KR20160112695A - Liquid crystal composition and liquid crystal cell comprising the same - Google Patents

Liquid crystal composition and liquid crystal cell comprising the same Download PDF

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KR20160112695A
KR20160112695A KR1020150038873A KR20150038873A KR20160112695A KR 20160112695 A KR20160112695 A KR 20160112695A KR 1020150038873 A KR1020150038873 A KR 1020150038873A KR 20150038873 A KR20150038873 A KR 20150038873A KR 20160112695 A KR20160112695 A KR 20160112695A
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liquid crystal
group
formula
carbon atoms
crystal composition
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이미경
김봉희
이선희
홍보라
김영국
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주식회사 동진쎄미켐
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings

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Abstract

The present invention relates to a liquid crystal composition and a liquid crystal cell comprising the same. The liquid crystal composition can provide a liquid crystal cell that exhibits excellent optical stability and thermal stability while maintaining the physical properties of the liquid crystal composition while blending a light stabilizer having a specific structure.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal composition,

The present invention relates to a liquid crystal composition having excellent light and heat stability and a liquid crystal cell comprising the same.

BACKGROUND ART Liquid crystal display devices (LCDs) are used in various electronic devices such as watches and electronic calculators, measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, and televisions. Typical examples of the liquid crystal display include TN (Twist nematic), STN (Super-twisted nematic), IPS (In-plane switching), FFS (Fringe field switching) and VA (Virtical alignment).

The liquid crystal material used for such a liquid crystal display device is required to be capable of low-voltage driving and high-speed response, and capable of operating in a wide temperature range. Specifically, in order to drive stably in a wide temperature range, it is required that the liquid crystal material exhibits stable physical properties at about -20 占 폚 or lower (low temperature stability) and has a transparent point of about 70 占 폚 or higher. For the low-voltage driving and the high-speed response, the liquid crystal material is required to have a large absolute value of the dielectric anisotropy, a small rotational viscosity, and a suitable modulus of elasticity (K 11 , K 22 , K 33 average value).

The required physical properties of such a liquid crystal material can not be satisfied by using one or two kinds of liquid crystal compounds, and usually 7 to 20 kinds of liquid crystal compounds are mixed and satisfied.

However, when the composition of the liquid crystal compound satisfying the required properties is exposed to heat or light for a long time or is left in an environment of moisture or oxygen atmosphere, the voltage retention rate of the composition is lowered and the reliability of the liquid crystal panel The problem of degradation occurs.

Accordingly, various stabilizers that can be added to the liquid crystal composition have been researched. With reference to Patent Documents 1 and 2, a stabilizer having a structure represented by the following formulas (p-1) and (p-2) has been proposed.

[Formula p-1]

Figure pat00001

[Formula p-2]

Figure pat00002

However, the stabilizer of the above structure adversely affects the physical properties of the liquid crystal material such as reducing the transparent point of the liquid crystal material, and the ester group as the thermally unstable structure is employed to improve the reliability of the liquid crystal material to a satisfactory level Respectively.

Japanese Patent No. 5036958 (registered on July 13, 2012) Korean Patent Publication No. 2014-0004119 (Disclosure Date: January 10, 2014)

According to one embodiment of the present invention, there is provided a liquid crystal composition having excellent optical and thermal stability.

According to another embodiment of the present invention, there is provided a liquid crystal cell comprising the liquid crystal composition.

According to an embodiment of the present invention, a light stabilizer represented by the following general formula (1); And at least one liquid crystal molecule selected from the group consisting of liquid crystal molecules represented by the following general formulas (2) and (3).

[Chemical Formula 1]

Figure pat00003

Wherein R 1 is a radical of any one of a straight chain alkyl group having 4 to 15 carbon atoms and a straight chain alkoxy group having 4 to 15 carbon atoms,

(2)

Figure pat00004

(3)

Figure pat00005

In the above Formulas 2 and 3,

R 2 to R 5 are each independently selected from the group consisting of hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with halogen, An alkenyl group having 2 to 12 carbon atoms and an alkoxy group having 1 to 12 carbon atoms substituted with halogen,

A 1 to A 5 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-

Z 1 to Z 3 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.

The liquid crystal composition may have a transparent point difference of less than 1 캜 in the following formula (1).

[Formula 1]

Transparent point difference (C) = | T a - T b |

In the formula (1), T a is a transparent point of a liquid crystal composition not containing a light stabilizer, and T b is a transparent point of a liquid crystal composition containing a light stabilizer at 0.1 wt%.

The light stabilizer can be the R 1 of Formula 1 is any one of a radical of a straight-chain alkoxy having 6 to 12 carbon atoms and straight-chain alkyl group having 6 to 12.

Such a light stabilizer may be contained in an amount of 0.005 to 5 parts by weight based on 100 parts by weight of the liquid crystal molecules.

As the liquid crystal molecules of Formula 2, R 2 and R 3 in Formula 2 are each independently a radical selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a vinyl group, and -CH = CHCH 3 Liquid crystal molecules can be used. More specifically, the liquid crystal molecule of Formula 2 may include a liquid crystal molecule of Formula 2-1.

[Formula 2-1]

Figure pat00006

In the general formula (2-1), R a and R b are each independently a radical of a methoxy group, an ethyl group, a propyl group, a vinyl group or -CH = CHCH 3 .

