KR101397695B1 - Optical adhesive composition, optical adhesive film comprising the same and display apparatus comprising the same - Google Patents

Abstract

The present invention relates to an optical adhesive composition and an optical adhesive film comprising the same. More specifically, the present invention relates to an optical adhesive composition comprising an ultraviolet non-curable compound and an optical adhesive film comprising the same. By reducing the hardening shrinkage ratio, the present invention can solve the leakage problem such as the light leakage phenomenon due to the shrinkage of the edge portion generated in the photo-curing and solve the problem of lowering the adhesion due to the temperature during driving the display.

Description

TECHNICAL FIELD The present invention relates to an optical adhesive composition, an optical adhesive film containing the same, and a display device including the same,

The present invention relates to an optical adhesive composition, an optical adhesive film containing the same, and a display device comprising the same. More specifically, the present invention relates to an optical pressure-sensitive adhesive composition comprising an ultraviolet non-curable compound, an optical pressure-sensitive adhesive film comprising the same, and a display device comprising the same. By reducing the hardening shrinkage ratio and increasing the elongation ratio, leakage problems such as light leakage due to shrinkage of the edge portion occurring during photo-curing can be solved, and the problem of deterioration of adhesion due to temperature during driving of the display can be solved.

As the touch screen market grows and the range of applications ranging from small size such as mobile phones to large size displays such as TVs has been diversified, the pressure sensitive adhesives acting between the upper window and lower TSP sensor glass to improve outdoor visibility and impact resistance Development is required.

Currently, in the turkscreen market, film-type optical clear adhesive (OCA) is used to laminate the window and TSP on the same principle as double-sided tape. However, when foreign matters or bubbles are generated in the lapping process, the bubbling process is not easy and a process failure problem may occur. In addition, there is a problem of a high price and the demand for a liquid resin type adhesive is increasing. In addition, in the case of small-sized and large-sized displays, the liquid resin type is more advantageous than the film type in view of the development trend in which curving is introduced like a flexible display.

However, in the case of a liquid resin type adhesive, light leakage may occur at the edge portions due to shrinkage upon photo-curing. Further, the adhesive force of the pressure-sensitive adhesive may be lowered due to the temperature generated during the driving of the display, or peeling or lifting of the edge portion may occur. This problem is especially problematic for large size displays.

An object of the present invention is to provide an optical pressure-sensitive adhesive composition which minimizes the hardening shrinkage upon curing.

Another object of the present invention is to provide an optical pressure-sensitive adhesive composition which minimizes light leakage and leakage during curing.

Another object of the present invention is to provide a liquid type optical pressure-sensitive adhesive composition which can be used for a large size display.

Another object of the present invention is to provide an optical adhesive film comprising the above optical adhesive composition.

Another object of the present invention relates to a display device comprising the optical adhesive composition or the optical adhesive film.

An optical adhesive composition which is an aspect of the present invention may comprise a compound having a structure represented by the following formula (1).

≪ Formula 1 >

(Wherein, n and m are each independently an integer of 0 to 10,

Except that n and m are both 0,

Wherein each of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 independently represents hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, CH2-) sO- [-CH2-CH2O-] t-CH2CH2OH wherein s is an integer from 0 to 5 and t is an integer from 0 to 5,

At least one of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 is selected from the group consisting of a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, - (-CH2-) -CH2CH2OH (s is an integer from 0 to 5 and t is an integer from 0 to 5).

Another aspect of the present invention is an optical pressure-sensitive adhesive composition comprising a compound having the structure of Formula 1, wherein the curing shrinkage ratio represented by Formula 1 may be 2% or less.

<Formula 1>

Cure shrinkage ratio = [(specific gravity of liquid composition before curing-specific gravity of solid after curing)] / specific gravity of liquid composition before curing x 100

, Preferably 1.5% or less, more preferably 0.8% -1.2%.

Another aspect of the present invention is an optical pressure-sensitive adhesive composition comprising a compound having the structure of Formula 1 and having an adhesive force of 35-60 kgf to a 1.5 cm x 1.5 cm glass plate.

The optical pressure-sensitive adhesive film according to another aspect of the present invention includes a compound having the structure of Formula 1, and may have an elongation of 400% or more, preferably 400 to 800% It can have elongation.

