KR101768307B1

KR101768307B1 - Silicone adhesive composition, silicone adhesive film prepared using the same and optical display apparatus comprising the same

Info

Publication number: KR101768307B1
Application number: KR1020150060934A
Authority: KR
Inventors: 유키나리 하리모토; 켄지 하마다; 김일진; 이우진
Original assignee: 삼성에스디아이 주식회사; 삼성전자주식회사
Priority date: 2015-04-29
Filing date: 2015-04-29
Publication date: 2017-08-16
Also published as: KR20160129219A

Abstract

(A) a silicone polymer having a (meth) acrylate group, (B) a silicone resin, (C) a silicone compound of the formula (1), a copolymer thereof or a mixture thereof, and (D) a photoinitiator A formed silicon adhesive film and an optical display device including the same are provided.

Description

TECHNICAL FIELD [0001] The present invention relates to a silicone adhesive composition, a silicone adhesive film formed therefrom, and an optical display device including the same. BACKGROUND ART [0002]

The present invention relates to a silicone adhesive composition, a silicone adhesive film formed therefrom, and an optical display device comprising the same.

The optical display device includes various flexible display devices such as a display unit including an organic light emitting device, a polarizing plate, a touch screen panel, and a window film. The above elements are adhered to each other by an adhesive film except for the case where they are self-adhesive. Therefore, the adhesive film should have good adhesion.

In recent years, as the development of flexible display devices has progressed, a good bending property has been demanded also in an adhesive film for sticking the above elements. In addition, conventional thermosetting adhesives including MQ silicone resin have been developed mainly for thermosetting compositions containing a radical reaction with a hydrosilylation reaction or a peroxide to increase the adhesive strength. However, the adhesive film produced therefrom has a limitation in satisfying both adhesion and bending properties. This is because, when the adhesive strength is increased, the modulus of the adhesive film is increased and the bending property is lowered. In addition, thermosetting compositions generally require high curing temperatures. Therefore, after the pressure-sensitive adhesive composition is coated on the release film, the release film may be deformed upon release, so that the flatness of the pressure-sensitive adhesive film is not good and the production may not be easy.

The background art of the present invention is disclosed in Korean Patent Publication No. 2007-0104379.

A problem to be solved by the present invention is to provide a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film having good bending properties.

Another object of the present invention is to provide a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film having both bending property and adhesive strength.

Another object of the present invention is to provide a silicone pressure-sensitive adhesive composition which is free from deformation of a release film and can be easily released from a release film.

Another object of the present invention is to provide a silicone adhesive composition capable of realizing a silicone adhesive film having excellent durability and light transparency.

Another object of the present invention is to provide a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film which prevents cracks, bubbles, exfoliation, peeling, or the like from occurring in a flexible display device.

Silicone pressure-sensitive adhesive composition of the present invention (A) (meth) silicone polymer, (B) M unit having an acrylate (R ') (R ") (R"') SiO 1/2 ( wherein, R ', R " And R "'each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms) and a Q unit SiO _4/2 , (C) a silicone compound represented by the following formula (1), a copolymer thereof, And (D) a photoinitiator:

&Lt; Formula 1 >

(Wherein X, R ¹ , R ² , R ³ and a are the same as in the detailed description of the present invention).

The silicone adhesive film of the present invention has a storage modulus of 0.05 MPa to 1.0 MPa at -20 캜, a storage modulus of 0.01 MPa to 0.10 MPa at 80 캜, a content of C = O bond relative to silicon (Si) of 0.3 mol% 5.0 mole%.

The silicon adhesive film of the present invention is produced by preparing a specimen in which a polyester film (thickness: 100 mu m), the silicon adhesive film (thickness: 25 mu m to 100 mu m) and an aluminum foil When a dynamic bending test rod (radius: 3 mm) is placed on the aluminum foil surface and the bending test is repeated with the specimen folded about the rod as one cycle, the minimum number of cycles in which cracks are generated in the aluminum foil is 900 or more , And the silicon adhesive film may have a content of C = O bond of 0.3 mol% to 5.0 mol% with respect to silicon (Si).

The silicone adhesive film of the present invention comprises 45 to 65% by weight of a copolymer of a silicone polymer having (A) a (meth) acrylate group and (C) a silicone compound of the following formula (1), a copolymer thereof or a mixture thereof; And (B) M units (R ') (R ") (R"') SiO _{1/2 wherein} R ', R "and R'" are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms ) And 35 wt% to 55 wt% of a silicone resin consisting of Q units SiO _4/2 :

&Lt; Formula 1 >

(Wherein X, R ¹ , R ² , R ³ , and a are the same as in the detailed description of the present invention).

The optical display device of the present invention may include the silicon adhesive film.

The present invention provides a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film having good bending properties.

The present invention provides a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film having both bending property and adhesive force.

The present invention provides a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive film having good durability and light transparency.

The present invention provides a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film which prevents cracks, bubbles, exfoliation, or entanglement from occurring in a flexible display device.

The present invention provides a silicone pressure-sensitive adhesive composition capable of realizing a silicone pressure-sensitive adhesive film which is free from deformation of a release film and easy to release from a release film.

The present invention provides a silicone adhesive film made of the silicone adhesive composition and an optical display device including the same.

1 is a cross-sectional view of a flexible display device according to an embodiment of the present invention.
2 is a cross-sectional view of a flexible display device according to another embodiment of the present invention.
3 is a cross-sectional view of a flexible display device according to another embodiment of the present invention.

Embodiments of the present application will now be described in more detail with reference to the accompanying drawings. However, the techniques disclosed in this application are not limited to the embodiments described herein but may be embodied in other forms. It should be understood, however, that the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art. In the drawings, the width, thickness, and the like of the components are enlarged in order to clearly illustrate the components of each device. Like numbers refer to like elements throughout the several views.

The terms "upper" and "lower" in this specification are defined with reference to the drawings, wherein "upper" may be changed to "lower", "lower" What is referred to as "on" may include not only superposition, but also intervening other structures in the middle. On the other hand, what is referred to as "directly on" or "directly above "

A plurality of adhesive films (thickness: 100 mu m) were laminated and cut to produce circular specimens having a thickness of 1 mm and a diameter of 8 mm, and a storage elasticity meter (ARES, (Temperature: -25 ° C to + 90 ° C, heating rate: 5 ° C / min) using a temperature sweep test (strain 1%, normal force 3N, And 80 ° C, respectively. The adhesive film can be prepared by coating the pressure-sensitive adhesive composition on a release film, curing the ultraviolet ray in an oxygen-shielded state, and releasing it from the release film, but is not limited thereto.

