JP2002249779A - Liquid crystal composition and liquid crystal display device - Google Patents

Abstract

(57) [Summary] (Problem corrected) [PROBLEMS] To improve a sharpness γ and a temperature dependency of a threshold voltage without increasing a threshold voltage, and provide a liquid crystal composition having a fast response speed at room temperature and low temperature and a liquid crystal composition having the same. Provide used liquid crystal display devices. SOLUTION: A general formula I is used as a first component. Wherein at least one of R ¹ and R ² is a C1-16 alkyl group or an alkoxyl group, and at least one of them is a C3-16 alkenyl group. (R ³ and R ⁴ are a C1-16 alkyl group or an alkoxyl group, a C3-16 alkenyl group). (Alkyl or alkoxyl group ^{R 5} is C1～16, alkenyl group C2~16.) Contain one or more compounds of and nematic phase - isotropic liquid phase transition temperature seventy-five to one hundred thirty ° C., smectic Liquid crystal composition having a phase or solid phase-nematic phase transition temperature of −60 to −10 ° C. and a refractive index anisotropy (Δn) of 0.07 to 0.30, and a liquid crystal display device using this composition .

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a nematic liquid crystal composition useful as an electro-optical liquid crystal display material, and a liquid crystal display device using the same.

[0002]

2. Description of the Related Art Since liquid crystal displays (LCDs) have appeared as calculator displays, they have progressed from computer development to TN-LCDs (twisted nematic liquid crystal displays) to STN-LCDs. It has responded to the expansion of capacity. STN-L
CDs include Scheffer and others [SID '85 Digest, 120
(1985)] or Kinukawa et al. [SID '86 Digest, 122
Page (1986)], and has begun to spread widely to displays for high information processing such as word processors and personal computers. Recently, an active addressing drive scheme has been proposed for the purpose of improving the response characteristics of an STN-LCD. (Proc. 12th International Display Res
earch Conference p.503 1992)
(Personal Digital Assistance) requires good display characteristics in a wider temperature range. Such a liquid crystal material is required to have a low viscosity, a low driving voltage and a constant value over a wide temperature range, or a driving voltage that does not fluctuate in a frequency range corresponding to various time divisions. I have. However, the response speed and contrast when incorporated into a display element cannot be said to be sufficient, and new liquid crystal compounds or liquid crystal compositions have been proposed at present.

[0003] With the rapid expansion of applications of LCDs, LCDs are not only used indoors, but are also used outdoors where temperature conditions are severe, such as displays for portable terminals of computers, in-vehicle instruments and displays for outdoor use. Has increased. For this reason, there has been a problem that the display contrast is lowered due to a change in the temperature of the environment in which the LCD is placed, and the display quality is deteriorated due to the lowered response speed at low temperatures. In addition, high reliability has been required for outdoor use.

There are various causes for the deterioration of LCD display quality due to a change in ambient temperature. The change is caused by a change in temperature such as an elastic constant or a dielectric constant of a nematic liquid crystal and a change in temperature of an intrinsic pitch of an added chiral substance. To suppress the temperature change of the threshold voltage Vth, to improve the temperature dependency of the threshold voltage by controlling the temperature change of the specific pitch of the chiral substance (JP-A-55-38869) is already known, There have been problems in that the effect varies depending on the combination of the base liquid crystal and the chiral substance, and that display properties such as response are adversely affected by increasing the amount of chiral.

[0005]

SUMMARY OF THE INVENTION The problem to be solved by the present invention is to increase the sharpness γ without increasing the threshold voltage.
And to improve the temperature dependence of the threshold voltage, to provide a liquid crystal composition with a fast response speed at room temperature and low temperature,
Another object of the present invention is to provide a liquid crystal display device having a high response speed using the composition.

