KR101815758B1 - Novel compound, adhesive composition, adhesive film and display device - Google Patents

Abstract

The present invention relates to a novel compound, a pressure sensitive adhesive composition containing the same, a pressure sensitive adhesive film formed of the pressure sensitive adhesive composition, and a pressure sensitive adhesive film. The present invention relates to a novel compound according to the present invention, diphenyl-oxadiazile) backbone and a monomer having an ester group and a terminal group capable of thermopolymerization with a linking ring, and is excellent in thermal stability and optical properties, and the pressure-sensitive adhesive film comprising the acrylic compound is excellent in transparency, heat Stability and flexibility can be realized.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, a pressure sensitive adhesive composition, a pressure sensitive adhesive film,

The present invention relates to a novel compound, a pressure sensitive adhesive composition containing the same, a pressure sensitive adhesive film formed of the pressure sensitive adhesive composition, and a display device including the pressure sensitive adhesive film.

With the recent development of display related technologies, display devices which can be deformed at the use stage such as folding, rolling, or stretching like rubber are being studied and developed. Since these displays can be modified into various forms, it is possible to satisfy both demands for enlargement of the display at the use stage and miniaturization of the display for carrying.

The deformable display device can be modified into various forms in accordance with the requirements of the user or the situation in which the display device is used. Therefore, it is necessary to recognize the deformed shape of the display and to control the display device in accordance with the recognized shape.

On the other hand, since the deformable display device has a problem that each configuration of the display device is damaged according to the modification, each of the configurations of the display device must satisfy the folding reliability and stability.

In order to meet the increased expectations for such deformable display devices, a more flexible touch panel is required and an optical adhesive film is required for this.

The optical adhesive film material is a material used for the purpose of improving the visibility by reducing the diffuse reflection and enhancing the impact resistance or rigidity of the display module by performing refractive index matching in addition to bonding between the respective constituents of the display device. , Heat resistance, mechanical properties, light transmittance, and optical properties.

Korean Patent Publication No. 2006-0072086

The present invention relates to a novel compound, a pressure sensitive adhesive composition containing the same, a pressure sensitive adhesive film formed of the pressure sensitive adhesive composition, and a display device including the pressure sensitive adhesive film. The present invention relates to an acrylic pressure sensitive adhesive composition containing a novel compound having excellent thermal stability and optical properties. .

The present invention is an example of a novel compound having excellent thermal stability and optical properties,

A compound represented by the following formula (1) can be provided.

[Chemical Formula 1]

In Formula 1,

R ₁ represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 1 to 30 carbon atoms,

At least one of the hydrogen of the R ₁ are each independently substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms or an alkyl group having 1 to 30,

R ₂ represents the following formula (2)

(2)

In Formula 2,

R ₃ represents methyl acrylate or methyl methacrylate,

n is an integer of 1 to 15;

Further, the present invention can provide a pressure-sensitive adhesive composition comprising the compound.

Further, the present invention can provide an adhesive film formed from the adhesive composition.

In addition, the present invention can provide a display device including the adhesive film.

The novel compound according to the present invention is an acrylic compound which is a copolymer obtained by copolymerizing a diphenyl-oxadiazine main chain in the molecular structure with a monomer having an ester group and a terminal group capable of thermopolymerization with a linking ring, And optical properties, and the pressure-sensitive adhesive film containing the same can realize excellent transparency, thermal stability and flexibility.

Figures 1 and 2 are ¹ H-NMR spectra of the compounds prepared in one embodiment, respectively.
Figures 3 to 5 are UV-vis transmission spectra of the compounds prepared in one embodiment, respectively.
Figure 6 is a DSC spectrum of the compound prepared in one embodiment.

While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are shown by way of example in the drawings and will herein be described in detail.

It should be understood, however, that the invention is not intended to be limited to the particular embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

In the present invention, the terms "comprises" or "having ", and the like, specify that there is a feature, number, step, operation, component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

Hereinafter, the present invention will be described in detail.