As used herein, "(meth) acrylic" means acrylic and / or methacrylic.

As used herein, the term " unsubstituted or substituted "means that at least one of the hydrogen atoms of the functional group is a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a hydroxyl group, an amino group, a C6 to C10 aryl group, A cyano group, a cycloalkyl group of C3 to C10, or an arylalkyl group of C7 to C10.

As used herein, the term "silicone pressure sensitive adhesive composition" may be expressed as "pressure sensitive adhesive composition".

In the present specification, the term "silicone adhesive film" may be referred to as "adhesive film".

Hereinafter, a silicone pressure sensitive adhesive composition according to an embodiment of the present invention will be described.

A silicone pressure sensitive adhesive composition according to an embodiment of the present invention includes a silicone polymer having a (meth) acrylate group; Silicone resin; A silicone compound of the formula (1), a copolymer thereof or a mixture thereof; And photoinitiators:

&Lt; Formula 1 >

(Wherein R ¹ , R ² , R ³ , X and a are as described below).

The silicone pressure sensitive adhesive composition according to this embodiment is a silicone polymer having a (meth) acrylate group; Silicone resin; And a silicone compound represented by Formula 1, a copolymer thereof, or a mixture thereof. As a result, the silicone pressure sensitive adhesive composition according to this embodiment can form an adhesive film which is easy to release from the release film. Further, the silicone pressure sensitive adhesive composition according to this embodiment can be used in a flexible optical display device by forming an adhesive film having good bending property even at a low temperature, a room temperature and / or a high temperature. The "good bending" is described below.

The silicone pressure sensitive adhesive composition according to this embodiment is a silicone polymer having a (meth) acrylate group; Silicone resin; The silicone compound of Formula 1, a copolymer thereof, or a mixture thereof; And photoinitiators. As a result, the pressure-sensitive adhesive composition according to this embodiment is easily photocured and can form an adhesive film without deforming the release film.

The silicone pressure sensitive adhesive composition according to this embodiment may have a viscosity of 2,000 cps to 500,000 cps at 25 ° C. Within the above range, the coating property of the pressure-sensitive adhesive composition is good, and the production of the pressure-sensitive adhesive film can be facilitated.

In the present invention, the silicone polymer having a (meth) acrylate group, the silicone resin, the silicone compound of the formula (1), and the photoinitiator are different from each other.

(A) a silicone polymer, (B) a silicone resin, (C) a silicone compound of the formula (1), a copolymer thereof or a mixture thereof (hereinafter may be referred to as a ' D) Photoinitiator will be described in detail.

(A) a silicone polymer

The silicone polymer together with the silicone compound of the formula (1) facilitates the formation of an adhesive film during the photo-curing of the silicone pressure-sensitive adhesive composition and can form an adhesive film easily releasing from the release film. The "release film" may include a polyester film including a fluorine-coated polyethylene terephthalate film, a polyethylene terephthalate film treated with fluorosilicone, and the like.

The silicone polymer has a storage modulus in a predetermined range at a specific temperature together with the silicone compound represented by the formula (1), and can form an adhesive film having "good bending" when used in a flexible optical display device.

The "good bending" was performed by preparing a specimen laminated in this order of a polyester film (thickness: 100 m) / adhesive film (thickness: 25 m to 100 m) / bending member A dynamic bending test rod (radius: 3 mm, flexural strength measuring device, manufacturer SDI) was placed on the bending member surface, and the test piece was placed on the bending member surface The number of cracks occurring in the bending member due to naked eye is 900 cycles or more when the bending cycle is repeated with 1 cycle. The adhesive film having a minimum cycle number means that the stress of the bending member due to bending can be easily relaxed, which means that the adhesive film can be used in a flexible display device. Specifically, the silicone adhesive film according to the present embodiment exhibits 900 cycles or more, specifically 900 to 2,000 cycles at the time of bending evaluation, and is excellent in bending property and flexibility, so that it can be used in a flexible display device. The adhesive film can be produced by coating the pressure-sensitive adhesive composition on a release film, curing the ultraviolet ray in an oxygen-cut state and separating the release film from the release film, but is not limited thereto. The bending member is an aluminum foil (manufacturer: Lotte). The aluminum foil may be a means for representing a transparent conductive film such as a metal nanowire-containing film, a polarizing plate, an OLED driving layer, or the like.

The silicone polymer is a photocurable silicone polymer and may include (meth) acrylate-based silicone polymers containing at least one (meth) acrylate group.

The silicone polymer may be a linear silicone polymer. As a result, a pressure-sensitive adhesive film having good bending properties can be produced.

The silicone polymer may comprise a silicone polymer having an alkyl group having a (meth) acrylate group.

In one embodiment, the silicone polymer comprises one or more D units R'R "SiO _2/2 wherein R 'and R" are each independently selected from the group consisting of an unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 A substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 arylalkyl group, or a C1 to C20 alkoxy group having a (meth) acrylate group, C10 alkyl group, at least one of R 'and R " (C1 to C10 alkyl group having a (meth) acrylate group).

In another embodiment, the silicone polymer comprises an alkyl group having a (meth) acrylate group at the terminal and one or more D units R "R""" SiO _{2/2 wherein} R " Or a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 2 to C 10 alkenyl group, a substituted or unsubstituted C 2 to C 10 alkynyl group, a substituted or unsubstituted C 6 to C 20 aryl group, A substituted C7 to C20 arylalkyl group), and the alkyl group may include a silicone polymer connected to the D unit.

In yet another embodiment, the silicone polymer comprises at least one of the D units R'R "SiO2 _/ D units "R""" SiO _2/2 .

Specifically, the silicone polymer may be represented by any one of the following general formulas (2) to (4)

(2)

(3)

(In the above Chemical Formulas 2 to 3,

R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ each independently represent a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group , A substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C7 to C20 arylalkyl group,

R ⁶ and R ⁷ each independently represent a substituted or unsubstituted C1 to C10 alkylene group,

R ⁸ and R ⁹ are each independently hydrogen or a methyl group,

and n is an integer of 1 to 1000)

&Lt; Formula 4 >

(In the formula 4,

Each of R ⁴ , R ⁵ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is independently a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 2 to C 10 A substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C7 to C20 arylalkyl group,

R < ⁶ > is a substituted or unsubstituted C1 to C10 alkylene group,

R ⁸ is hydrogen or a methyl group,

n is an integer of 0 to 200,

and m is an integer of 2 to 7).