[0006]

Means for Solving the Problems In order to solve the above-mentioned problems, the present invention has examined the liquid crystal compositions using various liquid crystal compounds, and has found the following liquid crystal compositions. General formula (I) as the first component

[0007]

Embedded image

(Wherein R ¹ and R ² are each independently an alkyl group or an alkoxyl group having 1 to 16 carbon atoms which may be substituted by fluorine, at least one of which has 3 to 16 carbon atoms. Represents an alkenyl group, provided that when R ¹ and R ² are alkenyl groups, the double bond present in R ¹ and R ² always separates one or more carbon atoms from the benzene ring.) Contains one or more compounds selected from the formula (II) as a second component

[0009]

Embedded image

(Wherein R ³ and R ⁴ each independently represent an alkyl or alkoxyl group having 1 to 16 carbon atoms and an alkenyl group having 3 to 16 carbon atoms, which may be substituted by fluorine. , R ³ , R ⁴ is an alkenyl group, R ³ ,
Double bonds present in R ⁴ is spaced exactly one or more carbon atoms from a benzene ring. ) Containing one or more compounds selected from the general formula (III) as the third component

[0011]

Embedded image

(Wherein, R ⁵ is independently selected from an alkyl or alkoxyl group having 1 to 16 carbon atoms and an alkenyl group having 2 to 16 carbon atoms which may be substituted by fluorine). It contains one or more compounds and has a nematic phase-isotropic liquid phase transition temperature of 75.
~ 130 ° C, the smectic phase or solid phase-nematic phase transition temperature is -60 ~ -10 ° C, and the refractive index anisotropy (Δ
A liquid crystal composition, wherein n) is in the range of 0.07 to 0.30. A liquid crystal display device using this composition can improve its temperature dependency without excessively increasing the threshold voltage. Further, the response speed, particularly at a low temperature of 0 ° C. or lower, can be improved.

[0013]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, examples of the present invention will be described. One or more compounds selected from the general formula (I) are contained as the first component, and one or two compounds are preferable. In the formula, R ¹ and R ² each represent an alkyl group having 1 to 16 carbon atoms or an alkenyl group having 3 to 16 carbon atoms, and at least one is preferably an alkenyl group, and the formulas (a) and (b) Is more preferable,

[0014]

Embedded image (The structural formula is connected to the ring at the right end.)

Formula (b) is particularly preferred. Further, it is more preferable that both R ¹ and R ² are alkenyl groups, and particularly, formula (b)
It is preferred that The second component contains one or more compounds selected from the general formula (II),
Species or two are preferred. Further, in the formula, R ³ and R ⁴ represent an alkyl group having 1 to 16 carbon atoms and an alkenyl group having ^{3 to} 16 carbon atoms, more preferably an alkenyl group, and the formula (a),
The structure of (b) is more preferable,

[0016]

Embedded image (The structural formula is connected to the ring at the right end.)

Formula (b) is particularly preferred. Further, it is more preferable that both R ³ and R ⁴ are alkenyl groups, and particularly formula (b)
It is preferred that Although containing one or more compounds selected from the general formula (III) as the third component,
One or two are preferred. Also, in the formula, each of R ⁵ may be independently fluorine-substituted, and has 1 to 16 carbon atoms.
Alkyl or alkoxyl group, having 2 to 16 carbon atoms
Represents an alkenyl group of, but is preferably an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and as the alkyl group or alkenyl group having 1 to 5
(a) to (e) are particularly preferred.

[0018]

Embedded image (The structural formula is connected to the ring at the right end.)

This liquid crystal composition has a maximum nematic phase temperature.
The temperature is from 75 ° C to 130 ° C, preferably from 80 ° C to 110 ° C, particularly preferably from 85 ° C to 105 ° C. In addition, the smectic phase or solid phase-nematic phase transition temperature is
-10 ° C, preferably -60 ° C to -25 ° C, and -55 ° C to -30 ° C
C is more preferred. Δn is characterized by being 0.07 to 0.30, preferably 0.08 to 0.22. General formulas (IV) and (V) as the fourth component

[0020]