A display device which is another aspect of the present invention may comprise the optical pressure-sensitive adhesive composition or the optical pressure-sensitive adhesive film.

The present invention provides an optical pressure-sensitive adhesive composition which minimizes the hardening shrinkage upon curing. The present invention provides an optical pressure-sensitive adhesive composition which minimizes light leakage and leakage during curing. The present invention provides a liquid type optical pressure-sensitive adhesive composition which can be used for a large size display.

An optical adhesive composition which is an aspect of the present invention may comprise a compound having a structure represented by the following formula (1).

&Lt; Formula 1 >

(Wherein, n and m are each independently an integer of 0 to 10,

Except that n and m are both 0,

Wherein each of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 independently represents hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, CH2-) sO- [-CH2-CH2O-] t-CH2CH2OH wherein s is an integer from 0 to 5 and t is an integer from 0 to 5,

At least one of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 is selected from the group consisting of a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, - (-CH2-) -CH2CH2OH (s is an integer from 0 to 5 and t is an integer from 0 to 5).

Preferably, n and m independently of each other may be an integer of 0 to 5, more preferably 0 to 1.

The aromatic ring may be included in the compound in an amount of 2 to 10, preferably 4 to 5.

- (CH2) sO- [-CH2-CH2O-] t-CH2CH2OH (s is an integer of 0 to 5, and t is an integer of 0 to 5), the hydroxyl group may be an alkyl group having 1 to 10 carbon atoms directly bonded to the aromatic ring or substituted with a hydroxyl group, An integer of 0 to 5), and the like. The hydroxyl group serves to increase the adhesive force of the optical pressure-sensitive adhesive composition.

The compound may be an ultraviolet non-curable compound.

The compound does not contain a functional group capable of participating in the ultraviolet curing reaction, for example, a double bond. Therefore, even when the optical pressure-sensitive adhesive composition is cured, it is not cured. Instead, the compound is a lipophilic molecule that occupies a large portion of aromatic rings in the molecule. The molecule is stabilized in the form of a planar structure by an aromatic ring, and is stacked by a strong attraction between electrons of the aromatic ring This is possible. As a result, the curing shrinkage ratio can be lowered by being present in the cured product of the pressure-sensitive adhesive composition without being cured, but not exiting into the liquid phase.

For example, the compound may have the structure of the following formula (2) or (3).

(2)

- (-CH2O-) n1- (-CH2-) m1-A2- (-CH2O-) n2- (-CH2-) m2-

(3)

- (-CH2O-) n3- (-CH2-) m1-A2- (-CH2O-) n2- (-CH2-) m2- (-CH2O-) n4- (-CH2-) m4-A5

(Wherein n1, n2, n3, n4, m1, m2, m3 and m4 are each independently an integer of 0 to 10,

When n1 and m1 are all 0, n2 and m2 are both 0, n3 and m3 are both 0, and n4 and m4 are both 0,

A1 to A5 may be any one of the following formulas (a), (b), (c), or (d).

(a)

 (b)

(c)

(d)

R 1, R 2, R 3, R 4 and R 5 may be the same or different from each other and each independently represent hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, (-CH2-) sO- [-CH2-CH2O-] t-CH2CH2OH wherein s is an integer from 0 to 5 and t is an integer from 0 to 5, and R1, R2, R3 , - (CH2) sO- [-CH2-CH2O-] t-CH2CH2OH (s is an integer of 0 to 5), and at least one of R4 and R5 is a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, , t is an integer from 0 to 5).

Preferably, n and m independently of each other may be an integer of 0 to 1.

Specific examples of the above compound may be selected from the group consisting of the following compounds, but are not limited thereto:

;

;

;

;

;

;

; 및

; And

(Wherein R is hydrogen, hydroxyl or methyl, and t is an integer of 0-5).

The refractive index of the compound may be 1.47 to 1.6. This can reduce the refractive index difference between the window and the TSP glass by raising the refractive index of the optical pressure-sensitive adhesive composition, thereby preventing the sharpness of the display screen from being deteriorated due to refraction or reflection of light.

The weight average molecular weight of the compound may be 50-3000 g / mol. Within the above range, it is possible to prevent the non-cured material from escaping to the outside of the film during curing to prevent occurrence of hardening defects.

