamp.

Further, the present composition can be used as a solvent-free system containing no solvent. By using it as a solvent-free system, it is possible to provide the advantage that the solvent does not remain and the heat resistance and light resistance are improved.

Further, the present composition is a pressure-sensitive adhesive article as a pressure-sensitive adhesive sheet with a release film, which is molded into a single-layer or multi-layered sheet on a release film, in addition to being directly applied to an adherend and cured. Can also Examples of the material of the release film include polyester film, polyolefin film, polycarbonate film, polystyrene film, acrylic film, triacetyl cellulose film, fluororesin film and the like. Among these, polyester film and polyolefin film are particularly preferable.

The release film may be used alone without a release layer as long as it has sufficient releasability, but one release film at the time of sticking an adhesive sheet to an adherend It is more preferable to form release layers having different peeling forces in order to prevent tearing when peeling. Examples of the release agent used in the release film include silicone, fluororesins, polyvinyl alcohol resins, resins having an alkyl group, and the like, modified products or mixtures thereof. Among these, fluorosilicone is particularly preferable because it can provide excellent releasability. The release film or the pressure-sensitive adhesive sheet with the release film may be subjected to embossing, die pressing, or the like.

When using a pressure-sensitive adhesive article as a molded product of a cured product of the present composition for an optical device constituting device or the like, using a molded article in a sheet shape, it is possible to use a pressure-sensitive adhesive article obtained by a bonding method, It is excellent in workability and more preferable.

When the pressure-sensitive adhesive article formed by molding the composition into a sheet is used, the pressure-sensitive adhesive article may have at least one pressure-sensitive adhesive layer (I layer) composed of the composition, and may have a single-layer structure. There is no limitation as to whether it is a laminated structure. A single-layer structure composed of a single composition can simplify the film forming process of the adhesive article. Further, when the pressure-sensitive adhesive article has a laminated structure having another layer (II layer) having different composition contents and composition ratios, various characteristics required for the transparent sealing layer can be achieved in a well-balanced manner.

When the pressure-sensitive adhesive article has a laminated structure, the pressure-sensitive adhesive article preferably has a pressure-sensitive adhesive layer (I layer) composed of the present composition on the surface layer. This makes it easy for the adhesive article to have both low temperature characteristics and room temperature adhesive characteristics. In the adhesive article, the II layer may have a laminated structure of different materials. For example, a structure having a transparent inorganic oxide film such as SiO ₂ or Al ₂ O ₃ , a barrier film, a retardation film for a display in an intermediate layer, a known pressure sensitive adhesive or a pressure sensitive adhesive may be used.

Examples of the laminated structure include a two-layer structure such as I layer/II layer and a two-kind three-layer structure such as I layer/II layer/I layer. Further, the number of layers may be increased to 4 layers, 5 layers, 6 layers, and 7 layers as needed. Further, the pressure-sensitive adhesive article may be in a form with a release film (a pressure-sensitive adhesive article with a release film) formed by laminating a release film on one side or both sides.

(Laminate for optical device configuration)
The optical device constituting laminate is, for example, an optical device comprising a combination obtained by selecting one or more of the present composition or the above-mentioned adhesive article and a group consisting of a touch panel, an image display panel and a surface protection panel. It is manufactured by using a member for construction. More specifically, it can be obtained by laminating two image display device constituting members via the present composition or the adhesive article. It should be noted that they may be attached one by one or two at the same time, and the attaching method and order are not limited at all. In addition, after the two optical device constituting members are bonded together, the present composition or the pressure-sensitive adhesive article can be cured by further irradiating light from the optical device constituting member side. By adopting such a method, due to the excellent step absorption performance of the present composition before curing, even an optical device constituting member having irregularities can be easily bonded smoothly, or the reliability after bonding can be improved. There are advantages such as excellent. When such a method is adopted, for example, the composition is primarily cured by irradiation with light before bonding the optical device-constituting member, and then, for example, the component (A) as the photoactive catalyst is activated. The component (A) may be activated by a light-shielding treatment so that the component (A) is not exposed to light, and the component (A) is activated again by light irradiation again after the member is bonded.