Embedded image

(Wherein, R ⁶ , R ⁷ and R ⁸ are each independently an alkyl or alkoxyl group having 1 to 16 carbon atoms which may be substituted by fluorine, an alkenyl group having 2 to 16 carbon atoms, Represents an alkenyloxy group having 3 to 16 carbon atoms, or an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyl group having 1 to 10 carbon atoms, ring A, ring B, ring C, ring D
And ring E may each independently be substituted with a fluorine atom 1,4-phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, naphthalene-2, 6-
Diyl group, phenanthrene-2,7-diyl group, fluorene-
2,7-diyl group, trans-1,4-cyclohexylene group, 1,
2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, trans-1,3-dioxane-2,5-diyl group, pyridine-2,5-diyl group , Pyrimidine
-2,5-diyl group, represents a pyrazine-2,5-diyl group or a pyridazine-2,5-diyl group, l and m are each independently 0,
1 or represents a ^{2, Z 1, Z 2,} Z 3 and Z ⁴ are each independently a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 O- , -CH = CH
-, -COO- or -C≡C-, wherein X ² is a cyano group, a fluorine atom, a chlorine atom, a trifluoromethoxy group, a trifluoromethyl group, a difluoromethoxy group, a hydrogen atom, Represents a fluoroethoxy group, R ′ or —OR ′, R ′ represents a linear alkyl group having 1 to 12 carbon atoms or a linear alkenyl group having 2 to 12 carbon atoms, and X ¹ and X ³ represent a hydrogen atom , A fluorine atom or a chlorine atom. )), Preferably contains one or more compounds selected from the group consisting of

The compound contains one or more compounds selected from the group consisting of the general formulas (IV) and (V), preferably 3 or more, more preferably 3 to 20 and more preferably 5 to 15 Species are particularly preferred, in which the compound of general formula (IV) is at least 2
More preferably, it contains more than one species. R ⁶ , R ⁷ , and R ⁸ each independently may have 1 to 16 carbon atoms which may be substituted by fluorine.
Alkyl or alkoxyl group, having 2 to 16 carbon atoms
Represents an alkenyl group, an alkenyloxy group having 3 to 16 carbon atoms, or an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyl group having 1 to 10 carbon atoms, but an alkyl group having 1 to 16 carbon atoms. Group, an alkenyl group having 2 to 16 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms,
2 to 8 alkenyl groups are more preferred, and formulas (a) to (e) are particularly preferred as 1 to 5 alkyl or alkenyl groups.

[0023]

Embedded image (The structural formula is connected to the ring at the right end.)

Each of ring A, ring B, ring C, ring D and ring E is
1,4-phenyl optionally substituted by a fluorine atom
Nylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-
Phenylene group, naphthalene-2,6-diyl group, phenanthate
Len-2,7-diyl group, fluorene-2,7-diyl group, tran
1,4-cyclohexylene group, 1,2,3,4-tetrahydrona
Phthalene-2,6-diyl group, decahydronaphthalene-2,6-di
Yl group, trans-1,3 dioxane-2,5-diyl group, pyri
Gin-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine
Represents a 2,5-diyl group or a pyridazine-2,5-diyl group
Is a 1,4-phenylene group, trans-1,4-cyclohexyl
In ring A, ring B, ring D, and ring E,
-1,4-cyclohexylene group is more preferable, and the ring C
In this case, a 1,4-phenylene group is more preferred. l and m are respectively
Independently represents 0, 1 or 2, preferably 0 or 1
No. Z¹, Z^Two, Z^Three, Z^FourAre each independently a single bond, -CH_TwoCH
_Two-,-(CH _Two)_Four-, -OCH_Two-, -CH_TwoO-, -COO-, -CH = CH- or -C
≡C- stands for Z¹, Z^TwoIs a single bond, -C≡C-, -CH_TwoCH
_TwoIs preferred, and a single bond is more preferred. Z^Three, Z^FourAt
Is preferably a single bond, -COO- or -C≡C-, more preferably a single bond.
Good. X^TwoIs a cyano group, a fluorine atom, a chlorine atom,
Fluoromethoxy group, trifluoromethyl group, difluoro
Methoxy group, hydrogen atom, 3,3,3-trifluoroethoxy
Represents a group, R ′ or —OR ′, wherein R ′ is a straight chain having 1 to 12 carbon atoms.
Represents a linear alkyl group or 2 to 12 linear alkenyl groups.
But cyano group, fluorine atom, trifluoromethoxy
Group, a difluoromethoxy group is preferred, and a fluorine atom,
More preferred are a trifluoromethoxy group and a difluoromethoxy group.
Particularly, a fluorine atom is particularly preferred. X¹, X^ThreeIs hydrogen field
Represents a hydrogen atom, a fluorine atom or a chlorine atom.
A nitrogen atom is preferred, and a fluorine atom is particularly preferred.

