KR20100071871A - Optically anisotropic compound and resin composition and optical member comprising the same - Google Patents

Abstract

The present invention relates to an optically anisotropic compound used to impart optical anisotropy of a polymer resin, a resin composition comprising the same, and an optical member. When the optically anisotropic compound according to the present invention is used in addition to a polymer resin, It is easy to control the optical properties of the polymer resin because of its high expression of optical anisotropy due to deformation and excellent compatibility with the polymer resin.

Description

Optically anisotropic compound and a resin composition and optical member including the same {OPTICALLY ANISOTROPIC COMPOUND AND RESIN COMPOSITION AND OPTICAL MEMBER COMPRISING THE SAME}

The present invention relates to an optically anisotropic compound used for imparting optical anisotropy of a polymer resin, and a resin composition and an optical member comprising the same.

Recently, with the development of the electronics industry, the use of optical polymer resins is rapidly increasing. For example, optical disc substrates used as storage media, optical lenses, optical fibers used for optical communication, Fresnel lenses for projection screens, and prism sheets used for liquid crystal displays, polarizer protective films, compensation films, etc. Demand is surging.

Such optical polymer resins generally require optically isotropy, but due to the structural or processing stress of the polymer resin itself, the polymer resin of the final product may have anisotropy. In addition, when the optical resin is inserted into the multilayer structure, the optical resin may have optical anisotropy due to thermal expansion and contraction with each layer. If a film, lens or the like having such anisotropy exists in the optical path, it is preferable to use an optical member composed of an optical resin which can change the properties of the image and adversely affect the signal reading, thereby suppressing the anisotropy as small as possible.

On the other hand, it may artificially impart optical birefringence. For example, especially when the polarizing plate is fixed by an adhesive, stress is concentrated and birefringence is generated in the TAC (Triacetylcellulose) layer due to the contraction or expansion of the polarizing plate under high temperature and high temperature and high humidity conditions, resulting in light leakage.

In order to suppress light leakage, it is possible to adjust so that the residual stress remains because the stress relaxation property of the adhesive fixed to the polarizing plate is very excellent. In this case, this can be achieved when the pressure-sensitive adhesive used is an uncrosslinked structure.

However, the pressure-sensitive adhesive layer requires high high temperature cohesive force in order to maintain durability, and for this, it exhibits suitable adhesive properties in the form of a partially crosslinked viscoelastic material. The introduction of the partial crosslinked structure into the pressure-sensitive adhesive layer has residual stress under a given stress, and the polymer in the crosslinked structure is oriented in a specific direction to exhibit birefringence. Under this orientation, the acrylic pressure sensitive adhesive will exhibit negative birefringence.

On the other hand, as the LCD panel is enlarged, the polarizing plate is also enlarged. Accordingly, the shrinkage of the polarizing plate is increased and the residual stress of the pressure-sensitive adhesive layer is increased under heat and moisture resistant conditions, resulting in a large birefringence of negative values, resulting in severe light leakage.

Accordingly, in order to minimize the light leakage phenomenon, it is possible to optically compensate for the birefringence of the negative value caused by the contraction of the polarizer when the birefringence of the negative value of the pressure-sensitive adhesive caused by the residual stress is adjusted to the positive birefringence. Therefore, in order to compensate the birefringence optically by using the pressure-sensitive adhesive, it is important that the pressure-sensitive adhesive exhibits a positive birefringence under residual stress using compounds having high optical anisotropy.

Korean Patent Laid-Open Publication No. 2003-0069461 discloses a technical idea of incorporating a low molecular weight material exhibiting positive birefringence under stress into an acrylic pressure sensitive adhesive layer to correct birefringence of negative value represented by an acrylic pressure sensitive adhesive layer under residual stress. However, the low molecular weight used may be a compatibility problem with the pressure-sensitive adhesive, and if an excessive amount is used, there is a high possibility of phase separation with the pressure-sensitive adhesive, which may cause a problem in light transmittance or durability. In addition, in the case of a single molecule, the degree of anisotropy may be insignificant because the degree of alignment is insignificant according to the arrangement of the polymer resin.