The liquid crystal molecules of Formula 3 include those wherein R 4 and R 5 are independently selected from the group consisting of fluorine, an alkyl group having 1 to 5 carbon atoms, a vinyl group, -CH = CHCH 3 , a trifluoromethoxy group, Lt; RTI ID = 0.0 > Cl-5 < / RTI > More specifically, at least one liquid crystal molecule among the liquid crystal molecules represented by the following formulas (3-1) to (3-6) may be included in the liquid crystal molecule of Formula (3).

[Formula 3-1]

Figure pat00007

In the above formula (3-1), R c is a radical of any of the alkyl groups having 2 to 5 carbon atoms, R d to R g are each independently hydrogen or fluorine,

[Formula 3-2]

Figure pat00008

In the formula (3-2), R h is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R i to R 1 are each independently hydrogen or fluorine,

[Formula 3-3]

Figure pat00009

Wherein R m is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R n and R o are each independently hydrogen or fluorine, R p is a fluorine or trifluoromethoxy group,

[Chemical Formula 3-4]

Figure pat00010

Wherein R s is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R t to R w are each independently hydrogen or fluorine, Z a is -CH 2 O- or -CF 2 O -ego,

[Formula 3-5]

Figure pat00011

R aa is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ab to R ae are each independently hydrogen or fluorine, Z b is a single bond, -CH 2 O- or - CF 2 O-,

[Chemical Formula 3-6]

Figure pat00012

In the above formula (3-6), R af is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ag to R aj are each independently hydrogen or fluorine, Z c is a single bond, -CH 2 O- or - CF 2 O-.

For example, the liquid crystal composition may include 10 to 50 parts by weight of a liquid crystal molecule represented by Formula 2 and 3 to 55 parts by weight of a liquid crystal molecule represented by Formula 3 when the total weight of the liquid crystal molecules is 100 parts by weight.

The liquid crystal composition may further include a liquid crystal molecule represented by the following formula (4).

[Chemical Formula 4]

Figure pat00013

In Formula 4,

R 6 and R 7 are each independently hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with halogen, An alkenyl group having 2 to 12 carbon atoms and an alkoxy group having 1 to 12 carbon atoms substituted with halogen,

A 6 to A 9 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-

Z 4 to Z 6 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.

According to another embodiment of the present invention, there is provided a plasma display panel comprising a first substrate and a second substrate arranged to face each other, and a spacer formed between the first and second substrates such that the first and second substrates are spaced apart from each other, , A liquid crystal cell into which the liquid crystal composition is injected is provided in a cell formed by the first and second substrates and the spacer.

The liquid crystal composition according to one embodiment of the present invention may exhibit excellent light stability and thermal stability while keeping the physical properties of the liquid crystal composition intact by blending a light stabilizer having a specific structure.

Hereinafter, a liquid crystal composition according to a specific embodiment of the present invention and a liquid crystal cell manufactured using the same will be described.

According to an embodiment of the present invention, a light stabilizer represented by the following general formula (1); And at least one liquid crystal molecule selected from the group consisting of liquid crystal molecules represented by the following general formulas (2) and (3).

[Chemical Formula 1]

Figure pat00014

Wherein R 1 is a radical of any one of a straight chain alkyl group having 4 to 15 carbon atoms and a straight chain alkoxy group having 4 to 15 carbon atoms,

(2)

Figure pat00015

(3)

Figure pat00016

In the above Formulas 2 and 3,

R 2 to R 5 are each independently selected from the group consisting of hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with halogen, An alkenyl group having 2 to 12 carbon atoms and an alkoxy group having 1 to 12 carbon atoms substituted with halogen,

A 1 to A 5 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-

Z 1 to Z 3 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.

The light stabilizer used in the conventional liquid crystal composition has problems such as lowering thermal stability and changing the transparent point of the liquid crystal composition. However, the liquid crystal composition according to one embodiment of the present invention may be prepared by blending a light stabilizer having the structure of the formula (1) in a composition containing liquid crystal molecules to obtain various liquid crystal compositions such as transparent point, elastic modulus, dielectric anisotropy or refractive index anisotropy It is possible to remarkably improve the resistance to heat and light of a liquid crystal composition or an element to which such a liquid crystal composition is applied without affecting physical properties. For example, the change of the transparent point by the light stabilizer calculated by the following formula 1 in the liquid crystal composition may be less than 1 占 폚, less than 0.5 占 폚, or less than 0.15 占 폚.

[Formula 1]

Transparent point difference (C) = | T a - T b |

In the formula (1), T a is a transparent point of a liquid crystal composition not containing a light stabilizer, and T b is a transparent point of a liquid crystal composition containing a light stabilizer at 0.1 wt%. As a method of measuring the transparent point, the method described in Test Examples described later can be referred to.

The light stabilizer is a liquid crystal display device which exhibits excellent heat and light stability and exhibits excellent reliability, as can be seen in the test examples described later, while maintaining the physical properties of the liquid crystal composition to which the light stabilizer is not added, .

The above effect may be attributed to the structure of Formula 1. Specifically, the light stabilizer adopts a structure in which R 1 is bonded to the meta position of OH bonded to the benzene ring as shown in Formula 1 above. Particularly, the above-mentioned light stabilizer is a compound wherein R 1 is selected from the group consisting of a straight-chain alkyl group having 4 to 15 carbon atoms and a straight-chain alkoxy group having 4 to 15 carbon atoms, so that the light stabilizer does not affect the physical properties of the liquid crystal composition, Can be improved.