In constituting the composition of the present invention,
Formulas (I), each containing one or more compounds selected from (II), the content is 5 to 60 mass each
%, And contains one or more compounds selected from the general formula (III), and the content is 5 to 40% by mass,
Furthermore, it is preferable that the fourth component contains one or more compounds selected from the group consisting of the general formulas (IV) and (V), and the content is 5 to 85% by mass. At this time, the general formula
(I), the content of the compound selected from (II) is 5 to 60 respectively
Although it is mass%, 5 to 30 mass% is preferable, and 5 to 20 mass% is particularly preferable. The content of the compound selected from the general formula (III) is 5 to 40% by mass, preferably 5 to 30% by mass,
0 mass% is more preferable. General formula (IV), the content of the compound selected from the group consisting of (V) is 5 to 85% by mass,
5 mass% is preferable, and 5 to 65 mass% is particularly preferable.

As the compound of the general formula (IV), ring A and ring B
Is a trans-1,4-cyclohexylene group, and Z ¹ and Z ² are each a single bond represented by the general formula (IV-a)

[0027]

Embedded image

(Wherein R ⁹ and R ¹⁰ have the same meanings as R ⁶ and R ⁷ , ring F represents a 1,4-phenylene group or trans-1,4-cyclohexylene group, and n represents 0 or It is preferable from the viewpoint of the effect of improving the response speed to contain one or more compounds selected from the group consisting of 1). Further, it is preferable that R ⁹ and R ¹⁰ are simultaneously or one of them is alkenyl from the viewpoint of steepness and response speed. The content of the general formula (IV-a) is
The content is 5 to 85% by mass, preferably 5 to 75% by mass, more preferably 5 to 65% by mass.

As the compound of the general formula (IV), the compound of the general formula (IV-b)

[0030]

Embedded image

(Wherein R ¹² and R ¹³ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine). It is effective for improving the speed, and its content is preferably 5 to 60% by mass.

As the compound of the general formula (IV), a compound of the general formula (IV-c)

[0033]

Embedded image

(Wherein R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine). It is preferable from the viewpoint of improvement and expansion of a wide liquid crystal temperature range. At this time, one or more compounds selected from the general formula (IV-b) are contained, and the content is 5 to 60% by mass, preferably 5 to 40% by mass, and 5 to 30% by mass. % Is more preferable. One or two compounds selected from the general formula (IV-c)
Containing at least 5 species, the content of which is 5 to 60% by mass,
-50 mass% is preferable, and 5-40 mass% is more preferable. In the formula, R ¹² , R ¹³ , R ¹⁴ , and R ¹⁵ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine. Formulas (a) to (e) are particularly preferable as the alkyl group or alkenyl group 5 from the viewpoint of improving response speed and steepness.

As the compound of the general formula (IV), the compound of the general formula (IV-b)

[0036]

Embedded image

(Wherein, R ¹² and R ¹³ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine). Contains one or more compounds, the content of which is 5 to 60% by mass, and further represented by the general formula (IV-c)

[0038]

Embedded image

(Wherein, R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine). Contains one or more, and the content is
The liquid crystal composition having a content of 5 to 60% by mass is preferable from the viewpoint of improving the response speed. In the formula, R ¹² , R ¹³ , R ¹⁴ , and R ¹⁵ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted with fluorine.
As the alkyl group or alkenyl group of formula (a)
(e) is particularly preferable from the viewpoint of improving the response speed and the steepness.