The present invention relates to a novel compound, a pressure sensitive adhesive composition containing the same, a pressure sensitive adhesive film formed of the pressure sensitive adhesive composition, and a pressure sensitive adhesive film,

The above compound may be an acrylic compound which is a copolymer obtained by copolymerizing a diphenyl-oxadiazine main chain in a molecular structure with a monomer having an ester group and a terminal group capable of thermopolymerization with a linking ring.

For example, the compound may have a structure represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ₁ represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 1 to 30 carbon atoms,

At least one of the hydrogen of the R ₁ are each independently substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms or an alkyl group having 1 to 30,

R ₂ represents the following formula (2)

(2)

In Formula 2,

R ₃ represents methyl acrylate or methyl methacrylate,

n is an integer of 1 to 15;

In the present invention, the "aryl group" is defined as a monovalent substituent derived from an aromatic hydrocarbon.

Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group, A tolyl group, a biphenylyl group, a terphenyl group, a chrycenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorene group, A perfluoroalkyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, group).

"Heteroaryl group" refers to an "aromatic heterocycle" or "heterocyclic" derived from a monocyclic or fused ring. The heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom.

Specific examples of the heteroaryl group include pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazolyl, tetrazolyl, benzotriazolyl, pyrazolyl, imidazolyl, An imidazolyl group, an isoindolyl group, an indolizinyl group, a pyridyl group, an indazolyl group, a quinolyl group, an isoquinolinyl group, a quinolizinyl group, a phthalazinyl group, a naphthyridinyl group, A carbazolyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, an imidazolyl group, A nitrogen-containing heteroaryl group including a phenanthryl group, a phenanthrolinyl group, a phenacyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, a pyrazolopyridinyl group and the like; A sulfur-containing heteroaryl group including a thienyl group, a benzothienyl group, a dibenzothienyl group and the like; An oxygen-containing heteroaryl group including a furyl group, a pyranyl group, a cyclopentapyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group and the like. Specific examples of the heteroaryl group include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, a phenothiazinyl group, an isoxazolyl group, a furazanyl group, a phenoxazinyl group, A compound containing at least two heteroatoms such as a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, .

"Alkyl group" is defined as a functional group derived from a linear or branched saturated hydrocarbon.

Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, , 2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, 2-ethylpropyl group, n-hexyl group, Methylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2- Dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group and 3-methylpentyl group.

As one example, the compound represented by the above formula (1)

R ₁ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 1 to 10 carbon atoms,

At least one of the hydrogen of the R ₁ are each independently substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms of,

R ₂ represents the following formula (2)

(2)

In Formula 2,

R ₃ represents methyl acrylate or methyl methacrylate,

and n is an integer of 1 to 10.

As another example, the compound represented by the general formula (1)

R ₁ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms,

R ₂ represents the following formula (2)

(2)

In Formula 2,

R ₃ represents methyl acrylate,

and n is an integer of 1 to 5.

The compound represented by the formula (1) may be at least one selected from the group consisting of the following structures 1 to 6.

<Structure 1>

<Structure 2>

<Structure 3>

<Structure 4>

<Structure 5>

<Structure 6>

The compound may have a light transmittance of 90% or more in a wavelength region of 400 to 800 nm. Specifically, a wavelength region of 400 to 800 nm may mean a visible light region. At this time, the compound according to the present invention may have a light transmittance of 90% or more, for example, 90 to 100%, 95 to 100% or 96 to 100% in the visible light region. Thus, the compound is excellent in light transmission to the visible light region and can be easily used as a material in the optical field.

The compound may have one or more endothermic peaks at 100 캜 or higher in differential scanning calorimetry (DSC) analysis. For example, the compound may have one or more endothermic peaks at 100 to 160 ° C, 100 to 140 ° C, or 100 to 120 ° C in differential scanning calorimetry analysis. In the differential scanning calorimetry analysis, by having at least one endothermic peak at 100 ° C or higher, the internal crystallinity of the particles formed by the compound is imparted, and excellent thermal stability is ensured by heat treatment at a high temperature .

