KR20200074814A - Reative light stablizer compound and liquid crystal composition including the same - Google Patents

Abstract

The present application relates to a reactive light stabilizer compound, a liquid crystal composition comprising the same, and a liquid crystal display device comprising the same. The reactive light stabilizer compound according to an embodiment of the present invention can achieve low-temperature stability and an afterimage alleviating effect at the same time without adversely affecting various properties of a liquid crystal composition such as a transparent point, modulus of elasticity, dielectric anisotropy or refractive index anisotropy and the like of a liquid crystal composition, and in a mode that requires an exposure process, the voltage retention rate (VHR) is increased and the RDC is decreased to alleviate afterimages.

Description

Reactive light stabilizer compound and liquid crystal composition comprising same {REATIVE LIGHT STABLIZER COMPOUND AND LIQUID CRYSTAL COMPOSITION INCLUDING THE SAME}

The present application relates to a reactive light stabilizer compound, a liquid crystal composition comprising the same, and a liquid crystal display device comprising the same.

A liquid crystal display (LCD) is one of the most widely used flat panel displays. The liquid crystal display device is capable of displaying ON/OFF by applying a voltage to the electric field generating electrode to generate an electric field in the liquid crystal layer to determine the direction of liquid crystal molecules in the liquid crystal layer and to control the transmittance of light passing through the liquid crystal layer. It can be applied to both transmissive and reflective types, such as TN (Twisted nematic), IPS (in-Plane Switching), OCB (Optically Compensatory Bend), VA (Vertically Aligned), ECB (Electrically Controlled Birefringence), STN (Super Twisted Nematic) ), and various modes of liquid crystal display devices have been developed.

Liquid crystal displays used in various industrial applications must meet various requirements, for example, it is required to operate in a low voltage driving, high speed response, and a wide temperature range. That is, a nematic phase-isotropic liquid phase transition temperature (Tni) having a large absolute value of Δε, a low rotational viscosity (η), and a high demand is required. In addition, proper dielectric anisotropy, refractive anisotropy and elastic modulus are required.

In addition to these various physical properties, the liquid crystal composition used in the liquid crystal display device also requires chemical resistance to external stimuli such as moisture, air, heat, and light (infrared rays, visible rays, and ultraviolet rays). In particular, since the liquid crystal display device receives light from the backlight, stability of the liquid crystal is a problem, and the light-induced reaction of the liquid crystal material may cause a display defect known as image sticking. This is a factor that significantly reduces the life of the liquid crystal display device.

To prevent this, a light stabilizer may be included in the liquid crystal composition. Typical light stabilizers include UV screeners, UV absorbers, quenchers, or radical scavengers, and in the field of liquid crystal displays, radical scavengers, HALS (Hindered) Amine Light Stabilzer) is commonly used.

For example, a nematic liquid crystal mixture having negative dielectric anisotropy, which contains a small amount of the compound of the following formula (TINUVIN®) 770 as a light stabilizer, is proposed in International Patent Publication No. WO 2009/129911 have. However, the corresponding liquid crystal mixtures have properties that are inappropriate for many practical applications. Among them, they are not stable enough for irradiation using a typical CCFL backlight.

In addition, some HALS known in the prior art have excellent low-temperature stability but do not have an afterimage improvement effect, while some other HALS have excellent afterimage-improving effect but have low temperature stability.

Therefore, it is possible to simultaneously achieve low temperature stability and afterimage improvement effect without affecting the physical properties of the liquid crystal composition, such as the transparent point, elastic modulus, dielectric anisotropy, or refractive anisotropy of the liquid crystal composition. VHR) is increased and RDC is lowered to develop a new light stabilizer compound capable of improving afterimages.

International Patent Publication No. WO 2009/129911

The problem to be solved by the present application is to achieve the low temperature stability and the afterimage improvement effect simultaneously without adversely affecting the physical properties of the liquid crystal composition, such as the transparent point, elastic modulus, dielectric anisotropy or refractive anisotropy of the liquid crystal composition, and the exposure process In a required mode, a voltage stabilizer (VHR) is increased and an RDC is lowered to provide a light stabilizer compound capable of improving an afterimage, and a liquid crystal composition comprising the compound.

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

The first aspect of the present application provides a reactive light stabilizer compound represented by the following formula (I):

[Formula I]

In the above formula I,

T ¹ to T ³ are each independently hydrogen (H), any one of the following formulas 1 to 4, or a polymerizable functional group (where at least one of T ¹ to T ³ is one of the following formulas 1 to 3) Any one, and at least one of the rest is the polymerizable functional group),

[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

Sp is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,

R ¹ is H, or C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is each independently an oxygen (O) atom Can be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a way that they are not directly connected to each other, C _1-10 straight chain Or one or more hydrogens of branched alkyl can be replaced by F, Cl or CF ₃ ),

R ² to R ⁵ are each independently C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is independently of each other, oxygen ( O) atoms can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other, C _{1 ~10} one or more hydrogens of straight chain or branched alkyl can be replaced by F, Cl or CF ₃ ),

Y is H, C _1-10 straight chain or branched alkyl, C _1-10 straight chain or branched alkoxy or C _2-10 straight chain or branched alkenyl (where C _1-10 straight chain or branched alkyl, C ₁ One or more non-adjacent methylene groups (-CH ₂ -) of _~10 straight chain or branched alkoxy or C _2-10 straight chain or branched alkenyl, each independently of each other, in such a way that oxygen (O) atoms are not directly connected to each other Can be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, one or more hydrogens of C _1-10 straight chain or branched alkyl Can be replaced by F, Cl or CF ₃ ),

n2 is an integer from 1 to 4,

A ¹ to A ³ are each independently represented by the formula (5),

[Formula 5]

L is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,

Z is a C _1-10 straight-chain or branched alkylenyl, or a C _5-20 cyclic alkylenyl group (wherein at least one methylene group of C _1-10 straight-chain or branched alkylenyl (-CH ₂ -) is each Independent of each other, oxygen (O) atoms are replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in such a way that they are not directly connected to each other And one or more hydrogen (H) of C _1-10 straight chain or branched alkylenyl may be replaced by F, Cl or CF ₃ , and one or more carbon (C) atoms of C _5-20 ring groups may be O, Can be substituted with N or S and one or more hydrogens of C _5-20 ring groups can be replaced by F, Cl or CF ₃ ),

n3 is an integer of 1 or 2, and when n3 is 2, L and Z may be the same or different from each other.

