JP2000026861A - Nematic liquid crystal composition and liquid crystal display element prepared by using same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a nematic liq. crystal compsn. which shows a nematic phase in a wide temp. range including room temp. and has various degrees of optical anisotropy and dielectric anisotropy by homogeneously mixing three specific compds. SOLUTION: Compds. of formulas I, II, and III are used. In formula I, R1 and R2 are each 1-12C alkyl, 1-12C alkoxy, cyano, halogen, or H; A and G are each phenylene, biphenylene, cyclohexylene, or methylated biphenylene; R3 is methyl, halogen, or H; and Z1 is a single bond or an ester bond. In formula II, R3 and R4 are each 1-12C alkyl or 1-12C alkoxy. In formula III, R3 and R4 are each 1-12C alkyl or 1-12C alkoxy; Z2 is H, cyano, or halogen; and E is phenylene, biphenylene, cyclohexylene, or a divalent phenylcyclohaxane group. Pref., the amounts of the compounds of formulas I, II and III are, by pts.wt. 1.0-60.0, 1.0-60 and 1.0-20.0, respectively.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal composition and a liquid crystal display device using the same, and more particularly to a liquid crystal composition which exhibits a nematic phase in a wide temperature range including room temperature, and has various sizes of optical anisotropy and dielectric constant. The present invention relates to a liquid crystal composition having anisotropy and a liquid crystal display device capable of performing multiple driving using the liquid crystal composition.

[0002]

2. Description of the Related Art A compound represented by the following structural formula (formula 1) is a non-polar liquid crystal compound having a low viscosity.
2,638,634 and DDR171,971.

[0003]

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[0004] Here, R ₁ and R ₂ are simultaneously or independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cyano group, a halogen atom, a hydrogen atom, A and G
Is simultaneously or independently phenylene, biphenylene, cyclohexylene, or biphenylene containing a methyl group, R ₃ is a methyl group, a halogen atom, or a hydrogen atom, and Z ₁ is a single bond or an ester bond (—COO—).
Are respectively shown.

A phenylalkyldioxaborinane (dioxaborina) represented by the following structural formula (Formula 4)
ne) The derivative is a polar liquid crystal compound having a high dielectric anisotropy Δε. The synthesis method and properties of the dioxaborinane derivative represented by the following structural formula are described in detail in US Pat. No. 4,853,150.

[0006]

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Here, R ₅ is an alkyl group having 1 to 12 carbon atoms, Y is a cyano group, a halogen atom, —OR,

[0008]

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Or

[0010]

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Wherein X, V and W are, simultaneously or independently, a hydrogen atom, a halogen atom, a cyano group, and
It shows a 12 alkyl group or a C1-C12 alkoxy group, and R shows a C1-C12 alkyl group.

The isothiocyanate derivative represented by the following structural formula (Formula 5) is a polar liquid crystal compound having low viscosity and high dielectric anisotropy. The properties of the isothiocyanate compound represented by the following structural formula are described in detail in PL 241,286 and U.S. Pat. No. 4,528,116.

[0013]

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Here, R ₁ is an alkyl group having 1 to 12 carbon atoms, J and D are phenylene, biphenylene, cyclohexylene or divalent phenylcyclohexane simultaneously or independently, and W is a single bond or ethylene. Group (-C
H ₂ CH ₂ -) indicates respectively.

The tolan derivative represented by the following structural formula (Formula 6) is a non-polar liquid crystal compound having a high optical anisotropy Δn, and its characteristics are described in US Pat. No. 3,529,
No. 482.

[0016]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

The pyrimidine-phenyl derivative represented by the following structural formula (Chemical Formula 2) is a liquid crystal having a low elastic modulus, and its synthesis is described in the following document [Mol. Crys. Liq. Cr
yst, 68, 57 (1981)] and patent DDR958
92.

[0019]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

The compound represented by the following structural formula (chemical formula 3) is a non-polar substance, and its characteristics are described in the following literature [Liqu
id Crystal, 5, 159 (1989)].

[0022]

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Here, R ₃ and R ₄ are simultaneously or independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and Z ₂ is a hydrogen atom, a cyano group or a halogen atom. , E represent phenylene, biphenylene, cyclohexylene, or divalent phenylcyclohexane, respectively.

