KR20080109238A - Retardation film and polarizing plate and liquid crystal display comprising the same - Google Patents

Abstract

A retardation film and a polarizing plate and a liquid crystal display having the same are provided to express the phase difference by aligning the anisotropic material with the extension process. A retardation film comprises a polymer resin, and a compound(formula 1). The retardation film is aligned by the extension process of the compound. The compound is an anisotropic compound having one or more meta substitutional material on one end of aromatic cyclic of mesogenic cores. The phase difference of the inside of the retardation film is 10~500nm, and thickness direction phase difference is 10~500nm.

Description

Retardation film, polarizing plate and liquid crystal display including the same {RETARDATION FILM AND POLARIZING PLATE AND LIQUID CRYSTAL DISPLAY COMPRISING THE SAME}

The present invention is a polymer resin; And a retardation film comprising an optically anisotropic compound having at least one meta substituent on an aromatic ring at one end of the mesogen core, and a polarizing plate including the retardation film. Moreover, this invention relates to the liquid crystal display device containing the said retardation film and / or a polarizing plate.

The recent expansion of the display market demands an optical material that demands a clearer image and is not simply a transparent material but is given higher optical characteristics. In particular, liquid crystal displays (LCDs) used in notebooks and monitor TVs have poor viewing angle characteristics compared to CRTs and PDPs, and various studies have been made to solve them.

For example, there exists a method of using the extension film obtained by uniaxial or biaxial stretching process to transparent films, such as a polycarbonate, a cellulose resin, or cyclic olefin resin, as a retardation film as a method of improving a viewing angle characteristic.

In the case of using polycarbonate, the phase difference due to stretching is relatively large. However, since the elastic modulus of light is large, the phase difference tends to change depending on the stretching process conditions or the use environment, and phase difference staining tends to occur.

On the other hand, in the case of cyclic olefin resin or cellulose acetate-based resin, the transparency of the film is very excellent, but the retardation of the phase difference due to the stretching process is small, and in order to obtain a large phase difference, a lot of stretching is necessary, and a lot of stretching causes phase difference staining. Can be.

Recently, Japanese Patent Laid-Open Publication No. 2004-035347 reported a case where a retardation film was prepared by introducing needle-shaped inorganic particles into a cyclic olefin film using a retardation film manufacturing method. However, in the case of inorganic fine particles, the solubility in solvents is low and the density is high. It is difficult to disperse | distribute evenly to a solvent, it is inferior to stability, and it is easy to aggregate, and there exists a possibility that it may inhibit transparency of a polymer film.

In addition, Japanese Laid-Open Patent Publication No. 2006-154760 expresses a retardation film by adding and stretching a low molecular organic compound in a transparent polymer film, but the anisotropy property of the used organic compound is low and the effect of retardation expression is limited by extension of the polymer film and desired phase difference Many stretches are required for expression.

In addition, compounds having high anisotropy generally have high crystallinity, low solubility in solvents, low compatibility in polymer films, and difficulty in preparing transparent films due to precipitation / phase separation after mixing and processing. There is no solution.

In order to solve this problem, the present invention provides a film containing a specific organic compound having high compatibility and high anisotropy and a polymer resin, comprising: a phase difference film in which the anisotropic material is oriented by extension processing to express a phase difference, and the It is to provide a polarizing plate comprising a retardation film.

In addition, the present invention is to provide a liquid crystal display including the retardation film and / or the polarizing plate.

The present invention (a) a polymer resin; And

(b) It provides a retardation film containing a compound represented by the following formula (1).

[Formula 1]

는

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Is

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Is;

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Is

or

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는

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Is

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Is;

Q ¹ to Q ¹⁵ are each independently -H, -F, -Cl, -Br, -I, -CN, -CF ₃ , -OCF ₃ , -R ³ , -OR ³ , -NHR ³ , -NR ³ R ³ or —C (═O) R ³ ;

Z is C or N, wherein if Z is N, there is no bond with that Q;

l, m and n are each independently an integer of 0 to 2, and l + m + n is an integer of 1 or more;