The present invention can provide a pressure-sensitive adhesive composition comprising the compound. For example, the pressure-sensitive adhesive composition may further include a crosslinking agent and the like, including the compound, and the adduct including the crosslinking agent is not specifically limited. At this time, the compound may include 10 to 60 parts by weight based on 100 parts by weight of the adhesive composition. For example, the compound may include 10 to 50 parts by weight and 10 to 40 parts by weight. The adhesive composition containing the compound in the content within the above range can realize excellent adhesive ability.

Further, the present invention can provide an adhesive film formed using the adhesive composition.

The pressure-sensitive adhesive film may have an average loss elastic modulus of 10 ⁴ to 10 ⁶ Pa measured in a temperature range of -20 ° C to 90 ° C. As described above, the pressure-sensitive adhesive film according to the present invention has a small loss elastic modulus change over a wide temperature range, is very flexible, and can be excellent in bending reliability. The loss elastic modulus of the adhesive film measured at a temperature range of -20 캜 to 90 캜 may be in the range of, for example, 10 ⁴ to 8 x 10 ⁵ , 10 ⁴ to 3 x 10 ^5, or 10 ⁴ to 10 ⁵ .

The adhesive film may be an optical clear adhesive film (Optical Clear Adhesive). Specifically, in order to be used as a pressure-sensitive adhesive film used in the optical field, it is required to have such properties as not to interfere with the path of light, and to have excellent light transmittance.

For example, the optical transparent adhesive film serves to bond the display with the protective substrate or the touch panel, and performs index matching to improve the visibility by reducing the diffuse reflection and improve the impact resistance or rigidity of the display module Or the like.

In addition, flexibility of an adhesive film is also required in order to meet the heightened substrate level of flexible display devices in recent years. On the other hand, the pressure-sensitive adhesive film of the present invention has excellent optical properties and flexibility and can be used as a transparent pressure-sensitive adhesive film for optical applications.

The present invention can provide a display device including the adhesive film. The display device is not particularly limited and may be a liquid crystal display (LCD), a cathode ray tube (CRT), a plasma display panel (PDP), a field emission display (FED) And can be applied to a TV, a computer, a notebook, a navigation, a smart phone, a tablet PC, an e-book, and a wrist watch in a real life.

As one example, the display device may include: a display; Touch panel; And a protective substrate,

The adhesive film may be formed between the display device and the touch panel, and between the touch panel and the protection substrate.

By adhering the components of the display device such as the display device, the touch panel, and the protective substrate using the adhesive film according to the present invention, it is possible to prevent the deterioration of the efficiency of the display device due to the excellent optical characteristics.

The display device may be a foldable display device.

The foldable display means a flexible display in which a folded portion is designed to be folded like a paper so that the folded portion has a radius of curvature of 5 mm or less.

Unlike the conventional adhesive film, the adhesive film used for the foldable display must satisfy the bending reliability. In order to have excellent bending reliability, it is preferable that the change in the loss elastic modulus is small in a wide temperature range.

On the other hand, as described above, the pressure-sensitive adhesive film according to the present invention has a loss elastic modulus ranging from 10 ⁴ to 10 ⁶ Pa and can satisfy the conditions required in the foldable display.

Hereinafter, the present invention will be described in more detail by way of examples and the like. The embodiments of the present invention are intended to be illustrative of the invention and are not intended to limit the scope of the invention.

Example  1: Preparation of compound of < structure 1 >

Compounds of structure 1 according to the invention are prepared via the following schemes 1 to 3.

[Reaction Scheme 1]

5 g of 4-methoxybenzonitrile (TCI), 3.66 g of sodium azide (Aldrich) and 3.01 g of ammonium chloride (mmonium chloride, Aldrich) were mixed, and after nitrogen substitution in vacuum, dimethylform Amide (DMF, Aldrich) and stirred at 100 ° C for 20 hours. Thereafter, the reaction solution was cooled to room temperature, distilled water was added thereto, and the reaction was terminated by filtration to obtain 4.74 g (71%) of Compound A (5-4 (methoxyphenyl) -2H-tetrazole).

