KR100569343B1 - Adhesive composition containing photoreactive polycyanurate polymer and an adhesive sheet using the same - Google Patents

Abstract

The present invention relates to an adhesive composition and an adhesive sheet using the same, wherein the adhesive composition according to the present invention is a curable adhesive component that is cured to bond between opposing substrates and a photosensitive polish as a precursor of a thickener that increases the viscosity of the curable adhesive component. An anurate type polymer is included. The photosensitive polycyanurate-based polymer forms a crosslinked polycyanurate having a network structure through a photocrosslinking reaction. Accordingly, when the adhesive composition including the photosensitive polycyanurate-based polymer is irradiated with light, not only excessive flowability is improved but also excellent adhesive properties such as dimensional stability, heat resistance, and adhesive strength can be obtained.

Adhesive composition, adhesive sheet, photosensitive, polycyanurate, triazine, photocrosslinking reaction

Description

Adhesive composition containing a photosensitive polycyanurate-based polymer and an adhesive sheet using the same {Adhesive composition containing photoreactive polycyanurate polymer and an adhesive sheet using the same}

1 is a cross-sectional view showing an adhesive sheet according to the present invention.

Figure 2 is a cross-sectional view showing another form of adhesive sheet according to the present invention.

<Description of Symbols for Main Parts of Drawings>

1 ... release paper 3 ... adhesive film 5 ... support film

10 ... Adhesive Sheet

The present invention relates to an adhesive composition used to bond between various substrates and an adhesive sheet using the same.

Adhesives are used to bond semiconductor chips and substrates, leadframes and chips, and a variety of opposing substrates such as chips and chips. In particular, as the miniaturization and thinning of the electronic and electronic fields rapidly occur, development of more precisely controllable adhesives to be applied to the connection between the fine circuits or the connection between the micro components and the microcircuits continues.

As the adhesive component of the adhesive, both a plastic adhesive component and a curable adhesive component are used. Since the plastic adhesive component can be used by solubilizing in a general-purpose solvent, it has a feature of excellent workability, but has a problem of weak heat resistance and high melting temperature. Therefore, recently, a curable adhesive component having excellent heat resistance and mechanical properties has been preferred.

The curable adhesive component is cured by heat or light to bond the substrates. Examples thereof include epoxy resins, acrylic resins, urethane resins, phenol resins, polyester resins, urea resins, and melamine resins. Among them, epoxy resins are mainly used. Epoxy resins can obtain high adhesive strength, have a very low reaction shrinkage rate, do not generate volatiles, and have excellent mechanical properties, electrical insulation, water resistance, and heat resistance. It is widely used for various purposes such as construction, automobile, aircraft, etc.

Curable adhesive components including such epoxy resins are widely used because they are inexpensive and easy to obtain, but generally have a disadvantage in that precise work is difficult because of their high flowability because they are prepared in a liquid phase having a low viscosity.

In order to compensate for this disadvantage, an adhesive composition in which a thickener is added to the curable adhesive component is used. For example, there is a method of controlling the viscosity of the adhesive by adding a monomer capable of forming a network structure by a photoreaction to the adhesive component as a precursor of a thickener and then irradiating with light. However, since the monomer is added to the adhesive component and then crosslinked by light irradiation, the photocrosslinking reaction does not occur smoothly in the adhesive component due to the characteristics of the monomer having a short molecular chain, thereby forming a network structure. In addition, there is a method of adding a linear polymer compound as a thickener, the linear polymer has a limitation in controlling the flowability of the adhesive component, there is a problem that the physical properties such as heat resistance of the adhesive due to the added linear polymer compound.

Therefore, the technical problem to be achieved by the present invention is to solve the problems described above, not only to improve the excessive flow during light irradiation but also to obtain an adhesive composition excellent in physical properties such as dimensional stability, heat resistance, adhesive strength, etc. To provide.

In addition, another technical problem to be achieved by the present invention is to provide an adhesive sheet excellent in physical properties such as dimensional stability, heat resistance, adhesive strength, as well as excessive flowability is improved.

