KR20160117723A - 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 is a composition represented by chemical formula 1 and 2. Also, provided are an adhesive composition for optical members including the same, and a composition for optical sheets including the same. More specifically, the purpose of the present invention is to provide a compound which has high refractive index and is curable.

Description

TECHNICAL FIELD [0001] The present invention relates to a high refractive index curable compound, a pressure sensitive adhesive composition for an optical member containing the same, and a composition for an optical sheet containing the same. BACKGROUND ART [0002]

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 containing the same.

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

A monomer having an aromatic group is used to increase the refractive index of the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member. However, the known monomer having an aromatic group has limitations in increasing the refractive index of the composition for optical sheets or the pressure-sensitive adhesive composition for optical members. Also, when the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member containing a monomer having a high refractive index has a high viscosity, the coating property may be problematic and it may be difficult to use. Therefore, the monomer having a high refractive index has a low viscosity, so that the coating property of the composition for an optical sheet or the pressure-sensitive adhesive composition for an optical member can be prevented from deteriorating.

The background art of the present invention is disclosed in Korean Patent Publication No. 2013-0074115.

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

Another object to be solved by the present invention is to provide a compound which has a low viscosity and can increase the coating property.

Another object 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 comprising the compound.

The high refractive index curable compound of the present invention can be represented by the following formula 1 or 2:

≪ Formula 1 >

(2)

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

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

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

The present invention provides a compound capable of improving the coating property due to its 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 techniques disclosed in this application are not limited to the embodiments described herein but may be embodied in other forms. It should be understood, however, that the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

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

As used herein, "(meth) acrylic" means acrylic and / or methacrylic.

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

As used herein, the term " substituted or unsubstituted "means that at least one hydrogen atom of the functional group is substituted with a substituent selected from the group consisting of a C1 to C10 alkyl group, a C6 to C20 aryl group, a C3 to C20 cycloalkyl group, a C7 to C20 arylalkyl group, Halogen, amino group or cyano group.

As used herein, the term "oligomer" means a compound consisting of a number of di-radicals (e.g., no more than 10 di-radicals) .

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

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

≪ Formula 1 >

(2)

(Wherein X is a methylene group, an oxygen atom, a sulfur atom, a group represented by the following formula (3) or (4)

(3)

(In the above formula (3), * is the connecting site of the element,

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

and m is an integer of 0 to 5)

≪ Formula 4 >

(In the formula (4), * is a connecting site of the element,

and n is an integer of 0 to 4)

R ₁ and R ₂ each independently represent the following formula (5)

≪ Formula 5 >

(Wherein, * is the connecting site of the element,

R ₃ is a substituted or unsubstituted C 1 to C 5 alkylene group

R ₄ is a substituted or unsubstituted C 2 to C 5 alkylene group,

R ₅ is * -R ₆ -VR ₆ - * or * -R ₆ -VR ₆ -VR ₆ - *, wherein * is the connecting site of the element and R ₆ is a substituted or unsubstituted C 1 to C 10 alkylene group V is an oxygen atom or a sulfur atom,

and k is an integer of 2 to 10).

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

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

When m is 0 in Formula (3), Y and Z are directly connected to each other in Formula (3). Quot; directly connected "means that no element is interposed between Y and Z (Y-Z).

)을 의미한다.In the formula (4), when n is 0, the carbon atom of the aromatic group in the formula (4) is directly connected. Said "direct link" means that no element is interposed between the aromatic group carbons

).

The compounds of the formulas (1) and (2) have high refractive indexes, including two methylene groups, oxygen atoms, sulfur atoms, or crosslinked structures of the spiro structure of the formula (3) . Accordingly, the compounds of the formulas (1) and (2) can be included in the pressure-sensitive adhesive composition or the composition for the optical sheet to increase the refractive index of each composition. Specifically, the mixture of the formulas (1), (2) and (2) or more and the mixture of the formulas (1) and (2) may have a refractive index of 1.53 or more, specifically 1.53 to 1.70. Within this range, the refractive index of the pressure-sensitive adhesive composition or the composition for an optical sheet can be increased.

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

≪ Formula (A)

(Wherein R ₁ , R ₂ , a and b are as defined in the above formula (1)).

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

≪ Formula B >

(Wherein R ₁ , R ₂ , a and b are as defined in the above formula (1)).

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

≪ EMI ID =

(Wherein R ₁ , R ₂ , a and b are the same as defined in the above formula (1)).