In order to solve the above problems, the present invention is to provide an optically anisotropic compound having a large optical anisotropy, effective control of the optical properties of the polymer resin even with a small amount of use, and excellent compatibility with the polymer resin.

In addition, the present invention is to provide a resin composition comprising the optically anisotropic compound and a polymer resin and an optical member using the resin composition.

The present invention provides a compound represented by the following formula (1). The compound represented by the following formula (1) is an optically anisotropic compound.

[Formula 1]

M ¹ -LM ²

In formula 1, L is C ₂ ~ C ₆₀ Alkylene oxide, C ₂ ~ C ₆₀ Alkylene, or C ₂ ~ C ₆₀ siloxane;

M ¹ and M ² are each independently a substituent represented by formula (2);

[Formula 2]

In Formula 2,

는

또는

이며;

Is

or

Is;

는

또는

이며;

Is

or

Is;

는

또는

이며;

Is

or

Is;

R ¹ to R ⁵ and the following R ⁶ to R ⁸ are each independently —H, C ₁ to C ₂₀ alkyl, C ₁ to C ₂₀ fluoroalkyl, C ₂ to C ₂₀ Alkenyl, C ₂ ~ C ₂₀ fluoroalkenyl, C ₂ ~ C ₂₀ alkynyl, C ₂ ~ C ₂₀ fluoroalkynyl,-(CH ₂ CH ₂ O) _o CH ₃ ,-(CH ₂ CHCH ₃ O) _o CH ₃ , or-(CHCH ₃ CH ₂ O) _o CH ₃ , o is an integer from 1 to 5;

X ¹ to X ⁵ are each independently —SiW ¹ W ² —, —O—, —NR ⁶ —, —S—, —SO—, —SO ₂ —, — (CH ₂ ) _p —, —C (= O) NR ^6- , -NR ⁶ C (= 0)-, -NR ⁶ C (= 0) NR ^6- , -C (= 0)-, -C (= 0) O-, -OC (= 0) )-Or -OC (= 0) O- and p is an integer of 0 to 2;

W ¹ is -R ⁷ , -NHR ⁷ , or -N (R ⁷ ) ₂ ;

W ² is -R ⁸ , -NHR ⁸ , or -N (R ⁸ ) ₂ ;

Q ¹ to Q ⁸ are each independently -H, -F, -Cl, -Br, -I, -CN, -CF ₃ , -OCF ₃ , -R ⁶ , -OR ⁶ , -NHR ⁶ , -NR ⁶ R ⁶ or —C (═O) R ⁶ ;

Z is C or N, wherein when Z is N, no bond with the corresponding Q ¹ to Q ⁸ is present;

Y and G are each independently — (CH ₂ ) _r SiW ¹ W ² (CH ₂ ) _s —, —O—, —NR ⁶ —, —S—, —SO—, —SO ₂ —, — (CH ₂₎ ) _q- , -CH = CH-, -C≡C-, -C (= O) O (CH ₂ ) _q- , -OC (= O) (CH ₂ ) _q -,-(CH ₂ ) _q C (= O) O-,-(CH ₂ ) _q OC (= O)-, -C (= O)-, -C (= O) NR ^6- , -NR ⁶ C (= O)-, -C (= O) S-, or -SC (= O)-, q is an integer from 0 to 5, and r and s are each independently 0 or 1;

l and m are each independently an integer of 0-2, and l + m is an integer of 1-4.

In addition, the present invention is a polymer resin; And it provides a resin composition comprising a compound represented by the formula (1).

In another aspect, the present invention provides an optical member comprising a polymer film or pressure-sensitive adhesive prepared from the resin composition.

When the optically anisotropic compound represented by the formula (1) according to the present invention is used in addition to the polymer resin, the optical anisotropy is largely expressed by the deformation of the polymer resin, and the compatibility with the polymer resin is excellent, thereby controlling the optical properties of the polymer resin. It is easy to

The compound represented by Formula 1 of the present invention is easily mixed with various polymer resins, and has excellent control of optical properties against deformation of the polymer resin, and is also physically and chemically stable under the conditions in which liquid crystal displays are commonly used. Not stable to heat and light.