[0024]

The technical problem to be solved by the present invention is that the liquid crystal exhibits a nematic phase in a wide temperature range including room temperature and has various sizes of optical anisotropy and dielectric anisotropy. Providing a composition.

Another technical problem to be solved by the present invention is that TN (tw) capable of multiple driving using the liquid crystal composition is used.
It is an object of the present invention to provide a liquid crystal display device.

[0026]

In order to achieve the above technical object, the present invention comprises a compound represented by the formula 1, a compound represented by the formula 2, and a compound represented by the formula 3. A nematic liquid crystal composition is provided.

[0027]

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Here, R ₁ and R ₂ are, simultaneously or independently, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cyano group, a halogen atom, a hydrogen atom, A and G
Is simultaneously or independently phenylene, biphenylene, cyclohexylene, or biphenylene containing a methyl group, R ₃ is a methyl group, a halogen atom, or a hydrogen atom, and Z ₁ is a single bond or an ester bond (—COO—).
Respectively,

[0029]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms,

[0031]

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Here, R ₁ and R ₂ are simultaneously or independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms; Z ₂ is a hydrogen atom, a cyano group or a halogen atom; Represents phenylene, biphenylene, cyclohexylene or divalent phenylcyclohexane, respectively.

The liquid crystal composition may further include a compound represented by Formula 4, 5, or 6.

[0034]

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Here, R ₅ is an alkyl group having 1 to 12 carbon atoms, Y is a cyano group, a halogen atom, —OR,

[0036]

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Or

[0038]

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Wherein X, V and W are, simultaneously or independently, a hydrogen atom, a halogen atom, a cyano group, and a
12 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms, R represents an alkyl group having 1 to 12 carbon atoms,

[0040]

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Here, R ₁ is an alkyl group having 1 to 12 carbon atoms, J and D are phenylene, biphenylene, cyclohexylene, or divalent phenylcyclohexane simultaneously or independently, and W is a single bond or ethylene. Group (-C
H ₂ CH ₂ —),

[0042]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

Another technical problem is to provide a liquid crystal display device characterized by being manufactured by inserting the liquid crystal composition according to the present invention between a pair of electrode substrates.

[0045]

BEST MODE FOR CARRYING OUT THE INVENTION The liquid crystal composition of the present invention contains compounds of formulas 1 to 3 as essential constituents.

[0046]

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Here, R ₁ and R ₂ are, simultaneously or independently, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cyano group, a halogen atom, a hydrogen atom, A and G
Is a phenylene, biphenylene, cyclohexylene or biphenylene containing a methyl group, simultaneously or independently, R ₃ is a methyl group, a halogen atom or a hydrogen atom, Z1 is a single bond or an ester bond (—COO—)
Respectively,

[0048]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms,

[0050]

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Here, R ₃ and R ₄ are simultaneously or independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, Z ₂ is a hydrogen atom, a cyano group or a halogen atom, Represents phenylene, biphenylene, cyclohexylene or divalent phenylcyclohexane, respectively.

In the liquid crystal composition, the content of the compound represented by Chemical Formulas 1 to 3 is slightly changed according to the characteristics of the device to be manufactured, but the content of the compound represented by Chemical Formula 1 is 1.0 to 60. It is preferable that the content of the compound represented by Formula 2 is 1.0 to 60.0 parts by weight, and the content of the compound represented by Formula 3 is 1.0 to 20.0 parts by weight. In this case, the total of the compounds represented by Chemical Formulas 1 to 3 is 100 parts by weight. Here, the chemical formula 1
When the content of the compound is out of the above range, the non-polarity of the liquid crystal composition becomes excessively large and the threshold voltage of the liquid crystal composition increases. If the viscosity of the compound is excessively high and the content of the compound of Formula 3 is out of the above range, the viscosity of the liquid crystal composition is excessively high, which is not desirable.

Further, the liquid crystal composition of the present invention may further include a compound represented by Formula 4, 5, or 6.

[0054]

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Here, R ₅ is an alkyl group having 1 to 12 carbon atoms, Y is a cyano group, a halogen atom, —OR,

[0056]

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Or

[0058]

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X, V, and W are simultaneously or independently a hydrogen atom, a halogen atom, a cyano group, and a
12 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms, R represents an alkyl group having 1 to 12 carbon atoms,

[0060]

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Here, R ₁ is an alkyl group having 1 to 12 carbon atoms, j and D are phenylene, biphenylene, cyclohexylene, or divalent phenylcyclohexane simultaneously or independently, and W is a single bond or ethylene. Group (-C
H ₂ CH ₂ —),

[0062]

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Here, R ₃ and R ₄ simultaneously or independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

The content of the liquid crystal compounds of Formulas 4 to 6 slightly varies according to the characteristics of the device to be manufactured.
The content of the compound of Formula 4 is 1.0 to 20.0 parts by weight, the content of the compound of Formula 5 is 1.0 to 20.0 parts by weight, and the content of the compound of Formula 6 is 1.0 to 20.0 parts by weight. It is desirable that In this case, the total of the compounds represented by the compounds represented by the chemical formulas 4 to 6 and the compound represented by the chemical formulas 4 to 6 arbitrarily compounded is 100 parts by weight. Here, when the content of the compound of Formula 4 is out of the range, the viscosity of the liquid crystal composition becomes excessively large, and
When the content of the compound is out of the range, the viscosity of the liquid crystal composition becomes excessively high. When the content of the compound of the formula 6 is out of the range, the non-polarity of the liquid crystal composition becomes excessively large. There is a problem that the threshold voltage becomes excessively large.

[0065]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited only to the following Examples.

Example 1 Compound 1 represented by Chemical Formula 1a as shown in Tables 1 to 3
4.4% by weight, 2.5% by weight of the compound represented by Formula 1b, 16.2% by weight of the compound represented by Formula 1c, 2.7% by weight of the compound represented by Formula 1d, and represented by Formula 1e 4.4% by weight of the compound, 8.9% by weight of the compound represented by Formula 2a, 9.9% by weight of the compound represented by Formula 2b, 12.0% by weight of the compound represented by Formula 2c, and 2% by weight of Formula 2d 9.1% by weight of the compound represented by the formula, 7.5% by weight of the compound represented by the chemical formula 2e, 6.2% by weight of the compound represented by the chemical formula 2f, and 4.7 of the compound represented by the chemical formula 3a
% By weight, and 1.5% by weight of the compound represented by the chemical formula 3b.
A liquid crystal composition comprising: The liquid crystal composition is heated and stirred at a temperature higher than the temperature at which the liquid crystal composition exhibits an isotropic phase, and then the temperature of the liquid crystal composition is cooled to room temperature again, and the nematic phase liquid crystal is uniformly mixed. A composition was obtained.

The liquid crystal composition thus obtained was twisted at 90 ° to a 6 μm twisted nematic (TN).
c) After injecting the liquid crystal composition into the cell, at room temperature, an electro-optical property is obtained.
ties) was measured. Table 9 shows the obtained electro-optical characteristics.
It was shown to. Referring to Table 9, the nematic phase for temperature of the liquid crystal composition is shown.
T _NI of mation temperature) 6
6.5 ° C. Therefore, it was found that the present liquid crystal composition exhibited a nematic phase up to 66.5 ° C. including room temperature.
On the other hand, optical anisotropy (optical anisotro
py) Δn is 0.133, dielectric anisotropy (positivity)
ve anisotropy of permitti
(vity) Δε is 15.0, 10 of light projected on the cell
% At the time of passing (%)
who the cell passes 10
% Of the light falling on
saturation voltage (saturation voltage) V ₉₀ of the voltage when the threshold voltage V ₁₀ is to pass 90% of the light to be administered 1.36 V, the cell of it) is 1.
95V, duty number (th
enumberofduties) N ₉₀ was 8.37.

[0068]

(Equation 1)

Examples 2 to 13 Liquid crystal compositions were prepared in the same manner as in Example 1 except that the components of the liquid crystal composition were changed as shown in Tables 1 to 8. Then, after injecting the obtained liquid crystal composition into a 6 μm TN cell twisted by 90 ° as in Example 1, the electro-optical characteristics were measured at room temperature. Table 2 shows the obtained electro-optical characteristics.

Referring to Table 9, it can be seen that the liquid crystal composition of the present invention has a T _NI of 63.2 to 80.7 ° C. and maintains a nematic phase in a wide temperature range including room temperature. Further, referring to Tables 1 to 9, it can be seen that the liquid crystal composition of the present invention can variously adjust the optical anisotropy and the dielectric anisotropy by adjusting the ratio of each component. Further, the range of N ₉₀ of the liquid crystal composition according to the present invention is from 8.37 to 10.8
Since the liquid crystal composition according to the present invention is 5, a liquid crystal display device capable of multiple driving can be manufactured. On the other hand, Tables 1 to
In 8, the alkyl group portion of the alkyl group or the alkoxy group indicates an alkyl group having a normal structure.

[0071]

[Table 1]

[0072]

[Table 2]

[0073]

[Table 3]

[0074]

[Table 4]

[0075]

[Table 5]

[0076]

[Table 6]

[0077]

[Table 7]

[0078]

[Table 8]

[0079]

[Table 9]

[0080]

As described above, the liquid crystal composition according to the present invention exhibits a nematic phase in a wide temperature range including room temperature, and has various sizes of optical anisotropy and dielectric anisotropy. In addition, a TN liquid crystal display device manufactured using the liquid crystal composition of the present invention can be driven multiple times.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09K 19/34 C09K 19/34 G02F 1/13 500 G02F 1/13 500 (72) Inventor Shigeru Hayashi South Korea Theory of Gangnam-gu, Seoul ▲ ken ▼ 1 9-12, Dong-dong (72) Inventor Jeong Dong Chin, Seoul, Seoul, Korea 110-1 Sento 3-dong, 72-72 (72) Inventor Uo-Kan Han, Yongin-si, Gyeonggi-do, Republic of Korea 629 Toyotokuri, Mizue-emura

Claims (16)