Examples of the member for forming an optical device include a surface protection panel, a touch panel and an image display panel. For example, one is a surface protection panel and the other is an image display panel, and one is a surface protection panel and the other is A combination of a touch panel and one of which is a touch panel and the other of which is an image display panel can be mentioned.

The material of the surface protection panel may be plastic such as acrylic resin, polycarbonate resin, and cycloolefin polymer other than glass.

Further, the surface protection panel may be one having a touch panel function integrated therein, and may be, for example, a touch-on-lens (TOL) type or a one glass solution (OGS) type. Further, the surface protection panel may have a print step portion printed in a frame shape on the peripheral portion thereof.

The touch panel may be of any of a resistance film type, a capacitance type, an electromagnetic induction type and the like.

The image display panel is composed of another optical film such as a polarizing film and other retardation film, a liquid crystal material, and a backlight system (usually, the adhered surface of the composition or the adhesive article to the image display panel is an optical film. There are STN method, VA method, IPS method, etc. depending on the control method of the liquid crystal material, but any method may be used. Further, the image display panel may be an in-cell type in which the touch panel function is built in the TFT-LCD, or an on-cell type in which the touch panel function is built in between the glass substrate provided with the polarizing plate and the color filter.

(Solar cell module)
The solar cell module is formed by laminating a front protective panel, a sealing material layer, a solar cell, a sealing material layer, and a back protective panel in this order from the sunlight receiving side. The present composition or the above-mentioned adhesive article can be used as a stopping material. Therefore, the solar cell module of the present invention comprises the composition or the above-mentioned adhesive article and a combination obtained by selecting any one or more of the group consisting of a solar cell, a front surface protection panel and a back surface protection panel. It is manufactured using a member.

(Organic EL element)
The organic EL element is formed by laminating a surface protection substrate, an adhesive layer, an organic EL element substrate, an adhesive layer, and a back surface protection substrate in this order from the viewing side. In the present invention, such an adhesive layer is used. The present composition or the pressure-sensitive adhesive article described above can be used. Therefore, the organic EL device of the present invention comprises a combination obtained by selecting any one or more of the present composition or the above-mentioned adhesive article, and a group consisting of a surface protection substrate, an organic EL device substrate and a back surface protection substrate. It is made of a combination with a substrate.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

[Example 1]
0.2 g of A-1 (trimethyl(methylcyclopentadienyl)platinum complex) as a photoactive catalyst and B-1 (vinyl group-containing polydimethylsiloxane, vinyl content 0.073% by mass) as a linear polyorganosiloxane , 130° C. melt viscosity 2700 Pa·s, refractive index 1.403) 400 g, branched polyorganosiloxane C-1 (MQ resin, M/Q=0.72) 600 g, crosslinking agent D-1 (hydro). 36 g of a gen group-containing silicone oil, a hydrogen content of 0.69% by mass, and a viscosity of 100 Pa·s at 25° C. were mixed to give a silicone adhesive composition 1 (melt viscosity (130° C.): 640 Pa·s, G′(30 C): 15 kPa, G′ (100° C.): 1.8 kPa) were prepared.

As a release film, the above-mentioned silicone pressure-sensitive adhesive composition 1 was shaped into a sheet on a release-treated polyethylene terephthalate film (“Bina YB100” manufactured by Fujimori Industry Co., Ltd., thickness: 100 μm) to a thickness of 150 μm. did. Furthermore, by coating the release film with a release-treated polyethylene terephthalate film (“Bina SF75” manufactured by Fujimori Industry Co., Ltd., thickness: 75 μm) as a new release film, the silicone adhesive composition 1 A three-layer silicone pressure-sensitive adhesive sheet laminate having laminated release films on both sides was produced. This laminated body is irradiated with ultraviolet rays through a release film so that the integrated light amount of 365 nm becomes ² J/cm ² by using a high-pressure mercury lamp, and allowed to stand still at 23° C. and 40% RH for 24 hours. Thus, a sheet-shaped pressure-sensitive adhesive article with release film 1 was obtained.