4.74 g of Compound A and 5.97 ml of 4-tert-butylbenzoyl chloride (Aldrich) were mixed, and the mixture was purged with nitrogen after vacuum, and then stirred. Then, 44 ml of pyridine (Aldrich) was mixed, stirred at 115 ° C for 2 hours, cooled to room temperature, and the reaction was terminated. Then, the solution was filtered to obtain a compound (B) (2-4 (tert-butylphenyl) -5- (4-methoxyphenyl) -1,3,4-oxadiazole (7.9 g, 95%).

7.9 g of compound B was dissolved in 76 ml of methyl chloride (Aldrich), and after vacuum replacement, 52 ml of boron tribromide (Aldrich) was slowly added to the solution at -78 캜. Then, the temperature was raised to 0 캜 and stirred for 3 hours, followed by stirring at room temperature for 14 hours. Then, the reaction was terminated with ether (Duksan Co., Ltd.) and distilled water, followed by extraction and column purification to obtain the compound C (4- (5- (tert-butylphenyl) -1,3,4-oxadiazole- ) (6.9 g, 91%).

[Reaction Scheme 2]

12.4 g of potassium carbonate (K ₂ CO ₃ , Aldrich) and 5 g of ethyl 4-hydroxybenzoate (Aldrich) were purged with nitrogen and then dissolved in dimethylformoamate (DMF, 8.00 ml of 6-chlorohexan-1-ol (Alfa aesar) was added slowly and the mixture was stirred in a microwave apparatus at 90 ° C and 300 W for 3 hours. After the completion of the reaction, the organic material was extracted and recrystallized to obtain 6 g of compound D (ethyl 4- (6-hydroxyhexyloxy) benzoate).

5 g of the obtained compound D, 5.05 g of methanol (methanol), potassium hydroxide (KOH, Sangen), and 50 ml of distilled water were added and ethanol was added thereto while stirring until the mixture became transparent. Lt; / RTI &gt; After completion of the reaction, 60 ml of hydrogen chloride (HCl, triple helium) and 120 ml of distilled water were added, and the mixture was evaporated under reduced pressure. The residue was recrystallized from methanol to obtain 6.77 g of 4- (6-hydroxyhexyloxy) benzoic acid.

3 g of the obtained compound E was dissolved in 60 ml of anhydrous tetrahydrofuran (THF, THF), 3.51 ml of triethylamine (Acros) was added, the temperature was lowered to 0 ° C, and the mixture was stirred for 30 minutes. 2.05 ml of acryloyl chloride (TCI) was dissolved in 12 ml of anhydrous tetrahydrofuran (THF, THF), stirred at 0 ° C for 1 hour, stirred for 24 hours while being warmed to room temperature. After completion of the reaction, the reaction mixture was removed under reduced pressure, and the obtained product was subjected to column purification to obtain 1.66 g of compound F (4- (6- (acryloyloxy) hexyloxy) benzoic acid.

[Reaction Scheme 3]

1.0 g of Compound F was dissolved in 100 ml of methyl chloride (Aldrich), 0.77 g of dicyclohexylcarbodiamide (Aldrich) and 0.41 g of dimethylaminopyridine (Aldrich) were added and stirred . Then, 1.01 g of Compound C dissolved in methyl chloride (Aldrich) was added slowly, followed by stirring at room temperature for 24 hours. After the completion of the reaction, the organic material was extracted and subjected to column purification to obtain the compound structure 1 (4- (5- (4-tert-butylphenyl) -1,3,4-oxadiazol- ) benzoate (62%).

At this time, ¹ H-NMR spectrum of the prepared structure 1 can be confirmed by referring to FIG.

Example  2: Preparation of compounds of < structure 2 >

Compounds of structure 2 according to the invention are prepared via the following schemes 4 to 5.