Specifically, in formulas (2) and (3), R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ each independently represent a C1 to C5 alkyl group, more specifically, a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group. Specifically, in formulas (2) and (3), R ⁶ and R ⁷ each independently represent a substituted or unsubstituted C 1 to C 5 alkylene group, more specifically, an ethylene group, a propylene group, a butylene group, or a pentylene group.

Specifically, each of R ⁴ , R ⁵ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ in Formula 4 is independently a C1 to C5 alkyl group, A propyl group, a butyl group or a pentyl group. Specifically, in the general formula (4), R ⁶ may each independently be a substituted or unsubstituted C1 to C5 alkylene group, more specifically, an ethylene group, a propylene group, a butylene group, or a pentylene group. Specifically, in Formula 4, m may be an integer of 2 to 5.

The content of the (meth) acrylate group relative to silicon (Si) in the silicone polymer may be from 0.20 mol% to 2.5 mol%, specifically from 0.25 mol% to 2.0 mol%. Within this range, it is possible to produce a pressure-sensitive adhesive film which exhibits remarkable bending properties and exhibits a high degree of flexibility, and has a high adhesive force even at room temperature and / or high temperature, thereby eliminating lifting, peeling or bubbling between the pressure-sensitive adhesive film and an adherend surface. The "adherend" may be an element for a flexible display including a transparent electrode film including a window film including a plastic or the like, a polarizing plate, a metal nanowire, an organic light emitting element including a flexible substrate, Do not. The "content of the (meth) acrylate group relative to the silicon (Si)" (the weight average molecular weight of the silicone polymer - (meth) acrylate group of one silicon polymer (Meth) acrylate groups in the silicone polymer (A) and the total number of (meth) acrylate groups in one silicone polymer (A) B) according to the following formula 1 and expressed in mol% units:

Content of (meth) acrylate group relative to silicon (Si) = (B) / (A + B) x 100

The silicone polymer may have a weight average molecular weight (Mw) of 10,000 to 100,000, specifically 20,000 to 80,000. In the above range, there is an effect of producing a pressure-sensitive adhesive film exhibiting good bending and having excellent flexibility.

The silicone polymer may have a viscosity at 25 占 폚 of 1,000 cSt to 50,0000 cSt, specifically 2,000 cSt to 50,000 cSt. Within this range, it may be easy to produce a film of the pressure-sensitive adhesive composition.

The silicone polymer may be contained in the silicone adhesive composition alone or in a mixture of two or more.

The silicone polymer may be included in an amount of 40% by weight to 60% by weight based on the total weight of (A), (B), (C) and (D) In the above range, it is possible to produce an adhesive film exhibiting good bending, having good flexibility, good adhesive strength and durability. Specifically, the silicone polymer may be contained in an amount of 40% by weight to 50% by weight based on the total weight of (A), (B), (C)

(B) a silicone resin

The silicone resin can increase the adhesive strength of the pressure-sensitive adhesive film made of the pressure-sensitive adhesive composition. The silicone resin can ensure a stable adhesive force even when the ultraviolet curing conditions are changed during ultraviolet curing of the pressure-sensitive adhesive composition.

The silicone resin may be a network-type silicone resin.

Specifically, the silicone resin may be an MQ silicone resin essentially comprising a monovalent siloxane unit M and a tetravalent siloxane unit Q. More specifically, the silicone resin is a copolymer of M units (R ') (R ") (R"') SiO _{1/2 wherein} R ', R "and R'" each independently represent a monovalent aliphatic saturated hydrocarbon group, Monovalent aromatic hydrocarbon group or monovalent aliphatic unsaturated hydrocarbon group) and a Q unit SiO _4/2 . For example, the monovalent aliphatic saturated hydrocarbon group may be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, the monovalent aromatic hydrocarbon group may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms. For example, a monovalent aliphatic unsaturated hydrocarbon group is an alkenyl group having an unsaturated group at an end, and an unsaturated group exists at two carbon atoms furthest from the silicon atom. For example, the monovalent aliphatic unsaturated hydrocarbon group may be an alkenyl group having 2 to 10 carbon atoms.

The silicone resin may be in a liquid or solid state, and may be adjusted depending on the ratio of the M unit to the Q unit in the silicone resin. Specifically, the ratio of the number of moles of M units to the number of moles of Q units in the silicone resin may be 0.5: 1 to 1.5: 1, specifically 0.6: 1 to 1: 1. Within the above range, an adhesive film which can be mixed well with the silicone polymer, the compound of formula (1) and the like and has good durability can be produced.

The silicone resin may have a weight average molecular weight of 1,000 to 50,000, specifically 2,000 to 10,000. In the above range, it is possible to produce an adhesive film exhibiting good bending, having good flexibility, good adhesive strength and durability.

The silicone resin may be contained in the silicone pressure-sensitive adhesive composition alone or in combination of two or more.

The silicone resin may be contained in an amount of 35% by weight to 55% by weight based on the total weight of (A), (B), (C) and (D). In the above range, the cohesive force and adhesive strength of the adhesive film can be increased to reduce the peeling of the adhesive film from the adherend surface and the occurrence of cracks on the adherend surface, and flexibility can be imparted to the adhesive film to enable use of the adhesive film in flexible display devices . Specifically, the silicone resin may specifically include 45% by weight to 50% by weight based on the total weight of (A), (B), (C) and (D).

A silicone compound of formula (I), a copolymer thereof or a mixture thereof

The silicone compound of formula (I), a copolymer thereof, or a mixture thereof, together with the above-mentioned silicone polymer, can form an adhesive film having the above-mentioned easy-to-mold bending.

In addition, the silicone compound of the formula (1), the copolymer thereof or the mixture thereof can realize a pressure-sensitive adhesive film having sufficient adhesion force together with the silicone polymer and the silicone resin, even if it does not contain an additional adhesion promoting agent.

The silicone compound represented by the general formula (1), a copolymer thereof, or a mixture thereof may be contained in the pressure-sensitive adhesive composition alone or in a mixture of two or more thereof.