In order to more effectively ensure this effect, the R 1 may be a radical of any one of a straight-chain alkyl group having 6 to 12 carbon atoms and a straight-chain alkoxy group having 6 to 12 carbon atoms.

The light stabilizer of Formula 1 is added in an amount of 0.005 to 5 parts by weight, 0.005 to 4 parts by weight, 0.005 to 3 parts by weight per 100 parts by weight of the liquid crystal molecules so as to impart excellent optical and thermal stability, Or 0.01 to 1 part by weight.

In addition, referring to Examples to be described later, a structure in which a substituent is bonded to the ortho and / or para positions of OH of the benzene ring in Formula 1 is employed, and a bulky substituent such as a t-butyl group When a nonlinear substituent such as an ester group having poor thermal stability is employed, it affects all properties of the liquid crystal composition and it is confirmed that the degree of improvement in resistance to heat is not sufficient. Accordingly, it is possible to provide a liquid crystal display element having a high reliability and showing no afterimage and unevenness by blending a light stabilizer having the structure of Formula 1 in the liquid crystal composition.

The liquid crystal composition may include at least one liquid crystal molecule represented by the general formulas (2) and (3). The term "liquid crystal molecule" as used herein refers to a liquid crystal molecule that can be changed in orientation by a change in the surrounding environment (for example, an applied voltage), as distinguished from a liquid crystal polymer contained in a polymerized state on an optical film or the like do.

The liquid crystal molecules represented by the formulas (2) and (3) are widely known as compounds that can be used for liquid crystal display devices and the like. However, a part of the liquid crystal molecules are vulnerable to heat and light, which may lower the stability and lifetime of the device. Therefore, there are many restrictions in applying the liquid crystal molecules to the liquid crystal display device. However, the liquid crystal composition according to one embodiment can provide a liquid crystal cell having excellent stability and lifetime even when liquid crystal molecules susceptible to heat and light are employed by employing the light stabilizer of Formula 1. Accordingly, it is expected that the use of the conventional liquid crystal molecules can be drastically solved due to the liquid crystal composition according to one embodiment.

The liquid crystal molecule of Formula 2 is a liquid crystal molecule in which R 2 and R 3 in Formula 2 are each independently any one of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a vinyl group, and -CH═CHCH 3 , Molecules can be used. More specifically, as the liquid crystal molecules of Formula 2, liquid crystal molecules represented by Formula 2-1 may be used.

[Formula 2-1]

Figure pat00017

In the general formula (2-1), R a and R b are each independently a radical of a methoxy group, an ethyl group, a propyl group, a vinyl group or -CH = CHCH 3 .

Particularly, when at least one of R a and R b is a vinyl group or -CH = CHCH 3 , the liquid crystal composition exhibits a weak property against heat and light. However, the liquid crystal composition according to one embodiment employs a light stabilizer having a specific structure, Or a liquid crystal molecule of a nature.

As the liquid crystal molecules of Formula 3, R 4 and R 5 in Formula 3 are each independently selected from the group consisting of fluorine, an alkyl group having 1 to 5 carbon atoms, a vinyl group, -CH = CHCH 3 , a trifluoromethoxy group, Lt; RTI ID = 0.0 > Rl, < / RTI > More specifically, as the liquid crystal molecules of Formula 3, at least one liquid crystal molecule among the liquid crystal molecules represented by the following Formulas 3-1 to 3-6 may be used.

[Formula 3-1]

Figure pat00018

In the above formula (3-1), R c is a radical of any of the alkyl groups having 2 to 5 carbon atoms, R d to R g are each independently hydrogen or fluorine,

[Formula 3-2]

Figure pat00019

In the formula (3-2), R h is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R i to R 1 are each independently hydrogen or fluorine,

[Formula 3-3]

Figure pat00020

Wherein R m is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R n and R o are each independently hydrogen or fluorine, R p is a fluorine or trifluoromethoxy group,

[Chemical Formula 3-4]

Figure pat00021

Wherein R s is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R t to R w are each independently hydrogen or fluorine, Z a is -CH 2 O- or -CF 2 O -ego,

[Formula 3-5]

Figure pat00022

R aa is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ab to R ae are each independently hydrogen or fluorine, Z b is a single bond, -CH 2 O- or - CF 2 O-,

[Chemical Formula 3-6]

Figure pat00023

In the above formula (3-6), R af is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ag to R aj are each independently hydrogen or fluorine, Z c is a single bond, -CH 2 O- or - CF 2 O-.

Particularly, a liquid crystal molecule containing a terphenyl group in the central group or a linking group of -CH 2 O- or -CF 2 O- as in the above formulas 3-5 and 3-6, Heat and light. However, the liquid crystal composition according to one embodiment may also include liquid crystal molecules of this nature by employing a light stabilizer having a specific structure.

The liquid crystal composition can further improve the optical and thermal stability effects of the light stabilizer of Formula 1, including the liquid crystal molecules represented by Formula 2 and the liquid crystal molecules represented by Formula 3. When the total weight of the liquid crystal molecules is 100 parts by weight, the liquid crystal composition may include 10 to 50 parts by weight of the liquid crystal molecules represented by the formula (2) and 3 to 55 parts by weight of the liquid crystal molecules represented by the formula (3) . It is possible to provide a liquid crystal composition having excellent physical properties within such a range and having excellent optical and thermal stability by the light stabilizer of the above formula (1).