Therefore, the compound represented by Chemical Formula 1 may be used to control optical properties of the polymer resin by mixing with various various polymer resins.

In the compound represented by Formula 1 of the present invention, L is a linker (linker) connecting M ¹ and M ² C ₂ ~ C ₆₀ Alkylene oxide, C ₂ ~ C ₆₀ Alkylene, or C ₂ ~ C ₆₀ siloxanes.

The alkylene oxide of C ₂ ~ C _{60 In} L is preferably an alkylene oxide represented by the following formula (3), more preferably C ₂ ~ C ₆₀ ethylene oxide or C ₃ ~ C ₆₀ propylene oxide.

(3)

In formula (3), R ⁹ and R ¹⁰ are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) u CH 3, - (CH 2 CHCH 3 O) u CH 3 Or-(CHCH ₃ CH ₂ O) _u CH ₃ , u is an integer from 1 to 5;

t is an integer of 1-30.

In addition, the alkylene of C ₂ ~ C _{60 In} L is preferably C ₃ ~ C ₆₀ Branched alkylene.

In addition, the siloxane of the C ₂ ~ C ₆₀ in L is preferably a siloxane represented by the following formula (4), more preferably a siloxane in which v is an integer of 2 to 30 in the formula (4).

[Formula 4]

In formula (4), R ¹¹ and R ¹² are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) w CH 3, - (CH 2 CHCH 3 O) w CH 3 Or-(CHCH ₃ CH ₂ O) _w CH ₃ , w is an integer from 1 to 5;

v is an integer of 1-30.

In the compound represented by the formula (1) of the present invention, M ¹ and M ² is a mesogen group as a substituent represented by the formula (2).

Substituents of Formula 2 are aromatic ring-single bond-aromatic ring, aromatic ring-double bond-aromatic ring, aromatic ring-triple bond-aromatic ring, aromatic ring-single bond-aromatic ring-ester-aromatic ring, aromatic ring- A double bond-aromatic ring-ester-aromatic ring, or aromatic ring-triple bond-aromatic ring-ester-aromatic ring structure is preferred, and more preferably aromatic ring-single bond-aromatic ring, or aromatic ring-single bond- Aromatic ring-ester-aromatic ring structures are preferred.

Further, in the general formula (2) of the present invention, of R ¹ to R ⁸ Alkyl of C ₁ to C ₂₀ is independently -CH ₃ , -CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₂ CH ₃ , -CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ CH ₃ , -CH Linear or branched alkyl such as (CH ₃ ) CH ₂ CH ₃ , or —CH ₂ CH (CH ₃ ) ₂ , but is not limited thereto. Further, in Formula 2, of R ¹ to R ⁸ Fluoroalkyl is one wherein at least one fluorine group is substituted for hydrogen in the alkyl as defined above.

In addition, in Formula 2 of R ¹ to R ⁸ Alkenyl of C ₂ ~ C ₂₀ are each independently -CH = CH ₂ , -CH = CHCH ₃ , -CCH ₃ = CH ₂ , -CH ₂ CH = CH ₂ , -CH = CHCH ₂ CH ₃ , -CH = C (CH ₃ ) ₂ , -CCH ₃ = CHCH ₃ , -CH ₂ CH = CHCH ₃ , -CH ₂ CCH ₃ = CH ₂ , -CHCH ₃ CH = CH ₂ , or -CH ₂ CH ₂ CH = CH _2, etc. It may be a linear or branched alkenyl of, but is not limited thereto. Further, in Formula 2, of R ¹ to R ⁸ Fluoroalkenyl is one in which at least one fluorine group is substituted for hydrogen in alkenyl as defined above.

In addition, in Formula 2 of R ¹ to R ⁸ Alkynyl of C ₂ to C ₂₀ is independently -C≡CH, -CH ₂ C≡CH, -C≡CCH ₃ , -CH ₂ CH ₂ C≡CH, -CHCH ₃ C≡CH, -CH ₂ C Linear or branched alkynyl such as —CCH ₃ or —C≡CCH ₂ CH ₃ , but is not limited thereto. Further, in Formula 2, of R ¹ to R ⁸ Fluoroalkynyl is one in which one or more fluorine groups are substituted for hydrogen in the alkynyl as defined above.

In more detail, the compound represented by the formula (1) of the present invention is the same as the following compounds, but the compound according to the present invention is not limited to those illustrated below.

The resin composition according to the present invention includes a polymer resin and a compound represented by Chemical Formula 1 of the present invention. In this case, the compound represented by Formula 1 may play a role of controlling the optical properties of the polymer resin.

When used for this purpose, the compound represented by Formula 1 may be used by mixing one or two or more kinds. In addition, the amount of the polymer resin and the compound represented by the formula (1) in the resin composition of the present invention is a polymer resin: the compound represented by the formula (1) in a weight ratio = 50: 50 ~ 99: 1, preferably 70: 30 ~ 95: 5, More preferably, it is 80: 20-95: 5.

The polymer resin that can be mixed with the compound represented by Formula 1 is not particularly limited, and a polymer resin generally used for optical purposes may be used. For example, the polymer resin may be polyimide, polyamideimide, polyamide, polyetherimide, polyetheretherketone, polyetherketone, polyketone sulfide, polyether sulfone, cycloolefin polymer, polysulfone, polyphenylene sulfide , Polyphenylene oxide, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacetal, polycarbonate, polyacrylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulose, triacetyl cellulose, epoxy resin, phenol Resin and the like, but is not limited thereto. In addition, these polymeric resins can be used individually or in mixture of 2 or more types.

In addition, the compound represented by the formula (1) of the present invention can be used as the polymer resin mixed with an optical pressure-sensitive adhesive resin, preferably acrylic pressure-sensitive adhesive resin.

In general, in order to improve light leakage, a method of adding a plasticizer or a low molecular weight to the high molecular weight copolymer or providing a stress relaxation function to the pressure-sensitive adhesive by controlling the crosslinking structure is used. However, it is difficult to completely suppress light leakage through stress relaxation only. This is because a partial crosslinked structure must be introduced into the pressure sensitive adhesive in order to maintain the durability reliability of the pressure sensitive adhesive for polarizing plate, and thus the residual stress of the pressure sensitive adhesive layer exhibited by the crosslinked structure cannot be completely removed. Therefore, there is a negative birefringence in the acrylic pressure-sensitive adhesive layer commonly used under such residual stress, which is a major cause that is difficult to further improve the light leakage with the negative birefringence present in the TAC layer of the contracted polarizer.

Therefore, in order to improve the light leakage phenomenon, a compound represented by Chemical Formula 1, which is a compound having a large optical anisotropy, is introduced into an acrylic pressure-sensitive adhesive resin exhibiting negative birefringence under residual stress to have a positive birefringence under residual stress. Optical compensation of negative birefringence present in the TAC layer is characterized by improving light leakage.

In addition, the resin composition of the present invention may include an organic solvent, if necessary, in addition to the polymer resin and the compound represented by the formula (1). By containing an organic solvent, it becomes easy to apply | coat (coat) on a base material using the resin composition of this invention.

The organic solvent is not particularly limited, and common ones known in the art may be used. Non-limiting examples thereof include hydrocarbons such as cyclohexane, cyclopentane, benzene, toluene, xylene and butylbenzene; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, esters such as ethyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and gamma-butyrolactone; Amides such as 2-pyrrolidone, N-methyl-2-pyrrolidone, dimethylformamide and dimethylacetamide; Halogens such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, tetrachloroethane, ketrachloroethylene and chlorobenzene; alcohols such as t-butyl alcohol, diacetone alcohol, glycerin, monoacetin, ethylene glycol, triethylene glycol, hexylene glycol, and ethylene glycol monomethyl ether; Phenols such as phenol and parachlorophenol; Methoxybenzene, 1,2-dimethoxybenzene, diethylene glycol dimethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, di Ethers such as ethylene glycol diethyl ether, dipropylene glycol dimethyl ether and dipropylene glycol diethyl ether. In addition, these organic solvents can be used individually or in mixture of 2 or more types, and the use amount is not specifically limited.