The silicone compound of formula (1) may be represented by the following formula (1)

&Lt; Formula 1 >

(In the formula 1,

X is a photocurable functional group,

R ¹ represents a substituted or unsubstituted C1 to C12 alkylene group or * - (R ') - O - ** (* represents a connecting site to X in the formula (1) , R 'is a substituted or unsubstituted C1 to C12 alkylene group)

R ² is a substituted or unsubstituted C1 to C12 alkyl group,

R ³ is a substituted or unsubstituted C1 to C12 alkyl group or a group represented by the following formula (1-1)

&Lt; Formula 1-1 >

(In the above formula 1-1,

* Is the connecting part of the element,

R ^a , R ^b , R ^c , R ^d , R ^e , R ^f and R ^g are each independently a substituted or unsubstituted C1 to C10 alkyl group,

and m is an integer of 0 to 200)

and a is an integer of 0 to 3).

In Formula (1), X may be a (meth) acrylate group. As a result, crosslinking with the silicone polymer can be facilitated.

In Formula (1), R ¹ may be a substituted or unsubstituted C1 to C10 alkylene group, specifically, a methylene group, an ethylene group, a propylene group, a butylene group, or a pentylene group.

In formula (1), R ² may be a substituted or unsubstituted C1 to C10 alkyl group, specifically a C1 to C5 alkyl group, more specifically a methyl group.

In formula 1, R ³ is an unsubstituted C1 to alkyl groups of C10, C1 to alkyl groups substituted with a C1 to C10 alkoxy group of C5, or R ^a, R ^b, R ^c, R ^d, R ^e, R ^f and R ^g is independently a substituted or unsubstituted C1 to C5 alkyl group, more specifically a methyl group.

Specifically, the silicone compound of formula (1) is selected from the group consisting of 3- (meth) acryloxypropyldimethylmethoxysilane, 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, 3- (Meth) acryloxymethyltrimethoxysilane, 3- (meth) acryloxymethyltrimethoxysilane, 3- (meth) acryloxymethyltrimethoxysilane, 3- (Meth) acryloxypropyltriethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, 3- Methoxyethoxy) silane. &Lt; / RTI >

The silicone compound of Formula 1 may include a compound wherein R ^a , R ^b , R ^c , R ^d , R ^e , R ^f, and R ^g in Formula 1-1 are methyl groups and X is a (meth) have. At this time, the silicone compound of formula (1) may have a weight average molecular weight of 1,000 to 50,000, specifically 1,500 to 10,000.

Specifically, m in the formula (1-1) may be an integer of 5 to 200, for example, 5 to 50. As m becomes larger, the compound of the formula (1) or the copolymer thereof becomes a linear shape, and as a result, the adhesive film becomes soft and can exhibit good bending properties.

In one embodiment, the pressure sensitive adhesive composition may comprise a silicone compound of formula (1). At this time, the silicone compound of the formula (1) may be included singly or in combination of two or more. As a result, an adhesive film having good bending property, durability, and adhesion strength can be produced, and a pressure-sensitive adhesive composition having excellent coating properties can be produced.

In another embodiment, the pressure sensitive adhesive composition may comprise a copolymer of the silicone compound of formula (I).

The copolymers may be included in the pressure-sensitive adhesive composition alone or in combination of two or more. The copolymer of the silicone compound of formula (1) can be formed by copolymerizing the silicone compound of formula (1) with a conventional polymerization. Specifically, the copolymer can be formed by adding a photoinitiator to the silicone compound of formula (1) and polymerizing a photo-curing functional group, for example, between (meth) acrylate groups. The photoinitiator may comprise conventional photoinitiators known to those skilled in the art. Examples of the photoinitiator include 2-hydroxy-2-methylpropiophenone and the like (e.g., trade name DC1173), 2,2-dimethoxy 1,2-diphenyl ethan-1-one and the like (for example, trade names Irgacure 651, IC651), 1-hydroxycyclohexyl phenyl ketone (e.g., Irgacure 184, IC184), or mixtures thereof. The copolymer may have a weight average molecular weight of 1,000 to 50,000. In the above range, coating can be smoothly performed in the production of an adhesive film.

In another embodiment, the pressure sensitive adhesive composition can comprise a mixture of a silicone compound of formula (1) and a silicone compound of formula (1). As a result, an adhesive film having remarkably excellent bending properties can be produced.

A mixture of the silicone compound of formula (1) and the silicone compound of formula (1) may be prepared by partial polymerization of the silicone compound of formula (1). Specifically, the mixture may be prepared by adding a photoinitiator to the silicone compound of formula (1) and polymerizing the mixture at a polymerization degree of more than 10% but not more than 90%, specifically 20% to 50%. The photoinitiator may comprise conventional photoinitiators known to those skilled in the art. The photoinitiator may be used in the same manner as the photoinitiator described above. The degree of polymerization can be measured by conventional methods known to those skilled in the art. The mixture is a viscous liquid and may have a viscosity of from 1,000 cps to 10,000 cps at 25 占 폚. Within the above range, the adhesive strength and durability of the pressure-sensitive adhesive film may be improved.

The silicone compound of formula (I), the copolymer thereof or the mixture thereof may be contained in an amount of 0.1 to 10% by weight based on the total weight of (A), (B), (C) and (D). In the above range, there may be an effect of improving the bending property and the recovery force. The silicone compound of formula (I), a copolymer thereof or a mixture thereof is specifically 0.1% by weight to 5% by weight based on the total weight of (A), (B), (C) % To 2% by weight.

Photoinitiator

The photoinitiator may photo-cure (A) a silicone polymer, (C) a silicone compound of Formula 1, a copolymer thereof, or a mixture thereof.

The photoinitiator may comprise conventional photoinitiators known to those skilled in the art. Specifically, the photoinitiator may include at least one of 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

The photoinitiator may be contained in the adhesive composition alone or in a mixture of two or more.

The photoinitiator may be included in an amount of 0.1 wt% to 5.0 wt% based on the total weight of (A), (B), (C), and (D). Within this range, it is possible to sufficiently cure the silicone polymer, the silicone compound of the formula (1), the copolymer thereof or the mixture thereof, and the remaining amount of the photoinitiator can be prevented from lowering the transparency of the adhesive film. The photoinitiator may be contained in an amount of 0.3% by weight to 1.0% by weight based on the total weight of (A), (B), (C) and (D).

The silicone pressure sensitive adhesive composition according to an embodiment of the present invention can be formed into a solventless type solventless type. For example, when the silicone pressure sensitive adhesive composition is of the non-solvent type, the weight% is preferably in the range of (A) silicone polymer, (B) silicone resin, (C) silicone compound, Based on the total weight of the photoinitiator.

The silicone pressure sensitive adhesive composition according to an embodiment of the present invention may further include a solvent. By further including a solvent, the coating property of the pressure-sensitive adhesive composition can be enhanced.

The silicone pressure sensitive adhesive composition according to an embodiment of the present invention may further include conventional additives in a range not affecting the performance of the pressure sensitive adhesive composition. Specifically, the additive may further include a silane coupling agent, an antistatic agent, a releasing agent, an antioxidant, a heat stabilizer, and the like.

Hereinafter, a silicon adhesive film according to an embodiment of the present invention will be described.

The silicone adhesive film according to an embodiment of the present invention has a storage modulus in a predetermined range at a specific temperature, and exhibits good bending property, so that it can be used in a flexible optical display device. Specifically, the silicone adhesive film may have a storage modulus of 0.05 MPa to 1.0 MPa at -20 캜. When used in a flexible display device in the above range, good bending properties can be exhibited at a low temperature. The silicone adhesive film may have a storage modulus of 0.01 MPa to 0.10 MPa at 25 占 폚. When used in a flexible optical display device in the above range, good bending properties can be exhibited at room temperature. The silicone adhesive film may have a storage modulus of 0.01 MPa to 0.10 MPa at 80 캜. When used in a flexible optical display device in the above range, good bending properties can be exhibited at a high temperature. More specifically, the pressure-sensitive adhesive film may have a storage modulus of 0.05 MPa to 0.5 MPa at -20 ° C, a storage modulus of 0.02 MPa to 0.1 MPa at 25 ° C, and a storage modulus of 0.02 MPa to 0.1 MPa at 80 ° C.

The silicone adhesive film may have a peel strength of 500 gf / in or more, specifically 600 gf / in to 1000 gf / in for a PET (polyethylene terephthalate) film corona-treated at 25 ° C. The adhesive film may have a peel strength of 200 gf / in or more, specifically 300 gf / in to 700 gf / in for a corona-treated PET (polyethylene terephthalate) film at 60 ° C. In the peel strength range, adhesiveness is good and can be used in a flexible display device.

The "corona treatment" includes, but is not necessarily limited to, treating the PET film twice, while discharging the plasma at a dose of 78 doses using a now plasma.

The thickness of the silicone adhesive film may be 15 占 퐉 to 200 占 퐉, specifically, 25 占 퐉 to 100 占 퐉. In the above range, it can be used in an optical display device.

The silicone adhesive film may be optically transparent. Specifically, the adhesive film may have a light transmittance of 90% or more, specifically 90% to 100% at a wavelength of 400 nm to 800 nm. In the above range, it can be used in an optical display device.

The silicone adhesive film exhibits 900 cycles or more, specifically 900 to 2,000 cycles at the time of the above-described bending evaluation, so that good bending properties can be exhibited.

The silicone adhesive film comprises (A) a silicone polymer having (meth) acrylate groups; And (C) a silicone compound of the above formula (1), a copolymer thereof or a mixture thereof (hereinafter referred to as a "copolymer of (A) and (C)") and (B) have. The copolymers of (A) and (C) can provide good bending properties to the adhesive film. The silicone resin can increase the adhesion of the adhesive film. The silicone adhesive film may contain 45% by weight to 65% by weight, specifically 50% by weight to 55% by weight of a copolymer of (A) and (C). The silicone adhesive film may contain 35 wt% to 55 wt%, specifically 45 wt% to 50 wt% of silicone resin. Within this range, both good bending and adhesion can be exhibited.

The silicon adhesive film may have a content of C═O bond of 0.3 mol% to 5.0 mol%, more specifically 0.3 mol% to 1.0 mol%, relative to silicon (Si) by Solid-NMR. In this range, film formation is easy, and good bending properties can be obtained. The total number of moles (A) of silicon M units, D units and Q units in the silicone adhesive film was determined by using Solid-NMR, and the content of C = O (B) of the bond of the compound represented by the formula

Content of C = O bond to silicon (Si) = B / A x 100

In one embodiment, a silicone adhesive film may be formed from a silicone adhesive composition according to one embodiment of the present invention. Specifically, the pressure-sensitive adhesive film can be produced by coating a pressure-sensitive adhesive composition onto a release film to a predetermined thickness and curing the pressure-sensitive adhesive composition. The release film is not particularly limited, but may include a fluorine-coated polyester film. Photocuring can be produced by irradiating with a UV wavelength of, for example, 200 nm to 380 nm at an intensity of 100 mJ / cm ² to 500 mJ / cm ² for 1 minute to 60 minutes. During photocuring, a release film may be placed on the coating layer to block contact with oxygen and photocured.

Hereinafter, a display member according to an embodiment of the present invention will be described.

The display member according to an embodiment of the present invention includes a silicon adhesive film and an optical member formed on at least one side of the silicon adhesive film, wherein the silicon adhesive film includes a silicon adhesive film according to an embodiment of the present invention . The silicone adhesive film has good bending properties and the display member can exhibit good bending properties. The optical member may include at least one of a window film, a polarizing plate, and a transparent conductive film. The transparent conductive film may include, but is not limited to, a metal nanowire-containing film and the like.

Hereinafter, an optical display device according to an embodiment of the present invention will be described.

The optical display device according to an embodiment of the present invention may include the silicon adhesive film of the embodiment of the present invention. Specifically, the optical display device may include a flexible display device.

Hereinafter, a flexible display device according to an embodiment of the present invention will be described with reference to FIG. 1 is a cross-sectional view of a flexible display device according to an embodiment of the present invention.

1, a flexible display device 100 according to an exemplary embodiment of the present invention includes a display unit 110, an adhesive layer 120, a polarizer 130, a touch screen panel 140, and a flexible window film 150, and the adhesive layer 120 may include a silicone adhesive film according to an embodiment of the present invention.

The display unit 110 is for driving the flexible display device 100 and may include an optical element including an OLED, an LED, or an LCD device formed on a substrate and a substrate. Although not shown in FIG. 1, the display unit 110 may include a lower substrate, a thin film transistor, an organic light emitting diode, a planarization layer, a protective layer, and an insulating layer.

The polarizing plate 130 may implement polarizing of the inner light or prevent reflection of the external light to realize the display or increase the contrast ratio of the display. The polarizing plate may be composed of a polarizer alone. Or the polarizing plate may include a polarizing film and a protective film formed on one or both sides of the polarizing film. Or the polarizing plate may include a polarizer and a protective coating layer formed on one or both sides of the polarizer. The polarizer, the protective film, and the protective coating layer may be conventional ones known to those skilled in the art.