The compound may be contained in an amount of 1-30% by weight of the optical adhesive composition. Within the above range, it is possible to prevent curing defects from escaping into the liquid phase without staying in the film which is a cured product upon curing. Preferably 5-30% by weight, more preferably 10-30% by weight.

While these compounds have oleophilicity due to aromatic rings, urethane (meth) acrylate copolymers, which occupy the largest portion in the pressure-sensitive adhesive composition described below, are hydrophilic. Therefore, it is important to set an appropriate mixing ratio between the above compound and the urethane (meth) acrylate copolymer described below.

In the optical pressure-sensitive adhesive composition, the compound: urethane (meth) acrylate copolymer may be contained in a weight ratio of 1: 0.5 to 1:10. Within this range, the compatibility between the hydrophilic molecule and the lipophilic molecule is good, and the shrinkage rate upon curing can be minimized. Preferably in a weight ratio of 1: 1.5 to 1: 6.

The optical adhesive composition of the present invention may further comprise a urethane (meth) acrylate copolymer, a reactive monomer and an initiator.

urethane ( Meta ) Acrylate  Copolymer

The urethane (meth) acrylate copolymer can be prepared by first polymerizing a polyol and a diisocyanate compound to prepare a urethane oligomer, and further polymerizing a (meth) acrylate monomer.

The viscosity of the urethane (meth) acrylate copolymer can be 25,000-140,000 cps at 25 占 폚. Within this range, the hardening shrinkage ratio can be reduced.

The weight average molecular weight of the urethane (meth) acrylate copolymer may be 10K-30K g / mol. Within the above range, the durability, adhesive strength, elongation, heat resistance and moisture resistance of the optical pressure-sensitive adhesive may be good. Preferably 10K-26K g / mol.

The PDI of the urethane (meth) acrylate copolymer may be 1.0-1.9. Within this range, the molecular weight distribution of the urethane (meth) acrylate copolymer is so small that the physical properties of the copolymer may be equivalent.

The polyol is at least one selected from the group consisting of polypropylene diol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, polytetramethylene glycol, tetramethylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, , A polycarbonate polyol, a polyester polyol, and 1,4-cyclohexane dimethanol, but is not limited thereto.

The diisocyanate compound may include at least one selected from the group consisting of isoprene, hexamethylene, and toluene compounds, but is not limited thereto. Examples of the diisocyanate compound include isophorone diisocyanate (IPDI), hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, xylene diisocyanate, hydrogenated diphenylmethane diisocyanate and naphthalene diisocyanate, and 2, Toluene diisocyanate, and 4-toluene diisocyanate.

The (meth) acrylate monomer may be a (meth) acrylic acid ester having a hydroxy group, and may include a (meth) acrylic acid ester having a terminal or a hydroxyl group in the structure and having an alkyl group of 2 to 10 carbon atoms. Preferably 2-hydroxyethyl methacrylate.

The polymerization reaction of the polyol, the diisocyanate compound, and the (meth) acrylate monomer can be carried out by conventional polymerization methods such as bulk polymerization, emulsion polymerization, suspension polymerization and the like, and there is no particular limitation. The polymerization reaction can be carried out, for example, at 40-80 DEG C for 2-24 hours.

The polymerization reaction can be carried out in the absence of a catalyst or in the presence of a catalyst, preferably a catalyst is used to prepare the copolymer. As the catalyst, for example, at least one selected from the group consisting of dibutyltin dilaurate (DBTDL), triethylenediamine (TEDA) and 1,4-diazabicyclo [2.2.2] , But are not limited thereto. The catalyst may be used in an amount of 0.05 to 2 parts by weight based on 100 parts by weight of the polyol.

The urethane (meth) acrylate copolymer may be contained in an amount of 25 to 83.7% by weight in the optical adhesive composition. Within this range, the viscosity of the material can be controlled to improve the workability and show a low value of the shrinkage shrinkage. Preferably 40 to 60% by weight.

Reactive monomer

The reactive monomer includes a vinyl monomer having a hydroxy group, a vinyl monomer having an alkyl group, a vinyl monomer having an alicyclic group, a (meth) acrylic monomer having an alicyclic heterocycle, a vinyl monomer having a carboxyl group, a monomer having a silyl group and a vinyl group Etc. may be used.