Y, G ¹ and G ² are each independently -O-, -NR ^3- , -S-, -SO-, -SO ₂ -,-(CH ₂ ) _q- , -CH = CH-, -C≡ C-, -C (= 0) O-, -OC (= 0)-, -C (= 0)-, -C (= 0) NR ^3- , -NR ³ C (= 0)-, -NR ³ C (= 0) NR ^3- , -C (= 0) S-, -SC (= 0)-, -COO (CH ₂ ) _q- , -OCO (CH ₂ ) _q -,-(CH ₂ ) _q OCO-, or-(CH ₂ ) _q COO-, q is an integer from 0 to 5;

E is -H, -F, -Cl, -Br, -I, -CN, -NCO, -NCS, -R ³ , -OR ³ , -CF ₃ , or -OCF ₃ ;

X ¹ and X ² are each independently —O—, —NR ³ —, —S—, —SO—, —SO ₂ —, — (CH ₂ ) _p —, —C (═O) NR ³ —, — NR ³ C (= 0)-, -NR ³ C (= 0) NR ^3- , -C (= 0) O-, -OC (= 0)-, or -OC (= 0) O-, and p Is an integer of 0 to 2;

R ¹ , R ² and R ³ are each independently -H, C ₁ -C ₂₀ alkyl, fluoroalkyl, C ₂ -C ₂₀ alkenyl, fluoroalkenyl , C ₂ ~ C ₂₀ of the alkynyl group (alkynyl), fluorinated alkynyl _{(fluoroalkynyl), - (CH 2} CH 2 O) r CH 3, - (CH 2 CHCH 3 O) r CH 3, or - (CHCH ₃ CH ₂ O) _r CH ₃ , r is an integer from 1 to 5;

At least one of X ¹ -R ¹ and X ² -R ² is not — (CH ₂ ) _p —H, where p is zero.

In addition, the present invention provides a polarizing plate comprising the retardation film.

In addition, the present invention provides a liquid crystal display device comprising the retardation film and / or the polarizing plate.

Hereinafter, the present invention will be described in detail.

Retardation film of the present invention, (a) a polymer resin; And (b) a compound represented by the formula (1), preferably a retardation film in which the compound represented by the formula (1) is oriented by extension processing. In this case, the compound represented by Formula 1 is an optically anisotropic compound having one or more meta substituents on the aromatic ring at one end of the mesogen core.

It is preferable that the retardation film of this invention is 10-500 nm in phase difference Ro in a film plane, and is 10-500 nm of retardation Rth of a thickness direction.

In addition, the retardation film of the present invention is preferably produced by extension processing, and due to the orientation of the compound represented by the general formula (1), which is a large anisotropic compound, it is possible to sufficiently express the desired phase difference without much extension. In addition, the compatibility of the compound represented by the formula (1) is excellent, the retardation film of the present invention is excellent in transparency.

In the present invention, the (a) polymer resin is not particularly limited as long as it is a polymer resin having excellent transparency.

The polymer resin is an alicyclic structure-containing polymer resin, polycarbonate resin, polyester resin, polysulfone resin, polyethersulfone resin, polyether ketone resin, polystyrene resin, chain polyolefin resin, polyvinyl alcohol resin, polyvinyl chloride 1 selected from the group consisting of resins, polyacrylate resins, polymethacrylate resins, polyimide resins, polyamide resins, polyketone sulfide resins, polyarylene sulfide resins, polyarylene ether resins, polyacetal resins and cellulose resins It may be a species or more, but is not limited thereto. Among these, alicyclic structure-containing polymer resins and / or cellulose resins which are excellent in optical characteristics are particularly preferred.

The alicyclic structure-containing polymer resin has an alicyclic structure in the repeating unit of the polymer resin. Specific examples of the alicyclic structure-containing polymer resin include, but are not limited to, norbornene-based polymers, monocyclic cyclic olefin polymers, cyclic conjugated diene-based polymers, vinyl alicyclic hydrocarbon polymers, and hydrides thereof. Preferably norbornene-based polymers can be used.

