KR20190012521A - Polymerizable compound and liquid crystal composition comprising the same - Google Patents

Abstract

The present invention relates to a polymerizable compound and a liquid crystal composition comprising the polymerizable compound. The polymerizable compound according to the present invention exhibits excellent solubility and low-temperature stability, and also can maintain a high voltage retention ratio even after photopolymerization by ultraviolet light. Therefore, the polymerizable compound enables a high-speed response and can provide the liquid crystal composition optimized for liquid crystal display devices of various modes, particularly liquid crystal display devices of PSA and PS-VA modes.

Description

POLYMERIZABLE COMPOUND AND LIQUID CRYSTAL COMPOSITION COMPRISING THE SAME [0002]

The present invention relates to a polymerizable compound and a liquid crystal composition comprising the same.

BACKGROUND ART [0002] Liquid crystal displays (LCDs) are one of the most widely used flat panel displays. The liquid crystal display device can turn ON / OFF by determining the direction of the liquid crystal molecules in the liquid crystal layer by controlling the electric field in the liquid crystal layer by applying a voltage to the electric field generating electrode and adjusting the transmittance of light passing through the liquid crystal layer. It can be applied to both transmission type and reflection type and can be applied to various types of devices such as Twisted Nematic (TN), In-Plane Switching (IPS), Optically Compensatory Bend (OCB), Field Fringe Switching (FFS), Vertically Aligned (VA), Electrically Controlled Birefringence ), STN (Super Twisted Nematic), and the like are being developed.

Among them, a VA (Vertical Alignment) mode liquid crystal display includes a liquid crystal having negative dielectric anisotropy between two transparent electrodes. The liquid crystal molecules are oriented in a direction perpendicular to the surface of the electrode when the voltage is not applied, and the liquid crystal molecules are oriented in parallel with the surface of the electrode in the on state in which a voltage is applied to the electrode. According to the vertical and horizontal alignment of the liquid crystal depending on whether or not the voltage is applied, the opening and closing of the light emitted from the backlight passing through the polarizer can be controlled. However, if the direction is not predetermined in parallel, There is a drawback.

Meanwhile, the Polymer Stabilized Alignment (PSA) or the Polymer Stabilized-Vertical Aligned (PS-VA) mode, which is one of the VA modes, is a method for controlling the tilt of the vertically aligned liquid crystal in the liquid crystal cell , And a polymerizable compound capable of being polymerized by ultraviolet rays together with the host liquid crystal is mixed in the liquid crystal cell. At this time, the polymerizable compound used must be moved in the direction in which the host liquid crystal lie when the voltage is applied to the electrode through interaction with the vertically aligned liquid crystal. When the polymerizable compound is cured by irradiating ultraviolet rays so that the liquid crystal has a pretilt angle of less than 90 degrees with respect to the substrate, even when the voltage is not applied, a certain inclination is maintained. When the voltage is applied again, So that it is possible to realize a high-speed response.

Generally, a liquid crystal composition used for implementing a PSA mode liquid crystal display contains a polymerizable compound, and the liquid crystal composition should maintain a stable liquid crystal state at a low temperature. If the polymerizable compound precipitates in the liquid crystal composition containing the polymerizable compound, the PSA mode can not be realized. Therefore, there is a demand for a polymerizable compound which has a high solubility in a liquid crystal composition and a low melting point, and maintains stability at low temperature when mixed with a liquid crystal.

High voltage retention (VHR) is essential in liquid crystal displays. The voltage retention is not only a parameter that predicts the long term reliability of a liquid crystal display but also a liquid crystal display having a low voltage retention rate causes various defects such as flickering, staining and sticking of an image. Therefore, even when a polymerizable compound is used for improving the response speed to the liquid crystal composition, it is required to have a high voltage maintaining ratio after ultraviolet ray irradiation. Even a polymerizable compound which can stably maintain the angle of incidence can not be used in a PSA mode liquid crystal display if the voltage holding ratio is lowered when mixed with the liquid crystal composition.

Japanese Patent Application Laid-Open No. 2006-301643

The present invention relates to a polymerizable compound which exhibits excellent solubility in a liquid crystal composition, low linear angle and excellent low-temperature stability, high transparency and high operating temperature range and a liquid crystal composition capable of maintaining a high voltage maintaining rate even after photopolymerization by ultraviolet rays, And a liquid crystal composition.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be understood by those skilled in the art from the following description.

One aspect of the present invention provides a polymerizable compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

P ¹ and P ² are each independently a polymerizable functional group, hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and one or more -CH ₂ - in that way, each independently _{-C≡C-, -CH = CH-, -CF 2} O -, - OCF 2 -, - O -, - or substituted by COO- or -OCO-, at least one in the radical Hydrogen may be substituted with halogen, provided that at least one of P ¹ and P ² is a polymerizable functional group,

Sp ¹ And Sp ² are each independently a single bond or an alkyl radical having from 1 to 15 carbon atoms, and at least one -CH ₂ - in the radical is independently selected from the group consisting of -C≡C-, -CH═CH-, - O-, -CO-O-, -O-CO- or -O-CO-O-, or at least one hydrogen in the radical may be substituted with halogen,

Rings A ¹ and A ² are each independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which one or more hydrogens are substituted with L,

Wherein L is halogen or an alkyl group having 1 to 5 carbon atoms, one or more -CH ₂ in the alkyl group - is such a way that oxygen atoms are not directly connected to each other, independently represent -O-, -S-, -NH- one another, - _{N (CH 3) -, -} CO -, - COO -, - OCO -, - OCOO -, - SCO -, - COS -, - may be replaced by CH = CH-, or -C≡C-, L is When there are plural Ls, L may be the same or different from each other,

Y ¹ and Y ² are each independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkenyl having 2 to 5 carbon atoms, Y ¹ and Y ² are not simultaneously hydrogen,

Z ¹ and Z ² are each independently a single bond, -CH ₂ CH ₂ -, -CH═CH-, -C≡C-, -COO-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ - , Or -CF ₂ O-,

n and m are each independently an integer of 0 to 2, n + m is an integer of 1 or more, and when n is 2, rings A ¹ are the same or different and when m is 2, rings A ² are the same or different from each other Do.