Preferably, the reactive monomer may include a vinyl monomer having a hydroxyl group, a vinyl monomer having an alkyl group, a vinyl monomer having an alicyclic group, and a (meth) acrylic monomer having an alicyclic heterocycle.

The reactive monomer may be contained in an amount of 15 to 40% by weight in the optical adhesive composition. Within this range, the viscosity of the material can be controlled to improve the workability and show a low shrinkage rate. Preferably 15-30% by weight.

The vinyl-based monomer having a hydroxy group is preferably a (meth) acrylic acid ester having a hydroxy group, and may be a (meth) acrylic acid ester having a terminal or an alkyl group having 2 to 10 carbon atoms in the structure and having a hydroxy group. (Meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 6- 1-chloro-2-hydroxypropyl (meth) acrylate, diethylene glycol mono (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, (Meth) acrylate, neopentyl glycol mono (meth) acrylate, trimethylol propane di (meth) acrylate, diethylene glycol mono (Meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, 4-hydroxycyclohexyl Oxy (meth) acrylate, 4-hydroxy Cycle as hexyl (meth) may include the acrylate and cyclohexane dimethanol mono (meth) at least one member selected from the group consisting of acrylate, not limited to these. The vinyl monomer having a hydroxyl group may be contained in an amount of 1-10% by weight, preferably 2-8% by weight, in the optical adhesive composition.

The vinyl-based monomer having an alkyl group may include a (meth) acrylic acid ester having 1 to 20 carbon atoms which is acyclic or non-cyclic and has a linear or branched alkyl group. (Meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, (Meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, (Meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate and lauryl (meth) acrylate. It is not. The vinyl-based monomer having an alkyl group may be contained in an amount of 1-10% by weight, preferably 1-5% by weight, in the optical adhesive composition. It is possible to obtain a result that the stress stress can be eliminated within the above range.

The vinyl monomer having an alicyclic group may include a (meth) acrylic acid ester or (meth) acrylic monomer having an alicyclic ring of a single ring or a heterocyclic ring having 4 to 20 carbon atoms. But are not limited to, for example, isobornyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate. The vinyl monomer having an alicyclic group may be contained in an amount of 5-20% by weight, preferably 6-18% by weight, in the optical adhesive composition. Within the above range, the viscosity of the optical pressure-sensitive adhesive is adjusted to facilitate the workability in coating.

The (meth) acrylic monomer having an alicyclic heterocycle is a (meth) acrylic monomer having 4 to 6 carbon atoms and having a single alicyclic ring containing at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, . But are not limited to, for example, acryloylmorpholine (ACMO). The (meth) acrylic monomer having an alicyclic heterocyclic ring may be contained in an amount of 1-10% by weight, preferably 1-5% by weight. Within this range, adhesion between the optical adhesive and the glass or ITO film can be increased.

Examples of the vinyl monomer having a carboxyl group include (meth) acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, vinyl acetic acid, acrylic acid, methacrylic acid, fumaric acid, , And the like, but is not limited thereto. The vinyl monomer having a carboxyl group may be contained in an amount of 1-10% by weight in the optical adhesive film. It is possible to obtain a result that the adhesive force of the optical adhesive is increased within the above range.

The monomer having a silane group and a vinyl group can increase adhesion to glass. Examples of such monomers include "(R1) (R2) (R3) Si-CH = CH2 wherein R1, R2 and R3 are independently hydrogen, halogen, alkyl of 1-10 carbon atoms or alkoxy of 1-10 carbon atoms ) ". &Lt; / RTI &gt; For example, the monomer may include at least one selected from the group consisting of vinyltrichlorosilane, vinyltrimethoxysilane, vinylmethyldimethoxysilane, and vinyltriethoxysilane, but is not limited thereto. The monomer having the vinyl group and the silane group may be contained in an amount of 1-10% by weight in the optical adhesive composition.

Initiator

The initiator can be used without limitation as long as it can exhibit excellent light response at an ultraviolet wavelength band of 150-500 nm. For example, at least one selected from the group consisting of? -Hydroxy ketone series and phenyl glyoxylate series may be used, but is not limited thereto. For example, 1-hydroxycyclohexyl phenyl ketone, oxyphenylacetic acid 2- [2-oxo-2-phenylacetoxyethoxy] -ethyl ester, benzophenone, 4-phenylbenzophenone, hydroxybenzophenone, Benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'-bis (dimethylamino) benzophenone, 2,2'-diethoxy Acetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 2,4,6-trichloro-s-triazine, (Trichloromethyl) -s-triazine, thioxanthone, 2-methylthioxanthone, 2-methylthioxanthone, , Benzoin or benzoin methyl ether may be used.

