KR20150037015A - Uv curable optical resin adhesive compositions - Google Patents
Uv curable optical resin adhesive compositions Download PDFInfo
- Publication number
- KR20150037015A KR20150037015A KR20130116160A KR20130116160A KR20150037015A KR 20150037015 A KR20150037015 A KR 20150037015A KR 20130116160 A KR20130116160 A KR 20130116160A KR 20130116160 A KR20130116160 A KR 20130116160A KR 20150037015 A KR20150037015 A KR 20150037015A
- Authority
- KR
- South Korea
- Prior art keywords
- acrylate
- main chain
- chain polymer
- resin adhesive
- optical resin
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06F—ELECTRIC DIGITAL DATA PROCESSING
- G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
Abstract
(A) at least one member selected from the group consisting of a polyurethane acrylate main chain polymer, a polyisoprene acrylate main chain polymer and a polybutadiene acrylate main chain polymer,
(B) a photopolymerization initiator
(C) a reactive monomer and
(D) an ultraviolet curable optical resin adhesive composition comprising a compound represented by the following formula (1).
[Chemical Formula 1]
In this formula,
R 1 is an alkylene group having 1 to 10 carbon atoms,
R 2 is an alkyl group having 10 to 30 carbon atoms.
Description
The present invention is used for laminating a touch panel and an image display panel (LCD or OLED Panel), or for laminating and bonding a protective cover plate and a touch panel or an image display panel, To an ultraviolet curing type optical resin adhesive composition excellent in image display quality, transparency, adhesion reliability and durability, and particularly excellent in rework ability, in keeping and maintaining high contrast.
BACKGROUND ART [0002] As a high-level information society has developed in recent years, many functional devices such as an organic EL display (OLED) and a liquid crystal display (LCD) have been proposed. In order to protect the display panel between the touch panel and the display panel (LCD, OLED panel) or between the display panel and the protective cover plate (the front cover: made of glass or acrylic resin) An air gap structure (hollow structure) composed of pores having a size of about 1.5 mm has been adopted (for example, Korean Patent Laid-Open Publication No. 2011-0131044).
However, since the air gap structure portion is an air layer, it is near 1.0, which is a large difference from the refractive index 1.5 of the liquid crystal display panel (LCD module) and the protective cover plate (front cover) to which various polarizing plates are attached. Diffusion or scattering occurs largely in this air layer, which causes a problem of deterioration of brightness and contrast. Therefore, it has been proposed to fill a transparent optical resin, which is close to the refractive index of glass or acrylic resin, in the air gap structure portion. By filling the air gap with the optical resin by using the optical resin, the optical interface between the touch panel and the display panel or between the display panel and the protective cover plate (front cover) is eliminated, and the reflection scattering of the image light is reduced to improve the luminance and the contrast It is possible to provide this large, high-quality image. Further, by filling the air gap with the optical resin, the strength of the entire image display device is increased. Even if the protective cover plate (front cover) is broken, the glass as a forming material is not scattered. And strength is improved.
However, when assembling the image display apparatus including the display panel, the touch panel plate, the protective cover plate, the lens plate, and the like, if the positions of the joints are shifted at the time of bonding between the respective plates, Loss is great. Particularly, in a large-sized image display apparatus, the unit price of the apparatus itself becomes higher, so it is essential to increase the yield of manufacturing and to rework the defective product when defective products are produced. A rework method has been adopted in which an adhesive resin layer is cut with a fine wire, the resin residue after cured is swollen and removed with a solvent, and the resin residue is transferred back to the assembling process.