The liquid crystal composition may further include various liquid crystal molecules known in the art to which the present invention belongs, in addition to the liquid crystal molecules described above. For example, the liquid crystal composition may further include a liquid crystal molecule represented by Formula 4 below.

[Chemical Formula 4]

Figure pat00024

In Formula 4, R 6 and R 7 are each independently selected from the group consisting of hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, An alkyl group, a halogen-substituted alkenyl group having 2 to 12 carbon atoms, and a halogen-substituted alkoxy group having 1 to 12 carbon atoms,

A 6 to A 9 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-

Z 4 to Z 6 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.

More specifically, as the liquid crystal molecules represented by the above formula (4), liquid crystal molecules represented by the following formula (4-1) can be used.

[Formula 4-1]

Figure pat00025

In Formula 4-1, R x is a radical of any one of the alkyl groups having 2 to 3 carbon atoms, and R y and R z are each independently hydrogen or fluorine.

In addition to the above-mentioned components, the liquid crystal composition may further include various additives commonly used in the art to which the present invention belongs.

According to another embodiment of the present invention, there is provided a liquid crystal cell using the liquid crystal composition. The liquid crystal composition may be used in a liquid crystal cell in various ways known to those skilled in the art. For example, the liquid crystal cell may include a first substrate and a second substrate disposed to face each other, and a spacer formed between the first and second substrates such that the first and second substrates are spaced apart from each other, And a structure in which the liquid crystal composition is injected into a cell formed by the second substrate and the spacer. An alignment layer for initially aligning the liquid crystal composition may be formed on the surfaces of the first and second substrates contacting the liquid crystal composition.

The liquid crystal cell may be fabricated by using various liquid crystal materials such as Twist nematic (TN), Super-twisted nematic (STN), In-plane switching (IPS), Fringe field switching (FFS) And can be driven in a display manner.

BRIEF DESCRIPTION OF THE DRAWINGS The above and other objects, features and advantages of the present invention will be more apparent from the following detailed description taken in conjunction with the accompanying drawings, in which: FIG. However, this is provided as an example of the invention, and the scope of the invention is not limited thereto in any sense.

Manufacturing example  1: Preparation of light stabilizer

Figure pat00026

Resorcinol (136.5 g, 1.24 mol) and 1-bromodecane (85 mL, 0.41 mol) were added to 600 mL ethanol. 75 ml of a potassium hydroxide solution was added dropwise thereto while refluxing, and the resulting mixture was refluxed for 3 hours.

Then, 1.5 L of water was poured into the mixture, the reaction product was extracted with toluene, and the toluene extract was dried with magnesium sulfate and then the solvent was removed. The residue was purified by silica gel column chromatography using dichloromethane as a developing solvent to give (1) substance.

Figure pat00027

To the reaction vessel were added 500 mL of water, 75% sulfuric acid solution and 1.0 g of dispersant, stirred at room temperature, and o-nitroaniline (138 g, 1 mol) was added dropwise while heating at 60 to 65 ° C. Then, the resulting mixture was emulsified at 70 to 75 ° C, and then water and 75% sulfuric acid solution were added thereto to emulsify at 40 ° C. The resulting mixture was cooled to 0 占 폚 and further cooled to -9 占 폚 or lower. Then, an aqueous solution of sodium nitrite (NaNO 2 , 205 g, 1.08 mol) was added dropwise to the mixture for 30 minutes and reacted for 2 hours while maintaining the temperature at 7 ° C or lower, followed by filtration to obtain a diazonium salt. The diazonium salt thus prepared was added to water to prepare a diazonium salt aqueous solution, and the aqueous solution was stored at 7 ° C or lower.

On the other hand, the above-prepared substance (1) (50 g, 0.2 mol) was added to 200 mL of water and 13 g of 48% sodium hydroxide and stirred. The thus-obtained mixture was cooled to 0 占 폚, and sodium carbonate (32 g, 0.3 mol) and 150 mL of water were added thereto.

Then, an aqueous solution of the diazonium salt synthesized before the above mixture was added dropwise for 2 hours, and the mixture was stirred at 0 to 10 ° C for 2 hours. The reaction product solution thus obtained was filtered to obtain crystals, and the crystals were washed with 1000 mL of water to remove inorganic salts to obtain a substance (2).

Figure pat00028

To the reaction vessel was added (2) 100 g (0.27 mol) of substance, 50 g of 48% sodium hydroxide, 400 g of toluene and 400 g of water, and the mixture was heated and stirred at a temperature of 65 to 70 ° C for 1 hour and then cooled to 58 ° C. Hydroquinone and hydrazine (excess) were added dropwise thereto over 2 hours, and the temperature was maintained at 70 to 75 占 폚. Then, the temperature was adjusted to 50 to 55 캜 and maintained for 26 hours, and then the pH was neutralized to 4 to 5 by adding 75% sulfuric acid solution. At this time, the temperature was maintained at 75 to 85 占 폚.

The neutralized reactant was separated into layers, and the lower layer (water layer) was removed and washed with water. Then, 300 g of water and 40 g of zinc powder were added to the obtained solution, and then 70 g of 75% sulfuric acid solution was added dropwise for 30 minutes, and the temperature was maintained at 75 to 85 캜. After stirring for 3 hours, the unreacted zinc powder was removed by filtration, and the lower layer (water layer) was removed by layer separation. The colorant was extracted with a sulfuric acid solution from the obtained organic layer, and the residue was decolorized with a decolorizing agent. Recrystallization was performed with methanol and purification was carried out by silica gel column chromatography to obtain a light stabilizer (about 5%, MS m / z 367.49).

