KR102264925B1 - Curable compound with high refractive index, adhesive composition for optical member comprising the same and composition for optical sheet comprising the same - Google Patents

Abstract

Provided are a compound of Formula 1 or 2, a pressure-sensitive adhesive composition for an optical member comprising the same, and a composition for an optical sheet comprising the same.

Description

CURABLE COMPOUND WITH HIGH REFRACTIVE INDEX, ADHESIVE COMPOSITION FOR OPTICAL MEMBER COMPRISING THE SAME AND COMPOSITION FOR OPTICAL SHEET COMPRISING THE SAME

The present invention relates to a high refractive index curable compound, a pressure-sensitive adhesive composition for an optical member comprising the same, and a composition for an optical sheet comprising the same.

The composition for an optical sheet and the pressure-sensitive adhesive composition for an optical member should have a high refractive index. An optical sheet made of a composition for an optical sheet having a low refractive index may have low luminance when used in an optical display device. A pressure-sensitive adhesive film made of a pressure-sensitive adhesive composition having a low refractive index may not be suitable for an optical member due to low light transmittance.

In order to increase the refractive index of the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member, a monomer having an aromatic group is used. However, the conventionally known monomer having an aromatic group has a limit in increasing the refractive index of the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member. In addition, when the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member including a monomer having a high refractive index has a high viscosity, it may be difficult to use because of a coating property problem. Therefore, the monomer having a high refractive index should be able to prevent deterioration of the coating properties of the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member because of its low viscosity.

Background art of the present invention is disclosed in Korean Patent Publication No. 2013-0074115 and the like.

The problem to be solved by the present invention is to provide a compound having a high refractive index and being curable.

Another problem to be solved by the present invention is to provide a compound capable of increasing coating properties due to low viscosity.

Another problem to be solved by the present invention is to provide a pressure-sensitive adhesive composition for an optical member or a composition for an optical sheet, including the compound.

The high refractive index curable compound of the present invention may be represented by the following Chemical Formula 1 or the following Chemical Formula 2:

<Formula 1>

<Formula 2>

(In Formula 1 and Formula 2, X, R ₁ , R ₂ , a and b are as defined in the detailed description of the invention below).

The pressure-sensitive adhesive composition for an optical member of the present invention may include at least one of a compound of Formula 1, a compound of Formula 2, an oligomer thereof, and a polymer thereof.

The composition for an optical sheet of the present invention may include at least one of a compound of Formula 1, a compound of Formula 2, an oligomer thereof, and a polymer thereof.

The present invention provides a high refractive index and curable compound.

The present invention provides a compound capable of increasing coating properties due to low viscosity.

The present invention provides a pressure-sensitive adhesive composition for an optical member or a composition for an optical sheet comprising the compound.

Hereinafter, embodiments of the present application will be described in more detail. However, the technology disclosed in the present application is not limited to the embodiments described herein and may be embodied in other forms. However, the embodiments introduced herein are provided so that the disclosed content may be thorough and complete and the spirit of the present application may be sufficiently conveyed to those skilled in the art.

In this specification, "refractive index" is a value measured using a refractometer (model name: 3T, ATAGO ABBE, Japan) under a D-ray sodium lamp having a wavelength of 589.3 nm.

As used herein, “(meth)acryl” means acrylic and/or methacrylic.

As used herein, "halogen" means fluorine, chlorine, bromine or iodine.

In the present specification, "substituted" in "substituted or unsubstituted" means that at least one hydrogen atom in the functional group is a C1 to C10 alkyl group, a C6 to C20 aryl group, a C3 to C20 cycloalkyl group, a C7 to C20 arylalkyl group, a hydroxyl group, It means substituted with a halogen, an amino group or a cyano group.

As used herein, "oligomer" means a compound composed of a plurality of (eg, 10 or less) diradicals, and "polymer" is a compound composed of a larger number (eg, more than 10) of diradicals compared to an oligomer. means

Hereinafter, a high refractive index curable compound according to an embodiment of the present invention will be described.

The high refractive index curable compound according to an embodiment of the present invention may be represented by the following Chemical Formula 1 or the following Chemical Formula 2:

<Formula 1>

<Formula 2>

(In Formula 1 and Formula 2, X is a methylene group, an oxygen atom, a sulfur atom, the following Formula 3, or the following Formula 4,

<Formula 3>

(In Formula 3, * is a connection site of an element,

Y and Z are each independently a methylene group or a sulfur atom,

m is an integer from 0 to 5)

<Formula 4>

(In Formula 4, * is a connection site of an element,

n is an integer from 0 to 4)

R ₁ and R ₂ are each independently Formula 5,

<Formula 5>

(In Formula 5, * is a connection site of an element,

R ₃ is a substituted or unsubstituted C1 to C5 alkylene group

R ₄ is a substituted or unsubstituted C2 to C5 alkylene group,

R ₅ is *-R ₆ -VR ₆ -* or *-R ₆ -VR ₆ -VR ₆ -*, wherein * is a linking moiety of an element, and R ₆ is a substituted or unsubstituted C1 to C10 alkylene group. and V is an oxygen atom or a sulfur atom,

k is an integer from 2 to 10).

a and b are each independently an integer of 0 to 4,

at least one of a and b is an integer from 1 to 4).

When m is 0 in Formula 3, it means that Y and Z in Formula 3 are directly connected. The "directly connected" means that no element is interposed between Y and Z (Y-Z).

)을 의미한다.When n is 0 in Formula 4, it means that the carbons of the aromatic group in Formula 4 are directly connected. The "directly linked" means that no element is interposed between the carbons of the aromatic group (

) means

The compounds of Formulas 1 and 2 have a high refractive index, including a cross-linked structure in which two phenyl groups of a biphenyl group are a methylene group, an oxygen atom, a sulfur atom, or a spiro structure of Formula 3 or Formula 4 . Accordingly, the compounds of Chemical Formulas 1 and 2 may be included in the pressure-sensitive adhesive composition or the composition for an optical sheet to increase the refractive index of each composition. Specifically, each of Chemical Formula 1, Chemical Formula 2, a mixture of two or more Chemical Formula 1, and two or more Chemical Formula 2 mixtures may have a refractive index of 1.53 or more, specifically 1.53 to 1.70. Within the above range, the refractive index of the pressure-sensitive adhesive composition or the composition for an optical sheet may be increased.

In one embodiment, the compound of Formula 1 wherein X is a methylene group, an oxygen atom, or a sulfur atom may be represented by any one of the structures listed in Formula A below:

<Formula A>

(In Formula A, R ₁ , R ₂ , a and b are as defined in Formula 1 above).

In another embodiment, the compound of Formula 1, wherein X is Formula 3, may be represented by any one of the structures listed in Formula B below:

<Formula B>

(In Formula B, R ₁ , R ₂ , a and b are as defined in Formula 1 above).

In another embodiment, the compound of Formula 1, wherein X is Formula 4, may be represented by any one of the structures listed in Formula C below:

<Formula C>

(In Formula C, R ₁ , R ₂ , a and b are as defined in Formula 1 above).

In one embodiment, the compound of Formula 2 wherein X is a methylene group, an oxygen atom, or a sulfur atom may be represented by any one of the structures listed in Formula D below:

<Formula D>

(In Formula D, R ₁ , R ₂ , a and b are as defined in Formula 2).

In another embodiment, the compound of Formula 2, wherein X is Formula 3, may be represented by any one of the structures listed in Formula E below:

<Formula E>

(In Formula E, R ₁ , R ₂ , a and b are as defined in Formula 2 above).

In another embodiment, the compound of Formula 2, wherein X is Formula 4, may be represented by any one of the structures listed in Formula F below:

<Formula F>

(In Formula F, R ₁ , R ₂ , a and b are as defined in Formula 2).