As the above-mentioned optical resin adhesive composition, there has been proposed a composition comprising a polyurethane acrylate main chain polymer, a polyisoprene acrylate main chain polymer, a polybutadiene acrylate main chain polymer, and an ultraviolet curable optical resin adhesive composition comprising a monomer (meth) acrylate as a main component (For example, Korean Patent Publication No. 2002-0030852). In this case, straight-chain hydrocarbon solvents such as hexane and heptane, aromatic hydrocarbon solvents such as toluene and xylene, and the like have been used as a solvent for swelling and removing the resin residue after being cut into the respective panels by the fine wires . However, these hydrocarbon solvents are also problematic in that the solvent also slowly penetrates and swells and damages the polarizing plate with respect to the diffusion plate, the retardation film, and the non-polar cycloolefin polymer (COP) .
Further, even in the case of an adhesive composition composed of a polymer other than the above, there is a problem that the swelling of the resin residue takes a long time. That is, it is strongly desired to develop an optical resin adhesive composition which can easily rework using a swelling solvent for a resin residue without adversely affecting each plate, which is a component of an image display apparatus.
An object of the present invention is to solve the above problems of the prior art and to provide an ultraviolet curable optical resin adhesive composition for interlayer filling which is excellent in transparency, adhesion reliability, durability and excellent in reworkability without adversely affecting luminance or contrast, The purpose is to provide.
In order to solve the above object,
The present invention
(A) at least one member selected from the group consisting of a polyurethane acrylate main chain polymer, a polyisoprene acrylate main chain polymer and a polybutadiene acrylate main chain polymer,
(B) a photopolymerization initiator,
(C) a reactive monomer and
(D) a compound represented by the following formula (1)
The present invention provides an ultraviolet curable optical resin adhesive composition.
[Chemical Formula 1]
In this formula,
R1 is an alkylene group having 1 to 10 carbon atoms,
R2 is an alkyl group having 10 to 30 carbon atoms.
Preferably, the composition is used for gap filling of an optical image display panel, a touch panel or a protective cover plate.
Preferably, the compound represented by the formula (1) is contained in an amount of 0.01 to 50 parts by weight based on 100 parts by weight of the component (A).
The composition of the present invention is useful for assembling an image display apparatus composed of a display panel, a touch panel plate, a protective cover plate, a lens plate, and the like, when the positional deviation of the bonding occurs at the time of bonding between the respective plates, It is excellent in the reworkability that the expensive display panel and the touch panel plate can be reused, and has excellent transparency, adhesion reliability, and durability without adversely affecting luminance and contrast.
The present invention
(A) at least one member selected from the group consisting of a polyurethane acrylate main chain polymer, a polyisoprene acrylate main chain polymer and a polybutadiene acrylate main chain polymer,
(B) a photopolymerization initiator,
(C) a reactive monomer and
(D) a compound represented by the following formula (1)
The present invention provides an ultraviolet curable optical resin adhesive composition.
[Chemical Formula 1]
In this formula,
R 1 is an alkylene group having 1 to 10 carbon atoms,
R 2 is an alkyl group having 10 to 30 carbon atoms.
Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to these embodiments.
The ultraviolet curable optical resin adhesive composition of the present invention can be used in a case where a touch panel and an image display panel (LCD or OLED Panel) are laminated or laminated, or a protective cover plate and a touch panel or an image display panel are laminated and adhered, It is used to fill the gap.
The ultraviolet curable optical resin adhesive composition (hereinafter, also referred to as an "optical resin adhesive composition" or "adhesive composition") of the present invention is preferably a polyurethane acrylate main chain polymer, a polyisoprene acrylate main chain polymer or a polybutadiene acrylate main chain Is obtained by using a polymer (component A) and a photopolymerization initiator (component B) as essential components.
polymer
The polyurethane acrylate type main chain polymer, polyisoprene acrylate type main chain polymer or polybutadiene acrylate type main chain polymer (component A) of the present invention is a liquid random copolymer having a weight average molecular weight of about 500 to 500,000.
The polymer is preferably a polyurethane acrylate backbone polymer.
The polyurethane acrylate main chain polymer, polyisoprene acrylate main chain polymer or polybutadiene acrylate main chain polymer (component A) may be contained in an amount of 30 to 90% by weight based on the entire composition.