Manufacturing example  2: Preparation of light stabilizer

A light stabilizer represented by the following formula 1-b was prepared in the same manner as in Production Example 1, except that 1-bromo octane was used instead of 1-bromodecane in Production Example 1.

[Chemical Formula 1-b]

Figure pat00029

Manufacturing example  3: Preparation of light stabilizer

Figure pat00030

Zn powder (5.25 g, 0.08 mol) was added to 120 mL of a PTS solution containing 2 wt% of Pd (amphos) Cl 2 (0.28 g, 0.4 mmol) under an argon atmosphere. Then, N, N, N ', N'-tetramethylethylenediamine (TMEDA, 11.6 g, 0.1 mol) was added to the mixture at room temperature, 1-bromodecane (0.06 mol) and 3-bromoanisole (0.02 mol) . The thus prepared mixture was reacted by stirring at room temperature. Then, quenched with 1M HCl solution, extracted with ethyl acetate, and then the organic solvent was removed and dried. The residue was purified by silica gel column chromatography to obtain 3-decyl anisole in 78% yield.

3-Decyl Anisole (0.15 mol) and ethylenediamine (0.11 mol) obtained in THF (300 mL) were purged with nitrogen to remove oxygen. The thus obtained mixture was cooled to -10 ℃, was added small pieces of lithium in the mixture under a N 2 environment. After a suitable period of time, the reaction mixture was quenched with 6M HCl solution (pH 3-4), extracted with brine solution and diethyl ether, and dried over Na 2 SO 4 . Thereafter, the product was purified by silica gel column chromatography (3) to obtain a substance.

A light stabilizer represented by the following formula (1-c) was prepared in the same manner as in Preparation Example 1, except that (1) the substance (3) prepared as described above was used instead of the substance (1) in Production Example 1.

[Chemical Formula 1-c]

Figure pat00031

Manufacturing example  4: Preparation of light stabilizer

A light stabilizer represented by the following Formula 1-d was prepared in the same manner as in Production Example 3, except that 1-bromo octane was used instead of 1-bromodecane in Production Example 3.

[Chemical formula 1-d]

Figure pat00032

Reference example , Example  1 to 12 and Comparative Example  1 to 12: Preparation of liquid crystal composition

The liquid crystal compositions according to the following Reference Examples, Examples, and Comparative Examples were prepared by mixing the ingredients listed in Table 1 below in the stated amounts.

Liquid crystal molecule Light stabilizer H-0 H-1 H-2 H-3 H-4 H-5 H-6 1-a 1-b 1-c 1-d p-1 p-2 Reference example 100 Example 1 100 0.1 Example 2 100 0.1 Example 3 100 0.1 Example 4 100 0.1 Example 5 100 0.1 Example 6 100 0.1 Example 7 100 0.1 Example 8 100 0.1 Example 9 100 0.1 Example 10 100 0.1 Example 11 100 0.1 Example 12 100 0.1 Comparative Example 1 100 Comparative Example 2 100 0.1 Comparative Example 3 100 Comparative Example 4 100 0.1 Comparative Example 5 100 Comparative Example 6 100 0.1 Comparative Example 7 100 Comparative Example 8 100 0.1 Comparative Example 9 100 Comparative Example 10 100 0.1 Comparative Example 11 100 Comparative Example 12 100 0.1

(Unit: g)

H-0, H-1, H-2, H-3, H-4, H-5 and H-6 in Table 1 are compositions of liquid crystal molecules mixed in the composition shown in Table 2, Meanings are shown in Table 3.

H-0 H-1 H-2 H-3 H-4 H-5 H-6 BA-3.O1 10.0 BB-2.3 36.6 36.6 BB-3.V 39.9 18.0 36.3 38.0 20.0 BB-3.U1 6.9 5.0 9.4 9.0 ACA-2.3 2.6 6.0 ACA-3.3 1.6 BAA-3.2 9.8 4.8 4.5 4.0 9.8 BAA-5.2 9.8 2.2 4.2 4.0 9.8 BBA-V.1 5.2 6.2 BBA-3.1 3.5 ACA-2.F 6.3 ACA-3.F 5.3 6.8 ACE-2.F 3.6 5.0 2.4 ACE-3.F 7.7 9.5 7.5 ACE-5.F 5.4 5.0 8.0 BAC-3.F 9.8 9.8 BAE-3.F 7.1 5.0 4.0 BCE-2.F 1.5 BCE-3.F 5.0 BBA-3.OCF3 6.5 6.0 4.5 2.0 BBC-3.OCF3 4.5 BBE-2.F 17.0 3.0 17.0 BBE-3.F 17.0 8.0 7.0 17.0 BBXE-3.F 13.0 BBXE-5.F 9.5 BBAE-3.F 2.2 BBCE-3.F 2.1 3.5 2.1 8.0 AEXE-3.F 15.0 ZEXE-1.F 9.0 ZCEXE-1.F 3.0 BF-5.O2 18.5 AFA-2.3 8.0 BAF-2.O2 10.0 BAF-3.O2 10.0 BBF-3.O2 12.5 BBF-2.1 8.5 BNF-4.O1 2.5 BBYF-3.O2 15.0

(Unit: g)

sign rescue Center group A

Figure pat00033
B
Figure pat00034
 C
Figure pat00035
 E
Figure pat00036
 F
Figure pat00037
 Z
Figure pat00038
 Connection group X -CF 2 O- Y -CH 2 O- N -CH 2 CH 2 - End group n -C n H 2n + 1
(The alkyl group is represented by the number of carbon atoms of the alkyl group) On -OC n H 2n + 1
(The alkoxy group is briefly expressed by the carbon number of the alkoxy group) V -CH = CH 2 U1 -CH = CHCH 3 (1) Insert a symbol '-' between the center group and the end group to separate the center group and the end group.
(2) The end group is described at the end of the code, and the end group is separated by inserting the symbol '.' Between the end group and the end group.