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)

<Formula D>

(Wherein R ₁ , R ₂ , a and b are as defined in the above 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:

(E)

Wherein R ₁ , R ₂ , a and b are the same as defined in the above formula (2).

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>

(Wherein R ₁ , R ₂ , a and b are as defined in the above formula (2)).

Formula (I), the compounds of the formula 1, general formula 2 of the phenyl group _{* -S- [R 5 -SS] k} -R 5 of formula (2) * (* is a connection portion of the element, R ₅ and k are the formula 1, (2)), the elasticity is imparted to the composition, the refractive index is high, and the viscosity is low. Specifically, the mixture of the formula (1), the formula (2), the mixture of the formula (1) and the mixture of the formula (2) may have a viscosity of 20 cps to 200 cps at 25 ° C. Within the above range, even when added to the composition for an optical sheet or the pressure-sensitive adhesive composition, the viscosity can be increased or the viscosity can be lowered to improve the coating property.

The compounds of the formulas (1) and (2) have curability by containing * -SH in the formulas (1) and (2), respectively. Accordingly, the compounds of formulas (1) and (2) can be cured with any one or more of the curing components contained in the pressure-sensitive adhesive composition or composition for an optical sheet. Specifically, the compounds of formulas (1) and (2) can be cured by thermal curing, photo-curing or a combination thereof.

Since the compounds of the formulas (1) and (2) have a high refractive index and curability, they can be incorporated in the pressure sensitive adhesive composition to increase the refractive index of the pressure sensitive adhesive composition and cure with any other component of the pressure sensitive adhesive composition to form a high refractive index pressure sensitive adhesive film. Therefore, the adhesive film may have high light transmittance. Further, the compounds of the formulas (1) and (2) have high refractive index, curability and high elasticity, so they are contained in the composition for optical sheets to increase the refractive index of the composition for optical sheets and cure with arbitrary other components of the pressure- A sheet can be formed. Therefore, the optical sheet can have high brightness and high elasticity.

Specifically, in the formulas (1) and (2), X may be an oxygen atom or a sulfur atom.

Specifically, in the formulas (1) and (2), R ₃ may be a substituted or unsubstituted methylene group, an ethylene group, a propylene group, a butylene group, or a pentylene group.

Specifically, in the general formulas (1) and (2), R ₄ is * -R ₇ -CH (R ₈ ) -CH ₂ - * (* is a connecting site of an element, and R ₇ is a single bond or a substituted or unsubstituted C1 to C3 And R &lt; ₈ &gt; is hydrogen or a C1 to C10 alkyl group). More specifically, R ₄ can be -CH ₂ -CH ₂ - or -CH (CH ₃ ) -CH ₂ -. That is directly connected to the (- The "single bond" is C = O and -CH (R ₈₎ -CH ₂ without interposition of any element in the general formula 1, general formula 2 (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 the connecting site of the element).

Specifically, the compound of the formula (1) can be represented by any one of the following formulas (1-1) to (1-4)

&Lt; Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

(In the above Chemical 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 the following formulas (2-1) to (2-4)

&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

<Formula 2-4>

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

The compound of the formula (1) is a compound of the formula (1), wherein a and b are independently an integer of 1 to 4, respectively, in which a is 0 and b is an integer of 1 to 4, The compound 1 'may be contained in an amount of 40 to 70 parts by weight, and the compound 1 "may be contained in an amount of 30 to 60 parts by weight in 100 parts by weight of the mixture. In the above range, high elongation and low viscosity as well as elastic effect can be obtained. Specifically, compound 1 'can be a compound of formula 1 wherein a is 0 and b is 1. Specifically, the compound 1 "may be a compound of the formula 1 in which a and b are each 1. Specifically, in 100 weight parts of the mixture, the compound 1 'is contained in an amount of 40 to 60 parts by weight, 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, the composition for an optical member or the pressure-sensitive adhesive composition may contain high refractive index. The above description can be equally applied to the compound of formula (2).

Hereinafter, a method for producing the compound represented by the formula (1) will be described.

The compound of formula (1) can be prepared by a conventional method.

In one embodiment, a is 0 and R ₂ is R ₄ is _{* -R 7 -CH (R 8)} -CH 2 in the formula (5) in the formula (I) - A * (* is a connection portion of the element, R ₇ is a single bond or a substituted or unsubstituted alkylene group unsubstituted C1 to C3, R ₈ is the compound of formula 1 is an alkyl group of hydrogen or C1 to C10) to the compound of formula (VI) may be prepared by reaction of a compound of formula (VII) have:

(6)

(Wherein X, R ₃ and b are as defined in the above formula (1), 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).