Moreover, the resin composition of this invention can contain surfactant as needed. Surfactants can be used to facilitate application onto the substrate. The surfactant is not particularly limited and conventional ones known in the art may be used, and the amount of the surfactant may vary depending on the kind of the surfactant, the composition ratio of the components of the mixture, the kind of the solvent, or the kind of the substrate.

In addition, the resin composition of the present invention may include a chiral dopant, a stress relaxer and / or a leveling agent, or the like as other additives.

The optical member which concerns on this invention contains the polymeric film or adhesive manufactured from the resin composition of the said invention.

The polymer film produced using the resin composition of the present invention may be a uniaxially stretched film or a biaxially stretched film, the polymer film may be a surface treated such as hydrophilic treatment or hydrophobic treatment, may be a laminated film or glass. .

The manufacturing method of the polymer film using the resin composition of this invention is not specifically limited, It can follow the conventional method known in the art. In addition, when preparing a polymer film using a resin composition containing an organic solvent according to the present invention, the resin solid content containing the compound represented by the formula (1) is usually 0.1 to 90% by weight relative to the total resin composition containing a solvent %, Preferably 1 to 50% by weight, more preferably 5 to 40% by weight. When the concentration of the resin composition is less than the lower limit, it is difficult to secure the thickness of the film. When the concentration of the resin composition is higher than the upper limit, the viscosity of the solution is too large to obtain a film having a uniform thickness.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

(Production Example 1)

98 parts by weight of n-butylacrylate (BA) and 2 parts by weight of 2-hydroxyethyl methacrylate (2-hydroxyethyl) in a 1 L reactor equipped with a refrigeration system to allow nitrogen gas to be refluxed and for easy temperature control. A mixture of monomers consisting of (metha) acrylate: 2-HEMA) was added. Then, 120 parts by weight of ethyl acetate (EtOAc) was added as a solvent. After purging with nitrogen gas for 60 minutes to remove oxygen, the temperature was maintained at 60 ° C., and 0.03 parts by weight of azobiisoisobutyronitrile (AIBN), a reaction initiator, was added and reacted for 8 hours. After the reaction was diluted with ethyl acetate (EAc) to prepare an acrylic copolymer having a solid content of 20% by weight, a weight average molecular weight of 1.5 million.

(Manufacture example 2)

After dissolving 1 equivalent of Tripropylene glycol in CH ₂ Cl ₂ solvent, 2.2 equivalents of TsCl (p-toluenesulfonyl chloride) and 2.4 equivalents of TEA (triethyl amine) were added at 0 ° C., and the temperature was raised to room temperature and stirred for about 20 hours. After completion of the reaction, work-up with water and CH ₂ Cl ₂ was purified by silica gel column, and Compound 1 was synthesized in a yield of 92%.

One equivalent of Compound 1 was dissolved in a butanone solvent, two equivalents of p-hydroxybenzoic acid methylester and 2.5 equivalents of K ₂ CO ₃ were added and stirred at 90 ° C. for about 40 hours. After the reaction, work-up was performed with water and ether. One equivalent of this compound was dissolved in a mixed solvent of water and methanol (3: 7), and 2.2 equivalent of KOH was added thereto, followed by stirring at 100 ° C for about 1 hour. After completion of the reaction, methanol was distilled off, and then water and hexane were added to thereby precipitate Compound 2 as crystals. Filtration gave Compound 2 in a yield of 85%.

Dissolve 1 equivalent of Compound 2 in CH ₂ Cl ₂ solvent and add 2 equivalents of p-hydroxybiphenyl, 2.2 equivalents of EDC (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide) and 0.1 equivalent of DMAP (p-dimethylaminopyridine) Stir at room temperature for 20 hours. After completion of the reaction, work-up with water and CH ₂ Cl ₂ was purified by silica gel column to obtain the final compound 3 in 80% yield.