Another aspect of the present invention provides a liquid crystal composition comprising the polymerizable compound represented by Formula 1 above.

Another aspect of the present invention provides a liquid crystal display device comprising a liquid crystal composition containing a polymerizable compound represented by the above formula (1).

The polymerizable compound according to one embodiment of the present invention is a furan compound having an alkyl group or an alkenyl group, and may have a low melting point and an excellent solubility. In addition, it has a high transparency point, has a wide operating temperature range, can improve the linear angle of liquid crystal in light polymerization by ultraviolet rays, and has a high voltage holding ratio. Such a polymerizable compound enables a high-speed response and can provide a liquid crystal composition optimized for liquid crystal display devices of various modes, particularly liquid crystal display devices of PSA and PS-VA modes.

1 is a cross-sectional view schematically showing a liquid crystal display device according to an embodiment of the present invention.
FIG. 2 is a graph showing the results of measuring the tilt angle and the response time of a liquid crystal composition comprising a known polymerizable compound and a polymerizable compound according to one embodiment of the present invention while sequentially increasing the ultraviolet irradiation dose.

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B". Furthermore, unless otherwise stated, the same symbols may have the same meanings.

Hereinafter, a polymerizable compound, a liquid crystal composition containing the same, and a liquid crystal display device including the polymerizable compound according to an embodiment of the present invention will be described in detail.

One aspect of the present invention provides a polymerizable compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

P ¹ and P ² are each independently a polymerizable functional group, hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and one or more -CH ₂ - in that way, each independently _{-C≡C-, -CH = CH-, -CF 2} O -, - OCF 2 -, - O -, - or substituted by COO- or -OCO-, at least one in the radical Hydrogen may be substituted with halogen, provided that at least one of P ¹ and P ² is a polymerizable functional group,

Sp ¹ And Sp ² are each independently a single bond or an alkyl radical having from 1 to 15 carbon atoms, and at least one -CH ₂ - in the radical is independently selected from the group consisting of -C≡C-, -CH═CH-, - O-, -CO-O-, -O-CO- or -O-CO-O-, or at least one hydrogen in the radical may be substituted with halogen,

Rings A ¹ and A ² are each independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which one or more hydrogens are substituted with L,

Wherein L is halogen or an alkyl group having 1 to 5 carbon atoms, one or more -CH ₂ in the alkyl group - is such a way that oxygen atoms are not directly connected to each other, independently represent -O-, -S-, -NH- one another, - _{N (CH 3) -, -} CO -, - COO -, - OCO -, - OCOO -, - SCO -, - COS -, - may be replaced by CH = CH-, or -C≡C-, L is When there are plural Ls, L may be the same or different from each other,

Y ¹ and Y ² are each independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkenyl having 2 to 5 carbon atoms, Y ¹ and Y ² are not simultaneously hydrogen,

Z ¹ and Z ² are each independently a single bond, -CH ₂ CH ₂ -, -CH═CH-, -C≡C-, -COO-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ - , Or -CF ₂ O-,

n and m are each independently an integer of 0 to 2, n + m is an integer of 1 or more, and when n is 2, rings A ¹ are the same or different and when m is 2, rings A ² are the same or different from each other Do.

The polymerizable compound represented by the above formula (1) is a furan compound having an alkyl group or an alkenyl group, has a low melting point, has good solubility in mixing with a liquid crystal compound, and can have excellent low temperature stability. In addition, when light curing by ultraviolet light is applied, the angle of incidence of the liquid crystal can be improved, and a high voltage holding ratio can be obtained. Such a polymerizable compound enables a high-speed response and can be used in liquid crystal display devices of various modes.

In particular, the polymerizable compound may be used in a liquid crystal composition of a polymer stabilized alignment (PSA) mode or a polymer stabilized-vertically aligned (PS-VA) mode. In the PSA mode, even if a liquid crystal composition contains a polymerizable compound, it is necessary to maintain a stable state at a low temperature in order to prevent blinking and after-image, and photopolymerization by ultraviolet rays should be effectively performed.

The polymerizable compound according to an embodiment of the present invention is excellent in solubility in a liquid crystal composition and the liquid crystal composition containing the polymerizable compound according to the present invention maintains a state in which the inclination angle is lower than 90 degrees even after ultraviolet irradiation, Can be implemented. In addition, when the polymerizable compound according to one embodiment of the present invention is incorporated into the liquid crystal composition, the transparent point of the liquid crystal composition can be increased to 75 캜 or higher, thereby widening the operating temperature range, and, even after photopolymerization by ultraviolet light, So that it is possible to provide a liquid crystal composition optimized for liquid crystal displays of PSA and PS-VA modes.

In one embodiment of the present invention, the polymerizable functional group may be any one of the following formulas, and specifically may be acrylate or methacrylate.

,

,

,

,

Further, in one embodiment of the present invention, both P ¹ and P ² may be represented by the following formulas.

In one embodiment of the present invention, the polymerizable compound represented by the formula (1) may be represented by any one of the following formulas (1-1) to (1-24). The compound represented by the following formulas 1-1 to 1-24 has a lower melting point and can have a higher solubility, and thus can have excellent low-temperature stability and a transparent point.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

[Chemical Formula 1-16]

[Formula 1-17]

[Chemical Formula 1-18]

[Chemical Formula 1-19]

[Chemical Formula 1-20]

[Formula 1-21]

[Formula 1-22]

[Formula 1-23]

[Formula 1-24]

In the above formulas 1-1 to 1-24,

X ₁ and X ₂ are each independently hydrogen (H), methyl (CH ₃ ) or methoxy (OCH ₃ ).