<Example>
ACE-3.F
Figure pat00039

1-a, 1-b, 1-c and 1-d in Table 1 are the light stabilizers of Formulas 1-a, 1-b, 1-c and 1-d prepared in Preparation Examples 1 to 4, p-1 and p-2 are light stabilizers used in conventional liquid crystal cells and are represented by the following formulas (p-1) and (p-2), respectively.

[Formula p-1]

Figure pat00040

[Formula p-2]

Figure pat00041

Test Example : A liquid crystal composition Transparent point  And The liquid crystal cell  Stability evaluation

Using the liquid crystal compositions prepared in Reference Examples 1 to 12 and Comparative Examples 1 to 12, transparent points were measured in the following manner, and liquid crystal cells were prepared from the liquid crystal compositions, and their stability was evaluated. The results are shown in Table 4.

(1) Evaluation of transparent points

Each of the liquid crystal compositions of Reference Examples 1 to 12 and Comparative Examples 1 to 12 was dropped on a slide glass by a dropper, and covered with a cover glass to prepare a sample for measurement of a transparent point.

The sample prepared above was put into a tool equipped with a METTLER TOLEDO FP90 temperature regulator and the change of the sample was observed by raising the temperature at a rate of 3 ° C / min with the FP82HT hot stage. The temperature at the point where the hole was formed in the sample was recorded, and this operation was repeated three times to derive an average value. This value was defined as the transparent point of the liquid crystal composition.

(2) Evaluation of thermal stability

- Measurement of initial voltage maintenance rate (VHR 0 )

A plurality of 4.0 [mu] m TN cells (obtained from Trujillo, China) were dried in a vacuum oven at 120 [deg.] C for about 4 hours.

The liquid crystal compositions prepared in Reference Examples, Examples 1 to 12 and Comparative Examples 1 to 12 were placed in an oven under nitrogen atmosphere and pretreated at a temperature of about 150 ° C for 1 hour. Thereafter, the pretreated liquid crystal composition was preliminarily dried and injected into each prepared 4.0 占 퐉 TN cell to prepare a liquid crystal cell.

Subsequently, a voltage of 1 V was applied for 60 seconds at 100 캜 using TOYO Corporation Model 6254C equipment, and the initial voltage holding ratio (VHR 0 ) of the liquid crystal cell of Reference Example, Example and Comparative Example was measured at 60 Hz or 30 Hz.

- Measurement of voltage maintenance rate after heat treatment

A cell was prepared using the liquid crystal compositions of Reference Examples, Examples 1 to 8 and Comparative Examples 1 to 8 in the same manner as the cell for measurement of the initial voltage holding ratio, and the cell was left at a temperature of 100 ° C for 240 hours Stress was applied to the cell.

Then, the voltage holding ratio was measured under the same conditions as those in which the initial voltage holding ratio was measured using the heat-treated cells.

- Calculation of change of voltage holding ratio after heat treatment

The initial voltage holding ratio (VHR 0 ) and the voltage holding ratio after heat treatment (VHR t ) measured above were substituted into the following equation (2), and the degree of change in the voltage holding ratio was calculated.

[Formula 2]

VHR = | VHR 0 - VHR t |

(3) Evaluation of UV stability

- Measurement of voltage retention rate after UV irradiation

Cells were prepared using the liquid crystal compositions of Reference Examples, Examples 1 to 8 and Comparative Examples 1 to 8 in the same manner as the cells for measurement of the initial voltage holding ratio, and after irradiating 3 J or 20 J of UV, The voltage holding ratio after UV irradiation was measured.

- Calculation of change of voltage holding ratio after UV irradiation

The initial voltage holding ratio (VHR 0 ) and the voltage holding ratio after UV irradiation (VHR t ) measured in the above manner were substituted into the equation (2), and the degree of change of the voltage holding ratio was calculated.

(4) Evaluation of thermal stability under more severe conditions

- Measurement of voltage retention after heat treatment in more severe conditions

The liquid crystal compositions prepared in Examples 9 to 12 and Comparative Examples 9 to 12 were pre-treated in an oven at about 150 DEG C for 4 hours in contact with oxygen. Thereafter, the preprocessed liquid crystal composition was poured into 4.0 占 퐉 TN cells prepared and dried beforehand, and the voltage retention ratio after the heat treatment was measured under the same conditions as those in which the initial voltage holding ratio was measured using the above cells.

- Calculation of changes in voltage holding ratio after heat treatment in more severe conditions

The initial voltage holding ratio (VHR 0 ) measured in the above manner and the voltage holding ratio (VHR t ) after heat treatment under more severe conditions were substituted into the above formula 2 to calculate the degree of change in the voltage holding ratio.