The second aspect of the present application provides a liquid crystal composition comprising a reactive light stabilizer compound represented by the formula (I).

A third aspect of the present application provides a liquid crystal display device including the liquid crystal composition.

The light stabilizer compound according to an embodiment of the present invention can simultaneously achieve low temperature stability and afterimage improvement effect without adversely affecting the physical properties of the liquid crystal composition, such as the transparent point, elastic modulus, dielectric anisotropy, or refractive anisotropy of the liquid crystal composition. In addition, in a mode in which an exposure process is required, a voltage retention rate (VHR) is increased and an RDC is lowered to exhibit an effect of improving afterimages.

1 shows an NMR spectrum of a reactive light stabilizer compound according to an embodiment of the present invention.
Figure 2 shows the NMR spectrum of the reactive light stabilizer compound according to an embodiment of the present invention.

Hereinafter, embodiments and examples of the present application will be described in detail with reference to the accompanying drawings so that those skilled in the art to which the present invention pertains can easily practice.

However, the present application may be implemented in various different forms, and is not limited to the embodiments and examples described herein. In addition, in order to clearly describe the present invention in the drawings, parts irrelevant to the description are omitted, and like reference numerals are assigned to similar parts throughout the specification.

Throughout this specification, when one member is said to be "on" another member, this includes not only the case where one member abuts another member, but also the case where another member exists between the two members.

Throughout the present specification, when a part “includes” a certain component, it means that the component may further include other components, rather than excluding other components, unless otherwise specified. The terms "about", "substantially", and the like, as used throughout this specification, are used in or at a value close to that value when manufacturing and material tolerances specific to the stated meaning are given, and are understood herein. To help, accurate or absolute figures are used to prevent unconscionable abusers from unduly using the disclosed disclosure. The term “~(steps)” or “steps of” as used in the present specification does not mean “steps for”.

Throughout the present specification, the term “combination of these” included in the expression of the marki form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the marki form, the component It means to include one or more selected from the group consisting of.

Throughout this specification, the description of “A and/or B” means “A or B, or A and B”.

Throughout this specification, the term “aryl” or “arylene” refers to a C _6-50 aromatic hydrocarbon ring group, such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthrenyl, tri Means to include aromatic rings such as phenylenyl, perenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocresenyl, anthracenyl, stilbenyl, pyrenyl, and the term "hetero aryl "or" heteroarylene "is a C _{2 ~ 50} aromatic ring containing at least one hetero atom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl , Isobenzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, And pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine Ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzo It may mean to include a heterocyclic group formed from an imidazole ring, a pyran ring, a dibenzofuran ring.

The term throughout the present specification, "substituted" or "which may be substituted" is a silane group or a C ₁ ~ ₃₀ alkyl group a nitro group, a heavy hydrogen, oxygen, a halogen, an amino group, a nitrile group,, C ₂ ~ ₃₀ alkenyl, C ₁ ~ ₃₀ alkoxy group, C ₃ ~ ₂₀ cycloalkyl group, C ₃ ~ ₂₀ heterocycloalkyl group, C ₆ ~ ₃₀ aryl group and C ₂ ~ ₃₀ heteroaryl group may be substituted with one or more groups selected from the group consisting of. In addition, the same symbols throughout the present specification may have the same meanings unless otherwise specified.

Reactive light stabilizer compound

The first aspect of the present application provides a reactive light stabilizer compound represented by the following formula (I):

[Formula I]

In the above formula I,

T ¹ to T ³ are each independently hydrogen (H), any one of the following Formulas 1 to 4, or a polymerizable functional group (where at least one of T ¹ to T ³ is one of the above Formulas 1 to 3) Any one, and at least one of the rest is the polymerizable functional group),

[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

Sp is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,

R ¹ is hydrogen (H), or C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is independently of each other, oxygen ( O) atoms can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other, C _{1 ~10} one or more hydrogen (H) of straight chain or branched alkyl can be replaced by F, Cl or CF ₃ ),

R ² to R ⁵ are each independently C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is independently of each other, oxygen ( O) atoms can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other, C _{1 ~10} one or more hydrogens of straight chain or branched alkyl can be replaced by F, Cl or CF ₃ ),

Y is H, C _1-10 straight chain or branched alkyl, C _1-10 straight chain or branched alkoxy, or C _2-10 straight chain or branched alkenyl (where C _1-10 straight chain or branched alkyl, C ₁ One or more non-adjacent methylene groups (-CH ₂ -) of _~10 straight chain or branched alkoxy or C _2-10 straight chain or branched alkenyl, each independently of each other, in such a way that oxygen (O) atoms are not directly connected to each other Can be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, one or more hydrogens of C _1-10 straight chain or branched alkyl Can be replaced by F, Cl or CF3),

n2 is an integer from 1 to 4,

A ¹ to A ³ are each independently represented by the formula (5),

[Formula 5]

L is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,

Z is a C _1-10 straight-chain or branched alkylenyl, or a C _5-20 cyclic alkylenyl group (wherein at least one methylene group of C _1-10 straight-chain or branched alkylenyl (-CH ₂ -) is each Independent of each other, oxygen (O) atoms are replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in such a way that they are not directly connected to each other And one or more hydrogen (H) of C _1-10 straight chain or branched alkylenyl may be replaced by F, Cl or CF ₃ , and one or more C atoms of the C _5-20 ring group may be O, N or S Can be substituted with one or more hydrogen (H) of the C _5-20 ring group can be replaced by F, Cl or CF ₃ ),

n3 is an integer of 1 or 2, and when n3 is 2, L and Z may be the same or different from each other.

That is, the light stabilizer compound of the present invention is characterized by having a multi-reactive group such as an amine as a core. Through this, by having a linking group such as an alkyl group, solubility is improved, and excellent low-temperature stability can be obtained. In addition, since at least one HALS functional group is introduced at the terminal of the amine, an afterimage of the liquid crystal display may be improved through this. In addition, since one or more polymerizers are introduced at the other end of the amine, it is possible to maintain high voltage retention (VHR) by directly combining with reactive mesogen (RM) in the exposure process.

According to an embodiment of the present invention, the polymerizable functional group may be any one of the following formulas, specifically acrylate or methacrylate:

,

,

.

,

,

.

According to an embodiment of the present invention, at least one of T ¹ to T ³ is at least one of the following Chemical Formula 1 or Chemical Formula 2, and at least any one of the other may be the polymerizable functional group. Through this, characteristics such as voltage retention (VHR), residual DC (RDC), and resistivity of the liquid crystal display may be improved to improve afterimages.

[Formula 1] [Formula 2]

In addition, according to an embodiment of the present invention, Sp is -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO- , -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-, and specifically -COO-.

Further, according to an embodiment of the present invention, R ¹ may be hydrogen (H).

Also, according to an embodiment of the present invention, n2 may be an integer of 1 or 2, and specifically n2 may be 2. When n2 is 2, it may be more structurally stable.

In addition, according to an embodiment of the present invention,

L is a single bond,

Z may LES C _{1 ~ 10} linear or branched alkyl imidazol (wherein one or more methylene groups of C _{1 ~ 10} linear or branched alkylenyl (-CH ₂ -) is, independently of each other, oxygen (O) atoms Can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other and C _1-10 straight chain or minute One or more hydrogen (H) of the terrestrial alkylenyl may be replaced by F, Cl or CF ₃ ). Through this, by having a linking group such as an alkyl group, solubility is improved and excellent low temperature stability can be obtained.

The reactive light stabilizer compound of Formula (I) according to an embodiment of the present invention has an amine core group and has a multi-function structure, solubility is improved and low-temperature stability is excellent. In addition, the reactive light stabilizer compound of Formula I serves as a scavenger capable of effectively capturing ions, radicals, etc. remaining in the liquid crystal composition or alignment layer by introducing a HALS (Hindered Amine Light Stabilzer) functional group at the terminal. Thereby, the afterimage improvement effect of a liquid crystal display device is excellent. In addition, the reactive light stabilizer compound of Formula I can directly bind to reactive mesogen (RM) in an exposure process to increase the binding force between molecules and effectively remove unreacted residual substances, thereby maintaining a high voltage retention rate (VHR).

In one embodiment of the present invention, the reactive light stabilizer compound represented by Formula I may be synthesized by the following Reaction Scheme 1, but is not limited thereto, and may also be synthesized by various methods.

[Scheme 1]

At this time, if there is one polymerizable functional group, it is synthesized in the same manner as in Scheme 1, but can be synthesized through an intermediate step process such as Scheme 2 below.

대신에

,

,

,

등을 사용하거나, 메타크릴산을 아크릴산 등으로 대체하여 다양한 형태의 상기 화학식 I 로 표시되는 반응성 광 안정제 화합물를 합성할 수 있다.In addition, in Scheme 1

Instead of

,

,

,

Reactive light stabilizer compounds represented by the above formula (I) in various forms can be synthesized by using or replacing methacrylic acid with acrylic acid.

In one embodiment of the present invention, the reactive compound represented by the formula (I) may be a compound presented below. However, it is not limited thereto.

Polymerizable compounds

In general, an appropriate pretilt angle is maintained by using a liquid crystal medium in which a polymerizable compound is mixed in a PSA mode or PS-VA mode liquid crystal display device. In the VA mode, it is appropriate to maintain a pretilt angle of 87 to 89°.

In one embodiment of the present invention, the polymerizable compound may be a compound represented by the following compound 11 and compound 12. However, it is not limited thereto.

[Compound 11]

[Compound 12]

Liquid crystal composition

The second aspect of the present application provides a liquid crystal composition comprising one or two or more reactive light stabilizer compounds represented by the formula (I). In the liquid crystal composition according to the present aspect, all of the contents described in the first aspect of the present application may be applied and may not be limited thereto.

The liquid crystal composition includes the reactive light stabilizer compound represented by the above-described formula (I), and thus has low temperature stability and afterimage without adversely affecting the physical properties of the liquid crystal composition, such as transparency, elastic modulus, dielectric anisotropy or refractive anisotropy of the liquid crystal composition. The improvement effect can be achieved at the same time, and in the mode in which the exposure process is required, the voltage retention (VHR) is increased and the RDC is lowered to improve the afterimage.

In addition, according to an embodiment of the present invention, the light stabilizer compound represented by the formula (I) is 0.001 to 5 parts by weight, 0.001 to 4 parts by weight, 0.001 to 3 parts by weight, 0.001 to 2 parts by weight based on 100 parts by weight of the liquid crystal composition , 0.001 to 1 part by weight, specifically 0.001 to 0.5 part by weight, 0.001 to 0.3 part by weight, 0.003 to 1 part by weight, 0.003 to 0.5 part by weight, or may be included as 0.003 to 0.3 part by weight, it may not be limited. The content of the light stabilizer compound may not be included in 100 parts by weight of the liquid crystal composition. If it exceeds the content range, the properties of the liquid crystal composition may change, and if it is less than the content range, the improvement effect may be deteriorated.

Meanwhile, in the liquid crystal composition, the reactive light stabilizer compound represented by the formula (I) may be combined with various kinds of liquid crystal compounds according to the characteristics of the liquid crystal panel to which the composition is applied.