In the compound represented by the above formula (1-1), when X ₁ is methyl, the melting point may be lowered by about 60 ° C or more as compared with the conventional polymerizable compound.

Another aspect of the present invention provides a liquid crystal composition comprising a polymerizable compound represented by the formula (1).

According to one embodiment of the present invention, when at least one compound represented by the formula (1) is contained, the pretilt angle can be more easily controlled.

According to one embodiment of the present invention, the polymerizable compound represented by Formula 1 may be contained in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the entire liquid crystal composition. More specifically in an amount of 0.01 to 2 parts by weight. If the content is less than 0.001 parts by weight, it is difficult to expect a role as a polymerizable compound. If the content is more than 5 parts by weight, the display characteristics may be deteriorated.

According to one embodiment of the present invention, other known polymerizable compounds can be used together with the polymerizable compound represented by the formula (1). In this case, the polymerizable compound represented by the formula (1) The maintenance rate can be more easily controlled.

The liquid crystal composition according to one embodiment of the present invention may include a liquid crystal compound together with the polymerizable compound represented by the formula (1). But is not limited to, for example, 8 to 15 kinds of liquid crystal compounds. In this case, it may be easier to implement the PSA mode.

According to an embodiment of the present invention, the liquid crystal composition may include a liquid crystal compound represented by the following formula (2). The liquid crystal compound represented by the following formula (2) is a compound capable of determining the response time of a display with a low viscosity liquid crystal.

(2)

In the above formula (2)

R ₁ and R ₂ are each independently hydrogen, an alkyl radical having 1 to 7 carbon atoms, or an alkoxy radical having 1 to 7 carbon atoms, and wherein at least one -CH ₂ - independently represents -C = C-, -CH = CH-, -CF 2 O-, -OCF 2 each other, substituted with -O-, -COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >

Ring A and B are each independently 1,4-cyclohexylene or 1,4-phenylene.

The liquid crystal compound represented by Formula 2 may be contained in an amount of 5 to 50 parts by weight based on 100 parts by weight of the entire liquid crystal composition. More specifically, it may be contained in an amount of 15 to 40 parts by weight. When the content of the liquid crystal compound represented by the above formula (2) is less than 5 parts by weight or exceeds 50 parts by weight, it is difficult to secure a transparent point, and the operating temperature range of the display is significantly lowered.

According to one embodiment of the present invention, the liquid crystal composition may contain at least one liquid crystal compound represented by the above formula (2).

According to one embodiment of the present invention, in the above formula (2), rings A and B are all 1,4-cyclohexylene, and R ₁ and R ₂ are all alkyl or any of R ₁ and R ₂ And one may be an alkenyl. In such a case, the response time can be improved by lowering the rotational viscosity while keeping the transparent point constant.

According to one embodiment of the present invention, the liquid crystal compound represented by the formula (2) may be any one of the following formulas (2-1) to (2-4) . ≪ / RTI >

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

In the above formulas (2-1) and (2-4)

R ₁ and R ₂ are the same as defined in the above formula (2)

R ₁₁ is hydrogen, an alkyl radical having from 1 to 7 carbon atoms or an alkoxy radical having from 1 to 7 carbon atoms, and at least one -CH ₂ - in the radical is independently selected from the group consisting of -C = -CF ₂ O-, -OCF ₂ -, -O-, -COO- or -OCO-, or at least one hydrogen in the radical may be substituted with halogen.

According to one embodiment of the present invention, in the above formulas (2-1) to (2-4), R ₁ and R ₂ are both an alkyl radical or any one of R ₁ and R ₂ is an alkoxy radical or alkenyl And a liquid crystal compound which is a radical. In this case, there is an effect of reducing the rotational viscosity.

Specifically, in the above formulas (2-1) and (2-2), R ₁ and R ₂ are each independently an alkyl radical having 2 to 5 carbon atoms, or any one of R ₁ and R ₂ is an alkyl radical having 2 to 5 carbon atoms And R < ₁₁ > may be hydrogen or an alkyl radical having 1 to 3 carbon atoms. In such a case, the rotational viscosity can be more effectively reduced and the response speed can be improved.

According to an embodiment of the present invention, the liquid crystal composition may further include a liquid crystal compound represented by the following formula (3). The liquid crystal compound represented by the following formula (3) may have a value whose absolute value of the dielectric constant is larger than 1.

(3)

In the above formula 3,

R ₃ and R ₄ are each independently hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and at least one of the radicals --CH ₂ - independently represents -C = C-, -CH = CH-, -CF 2 O-, -OCF 2 each other, substituted with -O-, -COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >

Z ₅ and Z ₆ are each independently a single bond, -CH ₂ O-, -OCH ₂ -, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH = CH-, -CF = CF-, -C = C-, -COO-, or -OCO-,

e and f are each independently an integer of 0 or 1,

Rings C, D and E are each independently any one of the following formulas.

,

,

,

,

,

,

,

,

,

,

,

,

The liquid crystal compound represented by the above formula (3) is a liquid crystal medium capable of exhibiting substantial display characteristics by increasing the dielectric anisotropy.

The liquid crystal compound represented by Formula 3 may be contained in an amount of 20 to 70 parts by weight based on 100 parts by weight of the entire liquid crystal composition. If the content is less than 20 parts by weight, the dielectric anisotropy is too low to drive the display voltage too high. If the content exceeds 70 parts by weight, the viscosity may become large. However, ) May be difficult to satisfy.

According to an embodiment of the present invention, the liquid crystal compound represented by Formula 3 may be any one of the following Formulas 3-1 to 3-9, and the liquid crystal composition may include at least one compound can do.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

[Chemical Formula 3-7]

[Chemical Formula 3-8]

[Chemical Formula 3-9]

In the above formulas [3-1] to [3-9]

R ₃ and R ₄ are the same as defined in the above formula (3), and (F) is hydrogen or fluorine.