(5) Evaluation of UV stability under harsher conditions

- Measurement of voltage retention after UV irradiation in more severe conditions

The liquid crystal compositions prepared in Examples 9 to 12 and Comparative Examples 9 to 12 were pretreated with 10 J of UV irradiation in an oxygen-contact environment. Thereafter, the preprocessed liquid crystal composition was injected into each of 4.0 占 퐉 TN cells prepared and dried in advance, and the voltage retention ratio after the UV irradiation was measured under the same conditions as those in which the initial voltage maintenance ratio was measured using the cell.

- Calculation of voltage maintenance rate change after more severe UV irradiation

The initial voltage holding ratio (VHR 0 ) measured in the above manner and the voltage holding ratio (VHR t ) after UV irradiation under severe conditions were substituted into the formula (2), and the degree of change of the voltage holding ratio was calculated.

Clear point [℃] Evaluation of thermal stability [%] UV stability evaluation [%] Evaluation of thermal stability [%] UV stability evaluation [%] ΔVHR (100 ° C., 60 Hz) ΔVHR (100 ° C., 60 Hz, 3 J) VHR (100 DEG C, 60 Hz, 20J) ΔVHR (100 ° C., 30 Hz) DELTA VHR (100 DEG C, 30 Hz, 3J) DELTA VHR (100 DEG C, 30 Hz, 20J) Example 1 74.9 One One One 1.5 One One Example 2 75 One One One 1.5 One One Example 3 79.8 One One One 1.5 One One Example 4 79.8 One One One 1.5 One One Example 5 78.7 One One One 1.5 One One Example 6 78.8 One One One 1.5 One One Example 7 78.4 One One One 1.5 One One Example 8 78.5 One One One 1.5 One One Reference example 76.2 Less than 1 Less than 1 Less than 1 Less than 1 Less than 1 Less than 1 Comparative Example 1 75 16 5 6 26 7 9 Comparative Example 2 73.8 4 3 3.5 5 5 6 Comparative Example 3 79.9 20 9 13 26 10 16 Comparative Example 4 78.6 5 3 4 6 5 6 Comparative Example 5 78.8 12 5 6 16 8 9 Comparative Example 6 77.7 4 3 3.5 5 5 6 Comparative Example 7 78.5 20 7 10 23 8 12 Comparative Example 8 77.5 5 4.5 5.5 6 5 6

Clear point [℃] Evaluation of thermal stability [%] UV stability evaluation [%] Evaluation of thermal stability [%] UV stability evaluation [%] ΔVHR (100 ° C., 60 Hz) ΔVHR (100 ° C., 60 Hz, 10 J) ΔVHR (100 ° C., 30 Hz) DELTA VHR (100 DEG C, 30 Hz, 10J) Example 9 76.4 3 2 3.5 3 Example 10 76.4 3.5 2 4.5 3 Example 11 84.6 5 3 6 4 Example 12 84.6 5 3 6 4 Comparative Example 9 76.5 30 10 35 11 Comparative Example 10 75.5 6 4 7 5 Comparative Example 11 84.7 40 20 46 22 Comparative Example 12 82.4 10 7 11 8

Referring to Tables 4 and 5, it is also possible to use a compound having a double bond at the terminal thereof, a terphenyl group at the center thereof, or a -CF 2 O- or -CF 2 O- group, as in Comparative Examples 1, 3, 5, 7, When a liquid crystal molecule containing a linking group such as CH 2 O- is used, it is confirmed that heat and light stability are poor as compared with the reference example not employing such a structure.

Compared with Comparative Examples 2, 4, 6, 8, 10 and 12 in which known light stabilizers were added to Comparative Examples 1, 3, 5, 7, 9 and 11 in which heat and light stability were poor, It is confirmed that both the thermal stability and the light stability are excellent in the examples in which the light stabilizer according to the present invention is incorporated. Compared with Comparative Examples 1, 3, 5, 7, 9, and 11 in which no light stabilizer was added, the transparent point decreased by 1 ° C or more in Comparative Examples in which conventional light stabilizers were added, It is confirmed that the change of the transparent point is hardly changed to 0.1 占 폚 or less in the embodiments in which the light stabilizer according to the present invention is incorporated.

That is, by using the light stabilizer according to one embodiment of the present invention, heat and light stability can be remarkably improved without changing the physical properties of the liquid crystal molecules having poor heat and light stability. Accordingly, the liquid crystal composition according to an embodiment of the present invention can admit various liquid crystal molecules that have been restricted in use due to adverse effects on the stability and lifetime of the liquid crystal display device, Devices. &Lt; / RTI &gt;

Claims (11)

A light stabilizer represented by the following formula (1); And
Wherein at least one liquid crystal molecule selected from the group consisting of liquid crystal molecules represented by the following general formulas (2) and (3)
[Chemical Formula 1]
Figure pat00042

Wherein R 1 is a radical of any one of a straight chain alkyl group having 4 to 15 carbon atoms and a straight chain alkoxy group having 4 to 15 carbon atoms,
(2)
Figure pat00043