The initiator may be included in an amount of 0.1 to 5% by weight in the optical adhesive composition. Within this range, the film after curing upon UV exposure can exhibit high elongation and low cure shrinkage values. Preferably 0.5 to 2% by weight.

The optical adhesive composition of the present invention may further comprise at least one member selected from the group consisting of an ultraviolet absorber and an antioxidant.

The ultraviolet absorber serves to improve the light stability of the pressure-sensitive adhesive film after curing. The ultraviolet absorber may include at least one selected from the group consisting of benzotriazole, benzophenone and triazine, but is not limited thereto. Preferably, a hydroxyphenylbenzotriazole-based ultraviolet absorber can be used. For example, the ultraviolet absorber may be selected from the group consisting of 7 to 9 linear or branched alkyl (meth) acrylates of 3- (2H-benzotriazol-2-yl) -5- (1,1-dimethylethyl) 4- Esters, 2- (benzotriazol-2-yl) -4- (2,4,4-trimethylpentan-2-yl) phenol, 2- (2'- 2- [2'-hydroxy-3 ', 5'-di-t-butyl (2'-hydroxybenzotriazole) Phenyl) benzotriazole, 2,4-hydroxybenzophenone, 2,4-hydroxy-4-methoxybenzophenone, 2,4-hydroxy-4-methoxybenzophenone- (2-hydroxy-4-methoxyphenyl) -1,3,5-triazine, 2,4-diphenyl-6- 1,3,5-triazine, 2,4-diphenyl-6- (2-hydroxy-4-propoxyphenyl) 2-hydroxy-4-butoxyphenyl) -1,3,5-triazine, and the like.

The ultraviolet absorber may be contained in an amount of 0.1 to 1% by weight, preferably 0.1 to 0.5% by weight, in the optical adhesive composition. Within the above range, the yellowing of the surface of the film after curing can be prevented.

The antioxidant serves to prevent the oxidation of the optical adhesive film after curing and to improve the thermal stability. The antioxidant may include, but is not limited to, at least one selected from the group consisting of a phenol compound, a quinone compound, an amine compound, and a phosphite compound. Examples of the antioxidant include pentaerythritol tetrakis (3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate), tris (2,4- ) Phosphite, and the like.

The antioxidant may be contained in an amount of 0.1 to 1% by weight in the optical adhesive composition. Preferably 0.1 to 0.5% by weight. Within the above range, it is possible to prevent the film after aging from being cured and to exhibit excellent thermal stability.

The optical pressure-sensitive adhesive film can be produced by coating an optical pressure-sensitive adhesive composition described below on a release film comprising PET (polyethylene terephthalate) or the like and drying the solvent.

The optical pressure-sensitive adhesive composition may further include a solvent commonly used in the field of optical pressure-sensitive adhesive composition. The solvent may be contained as a residual amount in the pressure-sensitive adhesive composition.

The optical pressure-sensitive adhesive composition according to another aspect of the present invention may have a hardening shrinkage of 2% or less. Within this range, it is possible to prevent leakage of the display screen edge particularly in a large size display. Preferably 1.5% or less.

The cure shrinkage ratio can be calculated from the specific gravity of the optical adhesive film of 200 μm thickness by coating the specific gravity of the liquid composition before curing and the optical pressure-sensitive adhesive composition on a release film comprising PET (polyethylene terephthalate) and curing at 3000-5000 mJ / have.

<Formula 1>

Cure shrinkage ratio = [(specific gravity of liquid composition before curing-specific gravity of solid after curing)] / specific gravity of liquid composition before curing x 100

In another aspect of the present invention, the optical pressure-sensitive adhesive composition may have an adhesive force of 35-60 kgf to a glass plate. The method of measuring the adhesive strength is not particularly limited. For example, when the size of the lower glass is 2 cm x 2 cm x 1 mm, the size of the upper glass is 1.5 cm x 1.5 cm x 1 mm, the optical pressure-sensitive adhesive composition is coated to a thickness of 500 m, By force, the upper glass can be measured by the force exerted by pushing it from the side.

The optical pressure-sensitive adhesive composition of the present invention may have a viscosity at 25 ° C of 500-2,000 cps. In order to improve processability and shorten the time for dispensing, it is preferable that the viscosity of the liquid resin is within the above range, so that the flow spreadability can be improved and the shrinkage rate can be lowered.

The optical pressure-sensitive adhesive film, which is another aspect of the present invention, may have an elongation of 400% or more, preferably 400-800%, with respect to a film thickness of 500 mu m after curing. Within this range, it is possible to prevent leakage of the display screen edge particularly in a large size display. The curing may be performed at 3000-5000 mJ / cm2, but is not limited thereto.

The elongation can be determined and evaluated by ASTM D368 method. Specifically, an optical pressure-sensitive adhesive composition for forming a film was coated on a release film containing polyethylene terephthalate (PET) or the like, and cured at 3000 mJ / cm ^{2. Then} , an instron Series 1X / s Automated materials tester-3343 Can be used to measure the distance when the specimen breaks.

A display device which is another aspect of the present invention may comprise the optical pressure-sensitive adhesive composition or the optical pressure-sensitive adhesive film. For example, between a cover window of a display and an ITO substrate.

Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to preferred embodiments of the present invention. It is to be understood, however, that the same is by way of illustration and example only and is not to be construed in a limiting sense.

The contents not described here are sufficiently technically inferior to those skilled in the art, and a description thereof will be omitted.

Manufacturing example  1: urethane ( Meta ) Acrylate  Preparation of Copolymer

A 2 L four-necked flask was charged with 80 g of polypropylene diol PPG300, and equipped with a reflux condenser, a thermometer and a dropping funnel. The temperature of the flask solution was raised to 60 占 폚. 0.1 g of DBTDL (dibutyltin dilaurate) diluted with toluene in a ratio of 10% was added, and 8.5 g of IPDI (isophorone diisoyanate) was added thereto. Then, the temperature of the flask solution was raised to 75 캜 and maintained. After confirming that the NCO- group was completely reacted, it was cooled to 60 캜 and 1.4 g of 2-hydroxyethyl methacrylate (HEMA) was added. After maintaining the temperature at 60 ° C for 2 hours, 0.4 g of MeOH was added. After maintaining the temperature at 60 占 폚 for 5 hours, the disappearance of the NCO- group was confirmed by IR and the resultant was cooled to 40 占 폚 to prepare a urethane (meth) acrylate copolymer. The viscosity, weight average molecular weight (Mw) and PDI of the copolymer were measured, and the results are shown in Table 1.

Manufacturing example  2-3: urethane ( Meta ) Acrylate  Preparation of Copolymer

A urethane (meth) acrylate copolymer was prepared in the same manner as in Preparation Example 1, except that the content of each component was changed as shown in Table 1.

Production Example 1 Production Example 2 Production Example 3 Polyol (g) PPG3000 80 80 80 Diisocyanate system (g) IPDI 8.5 8 7.5 The polymerization catalyst (g) DBTDL 0.1 0.1 0.1 Alcohol (g) MeOH 0.4 0.3 0.2 (Meth) acrylate system (g) HEMA 1.4 1.3 1.2 Viscosity (cps, 25 캜) 28,000 48,000 84,700 Solids (wt /%) 100 100 100 Mw 16.8K 19.0K 25.5K PDI 1.3 1.4 1.8

Specific specifications of the components used in the following examples and comparative examples are as follows.

(1) Urethane (meth) acrylate copolymer: The urethane (meth) acrylate copolymer prepared in Preparation Example 1-3

(2) Reactive monomers: 4-hydroxybutyl acrylate (4-HBA), 2-hydroxyethyl methacrylate (2-HEMA), isobornyl acrylate (IBXA), acryloylmorpholine , Isooctyl acrylate (IOA)

(3) Compound: Xylene resin (X-11) (manufactured by Anhui)

(4) Initiator: TPO, Irgacure 754

(5) Ultraviolet absorber: Tinuvin 384-2

(6) Antioxidant: Irganox 1010

Example  1-5, Comparative Example  1: Preparation of optical adhesive composition

The components were mixed in the amounts described in Table 2 (unit: parts by weight) without solvent and stirred for 1 hour to prepare an optical pressure-sensitive adhesive composition.