Examples of the norbornene-based polymer include a ring-opening polymer of a norbornene-based monomer, a ring-opening copolymer of another monomer capable of ring-opening copolymerization with a norbornene-based monomer, and an addition polymer of those hydrides and norbornene-based monomers, and copolymerizable with a norbornene-based monomer. Addition copolymers with other monomers, and the like, but are not limited thereto. The norbornene-based monomers, other monomers that can be ring-opened copolymerized with the norbornene-based monomers, and other monomers that can be additionally copolymerized with the norbornene monomers are not particularly limited and may be known ones commonly used.

In addition, the cellulose resin is preferably a lower fatty acid ester of cellulose. In the lower fatty acid ester of cellulose, lower fatty acid means fatty acids having 6 or less carbon atoms, and examples thereof include, but are not limited to, cellulose acetate, cellulose propionate, cellulose butyrate, and the like.

In the present invention, (b) the compound represented by the formula (1) is a compound having one or more meta substituents on the aromatic ring at one end of the mesogen core, preferably an optical refractive anisotropy of 0.2 or more It is an anisotropic compound. That is, in Formula 1, at least one of X ¹ -R ¹ and X ² -R ² is not-(CH ₂ ) _p -H where p is 0, and thus the compound represented by Formula 1 is formed at one end of the mesogen core. It is a compound in which a substituent was introduce | transduced into X ¹ -R ¹ and / or X ² -R ^{2 which} are meta positions.

The compound represented by Chemical Formula 1 has a high anisotropy value and is excellent in compatibility with the polymer resin for optical film, and does not cause phase separation during or after the manufacturing process. One or more meta substituents (X ¹ -R ¹ and / or X ² -R ² ) in the compound represented by the formula (1) increases the compatibility with the polymer resin, existing para (para) substituents or ortho (ortho ) It improves physical properties such as solubility and melting point compared to substituents.

In the compound represented by Formula 1, R ¹ , R ² and R ³ Examples of C ₁ to C ₂₀ alkyl groups include -CH ₃ , -CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₃ , -CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ CH ₃ , -CH (CH ₃ ) CH ₂ CH ₃ , -CH ₂ CH (CH ₃ ) _2, and the like, or a linear or branched alkyl, but is not limited thereto. In addition, R ¹ , R ² and R ³ Fluoroalkyl may be one in which one or more fluorine groups are substituted for hydrogen in the alkyl group as defined above.

In addition, R ¹ , R ² and R ³ Examples of alkenyl of C ₂ to C ₂₀ include -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 , -CH ₂ CH ₂ CH = Linear or branched alkenyl such as CH ₂ , but is not limited thereto. In addition, R ¹ , R ² and R ³ Fluoroalkenyl may be one in which one or more fluorine groups are substituted for hydrogen in the alkenyl group as defined above.

In addition, R ¹ , R ² and R ³ Examples of C ₂ -C ₂₀ alkynyl include -C≡CH, -CH ₂ C≡CH, -C≡CCH ₃ , -CH ₂ CH ₂ C≡CH, -CHCH ₃ C≡CH, Linear or branched alkynyl, such as —CH ₂ C≡CCH ₃ and —C≡CCH ₂ CH ₃ , but is not limited thereto. In addition, R ¹ , R ² and R ³ Fluoroalkynyl may be one in which one or more fluorine groups are substituted for hydrogen in the alkynyl group as defined above.

In addition, in the compound represented by Formula 1, alkyl, fluoroalkyl, alkenyl, fluoroalkenyl, alkynyl, fluoroalkynyl of R ¹ and R ² is preferably C ₃ ~ C ₁₂ linear or branched, Branches between C ₃ and C ₁₂ are more preferred.

In the compound represented by Formula 1, l + m + n is an integer of 1 or more, preferably an integer of 1 to 4, more preferably an integer of 1 to 3.

Further, in the compound represented by Formula 1, [ring A] _l -G ^1- [ring B] _m -G ^2- [ring C] _{n which} is a mesogen core between Y and E is [aromatic ring-single] Bond-aromatic ring], or [aromatic ring-double bond-aromatic ring], or [aromatic ring-triple bond-aromatic ring], wherein the single bond means that G ¹ and G ² in Formula 1 -(CH ₂ ) _q -and q = 0. More preferably, [ring A] _l -G ^1- [ring B] _m -G ^2- [ring C] _n is [aromatic ring-single bond-aromatic ring] or [aromatic ring-triple bond-aromatic ring] It may be a structure.