According to one embodiment of the present invention, the liquid crystal compound represented by Formula 3 may be used in Formula 3-2 or Formula 3-5. Such a liquid crystal compound promotes the polymerization reaction of the reactive compound represented by the formula (1) to increase the change of the tilt angle and improve the response time.

According to one embodiment of the present invention, there is provided a liquid crystal compound represented by the above formula (3), wherein the liquid crystal compound represented by the formula (3-2-1), the following formula (3-5-1) May be used as the liquid crystal compound. The liquid crystal compound represented by the following formula (3-2-1), (3-5-1), or (3-8) can be used in the PSA mode to promote the polymerization reaction of the polymerizable compound represented by the formula Thereby making it possible to increase the variation of the inclination angle and improve the response time.

[Formula 3-2-1]

[Formula 3-5-1]

In the above formulas (3-2-1) and (3-5-1)

R ₃ and R ₄ are the same as defined in the above formula (3).

Specifically, in the above formulas (3-2-1), (3-5-1) and (3-8), R ₃ and R ₄ are each independently an alkyl radical having 2 to 5 carbon atoms, an alkoxy radical, Or an alkenyl radical. As such, when R ₃ and R ₄ are alkyl radicals or alkoxy radicals having 2 to 5 carbon atoms, the negative dielectric anisotropy is increased. When at least one of R ₃ and R ₄ is an alkenyl radical having 2 to 5 carbon atoms, .

According to an embodiment of the present invention, the liquid crystal composition may further include a liquid crystal compound represented by Formula 4 below. The transparent point of the liquid crystal compound represented by the following formula 4 is a substance having a temperature of 80 ° C or higher and is an important material for determining the operating temperature in a display.

[Chemical Formula 4]

In the above formula (4)

R ₅ and R ₆ are each independently hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and at least one of the radicals --CH ₂ - independently represents -C = C-, -CH = CH-, -CF 2 O-, -OCF 2 each other, substituted with -O-, -COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >

The rings F, G and I are each independently 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which one or more hydrogens are substituted with halogen,

(F) is hydrogen or fluorine,

g and h are each independently an integer of 0 to 1, and g + h is an integer of 1 or 2.

The liquid crystal compound represented by Formula 4 may be contained in an amount of 5 to 60 parts by weight based on 100 parts by weight of the entire liquid crystal composition. If the content is less than 5 parts by weight or more than 60 parts by weight, the viscosity may decrease or increase and it may be difficult to secure a response time of a desired display.

According to one embodiment of the present invention, the liquid crystal compound represented by Formula 4 may be any one of the following Formulas 4-1 to 4-3, and the liquid crystal composition may include at least one liquid crystal compound ≪ / RTI > compounds.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In the above formulas (4-1) to (4-3)

R ₅ and R ₆ are the same as defined in the above formula (4).

Specifically, R ₅ and R ₆ in Formula 4-1 may independently be an alkyl radical having 1 to 5 carbon atoms or an alkenyl radical having 2 to 5 carbon atoms. In this case, the rotational viscosity of the liquid crystal composition and the elastic modulus It can be easily adjusted.

According to an embodiment of the present invention, the liquid crystal composition may further comprise at least one compound selected from the group consisting of a compound represented by the following formula (5) and a compound represented by the following formula (6).

[Chemical Formula 5]

In the above formula 5,

Ring J is independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is substituted with halogen,

R ₇ is alkyl having 1 to 12 carbon atoms,

i is an integer of 0 or 1.

The compound represented by the above formula (5) can improve the thermal stability of the liquid crystal composition as an antioxidant. May be contained in an amount of 0.01 to 0.05 parts by weight based on 100 parts by weight of the entire liquid crystal composition of the compound represented by the formula (5). If the content is less than 0.01 part by weight, it is difficult to expect a role as an antioxidant. If the content is more than 0.05 part by weight, the characteristics of the liquid crystal display device may be deteriorated.

[Chemical Formula 6]

In the above formula (6)

R ₈ and R ₉ are each independently hydrogen, oxygen, or alkyl having 1 to 12 carbon atoms,

k is an integer of 1 to 12;

The compound represented by the formula 6 may be contained as an ultraviolet stabilizer in an amount of 0.01 to 0.1 parts by weight based on 100 parts by weight of the whole liquid crystal composition. If the content is less than 0.01 parts by weight, it is difficult to expect a UV stabilizer. If the content exceeds 0.1 parts by weight, the display characteristics may be deteriorated.

Another aspect of the present invention provides a liquid crystal display device comprising a liquid crystal composition containing a polymerizable compound represented by the formula (1).

1 is a cross-sectional view of a liquid crystal display device according to an embodiment of the present invention. 1, a liquid crystal display device according to an embodiment of the present invention includes a first substrate SUB1, a second substrate SUB2 facing the first substrate SUB1, and a second substrate SUB2 facing the first substrate SUB1. And a liquid crystal layer LC formed between the second substrate SUB2 and the second substrate SUB2.

The first substrate SUB1 includes a wiring portion provided on the first base substrate BS1, a transistor TR connected to the wiring portion, a pixel electrode PE connected to the transistor TR, PE and a common electrode CE spaced apart from the PE.

The first base substrate BS1 has a substantially rectangular shape and is made of a transparent insulating material. The wiring portion includes a gate line GL and a data line GL.

A gate insulating film GI is provided on the first base substrate BS1 on which the gate lines GL are formed. The gate insulating layer GI may be made of an insulating material, for example, silicon nitride or silicon oxide.

The data line GL is provided extending in a second direction D2 intersecting the first direction D1 with the gate line GL and the gate insulating film GI interposed therebetween.

The transistor TR is connected to the gate line GL and the data line GL. The transistor TR includes a gate electrode GE, a semiconductor pattern SM, a source electrode SE, and a drain electrode DE.

The transistor TR includes a gate electrode GE, a semiconductor pattern SM, a source electrode SE, and a drain electrode DE.

