JPH10237076A - Liquid crystalline compound having minus anisotropic value of dielectric constant, liquid crystal composition containing the same liquid crystalline compound and liquid crystal display element using the same liquid crystal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound useful also for controlling many characteristics of a liquid crystal composition for various kinds of display systems using a compound or a composition having a specific structure and positive anisotropic value of dielectric constant. SOLUTION: This compound has a structure comprising 1,7- dioxaspiro-[5.5]undecane-3,9-diyl group in the skeleton structure and is preferably represented by formula I [R<1> and Y<1> are each a 1-20C alkyl, H, a halogen, cyano, etc.; X<1> to X<4> are each a single bond, (CH2 )2 , CH=CH, etc.; ring A<1> to ring A<5> are each 1,7-dioxaspiro[5.5]-undecane-3,9-diyl, etc.; (a<1> ) to (a<5> ) are each 0 or 1, with the proviso that (a<1> +a<2> +a<3> +a<4> +a<5> )>=1], e.g. 3-(2-trans-4-n- pentylcyclohexy)ethyl-9-(2,3-difuoro-4-n-proplphenyl)-1,7-dioxaspiro[5 .5]undecanbe. Furthermore, the compound is preferably obtained by using, e.g. a compound of formula II as a starting substance and passing through reaction of thionly chloride with methanol in the presence of sodium carbonate.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention mainly relates to a liquid crystal display device, for example, a vertical alignment system, IPS = in-plane switching, TFT = thin film transistor, TN = twisted nematic, or STN = super twisted nematic, etc., and especially vertical alignment. TECHNICAL FIELD The present invention relates to a novel liquid crystal compound capable of exhibiting various physical properties suitable for a liquid crystal composition for a system and an IPS, a liquid crystal composition having suitable physical properties using the same, and a liquid crystal display device using the liquid crystal composition. In the present application, the term “liquid crystalline compound” is used as a general term for a compound that exhibits a liquid crystal phase and a compound that does not exhibit a liquid crystal phase but is useful as a component of a liquid crystal composition.

[0002]

BACKGROUND ART Conventionally, various liquid crystal display systems have been proposed. As an example of them, the following display method is mentioned (Latest technology of liquid crystal, edited by the Industrial Research Council (1983)). As a method of using a liquid crystal composition having a positive dielectric anisotropy value, T
N, STN, or TN based AM = active matrix (TFT or MIM = metal, insulating film, metal, etc.) or a method using a liquid crystal composition having a negative dielectric anisotropy value , ECB = field controlled birefringence effect (HAN
= Hybrid molecular arrangement or DAP = vertical molecular arrangement, etc.), DS = dynamic scattering, GH = guest host or PC
= There is a method such as phase transition. Of these systems, the mainstream of those currently in practical use is a system using a liquid crystal composition having a positive dielectric anisotropy value. Compared to this, practical use of the method using a liquid crystal composition having a negative dielectric anisotropy value has been delayed. In connection with this, the development of liquid crystal compositions having a negative dielectric anisotropy value and the compounds used for the same were also compared with the development of liquid crystal compositions having a positive dielectric anisotropy value and the compounds used for the same. Then, it is not enough.

Under these circumstances, recently, attempts to improve the narrow viewing angle, which is one of the drawbacks of the liquid crystal display, have been actively made. One of the methods is
IPS (R. Kiefer et al, JAPAN DISPLAY'92,547
(1992), M. Oh-e et al, ASIADISPLAY '95, 577 (1995), JP-T5-505247, JP-A-7-128647.
No.). One of the features of the IPS is that, in the conventional liquid crystal panel, electrodes are provided on upper and lower substrates, respectively, whereas in the liquid crystal panel of this system, interdigital electrodes are provided only on one substrate. It is. Another feature of this method is that the liquid crystal composition can be used regardless of the positive or negative value of the dielectric anisotropy value. As another example of an attempt to improve the narrow viewing angle, there is a method in which the vertical angle of liquid crystal molecules is used to improve the viewing angle (Japanese Patent Laid-Open No. 2-176625). One of the features of this method is that a liquid crystal composition having a negative dielectric anisotropy is used. From such a background, liquid crystal compounds and liquid crystal compositions having a negative dielectric anisotropy value have been strongly demanded.

In all display systems, the liquid crystal composition used has not only an appropriate dielectric anisotropy value but also other characteristics such as a refractive index anisotropy value (△ n) and an elastic constant ratio K. _It is necessary to adjust various physical property values such as ₃₃ / K ₁₁ (K ₃₃ : bend elastic constant, K ₁₁ : splay elastic constant) to an optimum value, and that the liquid crystal phase is in an appropriate temperature range In addition, low viscosity is required even at a low temperature. None of the conventionally known liquid crystalline compounds satisfy all of these conditions alone. Therefore, in order to obtain a composition that can be usually used as a liquid crystal phase, it is prepared by mixing a compound having several to twenty and several kinds of liquid crystal phases and, if necessary, a compound having no more than several kinds of liquid crystal phases. . Therefore, each liquid crystal compound is
Characteristics such as good compatibility with other liquid crystal compounds and good compatibility in a low temperature range are also required due to demand for use in a low temperature environment.

However, as described above, the conventional display system mainly uses a liquid crystal composition containing a liquid crystal compound having a positive dielectric anisotropy value. However, the development of the compound or composition was not sufficient. For this reason, the method of diversification in this way and the corresponding various characteristics have been insufficient. For example, even if the dielectric anisotropy value is negative, the absolute value is small, the driving voltage cannot be reduced due to the large elastic constant, the compatibility is poor, and the compound cannot be used in large quantities. It is difficult to freely set the value of the refractive index anisotropy, there is a problem that the viscosity is large, and the chemical and physical stability is poor.

Prior to the present invention, a liquid crystalline compound having a dioxaspiro [5.5] undecane skeleton has already been reported (JP-A-64-19074). However, the compound disclosed herein, dioxaspiro [5.
5] The position of the oxygen atom in the undecane skeleton is at the 1,5-position. In addition, these compounds, for example, suitable dielectric anisotropy value and refractive index anisotropy value, small elastic constant, good compatibility,
Physical properties required for using these compounds in liquid crystal compositions, such as low viscosity and high chemical and physical stability, are not always satisfactory. No further improvement was required. Prior to the present invention, compounds having a 1,7-dioxaspiro [5.5] undecane skeleton have already been reported (R. Baker et al, J. Chem. Soc., Perkin Tran).
s 1, 5 , 1415 (1990)). However, the compounds disclosed herein have no liquid crystallinity, and further, there is no description that the compounds can be used for liquid crystal applications. For example, there is no description of an appropriate dielectric anisotropy value or refractive index anisotropy value, a small elastic constant, good compatibility, low viscosity, high chemical and physical stability, and the like. In particular, there is no idea in these reports that a compound having a dioxaspiro [5.5] undecane skeleton is converted into a liquid crystal compound having a negative dielectric anisotropy value. In particular, in order to obtain a negative dielectric anisotropy value having a large absolute value, a compound having a dioxaspiro [5.5] undecane skeleton is regioselectively introduced with an oxygen atom at the 1,7-position, and the liquid crystallinity is improved. There has been no idea to introduce a substituent in the long axis direction at the 3,9-position in order to keep. Thus, the compounds of the present invention are not readily conceivable from the prior art.

[0007]

An object of the present invention is to provide a vertical alignment system, IPS, ECB (HAN or DAP, etc.) as described in JP-A-2-176625,
Not only can it be used for various display methods using compounds or compositions having a negative dielectric anisotropy value such as S, GH or PC, but also TN, STN, or TN-based AM (TF
T or MIM), which solves the above-mentioned problem that can be used for adjusting various characteristics of a liquid crystal composition for various display systems using a compound or a composition having a positive dielectric anisotropy value. It is an object of the present invention to provide a novel liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal display device prepared using the liquid crystal composition.

[0008]

Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above-mentioned problems, and as a result, the compounds according to claims 1 to 2 have not only a large absolute value but a negative dielectric anisotropy value. ,
A liquid crystal composition having a suitable refractive index anisotropy value, a small elastic constant, good compatibility, low viscosity, high chemical and physical stability, and a compound according to claim 1 or 2. When used in a product, the liquid crystal composition has a small elastic constant, can appropriately set the dielectric anisotropy value and the refractive index anisotropy value, has a low viscosity, and has excellent chemical and physical stability. In particular, they have found that a liquid crystal composition having a large absolute value and a negative dielectric anisotropy value can be obtained, and that a liquid crystal display device can be obtained using the composition, thereby completing the present invention.

That is, the present invention provides the following [1] to [1]
2). [1] 1,7-dioxaspiro [5.
5] A liquid crystalline compound having an undecane-3,9-diyl group. [2] General formula (1)

[0010]

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(Where R¹And Y¹Are independently carbon numbers
1 to 20 alkyl groups, hydrogen atoms, halogen atoms, shea
, Cyanic acid, isocyano or isothiocyanic acid
Represents one or more non-adjacent ones in the above alkyl group
Is an oxygen atom, a sulfur atom, a nitrogen atom, -C≡
C- wherein at least one hydrogen atom has 1 to 10 carbon atoms
Silylene group or vinylene group which may be substituted with a group
May be substituted, and one of these alkyl groups
More than one hydrogen atom is replaced by a fluorine or chlorine atom
And these alkyl groups are optically active.
May be X¹, X^Two, X^ThreeAnd X^FourAre each independently connected
If-(CH_Two)_Two-, -CH = CH-, -C≡C-,-
COO-, -OCO-, -CH_TwoO-, -OCH_Two−, −
(CH _Two)_Four-,-(CH_Two)_ThreeO-, -O (CH_Two)_Three−,
-CH = CHCH_TwoCH_Two-, -CH_TwoCH = CHCH
_Two-, -CH_TwoCH_TwoCH = CH-, -CH = CHCH =
CH-, -CF_TwoO-, -OCF_Two-, -CH = CHCH
_TwoO-, -OCH_TwoCH = CH-, -CF = CF-, -C
H_TwoCF_Two-, -CF_TwoCH_Two−, − (CF_Two)_Two-,-(C
F_Two)_Four-,-(CH_Two)_TwoCOO-, -OCO (CH_Two)_Two
-, -CH = CHCOO-, -OCOCH = CH-,-
CH = CHC≡C- or -C≡CCH = CH-
And ring A¹, Ring A^Two, Ring A^Three, Ring A^FourAnd ring A^FiveAre independent
To give 1,7-dioxaspiro [5.5] undecane-
3,9-diyl, bicyclo [1.1.1] pentane-
1,3-diyl, trans-cyclohexane-1,4-
Diyl, cyclohex-1-ene-1,4-diyl, or
Represents 1,4-phenylene, and the carbon constituting these rings
Elementary atoms are replaced by nitrogen, oxygen or sulfur atoms
And the hydrogen atoms on these rings may be halogen atoms.
May be substituted with a substituent or a cyano group.
A¹, Ring A^Two, Ring A^Three, Ring A^FourAnd ring A^FiveAt least one of
Is 1,7-dioxaspiro [5.5] undecane-
3,9-diyl, a¹, A^Two, A^Three, A^FourAnd a^FiveIs
Each independently represents 0 or 1,¹+ A^Two+ A^Three+ A^Four+
a^Five≧ 1 and each atom constituting the compound is
It may be substituted with the isotope. )
The liquid crystal compound according to item [1].

[3] A liquid crystal composition comprising at least two components, comprising at least one kind of the liquid crystal compound described in [1] or [2]. [4] As a first component, at least one compound according to item [1] or [2] is contained, and as a second component,
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (2), (3) and (4).

[0013]

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(Wherein R ² represents an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group may be substituted with an oxygen atom or —CH ＝ CH—). In addition, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ² is a fluorine atom, a chlorine atom, —OCF ₃ , —OCF ₂ H, —C
_{F 3, -CF 2 H, -CFH} 2, -OCF 2 CF 2 H or -
Represents OCF ₂ CFHCF _3, L ¹ and L ² represents a hydrogen atom or a fluorine atom each independently, Z ¹ and Z ² are each independently _{- (CH 2) 2 -,} - (CH 2) 4 - , -COO-,-
CF ₂ O—, —OCF ₂ —, —CH ＝ CH— or a single bond, and ring Q ¹ is trans-cyclohexane-1,4-diyl, 1,3-dioxane-2,5-diyl, or a hydrogen atom Represents 1,4-phenylene which may be substituted by a fluorine atom, and ring Q2 represents trans-cyclohexane-
1,4-diyl or 1,4-phenylene in which a hydrogen atom may be substituted with a fluorine atom, and each atom constituting these compounds may be substituted with its isotope. )

[5] As the first component, at least one compound described in the item [1] or [2] is contained, and as the second component, a compound represented by the general formula (5) or (6) is used. A liquid crystal composition comprising at least one selected compound.

[0016]

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(Wherein R ³ and R ⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
May be substituted with CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ³ represents a cyano group or -C 環 C-CN; Q ³ is trans-cyclohexane-1,4-diyl,
Represents 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl, and ring Q ⁴ is trans-cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, Or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, and ring Q ⁵ is trans-cyclohexane-1,4-diyl or 1,4
Represents phenylene, and Z ³ represents — (CH ₂ ) ₂ —, —COO
Or represents a single bond, L ³ , L ⁴ and L ⁵ each independently represent a hydrogen atom or a fluorine atom, b, c and d each independently represent 0 or 1, and these compounds The constituent atoms may be substituted by their isotopes. )

[6] As the first component, at least one compound described in item [1] or [2] is contained, and as the second component, the compounds represented by the above general formulas (2), (3) and (4) At least one compound selected from the compound group consisting of: and at least one compound selected from the compound group consisting of general formulas (7), (8) and (9) as a third component: A liquid crystal composition characterized by the following.

[0019]

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(Wherein R ⁵ and R ⁶ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and ring Q ⁶ , ring Q ⁷ and ring Q ⁸ are each independently , Trans-cyclohexane-1,4-diyl, pyrimidine-
Represents 2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, and Z ⁴ and Z ⁵ each independently represent -C≡C-, -COO-,-( CH ₂ ) ₂
Represents-, -CH = CH- or a single bond, and atoms constituting these compounds may be substituted with an isotope thereof. )

[7] As the first component, at least one compound described in the item [1] or [2] is contained, and as the second component, the compounds represented by the above general formulas (10), (11) and (1)
A liquid crystal composition comprising at least one compound selected from the compound group consisting of 2).

[0022]

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(Wherein, R ⁷ and R ⁸ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are an oxygen atom or —CH ＝
CH-, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and ring Q ⁹ and ring Q ¹⁰ are each independently trans-
Represents cyclohexane-1,4-diyl or 1,4-phenylene, it represents an L ⁶ and L ⁷ each independently represent a hydrogen atom or a fluorine atom not represent simultaneously hydrogen atoms, Z ⁶
And Z ⁷ are each independently — (CH ₂ ) ₂ —, —COO—
Or a single bond, and the atoms constituting these compounds may be substituted with isotopes thereof. )

[8] As the first component, at least one compound described in item [1] or [2] is contained, and as the second component, the compounds represented by the above general formulas (7), (8) and (9) And at least one compound selected from the group consisting of the compounds represented by the above general formulas (10) and (1).
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds (1) and (12).

[9] As the first component, it contains at least one kind of the compound described in [1] or [2], and as the second component, it is selected from the compound group consisting of the general formulas (5) and (6). A liquid crystal composition comprising at least one compound selected from the group consisting of the general formulas (7), (8) and (9) as a third component. Stuff.

[10] As the first component, at least one compound described in item [1] or [2] is contained, and as the second component, the compounds represented by the above general formulas (2), (3) and (4) And at least one compound selected from the compound group consisting of the general formulas (5) and (6) as a third component, and a fourth component. A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (7), (8) and (9). [11] A liquid crystal composition, which further comprises one or more optically active compounds in addition to the liquid crystal composition according to any one of [3] to [10]. [12] A liquid crystal display device formed using the liquid crystal composition according to any one of the items [3] to [11].

The inventions of the items [7] and [8] relate to an N-type (negative Δε) liquid crystal composition. The N-type liquid crystal composition can be driven by various display methods such as a vertical alignment method described in JP-A-2-176625 and IPS. In addition, [4], [5],
[6],

The inventions of the items [9] and [10] relate to a P-type (Δε is positive) liquid crystal composition.
An N-type compound can also be used as a component of the liquid crystal composition. This not only allows the dielectric anisotropy value to be freely set according to the intended use of the liquid crystal composition, but also
Other characteristics, such as control of the refractive index anisotropy value and elastic constant of the liquid crystal composition, are also possible.

Preferred embodiments of the compound of the present invention represented by the general formula (1) are shown below. R ¹ and Y ¹ are each independently an alkyl group having 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a cyano group, a cyanate group, an isocyano group or an isothiocyanate group, and are not adjacent to each other in the alkyl group. One or more methylene groups are an oxygen atom, a sulfur atom, a nitrogen atom, -C≡C-, and one or more hydrogen atoms have 1 to 10 carbon atoms.
May be substituted with a silylene group which may be substituted with an alkyl group, or a vinylene group, and one or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or a chlorine atom. Also, these alkyl groups may be optically active.

As the alkyl group represented by R ¹ and Y ¹ in the general formula (1), specifically, a saturated alkyl group consisting only of carbon atoms and hydrogen atoms, a haloalkyl group,
Alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxyalkyl, haloalkoxyalkyl, alkoxyalkoxy Group, haloalkoxyalkoxy group, alkanoyl group,
Examples include a haloalkanoyl group, an alkanoyloxy group, a haloalkanoyloxy group, an alkoxycarbonyl group, and a haloalkoxycarbonyl group.

More specifically, examples of R ¹ and Y ¹ include the following groups or atoms. -CH _3, -C ₂ H
_{5, -C 3 H 7, -C} 4 H 9, -C 5 H 11, -C 6 H 13, -C 7
_{H 15, -C 8 H 17,} -C 9 H 19, -C 10 H 21, -CF
_{H 2, -CF 2 H, -CF} 3, -CH 2 CH 2 F, -CH 2 C
_{HF 2, -CH 2 CF 3,} -CF 2 CH 3, -CF 2 CF
_{2 H, -CFHCF 3, -CF 2} CF 3, - (CH 2) 2 CH
₂ F,-(CH ₂ ) ₂ CHF ₂ ,-(CH ₂ ) ₂ CF ₃ , -C
_{H 2 CF 2 CH 3, -CH} 2 CF 2 CF 3, -CF 2 C 2 H 5,
_{-C 3 F 7, -CF 2 CFHCF} 3, - (CH 2) 3 CH
_{2 F, - (CH 2)} 4 CH 2 F, - (CH 2) 5 CH 2 F, -
_{CF 2 C 3 H 7, -CH} 2 CF 2 C 2 H 5, - (CH 2) 2 CF 2
_{CH 3, -CF 2 C 4 H} 9, -CH 2 CF 2 CH 3, - (C
_{H 2) 2 CF 2 C 2} H 5, - (CH 2) 3 CF 2 CH 3,

-OCH ₃ , -OC ₂ H ₅ , -OC ₃ H ₇ ,-
_{OC 4 H 9, -OC 5 H} 11, -OC 6 H 1 3, -OC 7 H 15,
_{-OC 8 H 17, -OC 9 H} 19, -OC 10 H 21, -OCFH
_{2, -OCF 2 H, -OCF 3} , -OCH 2 CH 2 F, -O
_{CH 2 CHF 2, -OCH 2 CF} 3, -OCF 2 CH 3, -O
_{CF 2 CF 2 H, -OCFHCF 3} , -OCF 2 CF 3, -
O (CH ₂ ) ₂ CH ₂ F, —O (CH ₂ ) ₂ CHF ₂ , —O
(CH ₂ ) ₂ CF ₃ , —OCH ₂ CF ₂ CH ₃ , —OCH ₂ C
_{F 2 CF 3, -OCF 2 C} 2 H 5, -OC 3 F 7, -OCF 2 C
FHCF ₃ , —O (CH ₂ ) ₃ CH ₂ F, —O (CH ₂ ) ₄ C
_{H 2 F, -O (CH 2} ) 5 CH 2 F, -OCF 2 C 3 H 7, -
OCH ₂ CF ₂ C ₂ H ₅ , —O (CH ₂ ) ₂ CF ₂ CH ₃ , —O
_{CF 2 C 4 H 9, -OCH} 2 CF 2 CH 3, -O (CH 2) 2 C
_{F 2 C 2 H 5, -O} (CH 2) 3 CF 2 CH 3,

-CH = CH ₂ , -CH = CHCH ₃ , -C
_{H = CHC 2 H 5, -CH} = CHC 3 H 7, -CH = CHC
_{4 H 9, -CH 2 CH =} CHCH 3, -CH 2 CH = CHC 2
_{H 5, -CH 2 CH = CHC} 3 H 7, -CH 2 CH = CHC 4
_{H 9, - (CH 2)} 2 CH = CHCH 3, - (CH 2) 2 CH
_{= CHC 2 H 5, - (} CH 2) 2 CH = CHC 3 H 7, - (C
_{H 2) 2 CH = CHC 4} H 9, -CH 2 CH = CH 2, - (C
_{H 2) 2 CH = CH 2} , - (CH 2) 3 CH = CH 2, - (C
_{H 2) 4 CH = CH 2} , - (CH 2) 5 CH = CH 2, -CH
ＣＨCHCH ＝ CH ₂ , —CH ＝ CHCH ₂ CH ＝ CH ₂ ,
_{-CH = CH (CH 2) 2} CH = CH 2, -CH = CH
_{(CH 2) 3 CH = CH} 2, -CH 2 CH = CH (CH 2) 2
_{CH = CH 2, - (CH} 2) 2 CH = CH (CH 2) 2 CH
= CH ₂ ,

-CF = CF ₂ , -CH = CF ₂ , -CH =
_{CHF, -CH 2 CF = CF 2} , -CH 2 CH = CFH,
_{- (CH 2) 2 CH =} CF 2, - (CH 2) 2 CH = CH
_{F, - (CH 2) 3} CH = CF 2, - (CH 2) 3 CH = C
_{HF, - (CH 2) 4} CH = CF 2, - (CH 2) 4 CH =
_{CHF, - (CH 2) 5} CH = CF 2, - (CH 2) 5 CH
_{= CHF, -CH = CHCH 2 CH} 2 F, -CH = CHC
_{H 2 CH 2 Cl, -CH =} CHCH 2 CHF 2, -CH = C
_{HCH 2 CF 3, -CH = CH} (CH 2) 2 CH 2 F, -C
_{H = CH (CH 2) 2} CHF 2, -CH = CH (CH 2) 2
_{CF 3, -CH = CH (CH} 2) 3 CH 2 F, -CH = CH
(CH ₂ ) ₃ CHF ₂ , —CH ＝ CH (CH ₂ ) ₃ CF ₃ ,
_{CH = CH (CH 2) 4} CH 2 F, -CH = CH (CH 2)
₄ CHF ₂ , —CH ＝ CH (CH ₂ ) ₄ CF ₃ , —CH ₂ CH
_{= CH (CH 2) 2 CH} 2 F, -CH 2 CH = CHCH 2 C
_{H 2 F, - (CH 2} ) 2 CH = CH (CH 2) 2 CH 2 F, -
_{(CH 2) 2 CH = CHCH} 2 CH 2 F, -CH = CHCH
_{2 CH = CF 2, -CH =} CH (CH 2) 2 CH = CF 2,
_{-CH = CH (CH 2) 2} CF = CF 2, -CH = CH
(CH ₂ ) ₃ CHFCH ₃ ,

--OCH ₂ CH = CHCH ₃ , --OCH ₂ C
_{H = CHC 2 H 5, -OCH} 2 CH = CHC 3 H 7, -OC
_{H 2 CH = CHC 4 H 9} , -O (CH 2) 2 CH = CHC
_{H 3, -O (CH 2)} 2 CH = CHC 2 H 5, -O (CH 2)
₂ CH = CHC ₃ H ₇ , —O (CH ₂ ) ₂ CH = CHC
_{4 H 9, -OCH 2 CH =} CH 2, -O (CH 2) 2 CH = C
_{H 2, -O (CH 2)} 3 CH = CH 2, -O (CH 2) 4 CH
ＣＨCH ₂ , —O (CH ₂ ) ₅ CH ＝ CH ₂ , —OCH ₂ CH
ＣＨCH (CH ₂ ) ₂ CH 2CH ₂ , —O (CH ₂ ) ₂ CH =
CH (CH ₂ ) ₂ CH = CH ₂ ,

-OCH ₂ CF = CF ₂ , -OCH ₂ CH =
_{CF 2, -OCH 2 CF = CHF} , -O (CH 2) 2 CH =
_{CF 2, -O (CH 2)} 2 CH = CHF, -O (CH 2) 3
CH = CF ₂ , —O (CH ₂ ) ₃ CH = CHF, —O (C
_{H 2) 4 CH = CF 2} , -O (CH 2) 4 CH = CHF, -
_{O (CH 2) 5 CH =} CF 2, -O (CH 2) 5 CH = CH
_{F, -OCH 2 CH = CHCH 2} CH 2 F, -O (CH 2)
_{2 CH = CH (CH 2)} 2 CH 2 F, -O (CH 2) 2 CH =
CHCH ₂ CH ₂ F,

-C≡CH, -C≡CCH ₃ , -C≡CC _{2
H 5, -C≡CC 3 H 7,} -C≡CC 4 H 9, -CH 2 C≡C
_{H, -CH 2 C≡CCH 3, -CH} 2 C≡CC 2 H 5, -C
_{H 2 C≡CC 3 H 7, -CH} 2 C≡CC 4 H 9, - (CH 2) 2
C≡CH, — (CH ₂ ) ₂ C≡CCH ₃ , — (CH ₂ ) ₂ C
_{≡CC 2 H 5, - (CH} 2) 2 C≡CC 3 H 7, - (CH 2) 2
C≡CC ₄ H ₉ , — (CH ₂ ) ₃ C≡CH, — (CH ₂ ) ₃ C
{CCH ₃ ,-(CH ₂ ) ₃ C} CC ₂ H ₅ ,-(CH ₂ ) _{3
C≡CC 3 H 7, - (CH} 2) 3 C≡CC 4 H 9, -C≡CC
_{F 3, -C≡CC 2 F 5,} -C≡CC 3 F 7, -CH 2 C≡C
CF ₃ , — (CH ₂ ) ₂ C≡CCF ₃ ,

[0036] -OCH ₂ C≡CH, -OCH ₂ C≡CCH
₃ , —OCH ₂ C≡CC ₂ H ₅ , —OCH ₂ C≡CC ₃ H ₇ ,
—OCH ₂ C≡CC ₄ H ₉ , —O (CH ₂ ) ₂ C≡CH,
O (CH ₂ ) ₂ C≡CCH ₃ , —O (CH ₂ ) ₂ C≡CC ₂ H
_{5, -O (CH 2) 2} C≡CC 3 H 7, -O (CH 2) 2 C≡
CC ₄ H ₉ , —O (CH ₂ ) ₃ C≡CH, —O (CH ₂ ) ₃ C
{CCH ₃ , —O (CH ₂ ) ₃ C} CC ₂ H ₅ , —O (C
_{H 2) 3 C≡CC 3 H 7} , -O (CH 2) 3 C≡CC 4 H 9,

--OCH ₂ C≡CCF ₃ , --O (CH ₂ ) ₂ C
≡CCF ₃ , —CH ₂ OCH ₃ , —CH ₂ OC ₂ H ₅ , —CH
_{2 OC 3 H 7, -CH 2} OC 4 H 9, -CH 2 OC 5 H 11, -
_{(CH 2) 2 OCH 3,} - (CH 2) 2 OC 2 H 5, - (C
_{H 2) 2 OC 3 H 7} , - (CH 2) 2 OC 4 H 9, - (CH 2) 2
_{OC 5 H 11, - (CH} 2) 3 OCH 3, - (CH 2) 3 OC 2
_{H 5, - (CH 2)} 3 OC 3 H 7, - (CH 2) 3 OC 4 H 9,
— (CH ₂ ) ₃ OC ₅ H ₁₁ , — (CH ₂ ) ₄ OCH ₃ ,

--CF ₂ OCH ₃ , --CF ₂ OC ₂ H ₅ , --C
_{F 2 OC 3 H 7, -CF} 2 OC 4 H 9, -CF 2 OC 5 H 11, -
_{CH 2 OCF 3, -CH 2 OC} 2 F 5, -OCH 2 OCH 3,
_{-OCH 2 OC 2 H 5, -OCH} 2 OC 3 H 7, -OCH 2 O
_{C 4 H 9, -OCH 2 OC} 5 H 11, -O (CH 2) 2 OC
_{H 3, -O (CH 2)} 2 OC 2 H 5, -O (CH 2) 2 OC 3 H
_{7, -O (CH 2) 2} OC 4 H 9, -O (CH 2) 2 OC
_{5 H 11, -O (CH 2} ) 3 OCH 3, -O (CH 2) 3 OC 2
_{H 5, -O (CH 2)} 3 OC 3 H 7, -O (CH 2) 3 OC 4 H
_{9, -O (CH 2) 3} OC 5 H 11, -O (CH 2) 4 OC
H ₃ ,

--OCH ₂ OCF ₃ , --OCH ₂ OC ₂ F ₅ ,
_{-COCF 3, -COCHF 2, -COC 2} F 5, -COC
_{3 F 7, -COCH 2 CF 3} , -OCOCH 3, -OCOC 2
_{H 5, -OCOC 3 H 7,} -OCOC 5 H 11, -OCOC 7
H ₁₅ , —OCOCF ₃ , —OCOCHF ₂ , —OCOC _{2
F 5, -OCOC 3 F 7,} -OCOCH 2 CF 3, -COO
_{CH 3, -COOC 2 H 5,} -COOC 3 H 7, -COOC 4
_{H 9, -COOC 5 H 11,} -COOCH (CH 3) C
_{6 H 13, -COOCH 2 F,} -COOCH 2 CF 3, -CO
_{O (CH 2) 2 CF 3} , -COO (CH 2) 3 CF 3, -CO
O (CH ₂ ) ₄ CH ₂ F,

Hydrogen atom, halogen atom, cyano group, cyanate group, isocyano group and isothiocyanate group.

Chemical formula of the compound represented by the general formula (1)
When particular attention is paid to physical stability, R ¹ and Y ¹ are a saturated alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkoxyalkyl group, a haloalkoxyalkyl group consisting only of a carbon atom and a hydrogen atom, Alkoxyalkoxy group, haloalkoxyalkoxy group, alkanoyl group, haloalkanoyl group, alkanoyloxy group, haloalkanoyloxy group, alkoxycarbonyl group, haloalkoxycarbonyl group, hydrogen atom, halogen atom, cyano group, cyano group, or isocyano group And the like.

When it is desired to increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), R ¹ and Y ¹ are the same as those of a saturated alkyl composed of only carbon atoms and hydrogen atoms. Group, alkoxy group, alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkoxyalkyl group, alkoxyalkoxy group, alkanoyl group, alkanoyloxy group, alkoxycarbonyl group,
Alternatively, a substituent having a small polarity such as a hydrogen atom is preferable.

X ^{1 of} the compound represented by the general formula (1),
X ² , X ³ and X ⁴ are a single bond, — (CH ₂ ) ₂ —, —CH
= CH-, -C≡C-, -COO-, -OCO-, -C
_{H 2 O -, - OCH 2} -, - (CH 2) 4 -, - (CH 2) 3
_{O -, - O (CH 2} ) 3 -, - CH = CHCH 2 CH 2 -,
_{-CH 2 CH = CHCH 2 -,} - CH 2 CH 2 CH = CH
-, - CH = CHCH = CH -, - CF 2 O -, - OC
F ₂ —, —CH ＝ CHCH ₂ O—, —OCH ₂ CH ＝ CH
-, - CF = CF -, - CH 2 CF 2 -, - CF 2 CH
_{2 -, - (CF 2)} 2 -, - (CF 2) 4 -, - (CH 2) 2
_{COO -, - OCO (CH 2} ) 2 -, - CH = CHCOO
—, —OCOCH ＝ CH—, —CH ＝ CHC≡C—, or —C≡CCH ＝ CH—.

The chemical reaction of the compound represented by the general formula (1)
When paying particular attention to physical stability, X ¹ , X ² , X ³ and X ⁴ are each a single bond, — (CH ₂ ) ₂ —, —COO—, or —OC.
_{O -, - CH 2 O -} , - OCH 2 -, - (CH 2) 4 -, -
_{(CH 2) 3 O -,} - O (CH 2) 3 -, - CF 2 O -, -
_{OCF 2 -, - CH 2 CF} 2 -, - CF 2 CH 2 -, - (C
_{F 2) 2 -, - (} CF 2) 4 -, - (CH 2) 2 COO-, or -OCO (CH _{2) 2} - are preferred.

The ring A1 of the compound represented by the general formula (1),
At least one of ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ is 1,
7-dioxaspiro [5.5] undecane-3,9-diyl, but other preferred rings include bicyclo [1.1.1] pentane-1,3-diyl, trans-
Cyclohexane-1,4-diyl, cyclohex-1-
Ene-1,4-diyl and 1,4-phenylene; the carbon atoms constituting these rings may be substituted by nitrogen atoms, oxygen atoms or sulfur atoms, and the hydrogen atoms on the rings are halogen It may be substituted with an atom or a cyano group.

Specifically, 1-cyano-trans-cyclohexane-1,4-diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohex-1-ene-1, 4-diyl, 2,3-
Difluorobenzene-1,4-diyl and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. Further, a hydrogen atom on the ring is a fluorine atom,
The ring which may be substituted with a chlorine atom or a cyano group also includes the following rings. Bicyclo [1.1.
1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1,
4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyrazine-2,5-diyl, pyridazine-3, 6-diyl, tetrahydropyran-2,
5-diyl, 1,3-dithiane-2,5-diyl, 1,
3-oxathiane-2,5-diyl, and bicyclo [2.2.2] octane-1,4-diyl).

Chemical formula of the compound represented by the general formula (1)
When particular attention is paid to physical stability, ring A ¹ , ring A ² , ring A
^3, the preferred ring to the ring A ⁴ and ring A ⁵ are 1,7-dioxaspiro [5.5] undecane-3,9 is a diyl, in other rings, ring A ^1, ring A ^2, ring Preferred rings for A ³ , ring A ⁴ and ring A ⁵ include the following rings.
1-cyano-trans-cyclohexane-1,4-diyl, 2,2-difluoro-trans-cyclohexane-
1,4-diyl, 2-fluorocyclohex-1-ene-1,4-diyl, 2,3-difluorobenzene-1,
4-diyl and 2,2-dichlorobicyclo [1.1.
1] Pentane-1,3-diyl. As a ring in which a hydrogen atom on the ring may be substituted by a fluorine atom, a chlorine atom or a cyano group, bicyclo [1.1.1] pentane-1,3-
Diyl, trans-cyclohexane-1,4-diyl,
Cyclohex-1-ene-1,4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl,
Pyridazine-3,6-diyl, tetrahydropyran-
2,5-diyl, 1,3-dithiane-2,5-diyl,
And 1,3-oxathiane-2,5-diyl.

When it is desired to further increase the absolute value of the negative dielectric anisotropy value of the compound represented by the general formula (1), the ring A ¹ ,
Preferred rings for ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are 1,7
-Dioxaspiro [5.5] undecane-3,9-diyl, but in other rings, ring A ¹ , ring A ² , ring A ³ ,
Preferred rings for the ring A ⁴ and the ring A ⁵ include the following rings. 1-cyano-trans-cyclohexane-1,
4-diyl, 2,2-difluoro-trans-cyclohexane-1,4-diyl, 2-fluorocyclohexa-
1-ene-1,4-diyl, 2,3-difluorobenzene-1,4-diyl, and 2,2-dichlorobicyclo [1.1.1] pentane-1,3-diyl. As a ring in which a hydrogen atom on the ring may be substituted by a fluorine atom, a chlorine atom or a cyano group, trans-cyclohexane-1,
4-Diyl, cyclohex-1-en-1,4-diyl, pyridazine-3,6-diyl, and tetrahydropyran-2,5-diyl.

The compound of the present invention according to claim 1 or 2 has a negative value of a dielectric anisotropy having a large absolute value. Therefore, by mainly using the compound of the present invention,
A liquid crystal composition having a negative dielectric anisotropy value can be adjusted. This liquid crystal composition is disclosed, inter alia, in JP-A-2-17662.
No. 5, the vertical alignment method described in
It is useful for producing a device using a liquid crystal composition having a negative dielectric anisotropy value such as S. In addition, by mixing and using the compound of the present invention with another liquid crystal compound or composition, an appropriate setting of the dielectric anisotropy value can be performed. Can be spread. The compound of the present invention according to claim 1 or 2 has a small elastic constant and the temperature dependence of the constant is small. Therefore, a novel liquid crystal composition having a low driving voltage can be prepared by using the compound of the present invention.

The compound of the present invention described in claim 1 or 2 has good compatibility with other liquid crystal compounds. For this reason, when the compound of the present invention is compounded in a liquid crystal composition, problems such as precipitation of the compound hardly occur. In addition, the compound of the present invention can be incorporated in a large amount into a liquid crystal composition,
As a result, the excellent properties of the compound of the present invention can be strongly reflected in the liquid crystal composition.

The compound of the present invention described in claim 1 or 2 can obtain a desired magnitude of refractive index anisotropy value by appropriately designing its structure. That is, when a particularly high refractive index anisotropy value is required, a ring having many sites having a resonance structure such as an aromatic ring may be selected. When a low refractive index anisotropy value is required, a ring having many sites having no resonance structure, such as a trans-cyclohexane-1,4-diyl ring, may be selected. More specifically,
The compound of the present invention represented by the general formula (1) includes R ¹ , Y ¹ ,
X ¹ , X ² , X ³ , X ⁴ , ring A ¹ , ring A ² , ring A ³ , ring A ⁴ , ring A ⁵ , a ¹ , a ² , a ³ , a ⁴ and a ⁵ are appropriately selected. By doing so, a desired value of the refractive index anisotropy value can be obtained.
More specifically, the refractive index anisotropy value can be adjusted by appropriately selecting the ring A ¹ , the ring A ² , the ring A ³ , the ring A ⁴ and the ring A ⁵ . That is, when a particularly high refractive index anisotropy value is required, a ring having many sites having a resonance structure such as an aromatic ring may be selected. When a low refractive index anisotropy value is required, a ring having many sites having no resonance structure, such as a trans-cyclohexane-1,4-diyl ring, may be selected. By freely selecting the refractive index anisotropy value, the degree of freedom in designing the liquid crystal panel is increased.

Each of the compounds of the present invention according to claim 1 or 2 has a low viscosity, and does not significantly increase the viscosity of the whole liquid crystal composition even when used in a large amount in the liquid crystal composition. . Further, the temperature dependence of the viscosity, particularly at low temperatures, is extremely small. By using the liquid crystal compound having the excellent viscosity, a liquid crystal composition having a high-speed response can be adjusted. Each of the compounds of the present invention described in claim 1 or 2 is chemically and physically stable, and a liquid crystal composition using the compound has a high specific resistance and a high voltage holding ratio.
It has high stability against external factors such as ultraviolet rays and heating, and has sufficient chemical and physical stability as a component of a practical liquid crystal composition.

The phase transition temperature of the compound of the present invention according to claim 1 or 2 can be adjusted by appropriately selecting the number of rings. That is, when a particularly high clearing point is required, a compound having a large number of rings may be selected, and when a particularly low clearing point is required, a compound having a small number of rings may be selected.

As described above, the compound of the present invention described in claim 1 or 2 has various physical properties suitable as an electro-optical display material. By using the compound of the present invention, a novel liquid crystal composition having good characteristics can be prepared. In addition, a liquid crystal compound having desired characteristics, a liquid crystal composition and a liquid crystal display device using the same can be obtained by appropriately designing the structure according to the application. For example, although the compound of the present invention is characterized by exhibiting a large negative dielectric anisotropy value, it can be used not only for a liquid crystal composition having a negative dielectric anisotropy value but also for a positive liquid crystal composition. It can be added to a composition having a dielectric anisotropy value to adjust the dielectric anisotropy value and other properties. More specifically, the compound of the present invention or a liquid crystal composition using the same may be prepared in various display systems using a compound or a composition having a negative dielectric anisotropy value (for example, described in JP-A-2-176625). Vertical alignment method, IPS, ECB (HAN or DAP etc.), DS, GH or PC etc., especially vertical alignment method as described in JP-A-2-176625 or IPS. it can. However, not only can they be used in those methods, but also various display methods (for example, TN,
STN or TN based AM (TFT or MI
M) etc.) (for example, dielectric anisotropy value, elastic constant, refractive index anisotropy value, viscosity,
It can also be used to improve or adjust physical stability).

Hereinafter, the liquid crystal composition of the present invention will be described. The liquid crystal composition according to the present invention comprises at least one compound according to any one of claims 1 to 2 in the range of 0.1 to 99.9.
It is preferable that the content is contained in a ratio of% by weight in order to exhibit excellent characteristics. More specifically, the liquid crystal composition provided by the present invention comprises, in addition to a first component containing at least one compound according to any one of claims 1 to 2, a general formula ( It is completed by mixing the compounds selected from the compound group represented by 2) to (12) at an appropriate ratio. The compounds represented by the general formulas (2) to (4) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ² and Y ² represent the same meaning as described above.)

[0056]

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[0057]

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[0058]

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The compounds represented by the general formulas (2) to (4) are compounds having a positive dielectric anisotropy value, have excellent thermal stability and chemical stability, and have a high voltage holding ratio. T, which requires high reliability such as high resistance or large specific resistance
When a liquid crystal composition for FT is prepared, it is a particularly preferable compound. When adjusting the liquid crystal composition for TFT,
The compound represented by the general formulas (2) to (4) can be used in an amount of 0.1 to 99.9% by weight based on the total weight of the liquid crystal composition, but preferably 10 to 97% by weight. %, More preferably 40 to 95% by weight. Further, the compounds represented by the general formulas (7) to (9) may be further contained for the purpose of adjusting the viscosity. When preparing a liquid crystal composition for STN or TN, the compounds represented by general formulas (2) to (4) can also be used. In that case, the use amount of 50% by weight or less is preferable.

The compounds represented by formulas (5) and (6) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ³ , Y ³ and R ⁴
Represents the same meaning as described above. )

[0061]

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[0062]

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The compounds represented by the general formulas (5) and (6) have a positive and large dielectric anisotropy value, and are used particularly for the purpose of reducing the threshold voltage of the liquid crystal composition. Also,
It is also used for the purpose of expanding the nematic range such as adjusting the refractive index anisotropy value and increasing the clearing point. Further, it is also used for the purpose of improving the steepness of the VT curve of the liquid crystal composition for STN or TN.

The compounds represented by the general formulas (5) and (6) are preferable compounds particularly when preparing liquid crystal compositions for STN and TN. When the amount of the compounds represented by the general formulas (5) and (6) is increased, the threshold voltage of the liquid crystal composition decreases and the viscosity increases. Therefore,
As long as the viscosity of the liquid crystal composition satisfies the required characteristics, it is advantageous to use a large amount of the liquid crystal composition because low-voltage driving can be performed. The amount of the compounds represented by the general formulas (5) and (6) is 0.1 to 9 when adjusting the liquid crystal composition for STN or TN.
Although it can be used in the range of 9.9% by weight,
It is 97% by weight, more preferably 40 to 95% by weight.

The compounds represented by formulas (7) to (9) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ⁵ and R ⁶ represent the same meaning as described above.)

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The compounds represented by the general formulas (7) to (9) are compounds having a small absolute value of dielectric anisotropy and being almost neutral. The compound represented by the general formula (7) is mainly used for the purpose of adjusting the viscosity or adjusting the refractive index anisotropy value. Further, the compounds represented by the general formulas (8) and (9) are used for the purpose of expanding the nematic range such as increasing the clearing point or adjusting the refractive index anisotropy value. General formula (7)-
When the amount of the compound represented by (9) is increased, the threshold voltage of the liquid crystal composition increases, and the viscosity decreases.
Therefore, as long as the required value of the threshold voltage of the liquid crystal composition is satisfied, it can be used in a large amount. General formula (7)
When preparing a liquid crystal composition for TFT, the amount of the compound represented by (9) is preferably 40% by weight, more preferably 35% by weight or less. In addition, when adjusting the liquid crystal composition for STN or TN, preferably 7
0% by weight or less, more preferably 60% by weight or less.

The compounds represented by formulas (10) to (12) used in the liquid crystal composition of the present invention preferably include the following compounds. (R ⁷ and R ⁸ represent the same meaning as described above.)

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The compounds represented by the general formulas (10) to (12) are compounds having a negative value of dielectric anisotropy similarly to the compound according to claim 1 or 2 of the present invention. It is used as a base compound of an N-type liquid crystal composition or for controlling the dielectric anisotropy of a P-type liquid crystal composition. As another application, the compound represented by the general formula (10) is a bicyclic compound, and is mainly used for adjusting a threshold voltage, adjusting a viscosity, or adjusting a refractive index anisotropy value. The general formula (1
The compound represented by 1) is used for the purpose of widening the nematic range such as increasing the clearing point or adjusting the refractive index anisotropy value. The compound represented by the general formula (12) is used for the purpose of increasing the nematic range, reducing the threshold voltage, and increasing the refractive index anisotropy value.

The compounds represented by the general formulas (10) to (12) are mainly used for N-type liquid crystal compositions. Increasing the amount of the compounds decreases the threshold voltage of the liquid crystal composition. Becomes larger. Therefore, it is desirable to use a small amount as long as the required value of the threshold voltage of the liquid crystal composition is satisfied. However, the absolute value of the negative dielectric anisotropy is 5
If the amount is less than 40% by weight, low-voltage driving may not be performed. General formulas (10) to (1)
The amount of the compound represented by 2) is preferably 40% by weight or more, more preferably 50 to 95% by weight, when a liquid crystal composition for an N-type TFT is prepared. In order to control the elastic constant and control the voltage-transmittance curve (VT curve) of the liquid crystal composition, the general formula (10) is used.
The compound represented by (12) may be mixed with the P-type composition. In this case, the amount of the compounds represented by the general formulas (10) to (12) is preferably 30% by weight or less.

The liquid crystal composition of the present invention contains OCB
(Optically Compensated Bi
Except for a special case such as a liquid crystal composition for reference, usually, a helical structure of the liquid crystal composition is induced to adjust a required twist angle, and reverse twist (reverse twist) is performed.
For the purpose of preventing ist), an optically active compound is added. In the present invention, any of the known optically active compounds used for such a purpose can be used. Preferred examples of the compound include the following optically active compounds.

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In the liquid crystal composition of the present invention, these optically active compounds are usually added to adjust the twist pitch. The twist pitch is preferably adjusted in the range of 40 to 200 μm for a liquid crystal composition for TFT and TN. In the case of a liquid crystal composition for STN, it is preferable to adjust the composition to a range of 6 to 20 μm. In addition, bistable TN (Bis
In the case of table TN), the thickness is preferably adjusted to a range of 1.5 to 4 μm. Further, two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the pitch.

The liquid crystal composition of the present invention comprises a merocyanine compound,
A dichroic dye such as a styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye can be added to be used as a liquid crystal composition for GH. Alternatively, NCAP prepared by microencapsulating nematic liquid crystal, or polymer network liquid crystal display device (PN
Polymer-dispersed liquid crystal display device (P
It can also be used as a liquid crystal composition for DLCD). In addition, it can be used as a liquid crystal composition for DS.

The liquid crystal composition of the present invention is prepared by a conventional method. Generally, a method of dissolving various components at a high temperature is used.

The compound of the present invention described in claim 1 or 2 can be easily produced by a known organic synthetic chemistry technique. One example of the production method is shown in Reaction Formula 1.

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Hereinafter, the above synthesis route will be described. The compound represented by Formula 1 is commercially available. The compound represented by Formula 1 is reacted with thionyl chloride and methanol to be derived into a compound represented by Formula 2 . The compound represented by the formula 2 is reacted with ethylene glycol in the presence of an acid catalyst to be derived into a compound represented by the formula 3 .

The compound represented by the formula ( 4 ) is lithiated with sec-butyllithium and then reacted with bromine to form a compound represented by the formula ( 5)
To the compound represented by The compound represented by the formula 5 is reacted with magnesium to obtain a Grignard reagent, and then reacted with the compound represented by the formula 3 to be derived into a compound represented by the formula 6 . The compound represented by the formula ( 6 ) is reacted with an ylide obtained by reacting (methoxymethyl) triphenylphosphonium chloride with potassium t-butoxide to obtain a compound represented by the formula ( 7 ).

The compound represented by the formula ( 8 ) is reacted with magnesium to give a Grignard reagent, and then reacted with the compound represented by the formula ( 7 ) to be derived into the compound represented by the formula ( 9 ). The compound represented by the formula 9 is obtained by converting (methoxymethyl) chloride
The compound is reacted with ylide obtained by reacting triphenylphosphonium with potassium t-butoxide to obtain a compound represented by the formula ( 10 ). The compound represented by the formula ( 10 ) is deprotected by treatment with dilute hydrochloric acid to be derived into a compound represented by the formula ( 11 ). The compound represented by the formula 11 is represented by D
Reduction with IBAL (diisobutylaluminum hydride) leads to the compound of formula 12 . The compound represented by the formula 12 is treated with dilute hydrochloric acid to perform deprotection,
It is derived to the compound represented by 13 . The compound represented by the formula ( 13 ) is treated with an acid catalyst to effect cyclization, and is derived into the target compound represented by the formula ( 14 ).

[0082]

EXAMPLES The production method and use examples of the compound of the present invention will be described in more detail with reference to the following examples. The present invention is not limited by the embodiments. In the description of the examples, N is the specified concentration (gram equivalent / l), M
Represents a molar concentration (mol / l), and Δε of the liquid crystalline compound
(Dielectric anisotropy value) is an extrapolated value (2) from a composition comprising the following base liquid crystal A (85 wt%) and the compound (15 wt%).
Δn (measured at 5 ° C.)
Is the following mother liquid crystal B85wt% and the compound 15wt%
And the measured value (measured at 25 ° C.) of the composition consisting of: Composition of mother liquid crystal A

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Five types of ester compounds represented by the above general formula and having different alkyl groups (R ⁹ , R ¹⁰ ) at both terminals are represented by the following formula:
The following mixture was mixed to obtain mother liquid crystal A. Δε = -1.5

Composition of Mother Liquid Crystal B

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A mother liquid crystal B was prepared by mixing four types of compounds represented by the above general formula and having different terminal alkyl groups (R ¹¹ , R ¹² ) at the following ratios. Δn = 0.137

Example 1 3- (2- (trans-4-n-pentylcyclohexyl) ethyl) -9- (2,3-difluoro-4-n-propylphenyl) -1,7-dioxaspiro [5.5 ]
Synthesis of undecane ( 13 ) 1st step Synthesis of dimethyl 4-oxopimelate ( 2 ) 4-oxopimelic acid ( 1 ) (1742 g, 10.0 m)
ol) and methanol (4000 ml).
After cooling to 0 ° C., thionyl chloride (1428 g, 1
(2.0 mol) was added dropwise and reacted for 1 hour. After completion of the reaction, water (4000 ml) was added to the reaction solution under ice cooling,
Then it was extracted with hexane (10000 ml). The obtained organic layer was washed with water (5000 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 10/1) to give dimethyl 4-oxopimelate ( 2 ) (1897 g, 9.38 m).
ol; yield 94%). MS / 202 (M ^<+> ).

Second stage 2,2-bis (2-methoxycarbonylethyl) -1,
Synthesis of 3 -dioxolane ( 3 ) Dimethyl 4-oxopimelate ( 2 ) obtained in the first step
(1897 g, 9.38 mol), a mixture of ethylene glycol (698.8 g, 11.3 mol), p-toluenesulfonic acid monohydrate (89.23 g, 0.469 mol) and toluene (8000 ml) was heated, The mixture was heated under reflux for 5 hours while distilling off. After completion of the reaction, the resultant was cooled to room temperature and washed twice with water (5000 ml). The obtained organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2,2-bis (2-methoxycarbonylethyl) -1,3-dioxolane ( 3 ) (1915 g, 7.78 mol; yield 83
%). MS / 246 (M ^<+> ).

Third Step Synthesis of 1-bromo-2,3-difluoro-4-n-propylbenzene ( 5 ) 1,2-difluoro-3-n-propylbenzene ( 4 )
(3123 g, 20.0 mol) and a mixture of THF (tetrahydrofuran) (15000 ml) at -78 ° C.
Then, a 1.56 M sec-butyllithium hexane solution (22.0 mol, 14100 ml) was added dropwise over 30 minutes, and the reaction was allowed to proceed for 1 hour. At the same temperature, bromine (3835 g, 24.0 mol) was added dropwise to the reaction solution in 30 minutes, and then the temperature was gradually raised to 0 ° C., and the reaction was carried out at the same temperature for 1 hour. After the reaction was completed, water (20000 ml) was added to the reaction solution, and then extracted with heptane (50000 ml). The obtained organic layer was washed with water (15000 ml) and then dried over anhydrous magnesium sulfate. Purified by vacuum distillation,
1-bromo-2,3-difluoro-4-n-propylbenzene ( 5 ) (1899 g, 8.08 mol; yield 40)
%). MS / 235 (M ^<+> ).

Fourth stage 2- (2-methoxycarbonylethyl) -2- (3-oxo-3- (2,3-difluoro-4-n-propylphenyl) -n-propyl) -1,3-dioxolane Synthesis of ( 6 ) In magnesium (216.0 g, 8.89 mol),
1-bromo-2,3-difluoro-4 obtained in the third step
-N-propylbenzene ( 5 ) (1899 g, 8.08)
mol) in THF (3000 ml) was added dropwise and reacted at room temperature for 7 hours to obtain a Grignard reagent. In a separate container, 2,2-bis (2-methoxycarbonylethyl) -1,3-dioxolane ( 3 ) obtained in the second step (1809 g,
7.35 mol) and THF (2000 ml) were mixed and cooled to 0 ° C. In this, while keeping the same temperature,
After the above-prepared Grignard reagent was dropped, the mixture was reacted for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove THF, and water (5000 ml) was added dropwise, followed by extraction with toluene (7000 ml). The obtained organic layer was washed with water (5
000 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2- (2-methoxycarbonylethyl) -2
-(3-oxo-3- (2,3-difluoro-4-n-
(Propylphenyl) -n-propyl) -1,3-dioxolane ( 6 ) (590.4 g, 1.59 mol; yield 2)
2%). MS / 370 (M ^<+> ).

Fifth stage 2- (2-methoxycarbonylethyl) -2- (3-
(2,3-difluoro-4-n-propylphenyl)-
Synthesis of 4-methoxy-3-butenyl) -1,3-dioxolane ( 7 ) THF (30 g) of (methoxymethyl) triphenylphosphonium chloride (819.5 g, 2.39 mol) under ice cooling.
00 ml) solution and potassium t-butoxide (268.
(2 g, 2.39 mol) in THF (800 ml) was added dropwise, and the mixture was reacted at room temperature for 1 hour. Then, the 2- (2-methoxycarbonylethyl) -2- (3-oxo-3- (2,3-difluoro-4-n-propylphenyl) -n-propyl) obtained in the fourth step was added to this solution. -1,
3-dioxolane ( 6 ) (590.3 g, 1.59 mo
A solution of l) in THF (2500 ml) was added dropwise over 30 minutes under ice-cooling, followed by reaction at room temperature overnight. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove THF, and then water (2500 ml) was added to the reaction solution, and then toluene (6000 ml) was added.
Extracted in l). The obtained organic layer was washed with water (2500 ml).
And dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2-
(2-methoxycarbonylethyl) -2- (3- (2,
3-difluoro-4-n-propylphenyl) -4-methoxy-3-butenyl) -1,3-dioxolane ( 7 )
(575.3 g, 1.44 mol; yield: 91%) was obtained. MS / 398 (M ^<+> ).

Sixth stage 2- (3-oxo-5- (trans-4-n-pentylcyclohexyl) -n-pentyl) -2- (3- (2,
3-difluoro-4-n-propylphenyl) -4-methoxy-3-butenyl) -1,3-dioxolane ( 9 )
In magnesium (40.52 g, 1.67 mol),
TH of 1-n-pentyl-4- (2-bromoethyl) cyclohexane ( 8 ) (414.8 g, 1.59 mol)
A solution of F (1200 ml) was added dropwise and reacted at room temperature for 7 hours to obtain a Grignard reagent. In a separate container, the 2- (2-methoxycarbonylethyl) -2- (3-
(2,3-difluoro-4-n-propylphenyl)-
4-methoxy-3-butenyl) -1,3-dioxolane ( 7 ) (575.1 g, 1.44 mol) and THF (1
200 ml) and cooled to 0 ° C. In this,
While maintaining the same temperature, the previously prepared Grignard reagent was added dropwise, and then reacted for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove THF, and then water (1000 ml) was added dropwise. Extracted with toluene (2000 ml). The obtained organic layer was washed twice with water (1000 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene) to give 2- (3-oxo-5-
(Trans-4-n-pentylcyclohexyl) -n-
Pentyl) -2- (3- (2,3-difluoro-4-n
-Propylphenyl) -4-methoxy-3-butenyl)
-1,3-dioxolane ( 9 ) (386.5 g, 0.7
04 mol; yield 49%). MS / 549
(M ⁺ ).

Step 7 2- (3-methoxymethylene-5- (trans-4-n
-Pentylcyclohexyl) -n-pentyl) -2-
Synthesis of (3- (2,3-difluoro-4-n-propylphenyl) -4-methoxy-3-butenyl) -1,3-dioxolane ( 10 ) Under ice-cooling, (methoxymethyl) triphenylphosphonium chloride ( 361.9 g (1.06 mol) of THF (12
00 ml) solution and potassium t-butoxide (118.
(5 g, 1.06 mol) in THF (300 ml) was added dropwise, and the mixture was reacted at room temperature for 1 hour. Then, to this solution was added 2- (3-oxo-5- (trans-4-n-pentylcyclohexyl) -n-pentyl) -2- (3- (2,3-difluoro-4) obtained in the sixth step. -N-propylphenyl) -4-methoxy-3-butenyl) -1,
3-dioxolane ( 9 ) (386.2 g, 0.704 m)
ol) in THF (1200 ml) was added dropwise over 30 minutes under ice-cooling, followed by reaction at room temperature overnight. After the reaction,
The reaction solution was concentrated under reduced pressure to remove THF, and then water (150
0 ml) and then extracted with toluene (3000 ml). The obtained organic layer was washed with water (1500 ml) and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2- (3-methoxymethylene-5- (trans-4-n-pentylcyclohexyl) -n-pentyl. ) -2- (3- (2,3-
Difluoro-4-n-propylphenyl) -4-methoxy-3-butenyl) -1,3-dioxolane ( 10 )
(363.3 g, 0.630 mol; yield 90%) was obtained. MS / 577 (M ^<+> ).

Step 8 2- (3-formyl-5- (trans-4-n-pentylcyclohexyl) -n-pentyl) -2- (3-formyl-3- (2,3-difluoro-4-n) -Propylphenyl) -n-propyl) -1,3-dioxolane ( 1
1 ) Synthesis of 2- (3-methoxymethylene-5-
(Trans-4-n-pentylcyclohexyl) -n-
Pentyl) -2- (3- (2,3-difluoro-4-n
-Propylphenyl) -4-methoxy-3-butenyl)
-1,3-dioxolane ( 10 ) (363.1 g, 0.1.
629 mol) and THF (1200 ml), 1N diluted hydrochloric acid (300 ml) was added dropwise at 0 ° C., and the mixture was reacted at room temperature overnight. After completion of the reaction, add 1N
Sodium bicarbonate aqueous solution (400 ml), and then concentrated under reduced pressure to distill off THF.
00 ml). The obtained organic layer was washed with water (1000
ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene).
2- (3-formyl-5- (trans-4-n-pentylcyclohexyl) -n-pentyl) -2- (3-formyl-3- (2,3-difluoro-4-n-propylphenyl) -n -Propyl) -1,3-dioxolane ( 1
1 ) (322.3 g, 0.587 mol; yield 93%)
I got MS / 549 (M ^<+> ).

9th stage 2- (3-hydroxymethyl-5- (trans-4-n
-Pentylcyclohexyl) -n-pentyl) -2-
Synthesis of (3- (2,3-difluoro-4-n-propylphenyl) -4-hydroxybutyl) -1,3-dioxolane ( 12 ) 2- (3-formyl-5- (trans-4-n- Pentylcyclohexyl) -n-pentyl) -2- (3-formyl-3- (2,3-difluoro-4-n-propylphenyl) -n-propyl) -1,3-dioxolane ( 1
1 ) 1.52 M at −60 ° C. to a mixture of (322.0 g, 0.587 mol) and toluene (1200 ml).
DIBAL in toluene (1.17 mol, 772)
ml) was added dropwise over 30 minutes and allowed to react for 1 hour.
After completion of the reaction, water (1000 ml) was added to the reaction solution, and then extracted with toluene (1000 ml). The obtained organic layer was washed with water (1000 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2- (3-hydroxymethyl-5-
(Trans-4-n-pentylcyclohexyl) -n-
Pentyl) -2- (3- (2,3-difluoro-4-n
-Propylphenyl) -4-hydroxybutyl) -1,
3-Dioxolane ( 12 ) (232.6 g, 0.421)
mol; yield 72%). MS / 553 (M ^<+> ).

Step 10 2- (2,3-difluoro-4-n-propylphenyl) -5-oxo-8-hydroxymethyl-10- (trans-4-n-pentylcyclohexyl) -n-decanol ( 13 2- (3-hydroxymethyl-5-) obtained in the ninth step
(Trans-4-n-pentylcyclohexyl) -n-
Pentyl) -2- (3- (2,3-difluoro-4-n
-Propylphenyl) -4-hydroxybutyl) -1,
3-dioxolane ( 12 ) (232.4 g, 0.420)
mol) and acetone (800 ml) at 0 ° C.
Then, 1N diluted hydrochloric acid (300 ml) was added dropwise thereto, and the mixture was heated under reflux for 2 hours. After completion of the reaction, a 1N aqueous solution of sodium hydrogencarbonate (400 ml) was added to the reaction mixture under ice cooling, and the mixture was concentrated under reduced pressure to distill off acetone.
Extracted in l). After the obtained organic layer was washed with water (600 ml), it was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to give 2-
(2,3-difluoro-4-n-propylphenyl)-
5-oxo-8-hydroxymethyl-10- (trans-4-n-pentylcyclohexyl) -n-decanol ( 13 ) (125.3 g, 0.246 mol; yield 59)
%). MS / 509 (M ^<+> ).

Eleventh stage 3- (2- (trans-4-n-pentylcyclohexyl) ethyl) -9- (2,3-difluoro-4-n-propylphenyl) -1,7-dioxaspiro [5.5 ]
Synthesis of undecane ( 14 ) 2- (2,3-difluoro-4-n obtained in the 10th step
-Propylphenyl) -5-oxo-8-hydroxymethyl-10- (trans-4-n-pentylcyclohexyl) -n-decanol ( 13 ) (125.0 g, 0.1 g).
246 mol), p-toluenesulfonic acid monohydrate (2.34 g, 0.0123 mol) and toluene (5
00 ml) was heated to reflux for 20 hours while distilling off water. After completion of the reaction, the reaction mixture was cooled to room temperature, and water (400 m
Washed twice in l). The obtained organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene) and then recrystallized (hexane / toluene = 1/1) to give 3- (2- (trans-4-n -Pentylcyclohexyl) ethyl) -9- (2,3-difluoro-
4-n-propylphenyl) -1,7-dioxaspiro [5.5] undecane ( 14 ) (5.61 g, 0.01
14 mol; yield 5%). MS / 491
(M ⁺ ), Δε = -1.7, Δn = 0.127.

The following compounds can be synthesized according to the method of Example 1.

[0100]

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[0101]

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[0102]

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[0103]

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[0104]

As described above, according to the present invention, a low-viscosity, large-value negative dielectric anisotropy value, a controlled optical anisotropy value, a high specific resistance value and a high It is possible to provide a liquid crystal compound which has a voltage holding ratio and is stable against heat or ultraviolet irradiation, a liquid crystal composition containing the same, and a liquid crystal display element manufactured using the liquid crystal composition. Was.

Claims (12)

[Claims] 1. A liquid crystalline compound having a 1,7-dioxaspiro [5.5] undecane-3,9-diyl group in a skeletal structure. 2. A compound of the general formula (1) (Wherein, R ¹ and Y ¹ each independently represent an alkyl group having 1 to 20 carbon atoms, a hydrogen atom, a halogen atom, a cyano group, a cyanate group, an isocyano group, or an isothiocyanate group; One or more methylene groups which are not adjacent to each other are an oxygen atom, a sulfur atom, a nitrogen atom, -C≡C-, and a silylene group in which one or more hydrogen atoms may be substituted by an alkyl group having 1 to 10 carbon atoms Or one or more hydrogen atoms in these alkyl groups may be substituted with a fluorine atom or a chlorine atom, and these alkyl groups may be optically active. Well,
X ¹ , X ² , X ³ and X ⁴ are each independently a single bond,-(CH
₂ ) _2- , -CH = CH-, -C≡C-, -COO-,-
_{OCO -, - CH 2 O -} , - OCH 2 -, - (CH 2)
_{4 -, - (CH 2)} 3 O -, - O (CH 2) 3 -, - CH =
CHCH ₂ CH ₂ —, —CH ₂ CH = CHCH ₂ —, —CH
₂ CH ₂ CH = CH-, -CH = CHCH = CH-, -C
_{F 2 O -, - OCF 2} -, - CH = CHCH 2 O -, - O
_{CH 2 CH = CH -, -} CF = CF -, - CH 2 CF
_{2 -, - CF 2 CH 2} -, - (CF 2) 2 -, - (CF 2) 4
_{-, - (CH 2) 2} COO -, - OCO (CH 2) 2 -, -
CH = CHCOO-, -OCOCH = CH-, -CH =
CHC≡C— or —C≡CCH ＝ CH—, and a ring A
¹ , ring A ² , ring A ³ , ring A ⁴ and ring A ⁵ are each independently 1,
7-dioxaspiro [5.5] undecane-3,9-diyl, bicyclo [1.1.1] pentane-1,3-diyl, trans-cyclohexane-1,4-diyl, cyclohex-1-ene-1, Represents 4-diyl or 1,4-phenylene, and carbon atoms constituting these rings may be substituted with a nitrogen atom, an oxygen atom or a sulfur atom,
A hydrogen atom on these rings may be substituted with a halogen atom or a cyano group, but these rings A ¹ , A ² ,
At least one of ring A ³ , ring A ⁴ and ring A ⁵ is 1,7-
Dioxaspiro [5.5] undecane-3,9-diyl, wherein a ¹ , a ² , a ³ , a ⁴ and a ⁵ are each independently 0
Or 1, wherein a ¹ + a ² + a ³ + a ⁴ + a ⁵ ≧ 1, and each atom constituting the compound may be substituted with its isotope. The liquid crystalline compound according to claim 1, which is represented by the formula: 3. A liquid crystal composition comprising at least two components, comprising at least one kind of the liquid crystal compound according to claim 1. 4. A compound comprising at least one compound according to claim 1 or 2 as a first component, and a second component comprising
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (2), (3) and (4). Embedded image (Wherein, R ² represents an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group may be substituted with an oxygen atom or —CH ＝ CH—,
One or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and Y ² is a fluorine atom, a chlorine atom, —OCF ₃ , —OCF ₂ H, —CF ₃ , —CF ₂ H ,
-CFH _2, -OCF ₂ CF ₂ H or -OCF ₂ CFHCF
₃ represents, L ¹ and L ² represents a hydrogen atom or a fluorine atom each independently, Z ¹ and Z ² are each independently - (CH _{2) 2
-, - (CH 2) 4} -, - COO -, - CF 2 O -, - O
CF ₂ —, —CH ＝ CH— or a single bond, and ring Q ¹ is trans-cyclohexane-1,4-diyl, 1,3-dioxane-2,5-diyl, or a hydrogen atom is substituted by a fluorine atom. And ring Q ² is trans-cyclohexane-1,4-diyl or 1,4 optionally substituted with a hydrogen atom by a fluorine atom.
Represents phenylene, and each atom constituting these compounds may be substituted with its isotope. ) 5. A compound comprising at least one compound according to claim 1 or 2 as a first component, and
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (5) and (6). Embedded image (Wherein, R ³ and R ⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. may be, also, one or more hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y ³
Represents a cyano group or —C≡C—CN, and ring Q ³ represents trans-cyclohexane-1,4-diyl, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5. A ring Q ⁴ represents trans-cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom; ⁵ represents trans-cyclohexane-1,4-diyl or 1,4-phenylene, Z ³ represents — (CH ₂ ) ₂ —, —COO— or a single bond, and L ³ , L ⁴ and L ⁵ each represent Each independently represents a hydrogen atom or a fluorine atom, and b, c and d each independently represent 0 or 1
And the atoms constituting these compounds may be substituted with their isotopes. ) 6. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (2), (3) and (4), and as a third component, consists of the general formulas (7), (8) and (9) A liquid crystal composition comprising at least one compound selected from a compound group. Embedded image (Wherein, R ⁵ and R ⁶ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. And at least one hydrogen atom in the alkyl group may be substituted with a fluorine atom.
^6, ring Q ⁷ and ring Q ⁸ are each independently trans - cyclohexane-1,4-diyl, pyrimidine-2,5-diyl, or a hydrogen atom may be substituted with a fluorine atom 1,4 Represents phenylene, and Z ⁴ and Z ⁵ are each independently —C≡C—, —COO—, — (CH ₂ ) ₂ —, —CH
ＣＨCH— or a single bond, and the atoms constituting these compounds may be substituted with their isotopes. ) 7. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
A liquid crystal composition comprising at least one compound selected from the group consisting of compounds represented by formulas (10), (11) and (12). Embedded image (Wherein, R ⁷ and R ⁸ each independently represent an alkyl group having 1 to 10 carbon atoms, and one or more non-adjacent methylene groups in the alkyl group are substituted with an oxygen atom or —CH ＝ CH—. And at least one hydrogen atom in the alkyl group may be substituted with a fluorine atom.
⁹ and ring Q ¹⁰ are each independently trans - represents a cyclohexane-1,4-diyl or 1,4-phenylene, L
⁶ and L ⁷ each independently represent a hydrogen atom or a fluorine atom but do not represent a hydrogen atom at the same time, and Z ⁶ and Z ⁷ each independently represent-(CH ₂ ) _2- , -COO- or The atoms representing a bond and constituting these compounds may be substituted with their isotopes. ) 8. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (7), (8) and (9), and as a third component, the general formulas (10), (11) and (1)
A liquid crystal composition comprising at least one compound selected from the compound group consisting of 2). 9. As a first component, at least one compound according to claim 1 or 2 is contained, and as a second component,
It contains at least one compound selected from the compound group consisting of the general formulas (5) and (6), and as a third component, a compound selected from the compound group consisting of the general formulas (7), (8) and (9). A liquid crystal composition comprising at least one selected compound. 10. A compound comprising at least one compound according to claim 1 or 2 as a first component, and a compound consisting of the general formulas (2), (3) and (4) as a second component. Containing at least one compound selected,
The third component contains at least one compound selected from the compound group consisting of the general formulas (5) and (6), and the fourth component contains the general formulas (7), (8) and (9) A liquid crystal composition comprising at least one compound selected from the group consisting of: 11. A liquid crystal composition comprising at least one optically active compound in addition to the liquid crystal composition according to claim 3. Description: 12. A liquid crystal display device comprising the liquid crystal composition according to claim 3. Description: