KR20170040830A - Adhesive film and method of producing the same - Google Patents
Adhesive film and method of producing the same Download PDFInfo
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- KR20170040830A KR20170040830A KR1020150139600A KR20150139600A KR20170040830A KR 20170040830 A KR20170040830 A KR 20170040830A KR 1020150139600 A KR1020150139600 A KR 1020150139600A KR 20150139600 A KR20150139600 A KR 20150139600A KR 20170040830 A KR20170040830 A KR 20170040830A
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- sensitive adhesive
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- adhesive film
- adhesive layer
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- 0 *CNC(ON)=O Chemical compound *CNC(ON)=O 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N CC(C)(C)N=C=O Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
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- C09J7/0207—
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
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- C09J7/0217—
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- C09J2201/36—
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- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
A pressure-sensitive adhesive composition comprising a modified phenoxy resin having a functional group represented by the following formula (1), or a pressure-sensitive adhesive composition formed by progressing a thermosetting reaction or a photo- layer; An intermediate substrate layer; And a (meth) acrylic adhesive layer, and a process for producing the same.
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
Description
An adhesive film and a method for producing the same.
Various colors or images of the display device or the display device can be expressed by passing light generated from, for example, a backlight, which is a light source of the TFT-LCD, or a light emitting diode, through the color filter.
Accordingly, the manufacturing process of the display device or the display device involves a color filter process, a so-called C / F process, in which a color filter is formed on a predetermined substrate, and the color filter includes a black matrix, .
At this time, in the case of a flat display, a color filter process is directly applied on a substrate. In the case of a flexible or foldable display device in which a recent attention is being paid, When the filter is applied, there is a problem that it is difficult to stably form the color filter because the substrate used in the color filter process has a high flexibility.
In one embodiment of the present invention, there is provided an adhesive film which simultaneously realizes excellent tackiness, excellent heat resistance and excellent releasability.
In another embodiment of the present invention, there is provided a process for producing an adhesive film which simultaneously realizes excellent adhesiveness, excellent heat resistance and excellent releasability.
However, the technical problem to be solved by the present invention is not limited to the above-mentioned problems, and other matters not mentioned can be clearly understood by those skilled in the art from the following description.
In one embodiment of the present invention, a pressure-sensitive adhesive composition comprising a modified phenoxy resin having a functional group represented by the following formula (1) is subjected to a thermosetting reaction or a thermosetting reaction and a photocuring reaction A pressure-sensitive adhesive layer formed by advancing the pressure-sensitive adhesive layer; An intermediate substrate layer; And a (meth) acrylic adhesive layer.
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
The pressure-sensitive adhesive layer has an advantage that both excellent heat resistance and excellent releasability can be realized at the same time.
The pressure sensitive adhesive layer includes the pressure sensitive adhesive layer on one side and the (meth) acrylic pressure sensitive adhesive layer on the other side, wherein the pressure sensitive adhesive layer is applied to the color filter process The (meth) acrylic adhesive layer can be adhered to the glass substrate while being adhered to a predetermined substrate, and the adhesive film realizes excellent adhesiveness to both the predetermined substrate and the glass substrate, It can be supported more stably.
Further, the adhesive film includes the intermediate base layer, and the overall thermal expansion coefficient thereof is lowered, so that a difference in thermal expansion coefficient between the predetermined base material and the glass substrate can be reduced, and accordingly, It is possible to prevent the adhesive film from being wrinkled or detached.
The pressure-sensitive adhesive layer has a peeling force measured at a room temperature, a peeling speed of about 600 mm / min, and a peeling angle of about 90 degrees with respect to a base material made of plastic, for example, about 25 gf / 80 mm to about 3,000 gf / 80 mm, and may be specifically about 100 gf / 80 mm to about 1,000 gf / 80 mm.
By having a peeling force within the above range, an excellent adhesive force is realized in the color filter process, and the substrate can be stably supported while being easily peeled and removed without damaging the substrate at an appropriate time after the color filter process is completed.
The pressure-sensitive adhesive layer may have a rate of change (R) of the peeling force according to the following equation 1 with respect to a base material made of a plastic material, for example, about -500% to about 2000%, and specifically about -100% It can be 1000%:
[Equation 1]
(R,%) = {(F 2 - F 1 ) / F 1 }
By having a rate of change of the low peeling force within the above range, the heat resistance can be further improved, and the phenomenon of sticking or expanding to the substrate can be effectively prevented even in a high temperature process.
The glass transition temperature of the pressure-sensitive adhesive layer may be, for example, about 30 캜 to about 90 캜, and specifically about 40 캜 to about 80 캜. By having a high glass transition temperature within the above range, even if a high temperature process is applied, it can be melted or deteriorated, and excellent heat resistance can be realized.
As described above, the pressure-sensitive adhesive film may include the intermediate substrate layer between the pressure-sensitive adhesive layer and the (meth) acrylic pressure-sensitive adhesive layer.
Accordingly, the pressure-sensitive adhesive film can exhibit excellent tackiness for both the predetermined substrate and the glass substrate, and the overall thermal expansion coefficient thereof can be lowered compared with the pressure-sensitive adhesive film containing the pressure-sensitive adhesive layer alone, It is possible to effectively prevent the phenomenon that the adhesive film is wrinkled or detached in a process of lowering the temperature.
Further, when the adhesive film is removed at an appropriate time after the completion of the color filter process, when the area of the predetermined substrate to which the adhesive film is adhered is large as well as large, for example, The adhesive film can be easily peeled and removed at once without breaking the adhesive film.
The (meth) acrylic adhesive layer may have a glass transition temperature of about -60 캜 to about -30 캜.
Since the (meth) acrylic adhesive layer is not in contact with a predetermined substrate to which a color filter process is to be applied, it is not necessary to consider the heat resistance as an important factor, so that the glass transition temperature More excellent tackiness and wettability can be realized.
The (meth) acrylic adhesive layer may have a peeling force of about 100 gf / 80 mm to about 600 gf / 80 mm measured on a glass substrate under a peeling speed of about 600 mm / min and a peeling angle of about 180 °.
By having the peeling force within the above range, the glass substrate can be more easily peeled and removed without damaging the glass substrate, so that it can be reused repeatedly in the manufacturing process of the display device, thereby realizing excellent economical efficiency.
In another embodiment of the present invention, a step (S1) of forming a (meth) acrylic adhesive layer on one side of the intermediate substrate layer; And a step (S2) of forming a pressure-sensitive adhesive layer on the other surface of the intermediate substrate layer, wherein the pressure-sensitive adhesive layer comprises a modified phenoxy resin having a functional group represented by the following formula (1) -Sensitive Adhesive) composition of the present invention, or sequentially advancing a thermosetting reaction and a photo-curing reaction, the method comprising:
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
The above-mentioned pressure-sensitive adhesive film can simultaneously realize excellent adhesiveness, excellent heat resistance and excellent releasability.
1 is a schematic cross-sectional view of an adhesive film according to an embodiment of the present invention.
2 is a schematic process flow diagram of a method for producing an adhesive film according to another embodiment of the present invention.
Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains. The present invention may be embodied in many different forms and is not limited to the embodiments described herein.
In order to clearly illustrate the present invention, parts not related to the description are omitted, and the same or similar components are denoted by the same reference numerals throughout the specification.
In the drawings, the thickness is enlarged to clearly represent the layers and regions. In the drawings, for the convenience of explanation, the thicknesses of some layers and regions are exaggerated.
Hereinafter, formation of an arbitrary structure in the upper part (or lower part) or the upper part (or lower part) of the substrate means not only that an arbitrary constitution is formed in contact with the upper surface (or lower surface) of the substrate, And any configuration formed on (or under) the substrate.
In the present specification, "*" may mean the same or different atom or part connected to the formula
1 is a schematic cross-sectional view of an
In one embodiment of the present invention, a pressure-sensitive adhesive composition comprising a modified phenoxy resin having a functional group represented by the following formula (1) is subjected to a thermosetting reaction or a thermosetting reaction and a photocuring reaction A pressure-sensitive
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
In general, in the case of a flat display, a color filter process is directly applied on a substrate. In the case of a flexible or foldable display device, There is a problem that it is difficult to stably form a color filter if a color filter is directly applied on a substrate as in the case of a flat panel display because the substrate used has a high flexibility.
Thus, in one embodiment of the present invention, in the production of a flexible or foldable display device, in order to stably form a color filter, for example, a pressure sensitive adhesive And a color filter process is performed on the upper part of the substrate. The pressure-sensitive adhesive composition of the present invention can be used for the above-mentioned pressure-sensitive adhesive in this method.
As described above, in the newly-investigated method, the pressure-sensitive adhesive and the glass substrate adhered to the lower portion of the substrate having completed the color filter process must be peeled off from the above substrates before the subsequent process is applied or during the process of assembling the product, Accordingly, in the pressure-sensitive adhesive composition, each peeling force at high temperature, normal temperature and low temperature is considered as one of the main physical properties.
Further, the color filter process includes a process of progressing at a high temperature of about 100 ° C to about 250 ° C several times, and in the case of a pressure-sensitive adhesive having a low heat resistance, a problem that the pressure- , And accordingly, in the pressure-sensitive adhesive composition, heat resistance together with the peeling force described above is considered as one of the main physical properties.
For example, when a pressure sensitive adhesive comprising a conventional phenoxy resin is used, the heat resistance is good, but since the conventional phenoxy resin contains a large number of hydroxy groups, the adhesive force to the base material does not decrease below a certain level at low temperatures It may be difficult to remove without damage from the substrate after completion of the color filter process.
Further, for example, when a pressure-sensitive adhesive containing a (meth) acrylic resin having a low cross-linking density is used, the heat resistance of the pressure-sensitive adhesive is low, so that a problem of sticking or expanding to the substrate after the high temperature process can easily occur.
In order to prevent the above-mentioned problems, in one embodiment of the present invention, as described later, the pressure-sensitive adhesive composition may contain a part of the hydroxyl groups contained therein from a conventional phenoxy resin not modified or modified, Functional phenoxy resin, and the modified phenoxy resin has a lower hydroxyl group equivalent as compared with a conventional phenoxy resin, so that the adhesive strength to the substrate can be suitably lowered, and the (meth) acrylic resin It is possible to improve the heat resistance by forming the crosslinking density and the glass transition temperature at a high level.
Accordingly, the pressure-sensitive
The
In addition, the
In one embodiment, the modified phenoxy resin may be formed by a chemical reaction between a phenoxy resin and a compound represented by the following formula (2):
(2)
In Formula 2, R 1 is H or a methyl group, and n is 1, 2, or 3.
The phenoxy resin refers to a conventional phenoxy resin known in the art as one of thermoplastic resins and includes, for example, bisphenol A phenoxy resin, bisphenol F phenoxy resin, bromine phenoxy resin, But is not limited to, at least one selected from the group consisting of phenoxy resins, bisphenol S-type phenoxy resins, caprolactone-modified phenoxy resins, and combinations thereof.
Such a phenoxy resin may contain a plurality of hydroxy groups, for example, a hydroxyl group equivalent of about 100 to about 300.
The compound represented by Formula 2 is an isocyanate having a (meth) acryloyloxyalkyl group, for example, methacryloyloxymethyl isocyanate, acryloyloxymethyl isocyanate 2-methacryloyloxyethyl isocyanate, 2 But are not limited to, acryloyloxyethyl isocyanate, 3-methacryloyloxypropyl isocyanate, 3-acryloyloxypropyl isocyanate, and the like.
A part of the hydroxyl groups of the phenoxy resin may be chemically reacted with the compound represented by the formula (2) to form the functional group represented by the formula (1).
Specifically, some of the hydroxyl groups present in the phenoxy resin may undergo a chemical reaction with an isocyanate group of the compound represented by the formula (2) to form a urethane bond, thereby changing to a functional group represented by the formula (1) In the phenoxy resin, the acryloyloxyalkyl group may be bonded to the side chain through a urethane bond.
As described above, since the predetermined hydroxy group present in the phenoxy resin is formed of the functional group represented by the formula (1), the weight average molecular weight and the glass transition temperature of the modified phenoxy resin can be further improved, The crosslinking density of the pressure-sensitive adhesive obtained by curing the pressure-sensitive adhesive is increased, so that excellent heat resistance and excellent releasability can be realized.
For example, the phenoxystyrene resin and the compound represented by Formula 2 may be mixed and stirred, followed by heat treatment to proceed the chemical reaction.
The temperature and time of the heat treatment may be suitably selected in a range necessary for advancing the chemical reaction, for example, the heat treatment may be performed at a temperature of about 100 ° C to about 150 ° C and for a time of about 10 hours to about 20 hours , But is not limited thereto.
The modified phenoxy resin may be formed by chemical reaction of about 70 parts by weight to about 110 parts by weight of the compound represented by Formula 2 with respect to 100 parts by weight of the phenoxy resin.
The weight average molecular weight and the glass transition temperature of the modified phenoxy resin can be suitably improved and the hydroxyl group equivalent can be appropriately formed by chemical reaction at a content within the above range.
The weight average molecular weight of the modified phenoxy resin may be, for example, from about 10,000 g / mol to about 100,000 g / mol, and specifically from about 40,000 g / mol to about 60,000 g / mol.
By having a weight average molecular weight within the above range, the cured product of the pressure-sensitive adhesive composition comprising the same, that is, the pressure-sensitive adhesive, can exhibit excellent adhesive properties and can deteriorate physical properties at high temperatures. Specifically, less than about 10,000 g / mol can increase the hardness of the pressure-sensitive adhesive to reduce the wetting property to the substrate, and if it exceeds about 100,000 g / mol, There is a problem in that a large number of cured hydroxy groups may significantly increase the rate of change with time at a high temperature.
The glass transition temperature of the modified phenoxy resin may be, for example, from about 10 캜 to about 90 캜, and specifically from about 30 캜 to about 80 캜.
By having a high glass transition temperature within the above range, the heat resistance can be improved, and the pressure sensitive adhesive formed by curing the pressure-sensitive adhesive composition can be prevented from sticking to the base material or expanding at high temperature.
In general, the color filter process can be repeated about 4 times while high temperature and normal temperature conditions are alternately applied. At this time, the process can be repeated in the process of returning to the original shape after the expansion and contraction process. In this process, when the glass transition temperature is less than about 10 ° C, since the glass transition temperature has a high coefficient of thermal expansion, deformation occurs at a high temperature and the glass transition temperature does not return to its original state. As a result, steps, If the temperature is higher than 90 DEG C, the tack property is too low to be desorbed from the substrate before the color filter process is completed.
The modified phenoxy resin may have a hydroxyl group equivalent of about 10 to about 50.
By having a low hydroxyl equivalent within the above range, the pressure-sensitive adhesive formed from the pressure-sensitive adhesive composition realizes excellent releasability and can be easily peeled off without damaging the substrate at an appropriate time.
In one embodiment, the pressure sensitive adhesive composition may further comprise a (meth) acrylic polymer.
The (meth) acrylic polymer acts as a cross-linking agent for cross-linking the modified phenoxy resin, thereby improving the cross-linking density, and the cured product of the pressure-sensitive adhesive composition containing the cross-linking agent can exhibit excellent adhesiveness at room temperature.
For example, the (meth) acrylic polymer may be formed by polymerizing a monomer component containing a (meth) acrylate monomer having 1 to 12 carbon atoms.
The monomer component may not include, for example, an isobonyl (meth) acrylate monomer, whereby the adhesive force or adhesion of the pressure-sensitive adhesive formed by curing the pressure-sensitive adhesive composition to the substrate is significantly increased Can be prevented.
(Meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, Butyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, 2-ethylhexyl (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, isooctyl (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl Or 2-hydroxypropylene glycol (meth) acrylate Sites, methacrylic acid, but may include at least one selected from the group including acrylic acid, and combinations thereof, and the like.
The weight average molecular weight of the (meth) acrylic polymer may be about 1,000 g / mol to about 100,000 g / mol. By having a weight average molecular weight within the above range, flexibility can be appropriately adjusted while realizing excellent crosslink density.
The glass transition temperature of the (meth) acrylic polymer which may further be included in the pressure-sensitive adhesive composition may be about -60 캜 to about 15 캜. By having a glass transition temperature within the above range, it is possible to improve the heat resistance of the pressure-sensitive adhesive composition while realizing an initial level of ordinary temperature and tackiness at an appropriate level.
The pressure-sensitive adhesive composition may include about 1 part by weight to about 20 parts by weight of the (meth) acrylic polymer based on 100 parts by weight of the modified phenoxy resin.
By including it in the content within the above range, excellent tackiness, excellent wettability and excellent heat resistance can be realized. Specifically, when the amount of the crosslinking agent is less than about 1 part by weight, the crosslinking agent can not sufficiently perform its function. When the amount of the crosslinking agent is more than about 20 parts by weight, the crosslinking density after thermal curing and before photocuring becomes significantly high, have.
The pressure-sensitive adhesive composition may further include at least one selected from the group consisting of, for example, a heat curing agent, a photoinitiator, a solvent, and combinations thereof.
The thermosetting agent may include at least one selected from the group consisting of, for example, a melamine-based curing agent, a urea-formaldehyde-based curing agent, an isocyanate-based curing agent, a phenol-based curing agent, an amino-based curing agent and combinations thereof.
The thermosetting agent may be included in an amount of about 1 part by weight to about 10 parts by weight based on 100 parts by weight of the modified phenoxy resin.
Also, the photoinitiator may include at least one selected from the group consisting of benzophenone-based initiators, alpha-hydroxyketone-based initiators, alpha-amino ketone-based initiators, phenylglyoxylate-based initiators, Methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one, diphenyl- (2,4,6-trimethylbenzoyl) -phosphine Hydroxy-2-methyl-1-phenyl-propan-1-one, 1 -hydroxy-cyclohexylphenyl-ketone, benzophenone, 4-benzoyl-4'-methyldiphenylsulfide , Methyl-2-benzoylbenzoate, isopropylthioxanthone, ethyl-4- (dimethylamino) benzoate, 2-ethylhexyl-4-dimethylaminobenzoate, hydroxydimethylacetophenone, Xanthone, xanthone, 4-phenylbenzophenone, and combinations thereof. It is not limited.
The photoinitiator may be included in an amount of about 1 part by weight to about 20 parts by weight based on 100 parts by weight of the modified phenoxy resin.
The heat curing agent or the photoinitiator is contained in the content within the respective ranges so that the thermosetting reaction or the photo-curing reaction proceeds sufficiently and the unreacted thermosetting agent or the unreacted photoinitiator does not remain in the cured product of the pressure- The migration phenomenon thereof can be prevented.
The solvent may include, but is not limited to, at least one selected from the group consisting of toluene, tetrahydrofuran, xylene, chloroform, dimethylsulfoxide, m-cresol, N-methylpyrrolidone and combinations thereof.
A thermosetting reaction for the pressure-sensitive adhesive composition; Or sequentially a thermal curing reaction and a photo-curing reaction may be carried out to form the pressure-
Specifically, when the pressure-sensitive adhesive composition contains the modified phenoxy resin and does not further include the (meth) acrylic polymer, the pressure-
The thermosetting reaction can be conducted, for example, by subjecting the pressure-sensitive adhesive composition to a heat treatment at a temperature of about 60 캜 to about 130 캜 for about 3 minutes to about 5 minutes. By performing the heat treatment for the temperature and the time within the above range, the thermosetting reaction can sufficiently proceed and the solvent can be easily evaporated.
When the photocuring reaction proceeds after the thermosetting reaction is advanced, the pressure-sensitive adhesive composition is subjected to UV irradiation at an irradiation dose of, for example, about 4,000 mJ / cm 2 to about 6,000 mJ / cm 2 The photocuring reaction can proceed. By performing UV irradiation at the irradiation amount within the above range, the photocuring reaction can be sufficiently advanced.
In one embodiment, the pressure-
In this case, the peeling force may mean a peeling force measured in a state where the peeling force is maintained at room temperature without any additional heat treatment immediately after the pressure-
By having a peeling force within the above range, an excellent adhesive force is realized in the color filter process, and the substrate can be stably supported while being easily peeled and removed without damaging the substrate at an appropriate time after the color filter process is completed.
The pressure-
[Equation 1]
(R,%) = {(F 2 - F 1 ) / F 1 }
In the above formula 1, wherein F 1 is the pressure-
When the peel force is measured according to the above-described F 1 , the holding time at the room temperature may be, for example, about 20 minutes or about 60 minutes. However, if the peeling force is not further processed as described above, The time is not particularly limited. However, in the case of measuring the peeling force according to the above-mentioned F 2 , the temperature may be gradually lowered as the condition is changed from high temperature to room temperature, and the time for which the temperature is maintained at the room temperature may be about 20 minutes or more. It does not.
By having a rate of change of the low peeling force within the above range, the heat resistance can be further improved, and the phenomenon of sticking or expanding to the substrate can be effectively prevented even in a high temperature process.
The glass transition temperature of the pressure-
The pressure-
By having a thickness within the above range, sufficient adhesion can be realized without excessively increasing the total thickness of the
In one embodiment, the
Accordingly, the
Further, when the
The
The thermoplastic resin film may be made of, for example, polyethylene, polypropylene, polyurethane, polyethyleneterephthalate, polybutylene tererephthalate, polyurea, But are not limited to, polyvinylchloride, polyvinylacetate, ethylenevinylacetate, polyphenylene sulfide, polyamide, polyimide, polybenzimidazole, Polyetheretherketone, and a combination thereof. In particular, it may include polyethylene terephthalate to realize more excellent dimensional stability.
The
In one embodiment, the (meth)
The (meth)
The (meth)
Since the (meth)
The (meth)
By having the peeling force within the above range, the glass substrate can be more easily peeled and removed without damaging the glass substrate, so that it can be reused repeatedly in the manufacturing process of the display device, thereby realizing excellent economical efficiency.
And may be about 5 탆 to about 25 탆 of the (meth)
In one embodiment, the
In another embodiment of the present invention, a step (S1) of forming a (meth) acrylic adhesive layer on one side of the intermediate substrate layer; And a step (S2) of forming a pressure-sensitive adhesive layer (110) on the other surface of the intermediate substrate layer, wherein the pressure-sensitive adhesive layer comprises a modified phenoxy resin having a functional group represented by the following formula There is provided a process for producing a pressure-sensitive adhesive composition which is formed by causing a thermosetting reaction or a thermosetting reaction and a photo-curing reaction sequentially to a pressure-sensitive adhesive composition:
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
In the above production method, the order of forming the (meth) acrylic adhesive layer and the pressure-sensitive adhesive layer may be different and not particularly limited, so that the (meth) acrylic adhesive layer is formed on one side of the intermediate base layer, The pressure sensitive adhesive layer may be formed on one surface of the intermediate base layer or the pressure sensitive adhesive layer may be formed on the other surface of the intermediate base layer. That is, in this specification, one surface and the other surface of the intermediate substrate layer refer to different surfaces and do not mean a temporal relationship in which a separate layer is formed on the upper or lower surface thereof.
The pressure-sensitive adhesive layer, the intermediate substrate layer and the (meth) acrylic adhesive layer are as described above in one embodiment.
The method may further include a step of chemically reacting a phenoxy resin and a compound represented by the following general formula (2) to form a modified phenoxy resin having a functional group represented by the general formula (1)
[Chemical Formula 1]
(2)
In the general formulas (1) and (2), R 1 is H or a methyl group, and n is 1, 2, or 3.
The phenoxystyrene resin and the compound represented by Formula 2 are as described above in one embodiment.
In the above manufacturing method, the modified phenoxy resin can be formed by chemically reacting about 70 parts by weight to about 110 parts by weight of the compound represented by Formula 2 with respect to 100 parts by weight of the phenoxy resin. The weight average molecular weight and the glass transition temperature of the modified phenoxy resin can be suitably increased and the hydroxyl group equivalent can be suitably formed by chemical reaction at a content within the above range.
For example, the phenoxystyrene resin and the compound represented by Formula 2 may be mixed and stirred, followed by heat treatment to proceed the chemical reaction.
The temperature and time of the heat treatment may be suitably selected in a range necessary for advancing the chemical reaction, for example, the heat treatment may be performed at a temperature of about 100 ° C to about 150 ° C and for a time of about 10 hours to about 20 hours , But is not limited thereto.
A part of the hydroxyl groups of the phenoxystyrene resin may be chemically reacted with the compound represented by the general formula (2) by the chemical reaction to form the functional group represented by the general formula (1).
Specifically, some of the hydroxyl groups present in the phenoxy resin may undergo a chemical reaction with an isocyanate group of the compound represented by the formula (2) to form a urethane bond, thereby changing to a functional group represented by the formula (1) In the phenoxy resin, the acryloyloxyalkyl group may be bonded to the side chain through a urethane bond.
As described above, since the predetermined hydroxy group present in the phenoxy resin is formed of the functional group represented by the formula (1), the weight average molecular weight and the glass transition temperature of the modified phenoxy resin can be further improved, The crosslinking density of the pressure-sensitive adhesive obtained by curing the pressure-sensitive adhesive is increased, so that excellent heat resistance and excellent releasability can be realized.
In the above production process, the weight average molecular weight of the modified phenoxy resin may be, for example, from about 10,000 g / mol to about 100,000 g / mol, and specifically about 40,000 g / mol to about 60,000 g / mol. < / RTI >
The cured product of the pressure-sensitive adhesive composition comprising the curable composition, which has a high weight average molecular weight within the above range, may exhibit excellent adhesive properties and may deteriorate physical properties at high temperatures. Specifically, less than about 10,000 g / mol can increase the hardness of the pressure-sensitive adhesive to reduce the wetting property to the substrate, and if it exceeds about 100,000 g / mol, There is a problem in that a large number of cured hydroxy groups may significantly increase the rate of change with time at a high temperature.
The glass transition temperature of the modified phenoxy resin may be, for example, from about 10 캜 to about 90 캜, and specifically from about 30 캜 to about 80 캜.
By forming the pressure sensitive adhesive composition to have a high glass transition temperature within the above range, the heat resistance can be effectively improved, and the pressure sensitive adhesive formed by curing the pressure sensitive adhesive composition can be prevented from sticking to the base material or expanding at high temperature.
The modified phenoxy resin may have a hydroxyl group equivalent of about 10 to about 50.
By having a low hydroxyl equivalent within the above range, the pressure-sensitive adhesive formed from the pressure-sensitive adhesive composition realizes excellent releasability and can be easily peeled off without damaging the substrate at an appropriate time.
In the above manufacturing method, the step of preparing the pressure-sensitive adhesive composition containing the modified phenoxy resin may be further included.
The pressure-sensitive adhesive composition may be prepared by mixing the modified phenoxy resin and the (meth) acrylic polymer. In this case, the pressure-sensitive adhesive composition may be mixed more uniformly by stirring at the same time. The (meth) acrylic polymer is as described above in one embodiment.
About 1 part by weight to about 20 parts by weight of the (meth) acrylic polymer may be mixed with 100 parts by weight of the modified phenoxy resin. By including it in the content within the above range, excellent tackiness, excellent wettability and excellent heat resistance can be realized. Specifically, when the amount of the crosslinking agent is less than about 1 part by weight, the crosslinking agent can not sufficiently perform its function. When the amount of the crosslinking agent is more than about 20 parts by weight, the crosslinking density after thermal curing and before photocuring becomes significantly high, have.
In the above manufacturing method, the step of forming the (meth) acrylic polymer to be mixed with the pressure-sensitive adhesive composition may be further included.
The (meth) acrylic polymer may be formed by polymerizing a monomer component containing 1 to 12 carbon atoms (meth) acrylate monomers. The monomer component is as described above in one embodiment.
The monomer component may not include, for example, an isobonyl (meth) acrylate monomer, whereby the adhesive force or adhesion of the pressure-sensitive adhesive formed by curing the pressure-sensitive adhesive composition to the substrate is significantly increased Can be prevented.
For example, the monomer component can be formed by conducting a thermal polymerization reaction or a photopolymerization reaction, and the thermal polymerization reaction or the photopolymerization reaction can be carried out by any method known in the art, and is not particularly limited.
The weight average molecular weight of the (meth) acrylic polymer may be about 10,000 g / mol to about 100,000 g / mol. By having a weight average molecular weight within the above range, flexibility can be appropriately adjusted while realizing excellent crosslink density. And the glass transition temperature of the (meth) acrylic polymer is about -60 캜 to about 15 캜. By having a glass transition temperature within the above range, it is possible to improve the heat resistance of the pressure-sensitive adhesive composition while realizing an initial level of ordinary temperature and tackiness at an appropriate level.
Further, in the step of preparing the pressure-sensitive adhesive composition, the pressure-sensitive adhesive composition may be prepared by further mixing at least one selected from the group consisting of, for example, a heat curing agent, a photoinitiator, a solvent, and a combination thereof. The thermosetting agent, the photoinitiator, and the solvent are as described above in one embodiment.
In one embodiment, the (meth) acrylic adhesive layer comprises, for example, from about 70% to about 99% by weight of a (meth) acrylic based prepolymer having a weight average molecular weight of about 1,000,000 g / mol to about 2,000,000 g / mol (Meth) acrylic pressure sensitive adhesive composition is subjected to a heat treatment to advance the thermosetting reaction. At this time, the temperature and time of the heat treatment can be performed according to methods and conditions known in the art, and are not particularly limited.
For example, the (meth) acrylic adhesive layer may be formed by applying and curing the (meth) acrylic adhesive composition on one side of the intermediate substrate layer, or the (meth) acrylic adhesive composition may be previously An adhesive sheet, and laminated on one side of the intermediate substrate using a method such as thermal plywood.
On the other hand, when the (meth) acrylic adhesive composition is previously formed into a separate pressure sensitive adhesive sheet, a method of applying and curing the (meth) acrylic pressure sensitive adhesive composition on the release film or a car rendering process may be used. But is not limited to.
Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and the present invention should not be limited thereto.
Example
Example One
An intermediate substrate layer having a thickness of 12 mu m was prepared from a polyethylene terephthalate (PET) film.
Further, 100 parts by weight of a phenoxy resin (Inchem, a mixture of PKCP-80 and PKFE in a ratio of 1: 2) and 70 parts by weight of methacryloyloxyethyl isocyanate were mixed, followed by heating at 45 DEG C for 16 hours These were chemically reacted to form a modified phenoxy resin having a weight average molecular weight of 55,000 g / mol, a glass transition temperature of 75 캜 and a hydroxyl group equivalent of 47.
Subsequently, a pressure-sensitive adhesive composition was prepared by mixing and stirring 100 parts by weight of the modified phenoxy resin, 5.3 parts by weight of a thermosetting agent, 2 parts by weight of acrylic acid (AA), and a solvent (MEK).
Further, a (meth) acrylic adhesive composition comprising 95% by weight of a (meth) acrylic prepolymer having a weight average molecular weight of about 1,000,000 g / mol to about 2,000,000 g / mol and a thermosetting agent was prepared.
Subsequently, the pressure-sensitive adhesive composition was applied to one surface of the intermediate substrate layer and heat-treated at 130 ° C for 3 minutes to form a pressure-sensitive adhesive layer having a thickness of 6 μm, A release PET film was attached on the layer. Then, the (meth) acrylic adhesive composition is coated and thermally cured on another release type PET film to form a (meth) acrylic adhesive layer having a thickness of 6 탆, and the other surface of the intermediate base layer is coated with the And adhered to the adhesive layer to produce an adhesive film.
Comparative Example 1 (when a single-layer pressure-sensitive adhesive film was produced by a pressure-sensitive adhesive composition containing an acrylic polymer without a phenoxy resin)
A monomer component comprising 85% by weight of ethylhexyl acrylate, 10% by weight of butyl acrylate and 5% by weight of hexyl ethyl acrylate was thermally polymerized to obtain an acrylic polymer having a weight average molecular weight of 1,000,000 g / mol and a glass transition temperature of -56 ° C .
100 parts by weight of the acrylic polymer, 5 parts by weight of the thermosetting agent, 2 parts by weight of acrylic acid, and a solvent (MEK) were mixed and stirred to prepare a pressure-sensitive adhesive composition.
Then, the pressure-sensitive adhesive composition was subjected to a heat treatment at a temperature of 130 캜 for 3 minutes to conduct a thermosetting reaction, thereby producing a pressure-sensitive adhesive film having a thickness of 25 탆.
Comparative Example 2 (when a single-layer pressure-sensitive adhesive film was produced by a pressure-sensitive adhesive composition containing a conventional phenoxy resin)
100 parts by weight of a modified or unmodified phenoxy resin (Inchem, a mixture of PKCP-80 and PKFE in a ratio of 1: 2), 16.3 parts by weight of a thermosetting agent, 2.5 parts by weight of acrylic acid, and a solvent (MEK) And stirred to prepare a pressure-sensitive adhesive composition.
Then, the pressure-sensitive adhesive composition was subjected to a heat treatment at a temperature of 130 캜 for 3 minutes to conduct a thermosetting reaction, thereby producing a pressure-sensitive adhesive film having a thickness of 25 탆.
Comparative Example 3 (in the case of producing a multi-layer pressure-sensitive adhesive film comprising a pressure-sensitive adhesive layer formed of a pressure-sensitive adhesive composition containing a conventional phenoxy resin as compared with Example 1)
100 parts by weight of a modified or unmodified phenoxy resin (Inchem, a mixture of PKCP-80 and PKFE in a ratio of 1: 2), 16.3 parts by weight of a thermosetting agent, 2.5 parts by weight of acrylic acid, and a solvent (MEK) And the mixture was stirred to prepare a pressure-sensitive adhesive composition, and a pressure-sensitive adhesive layer was formed from the pressure-sensitive adhesive composition.
evaluation
Various properties of the respective pressure-sensitive adhesive films according to Example 1 and Comparative Example 1-3 were evaluated and are shown in Tables 1 and 2 below.
Experimental Example 1: Glass transition temperature
Measurement method: The pressure-sensitive adhesive layer included in the pressure-sensitive adhesive film according to Example 1 and the pressure-sensitive adhesive film according to Comparative Example 3, and the pressure-sensitive adhesive film according to Comparative Examples 1 and 2 were subjected to a temperature of -80 to 150 캜 at a rate of 10 캜 / min The glass transition temperature was measured using differential scanning calorimetry (DSC) (Perkin-Elmer DSC8000) under the condition of raising the temperature, and the results are shown in Table 1 below.
Experimental Example 2: Peel force
Measurement method: The pressure-sensitive adhesive film according to Example 1 and the pressure-sensitive adhesive film according to Comparative Example 1-3 were prepared as specimens each having a size of 130 mm x 80 mm x 30 m.
A 140 mm x 80 mm glass plate was attached to one surface of each of the above specimens. At this time, the specimen was mounted on the glass plate in such a manner that the specimen was positioned at the center of the specimen, In the case of Example 1 and Comparative Example 3, the (meth) acrylic adhesive layer adhered to the glass plate.
A polyimide film having a size of 140 mm x 90 mm was attached to the other surface of the specimen to form a laminate of a glass plate / specimen / polyimide film. At this time, a 140 mm portion of the polyimide film had a width of 130 mm And the other edge portions of 140 mm of the polyimide film were spaced apart from other edge portions of 130 mm of the specimen at intervals of about 10 mm. In the case of Example 1 and Comparative Example 3, the pressure-sensitive adhesive layer And was attached so as to be in contact with the polyimide film.
Then, the laminate was fixed between push zigs of a cylinder type having a diameter of 2 mm in a texture analyzer (TAXT.plush / EXT Texture Analyzer), and the polyimide film The pressure-sensitive adhesive layer of the pressure-sensitive adhesive films according to Example 1 and Comparative Example 3 and the pressure-sensitive adhesive layer according to Comparative Examples 1 and 2 were measured by measuring the force when the specimen was peeled off by applying a pressure vertically to the central portion of the protrusions The peeling force of the film on the polyimide film was measured, and the results are shown in Table 1 below.
Specifically, the peeling force on the polyimide film was measured at a temperature of 25 ° C, a peeling rate of 600 mm / min, and a peeling angle of 90 °. Further, immediately after the respective adhesive films were formed, The maximum value of the forces measured from the start of peeling to the completion of peeling of the polyimide film was evaluated as the peeling force.
Subsequently, each of the laminated glass plates / specimens remaining after peeling off the polyimide film by the above peeling force measurement was fixed again to the jig of the above-mentioned Texture Analyzer (TAXT.plush / EXT Texture Analyzer) at 90 ° (Meth) acrylic pressure-sensitive adhesive layer of the pressure-sensitive adhesive film according to Example 1 and Comparative Example 3 and the glass plate of the pressure-sensitive adhesive film according to Comparative Examples 1 and 2, by measuring the force when the specimen was peeled off from the glass plate Respectively, and the results are shown in Table 1. The results are shown in Table 1. < tb > < TABLE >
Specifically, the peeling force on the glass plate was measured under the conditions of a temperature of 25 ° C, a peeling rate of 600 mm / min, and a peeling angle of 180 °. At this time, The average value was evaluated as the peeling force.
Experimental Example 3: Heat resistance ( Exfoliation Change rate)
Measurement method: The pressure-sensitive adhesive films according to Example 1 and Comparative Example 3 and the pressure-sensitive adhesive films according to Comparative Examples 1 and 2 were prepared as specimens each having a size of 130 mm x 80 mm x 30 m.
Using the respective adhesive films, two laminated layers of a glass plate / specimen / polyimide film were formed under the same conditions and in the same manner as in Experimental Example 2 for the peeling force.
For each laminate, the pressure-sensitive adhesive layer of the pressure-sensitive adhesive film according to Example 1 and the pressure-sensitive adhesive film according to Comparative Example 3 and the peeling of the pressure-sensitive adhesive film according to Comparative Examples 1 and 2 on the polyimide film of Experimental Example 2 The peel force, F 1, was measured according to the same conditions and methods as for the force measurement.
Also, each of the other laminate was allowed to stand at a temperature of 150 캜 for 30 minutes immediately after the respective adhesive films were formed, and then kept at room temperature for 20 minutes. Using the Texture Analyzer, The peeling force, F 2, was measured under the conditions of the temperature, the peeling speed of 600 mm / min and the peeling angle of 90 °.
The heat resistance was evaluated by calculating the rate of change of the peeling force by substituting the above measured F 1 and F 2 into the above-mentioned calculation formula 1, and it is shown in Table 1 below. When the rate of change of the peeling force is -500% to 2,000% Quot ;, and when it is less than -500% or more than 2000%, or when it can not be measured due to sticking to the substrate, it is evaluated that the heat resistance is inferior, and is indicated by " X ".
Experimental Example 4: Ease of removal after high temperature process (low temperature Peel force )
Measurement method: The pressure-sensitive adhesive films according to Example 1 and Comparative Example 3 and the pressure-sensitive adhesive films according to Comparative Examples 1 and 2 were prepared as specimens each having a size of 130 mm x 80 mm x 30 m.
In order to evaluate the ease of removal under low temperature conditions after the application of the high temperature process, the peeling force was compared when the conditions of room temperature, high temperature and low temperature were sequentially applied to the respective pressure sensitive adhesive films.
Using the respective adhesive films, three laminated layers of a glass plate / specimen / polyimide film were formed under the same conditions and in the same manner as in Experimental Example 2 for the peeling force.
The first peeling force was measured for each of the laminated bodies according to the peeling force measured at room temperature in Experimental Example 3 with respect to the peeling force, that is, the same conditions and methods as those for F 1 .
For each of the other laminate, the second peeling force was measured according to the same peeling force measured at high temperature of Experimental Example 3 against the peeling force, that is, the same conditions and method as F 2 .
Immediately after the respective adhesive films were formed with respect to the peel force of another laminate, the laminate was allowed to stand at a temperature of 150 캜 for 30 minutes, then at -20 캜 for 10 minutes, then at room temperature for 10 minutes The third peeling force was measured at a temperature of 25 DEG C, a peeling rate of 600 mm / min, and a peeling angle of 90 DEG, using a Texture Analyzer.
Table 2 shows changes in the peeling force when the conditions of room temperature, high temperature and low temperature thus obtained are sequentially applied.
(° C)
(gf / 80 mm)
(-69)
(Measurement impossible)
(147)
(117,900)
(Kept at 25 < 0 > C)
(Left at 150 DEG C for 30 minutes)
(Left at 150 DEG C for 30 minutes and left at -20 DEG C for 10 minutes)
As shown in Table 1, the pressure-sensitive adhesive layer of the pressure-sensitive adhesive film according to Example 1 exhibited excellent heat resistance in a range of 75 占 폚, exhibiting a peel force of 130 gf / 80 mm at room temperature, It can be clearly predicted that the base material can be stably supported and that the rate of change of the peeling force is -69%, so that the phenomenon of sticking or expanding to the substrate in the high temperature process will be prevented.
Particularly, as shown in Table 2, the adhesive film according to Example 1 can sufficiently lower the peeling force under the low-temperature condition after sequentially applying the normal temperature and high-temperature conditions, and accordingly, It can be clearly predicted that the glass substrate can be easily peeled off without damaging both the plastic substrate and the glass plate when the glass substrate is removed under low temperature conditions.
In addition, the adhesive film according to Example 1 can realize excellent tackiness for both the plastic substrate and the glass plate by including the intermediate substrate layer, and the overall thermal expansion coefficient thereof is also lowered, so that the difference in thermal expansion coefficient between the plastic substrate and the glass plate And it is possible to clearly prevent the phenomenon that the adhesive film is wrinkled or detached in a process of lowering the temperature from a high temperature to a normal temperature.
On the other hand, as shown in Table 1, the adhesive film of Comparative Example 1 had a glass transition temperature of -56.2 DEG C, which was low in heat resistance, and had a high peeling force against glass sheets at room temperature, , It was clearly confirmed that the heat resistance was inferior due to the increase in the peeling force after the application of the normal temperature and high temperature conditions in succession.
In addition, the adhesive film according to Comparative Example 2 can not easily support the substrate used in the color filter process of the flexible or foldable display because the peeling force against the glass plate is too low at room temperature and can be easily attached and detached, It can be clearly predicted that it can not be formed.
In addition, the adhesive film of Comparative Example 3 has a problem that the peeling force against the plastic film is too low at room temperature and can be easily attached and detached, so that there is a problem that the color filter can not be stably formed as described above. It can be confirmed that the heat resistance is inferior because the peeling force is rapidly increased and the rate of change of the peeling force exceeds 2000%.
100: Adhesive film
110: Pressure sensitive adhesive layer
120: intermediate substrate layer
130: (meth) acrylic adhesive layer
Claims (20)
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
The pressure-sensitive adhesive layer has a peeling force of 25 gf / 80 mm to 3,000 gf / 80 mm measured at room temperature, a peeling rate of 600 mm / min and a peeling angle of 90 deg.
Adhesive film.
The pressure-sensitive adhesive layer preferably has a rate of change (R) of the peeling force according to the following equation 1 with respect to a base material made of a plastic material of -500% to 2,000%
Adhesive film:
[Equation 1]
(R,%) = {(F 2 - F 1 ) / F 1 } X 100
In the above formula 1, F 1 means a peeling force measured in a state where the pressure-sensitive adhesive layer is continuously maintained at room temperature without any additional heat treatment immediately after the pressure-sensitive adhesive layer is formed, and F 2 is a temperature And the peel strength measured in a state where the peel strength is maintained at room temperature for 30 minutes, and both F 1 and F 2 are measured at a peel rate of about 600 mm / min and a peel angle of about 90 ° to be.
Wherein the pressure-sensitive adhesive layer has a glass transition temperature of 30 캜 to 80 캜
Adhesive film.
The modified phenoxy resin preferably has a weight average molecular weight of 10,000 g / mol to 100,000 g / mol
Adhesive film.
The glass transition temperature of the modified phenoxy resin is from 10 캜 to 90 캜
Adhesive film.
Wherein the modified phenoxy resin has a hydroxyl group equivalent of 10 to 50
Adhesive film.
The modified phenoxy resin is obtained by a reaction between a phenoxystyrene resin and a compound represented by the following formula (2)
Adhesive film:
(2)
In Formula 2, R 1 is H or a methyl group, and n is 1, 2, or 3.
A part of the hydroxyl groups of the phenoxy resin is chemically reacted with the compound represented by the formula 2 to form a functional group represented by the formula 1
Adhesive film.
The modified phenoxy resin may be prepared by reacting 70 parts by weight to 110 parts by weight of the compound represented by Formula 2 with 100 parts by weight of phenoxystyrene resin
Adhesive film.
The (meth) acrylic adhesive layer comprises a thermosetting composition of a (meth) acrylic adhesive composition comprising 70 to 99% by weight of a (meth) acrylic prepolymer having a weight average molecular weight of 1,000,000 g / mol to 2,000,000 g /
Adhesive film.
The (meth) acrylic adhesive layer has a peeling strength of 100 gf / 80 mm to 600 gf / 80 mm measured at a peeling speed of 600 mm / min and a peeling angle of 180 deg.
Adhesive film.
Wherein the (meth) acrylic adhesive layer has a glass transition temperature of -60 캜 to about -30 캜
Adhesive film.
Wherein the intermediate substrate layer comprises a film of a thermoplastic resin material
Adhesive film.
And forming a pressure-sensitive adhesive layer on the other surface of the intermediate substrate layer,
Wherein the pressure-sensitive adhesive layer is formed by curing a pressure-sensitive adhesive composition comprising a modified phenoxy resin having a functional group represented by the following Formula 1:
[Chemical Formula 1]
In Formula 1, R 1 is H or a methyl group, and n is 1, 2, or 3.
Phenoxystyrene resin and a compound represented by the following formula 2 to form a modified phenoxy resin having the functional group represented by the formula 1
Method of producing adhesive film:
(2)
In Formula 2, R 1 is H or a methyl group, and n is 1, 2, or 3.
70 parts by weight to 110 parts by weight of the compound represented by the general formula (2) is chemically reacted with 100 parts by weight of the phenoxy resin
A method for producing an adhesive film.
The (meth) acrylic adhesive layer is heat-treated on a (meth) acrylic adhesive composition comprising 70 to 99% by weight of a (meth) acrylic prepolymer having a weight average molecular weight of 1,000,000 to 2,000,000 g / Thereby forming a thermosetting reaction
A method for producing an adhesive film.
The pressure-sensitive adhesive layer is formed to have a peel force of 25 gf / 80 mm to 3,000 gf / 80 mm measured at room temperature, a peeling speed of 600 mm / min, and a peeling angle of 90 ° with respect to a base material made of plastic
A method for producing an adhesive film.
The (meth) acrylic adhesive layer is formed on a glass substrate so that the peeling force measured at a peeling rate of 600 mm / min and a peeling angle of 180 is 100 gf / 80 mm to 600 gf / 80 mm
A method for producing an adhesive film.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20190036954A (en) * | 2017-09-28 | 2019-04-05 | 타이미드 테크 인코퍼레이티드 | Thermal-curable adhesive composition and adhesive sheet |
| KR20190087768A (en) * | 2018-01-17 | 2019-07-25 | 주식회사 엘지화학 | Low reflection adhesive composition, adhesive film comprising the cured product thereof, and optical member comprising thereof |
| US10947417B2 (en) | 2017-09-29 | 2021-03-16 | Taimide Tech. Inc. | Thermal-curable adhesive composition and adhesive sheet |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002327160A (en) * | 2001-05-07 | 2002-11-15 | Soken Chem & Eng Co Ltd | Adhesive composition and adhesive sheet for display obtained by using the composition |
| JP2007009201A (en) * | 2006-06-16 | 2007-01-18 | Hitachi Chem Co Ltd | Electrode-connecting adhesive and connecting structure of fine electrode given by using the same |
| KR20140094216A (en) * | 2013-01-21 | 2014-07-30 | 제일모직주식회사 | Adhesive film, adhesive composition for the same and display member comprising the same |
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2015
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002327160A (en) * | 2001-05-07 | 2002-11-15 | Soken Chem & Eng Co Ltd | Adhesive composition and adhesive sheet for display obtained by using the composition |
| JP2007009201A (en) * | 2006-06-16 | 2007-01-18 | Hitachi Chem Co Ltd | Electrode-connecting adhesive and connecting structure of fine electrode given by using the same |
| KR20140094216A (en) * | 2013-01-21 | 2014-07-30 | 제일모직주식회사 | Adhesive film, adhesive composition for the same and display member comprising the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190036954A (en) * | 2017-09-28 | 2019-04-05 | 타이미드 테크 인코퍼레이티드 | Thermal-curable adhesive composition and adhesive sheet |
| US10947417B2 (en) | 2017-09-29 | 2021-03-16 | Taimide Tech. Inc. | Thermal-curable adhesive composition and adhesive sheet |
| KR20190087768A (en) * | 2018-01-17 | 2019-07-25 | 주식회사 엘지화학 | Low reflection adhesive composition, adhesive film comprising the cured product thereof, and optical member comprising thereof |
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