The touch screen panel 140 senses a change in capacitance caused when a conductor such as a human body or a stylus touches, and generates an electrical signal. The display unit 110 can be driven by this signal. The touch screen panel 140 may include a first sensor electrode and a second sensor electrode formed between the first sensor electrode and the first sensor electrode, which are formed by patterning a conductive conductive material. have. The conductor for the touch screen panel 140 may include, but is not limited to, metal nanowires, conductive polymers, carbon nanotubes, and the like.

The flexible window film 150 may be formed at the outermost portion of the flexible display device 100 to protect the display device.

1, an adhesive layer is further formed between the polarizer 130 and the touch screen panel 140 and / or between the touch screen panel 140 and the flexible window film 150, thereby forming a polarizing plate, a touch screen panel, It is possible to strengthen the bonding between the window films. In one embodiment, the adhesive layer may be formed of a pressure sensitive adhesive composition comprising a (meth) acrylate based resin, a curing agent, an initiator, and a silane coupling agent. In other embodiments, the adhesive layer may comprise an adhesive film according to one embodiment of the present invention.

Further, although not shown in FIG. 1, a polarizing plate is further provided under the display unit 110, so that polarized light can be realized.

Hereinafter, a flexible display device according to another embodiment of the present invention will be described with reference to FIG. 2 is a cross-sectional view of a flexible display device according to another embodiment of the present invention.

2, a flexible display device 200 according to another embodiment of the present invention includes a display unit 110, an adhesive layer 120, a touch screen panel 140, a polarizer 130, a flexible window film 150 , And the adhesive layer 120 may include an adhesive film according to an embodiment of the present invention. Except that the positions of the touch screen panel 140 and the polarizing plate 130 are changed. The display device of the present invention is substantially the same as that of the flexible display device of the embodiment of the present invention.

Although not shown in FIG. 2, an adhesive layer is further formed between the touch screen panel 140 and the polarizer 130 and / or between the polarizer 130 and the flexible window film 150, thereby increasing the mechanical strength of the display device . In one embodiment, the adhesive layer may be formed of a pressure sensitive adhesive composition comprising a (meth) acrylate based resin, a curing agent, an initiator, and a silane coupling agent. In another embodiment, the adhesive layer may comprise an adhesive film according to an embodiment of the present invention.

Further, although not shown in FIG. 2, a polarizing plate is further formed under the display unit 110 to induce the polarization of the internal light to improve the display image.

Hereinafter, a flexible display device according to another embodiment of the present invention will be described with reference to FIG. 3 is a cross-sectional view of a flexible display device according to another embodiment of the present invention. 3, the flexible display device 300 according to another embodiment of the present invention includes a display 110 ', an adhesive layer 120, and a flexible window film 150, and the adhesive layer 120' May include an adhesive film according to an embodiment of the present invention. The display unit 110 'may include a substrate and an optical element including an LCD, OLED, or LED device formed on the substrate, and the display unit 110' may have a touch screen panel formed therein.

Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to embodiments of the present invention. However, the following examples are provided to aid understanding of the present invention, and the scope of the present invention is not limited to the following examples.

Specific specifications of the components used in Examples and Comparative Examples are as follows.

A. Silicone polymer: DMS-R31 (polydimethylsiloxane polymer having a methacryloxypropyl group at both terminals, Gelest, weight average molecular weight: 25,000, methacrylate group relative to silicon (Si) 0.6 mol%)

B. Silicone resin: MQ silicone resin prepared according to US3627851 with trimethylchlorosilane and water soluble silica sol. (CH ₃ ) ₃ SiO _1/2 : SiO _4/2 molar ratio of 0.8: 1.0 and Mw = 4,500 (measured by GPC).

C. Silicone compounds of formula (I) or copolymers thereof or mixtures thereof

C-1: SIA190 (acryloxypropyldimethylmethoxysilane, Gelest)

C-2: Viscous liquid prepared in the following Production Example 1

C-3: Viscous liquid prepared in the following Production Example 2

D. Photoinitiator: DC1173 (Ciba)

Production Example 1

100 parts by weight of SIA190 (3-acryloxypropyldimethylmethoxysilane, Gelest), 100 parts by weight of SIA198 (3-acryloxypropylmethyldimethoxysilane, Gelest) and 2 parts of 2-Hydroxy-2-methylpropiophenone, CIBA ) Were mixed in a glass container. The oxygen in the glass container was replaced with nitrogen gas, and the mixture was partially polymerized by irradiation with ultraviolet rays for 6 seconds in a low pressure lamp (Sylvania BL Lamp) at a power of 105 mJ / cm ² to obtain a viscous liquid. The viscous liquid was used as silicone compound C-2.

Production Example 2

100 parts by weight of SIA190, 100 parts by weight of SIA198, 50 parts by weight of APMS45 (polydimethylsiloxane having monoacryloxy group, Mw: 2000, KCC) and 0.1 part by weight of 2-Hydroxy-2-methylpropiophenone (CIBA) And mixed in a container. Oxygen in the glass container was replaced with nitrogen gas, and the mixture was partially polymerized by irradiating ultraviolet rays for 10 seconds with a low pressure lamp (Sylvania BL Lamp) at a power of 105 mJ / cm ² to obtain a viscous liquid. The viscous liquid was used as the silicone compound C-3.

Example One

49 parts by weight of DMS-R31, 50 parts by weight of MQ silicone resin, 0.5 part by weight of silicone compound C-1 and 0.5 part by weight of a photoinitiator were mixed in a glass container to prepare a pressure-sensitive adhesive composition. The release film of a fluorine coating a pressure-sensitive adhesive composition made of polyethylene terephthalate film (thickness: 50㎛) in thickness and coated with 100㎛, covering the same release film, 105mJ / cm ² intensity low-pressure lamp (Sylvania BL lamp, the wavelength of: 356 nm) for 6 minutes to produce a pressure-sensitive adhesive sheet in which an adhesive film (thickness: 100 占 퐉) was formed between the release films.

Examples 2 to 4

A pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1, except that the components and contents of A, B, C and D were changed as shown in Table 1 (unit: parts by weight).

Comparative Example 1 and Comparative Example 2

A pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1, except that the components and contents of A, B, C and D were changed as shown in Table 1 below.

The pressure-sensitive adhesive composition and ultraviolet irradiation time of Examples and Comparative Examples are shown in Table 1 below. The pressure-sensitive adhesive compositions and pressure-sensitive adhesive sheets of Examples and Comparative Examples were evaluated for physical properties shown in Table 1 below.