When the content is less than 30%, the content of other components (particularly, the component B) is high, which causes severe shrinkage during film formation.
Light curing
Initiator
The photopolymerization initiator (component B) used together with the polymer (component A) acts as an ultraviolet (UV) curing agent, and various photopolymerization initiators such as photo radical polymerization initiators and photocationic polymerization initiators are used. In the present invention, when a touch panel in which a transparent electrode such as indium tin oxide (ITO) is formed on a liquid crystal display device is used, for the purpose of avoiding ITO corrosion by ions (particularly counter anion) derived from a photopolymerization initiator, More preferably, a photo-radical polymerization initiator can be used.
Examples of the photo-radical polymerization initiator include, but are not limited to, Igacure 184, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1 -hydroxy-cyclohexyl- Methyl-1-phenyl-propan-1-one, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy- Benzyl-2-methyl-propan-1-one, 2-benzyl-2-dimethylamino-1- (4 (4-methylthiophenyl) -2-morpholinopropane-1-one, bis (2,4,6-trimethylbenzoyl) -phenyl Phosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis (? 5-2,4-cyclopentadien-1-yl) 2-methyl-propyl) - < / RTI > 1-on. These may be used alone or in combination of two or more. Among them, 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy- - {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methyl-propan-1-one.
Examples of the photocationic polymerization initiator include triarylsulfonium salts and bismuth nitrite photo cationic polymerization initiators.
The blending amount of the photopolymerization initiator is preferably in the range of 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the component A used in the present invention.
When the blending amount of the photopolymerization initiator is too small, the degree of polymerization tends to become insufficient. When the blending amount of the photopolymerization initiator is too small, the durability of the ultraviolet curing type optical resin adhesive composition is lowered and the solvent resistance and chemical resistance tend to be lowered.
Reactive monomer
In the ultraviolet curable optical resin adhesive composition of the present invention, various monofunctional (meth) acrylate compounds may be contained as the reactive monomer (Component C).
Examples of the monofunctional (meth) acrylate compounds include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (Meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, neopentyl Acrylate, dicyclopentanyl (meth) acrylate, tricyclodecyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, lauryl (Meth) acrylate, glycidyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, dimethylaminoethyl , tree Hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, pentaerythritol (meth) acrylate, glycerin ( Acrylate and monofunctional (meth) acrylates such as methacrylate and methacrylate. These may be used alone or in combination of two or more.
Particularly, in order to improve the adhesiveness of the resulting cured product, it is preferable to use an ester of tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, and (meth) acrylate in which the ester residue of (meth) Hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, pentaerythritol (meth) acrylate, glycerin (meth) acrylate And the like are preferably used. More preferably, 2-hydroxyethyl (meth) acrylate and tetrahydrofurfuryl (meth) acrylate are used.
The content of the (meth) acrylate compounds is preferably 5 to 200 parts by weight based on 100 parts by weight of the polyurethane acrylate main chain polymer, polyisoprene acrylate main chain polymer or polybutadiene acrylate main chain polymer (component A) And more preferably 10 to 100 parts by weight.
If the amount is less than the above range, it is difficult to obtain the effect of improving the adhesion, while if it is excessively large, the viscosity tends to be lowered and the coating property tends to be lowered.
The compound represented by the formula (1)
[Chemical Formula 1]
In this formula,
R 1 is an alkylene group having 1 to 10 carbon atoms,
R 2 is an alkyl group having 10 to 30 carbon atoms.
When the compound represented by the above formula (1) is used, an ultraviolet curable optical resin adhesive composition for interlayer filling which is excellent in transparency, adhesion reliability and durability while maintaining a level equivalent to that of the conventional composition and having excellent high workability can be obtained.
The compound (component D) represented by the formula (1) is 0.01 to 50 parts by weight based on 100 parts by weight of the polyurethane acrylate main chain polymer, polyisoprene acrylate main chain polymer or polybutadiene acrylate main chain polymer (component A) And more preferably 0.1 to 20 parts by weight.