According to an embodiment of the present invention, the liquid crystal composition may further include a compound represented by Formula II:

[Formula II]

In the above formula II,

Ring A and Ring B are each independently 1,4-cyclohexylene in which carbon (C) in the ring is substituted or unsubstituted with one or more oxygen (O), or one or more hydrogen (H) is substituted or unsubstituted with halogen. Is 1,4-phenylene,

R ⁶ and R ⁷ are each independently C _1-7 alkyl, C _1-7 alkoxy, or C _2-7 alkenyl,

n4 is an integer from 1 to 3, and when n4 is 2 or 3, ring B may be the same or different from each other.

According to one embodiment of the invention, the halogen may be fluorine (F).

According to one embodiment of the present invention, the compound represented by Formula II may include a compound represented by Formulas II-1 to II-6 below.

[Formula II-1]

[Formula II-2]

[Formula II-3]

[Formula II-4]

[Formula II-5]

[Formula II-6]

In Formulas II-1 to II-6,

R ₆ and R ₇ are the same as defined in Formula II above.

The compound represented by Chemical Formula II-1 may serve to maintain the low viscosity of the liquid crystal composition.

In one embodiment of the present invention, the compound represented by Formula II-1 may include a compound represented by Formulas II-1-1 to II-1-7 below. These compounds may have a particularly useful effect in maintaining the low viscosity of the liquid crystal composition.

[Formula II-1-1]

[Formula II-1-2]

[Formula II-1-3]

[Formula II-1-4]

[Formula II-1-5]

[Formula II-1-6]

[Formula II-1-7]

The compound represented by Chemical Formula II is a compound having a dielectric anisotropy of about -1 to 3, and is a compound capable of maintaining a wide liquid crystal phase range while the liquid crystal composition has a low rotational viscosity.

In one embodiment of the present invention, the compound represented by Formula II may be included in 10 to 50 parts by weight based on 100 parts by weight of the liquid crystal composition, and may not be limited thereto. If it contains less than 10 parts by weight, the liquid crystal composition outside the range of the liquid crystal phase at room temperature or low rotation viscosity may be difficult to implement, and if it exceeds 50 parts by weight, the dielectric anisotropy of the liquid crystal composition decreases, so it may be difficult to control the driving voltage of the display. have.

In particular, a material having a double bond at the terminal, such as the compound of Formula II-1-2, is a material vulnerable to afterimages by UV. When the compound of Formula I is added to the liquid crystal composition containing 10 to 50 parts by weight of the compound of Formula II-1-2, the afterimage of the composition may be improved.

In the present invention, 100 parts by weight of the total liquid crystal composition may be calculated by the content of all components included in the liquid crystal composition, but is not limited thereto, for example, it may be calculated by including a liquid crystal compound, a light stabilizer compound, and other additives. have.

However, the present application may be implemented in combination with various different types of compounds, and is not limited to Formula II described herein.

Liquid crystal display

A third aspect of the present application provides a liquid crystal display device including the liquid crystal composition. In the liquid crystal display device according to this aspect, all of the contents described in the first aspect or the second aspect of the present application may be applied, and may not be limited thereto.

The liquid crystal composition includes a reactive light stabilizer compound represented by the above formula (I), thereby improving low temperature stability and afterimage without affecting the physical properties of the liquid crystal composition, such as transparency, elastic modulus, dielectric anisotropy or refractive anisotropy of the liquid crystal composition. The effect can be achieved at the same time, and in the mode in which the exposure process is required, the voltage retention (VHR) is increased and the RDC is lowered to improve the afterimage.

Accordingly, the liquid crystal composition may be applied to a liquid crystal display device through various methods known in the art to which the present invention pertains, VA (Vertical Alignment), MVA (Multidomain Vertical Alignment), PVA (Patterned Vertical Alignment), PSA (Polymer Stabilized) Manufactured with various modes of liquid crystal display devices such as Vertical Alignment (PS-VA), Polymer Stabilized Vertical Alignment (PS-VA) or IPS (In-Plane Switching), FFS (Fringe Field Switching) PLS (Plane to Line Switching), TN (Twisted Nemactic) Can be.

However, the present application is not limited to the liquid crystal display device described herein, as long as it can be applied to various different types of liquid crystal display devices.

Example

Hereinafter, it will be described in more detail through examples of the present application, and the scope of the present application is not limited by the present examples.

The liquid crystal compounds used in Examples and Comparative Examples are indicated by codes. In the above code, the symbols of the rings constituting the central group of the liquid crystal compound are sequentially written from the left, the connecting groups connecting the rings of the central group are described in order, and the terminal groups are written on the right. At this time, there is no distinction between the ring of the central group and the linking group connecting the ring of the central group, but the center group and the end group are separated by specifying "-", and both end groups are described by "." To distinguish. The individual abbreviated symbols (codes) of the substances are summarized in Table 1 below.

Referring to Table 1 above, the following code means a liquid crystal compound having the structure shown below.

<Example>

BAF-3.O2

Preparation Examples 1 to 3: Preparation of mixed liquid crystal having negative dielectric constant

The components described in Table 2 below were mixed at the contents described to prepare a liquid crystal composition according to the following examples.

The liquid crystal composition prepared above shows the properties summarized in Table 3 below.

Production Example 4: Preparation of mixed liquid crystal having a positive dielectric constant

To prepare the liquid crystal composition according to the following examples by mixing the components listed in Table 4 to the described content, it showed the summarized properties.

Example 1: Synthesis of Compound 5

[Synthesis Example 1] Synthesis of Compound 1

As shown in Scheme 1 below, 5-bromo-1-pentanol (50.00 g, 299.31 mmol) and 3,4-dihydro-2 H -pyran (3,4- and toluene sulfonic acid (p -toluenesulfonic acid) (0.57 g , 2.99 mmol) was added - mixed dihydro-2 H -pyran) (30.21 g, 359.17 mmol) in 500 mL of tetrahydrofuran (tetrahydrofuran), and where the para Stir for 1 hour. After the reaction solution was extracted with ethyl acetate and water, the reaction mixture obtained by concentrating the organic layer was purified by silica column chromatography to obtain a colorless transparent liquid compound 1 (64.50 g, 86% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 4.55-4.56 (1H, m), 3.82-3.87 (1H, m), 3.71-3.77 (1H, m), 3.48-3.50 (1H, m) , 3.35-3.43 (3H, m), 1.49-1.92 (12H, m)

[Scheme 1]

[Synthesis Example 2] Synthesis of Compound 2

As shown in Scheme 2 below, compound 1 (30.30 g, 120.64 mmol) and glycine methyl ester hydrochloride (7.57 g, 60.32 mmol) were mixed in 200 mL of acetonitrile, and here To potassium carbonate (potassium carbonate) (33.35 g, 241.28 mmol) and potassium iodide (40.05 g, 241.28 mmol) were added, and a reflux reaction was performed for 48 hours. After the reaction solution was extracted with ethyl acetate and water, the reaction mixture obtained by concentrating the organic layer was purified by silica column chromatography to obtain a colorless transparent liquid compound 2 (18.74 g, 72% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 4.55-4.56 (2H, m), 3.83-3.88 (2H, m), 3.71-3.75 (2H, m), 3.69 (3H, s), 3.48 -3.50 (2H, m), 3.34-3.40 (2H, m), 3.32 (2H, s), 2.56 (4H, t, J = 7.2 Hz), 1.32-1.85 (24H, m)

[Scheme 2]

[Synthesis Example 3] Synthesis of Compound 3

As shown in Scheme 3 below, Compound 2 (15.44 g, 35.94 mmol) and 4-hydroxy-2,2,6,6-tetramethylpiperidine (4-hydroxy-2,2,6,6-tetramethylpiperinde) ) (11.00 g, 71.88 mmol) was mixed with toluene (200 mL), and titanium isopropoxide (2.13 mL, 7.19 mmol) was added thereto, followed by reflux reaction for 24 hours. The reaction solution was concentrated, and the concentrated reaction was purified by silica column chromatography to obtain yellow liquid compound 3 (13.50 g, 68% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 5.22 (1H, tt, J = 11.2, 4.0 Hz), 4.55-4.57 (2H, m), 3.83-3.89 (2H, m), 3.70-3.76 (2H, m), 3.47-3.50 (2H, m), 3.35-3.39 (2H, m), 3.30 (2H, s), 2.58 (4H, t, J = 7.2 Hz), 1.91 (2H, dd, J = 12.0, 4.0 Hz), 1.31-1.85 (24H, m), 1.23 (6H, s), 1.11-1.17 (8H, m)

[Scheme 3]

[Synthesis Example 4] Synthesis of Compound 4

As shown in Scheme 4 below, compound 3 (13.50 g, 23.33 mmol) was mixed in 90 mL of methanol, and 1 N aqueous hydrochloric acid (90 mL) was added thereto for 30 min. It was stirred. The reaction solution was extracted with ethyl acetate and 2 M sodium hydroxide solution (2 M NaOH solution), and then the reaction obtained by concentrating the organic layer was purified by silica column chromatography to give a colorless transparent liquid compound 4 (5.60 g , 60% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 5.22 (1H, tt, J = 11.2, 4.0 Hz), 3.63 (4H, t, J = 6.4 Hz), 3.28 (2H, s), 2.58 ( 4H, t, J = 7.2 Hz), 1.92 (2H, dd, J = 12.4, 4.4 Hz), 1.34-1.61 (12H, m), 1.23 (6H, s), 1.12-1.18 (8H, m)

[Scheme 4]

[Synthesis Example 5] Synthesis of Compound 5

As shown in Scheme 5 below, compound 4 (3.10 g, 8.02 mmol) and methacrylic acid (1.70 mL, 20.05 mmol) were mixed in 120 mL of dichloromethane, and N,N` -N-N-dicyclohexylcarbodiimide (4.14 g, 20.05 mmol) and 4-dimethylaminopyridine (0.98 g, 8.02 mmol) were added and stirred for 24 hours. The reaction solution was extracted with ethyl acetate and water, and then the reaction obtained by concentrating the organic layer was purified by silica column chromatography to obtain an off-white transparent liquid compound 5 (1.10 g, 26% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 6.08 (2H, s), 5.54 (2H, s), 5.22 (1H, tt, J = 11.2, 4.0 Hz), 4.13 (4H, t, J = 6.4 Hz), 3.29 (2H, s), 2.58 (4H, t, J = 6.4 Hz), 1.89-1.93 (8H, m), 1.68 (4H, quintet, J = 6.8 Hz), 1.48 (4H, quintet , J = 7.2 Hz), 1.38 (4H, quintet, J = 7.2 Hz), 1.23 (6H, s), 1.11-1.17 (8H, m)

[Scheme 5]

¹ H NMR (CDCl ₃ , Varian 400 MHz): as shown in FIG. 1.

Example 2: Synthesis of Compound 9

[Synthesis Example 6] Synthesis of Compound 6

As shown in Scheme 6 below, Compound 1 (20.00 g, 79.63 mmol) and dimethyl iminodiacetate hydrochloride (15.74 g, 79.63 mmol) were mixed in 400 mL of acetonitrile, here To potassium carbonate (potassium carbonate) (44.00 g, 318.52 mmol) and potassium iodide (52.87 g, 318.52 mmol) were added, and reflux reaction was performed for 48 hours. After the reaction solution was extracted with ethyl acetate and water, the reaction mixture obtained by concentrating the organic layer was purified by silica column chromatography to obtain a colorless transparent liquid compound 6 (19.12 g, 72% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 4.55-4.57 (1H, m), 3.82-3.88 (1H, m), 3.71-3.75 (1H, m), 3.70 (6H, s), 3.54 (4H, s), 3.46-3.53 (1H, m), 3.34-3.40 (1H, m), 2.69 (2H, t, J = 7.2 Hz), 1.32-1.85 (12H, m)

[Scheme 6]

[Synthesis Example 7] Synthesis of Compound 7

As shown in Scheme 7 below, Compound 6 (19.12 g, 57.70 mmol) and 4-hydroxy-2,2,6,6-tetramethylpiperidine (4-hydroxy-2,2,6,6-tetramethylpiperinde) ) (45.36 g, 288.47 mmol) was mixed with 250 mL of toluene, and titanium isopropoxide (3.42 mL, 11.54 mmol) was added thereto to carry out a reflux reaction for 24 hours. The reaction solution was concentrated, and the concentrated reaction was purified by silica column chromatography to obtain a yellow liquid compound 7 (19.00 g, 57% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 5.22 (2H, quintet, J = 11.2, 4.4 Hz), 4.55-4.57 (1H, m), 3.83-3.88 (1H, m), 3.70-3.76 (1H, m), 3.52 (4H, s), 3.46-3.50 (1H, m), 3.35-3.40 (1H, m), 2.71 (2H, t, J = 7.6 Hz), 1.93 (4H, dd, J = 12.4, 4.0 Hz), 1.33-1.83 (12H, m), 1.23 (12H, s), 1.12-1.18 (16H, m)

[Scheme 7]

[Synthesis Example 8] Synthesis of Compound 8

As shown in Reaction Scheme 8 below, compound 7 (19.00 g, 32.66 mmol) was mixed in 125 mL of methanol, and 1 N aqueous hydrochloric acid (125 mL) was added thereto for 30 minutes. It was stirred. The reaction solution was extracted using ethyl acetate and a 2 M sodium hydroxide solution, and the reaction obtained by concentrating the organic layer was recrystallized from hexane to give a white solid compound 8 (11.18 g, 69 % yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 5.22 (2H, quintet, J = 11.2, 4.4 Hz), 3.64 (2H, t, J = 6.8 Hz), 3.51 (4H, s), 2.72 ( 2H, t, J = 7.2 Hz), 1.93 (4H, dd, J = 12.0, 4.0 Hz), 1.38-1.60 (6H, m), 1.23 (12H, s), 1.12-1.18 (16H, m)

[Scheme 8]

[Synthesis Example 9] Synthesis of Compound 9

As shown in Scheme 9 below, compound 8 (2.00 g, 4.02 mmol) and methacrylic acid (0.36 mL, 4.22 mmol) were mixed in dichloromethane 40 mL, and N,N` -Dicyclohexylcarbodiimide (N,N`-dicyclohexylcarbodiimide) (1.00 g, 4.82 mmol) and 4-dimethylaminopyridine (0.25 g, 2.01 mmol) were added and stirred for 24 hours. The reaction solution was extracted with ethyl acetate and water, and then the reaction obtained by concentrating the organic layer was purified by silica column chromatography to obtain an off-white transparent liquid compound 9 (1.00 g, 44% yield).

¹ H-NMR (CDCl ₃ , Varian 400 MHz): δ = 6.08 (1H, s), 5.54 (1H, s), 5.22 (2H, tt, J = 11.2, 4.0 Hz), 4.13 (2H, t, J = 6.8 Hz), 3.51 (4H, s), 2.71 (2H, t, J = 7.2 Hz), 1.90-1.93 (7H, m), 1.69 (2H, quintet, J = 7.2 Hz), 1.52 (2H, quintet , J = 6.8 Hz), 1.41 (2H, quintet, J = 6.8 Hz), 1.24 (12H, s), 1.13-1.19 (16H, m)

[Scheme 9]

¹ H NMR (CDCl ₃ , Varian 400 MHz): as shown in FIG. 2.

In order to confirm the physical properties of the synthesized reactive light stabilizer compound, it was evaluated according to the method described below in comparison with known materials. The following compound 10 was used as a comparative example.

Formula 10

Polymerizable compounds

Prior to confirming the physical properties of the synthesized reactive light stabilizer compound, known polymerizable compound materials Compound 11 and Compound 12 were used as examples and comparative examples to form an appropriate pretilt angle.

Preparation of liquid crystal composition

Liquid crystal compositions of Examples 3 to 13 and Comparative Examples 1 to 7 were prepared with the composition of Table 5 below.

Evaluation method of liquid crystal compound and liquid crystal composition

The low temperature stability and physical properties of the liquid crystal compound and the liquid crystal composition were evaluated according to the methods described below.

(1) Low temperature stability

A liquid crystal composition in 10mL vial (mixed liquid crystal, and 0.001 parts by weight of the compound represented by the general formula (I) to the liquid crystal 100 parts by weight of the mixture, 0.005 part by weight or 0.01 parts by weight liquid crystal composition of Tinuvin (TINUVIN) ^® 770 mixed liquid crystal 100 mixing portion 2 g of 0.001 part by weight, 0.005 part by weight or a liquid crystal composition mixed with 0.01 part by weight) was added to the weight part and stored in a freezer at -25°C. It was checked whether recrystallization was performed every 1 day. When recrystallization occurred 20 days before the initial freezer storage date, it was marked as "precipitation." If the liquid crystal phase was maintained after 20 days, it was expressed as "excellent".

(2) Transparent point (Tc)

After dropping a drop of the liquid crystal composition to measure the transparent point onto the slide glass with an eyedropper, a sample for measuring the transparent point was prepared by covering it with a cover glass.

The sample was placed in an instrument equipped with a METTLER TOLEDO FP90 temperature controller, and the change in the sample was observed while raising the temperature at a rate of 3°C/min with the FP82HT hot stage. The temperature at the spot where the sample was formed was recorded, and this operation was repeated three times to obtain an average value. And this value was defined as the transparent point of a liquid crystal composition.

(3) refractive index anisotropy (n)

The refractive anisotropy (n) of the liquid crystal composition was measured by an Abbe refractometer equipped with a polarizing plate on the eyepiece using light having a wavelength of 589 nm at 20°C. After rubbing the surface of the main prism in one direction, the liquid crystal composition to be measured was dropped into the main prism. Then, the refractive index (n∥) when the direction of polarization was parallel to the direction of rubbing and the refractive index (n⊥) when the direction of polarization was perpendicular to the direction of rubbing were measured. Then, the refractive index anisotropy (n) was measured by substituting the refractive index value into Equation 1.

[Equation 1]

n = n∥-n⊥

(4) Dielectric constant anisotropy (ε)

The dielectric anisotropy (ε) of the liquid crystal composition was calculated by substituting Equation 2 for εε∥ and ε⊥ measured as follows.

[Equation 2]

ε = ε∥-ε⊥

① Measurement of dielectric constant ε∥: A vertical alignment film was formed by applying a vertical alignment agent to the surfaces of the two glass substrates on which the ITO pattern was formed. Subsequently, a spacer was applied to any one of the two glass substrates so that the vertical alignment film faced each other and the gap (cell gap) between the two glass substrates was 4 μm, and then the two glass substrates were bonded. Then, the liquid crystal composition to be measured was injected into the device and sealed with an adhesive that cured with ultraviolet rays. Then, using a 4294A equipment manufactured by Agilent, the dielectric constant (ε∥) of the device at 1 kHz, 0.3 V and 20° C. was measured.

② Measurement of dielectric constant ε⊥: A horizontal alignment layer was formed by applying a horizontal alignment agent to the surfaces of the two glass substrates on which the ITO pattern was formed. Subsequently, a spacer was applied to any one of the two glass substrates so that the horizontal alignment film faced each other and the gap (cell gap) between the two glass substrates was 4 μm, and then the two glass substrates were bonded. Then, the liquid crystal composition to be measured was injected into the device and sealed with an adhesive that cured with ultraviolet rays. Then, using a 4294A equipment manufactured by Agilent, the dielectric constant (ε,) of the device at 1 kHz, 0.3 V and 20° C. was measured.

(5) Rotational viscosity (γ1)

A horizontal alignment layer was formed by applying a horizontal alignment agent to the surfaces of the two glass substrates on which the ITO pattern was formed. Subsequently, a spacer was applied to any one of the two glass substrates so that the horizontal alignment film faced each other and the distance (cell gap) between the two glass substrates was 20 μm, and then the two glass substrates were bonded. Then, a liquid crystal composition was injected into the device and sealed. Subsequently, the rotational viscosity of this device was measured at 20°C using a Model 6254 device of Toyo Corp. equipped with a temperature controller (Model SU-241) manufactured by ESPEC Corp.

(6) Voltage retention rate (VHR)

-Measurement of initial voltage retention rate (VHR ₀ )

A horizontal alignment layer was formed by applying a horizontal alignment agent to the surfaces of the two glass substrates on which the ITO pattern was formed. Subsequently, a spacer is applied to any one of the two glass substrates so that the horizontal alignment film faces each other and the gap (cell gap) between the two glass substrates becomes 4 μm, and then the two glass substrates are adhered to each other at 120° C. Dry in a vacuum oven for about 4 hours. Then, the liquid crystal compositions of Examples and Comparative Examples were injected into the device and sealed.

Subsequently, using a TOYO Corporation Model 6254C equipment, a voltage of 1V was applied between 60us at 100°C, and the initial voltage retention rate (VHR ₀ ) of the liquid crystal cells of Reference Examples, Examples, and Comparative Examples was measured under 60Hz, 3Hz, or 0.6Hz Did.

-Measurement of voltage retention (VHR _t ) after UV irradiation

The same cell as the cell for measuring the initial voltage retention was prepared, and while applying a voltage of AC 120 Hz and 10 V, UV of 3 to 5 J at 365 nm was irradiated to form an appropriate pretilt angle of 87 to 89°. At this time, a visible light of 300 nm or less was blocked by using a band-pass filter.

In some cases, in order to minimize residual reactive mesogen, a separate UV was additionally irradiated in a voltage-free state.

The voltage retention after UV irradiation was measured under the same conditions as the conditions under which the initial voltage retention was measured.

(7) RDC (Residual DC)

Cells were prepared using the liquid crystal compositions of Examples 3 to 13 and Comparative Examples 1 to 7 in the same manner as the cells for measuring the initial voltage retention, and RDC was measured under the following conditions using TOYO Corporation Model 6254C equipment. Did. It was carried out.

V _max and V ₂₁₀₀ values were derived by setting relaxation time 2,900 sec and warming up time to 5 hrs at a measurement temperature of 60°C and a measurement voltage of DC 5V and 600 sec.

(8) Ion density (pC)

The ion density was measured by setting the measurement voltage to 10V and 0.1Hz at a measurement temperature of 60°C or 100°C using the same cell and equipment as the cell for RDC measurement.

The ion density can be obtained based on Equation 3 below.

[Equation 3]

Physical properties of Examples 3 to 6 were confirmed to confirm changes in basic properties depending on the presence or absence of a reactive light stabilizer. The results are shown in Table 6 below.

In Examples 3 to 6, when compared with the physical properties of Preparation Examples 1 to 4 described above, it was confirmed that physical properties such as transparent point, refractive anisotropy, dielectric anisotropy and rotational viscosity were not changed even though a reactive light stabilizer was added.

In order to confirm the effect of improving the afterimage by content of the reactive light stabilizer developed herein, the characteristics of Examples 7 to 9 and Preparation Examples 1 to 3 were compared by measuring voltage retention (VHR), RDC and ion density after the exposure process, The results are shown in Table 7 below.

In Examples 7 to 9, as the content of the reactive light stabilizer of the present application was increased, the ion density increased, but it was insignificant, whereas the VHR increased and the RDC value decreased to gradually improve. Particularly, in Example 7, the voltage retention ratio (VHR) and the ion density are equivalent to those of Comparative Example 1 without the addition of a reactive light stabilizer, but RDC is very excellent. On the other hand, in Comparative Examples 2 to 3, as the content of the existing reactive light stabilizer increased, the ionic density increased with the voltage retention (VHR) and RDC. Example 7 has an ion density of less than half at 100°C in a measurement environment, although the reactive light stabilizer content is twice as high as in Comparative Example 3. In general, it is known that the higher the VHR value, the lower the RDC and ion density, the better the afterimage improvement effect.

The characteristics of Examples 10 to 13 and Comparative Examples 4 to 7 were compared by measuring voltage retention (VHR), RDC, and ion density for each of the liquid crystal composition types and polymerizable compound types before and after the exposure process. As shown in Table 8.