In order to achieve the above technical problem, the adhesive composition of the present invention is an adhesive composition comprising a curable adhesive component for curing and adhering between opposing substrates and a precursor of a thickener for increasing the viscosity of the curable adhesive component, As a precursor, a photosensitive polycyanurate polymer represented by the following formula (1) is used.

In Formula 1, m + n = 1, 0 ≦ m ≦ 1, and 0 ≦ n ≦ 1, and R ₁ is each independently selected from the group consisting of (1a) to (4a) of Formula 2 below.

In (1a) of the formula (2), X is any one selected from the group represented by the following formula (3),

In Formula 3, m and n are each 0 to 10.

In (1a) of the formula (2), Y is any one selected from the group represented by the following formula (4).

In Formula 4, 1,2,3,4,5,6,7,8,9 are each independently selected from the group represented by the following formula (5),

In Formula 5, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . .

In (2a) and (3a) of Formula 2, n is 0 to 10, 1,2,3,4,5 are each independently selected from the group represented by the following formula (6),

In Formula 6, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ .

In (4a) of the formula (2), Y is any one selected from the group represented by the following formula (7),

In Formula 7 n is 0 to 10.

In (4a) of the formula (2), 1 and 2 are each independently selected from the group represented by the following formula (8),

In Formula 8, A is any one selected from the group consisting of H, F, CH ₃ , CF _3, and CN.

In Formula 1, R ₂ and R ₃ are each independently selected from the group represented by the following formula (9),

In Formula 9, m and n are each 0 to 10, and 1, 2, 3, 4, 5, 6, 7, and 8 are each independently H, F, Cl, CN, CH ₃ , OCH ₃ , and CF Any one selected from the group consisting of ₃ , X is any one selected from the group consisting of H, F, Cl, CN, CH ₃ , OCH ₃ , and CF ₃ , and Y is CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , O, S, SO ₂ , CO, and CO ₂ is any one selected from the group consisting of.

When a substituent of a ring structure such as a benzene ring is used to penetrate the ring in the chemical formula used herein, it means that the substituent may be substituted at any carbon position of the ring which is not substituted with another substituent. That is, in the relationship with a substituent substituted at a predetermined position, it indicates that it can be substituted at any position such as ortho, meta, para, and the like.

Since the triazine ring having a photoactive side chain is introduced into the main chain, the photosensitive polycyanurate polymer forms a crosslinked polycyanurate having a network structure which can function as a thickener through a photocrosslinking reaction.

In addition, in order to solve the another technical problem, the adhesive sheet of the present invention is an adhesive sheet consisting of a release paper and the adhesive film laminated on the release paper surface, the adhesive film is cured adhesive to cure the adhesive between the opposing substrates It is formed by including a component and a thickener for increasing the viscosity of the curable adhesive component, the thickener includes a crosslinked polycyanurate formed by the photocrosslinking reaction of the photosensitive polycyanurate-based polymer represented by the above formula (1).

According to another aspect of the invention, the adhesive sheet of the present invention is an adhesive sheet consisting of a support film, a first adhesive film laminated on the upper surface of the support film and a second adhesive film laminated on the lower surface of the support film, The first and second adhesive films are each cured to form a curable adhesive component for adhering between the opposing substrates, and a thickener for increasing the viscosity of the curable adhesive component, wherein the thickener is represented by the formula (1) It includes a crosslinked polycyanurate formed by photocrosslinking of the photosensitive polycyanurate-based polymer.

The adhesive sheet of the present invention is provided with an adhesive film having excellent physical properties such as dimensional stability, heat resistance, adhesive strength, etc. due to the crosslinked polycyanurate of the network structure is improved.

Hereinafter, the present invention will be described in detail.

The adhesive composition according to the invention comprises a curable adhesive component which is cured to bond between opposing substrates.

As the curable adhesive component, commonly used curable resins such as epoxy resins, phenol resins, acrylic resins, polyimide resins, melamine resins, and urea resins can be used. Moreover, a plastic resin can further be added within the range which does not impair the objective of this invention.

As described above, the curable adhesive component is widely used because it is inexpensive and easy to obtain, but has a disadvantage in that precise work is difficult because of its high flowability because it is manufactured in a liquid phase having a low viscosity. In order to solve this problem, the adhesive composition of the present invention includes a photosensitive polycyanurate-based polymer represented by the formula (1) as a precursor of a thickener to increase the viscosity so that an adhesive having an appropriate viscosity can be produced.

Referring to Formula 1, a triazine ring having a photoactive side chain is introduced into the main chain in the photosensitive polycyanurate-based polymer. The triazine ring is a hexagonal aromatic compound, which contains three nitrogen atoms, and has an excellent ability to attract electrons. By introducing such a triazine ring into the main chain, physical properties such as heat resistance and dielectric constant of the polymer resin are improved, and photoreaction occurring in the photoactive side chain is promoted.

R _{1, which} is a photoactive side chain of the triazine ring, is composed of cinnamate, coumarin, chalcone, maleimide derivative, and the like, as shown in Formula 2. Such side chains are crosslinked due to cycloaddition between them by light such as ultraviolet rays. Examples of photocrosslinking reactions that can occur between these side chains are shown in Scheme 1 below.

As described above, the photosensitive polycyanurate-based polymer included in the adhesive composition according to the present invention may form a crosslinked polycyanurate having a network structure through a photocrosslinking reaction as in Scheme 1. The crosslinked polycyanurate thus formed acts as a thickener to enhance the viscosity of the adhesive composition to improve excessive flow of the adhesive composition. In addition, due to the excellent heat resistance, dimensional stability and mechanical properties of the crosslinked polycyanurate itself, the physical properties of the adhesive including the same are also improved.

In the adhesive composition of the present invention, the content of the photosensitive polycyanurate-based polymer is preferably 0.1 to 20% by weight based on the total amount of the curable adhesive component in consideration of the physical properties of the adhesive, the number average molecular weight is about 1000 to 1000000 It is preferable.

A hardener may be further added to the adhesive composition according to the present invention. As a hardening | curing agent normally used, there are a thermosetting agent and a photocuring agent, and mainly amines, imidazoles, tertiary amines, fast curing mercaptans, acid anhydrides, etc. are used.

In addition, a curing aid, filler, softener, accelerator, colorant, flame retardant, light stabilizer, coupling agent, polymerization inhibitor, and the like may be further added to the adhesive composition of the present invention if necessary. These additives are optionally added depending on the purpose of use, use, treatment conditions, and the like.

By using the adhesive composition prepared in this way it can be prepared in the form of an adhesive sheet (10). An example of a preferred manufacturing method will be described with reference to the drawings.

 First, the photosensitive polycyanurate polymer of Formula 1 is dissolved in a suitable organic solvent, and then mixed well with a curable adhesive component such as an epoxy resin. If necessary, a curing agent and the like are added, degassed and filtered to prepare an adhesive composition. The prepared adhesive composition is applied onto release paper 1 such as polyimide film, polyester film, polycarbonate film, polyolefin film and the like. Subsequently, the solvent is removed by gradually warming, depressurizing or flowing the air, and irradiating ultraviolet rays to induce photocrosslinking reaction of the photosensitive polycyanurate-based polymer contained in the applied adhesive composition. 3) to form an adhesive sheet 10 is formed (see Fig. 1). When the adhesive sheets 10 prepared as described above are bonded between the substrates facing each other, the release paper 1 is separated from the adhesive film 3.

As another method of manufacturing the adhesive sheet, the adhesive film 3 is formed on the upper and lower surfaces of the support film 5 by using the adhesive composition prepared in the above-described process, respectively. One adhesive film-supporting film-second adhesive film can be produced in the three-layer adhesive sheet 10 (see Fig. 2). The adhesive sheet 10 having a three-layer structure manufactured as described above may be applied between substrates facing each other to firmly bond both substrates. In this case, a polyimide film or the like may be used as the support film.

The adhesive sheet prepared as described above may further attach a protective film such as polyethylene film on the adhesive film as needed.

In the adhesive film constituting the adhesive sheet according to the present invention, a crosslinked polycyanurate of a network structure in which a curable adhesive component and the photosensitive polycyanurate polymer represented by Chemical Formula 1 is formed through a photocrosslinking reaction as in Scheme 2 is Included. Therefore, since the formed adhesive film has appropriate adhesiveness and rigidity due to the contained crosslinked polycyanurate, it is possible to precisely bond between the substrates. In addition, due to the contained crosslinked polycyanurate, physical properties such as dimensional stability, heat resistance, and adhesion of the adhesive film are also improved.

In the adhesive sheet of the present invention, the curable adhesive component of the adhesive film is the same as in the adhesive composition described above, and the preferable content of the crosslinked polycyanurate is 0.1 to 20% by weight based on the total amount of the curable adhesive component. In addition, the thickness of the adhesive film can be adjusted depending on the purpose of use is preferably 5 to 200 ㎛.

Adhesive sheet prepared using the adhesive composition of the present invention can be usefully used to bond between various substrates including electronic components such as chips and substrates, lead frames and chips, chips and chips. In particular, when the conductive particles such as silver, nickel and copper are dispersed in the curable adhesive component, they may be very useful as an anisotropic conductive adhesive.

Hereinafter, examples will be described in detail to help understand the present invention. However, embodiments according to the present invention can be modified in many different forms, the scope of the invention should not be construed as limited to the following examples.

Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.

Preparation Example: Preparation of Photosensitive Polycyanurate-Based Polymer

Preparation Example 1 Preparation of Photosensitive Polycyanurate-Based Polymer Having Cinnamate Photoactive Side Chain

(1) Monomer Synthesis Including Triazine Ring

10 g of 4- (2-tetrahydropyranyloxy) bromobenzene was dissolved in a three-necked flask filled with nitrogen with 50 ml of tetrahydrofuran and reacted with magnesium for 24 hours. This solution was slowly added dropwise to a solution of 7.17 g of 2,4,6-trichloro-1,3,5-s-triazine dissolved in 200 ml of tetrahydrofuran in a three-necked flask filled with nitrogen, at -20 ° C. The reaction was carried out for 12 hours. After the reaction was terminated, the reaction solution was decompressed at room temperature to remove tetrahydrofuran, and then dissolved in ethyl acetate. The solution was mixed with a basic aqueous solution, and impurities were extracted with vigorous stirring. Then, the aqueous phase was separated and removed under reduced pressure at room temperature to remove ethyl acetate. The solvent was removed and the remaining solid material was recrystallized from normal hexane to give 8.2 g of triazine monomer.

(2) Polymerization of Polycyanurate

3.77 g of bisphenol A, 1.23 g of sodium hydroxide, and 0.59 g of cetyldimethylbenzylammonium chloride were dissolved in 100 ml of distilled water. 5.13 g of the monomer synthesized in Preparation Example 1 (1) was transferred to a 1-neck flask dissolved in 50 ml of chloroform and stirred for 12 hours. After the reaction was completed, the solution was slowly dropped into methanol to form a precipitate, and the precipitate was separated by filtration under reduced pressure. The precipitate was dissolved in tetrahydrofuran and then reprecipitated in normal hexane and filtered under reduced pressure. 40 folds of the obtained solid substance were vacuum-dried to obtain 4.4 g of polycyanurates.

(3) Modification of Polycyanurate

Preparation Example 1 0.12 g of pyridinium para toluenesulfonate was added to a solution of 3.5 g of polycyanurate polymerized in 40 ml of tetrahydrofuran and ethanol, followed by reaction at room temperature for 24 hours. After completion of the reaction, the solution was slowly dropped into methanol to form a precipitate, which was filtered under reduced pressure to separate the precipitate. The precipitate was vacuum dried at 40 deg. C to obtain 2.1 g of polycyanurate with a hydroxy functional group.

(4) Introduction of cinnamate photosensitive group

3 g of polycyanurate containing a hydroxy functional group was dissolved in 25 ml of tetrahydrofuran and 5.57 ml of triethylamine. A solution in which 7.16 g of cinnamoyl chloride was dissolved in 5 ml of tetrahydrofuran was added dropwise at 0 ° C, followed by reaction for 2 hours. After completion of the reaction, the solution was slowly dropped in methanol to precipitate the polymer material. This process was repeated twice. The precipitate obtained was filtered under reduced pressure and dried under vacuum at 40 ° C. to obtain 3.2 g of a photosensitive polycyanurate polymer having a triazine ring having a cinnamate photoactive side chain finally introduced into the main chain.

Preparation Example 2: Photosensitive polycyanurate polymer having a chalcone photosensitive functional group

(1) Synthesis of Chalcon Photosensitive Group

10 g of 4-methoxychalcone and 2.05 g of sodium cyanide were dissolved in 100 ml of methyl sulfoxide and allowed to react for 24 hours. After completion of the reaction, the reaction solution was mixed with chloroform and stirred with distilled water to extract impurities. After removing the aqueous phase, the chloroform was removed under reduced pressure at room temperature. The remaining solid phase was recrystallized in methanol and then dried in vacuo at 40 ° C. to obtain 5.4 g of 4-hydroxychalcone which could function as a side chain for the photoreaction.

(2) Introduction of the Calcon photosensitive functional group

5 g of 4-hydroxychalcone and 6.14 g of polycyanurate with hydroxy functional groups synthesized in (3) of Preparation Example 1 were dissolved in 60 ml of tetrahydrofuran, followed by 0.38 g of diethylazodicarboxylate and triphenylphosphate. After 0.58 g of pin was added, the mixture was reacted at room temperature for 24 hours. After completion of the reaction, precipitated twice in methanol and filtered under reduced pressure. The obtained compound was vacuum-dried at 40 degreeC, and 5.7 g of the photosensitive polycyanurate type polymer which the triazine ring which has a chalcone photoactive side chain was introduce | transduced into the main chain was obtained.

Preparation Example 3: Photosensitive polycyanurate polymer having a coumarin photosensitive functional group

(1) Introduction of coumarin photosensitive functional group

3.57 g of 7-hydroxycoumarin and 6.14 g of polycyanurate with hydroxy synthesized in Preparation Example 1 (3) were dissolved in 60 ml of tetrahydrofuran, followed by 0.38 g of diethylazodicaroxylate and triphenylphosphine. 0.58 g was added and reacted at room temperature for 24 hours. After completion of the reaction, the reaction solution was precipitated twice in methanol to obtain a polymer precipitate. The polymer precipitate was vacuum dried at 40 ° C. after filtration under reduced pressure to obtain 5.3 g of a photosensitive polycyanurate polymer having a triazine ring having a coumarin photoactive side chain introduced into the main chain.

Example 1

According to the ingredients and contents shown in Table 1 below, an adhesive composition was prepared.

The photosensitive polycyanurate polymer obtained in Preparation Example 1 was mixed with liquid and solid epoxy resin, rubber, UV curing agent and UV curing aid using MEK (methyl ethyl ketone) as a solvent. The adhesive composition was then prepared by adding an epoxy curing agent, defoaming and filtering.

Thereafter, the prepared adhesive composition was applied on a polyimide film having a thickness of 50 μm, gradually raised to room temperature at 120 ° C., and gradually reduced to 30 tor at normal pressure to remove the solvent to form a coating film. Subsequently, ultraviolet rays were irradiated onto the formed coating film, and a 25 μm polyethylene protective film was laminated thereon, thereby preparing an adhesive sheet having a thickness of 25 μm.

Examples 2 and 3

The same method as in Example 1, except that the photosensitive polycyanurate-based polymer obtained in Preparation Example 2 (Example 2) and Preparation Example 3 (Example 3) was used instead of the photosensitive polycyanurate-based polymer obtained in Preparation Example 1. An adhesive sheet was prepared.

Comparative example

An adhesive sheet was prepared in the same manner as in Example 1 except that the photosensitive polycyanurate-based polymer was not added.

In Table 1, phr is an abbreviation of parts per resin, and represents a weight ratio to the total amount of resin in the adhesive composition.

The physical properties of the adhesive films prepared in Examples 1 to 3 and Comparative Examples were measured, and the results are shown in Table 2.

As shown in Table 2, as in Examples 1 to 3, the adhesive film using the adhesive composition according to the present invention has improved flowability even at high temperatures, and shows excellent dimensional stability, heat resistance, adhesive strength, and the like.