The gate electrode GE protrudes from the gate line GL or is provided on a partial area of the gate line GL.

An interlayer film (IL) is provided on the source electrode (SE) and the drain electrode (DE). A protective film PSV is provided on the interlayer film IL and a contact hole CH exposing a part of the top surface of the drain electrode DE is provided in the interlayer film IL and the protective film PSV.

The second substrate SUB2 is provided opposite to the first substrate SUB1. The second substrate SUB2 may include a second base substrate BS2, a color filter CF, and a black matrix BM.

The liquid crystal layer LC includes the liquid crystal composition according to one embodiment of the present invention described above.

As described above, the liquid crystal composition according to one embodiment of the present invention includes the polymerizable compound represented by the formula (1), thereby exhibiting excellent low temperature stability and having a high voltage holding ratio even after photopolymerization by ultraviolet light. In addition, the liquid crystal composition may include at least one of the compounds represented by formulas (2) to (4). In addition, it may contain a compound represented by the formula (5) or (6). Specific descriptions of the compounds represented by the formulas (1) to (6) are as described above.

Although not limited thereto, the liquid crystal display according to an embodiment of the present invention may be a polymer stabilized alignment (PSA) mode or a polymer stabilized-vertically aligned (PS-VA) mode, More specifically, it may be a PSA mode.

The polymerizable compound represented by the general formula (1) can maintain a stable state at a low temperature when mixed with a liquid crystal compound, can effectively cause photopolymerization by ultraviolet rays, and can maintain a high voltage retention rate even after photopolymerization to enable a high-speed response.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the following examples.

[Chemical Formula 1] Polymerizable  Compound synthesis

The polymerizable compound represented by Formula 1 according to the present invention can be synthesized through the following Reaction Scheme 1 or Reaction Scheme 2, but is not limited thereto.

[Reaction Scheme 1]

[Reaction Scheme 2]

Hereinafter, a method of synthesizing the polymerizable compound in the synthesis examples will be described in detail.

Synthetic example  One: Polymerizable  compound AP's 1A -M synthesis

(10 g, 37.6 mmol, codename M2), acrylic acid (8.1 g, 93.9 mmol), 4- (dimethylamino) ) Pyridine (2.3 g, 18.8 mmol) and DCC (23.2 g, 112.7 mmol) are diluted with 300 ml of dichloromethane and stirred at room temperature for 24 hours. Filter the by-products produced in the reaction solution and remove the solvent. A silica solid column was separated from the dichloromethane to obtain [3-methylfuran-2,5-diyl] bis [1,4-phenylene] bis [2-methacrylate] as a white solid.

MS (EI) m / z = 64, 402 (M < + >). Melting point 102.2 ℃.

Synthetic example  2: Polymerizable  compound AP's 2'A -M synthesis

(8 g, 28.7 mmol, codename M4), methacrylic acid (6.2 g, 71.9 mmol), 4- (dimethyl (4-methylphenyl) Amino) pyridine (1.8 g, 14.4 mmol) and DCC (17.8 g, 86.2 mmol) were diluted in 300 ml of dichloromethane and stirred at room temperature for 24 hours. Filter the by-products produced in the reaction solution and remove the solvent. A silica gel column was used to separate dichloromethane to obtain [3-vinylfuran-2,5-diyl] bis [1,4-phenylene] bis [2-methacrylate] as a white solid.

MS (EI) m / z = 64, 414 (M < + >).

Evaluation of physical properties of the polymerizable compound prepared in Synthesis Example

In order to confirm the physical properties of the synthesized polymerizable compound, evaluation was made according to the following methods in comparison with known polymerizable compounds. The known polymerizable compound, [Formula 7] in the following Table 3 was named AP'sA-M.

(1) Change in state depending on temperature (measurement of melting point and transparent point)

The synthesized material was placed in a capillary with a diameter of 1 mm, capillary tube was attached to the METTLER TOLEDO MP50, and the change in the permeability of the polymerizable compound was observed while raising the temperature at an interval of 3 ° C / min. The point at which the transmittance increases sharply using optical changes is defined as melting point.

The transparent point of the liquid crystal composition containing the polymerizable compound was also measured by the same method.

(2) Low temperature stability

The polymerizable compound to be measured for its solubility at room temperature was mixed with 0.4 part by weight and 2.0 parts by weight of 100 parts by weight of the mother liquid crystal of the following item (8), stirred at a temperature of 90 DEG C for 15 minutes, Hour and then transferred to a 10 mL vial at 2 g and stored in a -30 < 0 > C freezer. Confirm the re-determination at intervals of one day. When the recrystallization occurs after 00 days from the date of the first freezer storage, it is indicated as "00 days NG." If the liquid crystal phase is maintained for 30 days or more, "30 days OK" is described.

(3) Pre-warping angle? P

For the measurement of the pretilt angle, liquid crystals were injected into the evaluation cell of item (6) below and then measured by a modified crystal rotation method. The measurement method was measured by using the refractive index anisotropy change of the cell in which the liquid crystal was injected, and the PAMS measuring device of Cecco Optoelectronics Technology Co., Ltd. was used.

(4) Response time

The main system of measurement was a system of "light source polarizer plate polarizer plate light receiver indicator" order, and LCMS meter of Attention Optoelectronics Technology Co., Ltd. was used. For the measurement of the response time, after the liquid crystal is injected into the evaluation cell of item (6) below, the polarizers of the upper and lower parts of the cell are made to be 90 degrees so that the initial state becomes a dark state. In this state, the response time was measured by applying a 60 Hz AC voltage from 0.0 V to 7.0 V and then applying the voltage from 7.0 V to 0.0 V. At this time, the time from when the voltage is applied from 0.0 V to 7.0 V until the change of the transmittance from 10% to 90% is called Ton, the time when the transmittance changes from 90% to 10% at 7.0 V to 0.0 V is called Toff . Also, the sum of Ton and Toff is indicated in the example as T (total), and unless otherwise mentioned, the response time means T (total).

(5) Refractive Index Anisotropy

The refractive index anisotropy was measured at 20 ° C by vertically aligning the liquid crystal using lecithin at 589 nm using an Abbe refractometer.

(6) Evaluation cell fabrication

The top plate of the glass cell was made of an ITO electrode having a width of 10 mm and a length of 10 mm which was connectable to a wire, and a vertical alignment agent was cured thereon. The vertical alignment agent was rotated (500 rpm) I rub it weakly. (Rubbing depth 0.3 mm) The lower plate of the cell is a striped ITO pattern of 5 μm intervals within 10 mm width / height, and the substrate with the vertical alignment agent cured. The upper and lower plates are bonded together with a thickness of 4 μm, and the electrodes of the upper and lower plates are connected to the wires separately to complete the evaluation cell.

(7) Ultraviolet irradiation method

The liquid crystal mixture to which the reactive compound was added was injected into the evaluation cell, and ultraviolet rays were irradiated while applying an alternating current of 10V. The ultraviolet light used was a light source having a major wavelength band of 365 nm when irradiated, and 40 J was irradiated in the present invention unless otherwise specified.

(8) Production of mother liquid crystal (Host LC)

To confirm the low temperature stability of the synthesized reactive compound, a mother liquid crystal having the composition shown in the following Table 1 was used, and the coded notation was represented by the method shown in Table 2 below.

compound Weight portion Mix A Properties BB-3.4 10.8 Transparent point 74.5
Refractive Index Anisotropy 0.112
Dielectric anisotropy -3.6
Low temperature stability 30 days OK BA-3.O2 One AF-3.O2 14 BF-3.O2 14 BF-3.O4 2.3 BF-5.O2 11.6 BBF-3.O1 4 BBF-3.O2 3.6 BBF-2.1 10 BBF-3.1 10.4 BAA-3.1 9.3 BAA-3.2 5.5 BAA-5.2 1.5 BAAB-3.3 2

Polymerizable  Compound Example  Property evaluation

The polymeric compound AP's1-M synthesized through the above Synthesis Example is shown in Table 3 below in comparison with a known polymerizable compound AP'sA-M.

In order to confirm the low-temperature stability of the polymerizable compound of the present invention, compositions prepared by mixing 2.0 parts by weight and 0.4 part by weight of polymerizable compounds in 100 parts by weight of the mother liquid crystals and the mother liquid crystals shown in Table 1 at -40 ° C The stability was measured.

In the case of AP'sA-M, 0.4% by weight of AP'sA-M was not precipitated at -40 ° C for 30 days, whereas when it was mixed at 2% by weight, precipitation occurred at -40 ° C within 4 days, . On the contrary, AP's 1A-M did not precipitate at -40 ℃ for 30 days and excellent low temperature stability was confirmed. This low temperature stability can be confirmed by melting point. For example, AP'sA-M has a melting point of 168.9 ° C., whereas AP's 1A-M, which is a polymerizable compound according to the present invention, has a melting point of 102.2 ° C. which is lower than about 60 ° C. to improve solubility and low temperature stability .

Fig. 2 shows the results obtained by mixing 0.4 wt part of AP'sA-M, a known polymeric compound and AP's1A-M, a polymerizable compound of the present invention, in 100 wt parts of the mother liquid crystal of Table 1, The tilt angle and response time were measured while sequentially increasing the dose.

Referring to FIG. 2, in the case of a liquid crystal composition containing AP's 1A-M, which is a polymerizable compound of the present invention, as compared with a liquid crystal containing AP'sA-M, .

Examples of a liquid crystal composition containing a polymerizable compound

division Substance / property Comparative Example 1 Example 1 Example 2 Example 3 Example 4 (2) BB-3.V - - - - 35.0 BB-2.3 - - - - - BB-3.4 10.8 15.0 4.2 - - BB-3.5 - - 4.3 6.6 - BA-3.O2 1.0 - 4.3 6.7 - (3) AF-3.O2 14.0 - 12.3 11.7 15.0 BF-3.O2 14.0 10.0 10.8 10.3 10.0 BF-3.O4 2.3 10.0 - - - BF-5.O2 11.6 15.0 11.4 10.8 - BBF-3.O1 4.0 5.0 8.5 6.7 8.0 BBF-3.O2 3.6 10.0 - 2.9 10.0 BBF-4.O2 - - - - - BBF-5.O2 - 10.0 - - - BBF-2.1 10.0 5.0 12.9 14.1 - BBF-3.1 10.4 12.9 12.3 - BAF-2.O2 - - - 5.0 BAF-3.O2 - - - 10.0 AFA-2.3 - 20 - - BYDF-3.O2 - - - 2.0 ANAF-3.O2 - - - - [Chemical Formula 4] BAA-3.1 9.3 10.0 5.1 6.6 5.0 BAA-3.2 5.5 5.0 5.2 7.1 - BAA-5.2 1.5 5.0 4.4 4.2 - BAAB-3.3 2.0 - 1.7 - - Sum 100 100 100 100 100 Polymerizable
compound AP'SA-M 0.4 - - - AP's 1A-M - 0.4 0.4 0.4 0.4 Properties Transparent point 74.5 83.1 80.5 80.6 75.1 Refractive index anisotropy 0.112 0.094 0.114 0.114 0.107 Pre-casting angle (0J) 88.2 87.9 88.5 88.5 88.0 Bending angle (40J) 79.0 78.0 78.5 78.9 78.3

division Substance / property Example 5 Example 6 Example 7 Example 8 Example
9 Example
10 Example
11 (2) BB-3.V 20.0 - - 25.0 15.0 15.0 15.0 BB-2.3 - - - 5.0 5.0 5.0 5.0 BB-3.4 - 4.6 14.1 - - - - BB-3.5 - - - - - - - BA-3.O2 - 10.2 - - - - - (3) AF-3.O2 15.0 7.1 12.3 10.0 - 10.0 10.0 BF-3.O2 10.0 13.2 14.9 10.0 10.0 10.0 10.0 BF-3.O4 - - - - 10.0 - - BF-5.O2 10.0 13.2 9.4 10.0 15.0 15.0 15.0 BBF-3.O1 10.0 - 6.2 - 5.0 5.0 5.0 BBF-3.O2 10.0 10.1 5.4 5.0 10.0 BBF-4.O2 - - - 10.0 10.0 10.0 10.0  BBF-5.O2 - - - - - - - BBF-2.1 - 12.2 7.3 - 5.0 5.0 - BBF-3.1 - 12.2 7.3 - - - - BAF-2.O2 4.0 - - - - - - BAF-3.O2 10.0 - - 13.0 - 10.0 10.0 AFA-2.3 - - 4.0 5.0 - - 5.0 BYDF-3.O2 - - - - - - - ANAF-3.O2 1.0 - - - - - - [Chemical Formula 4] BAA-3.1 - 5.0 8.6 5.0 5.0 5.0 5.0 BAA-3.2 5.0 5.1 7.7 - 5.0 5.0 5.0 BAA-5.2 5.0 5.1 2.8 - 5.0 5.0 5.0 BAAB-3.3 - 2.0 - 2.0 - - - Sum 100 100 100 100 100 100 100 Polymerizable
compound AP'SA-M - - - - - - - AP's 1A-M 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Properties Transparent point 75.4 81.0 78.9 76.9 80.7 79.2 80.7 Refractive index anisotropy 0.116 0.111 0.117 0.110 0.095 0.110 0.118 Pre-casting angle (0J) 88.2 87.8 87.7 88.1 88.1 87.8 87.9 Bending angle (40J) 77.7 76.4 77.4 78.7 76.4 77.1 76.2

Referring to the above Tables 4 and 5, it was confirmed from the result of pre-calorimetric measurement before and after application of 40 J ultraviolet radiation that the polymerizable compound AP of the present invention 's1A-M was added, it can be confirmed that the embodiment has more excellent squareness and higher transparency.

In general, the angle of the pre-curled mirror is as low as less than 90 degrees, and it is confirmed that the first to eleventh embodiments according to the present invention have a decrease in the angle of the front curved mirror (40J) up to 2.8 degrees as compared with the first comparative example.

Also, it can be seen that the transparency point in all the Examples is 0.6 to 8.6 higher than Comparative Example 1. [ Accordingly, the operating temperature range of the liquid crystal can be further widened.

Claims (14)

A polymerizable compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
P ¹ and P ² are each independently a polymerizable functional group, hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and one or more -CH ₂ - , -CF ₂ O-, -OCF ₂ -, -O-, -COO-, or -OCO-, or in the radicals At least one hydrogen may be substituted with halogen, provided that at least one of P ¹ and P ² is a polymerizable functional group,
Sp ¹ And Sp ² are each independently a single bond or an alkyl radical having 1 to 15 carbon atoms, and at least one -CH ₂ - in the radical may be replaced by -C═C-, -CH═CH-, - O-, -CO-O-, -O-CO- or -O-CO-O-, or at least one hydrogen in the radical may be substituted with halogen,
Rings A ¹ and A ² are each independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which one or more hydrogens are substituted with L,
Wherein L is halogen or an alkyl group having 1 to 5 carbon atoms, one or more -CH ₂ in the alkyl group - is such a way that oxygen atoms are not directly connected to each other, independently represent -O-, -S-, -NH- one another, - _{N (CH 3) -, -CO-} , -COO-, -OCO-, -OCOO-, -SCO-, -COS-, -CH = CH- or -C = C- may be substituted with, the L When there are plural Ls, L may be the same or different from each other,
Y ¹ and Y ² are each independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkenyl having 2 to 5 carbon atoms, Y ¹ and Y ² are not simultaneously hydrogen,
Z ¹ and Z ² are each independently a single _{bond, -CH 2 CH 2 -, -CH} = CH-, -C = C-, -COO-, -OCH 2 -, -CH 2 O-, -OCF 2 - , Or -CF ₂ O-,
n and m are each independently an integer of 0 to 2, n + m is an integer of 1 or more, and when n is 2, the rings A ¹ are the same or different and when m is 2, the rings A ² are the same It is different. The method according to claim 1,
Wherein the polymerizable functional group is represented by any one of the following formulas.

,

,

The method according to claim 1,
The polymerizable compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-24).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

[Chemical Formula 1-16]

[Formula 1-17]

[Chemical Formula 1-18]

[Chemical Formula 1-19]

[Chemical Formula 1-20]

[Formula 1-21]

[Formula 1-22]

[Formula 1-23]

[Formula 1-24]

In the above formulas 1-1 to 1-24,
X ₁ is each independently hydrogen (H), methyl (CH ₃ ), or methoxy (OCH ₃ ). 1. A liquid crystal composition comprising one or more polymerizable compounds represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,
P ¹ and P ² are each independently a polymerizable functional group, hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and at least one CH ₂ - , -CF ₂ O-, -OCF ₂ -, -O-, -COO-, or OCO-, or one or more of the radicals in the radical may be substituted independently of one another by -C≡C-, -CH═CH-, -CF ₂ O-, Hydrogen may be substituted with halogen, provided that at least one of P ¹ and P ² is a polymerizable functional group,
Sp ¹ And Sp ² are each independently a single bond or an alkyl radical having from 1 to 15 carbon atoms, and at least one -CH ₂ - in the radical is independently selected from the group consisting of -C≡C-, -CH═CH-, - O-, -CO-O-, -O-CO- or -O-CO-O-, or at least one hydrogen in the radical may be substituted with halogen,
Rings A ¹ and A ² are each independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which one or more hydrogens are substituted with L,
Wherein L is halogen or an alkyl group having 1 to 5 carbon atoms, one or more -CH ₂ in the alkyl group - is such a way that oxygen atoms are not directly connected to each other, independently represent -O-, -S-, -NH- one another, - _{N (CH 3) -, -} CO -, - COO -, - OCO -, - OCOO -, - SCO -, - COS -, - may be replaced by CH = CH-, or -C≡C-, L is When there are plural Ls, L may be the same or different from each other,
Y ¹ and Y ² are each independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkenyl having 2 to 5 carbon atoms, Y ¹ and Y ² are not simultaneously hydrogen,
Z ¹ and Z ² are each independently a single bond, -CH ₂ CH ₂ -, -CH═CH-, -C≡C-, -COO-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ - , Or -CF ₂ O-,
n and m are each independently an integer of 0 to 2, n + m is an integer of 1 or more, and when n is 2, rings A ¹ are the same or different and when m is 2, rings A ² are the same or different from each other Do. 5. The method of claim 4,
Wherein the liquid crystal composition comprises at least one of liquid crystal compounds represented by the following general formulas (2) to (4).
(2)