Compounds of Formulas 1 and 2 are *-S-[R ₅ -SS] _k -R ₅ -* (* is a connection site of an element, and R ₅ and k are Formula 1, As defined in Chemical Formula 2), elasticity is imparted to the composition and the refractive index may be increased but the viscosity may be low. Specifically, each of Chemical Formula 1, Chemical Formula 2, a mixture of two or more Chemical Formula 1, and a mixture of two or more Chemical Formula 2 may have a viscosity of 20 cps to 200 cps at 25°C. In the above range, even if it is added to the composition for an optical sheet or the pressure-sensitive adhesive composition, the coating property may be increased by not increasing the viscosity or by lowering the viscosity thereof.

The compounds of Formulas 1 and 2 have curability by containing *-SH in Formulas 1 and 2, respectively. Accordingly, the compounds of Chemical Formulas 1 and 2 may be cured and reacted with any one or more curing components included in the pressure-sensitive adhesive composition or the composition for an optical sheet. Specifically, the compounds of Formulas 1 and 2 may be cured by thermal curing, photocuring, or a combination thereof.

Since the compounds of Chemical Formulas 1 and 2 have high refractive index and curability, they are included in the pressure-sensitive adhesive composition to increase the refractive index of the pressure-sensitive adhesive composition, and can be cured with any other components of the pressure-sensitive adhesive composition to form a high refractive index pressure-sensitive adhesive film. Accordingly, the adhesive film may have high light transmittance. In addition, the compounds of Formulas 1 and 2 have a high refractive index and high curability and increase elasticity, so they are included in the composition for an optical sheet to increase the refractive index of the composition for an optical sheet and are cured with any other components of the pressure-sensitive adhesive composition to obtain high refractive index optics A sheet can be formed. Accordingly, the optical sheet may have high luminance and high elasticity.

Specifically, in Formulas 1 and 2, X may be an oxygen atom or a sulfur atom.

Specifically, in Formulas 1 and 2, R ₃ may be a substituted or unsubstituted, methylene group, ethylene group, propylene group, butylene group, or pentylene group.

Specifically, in Formulas 1 and 2, R ₄ is *-R ₇ -CH(R ₈ )-CH ₂ -*(* is a connection site of an element, and R ₇ is a single bond or substituted or unsubstituted C1 to C3 of an alkylene group, and R ₈ is hydrogen or a C1 to C10 alkyl group). More specifically, R ₄ may be -CH ₂ -CH ₂ - or -CH(CH ₃ )-CH ₂ -. The "single bond" refers to a direct connection of C=O and -CH(R ₈ )-CH ₂ - to (-(C=O)-CH(R ₈ )- CH ₂ -).

Specifically, formula (I), in the formula 2 R ₅ is R ₆ can be a substituted or unsubstituted C1 to C5 alkylene group of R _5. More specifically, R ₅ is *-C ₂ H ₄ -SC ₂ H ₄ -*, *-C ₂ H ₄ -OC ₂ H ₄ -OC ₂ H ₄ -*, *-C ₂ H ₄ -OC ₂ H ₄ -*, or *-C ₂ H ₄ -SC ₂ H ₄ -SC ₂ H ₄ -* (* is a connection site of an element).

Specifically, the compound of Formula 1 may be represented by any one of Formulas 1-1 to 1-4 below:

<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

(In Formulas 1-1 to 1-4, k is an integer of 2 to 10).

Specifically, the compound of Formula 2 may be represented by any one of Formulas 2-1 to 2-4 below:

<Formula 2-1>

<Formula 2-2>

<Formula 2-3>

<Formula 2-4>

(In Formulas 2-1 to 2-4, k is an integer of 2 to 10).

The compound of Formula 1 includes the compound of Formula 1 (Compound 1'), wherein a is 0 and b is an integer of 1 to 4, and the compound of Formula 1, wherein a and b are independently of each other an integer of 1 to 4 (Compound 1) "). Compound 1' may be included in an amount of 40 parts by weight to 70 parts by weight, and compound 1" may be included in an amount of 30 parts by weight to 60 parts by weight of 100 parts by weight of the mixture. In the above range, there may be a high refractive index, a low viscosity, and an elastic effect. Specifically, compound 1' may be a compound of Formula 1 wherein a is 0 and b is 1. Specifically, compound 1" may be a compound of Formula 1 wherein a and b are each 1. Specifically, 40 to 60 parts by weight of compound 1' is included in 100 parts by weight of the mixture, and compound 1" is It may be included in an amount of 40 parts by weight to 60 parts by weight. The mixture may have a refractive index of 1.640 or more, specifically 1.640 to 1.645. Within the above range, it may be included in the composition for an optical member or the pressure-sensitive adhesive composition to give a high refractive index. The above description can be equally applied to the compound of formula (2).

Hereinafter, a method for preparing the compound of Formula 1 will be described.

The compound of Formula 1 may be prepared by a conventional method.

In one embodiment, in Formula 1, a is 0 and R _{2 In} Formula 5, R ₄ is *-R ₇ -CH(R ₈ )-CH ₂ -*(* is a linking moiety of an element, and R ₇ is a single bond or a substituted or unsubstituted C1 to C3 alkylene group, and R ₈ is hydrogen or a C1 to C10 alkyl group), the compound of Formula 1 may be prepared by reacting a compound of Formula 6 with a compound of Formula 7 have:

<Formula 6>

(In Formula 6, X, R ₃ and b are as defined in Formula 1 above, R ₇ is a single bond or a substituted or unsubstituted C1 to C3 alkylene group, R ₈ is hydrogen or a C1 to C10 alkyl group to be).

<Formula 7>

(In Formula 7, R ₅ and k are as defined in Formula 1 above).

The compound of Formula 6 and the compound of Formula 7 may be reacted in a mole ratio of 1:1 to 1:8. Within the above range, the compound of Formula 1 can be prepared in high yield. The reaction of the compound of Formula 6 and the compound of Formula 7 may be performed in a solvent at -10°C to +100°C for 0.5 hour to 10 hours. In the above range, the compound of Formula 1 can be prepared in high yield. Solvents include tetrahydrofuran, acetone, dichloromethane, dichloroethane, chloroform, N-methylpyrrolidone, methylsulfoxide, N,N-dimethylacetamide, benzene, acetonitrile, dimethoxyethane, toluene, ethanol, methylene chloride , dimethyl sulfoxide, and water. In order to increase the reaction rate of the compound of Formula 6 and the compound of Formula 7, a basic catalyst may be further used. The basic catalyst may include at least one of triethylamine, diisopropylamine, tetramethylethylenediamine, pyridine, sodium hydroxide, potassium hydroxide, potassium carbonate, and an amine complex. The basic catalyst may be used in an amount of 1.0 to 8.0 moles based on 1 mole of the compound of Formula 6. In the above range, the compound of Formula 1 can be prepared in high yield.

The compound of Formula 6 may be synthesized by a conventional method to those skilled in the art, or commercially available products may be used.

The compound of Formula 7 can be synthesized by a conventional method. The compound of formula (7) can be prepared by aerobic oxidation of the compound of formula (8) in air:

<Formula 8>

(In Formula 8, R ₅ is as defined in Formula 1).

The oxidation reaction in air is carried out with oxygen in air by stirring the compound of formula 8 in air in the presence of a solvent. Accordingly, since no additional reactants are required, the compound of formula 7 can be prepared in an economically and environmentally useful manner. Specifically, the oxidation reaction in air may be performed in the above-described solvent or a mixture thereof. Specifically, the oxidation reaction in air may be performed at 0° C. to 150° C. for 1 hour to 72 hours. In the compound of Formula 7, k may be performed by controlling the time and temperature during the oxidation reaction in air.