As described above, the photosensitive polycyanurate-based polymer in which the triazine ring having a photoactive side chain included in the adhesive composition of the present invention is introduced into the main chain may form a crosslinked polycyanurate having a network structure by photocrosslinking. . Since the crosslinked polycyanurate lowers excessive flowability of the curable adhesive component, the adhesive including the same not only improves flowability but also shows excellent dimensional stability, heat resistance, and adhesion. Therefore, the adhesive sheet produced using the adhesive composition of the present invention can be usefully used for bonding between various substrates including electronic components.

Claims (10)

An adhesive composition comprising a curable adhesive component for curing and adhering between opposing substrates and a precursor of a thickener for increasing the viscosity of the curable adhesive component, The precursor of the thickener is an adhesive composition, characterized in that the photosensitive polycyanurate-based polymer represented by the formula (1); <Formula 1>

In Formula 1, m + n = 1, 0 ≤ m ≤ 1 and 0 ≤ n ≤ 1, R ₁ is each independently selected from the group consisting of (1a) to (4a) of the formula (2) , <Formula 2>

In (1a) of the formula (2), X is any one selected from the group represented by the following formula (3), <Formula 3>

In Formula 3, m and n are each 0 to 10, In (1a) of the formula (2), Y is one selected from the group represented by the following formula (4), <Formula 4>

In Formula 4, 1,2,3,4,5,6,7,8,9 are each independently selected from the group represented by the following formula (5), <Formula 5>

In Formula 5, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (2a) and (3a) of Formula 2, n is 0 to 10, 1,2,3,4,5 are each independently selected from the following Formula 6, <Formula 6>

In Formula 6, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (4a) of the formula (2), Y is any one selected from the group represented by the following formula (7), <Formula 7>

In Formula 7 n is 0 to 10, In (4a) of the formula (2), 1 and 2 are each independently selected from the group represented by the following formula (8), <Formula 8>

In Formula 8, A is any one selected from the group consisting of H, F, CH ₃ , CF ₃ and CN, In Formula 1, R ₂ and R ₃ are each independently selected from the group represented by Formula 9 below, <Formula 9>

In Formula 9, m and n are each 0 to 10, and 1, 2, 3, 4, 5, 6, 7, and 8 are each independently H, F, Cl, CN, CH ₃ , OCH ₃ , and CF Any one selected from the group consisting of ₃ , X is any one selected from the group consisting of H, F, Cl, CN, CH ₃ , OCH ₃ , and CF ₃ , and Y is CH ₂ , C (CH ₃ ) ₂ , Any one selected from the group consisting of C (CF ₃ ) ₂ , O, S, SO ₂ , CO, and CO ₂ . According to claim 1, wherein the content of the photosensitive polycyanurate-based polymer is an adhesive composition, characterized in that 0.1 to 20% by weight based on the total amount of the curable adhesive component. The adhesive composition according to claim 1, wherein the number average molecular weight (Mn) of the photosensitive polycyanurate-based polymer is 1000 to 1000000. The adhesive composition of claim 1, wherein the curable adhesive component is any one selected from the group consisting of epoxy resins, phenol resins, acrylic resins, polyimide resins, melamine resins, and urea resins. In the adhesive sheet consisting of a release paper and the adhesive film laminated on the surface of the release paper, The adhesive film is cured to form a curable adhesive component for bonding between the opposing substrates, and a thickener for increasing the viscosity of the curable adhesive component, the thickener is a photosensitive polycyanurate-based polymer represented by the formula An adhesive sheet comprising a crosslinked polycyanurate formed by the photocrosslinking reaction; <Formula 1>

In Formula 1, m + n = 1, 0 ≤ m ≤ 1 and 0 ≤ n ≤ 1, R ₁ is each independently selected from the group consisting of (1a) to (4a) of the formula (2) , <Formula 2>

In (1a) of the formula (2), X is any one selected from the group represented by the following formula (3), <Formula 3>

In Formula 3, m and n are each 0 to 10, In (1a) of the formula (2), Y is one selected from the group represented by the following formula (4), <Formula 4>

In Formula 4, 1,2,3,4,5,6,7,8,9 are each independently selected from the group represented by the following formula (5), <Formula 5>

In Formula 5, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (2a) and (3a) of Formula 2, n is 0 to 10, 1,2,3,4,5 are each independently selected from the following Formula 6, <Formula 6>

In Formula 6, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (4a) of the formula (2), Y is any one selected from the group represented by the following formula (7), <Formula 7>

In Formula 7 n is 0 to 10, In (4a) of the formula (2), 1 and 2 are each independently selected from the group represented by the following formula (8), <Formula 8>

In Formula 8, A is any one selected from the group consisting of H, F, CH ₃ , CF ₃ and CN, In Formula 1, R ₂ and R ₃ are each independently selected from the group represented by Formula 9 below, <Formula 9>

In Formula 9, m and n are each 0 to 10, and 1, 2, 3, 4, 5, 6, 7, and 8 are each independently H, F, Cl, CN, CH ₃ , OCH ₃ , and CF Any one selected from the group consisting of ₃ , X is any one selected from the group consisting of H, F, Cl, CN, CH ₃ , OCH ₃ , and CF ₃ , and Y is CH ₂ , C (CH ₃ ) ₂ , Any one selected from the group consisting of C (CF ₃ ) ₂ , O, S, SO ₂ , CO, and CO ₂ . The adhesive sheet according to claim 5, wherein the release paper is any one selected from the group consisting of a polyimide film, a polyester film, a polycarbonate film, and a polyolefin film. In the adhesive sheet consisting of a support film, a first adhesive film laminated on the upper surface of the support film and a second adhesive film laminated on the lower surface of the support film, The first and second adhesive films are each cured to form a curable adhesive component for adhering between the opposing substrates, and a thickener for increasing the viscosity of the curable adhesive component, the thickener is represented by the formula An adhesive sheet comprising a crosslinked polycyanurate formed by photocrosslinking of a photosensitive polycyanurate-based polymer; <Formula 1>

In Formula 1, m + n = 1, 0 ≤ m ≤ 1 and 0 ≤ n ≤ 1, R ₁ is each independently selected from the group consisting of (1a) to (4a) of the formula (2) , <Formula 2>

In (1a) of the formula (2), X is any one selected from the group represented by the following formula (3), <Formula 3>

In Formula 3, m and n are each 0 to 10, In (1a) of the formula (2), Y is one selected from the group represented by the following formula (4), <Formula 4>

In Formula 4, 1,2,3,4,5,6,7,8,9 are each independently selected from the group represented by the following formula (5), <Formula 5>

In Formula 5, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (2a) and (3a) of Formula 2, n is 0 to 10, 1,2,3,4,5 are each independently selected from the following Formula 6, <Formula 6>

In Formula 6, m and n are each 0 to 10, and A, B, C, D, and E are each independently selected from the group consisting of H, F, Cl, CN, CF _3, and CH ₃ . , In (4a) of the formula (2), Y is any one selected from the group represented by the following formula (7), <Formula 7>

In Formula 7 n is 0 to 10, In (4a) of the formula (2), 1 and 2 are each independently selected from the group represented by the following formula (8), <Formula 8>

In Formula 8, A is any one selected from the group consisting of H, F, CH ₃ , CF ₃ and CN, In Formula 1, R ₂ and R ₃ are each independently selected from the group represented by Formula 9 below, <Formula 9>

In Formula 9, m and n are each 0 to 10, and 1, 2, 3, 4, 5, 6, 7, and 8 are each independently H, F, Cl, CN, CH ₃ , OCH ₃ , and CF Any one selected from the group consisting of ₃ , X is any one selected from the group consisting of H, F, Cl, CN, CH ₃ , OCH ₃ , and CF ₃ , and Y is CH ₂ , C (CH ₃ ) ₂ , Any one selected from the group consisting of C (CF ₃ ) ₂ , O, S, SO ₂ , CO, and CO ₂ . The adhesive sheet according to claim 7, wherein the support film is a polyimide film. The adhesive sheet according to claim 5 or 7, wherein the content of the crosslinked polycyanurate is 0.1 to 20% by weight based on the total amount of the curable adhesive component. The adhesive sheet according to claim 5 or 7, wherein the curable adhesive component is any one selected from the group consisting of epoxy resins, phenol resins, acrylic resins, polyimide resins, melamine resins, and urea resins.

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