¹ HNMR (400 MHz, CDCl ₃ ): δ 1.19-1.24 (m, 3H), 1.24-1.40 (m, 6H), 3.45-4.10 (m, 8H), 4.53-4.62 (m, 1H), 6.99 (d, 4H), 7.10 (d, 4H), 7.31-7.43 (m, 6H), 7.47 (d, 4H), 7.56 (d, 4H), 7.79 (d, 4H).

(Production Example 3)

After dissolving 1 equivalent of p-Hydroxybenzoic acid methylester in CH ₂ Cl ₂ solvent, add 1.0 equivalent of TBSCl (tert-butyldimethylsilyl chloride) and 1.1 equivalent of TEA (triethyl amine) at 0 ℃, and raise the temperature to room temperature for about 5 hours. Stirred. After completion of the reaction, work-up with water and CH ₂ Cl ₂ was purified by silica gel column, and compound 4 was synthesized in a yield of 97%.

Dissolve 1 equivalent of Compound 4 in CH ₂ Cl ₂ solvent and add 1 equivalent of p-ydroxybiphenyl, 1.1 equivalent of EDC (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide) and 0.1 equivalent of DMAP (p-dimethylaminopyridine) Stirred at room temperature for about 10 hours. After completion of the reaction, work-up with water and CH ₂ Cl ₂ and then purified by silica gel column to give compound 5 in 95% yield.

1.2 equivalents of Compound 5 was dissolved in THF solvent followed by 1.2 equivalents of 10% aq. HCl was added and stirred for about 1 hour. After completion of the reaction, work-up with water and ether and hexane was added to give a solid compound in 80% yield. After dissolving 1 equivalent of Compound 6 and 2 equivalents of the solid compound in a CH ₂ Cl ₂ solvent, 2.2 equivalent of TEA (triethylamine) and 0.2 equivalent of DMAP (p-dimethylaminopyridine) were added thereto, and the resultant was stirred at room temperature for about 20 hours. After completion of the reaction, work-up with water and CH ₂ Cl ₂ was purified by silica gel column to obtain the final compound 7 in 70% yield.

¹ HNMR (400 MHz, CDCl ₃ ): δ 0.33 (s, 12H), 0.39 (s, 12H), 6.89 (d, 4H), 7.12 (d, 4H), 7.30-7.41 (m, 6H), 7.43 (d , 4H), 7.50 (d, 4H), 7.69 (d, 4H).

(Production Example 4)

Dissolve 1 equivalent of p-Hydroxybiphenyl in CH ₂ Cl ₂ solvent, add 1 equivalent of benzoic acid, 1.1 equivalent of EDC (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide) and 0.1 equivalent of DMAP (p-dimethylaminopyridine) Stir at room temperature for 5 hours. After completion of the reaction, work-up with water and CH ₂ Cl ₂ was purified by silica gel column to obtain compound 8 in 95% yield.

¹ HNMR (400 MHz, CDCl ₃ ): δ 6.95 (d, 2H), 7.08 (d, 2H), 7.29-7.73 (m, 2H), 7.37-7.44 (m, 2H), 7.45 (d, 2H), 7.58 (d, 2H), 7.71 (d, 2H).

(Example 1)

100 parts by weight (solid content) of the high molecular weight acrylic copolymer obtained in Preparation Example 1 and 5 parts by weight of the optically anisotropic compound obtained in Preparation Example 2 were uniformly mixed, and then dissolved in an ethyl acetate solvent in consideration of coating properties and thickness, Dilution to concentration produced a coating solution (resin composition).

(Example 2)

A coating solution (resin composition) was prepared in the same manner as in Example 1 except that the compound synthesized in Preparation Example 3 was used instead of the anisotropic compound synthesized in Preparation Example 2.

(Comparative Example 1)

A coating solution (resin composition) was prepared in the same manner as in Example 1 except that the compound synthesized in Preparation Example 4 was used instead of the anisotropic compound synthesized in Preparation Example 2.