In another embodiment, in Formula 1, R ₁ , R ₂ is each R ₄ in Formula 5 is *-R ₇ -CH(R ₈ )-CH ₂ -*(* is a linking site of an element, and R ₇ is a single bond or a substituted or unsubstituted C1 to C3 alkylene group, and R ₈ is hydrogen or a C1 to C10 alkyl group), the compound of Formula 1 is replaced with the compound of Formula 6, except for using the compound of Formula 9 below It can be prepared in the same way as described above:

<Formula 9>

(In Formula 9, X, R ₃ , a and b are as defined in Formula 1 above, R ₇ is a single bond or a substituted or unsubstituted C1 to C3 alkylene group, R ₈ is hydrogen or C1 to C10 of an alkyl group).

The compound of Formula 2 may also be prepared in a manner similar to the compound of Formula 1 above.

Hereinafter, an adhesive composition for an optical member according to an embodiment of the present invention will be described.

The pressure-sensitive adhesive composition for an optical member according to an embodiment of the present invention may include the compound of Formula 1, the compound of Formula 2, an oligomer thereof, a polymer thereof, or a mixture thereof. One or more of the compound of Formula 1, the compound of Formula 2, an oligomer thereof, and a polymer thereof may be included in the pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition for an optical member may have a high refractive index by including the compound of Formula 1 or the compound of Formula 2 above. Specifically, the pressure-sensitive adhesive composition may have a refractive index of 1.50 to 1.70.

The optical member may include various optical elements included in a liquid crystal display device or an organic light emitting display device. Specifically, the optical member may include, but is not limited to, a polarizer, a protective film, a polarizing plate, a transparent conductive layer, a liquid crystal panel of a liquid crystal display device, an organic light emitting diode, a window film, and the like.

Hereinafter, a composition for an optical sheet according to an embodiment of the present invention will be described.

The composition for an optical sheet according to an embodiment of the present invention may include the compound of Formula 1, the compound of Formula 2, an oligomer thereof, a polymer thereof, or a mixture thereof. One or more of the compound of Formula 1, the compound of Formula 2, an oligomer thereof, and a polymer thereof may be included in the composition for an optical sheet. The composition for an optical sheet may have a high refractive index by including the compound of Formula 1, an oligomer thereof, or a polymer thereof. Specifically, the composition for an optical sheet may have a refractive index of 1.58 to 1.70.

Hereinafter, the configuration and operation of the present invention will be described in more detail through embodiments of the present invention. However, the following examples are provided to help the understanding of the present invention, and the scope of the present invention is not limited thereto.

Example 1

Bis (2-mercaptoethyl) sulfide (refractive index: 1.594) of the following formula (i) (50 g, 324 mmol) was placed in a 2L Erlenmeyer flask. 320 ml of dimethyl sulfoxide (DMSO) and 1280 ml of distilled water were added to the Erlenmeyer flask, and bis(2-mercaptoethyl) sulfide was diluted at 25°C. While maintaining the temperature of the mixture in the Erlenmeyer flask at 20° C., it was stirred vigorously in the air for 36 hours to obtain a suspension. The suspension was diluted by adding 500 ml of ethyl acetate, and the layers were separated using a separatory funnel. The water layer was removed, the organic layer was washed with 200 ml of distilled water, and the layers were separated to obtain a glass layer, and this process was repeated 5 times. The obtained organic layer was washed with 100 ml of brine (NaCl aqueous solution), and the layers were separated to obtain an organic layer. Water was removed from the obtained organic layer with MgSO ₄ , and the obtained organic layer was concentrated under reduced pressure to obtain a mixture of a compound of the following formula ii (shape: colorless oil, refractive index: 1.618) (poly-(bismercaptoethylenedisulfide). ¹ H-NMR (300 MHz, CDCl ₃ ): 3.05-3.17 (m, 2 xd), 2.86-2092 (m, 1 xd), 2.67-2.84 (m, 16 xd), 1.69-1.78 (m, 4 xd), d is an integer of 2 to 6. The ¹ H-NMR is a result of a mixture of compounds of the following formula (ii), and is expressed to represent “peak range (shape of peak, relative integration ratio of the corresponding peak among all peaks)”.

<Formula i>

<Formula ii>

(In Formula ii, k is an integer of 2 to 6).

A mixture of the following formula (iii) and the following formula (iv) (6 g, refractive index: 1.649, in 100 parts by weight of the mixture, 64 parts by weight of formula iii, 36 parts by weight of formula iv, viscosity: 2000 to 300 cps at 25° C.) and the formula prepared above 2 g of the mixture of compound ii was diluted in 60 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The resulting reactant was stirred at 25 °C for 4 hours and distilled under reduced pressure to obtain a concentrate (shape: colorless oil, refractive index: 1.6268, viscosity: 41.0 cps at 25 °C). ¹ H-NMR (300 MHz, CDCl ₃ ): 8.09-8.23 (m, 2 xd), 7.77-7.93 (m, 2 xd), 7.39-7.56 (m, 3 xd), 5.25-5.46 (m, 2 xd) , 3.73-3.80 (m, 10 xd), 3.03-3.19 (m, 5 xd), 2.65-2.93 (m, 40 xd), 1.77-1.91 (m, 10 xd), 1.68-1.77 (m, 8 xd) , d = an integer from 2 to 6. The ¹ H-NMR is a result of a mixture of Chemical Formulas 1-1 and 1-2, and is expressed to indicate "peak range (shape of a peak, relative integration ratio of the corresponding peak among all peaks)".

<Formula iii>

<Formula iv>

The obtained concentrate was separated to obtain compounds of Formula 1-1 and Formula 1-2 below.

<Formula 1-1>

<Formula 1-2>

(In Formulas 1-1 and 1-2, k is an integer of 2 to 6)

Example 2

2,2'-(ethylenedioxy)diethanethiol (2,2'-(Ethylenedioxy)diethanethiol CAS Number 14970-87-7 ) (refractive index: 1.506) (102 g, 558 mmol) of the following formula v was placed in a 2L Erlenmeyer flask 125 ml of dimethyl sulfoxide and 5000 ml of distilled water were added to the Erlenmeyer flask to dilute 2,2'-(ethylenedioxy)diethanethiol at 25° C. While maintaining the temperature of the mixture in the Erlenmeyer flask at 20° C. Stir vigorously in air for 24 hours to obtain a suspension.To the suspension, add 500ml of ethyl acetate to dilute, and use a separatory funnel to separate the layers.Remove the water layer, wash the organic layer with 200ml distilled water, and layer Separated to obtain a glass layer, this process was repeated 5 times.The obtained organic layer was washed with 100 ml of brine (NaCl aqueous solution), and the layers were separated to obtain an organic layer.Water was removed _{from the obtained organic layer with MgSO 4 and obtained} The organic layer was concentrated under reduced pressure to obtain a mixture of a compound of the following formula (vi) (shape: colorless oil, refractive index: 1.533, viscosity: 20 cPs) (poly-(bisoxyethylene disulfide). ¹ H-NMR (300 MHz, CDCl ₃ ) : 3.78-3.79 (m, 2 xd), 3.59-3.67 (m, 6 xd), 2.85-2.97 (m, 2 xd), 2.67-2.74 (m, 2 xd), 1.57-1.62 (m, 2H), d = an integer of 2 to 6. The ¹ H-NMR is a result of a mixture of compounds of the following formula (vi), and is expressed to indicate "peak range (shape of a peak, relative integration ratio of the corresponding peak among all peaks)".