In addition, the compound represented by the formula (1) is [aromatic ring-single bond], [single bond-aromatic ring], [biphenyl-CN], [triple bond-aromatic ring] and [aromatic ring-triple bond] It is preferable to contain at least one structure selected from the group consisting of.

When the compound represented by the formula (1) is expressed in more detail as the following compounds, the compound represented by the formula (1) is not limited to those illustrated below.

The preparation method of the compound represented by Chemical Formula 1 is as follows. However, the following schemes are merely exemplary, and the method for preparing the compound according to the present invention is not limited by the following schemes.

The compound represented by Chemical Formula 1 may be prepared by the following Scheme 1.

Scheme 1

In Scheme 1, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in; L ¹ and L ² are each independently a living group such as halide, mesylate, tosylate, or triflate; M is a metal such as Li, Na, Mg, K, Ca, or Cs.

In Scheme 1, a base, an alkyl halide, or the like may be attached to a substituent on a meta position, and the like, followed by two Pd coupling reactions to prepare a tolane structure. In addition, the compound of the metal anion as a starting material can be obtained using BuLi, NaH, NaOH, NaHCO ₃ , Na ₂ CO ₃ , Mg, K ₂ CO ₃ , KOH, CaH, or Cs ₂ CO ₃ .

In addition, the compound represented by Formula 1 may be prepared by the following Scheme 2.

Scheme 2

In Scheme 2, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in; L ¹ is as defined in Scheme 1.

In addition, the compound represented by Formula 1 may be prepared by the following Scheme 3.

Scheme 3

In Scheme 3, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in.

In Schemes 2 and 3, aryl substitution reactions can be used to synthesize compounds with Y = NR ³ , O, S, and the like, and SO and SO ₂ can be introduced into the oxidation reaction.

In addition, the compound represented by Formula 1 may be prepared by the following Scheme 4.

Scheme 4

In Scheme 4, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in; L ¹ and L ² are as defined in Scheme 1.

As in Scheme 4, a compound in which Y = (CH ₂ ) _q , CH = CH, CO can be made from a nucleophilic substitution reaction.

In addition, the compound represented by Formula 1 may be prepared by the following Scheme 5.

Scheme 5

In Scheme 5, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in; M, L ¹ and L ² are as defined in Scheme 1.

In addition, the compound represented by Formula 1 may be prepared by the following Scheme 6.

Scheme 6

In Scheme 6, Ring A, Ring B, Ring C, l, m, n, G ¹ , G ² , R ¹ , R ² , Q ¹ , Q ² , Q ³ , X ¹ , X ² and E are represented by Formula 1 As defined in; M, L ¹ and L ² are as defined in Scheme 1; P is a protection group.

According to Scheme 5 and Scheme 6, it is possible to make a CO ₂ H group by bubbling CO ₂ gas, OH group can be introduced by using (Me ₃ SiO) ₂ . An ester compound may be prepared using SOCl ₂ , COCl ₂ , MsCl, TsCl, EDC, DCC, or the like, and esterification may be performed using Dean-Stark.

Method for producing a compound represented by Formula 1 according to the present invention, using a reactant exhibiting the same or similar effects as the reactants used in Schemes 1 to 6, or a scheme similar to Schemes 1 to 6 It also includes a production method by.

On the other hand, in the retardation film of the present invention, the compound represented by Formula 1 may include one kind or two or more kinds. In the retardation film of the present invention, the weight ratio of the polymer resin: the compound represented by Formula 1 may be 80:20 to 99: 1, preferably 85:15 to 98: 2.

The method for producing the retardation film according to the present invention is not particularly limited and may be in accordance with conventional methods known in the art.

As a non-limiting example, the retardation film of the present invention is prepared by forming a film from a mixture containing the polymer resin and the compound represented by Formula 1, and then extending the film to orient the compound represented by Formula 1. The birefringence of the retardation film can be easily controlled by adjusting the extension rate by such a production method.

In addition, in the preparation of the retardation film according to the present invention, the mixture containing the polymer resin and the compound represented by the formula (1) may include an organic solvent, if necessary in addition to these. The use of the mixture may be facilitated by the inclusion of an organic solvent.