As a compound of the general formula (V), ring D is trans
-1,4-cyclohexylene group, Z ^Three, Z^FourIs a single bond
Where m = 1 (V-a)

[0041]

Embedded image

(In the formula, R ¹¹ represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and the ring G represents 1,4-phenylene group or trans-1,4-cyclohexylene group. X ⁵ represents a cyano group, a fluorine atom, a trifluoromethoxy group or a difluoromethoxy group, and X ⁴ and X ⁶ each independently represent a hydrogen atom or a fluorine atom.) It is preferable to contain more than one species from the viewpoint of further improving the temperature dependency of the threshold voltage. The content of the general formula (Va) is preferably from 5 to 85% by mass, and more preferably from 5 to 75% by mass, in order to maximize the effect.
5 to 65% by mass is more preferred. General formula (Vb) as general formula (V) or (Va)

[0043]

Embedded image

(Wherein R ¹⁶ represents an alkyl group having 1 to ¹⁶ carbon atoms or an alkenyl group having 2 to 8 carbon atoms), and contains one or more compounds selected from the group consisting of The ratio is preferably 5 to 40% by mass, more preferably 5 to 30% by mass, and more preferably 5 to 20% by mass for more effective use. In addition, as the general formula (V) or (Va), the general formula (V
-c)

[0045]

Embedded image

Wherein R ¹⁷ represents one or more compounds selected from the group consisting of alkyl groups having 1 to 16 carbon atoms and alkenyl groups having 2 to 8 carbon atoms. The rate is 5 to 40% by mass, preferably 5 to 30% by mass, and more preferably 5 to 20% by mass from the viewpoint of improving the temperature dependency of the threshold voltage.

One of the liquid crystal compositions which can best obtain the effects of the invention is represented by the following formula (Ia):

[0048]

Embedded image

Formula (II-a):

[0050]

Embedded image

And their contents are respectively
5 to 60% by mass, and represented by the general formula (III):
a)

[0052]

Embedded image

Having a content of 5 to 40% by mass, and a compound of the general formula (IV)

[0054]

Embedded image

(Wherein, R ¹² and R ¹³ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms which may be substituted by fluorine). Contains one or more compounds, the content of which is 5 to 60% by mass, and further represented by the general formula (IV-c)

[0056]

Embedded image

(Wherein, R ¹³ and R ¹⁴ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, which may be substituted by fluorine). Most preferably, the compound contains one or more compounds, and the content is 5 to 60% by mass. At this time, the formula (I
-a), the content of (II-a) is 5 to 60% by mass, respectively.
Is preferably from 30 to 30% by mass, particularly preferably from 5 to 20% by mass. formula
The content of (III-a) is 5 to 40% by mass, preferably 5 to 30% by mass, and more preferably 5 to 20% by mass.

A liquid crystal display device using the above liquid crystal composition is useful because its response speed is improved. A super-twisted nematic (STN) liquid crystal display device using the above liquid crystal composition and having a twist angle of 180 ° to 270 ° is excellent in response and contrast and useful.

The above nematic liquid crystal composition is TN-LCD or STN-LCD.
Useful for LCDs, but especially useful for STN-LCDs, for example
Suitable for application to 1/64 Duty to 1/160 Duty video compatible color STN-LCD. Further, it can be used for a transmissive or reflective liquid crystal display device. The liquid crystal composition of the present invention may contain a normal nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, and the like, in addition to the above compounds.

[0060]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.