<Formula v>

<Formula vi>

(In the above formula (vi), k is an integer of 2 to 6).

A mixture of Formula iii and Formula iv (1.09 g, refractive index: 1.649, in 100 parts by weight of the mixture, 64 parts by weight of Formula iii and 36 parts by weight of Formula iv) and 7.3 g of the compound of Formula vi prepared above with tetrahydro It was diluted in 133 ml of furan. To the resulting mixture was added 0.56 ml of triethylamine. The resulting reactant was stirred at 25 °C for 4 hours and distilled under reduced pressure to obtain a concentrate (shape: colorless oil, refractive index: 1.551, viscosity: 52.3 cps at 25 °C). ¹ H-NMR (300 MHz, CDCl ₃ ) 8.11-8.22 (m, 1x), 7.79-7.90 (m, 1 xd), 7.39-7.53 (m, 1.5 xd), 5.28-5.46 (m, 1.8 xd), 3.71-3.79 (m, 8 xd), 3.55 -3.65 (m, 36 xd), 2.85-2.92 (m, 8 xd), 2.61-2.74 (m, 14 xd), 1.57-1.68 (m, 9 xd), d = an integer from 2 to 6, the ¹ H -NMR is a result of a mixture of compounds of Formulas 1-3 and 1-4 below, and represents "peak range (shape of a peak, relative integration ratio of the corresponding peak among all peaks)".

The obtained concentrate was separated to obtain compounds of Chemical Formulas 1-3 and 1-4 below.

<Formula 1-3>

<Formula 1-4>

(In Formulas 1-3 and 1-4, k is an integer of 2 to 6).

Example 3

23g of the compound of Formula ii was prepared in the same manner as in Example 1.

A mixture of the following formula (vii) and formula (viii) (7 g, refractive index: 1.649, in 100 parts by weight of the mixture, 62 parts by weight of formula (vii), 38 parts by weight of formula (viii), viscosity: 20 to 30 cps at 25°C) and the formula (ii) 23 g of compound was diluted in 70 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The resulting reactant was stirred at 25 °C for 4 hours and distilled under reduced pressure to obtain a concentrate (shape: colorless oil, refractive index: 1.6234, viscosity: 101.5 cps at 25 °C). ¹ H-NMR (300 MHz, CDCl ₃ ): 7.16-7.44 (m, 9 xd), 5.08-5.20 (m, 2 xd), 3.69-3.80 (m, 2 xd), 3.58-3.69 (m, 2 xd) , 2.79 (m, 4 xd), 2.61 (m, 4 xd). d = an integer from 2 to 6. The ¹ H-NMR is a result of a mixture of compounds of the following formulas 2-1 and 2-2, and is indicated to indicate "peak range (shape of a peak, relative integration ratio of the corresponding peak among all peaks)".

<Formula vii>

<Formula viii>

The obtained concentrate was separated to obtain compounds of the following Chemical Formula 2-1 and the following Chemical Formula 2-2.

<Formula 2-1>

<Formula 2-2>

(In Formulas 2-1 and 2-2, k is an integer of 2 to 6).

Example 4

A compound of Formula (vi) was prepared in the same manner as in Example 2.

A mixture of Formula vii and Formula viii (7.3 g, refractive index: 1.649, in 100 parts by weight of the mixture, 62 parts by weight of Formula vii, 38 parts by weight of Formula viii, viscosity: 20 to 30 cps at 25° C.) and the prepared 7.3 g of compound (vi) was diluted in 60 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The resulting reactant was stirred at 25 °C for 4 hours and distilled under reduced pressure to obtain a concentrate (shape: colorless oil, refractive index: 1.5778, viscosity: 178.5 cps at 25 °C). ¹ H-NMR (300 MHz, CDCl ₃ ) 7.22-7.42 (m, 9 xd), 5.05-5.15 (m, 2 xd), 3.69-3.84 (m, 18 xd), 3.02-3.17 (m, 14 xd), 2.61-2.92 (m, 38 xd), 1.84-1.91 (m, 18 xd), 1.72-1.79 (m, 4 xd), d = integers from 2 to 6. The ¹ H-NMR is a result of a mixture of compounds of the following formulas 2-3 and 2-4, and is indicated to indicate "peak range (shape of a peak, relative integration ratio of the corresponding peak among all peaks)".