&Lt; Formula 7 >

(Wherein R ₅ and k are the same as defined in Formula 1).

The compound of formula (6) and the compound of formula (7) can be reacted at a mole ratio of 1: 1 to 1: 8. Within this range, the compound of formula (1) can be prepared in high yield. The reaction of the compound of formula (6) with the compound of formula (7) can be carried out in a solvent at -10 ° C to + 100 ° C for 0.5 to 10 hours. Compounds of formula (1) can be prepared in high yields in the above range. The solvent is selected from the group consisting of tetrahydrofuran, acetone, dichloromethane, dichloroethane, chloroform, N-methylpyrrolidone, methylsulfoxide, N, N-dimethylacetamide, benzene, acetonitrile, dimethoxyethane, toluene, , Dimethylsulfoxide, and water. A basic catalyst may be further used to increase the reaction rate of the compound of Formula 6 with the compound of Formula 7. The basic catalyst may include at least one of triethylamine, diisopropylamine, tetramethylethylenediamine, pyridine, sodium hydroxide, potassium hydroxide, potassium carbonate, and amine complexes. The basic catalyst may be used in an amount of from 1.0 mol to 8.0 mol based on 1 mol of the compound of formula (VI). Compounds of formula (1) can be prepared in high yields in the above range.

The compound of formula (6) can be synthesized by a conventional method for a person skilled in the art, or a commercially available product can 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 a compound of formula (8)

(8)

(In the formula (8), R ₅ is the same as defined in the above formula (1)).

The oxidation reaction in air is carried out by oxygen in air by stirring the compound of formula (8) in the presence of a solvent in air. Thus, since no further reactants are required, the compounds of formula (VII) can be prepared in economically and environmentally useful ways. Specifically, the oxidation reaction in air can be carried out in the above-mentioned solvent or a mixture thereof. Specifically, the oxidation reaction in air may be carried out at 0 ° C to 150 ° C for 1 to 72 hours. Among the compounds represented by the general formula (7), k can be performed by adjusting the time and temperature in the oxidation reaction in air.

In other embodiments, the R _1, R ₂ is R _4, respectively in formula (5) in the formula _{1 * -R 7 -CH (R 8} ) -CH 2 - * (* is a connection portion of the element, R ₇ is a single bond or a substituted or unsubstituted C1 to an alkylene group of C3 ring, R ₈ is an alkyl group of hydrogen or C1 to C10), a compound of formula (1), except that to the place of the compound of formula 6 using a compound of formula (9) Can be prepared in the same manner as described above:

&Lt; Formula 9 >

(Wherein X, R ₃ , a and b are as defined in the above formula (1), 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 Lt; / RTI &gt;

Compounds of formula (2) may also be prepared by methods analogous to those of formula (1).

Hereinafter, a pressure-sensitive 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. The compound of Formula 1, the compound of Formula 2, the oligomer thereof, and the polymer thereof may be contained in one or more of the pressure-sensitive adhesive compositions. The refractive index of the pressure-sensitive adhesive composition for an optical member may be high by including the compound of the formula (1) or the compound of the formula (2). 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 or an organic light emitting display. 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, 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. The compound of Formula 1, the compound of Formula 2, the oligomer thereof, and the polymer thereof may be contained in one or more of the compositions for optical sheets. The refractive index of the composition for an optical sheet may be high by including the compound of Formula 1, an oligomer thereof, or a polymer thereof. Specifically, the composition for optical sheets 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 with reference to embodiments of the present invention. However, the following examples are provided to aid understanding of the present invention, and the scope of the present invention is not limited to the following examples.

Example 1

Bis (2-mercaptoethyl) sulfide (refractive index: 1.594) (50 g, 324 mmol) of the following formula i was placed in a 2 L Erlenmeyer flask. 320 ml of dimethylsulfoxide (DMSO) and 1280 ml of distilled water were added to the Erlenmeyer flask, and bis (2-mercaptoethyl) sulfide was diluted at 25 占 폚. The mixture in the Erlenmeyer flask was stirred vigorously in the air for 36 hours while maintaining the temperature at 20 ° C to obtain a suspension. To the suspension was added 500 ml of ethyl acetate and diluted, 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 layer was separated to obtain a glass layer. This process was repeated five 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. Removing water by MgSO ₄ in the obtained organic layer, was concentrated under reduced pressure to obtain an organic layer, the following compound of formula ii. (Shape: a colorless oil, a refractive index: 1.618) (poly- (bis-mercapto ethylene to give a mixture of the disulfide) ¹ _{H-NMR (300MHz, 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 from 2 to 6. The ¹ H-NMR is a result of a mixture of compounds of the following formula (ii) and is indicated to indicate "peak range (peak shape, relative integration ratio of corresponding peak in total peak)".