(Comparative Example 2)

The coating solution (resin composition) was prepared in the same manner as in Example 1 except that only the adhesive resin synthesized in Preparation Example 1 was used and the anisotropic compound synthesized in Preparation Example 2 was not used.

Experimental Example

The physical properties of each of the coating liquids (resin compositions) prepared in Examples 1 and 2 and Comparative Examples 1 and 2 were measured by the following method.

1. Compatibility test of polymer resin and anisotropic material

The coating solution was coated on the release film to have a thickness of 3 μm, dried at 100 ° C. for 2 minutes, and stored at room temperature to determine whether crystallization of the optically anisotropic compound occurred.

2. Anisotropy Experiment

The coating liquid was uniformly coated on the glass substrate to have a thickness of 25 μm, and then the glass substrate was bonded onto the formed film. Each glass substrate was pulled in the opposite direction using a universal tester (UTM, ZWICK Co., Ltd.) to stretch the film layer by 200%, and the thickness change was measured by a micrometer. The phase difference change of the film layer was measured by the phase difference measuring instrument (axoscan, Axometrics company).

The in-plane retardation Re and the retardation Rth in the thickness direction of the film are defined by the following equation. Where n _x and n _y are in-plane refractive indices, n _x is the direction in which the refractive index is largest in plane, and n _y is the in-plane vertical direction of n _x . n _z is a refractive index in the thickness direction, d is the thickness (nm) of the film.

Re = (n _x- n _y ) xd

Rth = ((n _x + n _y ) / 2-n _z ) xd

The measured physical properties are shown in Table 1 below.

n _y direction Re Rth Example 1 Drawing direction 11.2 6.5 Example 2 Drawing direction 14.5 10.2 Comparative Example 1 Drawing direction 7.1 5.7 Comparative Example 2 Stretching vertical direction 1.7 0.9

As can be seen in Table 1 above, when the anisotropic compound of the present invention is used in addition to the acrylic resin (Examples 1 to 2), the anisotropy property according to the deformation of the resin is excellent, and thus it is easy to control the optical properties.

In addition, in Examples 1 to 2, the anisotropic material did not crystallize even after 1 week storage at room temperature. In contrast, in Comparative Example 1, after one week, some crystallized particles were observed.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. It is natural to belong.

Claims (10)

Compound represented by the following formula (1): [Formula 1] M ¹ -LM ² In formula 1, L is C ₂ ~ C ₆₀ Alkylene oxide, C ₂ ~ C ₆₀ Alkylene, or C ₂ ~ C ₆₀ siloxane; M ¹ and M ² are each independently a substituent represented by formula (2); [Formula 2]

In Formula 2,

Is

or

Is;

Is

or

Is;

Is

or

Is; R ¹ to R ⁵ and the following R ⁶ to R ⁸ are each independently —H, C ₁ to C ₂₀ alkyl, C ₁ to C ₂₀ fluoroalkyl, C ₂ to C ₂₀ alkenyl, C ₂ to C ₂₀ fluoroalkenyl, C ₂ -C ₂₀ alkynyl, C ₂ -C ₂₀ fluoroalkynyl,-(CH ₂ CH ₂ O) _o CH ₃ ,-(CH ₂ CHCH ₃ O) _o CH ₃ , or — (CHCH ₃ CH ₂ O) _o CH ₃ , o is an integer from 1 to 5; X ¹ to X ⁵ are each independently —SiW ¹ W ² —, —O—, —NR ⁶ —, —S—, —SO—, —SO ₂ —, — (CH ₂ ) _p —, —C (= O) NR ^6- , -NR ⁶ C (= 0)-, -NR ⁶ C (= 0) NR ^6- , -C (= 0)-, -C (= 0) O-, -OC (= 0) )-Or -OC (= 0) O- and p is an integer of 0 to 2; W ¹ is -R ⁷ , -NHR ⁷ , or -N (R ⁷ ) ₂ ; W ² is -R ⁸ , -NHR ⁸ , or -N (R ⁸ ) ₂ ; Q ¹ to Q ⁸ are each independently -H, -F, -Cl, -Br, -I, -CN, -CF ₃ , -OCF ₃ , -R ⁶ , -OR ⁶ , -NHR ⁶ , -NR ⁶ R ⁶ or —C (═O) R ⁶ ; Z is C or N, wherein when Z is N, no bond with the corresponding Q ¹ to Q ⁸ is present; Y and G are each independently — (CH ₂ ) _r SiW ¹ W ² (CH ₂ ) _s —, —O—, —NR ⁶ —, —S—, —SO—, —SO ₂ —, — (CH ₂₎ ) _q- , -CH = CH-, -C≡C-, -C (= O) O (CH ₂ ) _q- , -OC (= O) (CH ₂ ) _q -,-(CH ₂ ) _q C (= O) O-,-(CH ₂ ) _q OC (= O)-, -C (= O)-, -C (= O) NR ^6- , -NR ⁶ C (= O)-, -C (= O) S-, or -SC (= O)-, q is an integer from 0 to 5, and r and s are each independently 0 or 1; l and m are each independently an integer of 0-2, and l + m is an integer of 1-4. According to claim 1, wherein the alkylene oxide of C ₂ ~ C _{60 In} L is a compound represented by Formula 1, characterized in that the alkylene oxide represented by the formula (3): (3)

In formula (3), R ⁹ and R ¹⁰ are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) u CH 3, - (CH 2 CHCH 3 O) u CH 3 Or-(CHCH ₃ CH ₂ O) _u CH ₃ , u is an integer from 1 to 5; t is an integer of 1-30. The compound of claim 1, wherein the C ₂ to C ₆₀ siloxane in L is a siloxane represented by the following formula (4): [Formula 4]

In formula (4), R ¹¹ and R ¹² are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) w CH 3, - (CH 2 CHCH 3 O) w CH 3 Or-(CHCH ₃ CH ₂ O) _w CH ₃ , w is an integer from 1 to 5; v is an integer of 1-30. Polymer resins; And a resin composition comprising a compound represented by the formula (1) of claim 1. The method of claim 4, wherein the polymer resin is polyimide, polyamideimide, polyamide, polyetherimide, polyether ether ketone, polyether ketone, polyketone sulfide, polyether sulfone, cycloolefin polymer, polysulfone, polyphenyl Lensulfide, polyphenylene oxide, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacetal, polycarbonate, polyacrylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulose, triacetyl cellulose, epoxy resin And at least one selected from the group consisting of phenol resins. The resin composition according to claim 4, wherein the polymer resin is an acrylic pressure-sensitive adhesive resin. The resin composition of claim 4, wherein the alkylene oxide of C ₂ to C ₆₀ in L of the compound represented by Formula 1 is an alkylene oxide represented by Formula 3 below: (3)

In formula (3), R ⁹ and R ¹⁰ are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) u CH 3, - (CH 2 CHCH 3 O) u CH 3 Or-(CHCH ₃ CH ₂ O) _u CH ₃ , u is an integer from 1 to 5; t is an integer of 1-30. The resin composition of claim 4, wherein the C ₂ to C ₆₀ siloxane in L of the compound represented by Formula 1 is a siloxane represented by Formula 4. [Formula 4]

In formula (4), R ¹¹ and R ¹² are each independently -H, C ₁ ~ C ₂₀ Alkyl, halogen substituted C ₁ ~ C ₂₀ Alkyl, C ₂ ~ C ₂₀ Alkenyl, halogen substituted C ₂ ~ of C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, halogen substituted C ₂ ~ C ₂₀ of the _{alkynyl, - (CH 2 CH 2 O} ) w CH 3, - (CH 2 CHCH 3 O) w CH 3 Or-(CHCH ₃ CH ₂ O) _w CH ₃ , w is an integer from 1 to 5; v is an integer of 1-30. The resin composition of claim 4, wherein the weight ratio of the polymer resin: the compound represented by Formula 1 is 50:50 to 99: 1. An optical member comprising a polymer film or an adhesive prepared from the resin composition of any one of claims 4 to 9.