[Reaction Scheme 4]

12.4 g of potassium carbonate (K ₂ CO ₃ , Aldrich) and 5 g of ethyl 4-hydroxybenzoate (Aldrich) were purged with nitrogen and then dissolved in dimethylformoamate (DMF, 6.5 ml of chlorobutanol (4-chlorobutan-1-ol, Alfa aesar) was added slowly and the mixture was stirred in a microwave apparatus at 90 ° C and 300 W for 3 hours. After completion of the reaction, the organic material was extracted and recrystallized to obtain 5 g of compound D2 (ethyl 4- (4-hydroxybutoxy) benzoate).

5 g of the compound D2 obtained above, methanol (methanol), 5.05 g of potassium hydroxide (KOH, triangles) and 50 ml of distilled water were added and ethanol was added thereto while stirring until the mixture became transparent. Lt; / RTI &gt; After completion of the reaction, 60 ml of hydrogen chloride (HCl, triple helium) and 120 ml of distilled water were added, and the mixture was evaporated under reduced pressure. The residue was recrystallized from methanol to obtain 5.2 g of 4- (4-hydroxybutoxy) benzoic acid.

4 g of the obtained compound E2 was dissolved in 60 ml of anhydrous tetrahydrofuran (THF, THF), 5.5 ml of triethylamine (Acros) was added, the temperature was lowered to 0 ° C and the mixture was stirred for 30 minutes. 3.2 ml of acryloyl chloride (TCI) was dissolved in 12 ml of anhydrous tetrahydrofuran (THF, THF), stirred at 0 ° C for 1 hour, stirred for 24 hours while being warmed to room temperature. Then, after completion of the reaction, the reaction mixture was removed under reduced pressure, and the resultant product was subjected to column purification to obtain 2.36 g of compound F2 (4- (4- (acryloyloxy) butoxy) benzoic acid).

 [Reaction Scheme 5]

2.0 g of the compound F2 was dissolved in 100 ml of methyl chloride (Aldrich), 1.56 g of dicyclohexylcarbodiamide (Aldrich) and 0.1 g of dimethylaminopyridine (Aldrich) were mixed Lt; / RTI &gt; Subsequently, 1.2 g of Compound C dissolved in methyl chloride (Aldrich) was slowly added thereto, followed by stirring at room temperature for 24 hours. After the completion of the reaction, the organic material was extracted and subjected to column purification to obtain the compound structure 2 (4- (4- (4- (5- (4-tert-butylphenyl) -1,3,4-oxadiazol- 2-yl) benzoyl) phenoxy) butyl acrylate).

At this time, the ¹ H-NMR spectrum of the prepared structure 2 can be confirmed by referring to FIG.

Example  3: Preparation of compound of <structure 3>

Compounds of structure 3 according to the invention are prepared via the following schemes 6 to 7.

[Reaction Scheme 6]

4 g of Compound A and 6.2 g of 4'-butylbiphenyl-4-carbonyl chloride (Aldrich) were mixed, and the mixture was purged with nitrogen after vacuum, and then stirred. Then, 44 ml of pyridine (Aldrich) was mixed, stirred at 115 ° C for 2 hours, cooled to room temperature, and the reaction was terminated. Thereafter, the solution was filtered and then purified by column to obtain 8.5 g of compound B2 (2- (4'-butylbiphenyl-4-yl) -5- (4-methoxyphenyl) -1,3,4-oxadiazole.

8.3 g of compound B2 was dissolved in 76 ml of methyl chloride (Aldrich), and after vacuum replacement, 55 ml of boron tribromide (Aldrich) was slowly added thereto at -78 캜. Then, the temperature was raised to 0 캜 and stirred for 3 hours, followed by stirring at room temperature for 14 hours. Then, the reaction was terminated with ether (Duksan Co., Ltd.) and distilled water, and the resultant was extracted and subjected to column purification to obtain a compound C2 (4- (5- (4'-butylbiphenyl-4-yl) -1,3,4-oxadiazol- -yl) phenol).