The obtained concentrate was separated to obtain compounds of the following Chemical Formula 2-3 and the following Chemical Formula 2-4.

<Formula 2-3>

<Formula 2-4>

(In Formulas 2-3 and 2-4, k is an integer of 2 to 6).

Simple modifications or changes of the present invention can be easily carried out by those of ordinary skill in the art, and all such modifications or changes can be considered to be included in the scope of the present invention.

Claims (10)

A compound of Formula 1 or Formula 2:
<Formula 1>

<Formula 2>

(In Formula 1 and Formula 2, X is a methylene group, an oxygen atom, a sulfur atom, the following Formula 3, or the following Formula 4,
<Formula 3>

(In Formula 3, * is a connection site of an element,
Y and Z are each independently a methylene group or a sulfur atom,
m is an integer from 0 to 5)
<Formula 4>

(In Formula 4, * is a connection site of an element,
n is an integer from 0 to 4)
R ₁ and R ₂ are each independently Formula 5,
<Formula 5>

(In Formula 5, * is a connection site of an element,
R ₃ is a substituted or unsubstituted C1 to C5 alkylene group
R ₄ is a substituted or unsubstituted C2 to C5 alkylene group,
R ₅ is *-R ₆ -VR ₆ -* or *-R ₆ -VR ₆ -VR ₆ -*, wherein * is a linking moiety of an element, and R ₆ is a substituted or unsubstituted C1 to C10 alkylene group. and V is an oxygen atom or a sulfur atom,
k is an integer from 2 to 10)
a and b are each independently an integer from 0 to 4, and at least one of a and b is an integer from 1 to 4). The compound of claim 1, wherein the compound has a refractive index of 1.53 or greater. The compound of claim 1 , wherein X is a sulfur atom. The compound of claim 1, wherein R ₆ is a substituted or unsubstituted C1 to C5 alkylene group. According to claim 1, wherein R ₅ is *-C ₂ H ₄ -SC ₂ H ₄ -*, *-C ₂ H ₄ -OC ₂ H ₄ -OC ₂ H ₄ -*, *-C ₂ H ₄ - OC ₂ H ₄ -*, or *-C ₂ H ₄ -SC ₂ H ₄ -SC ₂ H ₄ -* (* is the linking site of the element). The compound of claim 1, wherein the compound of Formula 1 is represented by any one of the following Formulas 1-1 to 1-4:
<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

(In Formulas 1-1 to 1-4, k is an integer of 2 to 10). The compound of claim 1, wherein the compound of Formula 2 is represented by any one of the following Formulas 2-1 to 2-4:
<Formula 2-1>

<Formula 2-2>

<Formula 2-3>

<Formula 2-4>

(In Formulas 2-1 to 2-4, k is an integer of 2 to 6) According to claim 1, wherein the compound comprises a mixture of the compound of Formula 1, wherein a is 0 and b is 1, and the compound of Formula 1, wherein a and b are each 1,
Among 100 parts by weight of the mixture, the compound of Formula 1 in which a is 0 and b is 1 is included in an amount of 40 parts by weight to 70 parts by weight, and the compound of Formula 1 in which a and b are each 1 is 30 parts by weight to 60 parts by weight The compound which is included in parts by weight. A pressure-sensitive adhesive composition for an optical member comprising at least one of the compound of any one of claims 1 to 8, an oligomer thereof, and a polymer thereof. A composition for an optical sheet comprising at least one of the compound of any one of claims 1 to 8, an oligomer thereof, and a polymer thereof.