(I)

(Ii)

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

A mixture (6 g, refractive index: 1.649) of the following formula (iii) and iv: (refractive index: 1.649, 64 parts by weight of the compound of the formula (iii) and 36 parts by weight of the compound of the formula (iv), viscosity is 2000 to 300 cps at 25 ° C) A mixture of 2 g of the compound of ii was diluted in 60 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The obtained reaction product was stirred at 25 占 폚 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 占 폚). ^{1 H-NMR (300MHz, 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 x d), 3.03-3.19 (m, 5 x d), 2.65-2.93 (m, 40 x d), 1.77-1.91 , and d = an integer of 2 to 6. The ¹ H-NMR is a result of a mixture of the following formula (1-1) and the following formula (1-2), and is shown to indicate "peak range (peak shape, relative integration ratio of corresponding peak in total peak)".

(Iii)

(Iv)

The obtained concentrate was separated to obtain the compound of the following formula 1-1 or 1-2.

&Lt; Formula 1-1 >

(1-2)

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

Example 2

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 2 L Erlenmeyer flask To the Erlenmeyer flask, 125 ml of dimethyl sulfoxide and 5000 ml of distilled water were added, and 2,2 '- (ethylene dioxy) diethanethiol was diluted at 25 ° C. The temperature of the mixture in the Erlenmeyer flask was maintained at 20 ° C. The aqueous layer was removed, and the organic layer was washed with 200 ml of distilled water, and the organic layer was washed with water to remove the organic layer. The organic layer was washed with 200 ml of distilled water, The obtained organic layer was washed with 100 ml of brine (aqueous NaCl solution) and layered to obtain an organic layer. Water was removed from the obtained organic layer with MgSO ₄ , U Concentrated under reduced pressure to a layer, the following compounds of formula vi (shape: a colorless oil, a refractive index: 1.533, viscosity: 20cPs) (poly-isomer thereof (which is the bis oxyethylene ^{disulfide) 1 H-NMR (300MHz,} CDCl 3). 2H), 3.78-3.79 (m, 2 x d), 3.59-3.67 (m, 6 x d), 2.85-2.97 d = an integer from 2 to 6. The ¹ H-NMR is the result of a mixture of compounds of the formula (vi) and is indicated to indicate "peak range (peak shape, relative integration ratio of corresponding peak in total peak)".

&Lt; EMI ID =

&Lt;

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

7.3 g of the compound of formula (vi) prepared above and 7.3 g of the compound of formula (iv) were dissolved in tetrahydrofuran (100 ml) 0.0 &gt; ml &lt; / RTI &gt; To the obtained mixture, 0.56 ml of triethylamine was added. The obtained reaction product was stirred at 25 캜 for 4 hours and distilled under reduced pressure to obtain a concentrate (colorless oil, refractive index: 1.551, viscosity: 52.3 cps at 25 캜). ^{1 H-NMR (300MHz, CDCl} 3) (M, 1 x d), 7.39-7.53 (m, 1.5 x d), 5.28-5.46 (m, 1.8 x d), 3.71-3.79 (M, 8 x d), 2.61-2.74 (m, 14 x d), 1.57-1.68 (m, 9 x d), d = 2 to 6, ¹ H -NMR is the result of a mixture of the compounds of the formulas 1-3, 1-4 and indicates the "peak range (shape of peak, relative integration ratio of corresponding peak in total peak) &quot;.

 The obtained concentrate was separated to obtain the compound of the following formula 1-3 or the compound of the formula 1-4.

<Formula 1-3>

<Formula 1-4>

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

Example 3

23 g of the compound of the formula (ii) was prepared in the same manner as in Example 1.