[Example 2]
0.2 g of A-1 as a photoactive catalyst, 350 g of B-1 as a linear polyorganosiloxane, 650 g of C-1 as a branched polyorganosiloxane, and 32 g of D-1 as a crosslinking agent were mixed. Silicone adhesive composition 2 (melt viscosity (130° C.): 710 Pa·s, G′ (30° C.): 170 kPa, G′ (100° C.): 2.3 kPa) was prepared.

In the same manner as in Example 1, a three-layer silicone pressure-sensitive adhesive sheet laminate having a release film laminated on both surfaces of the silicone pressure-sensitive adhesive composition 2 was prepared. After that, using a high-pressure mercury lamp, ultraviolet rays are radiated through the release film so that the integrated light amount of 365 nm becomes ² J/cm ^2, and the sheet is left standing in an environment of 23° C. and 40% RH for 24 hours. A striped film-attached pressure-sensitive adhesive article 2 was obtained.

[Example 3]
0.2 g of A-1 as a photoactive catalyst, 300 g of B-1 as a linear polyorganosiloxane, 700 g of C-1 as a branched polyorganosiloxane, and 28 g of D-1 as a crosslinking agent were mixed, A silicone pressure-sensitive adhesive composition 3 (melt viscosity (130° C.): 941 Pa·s, G′ (30° C.): 4300 kPa, G′ (100° C.): 3.6 kPa) was prepared.

In the same manner as in Example 1, a three-layer silicone pressure-sensitive adhesive sheet laminate having a release film laminated on both surfaces of the silicone pressure-sensitive adhesive composition 3 was prepared. After that, using a high-pressure mercury lamp, ultraviolet rays are radiated through the release film so that the integrated light amount of 365 nm becomes ² J/cm ^2, and the sheet is left standing in an environment of 23° C. and 40% RH for 24 hours. A release film-attached pressure sensitive adhesive article 3 was obtained.

[Example 4]
0.2 g of A-2 (2,4,6,8-tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane platinum complex) as a photoactive catalyst and B-as a linear polyorganosiloxane 1 g (350 g), branched polyorganosiloxane (C-1) (650 g) and cross-linking agent (D-1) (32 g) were mixed to give a silicone adhesive composition 4 (melt viscosity: 720 Pa·s, G′ (30° C.): 160 kPa). , G′ (100° C.): 2.4 kPa) were produced.

In the same manner as in Example 1, a three-layer silicone pressure-sensitive adhesive sheet laminate in which a release film was laminated on both surfaces of the silicone pressure-sensitive adhesive composition 4 was prepared to obtain a sheet-shaped pressure-sensitive adhesive article with a release film 4. It was The pressure-sensitive adhesive article 4 was stored in a dark place at a low temperature after production and used for the subsequent evaluation.

[Comparative Example 1]
77 parts by mass of 2-ethylhexyl acrylate, 19 parts by mass of vinyl acetate and 4 parts by mass of acrylic acid are randomly copolymerized, and 1 kg of an acrylic acid ester copolymer (weight average molecular weight: 400,000) isocyanuric acid ε-caprolactam. 50 g of modified triacrylate was added and mixed to obtain an acrylic composition. To the acrylic composition, 12 g of A-3 (a mixture of 2,4,6-trimethylbenzophenone and 4-methylbenzophenone) as a photoactive catalyst was added and mixed to prepare an acrylic pressure-sensitive adhesive composition 5 (melted). Viscosity: 170 Pa·s) was prepared.

