KR100942355B1 - Photo Curable Pressure sensitive Adhesive Composition?containing ?liquid polyisoprene rubber?and?PSA tape Using?the Same - Google Patents

Abstract

The present invention relates to a photocurable acrylic pressure-sensitive adhesive composition comprising a liquid polyisoprene rubber, a photoinitiator, a thermosetting agent and a solvent, and a pressure-sensitive adhesive tape using the same. According to the present invention, by introducing a liquid polyisoprene rubber, The adhesive force and the pickup performance can be effectively applied to a dicing adhesive tape including an adhesive film layer for dicing and die bonding.

Liquid polyisoprene rubber, thermosetting agent, photoinitiator, adhesive tape, photocuring, adhesive composition.

Description

Photocurable pressure sensitive adhesive composition comprising liquid polyisoprene rubber and photocurable adhesive tape using the same

The present invention relates to a photocurable pressure-sensitive adhesive composition and a photocurable pressure-sensitive adhesive tape using the same, and more particularly, to a photocurable pressure-sensitive adhesive composition comprising a photocurable acrylic pressure-sensitive adhesive binder comprising a liquid polyisoprene rubber, a photoinitiator and a thermosetting agent, wherein the liquid poly Due to the introduction of isoprene rubber, it is possible to effectively apply the dicing adhesive tape including an adhesive film for dicing and die bonding, in which adhesion and pick-up performance are improved to require excellent peeling force.

Conventional dicing adhesive tapes including photocurable dicing and die-bonding adhesive film layers have been prepared as mixed adhesive compositions consisting of a small amount of photoinitiators and thermosetting agents in an acrylic adhesive binder and a photocurable oligomer mixture.

For example, Japanese Patent Application Laid-Open No. 1995-159393 discloses a mixed adhesive composition in which the ratio of the photocurable portion to the binder is 0.5% to 100%, a copolymer of 2-ethylhexyl acrylate and n-butyl acrylate, and polyisocyanate (coronate). L) and a compound having a carbon-carbon double bond (tris-2-acryloxy ethyl isocyanurate) is disclosed. However, the pressure-sensitive adhesive composition is a lot-by-lot variation in the preparation and coating process at the production site, can provide a non-uniform peeling force after UV curing. In addition, when applied to a dicing film having a wafer or a die-bonding adhesive film layer, the transition of the photocurable oligomer cannot be completely prevented, which may cause a problem in semiconductor reliability.

In order to improve the disadvantages of such a mixed composition has been researched to obtain more stable physical properties, Japanese Patent Laid-Open No. 2006-186305 is n-butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, methacrylic acid A method for producing a pressure-sensitive adhesive composition in which an adhesive binder portion and a photocuring portion are integrated by adding 2-hydroxy ethyl methacrylate synthesized from methacrylic acid and ethylene glycol after synthesizing a binder is disclosed.

However, in the case of the composition, a synthetic process of reacting methacrylic acid and 2-hydroxy ethyl methacrylate in an ester reaction should be additionally included, and condensation polymerization at a high temperature requires 2-hydroxy ethyl methacrylate. There is a fear that the double bond is broken during the addition condensation reaction. In addition, since the water generated in the condensation polymerization has to be removed, the process is very complicated and the productivity is very low.

Accordingly, there is a need for development of a photocurable pressure sensitive adhesive binder having excellent adhesion and pick-up performance and excellent productivity, and a photocurable pressure sensitive adhesive composition using the same.

The present invention is to solve the problems of the prior art as described above, one object of the present invention is to provide a photocurable pressure-sensitive adhesive composition having excellent adhesion to the substrate and pickup performance.

Another object of the present invention is to provide a photocurable adhesive tape using the adhesive composition.

The above and other objects of the present invention can be achieved by the present invention described below.

One aspect of the present invention for achieving the above object, (A) photocurable acrylic adhesive binder comprising a liquid polyisoprene rubber represented by the formula (1), (B) photoinitiator, (C) thermosetting agent and (D) It relates to a photocurable pressure-sensitive adhesive composition consisting of a solvent.

[Formula 1]

In Chemical Formula 1,

R is a C4-C9 alkyl group or a hydroxyl group, n is an integer of 400-700.

The photocurable adhesive composition containing the liquid polyisoprene rubber according to the present invention and the photocurable adhesive tape using the same exhibit excellent adhesion with a substrate (ring frame, wafer and die-bonding film ) before photocuring, and after the photocuring, Due to the plasticity and elasticity of the isoprene rubber, the adhesive composition according to the present invention includes an adhesive film layer for dicing and die bonding, because it has excellent peelability and pick-up performance to a substrate even when UV energy is not constant. It can be effectively applied to a dicing adhesive tape.

Hereinafter, the present invention will be described in more detail with reference to Examples.

The photocurable adhesive composition according to the present invention is 45 to 55 parts by weight of the photocurable acrylic pressure-sensitive adhesive binder containing (A) a liquid polyisoprene rubber represented by the following formula (1), (B) 0.2 to 1.0 part by weight of the photoinitiator , (C) 1 to 5 parts by weight of the thermosetting agent and 35 to 50 parts by weight of the (D) solvent.

[Formula 1]

In Chemical Formula 1,

R is a C4-C9 alkyl group or a hydroxyl group, n is an integer of 400-700.

Hereinafter, the present invention will be described in more detail for each composition component.

(A) Photocurable Acrylic Adhesive Binder

The photocurable acrylic pressure-sensitive adhesive binder according to the present invention can be prepared from a liquid polyisoprene rubber, an acrylic monomer, a functional acrylic monomer and a vinyl group introduction monomer.

The liquid polyisoprene rubber, which is a reactive plastic material capable of improving adhesion and pick-up processability to the adhesive composition according to the present invention, comprises the following Chemical Formula 1, and has a number average molecular weight of 20,000 to 100,000 and a viscosity of 100 to 2000. cps (25 ℃), the glass transition temperature is -100 ℃ ~ -50 ℃, characterized in that the specific gravity is 0.85 ~ 1.0.

[Formula 1]

In Chemical Formula 1,

R is a C4-C9 alkyl group or a hydroxyl group, n is an integer of 400-700.

In the case of the liquid polyisoprene rubber, the content thereof is appropriately 0.5 to 10 parts by weight based on the total monomers. More preferably, 0.5-5 weight part is more suitable. If it is less than 0.5 parts by weight, there is little effect of improving the initial adhesion. If it exceeds 10 parts by weight, gelation may occur in the polymerization process of the acrylic adhesive binder due to the vinyl group of the liquid polyisoprene rubber. Depending on the degree of the vinyl group of the isoprene rubber participating in the reaction, a non-uniform molecular weight may occur in each lot during synthesis.

The acrylic monomers according to the present invention include 2-ethylhexyl methacrylate, iso-oxyl acrylate, iso-butyl acrylate, 2-ethylhexyl acrylate, ethyl acrylate, n-butyl acrylate, and octadecyl meta. It is preferable to use one, or a mixture of two or more selected from the group consisting of acrylate and the like, but is not limited thereto.

More preferably, the acrylic monomer is used by mixing one or two or more of the monomers having a glass transition temperature of -100 ° C to 5 ° C.

50-70 weight part of said acrylic monomers is suitable with respect to all monomers. If it is less than 50 parts by weight, it is difficult to design a high initial adhesive force, and if it exceeds 70 parts by weight, it is difficult to introduce suitable functional monomers, making it difficult to obtain photocurable adhesive binder properties.

As the functional acrylic monomer according to one embodiment of the present invention, a hydroxy or epoxy group monomer may be used.

The functional acrylic monomer may be selected from the group consisting of hydroxy acryl monomers, 2-hydroxy ethyl methacrylate, hydroxy ethyl acrylate, 4-hydroxy butyl acrylate, hydroxy porophyll (meth) acrylate, vinyl caprolactam; And glycidyl methacrylate and glycidyl acrylate which are the epoxy group monomers. It may be used in at least one or a mixture of two or more selected from the group consisting of, but is not limited to.

The composition according to an embodiment of the present invention may use a vinyl group introduction monomer to introduce a vinyl group into the acrylic adhesive binder, the introduction monomer may be a monomer or oligomer having an isocyanate group at one end and a vinyl group at the other end Can be.

Examples of the vinyl group introduction monomers include α, α-dimethyl-m-isopropenylbenzyl isocyanate and 2-isocyanatoethyl methacrylate (2-Isocyanatoethyl Methacrylate). 2-Isocyanatoethyl acrylate, 2- (O- [1'-methylpropylideneamino] carboxyamino) ethyl methacrylate (2- (O- [1'-Methylpropylideneamino] carboxyamino) ethyl methacrylate), 2-Isocyanatoethyl 2-propenoate, 1,1-bisacryloyloxymethylethylisocyanate (1,1-bis (acryloyloxy methyl ethyl isocyanate) and the like, but may be used one or more selected from the group consisting of, but is not limited thereto.

The vinyl group-introducing monomer is preferably 5 to 30 parts by weight based on the total monomers. When the vinyl group-introduced monomer is less than 5 parts by weight, there is little loss of stickiness of the adhesive film during photocuring, and thus the probability of success during the semiconductor chip pick-up process is very low. In addition, when the amount of the vinyl monomer introduced exceeds 30 parts by weight, the adhesive strength before photocuring is small, and the adhesion to the ring frame is weakened. Therefore, there is a high possibility that an error occurs due to a chip phase difference in the pickup process.

In the adhesive binder according to the present invention, the acrylic monomer is selected as the main monomer, and a functional acrylic monomer and a liquid polyisoprene rubber are added to the monomer to synthesize an acrylic adhesive polyol binder, and a vinyl-based introduction monomer is added to the acrylic adhesive polyol binder. By applying a urethane addition reaction at a low temperature by applying it can be prepared in the step of synthesizing a photo-curable acrylic adhesive binder containing a vinyl group.

The glass transition temperature of the acrylic adhesive binder according to the present invention is -30 ℃ ~ -60 ℃, the weight average molecular weight is preferably from 150,000 to 700,000, more preferably from 200,000 to 600,000. Since the photocurable acryl-based adhesive binder according to the present invention introduces a liquid polyisoprene rubber containing a large amount of vinyl groups, there is a high risk of gelation during the reaction when the binder has a molecular weight of more than 700,000. There is a problem in that the physical properties are uneven due to the variation of the binder by the synthetic lot. On the other hand, if the molecular weight of the binder is less than 150,000, when the release PET (polyethylen terephthalate) film coating, the wetting property is low, the coating coating the surface is non-uniform, adhesion with the substrate before photocuring, loss of adhesion and after the photocuring The peeling force of the becomes uneven.

(B) photoinitiator

The photoinitiator according to the present invention is an alpha-hydroxy ketone type compound, such as 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy 2-methyl-1-phenyl-1-propanone, 2-hydroxy One or two or more kinds selected from the group consisting of -1- [4- (2-hydroxyethoxy) phenyl] -2-methyl-1-propane, etc. may be used, but are not limited thereto.

Melting point of the alpha-amino ketone type compound is characterized in that 4 ℃, specific gravity is 1.0 ~ 1.2 and boiling point 80 ~ 81 ℃, 0.5 to 2 parts by weight relative to the photocurable adhesive binder solids reference. When the content of the photoinitiator is less than 0.5 parts by weight, the loss of adhesion after photocuring is less, the pick-up property is worse after the photocuring, and when the content of the photoinitiator exceeds 2 parts by weight, the adhesion loss no longer occurs. In addition, the adhesive force with the wafer or the die-bonding adhesive film is increased to worsen the pick-up property after photocuring.

(C) thermosetting agent

The thermosetting agent according to the present invention is 2,4-trilene diisocyanate, 2,6-triene diisocyanate, hydrogenated triylene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, di Phenyl methane-4,4-diisocyanate, 1,3-bisisocyanatomethyl cyclohexane, tetra methyl xylene diisocyanate, 1,5-naphthalene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, 2,4 Selected from the group consisting of 4-trimethyl hexamethylene diisocyanate, triylene diisocyanate adduct of trimetholpropane, xylene diisocyanate adduct of trimetholpropane, toriphenylmethane isocyanate, methylene bistri isocyanate and the like One or more may be used, but is not limited thereto.

It is preferable to introduce 3 to 10 parts by weight of the thermosetting agent relative to the binder solids. If it is less than 3 parts by weight, the adhesion between the polyolefin film, which is the base film, is weak before the photocuring, and after the photocuring, the adhesion between the film and the adhesive coating layer is lowered, so that there is a problem that the transition to the wafer or die adhesion adhesive film surface may occur. . If the amount is more than 10 parts by weight, the peeling force with the die-bonding adhesive film is increased by the unreacted isocyanate, and thus the pickup performance is deteriorated.

(D) Solvent

The solvent (D) according to the present invention may be used by mixing one or more selected from the group consisting of methyl methyl ketone, methyl isobutyl ketone, methyl normal amyl ketone, cyclohexanone, and the like, but is not limited thereto. It is not.

The solvent is preferably introduced 70 to 80 parts by weight based on the binder solids. If it is less than 70 parts by weight, the viscosity is high at the time of coating, the surface leveling properties are poor, the uniformity of the surface is a problem occurs, if it exceeds 80 parts by weight, the viscosity of the coating liquid phase is too low, the wettability to the release PET film worsens, pinhole phenomenon This is because a problem that is likely to occur occurs.

Hereinafter, the present invention will be described in more detail with reference to Examples, which are only for the purpose of explanation and are not intended to limit the scope of the present invention.

Example 1

Preparation of Photocurable Adhesive Compositions Containing Liquid Polyisoprene Rubber

1. Acrylic adhesive Polyol  Preparation of binder resin HA -01)

The reagent was added to a 2 L four-necked flask under the following compounding conditions, and the reaction process was as follows. 540 g of organic solvent ethyl acetate was added first, a reflux cooler was installed on one side, a thermometer was installed on the other side, and a dropping panel was installed on the other side.

After raising the flask solution temperature to reflux (73-74 ° C.), 2-570 hexyl acrylate, isooxyl acrylate, 2-hydroxyethyl methacrylate, glycidyl methacrylate monomer 570 g, and toluene 30 g, liquid phase 30 g of polyisoprene rubber (LIR-30, KURARAY Co., LTD) was prepared and 0.18 g of azobisisobutyronitrile was prepared. The mixture was then dropped for 3 hours at 73 to 85 ° C. using a dropping panel. It was dripped for a while.

The stirring speed at the dropwise addition was 250rpm, after the completion of dropping, the reaction was aged at 80 to 85 ° C for 4 hours, and then 120g of toluene and 0.18g of azobisisobutylonitrile were added for 20 minutes. After maintaining for a time, the viscosity and solids were measured, and the reaction was stopped to prepare an acrylic adhesive polyol binder resin (HA-01), which is an acrylic copolymer. The viscosity after superposition | polymerization was 3000-4000 cps / 25 degreeC, and the content of solid content was corrected to 40%.

2. Manufacture of binders HAA -01)

The reagent was added to a 2 L four-necked flask under the following compounding conditions, and the reaction process was as follows. 2-Isocyanatoethyl Methacrylate is added to the synthesized acrylic adhesive polyol binder resin (250g, HA-1) in an amount of 20 parts by weight, and 30 ppm of DBTDL (dibutyltin dilaurate) 대비 relative to an acrylic adhesive polyol base solid, and reacted at 50 to 55 ° C. for 8 hr. -Isocyanato ethyl Methacrylate (2-isocyanate ethyl methacrylate) The isocyanate group of the monomer reacts with the hydroxyl group of the binder and disappears on the FT-IR as the end point of the reaction. (HAA-01) was synthesized.

3. Preparation of adhesive composition

Using photoHAA-01 as a photocurable acrylic adhesive binder, a photocurable adhesive composition was prepared by a conventional method with the following composition and content. 70 g of a photocurable acrylic adhesive binder containing liquid isoprene rubber, methyl ethyl ketone 47.6 g as a solvent, 0.4 g of photoinitiator (Darocur 1173, Ciba-chemical), and 2.2 g of isocyanate curing agent (AK-75, Aekyung Chemical) as a thermosetting agent Stirring for 1 hour or more to complete a pressure-sensitive adhesive composition of 25% solids.

Comparative Example 1

Preparation of Photocurable Adhesive Compositions Containing Liquid Polyisoprene Rubber

1. Acrylic adhesive Polyol  Preparation of binder resin HA -02)

The reagent was added to a 2 L four-necked flask under the following compounding conditions, and the reaction process was as follows. 540 g of organic solvent ethyl acetate was added first, a reflux cooler was installed on one side, a thermometer was installed on the other side, and a dropping panel was installed on the other side.

After raising the flask solution temperature to reflux (73-74 ° C.), 597 g of 2-ethylhexyl acrylate, isooxyl acrylate, 2-hydroxyethyl methacrylate and glycidyl methacrylate monomers and 30 g of toluene, liquid phase A mixture of 3 g of polyisoprene rubber and 0.18 g of azobisisobutyronitrile was prepared, and the mixed solution was added dropwise at 73 to 85 ° C. using a dropping panel for 3 hours.

The stirring speed at the dropwise addition was 250rpm, after the completion of dropping, the reaction was aged at 80 to 85 ° C for 4 hours, and then 120g of toluene and 0.18g of azobisisobutylonitrile were added for 20 minutes. After maintaining for a period of time, the viscosity and solids were measured, and the reaction was stopped to prepare an acrylic adhesive polyol binder resin (HA-02) as an acrylic copolymer. The viscosity after superposition | polymerization was 3000-4000cps / 25 degreeC, and content of the solid content was corrected to 40%.

2. Binder Manufacturing ( HAA -02)

The reagent was added to a 2 L four-necked flask under the following compounding conditions, and the reaction process was as follows. 2-Isocyanatoethyl Methacrylate is added to the synthesized acrylic adhesive polyol binder resin (250g, HA-02) in an amount of 20 parts by weight and 30 ppm of DBTDL, respectively, to 50-55 ° C × 8hr. With the end point of the reaction that the isocyanate group of the monomer reacts with the hydroxyl group of the binder and disappears on the FT-IR, ethyl acetate was added and cooled to synthesize a solid content 45% photocurable acrylic adhesive binder (HAA-02).

3. Preparation of adhesive composition

Using photoHAA-02 as a photocurable acrylic adhesive binder, a photocurable pressure-sensitive adhesive composition was prepared by a conventional method in the following composition and content. 70 g of a photocurable acrylic adhesive binder containing liquid isoprene rubber, 61.6 g of methyl ethyl ketone as a solvent, 0.4 g of photoinitiator (Darocur 1173, Ciba-chemical), and 2.2 g of an isocyanate curing agent (AK-75, Aekyung Chemical) as a thermosetting agent Stirring for 1 hour or more to complete a pressure-sensitive adhesive composition of 25% solids.

Comparative Example 2

Preparation of Photocurable Adhesive Composition

One. Polyol  Preparation of binder resin HA -03)

The reagent was added to a 2 L four-necked flask under the following mixing conditions, and the reaction process was as follows. 540 g of organic solvent ethyl acetate was added first, a reflux cooler was installed on one side, a thermometer was installed on the other side, and a dropping panel was installed on the other side.

After raising the flask solution temperature to reflux (73-74 ° C.), 2-ethylhexyl acrylate, isooxyl acrylate, 2-hydroxyethyl methacrylate, glycidyl methacrylate monomer 600 g and toluene 30 g, azo A bisisobutylonitrile 0.18 g 'mixture was prepared, and the mixed solution was added dropwise at 73 to 85 DEG C using a dropping panel for 3 hours.

The stirring speed at the dropwise addition was 250rpm, after the completion of dropping, the reaction was aged at 80 to 85 ° C for 4 hours, and then 120g of toluene and 0.18g of azobisisobutylonitrile were added for 20 minutes. After maintaining for a time, the viscosity and solids were measured, and the reaction was stopped to prepare an acrylic adhesive polyol binder resin (HA-03) which is an acrylic copolymer. The viscosity after superposition | polymerization was 3000-4000 cps / 25 degreeC, and the content of solid content was corrected to 40%.

2. Binder Manufacturing ( HAA -03)

The reagent was added to a 2 L four-necked flask under the following compounding conditions, and the reaction process was as follows. 2-Isocyanatoethyl Methacrylate is added to the synthesized acrylic adhesive polyol binder resin (250 g, # HA-3) in an amount of 20 parts by weight, and 30 ppm of DBTDL, respectively, to 50-55 ° C. × 8hr. With the end point of the reaction that the isocyanate group of the monomer reacts with the hydroxyl group of the binder and disappears on FT-IR, ethyl acetate was added and cooled to synthesize a solid content 45% photocurable acrylic adhesive binder (HAA-03).

3. Preparation of Adhesion Composition

Using HAA-03 as a photocurable acrylic adhesive binder, a photocurable adhesive composition was prepared by a conventional method with the following composition and content. 70 g of a photocurable acrylic adhesive binder containing liquid isoprene rubber, 61.6 g of methyl ethyl ketone as a solvent, 0.4 g of photoinitiator (Darocur 1173, Ciba-chemical), 2.2 g of isocyanate curing agent (AK-75, Aekyung Chemical) as a thermosetting agent Stirring for 1 hour or more to complete a pressure-sensitive adhesive composition of 25% solids.

The compositions of Example 1 and Comparative Examples 1 and 2 are shown in Table 1 below.

Property evaluation method

Test Example 1: Measurement of peeling force of the adhesive composition

In order to test the physical properties of the pressure-sensitive adhesive composition according to the present invention, the pressure-sensitive adhesive compositions prepared in Examples 1 and Comparative Examples 1 and 2 were coated on a polyethylene terephthalate film, dried, and coated with a coating thickness of 8 to 12 μm. After transferring to a polyolefin film and aging for 3 to 7 days at 25 ~ 60 ℃ was measured the adhesion and peel force of the pressure-sensitive adhesive composition.

Adhesion measurement was tested in accordance with Clause 8 of Korean Industrial Standard KS-A-01107 (Test Method of Adhesive Tape and Adhesive Sheet). After attaching a sample having a thickness of 25 mm and a length of 250 mm to the die-bonding adhesive film, the adhesive tape was attached to the die-bonding adhesive film surface, and then reciprocated once by a speed of 300 mm / min using a 2 kg load roller. After 30 minutes after crimping, turn the folded part of the test piece to 180 ° and peel it off about 25mm.Then, fix the test piece to the upper clip of the tensile strength tester, and then attach the die-bonding adhesive film to the lower test clip of the test plate and pull it at a tensile speed of 300mm / min. The load at the time of peeling was measured.

Tensile tester used Instron Series lX / s Automated materials Tester-3343. After laminating with organic adhesive film or wafer and photocurable adhesive film, the result of measuring before and after irradiation with high pressure mercury lamp 30mJ / ㎠ ~ 300mJ / ㎠ Shown in

Test Example 2 Measurement of Tackiness of Photocurable Adhesive Composition

Table 2 shows the results of measuring tackiness using a probe tack tester (tacktoc-2000) using the test specimen prepared in Test Example 1.

The measuring method is based on ASTM D2979-71. The tip of the clean probe is contacted with the adhesive for 1.0 + 0.01 seconds at a speed of 10 + 0.1mm / sec and a contact load of 9.79 + 1.01kPa, and then the maximum force required to release the adhesive It was set as the (tackiness) value.

Test Example 3 Measurement of Light Curing Degree by Light Amount

Photocuring degree before and after photocuring was measured in light quantity 30, 100, 200, 300mJ / cm <2>. The measured results are shown in Table 2.

The measurement method was compared to the degree of reduction of free-NCO peak in the vicinity of 2270cm ^-1 using the FT-IR Spectrometer (Varian Model Scimitar 800) measuring device. There is no constant proportionality between the pickup success rate and the photocurability, but at least 80% of the photocuring efficiency is advantageous for the pickup success rate. The measured results are shown in Table 2.

Test Example 4 Surface Energy Measurement

The surface energy of the adhesive film produced in Experimental Example 1 was measured using a surface tension meter (CAM 200-Optical Surface Tension / Contact angle meter).

The measurement method was measured by the Sessile Drop Method. It is a method of measuring the contact angle of water droplets generated by dropping water on the film surface. The greater the contact angle, the lower the surface energy, and the lower the surface energy, the better the peeling force after photocuring. In addition, before photocuring, the smaller the contact angle, the higher the surface energy, and the higher the surface energy, the better the adhesion with the wafer or die-bonding adhesive film. The measured results are shown in Table 2.

Test Example 5: Pickup Success Rate

The chip pick-up process refers to a process of mounting a chipped wafer on a PCB substrate or stacked chips after the wafer cutting process. The success rate is improved only when the dicing film has excellent peeling force with the chipped wafer after photocuring. The measured results are shown in Table 2.

The adhesive tape according to the present invention is characterized in that the photocuring efficiency is 80% or more in the ultraviolet light amount 30mJ / ㎠ ~ 300mJ / ㎠ region. Therefore, it has excellent curability even in photocuring conditions in which the amount of energy during ultraviolet curing is not constant. Prior to photocuring, the pressure-sensitive adhesive composition of Example 1 was superior to the pressure-sensitive adhesive composition of the wafer or die bonding film after photocuring, and to the ring frame and wafer before photocuring, compared to the pressure-sensitive adhesive compositions of Comparative Example 1 and Comparative Example 2. In addition, since the plasticity and elasticity of the liquid polyisoprene rubber is exhibited after the photocuring, Example 1 has superior peeling force as compared to Comparative Examples 1 and 2, and thus the pickup success rate may be increased. Accordingly, the present invention can provide a photocurable pressure-sensitive adhesive composition and a film having excellent adhesion before photocuring and at the same time having a high pick-up success rate after photocuring.

Claims (14)

45 to 55 parts by weight of the photocurable acrylic adhesive binder including the liquid polyisoprene rubber represented by the following formula (1), 0.2 to 1.0 parts by weight of the photoinitiator, 1 to 5 parts by weight of the heat curing agent and 35 to 50 parts by weight of the total composition Photocurable adhesive composition. [Formula 1]

In Chemical Formula 1, R is a C4-C9 alkyl group or a hydroxyl group, n is an integer of 400-700. delete delete The photocurable pressure-sensitive adhesive composition of claim 1, wherein the liquid polyisoprene rubber is 0.5 to 10 parts by weight based on the total monomers. According to claim 1, wherein the liquid polyisoprene rubber has a number average molecular weight of 20,000 ~ 100,000, glass transition temperature of -100 ℃ ~ -50 ℃, specific gravity 0.85 ~ 1.0 and viscosity of 100 ~ 2000 cps (25 ℃) Photocurable pressure-sensitive adhesive composition characterized by. delete delete delete The photocurable pressure-sensitive adhesive composition of claim 1, wherein the photocurable pressure-sensitive adhesive binder has a molecular weight of 150,000 to 700,000. The photocurable pressure-sensitive adhesive composition of claim 1, wherein the photoinitiator uses an alpha-amino ketone type compound having a melting point of 4 ° C, a boiling point of 80 ° C to 81 ° C, and a specific gravity of 1.0 to 1.2. The photoinitiator of claim 10, wherein the photoinitiator is 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy 2-methyl-1-phenyl-1-propanone, 2-hydroxy-1- [4- (2 -Hydroxyethoxy) phenyl] -2-methyl-1-propanone. The photocurable pressure-sensitive adhesive composition, characterized in that one or two or more selected from the group consisting of. The method of claim 1, wherein the thermosetting agent is 2,4-trilene diisocyanate, 2,6-triene diisocyanate, hydrogenated triylene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, Diphenyl methane-4,4-diisocyanate, 1,3-bisisocyanatomethyl cyclohexane, tetra methyl xylene diisocyanate, 1,5-naphthalene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, 2, 4,4-trimethyl hexamethylene diisocyanate, triylene diisocyanate adduct of trimetholpropane, xylene diisocyanate adduct of trimetholpropane, toriphenylmethanetoriisocyanato, methylene bistri isocyanate It is 1 or more types, the photocurable adhesive composition. The photocurable adhesive composition according to claim 1, wherein the solvent is one or a mixture of two or more selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, methyl normal amyl ketone, and cyclohexanone. The photocurable pressure-sensitive adhesive tape using the photocurable pressure-sensitive adhesive composition according to any one of claims 1, 4, 5 or 9 to 13.