In the preparation of the retardation film according to the present invention, the solid content of the polymer resin and the compound represented by the formula (1) is 0.1 to 90% by weight, preferably 1 to 50% by weight, more preferably based on the total mixture including the solvent Preferably 5 to 40% by weight. If the concentration of the solids relative to the total mixture is less than 0.1% by weight, it is difficult to secure the thickness of the film, and if it is more than 90% by weight, the viscosity of the entire mixture is so large that it is difficult to obtain a film of uniform thickness.

The organic solvent is not particularly limited, and conventional organic solvents 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, tetrachloroethylene 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, die 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.

In addition, in the preparation of the retardation film according to the present invention, the method of forming a film using the mixture containing the polymer resin and the compound represented by the formula (1) is not particularly limited, for example, the solvent cast method or It can manufacture by an extrusion method. In addition, the formed film is preferably a transparent film.

In the case of manufacturing the transparent film by the solvent cast method, the mixture is applied on a support such as a metal drum, still belt, polyester film, Teflon, and the solvent is dried in a drying furnace using a roller to peel off the film from the support. Can be prepared. The amount of residual solvent in a film is 10 weight% or less normally, Preferably it is 5 weight% or less, More preferably, it is 1 weight% or less. When the amount of residual solvent exceeds the above upper limit, the heat resistance of the film tends to be low.

As described above, the film formed from the mixture containing the polymer resin and the compound represented by Chemical Formula 1, preferably, the transparent film may be extended. By extension of the film, the molecules of the polymer resin are oriented, and with the orientation of the polymer resin, the compound represented by the formula (1), which is an anisotropic compound, is arranged in parallel with respect to the film plane, and the degree of alignment depends on the degree of extension. Can be adjusted.

At this time, the phase difference imparting performance may be controlled by the kind, content and extension ratio of the compound represented by the formula (1) that is the anisotropic compound. That is, when the film before extension has a constant thickness, the absolute value of the retardation tends to increase depending on the degree of the large number of the anisotropic compounds or the film having the large extension ratio, and thus the phase difference having the desired phase difference by changing the content and extension magnification of the anisotropic compound. A film can be obtained.

In the present invention, the compound represented by Chemical Formula 1, which is an anisotropic compound, has a large anisotropy, so that the phase retardation expression for the extension is large and the desired phase difference can be expressed even with a small extension. In addition, the compound represented by Chemical Formula 1, which is an anisotropic compound, is excellent in compatibility with the polymer resin, and thus, a film containing a large amount of the compound represented by Chemical Formula 1 can be prepared, and the phase difference can be expressed even with a small extension. It is easy to produce a uniform retardation film with little generation | occurrence | production of a stain.

The polarizing plate according to the present invention is characterized by including the retardation film of the present invention, and the liquid crystal display device according to the present invention is characterized by including the retardation film and / or the polarizing plate of the present invention.

Other components and manufacturing methods of the polarizing plate and the liquid crystal display are well known in the art, and thus, description thereof will be omitted since the present invention may be sufficiently reproduced without a separate description.

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.

Synthesis Example 1

1.0 equivalent of m-hydroxybenzoic acid was dissolved in ethanol: water = 7: 3 mixed solvent, and then 1.0 equivalent of 1-bromohexane and 2.2 equivalent KOH were added thereto and stirred at 90 ° C. for 10 hours. Ethanol was distilled off under reduced pressure to further remove water. 10% HCl (aq) was slowly added thereto to adjust the pH between 1 and 3 to obtain Compound 1 in a yield of 90% or more. 1.0 equivalent of compound 1 and 1.0 equivalent of 4-cyano-4'-hydroxybiphenyl were dissolved in CH ₂ Cl ₂ . 1.2 equivalent of EDC and 0.1 equivalent of DMAP were added thereto, followed by stirring at room temperature for 10 hours. After completion of the reaction, work-up with CH ₂ Cl ₂ and purification with silica gel, Compound 2 was prepared in a yield of 88% or more.

¹ HNMR (400 MHz, CDCl ₃ ): δ 0.93 (t, 3H), 1.29-1.45 (m, 4H), 1.46-1.57 (m, 2H), 1.78-1.89 (m, 2H), 4.05 (t, 2H) , 7.20 (dd, 1H), 7.35 (d, 2H), 7.43 (t, 1H), 7.67 (d, 2H), 7.69-7.80 (m, 5H), 7.83 (d, 1H).

Synthesis Example 2

After dissolving p-Hydroxybenzoic acid in ethanol: water = 7: 3 mixed solvent, 1.0 equivalent of 1-bromohexane and 2.2 equivalent KOH were added thereto, and the mixture was stirred at 90 ° C for 10 hours. After distilling under reduced pressure of ethanol, 10% HCl (aq) was slowly added to adjust the pH to 1-3. The resulting solid was filtered and dried, and then dissolved in CH ₂ Cl ₂ with 1.0 equivalent of 4-cyano-4'-hydroxybiphenyl. 1.1 equivalent of EDC and 0.1 equivalent of DMAP were added thereto, followed by stirring at room temperature for 10 hours. After completion of the reaction, work-up with CH ₂ Cl ₂ and purification with silica gel to prepare a final compound 3.

¹ HNMR (400 MHz, CDCl ₃ ): δ 0.94 (t, 3H), 1.29-1.46 (m, 4H), 1.46-1.58 (m, 2H), 1.78-1.90 (m, 2H), 4.05 (t, 2H) , 7.00 (d, 2H), 7.34 (d, 2H), 7.65 (d, 2H), 7.69 (d, 2H), 7.72 (d, 2H), 8.17 (d, 2H).

(Example 1)

5 parts by weight of the anisotropic compound prepared in Synthesis Example 1 was dissolved in toluene based on 100 parts by weight of cellulose triacetate (acetyl substitution degree 2.88), and the mixture was prepared using a bar coater so that the thickness of the film was 100 microns. It was. The film was extended at a draw ratio of 1.5 to prepare a retardation film, and the in-plane retardation value at a wavelength of 590 nm was measured using the prepared retardation film.

The stretched film was transparent and the planar phase difference (Ro) was 70.

(Comparative Example 1)

A retardation film was prepared in the same manner as in Example 1, except that the anisotropic compound prepared in Synthesis Example 1 was not used.

The stretched film was transparent and the phase retardation (Ro) was 40.

(Comparative Example 2)

A retardation film was manufactured in the same manner as in Example 1, except that the anisotropic compound prepared in Synthesis Example 2 was used instead of the anisotropic compound prepared in Synthesis Example 1. The stretched film was opaque due to phase separation.

(Comparative Example 3)

A retardation film was prepared in the same manner as in Example 1, except that 4-methyl phenyl benzoate was used instead of the anisotropic compound prepared in Synthesis Example 1.

The stretched film was transparent and the phase retardation (Ro) was 45.

(result)

When the phase difference is expressed by the extension of the film containing the anisotropic compound and the polymer resin represented by the general formula (1) of the present invention as in the results of Examples 1 and Comparative Examples 1 to 3 (Example 1), it contains an anisotropic compound It can be seen that very large phase difference can be expressed by stretching which is much smaller than the case where the phase difference is expressed only by the polymer resin (Comparative Example 1).

In addition, as in Comparative Example 2, an anisotropic substance containing a substituent (hexyloxy group) at a para position other than meta of the terminal aromatic ring was difficult to prepare a transparent film due to poor compatibility with the polymer resin.

In addition, as in Comparative Example 3, in general, the compounds having small anisotropy may be found to have insufficient effect of improving the expression of anisotropy by extension of the film.

The retardation film of the present invention includes a compound represented by the formula (1) having a high birefringence and excellent compatibility with the polymer resin. Therefore, according to the present invention, there is no phase separation phenomenon, and even with a small extension, it is possible to express a large phase difference, which makes it possible to produce a uniform phase difference film with less occurrence of phase difference stains.