A mixture (7g, refractive index: 1.649) of the following formula (vii) and the following formula (viii), 62 parts by weight of the compound of the formula (vii) and 38 parts by weight of the compound of the formula (viii), 20-30 cps at 25 ° C) 23 g of the compound was diluted with 70 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The obtained reaction product was stirred at 25 占 폚 for 4 hours and distilled under reduced pressure to obtain a concentrate (colorless oil, refractive index: 1.6234, viscosity: 101.5 cps at 25 占 폚). ^{1 H-NMR (300MHz, 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 * d), 2.61 (m, 4 * d). d = an integer from 2 to 6; The ¹ H-NMR is a result of a mixture of the compounds of the following general formulas (2-1) and (2-2), and is shown to indicate "peak range (peak shape, relative integration ratio of corresponding peak in total peak)".

<Formula vii>

<Formula viii>

The obtained concentrate was separated to obtain a compound represented by the following formula (2-1) or (2-2).

&Lt; Formula (2-1)

&Lt; Formula (2-2)

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

Example 4

The compound of formula (vi) was prepared in the same manner as in Example 2.

The mixture (7.3 g, the refractive index: 1.649) of the compound of the formula (vii) and the compound of the formula (viii) contained 62 parts by weight of the compound of the formula (vii) and 38 parts by weight of the compound of the formula (viii), 20-30 cps at 25 ° C, 7.3 g of the compound of formula (vi) was diluted in 60 ml of tetrahydrofuran. To the resulting mixture was added 0.5 ml of triethylamine. The obtained reaction product was stirred at 25 占 폚 for 4 hours and distilled under reduced pressure to obtain a concentrate (colorless oil, refractive index: 1.5778, viscosity: 178.5 cps at 25 占 폚). ¹ H-NMR (300 MHz, CDCl ₃ ) 7.22-7.42 (m, 9 x d), 5.05-5.15 (m, 2 x d), 3.69-3.84 An integer of 2.61-2.92 (m, 38 x d), 1.84-1.91 (m, 18 x d), 1.72-1.79 (m, 4 x d), d = 2-6. The ¹ H-NMR is a result of a mixture of the compounds of the following formulas (2-3) and (2-4) and is shown to indicate "peak range (peak shape, relative integration ratio of corresponding peak in total peak)".

The obtained concentrate was separated to obtain the compound of the following formula (2-3) and the compound of the following formula (2-4).

<Formula 2-3>

<Formula 2-4>

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

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (10)

A compound of the formula 1 or 2:
&Lt; Formula 1 >

(2)

(Wherein X is a methylene group, an oxygen atom, a sulfur atom, a group represented by the following formula (3) or (4)
(3)

(In the above formula (3), * is the connecting site of the element,
Y and Z are each independently a methylene group or a sulfur atom,
and m is an integer of 0 to 5)
&Lt; Formula 4 >

(In the formula (4), * is a connecting site of the element,
and n is an integer of 0 to 4)
R ₁ and R ₂ each independently represent the following formula (5)
&Lt; Formula 5 >

(Wherein, * is the connecting site of the element,
R ₃ is a substituted or unsubstituted C 1 to C 5 alkylene group
R ₄ is a substituted or unsubstituted C 2 to C 5 alkylene group,
R ₅ is * -R ₆ -VR ₆ - * or * -R ₆ -VR ₆ -VR ₆ - *, wherein * is the connecting site of the element and R ₆ is a substituted or unsubstituted C 1 to C 10 alkylene group V is an oxygen atom or a sulfur atom,
and k is an integer of 2 to 10)
a and b are each independently an integer of 0 to 4, and at least one of a and b is an integer of 1 to 4). The compound according to claim 1, wherein the compound has a refractive index of 1.53 or more. The compound according to claim 1, wherein X is a sulfur atom. The compound according to claim 1, wherein R &lt; ₆ &gt; is a substituted or unsubstituted C1 to C5 alkylene group. 2. The method of 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 connecting site of the element). The compound according to claim 1, wherein the compound of formula (1) is represented by any one of the following formulas (1-1) to (1-4):
&Lt; Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

(In the above Chemical Formulas 1-1 to 1-4, k is an integer of 2 to 10). The compound according to claim 1, wherein the compound of formula (2) is represented by any one of the following formulas (2-1) to (2-4)
&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

<Formula 2-4>

(In the formulas (2-1) to (2-4), k is an integer of 2 to 6) The compound of 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,
The compound of the formula 1 wherein a is 0 and b is 1 is contained in an amount of 40 to 70 parts by weight and 100 parts by weight of the mixture contains 30 to 60 parts by weight of the compound of the formula 1, &Lt; / RTI &gt; by weight. 9. 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. 9. 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.