In addition, the ultraviolet curable optical resin adhesive composition of the present invention may contain additives such as a silane coupling agent, an antioxidant, a defoaming agent, a surfactant, a colorant, an organic filler, various spacers, And may be appropriately blended as required. These may be used alone or in combination of two or more.
The ultraviolet curable optical resin adhesive composition of the present invention can be produced, for example, by mixing a specific polymer (component A), a photopolymerization initiator (component B), a reactive monomer (component C), a compound And mixing the mixture by stirring with a stirring mixer or a glass stirrer.
The ultraviolet curable optical resin adhesive composition of the present invention thus obtained can be used as follows.
The composition thus prepared
1) Coat with a thickness of 100 ~ 500 um between the middle layer and the light layer,
2) UV irradiation (exposure dose: 100 to 10000 mJ / cm 2 ) is applied to the coating to make a film.
The ultraviolet curing type optical resin adhesive film prepared as described above is used for lamination adhesion of a touch panel and an image display panel (LCD or OLED Panel), lamination adhesion of a protective cover plate and a touch panel or an image display panel, .
As the light source used in the ultraviolet ray irradiation, various known light sources such as carbon arc, mercury vapor arc, ultrahigh pressure mercury lamp, high pressure mercury lamp, and xenon lamp can be used.
When the display panel has a problem after the display panel is assembled, the adhesive layer is cut using the above-mentioned fine wire to peel off each panel plate, and then the resin residue remaining on the release surface is swollen with the solvent .
In general, the nonwoven fabric wiper is provided with a repairing agent (swelling solvent) so as to stand on the resin residue to swell.
Examples of the swelling agent include non-erosive swelling agents such as ketone type, ester type, ether type, and cellosolve type such as methyl isobutyl ketone (MIBK) from the standpoint of non-erosive property against nonpolar cycloolefin polymer (COP) Solvent (repair solvent) and the like can be used.
The resin residue is removed and then cleaned with an alcohol-based solvent, so that it can be returned to the assembling step.
It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the inventions.
Example
And
Comparative Example
1. Examples 1 to 6 were prepared as shown in the following Table 1. (Unit: parts by weight)
(A) a polyurethane acrylate-based backbone polymer
(B) a photopolymerization initiator
(C) a reactive monomer
(D) a compound represented by the formula (1)
Component (A): Miwon Specialty Chemical: UA5210
Ingredient (B): Ciba Igacure 184
Component (C) - Monomer 1: isobonyl (meth) acrylate
Component (C) - monomer 2: dicyclopentanyl (meth) acrylate
Component (D): NOF Corporation (Sun): ALFLOW H50 (compound represented by the formula (1)
2. Comparative Examples 1 to 3 were prepared as shown in Table 2 below (unit: parts by weight)
(A) a polyurethane acrylate-based backbone polymer
(B) a photopolymerization initiator
(C) a reactive monomer
Component (A): Miwon Specialty Chemical: UA5210
Component (B): Igacure 184
Component (C) - Monomer 1: isobonyl (meth) acrylate
Component (C) - monomer 2: dicyclopentanyl (meth) acrylate
Various properties tests were conducted on the thus prepared examples and comparative compositions according to the methods described below and evaluated. The results are shown in Table 3 below.
1) Total light transmittance: TT
The compositions of the above examples and comparative examples were applied between the light peel and the middle thick two films and coated with a thickness of 200 mu m using an applicator. An exposure dose of 1,500 mJ / cm < 2 > Thereafter, the fabricated sample was removed from the delamination and laminated on a slide glass. Subsequently, heavy lifting was also removed. The measurement sample thus obtained was measured with a Murakami Color Research Lab. Total light transmittance (TT) was measured using Hazemeter HM-150.
2) Haze: Hz
Using the same measuring sample as above, the same Murakami Color Research Lab. Haze (Hz) values were measured using Hazemeter HM-150.