Claims (10)

(a) a polymer resin; And (b) Retardation film containing the compound represented by following formula (1). [Formula 1] In Formula 1,

Is

or

Is;

Is

or

Is;

Is

or

Is; Q ¹ to Q ¹⁵ are each independently -H, -F, -Cl, -Br, -I, -CN, -CF ₃ , -OCF ₃ , -R ³ , -OR ³ , -NHR ³ , -NR ³ R ³ or —C (═O) R ³ ; Z is C or N, wherein if Z is N, there is no bond with that Q; l, m and n are each independently an integer of 0 to 2, and l + m + n is an integer of 1 or more; Y, G ¹ and G ² are each independently -O-, -NR ^3- , -S-, -SO-, -SO ₂ -,-(CH ₂ ) _q- , -CH = CH-, -C≡ C-, -C (= 0) O-, -OC (= 0)-, -C (= 0)-, -C (= 0) NR ^3- , -NR ³ C (= 0)-, -NR ³ C (= 0) NR ^3- , -C (= 0) S-, -SC (= 0)-, -COO (CH ₂ ) _q- , -OCO (CH ₂ ) _q -,-(CH ₂ ) _q OCO-, or-(CH ₂ ) _q COO-, q is an integer from 0 to 5; E is -H, -F, -Cl, -Br, -I, -CN, -NCO, -NCS, -R ³ , -OR ³ , -CF ₃ , or -OCF ₃ ; X ¹ and X ² are each independently —O—, —NR ³ —, —S—, —SO—, —SO ₂ —, — (CH ₂ ) _p —, —C (═O) NR ³ —, — NR ³ C (= 0)-, -NR ³ C (= 0) NR ^3- , -C (= 0) O-, -OC (= 0)-, or -OC (= 0) O-, and p Is an integer of 0 to 2; R ¹ , R ² and R ³ are each independently -H, C ₁ -C ₂₀ alkyl, fluoroalkyl, C ₂ -C ₂₀ alkenyl, fluoroalkenyl, C ₂ -C ₂₀ alkynyl, fluoroalky Nil, — (CH ₂ CH ₂ O) _r CH ₃ , — (CH ₂ CHCH ₃ O) _r CH ₃ , or — (CHCH ₃ CH ₂ O) _r CH ₃ , r is an integer from 1 to 5; At least one of X ¹ -R ¹ and X ² -R ² is not — (CH ₂ ) _p —H, where p is zero. The method of claim 1, wherein the polymer resin is an alicyclic structure-containing polymer resin, polycarbonate resin, polyester resin, polysulfone resin, polyethersulfone resin, polyether ketone resin, polystyrene resin, chain polyolefin resin, polyvinyl alcohol Resin, polyvinyl chloride resin, polyacrylate resin, polymethacrylate resin, polyimide resin, polyamide resin, polyketone sulfide resin, polyarylene sulfide resin, polyarylene ether resin, polyacetal resin and cellulose resin Retardation film characterized in that at least one selected from the group consisting of. The retardation film of claim 1, wherein the compound represented by Chemical Formula 1 has a refractive anisotropy of 0.2 or more. The retardation film of claim 1, wherein in the compound represented by Chemical Formula 1, l + m + n is an integer of 1 to 3. 3. According to claim 1, wherein in the compound represented by Formula 1 [A] _l -G ^1- [Ring B] _m -G ^2- [Ring C] _n is an [aromatic ring-single bond-aromatic ring], [Aromatic ring-double bond-aromatic ring], or [aromatic ring-triple bond-aromatic ring], The single bond in the [aromatic ring-single bond-aromatic ring] is characterized in that the G ¹ and G ² are-(CH ₂ ) _q -and q = 0. The retardation film of claim 1, wherein the weight ratio of the polymer resin: the compound represented by Formula 1 is 80: 20 to 99: 1. The retardation film according to claim 1, wherein the retardation film has a retardation (Ro) in the film plane of 10 to 500 nm and a retardation (Rth) in the thickness direction of 10 to 500 or more. The retardation film according to claim 1, wherein after forming a film from the mixture containing the polymer resin and the compound represented by the formula (1), the film is extended to orient the compound represented by the formula (1). The polarizing plate containing the retardation film of any one of Claims 1-8. The retardation film of any one of Claims 1-8, or (ii) The polarizing plate containing the retardation film of any one of Claims 1-8, or the retardation film of (i), and (ii Liquid crystal display device containing a polarizing plate.