In the above formula (2)
R ₁ and R ₂ are each independently hydrogen, an alkyl radical having 1 to 7 carbon atoms, or an alkoxy radical having 1 to 7 carbon atoms, and wherein at least one -CH ₂ - independently represent _{-C≡C-, -CH = CH-, -CF 2} O together _{-, - OCF 2 -, -} O -, - or substituted by COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >
Ring A and B are each independently 1,4-cyclohexylene or 1,4-phenylene.

(3)

In the above formula 3,
R ₃ and R ₄ are each independently hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and at least one of the radicals --CH ₂ - independently represent _{-C≡C-, -CH = CH-, -CF 2} O together _{-, - OCF 2 -, -} O -, - or substituted by COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >
Z ₅ and Z ₆ are each independently a single bond, -CH ₂ O-, -OCH ₂ -, -CH ₂ CH ₂ -, -CF ₂ O-, -OCF ₂ -, -CH═CH-, CF-, -C? C-, -COO-, or -OCO-,
e and f are each independently an integer of 0 or 1,
Rings C, D and E are each independently any one of the following formulas.

[Chemical Formula 4]

In the above formula (4)
R ₅ and R ₆ are each independently hydrogen, an alkyl radical having from 1 to 7 carbon atoms or an alkoxy radical having from 1 to 7 carbon atoms, and at least one of the radicals --CH ₂ - independently represent _{-C≡C-, -CH = CH-, -CF 2} O together _{-, - OCF 2 -, -} O -, - or substituted by COO- or -OCO-, at least one hydrogen in said radical by halogen, Lt; / RTI >
The rings F, G and I are each independently 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which one or more hydrogen is substituted by halogen,
(F) is hydrogen or fluorine,
g and h are each independently an integer of 0 to 1, and g + h is an integer of 1 or 2. 6. The method of claim 5,
Wherein the compound represented by Formula 2 comprises at least one compound selected from compounds represented by Formulas 2-1 to 2-4.
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

In the above Chemical Formulas 2-1 to 2-4,
R ₁ and R ₂ are the same as defined in the formula 2 and R ₁₂ is hydrogen, an alkyl radical having 1 to 7 carbon atoms or an alkoxy radical having 1 to 7 carbon atoms, and at least one -CH ₂ - Are independently selected from the group consisting of -C≡C-, -CH═CH-, -CF ₂ O-, -OCF ₂ -, -O-, -COO- or -OCO-, in such a way that oxygen atoms are not directly connected to each other Or at least one hydrogen in the radical may be substituted with halogen. 6. The method of claim 5,
And at least one compound selected from the group consisting of compounds represented by the following formulas (3-1) to (3-9) as the compound represented by the formula (3).
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

[Chemical Formula 3-7]

[Chemical Formula 3-8]

[Chemical Formula 3-9]

In the above Formulas 3-1 to 3-9,
R ₃ and R ₄ are the same as defined in the above formula (3)
(F) is hydrogen or fluorine. 6. The method of claim 5,
Wherein the compound represented by Formula 3 comprises at least one compound selected from the following Formulas 3-2-1, 3-5-1, and 3-8.
[Formula 3-2-1]

[Formula 3-5-1]

[Chemical Formula 3-8]

In the above formulas (3-2-1), (3-5-1) and (3-8)
R ₃ and R ₄ are the same as defined in the above formula (3)
(F) is hydrogen or fluorine. 6. The method of claim 5,
Wherein the compound represented by Formula 4 comprises at least one compound selected from compounds represented by the following Formulas 4-1 to 4-3.
[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In the above Chemical Formulas 4-1 to 4-3,
R ₅ and R ₆ are the same as defined in the above formula (4). 6. The method of claim 5,
And at least one compound represented by the following general formula (5) and (6).
[Chemical Formula 5]

In Formula 5,
Ring J is independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is substituted with halogen,
R ₇ is alkyl having 1 to 12 carbon atoms,
i is an integer of 0 or 1.

[Chemical Formula 6]

In Formula 6,
R ₈ and R ₉ are each independently hydrogen, oxygen, or alkyl having 1 to 12 carbon atoms,
k is an integer of 1 to 12; 6. The method of claim 5,
Wherein the polymerizable compound represented by Formula 1 is contained in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the total liquid crystal composition. 6. The method of claim 5,
With respect to 100 parts by weight of the total liquid crystal composition,
The compound represented by Formula 2 is contained in an amount of 5 to 50 parts by weight;
The compound represented by Formula 3 is contained in an amount of 20 to 70 parts by weight;
And 5 to 60 parts by weight of the compound represented by the general formula (4). A liquid crystal display comprising the liquid crystal composition according to any one of claims 4 to 12. 14. The method of claim 13,
Wherein the liquid crystal display device is a Polymer Stabilized Alignment (PSA) mode or a Polymer Stabilized-Vertical Aligned (PS-VA) mode.

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