3) Adhesiveness
The compositions of the above examples and comparative examples were applied between the light peel and the middle thick two films and coated with a thickness of 200 mu m using an applicator. An exposure dose of 1,500 mJ / cm < 2 > Thereafter, the fabricated sample was removed from the delamination and laminated on a slide glass. Subsequently, heavy lifting was also removed. A new PET film was adhered onto the composition. (Width * length = 30 mm * 250 mm). After leaving for one day at 25 ° C, 50, RH%, adhesion was measured with an Instron at 180 ° peel off test.
4) Wire cutting strength
Two slide glass plates (thickness: 1 mm) sandwiching spacers having a thickness of 650 탆 were prepared, the above compositions were filled without bubbles, and irradiated with UV at a proper exposure dose (1500 mJ / cm 2 ) to cure the sample for measurement . With respect to the sample of the double-side slide glass plate, the wire was stretched in the cross-sectional direction of the cured product by using a SUS wire having a diameter of 500 탆, and the fracture strength of the cured product was measured using Instron.
5) swelling
(Non-woven fabric containing a solvent (methyl isobutyl ketone)) for a predetermined time (Examples 1 to 6: 10 minutes, Comparative Examples 1 to 3: 60 minutes) on a resin residue on a slide glass plate broken at room temperature ), And degree of swelling of the resin residue was evaluated in three stages according to the following criteria.
○: The resin residue completely swelled.
?: 10% or more of the total area of the resin residue swelled.
X: Less than 10% of the total area of the resin residue was swollen or not swollen at all.
6) Cleanliness
In the swelling property evaluation test, a test sample completely swollen by the area unit (evaluation in the swelling test) was wiped with a nonwoven fabric containing ethanol, and the result was evaluated in two steps according to the following criteria. Further, in the swelling property evaluation, the test samples for evaluation of? And X were not evaluated.
?: Residues such as resin residues were not confirmed.
X: Residue such as resin residue was confirmed.
The results showed that Examples 1 to 6 containing the compound represented by Chemical Formula 1 had the same level of physical properties as those of Comparative Examples 1 to 3 in terms of TT, Hz and adhesion, Since the swelling property was abundant, a good evaluation result was obtained with respect to the cleaning property. Therefore, it can be seen that the composition containing the compound represented by the formula (1) has good swelling property and excellent reworkability.
Claims (3)
(B) a photopolymerization initiator,
(C) a reactive monomer and
(D) a compound represented by the following formula (1)
Wherein the ultraviolet curing-type optical resin adhesive composition comprises:
[Chemical Formula 1]
In this formula,
R 1 is an alkylene group having 1 to 10 carbon atoms,
R 2 is an alkyl group having 10 to 30 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130116160A KR20150037015A (en) | 2013-09-30 | 2013-09-30 | Uv curable optical resin adhesive compositions |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130116160A KR20150037015A (en) | 2013-09-30 | 2013-09-30 | Uv curable optical resin adhesive compositions |
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| KR20150037015A true KR20150037015A (en) | 2015-04-08 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108485589A (en) * | 2018-04-18 | 2018-09-04 | 东莞市新懿电子材料技术有限公司 | A kind of anti-ultraviolet UV glue and preparation method thereof |
| KR20200109513A (en) | 2019-03-13 | 2020-09-23 | 도우성 | Low-intensity ultraviolet-curing hybrid point-adhesive composition and method of manufacturing thereof |
-
2013
- 2013-09-30 KR KR20130116160A patent/KR20150037015A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108485589A (en) * | 2018-04-18 | 2018-09-04 | 东莞市新懿电子材料技术有限公司 | A kind of anti-ultraviolet UV glue and preparation method thereof |
| KR20200109513A (en) | 2019-03-13 | 2020-09-23 | 도우성 | Low-intensity ultraviolet-curing hybrid point-adhesive composition and method of manufacturing thereof |
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