(3)
Figure pat00044

In the above Formulas 2 and 3,
R 2 to R 5 are each independently selected from the group consisting of hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with halogen, An alkenyl group having 2 to 12 carbon atoms and an alkoxy group having 1 to 12 carbon atoms substituted with halogen,
A 1 to A 5 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-
Z 1 to Z 3 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.
The liquid crystal composition according to claim 1, wherein the difference in the transparent point of the formula (1)
[Formula 1]
Transparent point difference (C) = | T a - T b |
In the formula (1), T a is a transparent point of a liquid crystal composition not containing a light stabilizer, and T b is a transparent point of a liquid crystal composition containing a light stabilizer at 0.1 wt%.
The liquid crystal composition according to claim 1, wherein R 1 in the formula (1) is a radical of any one of a straight-chain alkyl group having 6 to 12 carbon atoms and a straight-chain alkoxy group having 6 to 12 carbon atoms.
The liquid crystal composition according to claim 1, wherein the light stabilizer is contained in an amount of 0.005 to 5 parts by weight based on 100 parts by weight of liquid crystal molecules.
The liquid crystal composition according to claim 1, wherein R 2 and R 3 in Formula (2) are each independently any one of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a vinyl group, and -CH = CHCH 3 .
The liquid crystal composition according to claim 1, wherein the liquid crystal molecule represented by formula (2) comprises a liquid crystal molecule represented by formula (2-1)
[Formula 2-1]
Figure pat00045

In the general formula (2-1), R a and R b are each independently a radical of a methoxy group, an ethyl group, a propyl group, a vinyl group or -CH = CHCH 3 .
The method of claim 1, wherein the alkoxy group of the formula (III) of R 4 and R 5 are each independently fluorine, an alkyl group having 1 to 5 carbon atoms, a vinyl group, -CH = CHCH 3, trifluoromethoxy Messenger group and having 1-5 carbon atoms Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;
The liquid crystal composition according to claim 1, wherein the liquid crystal molecule of formula (3) comprises at least one liquid crystal molecule of liquid crystal molecules represented by the following formulas (3-1) to (3-6)
[Formula 3-1]
Figure pat00046

In the above formula (3-1), R c is a radical of any of the alkyl groups having 2 to 5 carbon atoms, R d to R g are each independently hydrogen or fluorine,
[Formula 3-2]
Figure pat00047

In the formula (3-2), R h is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R i to R 1 are each independently hydrogen or fluorine,
[Formula 3-3]
Figure pat00048

Wherein R m is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R n and R o are each independently hydrogen or fluorine, R p is a fluorine or trifluoromethoxy group,
[Chemical Formula 3-4]
Figure pat00049

Wherein R s is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R t to R w are each independently hydrogen or fluorine, Z a is -CH 2 O- or -CF 2 O -ego,
[Formula 3-5]
Figure pat00050

R aa is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ab to R ae are each independently hydrogen or fluorine, Z b is a single bond, -CH 2 O- or - CF 2 O-,
[Chemical Formula 3-6]
Figure pat00051

In the above formula (3-6), R af is a radical of any of the alkyl groups having 2 to 3 carbon atoms, R ag to R aj are each independently hydrogen or fluorine, Z c is a single bond, -CH 2 O- or - CF 2 O-.
The liquid crystal composition according to claim 1, which comprises 10 to 50 parts by weight of a liquid crystal molecule represented by the formula (2) and 3 to 55 parts by weight of the liquid crystal molecule represented by the formula (3) when the total weight of the liquid crystal molecules is 100 parts by weight.
The liquid crystal composition according to claim 1, further comprising a liquid crystal molecule represented by the following formula (4):
[Chemical Formula 4]
Figure pat00052

In Formula 4,
R 6 and R 7 are each independently hydrogen, halogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with halogen, An alkenyl group having 2 to 12 carbon atoms and an alkoxy group having 1 to 12 carbon atoms substituted with halogen,
A 6 to A 9 each independently represent a cyclohexylene group, a phenylene group, a cyclohexylene group in which at least one hydrogen is substituted with a methyl group or a halogen, or a phenylene group in which at least one of the hydrogen atoms is a methyl group or a halogen-
Z 4 to Z 6 each independently represents a single bond, -CH 2 CH 2 -, -CHFCH 2 -, -CH 2 CHF-, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - , -CH 2 O- or -CF 2 O-.
A first substrate and a second substrate arranged to face each other and spacers formed between the first and second substrates so as to be spaced apart from each other,
The liquid crystal cell according to claim 1, wherein the liquid crystal composition according to claim 1 is injected into a cell formed by the first and second substrates and the spacer.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019069550A1 (en) * 2017-10-04 2019-04-11 Jnc株式会社 Liquid crystal composition and liquid crystal display element

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0536958A (en) 1991-07-24 1993-02-12 Fujitsu Ltd Solid-state image pick up device and manufacture thereof
KR20140004119A (en) 2010-12-07 2014-01-10 메르크 파텐트 게엠베하 Liquid crystal medium and electrooptic display

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0536958A (en) 1991-07-24 1993-02-12 Fujitsu Ltd Solid-state image pick up device and manufacture thereof
KR20140004119A (en) 2010-12-07 2014-01-10 메르크 파텐트 게엠베하 Liquid crystal medium and electrooptic display

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019069550A1 (en) * 2017-10-04 2019-04-11 Jnc株式会社 Liquid crystal composition and liquid crystal display element
CN111032827A (en) * 2017-10-04 2020-04-17 捷恩智株式会社 Liquid crystal composition and liquid crystal display element
JPWO2019069550A1 (en) * 2017-10-04 2020-09-10 Jnc株式会社 Liquid crystal composition and liquid crystal display element

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