The characteristics measured in the examples are as follows. T _NI : Nematic phase-isotropic liquid phase transition temperature (° C) T → _N : Solid phase or smectic phase-nematic phase transition temperature (° C) Vth: Applied at 90% luminance when a 240 ° twist cell is configured Voltage (V) Vsat: Applied voltage (V) at a luminance of 10% when a 240 ° twist cell is configured γ: Luminance 90% and 10% measured with a 240 ° twist cell
Steepness γ = Vsat / Vth Δn: birefringence η: viscosity at 20 ° C. (mPa · s) τ _{50 ° C .} : response at 50 ° C. (msec) (rise time and rise _{25 ° C} : Response at 25 ° C (msec) (Average of rise time and fall time) τ _{-20 ° C} : Response at -20 ° C (msec) (Average of rise time and fall time) value) dV / dT: a temperature range t ₁ (℃) ~t ₂ (temperature dependence of threshold voltage in ℃) (mV / ℃), is expressed by the following equation. dV / dT = (Vth ^t1 −Vth ^t2 ) / (t ₁ −t ₂ )

The production of the STN-LCD display element was performed as follows. Chiral substance "S-811" in nematic liquid crystal composition
(Merck) was added to prepare a mixed liquid crystal, and a twist angle of 240 ° was formed by rubbing an organic film of `` San Ever 150 '' (manufactured by Nissan Chemical Industries, Ltd.) on the opposed flat transparent electrode to form an alignment film.
Was injected into the STN-LCD display cell. The chiral substance has a specific helical pitch P of the mixed liquid crystal and the cell thickness d of the display cell due to the addition of the chiral substance, Δnd = 0.90, d / P = 0.50.
Was added so that

The following abbreviations are used in describing the compounds. -Terminal n (number): -C _n H _{2n + 1} ndm-: C _n H _{2n + 1} -CH = CH- (CH ₂ ) _m-1 --T-: -C≡C- -ndm:- (C _n H _{2n + 1} -CH = CH- (CH ₂ ) _m-1 ) -F: -F -On: -OC _n H _{2n + 1} -VO-: -COO- -CN-: -C≡N -Z-: -CH = N-N = CH-

[0064]

Embedded image

For example, abbreviations are used as shown below.

[0066]

Embedded image

(Example 1, Comparative Example 1) Nematic liquid crystal composition
Table 1 shows the results of preparing No. 1 and measuring various properties of the composition together with Comparative Example 1.

[0068]

[Table 1]

In Comparative Example 1, 3-Ph-T-Ph-1, 3-Ph-T-Ph-O2,
4-Ph-T-Ph-O2, 5-Ph-T-Ph-O1 is a compound of the formula (Ia) 0
d3-Ph-T-Ph-3d0, substituted with the formula (II-a), compound 5-Ph-VO-Ph
Example 1 was made by removing 3-CN and using the compound of formula (III-a). As a result, the steepness γ is 1.068 to 1.06
5, the response speed τ _{50 ° C} was improved from 56 msec to 51 msec, the response speed τ _{25 ° C} was improved from 114 msec to 97 msec, and the response speed τ _{-20 ° C} was greatly improved from 1764 msec to 1001 msec. Also, the temperature dependency dV / dT of the threshold voltage is
-3.3 (mV / ℃) to -2.6 (mV /
° C).

[0070]

According to the combination of the liquid crystal materials of the present invention, the steepness γ and the temperature dependency of the threshold voltage are improved without increasing the threshold voltage, and the response speed at room temperature and low temperature is increased. When this composition was used as a liquid crystal display device, the contrast was improved while maintaining the driving voltage, and a high-speed response in a wide temperature range was realized. This liquid crystal display is very useful as STN and TN-LCD.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09K 19/30 C09K 19/30 19/32 19/32 19/34 19/34 G02F 1/13 500 G02F 1 / 13 500 1/133 500 1/133 500 F term (reference) 2H089 QA16 RA10 SA07 4H027 BA01 BB03 BB04 BD02 BD05 BD06 BD07 BD08 BD20 BE04 BE05 CB01 CB02 CB03 CD04 CM04 CT01 CT03 CW02 DE04

Claims (13)

[Claims] 1. A compound represented by the general formula (I) as a first component: (In the formula, R ¹ and R ² are each independently an alkyl group or an alkoxyl group having 1 to 16 carbon atoms which may be substituted by fluorine, at least one of which is an alkenyl group having 3 to 16 carbon atoms. Wherein, when R ¹ and R ² are alkenyl groups, the double bond present in R ¹ and R ² is always at least one carbon atom separated from the benzene ring. And one or more of the following, and the second component is represented by the general formula (II): (Wherein, R ³ and R ⁴ each independently represent an alkyl or alkoxyl group having 1 to 16 carbon atoms, or an alkenyl group having ^{3 to} 16 carbon atoms, which may be substituted with fluorine. , When R ⁴ is an alkenyl group, the double bond present in R ³ and R ⁴ always separates one or more carbon atoms from the benzene ring.)
It contains two or more kinds, and has a general formula (III) as a third component. (Wherein R ⁵ independently represents an alkyl or alkoxyl group having 1 to 16 carbon atoms, which may be substituted by fluorine, or an alkenyl group having 2 to 16 carbon atoms). Containing one or more species, and having a nematic phase-isotropic liquid phase transition temperature of 75 to 130 ° C, a smectic phase or a solid phase-nematic phase transition temperature of -60 to -10 ° C, Rate anisotropy (Δn) is 0.07 ~
Liquid crystal composition characterized by being in the range of 0.30. 2. A compound represented by the general formula (IV) or (V) as a fourth component: (In the formula, R ⁶ , R ⁷ and R ⁸ are each independently an optionally substituted fluorine-substituted alkyl or alkoxyl group having 1 to 16 carbon atoms, an alkenyl group having 2 to 16 carbon atoms, 3-16 alkenyloxy group, or 1 carbon atom
Represents an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyl group of up to 10, and each of ring A, ring B, ring C, ring D and ring E may be independently substituted with a fluorine atom. ,
4-phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, naphthalene-2,6-diyl group, phenanthrene-2,7-diyl group, fluorene-2,7 -Diyl group,
Trans-1,4-cyclohexylene group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-
2,6-diyl group, trans-1,3-dioxane-2,5-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group or pyridazine Represents a -2,5-diyl group, l and m are each independently 0, 1 or 2
And Z ¹ , Z ² , Z ³ and Z ⁴ are each independently a single bond,
_{-CH 2 CH 2 -, - (} CH 2) 4 -, - OCH 2 -, - CH 2 O -, - CH = CH -, - COO- or represents -C≡C-, X ² is a cyano group, Fluorine atom, chlorine atom, trifluoromethoxy group, trifluoromethyl group,
Represents a difluoromethoxy group, a hydrogen atom, a 3,3,3-trifluoroethoxy group, R ′ or —OR ′, wherein R ′ has 1 to 1 carbon atoms.
2 represents a linear alkyl group or 2 to 12 linear alkenyl groups, and X ¹ and X ³ represent a hydrogen atom, a fluorine atom or a chlorine atom. 2. The liquid crystal composition according to claim 1, which comprises one or more compounds selected from the group consisting of: 3. A compound selected from the general formulas (I) and (II), each containing one or two or more compounds, each having a content of 5 to 60% by mass and a compound represented by the general formula (III) Contains one or more selected compounds, and the content is
5 to 40% by mass, further contains one or more compounds selected from the group consisting of general formulas (IV) and (V) as a fourth component, and the content is 5 to 85% by mass. 3. The liquid crystal composition according to claim 2, wherein: 4. The compound of the general formula (IV), wherein ring A and ring B are trans-1,4-cyclohexylene groups and Z ¹ , Z ²
Is a single bond of the general formula (IV-a) (Wherein, R ⁹ and R ¹⁰ represent the same meaning as R ⁶ and R ^7, and ring F is 1,4-
Represents a phenylene group or a trans-1,4-cyclohexylene group, and n represents 0 or 1. )
Claims characterized by containing one or more kinds
4. The liquid crystal composition according to any one of 1 to 3. 5. A compound selected from the general formulas (I) and (II), each containing one or two or more compounds, each having a content of 5 to 60% by mass and a compound represented by the general formula (III) Contains one or more selected compounds, and the content is
5 to 40% by mass, further containing one or more compounds selected from the general formula (IV-a) as a fourth component, characterized in that the content is 5 to 85% by mass 5. The liquid crystal composition according to claim 4. 6. The compound of the general formula (Va) wherein ring D is a trans-1,4-cyclohexylene group, Z ³ and Z ⁴ are single bonds, and m = 1. Formula 6 (In the formula, R ¹¹ is an alkyl group having 1 to 8 carbon atoms or 2 to 8
X represents a 1,4-phenylene group or trans-1,4-cyclohexylene group, X ⁵ represents a cyano group, a fluorine atom, a trifluoromethoxy group, a difluoromethoxy group, and X ⁴ , X ⁶ each independently represent a hydrogen atom or a fluorine atom. ) Containing one or more compounds selected from the claims 1 to 5
A liquid crystal composition according to any one of the above. 7. A compound selected from the general formulas (I) and (II), each containing one or two or more compounds, each having a content of 5 to 60% by mass and a compound represented by the general formula (III) Contains one or more selected compounds, and the content is
5 to 40% by mass, further containing one or more compounds selected from the general formula (Va) as a fourth component, the content of which is 5 to 85% by mass. 6. The liquid crystal composition according to 6. 8. A compound selected from the general formulas (I) and (II), each containing one or two or more compounds, each having a content of 5 to 60% by mass and a compound represented by the general formula (III) Contains one or more selected compounds, and the content is
5 to 40% by mass, a compound of the general formula (I)
Vb) (Wherein, R ¹² and R ¹³ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms which may be substituted by fluorine).
Contains two or more species, the content of which is 5 to 60% by mass
In addition, the general formula (IV-c) (Wherein, R ¹⁴ and R ¹⁵ are each independently an independently substituted fluorine-containing alkyl group having 1 to 8 carbon atoms or carbon atoms.
Represents 2 to 8 alkenyl groups. The liquid crystal composition according to any one of claims 1 to 7, wherein the liquid crystal composition contains one or more compounds selected from (1) and (2), and the content thereof is 5 to 60% by mass. 9. The compound represented by the general formula (V) as the general formula (V) or (Va):
-b) (Wherein, R ¹⁶ represents one or more compounds selected from an alkyl group having 1 to ¹⁶ carbon atoms or an alkenyl group having 2 to 8 carbon atoms.) ~ 40
The liquid crystal composition according to any one of claims 1 to 8, wherein the composition is mass%. 10. A compound represented by the general formula (V) or (Va):
(Vc) (In the formula, R ¹⁷ represents an alkyl group having 1 to 16 carbon atoms or an alkenyl group having 2 to 8 carbon atoms.) The compound contains one or more compounds selected from the group consisting of ~ 40
The liquid crystal composition according to any one of claims 1 to 9, wherein the composition is mass%. 11. A compound of the formula (Ia) represented by the general formula (I): Formula (II-a) as general formula (II) , Each having a content of 5 to 60% by mass, and having the general formula (III) represented by the formula (III-a): , The content of which is 5 to 40% by mass, and further represented by the general formula
As the compound of (IV), a compound of the general formula (IV-b) (Wherein, R ¹² and R ¹³ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms which may be substituted by fluorine).
Contains two or more species, the content of which is 5 to 60% by mass
And further represented by the general formula (IV-c): (Wherein R ¹³ and R ¹⁴ each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms which may be substituted with fluorine).
Contains two or more species, the content of which is 5 to 60% by mass
The liquid crystal composition according to any one of claims 1 to 10, wherein 12. A liquid crystal display device using the liquid crystal composition according to claim 1. 13. A super-twisted nematic (STN) liquid crystal display device using the liquid crystal composition according to claim 1 and having a twist angle of 180 ° to 270 °.