(1) film-forming or not: the pressure-sensitive adhesive composition of the fluorine-containing release film of polyethylene terephthalate film (thickness: 50㎛) in thickness and coated with 100㎛ between a low-pressure lamp of 105mJ / cm ² intensity (Sylvania BL lamp, wavelength: 356nm ) For 6 minutes and evaluated by the following criteria.

◎: Adhesive film is easily released when viewed from the naked eye.

X: No film formed when viewed from the naked eye.

(2) Storage elastic modulus: Both release films were separated from the pressure-sensitive adhesive sheet produced in Examples and Comparative Examples to obtain an adhesive film. A plurality of adhesive films (thickness: 100 占 퐉) were laminated and cut to produce circular specimens having a thickness of 1 mm and a diameter of 8 mm. The specimens were subjected to a temperature sweep test (strain 1%, normal force 3N, 1 rad / s, -25 ° C to + 90 ° C, heating rate 5 ° C / min) using a storage elasticity tester And the storage elastic moduli were obtained at -20 ° C, 25 ° C and 80 ° C, respectively.

(3) Peel strength at 25 캜: A pressure-sensitive adhesive sheet produced in Examples and Comparative Examples was obtained. Treatment with corona (total dose: 156 doses) was performed on a PET (polyethylene terephthalate) film of 10 cm x 20 cm (width x length) while discharging the plasma with a dose of 78 doses using a corona processor (now plasma) After the release film was peeled off from the pressure sensitive adhesive sheet, the pressure sensitive adhesive film (thickness: 100 μm) was adhered to the corona-treated PET film and aged at 25 ° C. for 24 hours to prepare a specimen. The specimen was measured for 90 ° peel strength on a corona-treated PET film at 25 ° C at a rate of 50 mm / min using a Texture Analyzer (TA.XT_Plus, Stable Micro System).

(4) Peel strength at 60 캜: A pressure-sensitive adhesive sheet produced in Examples and Comparative Examples was obtained. Treatment with corona (total dose: 156 doses) was performed on a PET (polyethylene terephthalate) film of 10 cm x 20 cm (width x length) while discharging the plasma with a dose of 78 doses using a corona processor (now plasma) The adhesive film (thickness: 100 mu m) was adhered to the corona-treated PET film, aged at 25 DEG C for 24 hours, and then heated at 60 DEG C for 30 minutes The samples were aged in an autoclave. The 90 ° peel strength of the corona-treated PET film was measured at 60 ° C at 50 mm / min using a Texture Analyzer (TA.XT_Plus, Stable Micro System).

(5) Light transmittance: Both release films were separated from the pressure-sensitive adhesive sheet produced in Examples and Comparative Examples to obtain an adhesive film (thickness: 100 m). The light transmittance of the adhesive film was measured at a wavelength of 400 nm to 800 nm using a Lambda 950 (Perkin Elmer).

(6) Dynamic bending test: Both release films were separated from the pressure-sensitive adhesive sheet prepared in Examples and Comparative Examples to obtain an adhesive film (thickness: 100 m). (Thickness: 100 占 퐉) / adhesive film (thickness: 100 占 퐉) / aluminum foil (thickness: 100 占 퐉, manufacturer: Lotte) were laminated in this order and cut into a size of width x length (25 mm x 130 mm) To prepare a specimen. A dynamic bending test rod (radius: 3 mm, flexural strength measuring device, manufacturer SDI) was placed in the center of the aluminum foil surface of the specimen in the longitudinal direction, and the specimen was folded around the rod and bending was repeated for 1 cycle , The minimum cycle number at which a crack occurred in the aluminum foil was visually measured. The adhesive film having a minimum cycle number means an adhesive film which can easily relax the stress of the aluminum foil by bending.

(7) Durability: Both release films were separated from the pressure-sensitive adhesive sheet produced in Examples and Comparative Examples to obtain an adhesive film (thickness: 100 m). ITO (indium tin oxide) film / adhesive film / glass plate in this order. The specimens were left at 85 ° C and 85% relative humidity for 480 hours. Whether lifting, peeling, or bubbling of the adhesive film on the adhered surface of the adhesive film was evaluated visually.

○: No bubbles or peeling

△: There are some bubbles or peeling.

X: There are many bubbles or peeling.

(8) C = O mol% vs. Si of the pressure-sensitive adhesive film The total number of moles (A) of silicone M units, D units and Q units in the silicone pressure-sensitive adhesive film was determined using Solid- The number of moles of bond (B) is obtained, and is obtained from the above-mentioned formula (2).

Example Comparative Example One 2 3 4 One 2 A 49 48 48 48 49.5 - B 50 50 50 50 50 99 C C-1 0.5 - - 0.5 - 0.5 C-2 - 1.5 - - - - C-3 - - 1.5 1.0 - - D 0.5 0.5 0.5 0.5 0.5 0.5 Time (minutes) 6 6 6 6 6 6 Whether the film is formed ◎ ◎ ◎ ◎ × × Storage modulus -20 < 0 > C, (MPa) 0.213 0.256 0.202 0.205 - - 25 DEG C, (MPa) 0.022 0.026 0.027 0.025 - - 80 < 0 > C, (MPa) 0.020 0.025 0.026 0.024 - - Peel strength 25 < 0 > C, (gf / in) 675 615 602 620 - - 60 < 0 > C, (gf / in) 464 412 357 400 - - Light transmittance
(%) 98 98 98 98 - - dynamic bending test (cycle) 920 1,500 1,770 1,600 - - durability ○ ○ △ ○ - - Mol% of C = O relative to Si of the adhesive film 0.46 0.81 0.71 0.76 -

As shown in Table 1, the pressure-sensitive adhesive composition according to the present invention has an appropriate range of modulus at -20 ° C, 25 ° C, and 80 ° C, thereby realizing an adhesive film having good bending properties. In addition, the pressure-sensitive adhesive composition according to the present embodiment has a high peeling strength, and can realize an adhesive film having excellent adhesive strength, excellent durability, and excellent light transmittance.

On the other hand, in Comparative Example 1, which does not include the compound of Formula 1 or the copolymer thereof, and Comparative Example 2, which does not include the silicone polymer, the film could not be formed and the physical properties of Table 1 could not be measured.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims

(A) a silicone polymer having (meth) acrylate groups,
(R ') (R "') SiO _{1/2 wherein} R ', R" and R "' are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, And a Q unit SiO _4/2 ,
(C) a silicone compound of the formula (1), a copolymer thereof or a mixture thereof, and
(D) a photoinitiator,
&Lt; Formula 1 >

(In the formula 1,
X is a photocurable functional group,
R ¹ represents a substituted or unsubstituted C1 to C12 alkylene group or * - (R ') - O - ** (* represents a connecting site to X in the formula (1) , R 'is a substituted or unsubstituted C1 to C12 alkylene group)
R ² is a substituted or unsubstituted C1 to C12 alkyl group,
R ³ is a substituted or unsubstituted C1 to C12 alkyl group or a group represented by the following formula (1-1)
&Lt; Formula 1-1 >

(In the above formula 1-1,
* Is the connecting part of the element,
R ^a , R ^b , R ^c , R ^d , R ^e , R ^f and R ^g are each independently a substituted or unsubstituted C1 to C10 alkyl group,
and m is an integer of 0 to 200)
a is an integer of 0 to 3,
The silicon pressure-sensitive adhesive film formed from the silicone pressure-sensitive adhesive composition has a storage modulus of 0.05 MPa to 1.0 MPa at -20 ° C, a storage modulus of 0.01 MPa to 0.10 MPa at 80 ° C, a content of C═O bond of 0.3 Mol% to 5.0 mol%.

The silicone pressure sensitive adhesive composition of claim 1, wherein X is a (meth) acrylate group.

The positive resist composition according to claim 1, wherein (C) is at least one compound selected from the group consisting of 3- (meth) acryloxypropyldimethylmethoxysilane, 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, (Meth) acryloxymethyltrimethoxysilane, 3- (meth) acryloxymethyldimethylethoxysilane, 3- (meth) acryloxymethyltriethoxysilane, 3- (Meth) acryloxypropyltriethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, 3- Wherein R ^a , R ^b , R ^c , R ^d , R ^e , R ^f and R ^g in formula (1-1) are methyl groups and X is a (meth) acrylate group, Based on the total weight of the composition.

The silicone pressure-sensitive adhesive composition according to claim 1, wherein (C) comprises a mixture of a compound of the formula (1) and a compound of the formula (1).

The silicone pressure-sensitive adhesive composition according to claim 1, wherein (C) comprises 0.1 wt% to 10 wt%, based on the total weight of (A), (B), (C) and (D).

The silicone pressure-sensitive adhesive composition according to claim 1, wherein (B) comprises from 35% by weight to 55% by weight based on the total weight of (A), (B), (C)

The silicone pressure-sensitive adhesive composition according to claim 1, wherein (A) comprises a silicone resin having a content of (meth) acrylate groups relative to silicon (Si) of 0.20 mol% to 2.5 mol%.

The silicone pressure-sensitive adhesive composition according to claim 1, wherein (A) has a weight average molecular weight (Mw) of 10,000 to 100,000.

A storage modulus of 0.05 MPa to 1.0 MPa at -20 캜,
A silicone adhesive film having a storage modulus of 0.01 MPa to 0.10 MPa at 80 DEG C,
Wherein the silicon adhesive film has a content of C = O bond of 0.3 mol% to 5.0 mol% with respect to silicon (Si).

The silicone adhesive film according to claim 9, wherein the silicone adhesive film has a storage modulus of 0.010 MPa to 0.10 MPa at 25 캜.

A silicone adhesive film,
The silicon adhesive film was produced by preparing a specimen in which a polyester film (thickness: 100 μm), the silicon adhesive film (thickness: 25 μm to 100 μm) and an aluminum foil (thickness: (Radius: 3 mm) was placed on the surface of the aluminum foil and the bending of the specimen folded about the rod was repeated for 1 cycle, the minimum cycle number of cracks in the aluminum foil was 900 or more,
Wherein the silicon adhesive film has a content of C = O bond of 0.3 mol% to 5.0 mol% with respect to silicon (Si).

The silicone adhesive film according to claim 11, wherein the cycle number of the silicone adhesive film is 900 to 2000.

The silicone adhesive film according to claim 9 or 11, wherein the silicone adhesive film comprises (C) a silicone compound represented by the following formula (1), a copolymer thereof, or a mixture thereof:
&Lt; Formula 1 >

(In the above formula 1-1,
* Is the connecting part of the element,
R ^a , R ^b , R ^c , R ^d , R ^e , R ^f and R ^g are each independently a substituted or unsubstituted C1 to C10 alkyl group,
and m is an integer of 0 to 200)
and a is an integer of 0 to 3).

The method of manufacturing a silicon adhesive film according to claim 9 or 11,
(A) a silicone polymer having (meth) acrylate groups,
(R ') (R "') SiO _{1/2 wherein} R ', R" and R "' are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, And a Q unit SiO _4/2 ,
(C) a silicone compound of the formula (1), a copolymer thereof or a mixture thereof, and
(D) a photoinitiator, wherein the pressure-sensitive adhesive composition comprises:
&Lt; Formula 1 >

45 to 65% by weight of a copolymer of (A) a silicone polymer having (meth) acrylate groups and (C) a silicone compound of the formula (1), a copolymer thereof or a mixture thereof; And
(R ') (R "') SiO _{1/2 wherein} R ', R" and R "' are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, And 35 wt% to 55 wt% of a silicone resin consisting of Q units SiO _4/2 ,
&Lt; Formula 1 >

(In the above formula 1-1,
* Is the connecting part of the element,
R ^a , R ^b , R ^c , R ^d , R ^e , R ^f and R ^g are each independently a substituted or unsubstituted C1 to C10 alkyl group,
and m is an integer of 0 to 200)
a is an integer of 0 to 3,
Wherein the silicone adhesive film has a storage modulus of 0.05 MPa to 1.0 MPa at -20 캜, a storage modulus of 0.01 MPa to 0.10 MPa at 80 캜 and a content of C = O bond of 0.3 to 5.0 mol% %. &Lt; / RTI >

The method of claim 15, wherein the silicone adhesive film
(A) 40% to 60% by weight of a silicone polymer having (meth) acrylate groups,
35% to 55% by weight of the silicone resin (B)
(C) 0.1% to 10% by weight of a silicone compound of the formula (1), a copolymer thereof or a mixture thereof, and
(D) 0.1% to 5% by weight of a photoinitiator.

delete

An optical display device comprising the silicon adhesive film according to any one of claims 9, 11 and 15.

The optical display device according to claim 18, wherein the optical display device comprises a flexible display device.