As the release film, the acrylic pressure-sensitive adhesive composition 5 was shaped into a sheet on a release-treated polyethylene terephthalate film (“MRA100” manufactured by Mitsubishi Plastics Co., Ltd., thickness: 100 μm) to a thickness of 150 μm. did. Further, as a new release film, a release-treated polyethylene terephthalate film (“MRF75” manufactured by Mitsubishi Plastics Co., Ltd., thickness: 75 μm) is coated on the release film to give an acrylic pressure-sensitive adhesive composition 5. A three-layer acrylic pressure-sensitive adhesive sheet laminate having laminated release films on both sides was produced. This laminated body is irradiated with ultraviolet rays through a release film so that the integrated light amount of 365 nm becomes 1 J/cm ² by using a high pressure mercury lamp, and left still at 23° C. and 40% RH for 1 day. Thus, a sheet-like pressure-sensitive adhesive article with release film 5 (G′ (30° C.): 55 kPa, G′ (100° C.): 7.2 kPa) was obtained.

[Comparative Example 2]
0.2 g of A-1 as a photoactive catalyst, 960 g of B-1 as a linear polyorganosiloxane, 40 g of C-1 as a branched polyorganosiloxane, and 100 g of D-1 as a crosslinking agent were mixed, A silicone pressure-sensitive adhesive composition 6 (melt viscosity (130° C.): 2300 Pa·s, G′ (30° C.): 20 kPa, G′ (100° C.): 7.1 kPa) was prepared.

In the same manner as in Example 1, a three-layer silicone pressure-sensitive adhesive sheet laminate having a release film laminated on both sides of the silicone pressure-sensitive adhesive composition 6 was produced. After that, using a high-pressure mercury lamp, ultraviolet rays are radiated through the release film so that the integrated light amount of 365 nm becomes ² J/cm ^2, and the sheet is left standing in an environment of 23° C. and 40% RH for 24 hours. A release film-attached pressure sensitive adhesive article 6 was obtained.

[Various evaluation results]
(Storage shear modulus G')
The storage shear modulus G′ was measured by using each rheometer (“MARS” manufactured by Eiko Seiki Co., Ltd.) as a sample (circle having a thickness of 1 to 2 mm and a diameter of 20 mm) prepared in Examples and Comparative Examples. The storage shear modulus G'(30°C) at 30°C and the storage modulus G'(100°C) at 100°C were determined from the obtained data. The adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1 were subjected to autoclave treatment and then cured with ultraviolet rays so that the accumulated light amount at 365 nm was ² J/cm ^2, and then 23 What was aged at 40°C and 40% RH for 24 hours was used as a sample for measurement. The measurement results are shown in Table 1.
<Measurement conditions>
・Adhesive jig: Φ25mm parallel plate,
・Distortion: 0.5%
・Frequency: 1 Hz
・Measuring temperature: -50 to 200°C
・Raising rate: 3°C/min condition

(Peak temperature of loss tangent (Tan δ))
The peak temperature of loss tangent (Tan δ) was measured using a viscoelasticity measuring device (“Viscoelasticity Spectrometer DVA-200” manufactured by IT Measurement Co., Ltd.) for each adhesive article prepared in Examples and Comparative Examples (length 4 mm). , Horizontal 60 mm), the storage tensile elastic modulus E′ was measured under the following measurement conditions, and the loss tangent (Tan δ) and the peak temperature (° C.) of the loss tangent (Tan δ) at each measurement temperature were obtained from the obtained data. It was measured by obtaining. The adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1 were subjected to autoclave treatment and then cured with ultraviolet rays so that the accumulated light amount at 365 nm was ² J/cm ^2, and then 23 What was aged at 40°C and 40% RH for 24 hours was used as a sample for measurement. The measurement results are shown in Table 1.
<Measurement conditions>
・Vibration frequency: 1 Hz
・Distortion: 0.1%
・Raising rate: 3°C/min ・Measuring temperature: -150°C to 200°C
・25mm between chucks

(Adhesive force)
One of the release films of each of the pressure-sensitive adhesive articles produced in Examples and Comparative Examples was peeled off, and a polyethylene terephthalate film (“DIAFOIL T100” manufactured by Mitsubishi Plastics Co., Ltd., thickness 50 μm) of 50 μm was laminated as a backing film to form a laminate Was produced. The measurement results are shown in Table 1.

Each of the laminated products was cut into a length of 150 mm and a width of 10 mm, the remaining release film was peeled off, and the exposed adhesive surface was roll-pressed onto soda lime glass. The glass-bonded product was subjected to autoclave treatment (80° C., gauge pressure 0.3 MPa, 20 minutes) and finish-bonded to prepare a sample for measuring adhesive strength. The adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1 were subjected to autoclave treatment and then cured with ultraviolet rays so that the accumulated light amount at 365 nm was ² J/cm ^2, and then 23 A sample that was aged at 40° C. and 40% RH for 24 hours was used as a sample for measuring the adhesive strength.

The respective adhesive force measurement samples were allowed to stand in an environment of −30° C. and 30° C. for 2 hours, then the peeling force was measured under the following measurement conditions, and the obtained value was taken as the adhesive force. The measurement results are shown in Table 1.
<Measurement conditions>
-Test temperature: -30°C and 30°C
・Peeling speed: 60 mm/min ・Peeling angle: 180°

(Haze)
The release films of the adhesive articles prepared in Examples and Comparative Examples were sequentially peeled off, and soda lime glass (82 mm×53 mm×0.5 mm thickness, 0.2% haze) was roll-bonded on both sides. The bonded product was subjected to autoclave treatment (80° C., gauge pressure: 0.3 MPa, 20 minutes) and finish-bonded to obtain a sample for measuring optical characteristics. The adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1 were subjected to autoclave treatment and then cured with ultraviolet rays so that the accumulated light amount at 365 nm was ² J/cm ^2, and then 23 What was aged at 40°C RH for 24 hours was used as a sample for measuring optical characteristics.

The haze of the sample for measuring optical characteristics was measured using a haze meter (NDH5000 manufactured by Nippon Denshoku Industries Co., Ltd.) according to JIS K7136. The measurement results are shown in Table 1.

(Moisture and heat resistance)
The release films of the adhesive articles produced in Examples and Comparative Examples were sequentially peeled off, and soda lime glass (82 mm×53 mm×0.5 mm thickness) and a transparent plastic plate (“MR58” manufactured by Mitsubishi Gas Chemical Company, thickness 1 mm) were used. ) And roll-bonding, and then using a vacuum laminator (“PVL0505S” manufactured by Nisshinbo Mechatronics, Inc.), press-bonding under the conditions of temperature: 80° C., press time: 5 minutes, press pressure: 0.04 MPa. did. The bonded product was subjected to autoclave treatment (80° C., gauge pressure: 0.3 MPa, 20 minutes) for final bonding, and used as a sample for measuring humidity and heat resistance reliability. In addition, regarding the adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1, after the final attachment, a high pressure mercury lamp was used so that the integrated light amount of ultraviolet rays of 365 nm was ² J/cm ^2. The sample was irradiated from the glass surface to cure the bonded product. A sample that was aged at 23° C. and 40% RH for 24 hours was used as a sample for measuring the resistance to moist heat. It should be noted that three samples were prepared for each measurement of moist heat resistance reliability.

When each of the samples for measuring the moisture and heat resistance reliability was allowed to stand still in a constant temperature and humidity bath at 80° C. and 90% RH for 300 hours, and then at 23° C. and 40% RH for 2 hours. The appearance of the three samples was observed and evaluated according to the following criteria. The evaluation results are shown in Table 1.
<Appearance standard>
⊚: No whitening, foaming, warpage, etc. occurred in all samples, and there was almost no change in appearance before and after the wet heat test.
◯: Some appearance of whitening can be confirmed after the wet heat test, but the appearance is relatively good.
Poor: At least one sample had foaming, peeling, warpage, etc. at the central portion or the end portion, and the appearance was obviously deteriorated.

(Relative permittivity)
One release film of each of the pressure-sensitive adhesive articles produced in Examples and Comparative Examples was peeled off, roll-pressed onto a SUS plate, and then autoclaved (80° C., gauge pressure 0.3 MPa, 20 minutes) and applied. I wore it. Next, the remaining release film was peeled off, and a 45 mmΦ aluminum foil was roll-pressed to prepare a sample for measuring the relative dielectric constant. The adhesive article 4 produced in Example 4 and the adhesive article 5 produced in Comparative Example 1 were subjected to autoclave treatment and then cured with ultraviolet rays so that the accumulated light amount at 365 nm was ² J/cm ^2, and then 23 What was aged at 40°C and 40% RH for 24 hours was used as a sample for measuring the relative dielectric constant.

Using the sample for measuring relative permittivity, the relative permittivity at 23° C., 40% RH, and frequency of 100 kHz was measured by an LCR meter (“HP4284A” manufactured by Agilent Technologies) in accordance with JIS C2138. The measurement results are shown in Table 1.

The pressure-sensitive adhesive articles 1 to 4 obtained by photocuring the pressure-sensitive adhesive compositions 1 to 4 prepared in Examples 1 to 4 have adhesive properties at low temperature (-30°C) and near room temperature (30°C) at the same time. In addition, it was excellent in optical characteristics, resistance to moist heat and low dielectric constant characteristics. In addition, in Example 4, by irradiating with light after bonding the member for forming the optical device, the moisture and heat resistance became more excellent.

On the other hand, in Comparative Example 1 of a pressure-sensitive adhesive article made of an acrylic pressure-sensitive adhesive composition, having a loss tangent (Tan δ) peak at −18° C. has sufficient pressure-sensitive adhesive force at room temperature, but low-temperature pressure-sensitive adhesive property is obtained. However, when used in a low temperature environment or subjected to an impact such as dropping, peeling was likely to occur.

Further, the pressure-sensitive adhesive article of Comparative Example 2 did not have a loss tangent (Tan δ) peak in the range of −50 to 100° C., so that the pressure-sensitive adhesive strength at room temperature was extremely low. As a result, peeling and floating due to wet heat resistance and the like were likely to occur.

The silicone pressure-sensitive adhesive composition of the present invention can simultaneously have room-temperature pressure-sensitive adhesive properties and low-temperature properties, and is excellent in optical properties, heat resistance reliability, weather resistance reliability, low dielectric constant properties, etc. It can also be used for display devices. The silicone pressure-sensitive adhesive composition of the present invention is also suitably used as a pressure-sensitive adhesive to an adherend that is generally difficult to adhere, particularly to an adherend such as a fluororesin-based molding or a silicone resin-based molding. be able to.

Claims (26)

On the release film, (A) a photoactive catalyst, (B) a linear organopolysiloxane having a silicon atom-bonded organic functional group and curable by the photoactive catalyst, and (C) a branch A pressure-sensitive adhesive layer formed from a composition containing the organopolysiloxane in the form of
The (B) linear organopolysiloxane and the (C) branched organopolysiloxane are incompatible,
The pressure-sensitive adhesive layer has a peak temperature of loss tangent at a frequency of 1 Hz measured by dynamic viscoelasticity after light irradiation under the following light irradiation conditions of −140° C. to −100° C. or lower, and −50° C. to 100° C. or lower. A release film-attached pressure-sensitive adhesive article that can be cured by irradiation with light and has one or more in each range.
[Light irradiation conditions] Ultraviolet rays are irradiated using a high-pressure mercury lamp so that the integrated light amount at a wavelength of 365 nm is ² J/cm ² . On the release film, (A) a photoactive catalyst, (B) a linear organopolysiloxane having a silicon atom-bonded organic functional group and curable by the photoactive catalyst, and (C) a branch A pressure-sensitive adhesive layer formed from a composition containing the organopolysiloxane in the form of
When the total amount of the (B) linear organopolysiloxane and the (C) branched organopolysiloxane is 100 parts by mass, the composition has the (B) linear organopolysiloxane. Including 5 to 70 parts by mass,
The adhesive layer has a peak temperature of loss tangent at a frequency of 1 Hz measured by dynamic viscoelasticity after light irradiation under the following light irradiation conditions of −140° C. to −100° C. or lower, and −50° C. to 100° C. or lower. A release film-attached pressure-sensitive adhesive article that can be cured by irradiation with light and has one or more in each range.
[Light irradiation conditions] Ultraviolet rays are irradiated using a high-pressure mercury lamp so that the integrated light amount at a wavelength of 365 nm is ² J/cm ² . On the release film, (A) a photoactive catalyst, (B) a linear organopolysiloxane having a silicon atom-bonded organic functional group and curable by the photoactive catalyst, and (C) a branch A pressure-sensitive adhesive layer formed from a composition containing the organopolysiloxane in the form of
The (B) linear organopolysiloxane and the (C) branched organopolysiloxane are incompatible,
The pressure-sensitive adhesive layer has a peak temperature of one or more loss tangents in a range of −140° C. to −100° C. or lower and −50° C. to 100° C. or lower at a frequency of 1 Hz,
The release film is a pressure-sensitive adhesive article with a release film having a release layer containing fluorosilicone. On the release film, (A) a photoactive catalyst, (B) a linear organopolysiloxane having a silicon atom-bonded organic functional group and curable by the photoactive catalyst, and (C) a branch A pressure-sensitive adhesive layer formed from a composition containing the organopolysiloxane in the form of
When the total amount of the (B) linear organopolysiloxane and the (C) branched organopolysiloxane is 100 parts by mass, the composition has the (B) linear organopolysiloxane. Including 5 to 70 parts by mass,
The pressure-sensitive adhesive layer has a peak temperature of one or more loss tangents in a range of −140° C. to −100° C. or lower and −50° C. to 100° C. or lower at a frequency of 1 Hz,
The release film is a pressure-sensitive adhesive article with a release film having a release layer containing fluorosilicone. The adhesive layer has a storage shear elastic modulus (G′) of 10 kPa or more and 5000 kPa or less at a temperature of 30° C. and a frequency of 1 Hz, and the adhesive layer has a storage shear elastic modulus (G′) of 1 kPa at a temperature of 100° C. and a frequency of 1 Hz. The pressure-sensitive adhesive article with a release film according to claim 3 or 4, which is 100 kPa or more. The pressure-sensitive adhesive article with a release film according to any one of claims 3 to 5, wherein the pressure-sensitive adhesive force of the pressure-sensitive adhesive layer is 3 N/cm or more at -30°C and 3 N/cm or more at 30°C. The release film-attached pressure-sensitive adhesive article according to any one of claims 3 to 6, wherein a haze of the pressure-sensitive adhesive layer after light irradiation under the light irradiation condition at a thickness of 150 µm is 2% or less. The pressure-sensitive adhesive article with a release film according to claim 1, wherein the release film has a release layer containing fluorosilicone. The pressure-sensitive adhesive article with a release film according to claim 1, wherein the composition further contains (D) a cross-linking agent. The pressure-sensitive adhesive article with a release film according to any one of claims 1 to 9, wherein the organic functional group is either a vinyl group or a (meth)acryloylalkenyl group. The pressure-sensitive adhesive article with a release film according to claim 1, wherein the composition has a melt viscosity at a temperature of 130° C. of 10 Pa·s or more and 5000 Pa·s