In Examples 10 to 13, the voltage retention ratio (VHR) decreased before the exposure process compared to Comparative Examples 4 to 7. However, after the exposure process, the voltage retention rate (VHR) is improved to the same level or higher. The ion density was the same level in Examples 10 to 13 as compared to Comparative Examples 4 to 7. On the other hand, in Examples 10 to 13, RDC was compared with Comparative Examples 4 to 7 before and after the exposure process, regardless of the liquid crystal composition and the polymerizable compound, and it was confirmed that RDC was measured to be very low and very excellent.

The above description of the present application is for illustrative purposes, and those skilled in the art to which the present application pertains will understand that it is possible to easily modify to other specific forms without changing the technical spirit or essential features of the present application. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present application is indicated by the claims, which will be described later, rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and equivalent concepts should be interpreted to be included in the scope of the present application. .

Claims (14)

Reactive light stabilizer compound represented by the formula (I):
[Formula I]

In the above formula I,
T ¹ to T ³ are each independently hydrogen (H), any one of the following Formulas 1 to 4, or a polymerizable functional group (wherein at least any one of T ¹ to T ³ is the following Formulas 1 to 3) Any one, and at least one of the other is the polymerizable functional group),
[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

Sp is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,
R ¹ is hydrogen (H), or C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is independently of each other, oxygen ( O) atoms can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other, C _{1 ~10} one or more hydrogen (H) of straight chain or branched alkyl can be replaced by F, Cl or CF ₃ ),
R ² to R ⁵ are each independently C _1-10 straight-chain or branched alkyl (wherein at least one methylene group of C _1-10 straight-chain or branched alkyl (-CH ₂ -) is independently of each other, oxygen ( O) atoms can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other, C _{1 ~10} one or more hydrogen (H) of straight chain or branched alkyl can be replaced by F, Cl or CF ₃ ),
Y is H, C _1-10 straight chain or branched alkyl, C _1-10 straight chain or branched alkoxy or C _2-10 straight chain or branched alkenyl (where C _1-10 straight chain or branched alkyl, C ₁ One or more non-adjacent methylene groups (-CH ₂ -) of _~10 straight chain or branched alkoxy or C _2-10 straight chain or branched alkenyl, each independently of each other, in such a way that oxygen (O) atoms are not directly connected to each other Can be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, one or more hydrogens of C _1-10 straight chain or branched alkyl Can be replaced by F, Cl or CF ₃ ),
n2 is an integer from 1 to 4,
A ¹ to A ³ are each independently represented by the formula (5),
[Formula 5]

L is a single bond, -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH ₂ -, -CH ₂ O-, -OCF ₂ -or -CF ₂ O-,
Z is a C _1-10 straight-chain or branched alkylenyl, or a C _5-20 cyclic alkylenyl group (wherein at least one methylene group of C _1-10 straight-chain or branched alkylenyl (-CH ₂ -) is each Independent of each other, oxygen (O) atoms are replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in such a way that they are not directly connected to each other And one or more hydrogen (H) of C _1-10 straight chain or branched alkylenyl may be replaced by F, Cl or CF ₃ , and one or more carbon (C) atoms of C _5-20 ring groups may be O, N or S and one or more hydrogen (H) of the C _5-20 ring group may be replaced by F, Cl or CF ₃ ),
n3 is an integer of 1 or 2, and when n3 is 2, L and Z may be the same or different from each other.
According to claim 1,
The polymerizable functional group is a polymerizable compound represented by any one of the following formulas:

,

,

.
According to claim 1,
At least one of T ¹ to T ³ is the following Chemical Formula 1 or Chemical Formula 2, and at least one of the remaining is the polymerizable functional group,
[Formula 1] [Formula 2]

Reactive light stabilizer compound.
According to claim 1,
The Sp is -CH=CH-, -C≡C-, -CH ₂ CH ₂ -, -(CH ₂ ) ₄ -, -COO-, -OCO-, -CO-, -O-, -OCH _2- , -CH ₂ O-, -OCF ₂ -or -CF ₂ O- phosphorus,
Reactive light stabilizer compound.
The method of claim 3,
The Sp is -COO- phosphorus, a reactive light stabilizer compound.
According to claim 1,
The R ¹ is hydrogen (H), a reactive light stabilizer compound.
According to claim 1,
The n2 is an integer of 1 or 2, a reactive light stabilizer compound.
According to claim 1,
L is a single bond,
Wherein Z is C _1-10 straight chain or branched alkylenyl (wherein at least one methylene group of C _1-10 straight chain or branched alkylenyl (-CH ₂ -) is independently of each other, oxygen (O) atoms are Can be replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- in a manner that is not directly connected to each other and C _1-10 straight chain or minute At least one hydrogen (H) of the terrestrial alkylenyl may be replaced by F, Cl or CF ₃ ),
Reactive light stabilizer compound.
According to claim 1,
The formula I is represented by the following formula, a reactive light stabilizer compound:

.
A liquid crystal composition comprising the reactive light stabilizer compound according to claim 1.
The method of claim 10,
A liquid crystal composition further comprising a compound represented by Formula II:
[Formula II]

In the above formula II,
Ring A and Ring B are each independently 1,4-cyclohexylene in which carbon (C) in the ring is substituted or unsubstituted with one or more oxygen (O), or one or more hydrogen (H) is substituted or unsubstituted with halogen. Is 1,4-phenylene,
R ⁶ and R ⁷ are each independently C _1-7 alkyl, C _1-7 alkoxy, or C _2-7 alkenyl,
n4 is an integer from 1 to 3, and when n4 is 2 or 3, ring B may be the same or different from each other.
The method of claim 11,
The halogen is fluorine (F) liquid crystal composition.
The method of claim 10,
The reactive light stabilizer compound is 0.001 to 5 parts by weight based on 100 parts by weight of the liquid crystal composition.
A liquid crystal display device comprising the liquid crystal composition of claim 10.

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