[Reaction Scheme 7]

2 g of Compound F was dissolved in 100 ml of methyl chloride (Aldrich), 1.2 g of dicyclohexylcarbodiamide (Aldrich) and 0.41 g of dimethylaminopyridine (Aldrich) were added and stirred. Then, 2.4 g of Compound C2 dissolved in methyl chloride (Aldrich) was slowly added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the organic material was extracted and subjected to column purification to obtain the compound structure 3 (6- (4- (5- (4'-butylbiphenyl-4-yl) -1,3,4-oxadiazol- phenoxy) hexyl acrylate.

Example  4: Preparation of compound of <Structure 4>

The compounds of structure 4 according to the invention are prepared via the following reaction scheme 8:

[Reaction Scheme 8]

1.8 g of the compound F2 was dissolved in 100 ml of methyl chloride (Aldrich), 0.91 g of dicyclohexylcarbodiamide (Aldrich) and 0.41 g of dimethylaminopyridine (Aldrich) were added and stirred . Then, 2.2 g of the compound dissolved in methyl chloride (Aldrich) was slowly added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the organic material was extracted and subjected to column purification to obtain the compound structure 4 (6- (4- (5- (4'-butylbiphenyl-4-yl) -1,3,4-oxadiazol- phenoxy) hexyl acrylate.

Example  5: Preparation of compound of < structure 5 >

Compounds of Structure 5 according to the invention are prepared via the following Schemes 9-10.

[Reaction Scheme 9]

5 g of Compound A and 6.1 g of 4'-butoxybiphenyl-4-carbonyl chloride (Aldrich) were mixed, and the mixture was purged with nitrogen after the vacuum, and then stirred. Then, 44 ml of pyridine (Aldrich) was mixed, stirred at 115 ° C for 2 hours, cooled to room temperature, and the reaction was terminated. Thereafter, the resultant was filtered and purified by column to obtain 7.8 g of compound B3 (2- (4'-butoxybiphenyl-4-yl) -5- (4-methoxyphenyl) -1,3,4-oxadiazole.

7.6 g of compound B3 was dissolved in 76 ml of methyl chloride (Aldrich), and after vacuum replacement, 52 ml of boron tribromide (Aldrich) was slowly added to the solution at -78 캜. Then, the temperature was raised to 0 캜 and stirred for 3 hours, followed by stirring at room temperature for 14 hours. Then, the reaction was terminated with ether (Duksan Co., Ltd.) and distilled water, followed by extraction and column purification to obtain a compound C3 (4- (5- (4'-butoxybiphenyl-4-yl) -1,3,4-oxadiazol- -yl) phenol.

[Reaction Scheme 10]

1.5 g of Compound F was dissolved in 100 ml of methyl chloride (Aldrich), 0.92 g of dicyclohexylcarbodiamide (Aldrich) and 0.41 g of dimethylaminopyridine (Aldrich) were added and stirred . Subsequently, 1.8 g of Compound C3 dissolved in methyl chloride (Aldrich) was slowly added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the organic material was extracted and subjected to column purification to obtain a compound structure 5 (6- (4- (5- (4'-butoxybiphenyl-4-yl) -1,3,4-oxadiazol- phenoxy) hexyl acrylate.

Example  6: Preparation of compound of < structure 6 >

The compounds of Structure 6 according to the present invention were prepared via the following Scheme 11.

[Reaction Scheme 11]

2 g of the compound F2 was dissolved in 100 ml of methyl chloride (Aldrich), 1.2 g of dicyclohexylcarbodiamide (Aldrich) and 0.41 g of dimethylaminopyridine Aldrich were added and stirred. Subsequently, 1.8 g of Compound C3 dissolved in methyl chloride (Aldrich) was slowly added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the organic material was extracted and subjected to column purification to obtain the compound structure 6 (4- (4- (5- (4'-butoxybiphenyl-4-yl) -1,3,4-oxadiazol- phenoxy) butyl acrylate.