or less. (A) a photoactive catalyst, (B) a linear organopolysiloxane having an organic functional group bonded to a silicon atom and curable by the photoactive catalyst, and (C) a branched organopolysiloxane. A composition containing siloxane, wherein when the total amount of the (B) straight-chain organopolysiloxane and the (C) branched organopolysiloxane is 100 parts by mass, the (B) direct composition The pressure-sensitive adhesive sheet laminate with a release film, which comprises a release film on at least one surface of a sheet having a pressure-sensitive adhesive layer made of a composition containing 5 to 70 parts by mass of a chain organopolysiloxane, after the light irradiation. The release film so that the layer has one or more peak temperatures of loss tangent (Tan δ) in the ranges of −140° C. to −100° C. and −50° C. to 100° C., respectively, at a frequency of 1 Hz. A method for producing an adhesive article with a release film, which comprises irradiating light through the article. The method for producing a pressure-sensitive adhesive article with a release film according to claim 12, wherein the composition further contains (D) a cross-linking agent. The method for producing a pressure-sensitive adhesive article with a release film according to claim 12 or 13, wherein the organic functional group is either a vinyl group or a (meth)acryloylalkenyl group. The method for producing a pressure-sensitive adhesive article with a release film according to claim 12, wherein the composition has a melt viscosity at a temperature of 130° C. of 10 Pa·s or more and 5000 Pa·s or less. The adhesive layer after light irradiation has a storage shear modulus (G′) at a temperature of 30° C. and a frequency of 1 Hz of 10 kPa or more and 5000 kPa or less, and the adhesive layer temperature after light irradiation of 100° C. and a storage shear at a frequency of 1 Hz. The method for producing a pressure-sensitive adhesive article with a release film according to claim 12, wherein the elastic modulus (G′) is 1 kPa or more and 100 kPa or less. The mold release according to any one of claims 12 to 16, wherein the adhesive force of the adhesive layer to glass after light irradiation is 3 N/cm or more at -30°C and 3 N/cm or more at 30°C. A method for producing an adhesive article with a film. The method for producing a pressure-sensitive adhesive article with a release film according to any one of claims 12 to 17, wherein the haze of the pressure-sensitive adhesive layer after light irradiation is 150% or less is 2% or less. The said release film is equipped with the release layer containing fluorosilicone, The manufacturing method of the adhesive article with a release film as described in any one of Claims 12-18 characterized by the above-mentioned. (A) a photoactive catalyst, (B) a linear organopolysiloxane having an organic functional group bonded to a silicon atom and curable by the photoactive catalyst, and (C) a branched organopolysiloxane. A composition containing siloxane, wherein when the total amount of the (B) straight-chain organopolysiloxane and the (C) branched organopolysiloxane is 100 parts by mass, the (B) direct composition After adhering the two image display constituting members via a sheet having an adhesive layer made of a composition containing 5 to 70 parts by mass of a chain organopolysiloxane,
The pressure-sensitive adhesive layer after irradiation with light has a peak temperature of one or more loss tangents (Tan δ) in a range of −140° C. to −100° C. or lower and −50° C. to 100° C. or lower at a frequency of 1 Hz. And irradiating light through any one of the image display constituent members. 21. The method for producing a laminate for optical device configuration according to claim 20, wherein the composition further contains (D) a cross-linking agent. 22. The method for producing a laminate for optical device configuration according to claim 20, wherein the organic functional group is either a vinyl group or a (meth)acryloylalkenyl group. 23. The method for producing a laminated body for forming an optical device according to claim 20, wherein the composition has a melt viscosity at a temperature of 130° C. of 10 Pa·s or more and 5000 Pa·s or less. The adhesive layer after light irradiation has a storage shear modulus (G′) at a temperature of 30° C. and a frequency of 1 Hz of 10 kPa or more and 5000 kPa or less, and the adhesive layer temperature after light irradiation of 100° C. and a storage shear at a frequency of 1 Hz. The method for manufacturing a laminate for optical device configuration according to any one of claims 20 to 23, wherein the elastic modulus (G') is 1 kPa or more and 100 kPa or less. The optical device according to any one of claims 20 to 24, wherein the adhesive strength of the adhesive layer to glass after light irradiation is 3 N/cm or more at -30°C and 3 N/cm or more at 30°C. Method of manufacturing laminated body for constitution. The method for producing a laminate for optical device configuration according to any one of claims 20 to 25, wherein a haze of the pressure-sensitive adhesive layer after light irradiation is 150% or less is 2% or less.