Example 1 Example 2 Example 3 Example 4 Example 5 Comparative Example 1 Copolymer Production Example 1 60 - - 50 50 65 Production Example 2 - 60 - - - - Production Example 3 - - 60 - - - Reactive monomer 4-HBA 3 3 3 0 3 3 2-HEMA 3 3 3 6 3 3 IBXA 16.3 16.3 16.3 16.3 6.3 21.3 ACMO 3 3 3 3 3 3 IOA 3 3 3 3 3 3 compound X-11 10 10 10 20 30 - Initiator TPO One One One One One One Irgacure754 0.5 0.5 0.5 0.5 0.5 0.5 Ultraviolet absorber Tinuvin 384-2 0.1 0.1 0.1 0.1 0.1 0.1 Antioxidant Irganox 1010 0.1 0.1 0.1 0.1 0.1 0.1 Total amount 100 100 100 100 100 100

Experimental Example : Measurement of physical properties of optical adhesive composition

The following properties were measured for the optical pressure-sensitive adhesive compositions prepared in Examples and Comparative Examples, and the results are shown in Table 3 below.

&Lt; Method for measuring physical properties &

(1) Curing shrinkage: The optical pressure-sensitive adhesive composition prepared in the above Examples and Comparative Examples was cured. The specific gravity of the optical pressure-sensitive adhesive film obtained by coating the specific gravity of the liquid composition and the pressure-sensitive adhesive composition on the release film comprising PET and curing at 3000 mJ / cm2 was measured with a digital solid viscometer DME-220E (Shinko) Respectively.

<Formula 1>

Cure shrinkage ratio = [(specific gravity of liquid composition before curing-specific gravity of solid after curing)] / specific gravity of liquid composition before curing x 100

(2) Elongation: Specimen preparation and evaluation were conducted according to ASTM D638. The optical pressure-sensitive adhesive composition prepared in Examples and Comparative Examples was coated on the release PET film and cured at 3000 mJ / cm 2. Then, when the specimen was broken using Instron series IX / s Automated materials Tester-3343 for a film thickness of 500 μm Was measured with the elongation.

(3) Adhesion: Measure the adhesion between glass and glass. The adhesive strength meter dage series 4000PXY was used to measure the force exerted by pushing the upper glass from the side with a force of 200 kgf at 25 캜. The lower glass had a size of 2 cm x 2 cm x 1 mm, the upper glass had a size of 1.5 cm x 1.5 cm x 1 mm, and the thickness of the optical adhesive composition was 200 m.

(4) Viscosity: The pressure-sensitive adhesive composition was stored in a thermostat (25 ° C) for 24 hours and then measured using a viscosity meter (Brookfield DV-III).

(5) Elastic modulus: Measured in the same manner as in the elongation measurement.

(6) Transmittance: Measured in the region of 400-800 nm with a Lambda 950 (perkin elmer) instrument.

(7) Refractive index: Measured by ASTM D1218 method. The cured PET film was cured to a thickness of 200 탆 after curing and cured at 3000 mJ / cm 2, and the refractive index was measured with an ABBE 5 (Bellingham / stanley Ltd) instrument.

(8) Re-workability: The test was carried out at the time of inspection, and the case where no residue remained on the surface after the reworking was indicated by o, the case where a part remained, and the case where a lot remained was indicated by x.

(9) Curability: Cured when the liquid phase was not left after curing at 3000 mJ / cm &lt; 2 &gt;

Example 1 Example 2 Example 3 Example 4 Example 5 Comparative Example 1 Cure shrinkage (%) 1.2 1.2 1.2 1.0 0.8 2.7 Elongation (%) 530 590 615 750 506 560 Adhesion (kgf) 42 50 60 45 45 30 Viscosity (cps) 830 1160 1600 750 800 750 Elastic Modulus (kgf / mm2) 0.001 0.002 0.004 0.001 0.002 0.002 Transmittance (%) 98 98 97 98 97 98 Refractive index 1.49 1.49 1.49 1.49 1.49 1.46 Re-workability ○ ○ ○ ○ ○ △ Hardenability ○ ○ ○ ○ ○ ○

As shown in Table 2, the optical pressure-sensitive adhesive composition comprising the non-curable compound of the present invention can minimize the hardening shrinkage upon curing, and exhibits excellent physical properties in terms of elongation and adhesion.

Claims (13)

1. A composition comprising a compound having the structure of Formula 1,
&Lt; Formula 1 >

(Wherein, n and m are each independently an integer of 0 to 10,
Except that n and m are both 0,
Wherein each of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 independently represents hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, CH2-) sO- [-CH2-CH2O-] t-CH2CH2OH wherein s is an integer from 0 to 5 and t is an integer from 0 to 5,
At least one of Q1, Q2, Q3, Q4, Q5, Q6, Q7 and Q8 is selected from the group consisting of a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, - (-CH2-) -CH 2 CH 2 OH (s is an integer of 0 to 5 and t is an integer of 0 to 5)),
Wherein the compound has a structure represented by the following formula (2) or (3): < EMI ID =
(2)
- (-CH2O-) n1- (-CH2-) m1-A2- (-CH2O-) n2- (-CH2-) m2-
(3)
- (-CH2O-) n3- (-CH2-) m1-A2- (-CH2O-) n2- (-CH2-) m2- (-CH2O-) n4- (-CH2-) m4-A5
(Wherein n1, n2, n3, n4, m1, m2, m3 and m4 are each independently an integer of 0 to 10,
When n1 and m1 are all 0, n2 and m2 are both 0, n3 and m3 are both 0, and n4 and m4 are both 0,
A1 to A5 may be any one of the following formulas (a), (b), (c), or (d).
(a)

(b)

(c)

(d)

R 1, R 2, R 3, R 4 and R 5 may be the same or different from each other and each independently represent hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group, (-CH2-) sO- [-CH2-CH2O-] t-CH2CH2OH, wherein s is an integer from 0 to 5 and t is an integer from 0 to 5,
At least one of R 1, R 2, R 3, R 4 and R 5 is a hydroxyl group, an alkyl group having 1 to 10 carbon atoms substituted with a hydroxyl group or - (CH 2 -) s O - [CH 2 -CH 2 O-] t- T is an integer from 0 to 5).
The optical pressure-sensitive adhesive composition according to claim 1, wherein the compound is ultraviolet-curable.
delete The optical pressure-sensitive adhesive composition according to claim 1, wherein the compound is contained in an amount of 1-30% by weight of the composition.
The optical pressure-sensitive adhesive composition according to claim 1, wherein the composition further comprises a urethane (meth) acrylate copolymer, a reactive monomer, and an initiator.
6. The method of claim 5, wherein the reactive monomer is selected from the group consisting of a vinyl monomer having a hydroxyl group, a vinyl monomer having an alkyl group, a vinyl monomer having an alicyclic group, a (meth) acrylic monomer having an alicyclic heterocycle, And a monomer having a silane group and a vinyl group.
The composition of claim 5, wherein the composition comprises 25-83.7 wt% of a urethane (meth) acrylate copolymer, 1-30 wt% of the compound, 15-40 wt% of a reactive monomer, and 0.1-5 wt% of an initiator By weight.
The optical pressure-sensitive adhesive composition according to claim 1, wherein the composition further comprises at least one selected from the group consisting of an ultraviolet absorber and an antioxidant.
The composition of claim 8, wherein the composition comprises 25-83.7 wt% of a urethane (meth) acrylate copolymer, 1-30 wt% of the compound, 15-40 wt% of a reactive monomer, 0.1-5 wt% of an initiator, 1% by weight of an antioxidant and 0.1-1% by weight of an antioxidant.
10. A pharmaceutical composition comprising a compound of claim 1,
An optical pressure-sensitive adhesive composition having a curing shrinkage ratio of 2% or less represented by the following formula
<Formula 1>
Cure shrinkage ratio = [(specific gravity of liquid composition before curing-specific gravity of solid after curing)] / specific gravity of liquid composition before curing x 100.
10. A pharmaceutical composition comprising a compound of claim 1,
And an adhesive force to a 5 cm x 1.5 cm glass plate of 35-60 kgf.
10. A pharmaceutical composition comprising a compound of claim 1,
An optical adhesive film having an elongation of 400-800% relative to a film thickness of 500 mu m after curing.
 A display device comprising the optical adhesive composition or optical adhesive film of any one of claims 1, 2, and 12 to 12.