Experimental Example  One

The UV-vis transmission spectra of the compounds of Structure 1, Structure 3 and Structure 4 prepared in Examples 1, 3 and 4 are shown in FIGS. Specifically, the UV-vis transmission spectrum for Structure 1 is shown in FIG. 3, the UV-vis transmission spectrum for Structure 3 is shown in FIG. 4, and the UV-vis transmission spectrum for Structure 4 is shown in FIG. 5 .

3 to 5, it was confirmed that the compounds according to the present invention had an average transmittance of 95% or more in the wavelength region of 400 to 800 nm, which is a visible light wavelength region.

Experimental Example  2

The DSC (differential scanning calorimetry) spectrum of the compound of Structure 1 prepared in Example 1 is shown in FIG. Referring to FIG. 6, one or more peaks were observed at 100 ° C or higher, indicating that the compounds according to the present invention had excellent thermal stability at high temperatures.

Experimental Example  3

Adhesive films were prepared using the compounds of Structures 1 to 6 prepared in Examples 1 to 6, and the loss elastic modulus of the adhesive films was measured by dynamic mechanical analysis (DMA). Specifically, the average of the loss elastic modulus measured in the temperature range of -20 to 90 캜 was measured, and the results are shown in Table 1 below.

Loss modulus (Pa) Example 1 5 x 10 ⁴ Example 2 5 x 10 ⁴ Example 3 9 x 10 ⁴ Example 4 8 x 10 ⁴ Example 5 6 x 10 ⁴ Example 6 7 x 10 ⁴

Referring to Table 1, it can be seen that the pressure-sensitive adhesive film prepared using the compound according to the present invention satisfies the loss elastic modulus in the range of 10 ⁴ to 10 ⁶ Pa and exhibits a loss modulus at the minimum of 5 x 10 ⁴ Pa . Thus, it can be seen that the adhesive film according to the present invention is excellent in bending reliability.

Experimental Example  4

Adhesive films were prepared using the compounds of Structures 1 to 6 prepared in Examples 1 to 6, and the adhesive films thus prepared were repeatedly folded at a room temperature for 4 to 20 times with a radius of curvature of 10 mm. Then, whether or not the bulging and bubble flooding of each of the adhesive films were observed was visually observed, but such defects were not observed.

Claims (13)

A pressure-sensitive adhesive composition comprising a compound represented by the following formula (1)
The average loss modulus measured at -20 ℃ to a temperature range of 90 ℃ 5x10 ⁴ to 9x10 ⁴ Pa of pressure-sensitive adhesive film:
[Chemical Formula 1]

In Formula 1,
R ₁ represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms,
At least one of the hydrogen of the R ₁ are each independently a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms,
R ₂ represents the following formula (2)
(2)

In Formula 2,
n is an integer of 1 to 5;
The compound according to claim 1, wherein in formula (1)
R ₁ represents t-butyl, n-butyl, or butoxy-substituted phenyl,
R ₂ represents the following formula (2)
(2)

In Formula 2,
and n is an integer of 1 to 5.
3. The method of claim 2,
In Formula 2,
and n is an integer of 2 or 3.
The method according to claim 1,
Wherein the compound represented by the formula (1) is at least one selected from the group consisting of the following structures 1 to 6.
<Structure 1>

<Structure 2>

<Structure 3>

<Structure 4>

<Structure 5>

<Structure 6>

The method according to claim 1,
Wherein the compound represented by the general formula (1) has a light transmittance of 90% or more in a wavelength region of 400 to 800 nm.
The method according to claim 1,
The compound represented by the general formula (1) has at least one endothermic peak at 100 占 폚 or higher during DSC (Differential Scanning Calorimetry) analysis.
delete delete delete The method according to claim 1,
The adhesive film is an optical clear adhesive film (Optical Clear Adhesive).
A display device comprising the adhesive film according to claim 1.
12. The method of claim 11,
The display device includes: a display; Touch panel; And a protective substrate,
Wherein the adhesive film is formed between the display device and the touch panel and between the touch panel and the protection substrate.
12. The method of claim 11,
Wherein the display device is a foldable display device.

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