[Claims] 1. A nematic liquid crystal composition comprising a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, and a compound represented by Chemical Formula 3. Embedded image Here, R ₁ and R ₂ are simultaneously or independently having 1 to 1 carbon atoms.
2 alkyl group, an alkoxy group having 1 to 12 carbon atoms, a cyano group, a halogen atom, a hydrogen atom, A and G are simultaneously or independently phenylene, biphenylene, biphenylene containing cyclohexylene or a methyl group,, R ₃ Represents a methyl group, a halogen atom, or a hydrogen atom; Z ₁ represents a single bond or an ester bond (—COO—); Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
2 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms; Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
An alkyl group of 2 or an alkoxy group having 1 to 12 carbon atoms, Z ₂ represents a hydrogen atom, a cyano group or a halogen atom,
E represents phenylene, biphenylene, cyclohexylene or divalent phenylcyclohexane, respectively. 2. The compound represented by Formula 1 has a content of 1.0 to 60.0 parts by weight, the compound represented by Formula 2 has a content of 1.0 to 60.0 parts by weight, and a compound represented by Formula 3. The content of the compound is 1.0 to 20.0 parts by weight (provided that
The total of the compounds represented by Chemical Formulas 1 to 3 is 100 parts by weight. 2. The nematic liquid crystal composition according to claim 1, wherein 3. The nematic liquid crystal composition according to claim 1, further comprising a compound represented by Formula 4. Embedded image Here, R ₅ is an alkyl group having 1 to 12 carbon atoms, Y is a cyano group, is a halogen atom, —OR, Or X, V, and W simultaneously or independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and R represents 1 carbon atom. ~
Represents 12 alkyl groups. 4. The content of the compound represented by Formula 4 is in a ratio of 1.0 to 20.0 parts by weight (however, the total of the compounds represented by Formulas 1 to 4 is 100 parts by weight). The nematic liquid crystal composition according to claim 3, wherein: 5. The nematic liquid crystal composition according to claim 1, further comprising a compound represented by Formula 5. Embedded image Here, R ₁ represents an alkyl group having 1 to 12 carbon atoms, and J and D
Represents phenylene, biphenylene, cyclohexylene, or divalent phenylcyclohexane simultaneously or independently, and W represents a single bond or an ethylene group (—CH ₂ CH ₂ —).
Are respectively shown. 6. The content of the compound represented by Formula 5 is in a ratio of 1.0 to 20.0 parts by weight (provided that the total amount of the compounds represented by Formulas 1 to 3 and 5 is 100 parts by weight. The nematic liquid crystal composition according to claim 5, wherein: 7. The nematic liquid crystal composition according to claim 1, further comprising a compound represented by Formula 6. Embedded image Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
2 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms. 8. The content of the compound represented by the chemical formula 6 is in a ratio of 1.0 to 20.0 parts by weight (provided that the total amount of the compounds represented by the chemical formulas 1 to 3 and 6 is 100 parts by weight. The nematic liquid crystal composition according to claim 7, wherein: 9. A nematic liquid crystal composition comprising a compound represented by Formula 1, a compound represented by Formula 2, and a compound represented by Formula 3 is inserted between a pair of electrode substrates. Liquid crystal display device. Embedded image Here, R ₁ and R ₂ are simultaneously or independently having 1 to 1 carbon atoms.
2 alkyl group, an alkoxy group having 1 to 12 carbon atoms, a cyano group, a halogen atom, a hydrogen atom, A and G are simultaneously or independently phenylene, biphenylene, biphenylene containing cyclohexylene or a methyl group,, R ₃ Represents a methyl group, a halogen atom, or a hydrogen atom; Z ₁ represents a single bond or an ester bond (—COO—); Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
2 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms; Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
An alkyl group of 2 or an alkoxy group having 1 to 12 carbon atoms, Z ₂ represents a hydrogen atom, a cyano group or a halogen atom,
E represents phenylene, biphenylene, cyclohexylene or divalent phenylcyclohexane, respectively. 10. The content of the compound represented by Formula 1 in the liquid crystal composition is 1.0 to 60.0 parts by weight, and the content of the associated product represented by Formula 2 is 1.0 to 60.0 parts by weight. ,
The content of the compound represented by Chemical Formula 3 is 1.0 to 20.0 parts by weight (however, the total of the compounds represented by Chemical Formulas 1 to 3 is 100 parts by weight). 10. The liquid crystal display device according to 9. 11. The liquid crystal display device according to claim 9, wherein the liquid crystal composition further includes a compound represented by Formula 4. Embedded image Here, R ₅ is an alkyl group having 1 to 12 carbon atoms, Y is a cyano group, a halogen atom, —OR, Or X, V, and W simultaneously or independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and R represents 1 carbon atom. ~
Represents 12 alkyl groups. 12. The content of the compound represented by Formula 4 is in a ratio of 1.0 to 20.0 parts by weight (however, the total amount of the compounds represented by Formulas 1 to 4 is 100 parts by weight. The liquid crystal display device according to claim 11, wherein: 13. The liquid crystal display device according to claim 9, wherein the liquid crystal composition further comprises a compound represented by Formula 5. Embedded image Here, R ₁ represents an alkyl group having 1 to 12 carbon atoms, and J and D
Represents phenylene, biphenylene, cyclohexylene, or divalent phenylcyclohexane simultaneously or independently, and W represents a single bond or an ethylene group (—CH ₂ CH ₂ —).
Are respectively shown. 14. The content of the compound represented by Formula 5 is in a ratio of 1.0 to 20.0 parts by weight (provided that the total amount of the compounds represented by Formulas 1 to 3 and 5 is 100 parts by weight. 14. The liquid crystal display device according to claim 13, wherein: 15. The liquid crystal display device according to claim 9, wherein the liquid crystal composition further comprises a compound represented by Formula 6. Embedded image Here, R ₃ and R ₄ may be simultaneously or independently and have 1 to 1 carbon atoms.
2 represents an alkyl group or an alkoxy group having 1 to 12 carbon atoms. 16. The content of the compound represented by Formula 6 is in a ratio of 1.0 to 20.0 parts by weight (provided that the total of the compounds represented by Formulas 1 to 3 and 6 is 100 parts by weight. 16. The liquid crystal display device according to claim 15, wherein: